3-Benzyl-4-(4-chloro­phenyl)-1H-1,2,4-triazole-5(4H)-thione

In the title mol­ecule, C₁₅H₁₂ClN₃S, the dihedral angles made by the substituted phenyl and benzyl rings with the triazole ring are 81.39 (10) and 63.59 (10)°, respectively. The crystal structure is stabilized by N—H...S, C—H...Cl and C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.073
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B    ..  CG1     ..       2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  CG1     ..       3.00 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Benzyl-4-(4-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione

Crystal data

C15H12ClN3S	F(000) = 624
Mr = 301.80	Dx = 1.404 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 124 reflections
a = 9.181 (5) Å	θ = 6.0–20.0°
b = 17.803 (5) Å	µ = 0.41 mm^−1
c = 9.231 (5) Å	T = 100 K
β = 108.882 (5)°	Block, colorless
V = 1427.6 (12) Å^3	0.25 × 0.21 × 0.18 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD diffractometer	3388 independent reflections
Radiation source: fine-focus sealed tube	2378 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
Detector resolution: 9 pixels mm^-1	θmax = 28.0°, θmin = 3.8°
ω scans with 1.90° and 57 sec per frame	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −23→22
Tmin = 0.905, Tmax = 0.930	l = −12→12
18622 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0253P)^2 + 0.481P] where P = (Fo^2 + 2Fc^2)/3
3388 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.16094 (6)	0.35119 (3)	0.54003 (6)	0.0259 (2)
S1	0.35470 (5)	0.10465 (3)	0.43408 (5)	0.0158 (1)
N1	0.20236 (16)	0.06995 (8)	0.63748 (16)	0.0115 (4)
N2	0.37330 (16)	−0.01059 (8)	0.63514 (17)	0.0132 (4)
N3	0.30688 (16)	−0.03810 (8)	0.73894 (17)	0.0138 (5)
C1	0.31301 (19)	0.05415 (10)	0.5704 (2)	0.0123 (5)
C2	0.20225 (19)	0.01192 (10)	0.7377 (2)	0.0124 (5)
C3	0.0925 (2)	0.00649 (10)	0.8270 (2)	0.0145 (5)
C4	0.1290 (2)	−0.05968 (10)	0.9360 (2)	0.0135 (5)
C5	0.2515 (2)	−0.05669 (11)	1.0730 (2)	0.0212 (6)
C6	0.2859 (2)	−0.11829 (11)	1.1704 (2)	0.0233 (6)
C7	0.1990 (2)	−0.18354 (11)	1.1324 (2)	0.0220 (6)
C8	0.0766 (2)	−0.18657 (11)	0.9982 (2)	0.0191 (6)
C9	0.0417 (2)	−0.12482 (10)	0.9000 (2)	0.0164 (6)
