N-(5-Chloro-3-methyl-1-phenyl­pyrazol-4-ylcarbon­yl)-N′-(2-methoxy­phen­yl)thio­urea

Du, H.; Du, H.; Lu, M.; Sun, L.

doi:10.1107/S1600536807068390

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o609

doi:10.1107/S1600536807068390

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N-(5-Chloro-3-methyl-1-phenylpyrazol-4-ylcarbonyl)-N′-(2-methoxyphenyl)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 Science, Guizhou University for Nationalites, Guiyang 550025, People's Republic of China, ^cSchool 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@sohu.com

(Received 17 November 2007; accepted 25 December 2007; online 20 February 2008)

In the title compound, C₁₉H₁₇ClN₄O₂S, the dihedral angle between the pyrazole and phenyl rings is 43.3 (3)°. The bridging unit between the pyrazole and methoxyphenyl rings is planar within 0.0169 Å and makes dihedral angles of 2.3 and 26.4°, respectively, with these two rings. This conformation is influenced by intramolecular N—H⋯O and N—H⋯Cl hydrogen bonds. The crystal packing is stabilized by C—H⋯π interactions.

Related literature

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

Experimental

Crystal data

C₁₉H₁₇ClN₄O₂S
M_r = 400.88
Monoclinic, P 2₁ /c
a = 20.339 (2) Å
b = 7.4408 (9) Å
c = 12.7919 (15) Å
β = 107.029 (2)°
V = 1851.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 294 (2) K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.922, T_max = 0.941
10087 measured reflections
3793 independent reflections
3065 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.04
3793 reflections
254 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Cl1	0.890 (9)	2.398 (14)	3.1657 (14)	144.6 (17)
N4—H4A⋯O1	0.895 (9)	1.913 (15)	2.6589 (19)	139.6 (18)
C2—H2⋯Cg1ⁱ	0.93	2.88	3.613 (2)	136
C10—H10B⋯Cg2ⁱⁱ	0.96	2.98	3.809 (2)	146
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068390/bq2053sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068390/bq2053Isup2.hkl

checkCIF report

Comment top

The molecular structure of (I) with the atom-numbering scheme is shown in Fig.1. The pyrazole ring makes dihedral angles of 43.3° and 24.5°, with C1—C6 and C13—C18 rings, respectively; these two six-membered rings are twisted by 19.6° with respect to each other. However, in the similar structure, N-(5-chloro-3-methyl-1-phenyl pyrazole-4-ylcarbonyl)-N'-(4-methphenyl)thiourea (Du et al., 2007), the two phenyl rings deviate from the central pyrazole system with dihedral angles of 74.3° and 2.9°, respectively, the dihedral angle between them being 71.6°. 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). There also exist two intramolecular N—H···O and N—H···Cl hydrogen bonds and two C—H···pi interaction (Table 1.). Investigation on the packing pattern demonstrates that those discrete molecules are interconnected by slightly weak contacts C2—H2···Cg1 and C10—H10B···Cg2 [Cg1=C1—C6 and Cg2=C13—C18] into a two-dimensional network, as shown in Fig. 2.

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 (0.15 mmol) and acetone (25 mL) were placed in a dried round-bottomed flask containing a magnetic stirrer bar and stirred at room temperature for 1 h. Then 2-methoxybenzenamine (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 DMF-EtOH to give N-(5-chloro-3-methyl-1-phenyl pyrazole-4-ylcarbonyl)-N'-(2-methoxyphenyl)thiourea. Single crystals of the title compound were obtained by slow evaporation of a solution in DMF-EtOH(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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The molecular structure of (I) with the atom numbering scheme, showing N—H···O and N—H···Cl intramolecular hydrogen bonds.
	Fig. 2. The two-dimensional supramolecular framework showing the C—H···pi contacts [Cg1=C1—C6, Cg2=C13—C18].

