4-Methyl-5-phenyl-1H-pyrazol-3-ol.

The title compound, C(10)H(10)N(2)O, crystallizes with two independent mol-ecules in the asymmetric unit, having closely comparable geometries. The dihedral angles between the 1H-pyrazole and benzene rings in the two mol-ecules are 39.57 (14) and 41.95 (13)°. The two mol-ecules are each connected to neighbouring mol-ecules by pairs of inter-molecular O-H⋯N hydrogen bonds, forming dimers with R(2) (2)(8) ring motifs. These dimers are further linked into R(4) (4)(10) ring motifs by inter-molecular N-H⋯O hydrogen bonds, forming chains along [101]. The crystal structure is further stabilized by a C-H⋯π inter-action.

Related literature

For the biological activity of 4-methyl-3-phenyl-1H-pyrazol-5-ol, see: Brogden (1986 ▶); Gursoy et al. (2000 ▶); Ragavan et al. (2009 ▶, 2010 ▶); Watanabe et al. (1984 ▶); Kawai et al. (1997 ▶); Wu et al. (2002 ▶). For related structures, see: Shahani et al. (2009 ▶, 2010a ▶,b ▶,c ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H10N2O

M = 174.20

Monoclinic,

a = 26.4082 (19) Å

b = 11.0972 (8) Å

c = 14.1245 (10) Å

β = 118.996 (1)°

V = 3620.4 (4) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.35 × 0.14 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.970, T max = 0.993

19166 measured reflections

5255 independent reflections

2907 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.204

S = 1.13

5255 reflections

243 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.26 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/S1600536810022828/is2561sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022828/is2561Isup2.hkl

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

C10H10N2O	F(000) = 1472
Mr = 174.20	Dx = 1.278 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3052 reflections
a = 26.4082 (19) Å	θ = 3.3–27.2°
b = 11.0972 (8) Å	µ = 0.09 mm−1
c = 14.1245 (10) Å	T = 100 K
β = 118.996 (1)°	Block, colourless
V = 3620.4 (4) Å3	0.35 × 0.14 × 0.08 mm
Z = 16

Bruker APEXII DUO CCD area-detector diffractometer	5255 independent reflections
Radiation source: fine-focus sealed tube	2907 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −37→28
Tmin = 0.970, Tmax = 0.993	k = −15→13
19166 measured reflections	l = −19→19

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0985P)2] where P = (Fo2 + 2Fc2)/3
5255 reflections	(Δ/σ)max = 0.001
243 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.26 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
O1A	0.30484 (5)	1.15234 (15)	0.48624 (10)	0.0513 (4)
H1OA	0.3021	1.1865	0.5356	0.077*
N1A	0.17011 (7)	1.19165 (16)	0.26752 (12)	0.0419 (4)
N2A	0.21137 (6)	1.22060 (17)	0.36985 (11)	0.0416 (4)
C1A	0.09436 (9)	1.0463 (3)	0.07114 (18)	0.0643 (7)
H1AA	0.0772	1.0599	0.1142	0.077*
C2A	0.06077 (11)	1.0113 (3)	−0.0353 (2)	0.0835 (10)
H2AA	0.0211	1.0019	−0.0634	0.100*
C3A	0.08503 (12)	0.9902 (3)	−0.09985 (19)	0.0704 (8)
H3AA	0.0621	0.9665	−0.1715	0.084*
C4A	0.14342 (12)	1.0042 (3)	−0.05821 (19)	0.0676 (7)
H4AA	0.1603	0.9906	−0.1017	0.081*
C5A	0.17726 (10)	1.0384 (3)	0.04793 (17)	0.0605 (6)
H5AA	0.2170	1.0462	0.0758	0.073*
C6A	0.15335 (8)	1.06126 (19)	0.11381 (14)	0.0412 (4)
C7A	0.18926 (8)	1.10453 (19)	0.22525 (14)	0.0386 (4)
C8A	0.24504 (8)	1.07398 (19)	0.30334 (14)	0.0406 (4)
C9A	0.25656 (7)	1.1493 (2)	0.39179 (14)	0.0404 (4)
C10A	0.28424 (9)	0.9785 (2)	0.30003 (17)	0.0526 (5)
H10A	0.2662	0.9409	0.2300	0.079*
H10B	0.2914	0.9190	0.3545	0.079*
H10C	0.3202	1.0143	0.3135	0.079*
O1B	−0.05992 (5)	0.70768 (16)	−0.21038 (10)	0.0515 (4)
H1OB	−0.0528	0.7049	−0.2616	0.077*
N1B	0.08261 (7)	0.69465 (18)	−0.01528 (12)	0.0468 (4)
N2B	0.04080 (6)	0.70277 (17)	−0.12057 (12)	0.0455 (4)
C1B	0.14424 (9)	0.7478 (2)	0.21872 (16)	0.0564 (6)
H1BA	0.1524	0.8034	0.1787	0.068*
C2B	0.17998 (11)	0.7390 (3)	0.32909 (18)	0.0725 (8)
H2BA	0.2123	0.7887	0.3631	0.087*
C3B	0.16837 (12)	0.6580 (3)	0.38904 (18)	0.0708 (8)
H3BA	0.1925	0.6531	0.4635	0.085*
C4B	0.12108 (10)	0.5843 (3)	0.33917 (17)	0.0630 (7)
H4BA	0.1134	0.5285	0.3797	0.076*
C5B	0.08471 (9)	0.5923 (2)	0.22872 (16)	0.0520 (5)
H5BA	0.0524	0.5426	0.1954	0.062*
C6B	0.09620 (8)	0.67397 (19)	0.16757 (14)	0.0409 (4)
C7B	0.05896 (8)	0.68061 (19)	0.04958 (14)	0.0400 (4)
C8B	−0.00068 (8)	0.6800 (2)	−0.01460 (14)	0.0411 (5)
C9B	−0.00976 (8)	0.69654 (19)	−0.12047 (14)	0.0406 (4)
C10B	−0.04620 (9)	0.6615 (3)	0.01754 (18)	0.0598 (6)
H10D	−0.0283	0.6528	0.0947	0.090*
H10E	−0.0679	0.5901	−0.0167	0.090*
H10F	−0.0717	0.7298	−0.0047	0.090*
H1NB	0.1235 (11)	0.687 (3)	0.0001 (19)	0.073 (8)*
H1NA	0.1316 (11)	1.224 (2)	0.2420 (18)	0.064 (7)*

