4-Methyl-5-phenyl-1H-pyrazol-3(2H)-one.

The asymmetric unit of the title compound, C(10)H(10)N(2)O, contains two crystallographically independent mol-ecules with similar geometries, which exist in the keto form. The C=O bond lengths are 1.2878 (12) Å in mol-ecule A and 1.2890 (12) Å in mol-ecule B, indicating that the compound undergoes enol-to-keto tautomerism during the crystallization process. In mol-ecule A, the pyrazole ring is approximately planar [maximum deviation = 0.007 (1) Å] and forms a dihedral angle of 36.67 (6)° with the attached phenyl ring. In mol-ecule B, the dihedral angle formed between the pyrazole ring [maximum deviation = 0.017 (1) Å] and the phenyl ring is 41.19 (6)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link neighbouring mol-ecules into dimers generating R(2) (2)(8) ring motifs. These dimers are linked into ribbons along [101] via inter-molecular N-H⋯O hydrogen bonds, forming R(4) (2)(10) ring motifs.

Related literature

For background to pyrazole derivatives and their anti­microbial activity, see: Ragavan et al. (2009 ▶, 2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the structure of the enol form of this mol­ecule, see: Shahani et al. (2010 ▶). For other related structures, see: Loh et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H10N2O

M = 174.20

Monoclinic,

a = 25.9337 (4) Å

b = 10.8100 (1) Å

c = 14.1426 (2) Å

β = 118.961 (1)°

V = 3468.98 (8) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.45 × 0.39 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.961, T max = 0.978

36992 measured reflections

5087 independent reflections

4389 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.03

5087 reflections

253 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.22 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/S160053681005213X/sj5074sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005213X/sj5074Isup2.hkl

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

C10H10N2O	F(000) = 1472
Mr = 174.20	Dx = 1.334 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9946 reflections
a = 25.9337 (4) Å	θ = 2.4–30.1°
b = 10.8100 (1) Å	µ = 0.09 mm−1
c = 14.1426 (2) Å	T = 100 K
β = 118.961 (1)°	Block, colourless
V = 3468.98 (8) Å3	0.45 × 0.39 × 0.25 mm
Z = 16

Bruker SMART APEXII CCD area-detector diffractometer	5087 independent reflections
Radiation source: fine-focus sealed tube	4389 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −36→36
Tmin = 0.961, Tmax = 0.978	k = −15→15
36992 measured reflections	l = −19→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0684P)2 + 2.050P] where P = (Fo2 + 2Fc2)/3
5087 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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	0.19371 (3)	0.15583 (7)	0.01430 (6)	0.01628 (16)
N1A	0.33170 (4)	0.19356 (8)	0.23566 (7)	0.01429 (17)
N2A	0.28884 (4)	0.22212 (8)	0.13372 (7)	0.01378 (17)
C1A	0.40804 (5)	0.05241 (11)	0.43463 (9)	0.0198 (2)
H1AA	0.4262	0.0681	0.3931	0.024*
C2A	0.44188 (5)	0.02010 (12)	0.54257 (10)	0.0249 (2)
H2AA	0.4826	0.0147	0.5730	0.030*
C3A	0.41532 (5)	−0.00418 (11)	0.60540 (10)	0.0222 (2)
H3AA	0.4382	−0.0251	0.6779	0.027*
C4A	0.35439 (5)	0.00296 (10)	0.55947 (9)	0.0209 (2)
H4AA	0.3364	−0.0139	0.6012	0.025*
C5A	0.32019 (5)	0.03512 (10)	0.45141 (9)	0.0188 (2)
H5AA	0.2794	0.0391	0.4211	0.023*
C6A	0.34665 (4)	0.06155 (9)	0.38784 (8)	0.01417 (19)
C7A	0.31075 (4)	0.10488 (9)	0.27595 (8)	0.01305 (19)
C8A	0.25384 (4)	0.07360 (9)	0.19815 (8)	0.01399 (19)
C9A	0.24055 (4)	0.14984 (9)	0.10712 (8)	0.01324 (19)
C10A	0.21385 (4)	−0.02449 (10)	0.20107 (9)	0.0171 (2)
H10A	0.2367	−0.0958	0.2385	0.026*
H10B	0.1855	−0.0472	0.1286	0.026*
H10C	0.1937	0.0066	0.2380	0.026*
O1B	0.43937 (3)	0.28341 (7)	0.28820 (6)	0.01641 (16)
N1B	0.58492 (4)	0.29961 (8)	0.48713 (7)	0.01537 (18)
N2B	0.54157 (4)	0.29083 (8)	0.38216 (7)	0.01525 (18)
C1B	0.64581 (5)	0.25037 (10)	0.72121 (9)	0.0177 (2)
H1BA	0.6549	0.1929	0.6825	0.021*
C2B	0.68154 (5)	0.26106 (11)	0.83201 (9)	0.0225 (2)
H2BA	0.7144	0.2102	0.8676	0.027*
C3B	0.66848 (5)	0.34762 (12)	0.89026 (10)	0.0233 (2)
H3BA	0.6926	0.3549	0.9645	0.028*
C4B	0.61925 (5)	0.42316 (11)	0.83712 (9)	0.0208 (2)
H4BA	0.6107	0.4816	0.8758	0.025*
C5B	0.58278 (5)	0.41160 (10)	0.72656 (9)	0.0168 (2)
H5BA	0.5494	0.4610	0.6916	0.020*
C6B	0.59605 (4)	0.32598 (9)	0.66741 (8)	0.01363 (19)
C7B	0.55927 (4)	0.31664 (9)	0.54975 (8)	0.01354 (19)
C8B	0.49830 (4)	0.31808 (9)	0.48467 (8)	0.01383 (19)
C9B	0.48786 (4)	0.29746 (9)	0.37751 (8)	0.01359 (19)
C10B	0.45201 (4)	0.34052 (10)	0.51676 (9)	0.0184 (2)
H10D	0.4627	0.2991	0.5838	0.028*
H10E	0.4149	0.3091	0.4617	0.028*
H10F	0.4487	0.4277	0.5254	0.028*
H1NB	0.6234 (7)	0.3100 (16)	0.5038 (13)	0.034 (4)*
H1NA	0.3696 (7)	0.2271 (15)	0.2649 (13)	0.030 (4)*
H2NA	0.2954 (8)	0.2691 (17)	0.0857 (14)	0.042 (5)*
H2NB	0.5490 (7)	0.2858 (15)	0.3239 (13)	0.032 (4)*

	U11	U22	U33	U12	U13	U23
O1A	0.0111 (3)	0.0236 (4)	0.0122 (4)	−0.0017 (3)	0.0041 (3)	0.0009 (3)
N1A	0.0108 (4)	0.0179 (4)	0.0116 (4)	−0.0012 (3)	0.0034 (3)	0.0017 (3)
N2A	0.0099 (4)	0.0182 (4)	0.0109 (4)	−0.0012 (3)	0.0031 (3)	0.0018 (3)
C1A	0.0151 (5)	0.0252 (5)	0.0193 (6)	0.0041 (4)	0.0084 (4)	0.0052 (4)
C2A	0.0156 (5)	0.0334 (6)	0.0210 (6)	0.0065 (4)	0.0051 (4)	0.0075 (5)
C3A	0.0239 (5)	0.0223 (5)	0.0155 (5)	0.0037 (4)	0.0057 (4)	0.0052 (4)
C4A	0.0249 (5)	0.0220 (5)	0.0180 (5)	0.0000 (4)	0.0122 (5)	0.0030 (4)
C5A	0.0163 (5)	0.0224 (5)	0.0179 (5)	−0.0006 (4)	0.0083 (4)	0.0020 (4)
C6A	0.0138 (4)	0.0135 (4)	0.0135 (5)	0.0002 (3)	0.0053 (4)	0.0003 (3)
C7A	0.0117 (4)	0.0148 (4)	0.0128 (5)	0.0005 (3)	0.0061 (4)	0.0005 (3)
C8A	0.0121 (4)	0.0157 (4)	0.0143 (5)	−0.0006 (3)	0.0065 (4)	−0.0001 (3)
C9A	0.0102 (4)	0.0165 (4)	0.0128 (5)	−0.0005 (3)	0.0054 (4)	−0.0010 (3)
C10A	0.0145 (4)	0.0183 (5)	0.0176 (5)	−0.0039 (3)	0.0071 (4)	0.0001 (4)
O1B	0.0108 (3)	0.0237 (4)	0.0127 (4)	−0.0020 (3)	0.0041 (3)	−0.0001 (3)
N1B	0.0097 (4)	0.0232 (4)	0.0108 (4)	−0.0011 (3)	0.0030 (3)	−0.0021 (3)
N2B	0.0110 (4)	0.0226 (4)	0.0110 (4)	−0.0009 (3)	0.0044 (3)	−0.0014 (3)
C1B	0.0163 (4)	0.0181 (5)	0.0158 (5)	0.0025 (4)	0.0056 (4)	0.0000 (4)
C2B	0.0198 (5)	0.0258 (5)	0.0163 (6)	0.0041 (4)	0.0042 (4)	0.0042 (4)
C3B	0.0227 (5)	0.0324 (6)	0.0121 (5)	−0.0028 (4)	0.0062 (4)	−0.0006 (4)
C4B	0.0222 (5)	0.0254 (5)	0.0177 (5)	−0.0039 (4)	0.0119 (4)	−0.0056 (4)
C5B	0.0151 (4)	0.0192 (5)	0.0160 (5)	0.0003 (3)	0.0073 (4)	−0.0017 (4)
C6B	0.0121 (4)	0.0155 (4)	0.0118 (5)	−0.0014 (3)	0.0046 (4)	−0.0004 (3)
C7B	0.0127 (4)	0.0142 (4)	0.0130 (5)	0.0005 (3)	0.0056 (4)	−0.0004 (3)
C8B	0.0123 (4)	0.0157 (4)	0.0131 (5)	0.0001 (3)	0.0058 (4)	0.0002 (3)
C9B	0.0116 (4)	0.0141 (4)	0.0146 (5)	−0.0004 (3)	0.0060 (4)	0.0006 (3)
C10B	0.0141 (4)	0.0243 (5)	0.0182 (5)	−0.0004 (4)	0.0089 (4)	−0.0020 (4)

O1A—C9A	1.2878 (12)	O1B—C9B	1.2890 (12)
N1A—C7A	1.3560 (13)	N1B—C7B	1.3533 (13)
N1A—N2A	1.3628 (12)	N1B—N2B	1.3640 (12)
N1A—H1NA	0.935 (16)	N1B—H1NB	0.913 (17)
N2A—C9A	1.3655 (12)	N2B—C9B	1.3641 (12)
N2A—H2NA	0.928 (19)	N2B—H2NB	0.933 (17)
C1A—C2A	1.3875 (16)	C1B—C2B	1.3861 (16)
C1A—C6A	1.4006 (14)	C1B—C6B	1.4004 (14)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.3878 (17)	C2B—C3B	1.3926 (17)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.3896 (16)	C3B—C4B	1.3901 (17)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.3893 (16)	C4B—C5B	1.3866 (16)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.3994 (14)	C5B—C6B	1.3979 (14)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.4708 (14)	C6B—C7B	1.4668 (14)
C7A—C8A	1.3895 (13)	C7B—C8B	1.3920 (13)
C8A—C9A	1.4233 (14)	C8B—C9B	1.4221 (14)
C8A—C10A	1.4978 (13)	C8B—C10B	1.4946 (14)
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C7A—N1A—N2A	108.49 (8)	C7B—N1B—N2B	108.33 (8)
C7A—N1A—H1NA	129.6 (10)	C7B—N1B—H1NB	129.5 (11)
N2A—N1A—H1NA	121.6 (10)	N2B—N1B—H1NB	120.7 (11)
N1A—N2A—C9A	109.34 (8)	N1B—N2B—C9B	109.45 (9)
N1A—N2A—H2NA	123.7 (11)	N1B—N2B—H2NB	123.4 (10)
C9A—N2A—H2NA	125.5 (11)	C9B—N2B—H2NB	127.0 (10)
C2A—C1A—C6A	120.42 (10)	C2B—C1B—C6B	120.09 (10)
C2A—C1A—H1AA	119.8	C2B—C1B—H1BA	120.0
C6A—C1A—H1AA	119.8	C6B—C1B—H1BA	120.0
C1A—C2A—C3A	120.42 (10)	C1B—C2B—C3B	120.25 (10)
C1A—C2A—H2AA	119.8	C1B—C2B—H2BA	119.9
C3A—C2A—H2AA	119.8	C3B—C2B—H2BA	119.9
C2A—C3A—C4A	119.66 (11)	C4B—C3B—C2B	119.85 (11)
C2A—C3A—H3AA	120.2	C4B—C3B—H3BA	120.1
C4A—C3A—H3AA	120.2	C2B—C3B—H3BA	120.1
C5A—C4A—C3A	120.25 (10)	C5B—C4B—C3B	120.20 (10)
C5A—C4A—H4AA	119.9	C5B—C4B—H4BA	119.9
C3A—C4A—H4AA	119.9	C3B—C4B—H4BA	119.9
C4A—C5A—C6A	120.49 (10)	C4B—C5B—C6B	120.22 (10)
C4A—C5A—H5AA	119.8	C4B—C5B—H5BA	119.9
C6A—C5A—H5AA	119.8	C6B—C5B—H5BA	119.9
C5A—C6A—C1A	118.74 (10)	C5B—C6B—C1B	119.37 (10)
C5A—C6A—C7A	120.29 (9)	C5B—C6B—C7B	120.73 (9)
C1A—C6A—C7A	120.89 (9)	C1B—C6B—C7B	119.89 (9)
N1A—C7A—C8A	109.11 (9)	N1B—C7B—C8B	109.25 (9)
N1A—C7A—C6A	120.23 (9)	N1B—C7B—C6B	119.73 (9)
C8A—C7A—C6A	130.60 (9)	C8B—C7B—C6B	130.99 (9)
C7A—C8A—C9A	105.93 (8)	C7B—C8B—C9B	105.79 (8)
C7A—C8A—C10A	129.40 (9)	C7B—C8B—C10B	128.55 (10)
C9A—C8A—C10A	124.56 (9)	C9B—C8B—C10B	125.63 (9)
O1A—C9A—N2A	122.59 (9)	O1B—C9B—N2B	121.99 (9)
O1A—C9A—C8A	130.31 (9)	O1B—C9B—C8B	130.90 (9)
N2A—C9A—C8A	107.10 (9)	N2B—C9B—C8B	107.09 (9)
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	−1.33 (11)	C7B—N1B—N2B—C9B	−2.31 (11)
C6A—C1A—C2A—C3A	0.33 (18)	C6B—C1B—C2B—C3B	−0.54 (17)
C1A—C2A—C3A—C4A	0.55 (19)	C1B—C2B—C3B—C4B	0.32 (18)
C2A—C3A—C4A—C5A	−0.48 (18)	C2B—C3B—C4B—C5B	0.73 (17)
C3A—C4A—C5A—C6A	−0.47 (17)	C3B—C4B—C5B—C6B	−1.54 (16)
C4A—C5A—C6A—C1A	1.33 (16)	C4B—C5B—C6B—C1B	1.30 (15)
C4A—C5A—C6A—C7A	−175.25 (10)	C4B—C5B—C6B—C7B	−177.31 (9)
C2A—C1A—C6A—C5A	−1.26 (16)	C2B—C1B—C6B—C5B	−0.27 (15)
C2A—C1A—C6A—C7A	175.29 (10)	C2B—C1B—C6B—C7B	178.36 (10)
N2A—N1A—C7A—C8A	1.22 (11)	N2B—N1B—C7B—C8B	0.43 (11)
N2A—N1A—C7A—C6A	−176.28 (8)	N2B—N1B—C7B—C6B	178.45 (8)
C5A—C6A—C7A—N1A	141.18 (10)	C5B—C6B—C7B—N1B	139.78 (10)
C1A—C6A—C7A—N1A	−35.32 (14)	C1B—C6B—C7B—N1B	−38.83 (14)
C5A—C6A—C7A—C8A	−35.71 (16)	C5B—C6B—C7B—C8B	−42.70 (16)
C1A—C6A—C7A—C8A	147.80 (11)	C1B—C6B—C7B—C8B	138.69 (11)
N1A—C7A—C8A—C9A	−0.64 (11)	N1B—C7B—C8B—C9B	1.50 (11)
C6A—C7A—C8A—C9A	176.51 (10)	C6B—C7B—C8B—C9B	−176.23 (10)
N1A—C7A—C8A—C10A	175.59 (10)	N1B—C7B—C8B—C10B	−176.60 (10)
C6A—C7A—C8A—C10A	−7.25 (18)	C6B—C7B—C8B—C10B	5.67 (18)
N1A—N2A—C9A—O1A	−178.72 (9)	N1B—N2B—C9B—O1B	−175.40 (9)
N1A—N2A—C9A—C8A	0.91 (11)	N1B—N2B—C9B—C8B	3.21 (11)
C7A—C8A—C9A—O1A	179.42 (10)	C7B—C8B—C9B—O1B	175.58 (10)
C10A—C8A—C9A—O1A	2.96 (17)	C10B—C8B—C9B—O1B	−6.24 (17)
C7A—C8A—C9A—N2A	−0.17 (11)	C7B—C8B—C9B—N2B	−2.85 (11)
C10A—C8A—C9A—N2A	−176.63 (9)	C10B—C8B—C9B—N2B	175.32 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1NB···O1Ai	0.913 (17)	1.796 (17)	2.7001 (11)	170.0 (16)
N1A—H1NA···O1B	0.935 (19)	1.78 (2)	2.6987 (14)	165.9 (16)
N2A—H2NA···O1Aii	0.93 (2)	1.768 (19)	2.6917 (12)	173.9 (17)
N2B—H2NB···O1Biii	0.934 (18)	1.752 (18)	2.6850 (13)	177.0 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1NB⋯O1Ai	0.913 (17)	1.796 (17)	2.7001 (11)	170.0 (16)
N1A—H1NA⋯O1B	0.935 (19)	1.78 (2)	2.6987 (14)	165.9 (16)
N2A—H2NA⋯O1Aii	0.93 (2)	1.768 (19)	2.6917 (12)	173.9 (17)
N2B—H2NB⋯O1Biii	0.934 (18)	1.752 (18)	2.6850 (13)	177.0 (16)

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