N-(5-Chloro-3-methyl-1-phenylpyrazol-4-ylcarbonyl)- N'-(2-methoxyphenyl)thiourea top

Crystal data top

C₁₉H₁₇ClN₄O₂S	F(000) = 832
M_r = 400.88	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 437 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 20.339 (2) Å	Cell parameters from 5493 reflections
b = 7.4408 (9) Å	θ = 2.7–26.4°
c = 12.7919 (15) Å	µ = 0.34 mm⁻¹
β = 107.029 (2)°	T = 294 K
V = 1851.0 (4) Å³	Prism, colorless
Z = 4	0.24 × 0.22 × 0.18 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3793 independent reflections
Radiation source: fine-focus sealed tube	3065 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→25
T_min = 0.922, T_max = 0.941	k = −9→7
10087 measured reflections	l = −15→15

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0493P)² + 0.4744P] where P = (F_o² + 2F_c²)/3
3793 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₁₇ClN₄O₂S	V = 1851.0 (4) Å³
M_r = 400.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.339 (2) Å	µ = 0.34 mm⁻¹
b = 7.4408 (9) Å	T = 294 K
c = 12.7919 (15) Å	0.24 × 0.22 × 0.18 mm
β = 107.029 (2)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3793 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3065 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.941	R_int = 0.024
10087 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
3793 reflections	Δρ_min = −0.23 e Å⁻³
254 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
S1	0.32848 (2)	0.38045 (8)	0.78067 (4)	0.05368 (16)
Cl1	0.39634 (2)	0.49010 (7)	0.47794 (3)	0.04935 (14)
O1	0.16432 (6)	0.5391 (2)	0.46861 (10)	0.0554 (4)
O2	0.06377 (6)	0.3605 (2)	0.62638 (10)	0.0530 (3)
N1	0.32052 (6)	0.59589 (19)	0.27986 (10)	0.0375 (3)
N2	0.25436 (7)	0.6246 (2)	0.21555 (11)	0.0419 (3)
N3	0.27109 (7)	0.4682 (2)	0.57720 (11)	0.0438 (4)
N4	0.19402 (7)	0.4401 (2)	0.67699 (11)	0.0418 (3)
C1	0.43578 (9)	0.6916 (3)	0.27971 (15)	0.0472 (4)
H1	0.4428	0.7452	0.3478	0.057*
C2	0.48659 (9)	0.6974 (3)	0.22681 (16)	0.0523 (5)
H2	0.5284	0.7528	0.2607	0.063*
C3	0.47554 (9)	0.6224 (3)	0.12530 (16)	0.0520 (5)
H3	0.5097	0.6276	0.0905	0.062*
C4	0.41394 (10)	0.5393 (3)	0.07479 (15)	0.0542 (5)
H4	0.4064	0.4903	0.0054	0.065*
C5	0.36327 (9)	0.5282 (3)	0.12681 (14)	0.0472 (4)
H5	0.3220	0.4700	0.0934	0.057*
C6	0.37472 (8)	0.6047 (2)	0.22901 (13)	0.0371 (4)
C7	0.32183 (8)	0.5520 (2)	0.38253 (13)	0.0357 (3)
C8	0.25474 (8)	0.5552 (2)	0.38879 (13)	0.0363 (4)
C9	0.21508 (8)	0.6007 (2)	0.28072 (13)	0.0384 (4)
C10	0.13868 (8)	0.6187 (3)	0.23440 (15)	0.0495 (5)
H10A	0.1276	0.6539	0.1590	0.074*
H10B	0.1223	0.7082	0.2747	0.074*
H10C	0.1172	0.5055	0.2398	0.074*
C11	0.22584 (8)	0.5214 (2)	0.47961 (13)	0.0387 (4)
C12	0.25973 (8)	0.4323 (2)	0.67773 (13)	0.0378 (4)