	U11	U22	U33	U12	U13	U23
O1A	0.0298 (6)	0.0806 (12)	0.0370 (7)	0.0088 (6)	0.0112 (5)	−0.0066 (7)
N1A	0.0321 (7)	0.0554 (11)	0.0348 (7)	0.0049 (7)	0.0134 (6)	−0.0018 (7)
N2A	0.0299 (7)	0.0569 (11)	0.0336 (7)	0.0034 (7)	0.0120 (6)	−0.0038 (7)
C1A	0.0429 (11)	0.093 (2)	0.0548 (12)	−0.0142 (12)	0.0221 (10)	−0.0223 (12)
C2A	0.0463 (13)	0.126 (3)	0.0661 (15)	−0.0210 (15)	0.0174 (12)	−0.0364 (17)
C3A	0.0739 (17)	0.079 (2)	0.0488 (12)	−0.0139 (14)	0.0223 (12)	−0.0220 (12)
C4A	0.0755 (16)	0.082 (2)	0.0516 (12)	−0.0043 (14)	0.0357 (12)	−0.0183 (12)
C5A	0.0478 (11)	0.0854 (19)	0.0496 (11)	−0.0037 (12)	0.0245 (10)	−0.0106 (12)
C6A	0.0393 (9)	0.0436 (12)	0.0394 (9)	−0.0020 (8)	0.0180 (8)	−0.0021 (8)
C7A	0.0342 (8)	0.0461 (12)	0.0385 (9)	−0.0015 (8)	0.0199 (7)	−0.0007 (8)
C8A	0.0330 (8)	0.0515 (13)	0.0383 (9)	0.0012 (8)	0.0181 (7)	−0.0002 (8)
C9A	0.0295 (8)	0.0549 (13)	0.0363 (9)	0.0031 (8)	0.0157 (7)	0.0020 (8)
C10A	0.0426 (10)	0.0601 (15)	0.0530 (11)	0.0109 (10)	0.0214 (9)	−0.0005 (10)
O1B	0.0298 (6)	0.0862 (12)	0.0357 (7)	0.0068 (7)	0.0135 (6)	−0.0007 (6)
N1B	0.0305 (8)	0.0740 (14)	0.0338 (7)	−0.0012 (8)	0.0139 (6)	0.0038 (7)
N2B	0.0291 (7)	0.0713 (13)	0.0316 (7)	0.0007 (7)	0.0113 (6)	0.0029 (7)
C1B	0.0556 (12)	0.0620 (16)	0.0418 (10)	−0.0101 (11)	0.0160 (9)	0.0013 (10)
C2B	0.0650 (15)	0.088 (2)	0.0436 (12)	−0.0171 (14)	0.0097 (11)	−0.0075 (12)
C3B	0.0685 (16)	0.102 (2)	0.0352 (10)	0.0073 (15)	0.0196 (11)	0.0036 (12)
C4B	0.0648 (14)	0.0853 (19)	0.0455 (11)	0.0113 (13)	0.0320 (11)	0.0194 (11)
C5B	0.0494 (11)	0.0626 (15)	0.0466 (10)	0.0015 (10)	0.0253 (9)	0.0098 (10)
C6B	0.0398 (9)	0.0474 (12)	0.0349 (8)	0.0043 (8)	0.0176 (8)	0.0034 (8)
C7B	0.0369 (9)	0.0481 (12)	0.0351 (9)	−0.0006 (8)	0.0174 (8)	0.0021 (8)
C8B	0.0338 (9)	0.0519 (13)	0.0384 (9)	−0.0004 (8)	0.0180 (8)	0.0009 (8)
C9B	0.0308 (8)	0.0524 (13)	0.0363 (9)	0.0002 (8)	0.0145 (7)	−0.0011 (8)
C10B	0.0405 (11)	0.0886 (19)	0.0561 (12)	0.0052 (11)	0.0280 (10)	0.0070 (12)

