2-Chloro-5-({[5-(4-meth-oxy-phen-yl)-1,3,4-oxadiazol-2-yl]-sulfanyl}-meth-yl)pyridine.

In the title compound, C(15)H(12)ClN(3)O(2)S, the central oxadiazole ring forms dihedral angles of 7.72 (14) and 69.86 (12)° with the benzene and pyridine rings, respectively. The crystal packing is governed only by van der Waals inter-actions.

Related literature

For background to the biological activity of heterocyclic compounds, see: Mamolo et al. (2001 ▶); Liu et al. (2001 ▶); Demirbas et al. (2004 ▶). For the synthesis, see: Zareef et al. (2008 ▶); Wu et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12ClN3O2S

M = 333.80

Orthorhombic,

a = 12.311 (2) Å

b = 8.1229 (15) Å

c = 29.956 (6) Å

V = 2995.6 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.40 mm−1

T = 298 K

0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.886, T max = 0.980

5300 measured reflections

2730 independent reflections

1514 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.147

S = 0.97

2730 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050410/rz2672sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050410/rz2672Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050410/rz2672Isup3.cml

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

C15H12ClN3O2S	F(000) = 1376
Mr = 333.80	Dx = 1.480 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2256 reflections
a = 12.311 (2) Å	θ = 4.2–26°
b = 8.1229 (15) Å	µ = 0.40 mm−1
c = 29.956 (6) Å	T = 298 K
V = 2995.6 (10) Å3	Needle, yellow
Z = 8	0.30 × 0.20 × 0.05 mm

Bruker SMART APEX area-detector diffractometer	2730 independent reflections
Radiation source: fine-focus sealed tube	1514 reflections with I > 2σ(I)
graphite	Rint = 0.089
ω scans	θmax = 25.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.886, Tmax = 0.980	k = −9→0
5300 measured reflections	l = 0→35

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0512P)2] where P = (Fo2 + 2Fc2)/3
2730 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.23 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
C1	0.5087 (4)	−0.2986 (7)	0.24553 (18)	0.0714 (16)
H1A	0.5338	−0.1867	0.2461	0.107*
H1B	0.5102	−0.3387	0.2154	0.107*
H1C	0.5552	−0.3654	0.2638	0.107*
C2	0.3779 (4)	−0.2211 (6)	0.29959 (14)	0.0472 (11)
C3	0.4536 (3)	−0.1655 (5)	0.33013 (14)	0.0455 (11)
H3	0.5271	−0.1861	0.3256	0.055*
C4	0.4201 (3)	−0.0794 (5)	0.36728 (13)	0.0420 (11)
H4	0.4715	−0.0414	0.3876	0.050*
C5	0.3108 (3)	−0.0486 (5)	0.37482 (13)	0.0371 (10)
C6	0.2359 (3)	−0.1103 (6)	0.34482 (14)	0.0507 (12)
H6	0.1621	−0.0936	0.3498	0.061*
C7	0.2693 (4)	−0.1962 (6)	0.30773 (15)	0.0600 (14)
H7	0.2179	−0.2379	0.2880	0.072*
C8	0.2797 (3)	0.0489 (5)	0.41334 (13)	0.0364 (10)
C9	0.1752 (3)	0.1674 (5)	0.46014 (14)	0.0396 (11)
C10	0.1054 (4)	0.3455 (5)	0.52966 (12)	0.0442 (11)
H10A	0.1658	0.4113	0.5190	0.053*
H10B	0.0493	0.4206	0.5397	0.053*
C11	0.1431 (3)	0.2446 (5)	0.56864 (13)	0.0384 (10)
C12	0.2518 (3)	0.2350 (6)	0.57983 (14)	0.0473 (11)
H12	0.3018	0.2869	0.5613	0.057*
C13	0.2170 (4)	0.0810 (6)	0.64102 (14)	0.0454 (12)
C14	0.1079 (4)	0.0776 (6)	0.63222 (15)	0.0518 (12)
H14	0.0604	0.0206	0.6507	0.062*
C15	0.0706 (3)	0.1604 (6)	0.59533 (14)	0.0481 (12)
H15	−0.0030	0.1597	0.5884	0.058*
N1	0.3412 (3)	0.1276 (4)	0.44087 (11)	0.0436 (9)
N2	0.2721 (3)	0.2060 (5)	0.47184 (11)	0.0447 (9)
N3	0.2897 (3)	0.1545 (5)	0.61608 (12)	0.0501 (10)
O1	0.4021 (3)	−0.3058 (5)	0.26198 (11)	0.0770 (12)
O2	0.1718 (2)	0.0681 (3)	0.42357 (9)	0.0415 (7)
S	0.05258 (9)	0.22470 (15)	0.48350 (4)	0.0480 (3)
Cl1	0.26557 (11)	−0.01868 (18)	0.68838 (4)	0.0683 (4)

