Crystal structure of 2-(2-methyl-phen-yl)-1,3-thia-zolo[4,5-b]pyridine.

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

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 ▸).

Experimental

Crystal data

C13H10N2S

M = 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

Δρmax = 0.17 e Å−3

Δρmin = −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 ▸).

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

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

Click here for additional data file.

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

Click here for additional data file.

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.

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

C13H10N2S	Dx = 1.348 Mg m−3
Mr = 226.29	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 3613 reflections
a = 7.6702 (1) Å	θ = 3.8–74.0°
b = 12.6492 (3) Å	µ = 2.33 mm−1
c = 22.9821 (5) Å	T = 293 K
V = 2229.77 (8) Å3	Block, colourless
Z = 8	0.26 × 0.17 × 0.05 mm
F(000) = 944

Agilent SuperNova Dual Source diffractometer with an Atlas CCD detector	1959 reflections with I > 2σ(I)
ω scans	Rint = 0.019
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	θmax = 74.0°, θmin = 3.9°
Tmin = 0.960, Tmax = 0.989	h = −9→6
7263 measured reflections	k = −12→15
2234 independent reflections	l = −28→27

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.2883P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2234 reflections	Δρmax = 0.17 e Å−3
146 parameters	Δρmin = −0.27 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.

	x	y	z	Uiso*/Ueq
C1	0.21789 (18)	0.50224 (11)	0.38130 (6)	0.0457 (3)
C2	0.03446 (19)	0.40362 (11)	0.43105 (6)	0.0496 (3)
C3	−0.07616 (19)	0.48902 (12)	0.42082 (6)	0.0527 (3)
C4	−0.1768 (3)	0.31679 (15)	0.48019 (8)	0.0706 (5)
H4	−0.2140	0.2579	0.5010	0.085*
C5	−0.2954 (2)	0.39752 (16)	0.47141 (8)	0.0705 (5)
H5	−0.4082	0.3917	0.4859	0.085*
C6	−0.2461 (2)	0.48645 (16)	0.44130 (8)	0.0670 (4)
H6	−0.3229	0.5422	0.4350	0.080*
C7	0.37539 (18)	0.54080 (11)	0.35116 (6)	0.0470 (3)
C8	0.48582 (19)	0.47301 (13)	0.31980 (6)	0.0527 (3)
C9	0.6265 (2)	0.51824 (15)	0.29070 (7)	0.0644 (4)
H9	0.6997	0.4749	0.2690	0.077*
C10	0.6608 (2)	0.62498 (15)	0.29292 (8)	0.0675 (4)
H10	0.7555	0.6528	0.2728	0.081*
C11	0.5547 (2)	0.69041 (14)	0.32501 (8)	0.0664 (4)
H11	0.5787	0.7623	0.3274	0.080*
C12	0.4124 (2)	0.64853 (12)	0.35362 (7)	0.0563 (4)
H12	0.3399	0.6930	0.3749	0.068*
C13	0.4583 (3)	0.35571 (14)	0.31637 (9)	0.0730 (5)
H13A	0.5337	0.3264	0.2872	0.109*
H13B	0.3391	0.3414	0.3064	0.109*
H13C	0.4845	0.3243	0.3534	0.109*
N1	0.20074 (17)	0.41287 (9)	0.40814 (5)	0.0514 (3)
N2	−0.0128 (2)	0.31754 (12)	0.46089 (7)	0.0659 (4)
S1	0.03278 (5)	0.58334 (3)	0.38069 (2)	0.06317 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0444 (7)	0.0476 (7)	0.0451 (7)	0.0040 (5)	−0.0043 (5)	−0.0027 (5)
C2	0.0486 (8)	0.0529 (8)	0.0471 (7)	0.0024 (6)	0.0008 (6)	−0.0006 (6)
C3	0.0452 (7)	0.0625 (8)	0.0502 (7)	0.0045 (6)	−0.0035 (6)	0.0007 (6)
C4	0.0698 (10)	0.0746 (11)	0.0673 (10)	−0.0082 (8)	0.0169 (8)	0.0047 (8)
C5	0.0526 (9)	0.0951 (13)	0.0637 (9)	−0.0068 (8)	0.0099 (7)	−0.0010 (9)
C6	0.0474 (8)	0.0870 (12)	0.0667 (9)	0.0106 (8)	0.0017 (7)	0.0036 (8)
C7	0.0441 (7)	0.0502 (7)	0.0468 (7)	0.0005 (6)	−0.0055 (5)	0.0007 (5)
C8	0.0497 (7)	0.0567 (8)	0.0517 (8)	0.0026 (6)	−0.0004 (6)	−0.0013 (6)
C9	0.0562 (9)	0.0778 (11)	0.0591 (9)	0.0018 (8)	0.0097 (7)	−0.0019 (8)
C10	0.0600 (9)	0.0795 (11)	0.0630 (9)	−0.0143 (8)	0.0057 (7)	0.0089 (8)
C11	0.0685 (10)	0.0609 (9)	0.0700 (10)	−0.0140 (8)	−0.0009 (8)	0.0052 (8)
C12	0.0555 (8)	0.0530 (8)	0.0605 (8)	−0.0010 (7)	−0.0038 (7)	−0.0009 (6)
C13	0.0769 (12)	0.0564 (9)	0.0856 (12)	0.0054 (8)	0.0211 (9)	−0.0104 (9)
N1	0.0490 (7)	0.0508 (7)	0.0544 (7)	0.0062 (5)	0.0033 (5)	0.0039 (5)
N2	0.0665 (8)	0.0622 (8)	0.0691 (8)	0.0026 (6)	0.0133 (7)	0.0116 (7)
S1	0.0491 (3)	0.0616 (3)	0.0789 (3)	0.01227 (16)	0.00281 (17)	0.01779 (18)

