1-[5-(2-Chloro­phen­yl)-5-hy­droxy-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]­ethanone

Guo, S.-H.; Wang, J.-L.; Guo, D.-Q.; Zhang, X.-Y.

doi:10.1107/S1600536812007283

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o839

doi:10.1107/S1600536812007283

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1-[5-(2-Chlorophenyl)-5-hydroxy-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Sheng-Hai Guo,^a Ji-Liang Wang,^a Dong-Qiang Guo ^a and Xin-Ying Zhang ^a ^*

^aSchool of Chemistry and Environmental Science, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China
^*Correspondence e-mail: xyzh518@sohu.com

(Received 15 February 2012; accepted 17 February 2012; online 24 February 2012)

The title compound, C₁₂H₁₃ClN₂O₂, crystallizes with two independent but very similar molecules (A and B) in the asymmetric unit. The pyrazole ring in each molecule has an envelope conformation. The dihedral angle between the pyrazole ring mean plane and the benzene ring is 86.07 (14)° in A and 85.99 (14)° in B. In the crystal, the A and B molecules are linked via a pair of O—H⋯O hydrogen bonds, forming dimers. These dimers are further linked via C—H⋯O interactions to form –A–B–A–B– chains propagating along the c-axis direction.

Related literature

For the bioactivities of 5-hydroxypyrazolines, see: Sauzem et al. (2008 ); Zhao et al. (2009 ); Idrees et al. (2009 ). For the crystal structures of related 5-hydroxypyrazolines, see: Kargar, Kia, Froozandeh et al. (2011 ); Kargar, Kia, Moghadamm et al. (2011 ).

Experimental

Crystal data

C₁₂H₁₃ClN₂O₂
M_r = 252.70
Monoclinic, P 2₁ /c
a = 10.320 (3) Å
b = 14.916 (4) Å
c = 16.346 (4) Å
β = 95.158 (3)°
V = 2506.0 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.39 × 0.25 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.893, T_max = 0.957
16979 measured reflections
4663 independent reflections
3077 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.159
S = 1.02
4663 reflections
313 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—–H1⋯..O4ⁱ	0.82	1.97	2.748 (3)	159
O3—–H3A⋯..O2ⁱⁱ	0.82	2.03	2.792 (3)	155
C8—–H8B⋯..O3ⁱⁱⁱ	0.97	2.53	3.410 (3)	151
C20—–H20B⋯..O1^iv	0.97	2.50	3.354 (3)	147
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) x-1, y, z.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007283/su2378sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007283/su2378Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007283/su2378Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812007283/su2378Isup4.cml

checkCIF report

Comment top

5-Hydroxypyrazolines have drawn much attention due to their interesting biological properties such as anti-inflammatory, antibiotic, and hypolipidemic activities (Sauzem et al., 2008; Zhao et al., 2009; Idrees et al., 2009). Crystal structures of some 5-hydroxypyrazoline derivatives have been reported (Kargar, Kia, Froozandeh et al., 2011; Kargar, Kia, Moghadamm et al., 2011). Herein, we report on the crystal structure of the new title 5-hydroxypyrazoline derivative.

The title compound crystallizes with two independent but very similar molecules (A and B) in the asymmetric unit (Fig. 1). All the bond lengths and bond angles are within normal ranges. The five-membered pyrazole rings have envelope conformations with atom C7 as the flap in molecule A, and atom C19 as the flap in molecule B. The dihedral angle between the pyrazole ring mean plane and the phenyl ring is 86.07 (14) ° in A and 85.99 (14) ° in B.

In the crystal, the A and B molecules are linked via a pair of O—H···O hydrogen bonds forming dimers. These dimers are further linked via C-H···O interactions to form -A-B-A-B- chains propagating along the c axis direction (Table 1 and Fig. 2).

Related literature top

For the bioactivities of 5-hydroxypyrazolines, see: Sauzem et al. (2008); Zhao et al. (2009); Idrees et al. (2009). For the crystal structures of related 5-hydroxypyrazolines, see: Kargar, Kia, Froozandeh et al. (2011); Kargar, Kia, Moghadamm et al. (2011).

