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allenai

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[ "supplementary", "materials", "C1—C2—H2A", "C3—C2—H2A", "C4—C3—C2", "C4—C3—H3A", "C2—C3—H3A", "C4—S1X—C1X", "C2X—C1X—S1X", "C2X—C1X—H1XA", "S1X—C1X—H1XA", "C1X—C2X—C3X", "C1X—C2X—H2XA", "C3X—C2X—H2XA", "C4—C3X—C2X", "C4—C3X—H3XA", "C2X—C3X—H3XA", "O1—C5—C6", "O1—C5—C4", "C6—C5—C4", "C7—C6—C5", "C7—C6—H6A", "C5—C6—H6A", "C6—C7—C8", "C3X—C4—S1—C1", "C3—C4—S1—C1", "C5—C4—S1—C1", "S1X—C4—S1—C1", "C4—S1—C1—C2", "S1—C1—C2—C3", "C3X—C4—C3—C2", "C5—C4—C3—C2", "S1X—C4—C3—C2", "S1—C4—C3—C2", "C1—C2—C3—C4", "C3X—C4—S1X—C1X", "C3—C4—S1X—C1X", "C5—C4—S1X—C1X", "S1—C4—S1X—C1X", "C4—S1X—C1X—C2X", "S1X—C1X—C2X—C3X", "C3—C4—C3X—C2X", "C5—C4—C3X—C2X", "S1X—C4—C3X—C2X", "S1—C4—C3X—C2X", "C1X—C2X—C3X—C4", "C3X—C4—C5—O1", "C3—C4—C5—O1", "S1X—C4—C5—O1", "S1—C4—C5—O1", "C3X—C4—C5—C6", "sup-6", "124.7", "124.7", "114.6", "(3)", "122.7", "122.7", "89.5", "(9)", "113.4", "(16)", "123.3", "123.3", "107.3", "(17)", "126.4", "126.4", "114.5", "(14)", "122.8", "122.8", "122.66", "(14)", "120.09", "(13)", "117.25", "(13)", "121.74", "(14)", "119.1", "119.1", "126.89", "(14)", "13", "(12)", "−0.2", "(4)", "178.97", "(18)", "−4.5", "(5)", "1.5", "(4)", "−2.2", "(7)", "−2.2", "(11)", "179.9", "(4)", "155", "(5)", "−1.0", "(7)", "2.1", "(8)", "6(2)", "−18", "(4)", "−175.8", "(18)", "7.8", "(19)", "−11", "(4)", "12", "(5)", "4(2)", "−178.2", "(17)", "0(3)", "−163", "(13)", "−8(4)", "6.3", "(12)", "−176.2", "(4)", "−171.6", "(5)", "4.8", "(2)", "−173.8", "(12)", "C13—C12—C11", "C12—C13—C8", "C12—C13—H13A", "C8—C13—H13A", "O2—C14—H14A", "O2—C14—H14B", "H14A—C14—H14B", "O2—C14—H14C", "H14A—C14—H14C", "H14B—C14—H14C", "O3—C15—H15A", "O3—C15—H15B", "H15A—C15—H15B", "O3—C15—H15C", "H15A—C15—H15C", "H15B—C15—H15C", "O4—C16—H16B", "O4—C16—H16C", "H16B—C16—H16C", "O4—C16—H16D", "H16B—C16—H16D", "H16C—C16—H16D", "S1—C4—C5—C6", "O1—C5—C6—C7", "C4—C5—C6—C7", "C5—C6—C7—C8", "C6—C7—C8—C9", "C6—C7—C8—C13", "C16—O4—C9—C10", "C16—O4—C9—C8", "C13—C8—C9—O4", "C7—C8—C9—O4", "C13—C8—C9—C10", "C7—C8—C9—C10", "O4—C9—C10—C11", "C8—C9—C10—C11", "C15—O3—C11—C10", "C15—O3—C11—C12", "C9—C10—C11—O3", "C9—C10—C11—C12", "C14—O2—C12—C13", "C14—O2—C12—C11", "O3—C11—C12—O2", "C10—C11—C12—O2", "O3—C11—C12—C13", "C10—C11—C12—C13", "O2—C12—C13—C8", "C11—C12—C13—C8", "C9—C8—C13—C12", "119.36", "(13)", "121.70", "(14)", "119.2", "119.2", "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", "−175.26", "(11)", "−7.0", "(3)", "173.08", "(15)", "179.63", "(14)", "173.21", "(16)", "−8.9", "(3)", "−16.9", "(2)", "164.24", "(14)", "−178.88", "(13)", "−0.9", "(2)", "2.2", "(2)", "−179.86", "(14)", "−179.94", "(14)", "−1.1", "(2)", "3.3", "(2)", "−175.89", "(14)", "179.05", "(13)", "−1.8", "(2)", "−2.3", "(2)", "175.38", "(14)", "4.99", "(19)", "−174.20", "(13)", "−177.23", "(13)", "3.6", "(2)", "175.11", "(14)", "−2.4", "(2)", "−0.4", "(2)" ]

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[ "supplementary", "materials", "Acta", "Cryst.", "(2008).", "E64,", "o75", "[", "doi:10.1107/S1600536807061739", "]", "Dibenzyl", "3,3',4,4'-tetramethyl-5,5'-(ethynediyl)bis(pyrrole-2-carboxylate)", "H.", "K.", "Tanui,", "F.", "R.", "Fronczek", "and", "M.", "G.", "H.", "Vicente", "Comment", "Di(5-benzyloxycarbornyl-3,4-dimethyl-2-pyrrolyl)-ethyne", "(I)", "is", "an", "important", "intermediate", "in", "the", "synthesis", "of", "porphyrin", "analogues", "containing", "a", "two-carbon", "interpyrrolic", "bridge", "as", "in", "corrphycenes", "(Vogel,", "1996).", "Compound", "(I)", "is", "also", "an", "interest-", "ing", "intermediate", "in", "the", "synthesis", "of", "dipyrroles", "with", "a", "two", "carbon", "bridge,", "which", "have", "shown", "selective", "binding", "properties", "to", "fluoride", "and", "other", "ions", "(Black", "et", "al.", "1999).", "The", "title", "compound", "was", "prepared", "via", "an", "improved", "Sonogashira", "coupling", "reaction", "(Chinchilla", "&", "Najera,", "2007),", "that", "took", "place", "between", "benzyl", "5-iodo-3,4-dimethyl-1H-pyrrole-2-carboxylate", "and", "trimethyl-", "silanyl-ethyne,", "in", "the", "presence", "of", "palladium(0)", "and", "copper(I)", "catalysts", "at", "room", "temperature.", "The", "exact", "experimental", "details", "are", "described", "below.", "The", "structure", "of", "the", "title", "compound", "(I),", "which", "lies", "on", "a", "crystallographic", "twofold", "axis,", "is", "shown", "in", "Fig", "1.", "The", "triple-bond", "distance", "is", "1.2088", "(17)", "Å,", "and", "the", "alkyne", "bridge", "is", "not", "quite", "linear,", "with", "C4—C5—C5i", "angle", "175.61", "(10)°", "(i", "=", "1", "−", "x,", "y,", "1/2", "−", "z).", "The", "pyrrole", "ring", "is", "essentially", "planar,", "its", "five", "atoms", "having", "a", "mean", "deviation", "0.003", "Å", "from", "their", "best", "plane,", "with", "maximum", "0.0051", "(7)", "Å", "for", "C4.", "The", "two", "pyrrole", "rings", "are", "not", "coplanar,", "but", "form", "a", "dihedral", "angle", "of", "40.49", "(4)°.", "The", "ester", "COO", "group", "lies", "nearly", "in", "the", "pyrrole", "plane,", "with", "N1—C1—C6—O2", "torsion", "angle", "3.67", "(13)°.", "The", "pyrrole", "N—H", "group", "and", "adjacent", "ester", "carbonyl", "form", "intermolecular", "hydrogen", "bonded", "rings", "about", "inversion", "cen-", "ters,", "having", "graph-set", "notation", "(Etter,", "1990)", "R22(10).", "Thus,", "each", "molecule", "engages", "in", "four", "hydrogen", "bonds", "with", "two", "other", "molecules,", "forming", "chains", "in", "the", "[0", "0", "1]", "direction,", "as", "shown", "in", "Fig.", "2.", "Experimental", "To", "a", "100", "ml", "round", "bottom", "flask", "was", "added", "benzyl", "5-iodo-3,4-dimethyl-1H-pyrrole-2-carboxylate", "(2.93", "g,", "10", "mmol)", "fol-", "lowed", "by", "Pd(PPh)2Cl2", "(0.7019", "g,", "0.1", "mmol)", "and", "CuI", "(0.191", "g", "0.1", "mmol).", "The", "flask", "was", "sealed", "and", "placed", "in", "a", "dry", "ice", "bath", "under", "N2.", "Trimethylsilanyl-ethyne", "(0.6996", "ml,", "5", "mmol),", "DBU", "(8.973", "ml,", "60", "mmol)", "and", "water", "(0.072", "ml,", "40", "molar", "equiv.)", "were", "dissolved", "in", "30", "ml", "of", "acetonitrile", "and", "added", "to", "the", "reaction", "flask.", "After", "the", "mixture", "froze", "in", "the", "dry", "ice", "bath,", "the", "flask", "was", "evacuated", "and", "N2", "gas", "added.", "The", "resulting", "reaction", "mixture", "was", "allowed", "to", "warm", "slowly", "to", "room", "temperature", "and", "was", "stirred", "until", "complete", "disappearance", "of", "the", "starting", "material", "by", "TLC.", "The", "reaction", "mixture", "was", "worked", "up", "by", "adding", "ethyl", "acetate", "(150", "ml),", "and", "washing", "the", "organic", "layer", "three", "times", "with", "saline.", "The", "organic", "phase", "was", "dried", "over", "anhydrous", "sodium", "bicarbonate", "and", "concentrated", "under", "reduced", "pressure.", "The", "crude", "mixture", "was", "purified", "by", "flash", "column", "chromatography", "using", "hexane/ethyl", "acetate", "(5:1)", "for", "elution.", "The", "dipyrrole-ethyne", "(I)", "was", "obtained", "(0.755", "g)", "in", "54%", "yield", "and", "recrystallized", "from", "dichloromethane", "to", "afford", "colorless", "crystals.", "Spectroscopic", "analysis,", "1H", "NMR", "(250", "MHz,", "CDCl3,", "293", "K,", "δ):", "11.99", "(2H,", "s,", "NH),", "7.47–7.32", "(10H,", "m,", "Ar—H),", "5.29", "(4H,", "s,", "CH2),", "2.2", "(6H,", "s,", "CH3),", "2.0", "(6H,", "s,", "CH3).", "MS", "(EI)", "m/z:", "480.129", "(M+).", "sup-1" ]

