4-Methyl-N-(4-methyl­phenyl­sulfon­yl)-N-[4-(4-methyl­phen­yl)-1,3-thia­zol-2-yl]benzene­sulfonamide

Rubén M Carballo; Simón Hernández-Ortega; Nayely Padilla-Montaño; Reyna Reyes-Martínez; Gumersindo Mirón-López

doi:10.1107/S1600536813032145

. 2013 Dec 4;70(Pt 1):o6–o7. doi: 10.1107/S1600536813032145

4-Methyl-N-(4-methylphenylsulfonyl)-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide

Rubén M Carballo ^a, Simón Hernández-Ortega ^b, Nayely Padilla-Montaño ^a, Reyna Reyes-Martínez ^a, Gumersindo Mirón-López ^a,^*

PMCID: PMC3914048 PMID: 24526999

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₂₄H₂₂N₂O₄S₃. In each, the sulfonamide N atoms reveal nearly a trigonal-planar geometry with two S atoms of the O=S=O groups and one C atom of the thiazole ring; the angles around the N atoms are between 117.00 (13) and 123.86 (9)°. The methylphenylsulfonyl groups are in anti conformations, forming dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)° with the trigonal S—N—S planes in the two molecules. The thiazole groups are rotated around the C—N bonds and are almost perpendicular to the S—N—S plane [dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)°]. In the crystal, pairs of C—H⋯O interactions, with the O atoms of the sulfonamide groups as acceptors, link each of the independent molecules into inversion dimers.

Related literature

For bioactive sulfonamide compounds, see: Annadurai et al. (2012 ▶); Farag et al. (2012 ▶); Xiao-Long et al. (2009 ▶). graphic file with name e-70-000o6-scheme1.jpg

Experimental

Crystal data

C₂₄H₂₂N₂O₄S₃
M _r = 498.61
Triclinic,
a = 8.3322 (2) Å
b = 12.0630 (3) Å
c = 23.5756 (6) Å
α = 84.615 (1)°
β = 87.022 (1)°
γ = 85.482 (1)°
V = 2349.46 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 298 K
0.44 × 0.38 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
18770 measured reflections
8539 independent reflections
6755 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.104
S = 0.98
8539 reflections
602 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813032145/kp2458sup1.cif

e-70-000o6-sup1.cif^{(35.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032145/kp2458Isup2.hkl

e-70-000o6-Isup2.hkl^{(467.7KB, hkl)}

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29B⋯O3ⁱ	0.96	2.54	3.148 (3)	122
C50—H50C⋯O5ⁱⁱ	0.96	2.47	3.397 (3)	162

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

Acknowledgments

This work was funded by PIFI-2011. The authors from the Universidad Autónoma de Yucatán are grateful to the Instituto de Química, Universidad Nacional Autónoma de México, for permission to the perform the X-ray analysis. We thank Br Hector Peniche Pavia for his participation in the synthetic procedure.

supplementary crystallographic information

1. Comment

Sulfonamide thiazoles are structural units frequently found as parts of skeletons of bioactive compounds including antimicrobials agents (Annadurai et al., 2012), anticonvulsant agents (Farag et al., 2012) or inhibitors of Nek2/Hec1 (Xiao-Long et al., 2009). Due to the importance of thiazole derivatives, we synthesized (I) N-[4-(p-tolyl)thiazol-2-yl]-4-methyl-N-(4- methylphenylsulfonyl)benzenesulfonamide, and discuss the geometry of the molecule and its conformation. The compound was obtained by the reaction of 4-p-tolyl-thiazol-2-ylamine in an excess of 4-methyl-benzenesulfonilchloride.

The title compound I crystallized with two independent molecules (A and B) in the asymmetric unit (Fig. 1). The geometries around the N13 and N42 atoms are almost trigonal planar with bonding angles ranging from 117.00° to 123.86°. The sulfonamide nitrogen atoms are bonded to a carbon atom of the thiazole ring and two sulfur atoms of the O=S=O groups, the distances of the C—N bonds are of 1.426 (2) Å for both molecules, and the N—S bonds are between 1.6902 (16) and 1.7040 (17) Å. The thiazole rings are rotated around C—N bond foming the dihedral angles of 85.57 (5)° and 89.28 (5)° with the planes O2S—N—SO2, in molecule A and B, respectively. The methylphenylsulfonyl groups keep anti-conformations forming a dihedral angles of 78.00 (7)°, 72.53 (5)° and 77.09 (6)°, 71.50 (7)° with the trigonal plane S—N—S, in the molecules A and B, respectively. The sulfur atoms of the sulfonamide groups are in a distorted tetrahedral geometry with angles varying from 103.43 (8) to 121.39 (1)°, and S=O bonds from 1.4175 (15) to 1.42358 (14) Å. The thiazole and p-tolyl groups in the molecule B exhibit a coplanar arrangement, while in the molecule A these moieties form an angle of 17.20 (7)° between these planes. Each independent molecule form a dimer arrangement by C—H···O interactions (Table 1, Fig. 2). The crystal packing in the title compound is stabilized by the C—H···O=S intermolecular interactions.

2. Experimental

A mixture of 4-p-tolyl-thiazol-2-ylamine (200 mg, 1.05 mmol), 4-methyl-benzenesulfonyl chloride (600 mg, 3.15 mmol), triethyl-amine (0.293 mL, 2.1 mmol) and dimethyl-pyridin-4-yl-amine (12.8 mg, 0.105 mmol) in dichloromethane (0.1 M, 11 mL) was stirred in a 50 mL round bottom flask at room temperature for 12 h, and the reaction was monitored by TLC. Then, the reaction solution was quenched by addition of water with stirring and extracted with dichloromethane. The organic layers were dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was crystallized from acetone to yield single crystals of the title compound (314 mg, 0.63 mmol, 60%).