C13	0.16530 (8)	0.4213 (2)	0.76497 (13)	0.0389 (4)
C14	0.20047 (9)	0.4519 (3)	0.87383 (14)	0.0521 (5)
H14	0.2469	0.4816	0.8937	0.063*
C15	0.16671 (11)	0.4384 (3)	0.95325 (15)	0.0604 (5)
H15	0.1905	0.4596	1.0262	0.072*
C16	0.09837 (11)	0.3938 (3)	0.92464 (16)	0.0601 (5)
H16	0.0763	0.3822	0.9785	0.072*
C17	0.06196 (9)	0.3661 (3)	0.81632 (16)	0.0516 (5)
H17	0.0154	0.3379	0.7973	0.062*
C18	0.09501 (8)	0.3806 (2)	0.73614 (14)	0.0404 (4)
C19	−0.00924 (9)	0.3381 (4)	0.59165 (18)	0.0673 (6)
H19A	−0.0211	0.2307	0.6236	0.101*
H19B	−0.0251	0.3286	0.5134	0.101*
H19C	−0.0305	0.4398	0.6146	0.101*
H3A	0.3155 (5)	0.467 (3)	0.5812 (17)	0.062 (6)*
H4A	0.1642 (8)	0.468 (3)	0.6123 (10)	0.057 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0354 (2)	0.0762 (4)	0.0463 (3)	0.0095 (2)	0.00703 (19)	0.0106 (2)
Cl1	0.0290 (2)	0.0731 (3)	0.0433 (2)	0.00205 (19)	0.00649 (17)	0.0023 (2)
O1	0.0294 (6)	0.0926 (11)	0.0459 (7)	0.0051 (6)	0.0140 (5)	0.0108 (7)
O2	0.0300 (6)	0.0846 (10)	0.0443 (7)	−0.0058 (6)	0.0108 (5)	−0.0054 (6)
N1	0.0276 (6)	0.0478 (8)	0.0377 (7)	−0.0009 (6)	0.0107 (5)	−0.0008 (6)
N2	0.0298 (7)	0.0543 (9)	0.0407 (7)	0.0017 (6)	0.0090 (6)	0.0021 (6)
N3	0.0279 (7)	0.0655 (10)	0.0395 (7)	0.0010 (7)	0.0124 (6)	0.0038 (7)
N4	0.0289 (7)	0.0627 (10)	0.0338 (7)	−0.0018 (6)	0.0092 (6)	0.0016 (7)
C1	0.0395 (9)	0.0516 (11)	0.0540 (10)	−0.0062 (8)	0.0190 (8)	−0.0106 (9)
C2	0.0363 (9)	0.0572 (12)	0.0672 (12)	−0.0069 (8)	0.0213 (8)	−0.0031 (10)
C3	0.0426 (10)	0.0635 (12)	0.0583 (11)	0.0045 (9)	0.0280 (9)	0.0085 (9)
C4	0.0472 (10)	0.0780 (14)	0.0410 (9)	0.0036 (10)	0.0186 (8)	0.0000 (9)
C5	0.0358 (9)	0.0651 (12)	0.0402 (9)	−0.0021 (8)	0.0104 (7)	−0.0014 (8)
C6	0.0302 (8)	0.0418 (9)	0.0420 (8)	0.0022 (7)	0.0146 (7)	0.0029 (7)
C7	0.0283 (7)	0.0413 (9)	0.0364 (8)	−0.0011 (7)	0.0077 (6)	−0.0023 (7)
C8	0.0277 (7)	0.0434 (9)	0.0384 (8)	−0.0007 (7)	0.0108 (6)	−0.0019 (7)
C9	0.0305 (8)	0.0438 (9)	0.0410 (8)	0.0001 (7)	0.0109 (7)	−0.0012 (7)
C10	0.0304 (9)	0.0670 (13)	0.0493 (10)	0.0014 (8)	0.0092 (7)	0.0046 (9)
C11	0.0306 (8)	0.0474 (10)	0.0389 (8)	−0.0011 (7)	0.0112 (7)	−0.0011 (7)
C12	0.0328 (8)	0.0422 (9)	0.0386 (8)	−0.0018 (7)	0.0106 (7)	−0.0003 (7)
C13	0.0348 (8)	0.0462 (10)	0.0382 (8)	0.0029 (7)	0.0145 (7)	0.0031 (7)
C14	0.0394 (9)	0.0748 (14)	0.0413 (9)	0.0019 (9)	0.0104 (8)	−0.0019 (9)
C15	0.0569 (12)	0.0878 (16)	0.0365 (9)	0.0121 (11)	0.0137 (9)	0.0016 (10)
C16	0.0612 (12)	0.0812 (15)	0.0474 (10)	0.0082 (11)	0.0306 (10)	0.0100 (10)
C17	0.0407 (9)	0.0642 (13)	0.0559 (11)	0.0001 (9)	0.0236 (8)	0.0053 (9)
C18	0.0362 (8)	0.0450 (10)	0.0416 (9)	0.0015 (7)	0.0140 (7)	0.0014 (7)
C19	0.0344 (10)	0.0985 (18)	0.0654 (13)	−0.0134 (10)	0.0090 (9)	−0.0023 (12)

