2,2-Dichloro-N-(4-chloro­phenyl­sulfon­yl)­acetamide

B Thimme Gowda; Sabine Foro; P G Nirmala; B P Sowmya; Hartmut Fuess

doi:10.1107/S1600536808021715

. 2008 Jul 19;64(Pt 8):o1521. doi: 10.1107/S1600536808021715

2,2-Dichloro-N-(4-chlorophenylsulfonyl)acetamide

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

PMCID: PMC2962147 PMID: 21203229

Abstract

In the crystal structure of the title compound (N4CPSDCAA), C₈H₆Cl₃NO₃S, the conformations of the N—H and C=O bonds in the SO₂—NH—CO—C group are trans to each other, similar to those observed in 2,2-dichloro-N-(phenylsulfonyl)acetamide (NPSDCAA), 2,2-dichloro-N-(4-methylphenylsulfonyl)acetamide (N4MPSDCAA) and N-(4-chlorophenylsulfonyl)-2,2,2-trimethylacetamide (N4CPSTMAA), with similar bond parameters. The –SNHCOC– unit in N4CPSDCAA is essentially planar and makes a dihedral angle of 79.67 (5)° with the benzene ring, comparable to 79.75 (8)° in NPSDCAA, 81.02 (5)° in N4MPSDCAA and 82.2 (1)° in N4CPSTMAA. The molecules in N4CPSDCAA are linked into layers parallel to the (001) plane by intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2006 ▶); Gowda, Foro, Nirmala et al. (2008 ▶); Gowda, Foro, Sowmya et al. (2008 ▶).

Experimental

Crystal data

C₈H₆Cl₃NO₃S
M _r = 302.55
Orthorhombic,
a = 9.5909 (5) Å
b = 10.1750 (5) Å
c = 23.256 (1) Å
V = 2269.49 (19) Å³
Z = 8
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 299 (2) K
0.32 × 0.28 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.745, T _max = 0.926
10378 measured reflections
2309 independent reflections
1642 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.073
S = 1.08
2309 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021715/ci2630sup1.cif

e-64-o1521-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021715/ci2630Isup2.hkl

e-64-o1521-Isup2.hkl^{(113.6KB, 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	0.86	1.97	2.814 (2)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the crystal structures of N-(aryl)-sulfonamides and substituted amides, in the present work, the structure of N-(4-chlorophenylsulfonyl)-2,2-dichloroacetamide (N4CPSDCAA) has been determined (Gowda et al., 2003, 2006; Gowda, Foro, Nirmala et al., 2008; Gowda, Foro, Sowmya et al., 2008). The conformations of the N—H and C═O bonds of the SO₂—NH—CO—C group in N4CPSDCAA are trans to each other (Fig. 1), similar to those observed in N-(phenylsulfonyl)-2,2-dichloroacetamide (NPSDCAA), N-(4-methylphenylsulfonyl)-2,2-dichloroacetamide (N4MPSDCAA) (Gowda, Foro, Nirmala et al., 2008) and (4-chlorophenylsulfonyl)-2,2,2- trimethylacetamide (N4CPSTMAA) (Gowda, Foro, Sowmya et al., 2008). The bond parameters in N4CPSDCAA are similar to those in NPSDCAA, N4MPSDCAA, N4CPSTMAA (Gowda, Foro, Nirmala et al., 2008; Gowda, Foro, Sowmya et al., 2008), N-(aryl)-2,2-dichloro- acetamides (Gowda et al., 2006) and 4-chlorobenzenesulfonamide (Gowda et al., 2003).

The packing diagram of N4CPSDCAA showing the N—H···O hydrogen bonds (Table 1) involved in the formation of layers parallel to the (0 0 1) plane is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing 4-chlorobenzenesulfonamide (0.10 mole) with excess dichloroacetyl 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 precipitated 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 characterized by recording its infrared and NMR spectra. Single crystals of the title compound used for X-ray diffraction studies were obtained by slow evaporation of an ethanolic solution.