N-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)carbon­yl]-N′-(4-hydroxy­phen­yl)thio­urea

Du, H.; Du, H.; An, Y.; Li, S.

doi:10.1107/S1600536808019417

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1404

doi:10.1107/S1600536808019417

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N-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)carbonyl]-N′-(4-hydroxyphenyl)thiourea

Haitang Du,^a ^* Haijun Du,^b Ying An ^c and Shengnan Li ^c

^aDepartment of Biology and Environment Technology, Guiyang College, Guiyang 550005, People's Republic of China, ^bSchool of Chemistry and Environment Science, Guizhou University for Nationalities, Guiyang 550025, People's Republic of China, and ^cDepartment of Chemistry, College of Science, Tianjin University, Tianjin 300072, People's Republic of China
^*Correspondence e-mail: haitangdu@gz139.com.cn

(Received 17 June 2008; accepted 26 June 2008; online 5 July 2008)

In the title compound, C₁₈H₁₅ClN₄O₂S, the pyrazole ring makes dihedral angles of 67.4 (1) and 12.5 (1)° with the phenyl and 4-hydroxyphenyl groups, respectively; the two benzene rings are twisted by 60.1 (1)° with respect to each other. The thiourea NH groups are involved in N—H⋯O and N—H⋯Cl intramolecular hydrogen bonds. A hydrogen bond between the phenolic OH group and the pyrazole N atom connects molecules into a one-dimensional polymeric structure.

Related literature

For related literature, see: Du et al. (2007 ); Saeed & Flörke (2007 ); Wang et al. (2007 ).

Experimental

Crystal data

C₁₈H₁₅ClN₄O₂S
M_r = 386.85
Triclinic, $[P \overline 1]$
a = 8.572 (2) Å
b = 10.429 (2) Å
c = 11.170 (2) Å
α = 99.936 (4)°
β = 105.817 (4)°
γ = 106.042 (4)°
V = 889.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 294 (2) K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.914, T_max = 0.933
4615 measured reflections
3118 independent reflections
2160 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.122
S = 1.04
3118 reflections
245 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 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
O2—H2⋯N2ⁱ	0.82	2.15	2.938 (3)	162
N3—H3A⋯Cl1	0.891 (10)	2.422 (19)	3.168 (2)	141 (2)
N4—H4A⋯O1	0.901 (10)	1.92 (2)	2.661 (3)	139 (2)
Symmetry code: (i) x, y-1, z-1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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/S1600536808019417/gk2153sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019417/gk2153Isup2.hkl

checkCIF report

Comment top

The title compound is similar to the previously reported N-(5-chloro-3-methyl-1-phenylpyrazole-4-ylcarbonyl)-N'- (4-methphenyl)thiourea (Du et al., 2007). The molecular structure of the title compound and the atom-numbering scheme are shown in Fig.1. The pyrazole ring makes dihedral angles of 67.4 (1) and 12.5 (1)°, with the C1—C6 and C13—C18 rings, respectively. These two six-membered rings are twisted by 60.1 (1)° with respect to each other. This geometry is stabilized by intramolecular N4-H4A ···O1 and N3-H3A···Cl hydrogen bonds (Fig.1, Table 1). In the crystal structure, molecules are linked by intermolecular N-H···O hydrogen bonds to form a one-dimensional polymeric structure (Fig.2). All bond lengths and angles are in the normal range (Du et al., 2007; Saeed & Flörke, 2007; Wang et al., 2007).

Related literature top

For related literature, see: Du et al. (2007); Saeed & Flörke (2007); Wang et al. (2007).

Experimental top

Powdered ammonium thiocyanate (15 mmol), 5-chloro-3-methyl-1-phenyl-pyrazole-4-carbonyl chloride (10 mmol), PEG-400 (0.5 mL) and acetone (25 mL) were placed in a dried round-bottom flask and stirred at room temperature for 1 h, then 4-aminophenol (9.5 mmol) was added, and the mixture was stirred for 5 h. The mixture was poured into water (20 mL). The resulting solid was filtered, dried and recrystallized from N,N-dimethylformamide/ethanol to give the title compound. Single crystals were obtained by slow evaporation of a solution in N,N-dimethylformamide/ethanol (1:1, v/v).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. The molecular structure of the title compound with the atom numbering scheme, showing displacement ellipsoids at the 50% probability level.
	Fig. 2. The polymeric structure via O-H···N hydrogen bonds. Hydrogen bonds are shown with dashed lines.

