N-(4-Chloro­phenyl­sulfon­yl)-2,2,2-tri­methyl­acetamide

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

doi:10.1107/S1600536808017583

. 2008 Jun 19;64(Pt 7):o1279. doi: 10.1107/S1600536808017583

N-(4-Chlorophenylsulfonyl)-2,2,2-trimethylacetamide

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

PMCID: PMC2961760 PMID: 21202911

Abstract

In the crystal structure of the title compound (N4CPSTMAA), C₁₁H₁₄ClNO₃S, the conformations of the N—H and C=O bonds in the amide group are anti to each other, similar to those observed in N-phenylsulfonyl-2,2,2-trimethylacetamide (NPSTMAA) and 2,2,2-trimethyl-N-(4-methylphenylsulfonyl)acetamide (N4MPSTMAA). The bond parameters in N4CPSTMAA are similar to those in NPSTMAA, N4MPSTMAA, N-aryl-2,2,2-trimethylacetamides and 4-chlorobenzenesulfonamide. The –SNHCOC– unit including the amide group is essentially planar and makes a dihedral angle of 82.2 (1)° with the benzene ring, comparable to the values of 79.1 (1) and 71.2 (1)° in NPSTMAA and N4MPSTMAA, respectively. The molecules in N4CPSTMAA are linked into a chain by intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2007 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

C₁₁H₁₄ClNO₃S
M _r = 275.74
Triclinic,
a = 6.034 (2) Å
b = 10.695 (2) Å
c = 11.134 (2) Å
α = 67.13 (2)°
β = 79.76 (2)°
γ = 88.46 (2)°
V = 650.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 299 (2) K
0.50 × 0.24 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.806, T _max = 0.948
7016 measured reflections
2595 independent reflections
1901 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.129
S = 1.10
2595 reflections
157 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); 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/S1600536808017583/is2303sup1.cif

e-64-o1279-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017583/is2303Isup2.hkl

e-64-o1279-Isup2.hkl^{(127.4KB, 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⋯O2ⁱ	0.82 (3)	2.19 (3)	2.986 (3)	165 (3)

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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

In the present work, as part of a study of the substituent effects on the solid state geometries of N-(aryl)-sulfonamides and substituted amides, the structure of N-(4-chlorophenylsulfonyl)-2,2,2-trimethylacetamide (N4CPSTMAA) has been determined (Gowda et al., 2003, 2007, 2008a,b). The conformations of the N—H and C=O bonds of the SO₂—NH—CO—C group in N4CPSTMAA are anti to each other (Fig. 1), similar to those observed in N-(phenylsulfonyl)-2,2,2-trimethylacetamide (NPSTMAA) and (4-methylphenylsulfonyl)-2,2,2-trimethylacetamide (N4MPSTMAA) (Gowda et al., 2008a,b). The bond parameters in N4CPSTMAA are similar to those in NPSTMAA, N4MPSTMAA, N-(aryl)-2,2,2-trimethylacetamides (Gowda et al., 2007) and 4-chlorobenzenesulfonamide (Gowda et al., 2003). The packing diagram of N4CPSTMAA molecules showing the hydrogen bonds N—H···O (Table 1) involved in the formation of molecular chains is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing 4-chlorobenzenesulfonamide with excess pivalyl chloride 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 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 were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.