5-Benzyl-4-phenyl-2,4-di­hydro-1,2,4-triazole-3-thione

As part of structural studies of 1,2,4-triazole derivatives, the crystal structure of the title compound, C₁₅H₁₃N₃S, 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.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.45 × 0.35 × 0.25 mm
Z = 4

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0538P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)

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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···H3^iii	3.0239
S1···C9^i	3.638 (2)	C6···H9B	2.9592
S1···N2^ii	3.2928 (15)	C7···H12^viii	2.9950
S1···H9B^i	3.1919	C7···H4^iii	3.0415
S1···H22^ii	2.4512	C8···H11	2.9658
S1···H3^iii	3.1508	C12···H9A^ix	2.9108
N1···N3	2.2046 (19)	C13···H5^v	2.9592
N2···N1	2.1242 (19)	H3···S1^v	3.1508
N2···S1^ii	3.2928 (15)	H3···C6^v	3.0239
N3···N1	2.2046 (19)	H4···N3^x	2.8909
N2···H4^iii	2.9163	H4···N2^v	2.9163
N3···H4^iv	2.8909	H4···C7^v	3.0415
N3···H5^iv	2.8406	H5···N3^x	2.8406
C1···C10	3.313 (2)	H5···C13^iii	2.9592
C1···C15	3.556 (3)	H6···C3^iii	2.9972
C2···S1	3.5556 (17)	H9A···C12^ix	2.9108
C3···C6^v	3.593 (3)	H9B···S1^vi	3.1919
C6···C3^iii	3.593 (3)	H9B···C1	3.0228
C6···C9	3.427 (3)	H9B···C6	2.9592
C9···S1^vi	3.638 (2)	H9B···H15	2.3180
C9···C6	3.427 (3)	H11···C8	2.9658
C10···C1	3.313 (2)	H12···C7^viii	2.9950
C15···C1	3.556 (3)	H14···C2^xi	3.0699
C1···H9B	3.0228	H14···C3^xi	2.9982
C2···H14^vii	3.0699	H15···H9B	2.3180
C3···H14^vii	2.9982	H22···S1^ii	2.4512
C3···H6^v	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)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H22···S1^ii	0.86	2.45	3.293 (2)	166
C4—H4···Cg1^v	0.93	2.95	3.715 (2)	141
C12—H12···Cg1^viii	0.93	2.98	3.796 (2)	147
C14—H14···Cg2^xi	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.