C10	0.11292 (19)	0.13835 (10)	0.61281 (19)	0.0119 (5)
C11	0.1888 (2)	0.20622 (10)	0.6535 (2)	0.0143 (6)
C12	0.1040 (2)	0.27246 (10)	0.6295 (2)	0.0159 (6)
C13	−0.0543 (2)	0.26845 (10)	0.5658 (2)	0.0160 (6)
C14	−0.1310 (2)	0.20083 (11)	0.5239 (2)	0.0176 (6)
C15	−0.0455 (2)	0.13491 (10)	0.5477 (2)	0.0164 (6)
H2	0.44680	−0.03320	0.61420	0.0160*
H3A	−0.01150	0.00130	0.75660	0.0170*
H3B	0.09720	0.05240	0.88480	0.0170*
H5	0.31040	−0.01320	1.09910	0.0250*
H6	0.36760	−0.11580	1.26170	0.0280*
H7	0.22330	−0.22500	1.19710	0.0260*
H8	0.01710	−0.22990	0.97300	0.0230*
H9	−0.04090	−0.12730	0.80950	0.0200*
H11	0.29540	0.20750	0.69640	0.0170*
H12	0.15290	0.31860	0.65580	0.0190*
H14	−0.23760	0.19960	0.48070	0.0210*
H15	−0.09430	0.08880	0.52010	0.0200*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0285 (3)	0.0193 (3)	0.0267 (3)	0.0149 (2)	0.0046 (2)	−0.0009 (2)
S1	0.0194 (2)	0.0151 (2)	0.0159 (2)	0.0069 (2)	0.0098 (2)	0.0050 (2)
N1	0.0117 (7)	0.0106 (8)	0.0120 (8)	0.0025 (6)	0.0037 (6)	0.0008 (6)
N2	0.0147 (7)	0.0117 (8)	0.0168 (8)	0.0040 (6)	0.0100 (6)	0.0026 (6)
N3	0.0142 (8)	0.0138 (8)	0.0147 (8)	0.0001 (6)	0.0064 (6)	0.0003 (6)
C1	0.0114 (9)	0.0115 (9)	0.0144 (9)	0.0005 (7)	0.0046 (7)	−0.0028 (7)
C2	0.0123 (8)	0.0109 (9)	0.0113 (9)	−0.0021 (7)	0.0001 (7)	−0.0008 (7)
C3	0.0144 (9)	0.0133 (9)	0.0168 (10)	−0.0004 (7)	0.0066 (8)	−0.0023 (7)
C4	0.0156 (9)	0.0134 (9)	0.0150 (9)	0.0020 (7)	0.0098 (7)	−0.0009 (7)
C5	0.0238 (10)	0.0188 (11)	0.0194 (10)	−0.0055 (8)	0.0046 (8)	−0.0023 (8)
C6	0.0261 (10)	0.0253 (12)	0.0157 (10)	−0.0015 (8)	0.0030 (8)	0.0032 (8)
C7	0.0309 (11)	0.0168 (10)	0.0235 (11)	0.0036 (8)	0.0159 (9)	0.0056 (8)
C8	0.0210 (10)	0.0137 (10)	0.0267 (11)	−0.0038 (7)	0.0134 (9)	−0.0002 (8)
C9	0.0145 (9)	0.0159 (10)	0.0192 (10)	−0.0008 (7)	0.0062 (8)	−0.0030 (8)
C10	0.0143 (9)	0.0130 (9)	0.0098 (8)	0.0044 (7)	0.0059 (7)	0.0006 (7)
C11	0.0128 (9)	0.0152 (10)	0.0159 (10)	0.0016 (7)	0.0059 (8)	0.0011 (7)
C12	0.0228 (10)	0.0108 (9)	0.0164 (10)	0.0004 (7)	0.0096 (8)	−0.0007 (7)
C13	0.0213 (10)	0.0163 (10)	0.0103 (9)	0.0102 (7)	0.0051 (8)	0.0020 (7)
C14	0.0129 (9)	0.0219 (11)	0.0159 (10)	0.0060 (7)	0.0019 (8)	0.0001 (8)
C15	0.0184 (10)	0.0141 (10)	0.0148 (9)	−0.0002 (7)	0.0026 (8)	−0.0027 (7)

Geometric parameters (Å, º)

Cl1—C13	1.742 (2)	C10—C15	1.384 (3)
S1—C1	1.688 (2)	C10—C11	1.385 (3)
N1—C1	1.379 (2)	C11—C12	1.391 (3)
N1—C2	1.387 (2)	C12—C13	1.382 (3)
N1—C10	1.445 (2)	C13—C14	1.385 (3)
N2—N3	1.381 (2)	C14—C15	1.389 (3)
N2—C1	1.333 (2)	C3—H3A	0.97
N3—C2	1.307 (2)	C3—H3B	0.97
N2—H2	0.86	C5—H5	0.93
C2—C3	1.497 (3)	C6—H6	0.93
C3—C4	1.515 (3)	C7—H7	0.93
C4—C5	1.395 (3)	C8—H8	0.93
C4—C9	1.388 (3)	C9—H9	0.93
C5—C6	1.388 (3)	C11—H11	0.93
C6—C7	1.389 (3)	C12—H12	0.93
C7—C8	1.378 (3)	C14—H14	0.93
C8—C9	1.395 (3)	C15—H15	0.93
Cl1···S1^i	3.679 (2)	C14···C7^x	3.440 (3)
Cl1···C2^ii	3.611 (3)	C15···C3	3.371 (3)
Cl1···C3^ii	3.540 (3)	C15···N3^vii	3.409 (3)
Cl1···C11^ii	3.535 (3)	C1···H6^vi	3.0436
Cl1···H3B^ii	2.8054	C1···H11	2.9923
Cl1···H5^ii	2.9628	C2···H15^vii	2.8869
S1···C11	3.419 (3)	C4···H3B^x	3.0479
S1···N2^iii	3.238 (2)	C8···H11^viii	3.0872
S1···Cl1^iv	3.679 (2)	C9···H3B^x	2.9790
S1···H8^v	3.1849	C10···H3B	2.9834
S1···H6^vi	3.1292	C14···H7^x	2.9914
S1···H9^vii	3.0538	C15···H3A	3.0140
S1···H2^iii	2.3798	H2···S1^iii	2.3798
N1···N3	2.217 (2)	H3A···C15	3.0140
N2···N1	2.131 (2)	H3A···H9	2.3745
N2···S1^iii	3.238 (2)	H3A···H15	2.5877
N3···N1	2.217 (2)	H3B···C10	2.9834
N3···C5	3.300 (3)	H3B···H5	2.5695
N3···C15^vii	3.409 (3)	H3B···C4^x	3.0479
N2···H15^vii	2.8597	H3B···C9^x	2.9790
N3···H12^viii	2.7123	H3B···Cl1^ix	2.8054
N3···H15^vii	2.7057	H5···H3B	2.5695
C2···Cl1^ix	3.611 (3)	H5···Cl1^ix	2.9628
C3···C15	3.371 (3)	H6···S1^vi	3.1292
C3···C4^x	3.563 (3)	H6···C1^vi	3.0436
C3···Cl1^ix	3.540 (3)	H7···C14^x	2.9914
C4···C3^x	3.563 (3)	H8···S1^viii	3.1849
C5···N3	3.300 (3)	H9···H3A	2.3745
C7···C12^viii	3.544 (3)	H9···S1^vii	3.0538
C7···C14^x	3.440 (3)	H11···C1	2.9923
C8···C12^viii	3.572 (3)	H11···C8^v	3.0872
C8···C11^viii	3.492 (3)	H12···N3^v	2.7123
C11···Cl1^ix	3.535 (3)	H15···H3A	2.5877
C11···S1	3.419 (3)	H15···N2^vii	2.8597
C11···C8^v	3.492 (3)	H15···N3^vii	2.7057
C12···C7^v	3.544 (3)	H15···C2^vii	2.8869
C12···C8^v	3.572 (3)
C1—N1—C2	107.89 (14)	Cl1—C13—C12	118.79 (14)
C1—N1—C10	124.39 (14)	C12—C13—C14	122.23 (17)
C2—N1—C10	127.57 (15)	C13—C14—C15	118.68 (17)
N3—N2—C1	113.89 (15)	C10—C15—C14	119.47 (17)
N2—N3—C2	103.92 (14)	C2—C3—H3A	109.22
N3—N2—H2	123.01	C2—C3—H3B	109.30
C1—N2—H2	123.10	C4—C3—H3A	109.22
N1—C1—N2	103.55 (15)	C4—C3—H3B	109.22
