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Journal of Chemical Crystallography

, Volume 37, Issue 6, pp 399–405 | Cite as

Syntheses and crystal structures of an organometallic thiosemicarbazone and an organometallic enehydrazide

  • Yao-Cheng Shi
  • Hong-Jian Cheng
  • Chun-Xia Sui
  • Bei-Bei Zhu
Article

Reactions of ferrocenoylacetone with thiosemicarbazide and isonicotinic acid hydrazide generate an organometallic thiosemicarbazone 1 and enehydrazide 2, respectively. The complexes 1 and 2, which can be formulated as [C5H5FeC5H4C(O)CH2C(=NNHCSNH2)CH3] and [C5H5FeC5H4C(O)CH=C(NHNHCOC5H4N-4)CH3], have been characterized by elemental analyses, IR, NMR, UV and were structurally characterized by single-crystal X-ray crystallography.

Complex 1 (C15H17FeN3OS) crystallizes in the monoclinic space group P21/c, with lattice constants: a = 13.939(3) Å, b = 8.2600(17) Å, c = 13.176(3) Å, β = 94.83(3)°, V = 1511.7(6) Å3, Z = 4, D c = 1.508 g cm−3, F(000) = 712, R 1 = 0.0602, wR 2 = 0.1526.

Two intermolecular hydrogen bonds N–H···S (N···S = 3.356(8) and 3.499(7) Å, N–H···S = 168 and 170°) form a chain in the [010] direction. The intermolecular hydrogen bond C–H···O (C···O = 3.432(10) Å, C–H···O = 151°) leads to a [010] double-chain through each unit cell. The intermolecular hydrogen bond C–H···O (C···O = 3.359(10) Å, C–H···O = 173°) makes the [010] double-chain pack along the c axis to result in a two-dimensional network.

Complex 2 (C20H19FeN3O2) crystallizes in the monoclinic space group P21/c, with lattice constants: a = 14.091(2) Å, b = 10.024(2) Å, c = 13.806(2) Å, β = 112.41(2)°, V = 1802.8(6) Å3, Z = 4, D c = 1.434 g cm−3, F(000) = 808, R 1 = 0.0576, wR 2 = 0.1593. The strong intramolecular hydrogen bond N–H···O from the enamine N atom and carbonyl O atom stabilizes the enehydrazide. The intermolecular hydrogen bonds N–H···O and C–H···O (N···O = 2.906(6) Å, N–H···O = 155° C···O = 3.364(6) Å, C–H···O = 153°) generate a [010] chain.

The intermolecular hydrogen bond N–H···O (N···O = 2.989(6) Å, N–H···O = 128°) forms a [010] double-chain through each unit cell. The π···π stacking interation involving the pyridyl groups makes the [010] double-chain pack along the c axis to lead to a two-dimensional network.

KEY WORDS:

Ferrocenoylacetone hydrazide thiosemicarbazone enehydrazide X-ray crystallography. 

Notes

Acknowledgments

The authors thank the National Nature Science Foundation of China (No. 20572091) and Nature Science Foundation of Jiangsu Province (No. 05KJB150151) for financial support of this work.

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Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Yao-Cheng Shi
    • 1
  • Hong-Jian Cheng
    • 1
  • Chun-Xia Sui
    • 1
  • Bei-Bei Zhu
    • 1
  1. 1.School of Chemistry, Yangzhou UniversityYangzhouP.R. China

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