N,N′-Bis(2-chloro­phenyl­sulfon­yl)suberamide

Vinola Z Rodrigues; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811009196

. 2011 Mar 15;67(Pt 4):o884. doi: 10.1107/S1600536811009196

N,N′-Bis(2-chlorophenylsulfonyl)suberamide

Vinola Z Rodrigues ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3099798 PMID: 21754161

Abstract

In the crystal of the title compound, C₂₀H₂₂Cl₂N₂O₆S₂, the asymmetric unit comprises half of a molecule, the remaining portion is generated via an inversion centre. The conformation of the N—H and C=O bonds in the SO₂–NH–C(O)–C segment is anti. The molecule is bent at the S atom with the C–SO₂–NH–C(O) torsion angle being 68.16 (19)°. The dihedral angle between the plane of the benzene ring and the SO₂–NH–C(O)–C segment is 77.5 (1)°. Hydrogen bonds of the type N—H⋯O(C) link molecules into supramolecular chains along the b axis.

Related literature

For the study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000 ▶). For the effect of substituents in N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ▶). For the effect of substituents on the structures of N-(arylsulfonyl)-amides, see: Rodrigues et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₂₂Cl₂N₂O₆S₂
M _r = 521.42
Monoclinic,
a = 7.8737 (9) Å
b = 9.717 (1) Å
c = 14.616 (2) Å
β = 94.575 (9)°
V = 1114.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 293 K
0.36 × 0.22 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.835, T _max = 0.950
4126 measured reflections
2276 independent reflections
1744 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.104
S = 1.05
2276 reflections
148 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.33 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/S1600536811009196/tk2727sup1.cif

e-67-0o884-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009196/tk2727Isup2.hkl

e-67-0o884-Isup2.hkl^{(111.9KB, 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⋯O3ⁱ	0.83 (2)	2.20 (2)	3.020 (2)	172 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship.

supplementary crystallographic information

Comment

The amide and sulfonamide moieties are important constituents of many biologically significant compounds. As part of an investigation studying the effect of substituents on the structures of this class of compounds (Gowda et al., 2000, 2005; Rodrigues et al., 2011), in the present work, the structure of N,N-bis(2-chlorophenylsulfonyl)-suberamide (I) has been determined (Fig. 1). The asymmetric unit comprises half of a molecule, the remaining portion is generated through an inversion centre, similar to that observed in N,N-bis(2-chlorophenylsulfonyl)-adipamide (II) (Rodrigues et al., 2011). The conformation of the N—H and C═O bonds in the SO₂—NH—C(═O)—C segment is anti. The molecule is bent at the S atom with the C—SO₂—NH—C(═O) torsion angle being 68.16 (19) °, compared to the value of -65.1 (6)° in (II). The torsion angles C2—C1—S1—N1 and C6—C1—S1—N1 are, respectively, 70.6 (2)° and -113.32 (17)°. The corresponding values in (II) are -69.5 (6) ° and 108.8 (5) °, respectively. The dihedral angle between the planes of the benzene ring and the SO₂—NH—C(═O)—C segment in (I) is 77.5 (1) °, compared to the value of 89.6 (2) ° in (II).

A series of N—H···O(C) intermolecular hydrogen bonds (Table 1) link the molecules into chains running along the b axis (Fig. 2).

Experimental

Compound (I) was prepared by refluxing a mixture of suberic acid (0.01 mol) with 2-chlorobenzenesulfonamide (0.02 mol) and POCl₃ for 1 h on a water bath. The reaction mixture was allowed to cool and diethyl ether added. The solid product obtained was filtered, washed thoroughly with ether and hot ethanol. The compound was recrystallized to a constant melting point. Colourless prisms were grown by the slow evaporation of its ethanol solution at room temperature.