Experimental top

1-(2-chlorophenyl)butane-1,3-dione (1.0 mmol), acetohydrazide (1.0 mmol), and a drop of concentrated H₂SO₄ were mixed and ground for 10 min in a mortar. Upon completion of the reaction, monitored by TLC, ethyl acetate and water were added to the reaction mixture. Then, the organic layer was washed with Na₂CO₃ solution and water, and dried over anhydrous Na₂SO₄. Ethyl acetate was removed under reduced pressure and the residue was purified by chromatography on silica-gel to provide the title product as a white solid. Colourless block-like crystals of the title compound, suitable for X-ray diffraction analysis, were obtained by slow evaporation of the solvent from a dichloromethane solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the two independent molecules (A right; B left) of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound, viewed along the a axis. The O—H···O hydrogen bonds and C-H···O interactions are shown as dashed lines (see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity).

1-[5-(2-Chlorophenyl)-5-hydroxy-3-methyl-4,5-dihydro-1H-pyrazol- 1-yl]ethanone top

Crystal data top

C₁₂H₁₃ClN₂O₂	F(000) = 1056
M_r = 252.70	D_x = 1.340 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3669 reflections
a = 10.320 (3) Å	θ = 2.4–25.9°
b = 14.916 (4) Å	µ = 0.30 mm⁻¹
c = 16.346 (4) Å	T = 296 K
β = 95.158 (3)°	Block, colourless
V = 2506.0 (12) Å³	0.39 × 0.25 × 0.15 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	4663 independent reflections
Radiation source: fine-focus sealed tube	3077 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
phi and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
T_min = 0.893, T_max = 0.957	k = −18→18
16979 measured reflections	l = −19→19

