N-(2-Chloro­benzo­yl)-4-methyl­benzene­sulfonamide

P A Suchetan; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812015681

. 2012 Apr 18;68(Pt 5):o1403. doi: 10.1107/S1600536812015681

N-(2-Chlorobenzoyl)-4-methylbenzenesulfonamide

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

PMCID: PMC3344529 PMID: 22590291

Abstract

In the title compound, C₁₄H₁₂ClNO₃S, the C=O bond is syn to the Cl substituent in the adjacent benzene ring. The C—S—N—C torsion angle is −80.6 (6)°. The chlorobenzoyl ring is disordered and was refined using a split model [occupancy ratio 0.537 (3):0.463 (3)]. In the crystal, molecules are linked by pairs of N—H⋯O(S) 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: Gowda et al. (2000 ▶, 2007 ▶), of N-(substitutedbenzoyl)-arylsulfonamides, see: Gowda et al. (2010 ▶), of N-chloroarylamides, see: Jyothi & Gowda (2004 ▶) and of N-bromoarylsulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO₃S
M _r = 309.76
Monoclinic,
a = 25.079 (4) Å
b = 8.1963 (7) Å
c = 18.397 (3) Å
β = 131.77 (1)°
V = 2820.4 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 293 K
0.48 × 0.20 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.822, T _max = 0.935
5253 measured reflections
2432 independent reflections
1623 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.071
wR(F ²) = 0.115
S = 1.16
2432 reflections
216 parameters
15 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.31 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 datablock(s) I, global. DOI: 10.1107/S1600536812015681/nc2273sup1.cif

e-68-o1403-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015681/nc2273Isup2.hkl

e-68-o1403-Isup2.hkl^{(119.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015681/nc2273Isup3.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	0.86	2.02	2.867 (4)	169

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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 faculty.

supplementary crystallographic information

Comment

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000, 2007), N-(substitutedbenzoyl)-arylsulfonamides (Gowda et al., 2010), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(2-chlorobenzoyl)-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 that observed in i>N-(2-chlorobenzoyl)-4-chlorobenzenesulfonamide (II)(Gowda et al., 2010). Further, the conformation of the C=O bond in the C—SO₂—NH—C(O) segment of (I) is syn to the ortho-Cl in the benzoyl ring, similar to that observed between in (II).

The molecules are twisted at the S atom with the torsional angle of -80.6 (6)°, compared to that of 65.7 (2)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 65.0 (5)°, compared to the value of 88.5 (1)° in (II).

Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 66.1 (2)°, compared to the value of 58.2 (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 2-chlorobenzoic acid, 4-methylbenzenesulfonamide and phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid 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 the solvent in its toluene solution at room temperature.