N-(2-Methyl­phenyl­sulfon­yl)propanamide

K Shakuntala; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811014164

. 2011 Apr 22;67(Pt 5):o1187. doi: 10.1107/S1600536811014164

N-(2-Methylphenylsulfonyl)propanamide

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

PMCID: PMC3089174 PMID: 21754489

Abstract

In the title compound, C₁₀H₁₃NO₃S, the conformations of the N—H and C=O bonds of the SO₂—NH—CO—C segment are anti to each other, while the amide H atom is syn with respect to the ortho-methyl group in the benzene ring. The C—S—N—C torsion angle is −66.7 (2)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

Related literature

For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2004 ▶); on the structures of N-(substitutedphenylsulfonyl)-substitutedamides, see: Shakuntala et al. (2011a ▶,b ▶) and on the oxidative strengths of N-chloro, N-arylsulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C₁₀H₁₃NO₃S
M _r = 227.27
Monoclinic,
a = 8.3050 (8) Å
b = 13.339 (1) Å
c = 9.9948 (9) Å
β = 97.876 (9)°
V = 1096.78 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.44 × 0.32 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.886, T _max = 0.956
4277 measured reflections
2241 independent reflections
1607 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.108
S = 1.04
2241 reflections
140 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014164/ds2108sup1.cif

e-67-o1187-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014164/ds2108Isup2.hkl

e-67-o1187-Isup2.hkl^{(110.2KB, 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⋯O1ⁱ	0.82 (2)	2.08 (2)	2.901 (2)	173 (3)

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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 hydrogen bonding preferences of sulfonamides has been investigated (Adsmond & Grant, 2001). The nature and position of substituents play a significant role on the crystal structures and other aspects of N-(aryl)-amides and N-(aryl)-sulfonamides (Gowda et al., 2003, 2004; Shakuntala et al., 2011a,b). As a part of studying the effects of substituents on the structures of this class of compounds, the structure of N-(2-methylphenylsulfonyl)-2-methylacetamide (I) has been determined (Fig. 1). The conformations of the N—H and C=O bonds of this segment in the structure are anti to each other, similar to that observed in N-(2-methylphenylsulfonyl)-acetamide (II) (Shakuntala et al., 2011b) and N-(2-methylphenylsulfonyl)-2,2,2-trimethylacetamide (III) (Shakuntala et al., 2011a). Further, the conformation of the amide H atom is syn to the ortho-methyl group in the benzene ring, similar to that observed between the amide H atom and the ortho-methyl group in (II) and (III).

The molecules in (I) are bent at the S-atom with a C—S—N—C torsion angle of -66.7 (2)°, compared to the values of -58.2 (2)° in (II) and -65.4 (2)° in (III).

In the crystal structure, the pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules through inversion-related dimers into chains running in the direction of b-axis. Part of the crystal structure is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing 2-methylbenzenesulfonamide (0.10 mole) with an excess of propanoyl chloride (0.20 mole) for one 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 reprecipitated 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 further characterized by recording its infrared spectra.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of an ethanolic solution of the compound.