	U11	U22	U33	U12	U13	U23
C1	0.066 (3)	0.076 (4)	0.072 (4)	0.002 (3)	0.013 (3)	−0.028 (3)
C2	0.049 (3)	0.043 (3)	0.049 (3)	−0.003 (2)	0.002 (2)	−0.007 (2)
C3	0.040 (2)	0.046 (3)	0.050 (3)	−0.002 (2)	0.003 (2)	0.000 (2)
C4	0.043 (3)	0.041 (3)	0.041 (3)	−0.003 (2)	−0.008 (2)	−0.002 (2)
C5	0.037 (2)	0.036 (2)	0.038 (2)	−0.004 (2)	−0.0005 (18)	0.008 (2)
C6	0.033 (2)	0.058 (3)	0.061 (3)	0.000 (2)	0.003 (2)	−0.007 (3)
C7	0.044 (3)	0.068 (4)	0.068 (3)	−0.007 (3)	−0.005 (2)	−0.021 (3)
C8	0.037 (2)	0.030 (2)	0.043 (2)	0.000 (2)	−0.0009 (19)	0.003 (2)
C9	0.044 (3)	0.032 (2)	0.043 (3)	0.001 (2)	0.001 (2)	0.004 (2)
C10	0.051 (3)	0.036 (2)	0.045 (3)	0.009 (2)	0.010 (2)	0.001 (2)
C11	0.043 (2)	0.029 (2)	0.044 (2)	0.004 (2)	0.005 (2)	−0.001 (2)
C12	0.046 (2)	0.046 (3)	0.049 (3)	−0.008 (2)	0.008 (2)	−0.001 (2)
C13	0.053 (3)	0.036 (3)	0.048 (3)	0.005 (2)	−0.012 (2)	0.000 (2)
C14	0.045 (3)	0.047 (3)	0.063 (3)	−0.009 (2)	0.005 (2)	0.020 (3)
C15	0.032 (2)	0.050 (3)	0.062 (3)	0.002 (2)	0.001 (2)	0.013 (2)
N1	0.039 (2)	0.043 (2)	0.049 (2)	0.0011 (19)	0.0011 (17)	−0.0014 (19)
N2	0.036 (2)	0.049 (2)	0.049 (2)	0.0006 (18)	0.0023 (16)	−0.0050 (19)
N3	0.042 (2)	0.054 (3)	0.054 (2)	0.000 (2)	0.0002 (19)	0.001 (2)
O1	0.061 (2)	0.098 (3)	0.072 (2)	−0.015 (2)	0.0116 (19)	−0.045 (2)
O2	0.0362 (16)	0.0386 (17)	0.0497 (19)	−0.0011 (14)	−0.0003 (13)	0.0021 (15)
S	0.0375 (6)	0.0510 (7)	0.0556 (7)	0.0047 (6)	0.0017 (5)	0.0007 (7)
Cl1	0.0728 (9)	0.0660 (9)	0.0661 (8)	−0.0008 (7)	−0.0169 (7)	0.0169 (7)

