1,3-Dimethyl-4-phenyl-sulfanyl-1H-pyrazol-5-ol.

In the title compound, C(11)H(12)N(2)OS, the pyrazole ring makes a dihedral angle of 85.40 (8)° with the phenyl ring. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link mol-ecules into a two-dimensional network parallel to the bc plane.

Related literature

For pyrazole derivatives and their microbial activity, see: Ragavan et al. (2009 ▶, 2010 ▶). For related structures, see: Shahani et al. (2009 ▶, 2010a ▶,b ▶,c ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H12N2OS

M = 220.30

Orthorhombic,

a = 10.9479 (2) Å

b = 11.3470 (3) Å

c = 17.7392 (4) Å

V = 2203.67 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.33 × 0.13 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.917, T max = 0.971

12209 measured reflections

3027 independent reflections

2406 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.04

3027 reflections

142 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004922/is2676sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004922/is2676Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H12N2OS	F(000) = 928
Mr = 220.30	Dx = 1.328 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2873 reflections
a = 10.9479 (2) Å	θ = 2.8–29.1°
b = 11.3470 (3) Å	µ = 0.27 mm−1
c = 17.7392 (4) Å	T = 100 K
V = 2203.67 (9) Å3	Block, colourless
Z = 8	0.33 × 0.13 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	3027 independent reflections
Radiation source: fine-focus sealed tube	2406 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 29.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→15
Tmin = 0.917, Tmax = 0.971	k = −15→15
12209 measured reflections	l = −16→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.8061P] where P = (Fo2 + 2Fc2)/3
3027 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
S1	0.09449 (3)	0.31932 (3)	0.09298 (2)	0.01802 (11)
O1	0.32686 (10)	0.34450 (8)	−0.02532 (6)	0.0207 (2)
N1	0.20240 (12)	0.61926 (10)	0.00845 (8)	0.0202 (3)
N2	0.28173 (12)	0.54374 (10)	−0.02791 (7)	0.0192 (3)
C1	0.28747 (15)	0.36136 (13)	0.19278 (9)	0.0225 (3)
H1A	0.3057	0.4285	0.1649	0.027*
C2	0.35663 (15)	0.33304 (13)	0.25590 (9)	0.0254 (3)
H2A	0.4211	0.3816	0.2700	0.031*
C3	0.33066 (15)	0.23327 (14)	0.29808 (9)	0.0236 (3)
H3A	0.3766	0.2154	0.3407	0.028*
C4	0.23531 (15)	0.16043 (13)	0.27606 (9)	0.0243 (3)
H4A	0.2180	0.0929	0.3037	0.029*
C5	0.16551 (14)	0.18758 (13)	0.21304 (9)	0.0212 (3)
H5A	0.1019	0.1382	0.1986	0.025*
C6	0.19092 (13)	0.28904 (12)	0.17148 (8)	0.0173 (3)
C7	0.16428 (13)	0.43840 (11)	0.04922 (8)	0.0166 (3)
C8	0.26321 (13)	0.43076 (11)	−0.00304 (8)	0.0164 (3)
C9	0.13144 (14)	0.55679 (12)	0.05474 (8)	0.0178 (3)
C10	0.38173 (15)	0.58669 (13)	−0.07387 (10)	0.0239 (3)
H10A	0.4171	0.5222	−0.1013	0.036*
H10B	0.4427	0.6217	−0.0420	0.036*
H10C	0.3517	0.6446	−0.1087	0.036*
C11	0.03683 (15)	0.61354 (14)	0.10271 (9)	0.0248 (3)
H11A	0.0198	0.6912	0.0839	0.037*
H11B	0.0661	0.6189	0.1536	0.037*
H11C	−0.0365	0.5672	0.1016	0.037*
H1N1	0.1983 (19)	0.700 (2)	−0.0036 (13)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.01876 (19)	0.01847 (18)	0.0168 (2)	−0.00372 (13)	−0.00109 (13)	0.00267 (13)
O1	0.0267 (6)	0.0139 (4)	0.0215 (6)	0.0008 (4)	0.0046 (4)	0.0000 (4)
N1	0.0264 (7)	0.0129 (5)	0.0212 (7)	0.0017 (5)	−0.0005 (5)	−0.0006 (5)
N2	0.0240 (6)	0.0131 (5)	0.0206 (7)	−0.0002 (5)	0.0034 (5)	0.0007 (5)
C1	0.0273 (8)	0.0198 (7)	0.0204 (8)	−0.0046 (6)	−0.0027 (6)	0.0034 (6)
C2	0.0285 (8)	0.0257 (7)	0.0221 (9)	−0.0037 (6)	−0.0065 (7)	−0.0002 (6)
C3	0.0255 (8)	0.0298 (8)	0.0155 (8)	0.0053 (6)	−0.0012 (6)	0.0006 (6)
C4	0.0247 (8)	0.0260 (7)	0.0222 (8)	0.0015 (6)	0.0032 (6)	0.0082 (6)
C5	0.0197 (7)	0.0213 (7)	0.0225 (8)	−0.0015 (6)	0.0013 (6)	0.0043 (6)
C6	0.0196 (7)	0.0188 (6)	0.0134 (7)	0.0007 (5)	0.0019 (5)	0.0003 (5)
C7	0.0193 (7)	0.0148 (6)	0.0156 (7)	−0.0014 (5)	−0.0003 (5)	0.0005 (5)
C8	0.0224 (7)	0.0127 (6)	0.0141 (7)	−0.0017 (5)	−0.0018 (6)	0.0001 (5)
C9	0.0207 (7)	0.0179 (6)	0.0149 (7)	0.0009 (5)	−0.0035 (6)	−0.0002 (5)
C10	0.0283 (8)	0.0184 (7)	0.0250 (8)	−0.0043 (6)	0.0050 (7)	0.0032 (6)
C11	0.0248 (8)	0.0250 (7)	0.0245 (9)	0.0071 (6)	−0.0008 (6)	−0.0021 (6)