N-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)carbonyl]- N'-(4-hydroxyphenyl)thiourea top

Crystal data top

C₁₈H₁₅ClN₄O₂S	Z = 2
M_r = 386.85	F(000) = 400
Triclinic, P1	D_x = 1.444 Mg m⁻³
Hall symbol: -P 1	Melting point: 456 K
a = 8.572 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.429 (2) Å	Cell parameters from 1626 reflections
c = 11.170 (2) Å	θ = 2.6–25.0°
α = 99.936 (4)°	µ = 0.35 mm⁻¹
β = 105.817 (4)°	T = 294 K
γ = 106.042 (4)°	Prism, colorless
V = 889.5 (3) Å³	0.26 × 0.24 × 0.20 mm

Data collection top

Bruker SMART 1K CCD diffractometer	3118 independent reflections
Radiation source: fine-focus sealed tube	2160 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→7
T_min = 0.914, T_max = 0.933	k = −12→12
4615 measured reflections	l = −10→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0601P)² + 0.0911P] where P = (F_o² + 2F_c²)/3
3118 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.20 e Å⁻³
2 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₈H₁₅ClN₄O₂S	γ = 106.042 (4)°
M_r = 386.85	V = 889.5 (3) Å³
Triclinic, P1	Z = 2
a = 8.572 (2) Å	Mo Kα radiation
b = 10.429 (2) Å	µ = 0.35 mm⁻¹
c = 11.170 (2) Å	T = 294 K
α = 99.936 (4)°	0.26 × 0.24 × 0.20 mm
β = 105.817 (4)°