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

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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "Dibenzyl", "3,30,4,40-tetramethyl-5,50-", "(ethynediyl)bis(pyrrole-2-carboxylate)", "Hillary", "K.", "Tanui,", "Frank", "R.", "Fronczek*", "and", "M.", "Grac¸a", "H.", "Vicente", "Department", "of", "Chemistry,", "Louisiana", "State", "University,", "Baton", "Rouge,", "LA", "70803-1804,", "USA", "Correspondence", "e-mail:", "ffroncz@lsu.edu", "Received", "20", "November", "2007;", "accepted", "21", "November", "2007", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "90", "K;", "mean", "(C–C)", "=", "0.001", "A˚;", "R", "factor", "=", "0.044;", "wR", "factor", "=", "0.124;", "data-to-parameter", "ratio", "=", "28.3.", "The", "title", "molecule,", "C30H28N2O4,", "has", "crystallographic", "twofold", "rotation", "symmetry,", "with", "the", "pyrrole", "planes", "forming", "a", "dihedral", "angle", "of", "40.49", "(4)", ".", "The", "pyrrole", "N—H", "donor", "and", "adjacent", "ester", "carbonyl", "acceptor", "form", "R22(10)", "hydrogen-bonded", "rings", "about", "inversion", "centers,", "leading", "to", "chains", "of", "hydrogen-bonded", "molecules", "along", "[001].", "Related", "literature", "For", "background", "literature,", "see:", "Chinchilla", "&", "Najera", "(2007);", "Black", "et", "al.", "(1999);", "Etter", "(1990);", "Vogel", "(1996).", "For", "related", "structures,", "see:", "Xie", "et", "al.", "(1996);", "Weghorn", "et", "al.", "(1995).", "Experimental", "Crystal", "data", "C30H28N2O4", "Mr", "=", "480.54", "Monoclinic,", "C2=c", "a", "=", "19.340", "(2)", "A˚", "b", "=", "9.8955", "(10)", "A˚", "c", "=", "13.8495", "(15)", "A˚", "=", "110.217", "(6)", "V", "=", "2487.2", "(5)", "A˚3", "Z", "=", "4", "Mo", "K", "radiation", "=", "0.09", "mm", "1", "T", "=", "90", "K", "0.30", "0.22", "0.15", "mm", "Data", "collection", "Nonius", "KappaCCD", "diffractometer", "with", "Oxford", "Cryostream", "Absorption", "correction:", "none", "28071", "measured", "reflections", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.044", "wR(F", "2)", "=", "0.124", "S", "=", "1.03", "4748", "reflections", "168", "parameters", "Table", "1", "Hydrogen-bond", "geometry", "(A˚", ",", ").", "organic", "compounds", "4748", "independent", "reflections", "3948", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.022", "H", "atoms", "treated", "by", "a", "mixture", "of", "independent", "and", "constrained", "refinement", "max", "=", "0.46", "e", "A˚", "3", "min", "=", "0.39", "e", "A˚", "3", "D—H", "A", "N1—H1N", "O2i", "D—H", "0.875", "(14)", "H", "A", "1.987", "(14)", "D", "A", "2.8565", "(10)", "D—H", "A", "172.1", "(12)", "Symmetry", "code:", "(i)", "x", "þ", "1;", "y;", "z", "þ", "1.", "Data", "collection:", "COLLECT", "(Nonius,", "2000);", "cell", "refinement:", "DENZO", "and", "SCALEPACK", "(Otwinowski", "&", "Minor,", "1997);", "data", "reduction:", "DENZO", "and", "SCALEPACK;", "program(s)", "used", "to", "solve", "structure:", "SIR97", "(Altomare", "et", "al.,", "1999);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "1997);", "molecular", "graphics:", "ORTEP-3", "(Farrugia,", "1997);", "software", "used", "to", "prepare", "material", "for", "publication:", "SHELXL97.", "The", "purchase", "of", "the", "diffractometer", "was", "made", "possible", "by", "grant", "No.", "LEQSF(1999–2000)-ENH-TR-13,", "administered", "by", "the", "Louisiana", "Board", "of", "Regents.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "DN2299).", "References", "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.", "Black,", "C.", "B.,", "Andrioletti,", "B.,", "Try,", "A.", "C.,", "Ruiperez,", "C.", "&", "Sessler,", "J.", "L.", "(1999).", "J.", "Am.", "Chem.", "Soc.", "121,", "10438–10439.", "Chinchilla,", "R.", "&", "Najera,", "C.", "(2007).", "Chem.", "Rev.", "107,", "874–922.", "Etter,", "M.", "C.", "(1990).", "Acc.", "Chem.", "Rev.", "23,", "120–126.", "Farrugia,", "L.", "J.", "(1997).", "J.", "Appl.", "Cryst.", "30,", "565.", "Nonius", "(2000).", "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.", "Sheldrick,", "G.", "M.", "(1997).", "SHELXL97.", "University", "of", "Go¨", "ttingen,", "Germany.", "Vogel,", "E.", "(1996).", "Pure", "Appl.", "Chem.", "68,", "1355–1360.", "Weghorn,", "S.", "J.,", "Lynch,", "V.", "&", "Sessler,", "J.", "L.", "(1995).", "Tetrahedron", "Lett.", "36,", "4713–", "4716.", "Xie,", "H.,", "Lee,", "D.", "A.,", "Wallace,", "D.", "M.,", "Senge,", "O.", "M.", "&", "Smith,", "K.", "M.", "(1996).", "J.", "Org.", "Chem.", "61,", "8508–8517.", "Acta", "Cryst.", "(2008).", "E64,", "o75", "doi:10.1107/S1600536807061739", "#", "2008", "International", "Union", "of", "Crystallography", "o75" ]

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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "(Methanolato-jO)[N0-(3-methoxy-2-", "oxidobenzylidene-jO2)-4-nitrobenzo-", "hydrazidato-j2N0,O]oxidovanadium(V)", "Chen-Yi", "Wang,*", "Hai-Yu", "Tu,", "Pei-Fei", "Zhu", "and", "Su-Jun", "Sheng", "Department", "of", "Chemistry,", "Huzhou", "University,", "Huzhou", "313000,", "People’s", "Republic", "of", "China", "Correspondence", "e-mail:", "chenyi_wang@163.com", "Received", "28", "September", "2011;", "accepted", "29", "September", "2011", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "298", "K;", "mean", "(C–C)", "=", "0.005", "A˚;", "R", "factor", "=", "0.051;", "wR", "factor", "=", "0.115;", "data-to-parameter", "ratio", "=", "14.4.", "The", "title", "oxidovanadium(V)", "complex,", "[V(C15H11N3O5)-", "(CH3O)O],", "was", "obtained", "by", "the", "reaction", "of", "2-hydroxy-3-", "methoxybenzaldehyde,", "4-nitrobenzohydrazide", "and", "vanadyl", "sulfate", "in", "methanol.", "The", "VV", "atom", "is", "five-coordinated", "by", "the", "two", "O", "and", "one", "N", "donor", "atoms", "of", "the", "Schiff", "base", "ligand,", "one", "methanolate", "O", "atom", "and", "one", "oxido", "O", "atom,", "forming", "a", "distorted", "square-pyramidal", "geometry.", "Related", "literature", "For", "Schiff", "base", "complexes,", "see:", "Wang", "(2009);", "Wang", "&", "Ye", "(2011).", "For", "similar", "oxidovanadium", "complexes,", "see:", "Deng", "et", "al.", "(2005);", "Gao", "et", "al.", "(2005);", "Huo", "et", "al.", "(2004).", "Experimental", "Crystal", "data", "[V(C15H11N3O5)(CH3O)O]", "Mr", "=", "411.24", "Triclinic,", "P1", "a", "=", "6.410", "(3)", "A˚", "b", "=", "10.253", "(3)", "A˚", "c", "=", "13.490", "(3)", "A˚", "metal-organic", "compounds", "Mo", "K", "radiation", "=", "0.64", "mm", "1", "T", "=", "298", "K", "0.20", "0.20", "0.20", "mm", "6739", "measured", "reflections", "3538", "independent", "reflections", "2686", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.029", "246", "parameters", "H-atom", "parameters", "constrained", "max", "=", "0.47", "e", "A˚", "3", "min", "=", "0.37", "e", "A˚", "3", "=", "71.111", "(2)", "=", "87.998", "(2)", "=", "86.473", "(2)", "V", "=", "837.2", "(5)", "A˚", "3", "Z", "=", "2", "Data", "collection", "Bruker", "SMART", "CCD", "area-detector", "diffractometer", "Absorption", "correction:", "multi-scan", "(SADABS;", "Sheldrick,", "1996)", "Tmin", "=", "0.883,", "Tmax", "=", "0.883", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.051", "wR(F", "2)", "=", "0.115", "S", "=", "1.15", "3538", "reflections", "Table", "1", "Selected", "bond", "lengths", "(A˚", ").", "V1—O6", "V1—O7", "V1—O1", "1.566", "(2)", "1.743", "(2)", "1.816", "(2)", "V1—O3", "V1—N1", "1.922", "(2)", "2.095", "(3)", "Data", "collection:", "SMART", "(Bruker,", "1998);", "cell", "refinement:", "SAINT", "(Bruker,", "1998);", "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:", "SHELXTL.", "This", "work", "was", "supported", "financially", "by", "the", "Natural", "Science", "Foundation", "of", "China", "(No.", "31071856),", "the", "Applied", "Research", "Project", "on", "Nonprofit", "Technology", "of", "Zhejiang", "Province", "(No.", "2010", "C32060),", "the", "Zhejiang", "Provincial", "Natural", "Science", "Foundation", "of", "China", "(No.", "Y407318),", "and", "the", "Technological", "Innovation", "Project", "(sinfonietta", "talent", "plan)", "of", "college", "students", "in", "Zhejiang", "Province", "(Nos.", "2010R42525", "and", "2011R425027).", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "QM2033).", "References", "Bruker", "(1998).", "SMART", "and", "SAINT.", "Bruker", "AXS", "Inc.,", "Madison,", "Wisconsin,", "USA.", "Deng,", "Z.-P.,", "Gao,", "S.,", "Huo,", "L.-H.", "&", "Zhao,", "H.", "(2005).", "Acta", "Cryst.", "E61,", "m2214–", "m2216.", "Gao,", "S.,", "Huo,", "L.-H.,", "Deng,", "Z.-P.", "&", "Zhao,", "H.", "(2005).", "Acta", "Cryst.", "E61,", "m978–", "m980.", "Huo,", "L.-H.,", "Gao,", "S.,", "Liu,", "J.-W.,", "Zhao,", "H.", "&", "Ng,", "S.", "W.", "(2004).", "Acta", "Cryst.", "E60,", "m606–m608.", "Sheldrick,", "G.", "M.", "(1996).", "SADABS.", "University", "of", "Go¨", "ttingen,", "Germany.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Wang,", "C.-Y.", "(2009).", "J.", "Coord.", "Chem.", "62,", "2860–2868.", "Wang,", "C.", "Y.", "&", "Ye,", "J.", "Y.", "(2011).", "Russ.", "J.", "Coord.", "Chem.", "37,", "235–241.", "Acta", "Cryst.", "(2011).", "E67,", "m1495", "doi:10.1107/S1600536811040207", "Wang", "et", "al.", "m1495" ]

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[ "Fig.", "2", "supplementary", "materials", "sup-7" ]

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[ "supplementary", "materials", "Acta", "Cryst.", "(2009).", "E65,", "m447", "[", "doi:10.1107/S1600536809010447", "]", "catena-Poly[[bis(4-methylbenzenethiolato)cadium(II)]-", "-1,3-di-4-pyridylpropane]", "Y.", "Zhang,", "Y.", "Zhou", "and", "L.", "Han", "Comment", "The", "search", "for", "new", "crystalline", "coordination", "polymers", "is", "fueled", "by", "the", "use", "of", "such", "materials", "in", "catalysis,", "separations,", "mag-", "netism,", "and", "optoelectronics", "(James,", "2003).", "Recently,", "interest", "has", "been", "devoted", "to", "the", "entanglement", "of", "1D", "coordination", "polymers", "resulting", "in", "the", "architectures", "of", "an", "overall", "higher", "dimensionality", "(Wang", "et", "al.,", "2005;", "Cheng", "et", "al.,", "2007).", "The", "organic", "ligand,", "1,3-bis(4-pyridyl)propane", "(bpp),", "is", "a", "long", "and", "flexible", "multi-functional", "linker,", "which", "can", "adopt", "different", "conformations", "with", "respect", "to", "the", "relative", "orientations", "of", "the", "CH2", "groups", "(Han", "et", "al.,", "2007;", "Carlucci", "et", "al.,", "2002).", "We", "have", "reported", "a", "2-D", "interwoven", "network", "entangled", "from", "zigzag", "chains", "using", "the", "bpp", "ligand", "as", "building", "unit", "(Han", "&", "Zhou,", "2008).", "In", "an", "attempt", "to", "synthesize", "further", "interwoven", "networks", "we", "have", "synthesized", "the", "one-dimensional", "polymer", "formed", "from", "Cd(SC6H4Me-4)2", "and", "bpp", "and", "its", "crystal", "structure", "is", "reported", "herein.", "The", "title", "compound,", "[Cd(SC6H4Me-4)2(bpp)]n,", "is", "a", "one-dimensional", "chain", "structure", "and", "the", "asymmetric", "unit", "is", "shown", "in", "Fig.", "1.", "The", "unique", "CdII", "ion", "is", "coordinated", "by", "two", "S", "atoms", "and", "two", "N", "atoms", "adopting", "a", "slightly", "distorted", "tetrahedral", "coordination", "geometry.", "In", "the", "chain", "structure,", "there", "are", "weak", "π···π", "stacking", "interactions", "between", "two", "symmetry", "related", "benzene", "rings", "of", "the", "4-methylbenzenethiolate", "groups,", "within", "the", "same", "chain.", "The", "centroid-to-centroid", "distance", "(Cg···Cgi)", "is", "3.825", "(7)", "Å", "(symmetry", "code:", "(i)", "-x,", "y,", "-z+1/2).", "The", "dihedral", "angle", "between", "two", "benzene", "rings", "is", "3.2", "(7)°", "(Fig.", "2).", "Figure", "3", "shows", "part", "of", "the", "crystal", "structure", "of", "the", "title", "compound", "illustrating", "two", "interdigitated", "1-D", "chains.", "Experimental", "Refinement", "Cd(SC6H4Me-4)2", "was", "synthesized", "according", "to", "the", "literature", "(Dance", "et", "al.,", "1987).", "A", "mixture", "of", "Cd(SC6H4Me-4)2", "(99.5", "mg)", "and", "1,3-bis(4-pyridyl)propane", "(50.1", "mg)", "in", "DMF", "(6.0", "g)", "solution", "was", "stirred", "for", "30", "min.", "The", "solution", "was", "allowed", "to", "stand", "at", "room", "temperature", "for", "5", "days.", "Colorless", "block", "crystals", "of", "the", "title", "complex", "were", "obtained", "and", "collected", "by", "filtration", "with", "a", "30%", "yield.", "The", "unique", "H", "atom", "on", "C1", "was", "located", "in", "a", "difference", "map", "and", "refined", "freely.", "Other", "H", "atoms", "were", "positioned", "geometrically", "and", "allowed", "to", "ride", "on", "their", "respective", "parent", "atoms,", "with", "C—H", "=", "0.93", "Å", "and", "Uiso(H)", "=", "1.2Ueq(C)", "for", "phenyl", "and", "pyridyl", "H", "atoms,", "C—H", "=", "0.96", "Å", "and", "Uiso(H)", "=1.5Ueq(C)", "for", "methyl,", "C—H", "=", "0.97", "Å", "and", "Uiso(H)", "=", "1.2Ueq(C)", "for", "methylene.", "sup-1" ]

