5-(2-Hydro­xy­phenyl)-4-(p-tolyl)-2,4-di­hydro-1,2,4-triazole-3-thione

In the structure of the title compound, C₁₅H₁₃N₃OS, the mol­ecules form centrosymmetric dimers through strong N—H...S hydrogen bonds, with an N...S distance of 3.271 (3) Å. In addition, the mol­ecule contains one O—H...N intramolecular hydrogen bond. The dimers are connected through weak intermolecular C—H...S hydrogen bonds into chains in the c direction, with a C...S distance of 3.742 (3) Å.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.148
• Data-to-parameter ratio = 13.8

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   0.143
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.14
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C15 H13 N3 O S

   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

   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
   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-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).

5-(2-Hydroxyphenyl)-4-(p-tolyl)-2,4-dihydro-1,2,4-triazole-3-thione

Crystal data

C15H13N3OS	F(000) = 1184
Mr = 283.34	Dx = 1.410 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 10560 reflections
a = 26.524 (3) Å	θ = 1.6–27.2°
b = 11.3288 (18) Å	µ = 0.24 mm^−1
c = 9.2310 (11) Å	T = 150 K
β = 104.643 (9)°	Plate, colourless
V = 2683.7 (6) Å^3	0.38 × 0.26 × 0.08 mm
Z = 8

Data collection

Stoe IPDS 2 diffractometer	2636 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1775 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.143
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
rotation method scans	h = −32→32
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
Tmin = 0.919, Tmax = 0.978	l = −11→11
9354 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0749P)^2] where P = (Fo^2 + 2Fc^2)/3
2636 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Special details

Experimental. Melting points were determined in open capillary tubes on a Gallenkamp digital melting-point apparatus and are uncorrected. The IR spectra were recorded as KBr disks with a Mattson 1000 F T—IR spectrometer. ¹H NMR spectra were recorded on an FX 90 Jeol 90 MHz NMR spectrometer in DMSO-d₆ with TMS as an internal standard.

