N-(4-Chloro-phen-yl)-1-(5-{[(2-phenyl-ethen-yl)sulfon-yl]meth-yl}-1,3,4-oxadiazol-2-yl)methane-sulfonamide.

In the title compound, C(18)H(16)ClN(3)O(5)S(2), the dihedral angles between the oxadiazole ring and the phenyl and chloro-benzene rings are 23.4 (2) and 45.4 (2)°, respectively. The C-S-N-C and C(ox)-C-S-C (ox = oxadiazole) torsion angles are 89.3 (5) and -69.1 (3)°, respectively. A short intra-molecular C-H⋯O contact closes an S(6) ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating C(10) chains propagating in [001]. The packing is consolidated by C-H⋯O, C-H⋯π and very weak aromatic π-π stacking inter-actions [centroid-centroid separation = 4.085 (2) Å].

Related literature

For the synthesis and biological activity of the title compound, see: Padmaja et al. (2011 ▶); Muralikrishna et al. (2012 ▶). For related structures, see: Ranjith et al. (2009 ▶); You et al. (2004 ▶).

Experimental

Crystal data

C18H16ClN3O5S2

M = 453.93

Monoclinic,

a = 21.1387 (12) Å

b = 5.4443 (2) Å

c = 18.3484 (11) Å

β = 107.810 (7)°

V = 2010.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.20 × 0.20 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.917, T max = 0.974

8939 measured reflections

3541 independent reflections

2114 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.171

S = 0.87

3541 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037300/hb6934sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037300/hb6934Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037300/hb6934Isup3.cml

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

C18H16ClN3O5S2	F(000) = 936
Mr = 453.93	Dx = 1.513 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 2041 reflections
a = 21.1387 (12) Å	θ = 2.6–29.2°
b = 5.4443 (2) Å	µ = 0.43 mm−1
c = 18.3484 (11) Å	T = 293 K
β = 107.810 (7)°	Plate, colourless
V = 2010.4 (2) Å3	0.20 × 0.20 × 0.06 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	3541 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2114 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 15.9821 pixels mm-1	θmax = 25.0°, θmin = 2.6°
ω scans	h = −25→22
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −6→6
Tmin = 0.917, Tmax = 0.974	l = −2→21
8939 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 0.87	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3541 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

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
S1	0.10737 (6)	0.1465 (2)	0.99341 (7)	0.0506 (4)
S2	0.20592 (5)	−0.11531 (16)	0.70760 (6)	0.0365 (3)
Cl	0.40975 (8)	0.2776 (3)	0.90563 (11)	0.0990 (6)
O1	0.09206 (13)	−0.0641 (5)	0.80065 (15)	0.0409 (7)
O5	0.21845 (15)	−0.2584 (5)	0.64804 (18)	0.0506 (8)
O4	0.22585 (15)	−0.2151 (5)	0.78332 (18)	0.0558 (9)
O2	0.08523 (16)	0.0536 (7)	1.05419 (19)	0.0720 (10)
N1	0.07298 (17)	0.2839 (6)	0.7363 (2)	0.0450 (9)
C1	0.09493 (18)	0.0632 (7)	0.7380 (2)	0.0348 (9)
O3	0.11247 (18)	0.4033 (6)	0.9846 (2)	0.0719 (10)
N3	0.17730 (17)	0.0164 (7)	1.0028 (2)	0.0574 (11)
H3	0.1836	−0.1171	1.0291	0.069*
N2	0.05241 (18)	0.3095 (7)	0.8019 (2)	0.0500 (10)
C10	0.11833 (19)	−0.0673 (7)	0.6803 (2)	0.0403 (10)
H10A	0.1050	0.0260	0.6331	0.048*
H10B	0.0963	−0.2256	0.6701	0.048*
C13	0.3483 (2)	0.0561 (7)	0.6906 (3)	0.0454 (11)
C14	0.3805 (2)	0.0969 (8)	0.6365 (3)	0.0577 (13)
H14	0.3684	0.2316	0.6040	0.069*
C7	0.3391 (2)	0.1971 (9)	0.9301 (3)	0.0568 (13)
C6	0.2849 (3)	0.3435 (8)	0.9081 (3)	0.0530 (12)
H6	0.2847	0.4818	0.8783	0.064*
C8	0.3399 (2)	−0.0127 (9)	0.9717 (3)	0.0557 (13)
H8	0.3767	−0.1158	0.9839	0.067*
C9	0.2858 (2)	−0.0691 (8)	0.9950 (3)	0.0496 (11)
H9	0.2863	−0.2097	1.0239	0.059*
C18	0.3694 (2)	−0.1416 (8)	0.7403 (3)	0.0526 (13)
H18	0.3497	−0.1715	0.7783	0.063*
C3	0.0515 (2)	0.0242 (9)	0.9082 (2)	0.0534 (12)
H3A	0.0535	−0.1537	0.9112	0.064*
H3B	0.0067	0.0730	0.9054	0.064*
C12	0.2957 (2)	0.2238 (7)	0.6963 (3)	0.0539 (13)
H12	0.3047	0.3894	0.6921	0.065*
C11	0.2379 (2)	0.1785 (7)	0.7066 (3)	0.0464 (12)
H11	0.2127	0.3112	0.7137	0.056*
C5	0.2297 (2)	0.2862 (8)	0.9301 (3)	0.0513 (12)
H5	0.1920	0.3848	0.9144	0.062*
C2	0.06481 (19)	0.1027 (8)	0.8369 (2)	0.0412 (10)
C4	0.2303 (2)	0.0831 (7)	0.9755 (2)	0.0442 (11)
C17	0.4193 (2)	−0.2922 (9)	0.7334 (3)	0.0633 (15)
H17	0.4330	−0.4230	0.7671	0.076*
C15	0.4302 (2)	−0.0575 (10)	0.6295 (3)	0.0667 (15)
H15	0.4507	−0.0283	0.5921	0.080*
C16	0.4491 (2)	−0.2543 (9)	0.6781 (4)	0.0674 (16)
H16	0.4820	−0.3610	0.6733	0.081*

