(S)-N-{1-[5-(4-Chloro-benzyl-sulfanyl)-1,3,4-oxadiazol-2-yl]eth-yl}-4-methyl-benzene-sulfonamide.

The title compound, C(18)H(18)ClN(3)O(3)S(2), adopts by folding the form of a distorted disc. Inter-planar 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 mol-ecules 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 = 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

Δρmax = 0.31 e Å−3

Δρmin = −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.

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

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

Supplementary material file. DOI: 10.1107/S1600536811039134/bt5653Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H18ClN3O3S2	Dx = 1.428 Mg m−3
Mr = 423.92	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 23563 reflections
a = 5.5928 (3) Å	θ = 3.3–75.8°
b = 17.5004 (7) Å	µ = 3.90 mm−1
c = 20.1431 (7) Å	T = 100 K
V = 1971.53 (15) Å3	Tablet, colourless
Z = 4	0.15 × 0.10 × 0.06 mm
F(000) = 880

Oxford Diffraction Xcalibur Nova A diffractometer	3762 independent reflections
Radiation source: Nova (Cu) X-ray Source	3625 reflections with I > 2σ(I)
mirror	Rint = 0.046
Detector resolution: 10.3543 pixels mm-1	θmax = 70.2°, θmin = 3.4°
ω–scan	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −21→20
Tmin = 0.785, Tmax = 1.000	l = −24→24
31188 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.4932P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3762 reflections	Δρmax = 0.31 e Å−3
250 parameters	Δρmin = −0.28 e Å−3
0 restraints	Absolute structure: Flack (1983), 1563 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.001 (11)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.Non-bonded contacts:3.1689 (0.0016) Cl - N3_$5 3.3148 (0.0013) Cl - O1_$6 3.7719 (0.0007) Cl - S1_$6166.31 (0.08) C19 - Cl - N3_$5 102.19 (0.11) Cl - N3_$5 - C2_$5 126.37 (0.07) C19 - Cl - O1_$6 109.03 (0.09) Cl - O1_$6 - C2_$6 114.16 (0.06) C19 - Cl - S1_$6 83.66 (0.06) Cl - S1_$6 - C2_$6Operators for generating equivalent atoms: $5 - x, y - 1/2, -z + 1/2 $6 - x + 1, y - 1/2, -z + 1/2===============================================================Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)2.6855 (0.0038) x - 4.6429 (0.0122) y + 16.8416 (0.0087) z = 2.0416 (0.0053)* -0.0119 (0.0012) C16 * 0.0104 (0.0013) C17 * 0.0005 (0.0013) C18 * -0.0099 (0.0013) C19 * 0.0082 (0.0013) C20 * 0.0027 (0.0013) C21Rms deviation of fitted atoms = 0.0084- 1.1391 (0.0042) x + 17.0266 (0.0034) y - 2.2001 (0.0174) z = 7.9763 (0.0084)Angle to previous plane (with approximate e.s.d.) = 63.43 (0.07)* -0.0027 (0.0009) O1 * 0.0047 (0.0010) C2 * -0.0046 (0.0010) N3 * 0.0027 (0.0010) N4 * -0.0002 (0.0010) C5Rms deviation of fitted atoms = 0.00342.6434 (0.0040) x - 12.9885 (0.0091) y + 9.5712 (0.0144) z = 1.4590 (0.0089)Angle to previous plane (with approximate e.s.d.) = 29.51 (0.07)* 0.0016 (0.0013) C8 * -0.0004 (0.0013) C9 * 0.0015 (0.0014) C10 * -0.0039 (0.0014) C11 * 0.0051 (0.0015) C12 * -0.0040 (0.0014) C13Rms deviation of fitted atoms = 0.00322.6855 (0.0038) x - 4.6429 (0.0122) y + 16.8416 (0.0087) z = 2.0416 (0.0053)Angle to previous plane (with approximate e.s.d.) = 34.80 (0.08)* -0.0119 (0.0012) C16 * 0.0104 (0.0013) C17 * 0.0005 (0.0013) C18 * -0.0099 (0.0013) C19 * 0.0082 (0.0013) C20 * 0.0027 (0.0013) C21Rms deviation of fitted atoms = 0.0084

