4-(3-Methyl-5-phenyl-1H-pyrazol-1-yl)benzene­sulfonamide

Abdullah M Asiri; Hassan M Faidallah; Abdulrahman O Al-Youbi; Salem A Basaif; Seik Weng Ng

doi:10.1107/S1600536811032855

. 2011 Aug 27;67(Pt 9):o2426. doi: 10.1107/S1600536811032855

4-(3-Methyl-5-phenyl-1H-pyrazol-1-yl)benzenesulfonamide

Abdullah M Asiri ^a,^b, Hassan M Faidallah ^a, Abdulrahman O Al-Youbi ^a, Salem A Basaif ^a, Seik Weng Ng ^c,^a,^*

PMCID: PMC3200729 PMID: 22059007

Abstract

With respect to the planar five-membered ring of the title compound, C₁₆H₁₅N₃O₂S, the phenyl ring is aligned at 47.0 (1)° and the phenylene ring at 37.6 (1)°. The amino group has the N atom in a pyramidal geometry; the group is a hydrogen-bond donor to the sulfonyl O atom of one molecule and to the pyrazole N atom of another molecule, resulting in the formation of a layer parallel to the bc plane.

Related literature

For the synthesis, see: Gosselin et al. (2006 ▶); Organ & Mayer (2003 ▶).

Experimental

Crystal data

C₁₆H₁₅N₃O₂S
M _r = 313.37
Monoclinic,
a = 28.2545 (8) Å
b = 11.9135 (4) Å
c = 9.3739 (3) Å
β = 91.016 (3)°
V = 3154.85 (17) Å³
Z = 8
Cu Kα radiation
μ = 1.91 mm⁻¹
T = 100 K
0.30 × 0.03 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.598, T _max = 0.945
6579 measured reflections
3137 independent reflections
2689 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.115
S = 1.03
3137 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.51 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032855/bt5609sup1.cif

e-67-o2426-sup1.cif^{(18KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032855/bt5609Isup2.hkl

e-67-o2426-Isup2.hkl^{(154KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811032855/bt5609Isup3.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
N1—H1⋯N3ⁱ	0.92 (2)	1.98 (2)	2.878 (2)	164 (2)
N1—H2⋯O1ⁱⁱ	0.86 (2)	2.07 (2)	2.930 (2)	177 (2)

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

Acknowledgments

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

supplementary crystallographic information

Comment

We are examining the medicinal properties of phenylpyrazolones of which the 4-benzenesulfamide derivative (Scheme I) is expected to show enhanced activity. As the inhibitory activity against cyclooxygenase-1 and cyclooxygenase-2 of the title compound (Scheme I) has been claimed in a number of patents, other researchers have attempted its synthesis in order to increase yield (Gosselin et al., 2006; Organ & Mayer, 2003). With respect to the planar five-membered ring, the phenyl ring is aligned at 47.0 (1) ° and the phenylene ring at 37.6 (1)°. The amino group is hydrogen bond donor to the sulfonyl O atom of one molecule and to the pyrazolyl N atom of another molecule to result in the formation of a layer parallel to the bc plane.

Experimental

1-Phenylbutan-1,3-dione (10 mmol) and 4-hydrazinobenzenesulfonamide hydrochloride (10 mmol) were heated in ethanol (50 ml) for 4 h; water was added to precipitate the product, which was collected and recrystallized from ethanol as light yellow crystals; m.p. 471–472 K.