Crystal structure of benzylthiazolo[5,4 b]pyridin 2 yl diazene, C13H10N4S Shi Hui Li, Rui Zhang* and Meng Yin Zhang College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 47[.]
Z Kristallogr NCS 230 (2015) 115-116 / DOI 10.1515/ncrs-2014-9090 115 © 2015 Walter de Gruyter GmbH, Berlin/Munich/Boston Crystal structure of benzylthiazolo[5,4-b]pyridin-2-yl-diazene, C13H10N4S Shi-Hui Li, Rui Zhang* and Meng-Yin Zhang College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, Henan Province, P R China Received November 05, 2014, accepted April 02, 2015, available online April 09, 2015, CCDC no 1267/4298 Abstract C13H10N4S, monoclinic, P21/c (no 14), a = 9.184(7) Å, b = 11.094(8) Å, c = 12.109(9) Å, ' = 104.287(8)°, V = 1195.6 Å3, Z = 4, Rgt(F) = 0.0303, wRref(F2) = 0.0847, T = 296 K Table Data collection and handling Crystal: Wavelength: -: Diffractometer, scan mode: 2+max: N(hkl)measured, N(hkl)unique: Criterion for Iobs, N(hkl)gt: N(param)refined: Programs: colourless blocks, size 0.23$0.31$0.36 mm Mo K, radiation (0.71073 Å) 2.56 cm)1 CCD area detector, ! and " 51° 8591, 2219 Iobs > &(Iobs), 1900 163 SHELX [15] Source of material The title compound was obtained from 2-amin-3-chloropyridine according to the literature method [14] Single crystals suitable for X-ray diffraction were obtained by crystallization of the title compound from methanol tioxidant activities [1–8] Meanwhile, hydrazones have also interesting properties because of the presence of several coordination sites, and thus their metal complexes are important for their possible biological applications [9] The thiazole ring is present in various biologically active molecules Thiazoles and their derivatives possess activities such as antitumor, antiviral, and antibacterial [10–12] In this paper we report the synthesis and crystal structure of a novel thiazolehydrazone compound The asymmetric unit contains one molecule of the title compound, which is constructed by the pyridinethiazole moiety, the hydrazone linker, and the bimethyl moiety The C7–N3, N3–N4, and C8–N4 bond lengths are 1.349(2) Å, 1.3736(19) Å, and 1.287(2) Å, respectively, which is in accord to similar compounds [e.g 13] The C6–S1 and C7–S1 bond lengths of 1.7581(19) Å and 1.7650(19) Å are shorter than the expected single bond value, showing some double bond character The C7–S1–C6 angle is 87.25(8)°, which is smaller than in simple thiazoles The S1–C6–N1–C4 torsion angles is 0.9(2)° In the crystal structure, adjacent molecules are linked by intermolecular N3–H3A -N1i hydrogen bond into one-dimensional chains along the c axis The distance of H3A -N1 is 2.00 Å, and the angle of N3–H3A -N1 is 174.7° Symmetry code i: x, –y+½, z-½ Table Atomic coordinates and displacement parameters (in Å2) Atom Site x H(2) H(3) H(4) H(8) H(10) H(11) H(12) H(13) H(14) H(3A) 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 1.3076 1.3380 1.1929 0.8351 0.6696 0.4725 0.3456 0.4192 0.6161 0.9781 y 0.0404 )0.0873 )0.0654 0.5585 0.7257 0.8528 0.8286 0.6795 0.5531 0.4029 z Uiso 0.9682 1.1239 1.2504 0.7641 0.6931 0.7013 0.8424 0.9789 0.9726 0.8103 0.054 0.062 0.062 0.045 0.049 0.057 0.060 0.061 0.053 0.054 Experimental details The hydrogen atoms were assigned with isotropic displacement factors Uiso(H) = 1.2Ueq (N and pyridine C), or Uiso(H) = 1.5Ueq (methyl C) and included in the final refinement by using geometrical restraints, with C–H = 0.93 Å (pyridine) or C–H = 0.96 Å (methyl), and N–H = 0.86 Å Discussion Hydrazones