N-(2-Acetyl­phen­yl)benzene­sulfonamide

R R Saravanan; V Dhayalan; A K Mohanakrishnan; G Chakkaravarthi; V Manivannan

doi:10.1107/S1600536809033273

. 2009 Aug 26;65(Pt 9):o2241. doi: 10.1107/S1600536809033273

N-(2-Acetylphenyl)benzenesulfonamide

R R Saravanan ^a, V Dhayalan ^b, A K Mohanakrishnan ^b, G Chakkaravarthi ^c, V Manivannan ^d,^*

PMCID: PMC2970053 PMID: 21577639

Abstract

In the title compound, C₁₄H₁₃NO₃S, the phenyl ring makes a dihedral angle of 81.5 (1)° with the benzene ring. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond and weak C—H⋯O interactions. In the crystal structure, molecules are linked by weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For the biological activity of benzenesulfonamide derivatives, see: Badr (2008 ▶); Hanafy et al. (2007 ▶); Yang et al. (2002 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶); Li & Yang (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₃S
M _r = 275.31
Triclinic,
a = 7.9909 (3) Å
b = 8.6860 (4) Å
c = 10.0701 (4) Å
α = 88.016 (2)°
β = 68.673 (3)°
γ = 83.424 (2)°
V = 646.79 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 295 K
0.24 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEX2 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.942, T _max = 0.951
18690 measured reflections
5104 independent reflections
3886 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.142
S = 1.03
5104 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536809033273/is2453sup1.cif

e-65-o2241-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033273/is2453Isup2.hkl

e-65-o2241-Isup2.hkl^{(244.9KB, 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—H1⋯O3	0.86	2.03	2.596 (2)	123
C2—H2⋯O1	0.93	2.52	2.893 (2)	104
C12—H12⋯O1	0.93	2.40	3.057 (2)	128
C11—H11⋯O1ⁱ	0.93	2.51	3.380 (2)	156
C14—H14C⋯Cg1ⁱⁱ	0.96	2.96	3.763 (2)	142

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the benzene C7–C12 ring.

Acknowledgments

The authors wish to acknowledge IIT, Madras for the data collection.

supplementary crystallographic information

Comment

The benzenesulfonamide derivatives are known to exhibit antitumor (Yang et al., 2002), anti-bacterial (Badr, 2008) and anti-fungal (Hanafy et al., 2007) activities. The geometric parameters in (I) (Fig. 1) agree with the reported values of similar structures (Chakkaravarthi et al., 2007; Li & Yang, 2006).

The phenyl ring C1—C6 makes the dihedral angle of 81.5 (1)° with the benzene ring C7—C12. A distorted tetrahedral geometry [O1—S1—N1 109.49 (6)° and O2—S1—N1 104.32 (6)°] is observed around the S1 atom. The molecular structure is stabilized by weak intramolecular C—H···O and N—H···O interactions and the molecules are linked by weak intermolecular C—H···O and C—H···π interactions (Fig. 2 & Table 1). The intramolecular N1—H1···O3 interaction generates a six-membered ring, with graph-set motif S(6) and the intermolecular C11—H11···O1 interaction generates a fourteen membered ring, with graph-set motif R₂²(14).

Experimental

To a stirred solution of 1-(2-aminophenyl)ethanone (3.0 g, 22.19 mmol) in dry DCM (50 ml) at room temperature, pyridine (1.75 g, 22.12 mmol) was slowly added. After 10 min, PhSO₂Cl (4.71 g, 26.61 mmol) was added and stirred at room temperature for 15 h. Then the reaction mixture was poured over crushed ice containing conc. HCl (10 ml), work up of the reaction followed by recrystallization from CDCl₃ gave the compound.