N-(4-Methyl­benzo­yl)-4-nitro­benzene­sulfonamide

P A Suchetan; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812007854

. 2012 Feb 29;68(Pt 3):o888. doi: 10.1107/S1600536812007854

N-(4-Methylbenzoyl)-4-nitrobenzenesulfonamide

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

PMCID: PMC3297935 PMID: 22412738

Abstract

In the title compound, C₁₄H₁₂N₂O₅S, the dihedral angle between the nitrophenyl group and the –S—NH—C—O fragment is 80.74 (17)° and that between the nitrophenyl and methylphenyl groups is 87.66 (14)°. The C—S—N—C torsion angle at the S—N bond is −67.0 (3)°. In the crystal, molecules are linked into C(4) chains via N—H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-arylamides, see: Gowda et al. (1999 ▶, 2006 ▶). For N-aryl-methanesulfonamides, see: Gowda et al. (2007 ▶). For N-(substituted-benzoyl)-arylsulfonamides, see: Suchetan et al. (2010 ▶). For N-chloroarylamides, see: Jyothi & Gowda (2004 ▶). For N-bromoarylsulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C₁₄H₁₂N₂O₅S
M _r = 320.32
Orthorhombic,
a = 13.969 (1) Å
b = 9.6591 (6) Å
c = 21.026 (2) Å
V = 2837.0 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.40 × 0.18 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.905, T _max = 0.956
7163 measured reflections
2864 independent reflections
1835 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.152
S = 1.16
2863 reflections
203 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 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/S1600536812007854/yk2044sup1.cif

e-68-0o888-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007854/yk2044Isup2.hkl

e-68-0o888-Isup2.hkl^{(140.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812007854/yk2044Isup3.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)	2.16 (2)	2.994 (4)	168 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the University Grants Commission, Government of India, New Delhi, for a UGC-BSR one-time Grant to Faculty.

supplementary crystallographic information

Comment

As part of our studies on the substituent effects on the structures and other aspects of N-arylamides (Gowda et al., 1999, 2006), N-aryl-methanesulfonamides (Gowda et al., 2007), N-(substituted-benzoyl)-arylsulfonamides (Suchetan et al., 2010), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(4-methylbenzoyl)-4-nitrobenzenesulfonamide has been determined (Fig.1).

The conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti with respect to the C=O bond (Fig.1), similar to that observed in N-(4-methylbenzoyl)-4-chlorobenzenesulfonamide (I) (Suchetan et al., 2010).

In the title compound, the molecules are twisted at the S–N bonds with the torsional angle of -67.0 (3)°, compared to the value of 69.0 (2)° in (I).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 79.6 (1)°, compared to the value of 77.2 (1)° in (I).

The dihedral angle between the sulfonyl and the benzoyl benzene rings is 89.3 (1)°, compared to the value of 89.5 (1)° in (I).

The packing of molecules linked by of N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing a mixture of 4-methylbenzoic acid, 4-nitrobenzenesulfonamide and phosphorous oxy chloride for 3 h 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 reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

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