O1A—C9A	1.326 (2)	O1B—C9B	1.323 (2)
O1A—H1OA	0.8273	O1B—H1OB	0.8317
N1A—C7A	1.356 (3)	N1B—C7B	1.345 (2)
N1A—N2A	1.3612 (19)	N1B—N2B	1.359 (2)
N1A—H1NA	0.97 (2)	N1B—H1NB	1.00 (3)
N2A—C9A	1.337 (2)	N2B—C9B	1.338 (2)
C1A—C2A	1.380 (3)	C1B—C2B	1.380 (3)
C1A—C6A	1.381 (3)	C1B—C6B	1.384 (3)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.365 (4)	C2B—C3B	1.368 (4)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.367 (4)	C3B—C4B	1.368 (4)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.375 (3)	C4B—C5B	1.383 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.378 (3)	C5B—C6B	1.383 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.470 (2)	C6B—C7B	1.470 (2)
C7A—C8A	1.388 (2)	C7B—C8B	1.385 (2)
C8A—C9A	1.409 (3)	C8B—C9B	1.407 (3)
C8A—C10A	1.498 (3)	C8B—C10B	1.491 (3)
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C9A—O1A—H1OA	115.1	C9B—O1B—H1OB	106.7
C7A—N1A—N2A	111.00 (15)	C7B—N1B—N2B	110.74 (15)
C7A—N1A—H1NA	130.4 (15)	C7B—N1B—H1NB	130.8 (14)
N2A—N1A—H1NA	117.7 (14)	N2B—N1B—H1NB	117.7 (14)
C9A—N2A—N1A	105.76 (15)	C9B—N2B—N1B	106.09 (15)
C2A—C1A—C6A	120.2 (2)	C2B—C1B—C6B	120.0 (2)
C2A—C1A—H1AA	119.9	C2B—C1B—H1BA	120.0
C6A—C1A—H1AA	119.9	C6B—C1B—H1BA	120.0
C3A—C2A—C1A	120.9 (2)	C3B—C2B—C1B	120.7 (2)
C3A—C2A—H2AA	119.5	C3B—C2B—H2BA	119.7
C1A—C2A—H2AA	119.5	C1B—C2B—H2BA	119.7
C2A—C3A—C4A	119.3 (2)	C4B—C3B—C2B	119.8 (2)
C2A—C3A—H3AA	120.3	C4B—C3B—H3BA	120.1
C4A—C3A—H3AA	120.3	C2B—C3B—H3BA	120.1
C3A—C4A—C5A	120.1 (2)	C3B—C4B—C5B	120.2 (2)
C3A—C4A—H4AA	119.9	C3B—C4B—H4BA	119.9
C5A—C4A—H4AA	119.9	C5B—C4B—H4BA	119.9
C4A—C5A—C6A	121.3 (2)	C4B—C5B—C6B	120.3 (2)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.9
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.9
C5A—C6A—C1A	118.19 (18)	C1B—C6B—C5B	119.03 (18)
C5A—C6A—C7A	120.97 (18)	C1B—C6B—C7B	120.16 (18)
C1A—C6A—C7A	120.81 (18)	C5B—C6B—C7B	120.79 (18)
N1A—C7A—C8A	107.63 (16)	N1B—C7B—C8B	108.12 (15)
N1A—C7A—C6A	121.31 (16)	N1B—C7B—C6B	120.11 (16)
C8A—C7A—C6A	131.04 (18)	C8B—C7B—C6B	131.71 (17)
C7A—C8A—C9A	104.45 (17)	C7B—C8B—C9B	104.41 (16)
C7A—C8A—C10A	129.14 (17)	C7B—C8B—C10B	129.08 (17)
C9A—C8A—C10A	126.32 (17)	C9B—C8B—C10B	126.47 (17)
O1A—C9A—N2A	122.24 (17)	O1B—C9B—N2B	121.95 (16)
O1A—C9A—C8A	126.60 (17)	O1B—C9B—C8B	127.43 (17)
