3-Hy­droxy-2-(4-meth­oxy­benzene­sulfonamido)­butanoic acid

Suman Sinha; Hasnah Osman; Habibah A Wahab; Madhukar Hemamalini; Hoong-Kun Fun

doi:10.1107/S1600536811046502

. 2011 Nov 12;67(Pt 12):o3275. doi: 10.1107/S1600536811046502

3-Hydroxy-2-(4-methoxybenzenesulfonamido)butanoic acid

Suman Sinha ^a, Hasnah Osman ^b, Habibah A Wahab ^a,^‡, Madhukar Hemamalini ^c, Hoong-Kun Fun ^c,^*,^§

PMCID: PMC3238932 PMID: 22199781

Abstract

The title compound, C₁₁H₁₅NO₆S, features a distorted tetrahedral geometry for the S atom. One of the sulfonamide O atoms is approximately coplanar with the benzene ring [C—C—S—O torsion angle = −160.81 (7)°], whereas the other lies well below the plane [C—C—S—O = −29.66 (8)°]. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains parallel to the b axis.

Related literature

For details and applications of sulfonamides, see: Supuran et al. (2003 ▶); Scozzafava et al. (2003 ▶); Robinson et al. (2003 ▶); Delaet et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₁H₁₅NO₆S
M _r = 289.30
Orthorhombic,
a = 5.6505 (2) Å
b = 9.9204 (3) Å
c = 23.0561 (6) Å
V = 1292.41 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.75 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.821, T _max = 0.954
35154 measured reflections
5756 independent reflections
5505 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.073
S = 1.07
5756 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.42 e Å⁻³
Absolute structure: Flack (1983 ▶), 2444 Friedel pairs
Flack parameter: 0.02 (4)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046502/rz2664sup1.cif

e-67-o3275-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046502/rz2664Isup2.hkl

e-67-o3275-Isup2.hkl^{(276.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811046502/rz2664Isup3.cml

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
O5—H1O5⋯O6ⁱ	0.844 (18)	1.816 (19)	2.6019 (10)	154.3 (17)
O6—H1O6⋯O3ⁱ	0.81 (2)	1.99 (2)	2.7990 (10)	174.2 (19)
C5—H5A⋯O4ⁱⁱ	0.93	2.52	3.3732 (11)	153
C8—H8A⋯O2ⁱⁱⁱ	0.98	2.48	3.4000 (11)	156

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

Acknowledgments

SS, HO and HAW gratefully acknowledge the Malaysian Ministry of Science, Technology and Innovation for the synthesis work funded by grant No. 09–05-lfn-meb-004. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

The chemistry of sulfonamides is of interest as they show distinct physical, chemical and biological properties. Sulfonamides are used as anticancer, anti-inflammatory and antiviral agents (Supuran et al., 2003; Scozzafava et al., 2003). Amino acid-derived sulfonamides are shown to be active against Procollagen C-terminal protease, which is a member of the metzincin enzyme family (Robinson et al., 2003; Delaet et al., 2003).

The asymmetric unit of the title compound is shown in Fig. 1. The S atom is tetrahedrally bonded within a CNO₂ donor set with the greatest deviation manifested in the O2—S1—O3 angle of 120.08 (5)°. The sulfonamide O2 atom is approximately co-planar with the benzene ring [the O2-S1-C1-C6 torsion angle is -160.81 (7)°] whereas the O3 atom lies well below the plane [O3-S1-C1-C6 = -29.66 (8)°].

In the crystal structure (Fig. 2), intermolecular O—H···O and C—H···O hydrogen bonds (Table 1) link the molecules into chains parallel to the b axis.

Experimental

To a solution of L-threonine (3 mmol, 0.618 g) in distilled water (10 ml), 4-methoxybenzene sulphonyl chloride (3 mmol, 0.357 g) was suspended. The pH of the solution was maintained at 8 by continuously adding 1M sodium carbonate solution throughout the reaction at room temperature. After the completion of the reaction, the pH was adjusted to 2 using 1N HCl solution which resulted in the formation of the precipitate which was filtered, dried and recrystallized in methanol to yield the title compound.