N,N′-Bis(4-chloro­phenyl­sulfon­yl)­adipamide

Vinola Z Rodrigues; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811030029

. 2011 Jul 30;67(Pt 8):o2179. doi: 10.1107/S1600536811030029

N,N′-Bis(4-chlorophenylsulfonyl)adipamide

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

PMCID: PMC3213613 PMID: 22091190

Abstract

In the title compound, C₁₈H₁₈Cl₂N₂O₆S₂, the asymmetric unit contains half a molecule with a center of symmetry at the mid-point of the central C—C bond. The dihedral angle between the benzene ring and the SO₂—NH—C(O) segment in the two halves of the molecule is 83.5 (2)°. In the crystal, N—H⋯O(S) intermolecular hydrogen bonds link the molecules into infinite chains running along the c axis. The O atom involved in the hydrogen bond has a longer S—O bond than the other O atom bonded to S [1.403 (4) versus 1.361 (4) Å].

Related literature

For hydrogen-bonding preferences of sulfonamides, see; Adsmond & Grant (2001 ▶). For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2000 ▶, 2007 ▶). For those on N-(arylsulfonyl)-amides, see: Rodrigues et al. (2011a ▶,b ▶). For those on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ▶).

Experimental

Crystal data

C₁₈H₁₈Cl₂N₂O₆S₂
M _r = 493.36
Triclinic,
a = 5.593 (1) Å
b = 8.827 (2) Å
c = 9.908 (2) Å
α = 89.28 (2)°
β = 87.75 (2)°
γ = 81.16 (1)°
V = 482.96 (17) Å³
Z = 1
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 293 K
0.12 × 0.08 × 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 = 0.932, T _max = 0.977
2942 measured reflections
1757 independent reflections
775 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.104
S = 0.99
1757 reflections
139 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.36 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 datablock(s) I, global. DOI: 10.1107/S1600536811030029/zj2018sup1.cif

e-67-o2179-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030029/zj2018Isup2.hkl

e-67-o2179-Isup2.hkl^{(86.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811030029/zj2018Isup3.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—H1N⋯O2ⁱ	0.85 (2)	2.03 (3)	2.839 (7)	160 (6)

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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 an RFSMS research fellowship.

supplementary crystallographic information

Comment

The amide moiety is an important constituent of many biologically significant compounds. As part of our studies on the effects of ring and side chain substitutions on the structures of N-(aryl)-amides (Bhat & Gowda, 2000; Gowda et al., 2000, 2007), N-(arylsulfonyl)-amides (Rodrigues et al., 2011a,b) and N-(aryl)-arylsulfonamides (Gowda et al., 2005), the crystal structure of N,N-bis(4-chlorophenylsulfonyl)- adipamide has been determined (I) (Fig. 1).

In the two C—SO₂—NH—CO—CH₂—CH₂ central segments of the structure, the N—H, C=O and C—H bonds are anti to the adjacent bonds, similar to that observed in N,N- bis(2-chlorophenylsulfonyl)-adipamide (II) (Rodrigues et al., 2011a) and N,N-bis(4-chlorophenylsulfonyl)-suberamide (III) (Rodrigues et al., 2011b). The orientations of sulfonamide groups with respect to the attached phenyl rings are given by the torsion angles of C2—C1—S1—N1 = -117.1 (6)° and C6—C1—S1—N1 = 60.5 (6)°. The molecule is bent at the S atom with the C1—S1—N1—C7 torsion angle of 55.0 (6)°, compared to the value of -65.1 (6)° in (II).

The dihedral angle between the benzene ring and the SO₂—NH—C(O) segment in the two halves of the molecule is 83.5 (2)°, compared to the values of 89.6 (2)° in (II) and 79.5 (2)° in (III).

N—H···O2(S) H-bond formation results in an S=O2 bond longer than the S=O1 bond [1.403 (4)Å versus 1.361 (4) Å]. A series of N—H···O(S) intermolecular hydrogen bonds (Table 1) link the molecules into infinite chains running along c-axis (Fig. 2). The hydrogen bonding preferences of sulfonamides is described elsewhere (Adsmond & Grant, 2001)

Experimental

N,N-Bis(4-chlorophenylsulfonyl)-adipamide was prepared by refluxing a mixture of adipic acid (0.01 mol) with 4-chlorobenzenesulfonamide (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.