Synthesis, Crystal Structure and Non-covalent Interactions Analysis of Novel N-Substituted Thiosemicarbazone

doi:10.1007/s40242-019-8354-8

高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (3): 471-477.doi: 10.1007/s40242-019-8354-8

Synthesis, Crystal Structure and Non-covalent Interactions Analysis of Novel N-Substituted Thiosemicarbazone

ZHANG Xing¹, HUANG Jie¹, ZHANG Yu¹, QI Fan¹, WANG Sifan¹, SONG Jirong²

1. Shaanxi Key Laboratory of Physico-inorganic Chemistry, School of Chemical Engineering, Northwest University, Xi'an 710069, P. R. China;
2. Ministry of Science and Technology, the Palace Museum, Beijing 100009, P. R. China

收稿日期:2018-11-09 修回日期:2018-12-10 出版日期:2019-06-01 发布日期:2019-02-25
通讯作者: HUANG Jie E-mail:huangjie@nwu.edu.cn
基金资助:
Supported by the Science and Technology Program of Shaanxi Province, China(No.2013K02-25), the Science and Techno- logy Program of Xi'an City, China(No.NC1404), the Science and Technology Research and Development Program of Shaanxi Province, China(No.14JF025) and the Natural Science Basic Research of Shaanxi Province, China(No.2018.JM2061).

Synthesis, Crystal Structure and Non-covalent Interactions Analysis of Novel N-Substituted Thiosemicarbazone

ZHANG Xing¹, HUANG Jie¹, ZHANG Yu¹, QI Fan¹, WANG Sifan¹, SONG Jirong²

1. Shaanxi Key Laboratory of Physico-inorganic Chemistry, School of Chemical Engineering, Northwest University, Xi'an 710069, P. R. China;
2. Ministry of Science and Technology, the Palace Museum, Beijing 100009, P. R. China

Received:2018-11-09 Revised:2018-12-10 Online:2019-06-01 Published:2019-02-25
Contact: HUANG Jie E-mail:huangjie@nwu.edu.cn
Supported by:
Supported by the Science and Technology Program of Shaanxi Province, China(No.2013K02-25), the Science and Techno- logy Program of Xi'an City, China(No.NC1404), the Science and Technology Research and Development Program of Shaanxi Province, China(No.14JF025) and the Natural Science Basic Research of Shaanxi Province, China(No.2018.JM2061).

摘要/Abstract

摘要： (E)-1-(4-Fluorobenzylidene)-4-(4-ethylphenyl)thiosemicarbazone was synthesized via the reaction of 4-(4-ethylphenyl)thiosemicarbazide and 4-fluorobenzaldehyde. The title compound was characterized by FTIR, ¹H and ¹³C NMR, mass spectrometry and elemental analysis techniques. Structural property of the title compound was displayed by the X-ray single crystal diffraction. The title compound crystallized in triclinic space group P1 with a=0.6494(4) nm, b=0.7971(5) nm, c=1.5492(10) nm, α=83.690(11)°, β=84.185(10)°, γ=84.348(11)°, molecular formula C₁₆H₁₆FN₃S, M_r=301.39, V=0.7868(9) nm³, Z=2, D_c=1.272 g/cm³, F(000)=316, μ=0.213 mm^-1, S=1.02, R=0.0513, and ωR[I>2σ(I)]=0.1662. The intermolecular interactions in the crystal structure were explained using the Hirshfeld surface and their associated two-dimensional fingerprint plots. The title compound showed C-H···S(1-x, -y, -z) and N-H···S(1-x, -y, -z) intermolecular interactions, and formed the supramolecular self-assemblies through R₂²(12) and R₂²(8) ring motifs. Shape index and curvedness were performed to further understand some unique weak interactions, for instance, the weak π…π stacking contacts in molecular structure with different characteristic regions. Besides, the reduced density gradient(RDG) function provided a real-space function for discussing non-covalent interactions within molecule, such as hydrogen bonds, weak van der Waals interactions and attractive or repulsive effects.

关键词: Novel N-substituted thiosemicarbazone, Non-covalent interaction, Reduced desity gradient(RDG) function, Hirshfeld surface analysis

Abstract: (E)-1-(4-Fluorobenzylidene)-4-(4-ethylphenyl)thiosemicarbazone was synthesized via the reaction of 4-(4-ethylphenyl)thiosemicarbazide and 4-fluorobenzaldehyde. The title compound was characterized by FTIR, ¹H and ¹³C NMR, mass spectrometry and elemental analysis techniques. Structural property of the title compound was displayed by the X-ray single crystal diffraction. The title compound crystallized in triclinic space group P1 with a=0.6494(4) nm, b=0.7971(5) nm, c=1.5492(10) nm, α=83.690(11)°, β=84.185(10)°, γ=84.348(11)°, molecular formula C₁₆H₁₆FN₃S, M_r=301.39, V=0.7868(9) nm³, Z=2, D_c=1.272 g/cm³, F(000)=316, μ=0.213 mm^-1, S=1.02, R=0.0513, and ωR[I>2σ(I)]=0.1662. The intermolecular interactions in the crystal structure were explained using the Hirshfeld surface and their associated two-dimensional fingerprint plots. The title compound showed C-H···S(1-x, -y, -z) and N-H···S(1-x, -y, -z) intermolecular interactions, and formed the supramolecular self-assemblies through R₂²(12) and R₂²(8) ring motifs. Shape index and curvedness were performed to further understand some unique weak interactions, for instance, the weak π…π stacking contacts in molecular structure with different characteristic regions. Besides, the reduced density gradient(RDG) function provided a real-space function for discussing non-covalent interactions within molecule, such as hydrogen bonds, weak van der Waals interactions and attractive or repulsive effects.

