N,N′-Bis[(2-methyl­phenyl)sulfon­yl]adipamide

Vinola Z Rodrigues; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811007203

. 2011 Mar 5;67(Pt 4):o789. doi: 10.1107/S1600536811007203

N,N′-Bis[(2-methylphenyl)sulfonyl]adipamide

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

PMCID: PMC3099916 PMID: 21754080

Abstract

The asymmetric unit of the title compound, C₂₀H₂₄N₂O₆S₂, comprises one half-molecule, the remaining portion being generated via an inversion centre. The dihedral angle between the plane of the benzene ring and the SO₂—NH—C(O)—C—C segment is 89.9 (1)°. In the crystal, intermolecular N—H⋯O(S) hydrogen bonds link the molecules into infinite chains in [101].

Related literature

For related structures, see: Gowda et al. (2007 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

C₂₀H₂₄N₂O₆S₂
M _r = 452.53
Monoclinic,
a = 11.928 (2) Å
b = 5.523 (1) Å
c = 16.447 (4) Å
β = 96.05 (2)°
V = 1077.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 K
0.48 × 0.12 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.875, T _max = 0.989
3521 measured reflections
2135 independent reflections
1571 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.076
wR(F ²) = 0.147
S = 1.31
2135 reflections
140 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.29 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/S1600536811007203/vm2082sup1.cif

e-67-0o789-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007203/vm2082Isup2.hkl

e-67-0o789-Isup2.hkl^{(105KB, 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	0.84 (2)	2.09 (2)	2.917 (4)	166 (4)

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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 sulfonamide moiety is an important constituent of many biologically important compounds. As a part of studying the substituent effects on the structures of this class of compounds (Gowda et al., 2007, 2010a,b), in the present work, the structure of N,N-bis(2-methylphenylsulfonyl)-adipamide has been determined (Fig.1). The asymmetric unit comprises half of a molecule, the remaining portion being generated via an inversion centre. The conformation of the N—H and C=O bonds in the C—SO₂—NH—C(O)—C—C segment is anti to each other and the amide O atom is also anti to the H atoms attached to the adjacent C atom. Further, the conformation of the N—H bond in the amide fragment is syn to the ortho-methyl group in the adjacent benzene ring. The molecule is bent at the S atom with the C—SO₂—NH—C(O) torsion angle of -63.7 (4)°. Further, the S1—N1—C7—C8 and C7—N1—S1—O1 segments are nearly linear. The torsion angles C2—C1—S1—N1 and C6—C1—S1—N1 are -71.3 (4)° and 106.9 (4)°, respectively.

The dihedral angle between the planes of the benzene ring and the SO₂—NH—C(O)—C—C segment is 89.9 (1)°.

N—H···O1(S) H-bond formation results in an S=O1 bond longer than the S=O2 bond. A series of N—H···O(S) intermolecular hydrogen bonds (Table 1) link the molecules into infinite chains running in the [101] direction (Fig. 2).

Experimental

N,N-Bis(2-methylphenylsulfonyl)-adipamide was prepared by refluxing a mixture of adipic acid (0.01 mol) with o-toluenesulfonamide (0.02 mol) and POCl₃ for 1 hr on a water bath. The reaction mixture was allowed to cool and added ether to it. The solid product obtained was filtered, washed thoroughly with ether and hot ethanol. The compound was recrystallized to the constant melting point and was characterized by its infrared and NMR spectra.

Needle like colorless single crystals used in the X-ray diffraction studies were grown by a slow evaporation of a solution of the compound in ethanol at room temperature.