N-(4-Meth­oxy­phen­yl)benzene­sulfonamide

Saba Ibrahim; M Nawaz Tahir; Nadeem Iqbal; Durre Shahwar; Muhammad Asam Raza

doi:10.1107/S1600536811000365

. 2011 Jan 8;67(Pt 2):o298. doi: 10.1107/S1600536811000365

N-(4-Methoxyphenyl)benzenesulfonamide

Saba Ibrahim ^a, M Nawaz Tahir ^b,^*, Nadeem Iqbal ^a, Durre Shahwar ^a, Muhammad Asam Raza ^a

PMCID: PMC3051711 PMID: 21522988

Abstract

In the title compound, C₁₃H₁₃NO₃S, the benzene ring of the benzenesulfonamide moiety is disordered with an occupancy ratio of 0.56 (3):0.44 (3), the disorder components being twisted at and angle of 21 (1)° to each other. The methoxybenzene group is roughly planar (r.m.s. deviation = 0.0144 Å) and the amide N atom is displaced from this plane by 0.090 (6) Å. The dihedral angles between the methoxybenzene group and the major and minor occupancy components of the disordered benzene ring are 54.6 (4) and 62.9 (5)°, respectively. In the crystal, infinite polymeric chains are formed along [100] due to intermolecular N—H⋯O hydrogen bonding. Weak C—H⋯π interactions are also present in the crystal.

Related literature

For related structures, see: Kato et al. (2006 ▶); Perlovich et al. (2009 ▶).

Experimental

Crystal data

C₁₃H₁₃NO₃S
M _r = 263.30
Orthorhombic,
a = 5.3094 (5) Å
b = 8.5309 (10) Å
c = 27.925 (3) Å
V = 1264.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.30 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.961, T _max = 0.970
7272 measured reflections
2457 independent reflections
1503 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.131
S = 1.02
2457 reflections
138 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 961 Friedel pairs
Flack parameter: 0.09 (16)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000365/bq2272sup1.cif

e-67-0o298-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000365/bq2272Isup2.hkl

e-67-0o298-Isup2.hkl^{(118.3KB, hkl)}

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

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

Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C7–C12 and C1B–C6B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.83 (2)	2.22 (2)	3.039 (4)	170 (4)
C8—H8⋯Cg2ⁱⁱ	0.93	2.93	3.613 (5)	132
C13—H13B⋯Cg1ⁱⁱⁱ	0.96	2.98	3.766 (6)	140
C13—H13B⋯Cg3ⁱⁱⁱ	0.96	2.96	3.763 (7)	143

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

Acknowledgments

The authors are grateful to Professor Dr Islam Ullah Khan for providing research facilities at Government College University, Lahore, Pakistan.

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) is a part of the synthesis of sulfonamides and consequently the study of their bioactivity. The crystal structures of 4-amino-N-(4-methoxyphenyl)benzenesulfonamide (Perlovich et al., 2009) and P-(+)-N-Phenyl-4-methoxybenzenesulfonamide (Kato, et al., 2006) have been published previously which are related to the title compound (I).

In (I), the phenyl ring of benzenethiol moiety is disordered over two set of sites A (C1A—C6A) and B (C1B—C6B) with occupancy ratio of 0.56 (3):0.44 (3). The dihedral angle between A/B is 21 (1)°. The methoxybenzene group C (C7—C13/O2) is almost planar with r. m. s. deviation of 0.0144 Å and amide atom N1 is at a distance of 0.0897 (55)Å. The dihedral angle between A/C and B/C is 54.63 (35)° and 62.86 (50)°, respectively. The sulfonyl group D (S1/O1/O2) is of course planar. The dihedral angles between A/D, B/D and C/D are 53.37 (43)°, 51.65 (50)° and 24.10 (28)°, respectively. The molecules are stabilized in the form of infinite one-dimensional polymeric chains due to N—H···O type (Table 1, Fig. 2) extending along the crystallographic a-axis. The C—H···π interactions (Table 1) also play important role in stabilizing the molecules.

Experimental

Equal molar (10 mmol) quantity of benzene sulfonyl chloride and para anisidine was mixed in 10 ml distilled water under stirring at room temperature. During the reaction pH was adjusted at 8 using dilute solution of sodium carbonate. The reaction was monitored using TLC. On the completion of reaction the pH was made acidified using 3 N HCl. The crude product was separated by filtration, dried and recrystalized in methanol to afford white needles of (I) after 72 h.