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

In the title mol­ecule, C₁₅H₁₃N₃OS, the triazole ring plane forms dihedral angles of 18.99 (7) and 89.35 (7)° with the hydroxy­phenyl and benzyl substituent ring planes, respectively. In the crystal structure, the mol­ecules exist as centrosymmetric N—H...S hydrogen-bonded dimers, with an N...S distance of 3.287 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.109
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.74 mm

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 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 for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

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

Crystal data

C15H13N3OS	F(000) = 592
Mr = 283.34	Dx = 1.380 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5446 reflections
a = 5.7387 (5) Å	θ = 1.7–26.0°
b = 23.842 (3) Å	µ = 0.24 mm^−1
c = 10.3045 (9) Å	T = 296 K
β = 104.655 (7)°	Plate, colourless
V = 1364.0 (2) Å^3	0.74 × 0.43 × 0.05 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	2673 independent reflections
Radiation source: sealed X-ray tube	1737 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.078
Detector resolution: 6.67 pixels mm^-1	θmax = 26.1°, θmin = 1.7°
ω scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −29→29
Tmin = 0.859, Tmax = 0.988	l = −12→12
7312 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0654P)^2] where P = (Fo^2 + 2Fc^2)/3
2673 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

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

	x	y	z	Uiso*/Ueq
S1	1.36193 (10)	−0.02084 (2)	0.17678 (6)	0.05650 (18)
O1	0.8270 (4)	0.18499 (8)	−0.17450 (19)	0.0874 (6)
H1	0.9308	0.1605	−0.1613	0.131*
N1	1.0596 (3)	0.06973 (7)	0.14217 (16)	0.0472 (4)
N2	1.1363 (3)	0.11347 (7)	−0.03084 (17)	0.0531 (4)
N3	1.2742 (3)	0.06623 (7)	0.00063 (16)	0.0517 (4)
H3	1.3765	0.0556	−0.0426	0.062*
C1	0.7406 (4)	0.19044 (9)	−0.0643 (3)	0.0653 (6)
C2	0.5610 (5)	0.22983 (11)	−0.0708 (3)	0.0823 (8)
H2	0.5036	0.2502	−0.1494	0.099*
C3	0.4662 (5)	0.23930 (11)	0.0369 (4)	0.0851 (8)
H3A	0.3450	0.2658	0.0305	0.102*
C4	0.5492 (5)	0.20992 (11)	0.1536 (3)	0.0757 (7)
H4	0.4867	0.2169	0.2269	0.091*
C5	0.7257 (4)	0.17008 (10)	0.1616 (2)	0.0657 (6)
H5	0.7812	0.1503	0.2411	0.079*