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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "catena-Poly[[bis(4-methylbenzene-", "thiolato)cadium(II)]-l-1,3-di-4-pyridyl-", "propane]", "Yan", "Zhang,", "Yan", "Zhou", "and", "Lei", "Han*", "Faculty", "of", "Materials", "Science", "&", "Chemical", "Engineering,", "Ningbo", "University,", "Ningbo,", "Zhejiang", "315211,", "People’s", "Republic", "of", "China", "Correspondence", "e-mail:", "hanlei@nbu.edu.cn", "Received", "18", "March", "2009;", "accepted", "21", "March", "2009", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "298", "K;", "mean", "(C–C)", "=", "0.004", "A˚;", "R", "factor", "=", "0.036;", "wR", "factor", "=", "0.090;", "data-to-parameter", "ratio", "=", "19.7.", "In", "the", "title", "compound,", "[Cd(C7H7S)2(C13H14N2)]n,", "the", "unique", "CdII", "ion,", "located", "on", "a", "twofold", "rotation", "axis,", "is", "coordinated", "by", "two", "S", "atoms", "and", "two", "N", "atoms", "in", "a", "slightly", "distorted", "tetrahedral", "environment.", "Symmetry-related", "CdII", "ions", "are", "linked", "via", "bridging", "1,3-di-4-pyridylpropane", "ligands,", "forming", "a", "zig-zag", "chain-structure", "parallel", "to", "[001].", "In", "the", "crystal", "structure,", "there", "are", "weak", "intrachain", "–", "stacking", "interactions", "between", "benzene", "rings,", "with", "a", "centroid–centroid", "distance", "of", "3.825", "(7)", "A˚", ",", "and", "pairs", "of", "chains", "are", "interdigitated", "with", "respect", "to", "the", "4-methylbenzenethiolate", "groups.", "Related", "literature", "For", "background", "information", "on", "coordination", "polymers,", "see:", "James", "(2003);", "Wang", "et", "al.", "(2005);", "Cheng", "et", "al.", "(2007);", "Han", "&", "Zhou", "(2008).", "For", "information", "on", "the", "1,3-bis(4-pyridyl)-", "propane", "ligand,", "see:", "Han", "et", "al.", "(2007);", "Carlucci", "et", "al.", "(2002).", "For", "the", "synthetic", "procedure,", "see:", "Dance", "et", "al.", "(1987).", "Experimental", "Crystal", "data", "[Cd(C7H7S)2(C13H14N2)]", "Mr", "=", "557.03", "Monoclinic,", "C2=c", "a", "=", "11.922", "(2)", "A˚", "metal-organic", "compounds", "b", "=", "16.792", "(3)", "A˚", "c", "=", "12.862", "(3)", "A˚", "=", "91.06", "(3)", "V", "=", "2574.5", "(9)", "A˚", "3", "Z", "=", "4", "Data", "collection", "Rigaku", "R-AXIS", "RAPID", "diffractometer", "Absorption", "correction:", "multi-scan", "(ABSCOR;", "Higashi,", "1995)", "Tmin", "=", "0.655,", "Tmax", "=", "0.837", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.036", "wR(F", "2)", "=", "0.090", "S", "=", "1.09", "2948", "reflections", "150", "parameters", "Mo", "K", "radiation", "=", "1.03", "mm", "1", "T", "=", "298", "K", "0.45", "0.25", "0.18", "mm", "12609", "measured", "reflections", "2948", "independent", "reflections", "2587", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.046", "H", "atoms", "treated", "by", "a", "mixture", "of", "independent", "and", "constrained", "refinement", "max", "=", "0.53", "e", "A˚", "3", "min", "=", "0.90", "e", "A˚", "3", "2.4370", "(9)", "108.77", "(7)", "131.71", "(4)", "Table", "1", "Selected", "geometric", "parameters", "(", "A˚,", ").", "Cd1—N1", "N1—Cd1—N1i", "N1—Cd1—S1", "Symmetry", "code:", "(i)", "x;", "y;", "z", "þ", "12.", "2.320", "(2)", "Cd1—S1", "93.43", "(11)", "103.83", "(7)", "N1i—Cd1—S1", "S1—Cd1—S1i", "Data", "collection:", "RAPID-AUTO", "(Rigaku,", "1998);", "cell", "refinement:", "RAPID-AUTO;", "data", "reduction:", "CrystalStructure", "(Rigaku/MSC,", "2004);", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "SHELXTL", "(Sheldrick,", "2008)", "and", "PLATON", "(Spek,", "2009);", "software", "used", "to", "prepare", "material", "for", "publication:", "SHELXL97.", "This", "work", "was", "supported", "by", "the", "Natural", "Science", "Founda-", "tion", "of", "Zhejiang", "Province", "(Y4080435),", "the", "Natural", "Science", "Foundation", "of", "Ningbo", "Municipal", "(2007A610024)", "and", "the", "K.C.", "Wong", "Magna", "Fund", "of", "Ningbo", "University.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "LH2791).", "References", "Carlucci,", "L.,", "Ciani,", "G.,", "Proserpio,", "D.-M.", "&", "Rizzato,", "S.", "(2002).", "Coord.", "Chem.", "Rev.", "4,", "121–129.", "Cheng,", "A.-L.,", "Liu,", "N.,", "Yue,", "Y.-F.,", "Jiang,", "Y.-W.,", "Gao,", "E.-Q.,", "Yan,", "C.-H.", "&", "He,", "M.-Y.", "(2007).", "Chem.", "Commun.", "pp.", "407–409.", "Dance,", "I.", "G.,", "Garbutt,", "R.", "G.,", "Craig,", "D.", "C.", "&", "Scudder,", "M.", "L.", "(1987).", "Inorg.", "Chem.", "26,", "4057–4064.", "Han,", "L.,", "Valle,", "H.", "&", "Bu,", "X.-H.", "(2007).", "Inorg.", "Chem.", "46,", "1511–1513.", "Han,", "L.", "&", "Zhou,", "Y.", "(2008).", "Inorg.", "Chem.", "Commun.", "11,", "385–387.", "Higashi,", "T.", "(1995).", "ABSCOR.", "Rigaku", "Corporation,", "Tokyo,", "Japan.", "James,", "S.", "L.", "(2003).", "Chem.", "Soc.", "Rev.", "32,", "276–288.", "Rigaku", "(1998).", "RAPID-AUTO.", "Rigaku", "Corporation,", "Tokyo,", "Japan.", "Rigaku/MSC", "(2004).", "CrystalStructure.", "Rigaku/MSC,", "The", "Woodlands,", "Texas,", "USA.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Spek,", "A.", "L.", "(2009).", "Acta", "Cryst.", "D65,", "148–155.", "Wang,", "X.-L.,", "Qin,", "C.,", "Wang,", "E.-B.,", "Li,", "Y.-G.,", "Su,", "Z.-M.,", "Xu,", "L.", "&", "Carlucci,", "L.", "(2005).", "Angew.", "Chem.", "Int.", "Ed.", "44,", "5824–5827.", "Acta", "Cryst.", "(2009).", "E65,", "m447", "doi:10.1107/S1600536809010447", "Zhang", "et", "al.", "m447" ]

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"data", "reduction:", "SAINT;", "program(s)", "used", "to", "solve", "structure:", "SHELXTL", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXTL;", "molecular", "graphics:", "SHELXTL;", "software", "used", "to", "prepare", "material", "for", "publication:", "SHELXTL", "and", "local", "programs.", "HPS", "is", "grateful", "to", "the", "University", "of", "Mysore", "for", "research", "facilities.", "HSY", "thanks", "R.", "L.", "Fine", "Chemicals,", "Bangalore,", "India,", "for", "the", "gift", "of", "a", "sample", "of", "the", "title", "compound.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "NC2267).", "References", "Bruker", "(2002).", "SMART", "and", "SAINT.", "Bruker", "AXS", "Inc.,", "Madison,", "Wisconsin,", "USA.", "Ferguson,", "G.,", "Carroll,", "C.", "D.,", "Glidewell,", "C.,", "Zakaria,", "C.", "M.", "&", "Lough,", "A.", "J.", "(1995).", "Acta", "Cryst.", "B51,", "367–377.", "Narayanan,", "P.,", "Sethusankar,", "K.,", "Ramachandiran,", "K.", "&", "Perumal,", "P.", "T.", "(2011).", "Acta", "Cryst.", "E67,", "o2658.", "Ohkuma,", "T.,", "Koizumi,", "M.,", "Ikehira,", "H.,", "Yokozawa,", "T.", "&", "Noyori,", "R.", "(2000).", "Org.", "Lett.", "2,", "659–662.", "Shah,", "K.,", "Raza", "Shah,", "M.", "&", "Ng,", "S.", "W.", "(2011).", "Acta", "Cryst.", "E67,", "o568.", "Sheldrick,", "G.", "M.", "(2004).", "SADABS.", "University", "of", "Go¨", "ttingen,", "Germany.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Siddaraju,", "B.", "P.,", "Yathirajan,", "H.", "S.,", "Narayana,", "B.,", "Ng,", "S.", "W.", "&", "Tiekink,", "E.", "R.", "T.", "(2010).", "Acta", "Cryst.", "E66,", "o2136.", "Zhang,", "W.,", "Yao,", "L.", "&", "Tao,", "R.-J.", "(2008).", "Acta", "Cryst.", "E64,", "o307.", "Zhang,", "C.-H.,", "Zhao,", "J.-M.", "&", "Chen,", "B.-G.", "(2011).", "Acta", "Cryst.", "E67,", "o150.", "o874", "Sumathi", "et", "al.", "doi:10.1107/S1600536812007982", "Acta", "Cryst.", "(2012).", "E68,", "o874" ]