Data collection top

Bruker SMART 1K CCD diffractometer	3118 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2160 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.933	R_int = 0.025
4615 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.20 e Å⁻³
3118 reflections	Δρ_min = −0.35 e Å⁻³
245 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
Cl1	0.12809 (11)	0.51284 (7)	0.87995 (7)	0.0638 (3)
S1	0.24176 (14)	0.24348 (8)	0.57180 (8)	0.0743 (3)
O1	0.2267 (3)	0.66532 (18)	0.52727 (17)	0.0588 (6)
O2	0.4029 (3)	0.19520 (19)	0.00036 (17)	0.0553 (5)
H2	0.3689	0.1104	−0.0168	0.083*
N1	0.1986 (3)	0.78380 (19)	0.93012 (18)	0.0391 (5)
N2	0.2336 (3)	0.8960 (2)	0.88065 (18)	0.0419 (5)
N3	0.2115 (3)	0.4873 (2)	0.6192 (2)	0.0462 (6)
N4	0.2649 (3)	0.4289 (2)	0.43005 (19)	0.0441 (5)
C1	0.1829 (3)	0.7990 (2)	1.0561 (2)	0.0380 (6)
C2	0.3043 (4)	0.7804 (3)	1.1543 (2)	0.0464 (7)
H2A	0.3950	0.7556	1.1394	0.056*
C3	0.2892 (4)	0.7994 (3)	1.2762 (3)	0.0533 (7)
H3	0.3708	0.7883	1.3442	0.064*
C4	0.1535 (4)	0.8345 (3)	1.2966 (3)	0.0582 (8)
H4	0.1431	0.8462	1.3782	0.070*
C5	0.0335 (4)	0.8525 (3)	1.1974 (3)	0.0622 (8)
H5	−0.0579	0.8763	1.2119	0.075*
C6	0.0477 (4)	0.8354 (3)	1.0758 (3)	0.0506 (7)
H6	−0.0329	0.8483	1.0084	0.061*
C7	0.2683 (4)	0.9426 (3)	0.6808 (2)	0.0564 (8)
H7A	0.2970	1.0362	0.7298	0.085*
H7B	0.1667	0.9190	0.6068	0.085*
H7C	0.3624	0.9343	0.6529	0.085*
C8	0.2354 (3)	0.8466 (2)	0.7635 (2)	0.0384 (6)
C9	0.2041 (3)	0.7020 (2)	0.7349 (2)	0.0362 (6)
C10	0.1803 (3)	0.6678 (2)	0.8446 (2)	0.0391 (6)
C11	0.2136 (3)	0.6184 (2)	0.6186 (2)	0.0388 (6)
C12	0.2401 (3)	0.3889 (3)	0.5323 (2)	0.0429 (6)
C13	0.3013 (3)	0.3615 (2)	0.3244 (2)	0.0395 (6)
C14	0.3412 (4)	0.4386 (3)	0.2413 (2)	0.0490 (7)
H14	0.3439	0.5298	0.2574	0.059*
C15	0.3771 (4)	0.3835 (3)	0.1354 (3)	0.0522 (7)
H15	0.4046	0.4376	0.0810	0.063*
C16	0.3726 (3)	0.2478 (3)	0.1094 (2)	0.0415 (6)
C17	0.3379 (4)	0.1723 (3)	0.1931 (2)	0.0504 (7)
H17	0.3389	0.0821	0.1780	0.061*
C18	0.3012 (4)	0.2268 (3)	0.2999 (3)	0.0535 (8)
H18	0.2765	0.1730	0.3551	0.064*
H3A	0.205 (4)	0.459 (3)	0.6890 (18)	0.066 (9)*
H4A	0.260 (4)	0.5134 (15)	0.426 (3)	0.064 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1074 (7)	0.0351 (4)	0.0593 (5)	0.0189 (4)	0.0486 (4)	0.0147 (3)
S1	0.1377 (9)	0.0495 (5)	0.0739 (6)	0.0502 (5)	0.0681 (6)	0.0290 (4)
O1	0.1072 (17)	0.0502 (11)	0.0377 (10)	0.0421 (12)	0.0355 (11)	0.0157 (9)
O2	0.0702 (14)	0.0514 (11)	0.0490 (11)	0.0212 (11)	0.0335 (10)	0.0029 (9)
N1	0.0546 (14)	0.0326 (11)	0.0314 (11)	0.0138 (10)	0.0196 (10)	0.0054 (9)
N2	0.0624 (15)	0.0350 (11)	0.0338 (11)	0.0189 (10)	0.0223 (10)	0.0096 (9)
N3	0.0740 (17)	0.0357 (12)	0.0405 (13)	0.0245 (11)	0.0317 (12)	0.0098 (10)
N4	0.0695 (16)	0.0334 (12)	0.0375 (12)	0.0248 (11)	0.0240 (11)	0.0082 (10)
C1	0.0495 (17)	0.0319 (13)	0.0332 (13)	0.0127 (12)	0.0187 (12)	0.0046 (10)
C2	0.0603 (19)	0.0426 (15)	0.0458 (16)	0.0244 (14)	0.0247 (14)	0.0135 (12)
C3	0.076 (2)	0.0499 (16)	0.0380 (15)	0.0244 (15)	0.0209 (14)	0.0154 (12)
C4	0.085 (2)	0.0532 (17)	0.0442 (17)	0.0223 (17)	0.0366 (17)	0.0110 (14)
C5	0.068 (2)	0.075 (2)	0.0599 (19)	0.0313 (17)	0.0414 (17)	0.0162 (16)
C6	0.0510 (18)	0.0583 (18)	0.0478 (16)	0.0229 (14)	0.0205 (13)	0.0142 (13)
C7	0.095 (2)	0.0413 (15)	0.0418 (15)	0.0289 (16)	0.0298 (16)	0.0146 (12)
C8	0.0502 (16)	0.0359 (13)	0.0311 (13)	0.0182 (12)	0.0142 (11)	0.0080 (11)
C9	0.0457 (16)	0.0332 (13)	0.0305 (12)	0.0154 (11)	0.0135 (11)	0.0062 (10)
C10	0.0493 (16)	0.0330 (13)	0.0366 (14)	0.0150 (12)	0.0175 (12)	0.0067 (11)
C11	0.0460 (16)	0.0373 (14)	0.0324 (13)	0.0164 (12)	0.0124 (11)	0.0054 (11)
C12	0.0509 (17)	0.0373 (14)	0.0398 (14)	0.0156 (12)	0.0183 (12)	0.0032 (11)
C13	0.0491 (16)	0.0352 (13)	0.0339 (13)	0.0164 (12)	0.0154 (12)	0.0028 (11)
C14	0.071 (2)	0.0328 (13)	0.0509 (16)	0.0221 (14)	0.0291 (15)	0.0094 (12)
C15	0.071 (2)	0.0446 (16)	0.0491 (16)	0.0214 (14)	0.0310 (15)	0.0135 (13)
C16	0.0436 (16)	0.0398 (14)	0.0379 (14)	0.0141 (12)	0.0155 (12)	−0.0001 (11)
C17	0.076 (2)	0.0356 (14)	0.0448 (15)	0.0237 (14)	0.0276 (14)	0.0049 (12)
C18	0.088 (2)	0.0389 (15)	0.0445 (16)	0.0248 (15)	0.0351 (15)	0.0126 (12)

