In the title molecule, C
15H
12ClN
3S, 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.
Supporting information
CCDC reference: 238811
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(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
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)-1
H-1,2,4-triazole-5(4
H)-thione
top
Crystal data top
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) Å3 | 0.25 × 0.21 × 0.18 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0253P)2 + 0.481P] where P = (Fo2 + 2Fc2)/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 top
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 F2 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 F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···S1i | 3.679 (2) | C14···C7x | 3.440 (3) |
Cl1···C2ii | 3.611 (3) | C15···C3 | 3.371 (3) |
Cl1···C3ii | 3.540 (3) | C15···N3vii | 3.409 (3) |
Cl1···C11ii | 3.535 (3) | C1···H6vi | 3.0436 |
Cl1···H3Bii | 2.8054 | C1···H11 | 2.9923 |
Cl1···H5ii | 2.9628 | C2···H15vii | 2.8869 |
S1···C11 | 3.419 (3) | C4···H3Bx | 3.0479 |
S1···N2iii | 3.238 (2) | C8···H11viii | 3.0872 |
S1···Cl1iv | 3.679 (2) | C9···H3Bx | 2.9790 |
S1···H8v | 3.1849 | C10···H3B | 2.9834 |
S1···H6vi | 3.1292 | C14···H7x | 2.9914 |
S1···H9vii | 3.0538 | C15···H3A | 3.0140 |
S1···H2iii | 2.3798 | H2···S1iii | 2.3798 |
N1···N3 | 2.217 (2) | H3A···C15 | 3.0140 |
N2···N1 | 2.131 (2) | H3A···H9 | 2.3745 |
N2···S1iii | 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···C15vii | 3.409 (3) | H3B···C4x | 3.0479 |
N2···H15vii | 2.8597 | H3B···C9x | 2.9790 |
N3···H12viii | 2.7123 | H3B···Cl1ix | 2.8054 |
N3···H15vii | 2.7057 | H5···H3B | 2.5695 |
C2···Cl1ix | 3.611 (3) | H5···Cl1ix | 2.9628 |
C3···C15 | 3.371 (3) | H6···S1vi | 3.1292 |
C3···C4x | 3.563 (3) | H6···C1vi | 3.0436 |
C3···Cl1ix | 3.540 (3) | H7···C14x | 2.9914 |
C4···C3x | 3.563 (3) | H8···S1viii | 3.1849 |
C5···N3 | 3.300 (3) | H9···H3A | 2.3745 |
C7···C12viii | 3.544 (3) | H9···S1vii | 3.0538 |
C7···C14x | 3.440 (3) | H11···C1 | 2.9923 |
C8···C12viii | 3.572 (3) | H11···C8v | 3.0872 |
C8···C11viii | 3.492 (3) | H12···N3v | 2.7123 |
C11···Cl1ix | 3.535 (3) | H15···H3A | 2.5877 |
C11···S1 | 3.419 (3) | H15···N2vii | 2.8597 |
C11···C8v | 3.492 (3) | H15···N3vii | 2.7057 |
C12···C7v | 3.544 (3) | H15···C2vii | 2.8869 |
C12···C8v | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···S1iii | 0.86 | 2.38 | 3.237 (2) | 175 |
C3—H3B···Cl1ix | 0.97 | 2.81 | 3.540 (3) | 133 |
C3—H3B···Cg1x | 0.97 | 2.99 | 3.648 (3) | 126 |
C12—H12···Cg1v | 0.93 | 3.00 | 3.535 (3) | 118 |
C15—H15···Cg2vii | 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. |