2,2,2-Trimethyl-N-(4-methyl­phenyl­sulfon­yl)acetamide

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

doi:10.1107/S1600536808017790

. 2008 Jun 19;64(Pt 7):o1274. doi: 10.1107/S1600536808017790

2,2,2-Trimethyl-N-(4-methylphenylsulfonyl)acetamide

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

PMCID: PMC2961849 PMID: 21202906

Abstract

The bond parameters and conformations of the N—H and C=O bonds of the SO₂—NH—CO—C group in the title compound, C₁₂H₁₇NO₃S, anti to each other, are similar to what has been observed in related structures. The benzene ring and the SO₂—NH—CO—C group make a dihedral angle of 71.2 (1)°. Intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

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

Experimental

Crystal data

C₁₂H₁₇NO₃S
M _r = 255.34
Triclinic,
a = 6.695 (1) Å
b = 8.953 (2) Å
c = 12.040 (2) Å
α = 80.21 (1)°
β = 78.51 (1)°
γ = 88.98 (1)°
V = 696.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 299 (2) K
0.50 × 0.32 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.894, T _max = 0.978
8562 measured reflections
2827 independent reflections
1947 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.142
S = 1.02
2827 reflections
182 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 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/S1600536808017790/rk2096sup1.cif

e-64-o1274-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017790/rk2096Isup2.hkl

e-64-o1274-Isup2.hkl^{(138.7KB, 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⋯O1ⁱ	0.79 (3)	2.19 (3)	2.955 (2)	164 (3)

Open in a new tab

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

The present work is a part of a study of the substituent effects on the solid state geometries of N–(aryl)–sulfonamides and substituted amides. The conformations of the N—H and C=O bonds of the SO₂—NH—CO—C group in N–(4–methylphenylsulfonyl)–2,2,2–trimethylacetamide, (I), are anti– to each other (Fig. 1), similar to that observed in N–(phenylsulfonyl)–2,2,2–trimethylacetamide, II, (Gowda et al., 2008). The bond parameters in I are similar to those in II, N–(aryl)–2,2,2–trimethylacetamides (Gowda et al., 2007) and 4–methylbenzenesulfonamide (Gowda et al., 2003). The packing diagram of molecules I shows the intermolecular hydrogen bonds N1—H1N···O1ⁱ which link the molecules into centrosymmetric dimers (Fig. 2). Symmetry code: (i) -x, -y+2, -z+2.

Experimental

The title compound was prepared by refluxing 4–methylbenzenesulfonamide 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 IR– 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.