C6	0.8244 (4)	0.15849 (8)	0.0527 (2)	0.0531 (5)
C7	1.0053 (4)	0.11520 (8)	0.0561 (2)	0.0482 (5)
C8	1.2340 (3)	0.03832 (8)	0.10510 (19)	0.0466 (5)
C9	0.9526 (4)	0.05143 (9)	0.2495 (2)	0.0540 (5)
H9A	0.9715	0.0111	0.2596	0.065*
H9B	0.7813	0.0594	0.2232	0.065*
C10	1.0586 (3)	0.07848 (8)	0.3829 (2)	0.0494 (5)
C11	1.2717 (4)	0.10784 (10)	0.4115 (2)	0.0621 (6)
H11	1.3554	0.1122	0.3458	0.075*
C12	1.3628 (4)	0.13096 (12)	0.5378 (2)	0.0725 (7)
H12	1.5071	0.1508	0.5562	0.087*
C13	1.2414 (5)	0.12471 (11)	0.6350 (2)	0.0699 (7)
H13	1.3022	0.1405	0.7193	0.084*
C14	1.0306 (5)	0.09525 (10)	0.6082 (2)	0.0691 (7)
H14	0.9488	0.0906	0.6748	0.083*
C15	0.9384 (4)	0.07232 (9)	0.4828 (2)	0.0618 (6)
H15	0.7941	0.0525	0.4652	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0555 (3)	0.0550 (3)	0.0632 (3)	0.0036 (2)	0.0228 (3)	0.0052 (3)
O1	0.1073 (14)	0.0805 (12)	0.0785 (12)	0.0197 (10)	0.0314 (11)	0.0242 (9)
N1	0.0463 (9)	0.0499 (9)	0.0463 (9)	−0.0025 (7)	0.0136 (7)	−0.0046 (7)
N2	0.0575 (10)	0.0511 (10)	0.0507 (10)	−0.0003 (8)	0.0138 (8)	−0.0022 (8)
N3	0.0542 (10)	0.0531 (10)	0.0519 (10)	0.0012 (8)	0.0214 (8)	−0.0015 (8)
C1	0.0695 (15)	0.0505 (12)	0.0729 (15)	−0.0024 (11)	0.0126 (12)	−0.0005 (11)
C2	0.0838 (18)	0.0564 (14)	0.098 (2)	0.0136 (13)	0.0076 (16)	0.0070 (14)
C3	0.0714 (16)	0.0565 (15)	0.121 (3)	0.0122 (13)	0.0120 (18)	−0.0142 (16)
C4	0.0685 (15)	0.0700 (16)	0.0871 (18)	0.0105 (13)	0.0172 (14)	−0.0224 (14)
C5	0.0645 (14)	0.0654 (14)	0.0639 (14)	0.0061 (11)	0.0098 (11)	−0.0158 (11)
C6	0.0508 (11)	0.0478 (11)	0.0567 (12)	−0.0016 (9)	0.0063 (10)	−0.0096 (9)
C7	0.0477 (11)	0.0478 (11)	0.0468 (10)	−0.0041 (9)	0.0075 (9)	−0.0044 (9)
C8	0.0428 (10)	0.0502 (11)	0.0474 (11)	−0.0050 (8)	0.0125 (9)	−0.0075 (9)
C9	0.0492 (11)	0.0569 (12)	0.0608 (13)	−0.0059 (10)	0.0230 (10)	−0.0041 (10)
C10	0.0499 (11)	0.0522 (11)	0.0490 (11)	0.0042 (9)	0.0180 (10)	0.0036 (9)
C11	0.0550 (12)	0.0807 (15)	0.0531 (12)	−0.0091 (11)	0.0182 (10)	−0.0047 (11)
C12	0.0610 (14)	0.0908 (18)	0.0628 (14)	−0.0101 (13)	0.0102 (12)	−0.0116 (13)
C13	0.0875 (18)	0.0724 (15)	0.0487 (12)	0.0118 (14)	0.0149 (12)	−0.0020 (11)
C14	0.0949 (18)	0.0655 (14)	0.0571 (14)	0.0065 (13)	0.0381 (13)	0.0036 (11)
C15	0.0641 (13)	0.0622 (13)	0.0662 (14)	−0.0027 (11)	0.0298 (12)	−0.0007 (11)

