(S)-N-{1-[5-(4-Chloro­benzyl­sulfanyl)-1,3,4-oxadiazol-2-yl]eth­yl}-4-methyl­benzene­sulfonamide

Tayyaba Syed; Shahid Hameed; Peter G Jones

doi:10.1107/S1600536811039134

. 2011 Sep 30;67(Pt 10):o2793. doi: 10.1107/S1600536811039134

(S)-N-{1-[5-(4-Chlorobenzylsulfanyl)-1,3,4-oxadiazol-2-yl]ethyl}-4-methylbenzenesulfonamide

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

PMCID: PMC3201458 PMID: 22064948

Abstract

The title compound, C₁₈H₁₈ClN₃O₃S₂, adopts by folding the form of a distorted disc. Interplanar angles are 29.51 (7) and 63.43 (7)° from the five-membered ring to the aromatic systems and 34.80 (6)° between these two latter rings. The absolute configuration was confirmed by determination of the Flack parameter. In the crystal, the molecules are linked by four hydrogen bonds, one classical (N—H⋯N) and three ‘weak’ (C—H⋯O), forming layers parallel to the ac plane; these are in turn linked in the third dimension by Cl⋯N [3.1689 (16) Å] and Cl⋯O [3.3148 (13) Å] contacts to the heterocyclic ring.

Related literature

For the chemotherapeutic effects of substituted-1,3,4-oxadiazole derivatives, see: Aboraia et al. (2006 ▶); Akhtar et al. (2008 ▶, 2010 ▶); Khan et al. (2005 ▶); Mishra et al. (2005 ▶); Zahid et al. (2009 ▶). Based on the known structures of 2,5-disubstituted-1,3,4-oxadiazoles with diverse biological activity, we have designed and synthesized several new derivatives of 1,3,4-oxadiazoles and evaluated their anti-HIV activity, see: Syed et al. (2011 ▶).

Experimental

Crystal data

C₁₈H₁₈ClN₃O₃S₂
M _r = 423.92
Orthorhombic,
a = 5.5928 (3) Å
b = 17.5004 (7) Å
c = 20.1431 (7) Å
V = 1971.53 (15) Å³
Z = 4
Cu Kα radiation
μ = 3.90 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Nova A diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.785, T _max = 1.000
31188 measured reflections
3762 independent reflections
3625 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.069
S = 1.04
3762 reflections
250 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 1563 Friedel pairs
Flack parameter: −0.001 (11)

Data collection: CrysAlis PRO Oxford Diffraction (2010 ▶); 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 ▶) and RPLUTO (CCDC, 2007 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039134/bt5653sup1.cif

e-67-o2793-sup1.cif^{(28.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039134/bt5653Isup2.hkl

e-67-o2793-Isup2.hkl^{(184.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039134/bt5653Isup3.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
N5—H05⋯N4ⁱ	0.90 (3)	2.19 (3)	3.068 (2)	166 (2)
C15—H15B⋯O2ⁱⁱ	0.99	2.41	3.301 (2)	149
C9—H9⋯O2ⁱⁱⁱ	0.95	2.43	3.178 (2)	136
C15—H15B⋯O3^iv	0.99	2.47	3.007 (2)	113

Open in a new tab

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

supplementary crystallographic information

Comment

Substituted-1,3,4-oxadiazole derivatives are of significant interest because of their chemotherapeutic effects such as anti-proliferative (Zahid et al., 2009), anti-tumour and anti-viral (Akhtar et al., 2008), anti-microbial (Mishra et al., 2005), urease inhibition (Akhtar et al., 2010), tyrosinase inhibition (Khan et al., 2005), and anti-mitotic (Aboraia et al., 2006) activities. Based on the known structures of 2,5-disubstituted-1,3,4-oxadiazoles with diverse biological activities, we have designed and synthesized several new derivatives of 1,3,4-oxadiazoles and evaluated their anti-HIV activity (Syed et al., 2011). In this paper, we report the crystal structure of one of these compounds.

The molecule of the enantiomerically pure title compound is shown in Fig. 1. Bond lengths and angles may be regarded as normal. The molecule has considerable potential for flexibility; the shape actually adopted is that of a short cylinder or disc, albeit distorted, in which the rings form part of the circumference. The smallest dimension of the molecular "box" is calculated by the program RPLUTO (CCDC, 2007) as 6.8 Å, which is close to the calculated distance between the para H atoms of a phenyl group (including van der Waals' radii). All three rings are planar within r.m.s. deviations of < 0.01 Å; interplanar angles are 29.51 (7)° and 63.43 (7)° from the five-membered ring to the aromatic systems C8–13 and C16–21 respectively, and 34.80 (6)° between these two latter rings. To close the circumference of the cylinder, the methyl hydrogen H14C approaches the centroid of the ring C16–21 at a distance of 3.08 Å.

The molecular packing is determined by four hydrogen bonds, one classical and three "weak" (including a three-centre system based on H15B), which link the molecules to form layers parallel to the ac plane (Fig. 2). It can be seen that the Cl atoms project out of this plane (the angle between the bond C19—Cl and the plane is 72°) and the Cl atoms thereby form short contacts Cl···N3 3.1689 (16) Å, operator -x, y - 1/2, -z + 1/2, and Cl···O1 3.3148 (13) Å, operator -x + 1, y - 1/2, -z + 1/2, to the oxadiazole ring, thus linking the layers (Fig. 3). The approximately linear angle C19—Cl···N3 166.31 (8)° is consistent with the description of Cl···N3 as a halogen bond.

Experimental

The title compound was prepared according to a reported procedure (Syed et al., 2011) and recrystallized from acetone/water.