C1—O1	1.404 (6)	C9—N2	1.282 (5)
C1—H1A	0.9600	C9—O2	1.361 (5)
C1—H1B	0.9600	C9—S	1.728 (4)
C1—H1C	0.9600	C10—C11	1.500 (5)
C2—O1	1.353 (5)	C10—S	1.816 (4)
C2—C3	1.381 (6)	C10—H10A	0.9700
C2—C7	1.375 (6)	C10—H10B	0.9700
C3—C4	1.378 (5)	C11—C15	1.379 (5)
C3—H3	0.9300	C11—C12	1.383 (6)
C4—C5	1.387 (5)	C12—N3	1.350 (5)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.382 (5)	C13—N3	1.310 (5)
C5—C8	1.451 (5)	C13—C14	1.368 (6)
C6—C7	1.375 (6)	C13—Cl1	1.740 (4)
C6—H6	0.9300	C14—C15	1.373 (6)
C7—H7	0.9300	C14—H14	0.9300
C8—N1	1.289 (5)	C15—H15	0.9300
C8—O2	1.372 (4)	N1—N2	1.411 (4)
O1—C1—H1A	109.5	O2—C9—S	117.3 (3)
O1—C1—H1B	109.5	C11—C10—S	114.1 (3)
H1A—C1—H1B	109.5	C11—C10—H10A	108.7
O1—C1—H1C	109.5	S—C10—H10A	108.7
H1A—C1—H1C	109.5	C11—C10—H10B	108.7
H1B—C1—H1C	109.5	S—C10—H10B	108.7
O1—C2—C3	124.7 (4)	H10A—C10—H10B	107.6
O1—C2—C7	115.9 (4)	C15—C11—C12	117.2 (4)
C3—C2—C7	119.4 (4)	C15—C11—C10	121.5 (4)
C4—C3—C2	120.0 (4)	C12—C11—C10	121.3 (4)
C4—C3—H3	120.0	N3—C12—C11	123.9 (4)
C2—C3—H3	120.0	N3—C12—H12	118.1
C3—C4—C5	120.9 (4)	C11—C12—H12	118.1
C3—C4—H4	119.6	N3—C13—C14	124.7 (4)
C5—C4—H4	119.6	N3—C13—Cl1	116.2 (3)
C6—C5—C4	118.4 (4)	C14—C13—Cl1	119.0 (4)
C6—C5—C8	122.6 (4)	C13—C14—C15	118.2 (4)
C4—C5—C8	119.0 (4)	C13—C14—H14	120.9
C7—C6—C5	120.7 (4)	C15—C14—H14	120.9
C7—C6—H6	119.7	C14—C15—C11	119.6 (4)
C5—C6—H6	119.7	C14—C15—H15	120.2
C6—C7—C2	120.6 (4)	C11—C15—H15	120.2
C6—C7—H7	119.7	C8—N1—N2	106.8 (3)
C2—C7—H7	119.7	C9—N2—N1	105.7 (3)
N1—C8—O2	111.7 (4)	C13—N3—C12	116.3 (4)
N1—C8—C5	128.6 (4)	C2—O1—C1	118.4 (4)
O2—C8—C5	119.7 (4)	C9—O2—C8	102.5 (3)
N2—C9—O2	113.2 (4)	C9—S—C10	98.1 (2)
N2—C9—S	129.5 (4)
O1—C2—C3—C4	179.6 (4)	C13—C14—C15—C11	−0.4 (7)
C7—C2—C3—C4	−3.0 (7)	C12—C11—C15—C14	2.6 (7)
C2—C3—C4—C5	0.6 (7)	C10—C11—C15—C14	−176.1 (4)
C3—C4—C5—C6	1.8 (6)	O2—C8—N1—N2	−0.1 (5)
C3—C4—C5—C8	−177.3 (4)	C5—C8—N1—N2	178.7 (4)
C4—C5—C6—C7	−1.8 (7)	O2—C9—N2—N1	0.2 (5)
C8—C5—C6—C7	177.2 (4)	S—C9—N2—N1	−179.1 (3)
C5—C6—C7—C2	−0.6 (7)	C8—N1—N2—C9	0.0 (4)
O1—C2—C7—C6	−179.4 (4)	C14—C13—N3—C12	1.6 (7)
C3—C2—C7—C6	3.0 (8)	Cl1—C13—N3—C12	−178.6 (3)
C6—C5—C8—N1	−171.9 (4)	C11—C12—N3—C13	0.9 (7)
C4—C5—C8—N1	7.2 (6)	C3—C2—O1—C1	−19.0 (7)
C6—C5—C8—O2	6.8 (6)	C7—C2—O1—C1	163.5 (5)
C4—C5—C8—O2	−174.1 (4)	N2—C9—O2—C8	−0.2 (4)
S—C10—C11—C15	−69.6 (5)	S—C9—O2—C8	179.1 (3)
S—C10—C11—C12	111.7 (4)	N1—C8—O2—C9	0.2 (4)
C15—C11—C12—N3	−3.0 (7)	C5—C8—O2—C9	−178.7 (3)
C10—C11—C12—N3	175.8 (4)	N2—C9—S—C10	−2.2 (5)
N3—C13—C14—C15	−1.8 (8)	O2—C9—S—C10	178.6 (3)
Cl1—C13—C14—C15	178.4 (4)	C11—C10—S—C9	−79.9 (3)