3-(2-Hydro­xy­phenyl)-4-phenyl-1H-1,2,4-triazole-5(4H)-thione

The title mol­ecule, C₁₄H₁₁N₃OS, is non-planar. The phenyl and hydroxy­phenyl rings form dihedral angles of 69.08 (9) and 24.57 (9)°, respectively, with the five-membered 2,4-di­hydro-1,2,4-triazole ring. The mol­ecules form centrosymmetric dimers through N—H...S hydrogen bonds, with an N...S distance of 3.279 (2) Å. In addition, the mol­ecule contains one O—H...N and one C—H...π(phenyl) intramolecular interactions. The dimers are connected through weak intermolecular C—H...π(hydroxy­phenyl) interactions into chains in the a direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.094
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.76 mm
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  CG1     ..       2.83 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 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-RED (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).

3-(2-Hydroxyphenyl)-4-phenyl-1H-1,2,4-triazole-5(4H)-thione

Crystal data

C14H11N3OS	F(000) = 560
Mr = 269.32	Dx = 1.436 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 26084 reflections
a = 5.7333 (4) Å	θ = 1.8–27.7°
b = 19.1695 (16) Å	µ = 0.25 mm^−1
c = 11.6547 (8) Å	T = 293 K
β = 103.441 (6)°	Rod, colourless
V = 1245.82 (16) Å^3	0.76 × 0.33 × 0.09 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	2800 independent reflections
Radiation source: fine-focus sealed tube	2202 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.061
Detector resolution: 6.67 pixels mm^-1	θmax = 27.4°, θmin = 2.1°
ω scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −24→24
Tmin = 0.889, Tmax = 0.981	l = −14→14
16413 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 0.1859P] where P = (Fo^2 + 2Fc^2)/3
2800 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.30 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	−0.00798 (7)	0.38077 (2)	0.01744 (4)	0.02773 (12)
O1	0.9997 (2)	0.52786 (6)	0.25363 (11)	0.0332 (3)
H1	0.8633	0.5333	0.2132	0.050*
N1	0.4259 (2)	0.38452 (7)	0.17926 (12)	0.0236 (3)
N2	0.3222 (2)	0.48210 (7)	0.09392 (13)	0.0282 (3)
H2N	0.2457	0.5133	0.0468	0.034*
N3	0.5337 (3)	0.49471 (7)	0.17365 (14)	0.0285 (3)
C1	1.0027 (3)	0.47291 (9)	0.32766 (15)	0.0274 (3)
C2	1.2114 (3)	0.46420 (9)	0.41482 (16)	0.0325 (4)
