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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "N-Acetyl-N-{2-[(Z)-2-chloro-3,3,3-tri-", "fluoroprop-1-enyl]phenyl}acetamide", "Jia-Jia", "Niu,a,b", "Zhi-Gang", "Lia,b", "and", "Jing-Wei", "Xua*", "aNational", "Analytical", "Research", "Center", "of", "Electrochemistry", "and", "Spectroscopy,", "Changchun", "Institute", "of", "Applied", "Chemistry,", "Chinese", "Academy", "of", "Sciences,", "Changchun", "130022,", "People’s", "Republic", "of", "China,", "and", "bGraduate", "School", "of", "the", "Chinese", "Academy", "of", "Sciences,", "Beijing", "100039,", "People’s", "Republic", "of", "China", "Correspondence", "e-mail:", "jwxu@ciac.jl.cn", "Received", "14", "March", "2009;", "accepted", "21", "April", "2009", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "293", "K;", "mean", "(C–C)", "=", "0.004", "A˚;", "R", "factor", "=", "0.052;", "wR", "factor", "=", "0.136;", "data-to-parameter", "ratio", "=", "14.5.", "The", "title", "compound,", "C13H11ClF3NO2,", "adopts", "a", "Z", "conforma-", "tion.", "Halogen", "oxygen", "interactions", "[Cl", "O", "=", "2.967", "(3)", "A˚", "]", "in", "the", "crystal", "packing", "lead", "to", "the", "formation", "of", "a", "dimer", "joined", "by", "two", "Cl", "O", "bonds.", "Related", "literature", "The", "title", "compound", "is", "an", "important", "medical", "intermediate,", "see:", "Zhou", "et", "al.", "(2009).", "For", "the", "van", "der", "Waals", "radii", "of", "chlorine", "and", "oxygen,", "see:", "Politzer", "et", "al.", "(2007).", "organic", "compounds", "Experimental", "Crystal", "data", "C13H11ClF3NO2", "Mr", "=", "305.68", "Triclinic,", "P1", "a", "=", "8.4408", "(19)", "A˚", "b", "=", "9.385", "(2)", "A˚", "c", "=", "9.455", "(2)", "A˚", "=", "64.599", "(3)", "=", "80.727", "(4)", "Data", "collection", "Bruker", "SMART", "APEX", "CCD", "area-", "detector", "diffractometer", "Absorption", "correction:", "multi-scan", "(SADABS;", "Bruker,", "2003)", "Tmin", "=", "0.958,", "Tmax", "=", "0.978", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.052", "wR(F", "2)", "=", "0.136", "S", "=", "1.03", "2562", "reflections", "=", "89.756", "(3)", "V", "=", "666.0", "(3)", "A˚3", "Z", "=", "2", "Mo", "K", "radiation", "=", "0.32", "mm", "1", "T", "=", "293", "K", "0.13", "0.13", "0.07", "mm", "3747", "measured", "reflections", "2562", "independent", "reflections", "2155", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.010", "177", "parameters", "H-atom", "parameters", "constrained", "max", "=", "0.37", "e", "A˚", "3", "min", "=", "0.38", "e", "A˚", "3", "Data", "collection:", "SMART", "(Bruker,", "1998);", "cell", "refinement:", "SAINT-", "Plus", "(Bruker,", "1998);", "data", "reduction:", "SAINT-Plus;", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "SHELXTL", "(Sheldrick,", "2008);", "software", "used", "to", "prepare", "material", "for", "publication:", "SHELXTL.", "This", "work", "was", "supported", "by", "the", "Changchun", "Institute", "of", "Applied", "Chemistry,", "Chinese", "Academy", "of", "Sciences.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "KJ2121).", "References", "Bruker", "(1998).", "SMART", "and", "SADABS.", "Bruker", "AXS", "Inc.,", "Madison,", "Wisconsin,", "USA.", "Bruker", "(2003).", "SAINT-Plus.", "Bruker", "AXS", "Inc.,", "Madison,", "Wisconsin,", "USA.", "Politzer,", "P.,", "Lane,", "P.,", "Concha,", "M.", "C.,", "Ma,", "Y.", "&", "Murray,", "J.", "S.", "(2007).", "J.", "Mol.", "Model.", "13,", "305–311.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Zhou,", "H.,", "Niu,", "J.-J.,", "Xu,", "J.-W.", "&", "Hu,", "S.-J.", "(2009).", "Synth.", "Commun.", "39,", "716–732.", "Acta", "Cryst.", "(2009).", "E65,", "o1305", "doi:10.1107/S1600536809014779", "Niu", "et", "al.", "o1305" ]
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04-2969518-4
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04-2969518-1
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20-3246952-5
[ "Li2—Li3", "Li3—O3", "Li3—O300", "Li3—O2", "Li3—O4", "Li3—Li4", "Li4—O4", "Li4—O1", "Li4—O3", "Li4—O400", "O1—B1", "B1—C21", "B1—C11", "O11—C22", "O11—C12", "C11—C12", "C11—C16", "C12—C13", "C13—C14", "C13—H13", "C14—C15", "C14—H14", "C15—C16", "C15—H15", "C16—H16", "C21—C22", "C21—C26", "C22—C23", "C23—C24", "C23—H23", "C24—C25", "C24—H24", "C25—C26", "C25—H25", "C26—H26", "O2—B2", "B2—C31", "B2—C41", "O21—C32", "O21—C42", "C31—C32", "C31—C36", "C32—C33", "C33—C34", "C33—H33", "C34—C35", "C34—H34", "C35—C36", "C35—H35", "2.673", "(18)", "1.938", "(16)", "2.001", "(16)", "2.031", "(15)", "2.055", "(16)", "2.689", "(19)", "1.953", "(15)", "1.991", "(16)", "2.058", "(16)", "2.079", "(17)", "1.367", "(13)", "1.518", "(14)", "1.532", "(14)", "1.376", "(11)", "1.392", "(11)", "1.435", "(11)", "1.450", "(13)", "1.379", "(14)", "1.389", "(16)", "0.9500", "1.394", "(14)", "0.9500", "1.394", "(13)", "0.9500", "0.9500", "1.416", "(11)", "1.430", "(14)", "1.375", "(13)", "1.360", "(16)", "0.9500", "1.431", "(14)", "0.9500", "1.358", "(14)", "0.9500", "0.9500", "1.322", "(12)", "1.602", "(15)", "1.608", "(14)", "1.370", "(11)", "1.367", "(13)", "1.293", "(13)", "1.388", "(14)", "1.472", "(15)", "1.375", "(17)", "0.9500", "1.379", "(15)", "0.9500", "1.373", "(14)", "0.9500", "O41—C82", "C71—C72", "C71—C76", "C72—C73", "C73—C74", "C73—H73", "C74—C75", "C74—H74", "C75—C76", "C75—H75", "C76—H76", "C81—C86", "C81—C82", "C82—C83", "C83—C84", "C83—H83", "C84—C85", "C84—H84", "C85—C86", "C85—H85", "C86—H86", "O100—C103", "O100—C101", "C101—C102", "C101—H10A", "C101—H10B", "C102—H10C", "C102—H10D", "C102—H10E", "C103—C104", "C103—H10F", "C103—H10G", "C104—H10H", "C104—H10I", "C104—H10J", "O200—C203", "O200—C201", "C201—C202", "C201—H20A", "C201—H20B", "C202—H20C", "C202—H20D", "C202—H20E", "C203—C204", "C203—H20F", "C203—H20G", "C204—H20H", "C204—H20I", "C204—H20J", "supplementary", "materials", "1.383", "(14)", "1.397", "(15)", "1.413", "(15)", "1.473", "(15)", "1.40", "(2)", "0.9500", "1.296", "(19)", "0.9500", "1.400", "(14)", "0.9500", "0.9500", "1.370", "(16)", "1.455", "(14)", "1.304", "(19)", "1.42", "(2)", "0.9500", "1.381", "(18)", "0.9500", "1.405", "(15)", "0.9500", "0.9500", "1.431", "(13)", "1.444", "(12)", "1.496", "(9)", "0.9900", "0.9900", "0.9800", "0.9800", "0.9800", "1.503", "(8)", "0.9900", "0.9900", "0.9800", "0.9800", "0.9800", "1.412", "(13)", "1.456", "(12)", "1.506", "(8)", "0.9900", "0.9900", "0.9800", "0.9800", "0.9800", "1.515", "(9)", "0.9900", "0.9900", "0.9800", "0.9800", "0.9800", "sup-9" ]
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20-3246952-10
[ "supplementary", "materials", "C21—C22—C23—C24", "C22—C23—C24—C25", "C23—C24—C25—C26", "C24—C25—C26—C21", "C22—C21—C26—C25", "B1—C21—C26—C25", "O1—Li1—O2—B2", "O100—Li1—O2—B2", "O4—Li1—O2—B2", "Li2—Li1—O2—B2", "Li4—Li1—O2—B2", "Li3—Li1—O2—B2", "O1—Li1—O2—Li2", "O100—Li1—O2—Li2", "O4—Li1—O2—Li2", "Li4—Li1—O2—Li2", "Li3—Li1—O2—Li2", "O1—Li1—O2—Li3", "O100—Li1—O2—Li3", "O4—Li1—O2—Li3", "Li2—Li1—O2—Li3", "Li4—Li1—O2—Li3", "O1—Li2—O2—B2", "O3—Li2—O2—B2", "O200—Li2—O2—B2", "Li1—Li2—O2—B2", "Li4—Li2—O2—B2", "Li3—Li2—O2—B2", "O1—Li2—O2—Li1", "O3—Li2—O2—Li1", "sup-20", "0.6", "(15)", "−1.1", "(16)", "1.4", "(16)", "−1.3", "(15)", "0.8", "(14)", "179.0", "(10)", "122.7", "(11)", "−5.2", "(17)", "−140.9", "(11)", "127.6", "(12)", "171.6", "(11)", "−148.9", "(13)", "−4.9", "(6)", "−132.8", "(9)", "91.5", "(6)", "44.0", "(5)", "83.5", "(6)", "−88.4", "(6)", "143.7", "(9)", "8.0", "(6)", "−83.5", "(6)", "−39.5", "(6)", "−144.7", "(7)", "117.2", "(7)", "−12.0", "(11)", "−149.6", "(8)", "167.2", "(7)", "123.4", "(8)", "4.9", "(6)", "−93.1", "(6)", "O4—Li3—O300—C301", "Li2—Li3—O300—C301", "Li4—Li3—O300—C301", "Li1—Li3—O300—C301", "O3—Li3—O300—C303", "O2—Li3—O300—C303", "O4—Li3—O300—C303", "Li2—Li3—O300—C303", "Li4—Li3—O300—C303", "Li1—Li3—O300—C303", "C303—O300—C301—C302", "Li3—O300—C301—C302", "C301—O300—C303—C304", "Li3—O300—C303—C304", "O4—Li4—O400—C403", "O1—Li4—O400—C403", "O3—Li4—O400—C403", "Li1—Li4—O400—C403", "Li2—Li4—O400—C403", "Li3—Li4—O400—C403", "O4—Li4—O400—C401", "O1—Li4—O400—C401", "O3—Li4—O400—C401", "Li1—Li4—O400—C401", "Li2—Li4—O400—C401", "Li3—Li4—O400—C401", "C403—O400—C401—C402", "Li4—O400—C401—C402", "C401—O400—C403—C404", "Li4—O400—C403—C404", "40.6", "(15)", "−154.9", "(17)", "−9(2)", "96.4", "(14)", "118.8", "(10)", "−8.1", "(12)", "−118.1", "(9)", "46", "(2)", "−167.4", "(13)", "−62.3", "(13)", "−174.2", "(11)", "24.9", "(19)", "79.8", "(15)", "−118.1", "(12)", "125.5", "(9)", "−5.3", "(13)", "−117.5", "(8)", "54.2", "(19)", "−64.6", "(13)", "−166.3", "(10)", "−73.3", "(13)", "155.8", "(9)", "43.7", "(11)", "−144.7", "(14)", "96.6", "(12)", "−5.2", "(16)", "−171.2", "(10)", "26.1", "(14)", "79.8", "(11)", "−117.0", "(10)" ]
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20-3246952-21
[ "O3—Li4—O1—B1", "O400—Li4—O1—B1", "Li1—Li4—O1—B1", "Li2—Li4—O1—B1", "Li3—Li4—O1—B1", "O4—Li4—O1—Li2", "O3—Li4—O1—Li2", "O400—Li4—O1—Li2", "Li1—Li4—O1—Li2", "Li3—Li4—O1—Li2", "O4—Li4—O1—Li1", "O3—Li4—O1—Li1", "O400—Li4—O1—Li1", "Li2—Li4—O1—Li1", "Li3—Li4—O1—Li1", "Li2—O1—B1—C21", "Li1—O1—B1—C21", "Li4—O1—B1—C21", "Li2—O1—B1—C11", "Li1—O1—B1—C11", "Li4—O1—B1—C11", "O1—B1—C11—C12", "C21—B1—C11—C12", "O1—B1—C11—C16", "C21—B1—C11—C16", "C22—O11—C12—C13", "C22—O11—C12—C11", "C16—C11—C12—C13", "B1—C11—C12—C13", "C16—C11—C12—O11", "B1—C11—C12—O11", "O11—C12—C13—C14", "C11—C12—C13—C14", "C12—C13—C14—C15", "C13—C14—C15—C16", "C14—C15—C16—C11", "C12—C11—C16—C15", "B1—C11—C16—C15", "O1—B1—C21—C22", "C11—B1—C21—C22", "O1—B1—C21—C26", "C11—B1—C21—C26", "C12—O11—C22—C23", "C12—O11—C22—C21", "C26—C21—C22—O11", "B1—C21—C22—O11", "C26—C21—C22—C23", "B1—C21—C22—C23", "O11—C22—C23—C24", "146.6", "(7)", "24.4", "(12)", "−124.7", "(9)", "153.4", "(8)", "−167.4", "(7)", "88.9", "(7)", "−6.9", "(6)", "−129.1", "(9)", "81.9", "(6)", "39.1", "(7)", "7.0", "(7)", "−88.7", "(7)", "149.1", "(10)", "−81.9", "(6)", "−42.8", "(7)", "4.7", "(18)", "136.4", "(9)", "−122.5", "(9)", "−175.6", "(10)", "−43.9", "(12)", "57.2", "(11)", "173.5", "(8)", "−6.8", "(11)", "−4.4", "(13)", "175.3", "(7)", "−172.5", "(8)", "7.1", "(11)", "−1.1", "(12)", "−179.3", "(9)", "179.4", "(7)", "1.2", "(11)", "180.0", "(9)", "0.5", "(15)", "−0.7", "(16)", "1.7", "(15)", "−2.6", "(14)", "2.2", "(12)", "−179.8", "(9)", "−175.3", "(8)", "5.0", "(12)", "6.7", "(14)", "−173.0", "(8)", "171.9", "(8)", "−9.1", "(12)", "−179.3", "(8)", "2.5", "(13)", "−0.4", "(13)", "−178.7", "(9)", "179.5", "(9)", "supplementary", "materials", "O4—B4—C81—C82", "C71—B4—C81—C82", "C72—O41—C82—C83", "C72—O41—C82—C81", "C86—C81—C82—C83", "B4—C81—C82—C83", "C86—C81—C82—O41", "B4—C81—C82—O41", "O41—C82—C83—C84", "C81—C82—C83—C84", "C82—C83—C84—C85", "C83—C84—C85—C86", "C82—C81—C86—C85", "B4—C81—C86—C85", "C84—C85—C86—C81", "O2—Li1—O100—C103", "O1—Li1—O100—C103", "O4—Li1—O100—C103", "Li2—Li1—O100—C103", "Li4—Li1—O100—C103", "Li3—Li1—O100—C103", "O2—Li1—O100—C101", "O1—Li1—O100—C101", "O4—Li1—O100—C101", "Li2—Li1—O100—C101", "Li4—Li1—O100—C101", "Li3—Li1—O100—C101", "C103—O100—C101—C102", "Li1—O100—C101—C102", "C101—O100—C103—C104", "Li1—O100—C103—C104", "O1—Li2—O200—C203", "O3—Li2—O200—C203", "O2—Li2—O200—C203", "Li1—Li2—O200—C203", "Li4—Li2—O200—C203", "Li3—Li2—O200—C203", "O1—Li2—O200—C201", "O3—Li2—O200—C201", "O2—Li2—O200—C201", "Li1—Li2—O200—C201", "Li4—Li2—O200—C201", "Li3—Li2—O200—C201", "C203—O200—C201—C202", "Li2—O200—C201—C202", "C201—O200—C203—C204", "Li2—O200—C203—C204", "O3—Li3—O300—C301", "O2—Li3—O300—C301", "−174.3", "(8)", "9.2", "(12)", "173.7", "(10)", "−10.0", "(13)", "−4.1", "(16)", "175.0", "(10)", "179.9", "(8)", "−1.0", "(13)", "−179.8", "(10)", "4.0", "(18)", "−0.7", "(19)", "−2.1", "(17)", "0.9", "(15)", "−178.1", "(10)", "1.9", "(17)", "−122.4", "(10)", "116.2", "(9)", "3.6", "(13)", "169.2", "(10)", "62.4", "(14)", "−56.7", "(19)", "61.7", "(11)", "−59.7", "(10)", "−172.3", "(8)", "−6.7", "(15)", "−113.5", "(11)", "127.4", "(15)", "−61.6", "(13)", "114.8", "(10)", "−66.1", "(12)", "118.1", "(11)", "76.9", "(12)", "−157.8", "(9)", "−43.0", "(12)", "11.9", "(15)", "138.6", "(15)", "−99.7", "(15)", "−125.3", "(9)", "−0.1", "(11)", "114.8", "(9)", "169.6", "(9)", "−63.7", "(16)", "58.1", "(15)", "−81.0", "(11)", "118.8", "(9)", "173.7", "(10)", "−26.9", "(14)", "−82.5", "(14)", "150.6", "(12)", "sup-19" ]
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20-3246952-20
