N-(4-Chloro­phenyl­sulfon­yl)-2-methyl­propanamide

P G Nirmala; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811031394

. 2011 Aug 6;67(Pt 9):o2274. doi: 10.1107/S1600536811031394

N-(4-Chlorophenylsulfonyl)-2-methylpropanamide

P G Nirmala ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3200645 PMID: 22064939

Abstract

In the crystal structure of the title compound, C₁₀H₁₂ClNO₃S, the N—C bond in the C—SO₂—NH—C segment has a gauche torsion with respect to the S=O bonds. The molecule is twisted at the S atom with a C—S—N—C torsion angle of −62.3 (3)°. The benzene ring and the SO₂—NH—CO—C segment form a dihedral angle of 89.3 (1)°. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds into inversion dimers.

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 studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004 ▶), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003 ▶) and on N-(arylsulfonyl)-amides, see: Gowda et al. (2008 ▶); Shakuntala et al. (2011 ▶).

Experimental

Crystal data

C₁₀H₁₂ClNO₃S
M _r = 261.72
Triclinic,
a = 6.207 (1) Å
b = 10.395 (3) Å
c = 10.497 (3) Å
α = 70.150 (2)°
β = 79.160 (2)°
γ = 86.010 (2)°
V = 625.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 293 K
0.46 × 0.20 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009 ▶) T _min = 0.815, T _max = 0.964
3846 measured reflections
2476 independent reflections
1842 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.126
S = 1.19
2476 reflections
148 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 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/S1600536811031394/nc2243sup1.cif

e-67-o2274-sup1.cif^{(16KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031394/nc2243Isup2.hkl

e-67-o2274-Isup2.hkl^{(121.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811031394/nc2243Isup3.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⋯O1ⁱ	0.84 (2)	2.08 (2)	2.912 (4)	169 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the University Grants Commission, Government of India, New Delhi, for a one time grant under its BSR scheme.

supplementary crystallographic information

Comment

The molecular structures of sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976). The propensity for hydrogen bonding in the solid state, due to the presence of various hydrogen bond donors and acceptors gives rise to polymorphism (Yang & Guillory, 1972). The hydrogen bonding preferences of sulfonamides has also been studied (Adsmond & Grant, 2001). The nature and position of substituents play a significant role on the crystal structures of this class of compounds. As part of our work on the effects of substituents on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Gowda et al., 2003) and N-(arylsulfonyl)-acetamides (Gowda et al., 2008, Shakuntala et al., 2011), in the present work, the crystal structure of N-(4-chlorophenylsulfonyl)-2,2-dimethylacetamide (I) has been determined. The N—C bond in the C—SO₂—NH—C segment has gauche torsion with respect to the S═O bonds. The molecule is twisted at the S-atom with a C—S—N—C torsion angle of -62.3 (3)°, compared to the values of -72.5 (2)° in N-(4-chlorophenylsulfonyl)-2,2-dichloroacetamide (II) (Gowda et al., 2008) and N-(2-chlorophenylsulfonyl)- 2,2-dimethylacetamide (III)(Shakuntala et al., 2011).

Further, the dihedral angle between the benzene ring and the SO₂—NH—CO—C segment in (I) is 89.3 (1)°, compared to the values of 79.7 (1)° in (II) and 87.4 (1)° in (III).

In the crystal structure, the moleucles are connected into centrosymmetrically dimers by intermolecular N–H···O hydrogen bonding (Table 1). Part of the crystal structure is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing 4-chlorobenzenesulfonamide (0.10 mole) with an excess of 2,2-dimethylacetyl chloride (0.20 mole) for about an 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 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.