H2	1.3403	0.4941	0.4178	0.039*
C3	1.2294 (3)	0.41162 (10)	0.49706 (17)	0.0346 (4)
H3	1.3704	0.4062	0.5548	0.042*
C4	1.0381 (3)	0.36672 (10)	0.49405 (16)	0.0327 (4)
H4	1.0490	0.3321	0.5510	0.039*
C5	0.8321 (3)	0.37366 (9)	0.40633 (15)	0.0282 (4)
H5	0.7045	0.3434	0.4044	0.034*
C6	0.8113 (3)	0.42585 (8)	0.31963 (15)	0.0252 (3)
C7	0.5957 (3)	0.43467 (8)	0.22568 (15)	0.0248 (3)
C8	0.2461 (3)	0.41614 (8)	0.09656 (14)	0.0248 (3)
C9	0.4351 (3)	0.31121 (8)	0.20753 (15)	0.0246 (3)
C10	0.6111 (3)	0.27048 (9)	0.17769 (16)	0.0299 (4)
H10	0.7125	0.2889	0.1336	0.036*
C11	0.6331 (3)	0.20157 (9)	0.21495 (18)	0.0364 (4)
H11	0.7507	0.1733	0.1963	0.044*
C12	0.4798 (3)	0.17501 (10)	0.27999 (19)	0.0402 (5)
H12	0.4968	0.1290	0.3059	0.048*
C13	0.3019 (4)	0.21613 (10)	0.30682 (18)	0.0381 (4)
H13	0.1982	0.1976	0.3495	0.046*
C14	0.2783 (3)	0.28490 (9)	0.27015 (16)	0.0303 (4)
H14	0.1585	0.3129	0.2874	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0274 (2)	0.0235 (2)	0.0295 (2)	−0.00014 (15)	0.00088 (16)	0.00092 (16)
O1	0.0330 (6)	0.0299 (6)	0.0346 (7)	−0.0056 (5)	0.0038 (5)	0.0043 (5)
N1	0.0239 (6)	0.0194 (6)	0.0262 (7)	0.0002 (5)	0.0030 (5)	0.0010 (5)
N2	0.0258 (7)	0.0220 (7)	0.0338 (8)	0.0010 (5)	0.0009 (6)	0.0042 (6)
N3	0.0260 (7)	0.0230 (7)	0.0343 (8)	0.0002 (5)	0.0020 (6)	0.0008 (5)
C1	0.0292 (8)	0.0259 (8)	0.0275 (9)	−0.0011 (6)	0.0075 (7)	−0.0032 (6)
C2	0.0288 (8)	0.0352 (10)	0.0325 (10)	−0.0051 (7)	0.0050 (7)	−0.0038 (7)
C3	0.0301 (9)	0.0410 (10)	0.0291 (9)	0.0002 (7)	−0.0006 (7)	−0.0028 (7)
C4	0.0349 (9)	0.0334 (9)	0.0281 (9)	0.0013 (7)	0.0040 (7)	0.0031 (7)
C5	0.0284 (8)	0.0281 (8)	0.0272 (9)	0.0000 (7)	0.0044 (7)	−0.0001 (7)
C6	0.0249 (8)	0.0241 (8)	0.0261 (8)	0.0016 (6)	0.0047 (6)	−0.0020 (6)
C7	0.0247 (8)	0.0215 (7)	0.0287 (8)	−0.0004 (6)	0.0072 (7)	−0.0015 (6)
C8	0.0258 (8)	0.0240 (8)	0.0247 (8)	0.0021 (6)	0.0063 (7)	0.0015 (6)
C9	0.0268 (8)	0.0193 (7)	0.0257 (8)	−0.0005 (6)	0.0017 (6)	0.0010 (6)
C10	0.0293 (8)	0.0258 (8)	0.0341 (9)	−0.0004 (7)	0.0061 (7)	−0.0006 (7)
C11	0.0334 (9)	0.0229 (8)	0.0484 (11)	0.0031 (7)	0.0006 (8)	−0.0013 (7)
C12	0.0411 (10)	0.0250 (9)	0.0465 (12)	−0.0045 (8)	−0.0065 (9)	0.0092 (8)
C13	0.0386 (10)	0.0357 (10)	0.0377 (10)	−0.0092 (8)	0.0044 (8)	0.0101 (8)
C14	0.0279 (8)	0.0314 (9)	0.0308 (9)	−0.0025 (7)	0.0055 (7)	0.0022 (7)