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0804P)² + 0.8196P] where P = (F_o² + 2F_c²)/3
4663 reflections	(Δ/σ)_max = 0.001
313 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₂H₁₃ClN₂O₂	V = 2506.0 (12) Å³
M_r = 252.70	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.320 (3) Å	µ = 0.30 mm⁻¹
b = 14.916 (4) Å	T = 296 K
c = 16.346 (4) Å	0.39 × 0.25 × 0.15 mm
β = 95.158 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4663 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3077 reflections with I > 2σ(I)
T_min = 0.893, T_max = 0.957	R_int = 0.038
16979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.02	Δρ_max = 0.39 e Å⁻³
4663 reflections	Δρ_min = −0.35 e Å⁻³
313 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5236 (3)	0.2945 (2)	0.27457 (16)	0.0630 (8)
C2	0.6517 (3)	0.32278 (17)	0.26911 (14)	0.0484 (6)
C3	0.6858 (3)	0.40628 (19)	0.30087 (17)	0.0643 (8)
H3	0.7701	0.4272	0.2977	0.077*
C4	0.5966 (5)	0.4597 (2)	0.3375 (2)	0.0904 (12)
H4	0.6214	0.5154	0.3591	0.109*
C5	0.4714 (5)	0.4294 (3)	0.3415 (2)	0.1025 (15)
H5	0.4112	0.4653	0.3650	0.123*
C6	0.4349 (4)	0.3468 (3)	0.3110 (2)	0.0891 (12)
H6	0.3506	0.3261	0.3148	0.107*
C7	0.7497 (2)	0.27082 (16)	0.22292 (14)	0.0427 (6)
C8	0.7104 (2)	0.26559 (16)	0.12996 (14)	0.0452 (6)
H8A	0.6204	0.2833	0.1172	0.054*
H8B	0.7656	0.3035	0.0997	0.054*
C9	0.7293 (2)	0.16951 (17)	0.11060 (15)	0.0470 (6)
C10	0.7195 (3)	0.1336 (2)	0.02506 (16)	0.0630 (8)
H10A	0.7276	0.0695	0.0267	0.094*
H10B	0.7879	0.1585	−0.0040	0.094*
H10C	0.6368	0.1497	−0.0026	0.094*
C11	0.7751 (3)	0.14051 (18)	0.32065 (16)	0.0514 (6)
C12	0.7807 (4)	0.0402 (2)	0.32863 (19)	0.0811 (10)
H12A	0.8560	0.0181	0.3047	0.122*
H12B	0.7038	0.0144	0.3006	0.122*
H12C	0.7857	0.0240	0.3857	0.122*
C13	0.3110 (3)	0.3263 (2)	−0.02266 (16)	0.0621 (8)
C14	0.1813 (3)	0.34881 (17)	−0.01755 (14)	0.0470 (6)
C15	0.1388 (3)	0.43010 (17)	−0.05224 (17)	0.0658 (8)
H15	0.0529	0.4476	−0.0491	0.079*
C16	0.2215 (5)	0.4854 (2)	−0.0913 (2)	0.0941 (13)
H16	0.1904	0.5387	−0.1151	0.113*
C17	0.3479 (5)	0.4620 (3)	−0.0950 (2)	0.1070 (15)
H17	0.4032	0.4998	−0.1207	0.128*
C18	0.3958 (4)	0.3819 (3)	−0.0606 (2)	0.0906 (12)
H18	0.4825	0.3659	−0.0628	0.109*
C19	0.0867 (2)	0.29137 (16)	0.02655 (14)	0.0427 (6)
C20	0.1250 (2)	0.27892 (16)	0.11897 (14)	0.0459 (6)
H20A	0.2142	0.2975	0.1335	0.055*
H20B	0.0680	0.3128	0.1515	0.055*
C21	0.1094 (2)	0.18061 (16)	0.13134 (15)	0.0457 (6)
C22	0.1166 (3)	0.13570 (19)	0.21316 (15)	0.0564 (7)
H22A	0.1115	0.0719	0.2057	0.085*
H22B	0.0455	0.1555	0.2427	0.085*
H22C	0.1974	0.1508	0.2438	0.085*
C23	0.0645 (2)	0.16960 (16)	−0.07964 (15)	0.0455 (6)
C24	0.0633 (3)	0.07144 (18)	−0.09644 (19)	0.0707 (9)
H24A	0.0579	0.0615	−0.1547	0.106*
H24B	−0.0106	0.0447	−0.0742	0.106*
H24C	0.1417	0.0449	−0.0712	0.106*
Cl1	0.46874 (8)	0.19108 (7)	0.23531 (5)	0.0841 (3)
Cl2	0.37469 (8)	0.22580 (7)	0.01857 (5)	0.0865 (3)
N1	0.7575 (2)	0.17426 (13)	0.24382 (12)	0.0457 (5)
N2	0.7540 (2)	0.11902 (14)	0.17364 (13)	0.0522 (5)
