N-(2-Methyl­phen­yl)-4-nitro­benzene­sulfonamide

U Chaithanya; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812036331

. 2012 Aug 25;68(Pt 9):o2766. doi: 10.1107/S1600536812036331

N-(2-Methylphenyl)-4-nitrobenzenesulfonamide

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

PMCID: PMC3435801 PMID: 22969647

Abstract

In the title compound, C₁₃H₁₂N₂O₄S, the dihedral angle between the planes of the rings is 51.11 (10)°. In the crystal, molecules are linked into inversion dimers through pairs of N—H⋯O(S) hydrogen bonds.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011 ▶); Bowes et al. (2003 ▶); Gowda & Weiss (1994 ▶); Saeed et al. (2010 ▶); Shahwar et al. (2012 ▶), of N-arylsulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2005 ▶) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C₁₃H₁₂N₂O₄S
M _r = 292.31
Monoclinic,
a = 14.106 (1) Å
b = 7.0082 (5) Å
c = 14.854 (2) Å
β = 110.84 (1)°
V = 1372.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.44 × 0.44 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.898, T _max = 0.942
4889 measured reflections
2781 independent reflections
2198 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.119
S = 1.08
2781 reflections
185 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 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 datablock(s) I, global. DOI: 10.1107/S1600536812036331/bt6824sup1.cif

e-68-o2766-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036331/bt6824Isup2.hkl

e-68-o2766-Isup2.hkl^{(136.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036331/bt6824Isup3.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	0.83 (2)	2.11 (2)	2.923 (2)	166 (2)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

UC thanks Mangalore University for the award of a research fellowship. 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 a part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Bowes et al., 2003; Gowda & Weiss, 1994; Saeed et al., 2010; Shahwar et al., 2012); N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2005) and N-chloroarylsulfonamides (Gowda & Shetty, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(2-methylphenyl)-4-nitrobenzenesulfonamide has been determined (Fig. 1).

The conformation of the N—C bond in the —SO₂—NH—C segment has gauche torsion with respect to the S═O bonds (Fig.1). Further, the conformation of the N—H bond in the —SO₂—NH— segment is syn to the ortho-methyl group in the anilino ring, compared to syn conformation observed between the N—H bond and ortho- nitro group in the sulfonyl benzene ring in N-(4-methylphenyl)-2-nitrobenzenesulfonamide (I) (Chaithanya et al., 2012). The molecule is twisted at the S—N bond with the torsional angle of -58.97 (21)°, compared to the value of 76.55 (18)° in (I).

The dihedral angle between the sulfonyl and the anilino rings is 51.11 (10)°, compared to the value of 72.64 (8)° in (I).

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

Experimental

The title compound was prepared by treating 4-nitrobenzenesulfonylchloride with 2-methylaniline 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-(2-methylphenyl)-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 (429 K) from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like light brown 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.