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[ "supplementary", "materials", "C22—N2—C21", "C11—N3—C15", "C11—N3—C14", "C15—N3—C14", "C26—N4—C29", "C26—N4—C30", "C29—N4—C30", "C2—C1—C6", "C2—C1—S2", "C6—C1—S2", "C3—C2—C1", "C3—C2—H2", "C1—C2—H2", "C4—C3—C2", "C4—C3—H3", "C2—C3—H3", "C3—C4—C5", "C3—C4—H4", "C5—C4—H4", "C4—C5—C6", "C4—C5—H5", "C6—C5—H5", "C1—C6—C5", "C1—C6—N1", "C5—C6—N1", "N1—C7—C8", "N1—C7—H7", "C8—C7—H7", "C13—C8—C9", "C13—C8—C7", "C9—C8—C7", "C10—C9—C8", "C10—C9—H9", "C8—C9—H9", "C9—C10—C11", "C9—C10—H10", "C11—C10—H10", "N3—C11—C10", "N3—C11—C12", "C10—C11—C12", "C13—C12—C11", "C13—C12—H12", "C11—C12—H12", "C12—C13—C8", "C12—C13—H13", "C8—C13—H13", "N3—C14—H14A", "N3—C14—H14B", "H14A—C14—H14B", "sup-6", "120.7", "(3)", "120.7", "(3)", "120.5", "(3)", "118.3", "(3)", "120.0", "(4)", "121.2", "(4)", "118.6", "(3)", "120.0", "(3)", "122.4", "(3)", "117.6", "(2)", "120.5", "(3)", "119.8", "119.8", "119.8", "(3)", "120.1", "120.1", "119.9", "(3)", "120.0", "120.0", "120.8", "(3)", "119.6", "119.6", "118.8", "(3)", "117.7", "(3)", "123.4", "(3)", "124.3", "(3)", "117.9", "117.9", "116.7", "(3)", "120.7", "(3)", "122.5", "(3)", "121.6", "(3)", "119.2", "119.2", "121.6", "(3)", "119.2", "119.2", "121.7", "(3)", "121.7", "(3)", "116.6", "(3)", "120.9", "(3)", "119.6", "119.6", "122.4", "(3)", "118.8", "118.8", "109.5", "109.5", "109.5", "H15A—C15—H15C", "H15B—C15—H15C", "C17—C16—C21", "C17—C16—S1", "C21—C16—S1", "C18—C17—C16", "C18—C17—H17", "C16—C17—H17", "C19—C18—C17", "C19—C18—H18", "C17—C18—H18", "C18—C19—C20", "C18—C19—H19", "C20—C19—H19", "C19—C20—C21", "C19—C20—H20", "C21—C20—H20", "C20—C21—C16", "C20—C21—N2", "C16—C21—N2", "N2—C22—C23", "N2—C22—H22", "C23—C22—H22", "C28—C23—C24", "C28—C23—C22", "C24—C23—C22", "C25—C24—C23", "C25—C24—H24", "C23—C24—H24", "C24—C25—C26", "C24—C25—H25", "C26—C25—H25", "N4—C26—C27", "N4—C26—C25", "C27—C26—C25", "C28—C27—C26", "C28—C27—H27", "C26—C27—H27", "C27—C28—C23", "C27—C28—H28", "C23—C28—H28", "N4—C29—H29A", "N4—C29—H29B", "H29A—C29—H29B", "N4—C29—H29C", "H29A—C29—H29C", "H29B—C29—H29C", "N4—C30—H30A", "N4—C30—H30B", "109.5", "109.5", "120.2", "(3)", "125.3", "(3)", "114.4", "(3)", "120.1", "(3)", "120.0", "120.0", "120.3", "(4)", "119.9", "119.9", "120.3", "(4)", "119.8", "119.8", "120.8", "(4)", "119.6", "119.6", "118.2", "(3)", "125.8", "(3)", "115.9", "(3)", "123.4", "(3)", "118.3", "118.3", "116.2", "(3)", "121.2", "(3)", "122.6", "(3)", "121.9", "(3)", "119.1", "119.1", "121.6", "(3)", "119.2", "119.2", "121.1", "(4)", "121.8", "(4)", "117.1", "(3)", "119.9", "(4)", "120.1", "120.1", "123.3", "(3)", "118.3", "118.3", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5" ]

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[ "supplementary", "materials", "Acta", "Cryst.", "(2009).", "E65,", "o729", "[", "doi:10.1107/S1600536809005844", "]", "anti-Tricyclo[4.2.1.12,5]deca-3,7-diene-9,10-dione", "M.", "P.", "Gidaly,", "A.", "D.", "Harris,", "M.", "del", "R.", "I.", "Amado-Sierra,", "D.", "S.", "Jones", "and", "M.", "Etzkorn", "Comment", "The", "polycyclic", "title", "compound,", "dione", "4,", "is", "formally", "a", "dimer", "of", "the", "elusive", "cyclopentadienone", "1.", "The", "latter", "compound", "has", "only", "a", "fleeting", "existence", "and", "could", "be", "trapped", "in", "the", "form", "of", "its", "Diels-Alder", "adduct", "3", "(Hafner", "&", "Goliasch,", "1961)", "or", "stabilized", "as", "an", "iron", "pentacarbonyl", "complex", "(Weiss", "et", "al.,", "1960),", "although", "derivatives", "with", "bulky", "substituents", "have", "been", "prepared", "as", "stable", "monomers", "(Dilthey", "&", "Quint,", "1930;", "Garbisch", "&", "Sprecher,", "1966;", "Saito", "&", "Ito,", "2008).", "The", "title", "compound", "4", "is", "accessible", "through", "photoisomerization", "of", "Diels-Alder", "adduct", "3,", "a", "transformation", "that", "has", "been", "thoroughly", "studied", "(Baggiolini", "et", "al.,", "1967;", "Klinsmann", "et", "al.,", "1972)", "since", "dione", "4", "–", "via", "diol", "5", "(Amman", "et", "al.,", "1980;", "Amman", "&", "Ganter,", "1977;", "Amman", "&", "Ganter,", "1981)", "-", "is", "a", "valuable", "precursor", "to", "an", "unusual", "bishomoaromatic", "dication", "(Prakash", "et", "al.,", "1987)", "and", "to", "heterodiamantanes", "and", "other", "oxa-cage", "compounds", "(Amman", "et", "al.,", "1980;", "Amman", "&", "Ganter,", "1977;", "Amman", "&", "Ganter,", "1981).", "We", "have", "recently", "reported", "the", "structure", "of", "diol", "derivative", "5", "(Harris", "et", "al.,", "2008)", "and", "herein", "report", "the", "structure", "of", "the", "parent", "dione", "4.", "Two", "independent", "molecules,", "each", "of", "which", "is", "situated", "on", "a", "center", "of", "symmetry,", "comprise", "the", "unit", "cell.", "Both", "molecules", "are", "in", "nearly", "identical", "\"chair\"", "conformations,", "with", "a", "maximum", "deviation", "between", "corresponding", "bond", "lengths", "of", "0.01", "Å.", "The", "molecular", "packing", "exhibits", "several", "short", "intermolecular", "contacts,", "with", "the", "shortest", "being", "0.15", "Å", "less", "than", "the", "sum", "of", "the", "van", "der", "Waals", "radii.", "Two", "related", "structures", "have", "been", "reported.", "The", "first", "(Eaton", "et", "al.,", "2002)", "has", "a", "chlorine", "atom", "in", "place", "of", "each", "hydrogen", "atom", "of", "the", "title", "compound,", "while", "the", "second", "(Masters", "et", "al.,", "1994)", "lacks", "the", "double", "bonds", "of", "the", "title", "compound", "and", "has", "methyl", "groups", "on", "each", "of", "the", "four", "bridgehead", "carbon", "atoms.", "Experimental", "Refinement", "Figures", "The", "synthesis", "of", "the", "title", "compound,", "4,", "is", "described", "in", "our", "previous", "structure", "report", "(Harris", "et", "al.,", "2008).", "Crystals", "for", "data", "collection", "were", "obtained", "from", "a", "chloroform", "solution.", "H", "atoms", "were", "constrained", "using", "a", "riding", "model.", "The", "olefinic", "C—H", "bond", "lengths", "were", "fixed", "at", "0.93", "Å", "and", "the", "methine", "C—H", "bond", "lengths", "at", "0.98", "Å,", "with", "Uiso(H)", "=", "1.2", "Ueq.", "(C).", "Fig.", "1.", "View", "of", "the", "two", "independent", "molecules", "of", "the", "title", "compound,", "4,", "with", "50%", "probability", "displacement", "ellipsoids.", "[Symmetry", "codes:", "(i)", "-x,", "-y", "+", "1,", "-z", "+", "2;", "(ii)", "-x", "+", "1,", "-y", "+", "2,", "-z", "+", "1]", "sup-1" ]

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

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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "anti-Tricyclo[4.2.1.1", "9,10-dione", "2,5", "]deca-3,7-diene-", "Matthew", "P.", "Gidaly,", "Andria", "D.", "Harris,", "Maria", "del", "Rosario", "I.", "Amado-Sierra,", "Daniel", "S.", "Jones*", "and", "Markus", "Etzkorn*", "Department", "of", "Chemistry,", "The", "University", "of", "North", "Carolina", "at", "Charlotte,", "9201", "University", "City", "Blvd,", "Charlotte,", "NC", "28223,", "USA", "Correspondence", "e-mail:", "djones@uncc.edu,", "metzkorn@uncc.edu", "Received", "31", "December", "2008;", "accepted", "18", "February", "2009", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "295", "K;", "mean", "(C–C)", "=", "0.002", "A˚;", "R", "factor", "=", "0.037;", "wR", "factor", "=", "0.092;", "data-to-parameter", "ratio", "=", "12.1.", "The", "title", "compound,", "C10H8O2,", "is", "a", "precursor", "to", "an", "unusual", "bis-", "homoaromatic", "dication", "and", "to", "heterodiamantanes", "and", "other", "oxa-cage", "compounds.", "Two", "independent", "molecules,", "each", "of", "which", "is", "situated", "on", "a", "center", "of", "symmetry,", "comprise", "the", "unit", "cell.", "Both", "molecules", "are", "in", "nearly", "identical", "chair", "conforma-", "tions.", "Related", "literature", "For", "related", "structures,", "see:", "Eaton", "et", "al.", "(2002);", "Harris", "et", "al.", "(2008);", "Masters", "et", "al.", "(1994).", "For", "the", "synthesis", "and", "related", "details,", "see:", "Hafner", "&", "Goliasch", "(1961);", "Weiss", "et", "al.", "(1960);", "Dilthey", "&", "Quint", "(1930);", "Garbisch", "&", "Sprecher", "(1966);", "Saito", "&", "Ito", "(2008);", "Baggiolini", "et", "al.", "(1967);", "Klinsmann", "et", "al.", "(1972);", "Amman", "et", "al.", "(1980);", "Amman", "&", "Ganter", "(1977,", "1981);", "Prakash", "et", "al.", "(1987);", "Harris", "et", "al.", "(2008).", "Experimental", "Crystal", "data", "C10H8O2", "Mr", "=", "160.16", "Triclinic,", "P1", "a", "=", "6.4458", "(7)", "A˚", "b", "=", "6.6120", "(6)", "A˚", "c", "=", "8.9758", "(6)", "A˚", "=", "81.671", "(8)", "=", "79.176", "(10)", "=", "84.745", "(8)", "V", "=", "370.96", "(6)", "A˚3", "Z", "=", "2", "Cu", "K", "radiation", "=", "0.82", "mm", "1", "T", "=", "295", "K", "Data", "collection", "Enraf–Nonius", "CAD-4", "diffractometer", "Absorption", "correction:", "none", "2624", "measured", "reflections", "1329", "independent", "reflections", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.037", "wR(F", "2)", "=", "0.092", "S", "=", "1.12", "1329", "reflections", "organic", "compounds", "0.3", "0.2", "0.2", "mm", "1179", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.045", "3", "standard", "reflections", "every", "82", "reflections", "intensity", "decay:", "1%", "110", "parameters", "H-atom", "parameters", "constrained", "max", "=", "0.2", "e", "A˚", "3", "min", "=", "0.15", "e", "A˚", "3", "Data", "collection:", "CAD-4", "EXPRESS", "(Enraf–Nonius,", "1994);", "cell", "refinement:", "CAD-4", "EXPRESS;", "data", "reduction:", "XCAD4", "(Harms", "&", "Wocadlo,", "1995);", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "ORTEP-3", "for", "Windows", "(Farrugia,", "1997);", "software", "used", "to", "prepare", "material", "for", "publication:", "WinGX", "(Farrugia,", "1999).", "Acknowledgement", "is", "made", "to", "the", "Donors", "of", "the", "American", "Chemical", "Society", "Petroleum", "Research", "Fund", "for", "partial", "support", "of", "this", "research.", "This", "work", "was", "supported", "in", "part", "by", "funds", "provided", "by", "The", "University", "of", "North", "Carolina", "at", "Charlotte.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "FL2229).", "References", "Amman,", "W.", "&", "Ganter,", "C.", "(1977).", "Helv.", "Chim.", "Acta,", "60,", "1924-1925.", "Amman,", "W.", "&", "Ganter,", "C.", "(1981).", "Helv.", "Chim.", "Acta,", "65,", "966-1022.", "Amman,", "W.,", "Ja¨", "ggi,", "F.", "J.", "&", "Ganter,", "C.", "(1980).", "Helv.", "Chim.", "Acta,", "63,", "2019-2041.", "Baggiolini,", "E.,", "Herzog,", "E.", "G.,", "Iwaski,", "S.,", "Schorta,", "R.", "&", "Schaffner,", "K.", "(1967).", "Helv.", "Chim.", "Acta,", "50,", "297-306.", "Dilthey,", "W.", "&", "Quint,", "F.", "J.", "(1930).", "J.", "Prakt.", "Chem.", "128,", "139-149.", "Eaton,", "P.", "E.,", "Tang,", "D.", "&", "Gilardi,", "R.", "(2002).", "Tetrahedron", "Lett.", "43,", "3-5.", "Enraf–Nonius", "(1994).", "CAD-4", "EXPRESS.", "Enraf–Nonius,", "Delft,", "The", "Nether-", "lands.", "Farrugia,", "L.", "J.", "(1997).", "J.", "Appl.", "Cryst.", "30,", "565.", "Farrugia,", "L.", "J.", "(1999).", "J.", "Appl.", "Cryst.", "32,", "837–838.", "Garbisch,", "E.", "W.", "&", "Sprecher,", "R.", "F.", "(1966).", "J.", "Am.", "Chem.", "Soc.", "88,", "3433-3436.", "Hafner,", "K.", "&", "Goliasch,", "K.", "(1961).", "Chem.", "Ber.", "94,", "2909-2921.", "Harms,", "K.", "&", "Wocadlo,", "S.", "(1995).", "XCAD4.", "University", "of", "Marburg,", "Germany.", "Harris,", "A.", "D.,", "Baucom,", "A.", "D.,", "Sierra,", "M.", "del", "R.", "I.", "A.,", "Jones,", "D.", "S.", "&", "Etzkorn,", "M.", "(2008).", "Acta", "Cryst.", "E64,", "o2270.", "Klinsmann,", "U.,", "Gauthier,", "J.,", "Schaffner,", "K.,", "Pasternak,", "M.", "&", "Fuchs,", "B.", "(1972).", "Helv.", "Chim.", "Acta,", "55,", "2643-2659.", "Masters,", "A.", "P.,", "Parvez,", "M.,", "Sorensen,", "T.", "S.", "&", "Sun,", "F.", "(1994).", "J.", "Am.", "Chem.", "Soc.", "116,", "2804-2811.", "Prakash,", "G.", "K.", "S.,", "Farnia,", "M.,", "Keyanian,", "S.,", "Olah,", "G.", "A.,", "Kuhn,", "H.", "J.", "&", "Schaffner,", "K.", "(1987).", "J.", "Am.", "Chem.", "Soc.", "109,", "911-912.", "Saito,", "M.", "&", "Ito,", "T.", "(2008).", "Acta", "Cryst.", "E64,", "o2121.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "Weiss,", "E.,", "Mer", "e´nyi,", "R.", "C.", "&", "Hu¨", "bel,", "W.", "(1960).", "Chem.", "Ind.", "15,", "407-408.", "Acta", "Cryst.", "(2009).", "E65,", "o729", "doi:10.1107/S1600536809005844", "Gidaly", "et", "al.", "o729" ]

