4-Methyl-N-(4-nitro­benzo­yl)benzene­sulfonamide

P A Suchetan; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536811009470

. 2011 Mar 19;67(Pt 4):o917. doi: 10.1107/S1600536811009470

4-Methyl-N-(4-nitrobenzoyl)benzenesulfonamide

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

PMCID: PMC3100041 PMID: 21754188

Abstract

In title compound, C₁₄H₁₂N₂O₅S, the dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 81.5 (2)° and that between the sulfonyl and the benzoyl benzene rings is 89.8 (1)°. In the crystal, molecules are linked into chains along the b axis via intermolecular N—H⋯O hydrogen bonds. C—H⋯O interactions are also observed.

Related literature

For background to our study of the effect of substituents on the structures of methanesulfonamides, see: Gowda et al. (2007 ▶). For the effect of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ▶). For the effect of substituents on the structures of N-(p-substituted benzoyl)-p-substituted benzenesulfonamides, see: Suchetan et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₂N₂O₅S
M _r = 320.32
Monoclinic,
a = 11.722 (3) Å
b = 5.137 (1) Å
c = 12.488 (3) Å
β = 105.09 (2)°
V = 726.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.40 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.907, T _max = 0.980
2664 measured reflections
2265 independent reflections
1993 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.128
S = 1.17
2265 reflections
203 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ▶), 605 Friedel pairs
Flack parameter: −0.05 (14)

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 datablocks I, global. DOI: 10.1107/S1600536811009470/vm2084sup1.cif

e-67-0o917-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009470/vm2084Isup2.hkl

e-67-0o917-Isup2.hkl^{(111.3KB, hkl)}

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	0.85 (3)	2.22 (3)	3.054 (4)	164 (4)
N1—H1N⋯O1ⁱⁱ	0.85 (3)	2.54 (4)	2.944 (5)	110 (3)
C9—H9⋯O3ⁱⁱⁱ	0.93	2.58	3.254 (5)	130
C13—H13⋯O2ⁱ	0.93	2.53	3.347 (5)	147

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

Acknowledgments

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

supplementary crystallographic information

Comment

The amide and sulfonamide moieties are important constituents of many biologically significant compounds. As a part of studying the effect of substituents on the structures of this class of compounds (Gowda et al., 2005, 2007; Suchetan et al., 2010a,b), the structure of 4-methyl-N-(4-nitrobenzoyl)-benzenesulfonamide (I) has been determined. The conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to those observed in N-(4-chlorobenzoyl)-4- methylbenzenesulfonamide (II) (Suchetan et al., 2010a) and 4-methyl-N-(4-methylbenzoyl)-benzenesulfonamide (III) (Suchetan et al., 2010b).

The molecules are twisted at the S atoms with the C—S(O₂)—NH—C(O) torsional angle of 58.7 (3)°, compared to the values of 67.1 (2)° (molecule 1) and 67.7 (2)° (molecule 2) in (II) and 62.0 (2)° in (III).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 81.5 (2)°, compared to the values of 83.6 (1)° (molecule 1) and 81.0 (1)° (molecule 2) in (II) and 84.9 (1)° in (III).

The dihedral angle between the sulfonyl and the benzoyl benzene rings is 89.8 (1)°, compared to the values of 81.0 (1)° (molecule 1) and 76.3 (1)° (molecule 2) in (II) and 89.0 (1)° in (III).

In the crystal packing the molecules are linked by intermolecular N—H···O hydrogen bonds (Table 1, Fig. 2). Two C—H···O interactions are also observed.

Experimental

The title compound was prepared by refluxing a mixture of 4-nitrobenzoic acid, 4-methylbenzenesulfonamide and phosphorous oxychloride for 3 hr on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid 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.

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