Key words: Novel N-substituted thiosemicarbazone, Non-covalent interaction, Reduced desity gradient(RDG) function, Hirshfeld surface analysis

ZHANG Xing, HUANG Jie, ZHANG Yu, QI Fan, WANG Sifan, SONG Jirong. Synthesis, Crystal Structure and Non-covalent Interactions Analysis of Novel N-Substituted Thiosemicarbazone[J]. 高等学校化学研究, 2019, 35(3): 471-477.

参考文献 49

[1]	Salman A. K., Praveen K., Eur. J. Med. Chem., 2008, 43, 2029
[2]	Vijey A. M., Shiny G., Vaidhyalingam V., J. Arkvioc., 2008, 41, 187
[3]	Rauf M. K., Talib A., Badshah A., Zaib S., Shoaid K., Floerke U., Imtiazed-Din U., Iqbal J., Eur. J. Med. Chem., 2013, 70, 487
[4]	Saeed A., Shaheen U., Hameed A., HaiderNaqvi S. Z., J. Flour. Chem., 2009, 130, 1028
[5]	Saeed A., Rashid N., Jones P. G., Al M., Hussain R., Eur. J. Med. Chem., 2010, 45, 1323
[6]	Andreas J. K., Eur. J. Med. Chem., 2011, 46, 1656
[7]	Wang B., Ma Y., Xiong L., Li Z., Chin. J. Chem., 2012, 30, 815
[8]	Bielenica A., Stefańska J., Stnpień K., Napiórkowska A., Augustynowicz-Kopen E., Sanna G., Madeddu S., Boi S., Giliberti G., Wrzosek M., Struga M., Eur. J. Med. Chem., 2015, 101, 111
[9]	Rauf M. K., Zaib S., Talib A., Ebihara A., Badshah A., Bolte M., Iqbal J., Bioorg. Med. Chem. Lett., 2016, 24, 4452
[10]	Samir G., Anup K. M., Gitika B., Khan M. M., Khanna A. K., Med. Chem. Lett., 2009, 19, 3863
[11]	Dipankar M., Subhendu N., Michael G. B. D., Shyamal K. C., J. Polyhedron., 2005, 24, 1861
[12]	Tevfik A., Erdal O., J. Termochim. Acta, 1995, 254, 371
[13]	Nez-Montenegro A., Carballo R., Ezequiel M., Vázquez-López., J. Polyhedron., 2009, 28, 3915
[14]	Aridoss G., Amirthaganesan S., Kim M. S., Kim J. T., Jeong Y. T., Eur. J. Med. Chem., 2009, 44, 3499
[15]	Neelam B., Fareeda A., Manna R. M., Amir A., J. Bioorg. Med. Chem. Lett., 2004, 12, 4679
[16]	Kakul H., Mohammad A., Amir A., Eur. J. Med. Chem., 2007, 35, 1300
[17]	Kakul H., Abdul R., Amir A., Eur. J. Med. Chem., 2008, 43, 2016
[18]	Lobana T. S., Sharma R., Bawa G., Khanna S., Coord. Chem. Rev., 2009, 253, 977
[19]	Guo Z. L., Richardson D. R., Kalinowski D. S., Kovacevic Z., Tan-Un K. C., Chan C. F. G., Journal of Hematology & Oncology, 2016, 1, 98
[20]	Bomfim L. F. O., Barbosa R. S., Burgos C. A. E., Rodrigues B. L., Teixeira R. L., J. Mol. Struct., 2017, 1150, 44
[21]	Saeed A., Bolte M., Erben M. F., Pérez H., CrystEngComm., 2015, 17, 7551
[22]	Cairo R. R., Stevens A. M. P., Oliveira T. D. D., Batista A. A., Castellano E. E., Duque J., Soria D. B., Fantoni A. C., Corrêa R. S., Erben M. F., Spectrochim. Acta A, 2017, 176, 8
[23]	McKinnon J. J., Jayatilaka D., Spackman M. A., Chem. Commun., 2007, 37, 3814
[24]	SpackmanM. A., Jayatilaka D., Cryst. Eng. Comm., 2009, 11, 19
[25]	Spackman M. A., Phys. Scr., 2013, 87, 48
[26]	McKinnon J. J., Spackman M. A., Mitchell A. S., Acta Crystallogr., 2004, 60, 627
[27]	McKinnon J. J., Fabbiani F. P. A., Spackman M. A., Cryst. Growth Des., 2007, 7, 755
[28]	Seth S. K., Saha I., Estarellas C., Frontera A., Kar T., Mukhopadhyay S., Cryst. Growth. Des., 2011, 11, 3250
[29]	Saeed A., Khurshid A., Bolte M., Fantoni A. C., Erben M. F., Spectrochim. Acta. A, 2015, 143, 59
