2-(2,5-Dichloro­benzene­sulfonamido)-3-methyl­butanoic acid

Islam Ullah Khan; Peter John; Haffsah Iqbal; Shahzad Sharif; Edward R T Tiekink

doi:10.1107/S1600536810041620

. 2010 Oct 23;66(Pt 11):o2888. doi: 10.1107/S1600536810041620

2-(2,5-Dichlorobenzenesulfonamido)-3-methylbutanoic acid

Islam Ullah Khan ^a,^‡, Peter John ^a, Haffsah Iqbal ^a, Shahzad Sharif ^a, Edward R T Tiekink ^b,^*

PMCID: PMC3009271 PMID: 21589068

Abstract

The structure of the title compound, C₁₁H₁₃Cl₂NO₄S, shows one sulfonamide-O atom to lie almost in the plane of the benzene ring [C—C—S—O = −178.7 (2) °] and the other to one side [C—C—S—O = −49.4 (3)°]. Lying to the other side is the amine residue, which occupies a position almost perpendicular to the plane [C—S—N—C = 70.2 (2)°]; the carboxylic acid group is orientated to lie over the benzene ring. In the crystal, the appearance of an 11-membered {⋯OH⋯OCOH⋯OC₂NH} synthon, which features the hydroxy group forming both donor (to a carbonyl-O) and acceptor (from the amine-H) interactions, leads to the formation of a supramolecular chain along the a axis. Chains are connected in the crystal structure by C—H⋯O contacts.

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

C₁₁H₁₃Cl₂NO₄S
M _r = 326.18
Orthorhombic,
a = 5.4584 (2) Å
b = 14.0623 (6) Å
c = 19.4545 (8) Å
V = 1493.28 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 293 K
0.19 × 0.13 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.805, T _max = 0.921
14542 measured reflections
3405 independent reflections
2876 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.127
S = 1.00
3405 reflections
180 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.51 e Å⁻³
Absolute structure: Flack (1983 ▶), 1415 Friedel pairs
Flack parameter: 0.09 (8)

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/S1600536810041620/hg2730sup1.cif

e-66-o2888-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041620/hg2730Isup2.hkl

e-66-o2888-Isup2.hkl^{(163.6KB, 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
O3—H3o⋯O4ⁱ	0.82 (3)	1.86 (2)	2.674 (3)	171 (3)
N1—H1n⋯O3ⁱⁱ	0.85 (2)	2.32 (2)	3.161 (3)	167 (3)
C7—H7⋯O1ⁱⁱⁱ	0.98	2.42	3.341 (3)	157
C4—H4⋯O2^iv	0.93	2.41	3.223 (5)	146

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

supplementary crystallographic information

Comment

The crystal structure of the title compound, (I), was determined in connection with on-going structural studies of sulfonamides (Sharif et al., 2010; Khan et al., 2010), of interest owing to their biological properties (Korolkovas, 1988; Mandell & Sande, 1992).

With reference to the benzene ring in (I), Fig. 1, the O2 atom lies in the plane [the O2—S1—C1—C2 torsion angle = -178.7 (2) °] but the O1 atom lies out of the plane [O1—S1—C1—C2 = -49.4 (3) °]. The amine group lies to the opposite side of the plane to the O1 atom and occupies a position almost perpendicular to it [C1—S1—N1—C7 = 70.2 (2) °]. Within the amine residue, the carboxylic acid group is co-planar with the amine-N1 [N1—C7—C11—O4 = -1.6 (4) °], and is folded to be orientated over the benzene ring with the carbonyl-O4 atom closest to it.

In the crystal packing, the hydroxyl-O3 group forms both donor and acceptor interactions, the former to a symmetry related carbonyl-O4 and the latter with a symmetry related amine-N1—H atom, Table 1. These lead to a linear supramolecular chain, Fig. 2, aligned along the a axis and mediated by an 11-membered {···OH···OCOH···OC₂NH} synthon; the chain is further stabilized by a C7—H7···O1 contact, Table 1. Chains are held in the crystal structure by C—H···O contacts, Fig. 3 and Table 1.

Experimental

To 2-amino-3-methylbutanoic acid (234 mg, 2 mmol) in distilled water (15 ml), was added 2,5-dichlorobenzenesulfonyl chloride (491 mg, 2 mmol) while maintaining the pH of reaction mixture at 8 by using 3% sodium carbonate solution. The consumption of the reactants was confirmed by TLC. The pH of reaction mixture was adjusted to 3 using 3 N HCl. The precipitates were washed with water and crystallized from methanol