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl	0.05592 (10)	0.18862 (3)	0.15994 (2)	0.03349 (12)
S1	0.52403 (8)	0.54474 (3)	0.263650 (19)	0.02387 (11)
S2	0.77730 (8)	0.45463 (3)	0.555955 (19)	0.02286 (11)
O1	0.5636 (2)	0.55679 (7)	0.39301 (5)	0.0211 (3)
O2	1.0271 (3)	0.44179 (8)	0.56672 (6)	0.0292 (3)
O3	0.6148 (3)	0.45159 (8)	0.61070 (6)	0.0303 (3)
C2	0.4061 (3)	0.54027 (10)	0.34332 (8)	0.0193 (3)
N3	0.1914 (3)	0.52799 (9)	0.36370 (7)	0.0235 (3)
N4	0.2027 (3)	0.53824 (9)	0.43387 (7)	0.0229 (3)
C5	0.4199 (3)	0.55439 (9)	0.44771 (8)	0.0202 (3)
N5	0.7624 (3)	0.54058 (9)	0.52475 (7)	0.0221 (3)
H05	0.879 (5)	0.5469 (14)	0.4944 (12)	0.034 (6)*
C6	0.5302 (3)	0.57714 (10)	0.51284 (8)	0.0225 (4)
H6	0.4186	0.5626	0.5495	0.027*
C7	0.5667 (4)	0.66361 (11)	0.51427 (9)	0.0311 (4)
H7A	0.6287	0.6788	0.5578	0.047*
H7B	0.4137	0.6892	0.5062	0.047*
H7C	0.6813	0.6783	0.4797	0.047*
C8	0.6782 (3)	0.38998 (10)	0.49450 (9)	0.0236 (4)
C9	0.4622 (4)	0.35176 (11)	0.50209 (10)	0.0289 (4)
H9	0.3651	0.3602	0.5401	0.035*
C10	0.3915 (4)	0.30098 (11)	0.45291 (11)	0.0332 (5)
H10	0.2447	0.2743	0.4577	0.040*
C11	0.5301 (4)	0.28842 (11)	0.39702 (10)	0.0317 (4)
C12	0.7460 (4)	0.32732 (12)	0.39112 (9)	0.0334 (5)
H12	0.8441	0.3185	0.3534	0.040*
C13	0.8207 (4)	0.37862 (11)	0.43917 (9)	0.0278 (4)
H13	0.9671	0.4056	0.4343	0.033*
C14	0.4505 (5)	0.23359 (13)	0.34315 (11)	0.0460 (6)
H14A	0.3121	0.2043	0.3588	0.069*
H14B	0.5816	0.1985	0.3325	0.069*
H14C	0.4062	0.2625	0.3033	0.069*
C15	0.2572 (4)	0.52048 (10)	0.21572 (8)	0.0243 (4)
H15A	0.1158	0.5422	0.2384	0.029*
H15B	0.2691	0.5450	0.1716	0.029*
C16	0.2174 (3)	0.43593 (10)	0.20602 (8)	0.0217 (4)
C17	0.0137 (3)	0.40140 (11)	0.23032 (9)	0.0267 (4)
H17	−0.0945	0.4301	0.2568	0.032*
C18	−0.0354 (4)	0.32510 (11)	0.21652 (9)	0.0273 (4)
H18	−0.1774	0.3020	0.2328	0.033*
C19	0.1239 (4)	0.28349 (11)	0.17903 (9)	0.0249 (4)
C20	0.3328 (4)	0.31573 (11)	0.15569 (9)	0.0284 (4)
H20	0.4433	0.2861	0.1308	0.034*
C21	0.3790 (3)	0.39220 (11)	0.16906 (9)	0.0264 (4)
H21	0.5218	0.4150	0.1529	0.032*

