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allenai

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layout_distribution_shift

like 0

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[ "supplementary", "materials" ]

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[ "supplementary", "materials", "H19A—C19—H19B", "N3—C20—C21", "N3—C20—H20A", "C21—C20—H20A", "N3—C20—H20B", "C21—C20—H20B", "H20A—C20—H20B", "C26—C21—C22", "C26—C21—C20", "C22—C21—C20", "C21—C22—C23", "C21—C22—H22", "C23—C22—H22", "C24—C23—C22", "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—O3", "C25—C26—C21", "O3—C26—C21", "O3—C27—C28", "O3—C27—H27A", "C6—C1—C2—C3", "C38—C1—C2—C3", "C1—C2—C3—C4", "C2—C3—C4—C5", "C3—C4—C5—C6", "C4—C5—C6—C1", "C4—C5—C6—O1", "C2—C1—C6—C5", "C38—C1—C6—C5", "C2—C1—C6—O1", "C38—C1—C6—O1", "O1—C9—C10—O2", "C16—C11—C12—C13", "O2—C11—C12—C13", "C11—C12—C13—C14", "C12—C13—C14—C15", "C13—C14—C15—C16", "C12—C11—C16—C15", "O2—C11—C16—C15", "C12—C11—C16—C17", "O2—C11—C16—C17", "sup-10", "108.4", "114.5", "(3)", "108.6", "108.6", "108.6", "108.6", "107.6", "118.3", "(4)", "119.8", "(4)", "121.8", "(4)", "119.8", "(5)", "120.1", "120.1", "120.2", "(5)", "119.9", "119.9", "121.1", "(5)", "119.5", "119.5", "119.2", "(5)", "120.4", "120.4", "123.3", "(4)", "121.3", "(4)", "115.4", "(3)", "110.2", "(4)", "109.6", "1.5", "(7)", "−177.8", "(4)", "0.3", "(8)", "−0.9", "(8)", "−0.4", "(8)", "2.3", "(7)", "−173.8", "(4)", "−2.8", "(6)", "176.5", "(4)", "173.6", "(4)", "−7.0", "(6)", "41.1", "(6)", "−1.6", "(7)", "−179.3", "(5)", "−0.5", "(9)", "1.7", "(10)", "−0.9", "(9)", "2.4", "(6)", "−179.8", "(4)", "−178.1", "(4)", "−0.2", "(6)", "C39—O6—Ni1", "C44—O7—Ni1ii", "C37—N1—C38", "C37—N1—Ni1", "C38—N1—Ni1", "C37—N1—H1N", "C38—N1—H1N", "Ni1—N1—H1N", "C35—N2—C36", "C35—N2—Ni1", "C36—N2—Ni1", "C35—N2—H2N", "C36—N2—H2N", "Ni1—N2—H2N", "C19—N3—C20", "C19—N3—Ni1", "C20—N3—Ni1", "C19—N3—H3N", "C20—N3—H3N", "Ni1—N3—H3N", "C18—N4—C17", "C18—N4—Ni1", "C17—N4—Ni1", "C18—N4—H4N", "C17—N4—H4N", "Ni1—N4—H4N", "C41—C40—C46—C45", "C39—C40—C46—C45", "C43—C45—C46—C40", "C10—C9—O1—C6", "C5—C6—O1—C9", "C1—C6—O1—C9", "C9—C10—O2—C11", "C16—C11—O2—C10", "C12—C11—O2—C10", "C25—C26—O3—C27", "C21—C26—O3—C27", "C28—C27—O3—C26", "C27—C28—O4—C29", "C34—C29—O4—C28", "C30—C29—O4—C28", "O5—C39—O6—Ni1", "C40—C39—O6—Ni1", "N1—Ni1—O6—C39", "N3—Ni1—O6—C39", "N4—Ni1—O6—C39", "N2—Ni1—O6—C39", "132.4", "(2)", "130.8", "(2)", "116.6", "(4)", "105.4", "(3)", "115.7", "(2)", "106", "(3)", "106", "(3)", "106", "(3)", "110.4", "(3)", "118.8", "(2)", "107.4", "(2)", "112", "(3)", "112", "(3)", "96", "(3)", "112.3", "(3)", "104.5", "(2)", "119.3", "(2)", "106", "(3)", "104", "(3)", "110", "(3)", "112.2", "(3)", "105.4", "(2)", "118.3", "(2)", "109", "(3)", "110", "(3)", "101", "(3)", "−2.4", "(5)", "174.2", "(3)", "−0.8", "(6)", "−178.7", "(4)", "−34.0", "(6)", "149.7", "(4)", "178.9", "(4)", "131.3", "(4)", "−50.8", "(6)", "−36.7", "(7)", "143.7", "(4)", "−160.0", "(4)", "176.2", "(4)", "140.7", "(5)", "−41.9", "(7)", "−4.2", "(6)", "175.8", "(2)", "78.3", "(3)", "−102.3", "(3)", "−19.1", "(3)", "159.4", "(3)" ]

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[ "C14—C15—C16—C11", "C14—C15—C16—C17", "C11—C16—C17—N4", "C15—C16—C17—N4", "N4—C18—C19—N3", "N3—C20—C21—C26", "N3—C20—C21—C22", "C26—C21—C22—C23", "C20—C21—C22—C23", "C21—C22—C23—C24", "C22—C23—C24—C25", "C23—C24—C25—C26", "C24—C25—C26—O3", "C24—C25—C26—C21", "C22—C21—C26—C25", "C20—C21—C26—C25", "C22—C21—C26—O3", "C20—C21—C26—O3", "O3—C27—C28—O4", "O4—C29—C30—C31", "C34—C29—C30—C31", "C29—C30—C31—C32", "C30—C31—C32—C33", "C31—C32—C33—C34", "O4—C29—C34—C33", "C30—C29—C34—C33", "O4—C29—C34—C35", "C30—C29—C34—C35", "C32—C33—C34—C29", "C32—C33—C34—C35", "C29—C34—C35—N2", "C33—C34—C35—N2", "N2—C36—C37—N1", "C6—C1—C38—N1", "C2—C1—C38—N1", "O5—C39—C40—C46", "O6—C39—C40—C46", "O5—C39—C40—C41", "O6—C39—C40—C41", "C46—C40—C41—C42", "C39—C40—C41—C42", "C40—C41—C42—C43", "C41—C42—C43—C45", "C41—C42—C43—C44", "C42—C43—C44—O8", "C45—C43—C44—O8", "C42—C43—C44—O7", "−1.1", "(7)", "179.3", "(5)", "83.3", "(5)", "−97.2", "(5)", "61.8", "(4)", "71.6", "(5)", "−110.4", "(4)", "−0.6", "(7)", "−178.6", "(4)", "0.8", "(8)", "−0.9", "(9)", "0.8", "(8)", "179.8", "(5)", "−0.6", "(7)", "0.5", "(7)", "178.6", "(4)", "−179.9", "(4)", "−1.8", "(6)", "56.8", "(7)", "−177.0", "(4)", "0.2", "(7)", "1.8", "(7)", "−1.4", "(8)", "−1.1", "(7)", "174.9", "(4)", "−2.4", "(6)", "−4.8", "(6)", "177.8", "(4)", "2.9", "(6)", "−177.4", "(4)", "−91.4", "(4)", "88.8", "(5)", "41.6", "(6)", "76.5", "(5)", "−104.2", "(5)", "166.5", "(4)", "−13.6", "(5)", "−16.9", "(5)", "163.0", "(3)", "3.2", "(5)", "−173.5", "(3)", "−0.8", "(6)", "−2.5", "(5)", "172.8", "(3)", "−177.9", "(4)", "−2.8", "(6)", "0.2", "(5)", "O8—C44—O7—Ni1ii", "C43—C44—O7—Ni1ii", "C36—C37—N1—C38", "C36—C37—N1—Ni1", "C1—C38—N1—C37", "C1—C38—N1—Ni1", "O6—Ni1—N1—C37", "O7i—Ni1—N1—C37", "N4—Ni1—N1—C37", "N2—Ni1—N1—C37", "O6—Ni1—N1—C38", "O7i—Ni1—N1—C38", "N4—Ni1—N1—C38", "N2—Ni1—N1—C38", "C34—C35—N2—C36", "C34—C35—N2—Ni1", "C37—C36—N2—C35", "C37—C36—N2—Ni1", "O6—Ni1—N2—C35", "O7i—Ni1—N2—C35", "N1—Ni1—N2—C35", "N3—Ni1—N2—C35", "O6—Ni1—N2—C36", "O7i—Ni1—N2—C36", "N1—Ni1—N2—C36", "N3—Ni1—N2—C36", "C18—C19—N3—C20", "C18—C19—N3—Ni1", "C21—C20—N3—C19", "C21—C20—N3—Ni1", "O6—Ni1—N3—C19", "O7i—Ni1—N3—C19", "N4—Ni1—N3—C19", "N2—Ni1—N3—C19", "O6—Ni1—N3—C20", "O7i—Ni1—N3—C20", "N4—Ni1—N3—C20", "N2—Ni1—N3—C20", "C19—C18—N4—C17", "C19—C18—N4—Ni1", "C16—C17—N4—C18", "C16—C17—N4—Ni1", "O6—Ni1—N4—C18", "O7i—Ni1—N4—C18", "N1—Ni1—N4—C18", "N3—Ni1—N4—C18", "O6—Ni1—N4—C17", "supplementary", "materials", "14.3", "(6)", "−163.6", "(2)", "81.0", "(5)", "−48.9", "(5)", "54.7", "(5)", "179.6", "(3)", "122.4", "(3)", "−57.8", "(3)", "−144.7", "(3)", "32.9", "(3)", "−8.1", "(3)", "171.7", "(3)", "84.8", "(3)", "−97.6", "(3)", "−66.6", "(4)", "168.8", "(3)", "−142.5", "(4)", "−11.6", "(5)", "18.2", "(3)", "−159.3", "(3)", "114.2", "(3)", "−71.2", "(3)", "−107.9", "(3)", "74.6", "(3)", "−11.9", "(3)", "162.6", "(3)", "83.7", "(4)", "−47.0", "(3)", "61.7", "(4)", "−175.6", "(3)", "111.2", "(2)", "−68.6", "(2)", "19.0", "(2)", "−158.5", "(2)", "−15.3", "(3)", "164.9", "(3)", "−107.5", "(3)", "75.0", "(3)", "89.0", "(4)", "−41.1", "(3)", "69.4", "(4)", "−167.5", "(2)", "−77.3", "(2)", "100.2", "(2)", "−173.6", "(2)", "11.9", "(2)", "156.3", "(2)", "sup-11" ]

