4-(5-Phenyl-3-trifluoro­meth­yl-1H-pyrazol-1-­yl)benzene­sulfonamide

Abdullah M Asiri; Abdulrahman O Al-Youbi; Hassan M Faidallah; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536811033435

. 2011 Aug 27;67(Pt 9):o2424. doi: 10.1107/S1600536811033435

4-(5-Phenyl-3-trifluoromethyl-1H-pyrazol-1-yl)benzenesulfonamide

Abdullah M Asiri ^a,^b,^‡, Abdulrahman O Al-Youbi ^a, Hassan M Faidallah ^a, Seik Weng Ng ^c,^a, Edward R T Tiekink ^c,^*

PMCID: PMC3200877 PMID: 22059006

Abstract

Significant twists between the aromatic rings are evident in the structure of the title compound, C₁₆H₁₂F₃N₃O₂S. With reference to the pyrazole plane, the N- and C-bound benzene rings form dihedral angles of 57.12 (11) and 29.75 (11)°, respectively. The dihedral angle between the benzene rings is 52.82 (11)°. The presence of N—H⋯O(sulfonamide) and N—H⋯N(pyrazole) hydrogen bonds lead to supramolecular tubes along the b-axis direction. These are connected into layers via C—H⋯O interactions involving a bifurcated O atom (not involved in the N—H⋯O hydrogen bonding). Layers stack along the a-axis direction.

Related literature

For background to the biological applications of related species, see: Faidallah et al. (2007 ▶); Al-Saadi et al. (2008 ▶). For the crystal structure of a related species, see: Dev et al. (1999 ▶).

Experimental

Crystal data

C₁₆H₁₂F₃N₃O₂S
M _r = 367.35
Monoclinic,
a = 16.2430 (7) Å
b = 4.9461 (2) Å
c = 21.2383 (8) Å
β = 111.231 (5)°
V = 1590.47 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.40 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.735, T _max = 1.000
7901 measured reflections
3560 independent reflections
2876 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.113
S = 1.06
3560 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033435/hg5083sup1.cif

e-67-o2424-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033435/hg5083Isup2.hkl

e-67-o2424-Isup2.hkl^{(174.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033435/hg5083Isup3.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
N3—H1⋯O1ⁱ	0.84 (3)	2.14 (3)	2.911 (2)	153 (2)
N3—H2⋯N2ⁱⁱ	0.87 (2)	2.21 (3)	3.049 (3)	164 (2)
C9—H9⋯O2ⁱⁱⁱ	0.95	2.49	3.376 (3)	155
C16—H16⋯O2^iv	0.95	2.55	3.137 (2)	120

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

Acknowledgments

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The crystallographic study of the title compound, (I), which is related to the anti-inflammatory drug, Celecoxib (Dev et al., 1999), was motivated by the recent reports of the biological activities exhibited by related pyrazole compounds (Faidallah et al., 2007; Al-Saadi et al., 2008).

Significant twists are evident in the molecule of (I), Fig. 1. With reference to the pyrazole (N1,N2,C2—C4) plane (r.m.s. deviation = 0,003 Å), the N-bound benzene ring (C11–C16) forms a dihedral angle of 57.12 (11) ° whereas the C-bound benzene ring (C5–C10) forms a dihedral angle of 29.75 (11) °; the dihedral angle formed between the two benzene rings is 52.82 (11) °. The orientations of the benzene rings in (I) differ from those in Celecoxib (Dev et al., 1999), the 4-methylphenyl derivative, with the dihedral angles formed between the N– and C-bound benzene rings and the pyrazole plane being 86.00 (12) and 15.25 (13) °, respectively.

Supramolecular tubes along the b axis feature in the crystal packing, Fig. 2. These are stabilized by amino-H hydrogen bonds to the pyrazole-N and to one of the sulfonamide-O atoms, Table 1. Tubes are linked into layers in the bc plane by C—H···O interactions whereby the sulfonamide-O2 atom is bifurcated, Table 1 and Fig. 3. Layers stack along the a axis, Fig. 4.

Experimental

A solution of 4,4,4-trifluoro-1-phenyl-1,3-butanedione (2.01 g, 10 mmol) in ethanol (50 ml) was refluxed with 4-hydrazinobenzenesulfonamide hydrochloride (2.2 g, 10 mmol) for 4 h, cooled and diluted with water. The precipitated crude product was filtered and recrystallized from ethanol as colourless crystals; M.pt. 431–433 K.