N-(2,5-Dimethyl­phen­yl)-2-nitro­benzene­sulfonamide

U Chaithanya; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812047630

. 2012 Nov 24;68(Pt 12):o3426. doi: 10.1107/S1600536812047630

N-(2,5-Dimethylphenyl)-2-nitrobenzenesulfonamide

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

PMCID: PMC3589009 PMID: 23476245

Abstract

In the crystal structure of the title compound, C₁₄H₁₄N₂O₄S, the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and anti to the ortho- and syn to the meta-methyl groups in the aniline ring. The molecule is twisted at the S—N bond with a torsion angle of 71.41 (18)°. The dihedral angle between the planes of the benzene rings is 51.07 (8)°. In the crystal, pairs of N—H⋯O_sulfonamide hydrogen bonds link the molecules into inversion dimers.

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-chloroarylsulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C₁₄H₁₄N₂O₄S
M _r = 306.33
Triclinic,
a = 8.1987 (7) Å
b = 9.6729 (9) Å
c = 9.9328 (9) Å
α = 84.386 (9)°
β = 72.096 (8)°
γ = 89.239 (9)°
V = 745.86 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.36 × 0.24 × 0.16 mm

Data collection

Oxford Diffraction Xcaliburdiffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.921, T _max = 0.964
4954 measured reflections
3027 independent reflections
2629 reflections with I > 2σ(I)
R _int = 0.011

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.108
S = 1.14
3027 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 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.^{(21.9KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047630/rz5026sup1.cif

e-68-o3426-sup1.cif^{(21.9KB, cif)}

Click here for additional data file.^{(148.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047630/rz5026Isup2.hkl

e-68-o3426-Isup2.hkl^{(148.5KB, hkl)}

Click here for additional data file.^{(5.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812047630/rz5026Isup3.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	0.82 (2)	2.27 (2)	3.023 (2)	152 (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 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-chloroarylsulfonamides (Gowda & Shetty, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(2,5-dimethylphenyl)-2-nitrobenzene- sulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and anti to the ortho-methyl and syn to the meta-methyl groups in the anilino ring, compared to the anti conformation observed between the N—H bond and both the ortho- and meta-methyl groups in the anilino ring observed in N-(2,3-dimethylphenyl)-2-nitrobenzene- sulfonamide (II) (Chaithanya et al., 2012).

The molecules in (I) are twisted at the S—N bond with the torsional angle of 71.41 (18)°, compared to the values of -60.37 (30) and 58.81 (34)° in the two independent molecules of (II).

The dihedral angle between the sulfonyl and the anilino rings is 51.07 (8)°, compared to the values of 53.67 (8) and 56.99 (9)° in the two molecules of (II).

The amide H-atom showed the intermolecular H-bonding with the sulfonyl oxygen atom of the other molecule, generating inversion dimers (Table 1, Fig. 2.)

In the crystal structure, N1—H1N···O2(S) intermolecular hydrogen bonds link the molecules into inversion dimers (Table 1, Fig. 2.)

Experimental

The title compound was prepared by treating 2-nitrobenzenesulfonyl- chloride with 2,5-dimethylaniline 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-(2,5-dimethylphenyl)-2-nitrobenzenesulfon- amide 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 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.