[ "supplementary", "materials", "C43—C44—H44", "C45—C44—H44", "C44—C45—C46", "C44—C45—H45", "C46—C45—H45", "C41—C46—C45", "C41—C46—H46", "C45—C46—H46", "B3—O3—Li3", "B3—O3—Li2", "Li3—O3—Li2", "B3—O3—Li4", "Li3—O3—Li4", "Li2—O3—Li4", "O3—B3—C61", "O3—B3—C51", "C61—B3—C51", "C52—O31—C62", "C52—C51—C56", "C52—C51—B3", "O2—Li1—Li2—O1", "O100—Li1—Li2—O1", "O4—Li1—Li2—O1", "Li4—Li1—Li2—O1", "Li3—Li1—Li2—O1", "O2—Li1—Li2—O3", "O1—Li1—Li2—O3", "O100—Li1—Li2—O3", "O4—Li1—Li2—O3", "Li4—Li1—Li2—O3", "Li3—Li1—Li2—O3", "O1—Li1—Li2—O2", "O100—Li1—Li2—O2", "O4—Li1—Li2—O2", "Li4—Li1—Li2—O2", "Li3—Li1—Li2—O2", "O2—Li1—Li2—O200", "O1—Li1—Li2—O200", "O100—Li1—Li2—O200", "O4—Li1—Li2—O200", "Li4—Li1—Li2—O200", "Li3—Li1—Li2—O200", "O2—Li1—Li2—Li4", "O1—Li1—Li2—Li4", "O100—Li1—Li2—Li4", "O4—Li1—Li2—Li4", "Li3—Li1—Li2—Li4", "O2—Li1—Li2—Li3", "O1—Li1—Li2—Li3", "sup-14", "120.0", "120.0", "118.4", "(11)", "120.8", "120.8", "122.6", "(10)", "118.7", "118.7", "141.3", "(8)", "123.0", "(7)", "85.6", "(6)", "121.5", "(7)", "84.5", "(6)", "82.5", "(6)", "122.9", "(9)", "127.5", "(9)", "109.6", "(8)", "121.3", "(7)", "116.0", "(9)", "122.0", "(8)", "−173.6", "(7)", "−75.7", "(12)", "92.0", "(6)", "58.0", "(5)", "127.9", "(6)", "91.5", "(6)", "−94.9", "(6)", "−170.5", "(11)", "−2.9", "(6)", "−36.9", "(5)", "33.1", "(5)", "173.6", "(7)", "97.9", "(12)", "−94.4", "(6)", "−128.4", "(6)", "−58.5", "(5)", "−79.7", "(11)", "93.9", "(11)", "18.2", "(19)", "−174.1", "(9)", "151.9", "(11)", "−138.2", "(12)", "128.4", "(6)", "−58.0", "(5)", "−133.7", "(12)", "34.0", "(5)", "69.9", "(5)", "58.5", "(5)", "−127.9", "(6)", "C402—C401—H40B", "H40A—C401—H40B", "C401—C402—H40C", "C401—C402—H40D", "H40C—C402—H40D", "C401—C402—H40E", "H40C—C402—H40E", "H40D—C402—H40E", "O400—C403—C404", "O400—C403—H40F", "C404—C403—H40F", "O400—C403—H40G", "C404—C403—H40G", "H40F—C403—H40G", "C403—C404—H40H", "C403—C404—H40I", "H40H—C404—H40I", "C403—C404—H40J", "H40H—C404—H40J", "H40I—C404—H40J", "O200—Li2—O2—Li1", "Li4—Li2—O2—Li1", "Li3—Li2—O2—Li1", "O1—Li2—O2—Li3", "O3—Li2—O2—Li3", "O200—Li2—O2—Li3", "Li1—Li2—O2—Li3", "Li4—Li2—O2—Li3", "O3—Li3—O2—B2", "O300—Li3—O2—B2", "O4—Li3—O2—B2", "Li2—Li3—O2—B2", "Li4—Li3—O2—B2", "Li1—Li3—O2—B2", "O3—Li3—O2—Li1", "O300—Li3—O2—Li1", "O4—Li3—O2—Li1", "Li2—Li3—O2—Li1", "Li4—Li3—O2—Li1", "O3—Li3—O2—Li2", "O300—Li3—O2—Li2", "O4—Li3—O2—Li2", "Li4—Li3—O2—Li2", "Li1—Li3—O2—Li2", "Li1—O2—B2—C31", "Li2—O2—B2—C31", "Li3—O2—B2—C31", "Li1—O2—B2—C41", "Li2—O2—B2—C41", "109.1", "107.8", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "112.4", "(9)", "109.1", "109.1", "109.1", "109.1", "107.9", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "137.6", "(8)", "−43.2", "(5)", "−87.0", "(6)", "91.9", "(6)", "−6.1", "(6)", "−135.4", "(8)", "87.0", "(6)", "43.8", "(6)", "−112.1", "(8)", "29.6", "(13)", "151.8", "(7)", "−118.4", "(9)", "−161.8", "(8)", "159.7", "(9)", "88.2", "(7)", "−130.1", "(9)", "−7.9", "(6)", "81.9", "(6)", "38.5", "(6)", "6.3", "(6)", "147.9", "(9)", "−89.8", "(6)", "−43.4", "(6)", "−81.9", "(6)", "−164.6", "(9)", "−46.7", "(11)", "53.2", "(12)", "15.8", "(17)", "133.6", "(9)" ]
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20-3246952-15
[ "supplementary", "materials", "O4—Li1—Li3—O2", "Li2—Li1—Li3—O2", "Li4—Li1—Li3—O2", "O2—Li1—Li3—O4", "O1—Li1—Li3—O4", "O100—Li1—Li3—O4", "Li2—Li1—Li3—O4", "Li4—Li1—Li3—O4", "O2—Li1—Li3—Li2", "O1—Li1—Li3—Li2", "O100—Li1—Li3—Li2", "O4—Li1—Li3—Li2", "Li4—Li1—Li3—Li2", "O2—Li1—Li3—Li4", "O1—Li1—Li3—Li4", "O100—Li1—Li3—Li4", "O4—Li1—Li3—Li4", "Li2—Li1—Li3—Li4", "O2—Li1—Li4—O4", "O1—Li1—Li4—O4", "O100—Li1—Li4—O4", "Li2—Li1—Li4—O4", "Li3—Li1—Li4—O4", "O2—Li1—Li4—O1", "O100—Li1—Li4—O1", "O4—Li1—Li4—O1", "Li2—Li1—Li4—O1", "Li3—Li1—Li4—O1", "O2—Li1—Li4—O3", "O1—Li1—Li4—O3", "O100—Li1—Li4—O3", "O4—Li1—Li4—O3", "Li2—Li1—Li4—O3", "Li3—Li1—Li4—O3", "O2—Li1—Li4—O400", "O1—Li1—Li4—O400", "O100—Li1—Li4—O400", "O4—Li1—Li4—O400", "Li2—Li1—Li4—O400", "Li3—Li1—Li4—O400", "O2—Li1—Li4—Li2", "O1—Li1—Li4—Li2", "O100—Li1—Li4—Li2", "O4—Li1—Li4—Li2", "Li3—Li1—Li4—Li2", "O2—Li1—Li4—Li3", "O1—Li1—Li4—Li3", "O100—Li1—Li4—Li3", "O4—Li1—Li4—Li3", "sup-16", "−169.5", "(8)", "61.3", "(5)", "133.4", "(7)", "169.5", "(8)", "−92.7", "(6)", "80.9", "(16)", "−129.2", "(7)", "−57.2", "(5)", "−61.3", "(5)", "36.5", "(5)", "−149.9", "(17)", "129.2", "(7)", "72.0", "(6)", "−133.4", "(7)", "−35.5", "(6)", "138.1", "(17)", "57.2", "(5)", "−72.0", "(6)", "93.1", "(7)", "−170.9", "(9)", "−90.9", "(11)", "130.6", "(7)", "59.8", "(5)", "−96.0", "(7)", "80.0", "(11)", "170.9", "(9)", "−58.5", "(5)", "−129.3", "(8)", "−2.1", "(6)", "93.9", "(7)", "173.9", "(10)", "−95.2", "(6)", "35.4", "(5)", "−35.4", "(5)", "−174.5", "(15)", "−78.4", "(16)", "2(2)", "92.5", "(17)", "−137.0", "(16)", "152.3", "(17)", "−37.5", "(5)", "58.5", "(5)", "138.5", "(12)", "−130.6", "(7)", "−70.8", "(6)", "33.3", "(5)", "129.3", "(8)", "−150.7", "(11)", "−59.8", "(5)", "Li2—Li3—O3—Li4", "Li1—Li3—O3—Li4", "O1—Li2—O3—B3", "O2—Li2—O3—B3", "O200—Li2—O3—B3", "Li1—Li2—O3—B3", "Li4—Li2—O3—B3", "Li3—Li2—O3—B3", "O1—Li2—O3—Li3", "O2—Li2—O3—Li3", "O200—Li2—O3—Li3", "Li1—Li2—O3—Li3", "Li4—Li2—O3—Li3", "O1—Li2—O3—Li4", "O2—Li2—O3—Li4", "O200—Li2—O3—Li4", "Li1—Li2—O3—Li4", "Li3—Li2—O3—Li4", "O4—Li4—O3—B3", "O1—Li4—O3—B3", "O400—Li4—O3—B3", "Li1—Li4—O3—B3", "Li2—Li4—O3—B3", "Li3—Li4—O3—B3", "O4—Li4—O3—Li3", "O1—Li4—O3—Li3", "O400—Li4—O3—Li3", "Li1—Li4—O3—Li3", "Li2—Li4—O3—Li3", "O4—Li4—O3—Li2", "O1—Li4—O3—Li2", "O400—Li4—O3—Li2", "Li1—Li4—O3—Li2", "Li3—Li4—O3—Li2", "Li3—O3—B3—C61", "Li2—O3—B3—C61", "Li4—O3—B3—C61", "Li3—O3—B3—C51", "Li2—O3—B3—C51", "Li4—O3—B3—C51", "O3—B3—C51—C52", "C61—B3—C51—C52", "O3—B3—C51—C56", "C61—B3—C51—C56", "C56—C51—C52—C53", "B3—C51—C52—C53", "C56—C51—C52—O31", "B3—C51—C52—O31", "C62—O31—C52—C51", "−82.8", "(6)", "−43.7", "(6)", "116.0", "(8)", "−145.6", "(8)", "−20.2", "(12)", "166.1", "(8)", "122.9", "(9)", "−152.1", "(10)", "−92.0", "(7)", "6.4", "(6)", "131.9", "(8)", "−41.8", "(6)", "−85.0", "(6)", "−6.9", "(6)", "91.4", "(7)", "−143.1", "(8)", "43.2", "(6)", "85.0", "(6)", "144.4", "(7)", "−117.5", "(8)", "10.5", "(10)", "−165.8", "(7)", "−124.3", "(8)", "149.4", "(8)", "−5.0", "(7)", "93.1", "(7)", "−138.9", "(8)", "44.8", "(6)", "86.3", "(6)", "−91.3", "(7)", "6.8", "(6)", "134.8", "(7)", "−41.5", "(5)", "−86.3", "(6)", "171.5", "(9)", "−56.9", "(12)", "45.6", "(11)", "−9.9", "(16)", "121.7", "(9)", "−135.8", "(9)", "174.5", "(8)", "−6.8", "(11)", "−5.3", "(14)", "173.4", "(8)", "−2.1", "(13)", "178.1", "(8)", "−179.4", "(8)", "0.7", "(12)", "7.2", "(11)" ]
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20-3246952-8
[ "supplementary", "materials", "O1—Li4—Li1", "O3—Li4—Li1", "O400—Li4—Li1", "O4—Li4—Li2", "O1—Li4—Li2", "O3—Li4—Li2", "O400—Li4—Li2", "Li1—Li4—Li2", "O4—Li4—Li3", "O1—Li4—Li3", "O3—Li4—Li3", "O400—Li4—Li3", "Li1—Li4—Li3", "Li2—Li4—Li3", "B1—O1—Li2", "B1—O1—Li1", "Li2—O1—Li1", "B1—O1—Li4", "Li2—O1—Li4", "Li1—O1—Li4", "O1—B1—C21", "O1—B1—C11", "C21—B1—C11", "C22—O11—C12", "C12—C11—C16", "C12—C11—B1", "C16—C11—B1", "C13—C12—O11", "C13—C12—C11", "O11—C12—C11", "C14—C13—C12", "C14—C13—H13", "C12—C13—H13", "C13—C14—C15", "C13—C14—H14", "C15—C14—H14", "C14—C15—C16", "C14—C15—H15", "C16—C15—H15", "C15—C16—C11", "C15—C16—H16", "C11—C16—H16", "C22—C21—C26", "C22—C21—B1", "C26—C21—B1", "O11—C22—C23", "O11—C22—C21", "C23—C22—C21", "C24—C23—C22", "sup-12", "48.2", "(5)", "91.8", "(7)", "153.6", "(8)", "94.4", "(7)", "46.8", "(5)", "47.7", "(5)", "138.8", "(7)", "57.8", "(6)", "49.5", "(5)", "95.1", "(7)", "45.8", "(5)", "141.2", "(8)", "60.9", "(6)", "59.8", "(5)", "145.9", "(7)", "123.7", "(7)", "81.4", "(6)", "117.6", "(7)", "85.2", "(6)", "83.4", "(6)", "125.5", "(9)", "122.4", "(9)", "112.1", "(9)", "122.4", "(7)", "112.8", "(8)", "122.2", "(8)", "125.0", "(8)", "115.7", "(8)", "125.0", "(9)", "119.4", "(8)", "118.8", "(9)", "120.6", "120.6", "120.9", "(9)", "119.5", "119.5", "119.5", "(10)", "120.2", "120.2", "122.9", "(9)", "118.5", "118.5", "112.5", "(8)", "121.2", "(9)", "126.2", "(8)", "113.2", "(7)", "122.0", "(8)", "124.8", "(9)", "117.6", "(9)", "C84—C83—H83", "C85—C84—C83", "C85—C84—H84", "C83—C84—H84", "C84—C85—C86", "C84—C85—H85", "C86—C85—H85", "C81—C86—C85", "C81—C86—H86", "C85—C86—H86", "C103—O100—C101", "C103—O100—Li1", "C101—O100—Li1", "O100—C101—C102", "O100—C101—H10A", "C102—C101—H10A", "O100—C101—H10B", "C102—C101—H10B", "H10A—C101—H10B", "C101—C102—H10C", "C101—C102—H10D", "H10C—C102—H10D", "C101—C102—H10E", "H10C—C102—H10E", "H10D—C102—H10E", "O100—C103—C104", "O100—C103—H10F", "C104—C103—H10F", "O100—C103—H10G", "C104—C103—H10G", "H10F—C103—H10G", "C103—C104—H10H", "C103—C104—H10I", "H10H—C104—H10I", "C103—C104—H10J", "H10H—C104—H10J", "H10I—C104—H10J", "C203—O200—C201", "C203—O200—Li2", "C201—O200—Li2", "O200—C201—C202", "O200—C201—H20A", "C202—C201—H20A", "O200—C201—H20B", "C202—C201—H20B", "H20A—C201—H20B", "C201—C202—H20C", "C201—C202—H20D", "H20C—C202—H20D", "120.7", "122.7", "(12)", "118.6", "118.6", "114.8", "(12)", "122.6", "122.6", "126.1", "(11)", "117.0", "117.0", "117.1", "(7)", "128.4", "(7)", "114.3", "(7)", "113.6", "(10)", "108.8", "108.8", "108.8", "108.8", "107.7", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "114.4", "(10)", "108.7", "108.7", "108.7", "108.7", "107.6", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "112.0", "(7)", "124.1", "(8)", "120.6", "(7)", "109.8", "(8)", "109.7", "109.7", "109.7", "109.7", "108.2", "109.5", "109.5", "109.5" ]
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20-3246952-4
[ "supplementary", "materials", "C36—H36", "C41—C46", "C41—C42", "C42—C43", "C43—C44", "C43—H43", "C44—C45", "C44—H44", "C45—C46", "C45—H45", "C46—H46", "O3—B3", "B3—C61", "B3—C51", "O31—C52", "O31—C62", "C51—C52", "C51—C56", "C52—C53", "C53—C54", "C53—H53", "C54—C55", "C54—H54", "C55—C56", "C55—H55", "C56—H56", "C61—C62", "C61—C66", "O2—Li1—O1", "O2—Li1—O100", "O1—Li1—O100", "O2—Li1—O4", "O1—Li1—O4", "O100—Li1—O4", "O2—Li1—Li2", "O1—Li1—Li2", "O100—Li1—Li2", "O4—Li1—Li2", "O2—Li1—Li4", "O1—Li1—Li4", "O100—Li1—Li4", "O4—Li1—Li4", "Li2—Li1—Li4", "O2—Li1—Li3", "O1—Li1—Li3", "O100—Li1—Li3", "O4—Li1—Li3", "Li2—Li1—Li3", "Li4—Li1—Li3", "sup-10", "0.9500", "1.368", "(14)", "1.401", "(13)", "1.409", "(14)", "1.328", "(16)", "0.9500", "1.394", "(15)", "0.9500", "1.395", "(15)", "0.9500", "0.9500", "1.322", "(11)", "1.569", "(14)", "1.589", "(15)", "1.381", "(12)", "1.400", "(12)", "1.367", "(13)", "1.409", "(14)", "1.360", "(13)", "1.29", "(2)", "0.9500", "1.44", "(2)", "0.9500", "1.422", "(13)", "0.9500", "0.9500", "1.402", "(14)", "1.447", "(13)", "99.0", "(7)", "124.7", "(7)", "114.2", "(7)", "96.9", "(7)", "95.1", "(6)", "121.1", "(8)", "50.5", "(5)", "48.8", "(5)", "142.5", "(8)", "95.5", "(7)", "96.9", "(7)", "48.4", "(4)", "138.3", "(8)", "47.1", "(4)", "61.6", "(6)", "48.5", "(4)", "94.7", "(7)", "150.9", "(7)", "48.9", "(4)", "60.9", "(6)", "60.3", "(5)", "O300—C301", "O300—C303", "C301—C302", "C301—H30A", "C301—H30B", "C302—H30C", "C302—H30D", "C302—H30E", "C303—C304", "C303—H30F", "C303—H30G", "C304—H30H", "C304—H30I", "C304—H30J", "O400—C403", "O400—C401", "C401—C402", "C401—H40A", "C401—H40B", "C402—H40C", "C402—H40D", "C402—H40E", "C403—C404", "C403—H40F", "C403—H40G", "C404—H40H", "C404—H40I", "C404—H40J", "C56—C51—B3", "C51—C52—C53", "C51—C52—O31", "C53—C52—O31", "C54—C53—C52", "C54—C53—H53", "C52—C53—H53", "C53—C54—C55", "C53—C54—H54", "C55—C54—H54", "C56—C55—C54", "C56—C55—H55", "C54—C55—H55", "C51—C56—C55", "C51—C56—H56", "C55—C56—H56", "C62—C61—C66", "C62—C61—B3", "C66—C61—B3", "C63—C62—C61", "C63—C62—O31", "1.425", "(14)", "1.487", "(13)", "1.496", "(8)", "0.9900", "0.9900", "0.9800", "0.9800", "0.9800", "1.499", "(8)", "0.9900", "0.9900", "0.9800", "0.9800", "0.9800", "1.422", "(12)", "1.429", "(12)", "1.505", "(8)", "0.9900", "0.9900", "0.9800", "0.9800", "0.9800", "1.495", "(8)", "0.9900", "0.9900", "0.9800", "0.9800", "0.9800", "122.0", "(8)", "124.1", "(10)", "122.9", "(8)", "112.9", "(8)", "120.1", "(11)", "119.9", "119.9", "122.9", "(11)", "118.5", "118.5", "115.0", "(11)", "122.5", "122.5", "121.7", "(10)", "119.2", "119.2", "115.1", "(8)", "121.5", "(8)", "123.4", "(8)", "122.9", "(9)", "115.1", "(9)" ]
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20-3246952-7
[ "Fig.", "1", "supplementary", "materials", "sup-21" ]
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20-3246952-22
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20-3246952-1
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20-3246952-18
[ "supplementary", "materials", "Fig.", "2", "sup-22" ]
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20-3246952-23
