N-(4-Methyl­phen­yl)-2-nitro­benzene­sulfonamide

U Chaithanya; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812035866

. 2012 Aug 23;68(Pt 9):o2745. doi: 10.1107/S1600536812035866

N-(4-Methylphenyl)-2-nitrobenzenesulfonamide

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

PMCID: PMC3435757 PMID: 22969628

Abstract

In the crystal of the title compound, C₁₃H₁₂N₂O₄S, the conformation of the N—H bond in the –SO₂—NH– segment is syn to the ortho-nitro group in the sulfonyl benzene ring. The molecule is twisted at the S—N bond with a torsion angle of 76.55 (18)°. The dihedral angle between the planes of the rings is 72.64 (8)°. In the crystal, molecules are linked by pairs of N—H⋯O(S) hydrogen bonds to form inversion dimers.

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 ▶). For N-arylsulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2005 ▶). For N-chloroarylsulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C₁₃H₁₂N₂O₄S
M _r = 292.32
Monoclinic,
a = 8.2787 (5) Å
b = 11.2017 (7) Å
c = 14.6435 (8) Å
β = 91.116 (5)°
V = 1357.72 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 295 K
0.48 × 0.40 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.888, T _max = 0.906
5351 measured reflections
2766 independent reflections
2353 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.108
S = 1.06
2766 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.42 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/S1600536812035866/rk2377sup1.cif

e-68-o2745-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035866/rk2377Isup2.hkl

e-68-o2745-Isup2.hkl^{(135.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812035866/rk2377Isup3.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)	2.27 (2)	3.099 (2)	169 (2)

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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 molecular structure of N-(4-methylphenyl)-2-nitrobenzenesulfonamide has been determined (Fig. 1).

The conformation of the N–H bond in the –SO₂–NH– segment is syn to the ortho-nitro group in the sulfonyl benzene ring, similar to that observed in N-(4-chlorophenyl)-2-nitrobenzenesulfonamide I (Chaithanya et al., 2012). The molecule is twisted at the S–N bond with the torsional angle of 76.55 (18)°, compared to the value of 79.17 (18)° in I.

The dihedral angle between the sulfonyl and the anilino rings is 72.64 (8)°, compared to the value of 70.27 (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 2-nitrobenzenesulfonylchloride with 4-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-(4-methylphenyl)-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 (385 K) from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like yellow 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.