N-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-ylcarbon­yl)-N′-(2,6-dimethyl­phen­yl)thio­urea

Du, H.-T.; Du, H.-J.; Lu, M.; Sun, L.-L.

doi:10.1107/S1600536807063544

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o157

https://doi.org/10.1107/S1600536807063544

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N-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-ylcarbonyl)-N′-(2,6-dimethylphenyl)thiourea

Hai-Tang Du,^a ^* Hai-Jun Du,^b Ming Lu ^c and Li-Li Sun ^d

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

(Received 15 November 2007; accepted 26 November 2007; online 6 December 2007)

In the title compound, C₂₀H₁₉ClN₄OS, the pyrazole ring makes dihedral angles of 89.2 (4) and 46.4 (4)° with the phenyl and substituted benzene rings, respectively; these two six-membered rings are twisted by 52.1 (4)° with respect to each other. There are intramolecular hydrogen bonds of types N—H⋯O and N—H⋯Cl.

Related literature

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

Experimental

Crystal data

C₂₀H₁₉ClN₄OS
M_r = 398.90
Monoclinic, P 2₁ /n
a = 12.0749 (12) Å
b = 7.6932 (8) Å
c = 21.090 (2) Å
β = 103.071 (4)°
V = 1908.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 113 (2) K
0.32 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.902, T_max = 0.950
23102 measured reflections
4554 independent reflections
4164 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.07
4554 reflections
256 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.87 (2)	1.97 (2)	2.6744 (15)	137 (2)
N2—H2⋯Cl1	0.82 (2)	2.41 (2)	3.1175 (12)	145 (2)

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807063544/pv2049sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063544/pv2049Isup2.hkl

checkCIF report

Comment top

In the structure of the title compound, (I), the pyrazole ring makes dihedral angles of 89.2 (4) and 46.4 (4)°, with the phenyl rings, C2—C7 and C15—C20, respectively, which are twisted by 52.1 (4)° with respect to each other (Fig. 1). However in a similar structure, N-(5-chloro-3-methyl-1-phenyl pyrazole-4-ylcarbonyl)-N' -(4-methphenyl)thiourea (Du et al., 2007), the corresponding phenyl rings from dihedral angles of 74.3 (3) and 2.9 (3)°, respectively, with the central pyrazole system and the dihedral angle between the phenyl rings is 71.6 (3)°. All the bond lengths and angles are in the normal range, corresponding to the related references (Du et al., 2007; Saeed & Flörke, 2007; Wang et al., 2007). The structure is stabilized by N—H···O and N—H···Cl intramolcular hydrogen bonds; details of hydrogen-bonding geometry have been given in the Table.

Related literature top

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

Experimental top

Powdered ammonium thiocyanate (1.14 g, 15 mmol), 5-chloro-3-methyl-1-phenyl-pyrazole-4-carbonyl chloride (2.54 g, 10 mmol), polyethylene glycol-400 (0.5 ml) and acetone (25 ml) were placed in a dried round-bottomed flask containing a magnetic stirrer bar and stirred at room temperature for 1 hr, then 2,6-dimethylbenzenamine (1.15 g, 9.5 mmol) was added, and the mixture was stirred for 5 hr. The mixture was poured into water (20 ml). The resulting solid was filtered, dried and recrystallized from N,N-dimethylformamide-ethanol (1:1, v/v) to yield single crystals of (I) by slow evaporation at room temperature.

Structure description top

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

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. The molecular structure of (I) with the atomic numbering scheme, showing displacement ellipsoids at 50% probability level. Intramolcular hydrogen bonds have been represented by dashed lines.

N-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-ylcarbonyl)-N'- (2,6-dimethylphenyl)thiourea top

Crystal data top

C₂₀H₁₉ClN₄OS	F(000) = 832
M_r = 398.90	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 459 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71070 Å
a = 12.0749 (12) Å	Cell parameters from 5929 reflections
b = 7.6932 (8) Å	θ = 1.8–27.9°
c = 21.090 (2) Å	µ = 0.33 mm⁻¹
β = 103.071 (4)°	T = 113 K
V = 1908.4 (3) Å³	Prism, colorless
Z = 4	0.32 × 0.18 × 0.16 mm

