Crystal structure of 2-(2-methyl­phen­yl)-1,3-thia­zolo[4,5-b]pyridine

Gamal A El-Hiti; Keith Smith; Amany S Hegazy; Saud A Alanazi; Benson M Kariuki

doi:10.1107/S2056989015012797

. 2015 Jul 8;71(Pt 8):o562–o563. doi: 10.1107/S2056989015012797

Crystal structure of 2-(2-methylphenyl)-1,3-thiazolo[4,5-b]pyridine

Gamal A El-Hiti ^a,^*, Keith Smith ^b, Amany S Hegazy ^b, Saud A Alanazi ^a, Benson M Kariuki ^b,^*

PMCID: PMC4571397 PMID: 26396797

Abstract

In the title molecule, C₁₃H₁₀N₂S, the dihedral angle between the planes through the non-H atoms of the methylbenzene and thiazolopyridine groups is 36.61 (5)°. In the crystal, the thiazolopyridine groups of inversion-related molecules overlap, with a minimum ring-centroid separation of 3.6721 (9) Å. Furthermore, the methylbenzene groups from neighbouring molecules interact edge-to-face at an angle of 71.66 (5)°. In addition, weak C—H⋯ N hydrogen bonds form chains exending along [100].

Keywords: crystal structure, thiazolopyridine, hydrogen bonding

Related literature

Various thiazolopyridine derivatives have been synthesised using different synthetic methods, see: Luo et al. (2015 ▸); Chaban et al. (2013 ▸); Leysen et al. (1984 ▸); Lee et al. (2010 ▸); Rao et al. (2009 ▸); Johnson et al. (2006 ▸); El-Hiti (2003 ▸); Smith et al. (1994 ▸, 1995 ▸). For the X-ray crystal structures of related compounds, see: El-Hiti et al. (2014 ▸; 2015 ▸); Yu et al. (2007 ▸). graphic file with name e-71-0o562-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₀N₂S
M _r = 226.29
Orthorhombic,
a = 7.6702 (1) Å
b = 12.6492 (3) Å
c = 22.9821 (5) Å
V = 2229.77 (8) Å³
Z = 8
Cu Kα radiation
μ = 2.33 mm⁻¹
T = 293 K
0.26 × 0.17 × 0.05 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas CCD detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T _min = 0.960, T _max = 0.989
7263 measured reflections
2234 independent reflections
1959 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.106
S = 1.03
2234 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and CHEMDRAW Ultra (Cambridge Soft, 2001 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015012797/zs2340sup1.cif

e-71-0o562-sup1.cif^{(274.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012797/zs2340Isup2.hkl

e-71-0o562-Isup2.hkl^{(123KB, hkl)}

Click here for additional data file.^{(4.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015012797/zs2340Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

13 10 2 . DOI: 10.1107/S2056989015012797/zs2340fig1.tif

The asymmetric unit of C₁₃H₁₀N₂O with atom labels and 50% probability displacement ellipsoids for non-hydrogen atoms.

Click here for additional data file.^{(1.8MB, tif)}

a . DOI: 10.1107/S2056989015012797/zs2340fig2.tif

The crystal packing viewed along the a axis of the unit cell.

CCDC reference: 1410117

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C4H4N2ⁱ	0.93	2.63	3.371(2)	137

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors extend their appreciation to the British Council, Riyadh, Saudi Arabia, for funding this research and to Cardiff University for continued support.

supplementary crystallographic information

S1. Introduction

Various thiazolopyridine derivatives have been synthesised using different synthetic methods (Luo et al., 2015; Chaban et al., 2013; Leysen et al., 1984; Lee et al., 2010; Rao et al., 2009; Johnson et al., 2006; El-Hiti, 2003; Smith et al., 1994, 1995). We have synthesized 2-(2-methylphenyl)-1,3-thiazolo[4,5-b]pyridine in high yield (El-Hiti, 2003; Smith et al., 1995) as a continuation of our research directed towards the development of novel synthetic routes towards heterocyclic derivatives. The X-ray structures for related compounds have been reported previously (El-Hiti et al., 2014, 2015; Yu et al., 2007).

S2. Experimental

S2.1. Synthesis and crystallization

2-(2-Methylphenyl)-1,3-thiazolo[4,5-b]pyridine was obtained in 89% yield from acid hydrolysis of 3-(diisopropylaminothiocarbonylthio)-2-(2-methylbenzoylamino)pyridine under reflux (Smith et al., 1995) or in 61% yield from the reaction of 3-(diisopropylaminothiocarbonylthio)-2-aminopyridine with 2-methylbenzoic acid in the presence of phosphorus oxychloride under reflux (El-Hiti, 2003). Crystallization from diethyl ether gave colourless crystals of the title compound. The NMR and mass spectral data for this compound were consistent with those reported (Smith et al., 1995).

S2.2. Refinement

H atoms were positioned geometrically and refined using a riding model with U_iso(H) constrained to be 1.2 times U_eq for the atom it is bonded to except for methyl groups where it was 1.5 times with free rotation about the C—C bond.

S3. Comment

The asymmetric unit consists of one molecule of C₁₃H₁₀N₂S (Fig. 1). In the molecule, the angle between the least squares planes through the nonhydrogen atoms of the methylphenyl and thiazolopyridine groups is 36.61 (5)°. In the crystal (Fig 2), the thiazolopyridine groups of adjacent inversion-related molecules are parallel and overlap fully with a minimum ring centroid separation of 3.6721 (9) Å between the 5-membered and 6-membered components of the groups (related by -x, -y +1.-z +1) . Methylphenyl groups from neighbouring molecules interact in an edge-to-face fashion with a dihedral angle between the rings of 71.66 (5)°. A weak intermolecular C4—H···N2ⁱ contact (Table 1) forms chains of molecules extending along [100].