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[ "organic", "compounds", "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "N-[4-(Morpholinodiazenyl)phenyl]-", "acetamide", "Taylor", "Chin,a", "Frank", "R.", "Fronczekb", "and", "Ralph", "Isovitscha*", "aDepartment", "of", "Chemistry,", "Whittier", "College,", "13406", "Philadelphia", "Street,", "Whittier,", "CA", "90608,", "USA,", "and", "bDepartment", "of", "Chemistry,", "Louisiana", "State", "University,", "Baton", "Rouge,", "LA", "70803,", "USA", "Correspondence", "e-mail:", "risovits@whittier.edu", "Received", "11", "November", "2009;", "accepted", "18", "November", "2009", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "90", "K;", "mean", "(C–C)", "=", "0.002", "A˚;", "R", "factor", "=", "0.038;", "wR", "factor", "=", "0.095;", "data-to-parameter", "ratio", "=", "13.4.", "The", "title", "compound,", "C12H16N4O2,", "is", "a", "member", "of", "a", "family", "of", "morpholine-substituted", "aromatic", "diazenes.", "Conjugation", "of", "the", "diazene", "group", "-system", "and", "the", "lone", "pair", "of", "electrons", "of", "the", "morpholine", "N", "atom", "is", "evidenced", "by", "a", "lengthened", "N", "N", "double", "bond", "of", "1.2707", "(19)", "A˚", "and", "a", "shortened", "N—N", "single", "bond", "of", "1.346", "(2)", "A˚", ".", "The", "bond", "angles", "at", "the", "morpholine", "N", "atom", "range", "from", "113.52", "(14)", "to", "121.12", "(14)", ",", "indicating", "some", "degree", "of", "sp2", "hybridization.", "The", "morpholine", "ring", "adopts", "a", "conventional", "chair", "conformation", "with", "the", "diazenyl", "group", "in", "the", "equatorial", "position.", "The", "diazenyl", "and", "acetamido", "groups", "are", "both", "twisted", "relative", "to", "the", "plane", "of", "the", "benzene", "ring", "by", "12.3", "(2)", "and", "25.5", "(3)", ",", "respectively.", "Related", "literature", "The", "title", "compound", "was", "synthesized", "using", "a", "modification", "of", "the", "method", "of", "Sengupta", "et", "al.", "(1998).", "For", "similar", "structures,", "see:", "Little", "et", "al.", "(2008).", "For", "information", "about", "diazene", "deri-", "vatives,", "see:", "Chen", "et", "al.", "(2005);", "Lalezari", "&", "Afgahi", "(1975).", "For", "bond-length", "data,", "see:", "Allen", "et", "al.", "(1987).", "Experimental", "Crystal", "data", "C12H16N4O2", "Mr", "=", "248.29", "Monoclinic,", "P21=c", "a", "=", "12.6013", "(4)", "A˚", "b", "=", "10.6114", "(3)", "A˚", "c", "=", "9.2967", "(2)", "A˚", "=", "93.874", "(2)", "Data", "collection", "Bruker", "Kappa", "APEXII", "CCD", "area-", "detector", "diffractometer", "Absorption", "correction:", "multi-scan", "(SADABS;", "Sheldrick,", "2004)", "Tmin", "=", "0.843,", "Tmax", "=", "0.992", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.038", "wR(F", "2)", "=", "0.095", "S", "=", "1.03", "2249", "reflections", "168", "parameters", "V", "=", "1240.29", "(6)", "A˚", "3", "Z", "=", "4", "Cu", "K", "radiation", "=", "0.77", "mm", "1", "T", "=", "90", "K", "0.23", "0.17", "0.01", "mm", "11437", "measured", "reflections", "2249", "independent", "reflections", "1655", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.053", "H", "atoms", "treated", "by", "a", "mixture", "of", "independent", "and", "constrained", "refinement", "max", "=", "0.20", "e", "A˚", "3", "min", "=", "0.20", "e", "A˚", "3", "Data", "collection:", "APEX2", "(Bruker,", "2006);", "cell", "refinement:", "SAINT", "(Bruker,", "2006);", "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", "for", "Windows", "(Farrugia,", "1997);", "software", "used", "to", "prepare", "material", "for", "publication:", "SHELXTL", "(Sheldrick,", "2008).", "RI", "acknowledges", "Whittier", "College", "for", "the", "faculty", "research", "grant", "that", "funded", "this", "research.", "TC", "thanks", "Whittier", "College", "for", "summer", "support.", "Mr", "Jonathan", "Attard", "is", "thanked", "for", "an", "initial", "trial", "synthesis", "of", "the", "title", "compound.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "GK2239).", "References", "Allen,", "F.", "H.,", "Kennard,", "O.,", "Watson,", "D.", "G.,", "Brammer,", "L.", "&", "Orpen,", "A.", "G.", "(1987).", "J.", "Chem.", "Soc.", "Perkin", "Trans.", "2,", "pp.", "S1–19.", "Bruker", "(2006).", "APEX2", "and", "SAINT.", "Bruker", "AXS", "Inc.,", "Madison,", "Wisconsin,", "USA.", "Chen,", "B.,", "Flatt,", "A.", "K.,", "Jian,", "H.,", "Hudson,", "J.", "L.", "&", "Tour,", "J.", "M.", "(2005).", "Chem.", "Mater.", "17,", "4832–4836.", "Farrugia,", "L.", "J.", "(1997).", "J.", "Appl.", "Cryst.", "30,", "565.", "Lalezari,", "I.", "&", "Afgahi,", "F.", "(1975).", "J.", "Pharm.", "Sci.", "64,", "698–699.", "Little,", "V.", "R.,", "Jenkins,", "H.", "&", "Vaughan,", "K.", "(2008).", "J.", "Chem.", "Crystallogr.", "38,", "447–", "452.", "Sengupta,", "S.,", "Bhattacharyya,", "S.", "&", "Sadhukhan,", "S.", "K.", "(1998).", "J.", "Chem.", "Soc.", "Perkin", "Trans.", "1,", "pp.", "275–277.", "Sheldrick,", "G.", "(2004).", "SADABS.", "University", "of", "Go¨", "ttingen,", "Germany.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", "o3206", "Chin", "et", "al.", "doi:10.1107/S160053680904937X", "Acta", "Cryst.", "(2009).", "E65,", "o3206" ]

