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

Haitang Du; Haijun Du; Ying An; Shengnan Li

doi:10.1107/S1600536808019417

. 2008 Jul 5;64(Pt 8):o1404. doi: 10.1107/S1600536808019417

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, Shengnan Li ^c

PMCID: PMC2962037 PMID: 21203124

Abstract

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,
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[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 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

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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019417/gk2153sup1.cif

e-64-o1404-sup1.cif^{(19.9KB, cif)}

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

e-64-o1404-Isup2.hkl^{(153KB, hkl)}

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

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)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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).