Methyl 2-(4-acetamido­benzene­sulfon­amido)­benzoate

Islam Ullah Khan; Shahzad Sharif; Salamat Ali; Waqar Ahmad; Edward R T Tiekink

doi:10.1107/S1600536811009500

. 2011 Mar 19;67(Pt 4):o903. doi: 10.1107/S1600536811009500

Methyl 2-(4-acetamidobenzenesulfonamido)benzoate

Islam Ullah Khan ^a,^‡, Shahzad Sharif ^a, Salamat Ali ^b, Waqar Ahmad ^a, Edward R T Tiekink ^c,^*

PMCID: PMC3099839 PMID: 21754177

Abstract

The molecule of the title compound, C₁₆H₁₆N₂O₅S, has the shape of the letter V but with a small twist; the dihedral angle formed between the benzene rings is 79.66 (9)°. The presence of an intramolecular N—H⋯O hydrogen bond, leading to an S(6) ring, correlates with the near coplanarity of the carboxylate ester group with the benzene ring to which it is connected. The acetamide residue is slightly twisted out of the plane of its benzene ring [C—C—N—C = 13.1 (3)°]. In the crystal, supramolecular chains along the a axis are mediated by N—H⋯O hydrogen bonds. These are connected into layers via C—H⋯O interactions.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Sharif et al. (2010 ▶); Khan et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₅S
M _r = 348.37
Triclinic,
a = 8.2835 (2) Å
b = 9.3722 (3) Å
c = 10.8299 (3) Å
α = 85.537 (1)°
β = 88.614 (1)°
γ = 72.203 (1)°
V = 798.11 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
13593 measured reflections
3604 independent reflections
3122 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.113
S = 1.07
3604 reflections
225 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009500/hb5817sup1.cif

e-67-0o903-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009500/hb5817Isup2.hkl

e-67-0o903-Isup2.hkl^{(173.1KB, 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⋯O3	0.86 (1)	1.90 (2)	2.6266 (18)	141 (2)
N2—H2n⋯O2ⁱ	0.86 (2)	2.31 (2)	3.0888 (19)	151 (2)
C10—H10⋯O1ⁱⁱ	0.93	2.57	3.330 (2)	140

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

supplementary crystallographic information

Comment

As part of on-going structural studies of sulfonamides (Sharif et al., 2010; Khan et al., 2010), the crystal structure of the title compound, (I), is described. Interest in these derivatives relate to their wide use in the treatment of certain infections caused by Gram-positive and Gram-negative microorganisms, some fungi, and certain protozoa (Korolkovas, 1988; Mandell & Sande, 1992).

The molecule of (I), Fig. 1, has an approximate V-shape with the dihedral angle formed between the benzene rings being 79.66 (9) °. The carboxylate ester substituent is co-planar with the benzene ring to which it is connected [the C1—C2—C7—O3 and torsion angle is 2.9 (2) °] but the acetamide residue is slightly twisted out of the plane [C11—C12—N2—C15 = 13.1 (3) °]. The planarity observed for the carboxylate ester group is readily rationalized in terms of an intramolecular N—H···O hydrogen bond, Table 1, which seals a six-membered ring. The most prominent intermolecular contact in the crystal structure is also of the type N—H···O, Table 1, and this serves to link molecules into a linear supramolecular chain along the a axis, Fig. 3. Chains are linked into layers in the ab plane via C—H···O contacts, Table 1, and these stack along the c axis via inter-digitation of the benzoate ester groups; there is no evidence for significant π-interactions between these, however.

Experimental

To methyl anthranilate (260 µl, 2 mmol) in water (10 ml) was added p-toluene sulfonyl chloride (380 mg, 2 mmol). With stirring at room temperature, the pH of the solution was maintained with 3% Na₂CO₃. The progress of the reaction was monitored by TLC. On completion of the reaction, the pH was adjusted to 3 with 3 N HCl. The white precipitates that formed were filtered, washed with distilled water and crystallized from methanol to yield colourless blocks of the title compound.