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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "Bis(1,10-phenanthroline-j", "N,N0)(phenyl-", "acetato-jO)copper(II)", "phenylacetate", "hexahydrate", "2", "Bing-Tian", "Tu,a", "Hong-Zhen", "Xie,b*", "Ying-Tao", "Rena,b", "and", "Jing-Zhong", "Chena", "aFaculty", "of", "Materials", "Science", "and", "Chemical", "Engineering,", "China", "University", "of", "Geoscience,", "Wuhan,", "Hubei", "430074,", "People’s", "Republic", "of", "China,", "and", "bState", "Key", "Laboratory", "Base", "of", "Novel", "Functional", "Materials", "&", "Preparation", "Science,", "Faculty", "of", "Materials", "Science", "&", "Chemical", "Engineering,", "Institute", "of", "Solid", "Materials", "Chemistry,", "Ningbo", "University,", "Ningbo,", "Zhejiang", "315211,", "People’s", "Republic", "of", "China", "Correspondence", "e-mail:", "zhengyueqing@nbu.edu.cn", "Received", "27", "August", "2008;", "accepted", "8", "October", "2008", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "293", "K;", "mean", "(C–C)", "=", "0.003", "A˚;", "R", "factor", "=", "0.034;", "wR", "factor", "=", "0.095;", "data-to-parameter", "ratio", "=", "17.3.", "In", "the", "title", "compound,", "[Cu(C8H7O2)(C12H8N2)2](C8H7O2)", "-", "6H2O,", "the", "Cu", "atom", "is", "in", "a", "distorted", "square-pyramidal", "coordination", "environment.", "The", "six", "crystallographically", "inde-", "pendent", "uncoordinated", "water", "molecules", "are", "interconnected", "by", "hydrogen", "bonds,", "completing", "dodecawater", "(H2O)12", "clusters", "which", "are", "hydrogen", "bonded", "to", "the", "carboxylate", "groups", "of", "phenylacetate", "anions,", "building", "up", "one-dimensional", "anionic", "chains", "propagating", "along", "[100].", "Between", "the", "cationic", "and", "anionic", "chains", "are", "hydrogen", "bonds", "from", "water", "molecules", "to", "the", "carboxylate", "O", "atoms", "belonging", "to", "the", "phenylacetato", "ligands.", "Related", "literature", "For", "general", "background,", "see:", "Kuroda-Sowa", "et", "al.", "(1997);", "Lehn", "(2007);", "Li", "et", "al.", "(2008).", "For", "related", "structures,", "see:", "Addison", "&", "Rao", "(1984);", "Baruah", "et", "al.", "(2007);", "Liu", "&", "Xu", "(2005);", "Ma", "et", "al.", "(2005);", "Sugimori", "et", "al.", "(1997);", "Zheng", "et", "al.", "(2001).", "metal-organic", "compounds", "Experimental", "Crystal", "data", "[Cu(C8H7O2)(C12H8N2)2]-", "(C8H7O2)", "6H2O", "Mr", "=", "802.33", "Triclinic,", "P1", "a", "=", "11.499", "(2)", "A˚", "b", "=", "11.903", "(2)", "A˚", "c", "=", "16.066", "(3)", "A˚", "=", "71.00", "(3)", "Data", "collection", "Rigaku", "R-AXIS", "RAPID", "diffractometer", "Absorption", "correction:", "multi-scan", "(ABSCOR;", "Higashi,", "1995)", "Tmin", "=", "0.793,", "Tmax", "=", "0.902", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.034", "wR(F", "2)", "=", "0.095", "S", "=", "1.08", "8680", "reflections", "=", "72.97", "(3)", "=", "68.93", "(3)", "V", "=", "1901.3", "(8)", "A˚", "3", "Z", "=", "2", "Mo", "K", "radiation", "=", "0.64", "mm", "1", "T", "=", "293", "(2)", "K", "0.37", "0.35", "0.17", "mm", "18689", "measured", "reflections", "8680", "independent", "reflections", "7070", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.030", "496", "parameters", "H-atom", "parameters", "constrained", "max", "=", "0.41", "e", "A˚", "3", "min", "=", "0.39", "e", "A˚", "3", "Data", "collection:", "RAPID-AUTO", "(Rigaku,", "1998);", "cell", "refinement:", "RAPID-AUTO;", "data", "reduction:", "CrystalStructure", "(Rigaku/MSC,", "2002);", "program(s)", "used", "to", "solve", "structure:", "SHELXS97", "(Sheldrick,", "2008);", "program(s)", "used", "to", "refine", "structure:", "SHELXL97", "(Sheldrick,", "2008);", "molecular", "graphics:", "ORTEPII", "(Johnson,", "1976);", "software", "used", "to", "prepare", "material", "for", "publication:", "SHELXL97.", "This", "project", "was", "sponsored", "by", "the", "K.", "C.", "Wong", "Magna", "Fund", "of", "Ningbo", "University", "and", "supported", "by", "the", "Expert", "Project", "of", "Key", "Basic", "Research", "of", "the", "Ministry", "of", "Science", "and", "Technology", "of", "China", "(grant", "No.", "2003CCA00800),", "the", "Zhejiang", "Provincial", "Natural", "Science", "Foundation", "(grant", "No.", "Z203067)", "and", "the", "Ningbo", "Municipal", "Natural", "Science", "Foundation", "(grant", "No.", "2006", "A610061).", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "PK2118).", "References", "Addison,", "A.", "W.", "&", "Rao,", "N.", "T.", "(1984).", "J.", "Chem.", "Soc.", "Dalton", "Trans.", "pp.", "1349–", "1984.", "Baruah,", "A.", "M.,", "Karmaker,", "A.", "&", "Baruah,", "J.", "B.", "(2007).", "Polyhedron,", "26,", "4479–", "4488.", "Higashi,", "T.", "(1995).", "ABSCOR.", "Rigaku", "Corporation,", "Tokyo,", "Japan.", "Johnson,", "C.", "K.", "(1976).", "ORTEPII.", "Report", "ORNL-5138.", "Oak", "Ridge", "National", "Laboratory,", "Tennessee,", "USA.", "Kuroda-Sowa,", "T.,", "Horino,", "T.,", "Yamamoto,", "M.,", "Ohno,", "Y.,", "Maekawa,", "M.", "&", "Munakata,", "M.", "(1997).", "Inorg.", "Chem.", "36,", "6382–6389.", "Lehn,", "J.", "M.", "(2007).", "Chem.", "Rev.", "36,", "151–160.", "Li,", "X.,", "Cheng,", "D.", "Y.,", "Li,", "Z.", "F.", "&", "Zheng,", "Y.", "Q.", "(2008).", "Cryst.", "Growth", "Des.", "8,", "2853–2861.", "Liu,", "Q.", "Y.", "&", "Xu,", "L.", "(2005).", "CrystEngComm,", "7,", "87–89.", "Ma,", "B.", "Q.,", "Sun,", "H.", "L.", "&", "Gao,", "S.", "(2005).", "Chem.", "Commun.", "pp.", "2336–2338.", "Rigaku", "(1998).", "RAPID-AUTO.", "Rigaku", "Corporation,", "Tokyo,", "Japan.", "Rigaku/MSC", "(2002).", "CrystalStructure.", "Rigaku/MSC", "Inc.,", "The", "Woodlands,", "Texas,", "USA.", "Sheldrick,", "G.", "M.", "(2008).", "Acta", "Cryst.", "A64,", "112–122.", 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[ "supplementary", "materials", "Acta", "Cryst.", "(2008).", "E64,", "m1475", "[", "doi:10.1107/S1600536808032480", "]", "Bis(1,10-phenanthroline-", "2N,N')(phenylacetato-", "O)copper(II)", "phenylacetate", "hexahydrate", "B.-T.", "Tu,", "H.-Z.", "Xie,", "Y.-T.", "Ren", "and", "J.-Z.", "Chen", "Comment", "Construction", "of", "supramolecular", "architectures", "with", "interesting", "physical", "properties", "has", "grown", "rapidly", "owing", "to", "their", "potential", "use", "as", "new", "functional", "materials", "(Lehn,", "2007).", "The", "most", "efficient", "and", "widely", "used", "approach", "for", "designing", "such", "materials", "is", "the", "self-assembly", "of", "organic", "ligands", "and", "metal", "ions", "(Kuroda-Sowa", "et", "al.,", "1997;", "Li", "et", "al.,", "2008).", "Here,", "we", "report", "a", "Cu(II)", "complex", "[Cu(C12H8N2)2(C8H7O2)](C8H7O2).6H2O", "from", "the", "self-assembly", "of", "Cu(OH)2,", "phenylacetatic", "acid", "and", "phenanthroline.", "The", "title", "compound", "consists", "of", "[Cu(C12H8N2)2(C8H7O2)]2+", "complex", "cations,", "phenylacetate", "anions,", "and", "water", "molecules", "of", "crystallization", "(Fig.1).", "The", "Cu", "atoms", "are", "each", "coordinated", "by", "two", "phenanthroline", "ligands", "and", "one", "phenylacetato", "ligand", "to", "complete", "a", "square-pyramidal", "CuN4O", "chromophore", "with", "the", "phenylacetic", "oxygen", "atom", "at", "the", "equatorial", "site.", "The", "equatorial", "Cu–N", "bond", "lengths", "fall", "in", "the", "range", "2.002–2.060", "Å", "and", "the", "Cu–O", "bond", "distance", "is", "equal", "to", "2.001", "(1)", "Å,", "while", "the", "axial", "Cu–N", "bond", "distance", "is", "2.187", "(2)", "Å.", "According", "to", "Addison's", "definition", "(Addison", "&", "Rao,", "1984),", "the", "τ", "index", "about", "the", "central", "Cu", "atom", "is", "0.233", "Å,", "suggesting", "that", "the", "square", "pyramidal", "coordination", "geometry", "is", "slightly", "distorted", "with", "the", "Cu", "atom", "deviated", "from", "the", "basal", "plane", "by", "0.1779", "(8)", "Å", "towards", "the", "apical", "N1", "atom.", "Within", "each", "complex", "cation,", "both", "phenanthroline", "ligands", "exhibit", "nearly", "perfect", "coplanarity", "and", "constitute", "an", "orthogonal", "system", "with", "the", "coordinating", "carboxylate", "group", "of", "the", "phenylacetate", "anion.", "The", "complex", "cation", "displays", "a", "similar", "configuration", "to", "those", "observed", "in", "a", "succinato", "complex", "[Cu(phen)2(C4H4O4)]", "previously", "reported", "by", "us", "(Zheng", "et", "al.,", "2001)", "and", "all", "the", "bonding", "parameters", "are", "normal", "(Baruah", "et", "al.,", "2007).", "As", "far", "as", "the", "phenylacetato", "ligand", "is", "concerned,", "the", "phenyl", "plane", "is", "found", "to", "be", "nearly", "perpendicular", "to", "the", "single", "bonded", "carbon", "backbone", "(dihedral", "angle:", "89.5", "(1)°),", "which", "is", "significantly", "larger", "than", "the", "corresponding", "one", "of", "68.6", "(2)°", "in", "the", "non-coordinating", "phenylacetate", "anion,", "and", "the", "carboxylate", "group", "is", "twisted", "from", "the", "single", "bonded", "carbon", "backbone", "by", "70.4", "(2)°", "in", "the", "former", "coordinating", "one,", "and", "is", "considerably", "larger", "the", "60.7", "(2)°", "in", "the", "non-coordinating", "anion.", "As", "expected,", "the", "C–O", "bond", "distance", "for", "the", "coordinating", "oxygen", "atom", "is", "1.281", "(2)", "Å,", "which", "is", "longer", "than", "those", "for", "non-coordinating", "ones", "(1.247–1.254", "Å).", "The", "complex", "cations", "are", "distributed", "in", "such", "a", "way", "that", "the", "symmetry-related", "phenanthroline", "ligands", "are", "oriented", "antiparallel", "with", "a", "mean", "interplanar", "distance", "of", "3.39", "(2)", "Å,", "indicating", "a", "significant", "face-to-face", "π-π", "stacking", "interaction", "(Sugimori", "et", "al.,", "1997).", "Owing", "to", "such", "intercationic", "π-π", "stacking", "interactions", "and", "weak", "intercationic", "C–H···O", "interactions", "with", "the", "uncoordinating", "carboxylate", "oxygen", "atom,", "two", "centrosymmetrically", "related", "complex", "cations", "form", "dimers,", "which", "are", "further", "assembled", "via", "interdimeric", "π-π", "stacking", "interactions", "into", "1D", "chains", "extending", "along", "the", "[101]", "direction.", "Furthermore,", "the", "resulting", "chains", "are", "arranged", "in", "planes", "parallel", "to", "(010),", "between", "which", "the", "lattice", "water", "molecules", "and", "the", "phenylacetate", "anions", "are", "sandwiched.", "Out", "of", "the", "six", "crystallographically", "distinct", "lattice", "water", "molecules,", "three", "water", "molecules", "together", "with", "their", "centrosym-", "metry-related", "partners", "are", "hydrogen", "bonded", "to", "one", "another", "to", "generate", "chair-like", "hexawater", "clusters", "(Fig.2),", "to", "which", "the", "remaining", "lattice", "water", "molecules", "are", "associated", "by", "hydrogen", "bonds", "to", "complete", "dodecawater", "(H2O)12", "clusters", "similar", "to", "those", "reported", "in", "the", "literature", "(Liu", "&", "Xu,", "2005;", "Ma", "et", "al.,", "2005).", "The", "resulting", "dodecawater", "(H2O)12", "clusters", "are", "hydrogen", "bonded", "to", "the", "carboxylate", "groups", "of", "phenylacetate", "anions", "to", "build", "up", "1D", "anionic", "chains", "propagating", "along", "[100].", "Between", "sup-1" ]