[ "supplementary", "materials", "O3—Li3—Li4—O400", "O300—Li3—Li4—O400", "O2—Li3—Li4—O400", "O4—Li3—Li4—O400", "Li2—Li3—Li4—O400", "Li1—Li3—Li4—O400", "O3—Li3—Li4—Li1", "O300—Li3—Li4—Li1", "O2—Li3—Li4—Li1", "O4—Li3—Li4—Li1", "Li2—Li3—Li4—Li1", "O3—Li3—Li4—Li2", "O300—Li3—Li4—Li2", "O2—Li3—Li4—Li2", "O4—Li3—Li4—Li2", "Li1—Li3—Li4—Li2", "O3—Li2—O1—B1", "O2—Li2—O1—B1", "O200—Li2—O1—B1", "Li1—Li2—O1—B1", "Li4—Li2—O1—B1", "Li3—Li2—O1—B1", "O3—Li2—O1—Li1", "O2—Li2—O1—Li1", "O200—Li2—O1—Li1", "Li4—Li2—O1—Li1", "Li3—Li2—O1—Li1", "O3—Li2—O1—Li4", "O2—Li2—O1—Li4", "O200—Li2—O1—Li4", "Li1—Li2—O1—Li4", "Li3—Li2—O1—Li4", "O2—Li1—O1—B1", "O100—Li1—O1—B1", "O4—Li1—O1—B1", "Li2—Li1—O1—B1", "Li4—Li1—O1—B1", "Li3—Li1—O1—B1", "O2—Li1—O1—Li2", "O100—Li1—O1—Li2", "O4—Li1—O1—Li2", "Li4—Li1—O1—Li2", "Li3—Li1—O1—Li2", "O2—Li1—O1—Li4", "O100—Li1—O1—Li4", "O4—Li1—O1—Li4", "Li2—Li1—O1—Li4", "Li3—Li1—O1—Li4", "O4—Li4—O1—B1", "sup-18", "73.1", "(12)", "−30", "(2)", "168.1", "(11)", "−100.4", "(13)", "131.8", "(13)", "−160.7", "(13)", "−126.2", "(7)", "130.6", "(16)", "−31.3", "(5)", "60.3", "(6)", "−67.5", "(6)", "−58.7", "(6)", "−161.8", "(16)", "36.3", "(5)", "127.9", "(8)", "67.5", "(6)", "−127.8", "(11)", "136.2", "(11)", "7.7", "(18)", "141.0", "(13)", "−135.0", "(13)", "−174.5", "(11)", "91.1", "(6)", "−4.8", "(5)", "−133.3", "(10)", "84.0", "(6)", "44.5", "(6)", "7.1", "(6)", "−88.8", "(7)", "142.7", "(9)", "−84.0", "(6)", "−39.5", "(7)", "−150.0", "(7)", "−15.3", "(11)", "112.2", "(8)", "−155.0", "(8)", "118.9", "(8)", "161.3", "(7)", "5.0", "(6)", "139.7", "(9)", "−92.8", "(7)", "−86.2", "(6)", "−43.7", "(6)", "91.2", "(7)", "−134.1", "(8)", "−6.7", "(7)", "86.2", "(6)", "42.4", "(6)", "−117.7", "(7)", "O100—Li1—O4—Li4", "Li2—Li1—O4—Li4", "Li3—Li1—O4—Li4", "O2—Li1—O4—Li3", "O1—Li1—O4—Li3", "O100—Li1—O4—Li3", "Li2—Li1—O4—Li3", "Li4—Li1—O4—Li3", "O3—Li3—O4—B4", "O300—Li3—O4—B4", "O2—Li3—O4—B4", "Li2—Li3—O4—B4", "Li4—Li3—O4—B4", "Li1—Li3—O4—B4", "O3—Li3—O4—Li4", "O300—Li3—O4—Li4", "O2—Li3—O4—Li4", "Li2—Li3—O4—Li4", "Li1—Li3—O4—Li4", "O3—Li3—O4—Li1", "O300—Li3—O4—Li1", "O2—Li3—O4—Li1", "Li2—Li3—O4—Li1", "Li4—Li3—O4—Li1", "Li4—O4—B4—C71", "Li1—O4—B4—C71", "Li3—O4—B4—C71", "Li4—O4—B4—C81", "Li1—O4—B4—C81", "Li3—O4—B4—C81", "O4—B4—C71—C72", "C81—B4—C71—C72", "O4—B4—C71—C76", "C81—B4—C71—C76", "C82—O41—C72—C71", "C82—O41—C72—C73", "C76—C71—C72—O41", "B4—C71—C72—O41", "C76—C71—C72—C73", "B4—C71—C72—C73", "O41—C72—C73—C74", "C71—C72—C73—C74", "C72—C73—C74—C75", "C73—C74—C75—C76", "C74—C75—C76—C71", "C72—C71—C76—C75", "B4—C71—C76—C75", "O4—B4—C81—C86", "C71—B4—C81—C86", "129.1", "(8)", "−42.2", "(7)", "−85.0", "(6)", "−7.9", "(6)", "91.8", "(7)", "−145.9", "(8)", "42.9", "(6)", "85.0", "(6)", "148.9", "(7)", "9.5", "(12)", "−114.9", "(7)", "−163.1", "(7)", "153.9", "(9)", "−122.4", "(8)", "−5.0", "(7)", "−144.4", "(9)", "91.2", "(7)", "43.1", "(6)", "83.7", "(6)", "−88.7", "(6)", "131.9", "(9)", "7.5", "(6)", "−40.6", "(6)", "−83.7", "(6)", "−6.8", "(18)", "121.5", "(9)", "−137.3", "(9)", "177.1", "(10)", "−54.6", "(12)", "46.6", "(12)", "176.2", "(8)", "−7.4", "(11)", "−5.2", "(14)", "171.2", "(9)", "12.5", "(14)", "−168.6", "(8)", "178.3", "(9)", "−3.0", "(13)", "−0.5", "(13)", "178.2", "(8)", "−177.5", "(9)", "1.5", "(15)", "−2.8", "(18)", "3.0", "(18)", "−1.8", "(16)", "0.6", "(14)", "−178.0", "(9)", "4.6", "(15)", "−171.8", "(9)" ]
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20-3246952-6
[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "Tetrakis(l3-9-oxa-10-boraanthracen-10-", "olato)tetrakis[(diethyl", "ether)lithium]", "Daniel", "Franz,", "Hans-Wolfram", "Lerner,", "Dominik", "Bu¨ttner", "and", "Michael", "Bolte*", "Institut", "fu¨", "r", "Anorganische", "Chemie,", "J.", "W.", "Goethe-Universita¨t", "Frankfurt,", "Max-von-Laue-", "Strasse", "7,", "60438", "Frankfurt/Main,", "Germany", "Correspondence", "e-mail:", "bolte@chemie.uni-frankfurt.de", "Received", "27", "September", "2011;", "accepted", "6", "October", "2011", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "173", "K;", "mean", "(C–C)", "=", "0.015", "A˚;", "R", "factor", "=", "0.077;", "wR", "factor", "=", "0.204;", "data-to-parameter", "ratio", "=", "8.3.", "The", "title", "compound,", "[Li4O4(C12H8BO)4(C4H10O)4],", "features", "a", "Li4O4", "cube.", "Each", "Li", "atom", "in", "the", "cube", "is", "additionally", "coordinated", "by", "a", "diethyl", "ether", "molecule", "and", "each", "O", "atom", "in", "the", "cube", "carries", "a", "9-oxa-10-boraanthracene", "residue.", "The", "crystal", "studied", "was", "a", "non-merohedral", "twin", "[twin", "law", "(-1", "0", "0", "/", "0", "0", "1", "/", "0", "1", "0);", "the", "contribution", "of", "the", "major", "twin", "component", "refined", "to", "0.553", "(3)]", "emulating", "apparent", "tetragonal", "symmetry,", "whereas", "the", "actual", "crystal", "system", "is", "just", "orthorhombic.", "Related", "literature", "For", "chalcogenolate", "ligands", "used", "to", "stabilize", "transition", "metal", "centers,", "see:", "Wolczanski", "(2009);", "Ku¨", "ckmann", "et", "al.", "(2005,", "2008,", "2010).", "For", "synthetic", "details,", "see:", "Davidson", "&", "French", "(1960);", "Mikoshiba", "et", "al.", "(2003);", "Zuideveld", "et", "al.", "(2002);", "Knizek", "&", "No¨", "th", "(2000).", "For", "related", "structures,", "see:", "Ku¨", "ckmann", "et", "al.", "(2007);", "Lerner", "et", "al.", "(2002).", "metal-organic", "compounds", "Experimental", "Crystal", "data", "[Li4O4(C12H8BO)4(C4H10O)4]", "Mr", "=", "1104.22", "Orthorhombic,", "Pna21", "a", "=", "21.4805", "(8)", "A˚", "b", "=", "17.6053", "(10)", "A˚", "c", "=", "17.5723", "(8)", "A˚", "Data", "collection", "Stoe", "IPDS", "II", "two-circle", "diffractometer", "77138", "measured", "reflections", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.077", "wR(F", "2)", "=", "0.204", "S", "=", "1.04", "6262", "reflections", "758", "parameters", "V", "=", "6645.3", "(5)", "A˚", "3", "Z", "=", "4", "Mo", "K", "radiation", "=", "0.07", "mm", "1", "T", "=", "173", "K", "0.30", "0.30", "0.25", "mm", "6262", "independent", "reflections", "4842", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.114", "29", "restraints", "H-atom", "parameters", "constrained", "max", "=", "1.10", "e", "A˚", "3", "min", "=", "0.35", "e", "A˚", "3", "Data", "collection:", "X-AREA", "(Stoe", "&", "Cie,", "2001);", "cell", "refinement:", "X-", "AREA;", "data", "reduction:", "X-AREA;", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "XP", "(Sheldrick,", "2008);", "software", "used", "to", "prepare", "material", "for", "publication:", "SHELXL97", "and", "PLATON", "(Spek,", "2009).", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "BG2423).", "References", "Davidson,", "J.", "M.", "&", "French,", "C.", "M.", "(1960).", "J.", "Chem.", "Soc.", "pp.", "191–195.", "Knizek,", "J.", "&", "No¨", "th,", "H.", "(2000).", "J.", "Organomet.", "Chem.", "614–615,", "168–187.", "Ku¨", "ckmann,", "T.", "I.,", "Bolte,", "M.,", "Wagner,", "M.", "&", "Lerner,", "H.-W.", "(2007).", "Z.", "Anorg.", "Allg.", "Chem.", "633,", "290–297.", "Ku¨", "ckmann,", "T.", "I.,", "Hermsen,", "M.,", "Bolte,", "M.,", "Wagner,", "M.", "&", "Lerner,", "H.-W.", "(2005).", "Inorg.", "Chem.", "44,", "3449–3458.", "Ku¨", "ckmann,", "T.", "I.,", "Scho¨", "del,", "F.,", "Sa¨", "nger,", "I.,", "Bolte,", "M.,", "Wagner,", "M.", "&", "Lerner,", "H.-W.", "(2008).", "Organometallics,", "27,", "3272–3278.", "Ku¨", "ckmann,", "T.,", "Scho¨", "del,", "F.,", "Sa¨", "nger,", "I.,", "Bolte,", "M.,", "Wagner,", "M.", "&", "Lerner,", "H.-W.", "(2010).", "Eur.", "J.", "Inorg.", "Chem.", "2010,", "468–475.", "Lerner,", "H.-W.,", "Scholz,", "S.", "&", "Bolte,", "M.", "(2002).", "Organometallics,", "21,", "3827–3830.", "Mikoshiba,", "K.,", "Iwasaki,", "H.,", "Maruyama,", "T.", "&", "Hamano,", "S.-I.", "(2003).", "Patent", "WO", "2003/033002.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Spek,", "A.", "L.", "(2009).", "Acta", "Cryst.", "D65,", "148–155.", "Stoe", "&", "Cie", "(2001).", "X-AREA.", "Stoe", "&", "Cie,", "Darmstadt,", "Germany.", "Wolczanski,", "P.", "T.", "(2009).", "Chem.", "Commun.", "pp.", "740–757.", "Zuideveld,", "M.", "A.,", "Swennenhuis,", "B.", "H.", "G.,", "Boele,", "M.", "D.", "K.,", "Guari,", "Y.,", "van", "Strijdonck,", "G.", "P.", "F.,", "Reek,", "J.", "N.", "H.,", "Kamer,", "P.", "C.", "J.,", "Goubitz,", "K.,", "Fraanje,", "J.,", "Lutz,", "M.,", "Spek,", "A.", "L.", "&", "van", "Leeuwen,", "P.", "W.", "N.", "M.", "(2002).", "J.", "Chem.", "Soc.", "Dalton", "Trans.", "pp.", "2308–2317.", "Acta", "Cryst.", "(2011).", "E67,", "m1525", "doi:10.1107/S1600536811041201", "Franz", "et", "al.", "m1525" ]
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20-3246952-9
[ "C24—C23—H23", "C22—C23—H23", "C23—C24—C25", "C23—C24—H24", "C25—C24—H24", "C26—C25—C24", "C26—C25—H25", "C24—C25—H25", "C25—C26—C21", "C25—C26—H26", "C21—C26—H26", "B2—O2—Li1", "B2—O2—Li2", "Li1—O2—Li2", "B2—O2—Li3", "Li1—O2—Li3", "Li2—O2—Li3", "O2—B2—C31", "O2—B2—C41", "C31—B2—C41", "C32—O21—C42", "C32—C31—C36", "C32—C31—B2", "C36—C31—B2", "C31—C32—O21", "C31—C32—C33", "O21—C32—C33", "C34—C33—C32", "C34—C33—H33", "C32—C33—H33", "C35—C34—C33", "C35—C34—H34", "C33—C34—H34", "C36—C35—C34", "C36—C35—H35", "C34—C35—H35", "C35—C36—C31", "C35—C36—H36", "C31—C36—H36", "C46—C41—C42", "C46—C41—B2", "C42—C41—B2", "O21—C42—C41", "O21—C42—C43", "C41—C42—C43", "C44—C43—C42", "C44—C43—H43", "C42—C43—H43", "C43—C44—C45", "121.2", "121.2", "123.6", "(10)", "118.2", "118.2", "114.8", "(10)", "122.6", "122.6", "126.6", "(9)", "116.7", "116.7", "145.6", "(7)", "117.6", "(7)", "81.5", "(6)", "122.7", "(7)", "86.0", "(6)", "83.0", "(6)", "125.8", "(9)", "124.0", "(9)", "110.2", "(8)", "118.8", "(7)", "118.8", "(9)", "120.2", "(9)", "121.0", "(9)", "127.3", "(9)", "122.2", "(9)", "110.6", "(8)", "117.2", "(10)", "121.4", "121.4", "120.1", "(10)", "120.0", "120.0", "119.5", "(10)", "120.2", "120.2", "122.1", "(9)", "118.9", "118.9", "117.7", "(9)", "124.8", "(9)", "117.4", "(9)", "125.1", "(9)", "115.7", "(9)", "119.1", "(10)", "122.0", "(10)", "119.0", "119.0", "120.1", "(10)", "C201—C202—H20E", "H20C—C202—H20E", "H20D—C202—H20E", "O200—C203—C204", "O200—C203—H20F", "C204—C203—H20F", "O200—C203—H20G", "C204—C203—H20G", "H20F—C203—H20G", "C203—C204—H20H", "C203—C204—H20I", "H20H—C204—H20I", "C203—C204—H20J", "H20H—C204—H20J", "H20I—C204—H20J", "C301—O300—C303", "C301—O300—Li3", "C303—O300—Li3", "C302—C301—O300", "C302—C301—H30A", "O300—C301—H30A", "C302—C301—H30B", "O300—C301—H30B", "H30A—C301—H30B", "C301—C302—H30C", "C301—C302—H30D", "H30C—C302—H30D", "C301—C302—H30E", "H30C—C302—H30E", "H30D—C302—H30E", "C304—C303—O300", "C304—C303—H30F", "O300—C303—H30F", "C304—C303—H30G", "O300—C303—H30G", "H30F—C303—H30G", "C303—C304—H30H", "C303—C304—H30I", "H30H—C304—H30I", "C303—C304—H30J", "H30H—C304—H30J", "H30I—C304—H30J", "C403—O400—C401", "C403—O400—Li4", "C401—O400—Li4", "O400—C401—C402", "O400—C401—H40A", "C402—C401—H40A", "O400—C401—H40B", "supplementary", "materials", "109.5", "109.5", "109.5", "108.5", "(9)", "110.0", "110.0", "110.0", "110.0", "108.4", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "108.9", "(8)", "126.8", "(8)", "121.4", "(7)", "109.1", "(10)", "109.9", "109.9", "109.9", "109.9", "108.3", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "116.5", "(9)", "108.2", "108.2", "108.2", "108.2", "107.3", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "112.1", "(7)", "121.4", "(7)", "124.1", "(7)", "112.7", "(8)", "109.1", "109.1", "109.1", "sup-13" ]
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20-3246952-14
[ "O100—Li1—Li2—Li3", "O4—Li1—Li2—Li3", "Li4—Li1—Li2—Li3", "O1—Li2—Li3—O3", "O2—Li2—Li3—O3", "O200—Li2—Li3—O3", "Li1—Li2—Li3—O3", "Li4—Li2—Li3—O3", "O1—Li2—Li3—O300", "O3—Li2—Li3—O300", "O2—Li2—Li3—O300", "O200—Li2—Li3—O300", "Li1—Li2—Li3—O300", "Li4—Li2—Li3—O300", "O1—Li2—Li3—O2", "O3—Li2—Li3—O2", "O200—Li2—Li3—O2", "Li1—Li2—Li3—O2", "Li4—Li2—Li3—O2", "O1—Li2—Li3—O4", "O3—Li2—Li3—O4", "O2—Li2—Li3—O4", "O200—Li2—Li3—O4", "Li1—Li2—Li3—O4", "Li4—Li2—Li3—O4", "O1—Li2—Li3—Li4", "O3—Li2—Li3—Li4", "O2—Li2—Li3—Li4", "O200—Li2—Li3—Li4", "Li1—Li2—Li3—Li4", "O1—Li2—Li3—Li1", "O3—Li2—Li3—Li1", "O2—Li2—Li3—Li1", "O200—Li2—Li3—Li1", "Li4—Li2—Li3—Li1", "O2—Li1—Li3—O3", "O1—Li1—Li3—O3", "O100—Li1—Li3—O3", "O4—Li1—Li3—O3", "Li2—Li1—Li3—O3", "Li4—Li1—Li3—O3", "O2—Li1—Li3—O300", "O1—Li1—Li3—O300", "O100—Li1—Li3—O300", "O4—Li1—Li3—O300", "Li2—Li1—Li3—O300", "Li4—Li1—Li3—O300", "O1—Li1—Li3—O2", "O100—Li1—Li3—O2", "156.4", "(12)", "−35.9", "(5)", "−69.9", "(5)", "94.0", "(7)", "−171.5", "(8)", "−88.9", "(13)", "131.3", "(7)", "61.0", "(6)", "−168.0", "(16)", "98.0", "(19)", "−73.5", "(17)", "9(3)", "−130.7", "(18)", "159.0", "(19)", "−94.5", "(7)", "171.5", "(8)", "82.6", "(13)", "−57.2", "(5)", "−127.4", "(8)", "−1.9", "(7)", "−95.9", "(6)", "92.6", "(7)", "175.2", "(11)", "35.4", "(6)", "−34.8", "(5)", "32.9", "(6)", "−61.0", "(6)", "127.4", "(8)", "−150.0", "(13)", "70.2", "(6)", "−37.3", "(5)", "−131.3", "(7)", "57.2", "(5)", "139.8", "(14)", "−70.2", "(6)", "−95.4", "(7)", "2.5", "(7)", "176.0", "(15)", "95.1", "(6)", "−34.0", "(5)", "38.0", "(5)", "85.5", "(10)", "−176.6", "(9)", "−3(2)", "−84.0", "(10)", "146.8", "(10)", "−141.1", "(11)", "97.9", "(7)", "−88.6", "(16)", "Li3—O2—B2—C41", "O2—B2—C31—C32", "C41—B2—C31—C32", "O2—B2—C31—C36", "C41—B2—C31—C36", "C36—C31—C32—O21", "B2—C31—C32—O21", "C36—C31—C32—C33", "B2—C31—C32—C33", "C42—O21—C32—C31", "C42—O21—C32—C33", "C31—C32—C33—C34", "O21—C32—C33—C34", "C32—C33—C34—C35", "C33—C34—C35—C36", "C34—C35—C36—C31", "C32—C31—C36—C35", "B2—C31—C36—C35", "O2—B2—C41—C46", "C31—B2—C41—C46", "O2—B2—C41—C42", "C31—B2—C41—C42", "C32—O21—C42—C41", "C32—O21—C42—C43", "C46—C41—C42—O21", "B2—C41—C42—O21", "C46—C41—C42—C43", "B2—C41—C42—C43", "O21—C42—C43—C44", "C41—C42—C43—C44", "C42—C43—C44—C45", "C43—C44—C45—C46", "C42—C41—C46—C45", "B2—C41—C46—C45", "C44—C45—C46—C41", "O300—Li3—O3—B3", "O2—Li3—O3—B3", "O4—Li3—O3—B3", "Li2—Li3—O3—B3", "Li4—Li3—O3—B3", "Li1—Li3—O3—B3", "O300—Li3—O3—Li2", "O2—Li3—O3—Li2", "O4—Li3—O3—Li2", "Li4—Li3—O3—Li2", "Li1—Li3—O3—Li2", "O300—Li3—O3—Li4", "O2—Li3—O3—Li4", "O4—Li3—O3—Li4", "supplementary", "materials", "−126.5", "(9)", "171.5", "(9)", "−8.8", "(11)", "−7.0", "(14)", "172.7", "(8)", "−179.2", "(9)", "2.3", "(14)", "1.2", "(14)", "−177.2", "(8)", "7.2", "(14)", "−173.2", "(8)", "−3.7", "(15)", "176.7", "(9)", "2.7", "(15)", "0.5", "(16)", "−3.2", "(16)", "2.3", "(15)", "−179.3", "(9)", "10.3", "(14)", "−169.4", "(9)", "−173.5", "(9)", "6.8", "(11)", "−9.1", "(13)", "171.5", "(8)", "178.0", "(9)", "1.6", "(13)", "−2.6", "(14)", "−179.1", "(8)", "−179.7", "(9)", "0.9", "(14)", "1.1", "(16)", "−1.4", "(16)", "2.4", "(15)", "178.6", "(9)", "−0.4", "(16)", "−0.5", "(17)", "134.7", "(10)", "−131.3", "(10)", "141.1", "(12)", "−136.1", "(12)", "−179.8", "(10)", "−141.6", "(9)", "−6.3", "(6)", "87.6", "(7)", "82.8", "(6)", "39.2", "(6)", "135.6", "(10)", "−89.2", "(7)", "4.8", "(6)", "sup-15" ]