N3	0.0850 (2)	0.19699 (13)	−0.00094 (11)	0.0443 (5)
N4	0.0897 (2)	0.13575 (14)	0.06455 (12)	0.0508 (5)
O1	0.87374 (17)	0.30941 (12)	0.23266 (10)	0.0525 (5)
H1	0.9088	0.2968	0.2782	0.079*
O2	0.7846 (2)	0.19093 (13)	0.37965 (11)	0.0621 (5)
O3	−0.03948 (17)	0.32648 (13)	0.01884 (10)	0.0548 (5)
H3A	−0.0705	0.3216	−0.0289	0.082*
O4	0.04921 (19)	0.22575 (12)	−0.13467 (10)	0.0562 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0586 (18)	0.090 (2)	0.0407 (16)	0.0137 (15)	0.0055 (13)	0.0096 (14)
C2	0.0569 (16)	0.0557 (16)	0.0319 (13)	0.0083 (12)	0.0006 (11)	0.0080 (11)
C3	0.092 (2)	0.0540 (17)	0.0465 (16)	0.0113 (15)	0.0059 (15)	0.0048 (13)
C4	0.148 (4)	0.068 (2)	0.056 (2)	0.040 (2)	0.015 (2)	0.0058 (17)
C5	0.125 (4)	0.124 (4)	0.061 (2)	0.076 (3)	0.025 (2)	0.014 (2)
C6	0.072 (2)	0.133 (3)	0.064 (2)	0.037 (2)	0.0174 (17)	0.017 (2)
C7	0.0456 (14)	0.0472 (14)	0.0348 (13)	−0.0022 (10)	0.0012 (10)	0.0062 (10)
C8	0.0484 (14)	0.0532 (15)	0.0333 (13)	−0.0031 (11)	0.0005 (10)	0.0055 (11)
C9	0.0489 (15)	0.0547 (15)	0.0366 (13)	−0.0019 (11)	0.0000 (11)	0.0008 (11)
C10	0.077 (2)	0.0695 (18)	0.0415 (15)	0.0044 (15)	−0.0013 (14)	−0.0070 (13)
C11	0.0562 (16)	0.0556 (16)	0.0412 (15)	−0.0062 (12)	−0.0019 (12)	0.0097 (12)
C12	0.123 (3)	0.0602 (19)	0.0563 (18)	−0.0050 (18)	−0.0099 (19)	0.0154 (15)
C13	0.0633 (19)	0.084 (2)	0.0388 (15)	−0.0168 (15)	0.0021 (13)	−0.0014 (14)
C14	0.0620 (17)	0.0494 (15)	0.0295 (12)	−0.0092 (12)	0.0039 (11)	−0.0054 (10)
C15	0.103 (2)	0.0453 (16)	0.0503 (17)	−0.0065 (15)	0.0106 (16)	−0.0037 (13)
C16	0.161 (4)	0.057 (2)	0.067 (2)	−0.032 (2)	0.019 (2)	0.0005 (16)
C17	0.145 (4)	0.108 (3)	0.072 (2)	−0.068 (3)	0.029 (3)	0.000 (2)
C18	0.080 (2)	0.133 (3)	0.061 (2)	−0.039 (2)	0.0171 (18)	−0.007 (2)
C19	0.0475 (14)	0.0461 (13)	0.0340 (13)	0.0015 (10)	0.0010 (10)	−0.0024 (10)
C20	0.0494 (15)	0.0553 (15)	0.0323 (13)	−0.0012 (11)	0.0003 (11)	−0.0026 (11)
C21	0.0447 (14)	0.0539 (15)	0.0383 (14)	0.0022 (11)	0.0022 (11)	0.0031 (11)
C22	0.0665 (18)	0.0631 (17)	0.0398 (14)	0.0044 (14)	0.0052 (12)	0.0092 (12)
C23	0.0493 (15)	0.0513 (14)	0.0355 (13)	0.0007 (11)	0.0009 (11)	−0.0032 (11)
C24	0.109 (3)	0.0518 (17)	0.0513 (17)	0.0034 (16)	0.0051 (16)	−0.0105 (13)
Cl1	0.0578 (5)	0.1235 (8)	0.0712 (6)	−0.0265 (4)	0.0062 (4)	−0.0022 (5)
Cl2	0.0548 (5)	0.1328 (8)	0.0718 (6)	0.0203 (5)	0.0049 (4)	0.0159 (5)
N1	0.0562 (13)	0.0474 (12)	0.0329 (11)	−0.0004 (9)	−0.0002 (9)	0.0033 (9)
N2	0.0632 (14)	0.0517 (13)	0.0409 (12)	−0.0004 (10)	0.0007 (10)	−0.0042 (10)
N3	0.0593 (13)	0.0433 (11)	0.0297 (10)	−0.0032 (9)	0.0010 (9)	0.0015 (8)
N4	0.0657 (14)	0.0487 (12)	0.0375 (12)	−0.0013 (10)	0.0016 (10)	0.0055 (10)
O1	0.0500 (11)	0.0672 (12)	0.0394 (10)	−0.0108 (8)	−0.0015 (8)	0.0060 (8)
O2	0.0814 (14)	0.0671 (12)	0.0357 (10)	−0.0027 (10)	−0.0057 (9)	0.0036 (9)
O3	0.0541 (11)	0.0728 (12)	0.0372 (10)	0.0132 (9)	0.0018 (8)	−0.0012 (9)
O4	0.0762 (13)	0.0562 (11)	0.0345 (10)	−0.0032 (9)	−0.0052 (9)	0.0011 (8)