	U11	U22	U33	U12	U13	U23
S1	0.0458 (7)	0.0765 (9)	0.0334 (7)	0.0029 (6)	0.0177 (5)	−0.0018 (6)
S2	0.0403 (6)	0.0290 (5)	0.0402 (7)	0.0032 (4)	0.0122 (5)	−0.0008 (5)
Cl	0.0756 (11)	0.1391 (14)	0.1018 (13)	−0.0272 (9)	0.0562 (10)	−0.0005 (10)
O1	0.0424 (17)	0.0491 (16)	0.0336 (17)	0.0029 (13)	0.0153 (14)	0.0082 (13)
O5	0.0518 (19)	0.0459 (16)	0.056 (2)	0.0031 (13)	0.0189 (16)	−0.0183 (14)
O4	0.053 (2)	0.0610 (18)	0.050 (2)	0.0075 (14)	0.0103 (16)	0.0195 (16)
O2	0.059 (2)	0.123 (3)	0.042 (2)	0.000 (2)	0.0281 (17)	0.003 (2)
N1	0.048 (2)	0.050 (2)	0.040 (2)	0.0115 (17)	0.0184 (18)	0.0058 (17)
C1	0.030 (2)	0.043 (2)	0.029 (2)	−0.0014 (17)	0.0059 (18)	0.0037 (18)
O3	0.091 (3)	0.063 (2)	0.066 (3)	0.0071 (18)	0.032 (2)	−0.0110 (17)
N3	0.039 (2)	0.078 (3)	0.057 (3)	0.0039 (19)	0.0164 (19)	0.027 (2)
N2	0.051 (2)	0.060 (2)	0.042 (2)	0.0137 (18)	0.0184 (19)	−0.0010 (19)
C10	0.043 (3)	0.043 (2)	0.037 (3)	0.0001 (19)	0.015 (2)	0.0014 (19)
C13	0.039 (3)	0.038 (2)	0.059 (3)	−0.0046 (19)	0.014 (2)	−0.004 (2)
C14	0.050 (3)	0.054 (3)	0.067 (4)	0.001 (2)	0.014 (3)	0.013 (2)
C7	0.060 (3)	0.070 (3)	0.048 (3)	−0.019 (3)	0.027 (3)	−0.014 (3)
C6	0.069 (4)	0.052 (3)	0.042 (3)	−0.006 (2)	0.023 (3)	0.008 (2)
C8	0.050 (3)	0.063 (3)	0.057 (3)	0.006 (2)	0.022 (3)	−0.005 (3)
C9	0.053 (3)	0.048 (2)	0.048 (3)	0.005 (2)	0.016 (2)	0.007 (2)
C18	0.039 (3)	0.049 (3)	0.069 (4)	−0.001 (2)	0.015 (2)	0.007 (2)
C3	0.044 (3)	0.083 (3)	0.037 (3)	−0.005 (2)	0.020 (2)	0.002 (2)
C12	0.051 (3)	0.034 (2)	0.080 (4)	0.002 (2)	0.026 (3)	0.006 (2)
C11	0.042 (3)	0.032 (2)	0.069 (3)	0.0069 (18)	0.023 (2)	−0.003 (2)
C5	0.047 (3)	0.053 (3)	0.053 (3)	0.000 (2)	0.013 (2)	0.013 (2)
C2	0.031 (2)	0.059 (3)	0.034 (3)	0.0007 (19)	0.0091 (19)	0.001 (2)
C4	0.041 (3)	0.057 (3)	0.033 (3)	−0.009 (2)	0.010 (2)	0.000 (2)
C17	0.039 (3)	0.057 (3)	0.087 (4)	0.005 (2)	0.010 (3)	0.015 (3)
C15	0.046 (3)	0.085 (4)	0.075 (4)	−0.003 (3)	0.027 (3)	−0.010 (3)
C16	0.043 (3)	0.061 (3)	0.096 (5)	0.002 (2)	0.018 (3)	−0.013 (3)

