2-Methyl-N-(4-methyl­benzo­yl)benzene­sulfonamide

B Thimme Gowda; Sabine Foro; P A Suchetan; Hartmut Fuess

doi:10.1107/S1600536810007440

. 2010 Mar 6;66(Pt 4):o747. doi: 10.1107/S1600536810007440

2-Methyl-N-(4-methylbenzoyl)benzenesulfonamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, P A Suchetan ^a, Hartmut Fuess ^b

PMCID: PMC2984015 PMID: 21580592

Abstract

The asymmetric unit of the title compound, C₁₅H₁₅NO₃S, contains two independent molecules. The conformations of the N—C bonds in the C—SO₂—NH—C(O) segments have gauche torsions with respect to the SO bonds. Further, the molecules are twisted at the S atoms with torsion angles of −53.1 (2) and 61.2 (2)° in the two molecules. The dihedral angles between the sulfonyl benzene rings and the —SO₂—NH—C—O segments are 86.0 (1) and 87.9 (1)°. Furthermore, the dihedral angles between the sulfonyl and the benzoyl benzene rings are 88.1 (1) and 83.5 (1)° in the two molecules. In the crystal, molecules are linked by N—H⋯O(S) hydrogen bonds.

Related literature

For background to our study of the effect of ring and the side-chain substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2009 ▶; 2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C₁₅H₁₅NO₃S
M _r = 289.34
Triclinic,
a = 10.9085 (8) Å
b = 12.1392 (9) Å
c = 12.3140 (9) Å
α = 118.846 (8)°
β = 95.965 (6)°
γ = 90.136 (6)°
V = 1417.98 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 299 K
0.48 × 0.44 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.896, T _max = 0.972
9669 measured reflections
5139 independent reflections
4302 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.105
S = 1.05
5139 reflections
371 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007440/bq2199sup1.cif

e-66-0o747-sup1.cif^{(25.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007440/bq2199Isup2.hkl

e-66-0o747-Isup2.hkl^{(251.6KB, hkl)}

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—H1N⋯O4ⁱ	0.82 (2)	2.18 (2)	2.978 (2)	165 (2)
N2—H2N⋯O2ⁱ	0.83 (2)	2.20 (2)	3.022 (2)	171 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

supplementary crystallographic information

Comment

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As a part of studying the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides (Gowda et al., 2009; 2010; Suchetan et al., 2010), the structure of 2-methyl-N-(4-methylbenzoyl)benzenesulfonamide (I) has been determined. The asymmetric unit of the structure contains two independent molecules (Fig. 1). The conformations of the N—C bonds in the C—SO₂—NH—C(O) segments have gauche torsions with respect to the SO bonds. Further, the conformations of the N—H bonds in the C—SO₂—NH—C(O) segments are anti to the C=O bonds, similar to those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009), 2-methyl-N-(3-methylbenzoyl)benzenesulfonamide (III) (Gowda et al., 2010) and N-(4-chlorobenzoyl)4-methyl- benzenesulfonamide (IV) (Suchetan et al., 2010).

The molecules are twisted at the S atoms with the torsion angles of -53.1 (2)° and 61.2 (2)° in the two independent molecules. The dihedral angles between the sulfonyl benzene rings and the —SO₂—NH—C—O segments are 86.0 (1)° (molecule 1) and 87.9 (1)° (molecule 2), compared to the values of 86.5 (1) in (II), 83.1 (1)° in (III), and 83.6 (1)° (molecule 1) and 81.0 (1)° (molecule 2) in (IV). Furthermore, the dihedral angles between the benzene rings are 88.1 (1)° (molecule 1) and 83.5 (1)° (molecule 2) in (I), compared to the values of 80.3 (1) in (II), 74.8 (1)° in (III), and 81.0 (1)° (molecule 1) and 76.3 (1)° (molecule 2) in (IV). The packing of molecules linked by of N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing a mixture of 4-methylbenzoic acid, 2-methylbenzenesulfonamide and phosphorous oxy chloride for 5 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid, 2-methyl-N-(4-methylbenzoyl)benzenesulfonamide obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried compound was recrystallized to the constant melting point. Plate like colorless single crystals of the title compound used in X-ray diffraction studies were grown from a slow evaporation of its toluene solution at room temperature.