Geometric parameters (Å, º) top

Cl1—C10	1.698 (2)	C4—H4	0.9300
S1—C12	1.654 (3)	C5—C6	1.382 (4)
O1—C11	1.224 (3)	C5—H5	0.9300
O2—C16	1.369 (3)	C6—H6	0.9300
O2—H2	0.8200	C7—C8	1.496 (3)
N1—C10	1.347 (3)	C7—H7A	0.9600
N1—N2	1.373 (3)	C7—H7B	0.9600
N1—C1	1.436 (3)	C7—H7C	0.9600
N2—C8	1.327 (3)	C8—C9	1.419 (3)
N3—C11	1.363 (3)	C9—C10	1.384 (3)
N3—C12	1.407 (3)	C9—C11	1.470 (3)
N3—H3A	0.891 (10)	C13—C14	1.380 (3)
N4—C12	1.331 (3)	C13—C18	1.384 (3)
N4—C13	1.421 (3)	C14—C15	1.374 (3)
N4—H4A	0.901 (10)	C14—H14	0.9300
C1—C6	1.374 (4)	C15—C16	1.382 (3)
C1—C2	1.374 (4)	C15—H15	0.9300
C2—C3	1.389 (4)	C16—C17	1.363 (4)
C2—H2A	0.9300	C17—C18	1.384 (3)
C3—C4	1.375 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.371 (4)

C16—O2—H2	109.5	H7B—C7—H7C	109.5
C10—N1—N2	110.66 (18)	N2—C8—C9	111.7 (2)
C10—N1—C1	128.6 (2)	N2—C8—C7	119.6 (2)
N2—N1—C1	120.68 (17)	C9—C8—C7	128.7 (2)
C8—N2—N1	105.50 (18)	C10—C9—C8	103.6 (2)
C11—N3—C12	130.5 (2)	C10—C9—C11	130.9 (2)
C11—N3—H3A	118.6 (19)	C8—C9—C11	125.2 (2)
C12—N3—H3A	110.4 (19)	N1—C10—C9	108.6 (2)
C12—N4—C13	130.9 (2)	N1—C10—Cl1	120.04 (18)
C12—N4—H4A	115.9 (18)	C9—C10—Cl1	131.33 (19)
C13—N4—H4A	113.2 (18)	O1—C11—N3	121.8 (2)
C6—C1—C2	121.7 (2)	O1—C11—C9	121.6 (2)
C6—C1—N1	118.6 (2)	N3—C11—C9	116.6 (2)
C2—C1—N1	119.7 (2)	N4—C12—N3	114.1 (2)
C1—C2—C3	118.7 (3)	N4—C12—S1	129.42 (19)
C1—C2—H2A	120.6	N3—C12—S1	116.46 (19)
C3—C2—H2A	120.6	C14—C13—C18	118.3 (2)
C4—C3—C2	120.1 (3)	C14—C13—N4	116.5 (2)
C4—C3—H3	120.0	C18—C13—N4	125.3 (2)
C2—C3—H3	120.0	C15—C14—C13	121.4 (2)
C5—C4—C3	120.4 (3)	C15—C14—H14	119.3
C5—C4—H4	119.8	C13—C14—H14	119.3
C3—C4—H4	119.8	C14—C15—C16	120.1 (2)
C4—C5—C6	120.3 (3)	C14—C15—H15	119.9
C4—C5—H5	119.9	C16—C15—H15	119.9
C6—C5—H5	119.9	C17—C16—O2	122.9 (2)
C1—C6—C5	118.9 (3)	C17—C16—C15	118.7 (2)
C1—C6—H6	120.5	O2—C16—C15	118.3 (2)
C5—C6—H6	120.5	C16—C17—C18	121.6 (2)
C8—C7—H7A	109.5	C16—C17—H17	119.2
C8—C7—H7B	109.5	C18—C17—H17	119.2
H7A—C7—H7B	109.5	C13—C18—C17	119.9 (2)
C8—C7—H7C	109.5	C13—C18—H18	120.1
H7A—C7—H7C	109.5	C17—C18—H18	120.1