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20-3246952-16
[ "supplementary", "materials", "Acta", "Cryst.", "(2011).", "E67,", "m1525", "[", "doi:10.1107/S1600536811041201", "]", "Tetrakis(", "3-9-oxa-10-boraanthracen-10-olato)tetrakis[(diethyl", "ether)lithium]", "D.", "Franz,", "H.-W.", "Lerner,", "D.", "Büttner", "and", "M.", "Bolte", "Comment", "In", "this", "study,", "the", "accordance", "of", "the", "structural", "characteristics", "between", "the", "alkali", "metal", "salts", "of", "borinic", "acids,", "M+[EBR2]-", "(E", "=", "O),", "and", "the", "related", "silyl", "chalcogenolates", "M+[ESiR3]-", "(E", "=", "O,", "S,", "Se,", "Te)", "is", "taken", "into", "account.", "It", "has", "been", "shown", "that", "chal-", "cogenolate", "ligands", "of", "the", "type", "[ESiR3]-", "(E", "=", "O,", "S,", "Se,", "Te)", "were", "used", "to", "stabilize", "transition", "metal", "centers", "(Wolczanski,", "2009;", "Kückmann", "et", "al.,", "2005,", "2008,", "and", "2010).", "These", "ligands", "have", "also", "been", "applied", "in", "the", "field", "of", "macromolecular", "chemistry.", "Normally,", "transition", "metal", "complexes", "possess", "6", "e-", "chalcogenolate", "ligands", "in", "a", "µ3", "binding", "mode.", "Recently,", "however,", "we", "have", "shown", "that", "the", "anion", "of", "the", "mixed", "valence", "Mn(I/II)", "complex", "[Na(thf)6][(OC)3Mn(µ-SSitBu3)3MnSSitBu3]", "contains", "a", "ter-", "minal", "thiolate", "ligand", "with", "a", "linear", "Mn—S—Si", "unit", "(Kückmann", "et", "al.,", "2008).", "The", "prerequisite", "for", "electronic", "communication", "between", "the", "metal", "center", "and", "the", "ligand", "is", "thus", "fulfilled.", "By", "an", "attempt", "to", "synthesize", "compound", "III", "(Fig.", "1)", "we", "obtained", "as", "a", "by-product", "single", "crystals", "of", "the", "title", "compound", "(IV).", "The", "starting", "materials", "I", "and", "II", "were", "synthesized", "by", "modification", "of", "the", "procedures", "reported", "in", "the", "literature", "(Mikoshiba", "et", "al.,", "2003;", "Davidson", "&", "French,", "1960;", "Zuideveld", "et", "al.,", "2002).", "IV", "displays", "a", "heterocubane", "structure", "in", "the", "solid", "state.", "Related", "structural", "motifs", "are", "found", "in", "the", "silyl", "chalcogenolates", "(Na[OSitBu3])4,", "(Na[OSiPhtBu2])4,", "and", "([Na(thf)][OSiMePh2])4", "(Lerner", "et", "al.", "2002;", "Kückmann", "et", "al.,", "2007).", "In", "conclusion,", "the", "solid-state", "structure", "of", "IV", "provides", "further", "evidence", "for", "the", "diagonal", "relationship", "between", "B", "and", "Si.", "The", "title", "compound", "(Fig.", "2)", "features", "a", "Li4O4", "cube.", "Each", "Li", "atom", "in", "the", "cube", "is", "additionally", "coordinated", "by", "a", "diethyl", "ether", "molecule", "and", "each", "O", "atom", "in", "the", "cube", "carries", "a", "9-oxa-10-bora-anthryl", "residue.", "Experimental", "All", "transformations", "were", "carried", "out", "under", "an", "atmosphere", "of", "dry", "nitrogen", "using", "standard", "Schlenk", "techniques", "and", "carefully", "dried", "solvents.", "The", "11B", "NMR", "spectrum", "was", "recorded", "on", "a", "Bruker", "Avance", "300.", "The", "borinic", "acid", "II", "(1.18", "g,", "6.0", "mmol)", "was", "dissolved", "in", "Et2O", "(40", "ml)", "and", "cooled", "to", "0", "°C.", "Under", "vigorous", "stirring", "a", "solution", "of", "Li[AlH4]", "(9", "mmol)", "in", "Et2O", "(19", "mL)", "was", "added", "dropwise", "over", "a", "period", "of", "30", "min", "(beforehand,", "few", "small", "crystallites", "of", "2,2'-biquinoline", "had", "been", "added", "to", "the", "ethereal", "Li[AlH4]", "solution", "as", "a", "color", "indicator", "for", "the", "consumption", "of", "Li[AlH4]).", "The", "mixture", "was", "allowed", "to", "warm", "to", "room", "temperature", "over", "night", "yielding", "a", "pale", "yellow", "suspension.", "In", "the", "11B", "NMR", "spectrum", "(in", "C6D6/THF", "(1:1),", "referenced", "to", "external", "BF3.Et2O)", "a", "triplet", "was", "observed", "at", "-24.0", "ppm", "(1JBH", "=", "78", "Hz)", "which", "indicated", "conversion", "into", "the", "putative", "9,9-dihydrido-9-oxa-10-borataanthracene", "(III)", "(cf.", "lithium", "9,9-dihydrido-9-boratafluorene:", "δ(11B)", "=", "-22.3", "(1J-H", "=", "77", "Hz)", "in", "CDCl3)", "(Knizek", "&", "Nöth,", "2000).", "The", "solid", "was", "removed", "by", "filtration.", "The", "clear", "solution", "was", "subject", "to", "a", "crystallization", "experiment", "implementing", "gas", "phase", "diffusion", "exchange", "of", "solvent", "with", "a", "reservoir", "containing", "a", "mixture", "of", "hexane/pentane", "(15", "ml/15", "ml).", "After", "three", "weeks", "a", "few", "cubic", "crystals", "of", "the", "title", "compound", "(IV)", "were", "obtained.", "sup-1" ]
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20-3246952-2
[ "O1—Li2—O3", "O1—Li2—O2", "O3—Li2—O2", "O1—Li2—O200", "O3—Li2—O200", "O2—Li2—O200", "O1—Li2—Li1", "O3—Li2—Li1", "O2—Li2—Li1", "O200—Li2—Li1", "O1—Li2—Li4", "O3—Li2—Li4", "O2—Li2—Li4", "O200—Li2—Li4", "Li1—Li2—Li4", "O1—Li2—Li3", "O3—Li2—Li3", "O2—Li2—Li3", "O200—Li2—Li3", "Li1—Li2—Li3", "Li4—Li2—Li3", "O3—Li3—O300", "O3—Li3—O2", "O300—Li3—O2", "O3—Li3—O4", "O300—Li3—O4", "O2—Li3—O4", "O3—Li3—Li2", "O300—Li3—Li2", "O2—Li3—Li2", "O4—Li3—Li2", "O3—Li3—Li4", "O300—Li3—Li4", "O2—Li3—Li4", "O4—Li3—Li4", "Li2—Li3—Li4", "O3—Li3—Li1", "O300—Li3—Li1", "O2—Li3—Li1", "O4—Li3—Li1", "Li2—Li3—Li1", "Li4—Li3—Li1", "O4—Li4—O1", "O4—Li4—O3", "O1—Li4—O3", "O4—Li4—O400", "O1—Li4—O400", "O3—Li4—O400", "O4—Li4—Li1", "97.3", "(6)", "97.6", "(7)", "94.9", "(6)", "122.8", "(7)", "121.8", "(8)", "116.5", "(7)", "49.8", "(5)", "95.6", "(6)", "48.0", "(5)", "142.2", "(8)", "48.0", "(5)", "49.8", "(4)", "94.2", "(6)", "149.2", "(7)", "60.6", "(6)", "96.5", "(6)", "46.3", "(4)", "48.9", "(5)", "140.7", "(7)", "62.0", "(6)", "60.4", "(5)", "129.4", "(9)", "95.8", "(6)", "118.8", "(7)", "95.7", "(6)", "116.1", "(7)", "93.3", "(7)", "48.1", "(5)", "151.0", "(7)", "48.1", "(5)", "92.0", "(6)", "49.6", "(5)", "146.3", "(7)", "93.1", "(7)", "46.3", "(4)", "59.8", "(5)", "92.8", "(6)", "137.8", "(8)", "45.5", "(5)", "48.4", "(5)", "57.1", "(5)", "58.8", "(6)", "97.6", "(8)", "95.1", "(6)", "94.1", "(7)", "126.3", "(8)", "122.0", "(6)", "114.4", "(8)", "49.8", "(5)", "C61—C62—O31", "C62—C63—C64", "C62—C63—H63", "C64—C63—H63", "C63—C64—C65", "C63—C64—H64", "C65—C64—H64", "C66—C65—C64", "C66—C65—H65", "C64—C65—H65", "C65—C66—C61", "C65—C66—H66", "C61—C66—H66", "B4—O4—Li4", "B4—O4—Li1", "Li4—O4—Li1", "B4—O4—Li3", "Li4—O4—Li3", "Li1—O4—Li3", "O4—B4—C71", "O4—B4—C81", "C71—B4—C81", "C72—O41—C82", "C72—C71—C76", "C72—C71—B4", "C76—C71—B4", "O41—C72—C71", "O41—C72—C73", "C71—C72—C73", "C74—C73—C72", "C74—C73—H73", "C72—C73—H73", "C75—C74—C73", "C75—C74—H74", "C73—C74—H74", "C74—C75—C76", "C74—C75—H75", "C76—C75—H75", "C75—C76—C71", "C75—C76—H76", "C71—C76—H76", "C86—C81—C82", "C86—C81—B4", "C82—C81—B4", "C83—C82—O41", "C83—C82—C81", "O41—C82—C81", "C82—C83—C84", "C82—C83—H83", "supplementary", "materials", "121.9", "(9)", "120.2", "(10)", "119.9", "119.9", "118.7", "(10)", "120.6", "120.6", "121.2", "(10)", "119.4", "119.4", "121.7", "(9)", "119.1", "119.1", "144.8", "(8)", "121.4", "(7)", "83.0", "(6)", "121.1", "(7)", "84.2", "(6)", "82.7", "(7)", "124.5", "(8)", "121.9", "(9)", "113.5", "(8)", "121.2", "(8)", "117.3", "(9)", "117.4", "(9)", "125.2", "(8)", "125.9", "(9)", "114.3", "(11)", "119.8", "(12)", "117.5", "(12)", "121.3", "121.3", "122.6", "(11)", "118.7", "118.7", "121.3", "(13)", "119.3", "119.3", "121.4", "(11)", "119.3", "119.3", "113.9", "(10)", "126.5", "(9)", "119.6", "(10)", "115.3", "(11)", "123.7", "(13)", "120.9", "(10)", "118.7", "(12)", "120.7", "sup-11" ]
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20-3246952-12
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20-3246952-3
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88-2961354-6
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88-2961354-7
[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "Methyl", "3-(4-bromophenyl)-2-(1H-indol-", "3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-", "oxo-2-phenylazetidin-2-yl]-4-nitro-", "pyrrolidine-2-carboxylate", "S.", "Nirmala,a", "E.", "Theboral", "Sugi", "Kamala,a", "L.", "Sudha,b*", "N.", "Arumugamc", "and", "R.", "Raghunathanc", "aDepartment", "of", "Physics,", "Easwari", "Engineering", "College,", "Ramapuram,", "Chennai", "600", "089,", "India,", "bDepartment", "of", "Physics,", "SRM", "University,", "Ramapuram", "Campus,", "Chennai", "600", "089,", "India,", "and", "cDepartment", "of", "Organic", "Chemistry,", "University", "of", "Madras,", "Guindy", "Campus,", "Chennai", "600", "025,", "India", "Correspondence", "e-mail:", "sudharose18@gmail.com", "Received", "10", "April", "2008;", "accepted", "12", "May", "2008", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "293", "K;", "mean", "(C–C)", "=", "0.004", "A˚;", "R", "factor", "=", "0.040;", "wR", "factor", "=", "0.120;", "data-to-parameter", "ratio", "=", "19.7.", "In", "the", "title", "compound,", "C37H33BrN4O6,", "the", "pyrrolidine", "ring", "adopts", "an", "envelope", "conformation.", "The", "-lactam", "ring", "is", "planar", "and", "makes", "dihedral", "angles", "of", "70.16", "(13)", "and", "28.32", "(13)", "with", "the", "phenyl", "and", "4-methoxyphenyl", "rings,", "respectively.", "The", "molecular", "packing", "is", "stabilized", "by", "intramolecular", "C—H", "O", "interactions", "and", "the", "crystal", "packing", "is", "determined", "by", "inter-", "molecular", "N—H", "O", "hydrogen", "bonds,", "and", "C—H", "O", "and", "C—H", "interactions.", "Related", "literature", "For", "related", "literature,", "see:", "Kamala", "et", "al.", "(2008);", "Lukacs", "&", "Ohno", "(1990);", "Sundari", "Bhaskaran", "et", "al.", "(2006);", "Suzuki", "et", "al.", "(1994);", "Yang", "et", "al.", "(1987);", "Amal", "Raj", "et", "al.", "(2003);", "Cremer", "&", "Pople", "(1975);", "Nardelli", "(1995);", "U¨", "lku¨", "et", "al.", "(1997).", "Experimental", "Crystal", "data", "C37H33BrN4O6", "Mr", "=", "709.58", "Monoclinic,", "Cc", "a", "=", "11.3988", "(4)", "A˚", "organic", "compounds", "b", "=", "34.8587", "(13)", "A˚", "c", "=", "8.7039", "(3)", "A˚", "=", "100.982", "(2)", "V", "=", "3395.1", "(2)", "A˚", "3", "Z", "=", "4", "Data", "collection", "Bruker", "Kappa", "APEX2", "diffractometer", "Absorption", "correction:", "multi-scan", "(Blessing,", "1995)", "Tmin", "=", "0.703,", "Tmax", "=", "0.769", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.040", "wR(F", "2)", "=", "0.120", "S", "=", "1.04", "8532", "reflections", "433", "parameters", "2", "restraints", "Table", "1", "Hydrogen-bond", "geometry", "(A˚", ",", ").", "D—H", "A", "C11—H11", "O4", "C4—H4", "O4i", "C31—H31", "O4ii", "N1—H1A", "O5iii", "C18—H18", "Cgiv", "D—H", "0.98", "0.93", "0.93", "0.86", "0.93", "Mo", "K", "radiation", "=", "1.26", "mm", "1", "T", "=", "293", "(2)", "K", "0.30", "0.22", "0.22", "mm", "37282", "measured", "reflections", "8532", "independent", "reflections", "6397", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.028", "H-atom", "parameters", "constrained", "max", "=", "0.43", "e", "A˚", "3", "0.37", "e", "A˚", "3", "min", "=", "Absolute", "structure:", "Flack", "(1983),", "4142", "Friedel", "pairs", "Flack", "parameter:", "0.008", "(6)", "H", "2.27", "2.57", "2.55", "2.02", "2.80", "A", "D", "A", "2.717", "(3)", "3.186", "(3)", "3.399", "(3)", "2.820", "(3)", "3.641", "(4)", "D—H", "A", "107", "124", "152", "155", "151", "Symmetry", "codes:", "(i)", "x;", "y;", "z", "1;", "(ii)", "x;", "y", "þ", "2;", "z", "12;", "(iii)", "x", "þ", "12;", "y", "þ", "32;", "z", "12;", "(iv)", "x;", "y;", "z", "þ", "1.", "Cg", "is", "the", "centroid", "of", "the", "indole", "benzene", "ring.", "Data", "collection:", "APEX2", "(Bruker,", "2004);", "cell", "refinement:", "APEX2", "and", "SAINT", "(Bruker,", "2004);", "data", "reduction:", "SAINT", "and", "XPREP", "(Bruker,", "2004);", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "ORTEP-3", "(Farrugia,", "1997);", "software", "used", "to", "prepare", "material", "for", "publication:", "PLATON", "(Spek,", "2003).", "SN", "thanks", "Professor", "M.", "N.", "Ponnuswamy,", "Department", "of", "Crystallography", "and", "Biophysics,", "University", "of", "Madras,", "India,", "for", "his", "guidance", "and", "valuable", "suggestions.", "SN", "thanks", "SRM", "management,", "India,", "for", "their", "support.