C1—N1	1.2944 (18)	C7—C12	1.393 (2)
C1—C7	1.476 (2)	C7—C8	1.404 (2)
C1—S1	1.7518 (14)	C8—C9	1.392 (2)
C2—N2	1.337 (2)	C8—C13	1.501 (2)
C2—N1	1.3848 (19)	C9—C10	1.377 (3)
C2—C3	1.394 (2)	C9—H9	0.9300
C3—C6	1.386 (2)	C10—C11	1.375 (3)
C3—S1	1.7240 (16)	C10—H10	0.9300
C4—N2	1.334 (2)	C11—C12	1.380 (2)
C4—C5	1.382 (3)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.374 (3)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—H6	0.9300	C13—H13C	0.9600
N1—C1—C7	126.56 (13)	C7—C8—C13	123.08 (14)
N1—C1—S1	115.65 (11)	C10—C9—C8	122.24 (16)
C7—C1—S1	117.79 (10)	C10—C9—H9	118.9
N2—C2—N1	120.92 (13)	C8—C9—H9	118.9
N2—C2—C3	123.54 (14)	C11—C10—C9	119.80 (15)
N1—C2—C3	115.54 (13)	C11—C10—H10	120.1
C6—C3—C2	119.80 (15)	C9—C10—H10	120.1
C6—C3—S1	130.81 (13)	C10—C11—C12	119.51 (16)
C2—C3—S1	109.37 (11)	C10—C11—H11	120.2
N2—C4—C5	124.51 (17)	C12—C11—H11	120.2
N2—C4—H4	117.7	C11—C12—C7	121.16 (16)
C5—C4—H4	117.7	C11—C12—H12	119.4
C6—C5—C4	119.85 (16)	C7—C12—H12	119.4
C6—C5—H5	120.1	C8—C13—H13A	109.5
C4—C5—H5	120.1	C8—C13—H13B	109.5
C5—C6—C3	116.67 (17)	H13A—C13—H13B	109.5
C5—C6—H6	121.7	C8—C13—H13C	109.5
C3—C6—H6	121.7	H13A—C13—H13C	109.5
C12—C7—C8	119.67 (14)	H13B—C13—H13C	109.5
C12—C7—C1	118.11 (13)	C1—N1—C2	110.40 (12)
C8—C7—C1	122.21 (13)	C4—N2—C2	115.61 (15)
C9—C8—C7	117.58 (15)	C3—S1—C1	89.04 (7)
C9—C8—C13	119.33 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2i	0.93	2.63	3.371 (2)	137

Table 1

Hydrogen-bond geometry (, )

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

Symmetry code: (i) .