Geometric parameters (Å, º) top

S1—C12	1.6612 (17)	C4—H4	0.9300
Cl1—C7	1.7072 (16)	C5—C6	1.382 (2)
O1—C11	1.2246 (19)	C5—H5	0.9300
O2—C18	1.369 (2)	C7—C8	1.390 (2)
O2—C19	1.430 (2)	C8—C9	1.422 (2)
N1—C7	1.346 (2)	C8—C11	1.469 (2)
N1—N2	1.3729 (18)	C9—C10	1.498 (2)
N1—C6	1.4361 (19)	C10—H10A	0.9600
N2—C9	1.325 (2)	C10—H10B	0.9600
N3—C11	1.374 (2)	C10—H10C	0.9600
N3—C12	1.397 (2)	C13—C14	1.385 (2)
N3—H3A	0.890 (9)	C13—C18	1.401 (2)
N4—C12	1.335 (2)	C14—C15	1.386 (3)
N4—C13	1.419 (2)	C14—H14	0.9300
N4—H4A	0.895 (9)	C15—C16	1.370 (3)
C1—C6	1.382 (2)	C15—H15	0.9300
C1—C2	1.392 (2)	C16—C17	1.382 (3)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.370 (3)	C17—C18	1.385 (2)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.377 (3)	C19—H19A	0.9600
C3—H3	0.9300	C19—H19B	0.9600
C4—C5	1.383 (2)	C19—H19C	0.9600

C18—O2—C19	117.33 (14)	C8—C9—C10	129.27 (14)
C7—N1—N2	110.99 (12)	C9—C10—H10A	109.5
C7—N1—C6	130.88 (13)	C9—C10—H10B	109.5
N2—N1—C6	117.99 (13)	H10A—C10—H10B	109.5
C9—N2—N1	105.54 (13)	C9—C10—H10C	109.5
C11—N3—C12	130.06 (14)	H10A—C10—H10C	109.5
C11—N3—H3A	117.0 (13)	H10B—C10—H10C	109.5
C12—N3—H3A	112.6 (13)	O1—C11—N3	121.70 (15)
C12—N4—C13	129.34 (14)	O1—C11—C8	121.50 (15)
C12—N4—H4A	114.9 (13)	N3—C11—C8	116.80 (14)
C13—N4—H4A	115.6 (13)	N4—C12—N3	114.84 (14)
C6—C1—C2	118.66 (17)	N4—C12—S1	128.64 (13)
C6—C1—H1	120.7	N3—C12—S1	116.50 (12)
C2—C1—H1	120.7	C14—C13—C18	119.13 (15)
C3—C2—C1	120.60 (17)	C14—C13—N4	124.74 (15)
C3—C2—H2	119.7	C18—C13—N4	115.98 (14)
C1—C2—H2	119.7	C13—C14—C15	120.26 (17)
C2—C3—C4	120.13 (17)	C13—C14—H14	119.9
C2—C3—H3	119.9	C15—C14—H14	119.9
C4—C3—H3	119.9	C16—C15—C14	120.21 (18)
C3—C4—C5	120.31 (18)	C16—C15—H15	119.9
C3—C4—H4	119.8	C14—C15—H15	119.9
C5—C4—H4	119.8	C15—C16—C17	120.51 (17)
C6—C5—C4	119.20 (17)	C15—C16—H16	119.7
C6—C5—H5	120.4	C17—C16—H16	119.7
C4—C5—H5	120.4	C16—C17—C18	119.80 (17)
C5—C6—C1	121.07 (15)	C16—C17—H17	120.1
C5—C6—N1	118.09 (14)	C18—C17—H17	120.1
C1—C6—N1	120.82 (15)	O2—C18—C17	124.80 (15)
N1—C7—C8	108.23 (13)	O2—C18—C13	115.14 (14)
N1—C7—Cl1	121.51 (11)	C17—C18—C13	120.06 (16)
C8—C7—Cl1	130.10 (13)	O2—C19—H19A	109.5
C7—C8—C9	103.59 (13)	O2—C19—H19B	109.5
C7—C8—C11	132.02 (14)	H19A—C19—H19B	109.5
C9—C8—C11	124.40 (14)	O2—C19—H19C	109.5
N2—C9—C8	111.64 (13)	H19A—C19—H19C	109.5
N2—C9—C10	119.07 (15)	H19B—C19—H19C	109.5