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "RK2086).", "References", "Amal", "Raj,", "A.,", "Raghunathan,", "R.,", "Sridevi", "Kumari,", "M.", "R.", "&", "Raman,", "N.", "(2003).", "Bioorg.", "Med.", "Chem.", "11,", "407–409.", "Blessing,", "R.", "H.", "(1995).", "Acta", "Cryst.", "A51,", "33–38.", "Bruker", "(2004).", "APEX2,", "SAINT", "and", "XPREP.", "Bruker", "AXS", "Inc.,", "Madison,", "Wisconsin,", "USA.", "Cremer,", "D.", "&", "Pople,", "J.", "A.", "(1975).", "J.", "Am.", "Chem.", "Soc.", "97,", "1354–1358.", "Farrugia,", "L.", "J.", "(1997).", "J.", "Appl.", "Cryst.", "30,", "565.", "Flack,", "H.", "D.", "(1983).", "Acta", "Cryst.", "A39,", "876–881.", "Kamala,", "E.", "T.", "S.,", "Nirmala,", "S.,", "Sudha,", "L.,", "Arumugam,", "N.", "&", "Raghanathan,", "R.", "(2008).", "Acta", "Cryst.", "E64,", "o716–o717.", "Lukacs,", "G.", "&", "Ohno,", "M.", "(1990).", "Editors.", "Recent", "Progress", "in", "the", "Chemical", "Synthesis", "of", "Antibiotics.", "Berlin:", "Springer.", "Nardelli,", "M.", "(1995).", "J.", "Appl.", "Cryst.", "28,", "659.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Spek,", "A.", "L.", "(2003).", "J.", "Appl.", "Cryst.", "36,", "7–13.", "Acta", "Cryst.", "(2008).", "E64,", "o1095–o1096", "doi:10.1107/S1600536808014190", "Nirmala", "et", "al.", "o1095" ]
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88-2961354-0
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88-2961354-1
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88-2961354-12
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88-2961354-11
[ "supplementary", "materials" ]
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88-2961354-2
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88-2961354-10
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88-2961354-9
[ "Fig.", "1", "supplementary", "materials", "sup-11" ]
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88-2961354-13
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[ "supplementary", "materials", "Acta", "Cryst.", "(2008).", "E64,", "o1095-o1096", "[", "doi:10.1107/S1600536808014190", "]", "Methyl", "3-(4-bromophenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo-2-phenylazetid-", "in-2-yl]-4-nitropyrrolidine-2-carboxylate", "S.", "Nirmala,", "E.", "T.", "S.", "Kamala,", "L.", "Sudha,", "N.", "Arumugam", "and", "R.", "Raghunathan", "Comment", "β–Lactams", "with", "a", "substituent", "at", "the", "N", "atom,", "which", "is", "easily", "removable", "under", "mild", "conditions", "have", "found", "wide", "applicability", "in", "the", "synthesis", "of", "bicyclic", "β–lactam", "antibiotics", "(Lukacs", "&", "Ohno,", "1990).", "Substituted", "pyrrolidines", "have", "gained", "much", "importance", "because", "they", "are", "the", "structural", "elements", "of", "many", "alkaloids.", "It", "has", "been", "found", "that", "they", "exhibit", "antifungal", "activity", "against", "various", "pathogens", "(Amal", "Raj", "et", "al.,", "2003).", "Optically", "active", "pyrrolidine", "derivatives", "have", "been", "used", "as", "intermediates", "in", "controlled", "asymmetric", "synthesis", "(Suzuki", "et", "al.,", "1994).", "Since", "the", "title", "compound,", "(I),", "also", "contains", "an", "indole", "unit", "it", "may", "also", "exhibit", "some", "biological", "activity.", "In", "view", "of", "these,", "the", "structure", "of", "title", "compound", "is", "determined", "to", "establish", "the", "conformation", "of", "the", "molecule", "(Fig.", "1).", "The", "bond", "lengths", "and", "angles", "in", "I", "are", "agree", "with", "those", "observed", "in", "a", "similar", "structure", "(Sundari", "Bhaskaran", "et", "al.,", "2006;", "Kamala", "et", "al.,", "2008).", "The", "β–lactam", "ring", "is", "planar", "with", "its", "internal", "angles", "in", "the", "range", "84.4", "(2)", "to", "95.5", "(2)°.", "The", "C–C–C", "bond", "angle", "in", "the", "β–lactam", "ring", "is", "comparable", "to", "the", "values", "in", "related", "reported", "structures", "(Ulku", "et", "al.,", "1997).", "The", "bond", "N4?C16,", "is", "shorter", "than", "the", "bond", "lengths,", "N4—C14", "and", "N4—C17", "and", "is", "close", "to", "the", "length", "of", "a", "double", "bond,", "a", "feature", "observed", "in", "β–propiolactam", "(Yang", "et", "al.,", "1987)", "and", "where", "C", "and", "N", "are", "sp2", "hybridized.", "The", "methoxy", "group", "is", "coplanar", "with", "the", "C17/C18/C19/C20/C21/C22", "benzene", "ring:", "dihedral", "angle", "C21–C20–O6–C23", "=", "161.0", "(4)°.", "The", "methoxyphenyl", "and", "the", "phenyl", "rings", "bridged", "by", "the", "β–lactam", "ring", "are", "oriented", "at", "an", "angle", "of", "42.32", "(11)°", "with", "respect", "to", "each", "other,", "whereas", "the", "β–lactam", "ring", "makes", "a", "dihedral", "angles", "of", "28.32", "(13)°", "and", "70.16", "(13)°", "with", "them", "respectively.", "The", "indole", "moiety", "is", "planar", "and", "makes", "a", "dihedral", "angle", "of", "38.01", "(11)°,", "62.8", "(7)°", "and", "73.8", "(9)°", "with", "the", "β–lactam,", "bromophenyl", "and", "phenyl", "rings", "respectively.", "The", "nitro–group", "is", "orthogonal", "to", "indole", "moiety", "[89.2", "(2)°]", "and", "makes", "a", "dihedral", "angle", "of", "66.6", "(3)°", "with", "the", "β–lactam", "ring.", "The", "pyrrolidine", "ring", "N2/C10/C11/C12/C13", "adopts", "an", "envelope", "conformation,", "with", "asymmetry", "parameters", "(Nardelli,", "1995),", "ΔCS", "(C13)", "=", "0.038", "(2)", "and", "puckering", "parameters", "(Cremer", "&", "Pople,", "1975)", "q2", "=", "0.377", "(2)Å", "and", "φ", "=", "150.8", "(3)°.", "Atom", "C13", "deviates", "from", "the", "mean", "plane", "defined", "by", "N2/C10/C11/C12", "on", "0.573", "(8)", "Å.", "In", "the", "crystal", "structure", "of", "I", "(Fig.2),", "adjacent", "molecules", "are", "linked", "by", "N—H···O", "and", "C—H···O", "hydrogen", "bonds", "into", "chains.", "In", "addition,", "the", "packing", "is", "stabilized", "by", "C—H···Cg", "interactions", "involving", "C3/C4/C5/C6/C7/C8", "rings", "with", "centroid", "Cg.", "Experimental", "The", "β–lactam", "aldehyde", "(1", "mol)", "was", "treated", "with", "tryptophanmethylester", "hydrochloride", "(1", "mol)", "in", "the", "presence", "of", "Et3N", "(2.5", "mol)", "and", "anhydrous", "MgSO4", "(2", "g)", "in", "dry", "dichloromethane", "(10", "ml)", "at", "room", "temperature", "for", "12", "h", "to", "give", "the", "imine.", "The", "imine", "was", "washed", "with", "water", "and", "dried", "over", "Na2SO4.", "The", "solvent", "was", "evaporated", "under", "vacuum.", "The", "imine", "(1", "mol)", "was", "then", "strirred", "with", "silver(I)", "acetate", "and", "p–bromo", "nitrostyrene", "(1", "mol)", "in", "the", "presence", "of", "Et3N", "(1.2", "mol)", "and", "molecular", "sieves", "in", "dry", "toluene", "(30", "ml)", "at", "room", "temperature", "for", "12", "h.", "The", "reaction", "mixture", "was", "filtered", "through", "a", "plug", "celite.", "The", "solvent", "was", "sup-1" ]
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88-2961354-4
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19-3052118-4
[ "supplementary", "materials", "C26—O2—Zn", "S1—O3—Zn", "C15—N1—C16", "C15—N1—Zn", "C16—N1—Zn", "C20—N2—C18", "C20—N2—Zn", "C18—N2—Zn", "O1—C1—C6", "O1—C1—C2", "C6—C1—C2", "C3—C2—C1", "C3—C2—C7", "C1—C2—C7", "C2—C3—C4", "C2—C3—H3", "C4—C3—H3", "C5—C4—C3", "C5—C4—C11", "C3—C4—C11", "C4—C5—C6", "C4—C5—H5", "C6—C5—H5", "C15—C6—C5", "C15—C6—C1", "C5—C6—C1", "C8—C7—C2", "C8—C7—C9", "C2—C7—C9", "C8—C7—C10", "C2—C7—C10", "C9—C7—C10", "C7—C8—H8A", "C7—C8—H8B", "H8A—C8—H8B", "C7—C8—H8C", "H8A—C8—H8C", "H8B—C8—H8C", "C7—C9—H9A", "C7—C9—H9B", "H9A—C9—H9B", "C7—C9—H9C", "H9A—C9—H9C", "H9B—C9—H9C", "C7—C10—H10A", "C7—C10—H10B", "H10A—C10—H10B", "C7—C10—H10C", "H10A—C10—H10C", "sup-8", "128.42", "(10)", "138.77", "(7)", "122.47", "(14)", "125.65", "(11)", "111.62", "(10)", "122.86", "(14)", "123.57", "(11)", "111.52", "(10)", "123.11", "(14)", "119.20", "(14)", "117.68", "(14)", "118.19", "(14)", "121.84", "(14)", "119.93", "(14)", "124.96", "(15)", "117.5", "117.5", "116.58", "(14)", "124.38", "(14)", "119.00", "(14)", "122.44", "(15)", "118.8", "118.8", "116.26", "(14)", "123.81", "(14)", "119.87", "(14)", "111.26", "(13)", "107.46", "(14)", "110.91", "(13)", "107.55", "(14)", "110.07", "(13)", "109.50", "(14)", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "C22—C23—C24", "C22—C23—C27", "C24—C23—C27", "C25—C24—C23", "C25—C24—H24", "C23—C24—H24", "C24—C25—C26", "C24—C25—C31", "C26—C25—C31", "O2—C26—C25", "O2—C26—C21", "C25—C26—C21", "C28—C27—C29", "C28—C27—C23", "C29—C27—C23", "C28—C27—C30", "C29—C27—C30", "C23—C27—C30", "C27—C28—H28A", "C27—C28—H28B", "H28A—C28—H28B", "C27—C28—H28C", "H28A—C28—H28C", "H28B—C28—H28C", "C27—C29—H29A", "C27—C29—H29B", "H29A—C29—H29B", "C27—C29—H29C", "H29A—C29—H29C", "H29B—C29—H29C", "C27—C30—H30A", "C27—C30—H30B", "H30A—C30—H30B", "C27—C30—H30C", "H30A—C30—H30C", "H30B—C30—H30C", "C32—C31—C33", "C32—C31—C25", "C33—C31—C25", "C32—C31—C34", "C33—C31—C34", "C25—C31—C34", "C31—C32—H32A", "C31—C32—H32B", "H32A—C32—H32B", "C31—C32—H32C", "H32A—C32—H32C", "H32B—C32—H32C", "C31—C33—H33A", "116.77", "(15)", "121.18", "(15)", "122.00", "(14)", "124.81", "(15)", "117.6", "117.6", "118.56", "(15)", "121.73", "(14)", "119.71", "(14)", "119.29", "(14)", "123.08", "(14)", "117.63", "(14)", "109.03", "(16)", "110.91", "(15)", "112.83", "(14)", "108.11", "(16)", "107.01", "(15)", "108.77", "(14)", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "107.50", "(15)", "111.81", "(14)", "109.75", "(14)", "107.25", "(15)", "110.41", "(14)", "110.06", "(14)", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5" ]
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19-3052118-10
[ "metal-organic", "compounds", "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "(Dimethyl", "sulfoxide-jO){4,40,6,60-tetra-", "tert-butyl-2,20-[1,2-dicyanoethene-1,2-", "diylbis(nitrilomethylidyne)]diphenolato-", "j4O,N,N0,O0", "}zinc(II)", "acetonitrile", "monosolvate", "E.", "S.", "Aazam,a‡", "Seik", "Weng", "Ngb", "and", "Edward", "R.", "T.", "Tiekinkb*", "aDepartment", "of", "Chemistry,", "Girls", "Campus,", "King", "Abdulaziz", "University,", "PO", "Box", "6171,", "Jeddah", "21442,", "Saudi", "Arabia,", "and", "bDepartment", "of", "Chemistry,", "University", "of", "Malaya,", "50603", "Kuala", "Lumpur,", "Malaysia", "Correspondence", "e-mail:", "edward.tiekink@gmail.com", "Received", "27", "January", "2011;", "accepted", "27", "January", "2011", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "100", "K;", "mean", "(C–C)", "=", "0.002", "A˚;", "R", "factor", "=", "0.032;", "wR", "factor", "=", "0.080;", "data-to-parameter", "ratio", "=", "19.4.", "The", "Zn", "atom", "in", "the", "title", "acetonitrile", "solvate,", "[Zn(C34H42N4O2)(C2H6OS)]", "CH3CN,", "exists", "in", "a", "distorted", "square-pyramidal", "geometry", "with", "the", "basal", "plane", "defined", "by", "the", "N2O2", "atoms", "of", "the", "tetradentate", "Schiff", "base", "and", "with", "the", "dimethyl", "sulfoxide", "O", "atom", "in", "the", "apical", "position.", "The", "tetradentate", "mode", "of", "coordination", "of", "the", "Schiff", "base", "ligand", "leads", "to", "a", "five-membered", "ZnN2C2", "chelate", "ring", "which", "adopts", "an", "envelope", "conformation", "with", "the", "Zn", "atom", "at", "the", "flap,", "and", "two", "six-membered", "ZnOC4N", "chelate", "rings,", "one", "of", "which", "is", "approximately", "planar", "(r.m.s.", "deviation", "=", "0.054", "A˚", ")", "but", "the", "other", "has", "significant", "puckering", "(r.m.s.", "deviation", "=", "0.203", "A˚", ").", "Related", "literature", "For", "background", "to", "metal", "salicylaldiminato", "complexes", "as", "optoelectronic", "materials,", "see:", "Liuzzo", "et", "al.", "(2010);", "Shirai", "et", "al.,", "(2000).", "For", "background", "to", "zinc", "complexes", "as", "organic", "light-", "emitting", "diodes,", "see:", "Chen", "et", "al.", "(2009).", "For", "related", "structures,", "see:", "MacLachlan", "et", "al.", "(1996).", "For", "geometrical", "analysis,", "see:", "Addison", "et", "al.", "(1984).", "‡", "Additional", "correspondence", "author,", "e-mail:", "wayfield8@yahoo.com.", "m314", "Aazam", "et", "al.", "doi:10.1107/S160053681100359X", "Acta", "Cryst.", "(2011).", "E67,", "m314–m315", "Experimental", "Crystal", "data", "[Zn(C34H42N4O2)(C2H6OS)]", "-", "C2H3N", "Mr", "=", "723.27", "Monoclinic,", "P21=n", "a", "=", "12.3288", "(7)", "A˚", "b", "=", "17.7043", "(9)", "A˚", "c", "=", "17.3932", "(9)", "A˚", "Data", "collection", "Bruker", "SMART", "APEX", "CCD", "diffractometer", "Absorption", "correction:", "multi-scan", "(SADABS;", "Sheldrick,", "1996)", "Tmin", "=", "0.603,", "Tmax", "=", "0.746", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.032", "wR(F", "2)", "=", "0.080", "S", "=", "1.02", "8699", "reflections", "Table", "1", "Selected", "bond", "lengths", "(A˚", ").", "Zn—O1", "Zn—O2", "Zn—O3", "1.9470", "(11)", "1.9390", "(11)", "2.0467", "(12)", "Zn—N1", "Zn—N2", "2.0939", "(14)", "2.1001", "(13)", "Data", "collection:", "APEX2", "(Bruker,", "2008);", "cell", "refinement:", "SAINT", "(Bruker,", "2008);", "data", "reduction:", "SAINT;", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "ORTEP-3", "(Farrugia,", "1997),", "DIAMOND", "(Brandenburg,", "2006);", "soft-", "ware", "used", "to", "prepare", "material", "for", "publication:", "publCIF", "(Westrip,", "2010)", "and", "PLATON", "(Spek,", "2009).", "The", "authors", "acknowledge", "King", "Abdulaziz", "University", "for", "financial", "support", "(grant", "No.", "17–013/430).", "The", "authors", "also", "thank", "the", "University", "of", "Malaya", "for", "support", "of", "the", "crystal-", "lographic", "facility.