Literature DB >> 22059067

3-[2-(2,6-Dichloro-anilino)benz-yl]-4-[(4-meth-oxy-benzyl-idene)amino]-1H-1,2,4-triazole-5(4H)-thione.

M Vinduvahini, K R Roopashree, Suman Bhattacharya, K Mohan Krishna, Venkatesh B Devaru.   

Abstract

In the title compound, C(23)H(19)Cl(2)N(5)OS, the triazole ring makes dihedral angles of 24.81 (18), 69.94 (19) and 35.68 (18)° with the dichloro-phenyl, benzene and meth-oxy-phenyl rings, respectively. An intra-molecular N-H⋯N hydrogen bond occurs. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds occur. In addition, there are weak C-H⋯π inter-actions involving the dichloro-phenyl and triazole rings.

Entities:  

Year:  2011        PMID： 22059067      PMCID： PMC3200723          DOI： 10.1107/S1600536811034799

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to Schiff bases, see: Dhar & Taploo (1982 ▶). For the biological and pharmaceutical activity of related compounds, see: Kiran et al. (2006 ▶); Shi et al. (2007 ▶); Dharmarajan et al. (2006 ▶); Hearn & Cynamon (2004 ▶); Dimova et al. (2001 ▶). For a related structure, see: Yang et al. (2005 ▶).