Data collection top

Rigaku Saturn diffractometer	4554 independent reflections
Radiation source: rotating anode	4164 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.041
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 1.8°
ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −10→10
T_min = 0.902, T_max = 0.950	l = −26→27
23102 measured reflections

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)] = 0.036	Hydrogen site location: geom/difmap
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0402P)² + 0.794P] where P = (F_o² + 2F_c²)/3
4554 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₀H₁₉ClN₄OS	V = 1908.4 (3) Å³
M_r = 398.90	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.0749 (12) Å	µ = 0.33 mm⁻¹
b = 7.6932 (8) Å	T = 113 K
c = 21.090 (2) Å	0.32 × 0.18 × 0.16 mm
β = 103.071 (4)°

Data collection top

Rigaku Saturn diffractometer	4554 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	4164 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.950	R_int = 0.041
23102 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.31 e Å⁻³
4554 reflections	Δρ_min = −0.27 e Å⁻³
256 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	0.43026 (3)	0.10904 (5)	0.202263 (15)	0.02133 (10)
S1	0.79209 (3)	−0.08648 (5)	0.266243 (16)	0.02236 (10)
O1	0.63163 (9)	0.16452 (16)	0.41897 (5)	0.0287 (3)
N1	0.81514 (9)	0.02276 (15)	0.38858 (5)	0.0172 (2)
N2	0.64393 (10)	0.08216 (15)	0.31685 (6)	0.0169 (2)
N3	0.28650 (10)	0.27287 (16)	0.33684 (5)	0.0194 (2)
N4	0.29269 (9)	0.22644 (15)	0.27493 (5)	0.0165 (2)
C1	0.75248 (11)	0.00996 (17)	0.32786 (6)	0.0160 (3)
C2	0.92637 (11)	−0.05169 (18)	0.40858 (6)	0.0162 (3)
C3	1.02093 (11)	0.05457 (18)	0.41050 (6)	0.0180 (3)
C4	1.12834 (11)	−0.0181 (2)	0.43418 (7)	0.0210 (3)
H4	1.1942	0.0515	0.4367	0.025*
C5	1.14034 (12)	−0.1897 (2)	0.45402 (6)	0.0211 (3)
H5	1.2140	−0.2368	0.4704	0.025*
C6	1.04501 (12)	−0.29323 (19)	0.45006 (6)	0.0198 (3)
H6	1.0541	−0.4117	0.4630	0.024*
C7	0.93592 (11)	−0.22569 (18)	0.42738 (6)	0.0173 (3)
C8	1.00655 (13)	0.23944 (19)	0.38786 (7)	0.0247 (3)
H8A	0.9586	0.2434	0.3437	0.037*
H8B	1.0812	0.2896	0.3879	0.037*
H8C	0.9704	0.3063	0.4172	0.037*
C9	0.83187 (12)	−0.3363 (2)	0.42329 (8)	0.0259 (3)
H9A	0.7848	−0.2863	0.4509	0.039*
H9B	0.8549	−0.4543	0.4382	0.039*
H9C	0.7882	−0.3405	0.3781	0.039*
C10	0.58681 (11)	0.14840 (18)	0.36088 (6)	0.0176 (3)
C11	0.46730 (11)	0.19453 (18)	0.33493 (6)	0.0164 (3)
C12	0.39116 (11)	0.25472 (19)	0.37263 (6)	0.0187 (3)
C13	0.39920 (11)	0.17882 (17)	0.27273 (6)	0.0161 (3)
C14	0.41480 (13)	0.2956 (2)	0.44358 (7)	0.0267 (3)
H14A	0.3477	0.3503	0.4539	0.040*