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "HB5794).", "=", "92.4391", "(8)", "V", "=", "3793.0", "(3)", "A˚", "3", "Z", "=", "4", "Mo", "K", "radiation", "=", "0.74", "mm", "1", "T", "=", "100", "K", "0.45", "0.30", "0.10", "mm", "35700", "measured", "reflections", "8699", "independent", "reflections", "7157", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.041", "448", "parameters", "H-atom", "parameters", "constrained", "max", "=", "0.56", "e", "A˚", "3", "min", "=", "0.29", "e", "A˚", "3" ]
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19-3052118-0
[ "Fig.", "1", "supplementary", "materials", "sup-11" ]
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19-3052118-13
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19-3052118-5
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19-3052118-11
[ "supplementary", "materials", "Acta", "Cryst.", "(2011).", "E67,", "m314-m315", "[", "doi:10.1107/S160053681100359X", "]", "(Dimethyl", "sulfoxide-", "O){4,4',6,6'-tetra-tert-butyl-2,2'-[1,2-dicyanoethene-1,2-", "diylbis(nitrilomethylidyne)]diphenolato-", "4O,N,N',O'}zinc(II)", "acetonitrile", "monosolvate", "E.", "S.", "Aazam,", "S.", "W.", "Ng", "and", "E.", "R.", "T.", "Tiekink", "Comment", "Metal", "complexes", "with", "salicylaldiminato", "ligands", "are", "promising", "materials", "for", "optoelectronic", "applications", "due", "to", "their", "out-", "standing", "photo-", "and", "electro-luminescent", "properties", "(Liuzzo", "et", "al.,", "2010;", "Shirai", "et", "al.,", "2000).", "One", "of", "the", "main", "appeals", "of", "this", "class", "of", "coordination", "complexes", "is", "that", "molecular", "engineering", "permits", "systematically", "the", "optimizing", "of", "spectroscopic", "and", "chemical", "properties.", "This", "chemical", "flexibility", "allows", "for", "the", "design", "of", "systems", "that", "respond", "to", "specific", "environment-", "al", "variables.", "Recently,", "zinc", "complexes", "have", "been", "introduced", "to", "OLED's", "(organic", "light-emitting", "diodes)", "and", "recognized", "as", "useful", "electron", "transport", "materials", "(Chen", "et", "al.,", "2009).", "The", "above", "motivated", "the", "synthesis", "and", "structural", "characterization", "of", "the", "title", "complex,", "(I).", "The", "Zn", "atom", "in", "(I),", "Fig.", "1,", "is", "tetracoordinated", "by", "the", "N2O2", "donor", "atoms", "of", "the", "tetradentate", "Schiff-base", "ligand", "and", "the", "O", "atom", "derived", "from", "the", "dimethyl", "sulfoxide", "ligand,", "Table", "1;", "the", "asymmetric", "unit", "is", "completed", "by", "a", "non-coordinating", "acetoni-", "trile", "molecule.", "The", "resulting", "N2O3", "donor", "set", "is", "based", "on", "a", "square", "pyramidal", "arrangement", "with", "the", "dimethyl", 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"significantly", "more", "distortion", "in", "the", "O2-containing", "chelate", "ring", "(r.m.s.", "=", "0.203", "Å).", "Schiff-", "base", "ligands", "derived", "from", "diaminomaleonitrile", "have", "been", "documented", "and", "shown", "to", "adopt", "comparable", "coordination", "modes", "towards", "transition", "metals", "(MacLachlan", "et", "al.,", "1996).", "Experimental", "A", "mixture", "of", "diaminemaleonitrile", "(0.1", "g,", "0.93", "mmol),", "3,5-di-tert-butyl-2-hydroxybenzaldehyde", "(0.1", "g,", "1.86", "mmol),", "zinc(II)", "acetate", "dihydrate", "(0.2", "g,", "0.93", "mmol)", "and", "ethanol", "(5", "ml)", "were", "placed", "in", "a", "glass", "Petri", "dish", "and", "capped", "with", "a", "glass", "cover.", "The", "dish", "was", "placed", "in", "a", "microwave", "oven", "(700", "W)", "and", "irradiated", "for", "1", "min.", "The", "reaction", "mixture", "was", "cooled", "and", "washed", "with", "15", "ml", "of", "ethanol.", "The", "purple", "solid", "was", 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"574,", "501,", "380,", "375,", "318,", "245", "nm.", "sup-1" ]
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19-3052118-8
[ "metal-organic", "compounds", "References", "Addison,", "A.", "W.,", "Rao,", "T.", "N.,", "Reedijk,", "J.,", "van", "Rijn,", "J.", "&", "Verschoor,", "G.", "C.", "(1984).", "J.", "Chem.", "Soc.", "Dalton", "Trans.", "pp.", "1349–1356.", "Brandenburg,", "K.", "(2006).", "DIAMOND.", "Crystal", "Impact", "GbR,", "Bonn,", "Germany.", "Bruker", "(2008).", "APEX2", "and", "SAINT.", "Bruker", "AXS", "Inc.,", "Madison,", "Wisconsin,", "USA.", "Chen,", "L.,", "Qiao,", "J.,", "Xie,", "J.,", "Duan,", "L.,", "Zhang,", "D.,", "Wang,", "L.", "&", "Qiu,", "Y.", "(2009).", "Inorg.", "Chim.", "Acta,", "362,", "2327–2333.", "Farrugia,", "L.", "J.", "(1997).", "J.", "Appl.", "Cryst.", "30,", "565.", "Liuzzo,", "V.,", "Oberhauser,", "W.", "&", "Pucci,", "A.", "(2010).", "Inorg.", "Chem.", "Commun.", "13,", "686–688.", "MacLachlan,", "M.", "J.,", "Park,", "M.", "K.", "&", "Thompson,", "L.", "K.", "(1996).", "Inorg.", "Chem.", "35,", "5492–5499.", "Sheldrick,", "G.", "M.", "(1996).", "SADABS.", "University", "of", "Go¨", "ttingen,", "Germany.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Shirai,", "K.,", "Matsuoka,", "M.", "&", "Fukunishi,", "K.", "(2000).", "Dyes", "Pigments,", "47,", "107–115.", "Spek,", "A.", "L.", "(2009).", "Acta", "Cryst.", "D65,", "148–155.", "Westrip,", "S.", "P.", "(2010).", "J.", "Appl.", "Cryst.", "43,", "920–925.", "Acta", "Cryst.", "(2011).", "E67,", "m314–m315", "Aazam", "et", "al.", "[Zn(C34H42N4O2)(C2H6OS)]", "C2H3N", "m315" ]
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19-3052118-1
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19-3052118-9
[ "supplementary", "materials" ]
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19-3052118-2
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19-3052118-12
[ "N1—C02—N2", "N1—C02—S1", "N2—C02—S1", "C04—C03—C08", "C04—C03—C01", "C08—C03—C01", "C05—C04—C03", "C05—C04—H04", "C03—C04—H04", "C04—C05—C06", "C04—C05—H05", "C06—C05—H05", "C07—C06—C05", "C07—C06—H06", "C05—C06—H06", "C06—C07—C08", "C06—C07—H07", "C08—C07—H07", "C07—C08—C03", "C07—C08—H08", "C03—C08—H08", "C14—C09—C10", "C14—C09—N2", "C10—C09—N2", "C09—C10—C11", "C09—C10—H10", "C11—C10—H10", "C12—C11—C10", "C12—C11—H11", "C10—C11—H11", "C11—C12—C13", "C11—C12—H12", "C13—C12—H12", "C12—C13—C14", "C12—C13—H13", "C14—C13—H13", "C09—C14—C13", "C09—C14—H14", "C13—C14—H14", "C16—C15—C20", "C16—C15—N2", "C20—C15—N2", "C15—C16—C17", "C15—C16—H16", "C17—C16—H16", "C16—C17—C18", "C16—C17—H17", "O5—C01—C03—C04", "Acta", "Cryst.", "(2012).", "E68,", "m1053–m1054", "113.29", "(18)", "130.18", "(16)", "116.53", "(15)", "119.53", "(19)", "120.11", "(19)", "120.36", "(18)", "120.4", "(2)", "119.8", "119.8", "120.1", "(2)", "120", "120", "119.9", "(2)", "120.1", "120.1", "120.5", "(2)", "119.7", "119.7", "119.6", "(2)", "120.2", "120.2", "121.27", "(19)", "119.49", "(19)", "119.20", "(19)", "119.0", "(2)", "120.5", "120.5", "120.3", "(2)", "119.9", "119.9", "120.1", "(2)", "119.9", "119.9", "120.4", "(2)", "119.8", "119.8", "118.9", "(2)", "120.6", "120.6", "120.8", "(2)", "120.08", "(19)", "119.10", "(19)", "119.7", "(2)", "120.1", "120.1", "119.9", "(2)", "120.1", "−5.8", "(3)", "supplementary", "materials", "C23—C22—Rh1", "C21—C22—H22", "C23—C22—H22", "Rh1—C22—H22", "C22—C23—C24", "C22—C23—H23A", "C24—C23—H23A", "C22—C23—H23B", "C24—C23—H23B", "H23A—C23—H23B", "C25—C24—C23", "C25—C24—H24A", "C23—C24—H24A", "C25—C24—H24B", "C23—C24—H24B", "H24A—C24—H24B", "C26—C25—C24", "C26—C25—Rh1", "C24—C25—Rh1", "C26—C25—H25", "C24—C25—H25", "Rh1—C25—H25", "C25—C26—C27", "C25—C26—Rh1", "C27—C26—Rh1", "C25—C26—H26", "C27—C26—H26", "Rh1—C26—H26", "C26—C27—C28", "C26—C27—H27A", "C28—C27—H27A", "C26—C27—H27B", "C28—C27—H27B", "H27A—C27—H27B", "C21—C28—C27", "C21—C28—H28A", "C27—C28—H28A", "C21—C28—H28B", "C27—C28—H28B", "H28A—C28—H28B", "C01—N1—C02", "C02—N2—C09", "C02—N2—C15", "C09—N2—C15", "C01—O5—Rh1", "C02—S1—Rh1", "113.14", "(14)", "114.1", "114.1", "114.1", "112.68", "(18)", "109.1", "109.1", "109.1", "109.1", "107.8", "112.62", "(18)", "109.1", "109.1", "109.1", "109.1", "107.8", "125.8", "(2)", "71.44", "(12)", "110.18", "(14)", "113.8", "113.8", "113.8", "123.3", "(2)", "70.90", "(12)", "112.49", "(14)", "114.2", "114.2", "114.2", "111.68", "(18)", "109.3", "109.3", "109.3", "109.3", "107.9", "113.09", "(19)", "109", "109", "109", "109", "107.8", "126.80", "(18)", "122.68", "(17)", "121.22", "(17)", "116.10", "(16)", "130.27", "(13)", "108.49", "(7)", "C21—Rh1—C25—C26", "−66.06", "(14)", "sup-7" ]
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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "(N-Benzoyl-N0,N0-diphenylthioureato-", "2", "4", "j", "S,O)(g", "-cycloocta-1,5-diene)-", "rhodium(I)", "Stefan", "Warsink*", "and", "Andreas", "Roodt", "Department", "of", "Chemistry,", "University", "of", "the", "Free", "State,", "PO", "Box", "339,", "Bloemfontein", "9300,", "South", "Africa", "Correspondence", "e-mail:", "2011009426@ufs4life.ac.za", "Received", "27", "June", "2012;", "accepted", "29", "June", "2012", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "100", "K;", "mean", "(C–C)", "=", "0.003", "A˚;", "R", "factor", "=", "0.028;", "wR", "factor", "=", "0.070;", "data-to-parameter", "ratio", "=", "18.7.", "The", "title", "complex,", "[Rh(C20H15N2OS)(C8H12)],", "exhibits", "an", "essentially", "square-planar", "coordination", "environment", "around", "the", "RhI", "atom,", "which", "bears", "a", "bidentate", "cyclooctadiene", "ligand", "as", "well", 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"cyclooctadiene,", "see:", "Kotze", "et", "al.", "(2010);", "Cauzzi", "et", "al.", "(1995).", "For", "trisubstituted", "thiourea", "ligands,", "see:", "Hernandez", "et", "al.", "(2003);", "Arslan", "et", "al.", "(2003).", "Experimental", "Crystal", "data", "[Rh(C20H15N2OS)(C8H12)]", "Mr", "=", "542.50", "Triclinic,", "P1", "a", "=", "9.8028", "(4)", "A˚", "metal-organic", "compounds", "Z", "=", "2", "Mo", "K", "radiation", "=", "0.84", "mm", "1", "T", "=", "100", "K", "0.22", "0.17", "0.09", "mm", "12388", "measured", "reflections", "5583", "independent", "reflections", "5014", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.025", "298", "parameters", "H-atom", "parameters", "constrained", "max", "=", "0.66", "e", "A˚", "3", "min", "=", "1.01", "e", "A˚", "3", "b", "=", "11.2293", "(5)", "A˚", "c", "=", "11.5316", "(5)", "A˚", "=", "90.408", "(2)", "=", "91.684", "(2)", "=", "112.1831", "(18)", "V", "=", "1174.69", "(9)", "A˚3", "Data", "collection", "Bruker", "X8", "APEXII", "4K", "KappaCCD", "diffractometer", "Absorption", "correction:", "multi-scan", "(SADABS;", "Bruker,", "2007)", "Tmin", "=", "0.843,", "Tmax", "=", "0.927", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.028", "wR(F", "2)", "=", "0.07", "S", "=", "1.04", "5583", "reflections", "Table", "1", "Selected", "bond", "lengths", "(A˚", ").", "Rh1—O5", "Rh1—C21", "Rh1—C22", "Rh1—C25", "Rh1—C26", "2.0537", "(16)", "2.116", "(2)", "2.131", "(2)", "2.148", "(2)", "2.155", "(2)", "Rh1—S1", "C01—O5", "C01—N1", "C02—N1", "C02—S1", "2.2942", "(10)", "1.263", "(2)", "1.330", "(3)", "1.346", "(3)", "1.726", "(2)", "Data", "collection:", "APEX2", "(Bruker,", "2007);", "cell", "refinement:", "SAINT-", "Plus", "(Bruker,", "2007);", "data", "reduction:", "SAINT-Plus;", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "Mercury", "(Macrae", "et", "al.,", "2008);", "software", "used", "to", "prepare", "material", "for", "publication:", "WinGX", "(Farrugia,", "1999).", "The", "authors", "thank", "SASOL,", "the", "South", "African", "NRF", "and", "THRIP,", "the", "University", "of", "the", "Free", "State", "Research", "Fund", "and", "the", "UFS", "Materials", "and", "Nanosciences", "SStrategic", "Research", "Cluster", "initiative", "for", "financial", "support.", "The", "views", "expressed", "do", "not", "necessarily", "represent", "those", "of", "the", "NRF.