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[ "supplementary", "materials", "O2—Cu2—N4—C24", "N5—Cu2—N4—C24", "O4—Cu2—N4—C24", "Cu1—O1—C1—C6", "Cu1—O1—C1—C2", "C8—N1—C2—C3", "Cu1—N1—C2—C3", "C8—N1—C2—C1", "Cu1—N1—C2—C1", "O1—C1—C2—C3", "C6—C1—C2—C3", "O1—C1—C2—N1", "C6—C1—C2—N1", "N1—C2—C3—C4", "C1—C2—C3—C4", "C2—C3—C4—C5", "C3—C4—C5—C6", "C4—C5—C6—C1", "O1—C1—C6—C5", "C2—C1—C6—C5", "Cu2—O2—C8—N1", "Cu2—O2—C8—C7", "C2—N1—C8—O2", "Cu1—N1—C8—O2", "C2—N1—C8—C7", "Cu1—N1—C8—C7", "Cu2—O3—C7—N2", "Cu2—O3—C7—C8", "C9—N2—C7—O3", "sup-10", "Hydrogen-bond", "geometry", "(Å,", "°)", "D—H···A", "O4—H4A···O1i", "O4—H4B···O5", "C19—H19···O4ii", "C21—H21···O5ii", "0.93", "Symmetry", "codes:", "(i)", "−x+1,", "−y+1,", "−z+1;", "(ii)", "−x,", "−y+1,", "−z.", "D—H", "0.91", "0.89", "0.93", "178.7", "(2)", "5.7", "(2)", "−84.2", "(2)", "−173.9", "(3)", "5.2", "(3)", "−6.4", "(5)", "173.9", "(3)", "176.8", "(3)", "−2.9", "(3)", "−178.6", "(3)", "0.6", "(4)", "−1.7", "(4)", "177.5", "(3)", "−177.1", "(3)", "−0.7", "(5)", "−0.3", "(5)", "1.4", "(5)", "−1.5", "(5)", "179.6", "(3)", "0.5", "(5)", "−173.3", "(3)", "9.0", "(3)", "0.2", "(5)", "179.9", "(3)", "177.9", "(3)", "−2.4", "(3)", "174.0", "(3)", "−7.2", "(3)", "0.0", "(5)", "C24—C20—C21—C22", "C19—C20—C21—C22", "C20—C21—C22—C23", "C24—N4—C23—C22", "Cu2—N4—C23—C22", "C21—C22—C23—N4", "C23—N4—C24—C20", "Cu2—N4—C24—C20", "C23—N4—C24—C25", "Cu2—N4—C24—C25", "C21—C20—C24—N4", "C19—C20—C24—N4", "C21—C20—C24—C25", "C19—C20—C24—C25", "C14—N5—C25—C17", "Cu2—N5—C25—C17", "C14—N5—C25—C24", "Cu2—N5—C25—C24", "C16—C17—C25—N5", "C18—C17—C25—N5", "C16—C17—C25—C24", "C18—C17—C25—C24", "N4—C24—C25—N5", "C20—C24—C25—N5", "N4—C24—C25—C17", "C20—C24—C25—C17", "O6—N6—O5—O5", "O7—N6—O5—O5", "H···A", "1.84", "1.97", "2.51", "2.53", "0.3", "(6)", "178.6", "(4)", "0.5", "(6)", "0.3", "(5)", "−172.1", "(3)", "−0.8", "(6)", "0.5", "(5)", "174.3", "(3)", "−178.4", "(3)", "−4.7", "(4)", "−0.8", "(5)", "−179.3", "(3)", "178.1", "(3)", "−0.4", "(5)", "−0.9", "(5)", "−173.7", "(3)", "177.7", "(3)", "4.9", "(4)", "1.1", "(5)", "179.9", "(3)", "−177.5", "(4)", "1.3", "(5)", "−0.1", "(5)", "−179.1", "(3)", "178.5", "(3)", "−0.5", "(5)", "0.0", "(3)", "0.00", "(17)", "D···A", "2.745", "(3)", "2.839", "(5)", "3.355", "(5)", "3.437", "(7)", "D—H···A", "172", "164", "152", "167" ]

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[ "supplementary", "materials", "Fig.", "2", "sup-12" ]

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[ "supplementary", "materials", "Acta", "Cryst.", "(2010).", "E66,", "m1249-m1250", "[", "doi:10.1107/S1600536810035919", "]", "Aqua{", "-N-[3-(dimethylamino)propyl]-N'-(2-oxidophenyl)oxamidato(3-)}(1,10-", "phenanthroline)dicopper(II)", "nitrate", "Z.", "Gao", "and", "Y.", "Wang", "Comment", "Much", "research", "effort", "has", "been", "dedicated", "to", "studying", "oxamide-bridged", "transition", "metal", "complexes", "because", "of", "their", "bioactiv-", "ities", "and", "the", "versatile", "bridging", "function", "(Kou", "et", "al.,", "1999;", "Ojima", "&", "Nonoyama,", "1988).", "The", "title", "compound,", "C25H25N6O4Cu2+,", "NO3-is", "a", "binuclear", "copper(II)", "complex", "and", "the", "structure", "is", "similar", "to", "that", "seen", "previously", "in", "a", "resemble", "compound", "(Wang", "et", "al.,", "2003)(Fig.", "1).", "In", "the", "dinuclear", "cation,", "the", "oxalate", "groups", "bridge", "the", "two", "copper(II)", "ions.", "The", "separation", "of", "copper", "atoms", "is", "5.192", "(2)", "Å.", "The", "Cu-atom", "coordination", "geometries", "are", "regarded", "as", "distorted", "square", "and", "square", "pyramid,", "respectively.", "The", "oxamide", "ligand", "has", "a", "cis", "geometry,", "is", "fully", "deprotonated", "and", "acts", "in", "a", "hexadentate", "fashion.", "Cu—O", "and", "Cu—N", "bond", "lengths", "are", "shown", "in", "Table", "1.", "For", "Cu1,", "the", "four", "atoms", "(O1,", "N1,", "N2,", "N3)", "from", "the", "oxalate", "groups", "build", "the", "square", "plane.", "The", "average", "value", "of", "the", "copper", "to", "N1,", "N2", "and", "N3", "bond", "distance", "is", "1.969", "Å.", "For", "Cu2,", "the", "donors", "on", "the", "oxamide", "(O2,", "O3)", "and", "the", "phen", "(N4,", "N5)", "offer", "the", "basal", "plane", "and", "the", "oxygen", "of", "a", "water", "molecule", "occupies", "an", "apical", "position", "with", "a", "bond", "length", "of", "2.275", "(2)", "Å.", "The", "maximum", "displacement", "from", "the", "least-square", "plane", "is", "0.0055", "(2)", "Å", "for", "O2", "and", "the", "Cu2", "atom", "lies", "0.1282", "(8)", "Å", "out", "of", "this", "plane.", "In", "the", "crystal,", "the", "neutral", "binuclear", "complexes", "and", "nitrate", "ions", "are", "connected", "by", "classcial", "O—H···O", "and", "non-classical", "C—H···O", "hydrogen", "bonds", "into", "a", "three-dimensional", "framework", "(Fig.", "2,", "Table", "2).", "Experimental", "A", "water", "solution", "(10ml)", "of", "Cu(NO3)2.3H2O", "(0.484g,", "2mmol)", "was", "added", "slowly", "into", "a", "ethanol", "solution", "(10ml)", "containing", "N-benzyl-N'-(3-amino-3-dimethylpropyl)oxamide", "(1mmol,", "0.262g)", "and", "sodium", "ethoxide", "(0.204", "g,", "3mmol).", "The", "mixture", "was", "stirred", "quickly", "for", "2h,", "then", "an", "aqueous", "solution", "(5ml)", "of", "1,10-phenanthroline", "(0.180", "g,", "1mmol)", "was", "added", "dropwise", "into", "the", "mixture.", "The", "reaction", "solution", "was", "heated", "at", "303K", "with", "stirring", "for", "12h.", "The", "resulting", "solution", "was", "filtered", "and", "the", "filtrate", "was", "kept", "at", "room", "temperature.", "Green", "crystals", "suitable", "for", "X-ray", "analysis", "were", "obtained", "from", "the", "filtrate", "by", "slow", "evaporation", "for", "about", "three", "weeks.", "Yield,", "69%,", "analysis,", "calculated", "for", "C25H26N6O7Cu2:", "C", "46.22,", "H,", "26.21;", "N", "12.94%;", "found:", "C", "46.26,", "H", "26.29,", "N,", "12.96%.", "Refinement", "H", "atoms", "were", "positioned", "geometrically", "[0.93", "(CH),", "0.97", "(CH2),", "0.96", "(CH3)", "and", "0.84", "(OH)Å]", "and", "constrained", "to", "ride", "on", "their", "parent", "atoms", "with", "Uiso(H)", "=1.2(1.5", "for", "methyl", "and", "hydroxy", "O)Ueq(C/N).", "sup-1" ]

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[ "C10B—C9—H9B", "H9A—C9—H9B", "N2—C9—H9C", "C10A—C9—H9C", "C10B—C9—H9C", "H9B—C9—H9C", "N2—C9—H9D", "C10A—C9—H9D", "C10B—C9—H9D", "N1—Cu1—O1—C1", "N2—Cu1—O1—C1", "N3—Cu1—O1—C1", "O3—Cu2—O2—C8", "N4—Cu2—O2—C8", "O4—Cu2—O2—C8", "O2—Cu2—O3—C7", "N5—Cu2—O3—C7", "O4—Cu2—O3—C7", "O1—Cu1—N1—C8", "N2—Cu1—N1—C8", "O1—Cu1—N1—C2", "N2—Cu1—N1—C2", "N1—Cu1—N2—C7", "O1—Cu1—N2—C7", "N3—Cu1—N2—C7", "N1—Cu1—N2—C9", "O1—Cu1—N2—C9", "N3—Cu1—N2—C9", "O1—Cu1—N3—C13A", "N2—Cu1—N3—C13A", "O1—Cu1—N3—C12B", "N2—Cu1—N3—C12B", "O1—Cu1—N3—C11B", "N2—Cu1—N3—C11B", "O1—Cu1—N3—C12A", "N2—Cu1—N3—C12A", "O1—Cu1—N3—C13B", "N2—Cu1—N3—C13B", "O1—Cu1—N3—C11A", "N2—Cu1—N3—C11A", "O3—Cu2—N5—C14", "N4—Cu2—N5—C14", "O4—Cu2—N5—C14", "O3—Cu2—N5—C25", "N4—Cu2—N5—C25", "O4—Cu2—N5—C25", "O2—Cu2—N4—C23", "N5—Cu2—N4—C23", "O4—Cu2—N4—C23", "85.6", "107.8", "109.4", "84.3", "109.7", "129.6", "109.7", "128.2", "109.5", "−5.2", "(2)", "−12.1", "(5)", "169.7", "(2)", "−10.2", "(2)", "177.5", "(2)", "84.6", "(2)", "9.6", "(2)", "−177.8", "(2)", "−87.0", "(2)", "−175.3", "(2)", "3.0", "(2)", "4.5", "(2)", "−177.2", "(2)", "−3.1", "(2)", "3.8", "(6)", "−178.0", "(2)", "178.6", "(3)", "−174.5", "(4)", "3.6", "(3)", "−76.3", "(5)", "104.2", "(5)", "62.0", "(8)", "−117.6", "(7)", "−161.2", "(4)", "19.3", "(4)", "47.8", "(7)", "−131.8", "(7)", "−51.6", "(4)", "128.9", "(4)", "158.3", "(3)", "−21.2", "(3)", "10.2", "(3)", "−177.6", "(3)", "−85.0", "(3)", "−177.9", "(2)", "−5.7", "(2)", "86.9", "(2)", "−8.5", "(3)", "178.5", "(3)", "88.6", "(3)", "supplementary", "materials", "N5—C25—C17", "N5—C25—C24", "C17—C25—C24", "O6—N6—O7", "O6—N6—O5", "O7—N6—O5", "O6—N6—O5", "O7—N6—O5", "Cu1—N2—C7—O3", "C9—N2—C7—C8", "Cu1—N2—C7—C8", "O2—C8—C7—O3", "N1—C8—C7—O3", "O2—C8—C7—N2", "N1—C8—C7—N2", "C7—N2—C9—C10A", "Cu1—N2—C9—C10A", "C7—N2—C9—C10B", "Cu1—N2—C9—C10B", "N2—C9—C10A—C11A", "C10B—C9—C10A—C11A", "C9—C10A—C11A—N3", "C13A—N3—C11A—C10A", "C12B—N3—C11A—C10A", "C11B—N3—C11A—C10A", "C12A—N3—C11A—C10A", "C13B—N3—C11A—C10A", "Cu1—N3—C11A—C10A", "N2—C9—C10B—C11B", "C10A—C9—C10B—C11B", "C13A—N3—C11B—C10B", "C12B—N3—C11B—C10B", "C12A—N3—C11B—C10B", "C13B—N3—C11B—C10B", "C11A—N3—C11B—C10B", "Cu1—N3—C11B—C10B", "C9—C10B—C11B—N3", "C25—N5—C14—C15", "Cu2—N5—C14—C15", "N5—C14—C15—C16", "C14—C15—C16—C17", "C15—C16—C17—C25", "C15—C16—C17—C18", "C16—C17—C18—C19", "C25—C17—C18—C19", "C17—C18—C19—C20", "C18—C19—C20—C21", "C18—C19—C20—C24", "122.3", "(4)", "117.4", "(3)", "120.3", "(4)", "115.5", "(7)", "129.4", "(7)", "114.5", "(6)", "129.4", "(7)", "114.5", "(6)", "−178.5", "(3)", "−178.8", "(3)", "2.6", "(3)", "−1.2", "(4)", "−179.3", "(2)", "177.8", "(2)", "−0.3", "(4)", "161.3", "(4)", "−20.4", "(5)", "−169.8", "(4)", "8.5", "(6)", "57.4", "(8)", "−33.0", "(10)", "−84.7", "(7)", "−65.0", "(8)", "176.4", "(12)", "−44.5", "(7)", "174.4", "(11)", "−74.9", "(9)", "61.0", "(5)", "−49.2", "(10)", "51.2", "(10)", "−163.7", "(9)", "82.0", "(13)", "88.3", "(14)", "−165.3", "(8)", "35.8", "(6)", "−54.7", "(8)", "77.8", "(11)", "0.2", "(6)", "171.6", "(3)", "0.1", "(7)", "0.1", "(7)", "−0.7", "(6)", "−179.3", "(4)", "177.3", "(5)", "−1.4", "(7)", "0.5", "(8)", "−177.9", "(4)", "0.4", "(6)", "sup-9" ]

