organic compounds
2-Chloro-5-({[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}methyl)pyridine
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
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 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).
see: MamoloExperimental
Crystal data
|
Data collection: SMART (Bruker, 1998); cell 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
https://doi.org/10.1107/S1600536811050410/rz2672sup1.cif
contains datablocks global, I. DOI: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
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
were obtained by evaporation of an ethanol solution.All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å, and with with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.
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
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 π···π interactions or C—H···π short contacts are observed, the structure being stabilized only by van der Waals interactions.
no hydrogen bonds,For background to the biological activity of
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).Data collection: SMART (Bruker, 1998); cell
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.Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids. |
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 monochromator | 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 |
C15H12ClN3O2S | V = 2995.6 (10) Å3 |
Mr = 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 |
Bruker SMART APEX area-detector diffractometer | 2730 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1514 reflections with I > 2σ(I) |
Tmin = 0.886, Tmax = 0.980 | Rint = 0.089 |
5300 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.24 e Å−3 |
2730 reflections | Δρmin = −0.23 e Å−3 |
201 parameters |
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) |
Experimental details
Crystal data | |
Chemical formula | C15H12ClN3O2S |
Mr | 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) |
Tmin, Tmax | 0.886, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5300, 2730, 1514 |
Rint | 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 |
Δρmax, Δρmin (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.
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.