N-(2-Chloro­phenyl­sulfon­yl)-2-methyl­propanamide

K Shakuntala; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811004284

. 2011 Feb 9;67(Pt 3):o595. doi: 10.1107/S1600536811004284

N-(2-Chlorophenylsulfonyl)-2-methylpropanamide

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

PMCID: PMC3052113 PMID: 21522354

Abstract

In the title compound, C₁₀H₁₂ClNO₃S, the amide H atom is syn with respect to the ortho-chloro group in the benzene ring and the C—S—N—C torsion angle is 64.35 (16)°. The benzene ring and the SO₂—NH—CO—C segment form a dihedral angle of 87.4 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

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 the hydrogen-bonding characteristics of sulfonamides, see; Adsmond & Grant (2001 ▶). For the effect of substituents on the crystal structures of sulfonoamides, see: Gowda et al. (2008 ▶, 2009 ▶, 2010 ▶)

Experimental

Crystal data

C₁₀H₁₂ClNO₃S
M _r = 261.72
Triclinic,
a = 8.365 (1) Å
b = 8.719 (1) Å
c = 9.143 (1) Å
α = 92.74 (1)°
β = 104.22 (1)°
γ = 108.75 (1)°
V = 606.24 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 293 K
0.45 × 0.35 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.814, T _max = 0.851
4031 measured reflections
2481 independent reflections
2200 reflections with I > 2σ(I)
R _int = 0.011

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.102
S = 1.04
2481 reflections
149 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.27 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/S1600536811004284/ds2091sup1.cif

e-67-0o595-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004284/ds2091Isup2.hkl

e-67-0o595-Isup2.hkl^{(121.9KB, 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⋯O1ⁱ	0.84 (2)	2.14 (2)	2.976 (2)	174 (2)

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Symmetry code: (i) Inline graphic .

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 molecular 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 can give rise to polymorphism (Yang & Guillory, 1972). The hydrogen bonding preferences of sulfonamides has also been investigated (Adsmond & Grant, 2001). The nature and position of substituents play a significant role on the crystal structures of N-(aryl)sulfonoamides (Gowda et al., 2008, 2009, 2010). As a part of studying the substituent effects on the structures of this class of compounds, the structure of N-(2-chlorophenylsulfonyl)-2,2-dimethylacetamide (I) has been determined. The conformations of the N—H and C=O bonds of the SO₂—NH—CO—C segment in the structure are anti to each other (Fig. 1), similar to that observed in N-(phenylsulfonyl)-acetamide (II) (Gowda et al., 2010), 2,2-dimethyl-N-(phenylsulfonyl)- acetamide (III)(Gowda et al., 2009) and 2,2-dichloro-N- (phenylsulfonyl)-acetamide (IV) (Gowda et al., 2008).

The molecule in (I) is bent at the S-atom with a C1—S1—N1—C7 torsion angle of 64.4 (2)°, compared to the values of -58.8 (4)° in (II), 67.1 (3)° in (III) and -66.3 (3)° in (IV). Further, the dihedral angle between the benzene ring and the SO2—NH—CO—C group in (I) is 87.4 (1)°, compared to the values of 89.0 (2)° in (II), 87.4 (1)° in (III) and 79.8 (1)° in (IV),

In the crystal structure, the intermolecular N–H···O hydrogen bonds (Table 1) link the molecules through inversion-related dimers into zigzag chains in the bc-plane. 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 2,2-dimethylacetyl 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.

Prism like colorless 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.