N-Benzoyl-2-nitro­benzene­sulfonamide

P A Suchetan; Sabine Foro; B Thimme Gowda; B Nirmala

doi:10.1107/S1600536811055917

. 2012 Jan 11;68(Pt 2):o339. doi: 10.1107/S1600536811055917

N-Benzoyl-2-nitrobenzenesulfonamide

P A Suchetan ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*, B Nirmala ^c

PMCID: PMC3275024 PMID: 22346969

Abstract

In the title compound, C₁₃H₁₀N₂O₅S, the N—C bond in the C—SO₂—NH—C segment has gauche torsion angles with respect to the S=O bonds. The conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn. The molecule is twisted at the S—N bond with a torsion angle of −63.4 (2)°. The sulfonyl benzene ring is tilted by 77.1 (1)° relative to the —SO₂—NH—C—O segment. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 88.6 (1)°. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link the molecules into inversion dimers, which are linked by weak C—H⋯O and C—H⋯π interactions along the b axis.

Related literature

For studies, including those by our group, on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (2006 ▶), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004 ▶), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003 ▶), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2010 ▶) and on N-chloroarylamides, see: Gowda & Mahadevappa (1983 ▶).

Experimental

Crystal data

C₁₃H₁₀N₂O₅S
M _r = 306.29
Orthorhombic,
a = 12.1127 (8) Å
b = 11.7625 (8) Å
c = 18.730 (1) Å
V = 2668.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.48 × 0.44 × 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 = 0.883, T _max = 0.901
6396 measured reflections
2711 independent reflections
2010 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.110
S = 1.04
2711 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 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/S1600536811055917/bq2330sup1.cif

e-68-0o339-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055917/bq2330Isup2.hkl

e-68-0o339-Isup2.hkl^{(133.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811055917/bq2330Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.84 (2)	2.21 (2)	3.003 (3)	158 (2)
C11—H11⋯O3ⁱⁱ	0.93	2.51	3.267 (3)	139
C13—H13⋯O2ⁱ	0.93	2.53	3.313 (3)	142
C6—H6⋯Cg1ⁱⁱⁱ	0.93	2.82	3.678 (13)	153

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

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

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2006), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2003); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2010) and N-chloro-arylsulfonamides (Gowda & Mahadevappa, 1983), in the present work, the crystal structure of N-(benzoyl)- 2-nitrobenzenesulfonamide (I) has been determined (Fig.1).

In (I), the conformation between the N—H and C=O bonds in the C—SO₂—NH—C(O) segment is anti (Fig.1), similar to that observed in N-(benzoyl)-2-methylbenzenesulfonamide (II) (Suchetan et al., 2010). Furthermore, the N—C bond in the segment has gauche torsion with respect to the S═O bonds, while, the conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn.

The molecule is twisted at the S—N bond with the torsional angle of -63.39 (22)°, compared to the value of 68.8 (4)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 77.1 (1)°, compared to the value of 84.8 (1)° in (II). Further, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 88.6 (1)°, compared to the value of 73.9 (1)° in (II).

In the crystal, intermolecular N1–H1N···O2 and C13—H13···O2 hydrogen bonds link the molecules as dimers and these dimers are also linked by C11—H11···O3 hydrogen bonds and C—H···π interactions along b-axis (Table 1). [C6—H6···Cg1, cg1 is the centroid of C8—C13 ring] Parts of the crystal structure are shown in Fig. 2., Fig. 3. and Fig. 4.

Experimental

The title compound was prepared by refluxing a mixture of benzoic acid (0.02 mole), 2-nitrobenzenesulfonamide (0.02 mole) and excess phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(benzoyl)-2-nitrobenzenesulfonamide, obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution at room temperature.