(2S)-Methyl 2-(4-chloro­benzene­sulfon­amido)-4-(methyl­sulfan­yl)butanoate

Tayyaba Syed; Shahid Hameed; Peter G Jones

doi:10.1107/S1600536809018297

. 2009 May 20;65(Pt 6):o1348. doi: 10.1107/S1600536809018297

(2S)-Methyl 2-(4-chlorobenzenesulfonamido)-4-(methylsulfanyl)butanoate

Tayyaba Syed ^a, Shahid Hameed ^a,^*, Peter G Jones ^b

PMCID: PMC2969768 PMID: 21583200

Abstract

The enantiomerically pure title compound, C₁₂H₁₆ClNO₄S₂, contains a pyramidal N atom with an S—N bond length of 1.6306 (15) Å. Molecules are linked to form chains parallel to the a axis by classical N—H⋯O hydrogen bonding involving a sulfonyl O atom, supported by three weak C—H⋯X interactions. (X = S, O).

Related literature

For the applications of esters in industry and as intermediates in the synthesis of heterocycles, see: Akhtar et al. (2007 ▶, 2008 ▶); Kashif et al. (2008 ▶); Serwar et al. (2009 ▶); Syed et al. (2009 ▶).

Experimental

Crystal data

C₁₂H₁₆ClNO₄S₂
M _r = 337.83
Orthorhombic,
a = 5.1814 (3) Å
b = 12.6089 (8) Å
c = 23.2137 (13) Å
V = 1516.59 (16) Å³
Z = 4
Cu Kα radiation
μ = 4.92 mm⁻¹
T = 100 K
0.20 × 0.12 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Nova A diffractometer
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2008 ▶) T _min = 0.548, T _max = 1.000 (expected range = 0.408–0.744)
14469 measured reflections
3093 independent reflections
3027 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.025
wR(F ²) = 0.062
S = 1.04
3093 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ▶), 1250 Friedel pairs
Flack parameter: 0.005 (12)

Data collection: CrysAlis Pro (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018297/bt2959sup1.cif

e-65-o1348-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018297/bt2959Isup2.hkl

e-65-o1348-Isup2.hkl^{(151.8KB, 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
N—H01⋯O3ⁱ	0.81 (3)	2.30 (3)	3.1048 (18)	169 (3)
C2—H2⋯O1ⁱⁱ	1.00	2.66	3.637 (2)	166
C12—H12⋯O1ⁱⁱ	0.95	2.37	3.315 (2)	173
C3—H3B⋯O3ⁱⁱⁱ	0.99	2.66	3.635 (2)	170
C5—H5B⋯S1^iv	0.98	2.97	3.892 (2)	157
C5—H5C⋯S1ⁱ	0.98	2.88	3.665 (2)	138

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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 through project No. 20-674/R&D/06/1764 under the National Research Program for Universities.

supplementary crystallographic information

Comment

Esters have attracted widespread attention due to their applications in industry and as intermediates in the synthesis of heterocycles (Syed et al., 2009; Akhtar et al., 2008, 2007; Serwar et al., 2009). several types of pharmacological activities have also been associated with sulfonamides (Akhtar et al., 2008, Kashif et al., 2008). The title compound (I), a methionine derivative, was synthesized in our laboratory as an intermediate for onward conversion to 1,3,4-oxadiazole derivatives, and here we report its structure.

Molecular dimensions of (I) may be considered normal. The nitrogen atom displays a pyramidal geometry (Syed et al., 2009), lying 0.27 (1) Å out of the plane of its substituents. The molecule adopts the general shape of a thick disc (as is reflected in the short a axis length), with the ester group folded under the aromatic ring (C1···C11 3.374 (2) Å, C11—S2···C2—C1 - 19.3 (1)°). The molecules are connected in chains parallel to the a axis by the classical hydrogen bond N—H01···O3 (H···O 2.30 (3) Å), supported by the "weak" hydrogen bonds H2···O1, H12···O1 (a bifurcated system) and H5C···S1 (H···X 2.66, 2.37, 2.88 Å respectively). Symmetry operators for all these H bonds involve a axis translation.

Experimental

The title compound was synthesized by the reaction of methionine (0.02 mol) and 4-chlorobenzenesulfonyl chloride according to a reported procedure (Syed et al., 2009). Recrystallization of the product from acetone/water afforded crystals suitable for X-ray analysis.