H14B	0.4796	0.3753	0.4547	0.040*
H14C	0.4326	0.1880	0.4687	0.040*
C15	0.19141 (11)	0.22612 (18)	0.22397 (6)	0.0164 (3)
C16	0.09328 (11)	0.15251 (19)	0.23588 (7)	0.0196 (3)
H16	0.0933	0.1027	0.2771	0.024*
C17	−0.00513 (12)	0.1527 (2)	0.18663 (7)	0.0236 (3)
H17	−0.0735	0.1053	0.1944	0.028*
C18	−0.00365 (12)	0.2219 (2)	0.12628 (7)	0.0247 (3)
H18	−0.0706	0.2192	0.0924	0.030*
C19	0.09488 (12)	0.2950 (2)	0.11495 (7)	0.0233 (3)
H19	0.0954	0.3421	0.0734	0.028*
C20	0.19313 (11)	0.29973 (18)	0.16438 (7)	0.0191 (3)
H20	0.2604	0.3527	0.1573	0.023*
H1	0.7828 (15)	0.073 (2)	0.4168 (9)	0.024 (4)*
H2	0.6098 (16)	0.072 (2)	0.2787 (10)	0.034 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01647 (16)	0.0336 (2)	0.01365 (15)	0.00392 (13)	0.00286 (12)	−0.00437 (12)
S1	0.02202 (18)	0.0291 (2)	0.01609 (17)	0.00740 (14)	0.00459 (13)	−0.00227 (13)
O1	0.0192 (5)	0.0482 (7)	0.0168 (5)	0.0090 (5)	0.0000 (4)	−0.0079 (5)
N1	0.0155 (5)	0.0217 (6)	0.0142 (5)	0.0046 (5)	0.0029 (4)	−0.0010 (4)
N2	0.0141 (5)	0.0235 (6)	0.0124 (5)	0.0036 (4)	0.0012 (4)	0.0006 (4)
N3	0.0177 (6)	0.0266 (6)	0.0141 (5)	0.0026 (5)	0.0043 (4)	−0.0020 (5)
N4	0.0146 (5)	0.0226 (6)	0.0121 (5)	0.0013 (4)	0.0024 (4)	−0.0007 (4)
C1	0.0161 (6)	0.0156 (6)	0.0165 (6)	0.0012 (5)	0.0043 (5)	0.0025 (5)
C2	0.0136 (6)	0.0222 (7)	0.0127 (6)	0.0033 (5)	0.0029 (5)	−0.0007 (5)
C3	0.0191 (6)	0.0215 (7)	0.0143 (6)	0.0007 (5)	0.0056 (5)	−0.0028 (5)
C4	0.0154 (6)	0.0297 (8)	0.0183 (6)	−0.0023 (6)	0.0048 (5)	−0.0065 (6)
C5	0.0148 (6)	0.0325 (8)	0.0152 (6)	0.0063 (6)	0.0014 (5)	−0.0037 (5)
C6	0.0211 (7)	0.0235 (7)	0.0144 (6)	0.0060 (5)	0.0033 (5)	0.0016 (5)
C7	0.0163 (6)	0.0218 (7)	0.0138 (6)	0.0026 (5)	0.0032 (5)	−0.0001 (5)
C8	0.0290 (8)	0.0213 (7)	0.0265 (7)	−0.0014 (6)	0.0116 (6)	−0.0007 (6)
C9	0.0215 (7)	0.0243 (8)	0.0306 (8)	−0.0002 (6)	0.0033 (6)	0.0075 (6)
C10	0.0153 (6)	0.0199 (6)	0.0170 (6)	0.0003 (5)	0.0025 (5)	−0.0007 (5)
C11	0.0151 (6)	0.0191 (7)	0.0145 (6)	0.0011 (5)	0.0024 (5)	−0.0004 (5)
C12	0.0174 (6)	0.0227 (7)	0.0160 (6)	0.0022 (5)	0.0037 (5)	−0.0013 (5)
C13	0.0158 (6)	0.0185 (6)	0.0145 (6)	0.0011 (5)	0.0046 (5)	−0.0001 (5)
C14	0.0216 (7)	0.0412 (9)	0.0168 (7)	0.0047 (6)	0.0035 (5)	−0.0062 (6)
C15	0.0140 (6)	0.0189 (6)	0.0155 (6)	0.0021 (5)	0.0014 (5)	−0.0026 (5)
C16	0.0177 (6)	0.0236 (7)	0.0183 (6)	0.0008 (5)	0.0056 (5)	0.0005 (5)
C17	0.0143 (6)	0.0296 (8)	0.0270 (7)	−0.0014 (6)	0.0047 (6)	−0.0025 (6)
C18	0.0169 (7)	0.0328 (8)	0.0218 (7)	0.0023 (6)	−0.0013 (5)	−0.0021 (6)
C19	0.0209 (7)	0.0295 (8)	0.0178 (6)	0.0033 (6)	0.0012 (5)	0.0032 (6)
C20	0.0155 (6)	0.0224 (7)	0.0191 (6)	0.0004 (5)	0.0031 (5)	0.0014 (5)