Geometric parameters (Å, º) top

C1—C6	1.378 (4)	C13—Cl2	1.748 (3)
C1—C2	1.398 (4)	C14—C15	1.393 (4)
C1—Cl1	1.746 (3)	C14—C19	1.527 (3)
C2—C3	1.383 (4)	C15—C16	1.383 (5)
C2—C7	1.527 (3)	C15—H15	0.9300
C3—C4	1.393 (5)	C16—C17	1.357 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.375 (6)	C17—C18	1.391 (6)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.369 (6)	C18—H18	0.9300
C5—H5	0.9300	C19—O3	1.399 (3)
C6—H6	0.9300	C19—N3	1.477 (3)
C7—O1	1.400 (3)	C19—C20	1.538 (3)
C7—N1	1.481 (3)	C20—C21	1.491 (3)
C7—C8	1.539 (3)	C20—H20A	0.9700
C8—C9	1.484 (4)	C20—H20B	0.9700
C8—H8A	0.9700	C21—N4	1.281 (3)
C8—H8B	0.9700	C21—C22	1.492 (3)
C9—N2	1.283 (3)	C22—H22A	0.9600
C9—C10	1.492 (3)	C22—H22B	0.9600
C10—H10A	0.9600	C22—H22C	0.9600
C10—H10B	0.9600	C23—O4	1.229 (3)
C10—H10C	0.9600	C23—N3	1.348 (3)
C11—O2	1.220 (3)	C23—C24	1.490 (4)
C11—N1	1.350 (3)	C24—H24A	0.9600
C11—C12	1.503 (4)	C24—H24B	0.9600
C12—H12A	0.9600	C24—H24C	0.9600
C12—H12B	0.9600	N1—N2	1.410 (3)
C12—H12C	0.9600	N3—N4	1.405 (3)
C13—C14	1.389 (4)	O1—H1	0.8200
C13—C18	1.391 (4)	O3—H3A	0.8200

C6—C1—C2	121.7 (3)	C15—C14—C19	119.3 (3)
C6—C1—Cl1	116.9 (3)	C16—C15—C14	121.5 (4)
C2—C1—Cl1	121.3 (2)	C16—C15—H15	119.3
C3—C2—C1	117.2 (3)	C14—C15—H15	119.3
C3—C2—C7	119.0 (2)	C17—C16—C15	120.2 (4)
C1—C2—C7	123.4 (2)	C17—C16—H16	119.9
C2—C3—C4	121.4 (3)	C15—C16—H16	119.9
C2—C3—H3	119.3	C16—C17—C18	120.7 (3)
C4—C3—H3	119.3	C16—C17—H17	119.6
C5—C4—C3	119.5 (4)	C18—C17—H17	119.6
C5—C4—H4	120.3	C13—C18—C17	118.5 (4)
C3—C4—H4	120.3	C13—C18—H18	120.8
C6—C5—C4	120.5 (3)	C17—C18—H18	120.8
C6—C5—H5	119.7	O3—C19—N3	110.10 (19)
C4—C5—H5	119.7	O3—C19—C14	112.1 (2)
C5—C6—C1	119.6 (4)	N3—C19—C14	112.44 (19)
C5—C6—H6	120.2	O3—C19—C20	106.78 (19)
C1—C6—H6	120.2	N3—C19—C20	100.30 (18)
O1—C7—N1	110.09 (19)	C14—C19—C20	114.4 (2)
O1—C7—C2	112.0 (2)	C21—C20—C19	103.33 (19)
N1—C7—C2	113.86 (19)	C21—C20—H20A	111.1
O1—C7—C8	106.87 (19)	C19—C20—H20A	111.1
N1—C7—C8	100.51 (18)	C21—C20—H20B	111.1
C2—C7—C8	112.74 (19)	C19—C20—H20B	111.1
C9—C8—C7	103.38 (19)	H20A—C20—H20B	109.1
C9—C8—H8A	111.1	N4—C21—C20	114.1 (2)
C7—C8—H8A	111.1	N4—C21—C22	121.4 (2)
C9—C8—H8B	111.1	C20—C21—C22	124.5 (2)
C7—C8—H8B	111.1	C21—C22—H22A	109.5
H8A—C8—H8B	109.1	C21—C22—H22B	109.5
N2—C9—C8	114.6 (2)	H22A—C22—H22B	109.5
N2—C9—C10	122.3 (2)	C21—C22—H22C	109.5
C8—C9—C10	123.2 (2)	H22A—C22—H22C	109.5
C9—C10—H10A	109.5	H22B—C22—H22C	109.5
C9—C10—H10B	109.5	O4—C23—N3	119.4 (2)
H10A—C10—H10B	109.5	O4—C23—C24	122.5 (2)
C9—C10—H10C	109.5	N3—C23—C24	118.2 (2)
H10A—C10—H10C	109.5	C23—C24—H24A	109.5
H10B—C10—H10C	109.5	C23—C24—H24B	109.5
O2—C11—N1	120.0 (2)	H24A—C24—H24B	109.5
O2—C11—C12	123.1 (2)	C23—C24—H24C	109.5
N1—C11—C12	116.9 (2)	H24A—C24—H24C	109.5
C11—C12—H12A	109.5	H24B—C24—H24C	109.5
C11—C12—H12B	109.5	C11—N1—N2	122.0 (2)
H12A—C12—H12B	109.5	C11—N1—C7	125.3 (2)
C11—C12—H12C	109.5	N2—N1—C7	112.58 (18)
H12A—C12—H12C	109.5	C9—N2—N1	107.4 (2)
H12B—C12—H12C	109.5	C23—N3—N4	121.4 (2)
C14—C13—C18	122.1 (3)	C23—N3—C19	125.1 (2)
C14—C13—Cl2	121.0 (2)	N4—N3—C19	112.90 (18)
C18—C13—Cl2	116.9 (3)	C21—N4—N3	107.6 (2)
C13—C14—C15	117.1 (3)	C7—O1—H1	109.5
C13—C14—C19	123.6 (2)	C19—O3—H3A	109.5

C6—C1—C2—C3	−0.8 (4)	C15—C14—C19—N3	130.6 (2)
Cl1—C1—C2—C3	179.10 (19)	C13—C14—C19—C20	61.5 (3)
C6—C1—C2—C7	−174.6 (2)	C15—C14—C19—C20	−115.9 (3)
Cl1—C1—C2—C7	5.4 (3)	O3—C19—C20—C21	102.6 (2)
C1—C2—C3—C4	0.6 (4)	N3—C19—C20—C21	−12.3 (2)
C7—C2—C3—C4	174.6 (2)	C14—C19—C20—C21	−132.8 (2)
C2—C3—C4—C5	−0.7 (5)	C19—C20—C21—N4	9.7 (3)
C3—C4—C5—C6	1.1 (5)	C19—C20—C21—C22	−170.9 (2)
C4—C5—C6—C1	−1.4 (5)	O2—C11—N1—N2	176.0 (2)
C2—C1—C6—C5	1.2 (5)	C12—C11—N1—N2	−4.6 (4)
Cl1—C1—C6—C5	−178.7 (3)	O2—C11—N1—C7	0.7 (4)
C3—C2—C7—O1	11.4 (3)	C12—C11—N1—C7	−179.8 (3)
C1—C2—C7—O1	−175.0 (2)	O1—C7—N1—C11	75.2 (3)
C3—C2—C7—N1	137.2 (2)	C2—C7—N1—C11	−51.5 (3)
C1—C2—C7—N1	−49.2 (3)	C8—C7—N1—C11	−172.3 (2)
C3—C2—C7—C8	−109.1 (2)	O1—C7—N1—N2	−100.4 (2)
C1—C2—C7—C8	64.5 (3)	C2—C7—N1—N2	132.8 (2)
O1—C7—C8—C9	103.5 (2)	C8—C7—N1—N2	12.0 (2)
N1—C7—C8—C9	−11.4 (2)	C8—C9—N2—N1	−1.1 (3)
C2—C7—C8—C9	−133.0 (2)	C10—C9—N2—N1	179.5 (2)
C7—C8—C9—N2	8.5 (3)	C11—N1—N2—C9	176.7 (2)
C7—C8—C9—C10	−172.0 (2)	C7—N1—N2—C9	−7.5 (3)
C18—C13—C14—C15	0.0 (4)	O4—C23—N3—N4	173.4 (2)
Cl2—C13—C14—C15	−179.9 (2)	C24—C23—N3—N4	−7.5 (4)
C18—C13—C14—C19	−177.4 (3)	O4—C23—N3—C19	2.1 (4)
Cl2—C13—C14—C19	2.7 (3)	C24—C23—N3—C19	−178.8 (2)
C13—C14—C15—C16	1.0 (4)	O3—C19—N3—C23	72.1 (3)
C19—C14—C15—C16	178.6 (3)	C14—C19—N3—C23	−53.7 (3)
C14—C15—C16—C17	−1.4 (5)	C20—C19—N3—C23	−175.6 (2)
C15—C16—C17—C18	0.8 (6)	O3—C19—N3—N4	−99.7 (2)
C14—C13—C18—C17	−0.7 (5)	C14—C19—N3—N4	134.4 (2)
Cl2—C13—C18—C17	179.2 (3)	C20—C19—N3—N4	12.5 (3)
C16—C17—C18—C13	0.3 (6)	C20—C21—N4—N3	−1.9 (3)
C13—C14—C19—O3	−176.7 (2)	C22—C21—N4—N3	178.6 (2)
C15—C14—C19—O3	5.9 (3)	C23—N3—N4—C21	−179.6 (2)
C13—C14—C19—N3	−52.0 (3)	C19—N3—N4—C21	−7.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—–H1···..O4ⁱ	0.82	1.97	2.748 (3)	159
O3—–H3A···..O2ⁱⁱ	0.82	2.03	2.792 (3)	155
C8—–H8B···..O3ⁱⁱⁱ	0.97	2.53	3.410 (3)	151
C20—–H20B···..O1^iv	0.97	2.50	3.354 (3)	147