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[ "C5—C6—O1", "C1—C6—O1", "O1—C9—C10", "O1—C9—H9A", "C10—C9—H9A", "O1—C9—H9B", "C10—C9—H9B", "H9A—C9—H9B", "O2—C10—C9", "O2—C10—H10A", "C9—C10—H10A", "O2—C10—H10B", "C9—C10—H10B", "H10A—C10—H10B", "C16—C11—C12", "C16—C11—O2", "C12—C11—O2", "C13—C12—C11", "C13—C12—H12", "C11—C12—H12", "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", "C11—C16—C15", "C11—C16—C17", "C15—C16—C17", "N4—C17—C16", "N4—C17—H17A", "C16—C17—H17A", "N4—C17—H17B", "C16—C17—H17B", "H17A—C17—H17B", "N4—C18—C19", "N4—C18—H18A", "C19—C18—H18A", "N4—C18—H18B", "C19—C18—H18B", "H18A—C18—H18B", "N3—C19—C18", "N3—C19—H19A", "C18—C19—H19A", "N3—C19—H19B", "C18—C19—H19B", "123.3", "(4)", "114.9", "(3)", "111.3", "(3)", "109.4", "109.4", "109.4", "109.4", "108.0", "112.6", "(4)", "109.1", "109.1", "109.1", "109.1", "107.8", "121.8", "(4)", "116.6", "(3)", "121.6", "(4)", "119.2", "(5)", "120.4", "120.4", "119.8", "(5)", "120.1", "120.1", "120.8", "(5)", "119.6", "119.6", "120.5", "(5)", "119.8", "119.8", "117.8", "(4)", "120.7", "(3)", "121.5", "(4)", "115.2", "(3)", "108.5", "108.5", "108.5", "108.5", "107.5", "109.1", "(3)", "109.9", "109.9", "109.9", "109.9", "108.3", "108.5", "(3)", "110.0", "110.0", "110.0", "110.0", "N2—C35—H35B", "C34—C35—H35B", "H35A—C35—H35B", "C37—C36—N2", "C37—C36—H36A", "N2—C36—H36A", "C37—C36—H36B", "N2—C36—H36B", "H36A—C36—H36B", "N1—C37—C36", "N1—C37—H37A", "C36—C37—H37A", "N1—C37—H37B", "C36—C37—H37B", "H37A—C37—H37B", "N1—C38—C1", "N1—C38—H38A", "C1—C38—H38A", "N1—C38—H38B", "C1—C38—H38B", "H38A—C38—H38B", "O5—C39—O6", "O5—C39—C40", "O6—C39—C40", "C46—C40—C41", "C46—C40—C39", "C41—C40—C39", "C42—C41—C40", "C42—C41—H41", "C40—C41—H41", "C43—C42—C41", "C43—C42—H42", "C41—C42—H42", "C42—C43—C45", "C42—C43—C44", "C45—C43—C44", "O8—C44—O7", "O8—C44—C43", "O7—C44—C43", "C46—C45—C43", "C46—C45—H45", "C43—C45—H45", "C40—C46—C45", "C40—C46—H46", "C45—C46—H46", "C9—O1—C6", "C10—O2—C11", "C26—O3—C27", "C28—O4—C29", "supplementary", "materials", "108.5", "108.5", "107.5", "115.0", "(4)", "108.5", "108.5", "108.5", "108.5", "107.5", "110.8", "(4)", "109.5", "109.5", "109.5", "109.5", "108.1", "115.0", "(3)", "108.5", "108.5", "108.5", "108.5", "107.5", "126.5", "(3)", "118.3", "(3)", "115.2", "(3)", "118.6", "(3)", "122.0", "(3)", "119.3", "(3)", "120.5", "(3)", "119.8", "119.8", "121.2", "(3)", "119.4", "119.4", "118.5", "(3)", "120.3", "(3)", "121.1", "(3)", "125.2", "(3)", "119.8", "(3)", "114.9", "(3)", "120.3", "(3)", "119.9", "119.9", "120.9", "(3)", "119.6", "119.6", "119.8", "(3)", "116.4", "(3)", "118.1", "(3)", "118.8", "(4)", "sup-9" ]

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[ "organic", "compounds", "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "2,20", "-(Diselane-1,2-diyl)dinicotinamide", "N,N0-dimethylformamide", "disolvate", "Aixia", "Feng,", "Ying", "Xu", "and", "Xuehong", "Wei*", "School", "of", "Chemistry", "and", "Chemical", "Engineering,", "Shanxi", "University,", "Shanxi", "Province,", "People’s", "Republic", "of", "China", "Correspondence", "e-mail:", "xhwei@sxu.edu.cn", "Received", "23", "March", "2010;", "accepted", "24", "April", "2010", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "298", "K;", "mean", "(C–C)", "=", "0.005", "A˚;", "R", "factor", "=", "0.036;", "wR", "factor", "=", "0.097;", "data-to-parameter", "ratio", "=", "14.3.", "The", "asymmetric", "unit", "of", "the", "title", "compound,", "C12H10N4O2Se2", "-", "2C3H7NO,", "contains", "two", "solvent", "molecules", "and", "two", "half", "molecules", "of", "the", "dinicotinamide,", "each", "of", "which", "sits", "on", "a", "center", "of", "symmetry", "passing", "through", "the", "middle", "of", "the", "Se—Se", "bond.", "In", "each", "molecule,", "the", "two", "pyridyl", "groups", "and", "diseleno", "group", "are", "approximately", "coplanar", "(r.m.s.", "deviations", "from", "planarity", "for", "all", "non-H", "atoms", "=", "0.011", "and", "0.008", "A˚", "in", "the", "two", "molecules).", "Intermolecular", "N—H", "O", "hydrogen", "bonds", "stabli-", "lize", "the", "crystal", "packing.", "Related", "literature", "For", "the", "potential", "applications", "of", "organoselenium", "compounds", "in", "organic", "synthesis,", "as", "precursors", "for", "semiconducting", "mate-", "rials", "and", "in", "ligand", "chemistry", "and", "biochemistry,", "see:", "Mugesh", "et", "al.", "(2001).", "For", "related", "diselenide", "compounds,", "see:", "Bhasin", "&", "Singh", "(2002);", "Kienitz", "et", "al.", "(1996).", "Experimental", "Crystal", "data", "C12H10N4O2Se2", "2C3H7NO", "Mr", "=", "546.34", "Triclinic,", "P1", "a", "=", "7.6101", "(17)", "A˚", "b", "=", "12.318", "(3)", "A˚", "c", "=", "13.420", "(3)", "A˚", "=", "114.175", "(2)", "=", "91.017", "(3)", "Data", "collection", "Siemens", "SMART", "CCD", "diffractometer", "Absorption", "correction:", "multi-scan", "(SADABS;", "Sheldrick,", "1996)", "Tmin", "=", "0.439,", "Tmax", "=", "0.560", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.036", "wR(F", "2)", "=", "0.097", "S", "=", "1.03", "3937", "reflections", "Table", "1", "Hydrogen-bond", "geometry", "(A˚", ",", ").", "D—H", "A", "N1—H1A", "N1—H1B", "N3—H3B", "N3—H3A", "O4", "O3", "O4", "O1i", "D—H", "0.86", "0.86", "0.86", "0.86", "Symmetry", "code:", "(i)", "x;", "y", "þ", "1;", "z", "þ", "1.", "=", "95.833", "(3)", "V", "=", "1139.3", "(4)", "A˚", "3", "Z", "=", "2", "Mo", "K", "radiation", "=", "3.28", "mm", "1", "T", "=", "298", "K", "0.30", "0.20", "0.20", "mm", "3937", "measured", "reflections", "3937", "independent", "reflections", "3359", "reflections", "with", "I", ">", "2", "(I)", "275", "parameters", "H-atom", "parameters", "constrained", "max", "=", "0.38", "e", "A˚", "3", "min", "=", "0.73", "e", "A˚", "3", "H", "2.09", "2.03", "2.10", "2.31", "A", "D", "A", "2.946", "(4)", "2.869", "(5)", "2.919", "(4)", "3.081", "(4)", "D—H", "A", "170", "163", "158", "150", "Data", "collection:", "SMART", "(Siemens,", "1996);", "cell", "refinement:", "SAINT", "(Siemens,", "1996);", "data", "reduction:", "SAINT;", "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:", "SHELXL97.", "We", "thank", "the", "SNSF", "(Nos.", "2008011021", "and", "2008012013-2)", "and", "the", "Homecoming", "Foundation", "of", "Shanxi", "Province", "for", "support.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "FL2299).", "References", "Bhasin,", "K.", "K.", "&", "Singh,", "J.", "(2002).", "J.", "Organomet.", "Chem.", "658,", "71–76.", "Kienitz,", "C.", "O.,", "Tho1ne,", "C.,", "and", "Jones.", "P.", "G.", "(1996).", "Inorg.", "Chem.", "35,", "3990–3997.", "Mugesh,", "G.,", "Mont,", "W.-W.", "&", "Sies,", "H.", "(2001).", "Chem.", "Rev.", "101,", "2125–2179.", "Sheldrick,", "G.", "M.", "(1996).", "SADABS.", "University", "of", "Go¨", "ttingen,", "Germany.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Siemens", "(1996).", "SMART", "and", "SAINT.", "Siemens", "Analytical", "X-ray", "Instruments", "Inc.,", "Madison,", "Wisconsin,", "USA.", "o1216", "Feng", "et", "al.", "doi:10.1107/S1600536810015047", "Acta", "Cryst.", "(2010).", "E66,", "o1216" ]

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[ "supplementary", "materials", "Acta", "Cryst.", "(2010).", "E66,", "o1216", "[", "doi:10.1107/S1600536810015047", "]", "2,2'-(Diselane-1,2-diyl)dinicotinamide", "N,N'-dimethylformamide", "disolvate", "A.", "Feng,", "Y.", "Xu", "and", "X.", "Wei", "Comment", "Organoselenium", "compounds", "have", "attracted", "much", "atention", "because", "of", "their", "potential", "applications", "in", "organic", "synthesis,", "pre-", "cursors", "for", "semiconducting", "materials,", "ligand", "chemistry", "and", "biochemistry", "(Mugesh", "et", "al.,", "2001).", "During", "the", "past", "decade,", "many", "organoselenium", "compounds", "have", "been", "synthesized", "and", "well", "characterized.", "In", "contrast", "to", "alkyl,", "aryl,", "and", "mixed", "al-", "kylaryl", "senium", "compounds,", "the", "pyridyl", "selenium", "compounds", "are", "still", "rare.", "The", "unit", "cell", "contains", "two", "nicotinamide", "molecules", "and", "four", "of", "the", "solvent", "molecules.", "The", "asymmetric", "unit", "contains", "two", "solvent", "molecules", "and", "two", "half", "molecues", "of", "the", "nicotinamide", "each", "of", "which", "sits", "on", "a", "center", "of", "symmetry", "passing", "through", "the", "middle", "of", "the", "Se—Se", "bond", "(Fig.", "1).", "In", "(I),the", "two", "independent", "nicotinamides", "(molecule", "A", "containing", "Se1", "and", "molecule", "B", "containing", "Se2)", "have", "comparable", "conformations.", "In", "each", "nicotinamide,", "the", "two", "pyridyl", "groups", "and", "the", "diseleno", "group", "are", "approximately", "coplanar", "(r.m.s.", "deviations", "from", "planarity", "for", "all", "non-H", "atoms", "are", "0.011", "and", "0.008Å", "for", "molecules", "A", "and", "B,", "respectively", "while", "the", "two", "CONH2", "groups", "are", "rotated", "out", "of", "this", "plane", "by", "11.0", "(5)°", "and", "18.6", "(5)°", "for", "molecules", "A", "and", "B,", "respectively.", "Fig.", "2", "shows", "the", "sheets", "of", "molecules", "formed", "by", "intermolecular", "N-H···O", "hydrogen-bond", "interactions", "between", "the", "nicotinamides", "and", "neighbouring", "solvents", "with", "distances", "between", "2.869", "(5)", "and", "3.081", "(4)", "Å", "(Table", "1).", "The", "structure", "of", "(I)", "is", "similar", "to", "that", "of", "other", "diselenide", "compounds", "(Kienitz,", "et", "al.", "1996;", "Bhasin", "and", "Singh", "2002).The", "two", "neighbouring", "pyridyl", "groups", "can", "be", "brought", "into", "register", "by", "rotation", "about", "the", "Se—Se", "bond.", "The", "commonly", "observed", "approximate", "coplanarity", "of", "the", "rings", "and", "the", "Se—Se", "bonds", "(C—C—Se—Se", "or", "N—C—Se—Se", "torsion", "angles", "ca.", "0°)", "in", "these", "molecules", "has", "been", "explained", "in", "terms", "of", "a", "minimization", "of", "Se···Se", "lone", "pair", "repulsion.", "Experimental", "To", "a", "vigorously", "stirred", "solution", "of", "selenium", "powder", "(1.19", "g,", "15", "mmol)", "and", "absolute", "ethanol", "(30", "ml),", "sodium", "borohydride", "(0.40", "g,", "10.6", "mmol)", "was", "added", "at", "0", "°C.", "The", "mixture", "was", "warmed", "to", "room", "temperature", "and", "stirred", "for", "2", "h.", "2-Chloro-nicot-", "inamide", "(1.56", "g,", "10", "mmol)", "was", "added", "and", "stirred", "for", "7", "days.", "O2", "was", "passed", "through", "the", "solution", "slowly", "for", "2", "h", "after", "the", "reaction", "mixture", "was", "acidfied", "by", "glacial", "acetic.", "The", "solvents", "were", "removed", "in", "vacuo", "and", "the", "residue", "was", "extracted", "with", "hot", "dimethyl", "sulphoxide", "(DMSO)", "and", "filtered.", "The", "filtrate", "was", "poured", "into", "water(", "200", "ml,", "cooled", "to", "0", "°C).", "The", "precipitate", "was", "separated", "by", "filtration", "and", "recrystallized", "from", "DMSO-CH3OH(1:2)", "to", "give", "the", "product", "as", "yellow", "crystals,", "yield:", "1.56", "g,", "78%;", "m.p.", "124-125", "°C.", "1H-NMR", "(", "300", "MHz,", "DCCl3)", "δ", "(ppm):", "7.27", "(d,", "2H),", "7.81", "(s,", "2H),", "8.14", "(d,", "2H),", "8.32", "(s,", "2H),", "8.48", "(s,", "2H),", "8.65", "(s,", "2H);77Se-NMR", "(57", "MHz,", "DMSO-d6", ")", "δ(ppm):", "524.77.", "Refinement", "(type", "here", "to", "add", "refinement", "details)", "sup-1" ]

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[ "supplementary", "materials", "C5—O2—C6—O3", "C8—O4—C3—C4", "C3—O4—C8—O5", "C8—O4—C3—C2", "C3—O4—C8—C9", "C17—O9—C20—C21", "C20—O9—C17—C18", "C17—O9—C20—O10", "C20—O9—C17—C16", "C19—O11—C22—O12", "C22—O11—C19—C18", "C19—O11—C22—C23", "C18—O16—C15—N3", "C18—O16—C15—C16", "C15—O16—C18—C19", "C15—O16—C18—C17", "C10—N1—C1—O1", "C13—N1—C1—C2", "C13—N1—C10—N2", "C10—N1—C1—C2", "C13—N1—C10—O6", "C1—N1—C10—N2", "C1—N1—C13—C12", "C1—N1—C10—O6", "C10—N1—C13—C12", "C13—N1—C1—O1", "C11—N2—C10—N1", "C11—N2—C10—O6", "C10—N2—C11—O7", "C10—N2—C11—C12", "C15—N3—C24—N4", "C15—N3—C24—O13", "C27—N3—C24—N4", "C27—N3—C24—O13", "C24—N3—C27—C26", "C27—N3—C15—C16", "C15—N3—C27—C26", "Hydrogen-bond", "geometry", "(Å,", "°)", "D—H···A", "N2—H2···O6i", "N4—H4A···O5", "C3—H3···O13", "C13—H13···O2", "C16—H16A···O7ii", "C18—H18···O10iii", "C21—H21A···O4iv", "1.0", "(5)", "−167.3", "(2)", "3.2", "(4)", "80.8", "(3)", "−176.2", "(3)", "178.7", "(3)", "−170.0", "(3)", "−0.3", "(5)", "76.3", "(3)", "2.9", "(5)", "−168.1", "(3)", "−177.5", "(3)", "−146.0", "(2)", "−23.4", "(3)", "132.3", "(3)", "6.1", "(3)", "−116.1", "(3)", "−58.8", "(4)", "2.3", "(4)", "125.7", "(3)", "−178.3", "(3)", "177.7", "(3)", "−178.1", "(3)", "−2.8", "(5)", "−2.7", "(5)", "59.4", "(3)", "−2.0", "(5)", "178.6", "(3)", "−176.6", "(3)", "1.8", "(5)", "174.7", "(3)", "−5.2", "(5)", "−2.6", "(4)", "177.5", "(3)", "−1.8", "(5)", "−60.0", "(4)", "−179.1", "(3)", "D—H", "0.86", "0.86", "0.98", "0.93", "0.97", "0.98", "0.96", "C25—N4—C24—O13", "O1—C1—C2—C3", "N1—C1—C2—C3", "C1—C2—C3—C4", "C1—C2—C3—O4", "C2—C3—C4—C5", "O4—C3—C4—O1", "C2—C3—C4—O1", "O4—C3—C4—C5", "C3—C4—C5—O2", "O1—C4—C5—O2", "O7—C11—C12—C13", "O7—C11—C12—C14", "N2—C11—C12—C14", "N2—C11—C12—C13", "C13—C12—C14—O8", "C11—C12—C13—N1", "C11—C12—C14—O8", "C14—C12—C13—N1", "O16—C15—C16—C17", "N3—C15—C16—C17", "C15—C16—C17—O9", "C15—C16—C17—C18", "C16—C17—C18—O16", "O9—C17—C18—O16", "C16—C17—C18—C19", "O9—C17—C18—C19", "C17—C18—C19—O11", "O16—C18—C19—O11", "O14—C25—C26—C27", "N4—C25—C26—C28", "O14—C25—C26—C28", "N4—C25—C26—C27", "C25—C26—C27—N3", "C27—C26—C28—O15", "C28—C26—C27—N3", "C25—C26—C28—O15", "H···A", "1.96", "2.08", "2.57", "2.54", "2.41", "2.46", "2.51", "−174.5", "(3)", "31.3", "(3)", "150.1", "(2)", "−31.0", "(3)", "82.5", "(3)", "−101.1", "(3)", "−95.5", "(2)", "20.5", "(3)", "142.9", "(2)", "51.7", "(3)", "−67.3", "(3)", "176.4", "(3)", "−3.0", "(5)", "178.7", "(3)", "−2.0", "(5)", "−5.9", "(5)", "2.5", "(5)", "173.5", "(3)", "−178.1", "(3)", "30.7", "(3)", "148.1", "(3)", "88.9", "(3)", "−26.2", "(3)", "13.4", "(3)", "−105.0", "(3)", "−108.6", "(3)", "133.0", "(3)", "52.1", "(3)", "−68.2", "(3)", "177.7", "(4)", "177.8", "(3)", "−3.2", "(5)", "−1.2", "(5)", "3.9", "(5)", "−3.3", "(6)", "−175.1", "(3)", "177.7", "(4)", "D···A", "2.817", "(3)", "2.935", "(4)", "3.489", "(4)", "3.402", "(4)", "3.312", "(4)", "3.257", "(4)", "3.441", "(5)", "D—H···A", "172", "173", "156", "155", "155", "138", "162", "sup-9" ]

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"&", "Wang,", "J.-J.", "(2011).", "J.", "Org.", "Chem.", "76,", "982–985." ]

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[ "supplementary", "materials", "O2—C6—C7", "O2—C6—O3", "O3—C6—C7", "O5—C8—C9", "O4—C8—O5", "O4—C8—C9", "N1—C10—N2", "O6—C10—N2", "O6—C10—N1", "N2—C11—C12", "O7—C11—N2", "O7—C11—C12", "C13—C12—C14", "C11—C12—C14", "C11—C12—C13", "N1—C13—C12", "O8—C14—C12", "N1—C1—H1", "O1—C1—H1", "C2—C1—H1", "H2A—C2—H2B", "C3—C2—H2B", "C3—C2—H2A", "C1—C2—H2B", "C1—C2—H2A", "O4—C3—H3", "C4—C3—H3", "C2—C3—H3", "C5—C4—H4", "O1—C4—H4", "C3—C4—H4", "O2—C5—H5B", "O2—C5—H5A", "H5A—C5—H5B", "C4—C5—H5A", "C4—C5—H5B", "C6—C7—H7B", "C6—C7—H7C", "H7A—C7—H7B", "H7A—C7—H7C", "H7B—C7—H7C", "C6—C7—H7A", "C8—C9—H9C", "C4—O1—C1—N1", "C4—O1—C1—C2", "C1—O1—C4—C5", "C1—O1—C4—C3", "C5—O2—C6—C7", "C6—O2—C5—C4", "sup-8", "110.8", "(3)", "122.1", "(3)", "127.1", "(4)", "124.7", "(3)", "123.0", "(3)", "112.3", "(3)", "114.8", "(3)", "123.0", "(3)", "122.2", "(3)", "114.2", "(3)", "120.1", "(3)", "125.7", "(3)", "121.5", "(3)", "118.9", "(3)", "119.6", "(3)", "122.8", "(3)", "123.3", "(3)", "109.00", "109.00", "109.00", "109.00", "111.00", "111.00", "111.00", "111.00", "112.00", "112.00", "112.00", "109.00", "109.00", "109.00", "110.00", "110.00", "108.00", "110.00", "110.00", "109.00", "110.00", "109.00", "109.00", "110.00", "110.00", "109.00", "−142.9", "(2)", "−19.2", "(3)", "122.9", "(3)", "−1.0", "(3)", "−178.2", "(3)", "−147.9", "(3)", "O14—C25—N4", "N4—C25—C26", "O14—C25—C26", "C25—C26—C28", "C25—C26—C27", "C27—C26—C28", "N3—C27—C26", "O15—C28—C26", "O16—C15—H15", "N3—C15—H15", "C16—C15—H15", "C15—C16—H16A", "C15—C16—H16B", "C17—C16—H16A", "C17—C16—H16B", "H16A—C16—H16B", "O9—C17—H17", "C16—C17—H17", "C18—C17—H17", "O16—C18—H18", "C17—C18—H18", "C19—C18—H18", "O11—C19—H19A", "O11—C19—H19B", "C18—C19—H19A", "C18—C19—H19B", "H19A—C19—H19B", "C20—C21—H21A", "C20—C21—H21B", "C20—C21—H21C", "H21A—C21—H21B", "H21A—C21—H21C", "H21B—C21—H21C", "C22—C23—H23A", "C22—C23—H23B", "C22—C23—H23C", "H23A—C23—H23B", "H23A—C23—H23C", "H23B—C23—H23C", "N3—C27—H27", "C26—C27—H27", "O15—C28—H28", "C26—C28—H28", "C24—N3—C15—O16", "C27—N3—C15—O16", "C24—N3—C15—C16", "C24—N4—C25—C26", "C24—N4—C25—O14", "C25—N4—C24—N3", "120.7", "(3)", "113.2", "(3)", "126.0", "(3)", "118.8", "(3)", "120.2", "(3)", "121.0", "(3)", "123.0", "(3)", "124.1", "(3)", "110.00", "110.00", "110.00", "111.00", "111.00", "111.00", "111.00", "109.00", "111.00", "111.00", "111.00", "108.00", "108.00", "108.00", "110.00", "110.00", "110.00", "110.00", "108.00", "110.00", "109.00", "110.00", "110.00", "109.00", "109.00", "110.00", "109.00", "109.00", "109.00", "109.00", "110.00", "118.00", "119.00", "118.00", "118.00", "−120.1", "(3)", "57.3", "(4)", "122.7", "(3)", "−3.8", "(5)", "177.2", "(3)", "5.6", "(5)" ]

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[ "supplementary", "materials", "Acta", "Cryst.", "(2011).", "E67,", "o2951-o2952", "[", "doi:10.1107/S1600536811041304", "]", "[(2R,3S,5R)-3-Acetoxy-5-(5-formyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2,3,4,5-tetrahydro-", "furan-2-yl]methyl", "acetate", "X.-F.", "Jia,", "N.", "Liu,", "L.-L.", "Fang", "and", "X.-Y.", "Zhang", "Comment", "Many", "pyrimidine", "nucleosides", "with", "modification", "on", "the", "5-position", "of", "the", "pyrimidine", "ring", "have", "drawn", "much", "attention", "due", "to", "their", "interesting", "pharmacological", "properties,", "such", "as", "antitumor,", "antiviral,", "and", "antimicrobial", "activities", "(De", "Clercq", "et", "al.,", "2005;", "Agrofoglio", "et", "al.,", "2003,", "Lee", "et", "al.,", "2009).", "The", "title", "compound", "has", "been", "used", "as", "a", "powerful", "synthon", "for", "the", "preparation", "of", "a", "variety", "of", "nucleoside", "derivatives", "due", "to", "the", "rich", "and", "extensive", "chemistry", "of", "the", "aldehyde", "carbonyl", "(Fan", "et", "al.,", "2006a,", "2006b,", "2010,", "2011;", "Zhang", "et", "al.,", "2009).", "However,", "its", "crystal", "structure", "has", "not", "been", "reported", "as", "yet.", "The", "absolute", "structure", "of", "the", "title", "compound", "is", "known", "because", "the", "synthetic", "procedure", "does", "not", "affect", "stereogenic", "atoms", "of", "the", "starting", "compound.", "In", "the", "two", "independent", "(A", "&", "B)", "but", "very", "similar", "molecules", "of", "the", "title", "compound", "(Fig.", "1)", "all", "the", "bond", "lengths", "and", "bond", "angles", "are", "within", "normal", "ranges.", "In", "molecule", "A", "the", "O1—C4", "bond", "is", "a", "little", "longer", "than", "bond", "O1—C1,", "as", "is", "bond", "O16-C15", "compared", "to", "bond", "O16-C18", "in", "molecule", "B.", "This", "is", "similar", "to", "the", "situation", "in", "2'-deoxy-3',5'-di-O-acetyluridine", "(Luo", "et", "al.,", "2007),", "but", "different", "to", "that", "in", "2,3,5-triacetyluridine", "(Low", "&", "Wilson,", "1984).", "The", "pyrimidine", "rings", "in", "both", "molecules", "are", "planar", "[maximum", "deviations", "being", "0.010", "(3)", "Å", "in", "A", "and", "0.028", "(3)", "Å", "in", "B].", "The", "atoms", "connected", "directly", "with", "the", "pyrimidine", "ring", "and", "the", "atoms", "in", "the", "aldehyde", "carbonyl", "group", "in", "the", "5-position", "of", "the", "pyrimidine", "ring", "are", "coplanar", "with", "the", "pyrimidine", "ring,", "which", "means", "there", "is", "an", "exstensive", "conjugated", "system", "in", "each", "molecule.", "The", "five-membered", "furanose", "ring", "in", "molecule", "A", "adopts", "an", "envelope", "conformation", "with", "atom", "C2", "at", "the", "flap,", "while", "in", "molecule", "B", "the", "five-membered", "ring", "is", "twisted", "on", "bond", "C15-C16.", "In", "the", "crystal,", "two", "A", "molecules", "form", "a", "pseudosymmetric", "dimer", "connected", "via", "N—H···O", "hydrogen", "bonds,", "involving", "the", "N", "atom", "of", "the", "pyrimidine", "base", "and", "the", "adjacent", "carbonyl", "O", "atom", "of", "the", "pyrimidine", "base.", "Each", "A", "molecule", "is", "further", "connected", "to", "a", "B", "molecule", "via", "an", "N—H···O", "hydrogen", "bond", "involving", "the", "N", "atom", "of", "the", "pyrimidine", "base", "and", "carbonyl", "O", "atom", "of", "the", "acetoxy", "groups", "in", "the", "3'-position", "of", "the", "furanose", "ring", "(see", "Table", "1", "and", "Fig.", "2", "for", "details).", "There", "are", "also", "a", "number", "of", "C-H···O", "interactions", "present", "leading", "to", "the", "formation", "of", "a", "three-dimensional", "network", "(Table", "1).", "Experimental", "Refinement", "The", "title", "compound", "was", "synthesized", "following", "the", "previously", "reported", "procedure", "(Fan,", "et", "al.,", "2006b).", "Single", "crystals,", "suit-", "able", "for", "X-ray", "diffraction", "analysis,", "were", "obtained", "by", "slow", "evaporation", "of", "the", "solvents", "from", "a", "dichloromethane-petroleum", "ether", "(1:1", "v/v)", "solution", "of", "the", "title", "compound.", "The", "H", "atoms", "were", "positioned", "geometrically", "and", "refined", "as", "riding", "atoms:", "N—H", "=", "0.86", "Å,", "and", "C—H", "=", "0.93,", "0.98,", "0.97,", "and", "0.96", "Å", "for", "aromatic,", "methine,", "methylene,", "and", "methyl", "H", "atoms,", "respectively,", "with", "Uiso(H)", "=", "x", "×", "Ueq(N,C),", "where", "x", "=", "1.5", "for", "sup-1" ]

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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "trans-Dichlorido(2,2-dimethylpropane-", "1,3-diamine)bis(triphenylphosphane)-", "ruthenium(II)", "Monther", "A.", "Khanfar,a*", "Ismail", "Waradb", "and", "Murad", "A.", "AlDamena", "aDepartment", "of", "Chemistry,", "The", "University", "of", "Jordan,", "Amman", "11942,", "Jordan,", "and", "bDepartment", "of", "Chemistry,", "King", "Saud", "University,", "PO", "Box", "2455,", "Riyadh-11451,", "Saudi", "Arabia", "Correspondence", "e-mail:", "m.khanfar@ju.edu.jo", "Received", "15", "May", "2010;", "accepted", "22", "May", "2010", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "293", "K;", "mean", "(C–C)", "=", "0.005", "A˚;", "R", "factor", "=", "0.034;", "wR", "factor", "=", "0.078;", "data-to-parameter", "ratio", "=", "16.8.", "In", "the", "title", "compound,", "[RuCl2(C5H14N2)(C18H15P)2],", "the", "RuII", "atom", "is", "six-coordinated,", "forming", "a", "slightly", "distorted", "octa-", "hedral", "geometry,", "with", "two", "chloride", "ions", "in", "an", "axial", "arrange-", "ment,", "and", "two", "P", "atoms", "of", "two", "triphenylphosphane", "and", "two", "chelating", "N", "atoms", "of", "the", "bidentate", "2,2-dimethylpropane-1,3-", "diamine", "ligand", "located", "in", "the", "equatorial", "plane.", "The", "average", "Ru—P,", "Ru—N", "and", "Ru—Cl", "bond", "lengths", "are", "2.325", "(18),", "2.1845", "(7)", "and", "2.4123", "(12)", "A˚", ",", "respectively.", "Related", "literature", "For", "the", "reduction", "of", "ketones", "to", "secondary", "alcohols,", "see:", "Noyori", "(1994).", "For", "enantioselective", "hydrogenation", "of", "prochiral", "carbonyl", "compounds", "to", "chiral", "alcohols,", "see:", "Drozdzak", "et", "al.", "(2005).", "For", "background", "to", "stereo-,", "regio-", "and", "enantio-selective", "ruthenium", "catalysis,", "see:", "Clarke", "(2002);", "Noyori", "(2003)", "and", "references", "therein.", "For", "RuII", "catalysts,", "see:", "Noyori", "&", "Ohkuma", "(2001);", "Ohkuma", "et", "al.", "(2002);", "Lindner", "et", "al.", "(2005).", "For", "related", "structures,", "see:", "Nachtigall", "et", "al.", "(2002);", "Lindner", "et", "al.", "(2003a,b);", "Doucet", "et", "al.", "(1998);", "Warad", "et", "al.", "(2006).", "metal-organic", "compounds", "Experimental", "Crystal", "data", "[RuCl2(C5H14N2)(C18H15P)2]", "Mr", "=", "798.69", "Monoclinic,", "P21=c", "a", "=", "17.393", "(2)", "A˚", "b", "=", "10.3493", "(16)", "A˚", "c", "=", "21.315", "(2)", "A˚", "=", "102.181", "(15)", "Data", "collection", "Enraf–Nonius", "CAD-4", "diffractometer", "Absorption", "correction:", "scan", "(North", "et", "al.,", "1968)", "Tmin", "=", "0.687,", "Tmax", "=", "0.967", "7922", "measured", "reflections", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.034", "wR(F", "2)", "=", "0.078", "S", "=", "1.03", "7319", "reflections", "V", "=", "3750.4", "(9)", "A˚", "3", "Z", "=", "4", "Mo", "K", "radiation", "=", "0.68", "mm", "1", "T", "=", "293", "K", "0.60", "0.60", "0.05", "mm", "7319", "independent", "reflections", "5387", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.025", "3", "standard", "reflections", "every", "400", "reflections", "intensity", "decay:", "2%", "436", "parameters", "Only", "H-atom", "coordinates", "refined", "max", "=", "0.39", "e", "A˚", "3", "min", "=", "0.51", "e", "A˚", "3", "Data", "collection:", "CAD-4", "EXPRESS", "(Enraf–Nonius,", "1994);", "cell", "refinement:", "CAD-4", "EXPRESS;", "data", "reduction:", "HELENA", "(Spek,", "1996);", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "PLATON", "(Spek,", "2009);", "software", "used", "to", "prepare", "material", "for", "publication:", "XCIF", "in", "SHELXTL", "(Sheldrick,", "2008).", "The", "authors", "gratefully", "acknowledge", "The", "Deanship", "of", "Scientific", "Research", "at", "The", "University", "of", "Jordan", "for", "financial", "support", "and", "Universita¨", "t", "Tu¨", "bingen", "for", "the", "use", "of", "the", "measurement", "facilities.", "They", "also", "thank", "Dr", "C.", "Maichle-", "Moessmer", "for", "assistance", "with", "the", "data", "collection.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "TK2679).", "References", "Clarke,", "M.", "(2002).", "Coord.", "Chem.", "Rev.", "232,", "69–93.", "Doucet,", "H.,", "Ohkuma,", "T.,", "Murata,", "K.,", "Yokozawa,", "T.,", "Kozawa,", "M.,", "Katayama,", "E.,", "England,", "A.,", "Ikariya,", "T.", "&", "Noyori,", "R.", "(1998).", "Angew.", "Chem.", "Int.", "Ed.", "37,", "1703–1707.", "Drozdzak,", "R.,", "Allaert,", "B.,", "Ledoux,", "N.,", "Dragutan,", "I.,", "Dragutan,", "V.", "&", "Verpoort,", "F.", "(2005).", "Coord.", "Chem.", "Rev.", "249,", "3055–3074.", "Enraf–Nonius", "(1994).", "CAD-4", "EXPRESS.", "Enraf–Nonius,", "Delft,", "The", "Nether-", "lands.", "Lindner,", "E.,", "Lu,", "Z.-L.,", "Mayer,", "A.", "H.,", "Speiser,", "B.,", "Tittel,", "C.", "&", "Warad,", "I.", "(2005).", "Electrochem.", "Commun.", "7,", "1013–1020.", "Lindner,", "E.,", "Mayer,", "H.", "A.,", "Warad,", "I.", "&", "Eichele,", "K.", "(2003a).", "J.", "Organomet.", "Chem.", "665,", "176–185.", "Lindner,", "E.,", "Warad,", "I.,", "Eichele,", "K.", "&", "Mayer,", "H.", "A.", "(2003b).", "Inorg.", "Chim.", "Acta,", "350,", "49–56.", "Nachtigall,", "C.,", "Al-Gharabli,", "S.,", "Eichele,", "K.,", "Lindner,", "E.", "&", "Mayer,", "H.", "A.", "(2002).", "Organometallics,", "21,", "105–112.", "North,", "A.", "C.", "T.,", "Phillips,", "D.", "C.", "&", "Mathews,", "F.", "S.", "(1968).", "Acta", "Cryst.", "A24,", "351–", "359.", "Noyori,", "R.", "(1994).", "Asymmetric", "Catalysis", "in", "Organic", "Synthesis.", "New", "York:", "J.", "Wiley", "&", "Sons.", "Noyori,", "R.", "(2003).", "Adv.", "Synth.", "Catal.", "345,", "15–32.", "Noyori,", "R.", "&", "Ohkuma,", "T.", "(2001).", "Angew.", "Chem.", "Int.", "Ed.", "40,", "40–73.", "Acta", "Cryst.", "(2010).", "E66,", "m731–m732", "doi:10.1107/S1600536810019276", "Khanfar", "et", "al.", "m731" ]

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[ "metal-organic", "compounds", "Ohkuma,", "T.,", "Koizumi,", "M.,", "Muniz,", "K.,", "Hilt,", "G.,", "Kabuta,", "C.", "&", "Noyori,", "R.", "(2002).", "J.", "Am.", "Chem.", "Soc.", "124,", "6508–6509.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Spek,", "A.", "L.", "(1996).", "HELENA.", "University", "of", "Utrecht,", "The", "Netherlands.", "Spek,", "A.", "L.", "(2009).", "Acta", "Cryst.", "D65,", "148–155.", "Warad,", "I.,", "Al-Resayes,", "S.", "&", "Eichele,", "K.", "(2006).", "Z.", "Kristallogr.", "221,", "275–276.", "m732", "Khanfar", "et", "al.", "[RuCl2(C5H14N2)(C18H15P)2]", "Acta", "Cryst.", "(2010).", "E66,", "m731–m732" ]

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[ "supplementary", "materials", "C111—P1—C121", "C111—P1—C131", "C121—P1—C131", "C111—P1—Ru1", "C121—P1—Ru1", "C131—P1—Ru1", "C112—C111—C116", "C112—C111—P1", "C116—C111—P1", "C113—C112—C111", "C113—C112—H11A", "C111—C112—H11A", "C114—C113—C112", "C114—C113—H11B", "C112—C113—H11B", "C115—C114—C113", "C115—C114—H11C", "C113—C114—H11C", "C114—C115—C116", "C114—C115—H11D", "C116—C115—H11D", "C115—C116—C111", "C115—C116—H11E", "C111—C116—H11E", "C126—C121—C122", "C126—C121—P1", "C122—C121—P1", "C123—C122—C121", "C123—C122—H12A", "C121—C122—H12A", "C124—C123—C122", "C124—C123—H12B", "C122—C123—H12B", "C123—C124—C125", "C123—C124—H12C", "C125—C124—H12C", "C124—C125—C126", "C124—C125—H12D", "C126—C125—H12D", "C121—C126—C125", "C121—C126—H12E", "C125—C126—H12E", "C132—C131—C136", "C132—C131—P1", "C136—C131—P1", "C131—C132—C133", "C131—C132—H13A", "C133—C132—H13A", "C134—C133—C132", "sup-8", "104.52", "(14)", "99.29", "(13)", "97.63", "(14)", "119.59", "(9)", "117.61", "(10)", "114.61", "(10)", "118.3", "(3)", "120.5", "(2)", "121.1", "(2)", "120.5", "(3)", "119.8", "119.8", "120.5", "(3)", "119.8", "119.8", "119.7", "(3)", "120.1", "120.1", "120.6", "(3)", "119.7", "119.7", "120.5", "(3)", "119.8", "119.8", "117.7", "(3)", "125.9", "(2)", "116.5", "(2)", "120.9", "(3)", "119.6", "119.6", "120.5", "(3)", "119.8", "119.8", "120.0", "(3)", "120.0", "120.0", "119.8", "(3)", "120.1", "120.1", "121.1", "(3)", "119.4", "119.4", "116.9", "(3)", "121.2", "(3)", "121.7", "(2)", "121.8", "(4)", "119.1", "119.1", "120.0", "(4)", "C221—C222—H22A", "C224—C223—C222", "C224—C223—H22B", "C222—C223—H22B", "C223—C224—C225", "C223—C224—H22C", "C225—C224—H22C", "C224—C225—C226", "C224—C225—H22D", "C226—C225—H22D", "C225—C226—C221", "C225—C226—H22E", "C221—C226—H22E", "C236—C231—C232", "C236—C231—P2", "C232—C231—P2", "C231—C232—C233", "C231—C232—H23A", "C233—C232—H23A", "C234—C233—C232", "C234—C233—H23B", "C232—C233—H23B", "C235—C234—C233", "C235—C234—H23C", "C233—C234—H23C", "C234—C235—C236", "C234—C235—H23D", "C236—C235—H23D", "C235—C236—C231", "C235—C236—H23E", "C231—C236—H23E", "C1—N1—Ru1", "C1—N1—H1N1", "Ru1—N1—H1N1", "C1—N1—H2N1", "Ru1—N1—H2N1", "H1N1—N1—H2N1", "C2—N2—Ru1", "C2—N2—H1N2", "Ru1—N2—H1N2", "C2—N2—H2N2", "Ru1—N2—H2N2", "H1N2—N2—H2N2", "N1—C1—C3", "N1—C1—H1B", "C3—C1—H1B", "N1—C1—H1C", "C3—C1—H1C", "H1B—C1—H1C", "119.4", "120.2", "(4)", "119.9", "119.9", "119.6", "(4)", "120.2", "120.2", "120.8", "(4)", "119.6", "119.6", "120.3", "(4)", "119.8", "119.8", "118.6", "(3)", "120.8", "(3)", "119.7", "(3)", "119.7", "(4)", "120.1", "120.1", "120.3", "(4)", "119.8", "119.8", "120.1", "(4)", "120.0", "120.0", "120.5", "(4)", "119.7", "119.7", "120.8", "(4)", "119.6", "119.6", "123.7", "(2)", "106.4", "106.4", "106.4", "106.4", "106.5", "123.7", "(2)", "106.4", "106.4", "106.4", "106.4", "106.5", "114.7", "(3)", "108.6", "108.6", "108.6", "108.6", "107.6" ]

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[ "supplementary", "materials", "Acta", "Cryst.", "(2010).", "E66,", "m731-m732", "[", "doi:10.1107/S1600536810019276", "]", "trans-Dichlorido(2,2-dimethylpropane-1,3-diamine)bis(triphenylphosphane)ruthenium(II)", "M.", "A.", "Khanfar,", "I.", "Warad", "and", "M.", "A.", "AlDamen", "Comment", "One", "of", "the", "important", "transformations", "in", "the", "organic", "synthesis", "is", "the", "reduction", "of", "ketones", "to", "secondary", "alcohol", "(Noyori,", "1994).", "The", "enantioselective", "hydrogenation", "of", "prochiral", "carbonyl", "compounds", "to", "chiral", "alcohols", "is", "among", "the", "most", "valuable", "method", "in", "organic", "chemistry", "(Drozdzak", "et", "al.,", "2005;", "Lindner", "et", "al.,", "2005).", "Furthermore,", "stereo-,", "regio-", "and", "enantioselective", "ruthenium-catalysis", "lies", "at", "the", "heart", "of", "current", "developments", "in", "pharmaceutical,", "agrochemical", "and", "similar", "industries", "(Noyori,", "2003;", "Clarke,", "2002).", "Recently", "Noyori", "et", "al.", "(Ohkuma", "et", "al.,", "2002;", "Noyori", "&", "Ohkuma,", "2001)", "discovered", "a", "ruthenium(II)", "complex", "system", "containing", "diphosphine", "and", "1,2-diamine", "ligands", "which,", "in", "the", "presence", "of", "a", "base", "and", "2-propanol,", "proved", "to", "be", "excellent", "catalysts", "(regarding", "efficiency,", "enantioselectivity,", "and", "flexibility)", "for", "the", "hydrogenation", "of", "ketones", "under", "mild", "conditions", "(Lindner", "et", "al.,", "2005;", "Noyori", "&", "Ohkuma,", "2001).", "The", "title", "complex", "is", "crystallized", "as", "free", "solvated", "trans-di-", "chloro-cis-bis(triphenylphosphane)", "isomer", "with", "approximate", "C2v", "symmetry.", "The", "ruthenium", "atom", "is", "coordinated", "with", "two", "chlorine", "species", "in", "trans", "form,", "one", "diamine", "co-ligand", "via", "the", "nitrogen", "atoms", "and", "two", "triphenylphosphane", "ligands", "via", "the", "phosphorus", "atoms", "in", "cis", "forms.", "The", "complex", "exhibits", "distorted", "octahedron", "geometry", "around", "the", "ruthenium", "center", "atom", "with", "two", "Ru–N", "distances", "of", "2.183", "(3)Å", "and", "2.185", "(3)", "Å,", "two", "Ru–Cl", "distances", "of", "2.4114", "(8)Å", "and", "2.4130", "(8)Å", "and", "two", "Ru–P", "distances", "equal", "2.3120", "(8)Å", "and", "2.3370", "(8)", "Å.", "The", "diamine", "and", "phosphine", "ligands", "are", "practically", "planar.", "The", "coordination", "angle", "of", "the", "diamine", "chelate", "ring", "results", "in", "distinctly", "N–Ru–N", "angle", "of", "82.35", "(11)°", "departs", "from", "ideal", "value", "by", "up", "to", "ap-", "proximately", "7.6°,", "due", "to", "the", "six-membered", "ring", "chelating", "nature", "of", "1,3-propanediamine", "ligand,", "while", "the", "P–Ru–P", "angle", "is", "equal", "98.55", "(3)°.", "The", "dichloro", "ligands", "are", "bent", "away", "from", "their", "axial", "positions", "toward", "the", "diamine", "ligand", "forming", "Cl–Ru–Cl", "angle", "of", "166.32", "(3)°,", "resonating", "to", "the", "steric", "effect", "of", "the", "phenyls", "in", "the", "phosphine", "ligands.", "In", "the", "crystal", "structure", "there", "are", "a", "number", "of", "RuCl···HN", "contacts", "smaller", "than", "3.0", "Å,", "indicating", "the", "presence", "of", "unconventional", "intra-hydrogen", "bonds", "(Doucet", "et", "al.,", "1998;", "Warad", "et", "al.,", "2006).", "Experimental", "All", "the", "reactions", "were", "performed", "using", "Schlenk-type", "flask", "under", "argon", "and", "standard", "high", "vacuum-line", "techniques.", "Solvents", "were", "of", "analytical", "grade", "and", "distilled", "under", "argon.", "The", "title", "compound", "was", "prepared", "starting", "from", "trans-RuCl2(PPh3)3", "in", "a", "similar", "procedure", "described", "previously", "(Lindner", "et", "al.,", "2003b).", "Mixing", "of", "2,2-dimethylpropane-1,3-diamine", "(0.059", "ml,", "0.49", "mmol)", "in", "dichloromethane", "(10", "ml)", "dropwise", "with", "trans-RuCl2(PPh3)3", "(0.454", "mmol)", "dissolved", "in", "the", "same", "solvent", "(15", "ml).", "The", "reaction", "mixture", "was", "stirred", "at", "room", "temperature", "for", "2", "h.", "The", "solvent", "was", "removed", "in", "vacuo.", "Then", "the", "residue", "was", "washed", "well", "with", "hexane", "then", "diethylether", "and", "dried,", "to", "yield", "310", "mg", "(90%)", "of", "yellow", "powder.", "The", "recrystallization", "was", "performed", "by", "slow", "diffusion", "of", "diethylether", "into", "a", "solution", "of", "the", "complex", "in", "dichloromethane", "to", "yield", "orange-brown-plated", "crystals.", "1H", "NMR", "(CD2Cl2):", "δ", "(p.p.m.)", "0.79", "(s,", "6H,", "C(CH3)2),", "2.57", "(m,", "4H,", "NCH2),", "3.12", "(br,", "s,", "4H,", "NH2),", "7.2–7.7", "(m,", "20H,", "C6H5).", "31P{1H}", "NMR", "(CD2Cl2):δ", "(p.p.m.)", "46.02", "(s).", "13C{1H}", "NMR", "(CD2Cl2):", "δ", "(p.p.m.)", "25.3", "(s,", "C(CH3)2),", "34.2", "(s,", "C(CH3)2),", "49.2", "(s,", "CH2N),", "127.7", "(t,", "N", "=", "4.04", "Hz,", "m-C6H5),", "129.3", "(s,", "p-C6H5),", "135.4", "(t,", "N=7.42", "Hz,o-C6H5),", "135.8", "(d,", "N", "=", "18.8", "Hz,", "1-C6H5).", "FAB", "MS:", "(m/z)", "798.1", "(M+).", "Anal.", "Calc.", "for", "C41H44Cl2N2P2Ru:", "C,", "66.65.12;", "H,", "5.55;", "Cl,", "8.88;", "N,", "3.51.", "Found:", "C,", "66.94;", "H,", "5.52;", "Cl,", "9.20;", "N,", "3.59%.", "sup-1" ]