Geometric parameters (Å, º)

S1—C8	1.6757 (17)	C4—C5	1.377 (2)
O1—C1	1.359 (2)	C4—H4	0.93
O1—H1	0.82	C5—C6	1.407 (2)
N1—C8	1.377 (2)	C5—H5	0.93
N1—C7	1.385 (2)	C6—C7	1.458 (2)
N1—C9	1.442 (2)	C9—C14	1.378 (2)
N2—C8	1.340 (2)	C9—C10	1.383 (2)
N2—N3	1.367 (2)	C10—C11	1.387 (2)
N2—H2N	0.86	C10—H10	0.93
N3—C7	1.311 (2)	C11—C12	1.384 (3)
C1—C2	1.388 (3)	C11—H11	0.93
C1—C6	1.407 (2)	C12—C13	1.381 (3)
C2—C3	1.378 (3)	C12—H12	0.93
C2—H2	0.93	C13—C14	1.383 (3)
C3—C4	1.388 (3)	C13—H13	0.93
C3—H3	0.93	C14—H14	0.93
C1—O1—H1	109.5	C5—C6—C7	122.47 (15)
C8—N1—C7	108.15 (13)	N3—C7—N1	109.77 (15)
C8—N1—C9	124.78 (13)	N3—C7—C6	122.71 (15)
C7—N1—C9	127.03 (14)	N1—C7—C6	127.50 (15)
C8—N2—N3	113.16 (14)	N2—C8—N1	103.69 (14)
C8—N2—H2N	123.4	N2—C8—S1	127.96 (13)
N3—N2—H2N	123.4	N1—C8—S1	128.36 (12)
C7—N3—N2	105.15 (13)	C14—C9—C10	122.05 (15)
O1—C1—C2	116.09 (15)	C14—C9—N1	118.95 (14)
O1—C1—C6	124.05 (16)	C10—C9—N1	118.86 (14)
C2—C1—C6	119.86 (16)	C9—C10—C11	118.52 (16)
C3—C2—C1	120.64 (16)	C9—C10—H10	120.7
C3—C2—H2	119.7	C11—C10—H10	120.7
C1—C2—H2	119.7	C12—C11—C10	119.91 (17)
C2—C3—C4	120.32 (17)	C12—C11—H11	120.0
C2—C3—H3	119.8	C10—C11—H11	120.0
C4—C3—H3	119.8	C13—C12—C11	120.68 (17)
C5—C4—C3	119.68 (17)	C13—C12—H12	119.7
C5—C4—H4	120.2	C11—C12—H12	119.7
C3—C4—H4	120.2	C12—C13—C14	119.92 (17)
C4—C5—C6	121.09 (16)	C12—C13—H13	120.0
C4—C5—H5	119.5	C14—C13—H13	120.0
C6—C5—H5	119.5	C9—C14—C13	118.88 (17)
C1—C6—C5	118.28 (16)	C9—C14—H14	120.6
C1—C6—C7	119.19 (15)	C13—C14—H14	120.6
C8—N2—N3—C7	1.66 (19)	C1—C6—C7—N1	157.61 (16)
O1—C1—C2—C3	177.59 (16)	C5—C6—C7—N1	−25.2 (3)
C6—C1—C2—C3	−2.8 (3)	N3—N2—C8—N1	−2.74 (18)
C1—C2—C3—C4	−0.3 (3)	N3—N2—C8—S1	177.35 (12)
C2—C3—C4—C5	1.9 (3)	C7—N1—C8—N2	2.71 (17)
C3—C4—C5—C6	−0.3 (3)	C9—N1—C8—N2	−175.23 (14)
O1—C1—C6—C5	−176.19 (15)	C7—N1—C8—S1	−177.38 (12)
C2—C1—C6—C5	4.3 (2)	C9—N1—C8—S1	4.7 (2)
O1—C1—C6—C7	1.1 (2)	C8—N1—C9—C14	−72.3 (2)
C2—C1—C6—C7	−178.44 (15)	C7—N1—C9—C14	110.18 (18)
C4—C5—C6—C1	−2.8 (2)	C8—N1—C9—C10	111.90 (18)
C4—C5—C6—C7	−179.92 (15)	C7—N1—C9—C10	−65.6 (2)
N2—N3—C7—N1	0.19 (18)	C14—C9—C10—C11	−1.7 (3)
N2—N3—C7—C6	−178.68 (14)	N1—C9—C10—C11	173.99 (16)
C8—N1—C7—N3	−1.87 (18)	C9—C10—C11—C12	0.3 (3)
C9—N1—C7—N3	176.00 (14)	C10—C11—C12—C13	1.0 (3)
C8—N1—C7—C6	176.93 (15)	C11—C12—C13—C14	−1.0 (3)
C9—N1—C7—C6	−5.2 (3)	C10—C9—C14—C13	1.7 (3)
C1—C6—C7—N3	−23.7 (2)	N1—C9—C14—C13	−173.98 (16)
C5—C6—C7—N3	153.42 (17)	C12—C13—C14—C9	−0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.82	1.98	2.693 (2)	145
N2—H2N···S1^i	0.86	2.46	3.279 (2)	159
C12—H12···N3^ii	0.93	2.59	3.502 (2)	165
C5—H5···Cg1	0.93	2.83	3.551 (2)	135
C14—H14···Cg2^iii	0.93	2.71	3.546 (2)	150

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) x−1, y, z.