2,2,2-Trimethyl-N-(phenyl­sulfon­yl)­acetamide

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

doi:10.1107/S1600536808019983

. 2008 Jul 5;64(Pt 8):o1410. doi: 10.1107/S1600536808019983

2,2,2-Trimethyl-N-(phenylsulfonyl)acetamide

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

PMCID: PMC2962045 PMID: 21203130

Abstract

The N—H and C=O bonds of the SO₂—NH—CO group in the title compound, C₁₁H₁₅NO₃S, are anti to each other. The asymmetric unit contains two independent molecules. The benzene rings form dihedral angles of 83.19 (8) and 76.01 (10)° with the mean planes of the C₂NOS fragments. The molecules are linked into chains parallel to the b axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda, Nayak et al. (2007 ▶); Gowda, Foro & Fuess (2007 ▶); Gowda, Kožíšek et al. (2007 ▶); Gowda, Svoboda et al. (2007 ▶).

Experimental

Crystal data

C₁₁H₁₅NO₃S
M _r = 241.30
Monoclinic,
a = 12.3045 (9) Å
b = 11.3016 (7) Å
c = 18.466 (1) Å
β = 103.117 (6)°
V = 2500.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 299 (2) K
0.50 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.885, T _max = 0.906
15589 measured reflections
4985 independent reflections
3639 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.167
S = 1.16
4985 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.40 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/S1600536808019983/rz2222sup1.cif

e-64-o1410-sup1.cif^{(23.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019983/rz2222Isup2.hkl

e-64-o1410-Isup2.hkl^{(244.2KB, 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⋯O4ⁱ	0.86	2.09	2.946 (3)	171
N2—H2N⋯O2ⁱⁱ	0.86	2.32	3.094 (3)	151

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Symmetry codes: (i) Inline graphic ; (ii) .

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-(phenylsulfonyl)-2,2,2-trimethylacetamide (NPSTMAA) has been determined. The conformations of the N—H and C=O bonds of the SO₂—NH—CO group in NPSTMAA are anti to each other (Fig. 1). The asymmetric unit of the structure contains two molecules. The bond parameters in NPSTMAA are similar to those in N-(aryl)-2,2,2-trimethylacetamides (Gowda, Foro & Fuess, 2007; Gowda, Kožíšek et al., 2007; Gowda, Svoboda et al., 2007) and benzenesulfonamide (Gowda, Nayak et al., 2007). The benzene rings form dihedral angles of 83.19 (8) and 76.01 (10)° with the mean planes of the C₂NOS fragments. A packing diagram of NPSTMAA molecules showing the formation of molecular chains parallel to the b axis through N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing benzenesulfonamide (0.10 mol) in excess pivalyl chloride (0.20 mol) 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 a 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 suitable for X-ray diffraction studies were obtained by slow evaporation of an ethanol solution.