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[ "supplementary", "materials", "C11B—N3—C13B", "C12A—N3—C13B", "C13A—N3—C11A", "C12B—N3—C11A", "C12A—N3—C11A", "C13B—N3—C11A", "C13A—N3—Cu1", "C12B—N3—Cu1", "C11B—N3—Cu1", "C12A—N3—Cu1", "C13B—N3—Cu1", "C11A—N3—Cu1", "C14—N5—C25", "C14—N5—Cu2", "C25—N5—Cu2", "C23—N4—C24", "C23—N4—Cu2", "C24—N4—Cu2", "O1—C1—C6", "O1—C1—C2", "C6—C1—C2", "C3—C2—N1", "C3—C2—C1", "N1—C2—C1", "C4—C3—C2", "C4—C3—H3", "C2—C3—H3", "C3—C4—C5", "C3—C4—H4", "C5—C4—H4", "C4—C5—C6", "C4—C5—H5", "C6—C5—H5", "C5—C6—C1", "C5—C6—H6", "C1—C6—H6", "O2—C8—N1", "O2—C8—C7", "N1—C8—C7", "O3—C7—N2", "O3—C7—C8", "N2—C7—C8", "N2—C9—C10A", "N2—C9—C10B", "N2—C9—H9A", "C10A—C9—H9A", "C10B—C9—H9A", "N2—C9—H9B", "C10A—C9—H9B", "sup-8", "101.5", "(4)", "94.9", "(9)", "111.8", "(5)", "87.3", "(6)", "102.6", "(5)", "135.8", "(4)", "112.8", "(6)", "114.8", "(10)", "114.9", "(4)", "106.9", "(9)", "103.2", "(5)", "109.7", "(3)", "119.3", "(3)", "129.2", "(3)", "111.0", "(3)", "118.1", "(4)", "130.2", "(3)", "111.3", "(3)", "123.6", "(3)", "118.6", "(3)", "117.8", "(3)", "127.4", "(3)", "121.2", "(3)", "111.4", "(3)", "119.6", "(3)", "120.2", "120.2", "119.7", "(3)", "120.2", "120.2", "121.4", "(3)", "119.3", "119.3", "120.2", "(3)", "119.9", "119.9", "129.6", "(3)", "117.3", "(3)", "113.0", "(3)", "129.5", "(3)", "115.4", "(3)", "115.1", "(3)", "112.8", "(4)", "110.3", "(5)", "109.0", "109.0", "131.0", "109.0", "109.0", "C10B—C11B—H11C", "N3—C11B—H11D", "C10B—C11B—H11D", "H11C—C11B—H11D", "N3—C12B—H12D", "N3—C12B—H12E", "H12D—C12B—H12E", "N3—C12B—H12F", "H12D—C12B—H12F", "H12E—C12B—H12F", "N3—C13B—H13D", "N3—C13B—H13E", "H13D—C13B—H13E", "N3—C13B—H13F", "H13D—C13B—H13F", "H13E—C13B—H13F", "N5—C14—C15", "N5—C14—H14", "C15—C14—H14", "C16—C15—C14", "C16—C15—H15", "C14—C15—H15", "C15—C16—C17", "C15—C16—H16", "C17—C16—H16", "C16—C17—C25", "C16—C17—C18", "C25—C17—C18", "C19—C18—C17", "C19—C18—H18", "C17—C18—H18", "C18—C19—C20", "C18—C19—H19", "C20—C19—H19", "C21—C20—C24", "C21—C20—C19", "C24—C20—C19", "C22—C21—C20", "C22—C21—H21", "C20—C21—H21", "C21—C22—C23", "C21—C22—H22", "C23—C22—H22", "N4—C23—C22", "N4—C23—H23", "C22—C23—H23", "N4—C24—C20", "N4—C24—C25", "C20—C24—C25", "109.4", "109.4", "109.4", "108.0", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "109.5", "121.7", "(4)", "119.2", "119.2", "119.0", "(5)", "120.5", "120.5", "121.4", "(4)", "119.3", "119.3", "116.4", "(4)", "126.5", "(5)", "117.1", "(5)", "122.8", "(5)", "118.6", "118.6", "122.1", "(5)", "118.9", "118.9", "117.1", "(4)", "126.1", "(5)", "116.8", "(5)", "120.5", "(4)", "119.7", "119.7", "118.1", "(5)", "121.0", "121.0", "123.4", "(4)", "118.3", "118.3", "122.8", "(4)", "116.4", "(3)", "120.9", "(4)" ]

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[ "Acta", "Crystallographica", "Section", "E", "Structure", "Reports", "Online", "ISSN", "1600-5368", "Aqua{l-N-[3-(dimethylamino)propyl]-N0-", "(2-oxidophenyl)oxamidato(3", ")}(1,10-", "phenanthroline)dicopper(II)", "nitrate", "Zhongjun", "Gao*", "and", "Yanbao", "Wang", "Department", "of", "Chemistry,", "Jining", "University,", "Shandong", "273155,", "People’s", "Republic", "of", "China", "Correspondence", "e-mail:", "zhongjungao@yahoo.cn", "Received", "12", "August", "2010;", "accepted", "7", "September", "2010", "Key", "indicators:", "single-crystal", "X-ray", "study;", "T", "=", "296", "K;", "mean", "(C–C)", "=", "0.007", "A˚;", "disorder", "in", "main", "residue;", "R", "factor", "=", "0.042;", "wR", "factor", "=", "0.129;", "data-to-parameter", "ratio", "=", "15.1.", "The", "title", "complex,", "[Cu2(C13H16N3O3)(C12H8N2)(H2O)]NO3,", "consists", "of", "a", "nitrate", "ion", "and", "a", "binuclear", "CuII", "unit", "in", "which", "the", "oxamide", "ligand", "has", "a", "cis", "geometry,", "is", "fully", "deprotonated", "and", "acts", "in", "a", "bidentate", "fashion", "to", "one", "CuII", "atom", "and", "in", "a", "tetradentate", "fashion", "to", "the", "other", "CuII", "atom.", "The", "CuII", "atom", "coordination", "geometries", "are", "distorted", "square-planar", "and", "distorted", "square-pyramidal.", "In", "the", "crystal", "structure,", "binuclear", "complexes", "and", "nitrate", "ions", "are", "connected", "by", "classical", "O—", "H", "O", "and", "non-classical", "C—H", "O", "hydrogen", "bonds", "into", "a", "three-dimensional", "framework.", "The", "alkyl", "chains", "of", "the", "anion", "are", "equally", "disorded", "over", "two", "positions.", "Related", "literature", "For", "to", "background", "oxamide-bridged", "metal", "complexes,", "see:", "Kou", "et", "al.", "(1999);", "Ojima", "&", "Nonoyama", "(1988).", "For", "a", "related", "structure,", "see:", "Wang", "et", "al.", "(2003).", "transition", "Experimental", "Crystal", "data", "[Cu2(C13H16N3O3)(C12H8N2)-", "(H2O)]NO3", "Mr", "=", "649.60", "Triclinic,", "P1", "a", "=", "10.543", "(2)", "A˚", "b", "=", "11.070", "(2)", "A˚", "c", "=", "11.404", "(2)", "A˚", "=", "89.88", "(3)", "Data", "collection", "Bruker", "SMART", "CCD", "diffractometer", "Absorption", "correction:", "multi-scan", "(SADABS;", "Sheldrick,", "1996)", "Tmin", "=", "0.448,", "Tmax", "=", "0.508", "Refinement", "R[F", "2", ">", "2", "(F", "2)]", "=", "0.042", "wR(F", "2)", "=", "0.129", "S", "=", "1.00", "5984", "reflections", "397", "parameters", "Table", "1", "Selected", "bond", "lengths", "(A˚", ").", "Cu2—O2", "Cu2—O3", "Cu2—N5", "Cu2—N4", "Cu2—O4", "=", "82.28", "(3)", "=", "78.24", "(3)", "V", "=", "1290.7", "(4)", "A˚", "3", "Z", "=", "2", "Mo", "K", "radiation", "=", "1.71", "mm", "1", "T", "=", "296", "K", "0.56", "0.51", "0.46", "mm", "12596", "measured", "reflections", "5984", "independent", "reflections", "4281", "reflections", "with", "I", ">", "2", "(I)", "Rint", "=", "0.022", "24", "restraints", "H-atom", "parameters", "constrained", "max", "=", "0.62", "e", "A˚", "3", "min", "=", "0.36", "e", "A˚", "3", "1.924", "(3)", "1.950", "(2)", "1.976", "(2)", "2.007", "(3)", "D—H", "A", "172", "164", "152", "167", "metal-organic", "compounds", "Acta", "Cryst.", "(2010).", "E66,", "m1249–m1250", "doi:10.1107/S1600536810035919", "Gao", "and", "Wang", "m1249", "1.938", "(2)", "1.967", "(2)", "1.986", "(3)", "1.998", "(3)", "2.275", "(2)", "Cu1—N1", "Cu1—O1", "Cu1—N2", "Cu1—N3", "Table", "2", "Hydrogen-bond", "geometry", "(A˚", ",", ").", "D—H", "A", "O4—H4A", "O4—H4B", "C19—H19", "C21—H21", "O1i", "O5", "O4ii", "O5ii", "D—H", "0.91", "0.89", "0.93", "0.93", "H", "1.84", "1.97", "2.51", "2.53", "A", "D", "A", "2.745", "(3)", "2.839", "(5)", "3.355", "(5)", "3.437", "(7)", "Symmetry", "codes:", "(i)", "x", "þ", "1;", "y", "þ", "1;", "z", "þ", "1;", "(ii)", "x;", "y", "þ", "1;", "z.", "Data", "collection:", "SMART", "(Bruker,", "1998);", "cell", "refinement:", "SAINT", "(Bruker,", "1998);", "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", "and", "PLATON", "(Spek,", "2009).", "We", "acknowledge", "the", "financial", "support", "of", "the", "Science", "Foundation", "of", "Shandong.", "Supplementary", "data", "and", "figures", "for", "this", "paper", "are", "available", "from", "the", "IUCr", "electronic", "archives", "(Reference:", "JJ2053).", "References", "Bruker", "(1998).", "SMART", "and", "SAINT.", "Bruker", "AXS", "Inc.,", "Madison,", "Wisconsin,", "USA.", "Kou,", "H.", "Z.,", "Zhou,", "B.", "C.,", "Gao,", "S.", "&", "Wang,", "R.", "J.", "(1999).", "Angew.", "Chem.", "Int.", "Ed.", "42,", "3288–3291." ]

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[ "Fig.", "1", "supplementary", "materials", "sup-13" ]

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