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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "Tetrakis{l3-2-[(2-hydroxyethyl)amino]-", "ethanolato}tetrakis[chloridonickel(II)]", "methanol", "solvate", "Youzhu", "Yu,a", "Yuhua", "Guo,a", "Lei", "Lvb", "and", "Dacheng", "Lib*", "aDepartment", "of", "Chemistry", "and", "Environmental", "Engineering,", "Anyang", "Institute", "of", "Technology,", "Henan", "455000,", "People’s", "Republic", "of", "China,", "and", "bCollege", "of", "Chemistry", "and", "Chemical", "Engineering,", "Liaocheng", "University,", "Shandong", "252059,", "People’s", "Republic", "of", "China", "Correspondence", "e-mail:", "lidacheng@lcu.edu.cn", "Received", "13", "June", "2010;", "accepted", "23", "June", "2010", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "298", "K;", "mean", "(C–C)", "=", "0.009", "A˚;", "R", "factor", "=", "0.043;", "wR", "factor", "=", "0.141;", "data-to-parameter", "ratio", "=", "15.6.", "The", "complex", 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[ "O3—Ni2—O6", "N3—Ni2—O6", "O7—Ni2—O6", "O5—Ni2—Cl2", "O3—Ni2—Cl2", "N3—Ni2—Cl2", "O7—Ni2—Cl2", "O6—Ni2—Cl2", "O3—Ni3—O7", "O3—Ni3—O1", "O7—Ni3—O1", "O3—Ni3—N2", "O7—Ni3—N2", "O1—Ni3—N2", "O3—Ni3—O4", "O7—Ni3—O4", "O1—Ni3—O4", "N2—Ni3—O4", "O3—Ni3—Cl3", "O7—Ni3—Cl3", "O1—Ni3—Cl3", "N2—Ni3—Cl3", "O4—Ni3—Cl3", "O7—Ni4—O1", "O7—Ni4—N4", "O1—Ni4—N4", "O7—Ni4—O5", "O1—Ni4—O5", "N4—Ni4—O5", "O7—Ni4—O8", "O1—Ni4—O8", "N4—Ni4—O8", "O5—Ni4—O8", "O7—Ni4—Cl4", "O1—Ni4—Cl4", "N4—Ni4—Cl4", "O5—Ni4—Cl4", "O8—Ni4—Cl4", "C1—O1—Ni4", "C1—O1—Ni1", "Ni4—O1—Ni1", "C1—O1—Ni3", "Ni4—O1—Ni3", "Ni1—O1—Ni3", "C5—O3—Ni3", "C5—O3—Ni2", "Ni3—O3—Ni2", "C5—O3—Ni1", "Ni3—O3—Ni1", "86.76", "(15)", "79.46", "(17)", "167.40", "(14)", "170.64", "(11)", "100.80", "(11)", "94.61", "(14)", "93.16", "(10)", "93.12", "(12)", "82.80", "(13)", "79.64", "(14)", "81.65", "(13)", "83.21", "(16)", "158.91", "(17)", "111.15", "(16)", "97.16", "(15)", "87.04", "(14)", "168.54", "(14)", "79.14", "(16)", "171.15", "(11)", "101.82", "(11)", "93.46", "(10)", "94.26", "(14)", "90.66", "(12)", "83.25", "(14)", "83.12", "(16)", "159.57", "(17)", "78.83", "(14)", "80.81", "(13)", "111.26", "(17)", "97.15", "(15)", "87.13", "(14)", "79.56", "(17)", "167.63", "(14)", "170.45", "(11)", "101.52", "(11)", "94.28", "(14)", "93.67", "(10)", "91.39", "(12)", "124.9", "(3)", "110.1", "(3)", "98.59", "(14)", "122.1", "(3)", "95.45", "(14)", "101.20", "(15)", "109.6", "(3)", "123.2", "(3)", "98.34", "(14)", "125.0", "(3)", "100.17", "(15)", "C2—C1—H1A", "O1—C1—H1B", "C2—C1—H1B", "H1A—C1—H1B", "N4—C16—C15", "N4—C16—H16A", "C15—C16—H16A", "N4—C16—H16B", "C15—C16—H16B", "H16A—C16—H16B", "N2—C8—C7", "N2—C8—H8A", "C7—C8—H8A", "N2—C8—H8B", "C7—C8—H8B", "H8A—C8—H8B", "C16—N4—C14", "C16—N4—Ni4", "C14—N4—Ni4", "C16—N4—H4AA", "C14—N4—H4AA", "Ni4—N4—H4AA", "C8—N2—C6", "C8—N2—Ni3", "C6—N2—Ni3", "C8—N2—H2AA", "C6—N2—H2AA", "Ni3—N2—H2AA", "N3—C12—C11", "N3—C12—H12A", "C11—C12—H12A", "N3—C12—H12B", "C11—C12—H12B", "H12A—C12—H12B", "N1—C4—C3", "N1—C4—H4A", "C3—C4—H4A", "N1—C4—H4B", "C3—C4—H4B", "H4A—C4—H4B", "N4—C14—C13", "N4—C14—H14A", "C13—C14—H14A", "N4—C14—H14B", "C13—C14—H14B", "H14A—C14—H14B", "N2—C6—C5", "N2—C6—H6A", "C5—C6—H6A", "supplementary", "materials", "109.9", "109.9", "109.9", "108.3", "111.5", "(5)", "109.3", "109.3", "109.3", "109.3", "108.0", "110.4", "(5)", "109.6", "109.6", "109.6", "109.6", "108.1", "115.2", "(5)", "107.8", "(4)", "107.2", "(3)", "108.8", "108.8", "108.8", "115.5", "(5)", "107.0", "(3)", "107.9", "(3)", "108.7", "108.7", "108.7", "110.6", "(5)", "109.5", "109.5", "109.5", "109.5", "108.1", "111.3", "(5)", "109.4", "109.4", "109.4", "109.4", "108.0", "111.1", "(4)", "109.4", "109.4", "109.4", "109.4", "108.0", "112.1", "(4)", "109.2", "109.2", "sup-7" ]

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[ "supplementary", "materials" ]

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[ "metal-organic", "compounds", "Data", "collection:", "CrystalClear", "(Rigaku/MSC,", "2006);", "cell", "refinement:", "CrystalClear;", "data", "reduction:", "CrystalClear;", "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:", "publCIF", "(Westrip,", "2010).", "This", "study", "was", "supported", "by", "the", "Doctoral", "Research", "Fund", "of", "Henan", "Chinese", "Medicine", "(BSJJ2009–38)", "and", "the", "Science", "and", "Technology", "Department", "of", "Henan", "Province", "(082102330003).", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "WM2438).", "References", "Jacobson,", "R.", "(1998).", "REQAB.", "Private", "communication", "to", "the", "Rigaku", "Corporation,", "Tokyo,", "Japan.", "Liu,", "T.,", "Zhang,", "Y.-J.,", "Wang,", "Z.-M.", "&", "Gao,", "S.", "(2006).", "Inorg.", "Chem.", "45,", "2782–", "2784.", "Liu,", "T.,", "Zhang,", "Y.-J.,", "Wang,", "Z.-M.", "&", "Gao,", "S.", "(2008).", "J.", "Am.", "Chem.", "Soc.", "130,", "10500–10511.", "Rigaku/MSC", "(2006).", "CrystalClear.", "Rigaku/MSC,", "The", "Woodlands,", "Texas,", "USA.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Wang,", "X.-T.,", "Wang,", "B.-W.,", "Wang,", "Z.-M.,", "Zhang,", "W.", "&", "Gao,", "S.", "(2008).", "Inorg.", "Chim.", "Acta,", "361,", "3895–3902.", "Westrip,", "S.", "P.", "(2010).", "J.", "Appl.", "Cryst.", "43,", "920–925.", "m308", "Liu", "et", "al.", "[Ni6(C13H10NO2)4(N3)8(CH4O)8]", "6CH4O", "Acta", "Cryst.", "(2011).", "E67,", "m307–m308" ]

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[ "supplementary", "materials", "Acta", "Cryst.", "(2011).", "E67,", "m307-m308", "[", "doi:10.1107/S1600536811003473", "]", "Poly[[tetrakis(", "-2-anilinobenzoato-", "2O:O')tetra-", "1,1,1-azido-tetra-", "1,1-azido-", "octamethanolhexanickel(II)]", "methanol", "hexasolvate]", "Y.-J.", "Liu,", "X.-J.", "Fu,", "X.-F.", "Li,", "T.-B.", "Qiu", "and", "H.-X.", "Yang", "Comment", "The", "design", "and", "synthesis", "of", "new", "polynuclear", "metal", "complexes", "for", "single", "molecule", "magnets", "have", "attracted", "great", "interest", "in", "coordination", "chemsitry,", "because", "single", "molecule", "magnets", "not", "only", "show", "fascinating", "physical", "properties,", "but", "also", "have", "potential", "application", "in", "information", "storage", "and", "quantum", "computing", "at", "the", "molecular", "level", "(Liu", "et", "al.,", "2008).", "To", "date,", "although", "it", "is", "difficult", "to", "predict", "which", "kind", "of", "topology", "and", "structure", "will", "lead", "to", "high-nuclearity", "compounds", "in", "advance,", "many", "synthetic", "approaches", "have", "been", "employed", "to", "obtain", "well-isolated", "polynuclear", "complexes,", "e.g.", "by", "using", "new", "blocking", "ligands", "with", "short", "bridges.", "Many", "single", "molecule", "magnets", "are", "based", "on", "MnIII,", "FeIII,", "and", "NiII.", "In", "most", "of", "these", "compounds,", "magnetic", "exchange", "interactions", "are", "mainly", "propagated", "by", "bridging", "OH-,", "OR-,", "O2-,", "or", "RCO2-", "groups,", "which", "often", "transmit", "antiferromagnetic", "interactions.", "An", "attractive", "strategy", "to", "facilitate", "the", "formation", "of", "ferromagnetic", "coupled", "clusters", "is", "to", "utilize", "azide", "and", "carboxalate-containing", "ligands", "simultaneously", "(Liu", "et", "al.,", "2006).", "Herein,", "we", "report", "the", "synthesis", "and", "structure", "of", "the", "hexanuclear", "Ni(II)", "complex,", "[Ni6(C13H10NO2)4(N3)8(CH3OH)8].6CH3OH.", "The", "structure", "of", "the", "title", "compound", "consists", "of", "neutral", "hexanuclear", "[NiII6(C13H10NO2)4(N3)8(CH3OH)8]", "molecules", "and", "six", "methanol", "solvate", "molecules", "situated", "between", "the", "hexanuclear", "units.", "The", "complete", "molecule", "has", "inversion", "symmetry.", "In", "the", "neutral", "hexanuclear", "unit,", "six", "octahedrally", "coordinated", "NiII", "atoms", "are", "linked", "by", "four", "µ1,1,1-azido", "and", "four", "µ1,1-azido", "bridges,", "forming", "face-sharing", "tetracubane", "units", "with", "four", "missing", "corners", "based", "on", "the", "Ni6N8", "core.", "The", "NiII", "atoms", "are", "further", "bridged", "by", "four", "µ1,2-carboxalate", "ligands", "(Fig.", "1).", "The", "Ni—O", "distances", "range", "between", "2.000", "(3)–2.094", "(3)", "Å,", "and", "the", "Ni—N", "distances", "between", "2.052", "(4)–2.165", "(3)", "Å.", "These", "bond", "lengths", "indicate", "that", "the", "NiII", "ions", "are", "in", "the", "divalent", "state,", "and", "are", "in", "agreement", "with", "other", "NiII", "complexes", "(Wang", "et", "al.,", "2008).", "The", "hexanuclear", "units", "are", "connected", "via", "N—H···O", "hydrogen", "bonding", "into", "a", "three-dimensional", "structure", "(Fig.", "2).", "The", "N—H···O", "hydrogen", "bonding", "(Table", "2)", "is", "accomplished", "through", "the", "N", "atoms", "of", "2-phenylamino-benzoate", "and", "O", "atoms", "of", "carboxylate", "groups,", "with", "the", "N···O", "distances", "being", "2.667···2.676", "Å.", "Although", "the", "H", "atoms", "of", "the", "methanol", "OH", "groups", "could", "not", "be", "located,", "short", "O···N/O", "contacts", "suggest", "that", "these", "molecules", "participate", "in", "hydrogen", "bonding", "between", "O", "atoms", "of", "methanol", "as", "donors", "and", "acceptors,", "and", "between", "O", "atoms", "of", "methanol", "and", "N", "atoms", "of", "azido", "bridges,", "with", "O···O", "distances", "in", "the", "range", "of", "2.65···2.72", "Å,", "and", "O···N", "distances", "in", "the", "range", "of", "2.79···2.86", "Å.", "Experimental", "Under", "stirring,", "2.0", "mmol", "2-phenylamino-benzoic", "acid,", "4.0", "mmol", "NaN3", "were", "added,", "one", "after", "another,", "into", "a", "20", "ml", "methanol", "solution", "containing", "1.0", "mol", "Ni(ClO4)2.6H2O.", "The", "resulting", "solution", "was", "kept", "stirred", "for", "another", "hour,", "and", "then", "filtered", "off.", "The", "filtered", "solution", "was", "allowed", "to", "stand", "undisturbed", "in", "a", "sealed", "vessel.", "Crystallization", "took", "one", "week", "and", "gave", "sup-1" ]