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "WM2654).", "References", "Arslan,", "H.,", "Flo¨", "rke,", "U.", "&", "Ku¨", "lcu¨", ",", "N.", "(2003).", "Acta", "Cryst.", "E59,", "o641–o642.", "Bruker", "(2007).", "APEX2,", "SAINT-Plus", "and", "SADABS.", "Bruker", "AXS", "Inc.,", "Madison,", "Wisconsin,", "USA.", "Cauzzi,", "D.,", "Lanfranchi,", "M.,", "Marzolini,", "G.,", "Predieri,", "G.,", "Tiripicchio,", "A.,", "Costa,", "M.", "&", "Zanoni,", "R.", "(1995).", "J.", "Organomet.", "Chem.", "488,", "115–125.", "Crous,", "R.,", "Datt,", "M.,", "Foster,", "D.,", "Bennie,", "L.,", "Steenkamp,", "C.,", "Huyser,", "J.,", "Kirsten,", "L.,", "Steyl,", "G.", "&", "Roodt,", "A.", "(2005).", "Dalton", "Trans.", "pp.", "1108–1116.", "Farrugia,", "L.", "J.", "(1999).", "J.", "Appl.", "Cryst.", "32,", "837–838.", "Grim,", "S.", "O.,", "Kettler,", "P.", "B.", "&", "Thoden,", "J.", "B.", "(1991).", "Organometallics,", "10,", "2399–", "2403.", "Guiseppe,", "A.", "D.,", "Casterlenas,", "R.,", "Perez-Torrente,", "J.", "J.,", "Lahoz,", "F.", "H.,", "Polo,", "V.", "&", "Oro,", "L.", "A.", "(2011).", "Angew.", "Chem.", "Int.", "Ed.", "50,", "3938–3942.", "Hernandez,", "W.,", "Spodine,", "E.,", "Munoz,", "J.", "C.,", "Beyer,", "L.,", "Schroder,", "U.,", "Ferreira,", "J.", "&", "Pavani,", "M.", "(2003).", "Bioinorg.", "Chem.", "Appl.", "1,", "271–284.", 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33-3414120-5
[ "supplementary", "materials", "Rh1—C22—C23—C24", "C22—C23—C24—C25", "C23—C24—C25—C26", "C23—C24—C25—Rh1", "O5—Rh1—C25—C26", "−12.0", "(3)", "30.3", "(3)", "47.4", "(3)", "−33.8", "(2)", "94.60", "(13)", "O5—Rh1—S1—C02", "C21—Rh1—S1—C02", "C22—Rh1—S1—C02", "C25—Rh1—S1—C02", "C26—Rh1—S1—C02", "4.43", "(9)", "164.79", "(10)", "−156.91", "(10)", "−82.05", "(19)", "102.1", "(2)", "Acta", "Cryst.", "(2012).", "E68,", "m1053–m1054", "sup-9" ]
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33-3414120-10
[ "metal-organic", "compounds", "Macrae,", "C.", "F.,", "Bruno,", "I.", "J.,", "Chisholm,", "J.", "A.,", "Edgington,", "P.", "R.,", "McCabe,", "P.,", "Pidcock,", "E.,", "Rodriguez-Monge,", "L.,", "Taylor,", "R.,", "van", "de", "Streek,", "J.", "&", "Wood,", "P.", "A.", "(2008).", "J.", "Appl.", "Cryst.", "41,", "466–470.", "Roodt,", "A.,", "Visser,", "H.", "G.", "&", "Brink,", "A.", "(2011).", "Crystallogr.", "Rev.", "17,", "241–280.", "Sacht,", "C.", "I.,", "Datt,", "M.", "S.,", "Otto,", "S.", "&", "Roodt,", "A.", "(2000a).", "J.", "Chem.", "Soc.", "Dalton", "Trans.", "pp.", "727–73.", "Sacht,", "C.", "I.,", "Datt,", "M.", "S.,", "Otto,", "S.", "&", "Roodt,", "A.", "(2000b).", "J.", "Chem.", "Soc.", "Dalton", "Trans.", "pp.", "4579–4586.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Trzeciak,", "A.", "M.,", "Borak,", "B.,", "Cinnik,", "Z.,", "Ziolkowski,", "J.", "J.,", "Guedes", "da", "Silva,", "M.", "F.", "C.", "&", "Pombeiro,", "A.", "J.", "L.", "(2004).", "Eur.", "J.", "Inorg.", "Chem.", "pp.", "1411–1419.", "Venter,", "J.", "A.,", "Purcell,", "W.,", "Visser,", "H.", "G.", "&", "Muller,", "T.", "J.", "(2009).", "Acta", "Cryst.", "E65,", "m1578.", "m1054", "Warsink", "and", "Roodt", "[Rh(C20H15N2OS)(C8H12)]", "Acta", "Cryst.", "(2012).", "E68,", "m1053–m1054" ]
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33-3414120-1
[ "supplementary", "materials", "supplementary", "materials", "Acta", "Cryst.", "(2012).", "E68,", "m1053–m1054", "[doi:10.1107/S1600536812029753]", "(N-Benzoyl-N′,N′-diphenylthioureato-κ2S,O)(η4-cycloocta-1,5-diene)rhodium(I)", "Stefan", "Warsink", "and", "Andreas", "Roodt", "Comment", "Rhodium", "complexes", "bearing", "bidentate", "ligands", "that", "bond", "through", "σ-interactions,", "such", "as", "β-diketonates", "and", "8-hydroxy-", "quinolates", "are", "well", "known", "(Trzeciak", "et", "al.,", "2004;", "Guiseppe", "et", "al.,", "2011).", "These", "bidentate", "ligands", "are", "compatible", "with", "a", "wide", "range", "of", "other", "ligands", "such", "as", "carbonyls", "and", "phosphines", "(Crous", "et", "al.,", "2005;", "Venter", "et", "al.,", "2009;", "Roodt", "et", "al.,", "2011).", "Also", "regularly", "employed", "are", "thioureato", "ligands", "(Sacht", "et", "al.,", "2000a,b;", "Kemp", "et", "al.,", "1997).", "The", "title", "compound", "[Rh(C8H12)(C20H15N2OS)],", "(I),", "bears", "a", "benzoyl-functionalized", "thioureato", "moiety", "(Arslan", "et", "al.,", "2003),", "which", "can", "coordinate", "as", "a", "mono-", "or", "a", "bidentate", "ligand,", "depending", "on", "the", "metal", "and", "the", "other", "ligands", "present.", "With", "this", "specific", "ligand", "class,", "it", "was", "found", "that", "the", "peripheral", "substitution", "pattern", "significantly", "influences", "the", "coordination", "behaviour.", "When", "an", "N,N′,N′-trisubstituted", "thiourea", "ligand", "was", "employed,", "as", "is", "the", "case", "in", "this", "study,", "the", "thiourea", "coordinates", "as", "a", "monoanionic", "bidentate", "ligand,", "whereas", "an", "N,N′-disubstituted", "thiourea", "coordinates", "only", "through", "its", "sulfur-atom", "as", "a", "neutral", "monodentate", "ligand", "which", "is", "stabilized", "through", "intramolecular", "hydrogen", "bonding", "(Cauzzi", "et", "al.,", "1995;", "Kotze", "et", "al.,", "2010).", "One", "of", "these", "hydrogen", "bonds", "ensures", "that", "the", "sulfur", "and", "oxygen", "atoms", "are", "in", "a", "mutual", "trans-", "position,", "which", "stabilizes", "the", "pre-ligand", "in", "such", "a", "way", "that", "bidentate", "coordination", "is", "prevented.", "In", "the", "trisubstituted", "variation", "used", "in", "this", "study,", "this", "intramolecular", "interaction", "is", "not", "possible", "(Hernandez", "et", "al.,", "2003),", "which", "enables", "the", "ligand", "to", "coordinate", "through", "its", "sulfur", "and", "oxygen", "atoms", "simultaneously.", "This", "structural", "report", "is", "only", "the", "third", "in", "which", "a", "rhodium", "complex", "bears", "both", "cyclooctadiene", "and", "S,O-bidentate", "ligands", "(Grim", "et", "al.,", "1991;", "Hesp", "et", "al.,", "2007).", "The", "geometric", "parameters", "show", "that", "the", "rhodium(I)", "atom", "in", "the", "title", "compound", "has", "an", "essentially", "square", "planar", "coordination", "sphere.", "The", "deviation", "of", "the", "rhodium", "ion", "from", "the", "least", "mean", "squares", "plane,", "defined", "by", "the", "rhodium,", "oxygen", "and", "sulfur", "atoms", "and", "the", "centroids", "of", "the", "cyclooctadiene", "alkene", "bonds,", "is", "0.001", "Å.", "The", "donor", "atoms", "of", "the", "thioureato", "ligand", "and", "the", "centroids", "do", "not", "deviate", "more", "than", "0.031", "and", "0.011", "Å,", "respectively.", "The", "S,O-ligand", "exhibits", "a", "bite", "angle", "of", "92.60", "(5)°,", "and", "the", "cyclooctadiene", "ligand", "shows", "a", "bite", "angle", "of", "87.90", "(8)°.", "The", "bond", "lengths", "of", "the", "ligands", "to", "rhodium", "are", "all", "within", "the", "expected", "range", "for", "a", "compound", "of", "this", "type.", "The", "monoanionic", "ligand", "shows", "electron", "delocalization", "so", "that", "the", "bond", "lengths", "fall", "between", "those", "of", "single", "and", "double", "C—O,", "C—S", "and", "C—N", "bonds.", "There", "are", "no", "significant", "intermolecular", "interactions.", "Experimental", "The", "title", "compound", "was", "prepared", "by", "adding", "0.4", "mmol", "of", "N-benzoyl-N,N′-diphenyl", "thiourea", "to", "a", "suspension", "of", "0.2", "mmol", "[RhCl(cod)]2", "(cod", "is", "cyclooctadiene)", "in", "5", "ml", "of", "dichloromethane.", "The", "orange", "suspension", "changed", "into", "an", "orange", "solution,", "from", "which", "a", "yellow", "precipitate", "formed.", "After", "one", "hour", "of", "stirring,", "the", "yellow", "solid", "was", "isolated", "by", "filtration", "with", "a", "yield", "of", "197", "mg", "(90%,", "0.36", "mmol).", "1H", "NMR", "(300", "MHz,", "CDCl3):", "δ", "7.66", "(d,", "3J(HH)", "=", "7.4", "Hz,", "2H,", "o-benzoyl-H),", "7.5–7.2", "(m,", "13H,", "2x", "Ph,", "benzoyl),", "4.71", "(m,", "2H,", "cod-alkene),", "3.84", "(m,", "2H,", "cod-alkene),", "2.6–2.4", "(m,", "4H,", "cod-alkane),", "2.1–1.9", "(m,", "4H,", "cod-alkane).", "Yellow", "crystals", "of", "(I)", "were", "obtained", "by", "slow", "evaporation", "of", "a", "dichloromethane", "solution.", "Acta", "Cryst.", "(2012).", "E68,", "m1053–m1054", "sup-1" ]
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33-3414120-4
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33-3414120-3
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38-2970489-6
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38-2970489-3
[ "supplementary", "materials", "Fig.", "1", "sup-6" ]
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38-2970489-7
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79-2979940-4
[ "supplementary", "materials", "Fig.", "2", "sup-12" ]
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79-2979940-13
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79-2979940-3
[ "supplementary", "materials", "Acta", "Cryst.", "(2010).", "E66,", "m212", "[", "doi:10.1107/S1600536810002886", "]", "Bis(tribenzylammonium)", "tetrachloridoaurate(III)", "chloride", "Y.", "Fazaeli,", "V.", "Amani,", "M.", "M.", "Amini", "and", "H.", "R.", "Khavasi", "Comment", "There", "are", "several", "proton", "transfer", "systems", "using", "tribenzylamine,", "with", "proton", "donor", "molecules,", "such", "as", "{(TBA)(DBA)[CuCl4]},", "(II),", "(Zeng", "et", "al.,", "1994),", "(TBA)[DCHSTO],", "(III),", "(Jarvine", "et", "al.,", "1988)", "and", "{(TBA)3[PtCl6]Cl},", "(IV),", "(Yousefi", "et", "al.,", "2007)", "[where", "TBA", "is", "tribenzylammonium,", "DBA", "is", "dibenzylammonium", "and", "DCHSTO", "is", "1,1,1,1,2,2,2,3,3,3-decacarbonyl-2,3-(µ-hydrido)", "-2,3-(µ-sulfonyl)-triangulo-tri-osmium]", "have", "been", "synthesized", "and", "char-", "acterized", "by", "single-crystal", "X-ray", "diffraction", "methods.", "There", "are", "also", "several", "proton", "transfer", "systems", "using", "HAuCl4", "with", "proton", "acceptor", "molecules,", "such", "as", "[EMI][AuCl4],", "(V)", "and", "[BMI]2[AuCl4].2H2O,", "(VI),", "(Hasan", "et", "al.,", "1999),", "[H2bipy][AuCl4][Cl],", "(VII),", "(Zhang", "et", "al.,", "2006),", "[H7O3][15-", "crown-5][AuCl4],", "(VIII)", "and", "[H5O2][benzo-15-crown-5]2[AuCl4],", "(IX),", "(Johnson", "&", "Steed,", "1998),", "[H5O2]2[12-crown-", "4]2[AuCl4]2,", "(X),", "[H3O][18-crown-6][AuCl4],", "(XI)", "and", "[H3O]", "[4-nitrobenzo-18-crown-6][AuCl4],", "(XII),", "(Calleja", "et", "al.,", "2001),", "[DPpy.H][AuCl4],", "(XIII),", "(Yap", "et", "al.,", "1995),", "[H2DA18C6][AuCl4].2H2O,", "(XIV),", "(Hojjat", "Kashani", "et", "al.,", "2008),", "[dafonium][dafone][AuCl4],", "(XV),", "(Safari", "et", "al.,", "2009),", "[pz(py)2.H][AuCl4],", "(XVI),", "(Yıldırım,", "Akkurt,", "Safari", "et", "al.,", "2009a),", "[Ph2Phen.H][AuCl4],", "(XVII),", "(Yıldırım,", "Akkurt,", "Safari,", "Abedi", "et", "al.,", "2009b)", "[Where", "EMI", "is", "1-ethyl-3-methylimidazoli-", "um,", "BMI", "is", "1-butyl-3-methylimidazolium,", "H2bipy", "is", "2,2'-bipyridinium,", "DPpy.H", "is", "2,6-diphenylpyridinium,", "H2DA18C6", "is", "1,10-diazonia-18-crown-6,", "dafonium", "is", "9-oxo-4,5-diazafluoren-4-ium,", "dafone", "is", "4,5-diazafluoren-9-one,", "pz(py)2.H", "is", "2-", "(3-pyridin-2-ylpyrazin-2-yl)pyridinium", "and", "Ph2Phen.H", "is", "2,9-dimethyl-4,7-diphenyl-1,10-", "phenanthrolin-1-ium]", "have", "been", "synthesized", "and", "characterized", "by", "single-crystal", "X-ray", "diffraction", "methods.", "We", "report", "herein", "the", "synthesis", "and", "crystal", "struc-", "ture", "of", "the", "title", "compound,", "(I).", "The", "molecule", "of", "the", "title", "compound,", "(I),", "(Fig.", "1),", "contains", "two", "independent", "protonated", "tribenzylammonium", "cations", "and", "[AuCl4]-", "and", "Cl-", "anions.", "The", "AuIII", "atom", "has", "a", "squareplanar", "environment", "defined", "by", "four", "Cl", "atoms.", "The", "bond", "lengths", "and", "angles,", "in", "cation,", "are", "in", "good", "agreement", "with", "the", "corresponding", "values", "in", "(II),", "(III)", "and", "(IV).", "In", "[AuCl4]-", "anion,", "the", "Au—Cl", "bond", "lengths", "and", "angles", "(Table", "1)", "are", "within", "normal", "range", "(X,", "XIII,", "XIV,", "XV", "and", "XVI).", "In", "the", "crystal", "structure,", "intermolecular", "N—H···Cl", "hydrogen", "bonds", "(Table", "2)", "result", "in", "the", "formation", "of", "a", "supramolecular", "structure", "(Fig.", "2).", "Experimental", "A", "solution", "of", "tribenzylamine", "(0.22", "g,", "0.74", "mmol)", "in", "methanol", "(15", "ml)", "was", "added", "to", "a", "solution", "of", "HAuCl4.3H2O,", "(0.29", "g,", "0.74", "mmol)", "in", "acetonitrile", "(15", "ml)", "and", "the", "resulting", "yellow", "solution", "was", "stirred", "for", "30", "min", "at", "313", "K.", "Then,", "it", "was", "left", "to", "evaporate", "slowly", "at", "room", "temperature.", "After", "five", "days,", "yellow", "blocks", "of", "(I)", "were", "isolated", "(yield", "0.50", "g;", "71.1%;", "m.p.", "<", "573", "K).", "sup-1" ]
