N-(3-Chloro­phen­yl)-4-nitro­benzene­sulfonamide

U Chaithanya; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812047496

. 2012 Nov 24;68(Pt 12):o3424. doi: 10.1107/S1600536812047496

N-(3-Chlorophenyl)-4-nitrobenzenesulfonamide

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

PMCID: PMC3589007 PMID: 23476243

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₁₂H₉ClN₂O₄S, in which the dihedral angles between the planes of the benzene rings are 46.90 (14) and 44.50 (14)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into zigzag chains parallel to the a axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-arylsulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2002 ▶) and of N-chloroarylamides, see: Gowda & Shetty (2004 ▶); Gowda & Weiss (1994 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C₁₂H₉ClN₂O₄S
M _r = 312.72
Monoclinic,
a = 14.3419 (8) Å
b = 7.7579 (4) Å
c = 23.895 (1) Å
β = 90.345 (5)°
V = 2658.6 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 293 K
0.48 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.810, T _max = 0.914
9649 measured reflections
4839 independent reflections
3112 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.163
S = 1.05
4839 reflections
367 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.29 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

Click here for additional data file.^{(30.1KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047496/bt6857sup1.cif

e-68-o3424-sup1.cif^{(30.1KB, cif)}

Click here for additional data file.^{(237KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047496/bt6857Isup2.hkl

e-68-o3424-Isup2.hkl^{(237KB, hkl)}

Click here for additional data file.^{(4.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812047496/bt6857Isup3.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⋯O8	0.87 (2)	2.22 (2)	3.052 (4)	163 (3)
N3—H3N⋯O4ⁱ	0.85 (2)	2.36 (2)	3.135 (4)	153 (4)

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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 UGC–BSR one-time grant to faculty and the Department of Science and Technology, Government of India, New Delhi, for the research grant under its promotion of university research and scientific excellence programme.

supplementary crystallographic information

Comment

As a part of studying the effect of substituents on the structures and other aspects of N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2002) and N-chloroarylamides (Gowda & Shetty, 2004; Gowda & Weiss, 1994; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(3-chlorophenyl)-4-nitrobenzenesulfonamide (I) has been determined (Fig. 1). The asymmetric unit of the structure contains two independent molecules. The N—C bonds in the C—SO₂—NH—C segments have gauche torsions with respect to the S═O bonds.

The molecules in (I) are twisted at the S—N bonds with the torsional angles of -58.67 (30) and 61.49 (30)°, compared to the value of 48.46 (18)° in N-(3-chlorophenyl)-2-nitrobenzenesulfonamide (II) (Chaithanya et al., 2012).

The dihedral angle between the sulfonyl and the anilino rings are 46.90 (14) and 44.50 (14)°, compared to the value of 73.65 (7)° in (II).

N—H···O hydrogen bonds link the molecules into zigzag chains parallel to the a-axis. (Table 1, Fig. 2.)

Experimental

The title compound was prepared by treating 4-nitrobenzenesulfonyl- chloride with 3-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 resultant solid N-(3-chlorophenyl)-4-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 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.