N-Benzoyl-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536810011967

. 2010 Apr 10;66(Pt 5):o1039. doi: 10.1107/S1600536810011967

N-Benzoyl-4-methylbenzenesulfonamide

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

PMCID: PMC2979201 PMID: 21579100

Abstract

In the title compound, C₁₄H₁₃NO₃S, the N—H bond in is anti to the C=O bond. The dihedral angle between the two aromatic rings is 79.4 (1)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating C(4) chains.

Related literature

For related structures, see: Gowda et al. (2009 ▶); Suchetan et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₃NO₃S
M _r = 275.31
Orthorhombic,
a = 5.1723 (5) Å
b = 14.785 (1) Å
c = 17.431 (1) Å
V = 1332.99 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 299 K
0.40 × 0.20 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.908, T _max = 0.966
5515 measured reflections
2644 independent reflections
2388 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.084
S = 1.12
2644 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1025 Friedel pairs
Flack parameter: 0.18 (8)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED 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/S1600536810011967/bt5236sup1.cif

e-66-o1039-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011967/bt5236Isup2.hkl

e-66-o1039-Isup2.hkl^{(129.9KB, 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⋯O2ⁱ	0.83 (2)	2.08 (2)	2.905 (2)	175 (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; Suchetan et al., 2010a,b), the structure of N-(benzoyl)4-methylbenzenesulfonamide (I) has been determined. The conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009), N-(benzoyl)4-chlorobenzenesulfonamide (III)(Suchetan et al., 2010b) and N-(4-chlorobenzoyl)4-methylbenzenesulfonamide (IV)(Suchetan et al., 2010a).

The dihedral angles between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 76.5 (1)°, compared to the values of 86.5(0.1) in (II), 72.0 (1)° (molecule 1) and 77.3 (1)° (molecule 2) in (III), and 83.6 (1)° and 81.0 (1)° in the two independent molecules of (IV). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 79.4 (1)°, compared to the vlues of 80.3(0.1) in (II), 62.8 (1)° (molecule 1) and 78.6 (1)° (molecule 2) in (III), and 81.0 (1)° and 76.3 (1)° in the two molecules of (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 benzoic acid, 4-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, N-(benzoyl)4-methylbenzenesulfonamide 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.

Thick needle like colourless single crystals were grown from a slow evaporation of its toluene solution at room temperature.