S1—O3	1.415 (3)	C7—C6	1.353 (7)
S1—O2	1.428 (3)	C7—C8	1.370 (7)
S1—N3	1.600 (4)	C6—C5	1.383 (6)
S1—C3	1.775 (5)	C6—H6	0.9300
S2—O4	1.430 (3)	C8—C9	1.373 (6)
S2—O5	1.431 (3)	C8—H8	0.9300
S2—C11	1.739 (4)	C9—C4	1.391 (6)
S2—C10	1.783 (4)	C9—H9	0.9300
Cl—C7	1.741 (5)	C18—C17	1.371 (6)
O1—C2	1.354 (5)	C18—H18	0.9300
O1—C1	1.359 (4)	C3—C2	1.484 (6)
N1—C1	1.285 (5)	C3—H3A	0.9700
N1—N2	1.406 (5)	C3—H3B	0.9700
C1—C10	1.480 (5)	C12—C11	1.315 (6)
N3—C4	1.409 (5)	C12—H12	0.9300
N3—H3	0.8600	C11—H11	0.9300
N2—C2	1.283 (5)	C5—C4	1.381 (6)
C10—H10A	0.9700	C5—H5	0.9300
C10—H10B	0.9700	C17—C16	1.365 (7)
C13—C14	1.382 (6)	C17—H17	0.9300
C13—C18	1.393 (6)	C15—C16	1.373 (7)
C13—C12	1.468 (6)	C15—H15	0.9300
C14—C15	1.382 (6)	C16—H16	0.9300
C14—H14	0.9300
O3—S1—O2	119.6 (2)	C5—C6—H6	120.2
O3—S1—O2	119.6 (2)	C7—C8—C9	119.4 (4)
O3—S1—N3	110.4 (2)	C7—C8—H8	120.3
O3—S1—N3	110.4 (2)	C9—C8—H8	120.3
O2—S1—N3	105.8 (2)	C8—C9—C4	120.3 (4)
O3—S1—C3	108.9 (2)	C8—C9—H9	119.9
O3—S1—C3	108.9 (2)	C4—C9—H9	119.9
O2—S1—C3	105.4 (2)	C17—C18—C13	120.1 (5)
N3—S1—C3	105.8 (2)	C17—C18—H18	119.9
O4—S2—O5	117.81 (18)	C13—C18—H18	119.9
O4—S2—C11	111.1 (2)	C2—C3—S1	114.5 (3)
O5—S2—C11	109.2 (2)	C2—C3—H3A	108.6
O4—S2—C10	107.48 (19)	S1—C3—H3A	108.6
O5—S2—C10	106.52 (18)	C2—C3—H3B	108.6
C11—S2—C10	103.63 (19)	S1—C3—H3B	108.6
C2—O1—C1	102.1 (3)	H3A—C3—H3B	107.6
C1—N1—N2	106.0 (3)	C11—C12—C13	130.7 (4)
N1—C1—O1	112.8 (4)	C11—C12—H12	114.7
N1—C1—C10	129.0 (4)	C13—C12—H12	114.7
O1—C1—C10	118.1 (3)	C12—C11—S2	123.7 (3)
C4—N3—S1	131.0 (3)	C12—C11—H11	118.1
C4—N3—H3	114.5	S2—C11—H11	118.1
S1—N3—H3	114.5	C4—C5—C6	120.2 (4)
C2—N2—N1	105.8 (3)	C4—C5—H5	119.9
C1—C10—S2	114.5 (3)	C6—C5—H5	119.9
C1—C10—H10A	108.6	N2—C2—O1	113.3 (4)
S2—C10—H10A	108.6	N2—C2—C3	129.0 (4)
C1—C10—H10B	108.6	O1—C2—C3	117.7 (4)
S2—C10—H10B	108.6	C5—C4—C9	118.9 (4)
H10A—C10—H10B	107.6	C5—C4—N3	124.0 (4)
C14—C13—C18	117.8 (4)	C9—C4—N3	117.1 (4)
C14—C13—C12	120.1 (4)	C16—C17—C18	121.5 (5)
C18—C13—C12	122.0 (4)	C16—C17—H17	119.3