Geometric parameters (Å, º) top

Cl1—C13	1.6998 (13)	C8—H8A	0.9800
S1—C1	1.6581 (13)	C8—H8B	0.9800
O1—C10	1.2284 (16)	C8—H8C	0.9800
N1—C1	1.3355 (17)	C9—H9A	0.9800
N1—C2	1.4331 (16)	C9—H9B	0.9800
N1—H1	0.87 (2)	C9—H9C	0.9800
N2—C10	1.3738 (17)	C10—C11	1.4665 (18)
N2—C1	1.3939 (17)	C11—C13	1.3869 (18)
N2—H2	0.82 (2)	C11—C12	1.4222 (18)
N3—C12	1.3247 (17)	C12—C14	1.4920 (18)
N3—N4	1.3719 (15)	C14—H14A	0.9800
N4—C13	1.3482 (17)	C14—H14B	0.9800
N4—C15	1.4339 (16)	C14—H14C	0.9800
C2—C7	1.3935 (19)	C15—C20	1.3828 (19)
C2—C3	1.3974 (19)	C15—C16	1.3865 (19)
C3—C4	1.3968 (19)	C16—C17	1.3902 (19)
C3—C8	1.498 (2)	C16—H16	0.9500
C4—C5	1.383 (2)	C17—C18	1.383 (2)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.387 (2)	C18—C19	1.385 (2)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.3960 (18)	C19—C20	1.3915 (19)
C6—H6	0.9500	C19—H19	0.9500
C7—C9	1.5038 (19)	C20—H20	0.9500

C1—N1—C2	122.87 (11)	C7—C9—H9C	109.5
C1—N1—H1	116.2 (11)	H9A—C9—H9C	109.5
C2—N1—H1	120.8 (11)	H9B—C9—H9C	109.5
C10—N2—C1	129.21 (11)	O1—C10—N2	122.43 (12)
C10—N2—H2	118.6 (14)	O1—C10—C11	121.48 (12)
C1—N2—H2	111.8 (13)	N2—C10—C11	116.07 (11)
C12—N3—N4	105.34 (11)	C13—C11—C12	103.72 (11)
C13—N4—N3	111.18 (10)	C13—C11—C10	130.91 (12)
C13—N4—C15	129.22 (11)	C12—C11—C10	125.17 (12)
N3—N4—C15	119.54 (10)	N3—C12—C11	111.70 (12)
N1—C1—N2	115.97 (12)	N3—C12—C14	119.38 (12)
N1—C1—S1	125.67 (10)	C11—C12—C14	128.91 (12)
N2—C1—S1	118.35 (10)	N4—C13—C11	108.05 (11)
C7—C2—C3	122.63 (12)	N4—C13—Cl1	121.12 (10)
C7—C2—N1	118.65 (12)	C11—C13—Cl1	130.81 (11)
C3—C2—N1	118.69 (12)	C12—C14—H14A	109.5
C4—C3—C2	117.57 (13)	C12—C14—H14B	109.5
C4—C3—C8	121.68 (13)	H14A—C14—H14B	109.5
C2—C3—C8	120.75 (12)	C12—C14—H14C	109.5
C5—C4—C3	121.03 (13)	H14A—C14—H14C	109.5
C5—C4—H4	119.5	H14B—C14—H14C	109.5
C3—C4—H4	119.5	C20—C15—C16	121.40 (12)
C4—C5—C6	120.10 (13)	C20—C15—N4	119.66 (12)
C4—C5—H5	119.9	C16—C15—N4	118.94 (12)
C6—C5—H5	119.9	C15—C16—C17	119.03 (13)
C5—C6—C7	120.86 (13)	C15—C16—H16	120.5
C5—C6—H6	119.6	C17—C16—H16	120.5
C7—C6—H6	119.6	C18—C17—C16	120.08 (13)
C2—C7—C6	117.78 (13)	C18—C17—H17	120.0
C2—C7—C9	120.86 (12)	C16—C17—H17	120.0
C6—C7—C9	121.36 (13)	C17—C18—C19	120.36 (13)
C3—C8—H8A	109.5	C17—C18—H18	119.8
C3—C8—H8B	109.5	C19—C18—H18	119.8
H8A—C8—H8B	109.5	C18—C19—C20	120.09 (13)
C3—C8—H8C	109.5	C18—C19—H19	120.0
H8A—C8—H8C	109.5	C20—C19—H19	120.0
H8B—C8—H8C	109.5	C15—C20—C19	119.00 (13)
C7—C9—H9A	109.5	C15—C20—H20	120.5
C7—C9—H9B	109.5	C19—C20—H20	120.5
H9A—C9—H9B	109.5

