N-(2-Chloro­phenyl­sulfon­yl)-2,2-dimethyl­propanamide

K Shakuntala; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811017429

. 2011 May 14;67(Pt 6):o1400. doi: 10.1107/S1600536811017429

N-(2-Chlorophenylsulfonyl)-2,2-dimethylpropanamide

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

PMCID: PMC3120501 PMID: 21754785

Abstract

In the title compound, C₁₁H₁₄ClNO₃S, the C—S—N—C torsion angle is −61.69 (17)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur, generating R ₂ ²(8) loops.

Related literature

For the sulfanilamide moiety in sulfonamide drugs, see: Maren (1976 ▶). For the ability of sulfonamides 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)-methanesulfonamides, see: Gowda et al. (2007 ▶). For related structures, see: Gowda et al. (2008 ▶); Shakuntala et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₁₁H₁₄ClNO₃S
M _r = 275.74
Triclinic,
a = 8.785 (1) Å
b = 8.914 (1) Å
c = 9.313 (1) Å
α = 103.12 (1)°
β = 107.14 (1)°
γ = 94.20 (1)°
V = 670.98 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 293 K
0.44 × 0.40 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.831, T _max = 0.852
4355 measured reflections
2730 independent reflections
2321 reflections with I > 2σ(I)
R _int = 0.012

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.107
S = 1.06
2730 reflections
158 parameters
1 restraint
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/S1600536811017429/tk2742sup1.cif

e-67-o1400-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017429/tk2742Isup2.hkl

e-67-o1400-Isup2.hkl^{(134KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811017429/tk2742Isup3.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	0.83 (2)	2.22 (2)	3.042 (2)	178 (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 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 investigated (Adsmond & Grant, 2001). The nature and position of substituents in N-(aryl)sulfonoamides play a significant role on their crystal structures. As a part of a study of the substituent effects upon their crystal structures (Gowda et al., 2007, 2008; Shakuntala et al., 2011a,b), in the present work, the crystal structure of N-(2-chlorophenylsulfonyl)-2,2,2-trimethylacetamide (I) has been determined. The N—H and C═O bonds in the SO₂—NH—CO—C segment of (I) are anti to each other (Fig. 1), similar to that observed in N-(2-methylphenylsulfonyl)-2,2,2- trimethylacetamide (II) (Shakuntala et al., 2011a), N-(phenylsulfonyl)-2,2,2-trimethylacetamide (III) (Gowda et al., 2008) and N-(2-chlorophenylsulfonyl)-acetamide (IV) (Shakuntala et al., 2011b). Further, the amide hydrogen is syn to the ortho-chloro group in the benzene ring.

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 -61.7 (2) °, compared to the values of -65.4 (2) ° in (II), -64.5 (3) ° in (III), and -71.7 (3) ° and 61.2 (3) ° in the two independent molecules of (IV).

In the crystal structure, the pairs of intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into inversion-related dimers; a view of the crystal packing is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing 2-chlorobenzenesulfonamide (0.10 mole) with an excess of pivalyl 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 re-precipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. Colorless prisms of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of an ethanolic solution of the compound.