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

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

doi:10.1107/S1600536808019375

. 2008 Jul 5;64(Pt 8):o1389. doi: 10.1107/S1600536808019375

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

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

PMCID: PMC2962022 PMID: 21203109

Abstract

The conformations of the N—H and C=O bonds in the SO₂—NH—CO—C group of the title compound (N4BPSTMAA), C₁₁H₁₄BrNO₃S, are trans to each other, similar to what is observed in N-(4-chlorophenylsulfonyl)-2,2,2-trimethylacetamide (N4CPSTMAA) and 2,2,2-trimethyl-N-(4-methylphenylsulfonyl)acetamide (N4MPSTMAA). The bond parameters in N4BPSTMAA are similar to those in N4CPSTMAA, N4MPSTMAA, N-aryl-2,2,2-trimethylacetamides and 4-bromobenzenesulfonamide. The benzene ring and the SO₂—NH—CO—C group in N4BPSTMAA form a dihedral angle of 82.8 (1)°, comparable with the values of 82.2 (1)° in N4CPSTMAA and 71.2 (1)° in N4MPSTMAA. N—H⋯O hydrogen bonds form a centrosymmetric ring characterized by an R ₂ ²(8) motif.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2007 ▶, 2008 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₁₄BrNO₃S
M _r = 320.20
Triclinic,
a = 6.066 (1) Å
b = 10.858 (1) Å
c = 11.092 (2) Å
α = 68.19 (1)°
β = 78.66 (2)°
γ = 88.10 (2)°
V = 664.40 (17) Å³
Z = 2
Mo Kα radiation
μ = 3.25 mm⁻¹
T = 299 (2) K
0.20 × 0.08 × 0.04 mm

Data collection

Oxford Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.563, T _max = 0.881
6843 measured reflections
2692 independent reflections
1551 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.101
S = 0.97
2692 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.29 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/S1600536808019375/bx2154sup1.cif

e-64-o1389-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019375/bx2154Isup2.hkl

e-64-o1389-Isup2.hkl^{(132.2KB, 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⋯O2ⁱ	0.86	2.23	2.982 (3)	146

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

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-bromophenylsulfonyl)-2,2,2-trimethylacetamide (N4BPSTMAA) has been determined (Gowda et al., 2003, 2007, 2008). 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 that observed in N-(4-chlorophenylsulfonyl)-2,2,2-trimethylacetamide (N4CPSTMAA) and (4-methylphenylsulfonyl)-2,2,2-trimethylacetamide (N4MPSTMAA) (Gowda et al., 2008). The bond parameters in N4BPSTMAA are similar to those in N4CPSTMAA, N4MPSTMAA (Gowda et al., 2008), N-(aryl)-2,2,2-trimethylacetamides (Gowda et al., 2007) and 4-bromobenzenesulfonamide (Gowda et al., 2003). The N—H···O hydrogen bonds form a centrosymmetric macro-ring characterized by R₂²(8) motif (Bernstein et al., 1995) ( Table 1, Fig. 2).

Experimental

The title compound was prepared by refluxing 4-bromobenzenesulfonamide (0.10 mole) with an excess 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 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 from a slow evaporation of an ethanolic solution.