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[ "Fig.", "1", "supplementary", "materials", "sup-11" ]

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[ "Fig.", "1", "supplementary", "materials", "sup-7" ]

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[ "supplementary", "materials", "Acta", "Cryst.", "(2010).", "E66,", "o137", "[", "doi:10.1107/S1600536809052386", "]", "(Z)-Ethyl", "2-hydroxyimino-2-(4-nitrobenzyl)ethanoate", "I.", "Caracelli,", "A.", "C.", "Trindade,", "P.", "J.", "S.", "Moran,", "L.", "Hinoue,", "J.", "Zukerman-Schpector", "and", "E.", "R.", "T.", "Tiekink", "Comment", "The", "title", "compound", "(I)", "was", "prepared", "as", "an", "intermediary", "during", "the", "synthesis", "of", "chiral", "hydroxyaminoacids", "and", "hy-", "droxyaminoalcohols,", "as", "α-ketomethoxyimino", "compounds", "are", "reduced", "by", "sodium", "borohydride", "(Corrêa", "&", "Moran,", "1999)", "and", "enantioselectively", "bio-reduced", "by", "whole", "cells", "of", "yeast", "(Kreutz", "et", "al.,", "1997;", "Kreutz", "et", "al.,", "2000).", "The", "structure", "of", "(I)", "is", "non-planar", "as", "seen", "by", "the", "values", "of", "the", "C3–C4–C7–O3", "and", "C4–C7–C8–N2", "torsion", "angles", "within", "the", "central", "moiety", "of", "8.8", "(2)", "and", "15.8", "(2)", "°,", "respectively.", "The", "peripheral", "residues", "are", "twisted", "with", "respect", "to", "the", "inner", "atoms.", "Thus,", "the", "nitro", "ring", "is", "twisted", "out", "of", "the", "plane", "of", "the", "benzene", "ring", "to", "which", "it", "is", "connected:", "the", "C2–C1–N1–O1", "torsion", "angle", "is", "-13.7", "(3)", "°.", "Even", "more", "dramatic", "is", "the", "twist", "about", "the", "C8—C9", "bond", "with", "the", "C7–C8–C9–O6", "torsion", "angle", "being", "94.77", "(17)°,", "indicating", "the", "terminal", "ester", "group", "is", "orthogonal", "to", "the", "hydroxyimino", "residue.", "With", "respect", "to", "the", "C8═N2", "bond,", "the", "conformation", "is", "Z.", "There", "are", "two", "other", "structures", "in", "the", "literature", "containing", "the", "basic", "C(═O)C(═NOH)C(═O)OC", "frame-", "work.", "In", "benzyl", "2-(hydroxyimino)acetoacetate", "a", "Z", "conformation", "is", "found", "for", "the", "oxime", "group", "(Forsyth", "et", "al.,", "2006)", "whereas", "in", "each", "of", "the", "two", "independent", "molecules", "comprising", "the", "asymmetric", "unit", "in", "ethyl", "2-(hydroxyimino)-3-oxo-3-phenylpropi-", "onate,", "an", "E", "conformation", "is", "found", "(Ramos", "Silva", "et", "al.,", "2004).", "The", "crystal", "packing", "of", "(I)", "is", "dominated", "by", "O—H···O", "hydrogen", "bonding", "involving", "the", "oxime-O4—H", "and", "benzoyl-O3", "atoms", "which", "leads", "to", "the", "formation", "of", "supramolecular", "chains", "along", "[0", "1", "0]", "with", "a", "flat", "topology,", "Fig.", "2", "and", "Table", "1.", "The", "pres-", "ence", "of", "C–H···O", "contacts", "provide", "stability", "to", "the", "chain.", "These", "C5–H···O5", "contacts", "close", "13-membered", "{···OC3O···HC4NOH}", "synthons,", "Fig.", "3", "and", "Table", "1.", "The", "chains", "are", "linked", "into", "2-D", "arrays", "in", "the", "[3", "0", "1]", "plane", "by", "further", "C–H···O", "contacts", "involving", "the", "nitro", "groups", "and", "centrosymmetric", "10-membered", "{···ONC2H}2", "synthons,", "Fig.", "3", "and", "Table", "1.", "The", "resultant", "layer", "is", "es-", "sentially", "flat", "with", "the", "ethoxy", "groups", "lying", "above", "and", "below", "the", "layer.", "The", "methyl-H", "atoms", "of", "one", "of", "the", "disordered", "ethoxy", "groups", "form", "C–H···O", "contacts", "with", "the", "nitro-O1", "atoms", "providing", "stability", "to", "the", "stacked", "layers,", "Fig.", "4", "and", "Table", "1.", "Experimental", "Refinement", "The", "title", "compound,", "(I),", "was", "prepared", "following", "a", "modified", "literature", "method", "(Adkins", "and", "Reeve,", "1938).", "A", "solution", "of", "sodium", "nitrite", "(5", "mmol)", "and", "water", "(2", "ml)", "was", "added", "drop-wise", "to", "a", "solution", "of", "ethyl", "3-oxo-3-(4-nitrophenyl)propanoate", "(2", "mmol)", "in", "glacial", "acetic", "acid", "(3", "ml)", "at", "273", "K.", "The", "resulting", "solution", "was", "stirred", "for", "1", "h", "at", "273", "K.", "The", "temperature", "was", "then", "raised", "to", "303", "K", "and", "the", "reaction", "left", "for", "a", "further", "hour.", "The", "reaction", "mixture", "was", "quenched", "with", "water", "(2.5", "ml)", "and", "treated", "with", "ether", "(4", "x", "5", "ml).", "The", "organic", "layer", "was", "dried", "with", "Mg(SO4)", "and", "the", "solvent", "evaporated", "to", "afford", "a", "mixture", "of", "Z:E", "(40:60)", "isomers", "in", "87%", "yield", "that", "were", "separated", "by", "dissolving", "in", "ethyl", "acetate", "and", "precipitating", "with", "hexane.", "The", "O–", "and", "C-bound", "H", "atoms", "were", "geometrically", "placed", "(O–H", "=", "0.82", "Å", "and", "C–H", "=", "0.9–0.97", "Å)", "and", "refined", "as", "riding", "with", "Uiso(H)", "=", "1.2Ueq(C)", "and", "1.5Ueq(O", "and", "methyl-C).", "sup-1" ]

