N-(2-Methyl­phen­yl)-2-nitro­benzene­sulfonamide

U Chaithanya; Sabine Foro; B Thimme Gowda

doi:10.1107/S160053681203423X

. 2012 Aug 4;68(Pt 9):o2649. doi: 10.1107/S160053681203423X

N-(2-Methylphenyl)-2-nitrobenzenesulfonamide

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

PMCID: PMC3435676 PMID: 22969547

Abstract

In the title compound, C₁₃H₁₂N₂O₄S, the dihedral angle between the benzene rings is 53.44 (14)°. The amide H atom exhibits bifurcated hydrogen bonding: an intramolecular N—H⋯O hydrogen bond generates an S(7) motif while in the crystal, N—H⋯O(S) hydrogen bonds link the molecules into zigzag C(4) chains along the c axis.

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. (2002 ▶) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001 ▶); Allen et al. (1998 ▶); Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C₁₃H₁₂N₂O₄S
M _r = 292.31
Monoclinic,
a = 9.2409 (7) Å
b = 15.1531 (9) Å
c = 10.5376 (8) Å
β = 107.775 (8)°
V = 1405.13 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.30 × 0.28 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.930, T _max = 0.967
5234 measured reflections
2538 independent reflections
2020 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.114
S = 1.21
2538 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.36 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/S160053681203423X/bt5990sup1.cif

e-68-o2649-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203423X/bt5990Isup2.hkl

e-68-o2649-Isup2.hkl^{(124.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681203423X/bt5990Isup3.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)	2.16 (2)	2.897 (3)	146 (3)
N1—H1N⋯O3	0.84 (2)	2.57 (3)	3.132 (4)	125 (3)

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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 studying the substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Bowes et al., 2003; Gowda et al., 1994; Saeed et al., 2010; Shahwar et al., 2012); N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2002) and N-chloroarylsulfonamides (Gowda & Shetty, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(2-methylphenyl)-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-methyl group in the anilino ring. similar to that observed in N-(2-chlorophenyl)-2-nitrobenzenesulfonamide (I) (Chaithanya et al., 2012). The molecule is twisted at the S—N bond with the torsional angle of 73.90 (26)°, compared to the value of 74.97 (20)° in (I).

The dihedral angle between the sulfonyl and the anilino rings is 53.44 (14)°, compared to the value of 54.97 (11)° in (I).

The amide H-atom showed bifurcated intramolecular H-bonding with the O-atom of the ortho-nitro group in the sulfonyl benzene ring, generating S(7) motifs and the intermolecular H-bonding with the sulfonyl oxygen atom of the other molecule, generating C(4) motifs (Adsmond et al., 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 zigzag chains. Part of the crystal structure is shown in Fig. 2.

Experimental

The title compound was prepared by treating 2-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)-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 (138° 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.