[30]	Johnson E. R., Keinan S., Mori-Sanchez P., Contreras-Garcia J., Cohen A. J., Yang W. T., J. Am. Chem. Soc., 2010, 132, 6498
[31]	Meyer E. A., Castellano P. K., Diederich F., Angew. Chem. Int. Ed., 2003, 42, 1210
[32]	Steiner T., Angew. Chem. Int. Ed., 2002, 41, 48
[33]	Erdelyi M., Chem. Soc. Rev., 2012, 41, 3547
[34]	Parisini E., Metrangolo P., Pilati T., Resnati G., Terraneo G., Chem. Soc. Rev., 2011, 40, 2267
[35]	Gumus I. U., Solmaz., Binzet G., Keskin E., Arslan B., Arslan H., J. Mol. Struct. 2018, 1157, 78
[36]	Samanta T., Dey L., Dinda J., Chattopadhyay S. K., Seth S. K., J. Mol. Struct., 2014, 1068, 58
[37]	Sheldrick G.M., SHELXL-97, Program for X-ray Crystal Structure Refinement, University of Göttingen, Göttingen, 1997
[38]	Spek A. L., Acta Crystallogr., 2009, D65, 148
[39]	Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J. A. Jr., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R. L., Fox D. J., Keith T., AleLaham M. A., Peng C. Y., Nanayakkara A., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C., Pople J. A., Gaussian 09. Revision D.01, Gaussian Inc., Wallingford, CT 2009
[40]	Frisch M. J., Pople J. A., Binkley J. S., J. Chem. Phys., 1984, 80, 3265
[41]	Wolff S K., Grimwood D. J., McKinnon J. J., Turner M. J., Jayatilaka D., Spackman, M. A., Crystal Explorer Version 3.1., University of Western Australia, Perth, 2012
[42]	Qiao L., Huang J., Hu W., Zhang Y., Guo J. J., Cao W. L., Miao K. H., Qin B. F., Song J. R., J. Mol. Struct., 2017, 1139, 149
[43]	Qiao L., Zhang Y., Hu W., Guo J. J., Cao W. L., Ding Z. M., Guo Z. W., Fan A., Song J. R., Huang J., J. Mol. Struct., 2017, 1141, 309
[44]	Qiao L., Huang J., Hu W., Zhang Y., Qin B. F., Song J. R., GaoY., Chin. J. Struct. Chem., 2017, 11, 1759
[45]	Zhang Y., Hu W., Qiao L., Zhang X., Song J. R., Huang J., Chin. J. Struct. Chem., 2018, 37, 693
[46]	Kinnon M. J. J., Spackman M. A., Mitchell A. S., Acta Crystallogr. Sect. B:Struct. Sci., 2004, 60, 627
[47]	Manna P., Seth S. K., Das A., Hemming J., Prendergast R., Helliwell M., Choudhury S. R., Frontera A., Mukhopadhyay S., Inorg. Chem., 2012, 51, 3557
[48]	Sun Y., Fu S., Zhang J., Wang X., Wang D. Acta Cryst., 2009, 65, 237
[49]	Bourosh P. N., Revenko M. D., Gdaniec M., Stratulat E. F., Simonov Y. A., J. Struct. Chem., 2009, 50, 510

Synthesis, Crystal Structure and Non-covalent Interactions Analysis of Novel N-Substituted Thiosemicarbazone

Synthesis, Crystal Structure and Non-covalent Interactions Analysis of Novel N-Substituted Thiosemicarbazone

可视化

摘要/Abstract

引用本文

使用本文

参考文献 49

相关文章 2

编辑推荐

Metrics

本文评价

[1]	WANG Dawei, WANG Ying, ZHUANG Changfu, ZHAO Ping, YANG Jing, SHI Zhengjun. Two Zinc(Ⅱ) Complexes Based on Trans-(1R,2R)-cyclohexanediamine: Molecular Structure Analyses and Preparation of Composite Membrane[J]. 高等学校化学研究, 2019, 35(5): 749-754.
[2]	Nabaa BOUZIDIA, Besma HAMDI, Abdelhamid BEN SALAH. A New Non-centrosymmetric Microporous Fluorinated Iron Phosphate: Structural Elucidation, Spectroscopic Study and Hirshfeld Surface Analysis[J]. 高等学校化学研究, 2016, 32(4): 519-526.