N-(3-Chloro­benzo­yl)-2-methyl­benzene­sulfonamide

P A Suchetan; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811050574

. 2011 Nov 30;67(Pt 12):o3489. doi: 10.1107/S1600536811050574

N-(3-Chlorobenzoyl)-2-methylbenzenesulfonamide

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

PMCID: PMC3239113 PMID: 22199961

Abstract

In the title compound, C₁₄H₁₂ClNO₃S, the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond. Further, the C=O bond and the meta-Cl atom in the benzoyl ring are also anti to each other. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (2004 ▶), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004 ▶), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003 ▶), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2010 ▶) and on N-chloroarylamides, see: Gowda et al. (1996 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO₃S
M _r = 309.76
Monoclinic,
a = 18.043 (2) Å
b = 12.046 (1) Å
c = 15.596 (2) Å
β = 118.77 (2)°
V = 2971.3 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 293 K
0.40 × 0.36 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.856, T _max = 0.882
5996 measured reflections
3024 independent reflections
2463 reflections with I > 2σ(I)
R _int = 0.012

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.113
S = 1.03
3024 reflections
185 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD); data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶; 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 datablock(s) I, global. DOI: 10.1107/S1600536811050574/bt5728sup1.cif

e-67-o3489-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050574/bt5728Isup2.hkl

e-67-o3489-Isup2.hkl^{(148.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050574/bt5728Isup3.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—H1N⋯O2ⁱ	0.82 (2)	2.06 (2)	2.876 (2)	174 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to the faculty.

supplementary crystallographic information

Comment

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2004), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2003); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2010) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, the crystal structure of N-(3-Chlorobenzoyl)- 2-methylbenzenesulfonamide (I) has been determined (Fig.1).

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 that observed in N-(benzoyl)-2-methylbenzenesulfonamide (II)(Suchetan et al., 2010). Further, the conformation between the C=O bond and the meta-Cl in the benzoyl ring is also anti to each other.

The molecules are twisted at the S atom with the torsional angle of 66.9 (2)°, compared to the value of 68.8 (4)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 82.4 (1)°, compared to the value of 84.8 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°, compared to the value of 73.9 (1)° in (II).

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 3-chlorobenzoic acid (0.02 mole), 2-methylbenzenesulfonamide (0.02 mole) and excess phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(3-chlorobenzoyl)2-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. It was filtered, dried and recrystallized.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution at room temperature.