C15—C14—C13	121.6 (5)	C18—C17—H17	119.3
C15—C14—H14	119.2	C16—C15—C14	119.5 (5)
C13—C14—H14	119.2	C16—C15—H15	120.2
C6—C7—C8	121.5 (4)	C14—C15—H15	120.2
C6—C7—Cl	119.3 (4)	C17—C16—C15	119.5 (5)
C8—C7—Cl	119.2 (4)	C17—C16—H16	120.3
C7—C6—C5	119.6 (4)	C15—C16—H16	120.3
C7—C6—H6	120.2
N2—N1—C1—O1	−1.1 (4)	O2—S1—C3—C2	178.8 (3)
N2—N1—C1—C10	175.3 (4)	N3—S1—C3—C2	−69.4 (4)
C2—O1—C1—N1	0.9 (4)	C14—C13—C12—C11	138.1 (6)
C2—O1—C1—C10	−175.9 (3)	C18—C13—C12—C11	−44.4 (8)
O3—S1—N3—C4	−28.4 (5)	C13—C12—C11—S2	−6.0 (9)
O3—S1—N3—C4	−28.4 (5)	O4—S2—C11—C12	89.9 (5)
O2—S1—N3—C4	−159.1 (4)	O5—S2—C11—C12	−41.7 (5)
C3—S1—N3—C4	89.3 (5)	C10—S2—C11—C12	−154.9 (5)
C1—N1—N2—C2	0.8 (4)	C7—C6—C5—C4	1.1 (7)
N1—C1—C10—S2	108.0 (4)	N1—N2—C2—O1	−0.2 (5)
O1—C1—C10—S2	−75.8 (4)	N1—N2—C2—C3	−178.2 (4)
O4—S2—C10—C1	48.6 (3)	C1—O1—C2—N2	−0.4 (4)
O5—S2—C10—C1	175.8 (3)	C1—O1—C2—C3	177.8 (3)
C11—S2—C10—C1	−69.1 (3)	S1—C3—C2—N2	−76.1 (6)
C18—C13—C14—C15	2.5 (7)	S1—C3—C2—O1	106.1 (4)
C12—C13—C14—C15	−179.9 (5)	C6—C5—C4—C9	−3.4 (7)
C8—C7—C6—C5	2.4 (7)	C6—C5—C4—N3	177.6 (4)
Cl—C7—C6—C5	−177.2 (4)	C8—C9—C4—C5	2.3 (7)
C6—C7—C8—C9	−3.5 (7)	C8—C9—C4—N3	−178.6 (4)
Cl—C7—C8—C9	176.2 (4)	S1—N3—C4—C5	−2.1 (7)
C7—C8—C9—C4	1.1 (7)	S1—N3—C4—C9	178.9 (3)
C14—C13—C18—C17	−1.8 (7)	C13—C18—C17—C16	−0.3 (7)
C12—C13—C18—C17	−179.3 (4)	C13—C14—C15—C16	−1.1 (8)
O3—S1—C3—C2	49.3 (4)	C18—C17—C16—C15	1.8 (8)
O3—S1—C3—C2	49.3 (4)	C14—C15—C16—C17	−1.0 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3	0.93	2.41	3.010 (6)	122
N3—H3···O5i	0.86	2.19	2.900 (5)	140
C3—H3B···O2ii	0.97	2.38	3.198 (5)	141
C6—H6···O4iii	0.93	2.45	3.290 (5)	151
C12—H12···O5iii	0.93	2.60	3.242 (5)	127
C14—H14···Cgiv	0.93	2.90	3.670 (5)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3	0.93	2.41	3.010 (6)	122
N3—H3⋯O5i	0.86	2.19	2.900 (5)	140
C3—H3B⋯O2ii	0.97	2.38	3.198 (5)	141
C6—H6⋯O4iii	0.93	2.45	3.290 (5)	151
C12—H12⋯O5iii	0.93	2.60	3.242 (5)	127
C14—H14⋯Cg iv	0.93	2.90	3.670 (5)	141

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