N-(2-Chloro­phen­yl)-2-nitro­benzene­sulfonamide

U Chaithanya; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812033107

. 2012 Jul 28;68(Pt 8):o2575. doi: 10.1107/S1600536812033107

N-(2-Chlorophenyl)-2-nitrobenzenesulfonamide

U Chaithanya ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3415015 PMID: 22905002

Abstract

In the title compound, C₁₂H₉ClN₂O₄S, the N—H bond in the –SO₂—NH– segment is syn to both the ortho-nitro group in the sulfonylbenzene ring and the ortho-Cl atom in the aniline ring. The molecule is twisted at the S—N bond with a torsion angle of 75.0 (2)°. The dihedral angle between the sulfonylbenzene and aniline rings is 54.97 (11)°. The amide H atom shows bifurcated hydrogen bonding, generating S(7) and C(4) motifs. In the crystal, N—H⋯O(S) hydrogen bonds link the molecules into chains.

Related literature

For studies of the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011 ▶); Bowes et al. (2003 ▶); Gowda et al. (2000 ▶), Saeed et al. (2010 ▶); Shahwar et al. (2012 ▶), of N-aroylsulfonamides, see: Suchetan et al. (2012 ▶), of N-chloroarylsulfonamides, see: Gowda et al. (2005 ▶); Shetty & Gowda (2004 ▶) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983 ▶); Usha & Gowda (2006 ▶). For hydrogen-bonding patterns and motifs, see: Adsmond & Grant (2001 ▶); Allen et al. (1998 ▶); Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C₁₂H₉ClN₂O₄S
M _r = 312.72
Monoclinic,
a = 9.2477 (9) Å
b = 15.293 (1) Å
c = 10.4671 (9) Å
β = 108.66 (1)°
V = 1402.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 293 K
0.40 × 0.32 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.845, T _max = 0.934
5456 measured reflections
2847 independent reflections
2331 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.098
S = 1.13
2847 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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/S1600536812033107/sj5261sup1.cif

e-68-o2575-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033107/sj5261Isup2.hkl

e-68-o2575-Isup2.hkl^{(139.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812033107/sj5261Isup3.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⋯O1ⁱ	0.84 (2)	2.17 (2)	2.844 (2)	138 (2)
N1—H1N⋯O3	0.84 (2)	2.49 (2)	3.099 (3)	130 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

supplementary crystallographic information

Comment

As part of our studies of substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Bowes et al., 2003; Gowda et al., 2000; Saeed et al., 2010; Shahwar et al., 2012); N-aroylsulfonamides (Suchetan et al., 2012); N-chloroarylsulfonamides (Gowda et al., 2005; Shetty & Gowda, 2004) and N-bromoarylsulfonamides (Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of N-(2-Chlorophenyl)-2-nitrobenzenesulfonamide has been determined (Fig. 1).

The conformation of the N—H bond in the —SO₂—NH— segment is syn to both the ortho-nitro group in the sulfonyl benzene ring and ortho-Cl atom in the anilino ring. similar to that observed in N-(2-chlorobenzoyl)-2-nitrobenzenesulfonamide (I) (Suchetan et al., 2012). The molecule is twisted at the S—N bond with the torsional angle of 74.97 (20)°, compared to the value of -59.68 (17)° in (I).

The dihedral angle between the sulfonyl and the anilino rings is 54.97 (11)°, compared to the value of 71.2 (1)° in (I).

The amide H-atom shows bifurcated intramolecular H-bonding with the O-atom of the ortho-nitro group in the sulfonyl benzene ring and the intermolecular H-bonding with the sulfonyl oxygen atom of the other molecule, generating S(7) and C(4) motifs (Adsmond & Grant 2001; Allen et al., 1998; Bernstein et al., 1995; Etter, 1990).

In the crystal, the intermolecular N–H···O (S) hydrogen bonds (Table 1) link the molecules into chains. Part of the crystal structure is shown in Fig. 2.

Experimental

The title compound was prepared by treating 2-nitrobenzenesulfonylchloride with 2-chloroaniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resulting solid N-(2-chlorophenyl)-2-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point (145° C) from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.