Experimental

Crystal data

C23H19Cl2N5OS M = 484.39 Triclinic, a = 7.9438 (4) Å b = 10.9163 (7) Å c = 14.0384 (8) Å α = 75.332 (5)° β = 75.807 (5)° γ = 88.410 (5)° V = 1140.98 (11) Å3 Z = 2 Mo Kα radiation μ = 0.40 mm−1 T = 293 K 0.22 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 ▶) T min = 0.790, T max = 1.000 7560 measured reflections 4009 independent reflections 2735 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.159 S = 1.06 4009 reflections 289 parameters H-atom parameters constrained Δρmax = 0.37 e Å−3 Δρmin = −0.44 e Å−3 Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034799/wn2450sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034799/wn2450Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811034799/wn2450Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H19Cl2N5OSZ = 2
Mr = 484.39F(000) = 500
Triclinic, P1Dx = 1.410 Mg m−3
Hall symbol: -P 1Melting point: 509 K
a = 7.9438 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.9163 (7) ÅCell parameters from 4009 reflections
c = 14.0384 (8) Åθ = 2.7–25.0°
α = 75.332 (5)°µ = 0.40 mm−1
β = 75.807 (5)°T = 293 K
γ = 88.410 (5)°Prism, colourless
V = 1140.98 (11) Å30.22 × 0.15 × 0.12 mm
Oxford Diffraction Xcalibur diffractometer4009 independent reflections
Radiation source: fine-focus sealed tube2735 reflections with I > 2σ(I)
graphiteRint = 0.025
Detector resolution: 15.9821 pixels mm-1θmax = 25.0°, θmin = 2.7°
ω scansh = −9→9
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)k = −12→12
Tmin = 0.790, Tmax = 1.000l = −16→16
7560 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0714P)2 + 0.2386P] where P = (Fo2 + 2Fc2)/3
4009 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.44 e Å−3
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05–01–2010 CrysAlis171. NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.Elemental analysis for C23H19Cl2N5OS (484): Calculated C 57.03, H 3.95, N 14.46; Found C 56.65, H 3.87, N 14.39. IR (ν cm-1, KBr): 3331 (NH), 2931 (C—H aliphatic), 1604 (C═N imine linkage), 1257 (C═S), 1153 (C—O of methoxy group). 1H NMR (DMSO):δ (p.p.m.) = 3.80 (s, 3H, 4- OCH3), 4.23 (s, 2H, Ar—CH2), 6.19 (s, 1H, Ar—NH), 7.27–6.97 (m, 5H, Ar—H), 7.35 (d, 2H, Ar—H), 7.48 (d, 2H, Ar—H), 7.64 (d, 2H, Ar—H), 9.85 (s, 1H, CH), 13.46 (s, 1H, NH). 13 C NMR:δ (p.p.m.) = 28.05 (Ar—CH2), 121–134 (aromatic carbons), 149.52 (C5-of 1,2,4-triazole), 161.65 (C of imine linkage), 163.17 (C3-of 1,2,4-triazole).
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
Cl1−0.18788 (15)0.88750 (10)0.85215 (8)0.0827 (4)
Cl20.24757 (15)0.78540 (10)1.10115 (8)0.0812 (4)
S30.22012 (14)0.90073 (10)0.41182 (7)0.0742 (3)
O41.0724 (3)0.4658 (2)0.3076 (2)0.0755 (7)
N50.1553 (4)0.8259 (2)0.89938 (19)0.0510 (7)
H50.18320.89400.85130.061*
N60.2131 (4)0.9612 (3)0.6750 (2)0.0594 (8)
N70.3781 (3)0.8614 (2)0.57024 (18)0.0495 (7)
N80.1506 (4)0.9675 (3)0.5909 (2)0.0597 (8)
H80.05721.00540.58210.072*
N90.5297 (4)0.8041 (3)0.53284 (19)0.0546 (7)
C10−0.2520 (6)0.8508 (3)1.1467 (3)0.0814 (14)
H10−0.34290.85621.20150.098*
C11−0.0915 (6)0.8223 (3)1.1616 (3)0.0696 (11)
H11−0.07260.80841.22620.083*
C120.0435 (5)0.8140 (3)1.0804 (3)0.0561 (9)
C130.0187 (4)0.8306 (3)0.9827 (2)0.0461 (8)
C14−0.1480 (5)0.8606 (3)0.9718 (3)0.0543 (9)
C15−0.2817 (5)0.8718 (3)1.0521 (3)0.0702 (11)
H15−0.39130.89341.04220.084*
C160.2500 (4)0.7173 (3)0.8888 (2)0.0464 (8)
C170.2012 (5)0.6003 (3)0.9570 (3)0.0574 (9)
H170.10390.59251.01110.069*
C180.2970 (6)0.4949 (3)0.9447 (3)0.0718 (11)
H180.26480.41710.99160.086*
C190.4378 (6)0.5039 (4)0.8646 (4)0.0759 (12)
H190.50030.43260.85600.091*
C200.4865 (5)0.6194 (4)0.7968 (3)0.0650 (10)