S1—C1—N1	127.14 (14)	H3A—C3—H3B	107.93
S1—C1—N2	129.28 (14)	C4—C5—H5	119.80
N3—C2—C3	125.08 (16)	C6—C5—H5	119.89
N1—C2—N3	110.74 (16)	C5—C6—H6	119.79
N1—C2—C3	124.14 (16)	C7—C6—H6	119.84
C2—C3—C4	111.86 (15)	C6—C7—H7	120.19
C5—C4—C9	118.86 (17)	C8—C7—H7	120.17
C3—C4—C5	120.84 (16)	C7—C8—H8	119.95
C3—C4—C9	120.30 (16)	C9—C8—H8	119.89
C4—C5—C6	120.31 (17)	C4—C9—H9	119.65
C5—C6—C7	120.37 (17)	C8—C9—H9	119.70
C6—C7—C8	119.64 (17)	C10—C11—H11	120.32
C7—C8—C9	120.16 (18)	C12—C11—H11	120.33
C4—C9—C8	120.65 (17)	C11—C12—H12	120.62
C11—C10—C15	121.49 (17)	C13—C12—H12	120.60
N1—C10—C11	118.84 (16)	C13—C14—H14	120.64
N1—C10—C15	119.67 (16)	C15—C14—H14	120.68
C10—C11—C12	119.35 (17)	C10—C15—H15	120.22
C11—C12—C13	118.78 (17)	C14—C15—H15	120.31
Cl1—C13—C14	118.97 (15)
C1—N1—C2—N3	1.0 (2)	C2—C3—C4—C5	76.7 (2)
C2—N1—C1—S1	177.07 (14)	C9—C4—C5—C6	0.7 (3)
C10—N1—C1—S1	−7.1 (3)	C5—C4—C9—C8	−0.6 (3)
C2—N1—C1—N2	−0.99 (18)	C3—C4—C5—C6	−178.59 (17)
C10—N1—C1—N2	174.87 (15)	C3—C4—C9—C8	178.62 (17)
C1—N1—C10—C15	118.30 (19)	C4—C5—C6—C7	0.1 (3)
C2—N1—C10—C15	−66.7 (2)	C5—C6—C7—C8	−1.0 (3)
C10—N1—C2—C3	7.5 (3)	C6—C7—C8—C9	1.0 (3)
C10—N1—C2—N3	−174.71 (16)	C7—C8—C9—C4	−0.2 (3)
C1—N1—C2—C3	−176.82 (16)	N1—C10—C11—C12	179.64 (16)
C2—N1—C10—C11	114.1 (2)	C15—C10—C11—C12	0.5 (3)
C1—N1—C10—C11	−60.9 (2)	N1—C10—C15—C14	−179.87 (16)
C1—N2—N3—C2	−0.15 (19)	C11—C10—C15—C14	−0.7 (3)
N3—N2—C1—N1	0.73 (19)	C10—C11—C12—C13	0.2 (3)
N3—N2—C1—S1	−177.28 (14)	C11—C12—C13—C14	−0.6 (3)
N2—N3—C2—C3	177.27 (16)	C11—C12—C13—Cl1	178.45 (14)
N2—N3—C2—N1	−0.51 (19)	Cl1—C13—C14—C15	−178.68 (14)
N1—C2—C3—C4	−175.38 (16)	C12—C13—C14—C15	0.4 (3)
N3—C2—C3—C4	7.1 (2)	C13—C14—C15—C10	0.3 (3)
C2—C3—C4—C9	−102.5 (2)

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1, −y, −z+1; (iv) x+1/2, −y+1/2, z−1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) −x+1, −y, −z+2; (vii) −x, −y, −z+1; (viii) −x+1/2, y−1/2, −z+3/2; (ix) x+1/2, −y+1/2, z+1/2; (x) −x, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1^iii	0.86	2.38	3.237 (2)	175
C3—H3B···Cl1^ix	0.97	2.81	3.540 (3)	133
C3—H3B···Cg1^x	0.97	2.99	3.648 (3)	126
C12—H12···Cg1^v	0.93	3.00	3.535 (3)	118
C15—H15···Cg2^vii	0.93	2.74	3.616 (3)	158

Symmetry codes: (iii) −x+1, −y, −z+1; (v) −x+1/2, y+1/2, −z+3/2; (vii) −x, −y, −z+1; (ix) x+1/2, −y+1/2, z+1/2; (x) −x, −y, −z+2.