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79-2979940-7
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79-2979940-10
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[ "supplementary", "materials", "C2—C3—H3", "C5—C4—C3", "C5—C4—H4", "C3—C4—H4", "C4—C5—C6", "C4—C5—H5", "C6—C5—H5", "C5—C6—C7", "C5—C6—H6", "C7—C6—H6", "C2—C7—C6", "C2—C7—H7", "C6—C7—H7", "C9—C8—N1", "C9—C8—H8A", "N1—C8—H8A", "C9—C8—H8B", "N1—C8—H8B", "H8A—C8—H8B", "C10—C9—C14", "C10—C9—C8", "C14—C9—C8", "C9—C10—C11", "C9—C10—H10", "C11—C10—H10", "C12—C11—C10", "C12—C11—H11", "C10—C11—H11", "C13—C12—C11", "C13—C12—H12", "C11—C12—H12", "C12—C13—C14", "C12—C13—H13", "C14—C13—H13", "C13—C14—C9", "C13—C14—H14", "C9—C14—H14", "N1—C15—C16", "N1—C15—H15A", "C16—C15—H15A", "N1—C15—H15B", "C16—C15—H15B", "H15A—C15—H15B", "C17—C16—C21", "C17—C16—C15", "C21—C16—C15", "C18—C17—C16", "C18—C17—H17", "C16—C17—H17", "sup-8", "119.7", "120.1", "(7)", "120.0", "120.0", "121.2", "(8)", "119.4", "119.4", "118.9", "(7)", "120.6", "120.6", "120.3", "(6)", "119.8", "119.8", "116.9", "(4)", "108.1", "108.1", "108.1", "108.1", "107.3", "119.0", "(6)", "120.9", "(6)", "119.8", "(6)", "120.6", "(8)", "119.7", "119.7", "119.6", "(8)", "120.2", "120.2", "119.7", "(8)", "120.1", "120.1", "121.1", "(8)", "119.4", "119.4", "119.8", "(7)", "120.1", "120.1", "112.6", "(4)", "109.1", "109.1", "109.1", "109.1", "107.8", "118.8", "(5)", "122.0", "(5)", "119.2", "(5)", "120.3", "(6)", "119.8", "119.8", "C28—C27—H27", "C23—C28—C27", "C23—C28—H28", "C27—C28—H28", "C30—C29—N2", "C30—C29—H29A", "N2—C29—H29A", "C30—C29—H29B", "N2—C29—H29B", "H29A—C29—H29B", "C35—C30—C31", "C35—C30—C29", "C31—C30—C29", "C30—C31—C32", "C30—C31—H31", "C32—C31—H31", "C33—C32—C31", "C33—C32—H32", "C31—C32—H32", "C32—C33—C34", "C32—C33—H33", "C34—C33—H33", "C33—C34—C35", "C33—C34—H34", "C35—C34—H34", "C30—C35—C34", "C30—C35—H35", "C34—C35—H35", "N2—C36—C37", "N2—C36—H36A", "C37—C36—H36A", "N2—C36—H36B", "C37—C36—H36B", "H36A—C36—H36B", "C38—C37—C42", "C38—C37—C36", "C42—C37—C36", "C37—C38—C39", "C37—C38—H38", "C39—C38—H38", "C40—C39—C38", "C40—C39—H39", "C38—C39—H39", "C39—C40—C41", "C39—C40—H40", "C41—C40—H40", "C40—C41—C42", "C40—C41—H41", "C42—C41—H41", "119.9", "120.1", "(6)", "120.0", "120.0", "113.9", "(4)", "108.8", "108.8", "108.8", "108.8", "107.7", "119.3", "(6)", "120.6", "(5)", "120.0", "(6)", "119.8", "(10)", "120.1", "120.1", "120.5", "(9)", "119.7", "119.7", "120.7", "(8)", "119.6", "119.6", "119.9", "(10)", "120.0", "120.0", "119.7", "(8)", "120.2", "120.2", "114.2", "(4)", "108.7", "108.7", "108.7", "108.7", "107.6", "118.7", "(5)", "120.9", "(5)", "120.2", "(5)", "119.6", "(7)", "120.2", "120.2", "121.3", "(7)", "119.3", "119.3", "119.8", "(7)", "120.1", "120.1", "120.5", "(7)", "119.8", "119.8" ]
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79-2979940-6
[ "C5—C6", "C5—H5", "C6—C7", "C6—H6", "C7—H7", "C8—C9", "C8—N1", "C8—H8A", "C8—H8B", "C9—C10", "C9—C14", "C10—C11", "C10—H10", "C11—C12", "C11—H11", "C12—C13", "C12—H12", "C13—C14", "C13—H13", "C14—H14", "C15—N1", "C15—C16", "C15—H15A", "C15—H15B", "C16—C17", "C16—C21", "C17—C18", "C17—H17", "C18—C19", "C18—H18", "C19—C20", "C19—H19", "C20—C21", "C20—H20", "C21—H21", "C22—C23", "C22—N2", "C22—H22A", "C2—C1—N1", "C2—C1—H1A", "N1—C1—H1A", "C2—C1—H1B", "N1—C1—H1B", "H1A—C1—H1B", "C7—C2—C3", "C7—C2—C1", "C3—C2—C1", "C4—C3—C2", "C4—C3—H3", "1.386", "(13)", "0.9300", "1.388", "(11)", "0.9300", "0.9300", "1.496", "(8)", "1.518", "(7)", "0.9700", "0.9700", "1.374", "(9)", "1.387", "(8)", "1.394", "(13)", "0.9300", "1.375", "(16)", "0.9300", "1.361", "(14)", "0.9300", "1.384", "(9)", "0.9300", "0.9300", "1.497", "(6)", "1.505", "(7)", "0.9700", "0.9700", "1.390", "(7)", "1.399", "(8)", "1.369", "(10)", "0.9300", "1.385", "(11)", "0.9300", "1.364", "(11)", "0.9300", "1.371", "(9)", "0.9300", "0.9300", "1.510", "(7)", "1.514", "(6)", "0.9700", "113.4", "(4)", "108.9", "108.9", "108.9", "108.9", "107.7", "118.8", "(6)", "120.5", "(5)", "120.7", "(5)", "120.7", "(7)", "119.7", "C27—H27", "C28—H28", "C29—C30", "C29—N2", "C29—H29A", "C29—H29B", "C30—C35", "C30—C31", "C31—C32", "C31—H31", "C32—C33", "C32—H32", "C33—C34", "C33—H33", "C34—C35", "C34—H34", "C35—H35", "C36—N2", "C36—C37", "C36—H36A", "C36—H36B", "C37—C38", "C37—C42", "C38—C39", "C38—H38", "C39—C40", "C39—H39", "C40—C41", "C40—H40", "C41—C42", "C41—H41", "C42—H42", "N1—H1C", "N2—H2", "Au1—Cl1", "Au1—Cl2", "Au1—Cl3", "Au1—Cl4", "C25—C24—C23", "C25—C24—H24", "C23—C24—H24", "C26—C25—C24", "C26—C25—H25", "C24—C25—H25", "C27—C26—C25", "C27—C26—H26", "C25—C26—H26", "C26—C27—C28", "C26—C27—H27", "supplementary", "materials", "0.9300", "0.9300", "1.496", "(7)", "1.525", "(6)", "0.9700", "0.9700", "1.375", "(9)", "1.378", "(8)", "1.388", "(13)", "0.9300", "1.339", "(18)", "0.9300", "1.363", "(16)", "0.9300", "1.393", "(10)", "0.9300", "0.9300", "1.501", "(6)", "1.506", "(7)", "0.9700", "0.9700", "1.373", "(8)", "1.387", "(7)", "1.400", "(11)", "0.9300", "1.332", "(13)", "0.9300", "1.364", "(12)", "0.9300", "1.386", "(9)", "0.9300", "0.9300", "0.9100", "0.9100", "2.259", "(2)", "2.2891", "(15)", "2.2574", "(17)", "2.2703", "(15)", "121.5", "(5)", "119.2", "119.2", "119.3", "(6)", "120.4", "120.4", "120.4", "(6)", "119.8", "119.8", "120.2", "(6)", "119.9", "sup-7" ]
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79-2979940-8
[ "supplementary", "materials", "C17—C16—C21—C20", "C15—C16—C21—C20", "N2—C22—C23—C28", "N2—C22—C23—C24", "C28—C23—C24—C25", "C22—C23—C24—C25", "C23—C24—C25—C26", "C24—C25—C26—C27", "Hydrogen-bond", "geometry", "(Å,", "°)", "D—H···A", "N1—H1C···Cl5", "N2—H2···Cl5i", "Symmetry", "codes:", "(i)", "−x,", "−y+1,", "−z+1.", "1.7", "(9)", "−177.3", "(6)", "85.7", "(6)", "−94.9", "(6)", "−1.9", "(8)", "178.7", "(5)", "1.5", "(9)", "0.1", "(10)", "C2—C1—N1—C15", "C2—C1—N1—C8", "C37—C36—N2—C22", "C37—C36—N2—C29", "C23—C22—N2—C36", "C23—C22—N2—C29", "C30—C29—N2—C36", "C30—C29—N2—C22", "−129.7", "(5)", "104.2", "(5)", "63.1", "(5)", "−172.6", "(4)", "175.0", "(4)", "50.7", "(6)", "54.2", "(6)", "178.8", "(4)", "D—H", "0.91", "0.91", "H···A", "2.19", "2.16", "D···A", "3.089", "(5)", "3.066", "(4)", "D—H···A", "168", "172", "sup-10" ]
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79-2979940-11
[ "Fig.", "1", "supplementary", "materials", "sup-11" ]
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79-2979940-12
[ "metal-organic", "compounds", "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "Bis(tribenzylammonium)", "tetra-", "chloridoaurate(III)", "chloride", "Yousef", "Fazaeli,", "Vahid", "Amani,", "Mostafa", "M.", "Amini*", "and", "Hamid", "Reza", "Khavasi", "Department", "of", "Chemistry,", "Shahid", "Beheshti", "University,", "G.", "C.,", "Evin,", "Tehran", "1983963113,", "Iran", "Correspondence", "e-mail:", "m-pouramini@cc.sbu.ac.ir", "Received", "22", "December", "2009;", "accepted", "23", "January", "2010", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "298", "K;", "mean", "(C–C)", "=", "0.010", "A˚;", "R", "factor", "=", "0.051;", "wR", "factor", "=", "0.144;", "data-to-parameter", "ratio", "=", "27.7.", "In", "the", "title", "compound,", "(C21H22N)2[AuCl4]Cl,", "the", "AuIII", "atom", "adopts", "a", "square-planar", "coordination", "geometry", "defined", "by", "four", "chloride", "ions.", "In", "the", "crystal", "structure,", "intermolecular", "N—", "H", "Cl", "hydrogen", "bonds", "link", "the", "organic", "cations", "and", "the", "uncoordinated", "chloride", "ion.", "Related", "literature", "For", "related", "structures,", "see:", "Calleja", "et", "al.", "(2001);", "Hasan", "et", "al.", "(1999);", "Hojjat", "Kashani", "et", "al.", "(2008);", "Jarvinen", "et", "al.", "(1988);", "Johnson", "&", "Steed", "(1998);", "Safari", "et", "al.", "(2009);", "Yıldırım", "et", "al.", "(2009a,b);", "Yap", "et", "al.", "(1995);", "Yousefi", "et", "al.", "(2007);", "Zeng", "et", "al.", "(1994);", "Zhang", "et", "al.", "(2006).", "Experimental", "Crystal", "data", "(C21H22N)2[AuCl4]Cl", "Mr", "=", "951.01", "Triclinic,", "P1", "a", "=", "11.135", "(1)", "A˚", "b", "=", "13.7920", "(11)", "A˚", "c", "=", "13.8417", "(12)", "A˚", "=", "95.894", "(7)", "=", "100.300", "(7)", "Data", "collection", "=", "95.222", "(7)", "V", "=", "2067.4", "(3)", "A˚3", "Z", "=", "2", "Mo", "K", "radiation", "=", "3.91", "mm", "1", "T", "=", "298", "K", "0.35", "0.32", "0.27", "mm", "Stoe", "IPDS", "II", "diffractometer", "Absorption", "correction:", "numerical", "(X-RED;", "Stoe", "&", "Cie,", "2005)", "Tmin", "=", "0.280,", "Tmax", "=", "0.350", "28425", "measured", "reflections", "12513", "independent", "reflections", "10542", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.075", "m212", "Fazaeli", "et", "al.", "doi:10.1107/S1600536810002886", "Acta", "Cryst.", "(2010).", "E66,", "m212", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.051", "wR(F", "2)", "=", "0.144", "S", "=", "1.11", "12513", "reflections", "Table", "1", "Selected", "bond", "lengths", "(A˚", ").", "Au1—Cl1", "Au1—Cl2", "451", "parameters", "H-atom", "parameters", "constrained", "max", "=", "1.82", "e", "A˚", "3", "min", "=", "2.10", "e", "A˚", "3", "2.2574", "(17)", "2.2703", "(15)", "D—H", "A", "168", "172", "2.259", "(2)", "2.2891", "(15)", "Au1—Cl3", "Au1—Cl4", "Table", "2", "Hydrogen-bond", "geometry", "(A˚", ",", ").", "D—H", "A", "N1—H1C", "N2—H2", "Cl5", "Cl5i", "D—H", "0.91", "0.91", "H", "2.19", "2.16", "A", "D", "A", "3.089", "(5)", "3.066", "(4)", "Symmetry", "code:", "(i)", "x;", "y", "þ", "1;", "z", "þ", "1.", "Data", "collection:", "X-AREA", "(Stoe", "&", "Cie,", "2005);", "cell", "refinement:", "X-", "AREA;", "data", "reduction:", "X-RED", "(Stoe", "&", "Cie,", "2005);", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "ORTEP-3", "(Farrugia,", "1997);", "software", "used", "to", "prepare", "material", "for", "publication:", "WinGX", "(Farrugia,", "1999).", "We", "are", "grateful", "to", "Shahid", "Beheshti", "University", "for", "financial", "support.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "HB5291).", "References", "Calleja,", "M.,", "Johnson,", "K.,", "Belcher,", "W.", "J.", "&", "Steed,", "W.", "(2001).", "Inorg.", "Chem.", "40,", "4978–4985.", "Farrugia,", "L.", "J.", "(1997).", "J.", "Appl.", "Cryst.", "30,", "565.", "Farrugia,", "L.", "J.", "(1999).", "J.", "Appl.", "Cryst.", "32,", "837–838.", "Hasan,", "M.,", "Kozhevnikov,", "I.", "V.,", "Siddiqu,", "M.", "R.", "H.,", "Steiner,", "A.", "&", "Winterton,", "N.", "(1999).", "Inorg.", "Chem.", "38,", "5637–5641.", "Hojjat", "Kashani,", "L.,", "Yousefi,", "M.,", "Amani,", "V.", "&", "Khavasi,", "H.", "R.", "(2008).", "Acta", "Cryst.", "E64,", "m840–m841.", "Jarvinen,", "G.", "D.,", "Larson,", "E.", "M.,", "Wasserman,", "H.", "J.,", "Burns,", "C.", "J.", "&", "Ryan,", "R.", "R.", "(1988).", "Acta", "Cryst.", "C44,", "1701–1703.", "Johnson,", "K.", "&", "Steed,", "J.", "W.", "(1998).", "Chem.", "Commun.", "pp.", "1479–1480.", "Safari,", "N.,", "Amani,", "V.,", "Notash,", "B.", "&", "Ng,", "S.", "W.", "(2009).", "Acta", "Cryst.", "E65,", "m344.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Stoe", "&", "Cie", "(2005).", "X-AREA", "and", "X-RED.", "Stoe", "&", "Cie,", "Darmstadt,", "Germany.", "Yap,", "G.", "P.", "A.,", "Rheingold,", "A.", "R.,", "Das,", "P.", "&", "Crabtree,", "R.", "H.", "(1995).", "Inorg.", "Chem.", "34,", "3474–3476.", "Yıldırım,", "S.", "O¨", ".,", "Akkurt,", "M.,", "Safari,", "N.,", "Abedi,", "A.,", "Amani,", "V.", "&", "McKee,", "V.", "(2009a).", "Acta", "Cryst.", "E65,", "m479–m480.", "Yıldırım,", "S.", "O¨", ".,", "Akkurt,", "M.,", "Safari,", "N.,", "Amani,", "V.", "&", "McKee,", "V.", "(2009b).", "Acta", "Cryst.", "E65,", "m491–m492.", "Yousefi,", "M.,", "Teimouri,", "S.,", "Amani,", "V.", "&", "Khavasi,", "H.", "R.", "(2007).", "Acta", "Cryst.", "E63,", "m2748–m2749.", "Zeng,", "G.-F.,", "Qin,", "M.,", "Lin,", "Y.-H.", "&", "Xi,", "S.-Q.", "(1994).", "Acta", "Cryst.", "C50,", "200–202.", "Zhang,", "X.-P.,", "Yang,", "G.", "&", "Ng,", "S.", "W.", "(2006).", "Acta", "Cryst.", "E62,", "m2018–m2020." ]
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