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃ClN₂O₂
M_r	252.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.320 (3), 14.916 (4), 16.346 (4)
β (°)	95.158 (3)
V (Å³)	2506.0 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.39 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.893, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	16979, 4663, 3077
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.159, 1.02
No. of reflections	4663
No. of parameters	313
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.35

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—–H1···..O4ⁱ	0.82	1.97	2.748 (3)	159
O3—–H3A···..O2ⁱⁱ	0.82	2.03	2.792 (3)	155
C8—–H8B···..O3ⁱⁱⁱ	0.97	2.53	3.410 (3)	151
C20—–H20B···..O1^iv	0.97	2.50	3.354 (3)	147

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21172057).

References

Bruker (2007). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Idrees, G. A., Aly, O. M., Abuo-Rahma, G. E.-D. A. A. & Radwan, M. F. (2009). Eur. J. Med. Chem. 44, 3973–3980. Web of Science CrossRef PubMed CAS Google Scholar
Kargar, H., Kia, R., Froozandeh, F., Hossaini Sadr, M. & Tahir, M. N. (2011). Acta Cryst. E67, o209. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kargar, H., Kia, R., Moghadamm, M. & Tahir, M. N. (2011). Acta Cryst. E67, o367. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sauzem, P. D., Machado, P., Rubin, M. A., Sant'Anna, G. S., Faber, H. B., de Souza, A. H., Mello, C. F., Beck, P., Burrow, R. A., Bonacorso, H. G., Zanatta, N. & Martins, M. A. P. (2008). Eur. J. Med. Chem. 43, 1237–1247. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, Y., Bacher, A., Illarionov, B., Fischer, M., Georg, G., Ye, Q.-Z., Fanwick, P. E., Franzblau, S. G., Wan, B. & Cushman, M. (2009). J. Org. Chem. 74, 5297–5303. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 68| Part 3| March 2012| Page o839

doi:10.1107/S1600536812007283

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[5-(2-Chloro­phen­yl)-5-hy­dr­oxy-3-methyl-4,5-di­hydro-1H-pyrazol-1-yl]­ethanone

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Experimental

Crystal data

Data collection

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Supporting information

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organic compounds

1-[5-(2-Chlorophenyl)-5-hydroxy-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone