Ethyl 2-[N-(2-formyl­phen­yl)benzene­sulfonamido]acetate

S Ranjith; P Sugumar; R Sureshbabu; A K Mohanakrishnan; M N Ponnuswamy

doi:10.1107/S160053680900292X

. 2009 Feb 6;65(Pt 3):o483. doi: 10.1107/S160053680900292X

Ethyl 2-[N-(2-formylphenyl)benzenesulfonamido]acetate

S Ranjith ^a, P Sugumar ^a, R Sureshbabu ^b, A K Mohanakrishnan ^b, M N Ponnuswamy ^a,^*

PMCID: PMC2968473 PMID: 21582152

Abstract

In the molecule of the title compound, C₁₇H₁₇NO₅S, the two aromatic rings are oriented at an angle of 30.13 (10)°. The ethyl acetate group assumes an extended conformation. Molecules are linked into C(7) chains running along the a axis by intermolecular C—H⋯O hydrogen bonds, and the chains are crosslinked via C—H⋯π interactions, with the sulfonyl-bound phenyl ring acting as an acceptor.

Related literature

For the activities of sulfonamides, see: Krishnaiah et al. (1995 ▶); Dupont et al. (1978 ▶); Sethu Sankar et al. (2002 ▶). For related literature, see: Bassindale (1984 ▶).

Experimental

Crystal data

C₁₇H₁₇NO₅S
M _r = 347.38
Orthorhombic,
a = 11.3512 (6) Å
b = 11.7820 (6) Å
c = 12.8045 (6) Å
V = 1712.47 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 (2) K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.948, T _max = 0.960
13978 measured reflections
5831 independent reflections
3738 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.109
S = 1.02
5831 reflections
218 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ▶), with 2533 Friedel pairs
Flack parameter: 0.04 (6)

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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900292X/ci2739sup1.cif

e-65-0o483-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900292X/ci2739Isup2.hkl

e-65-0o483-Isup2.hkl^{(279.7KB, hkl)}

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
C5—H5⋯O4ⁱ	0.93	2.57	3.220 (2)	127
C16—H16B⋯Cg1ⁱⁱ	0.97	2.75	3.615 (2)	150

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

Acknowledgments

SR and MNP thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

The title compound is a potential intermediate for the synthesis of 2-alkylbenzoic acid and exhibits insecticidal, germicidal and antimicrobial activities (Krishnaiah et al., 1995; Dupont et al., 1978). The sulfonamides inhibit the growth of bacterial organism and are also useful for treating urinary and gastrointestinal infections (Sethu Sankar et al., 2002).

Atom S1 has a distorted tetrahedral configuration. The widening of angle O2—S1—O3 [120.46 (10)°] and narrowing of angle C8—S1—N1 [105.97 (8)°] from the ideal tetrahedral value are attributed to the Thorpe-Ingold effect (Bassindale, 1984). The two phenyl rings are oriented at an angle of 30.13 (10)°. The ethylacetate moiety assumes an extended conformation as can be seen from torsion angles C14—C15—O5—C16 of 178.12 (15)° and C15—O5—C16—C17 of 173.12 (19)°.

The molecules are linked into C(7) chains running along the a axis by C—H···O hydrogen bonding (Table 1). In addition C—H···π interactions (Table 1) with C8–C13 ring (centroid Cg1) as an acceptor is observed.

Experimental

2-(Benzenesulfonylamino)benzaldehyde (2 mmol) was added with ethyl bromoacetate (2.2 mmol) in the presence of potassium carbonate (4.7 mmol) and dimethyl acetamide (15 ml). The mixture was stirred at room temperature for 6 h. The reaction mass was poured into crushed ice (50 g) containing 4 to 5 drops of concentrated HCl and extracted with ethyl acetate. The product was obtained by column chromatography (hexane-ethyl acetate 9:1). The removal of the solvent followed by column chromatography of the residue (ethyl acetate) afforded white crystalline solid (yield 25%, m.p. 381-383 K). Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution of the title compound at room temperature.