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	0.01200 (2)	0.69821 (7)	0.02543 (9)	0.0327 (3)
O1	0.15575 (7)	0.41156 (17)	−0.3164 (2)	0.0368 (6)
H1	0.1382	0.4075	−0.2551	0.055*
N1	0.09264 (7)	0.69074 (19)	−0.1113 (3)	0.0261 (6)
N2	0.09765 (8)	0.5010 (2)	−0.1596 (3)	0.0319 (6)
N3	0.05803 (8)	0.5225 (2)	−0.0939 (3)	0.0324 (6)
H3	0.0377	0.4683	−0.0759	0.039*
C1	0.17960 (9)	0.5179 (3)	−0.3051 (3)	0.0299 (7)
C2	0.22122 (9)	0.5277 (3)	−0.3695 (4)	0.0343 (7)
H2	0.2305	0.4634	−0.4199	0.041*
C3	0.24902 (9)	0.6307 (3)	−0.3601 (4)	0.0362 (8)
H3A	0.2770	0.6357	−0.4035	0.043*
C4	0.23540 (9)	0.7272 (3)	−0.2859 (4)	0.0368 (8)
H4	0.2546	0.7968	−0.2776	0.044*
C5	0.19327 (9)	0.7195 (3)	−0.2244 (4)	0.0332 (7)
H5	0.1842	0.7851	−0.1760	0.040*
C6	0.16385 (9)	0.6166 (3)	−0.2325 (3)	0.0267 (6)
C7	0.11891 (9)	0.6040 (2)	−0.1687 (3)	0.0266 (6)
C8	0.05382 (9)	0.6361 (2)	−0.0602 (3)	0.0269 (7)
C9	0.09922 (9)	0.8174 (2)	−0.1062 (3)	0.0250 (6)
C10	0.13459 (9)	0.8698 (3)	0.0140 (3)	0.0295 (7)
H10	0.1548	0.8238	0.0904	0.035*
C11	0.13906 (10)	0.9907 (3)	0.0177 (3)	0.0316 (7)
H11	0.1633	1.0261	0.0963	0.038*
C12	0.10809 (9)	1.0616 (3)	−0.0934 (3)	0.0291 (7)
C13	0.07306 (10)	1.0065 (3)	−0.2112 (4)	0.0330 (7)
H13	0.0523	1.0522	−0.2869	0.040*
C14	0.06843 (9)	0.8848 (3)	−0.2182 (4)	0.0317 (7)
H14	0.0447	0.8490	−0.2977	0.038*
C15	0.11145 (10)	1.1944 (3)	−0.0873 (4)	0.0387 (8)
H15A	0.1003	1.2224	−0.0023	0.058*
H15B	0.0894	1.2269	−0.1772	0.058*
H15C	0.1468	1.2184	−0.0785	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0210 (3)	0.0297 (5)	0.0499 (6)	−0.0004 (3)	0.0139 (3)	0.0015 (4)
O1	0.0296 (9)	0.0327 (12)	0.0510 (15)	−0.0052 (8)	0.0156 (9)	−0.0063 (11)
N1	0.0184 (9)	0.0244 (12)	0.0357 (15)	−0.0015 (8)	0.0074 (9)	0.0000 (11)
N2	0.0207 (10)	0.0300 (14)	0.0469 (17)	−0.0030 (9)	0.0123 (10)	−0.0032 (12)
N3	0.0204 (10)	0.0274 (13)	0.0522 (18)	−0.0048 (9)	0.0146 (10)	0.0017 (12)
C1	0.0197 (11)	0.0337 (16)	0.0334 (18)	−0.0001 (11)	0.0016 (11)	−0.0023 (13)
C2	0.0234 (12)	0.0391 (18)	0.0403 (19)	0.0030 (12)	0.0079 (11)	−0.0040 (15)
C3	0.0201 (12)	0.052 (2)	0.039 (2)	0.0008 (12)	0.0113 (11)	0.0013 (15)
C4	0.0229 (13)	0.0407 (18)	0.048 (2)	−0.0076 (12)	0.0104 (12)	0.0007 (16)
C5	0.0256 (13)	0.0326 (17)	0.042 (2)	−0.0034 (11)	0.0095 (12)	−0.0064 (14)
C6	0.0191 (11)	0.0317 (15)	0.0289 (17)	−0.0006 (11)	0.0055 (10)	0.0011 (13)
C7	0.0193 (11)	0.0271 (15)	0.0317 (17)	−0.0001 (10)	0.0032 (10)	−0.0032 (13)
C8	0.0183 (11)	0.0285 (15)	0.0326 (18)	−0.0035 (10)	0.0038 (10)	0.0033 (13)
C9	0.0187 (11)	0.0254 (14)	0.0322 (17)	−0.0008 (10)	0.0086 (10)	0.0003 (13)
C10	0.0233 (12)	0.0308 (16)	0.0322 (18)	−0.0002 (10)	0.0028 (11)	0.0026 (13)
C11	0.0232 (12)	0.0354 (17)	0.0342 (18)	−0.0048 (11)	0.0038 (11)	−0.0050 (14)
C12	0.0216 (11)	0.0284 (15)	0.0400 (19)	−0.0005 (11)	0.0126 (11)	−0.0015 (13)
C13	0.0214 (11)	0.0345 (17)	0.041 (2)	0.0016 (11)	0.0039 (12)	0.0075 (15)
C14	0.0171 (11)	0.0380 (17)	0.0374 (19)	−0.0035 (11)	0.0024 (11)	−0.0001 (14)
C15	0.0268 (13)	0.0313 (17)	0.058 (2)	0.0006 (11)	0.0116 (13)	−0.0009 (15)

Geometric parameters (Å, º)