C7—N1—N2—C9	1.05 (18)	C11—C8—C9—C10	−2.0 (3)
C6—N1—N2—C9	177.15 (14)	C12—N3—C11—O1	−2.6 (3)
C6—C1—C2—C3	1.6 (3)	C12—N3—C11—C8	177.70 (17)
C1—C2—C3—C4	−0.4 (3)	C7—C8—C11—O1	176.78 (18)
C2—C3—C4—C5	−1.1 (3)	C9—C8—C11—O1	−3.6 (3)
C3—C4—C5—C6	1.3 (3)	C7—C8—C11—N3	−3.5 (3)
C4—C5—C6—C1	0.0 (3)	C9—C8—C11—N3	176.15 (16)
C4—C5—C6—N1	178.21 (16)	C13—N4—C12—N3	−176.04 (17)
C2—C1—C6—C5	−1.4 (3)	C13—N4—C12—S1	5.8 (3)
C2—C1—C6—N1	−179.60 (16)	C11—N3—C12—N4	4.6 (3)
C7—N1—C6—C5	134.17 (19)	C11—N3—C12—S1	−176.95 (15)
N2—N1—C6—C5	−41.0 (2)	C12—N4—C13—C14	23.6 (3)
C7—N1—C6—C1	−47.6 (3)	C12—N4—C13—C18	−160.93 (18)
N2—N1—C6—C1	137.20 (17)	C18—C13—C14—C15	1.4 (3)
N2—N1—C7—C8	−1.46 (19)	N4—C13—C14—C15	176.77 (19)
C6—N1—C7—C8	−176.90 (16)	C13—C14—C15—C16	0.3 (3)
N2—N1—C7—Cl1	174.41 (12)	C14—C15—C16—C17	−1.5 (3)
C6—N1—C7—Cl1	−1.0 (3)	C15—C16—C17—C18	1.0 (3)
N1—C7—C8—C9	1.22 (18)	C19—O2—C18—C17	5.6 (3)
Cl1—C7—C8—C9	−174.18 (14)	C19—O2—C18—C13	−173.48 (18)
N1—C7—C8—C11	−179.09 (17)	C16—C17—C18—O2	−178.28 (19)
Cl1—C7—C8—C11	5.5 (3)	C16—C17—C18—C13	0.7 (3)
N1—N2—C9—C8	−0.24 (19)	C14—C13—C18—O2	177.16 (17)
N1—N2—C9—C10	−178.72 (16)	N4—C13—C18—O2	1.4 (2)
C7—C8—C9—N2	−0.61 (19)	C14—C13—C18—C17	−1.9 (3)
C11—C8—C9—N2	179.67 (16)	N4—C13—C18—C17	−177.68 (17)
C7—C8—C9—C10	177.68 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1	0.89 (1)	2.40 (1)	3.1657 (14)	145 (2)
N4—H4A···O1	0.90 (1)	1.91 (2)	2.6589 (19)	140 (2)
C2—H2···Cg1ⁱ	0.93	2.88	3.613 (2)	136
C10—H10B···Cg2ⁱⁱ	0.96	2.98	3.809 (2)	146

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇ClN₄O₂S
M_r	400.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	20.339 (2), 7.4408 (9), 12.7919 (15)
β (°)	107.029 (2)
V (Å³)	1851.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.922, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	10087, 3793, 3065
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.04
No. of reflections	3793
No. of parameters	254
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)	0.22, −0.23

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1	0.890 (9)	2.398 (14)	3.1657 (14)	144.6 (17)
N4—H4A···O1	0.895 (9)	1.913 (15)	2.6589 (19)	139.6 (18)
C2—H2···Cg1ⁱ	0.93	2.88	3.613 (2)	136
C10—H10B···Cg2ⁱⁱ	0.96	2.98	3.809 (2)	146

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.

Acknowledgements

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

References

Bruker (1997). SMART (Version 5.611) and SAINT (Version 6.0). 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. Version 2.03. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA. 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 3| March 2008| Page o609

doi:10.1107/S1600536807068390

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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-phenyl­pyrazol-4-ylcarbon­yl)-N′-(2-meth­oxy­phen­yl)thio­urea

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(5-Chloro-3-methyl-1-phenylpyrazol-4-ylcarbonyl)-N′-(2-methoxyphenyl)thiourea