2-(N-Cyclo­hexyl­carbamo­yl)benzene­sulfonamide

Waseeq Ahmad Siddiqui; Adnan Ashraf; Hamid Latif Siddiqui; Muhammad Akram; Masood Parvez

doi:10.1107/S1600536812000633

. 2012 Jan 14;68(Pt 2):o370. doi: 10.1107/S1600536812000633

2-(N-Cyclohexylcarbamoyl)benzenesulfonamide

Waseeq Ahmad Siddiqui ^a,^*, Adnan Ashraf ^a, Hamid Latif Siddiqui ^b, Muhammad Akram ^b, Masood Parvez ^c

PMCID: PMC3275049 PMID: 22346994

Abstract

The asymmetric unit of the title compound, C₁₃H₁₈N₂O₃S, contains two molecules with similar conformations. In both molecules, the cyclohexyl rings adopt chair conformations, with the attached N atom in an equatorial orientation and an intramolecular N—H⋯O hydrogen bond generates an S(7) ring. In the crystal, N—H⋯O hydrogen bonds link the molecules and a C—H⋯O hydrogen bond is also observed. The crystal studied was a racemic twin.

Related literature

For the biological activity of benzenesulfonamide derivatives, see: Petrov et al. (2006 ▶); Eatedal et al. (2002 ▶); Ahmad et al. (2010 ▶). For related structures, see: Siddiqui et al. (2007 ▶, 2008 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₃H₁₈N₂O₃S
M _r = 282.35
Orthorhombic,
a = 16.1869 (5) Å
b = 10.8467 (3) Å
c = 15.9353 (4) Å
V = 2797.83 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.20 × 0.14 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.954, T _max = 0.981
5929 measured reflections
5929 independent reflections
5451 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.110
S = 1.14
5929 reflections
362 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶)
Flack parameter: 0.52 (8)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000633/hb6585sup1.cif

e-68-0o370-sup1.cif^{(26.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000633/hb6585Isup2.hkl

e-68-0o370-Isup2.hkl^{(284.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812000633/hb6585Isup3.cml

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—H11N⋯O4ⁱ	0.92 (4)	2.05 (4)	2.935 (4)	161 (4)
N2—H2N⋯O6ⁱⁱ	0.91 (4)	1.96 (4)	2.874 (4)	175 (4)
N3—H32N⋯O2ⁱⁱⁱ	0.88 (4)	2.23 (4)	2.943 (4)	138 (4)
C3—H3⋯O1^iv	0.95	2.54	3.254 (4)	132
N1—H12N⋯O3	0.86 (4)	2.18 (4)	2.938 (4)	146 (4)
N3—H31N⋯O6	0.85 (4)	2.09 (4)	2.831 (4)	145 (4)
N4—H4N⋯O3	0.85 (4)	2.11 (4)	2.952 (4)	171 (3)

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

Acknowledgments

WAS is grateful to the University of Sargodha, Sargodha, Pakistan, for providing research facilities.

supplementary crystallographic information

Comment

Derivatives of benzenesulfonamide find wide spread applications for the synthesis of pharmaceutical products which have bactericidal properties, various bioactive agents, artificial fibers, dyes, plasticizers and high molecular weight substances (Petrov et al., 2006). Several pyrazole and oxadiazole derivatives have been reported to exhibit analgesic and anti-inflammatory activities and many drugs containing them are still in use in the market (Eatedal et al., 2002). In continuation of our research on the synthesis of biological active benzothiazine derivatives (Siddiqui et al., 2007) we report the synthesis and crystal structure of the title compound in this article.

There are two independent molecules in an asymmetric unit of the title compound, labeled as molecules A (Fig. 1) and B (Fig. 2) containing the S1 and S2 atoms, respectively. There are insignificant differences in the conformations of the two molecules, e.g., the torsion angles C6–C7–N2–C8 and C19–C20–N4–C21 in molecules A and B are 177.3 (3) and -179.2 (3)°, respectively. In both molecules, the cyclohexyl rings adopt chair conformations with puckering parameters (Cremer & Pople, 1975) in molecules A and B being Q = 0.564 (4) and 0.573 (4) Å, θ = 3.1 (4) and 2.3 (4) ° and ω = 273 (8) and 251 (8) °, respectively. The bond distances and angles in both molecules agree very well with the cortresponding bond distances and angles reported in a closely related compound (Siddiqui et al., 2007).

In the solid state, the molecules A and B are linked with each other via hydrogen bonds involving amino and O-atoms of the sulfonamide groups with N1···O4 = 2.935 (4) and N3···O2 = 2.943 (4) Å. The molecules A are linked into chains involving intermolecular interactions C3···O1 = 3.254 (4) Å. The molecules B do not show any such interactions. The molecules are stabilized by intramolecular interactions of the types N—H···O and C—H···O (Table 1 and Figure 3).

Experimental

For the synthesis of the title compound, cyclohexylamine and saccharin were used as the starting materials following a reported procedure (Siddiqui et al., 2008). Crystals of the title compound suitable for X-ray crystallographic study were grown from methanol at room temperature; m.p. = 512 – 513 K.