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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "(Z)-Ethyl", "2-hydroxyimino-2-(4-nitro-", "benzyl)ethanoate", "Ignez", "Caracelli,a*", "Antonio", "C.", "Trindade,b", "Paulo", "J.", "S.", "Moran,c", "Luciana", "Hinoue,c", "Julio", "Zukerman-Schpectord", "and", "Edward", "R.", "T.", "Tiekinke", "aBioMat-Physics", "Department,", "UNESP", "–", "Univ", "Estadual", "Paulista,", "17033-360", "Bauru,", "SP,", "Brazil,", "bInstituto", "de", "Qu´ımica", "e", "Biotecnologia,", "Universidade", "Federal", "de", "Alagoas,", "57072-970", "Maceio´", ",", "AL,", "Brazil,", "cInstituto", "de", "Qu´ımica,", "Universidade", "Estadual", "de", "Campinas,", "CP", "6154,", "13083-970", "Campinas,", "SP,", "Brazil,", "dDepartment", "of", "Chemistry,", "Universidade", "Federal", "de", "S˜ao", "Carlos,", "13565-905", "S˜ao", "Carlos,", "SP,", "Brazil,", "and", "eDepartment", "of", "Chemistry,", "University", "of", "Malaya,", "50603", "Kuala", "Lumpur,", "Malaysia", "Correspondence", "e-mail:", "ignez@fc.unesp.br", "Received", "29", "November", "2009;", "accepted", "5", "December", "2009", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "290", "K;", "mean", "(C–C)", "=", "0.002", "A˚;", "disorder", "in", "main", "residue;", "R", "factor", "=", "0.048;", "wR", "factor", "=", "0.128;", "data-to-parameter", "ratio", "=", "14.6.", "The", "title", "molecule,", "C11H10N2O6,", "has", "a", "Z", "conformation", "about", "the", "C", "N", "bond", "of", "the", "oxime", "unit.", "There", "are", "significant", "twists", "from", "planarity", "throughout", "the", "molecule,", "the", "most", "significant", "being", "between", "the", "hydroxyimino", "and", "ester", "groups", "which", "are", "effectively", "orthogonal", "with", "an", "N—C—C—Ocarbonyl", "torsion", "angle", "of", "91.4", "(2)", ".", "The", "crystal", "packing", "features", "oxime–benzoyl", "O—H", "O", "contacts", "that", "lead", "to", "chains", "along", "[010]", "and", "C—", "H", "O", "interactions", "also", "occur.", "Related", "literature", "For", "background", "to", "the", "synthesis", "of", "chiral", "hydroxyaminoacids", "and", "hydroxyaminoalcohols,", "see:", "Corr", "eˆa", "&", "Moran", "(1999);", "Kreutz", "et", "al.", "(1997,", "2000).", "For", "related", "structures,", "see:", "Ramos", "Silva", "et", "al.", "(2004);", "Forsyth", "et", "al.", "(2006).", "For", "the", "synthesis,", "see:", "Adkins", "&", "Reeve", "(1938).", "Experimental", "Crystal", "data", "C11H10N2O6", "Mr", "=", "266.21", "Monoclinic,", "C2=c", "a", "=", "23.2347", "(7)", "A˚", "b", "=", "12.0698", "(6)", "A˚", "c", "=", "8.9698", "(4)", "A˚", "=", "106.100", "(2)", "V", "=", "2416.82", "(18)", "A˚", "3", "Z", "=", "8", "Mo", "K", "radiation", "=", "0.12", "mm", "1", "Data", "collection", "Nonius", "KappaCCD", "diffractometer", "8147", "measured", "reflections", "2752", "independent", "reflections", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.048", "wR(F", "2)", "=", "0.128", "S", "=", "1.05", "2752", "reflections", "Table", "1", "Hydrogen-bond", "geometry", "(A˚", ",", ").", "D—H", "A", "O3i", "O4—H4o", "O5i", "C5—H5", "O1ii", "C2—H2", "O1iii", "C11—H11a", "Symmetry", "x", "12;", "y", "12;", "z", "codes:", "(i)", "1.", "D—H", "0.82", "0.93", "0.93", "0.96", "organic", "compounds", "T", "=", "290", "K", "0.18", "0.15", "0.12", "mm", "2004", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.033", "189", "parameters", "H-atom", "parameters", "constrained", "max", "=", "0.20", "e", "A˚", "3", "min", "=", "0.19", "e", "A˚", "3", "H", "1.91", "2.58", "2.55", "2.52", "A", "D", "A", "2.7165", "(16)", "3.371", "(2)", "3.393", "(3)", "3.426", "(5)", "D—H", "A", "166", "144", "151", "158", "x", "þ", "12;", "y", "þ", "12;", "z", "þ", "12;", "(ii)", "x", "þ", "1;", "y;", "z", "þ", "2;", "(iii)", "Data", "collection:", "COLLECT", "(Nonius,", "1999);", "cell", "refinement:", "SCALEPACK", "(Otwinowski", "&", "Minor,", "1997);", "data", "reduction:", "DENZO", "(Otwinowski", "&", "Minor,", "1997)", "and", "SCALEPACK;", "program(s)", "used", "to", "solve", "structure:", "SIR97", "(Altomare", "et", "al.,", "1999);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "DIAMOND", "(Brandenburg,", "2006);", "software", "used", "to", "prepare", "material", "for", "publication:", "WinGX", "(Farrugia,", "1999),", "PARST", "(Nardelli,", "1995)", "and", "publCIF", "(Westrip,", "2009).", "We", "thank", "FAPESP,", "CNPq", "and", "CAPES", "for", "financial", "support.", "Publication", "costs", "were", "met", "by", "FAPESP", "(Proc.", "2008/02531–5).", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "HG2614).", "References", "Adkins,", "H.", "&", "Reeve,", "E.", "W.", "(1938).", "J.", "Am.", "Chem.", "Soc.", "60,", "1328–1331.", "Altomare,", "A.,", "Burla,", "M.", "C.,", "Camalli,", "M.,", "Cascarano,", "G.", "L.,", "Giacovazzo,", "C.,", "Guagliardi,", "A.,", "Moliterni,", "A.", "G.", "G.,", "Polidori,", "G.", "&", "Spagna,", "R.", "(1999).", "J.", "Appl.", "Cryst.", "32,", "115–119.", "Brandenburg,", "K.", "(2006).", "DIAMOND.", "Crystal", "Impact", "GbR,", "Bonn,", "Germany.", "Correˆ", "a,", "I.", "R.", "&", "Moran,", "P.", "J.", "S.", "(1999).", "Tetrahedron,", "55,", "14221–14232.", "Farrugia,", "L.", "J.", "(1999).", "J.", "Appl.", "Cryst.", "32,", "837–838.", "Forsyth,", "C.", "M.,", "Langford,", "S.", "J.", "&", "Lee,", "K.", "A.", "(2006).", "Acta", "Cryst.", "E62,", "o5654–", "o5655.", "Kreutz,", "O.", "C.,", "Moran,", "P.", "J.", "S.", "&", "Rodrigues,", "J.", "A.", "R.", "(1997).", "Tetrahedron", "Asymmetry,", "8,", "2649–2653.", "Kreutz,", "O.", "C.,", "Segura,", "R.", "C.", "M.,", "Rodrigues,", "J.", "A.", "R.", "&", "Moran,", "P.", "J.", "S.", "(2000).", "Tetrahedron", "Asymmetry,", "11,", "2107–2115.", "Nardelli,", "M.", "(1995).", "J.", "Appl.", "Cryst.", "28,", "659.", "Nonius", "(1999).", "COLLECT.", "Nonius", "BV,", "Delft,", "The", "Netherlands.", "Otwinowski,", "Z.", "&", "Minor,", "W.", "(1997).", "Methods", "in", "Enzymology,", "Vol.", "276,", "Macromolecular", "Crystallography,", "Part", "A,", "edited", "by", "C.", "W.", "Carter", "Jr", "&", "R.", "M.", "Sweet,", "pp.", "307–326.", "New", "York:", "Academic", "Press.", "Ramos", "Silva,", "M.,", "Matos", "Beja,", "A.,", "Paix", "a˜o,", "J.", "A.,", "Lopes,", "S.", "H.,", "Cabral,", "A.", "M.", "T.", "D.", "P.", "V.,", "d’A.", "Rocha", "Gonsalves,", "A.", "M.", "&", "Sobral,", "A.", "J.", "F.", "N.", "(2004).", "Z.", "Kristallogr.", "New", "Cryst.", "Struct.", "219,", "145–146.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Westrip,", "S.", "P.", "(2009).", "publCIF.", "In", "preparation.", "Acta", "Cryst.", "(2010).", "E66,", "o137", "doi:10.1107/S1600536809052386", "Caracelli", "et", "al.", "o137" ]

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[ "metal-organic", "compounds", "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "catena-Poly[[diacetonitrilecopper(I)]-l-", "dicyanamido]", "Benjamin", "Oelkers,", "Marion", "Stricker", "and", "Jo¨rg", "Sundermeyer*", "Philipps-Universita¨t", "Marburg,", "Fachbereich", "Chemie,", "Hans-Meerwein-Strasse,", "35032", "Marburg,", "Germany", "Correspondence", "e-mail:", "jsu@staff.uni-marburg.de", "Received", "4", "November", "2011;", "accepted", "7", "November", "2011", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "100", "K;", "mean", "(C–C)", "=", "0.003", "A˚;", "R", "factor", "=", "0.032;", "wR", "factor", "=", "0.066;", "data-to-parameter", "ratio", "=", "13.5.", "The", "crystal", "structure", "of", "the", "title", "compound,", "[Cu(C2N3)-", "(C2H3N)2]n,", "features", "zigzag", "chains", "along", "the", "a", "axis", "that", "consist", "of", "alternating", "[Cu(MeCN)2]", "and", "dicyanamide", "units,", "the", "latter", "acting", "as", "bidentate", "ligands", "via", "both", "terminal", "N", "atoms.", "The", "Cu", "atom", "shows", "a", "slightly", "distorted", "tetrahedral", "coordination", "sphere.", "The", "anionic", "and", "neutral", "ligands", "lie", "on", "different", "mirror", "planes", "(perpendicular", "to", "the", "b", "and", "a", "axis,", "respectively),", "while", "the", "Cu", "atom", "is", "situated", "on", "their", "intersection.", "The", "asymmetric", "unit", "comprises", "one", "fourth", "of", "the", "formula", "unit.", "Related", "literature", "For", "ionic", "liquids", "(ILs)", "with", "dicyanamide", "anions,", "see:", "MacFarlane", "et", "al.", "(2001).", "For", "copper-based", "ILs,", "see:", "Stricker", "et", "al.", "(2010).", "For", "solvent-free", "[Cu(dicyanamide)]", "and", "its", "mono-", "adduct", "with", "acetonitrile,", "see:", "Bessler", "et", "al.", "(2000);", "Batten", "et", "al.", "(2000).", "Experimental", "Crystal", "data", "[Cu(C2N3)(C2H3N)2]", "Mr", "=", "211.71", "Orthorhombic,", "Pmmn", "a", "=", "7.5222", "(5)", "A˚", "b", "=", "10.5307", "(11)", "A˚", "c", "=", "5.5378", "(4)", "A˚", "V", "=", "438.67", "(6)", "A˚", "3", "Z", "=", "2", "Mo", "K", "radiation", "Data", "collection", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.032", "wR(F", "2)", "=", "0.066", "S", "=", "1.13", "528", "reflections", "Stoe", "IPDS", "2", "diffractometer", "Absorption", "correction:", "multi-scan", "(Blessing,", "1995)", "Tmin", "=", "0.375,", "Tmax", "=", "0.783", "4132", "measured", "reflections", "528", "independent", "reflections", "510", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.097", "=", "2.44", "mm", "1", "T", "=", "100", "K", "0.45", "0.27", "0.12", "mm", "39", "parameters", "H-atom", "parameters", "constrained", "max", "=", "0.89", "e", "A˚", "3", "min", "=", "1.05", "e", "A˚", "3", "1.312", "(3)", "1.155", "(3)", "117.0", "(3)", "172.85", "(18)", "176.2", "(2)", "Table", "1", "Selected", "geometric", "parameters", "(", "A˚,", ").", "Cu1—N2", "Cu1—N3", "N2i—Cu1—N2", "N2—Cu1—N3", "N3i—Cu1—N3", "1.974", "(2)", "2.021", "(2)", "110.34", "(11)", "111.79", "(4)", "98.91", "(11)", "N1—C1", "N2—C1", "C1ii—N1—C1", "C1—N2—Cu1", "N2—C1—N1", "Symmetry", "codes:", "(i)", "x", "þ", "32;", "y", "þ", "32;", "z;", "(ii)", "x", "þ", "12;", "y", "þ", "32;", "z.", "Data", "collection:", "X-AREA", "(Stoe", "&", "Cie,", "2001);", "cell", "refinement:", "X-", "AREA;", "data", "reduction:", "X-AREA;", "program(s)", "used", "to", "solve", "structure:", "SIR92", "(Altomare", "et", "al.,", "1993);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "DIAMOND", "(Brandenburg,", "2007);", "software", "used", "to", "prepare", "material", "for", "publi-", "cation:", "WinGX", "(Farrugia,", "1999).", "Routine", "data", "collection", "was", "performed", "by", "the", "XRD", "service", "department", "(Dr", "K.", "Harms,", "G.", "Geiseler", "and", "R.", "Riedel)", "of", "the", "Chemistry", "Department,", "Philipps-University,", "and", "is", "gratefully", "acknowledged.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "HP2020).", "References", "Altomare,", "A.,", "Cascarano,", "G.,", "Giacovazzo,", "C.", "&", "Guagliardi,", "A.", "(1993).", "J.", "Appl.", "Cryst.", "26,", "343–350.", "Batten,", "S.", "R.,", "Harris,", "A.", "R.,", "Jensen,", "P.,", "Murray,", "K.", "S.", "&", "Ziebell,", "A.", "(2000).", "J.", "Chem.", "Soc.", "Dalton", "Trans.", "pp.", "3829–3835.", "Bessler,", "K.", "E.,", "Romualdo,", "L.", "L.,", "Deflon,", "V.", "M.", "&", "Hagenbach,", "A.", "(2000).", "Z.", "Anorg.", "Allg.", "Chem.", "626,", "1942–1945.", "Blessing,", "R.", "H.", "(1995).", "Acta", "Cryst.", "A51,", "33–38.", "Brandenburg,", "K.", "(2007).", "DIAMOND.", "Crystal", "Impact", "GbR,", "Bonn,", "Germany.", "Farrugia,", "L.", "J.", "(1999).", "J.", "Appl.", "Cryst.", "32,", "837–838.", "MacFarlane,", "D.", "R.,", "Golding,", "J.,", "Forsyth,", "M.", "&", "Deacon,", "G.", "B.", "(2001).", "Chem.", "Commun.", "pp.", "1430–1431.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Stoe", "&", "Cie", "(2001).", "X-AREA", "and", "X-RED.", "Stoe", "&", "Cie,", "Darmstadt,", "Germany.", "Stricker,", "M.,", "Linder,", "T.,", "Oelkers,", "B.", "&", "Sundermeyer,", "J.", "(2010).", "Green", "Chem.", "12,", "1589–1598.", "m1784", "Oelkers", "et", "al.", "doi:10.1107/S1600536811047052", "Acta", "Cryst.", "(2011).", "E67,", "m1784" ]

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[ "Fig.", "1", "supplementary", "materials", "sup-5" ]

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