	U11	U22	U33	U12	U13	U23
Cl	0.0429 (3)	0.0264 (2)	0.0311 (2)	−0.00061 (19)	−0.0014 (2)	−0.00327 (18)
S1	0.0258 (2)	0.0332 (2)	0.01268 (18)	−0.00294 (18)	0.00137 (15)	−0.00194 (16)
S2	0.0256 (2)	0.0304 (2)	0.01258 (18)	0.00513 (18)	0.00069 (15)	0.00086 (15)
O1	0.0218 (6)	0.0281 (6)	0.0133 (5)	−0.0008 (5)	0.0012 (5)	−0.0009 (5)
O2	0.0297 (7)	0.0400 (7)	0.0179 (6)	0.0082 (6)	−0.0051 (5)	−0.0023 (5)
O3	0.0356 (8)	0.0373 (7)	0.0180 (6)	0.0076 (6)	0.0067 (5)	0.0046 (5)
C2	0.0219 (9)	0.0211 (8)	0.0150 (7)	0.0014 (6)	−0.0008 (6)	0.0002 (6)
N3	0.0288 (9)	0.0297 (8)	0.0121 (7)	−0.0004 (6)	0.0004 (6)	0.0000 (5)
N4	0.0251 (8)	0.0292 (8)	0.0144 (6)	−0.0015 (7)	0.0012 (6)	0.0013 (6)
C5	0.0242 (9)	0.0207 (8)	0.0155 (8)	0.0024 (7)	0.0033 (7)	0.0013 (6)
N5	0.0215 (8)	0.0292 (8)	0.0154 (7)	−0.0007 (6)	0.0006 (6)	−0.0004 (6)
C6	0.0243 (10)	0.0268 (9)	0.0162 (8)	0.0011 (7)	0.0025 (7)	0.0002 (6)
C7	0.0442 (12)	0.0287 (10)	0.0205 (9)	0.0013 (9)	−0.0028 (8)	−0.0057 (7)
C8	0.0266 (10)	0.0238 (9)	0.0202 (8)	0.0032 (7)	−0.0008 (7)	0.0038 (7)
C9	0.0259 (10)	0.0289 (9)	0.0320 (10)	0.0040 (8)	0.0047 (8)	0.0044 (7)
C10	0.0264 (11)	0.0277 (9)	0.0454 (12)	−0.0036 (8)	−0.0050 (8)	0.0063 (8)
C11	0.0428 (12)	0.0263 (9)	0.0259 (9)	−0.0046 (9)	−0.0113 (9)	0.0055 (7)
C12	0.0459 (13)	0.0366 (11)	0.0175 (8)	−0.0087 (9)	0.0011 (8)	−0.0015 (7)
C13	0.0319 (11)	0.0328 (10)	0.0187 (8)	−0.0066 (8)	0.0035 (7)	0.0016 (7)
C14	0.0648 (16)	0.0385 (11)	0.0349 (11)	−0.0163 (11)	−0.0161 (12)	0.0023 (9)
C15	0.0284 (10)	0.0299 (9)	0.0146 (8)	0.0006 (7)	−0.0036 (7)	0.0011 (7)
C16	0.0238 (9)	0.0300 (9)	0.0112 (7)	0.0026 (7)	−0.0036 (6)	0.0007 (6)
C17	0.0270 (10)	0.0331 (9)	0.0199 (8)	0.0032 (8)	0.0011 (7)	−0.0022 (7)
C18	0.0261 (10)	0.0347 (10)	0.0211 (8)	0.0001 (8)	0.0011 (7)	0.0012 (7)
C19	0.0314 (10)	0.0258 (9)	0.0173 (8)	0.0007 (7)	−0.0056 (7)	−0.0004 (7)
C20	0.0314 (10)	0.0335 (10)	0.0202 (8)	0.0041 (8)	0.0018 (7)	−0.0041 (7)
C21	0.0252 (10)	0.0346 (10)	0.0194 (8)	−0.0008 (7)	0.0028 (7)	−0.0003 (7)