are an emerging class of materials, which have been demonstrated to possess a wide range of biological and pharmaceutical activities such as antimicrobial, anti-convulsant, antifungal, anticancer, antitubercular, antiviral, antibacterial, and an _ * Correspondence author (e-mail: zhangruihxx@126.com) Unauthenticated Download Date | 1/9/17 3:14 AM 116 C13H10N4S Table Atomic coordinates and displacement parameters (in Å2) Atom Site x C(1) C(2) C(3) C(4) C(6) C(7) C(8) C(9) C(10) C(11) C(12) C(13) C(14) N(1) N(2) N(3) N(4) S(1) 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 1.1404(2) 1.2489(2) 1.2662(2) 1.1783(2) 1.0575(2) 0.9989(2) 0.7856(2) 0.6626(2) 0.6192(2) 0.5009(2) 0.4256(2) 0.4693(2) 0.5869(2) 1.0720(2) 1.1046(2) 0.9423(2) 0.8273(1) 0.92952(5) y 0.1393(1) 0.0492(2) )0.0264(2) )0.0126(2) 0.1460(1) 0.2944(1) 0.5442(1) 0.6242(1) 0.7158(1) 0.7920(2) 0.7781(2) 0.6884(2) 0.6125(2) 0.0735(1) 0.2242(1) 0.3867(1) 0.4547(1) 0.26650(4) z U11 U22 U33 1.0071(1) 1.0202(1) 1.1128(2) 1.1890(2) 1.0902(1) 0.9379(1) 0.8212(1) 0.8309(1) 0.7503(1) 0.7553(2) 0.8400(2) 0.9214(2) 0.9174(2) 1.1792(1) 0.9206(1) 0.8680(1) 0.8893(1) 1.05907(4) 0.0378(8) 0.0421(9) 0.051(1) 0.057(1) 0.0372(8) 0.0347(8) 0.0368(8) 0.0343(8) 0.0445(9) 0.052(1) 0.044(1) 0.049(1) 0.0466(9) 0.0529(9) 0.0396(7) 0.0463(8) 0.0349(7) 0.0423(2) 0.0366(8) 0.046(1) 0.0416(9) 0.045(1) 0.0363(8) 0.0365(8) 0.0374(8) 0.0321(8) 0.0393(9) 0.0389(9) 0.047(1) 0.054(1) 0.0419(9) 0.0441(8) 0.0421(8) 0.0472(8) 0.0370(7) 0.0406(2) 0.0357(8) 0.047(1) 0.058(1) 0.048(1) 0.0370(8) 0.0377(8) 0.0400(8) 0.0427(9) 0.0388(9) 0.049(1) 0.059(1) 0.055(1) 0.0469(9) 0.0419(8) 0.0385(7) 0.0452(8) 0.0459(8) 0.0469(3) Acknowledgments This work was supported from the Administration of Science and Technology of Henan province P R China (grant no 132102310257) References Ajani, O.O.; Obafemi, C A.; Nwinyi, O C.; Akinpelu, D A: Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3hydrazone derivatives Bioorg Med Chem 18 (2010) 214–221 Dimmock, J R.; Vashishtha, S C.; Stables, J P.: Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds Eur J Med Chem 35 (2000) 241–248 Loncle, C.; Brunel, J M.; Vidal, N.; Dherbomez, M.; Letourneux, Y.: Synthesis and antifungal activity of cholesterol-hydrazone derivatives Eur J Med Chem 39 (2004) 1067–1071 Zheng, L W.; Wu, L L.; Zhao, B X.; Dong, W L.; Miao, J Y.: Synthesis of novel substituted pyrazole-5-carbohydrazide hydrazone derivatives and discovery of a potent apoptosis inducer in A549 lung cancer cells Bioorg Med Chem 17 (2009) 1957–1962 Gemma, S.; 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397–408 15 Sheldrick, G M.: A short history of SHELX Acta Crystallogr A64 (2008) 112–122 Unauthenticated Download Date | 1/9/17 3:14 AM ... 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 1. 140 4 (2) 1. 24 8 9 (2) 1 .26 62( 2) 1.1783 (2) 1. 057 5 (2) 0.9989 (2) 0.7 856 (2) 0.6 626 (2) 0.61 92( 2) 0 .50 09 (2) 0 .4 25 6 (2) 0 .46 93 (2) 0 .58 69 (2) 1.0 720 (2) 1.1 046 (2) ... 1.1 046 (2) 0. 9 42 3 (2) 0. 827 3(1) 0. 92 9 52 (5) y 0.1393(1) 0. 049 2( 2) )0. 02 64( 2) )0.0 126 (2) 0. 146 0(1) 0 .2 944 (1) 0 . 54 42( 1) 0.6 24 2 (1) 0.7 158 (1) 0.7 920 (2) 0.7781 (2) 0.68 84( 2) 0.61 25 ( 2) 0.07 35( 1) 0 .2 2 42 (1) 0.3867(1)... 0.3867(1) 0. 45 4 7(1) 0 .26 650 (4) z U11 U 22 U33 1.0071(1) 1. 020 2(1) 1.1 128 (2) 1.1890 (2) 1.09 02( 1) 0.9379(1) 0. 821 2(1) 0.8309(1) 0. 750 3(1) 0. 755 3 (2) 0. 840 0 (2) 0. 92 14( 2) 0.91 74( 2) 1.17 92( 1) 0. 920 6(1) 0.8680(1)