C12—N3—N4—C13	0.60 (15)	N2—C10—C11—C12	175.91 (13)
C12—N3—N4—C15	177.88 (12)	N4—N3—C12—C11	−0.58 (16)
C2—N1—C1—N2	177.06 (12)	N4—N3—C12—C14	179.86 (13)
C2—N1—C1—S1	−1.7 (2)	C13—C11—C12—N3	0.36 (16)
C10—N2—C1—N1	−7.9 (2)	C10—C11—C12—N3	−174.98 (13)
C10—N2—C1—S1	170.98 (12)	C13—C11—C12—C14	179.87 (15)
C1—N1—C2—C7	−84.89 (16)	C10—C11—C12—C14	4.5 (2)
C1—N1—C2—C3	97.20 (16)	N3—N4—C13—C11	−0.38 (16)
C7—C2—C3—C4	−1.91 (19)	C15—N4—C13—C11	−177.33 (13)
N1—C2—C3—C4	175.92 (11)	N3—N4—C13—Cl1	178.12 (9)
C7—C2—C3—C8	178.10 (12)	C15—N4—C13—Cl1	1.2 (2)
N1—C2—C3—C8	−4.07 (19)	C12—C11—C13—N4	0.02 (15)
C2—C3—C4—C5	0.97 (19)	C10—C11—C13—N4	174.98 (14)
C8—C3—C4—C5	−179.04 (12)	C12—C11—C13—Cl1	−178.29 (11)
C3—C4—C5—C6	0.6 (2)	C10—C11—C13—Cl1	−3.3 (2)
C4—C5—C6—C7	−1.3 (2)	C13—N4—C15—C20	−48.8 (2)
C3—C2—C7—C6	1.24 (19)	N3—N4—C15—C20	134.47 (14)
N1—C2—C7—C6	−176.58 (11)	C13—N4—C15—C16	131.62 (15)
C3—C2—C7—C9	−178.78 (13)	N3—N4—C15—C16	−45.11 (18)
N1—C2—C7—C9	3.40 (19)	C20—C15—C16—C17	0.2 (2)
C5—C6—C7—C2	0.39 (19)	N4—C15—C16—C17	179.73 (12)
C5—C6—C7—C9	−179.59 (13)	C15—C16—C17—C18	1.5 (2)
C1—N2—C10—O1	6.0 (2)	C16—C17—C18—C19	−1.6 (2)
C1—N2—C10—C11	−172.25 (13)	C17—C18—C19—C20	−0.1 (2)
O1—C10—C11—C13	−176.38 (15)	C16—C15—C20—C19	−1.8 (2)
N2—C10—C11—C13	1.9 (2)	N4—C15—C20—C19	178.60 (12)
O1—C10—C11—C12	−2.4 (2)	C18—C19—C20—C15	1.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.87 (2)	1.97 (2)	2.6744 (15)	137 (2)
N2—H2···Cl1	0.82 (2)	2.41 (2)	3.1175 (12)	145 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉ClN₄OS
M_r	398.90
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	12.0749 (12), 7.6932 (8), 21.090 (2)
β (°)	103.071 (4)
V (Å³)	1908.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.32 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.902, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	23102, 4554, 4164
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.090, 1.07
No. of reflections	4554
No. of parameters	256
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.27

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.87 (2)	1.97 (2)	2.6744 (15)	137 (2)
N2—H2···Cl1	0.82 (2)	2.41 (2)	3.1175 (12)	145 (2)

Acknowledgements

The authors thank Guiyang College (No. 2007012) for financial support.

References

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
Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Saeed, A. & Flörke, U. (2007). Acta Cryst. E63, o3695. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. 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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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-ylcarbon­yl)-N′-(2,6-di­methyl­phen­yl)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-ylcarbonyl)-N′-(2,6-dimethylphenyl)thiourea