2,2-Dimethyl-N-(2-methyl­phenyl­sulfon­yl)propanamide

K Shakuntala; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811003400

. 2011 Jan 29;67(Pt 2):o536. doi: 10.1107/S1600536811003400

2,2-Dimethyl-N-(2-methylphenylsulfonyl)propanamide

K Shakuntala ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3051617 PMID: 21523184

Abstract

In the title compound, C₁₂H₁₇NO₃S, the amide H atom is syn to the ortho-methyl group of the benzene ring and the C—S—N—C torsion angle is −65.39 (17)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds in which the acceptor O atom is bound to the S atom.

Related literature

Sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976 ▶). Their tendency and preferences for hydrogen bonding in the solid state can give rise to polymorphism, see: Yang & Guillory (1972 ▶); Adsmond & Grant (2001 ▶). For our studies on the effect of substituents on the crystal structures of this class of compounds, see: Gowda et al. (2008a ▶,b ▶, 2010 ▶).

Experimental

Crystal data

C₁₂H₁₇NO₃S
M _r = 255.33
Monoclinic,
a = 7.3827 (6) Å
b = 21.986 (2) Å
c = 8.6060 (8) Å
β = 97.158 (9)°
V = 1386.0 (2) Å³
Z = 4
Cu Kα radiation
μ = 2.06 mm⁻¹
T = 299 K
0.30 × 0.25 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
3884 measured reflections
2472 independent reflections
2202 reflections with I > 2σ(I)
R _int = 0.050
3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.098
S = 1.05
2472 reflections
162 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003400/tk2712sup1.cif

e-67-0o536-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003400/tk2712Isup2.hkl

e-67-0o536-Isup2.hkl^{(121.5KB, 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	0.82 (2)	2.10 (2)	2.906 (2)	170 (2)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

supplementary crystallographic information

Comment

The molecular structures of sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976), and their propensity for hydrogen bonding in the solid state, due to the presence of various hydrogen bond donors and acceptors, can give rise to polymorphism (Yang & Guillory, 1972; Adsmond & Grant, 2001). Hence, the nature and position of substituents play a significant role on the crystal structures of N-(aryl)sulfonoamides. As a part of a study of the substituent effects on the crystal structures of this class of compounds (Gowda et al., 2008a,b, 2010), the structure of N-(2-methylphenylsulfonyl)-2,2,2- trimethylacetamide (I) has been determined.

The N—H and C=O bonds are anti to each other (Fig. 1), as observed in each of N-(phenylsulfonyl)acetamide (II) (Gowda et al., 2010), N-(phenylsulfonyl)-2,2,2-trimethylacetamide (III) (Gowda et al., 2008b) and N-(4-methylphenylsulfonyl)-2,2,2-trimethylacetamide (IV) (Gowda et al., 2008a). Further, the amide hydrogen is syn to the ortho-methyl group in the benzene ring. The molecule in (I) is bent at the S-atom with the C1—S1—N1—C7 torsion angle being -65.39 (17)°, compared to the values of -58.8 (4)° in (II), -64.5 (3)° in (III) and -68.2 (2)° in (IV).

In the crystal structure, the pairs of intermolecular N–H···O hydrogen bonds (Table 1) link inversion-related molecules into dimeric aggregates where the acceptor O atom is bound to the S atom; Fig. 2.

Experimental

Compound (I) was prepared by refluxing 2-methylbenzenesulfonamide (0.10 mole) with an excess of 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.Compound (I) was reprecipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. Prism like red crystals were obtained from a slow evaporation of an ethanolic solution of (I).