H200.58250.62500.74230.078*
C210.3969 (4)0.7281 (3)0.8072 (2)0.0494 (8)
C220.4599 (4)0.8547 (3)0.7349 (2)0.0547 (8)
H22A0.45750.91720.77350.066*
H22B0.57930.84880.69850.066*
C230.3522 (5)0.8972 (3)0.6606 (2)0.0521 (8)
C240.2465 (5)0.9101 (3)0.5241 (2)0.0544 (9)
C250.5168 (5)0.7271 (3)0.4798 (2)0.0581 (9)
H250.40860.71280.46940.070*
C260.6628 (5)0.6615 (3)0.4353 (2)0.0518 (8)
C270.8297 (5)0.6764 (3)0.4456 (2)0.0558 (9)
H270.85130.73160.48230.067*
C280.9630 (5)0.6107 (3)0.4021 (2)0.0573 (9)
H281.07450.62200.40910.069*
C290.9330 (5)0.5268 (3)0.3474 (2)0.0541 (8)
C300.7691 (5)0.5119 (3)0.3362 (3)0.0592 (9)
H300.74790.45640.29960.071*
C310.6365 (5)0.5787 (3)0.3789 (3)0.0640 (10)
H310.52590.56870.37000.077*
C321.0423 (6)0.3783 (5)0.2520 (4)0.1100 (17)
H32A1.14970.34090.22720.165*
H32B0.99730.42240.19560.165*
H32C0.95990.31300.29590.165*
U11U22U33U12U13U23
Cl10.0819 (8)0.0906 (7)0.1017 (8)0.0203 (6)−0.0537 (6)−0.0428 (6)
Cl20.0908 (8)0.0765 (7)0.0882 (7)0.0164 (6)−0.0510 (6)−0.0159 (5)
S30.0749 (7)0.0830 (7)0.0687 (6)0.0060 (6)−0.0279 (5)−0.0169 (5)
O40.0627 (17)0.0854 (18)0.0940 (18)0.0095 (14)−0.0230 (14)−0.0482 (15)
N50.0553 (18)0.0385 (14)0.0511 (15)0.0053 (12)−0.0086 (13)−0.0019 (12)
N60.061 (2)0.0668 (18)0.0522 (16)0.0066 (16)−0.0165 (14)−0.0156 (14)
N70.0478 (17)0.0534 (16)0.0455 (14)−0.0031 (13)−0.0115 (13)−0.0089 (12)
N80.0598 (19)0.0663 (18)0.0539 (16)0.0106 (15)−0.0212 (15)−0.0108 (14)
N90.0556 (19)0.0581 (17)0.0484 (15)0.0009 (14)−0.0095 (13)−0.0134 (13)
C100.088 (3)0.052 (2)0.075 (3)0.006 (2)0.022 (2)−0.004 (2)
C110.100 (3)0.049 (2)0.049 (2)0.010 (2)−0.009 (2)−0.0045 (16)
C120.070 (2)0.0380 (17)0.057 (2)0.0060 (16)−0.0170 (18)−0.0043 (15)
C130.054 (2)0.0304 (15)0.0510 (18)0.0007 (14)−0.0115 (16)−0.0068 (14)
C140.057 (2)0.0383 (17)0.071 (2)0.0026 (15)−0.0199 (19)−0.0160 (16)
C150.052 (2)0.051 (2)0.098 (3)0.0028 (17)−0.004 (2)−0.015 (2)
C160.0443 (19)0.0424 (17)0.0592 (19)0.0039 (15)−0.0234 (16)−0.0147 (15)
C170.060 (2)0.0435 (19)0.068 (2)−0.0002 (17)−0.0195 (18)−0.0086 (17)
C180.088 (3)0.045 (2)0.092 (3)0.011 (2)−0.043 (3)−0.017 (2)
C190.081 (3)0.063 (3)0.104 (3)0.035 (2)−0.049 (3)−0.036 (2)
C200.049 (2)0.083 (3)0.078 (2)0.022 (2)−0.0300 (19)−0.038 (2)
C210.0428 (19)0.059 (2)0.0560 (19)0.0041 (16)−0.0241 (16)−0.0199 (16)
C220.046 (2)0.071 (2)0.0493 (18)−0.0040 (17)−0.0130 (15)−0.0165 (17)
C230.055 (2)0.0539 (19)0.0455 (18)−0.0076 (17)−0.0093 (16)−0.0105 (15)
C240.056 (2)0.0509 (19)0.0497 (19)−0.0072 (17)−0.0087 (17)−0.0047 (16)
C250.055 (2)0.057 (2)0.059 (2)−0.0110 (17)−0.0118 (17)−0.0092 (18)
C260.055 (2)0.0504 (19)0.0457 (18)−0.0058 (17)−0.0056 (16)−0.0093 (15)
C270.066 (2)0.055 (2)0.0490 (19)−0.0101 (18)−0.0196 (17)−0.0111 (16)
C280.054 (2)0.062 (2)0.060 (2)0.0003 (18)−0.0215 (17)−0.0155 (17)
C290.059 (2)0.0513 (19)0.0526 (19)−0.0038 (17)−0.0164 (17)−0.0110 (16)
C300.059 (2)0.058 (2)0.066 (2)−0.0079 (18)−0.0129 (18)−0.0270 (17)
C310.054 (2)0.068 (2)0.074 (2)−0.0113 (19)−0.0163 (19)−0.0233 (19)
C320.078 (3)0.134 (4)0.151 (4)0.009 (3)−0.023 (3)−0.102 (4)
Cl1—C141.736 (3)C17—C181.385 (5)
Cl2—C121.722 (4)C17—H170.9300
S3—C241.668 (3)C18—C191.364 (5)
O4—C291.351 (4)C18—H180.9300
O4—C321.436 (5)C19—C201.372 (5)
N5—C131.398 (4)C19—H190.9300
N5—C161.406 (4)C20—C211.387 (4)
N5—H50.8600C20—H200.9300
N6—C231.291 (4)C21—C221.506 (5)
N6—N81.374 (4)C22—C231.485 (4)
N7—C241.387 (4)C22—H22A0.9700
N7—C231.387 (4)C22—H22B0.9700
N7—N91.390 (4)C25—C261.439 (5)
N8—C241.332 (4)C25—H250.9300
N8—H80.8600C26—C271.387 (5)
N9—C251.277 (4)C26—C311.394 (5)
C10—C111.358 (6)C27—C281.368 (5)
C10—C151.366 (6)C27—H270.9300
C10—H100.9300C28—C291.394 (5)
C11—C121.380 (5)C28—H280.9300
C11—H110.9300C29—C301.368 (5)
C12—C131.399 (4)C30—C311.368 (5)
C13—C141.392 (4)C30—H300.9300
C14—C151.374 (5)C31—H310.9300
C15—H150.9300C32—H32A0.9600
C16—C171.388 (4)C32—H32B0.9600
C16—C211.405 (4)C32—H32C0.9600
C29—O4—C32116.6 (3)C21—C20—H20119.0
C13—N5—C16124.4 (3)C20—C21—C16118.2 (3)
C13—N5—H5117.8C20—C21—C22120.7 (3)
C16—N5—H5117.8C16—C21—C22121.1 (3)
C23—N6—N8104.2 (3)C23—C22—C21112.3 (3)
C24—N7—C23108.2 (3)C23—C22—H22A109.2
C24—N7—N9130.0 (3)C21—C22—H22A109.2
C23—N7—N9121.0 (3)C23—C22—H22B109.2
C24—N8—N6114.6 (3)C21—C22—H22B109.2
C24—N8—H8122.7H22A—C22—H22B107.9
N6—N8—H8122.7N6—C23—N7110.6 (3)
C25—N9—N7116.4 (3)N6—C23—C22125.3 (3)
C11—C10—C15120.8 (4)N7—C23—C22123.8 (3)
C11—C10—H10119.6N8—C24—N7102.3 (3)
C15—C10—H10119.6N8—C24—S3129.5 (3)
C10—C11—C12119.7 (4)N7—C24—S3128.2 (3)
C10—C11—H11120.1N9—C25—C26122.7 (3)
C12—C11—H11120.1N9—C25—H25118.6
C11—C12—C13121.7 (4)C26—C25—H25118.6
C11—C12—Cl2118.4 (3)C27—C26—C31117.9 (3)
C13—C12—Cl2119.9 (3)C27—C26—C25123.3 (3)
C14—C13—N5121.6 (3)C31—C26—C25118.8 (3)
C14—C13—C12116.0 (3)C28—C27—C26120.6 (3)
N5—C13—C12122.3 (3)C28—C27—H27119.7
C15—C14—C13122.3 (3)C26—C27—H27119.7
C15—C14—Cl1118.8 (3)C27—C28—C29120.6 (3)
C13—C14—Cl1118.9 (3)C27—C28—H28119.7
C10—C15—C14119.4 (4)C29—C28—H28119.7
C10—C15—H15120.3O4—C29—C30124.3 (3)
C14—C15—H15120.3O4—C29—C28116.3 (3)
C17—C16—C21119.5 (3)C30—C29—C28119.4 (3)
C17—C16—N5121.5 (3)C31—C30—C29119.9 (3)
C21—C16—N5119.0 (3)C31—C30—H30120.0
C18—C17—C16120.2 (4)C29—C30—H30120.0
C18—C17—H17119.9C30—C31—C26121.7 (4)
C16—C17—H17119.9C30—C31—H31119.2
C19—C18—C17120.7 (4)C26—C31—H31119.2
C19—C18—H18119.7O4—C32—H32A109.5
C17—C18—H18119.7O4—C32—H32B109.5
C18—C19—C20119.3 (3)H32A—C32—H32B109.5
C18—C19—H19120.3O4—C32—H32C109.5
C20—C19—H19120.3H32A—C32—H32C109.5
C19—C20—C21122.1 (4)H32B—C32—H32C109.5
C19—C20—H20119.0
C23—N6—N8—C24−0.3 (4)C20—C21—C22—C23105.1 (4)
C24—N7—N9—C25−40.8 (4)C16—C21—C22—C23−77.1 (4)
C23—N7—N9—C25150.3 (3)N8—N6—C23—N7−0.8 (4)
C15—C10—C11—C12−0.2 (6)N8—N6—C23—C22−174.4 (3)
C10—C11—C12—C13−1.9 (5)C24—N7—C23—N61.5 (4)
C10—C11—C12—Cl2176.8 (3)N9—N7—C23—N6172.7 (3)
C16—N5—C13—C14−119.6 (3)C24—N7—C23—C22175.3 (3)
C16—N5—C13—C1264.8 (4)N9—N7—C23—C22−13.6 (5)
C11—C12—C13—C142.4 (5)C21—C22—C23—N687.7 (4)
Cl2—C12—C13—C14−176.3 (2)C21—C22—C23—N7−85.1 (4)
C11—C12—C13—N5178.2 (3)N6—N8—C24—N71.2 (4)
Cl2—C12—C13—N5−0.5 (4)N6—N8—C24—S3−177.5 (3)
N5—C13—C14—C15−176.7 (3)C23—N7—C24—N8−1.6 (3)
C12—C13—C14—C15−0.9 (5)N9—N7—C24—N8−171.6 (3)
N5—C13—C14—Cl12.2 (4)C23—N7—C24—S3177.1 (2)
C12—C13—C14—Cl1178.1 (2)N9—N7—C24—S37.1 (5)
C11—C10—C15—C141.6 (6)N7—N9—C25—C26179.4 (3)
C13—C14—C15—C10−1.1 (5)N9—C25—C26—C27−0.4 (5)
Cl1—C14—C15—C10180.0 (3)N9—C25—C26—C31179.7 (3)
C13—N5—C16—C177.4 (5)C31—C26—C27—C28−0.6 (5)
C13—N5—C16—C21−172.8 (3)C25—C26—C27—C28179.5 (3)
C21—C16—C17—C180.2 (5)C26—C27—C28—C29−0.5 (5)
N5—C16—C17—C18180.0 (3)C32—O4—C29—C30−1.3 (5)
C16—C17—C18—C19−1.4 (6)C32—O4—C29—C28179.4 (4)
C17—C18—C19—C201.2 (6)C27—C28—C29—O4−179.7 (3)
C18—C19—C20—C210.2 (6)C27—C28—C29—C300.9 (5)
C19—C20—C21—C16−1.4 (5)O4—C29—C30—C31−179.5 (3)
C19—C20—C21—C22176.4 (3)C28—C29—C30—C31−0.3 (5)
C17—C16—C21—C201.2 (4)C29—C30—C31—C26−0.8 (5)
N5—C16—C21—C20−178.6 (3)C27—C26—C31—C301.2 (5)
C17—C16—C21—C22−176.6 (3)C25—C26—C31—C30−178.9 (3)
N5—C16—C21—C223.6 (4)
Cg1 is the centroid of the triazole ring.
D—H···AD—HH···AD···AD—H···A
N5—H5···N60.862.353.047 (4)139
N8—H8···S3i0.862.403.246 (3)170
C11—H11···Cg1ii0.932.793.465 (4)125
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the triazole ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N5—H5⋯N60.862.353.047 (4)139
N8—H8⋯S3i0.862.403.246 (3)170
C11—H11⋯Cg1ii0.932.793.465 (4)125

