1-(4-Methyl­phen­yl)-3-phenyl-1H-pyrazol-5-yl 4-nitro­benzene­sulfonate

Solange M S V Wardell; Edward R T Tiekink; James L Wardell

doi:10.1107/S1600536812010598

. 2012 Mar 17;68(Pt 4):o1086–o1087. doi: 10.1107/S1600536812010598

1-(4-Methylphenyl)-3-phenyl-1H-pyrazol-5-yl 4-nitrobenzenesulfonate

Solange M S V Wardell ^a, Edward R T Tiekink ^b,^*, James L Wardell ^c,^‡

PMCID: PMC3344041 PMID: 22589950

Abstract

In the title molecule, C₂₂H₁₇N₃O₅S, the pyrazole ring is planar (r.m.s. deviation = 0.018 Å) and forms dihedral angles of 21.45 (10) and 6.96 (10)° with the N- and C-bound benzene rings, respectively. Supramolecular layers in the bc plane are formed in the crystal via C—H⋯O and π–π interactions involving the sulfonamide benzene ring interacting with the N- and C-bound benzene rings [centroid–centroid distances = 3.790 (2) and 3.730 (2) Å, respectively]. The crystal studied was found to be a merohedral twin (twin law 1 0 0.678, 0 -1 0, 0 0 -1), the fractional contribution of the minor component being approximately 36%.

Related literature

For related structures and background references to pyrazoles, see: Wardell et al. (2012 ▶); Baddeley et al. (2012 ▶). For the synthesis, see: Galoyan et al. (1969 ▶). For the treatment of twinned diffraction data, see: Spek (2009 ▶).

Experimental

Crystal data

C₂₂H₁₇N₃O₅S
M _r = 435.46
Monoclinic,
a = 13.5339 (12) Å
b = 10.4827 (10) Å
c = 14.9303 (13) Å
β = 111.975 (3)°
V = 1964.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 120 K
0.58 × 0.38 × 0.04 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.620, T _max = 0.746
4454 measured reflections
4454 independent reflections
3951 reflections with I > 2σ(I)

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.179
S = 1.19
4454 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; 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/S1600536812010598/hb6674sup1.cif

e-68-o1086-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010598/hb6674Isup2.hkl

e-68-o1086-Isup2.hkl^{(213.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010598/hb6674Isup3.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
C5—H5⋯O4ⁱ	0.95	2.50	3.387 (5)	155

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR/MOHE/SC/12) is gratefully acknowledged.

supplementary crystallographic information

Comment

The structure of the title compound is now reported in continuation of related structural studies (Wardell et al. 2012; Baddeley et al., 2012).

In the title compound, Fig. 2, the pyrazole ring is planar with a r.m.s. deviation for the fitted atoms of 0.018 Å; the maximum deviations from this plane are 0.015 (1) Å (for the N1 atom) and -0.015 (1) Å (C8). The N– and C-bound benzene rings are inclined to this plane forming dihedral angles of 21.45 (10) and 6.96 (10)°, respectively; the dihedral angle between the benzene rings is 20.42 (10)° consistent with a non-planar molecule.

In the crystal, molecules are assembled into supramolecular layers in the bc plane via C—H···O, Table 1, and π—π interactions involving the sulfonamide benzene ring interacting with the N– and C-bound benzene rings {ring centroid···ring centroid distances = 3.790 (2) Å [angle of inclination = 0.96 (17)° for symmetry operation 1 - x, 1 - y, -z] and 3.730 (2) Å [angle of inclination = 10.02 (17)° for symmetry operation 1 - x, -1/2 + y, -1/2 - z], respectively}, Fig. 3. Layers stack along the a axis with no specific interactions between them, Fig. 4.

Experimental

A solution of 4-MeC₆H₄NHNH₂.HCl (2 mmol) and PhCOCH₂CONHPh (2 mmol) in Me₂CO (20 ml) was refluxed for 1 h. A solution of 4-nitrobenzenesulfonyl chloride (2 mmol) in Me₂CO (10 ml) was added and the reaction mixture was refluxed for 30 min, rotary evaporated and the residue was recrystallized twice from EtOH as yellow plates, M.pt: 445–447 K.