N-Cyclo­hexyl-N-ethyl-4-methyl­benzene­sulfonamide

Zeeshan Haider; Muhammad Nadeem Arshad; Jim Simpson; Islam Ullah Khan; Muhammad Shafiq

doi:10.1107/S1600536809052593

. 2009 Dec 12;66(Pt 1):o102. doi: 10.1107/S1600536809052593

N-Cyclohexyl-N-ethyl-4-methylbenzenesulfonamide

Zeeshan Haider ^a, Muhammad Nadeem Arshad ^a, Jim Simpson ^b, Islam Ullah Khan ^a,^*, Muhammad Shafiq ^a

PMCID: PMC2980259 PMID: 21579993

Abstract

The title compound, C₁₅H₂₃NO₂S, contains cyclohexyl and ethyl substituents on the sulfonamide N atom and the cyclohexyl ring adopts a classic chair conformation. The dihedral angle between the benzene ring plane and the mean plane through the six atoms of the cyclohexyl ring is 59.92 (6)°. In the crystal structure, C—H⋯O hydrogen bonds link molecules into sheets extending in the bc plane.

Related literature

For ring conformations, see: Cremer & Pople (1975 ▶). For related structures, see: Arshad et al. (2008 ▶, 2009 ▶); Khan et al. (2009 ▶); Gowda et al. (2007a ▶,b ▶,c ▶).

Experimental

Crystal data

C₁₅H₂₃NO₂S
M _r = 281.40
Monoclinic,
a = 12.2269 (5) Å
b = 7.5818 (3) Å
c = 16.3045 (6) Å
β = 92.495 (2)°
V = 1510.03 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.43 × 0.32 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.914, T _max = 0.969
16676 measured reflections
3714 independent reflections
2251 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.122
S = 0.99
3713 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶)), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052593/bt5132sup1.cif

e-66-0o102-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052593/bt5132Isup2.hkl

e-66-0o102-Isup2.hkl^{(178.4KB, 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
C10—H10B⋯O2ⁱ	0.97	2.66	3.530 (3)	150
C13—H13A⋯O1ⁱⁱ	0.96	2.60	3.512 (3)	159

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

Acknowledgments

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant under the ‘Strengthening of the Materials Chemistry Laboratory’ project at GC University, Lahore, Pakistan.

supplementary crystallographic information

Comment

Our group has been involved in the synthesis and crystallographic studies of sulfonamide derivatives (Arshad et al., 2009).

The title compound is a benzenesulfonamide with cyclohexyl and ethyl substituents on the sulfonamide N1 atom, Fig. 1. Bond distances in the molecule are comparable to those in similar structures (Arshad et al., 2008; Khan et al., 2009; Gowda et al., 2007a,b,c). The cyclohexyl (C7···C12) ring adopts a classic chair conformation with puckering amplitude Q = 0.567 (2) Å, θ = 178.8 (2) °, φ = 214 (11) ° (Cremer & Pople, 1975) and the plane through this ring is inclined at 59.92 (6) ° to that of the C1···C6 benzene ring. In the crystal structure C—H···O hydrogen bonds involving the C13–H13 bond of the methyl group and the C10–H10B bond of the cyclohexyl ring link each molecule to the O1 and O2 atoms of individual sulphonamide units forming an extended two dimensional network in the bc plane (Table 1, Fig. 2).

Experimental

A mixture of N-cyclohexyl-4-methyl benzene sulfonamide (1.089 g, 4.3 mmol), sodium hydride (0.21 g, 8.6 mmol) and N, N-dimethylformamide (10 ml) was stirred at room temperature for half an hour followed by addition of ethyl iodode (1.32 g, 8.6 mmol). Stirring was continued further for a period of three hours and the contents were poured over crushed ice. Precipitated product was isolated, washed and crystallized from a methanol solution.