Symmetry codes: (i) ; (ii) .

  5 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde.

Authors:  Lei Shi; Hui-Ming Ge; Shu-Hua Tan; Huan-Qiu Li; Yong-Chun Song; Hai-Liang Zhu; Ren-Xiang Tan
Journal:  Eur J Med Chem       Date:  2006-11-29       Impact factor: 6.514

3.  Synthesis, characterization and biological studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with bidentate Schiff bases derived by heterocyclic ketone.

Authors:  Kiran Singh; Manjeet Singh Barwa; Parikshit Tyagi
Journal:  Eur J Med Chem       Date:  2005-11-03       Impact factor: 6.514

4.  Abacavir prodrugs: microwave-assisted synthesis and their evaluation of anti-HIV activities.

Authors:  Dharmarajan Sriram; Perumal Yogeeswari; Naga Sirisha Myneedu; Vivek Saraswat
Journal:  Bioorg Med Chem Lett       Date:  2006-02-03       Impact factor: 2.823

5.  Design and synthesis of antituberculars: preparation and evaluation against Mycobacterium tuberculosis of an isoniazid Schiff base.

Authors:  Michael J Hearn; Michael H Cynamon
Journal:  J Antimicrob Chemother       Date:  2003-12-19       Impact factor: 5.790
  5 in total
  3 in total

1.  4-[(E)-(4-Chloro-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Authors:  B K Sarojini; P S Manjula; Manpreet Kaur; Brian J Anderson; Jerry P Jasinski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-12-14

2.  4-[(E)-(4-Hy-droxy-benzyl-idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione.

Authors:  Balladka K Sarojini; Padmanabha S Manjula; B Narayana; Jerry P Jasinski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-05-31

3.  Crystal structure of 4-[(E)-(4-chloro-benzyl-idene)amino]-3-(2-methyl-benz-yl)-1H-1,2,4-triazole-5(4H)-thione.

Authors:  B K Sarojini; P S Manjula; B Narayana; Sumati Anthal; Rajni Kant
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-08-16
  3 in total

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