S1—C7	1.7356 (14)	C3—H3A	0.9300
S1—C6	1.7809 (15)	C4—C5	1.389 (2)
O1—C8	1.2648 (17)	C4—H4A	0.9300
N1—C9	1.3343 (19)	C5—C6	1.395 (2)
N1—N2	1.3801 (17)	C5—H5A	0.9300
N1—H1N1	0.94 (2)	C7—C9	1.3942 (19)
N2—C8	1.3708 (17)	C7—C8	1.428 (2)
N2—C10	1.4494 (19)	C9—C11	1.487 (2)
C1—C2	1.389 (2)	C10—H10A	0.9600
C1—C6	1.391 (2)	C10—H10B	0.9600
C1—H1A	0.9300	C10—H10C	0.9600
C2—C3	1.387 (2)	C11—H11A	0.9600
C2—H2A	0.9300	C11—H11B	0.9600
C3—C4	1.388 (2)	C11—H11C	0.9600
C7—S1—C6	103.83 (7)	C1—C6—S1	123.32 (11)
C9—N1—N2	108.92 (11)	C5—C6—S1	117.02 (11)
C9—N1—H1N1	129.0 (13)	C9—C7—C8	107.44 (12)
N2—N1—H1N1	121.9 (13)	C9—C7—S1	127.24 (12)
C8—N2—N1	109.70 (12)	C8—C7—S1	125.24 (10)
C8—N2—C10	127.39 (13)	O1—C8—N2	122.79 (13)
N1—N2—C10	121.97 (11)	O1—C8—C7	131.88 (13)
C2—C1—C6	119.79 (14)	N2—C8—C7	105.33 (12)
C2—C1—H1A	120.1	N1—C9—C7	108.57 (13)
C6—C1—H1A	120.1	N1—C9—C11	121.85 (13)
C3—C2—C1	120.80 (15)	C7—C9—C11	129.57 (14)
C3—C2—H2A	119.6	N2—C10—H10A	109.5
C1—C2—H2A	119.6	N2—C10—H10B	109.5
C2—C3—C4	119.26 (15)	H10A—C10—H10B	109.5
C2—C3—H3A	120.4	N2—C10—H10C	109.5
C4—C3—H3A	120.4	H10A—C10—H10C	109.5
C3—C4—C5	120.56 (14)	H10B—C10—H10C	109.5
C3—C4—H4A	119.7	C9—C11—H11A	109.5
C5—C4—H4A	119.7	C9—C11—H11B	109.5
C4—C5—C6	119.92 (14)	H11A—C11—H11B	109.5
C4—C5—H5A	120.0	C9—C11—H11C	109.5
C6—C5—H5A	120.0	H11A—C11—H11C	109.5
C1—C6—C5	119.66 (14)	H11B—C11—H11C	109.5
C9—N1—N2—C8	−1.48 (17)	N1—N2—C8—O1	−177.46 (13)
C9—N1—N2—C10	−171.15 (14)	C10—N2—C8—O1	−8.5 (2)
C6—C1—C2—C3	0.0 (2)	N1—N2—C8—C7	2.10 (16)
C1—C2—C3—C4	0.9 (2)	C10—N2—C8—C7	171.06 (14)
C2—C3—C4—C5	−0.8 (2)	C9—C7—C8—O1	177.55 (16)
C3—C4—C5—C6	−0.2 (2)	S1—C7—C8—O1	−5.6 (2)
C2—C1—C6—C5	−1.0 (2)	C9—C7—C8—N2	−1.96 (16)
C2—C1—C6—S1	178.43 (12)	S1—C7—C8—N2	174.91 (11)
C4—C5—C6—C1	1.1 (2)	N2—N1—C9—C7	0.18 (17)
C4—C5—C6—S1	−178.38 (12)	N2—N1—C9—C11	179.36 (13)
C7—S1—C6—C1	7.87 (15)	C8—C7—C9—N1	1.12 (17)
C7—S1—C6—C5	−172.70 (12)	S1—C7—C9—N1	−175.67 (11)
C6—S1—C7—C9	−100.38 (14)	C8—C7—C9—C11	−177.97 (15)
C6—S1—C7—C8	83.36 (14)	S1—C7—C9—C11	5.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.94 (2)	1.71 (2)	2.6446 (16)	173 (2)
C3—H3A···O1ii	0.93	2.53	3.2549 (19)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.94 (2)	1.71 (2)	2.6446 (16)	173 (2)
C3—H3A⋯O1ii	0.93	2.53	3.2549 (19)	135

Symmetry codes: (i) ; (ii) .