N2A—C9A—C8A	111.16 (15)	N2B—C9B—C8B	110.60 (15)
C8A—C10A—H10A	109.5	C8B—C10B—H10D	109.5
C8A—C10A—H10B	109.5	C8B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C8A—C10A—H10C	109.5	C8B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C7A—N1A—N2A—C9A	−0.7 (2)	C7B—N1B—N2B—C9B	1.5 (2)
C6A—C1A—C2A—C3A	0.3 (5)	C6B—C1B—C2B—C3B	−0.2 (4)
C1A—C2A—C3A—C4A	0.0 (5)	C1B—C2B—C3B—C4B	0.4 (5)
C2A—C3A—C4A—C5A	0.4 (5)	C2B—C3B—C4B—C5B	−0.7 (4)
C3A—C4A—C5A—C6A	−1.2 (4)	C3B—C4B—C5B—C6B	0.8 (4)
C4A—C5A—C6A—C1A	1.4 (4)	C2B—C1B—C6B—C5B	0.2 (4)
C4A—C5A—C6A—C7A	−176.4 (2)	C2B—C1B—C6B—C7B	−178.2 (2)
C2A—C1A—C6A—C5A	−1.0 (4)	C4B—C5B—C6B—C1B	−0.5 (3)
C2A—C1A—C6A—C7A	176.8 (3)	C4B—C5B—C6B—C7B	178.0 (2)
N2A—N1A—C7A—C8A	0.7 (2)	N2B—N1B—C7B—C8B	−0.3 (2)
N2A—N1A—C7A—C6A	−177.51 (17)	N2B—N1B—C7B—C6B	−177.91 (18)
C5A—C6A—C7A—N1A	138.9 (2)	C1B—C6B—C7B—N1B	39.6 (3)
C1A—C6A—C7A—N1A	−38.9 (3)	C5B—C6B—C7B—N1B	−138.8 (2)
C5A—C6A—C7A—C8A	−38.9 (3)	C1B—C6B—C7B—C8B	−137.3 (2)
C1A—C6A—C7A—C8A	143.3 (2)	C5B—C6B—C7B—C8B	44.2 (3)
N1A—C7A—C8A—C9A	−0.5 (2)	N1B—C7B—C8B—C9B	−0.9 (2)
C6A—C7A—C8A—C9A	177.5 (2)	C6B—C7B—C8B—C9B	176.3 (2)
N1A—C7A—C8A—C10A	176.4 (2)	N1B—C7B—C8B—C10B	177.0 (2)
C6A—C7A—C8A—C10A	−5.6 (4)	C6B—C7B—C8B—C10B	−5.9 (4)
N1A—N2A—C9A—O1A	−179.23 (17)	N1B—N2B—C9B—O1B	176.63 (19)
N1A—N2A—C9A—C8A	0.4 (2)	N1B—N2B—C9B—C8B	−2.1 (2)
C7A—C8A—C9A—O1A	179.64 (19)	C7B—C8B—C9B—O1B	−176.7 (2)
C10A—C8A—C9A—O1A	2.7 (3)	C10B—C8B—C9B—O1B	5.3 (4)
C7A—C8A—C9A—N2A	0.1 (2)	C7B—C8B—C9B—N2B	1.9 (2)
C10A—C8A—C9A—N2A	−176.89 (19)	C10B—C8B—C9B—N2B	−176.1 (2)

Cg1 is the centroid of the C1B–C6B benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N2Ai	0.83	1.85	2.673 (2)	171
O1B—H1OB···N2Bii	0.83	1.84	2.670 (2)	177
N1B—H1NB···O1Aiii	1.00 (3)	1.85 (3)	2.836 (3)	171 (3)
N1A—H1NA···O1Biv	0.97 (3)	1.88 (3)	2.844 (2)	173 (2)
C10A—H10C···Cg1v	0.96	2.77	3.575 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1B–C6B benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯N2Ai	0.83	1.85	2.673 (2)	171
O1B—H1OB⋯N2Bii	0.83	1.84	2.670 (2)	177
N1B—H1NB⋯O1Aiii	1.00 (3)	1.85 (3)	2.836 (3)	171 (3)
N1A—H1NA⋯O1Biv	0.97 (3)	1.88 (3)	2.844 (2)	173 (2)
C10A—H10C⋯Cg1v	0.96	2.77	3.575 (3)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .