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As part of structural studies of 1,2,4-triazole derivatives, the crystal structure of the title compound, C
15H
13N
3S, has been investigated. The structure shows a V-shape in the molecular skeleton, as found for similar compounds. The crystal structure is stabilized by an N—H
S and three C—H
π intermolecular interactions.
Supporting information
CCDC reference: 251711
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.096
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.109
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. CG1 .. 2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. CG1 .. 2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. CG2 .. 2.99 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
5-Benzyl-4-phenyl-2,4-dihydro-1,2,4-triazole-3-thione
top
Crystal data top
C15H13N3S | F(000) = 560 |
Mr = 267.35 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2998 reflections |
a = 7.0467 (5) Å | θ = 2.2–27.2° |
b = 17.6802 (13) Å | µ = 0.23 mm−1 |
c = 11.2725 (7) Å | T = 296 K |
β = 104.355 (5)° | Prism, colorless |
V = 1360.56 (17) Å3 | 0.45 × 0.35 × 0.25 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 2023 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.109 |
Plane graphite monochromator | θmax = 27.1°, θmin = 2.2° |
Detector resolution: 6.67 pixels mm-1 | h = −8→9 |
ω scans | k = −22→22 |
21276 measured reflections | l = −14→14 |
2998 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0538P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max < 0.001 |
2998 reflections | Δρmax = 0.33 e Å−3 |
173 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.012 (2) |
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 | |
S1 | 0.59031 (6) | 0.12047 (2) | 0.06279 (4) | 0.0448 (2) | |
N1 | 0.31980 (18) | 0.12316 (7) | 0.20129 (12) | 0.0361 (4) | |
N2 | 0.3003 (2) | 0.02542 (8) | 0.08932 (13) | 0.0450 (5) | |
N3 | 0.1540 (2) | 0.01749 (8) | 0.14915 (14) | 0.0487 (5) | |
C1 | 0.3819 (2) | 0.19360 (9) | 0.26258 (14) | 0.0367 (5) | |
C2 | 0.5575 (2) | 0.19735 (10) | 0.34849 (15) | 0.0435 (5) | |
C3 | 0.6167 (3) | 0.26540 (11) | 0.40688 (17) | 0.0522 (6) | |
C4 | 0.4989 (3) | 0.32831 (11) | 0.37930 (19) | 0.0581 (7) | |
C5 | 0.3236 (3) | 0.32383 (11) | 0.2937 (2) | 0.0598 (7) | |
C6 | 0.2637 (3) | 0.25627 (10) | 0.23384 (17) | 0.0482 (6) | |
C7 | 0.4051 (2) | 0.08890 (9) | 0.11751 (13) | 0.0358 (5) | |
C8 | 0.1685 (2) | 0.07759 (10) | 0.21668 (15) | 0.0413 (5) | |
C9 | 0.0410 (3) | 0.09483 (12) | 0.30001 (17) | 0.0504 (6) | |
C10 | 0.1453 (2) | 0.09751 (10) | 0.43353 (16) | 0.0431 (5) | |
C11 | 0.2409 (3) | 0.03485 (11) | 0.4927 (2) | 0.0571 (7) | |
C12 | 0.3288 (3) | 0.03720 (14) | 0.6163 (2) | 0.0672 (8) | |
C13 | 0.3211 (3) | 0.10145 (15) | 0.6827 (2) | 0.0684 (9) | |
C14 | 0.2284 (3) | 0.16446 (14) | 0.6246 (2) | 0.0684 (8) | |
C15 | 0.1426 (3) | 0.16243 (11) | 0.50140 (18) | 0.0555 (7) | |
H2 | 0.63610 | 0.15460 | 0.36740 | 0.0520* | |
H3 | 0.73620 | 0.26860 | 0.46470 | 0.0630* | |
H4 | 0.53850 | 0.37390 | 0.41890 | 0.0700* | |
H5 | 0.24410 | 0.36640 | 0.27560 | 0.0720* | |
H6 | 0.14520 | 0.25330 | 0.17500 | 0.0580* | |
H9A | −0.06120 | 0.05680 | 0.28850 | 0.0610* | |
H9B | −0.02180 | 0.14330 | 0.27690 | 0.0610* | |
H11 | 0.24610 | −0.00930 | 0.44880 | 0.0690* | |
H12 | 0.39400 | −0.00530 | 0.65490 | 0.0810* | |
H13 | 0.37810 | 0.10240 | 0.76650 | 0.0820* | |
H14 | 0.22380 | 0.20850 | 0.66880 | 0.0820* | |
H15 | 0.08130 | 0.20560 | 0.46270 | 0.0670* | |
H22 | 0.32260 | −0.00750 | 0.03820 | 0.0540* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0532 (3) | 0.0388 (2) | 0.0459 (3) | −0.0015 (2) | 0.0187 (2) | −0.0084 (2) |
N1 | 0.0423 (7) | 0.0319 (7) | 0.0337 (7) | 0.0009 (5) | 0.0087 (5) | −0.0056 (5) |
N2 | 0.0608 (9) | 0.0335 (8) | 0.0432 (8) | −0.0031 (6) | 0.0177 (7) | −0.0110 (6) |
N3 | 0.0591 (9) | 0.0430 (9) | 0.0460 (9) | −0.0093 (7) | 0.0170 (7) | −0.0068 (7) |
C1 | 0.0464 (9) | 0.0327 (8) | 0.0323 (8) | −0.0004 (6) | 0.0124 (7) | −0.0063 (6) |
C2 | 0.0480 (9) | 0.0416 (9) | 0.0400 (9) | 0.0039 (7) | 0.0091 (7) | −0.0053 (7) |
C3 | 0.0546 (10) | 0.0570 (12) | 0.0422 (10) | −0.0079 (9) | 0.0067 (8) | −0.0140 (8) |
C4 | 0.0726 (13) | 0.0445 (11) | 0.0581 (12) | −0.0076 (9) | 0.0178 (10) | −0.0210 (9) |
C5 | 0.0724 (13) | 0.0370 (10) | 0.0687 (13) | 0.0114 (9) | 0.0152 (11) | −0.0108 (9) |
C6 | 0.0522 (10) | 0.0435 (10) | 0.0456 (10) | 0.0071 (8) | 0.0059 (8) | −0.0082 (8) |
C7 | 0.0454 (8) | 0.0301 (8) | 0.0301 (8) | 0.0045 (6) | 0.0058 (6) | −0.0042 (6) |
C8 | 0.0435 (8) | 0.0412 (10) | 0.0379 (9) | −0.0017 (7) | 0.0075 (7) | −0.0043 (7) |
C9 | 0.0440 (9) | 0.0610 (12) | 0.0485 (10) | −0.0016 (8) | 0.0157 (8) | −0.0043 (9) |
C10 | 0.0415 (8) | 0.0477 (10) | 0.0439 (9) | −0.0013 (7) | 0.0178 (7) | −0.0024 (7) |
C11 | 0.0643 (12) | 0.0470 (11) | 0.0625 (13) | 0.0065 (9) | 0.0202 (10) | 0.0008 (9) |
C12 | 0.0671 (12) | 0.0701 (15) | 0.0641 (14) | 0.0147 (10) | 0.0159 (10) | 0.0217 (12) |
C13 | 0.0654 (13) | 0.0965 (19) | 0.0441 (11) | 0.0001 (11) | 0.0149 (9) | 0.0037 (11) |
C14 | 0.0840 (15) | 0.0734 (15) | 0.0510 (12) | 0.0040 (12) | 0.0226 (11) | −0.0155 (11) |
C15 | 0.0662 (12) | 0.0524 (12) | 0.0518 (11) | 0.0116 (9) | 0.0218 (9) | −0.0023 (9) |
Geometric parameters (Å, º) top
S1—C7 | 1.6717 (15) | C10—C11 | 1.380 (3) |
N1—C1 | 1.439 (2) | C11—C12 | 1.378 (3) |
N1—C7 | 1.379 (2) | C12—C13 | 1.369 (3) |
N1—C8 | 1.381 (2) | C13—C14 | 1.373 (3) |
N2—N3 | 1.372 (2) | C14—C15 | 1.371 (3) |
N2—C7 | 1.338 (2) | C2—H2 | 0.9300 |
N3—C8 | 1.296 (2) | C3—H3 | 0.9300 |
N2—H22 | 0.8605 | C4—H4 | 0.9301 |
C1—C6 | 1.376 (2) | C5—H5 | 0.9302 |
C1—C2 | 1.371 (2) | C6—H6 | 0.9302 |
C2—C3 | 1.385 (3) | C9—H9A | 0.9702 |
C3—C4 | 1.377 (3) | C9—H9B | 0.9700 |
C4—C5 | 1.368 (3) | C11—H11 | 0.9298 |
C5—C6 | 1.385 (3) | C12—H12 | 0.9305 |
C8—C9 | 1.484 (3) | C13—H13 | 0.9305 |
C9—C10 | 1.503 (3) | C14—H14 | 0.9293 |
C10—C15 | 1.382 (3) | C15—H15 | 0.9306 |
| | | |
S1···C2 | 3.5556 (17) | C6···H3iii | 3.0239 |
S1···C9i | 3.638 (2) | C6···H9B | 2.9592 |
S1···N2ii | 3.2928 (15) | C7···H12viii | 2.9950 |
S1···H9Bi | 3.1919 | C7···H4iii | 3.0415 |
S1···H22ii | 2.4512 | C8···H11 | 2.9658 |
S1···H3iii | 3.1508 | C12···H9Aix | 2.9108 |
N1···N3 | 2.2046 (19) | C13···H5v | 2.9592 |
N2···N1 | 2.1242 (19) | H3···S1v | 3.1508 |
N2···S1ii | 3.2928 (15) | H3···C6v | 3.0239 |
N3···N1 | 2.2046 (19) | H4···N3x | 2.8909 |
N2···H4iii | 2.9163 | H4···N2v | 2.9163 |
N3···H4iv | 2.8909 | H4···C7v | 3.0415 |
N3···H5iv | 2.8406 | H5···N3x | 2.8406 |
C1···C10 | 3.313 (2) | H5···C13iii | 2.9592 |
C1···C15 | 3.556 (3) | H6···C3iii | 2.9972 |
C2···S1 | 3.5556 (17) | H9A···C12ix | 2.9108 |
C3···C6v | 3.593 (3) | H9B···S1vi | 3.1919 |
C6···C3iii | 3.593 (3) | H9B···C1 | 3.0228 |
C6···C9 | 3.427 (3) | H9B···C6 | 2.9592 |
C9···S1vi | 3.638 (2) | H9B···H15 | 2.3180 |
C9···C6 | 3.427 (3) | H11···C8 | 2.9658 |
C10···C1 | 3.313 (2) | H12···C7viii | 2.9950 |
C15···C1 | 3.556 (3) | H14···C2xi | 3.0699 |
C1···H9B | 3.0228 | H14···C3xi | 2.9982 |
C2···H14vii | 3.0699 | H15···H9B | 2.3180 |
C3···H14vii | 2.9982 | H22···S1ii | 2.4512 |
C3···H6v | 2.9972 | | |
| | | |
C1—N1—C7 | 125.22 (13) | C13—C14—C15 | 120.0 (2) |
C1—N1—C8 | 126.65 (13) | C10—C15—C14 | 121.29 (19) |
C7—N1—C8 | 108.11 (13) | C1—C2—H2 | 120.30 |
N3—N2—C7 | 114.01 (13) | C3—C2—H2 | 120.33 |
N2—N3—C8 | 104.21 (13) | C2—C3—H3 | 119.97 |
N3—N2—H22 | 122.98 | C4—C3—H3 | 119.98 |
C7—N2—H22 | 123.01 | C3—C4—H4 | 119.97 |
N1—C1—C2 | 119.66 (14) | C5—C4—H4 | 119.97 |
C2—C1—C6 | 121.01 (16) | C4—C5—H5 | 119.81 |
N1—C1—C6 | 119.33 (14) | C6—C5—H5 | 119.78 |
C1—C2—C3 | 119.37 (16) | C1—C6—H6 | 120.43 |
C2—C3—C4 | 120.05 (18) | C5—C6—H6 | 120.48 |
C3—C4—C5 | 120.06 (18) | C8—C9—H9A | 108.60 |
C4—C5—C6 | 120.41 (19) | C8—C9—H9B | 108.61 |
C1—C6—C5 | 119.09 (18) | C10—C9—H9A | 108.56 |
N1—C7—N2 | 102.86 (13) | C10—C9—H9B | 108.56 |
S1—C7—N2 | 128.90 (12) | H9A—C9—H9B | 107.59 |
S1—C7—N1 | 128.23 (12) | C10—C11—H11 | 119.72 |
N1—C8—C9 | 124.56 (16) | C12—C11—H11 | 119.76 |
N1—C8—N3 | 110.81 (14) | C11—C12—H12 | 119.64 |
N3—C8—C9 | 124.63 (16) | C13—C12—H12 | 119.76 |
C8—C9—C10 | 114.71 (16) | C12—C13—H13 | 120.29 |
C9—C10—C11 | 121.18 (17) | C14—C13—H13 | 120.28 |
C11—C10—C15 | 118.12 (17) | C13—C14—H14 | 119.99 |
C9—C10—C15 | 120.67 (17) | C15—C14—H14 | 119.99 |
C10—C11—C12 | 120.52 (19) | C10—C15—H15 | 119.35 |
C11—C12—C13 | 120.6 (2) | C14—C15—H15 | 119.36 |
C12—C13—C14 | 119.4 (2) | | |
| | | |
C1—N1—C7—N2 | 178.73 (14) | C2—C1—C6—C5 | −0.5 (3) |
C7—N1—C1—C2 | −69.3 (2) | C6—C1—C2—C3 | −0.2 (3) |
C8—N1—C1—C2 | 109.59 (18) | C1—C2—C3—C4 | 0.6 (3) |
C7—N1—C1—C6 | 110.66 (18) | C2—C3—C4—C5 | −0.3 (3) |
C8—N1—C1—C6 | −70.4 (2) | C3—C4—C5—C6 | −0.3 (3) |
C7—N1—C8—N3 | 0.26 (18) | C4—C5—C6—C1 | 0.7 (3) |
C1—N1—C8—C9 | 0.7 (3) | N3—C8—C9—C10 | 115.7 (2) |
C7—N1—C8—C9 | 179.79 (16) | N1—C8—C9—C10 | −63.8 (2) |
C8—N1—C7—S1 | 178.35 (12) | C8—C9—C10—C15 | 120.92 (19) |
C8—N1—C7—N2 | −0.34 (16) | C8—C9—C10—C11 | −61.2 (2) |
C1—N1—C7—S1 | −2.6 (2) | C9—C10—C15—C14 | 176.58 (19) |
C1—N1—C8—N3 | −178.79 (14) | C9—C10—C11—C12 | −177.24 (19) |
C7—N2—N3—C8 | −0.17 (19) | C15—C10—C11—C12 | 0.8 (3) |
N3—N2—C7—S1 | −178.35 (12) | C11—C10—C15—C14 | −1.4 (3) |
N3—N2—C7—N1 | 0.32 (17) | C10—C11—C12—C13 | 0.7 (3) |
N2—N3—C8—N1 | −0.06 (18) | C11—C12—C13—C14 | −1.4 (3) |
N2—N3—C8—C9 | −179.59 (16) | C12—C13—C14—C15 | 0.8 (3) |
N1—C1—C6—C5 | 179.58 (17) | C13—C14—C15—C10 | 0.7 (3) |
N1—C1—C2—C3 | 179.80 (15) | | |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) x+1/2, −y+1/2, z+1/2; (vi) x−1, y, z; (vii) x+1/2, −y+1/2, z−1/2; (viii) −x+1, −y, −z+1; (ix) −x, −y, −z+1; (x) −x+1/2, y+1/2, −z+1/2; (xi) x−1/2, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H22···S1ii | 0.86 | 2.45 | 3.293 (2) | 166 |
C4—H4···Cg1v | 0.93 | 2.95 | 3.715 (2) | 141 |
C12—H12···Cg1viii | 0.93 | 2.98 | 3.796 (2) | 147 |
C14—H14···Cg2xi | 0.93 | 2.99 | 3.603 (2) | 125 |
Symmetry codes: (ii) −x+1, −y, −z; (v) x+1/2, −y+1/2, z+1/2; (viii) −x+1, −y, −z+1; (xi) x−1/2, −y+1/2, z+1/2. |
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