S1—C8	1.671 (3)	C5—C6	1.395 (4)
O1—C1	1.353 (3)	C5—H5	0.9300
O1—H1	0.8200	C6—C7	1.464 (4)
N1—C8	1.382 (3)	C9—C14	1.376 (4)
N1—C7	1.385 (3)	C9—C10	1.392 (4)
N1—C9	1.445 (3)	C10—C11	1.374 (4)
N2—C7	1.308 (3)	C10—H10	0.9300
N2—N3	1.361 (3)	C11—C12	1.396 (4)
N3—C8	1.335 (4)	C11—H11	0.9300
N3—H3	0.8600	C12—C13	1.387 (4)
C1—C2	1.384 (4)	C12—C15	1.507 (4)
C1—C6	1.420 (4)	C13—C14	1.384 (4)
C2—C3	1.371 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.387 (4)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.378 (4)	C15—H15C	0.9600
C4—H4	0.9300
C1—O1—H1	109.5	N1—C7—C6	128.6 (2)
C8—N1—C7	107.6 (2)	N3—C8—N1	103.8 (2)
C8—N1—C9	121.8 (2)	N3—C8—S1	128.4 (2)
C7—N1—C9	130.5 (2)	N1—C8—S1	127.9 (2)
C7—N2—N3	105.2 (2)	C14—C9—C10	121.0 (3)
C8—N3—N2	113.3 (2)	C14—C9—N1	118.9 (2)
C8—N3—H3	123.3	C10—C9—N1	120.1 (2)
N2—N3—H3	123.3	C11—C10—C9	118.8 (3)
O1—C1—C2	116.5 (3)	C11—C10—H10	120.6
O1—C1—C6	123.4 (2)	C9—C10—H10	120.6
C2—C1—C6	120.1 (3)	C10—C11—C12	121.7 (3)
C3—C2—C1	121.0 (3)	C10—C11—H11	119.2
C3—C2—H2	119.5	C12—C11—H11	119.2
C1—C2—H2	119.5	C13—C12—C11	118.0 (3)
C2—C3—C4	120.0 (3)	C13—C12—C15	120.0 (3)
C2—C3—H3A	120.0	C11—C12—C15	122.0 (3)
C4—C3—H3A	120.0	C14—C13—C12	121.2 (3)
C5—C4—C3	119.5 (3)	C14—C13—H13	119.4
C5—C4—H4	120.2	C12—C13—H13	119.4
C3—C4—H4	120.2	C9—C14—C13	119.3 (3)
C4—C5—C6	122.2 (3)	C9—C14—H14	120.3
C4—C5—H5	118.9	C13—C14—H14	120.3
C6—C5—H5	118.9	C12—C15—H15A	109.5
C5—C6—C1	117.1 (2)	C12—C15—H15B	109.5
C5—C6—C7	124.2 (3)	H15A—C15—H15B	109.5
C1—C6—C7	118.7 (2)	C12—C15—H15C	109.5
N2—C7—N1	110.0 (2)	H15A—C15—H15C	109.5
N2—C7—C6	121.4 (2)	H15B—C15—H15C	109.5
C7—N2—N3—C8	−0.5 (3)	C1—C6—C7—N1	−170.7 (3)
O1—C1—C2—C3	−177.9 (3)	N2—N3—C8—N1	1.5 (3)
C6—C1—C2—C3	2.3 (4)	N2—N3—C8—S1	−177.9 (2)
C1—C2—C3—C4	−0.3 (4)	C7—N1—C8—N3	−1.9 (3)
C2—C3—C4—C5	−1.2 (4)	C9—N1—C8—N3	175.5 (2)
C3—C4—C5—C6	0.8 (5)	C7—N1—C8—S1	177.5 (2)
C4—C5—C6—C1	1.1 (4)	C9—N1—C8—S1	−5.1 (4)
C4—C5—C6—C7	179.8 (3)	C8—N1—C9—C14	−82.1 (3)
O1—C1—C6—C5	177.6 (3)	C7—N1—C9—C14	94.6 (3)
C2—C1—C6—C5	−2.6 (4)	C8—N1—C9—C10	95.0 (3)
O1—C1—C6—C7	−1.2 (4)	C7—N1—C9—C10	−88.2 (4)
C2—C1—C6—C7	178.6 (2)	C14—C9—C10—C11	−1.3 (4)
N3—N2—C7—N1	−0.8 (3)	N1—C9—C10—C11	−178.4 (2)
N3—N2—C7—C6	179.3 (2)	C9—C10—C11—C12	1.8 (4)
C8—N1—C7—N2	1.8 (3)	C10—C11—C12—C13	−1.5 (4)
C9—N1—C7—N2	−175.3 (3)	C10—C11—C12—C15	177.8 (3)
C8—N1—C7—C6	−178.3 (3)	C11—C12—C13—C14	0.6 (4)
C9—N1—C7—C6	4.6 (5)	C15—C12—C13—C14	−178.7 (3)
C5—C6—C7—N2	−169.5 (3)	C10—C9—C14—C13	0.4 (4)
C1—C6—C7—N2	9.2 (4)	N1—C9—C14—C13	177.6 (3)
C5—C6—C7—N1	10.6 (4)	C12—C13—C14—C9	−0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1^i	0.86	2.41	3.271 (3)	174
C14—H14···S1^ii	0.93	2.83	3.742 (3)	168
O1—H1···N2	0.82	1.88	2.574 (3)	142

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