N-(2-Chloro­phenyl­sulfon­yl)acetamide

K Shakuntala; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811012785

. 2011 Apr 13;67(Pt 5):o1097. doi: 10.1107/S1600536811012785

N-(2-Chlorophenylsulfonyl)acetamide

K Shakuntala ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3089153 PMID: 21754417

Abstract

The asymmetric unit of the title compound, C₈H₈ClNO₃S, contains two independent molecules in which the C—S—N—C torsion angles are −71.7 (3) and 61.2 (3)°. The benzene rings and the SO₂—NH—CO—C segments form dihedral angles of 80.2 (1) and 88.1 (2)° in the two independent molecules. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains in the b-axis direction.

Related literature

For the sulfanilamide moiety in sulfonamide drugs, see; Maren (1976 ▶). For its ability to form hydrogen bonds in the solid state, see; Yang & Guillory (1972 ▶). For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001 ▶). For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000 ▶), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶) and of N-(substituted phenylsulfonyl)-substituted amides, see: Gowda et al. (2010 ▶).

Experimental

Crystal data

C₈H₈ClNO₃S
M _r = 233.66
Monoclinic,
a = 11.215 (2) Å
b = 9.393 (2) Å
c = 19.655 (3) Å
β = 98.61 (2)°
V = 2047.2 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 293 K
0.16 × 0.16 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.916, T _max = 0.978
8327 measured reflections
4168 independent reflections
1942 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.099
S = 0.95
4168 reflections
261 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 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/S1600536811012785/vm2086sup1.cif

e-67-o1097-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012785/vm2086Isup2.hkl

e-67-o1097-Isup2.hkl^{(204.3KB, 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⋯O3ⁱ	0.85 (2)	2.03 (2)	2.848 (4)	162 (3)
N2—H2N⋯O6ⁱⁱ	0.84 (2)	1.96 (2)	2.788 (4)	172 (3)

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

Acknowledgments

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

supplementary crystallographic information

Comment

The structures of sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976). The affinity for hydrogen bonding in the solid state due to the presence of various hydrogen bond donors and acceptors give rise to polymorphism (Yang & Guillory, 1972). The hydrogen bonding preferences of sulfonamides have also been investigated (Adsmond & Grant, 2001). The nature and position of substituents play a significant role on the crystal structures of N-(aryl)-amides and N-(aryl)- sulfonoamides (Gowda et al., 2000, 2007, 2010). As a part of studying the effects of substituents on the structures of this class of compounds, the structure of N-(2-chlorophenylsulfonyl)-acetamide (I) has been determined (Fig. 1). The asymmetric unit of (I) contains two independent molecules. The rms deviation of a fit of the inverted molecule 2 (containing Cl2) on molecule 1 (containing Cl1) is 0.278 Å for 12 fitted atoms (excluding H atoms and O atoms SO₂ groups). In one of the molecules, the conformation of the N—C bond in the C—SO₂—NH—C(O) segment has gauche torsions with respect to the S═O bonds, the torsional angles being C15—N2—S2—O5 = -54.0 (4)° and C15—N2—S2—O4 = 176.4 (3)°. The conformations of the N—H and C=O bonds of these segments are anti to each other, similar to that observed in N-(phenylsulfonyl)-acetamide (II) (Gowda et al., 2010).

The molecules in (I) are bent at the S-atom with a C—S—N—C torsion angles of -71.7 (3)° and 61.2 (3)° in the two independent molecules, compared to the values of -58.8 (4)° in (II),

Further, the dihedral angles between the benzene rings and the SO₂—NH—CO—C groups in (I) are 80.2 (1)° in molecule 1 and 88.1 (2)° in molecule 2, compared to the values of 89.0 (2)° in (II).

In the crystal structure, the intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into chains in the b-direction. Part of the crystal structure is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing 2-chlorobenzenesulfonamide (0.10 mole) with an excess of acetyl chloride (0.20 mole) for one hour on a water bath. The reaction mixture was cooled and poured into ice cold water. The resulting solid was separated, washed thoroughly with water and dissolved in warm dilute sodium hydrogen carbonate solution. The title compound was reprecipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. The purity of the compound was checked by determining its melting point. It was further characterized by recording its infrared spectra.

Plate like colourless single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of an ethanolic solution of the compound.