2-Chloro-5-({[5-(4-meth­oxy­phen­yl)-1,3,4-oxadiazol-2-yl]­sulfanyl}­meth­yl)pyridine

Ji, H.; Xu, X.-D.

doi:10.1107/S1600536811050410

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3490

https://doi.org/10.1107/S1600536811050410

Open

access

2-Chloro-5-({[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}methyl)pyridine

Hao Ji ^a and Xu-Dong Xu ^a ^*

^aDepartment of Bioengineering, College of Medicine, Southeast University, Nanjing 210009, People's Republic of China, and Jiangsu Tiansheng Pharmaceutical, Company Limited Jurong City 212415, Jiangsu Province, People's Republic of China
^*Correspondence e-mail: xuxd5555@163.com

(Received 12 November 2011; accepted 24 November 2011; online 30 November 2011)

In the title compound, C₁₅H₁₂ClN₃O₂S, 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 interactions.

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_r = 333.80
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.147
S = 0.97
2730 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811050410/rz2672sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050410/rz2672Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050410/rz2672Isup3.cml

checkCIF report

Comment top

Heterocyclic compounds have been of great interest since many years, in particular due to the important role these compouns play in the development of medicinal chemistry (Mamolo et al., 2001; Liu et al., 2001; Demirbas et al., 2004). As a contribution to the structural characterization of new heterocyclic compounds, we report here the structure of the title compound.

In the title compound (Fig. 1) all bond lengths are within normal ranges (Allen et al., 1987). The dihedral angle between the central oxadiazole ring (N1/N2/O2/C8/C9) and the benzene (C2–C7) and pyridine (N3/C11–C15) rings are of 7.72 (14) and 69.86 (12)°, respectively. In the crystal structure, no hydrogen bonds, π···π interactions or C—H···π short contacts are observed, the structure being stabilized only by van der Waals interactions.

Related literature top

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 top

The title compound was synthesized according to the previously reported literature methods (Zareef et al., 2008; Wu et al., 2011). Single crystals suitable for X-ray diffraction analysis were obtained by evaporation of an ethanol solution.

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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.

Figures top

Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids.

2-Chloro-5-({[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}methyl)pyridine top

Crystal data top

C₁₅H₁₂ClN₃O₂S	F(000) = 1376
M_r = 333.80	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0512P)²] where P = (F_o² + 2F_c²)/3
2730 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₂ClN₃O₂S	V = 2995.6 (10) Å³
M_r = 333.80	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.311 (2) Å	µ = 0.40 mm⁻¹
b = 8.1229 (15) Å	T = 298 K
c = 29.956 (6) Å	0.30 × 0.20 × 0.05 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	2730 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1514 reflections with I > 2σ(I)
T_min = 0.886, T_max = 0.980	R_int = 0.089
5300 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 0.97	Δρ_max = 0.24 e Å⁻³
2730 reflections	Δρ_min = −0.23 e Å⁻³
201 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂ClN₃O₂S
M_r	333.80
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	12.311 (2), 8.1229 (15), 29.956 (6)
V (Å³)	2995.6 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.886, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	5300, 2730, 1514
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.147, 0.97
No. of reflections	2730
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Winconsin, USA. Google Scholar
Demirbas, N., Karaoglu, S. A., Demirbas, A. & Sancak, K. (2004). Eur. J. Med. Chem. 39, 793–804. Web of Science CrossRef PubMed CAS Google Scholar
Liu, F., Luo, X. Q., Song, B. A., Bhadury, P. S., Yang, S., Jin, L. H., Xue, W. & Hu, D. Y. (2001). Bioorg. Med. Chem. 16, 3632–3640. Web of Science CrossRef Google Scholar
Mamolo, M. G., Falagiani, V., Zampieri, D., Vio, L. & Banfi, E. (2001). Farmaco, 56, 587–592. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, X. L., Zhu, C. F., Lü, Z. D., Wei, C. S. & Liao, X. C. (2011). Chin. J. Org. Chem. 31, 824–831. CAS Google Scholar
Zareef, M., Iqbal, R., Mirza, B., Khan, K. M., Manan, A., Asim, F. & Khan, S. W. (2008). ARKIVOC, ii, 141–152. CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.