N-(3,5-Dimethyl­phen­yl)-4-nitro­benzene­sulfonamide

U Chaithanya; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812047502

. 2012 Nov 24;68(Pt 12):o3425. doi: 10.1107/S1600536812047502

N-(3,5-Dimethylphenyl)-4-nitrobenzenesulfonamide

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

PMCID: PMC3589008 PMID: 23476244

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₁₄H₁₄N₂O₄S, in which the dihedral angles between the benzene rings are 56.22 (15) and 58.16 (14)°. In the crystal, N—H⋯O_nitro hydrogen bonds link the molecules into zigzag chains running along the a-axis direction.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994 ▶); Shahwar et al. (2012 ▶), of N-arylsulfonamides, see: Chaithanya et al. (2012 ▶) and of N-chloroarylsulfonamides, see: Shetty & Gowda (2004 ▶). For hydrogen-bonding patterns and motifs, see: Adsmond & Grant (2001 ▶).

Experimental

Crystal data

C₁₄H₁₄N₂O₄S
M _r = 306.33
Orthorhombic,
a = 14.708 (1) Å
b = 7.9410 (7) Å
c = 24.741 (2) Å
V = 2889.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.38 × 0.30 × 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 = 0.914, T _max = 0.944
6693 measured reflections
3714 independent reflections
2624 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.074
S = 1.00
3714 reflections
390 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ▶), 1005 Friedel pairs
Flack parameter: 0.04 (8)

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.^{(32.9KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047502/bt6865sup1.cif

e-68-o3425-sup1.cif^{(32.9KB, cif)}

Click here for additional data file.^{(182.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047502/bt6865Isup2.hkl

e-68-o3425-Isup2.hkl^{(182.1KB, hkl)}

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

Supplementary material file. DOI: 10.1107/S1600536812047502/bt6865Isup3.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⋯O3ⁱ	0.85 (2)	2.35 (2)	3.129 (5)	152 (3)
N3—H3N⋯O8ⁱⁱ	0.84 (2)	2.40 (2)	3.168 (5)	152 (3)

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Symmetry codes: (i) Inline graphic ; (ii) .

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 (Gowda & Weiss, 1994; Shahwar et al., 2012); N-arylsulfonamides (Chaithanya et al., 2012) and N-chloroarylsulfonamides (Shetty & Gowda, 2004),in the present work, the crystal structure of N-(3,5-dimethylphenyl)-4-nitrobenzenesulfonamide (I) has been determined (Fig. 1).

The asymmetric unit of the structure of (I) contains two crystallographically independent molecules, similar to that observed in N-(3,5-dimethylphenyl)-2-nitrobenzenesulfonamide (II) (Chaithanya et al., 2012). The molecules are twisted at the S—N bonds with the torsional angles of -66.67 (38) and -70.56 (39)°, compared to the values of 44.24 (26) and -49.34 (25)° in (II).

The dihedral angles between the sulfonyl and the anilino rings in the two molecules are 56.22 (15)° and 58.16 (14)°, compared to the values of 71.53 (7)° and 72.11 (7)° in (II).

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).

In the crystal, the intermolecular N–H···O (N) hydrogen bonds (Table 1) link the molecules into zigzag chains running along the a axis. Part of the crystal structure is shown in Fig. 2.

Experimental

The title compound was prepared by treating 4-nitrobenzenesulfonylchloride with 3,5-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-(3,5-dimethylphenyl)-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.