1-(1,5-Diphenyl-4-phenyl­sulfonyl-1H-pyrazol-3-yl)ethanone

Hoong-Kun Fun; Ching Kheng Quah; Hatem A Abdel-Aziz; Hazem A Ghabbour

doi:10.1107/S1600536812035027

. 2012 Aug 15;68(Pt 9):o2725. doi: 10.1107/S1600536812035027

1-(1,5-Diphenyl-4-phenylsulfonyl-1H-pyrazol-3-yl)ethanone

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Hatem A Abdel-Aziz ^b, Hazem A Ghabbour ^b

PMCID: PMC3435738 PMID: 22969609

Abstract

The asymmetric unit of the title compound, C₂₃H₁₈N₂O₃S, contains two molecules with comparable geometries. In one molecule, the pyrazole ring forms dihedral angles of 61.65 (11), 47.88 (11) and 63.20 (14)° with the three benzene rings. The corresponding values for the other molecule are 77.19 (11), 43.55 (11) and 63.56 (15)°. In the crystal, both molecules are linked into inversion dimers by pairs of C—H⋯S hydrogen bonds, generating R ₂ ²(14) loops in each case.

Related literature

For background to and pharmaceutical applications of pyrazole derivatives, see: Gürsoy et al. (2000 ▶); Kurumbail et al. (1996 ▶). For further synthetic details, see: Saleh & Abd El-Rahman (2009 ▶); Nassar et al. (2011 ▶).

Experimental

Crystal data

C₂₃H₁₈N₂O₃S
M _r = 402.45
Triclinic,
a = 10.4078 (2) Å
b = 14.0839 (3) Å
c = 14.2468 (3) Å
α = 87.595 (2)°
β = 80.875 (2)°
γ = 86.850 (2)°
V = 2057.62 (7) Å³
Z = 4
Cu Kα radiation
μ = 1.62 mm⁻¹
T = 296 K
0.66 × 0.55 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.415, T _max = 0.771
19520 measured reflections
6561 independent reflections
5618 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.123
S = 1.05
6561 reflections
525 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035027/hb6911sup1.cif

e-68-o2725-sup1.cif^{(45.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035027/hb6911Isup2.hkl

e-68-o2725-Isup2.hkl^{(321.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812035027/hb6911Isup3.cml

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
C11A—H11A⋯O2A ⁱ	0.93	2.59	3.428 (3)	149
C11B—H11B⋯O3B ⁱⁱ	0.93	2.57	3.370 (3)	144

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

Pyrazole derivatives have been attracted a great deal of research interest because of their various pharmaceutical applications (Gürsoy et al., 2000). N-arylpyrazoles were found to be a main pharmacophore in the famous anti-inflammatory drugs Celecoxib and SC-558 (Kurumbail et al., 1996). As part of our atudies in this area, we now describe the crystal structure of the title compound.

The asymmetric unit (Fig. 1) of the title compound consists of two independent molecules (A and B), with comparable geometries. In molecule A, pyrazol-3-yl ring (N1A/N2A/C1A-C3A) forms dihedral angles of 61.65 (11), 47.88 (11) and 63.20 (14)° with the three benzene rings (C6A-C11A, C12A-C17A, C18A-C23A), respectively. The corresponding dihedral angles for molecule B are 77.19 (11), 43.55 (11) and 63.56 (15)°, respectively.

In the crystal, Fig. 2, both independent molecules are linked into inversion dimers by pairs of C—H···S hydrogen bonds (Table 1), generating R₂²(14) loops in each case.

Experimental

The title compound was prepared by the reaction of (Z)-2-oxo-N'-phenylpropanehydrazonoyl chloride with 1-phenyl-2-(phenylsulfonyl)ethanone according to the reported method (Saleh & Abd El-Rahman, 2009; Nassar et al., 2011). Yellow plates were obtained by slowly evaporating an ethanol solution at room temperature.