Cl—C19	1.7462 (19)	C16—C21	1.399 (3)
S1—C2	1.7369 (17)	C17—C18	1.391 (3)
S1—C15	1.8272 (19)	C18—C19	1.376 (3)
S2—O3	1.4300 (13)	C19—C20	1.380 (3)
S2—O2	1.4314 (15)	C20—C21	1.389 (3)
S2—N5	1.6323 (15)	C6—H6	1.0000
S2—C8	1.7662 (19)	C7—H7A	0.9800
O1—C2	1.364 (2)	C7—H7B	0.9800
O1—C5	1.365 (2)	C7—H7C	0.9800
C2—N3	1.287 (2)	C9—H9	0.9500
N3—N4	1.4262 (19)	C10—H10	0.9500
N4—C5	1.278 (2)	C12—H12	0.9500
C5—C6	1.504 (2)	C13—H13	0.9500
N5—C6	1.468 (2)	C14—H14A	0.9800
C6—C7	1.527 (3)	C14—H14B	0.9800
C8—C13	1.384 (3)	C14—H14C	0.9800
C8—C9	1.389 (3)	C15—H15A	0.9900
C9—C10	1.388 (3)	C15—H15B	0.9900
C10—C11	1.384 (3)	C17—H17	0.9500
C11—C12	1.391 (3)	C18—H18	0.9500
C11—C14	1.515 (3)	C20—H20	0.9500
C12—C13	1.385 (3)	C21—H21	0.9500
C15—C16	1.509 (2)	N5—H05	0.90 (3)
C16—C17	1.380 (3)
C2—S1—C15	99.64 (8)	C20—C21—C16	120.64 (18)
O3—S2—O2	119.84 (8)	C6—N5—H05	118.5 (16)
O3—S2—N5	107.38 (8)	S2—N5—H05	109.7 (16)
O2—S2—N5	104.64 (8)	N5—C6—H6	108.7
O3—S2—C8	108.50 (9)	C5—C6—H6	108.7
O2—S2—C8	108.17 (8)	C7—C6—H6	108.7
N5—S2—C8	107.72 (8)	C6—C7—H7A	109.5
C2—O1—C5	101.85 (13)	C6—C7—H7B	109.5
N3—C2—O1	113.82 (14)	H7A—C7—H7B	109.5
N3—C2—S1	131.04 (13)	C6—C7—H7C	109.5
O1—C2—S1	115.02 (12)	H7A—C7—H7C	109.5
C2—N3—N4	104.70 (14)	H7B—C7—H7C	109.5
C5—N4—N3	106.62 (14)	C10—C9—H9	120.7
N4—C5—O1	113.00 (15)	C8—C9—H9	120.7
N4—C5—C6	129.72 (15)	C11—C10—H10	119.3
O1—C5—C6	117.03 (16)	C9—C10—H10	119.3
C6—N5—S2	120.65 (12)	C13—C12—H12	119.4
N5—C6—C5	112.98 (14)	C11—C12—H12	119.4
N5—C6—C7	108.09 (16)	C8—C13—H13	120.6
C5—C6—C7	109.49 (15)	C12—C13—H13	120.6
C13—C8—C9	121.33 (18)	C11—C14—H14A	109.5
C13—C8—S2	118.41 (15)	C11—C14—H14B	109.5
C9—C8—S2	120.27 (14)	H14A—C14—H14B	109.5
C10—C9—C8	118.51 (18)	C11—C14—H14C	109.5
C11—C10—C9	121.49 (19)	H14A—C14—H14C	109.5
C10—C11—C12	118.54 (18)	H14B—C14—H14C	109.5
C10—C11—C14	121.2 (2)	C16—C15—H15A	108.6
C12—C11—C14	120.2 (2)	S1—C15—H15A	108.6
C13—C12—C11	121.28 (19)	C16—C15—H15B	108.6
C8—C13—C12	118.84 (19)	S1—C15—H15B	108.6
C16—C15—S1	114.63 (13)	H15A—C15—H15B	107.6
C17—C16—C21	118.88 (17)	C16—C17—H17	119.6
C17—C16—C15	120.35 (17)	C18—C17—H17	119.6
C21—C16—C15	120.66 (17)	C19—C18—H18	120.3
C16—C17—C18	120.82 (17)	C17—C18—H18	120.3
C19—C18—C17	119.33 (18)	C19—C20—H20	120.5
C18—C19—C20	121.24 (18)	C21—C20—H20	120.5
C18—C19—Cl	118.89 (15)	C20—C21—H21	119.7
C20—C19—Cl	119.87 (15)	C16—C21—H21	119.7
C19—C20—C21	119.05 (17)
C5—O1—C2—N3	−0.76 (19)	N5—S2—C8—C9	−110.51 (15)
C5—O1—C2—S1	175.70 (11)	C13—C8—C9—C10	0.5 (3)
C15—S1—C2—N3	−3.60 (19)	S2—C8—C9—C10	−179.52 (15)
C15—S1—C2—O1	−179.31 (13)	C8—C9—C10—C11	−0.5 (3)
O1—C2—N3—N4	0.94 (19)	C9—C10—C11—C12	0.8 (3)
S1—C2—N3—N4	−174.82 (14)	C9—C10—C11—C14	−179.29 (19)
C2—N3—N4—C5	−0.73 (19)	C10—C11—C12—C13	−1.1 (3)
N3—N4—C5—O1	0.3 (2)	C14—C11—C12—C13	178.9 (2)
N3—N4—C5—C6	174.36 (16)	C9—C8—C13—C12	−0.8 (3)
C2—O1—C5—N4	0.24 (18)	S2—C8—C13—C12	179.18 (16)
C2—O1—C5—C6	−174.64 (14)	C11—C12—C13—C8	1.1 (3)
O3—S2—N5—C6	−45.79 (14)	C2—S1—C15—C16	−86.77 (14)
O2—S2—N5—C6	−174.15 (12)	S1—C15—C16—C17	118.83 (16)
C8—S2—N5—C6	70.90 (14)	S1—C15—C16—C21	−64.89 (19)
S2—N5—C6—C5	−83.75 (17)	C21—C16—C17—C18	−2.2 (3)
S2—N5—C6—C7	154.93 (12)	C15—C16—C17—C18	174.13 (16)
N4—C5—C6—N5	138.58 (19)	C16—C17—C18—C19	1.1 (3)
O1—C5—C6—N5	−47.6 (2)	C17—C18—C19—C20	0.9 (3)
N4—C5—C6—C7	−100.9 (2)	C17—C18—C19—Cl	−178.08 (14)
O1—C5—C6—C7	73.0 (2)	C18—C19—C20—C21	−1.6 (3)
O3—S2—C8—C13	−174.53 (14)	Cl—C19—C20—C21	177.35 (14)
O2—S2—C8—C13	−43.07 (17)	C19—C20—C21—C16	0.4 (3)
N5—S2—C8—C13	69.52 (17)	C17—C16—C21—C20	1.5 (3)
O3—S2—C8—C9	5.45 (17)	C15—C16—C21—C20	−174.86 (17)
O2—S2—C8—C9	136.91 (15)

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···O3iv	0.99	2.47	3.007 (2)	113.

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⋯O3iv	0.99	2.47	3.007 (2)	113

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