C10—N1—N2—C8	0.3 (3)	C11—C9—C10—N1	173.8 (3)
C1—N1—N2—C8	−178.5 (2)	C8—C9—C10—Cl1	176.7 (2)
C10—N1—C1—C6	−112.6 (3)	C11—C9—C10—Cl1	−8.8 (4)
N2—N1—C1—C6	66.0 (3)	C12—N3—C11—O1	7.4 (4)
C10—N1—C1—C2	69.0 (3)	C12—N3—C11—C9	−171.0 (3)
N2—N1—C1—C2	−112.5 (3)	C10—C9—C11—O1	176.2 (3)
C6—C1—C2—C3	−0.1 (4)	C8—C9—C11—O1	−10.4 (4)
N1—C1—C2—C3	178.2 (2)	C10—C9—C11—N3	−5.4 (4)
C1—C2—C3—C4	0.7 (4)	C8—C9—C11—N3	168.0 (2)
C2—C3—C4—C5	−0.7 (4)	C13—N4—C12—N3	178.3 (2)
C3—C4—C5—C6	0.0 (5)	C13—N4—C12—S1	−0.5 (4)
C2—C1—C6—C5	−0.5 (4)	C11—N3—C12—N4	−3.7 (4)
N1—C1—C6—C5	−178.9 (2)	C11—N3—C12—S1	175.3 (2)
C4—C5—C6—C1	0.6 (4)	C12—N4—C13—C14	−172.2 (3)
N1—N2—C8—C9	−0.8 (3)	C12—N4—C13—C18	7.1 (4)
N1—N2—C8—C7	179.3 (2)	C18—C13—C14—C15	1.2 (4)
N2—C8—C9—C10	1.0 (3)	N4—C13—C14—C15	−179.4 (3)
C7—C8—C9—C10	−179.2 (3)	C13—C14—C15—C16	0.5 (4)
N2—C8—C9—C11	−174.0 (2)	C14—C15—C16—C17	−2.2 (4)
C7—C8—C9—C11	5.9 (4)	C14—C15—C16—O2	177.6 (3)
N2—N1—C10—C9	0.3 (3)	O2—C16—C17—C18	−177.5 (3)
C1—N1—C10—C9	179.0 (2)	C15—C16—C17—C18	2.4 (4)
N2—N1—C10—Cl1	−177.47 (17)	C14—C13—C18—C17	−1.0 (4)
C1—N1—C10—Cl1	1.2 (4)	N4—C13—C18—C17	179.6 (3)
C8—C9—C10—N1	−0.7 (3)	C16—C17—C18—C13	−0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2ⁱ	0.82	2.15	2.938 (3)	162
N3—H3A···Cl1	0.89 (1)	2.42 (2)	3.168 (2)	141 (2)
N4—H4A···O1	0.90 (1)	1.92 (2)	2.661 (3)	139 (2)

Symmetry code: (i) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅ClN₄O₂S
M_r	386.85
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.572 (2), 10.429 (2), 11.170 (2)
α, β, γ (°)	99.936 (4), 105.817 (4), 106.042 (4)
V (Å³)	889.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.914, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	4615, 3118, 2160
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.123, 1.04
No. of reflections	3118
No. of parameters	245
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.35

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
O2—H2···N2ⁱ	0.82	2.15	2.938 (3)	162
N3—H3A···Cl1	0.891 (10)	2.422 (19)	3.168 (2)	141 (2)
N4—H4A···O1	0.901 (10)	1.92 (2)	2.661 (3)	139 (2)

Symmetry code: (i) x, y−1, z−1.

Acknowledgements

The authors thank Guiyang College (project No. 2008012) for financial support.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Du, H.-T., Lu, M., Zhou, W.-Y. & Sun, L.-L. (2007). Acta Cryst. E63, o4287. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saeed, A. & Flörke, U. (2007). Acta Cryst. E63, o3695. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J., Tian, L. & Liu, S.-Y. (2007). Acta Cryst. E63, o3667. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 8| August 2008| Page o1404

doi:10.1107/S1600536808019417

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

N-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)carbon­yl]-N′-(4-hy­droxy­phen­yl)thio­urea

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)carbonyl]-N′-(4-hydroxyphenyl)thiourea