Geometric parameters (Å, º)

S1—C8	1.673 (2)	C5—C6	1.407 (3)
O1—C1	1.355 (3)	C5—H5	0.93
O1—H1	0.82	C6—C7	1.458 (3)
N1—C8	1.379 (2)	C9—C10	1.500 (3)
N1—C7	1.385 (2)	C9—H9A	0.97
N1—C9	1.461 (2)	C9—H9B	0.97
N2—C7	1.308 (2)	C10—C11	1.375 (3)
N2—N3	1.368 (2)	C10—C15	1.384 (3)
N3—C8	1.334 (2)	C11—C12	1.388 (3)
N3—H3	0.86	C11—H11	0.93
C1—C2	1.383 (3)	C12—C13	1.366 (3)
C1—C6	1.404 (3)	C12—H12	0.93
C2—C3	1.372 (4)	C13—C14	1.365 (4)
C2—H2	0.93	C13—H13	0.93
C3—C4	1.369 (4)	C14—C15	1.380 (3)
C3—H3A	0.93	C14—H14	0.93
C4—C5	1.376 (3)	C15—H15	0.93
C4—H4	0.93
C1—O1—H1	109.5	N1—C7—C6	127.83 (17)
C8—N1—C7	108.02 (15)	N3—C8—N1	103.79 (17)
C8—N1—C9	121.40 (16)	N3—C8—S1	129.07 (15)
C7—N1—C9	130.44 (16)	N1—C8—S1	127.13 (15)
C7—N2—N3	105.19 (16)	N1—C9—C10	114.47 (16)
C8—N3—N2	113.21 (15)	N1—C9—H9A	108.6
C8—N3—H3	123.4	C10—C9—H9A	108.6
N2—N3—H3	123.4	N1—C9—H9B	108.6
O1—C1—C2	116.8 (2)	C10—C9—H9B	108.6
O1—C1—C6	123.3 (2)	H9A—C9—H9B	107.6
C2—C1—C6	119.9 (2)	C11—C10—C15	118.57 (19)
C3—C2—C1	121.0 (3)	C11—C10—C9	123.22 (17)
C3—C2—H2	119.5	C15—C10—C9	118.19 (18)
C1—C2—H2	119.5	C10—C11—C12	120.5 (2)
C4—C3—C2	120.3 (2)	C10—C11—H11	119.8
C4—C3—H3A	119.8	C12—C11—H11	119.8
C2—C3—H3A	119.8	C13—C12—C11	120.2 (2)
C3—C4—C5	119.6 (3)	C13—C12—H12	119.9
C3—C4—H4	120.2	C11—C12—H12	119.9
C5—C4—H4	120.2	C14—C13—C12	119.9 (2)
C4—C5—C6	121.8 (2)	C14—C13—H13	120.1
C4—C5—H5	119.1	C12—C13—H13	120.1
C6—C5—H5	119.1	C13—C14—C15	120.2 (2)
C1—C6—C5	117.3 (2)	C13—C14—H14	119.9
C1—C6—C7	119.48 (19)	C15—C14—H14	119.9
C5—C6—C7	123.2 (2)	C14—C15—C10	120.6 (2)
N2—C7—N1	109.79 (17)	C14—C15—H15	119.7
N2—C7—C6	122.33 (18)	C10—C15—H15	119.7
C7—N2—N3—C8	−0.2 (2)	C1—C6—C7—N1	−159.7 (2)
O1—C1—C2—C3	−178.4 (2)	C5—C6—C7—N1	19.8 (3)
C6—C1—C2—C3	1.5 (4)	N2—N3—C8—N1	0.1 (2)
C1—C2—C3—C4	0.3 (4)	N2—N3—C8—S1	−179.86 (15)
C2—C3—C4—C5	−1.1 (4)	C7—N1—C8—N3	0.0 (2)
C3—C4—C5—C6	0.0 (4)	C9—N1—C8—N3	176.14 (16)
O1—C1—C6—C5	177.5 (2)	C7—N1—C8—S1	179.98 (15)
C2—C1—C6—C5	−2.5 (3)	C9—N1—C8—S1	−3.9 (3)
O1—C1—C6—C7	−3.0 (3)	C8—N1—C9—C10	98.6 (2)
C2—C1—C6—C7	177.0 (2)	C7—N1—C9—C10	−86.2 (3)
C4—C5—C6—C1	1.8 (3)	N1—C9—C10—C11	−14.2 (3)
C4—C5—C6—C7	−177.8 (2)	N1—C9—C10—C15	167.40 (18)
N3—N2—C7—N1	0.2 (2)	C15—C10—C11—C12	−0.3 (3)
N3—N2—C7—C6	−177.20 (17)	C9—C10—C11—C12	−178.7 (2)
C8—N1—C7—N2	−0.2 (2)	C10—C11—C12—C13	0.0 (4)
C9—N1—C7—N2	−175.77 (18)	C11—C12—C13—C14	0.5 (4)
C8—N1—C7—C6	177.05 (19)	C12—C13—C14—C15	−0.7 (4)
C9—N1—C7—C6	1.4 (3)	C13—C14—C15—C10	0.5 (4)
C1—C6—C7—N2	17.1 (3)	C11—C10—C15—C14	0.1 (3)
C5—C6—C7—N2	−163.3 (2)	C9—C10—C15—C14	178.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1^i	0.86	2.43	3.287 (2)	175
O1—H1···N2	0.82	1.91	2.631 (3)	146

Symmetry code: (i) −x+3, −y, −z.