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

In the title mol-ecule, C9H10N2S, one of the methyl groups is almost co-planar with the thia-zolo-pyridine rings with a deviation of 0.311 (3) Å from the least-squares plane of the thia-zolo-pyridine group. In the crystal, weak C-H⋯N hydrogen-bonding inter-actions lead to the formation of chains along [011].

Related literature

For related compounds, see: Smith et al. (1994 ▸, 1995 ▸); El-Hiti (2003 ▸); Johnson et al. (2006 ▸); Thomae et al. (2008 ▸); Rao et al. (2009 ▸); Lee et al. (2010 ▸); Luo et al. (2015 ▸). For the X-ray crystal structures of related compounds, see: Yu et al. (2007 ▸); El-Hiti et al. (2014 ▸).

Experimental

Crystal data

C9H10N2S

M = 178.25

Orthorhombic,

a = 9.6376 (2) Å

b = 10.1602 (2) Å

c = 8.9254 (2) Å

V = 873.98 (3) Å3

Z = 4

Cu Kα radiation

μ = 2.81 mm−1

T = 150 K

0.23 × 0.20 × 0.14 mm

Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.897, T max = 0.940

2848 measured reflections

1366 independent reflections

1351 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.057

S = 1.08

1366 reflections

111 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 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/S2056989015006039/zs2329sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006039/zs2329Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006039/zs2329Isup3.cml

Click here for additional data file.

9 10 2 . DOI: 10.1107/S2056989015006039/zs2329fig1.tif

A mol­ecule of C9H10N2S with atom labels and 50% probability displacement ellipsoids for non-hydrogen atoms.

Click here for additional data file.

c . DOI: 10.1107/S2056989015006039/zs2329fig2.tif

Crystal structure packing viewed down the c axis with C—H⋯N inter­actions shown as dotted lines.

CCDC reference: 1056012

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

C9H10N2S	Dx = 1.355 Mg m−3
Mr = 178.25	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pna21	Cell parameters from 2276 reflections
a = 9.6376 (2) Å	θ = 6.3–73.8°
b = 10.1602 (2) Å	µ = 2.81 mm−1
c = 8.9254 (2) Å	T = 150 K
V = 873.98 (3) Å3	Block, colourless
Z = 4	0.23 × 0.20 × 0.14 mm
F(000) = 376

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	1366 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	1351 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.012
Detector resolution: 10.5082 pixels mm-1	θmax = 74.0°, θmin = 6.3°
ω scans	h = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −12→8
Tmin = 0.897, Tmax = 0.940	l = −10→10
2848 measured reflections

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H-atom parameters constrained
wR(F2) = 0.057	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.1081P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1366 reflections	Δρmax = 0.19 e Å−3
111 parameters	Δρmin = −0.20 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	0.13501 (18)	0.59856 (18)	0.8660 (2)	0.0227 (4)
C2	0.23657 (17)	0.67547 (17)	1.1015 (2)	0.0208 (3)
C3	0.29550 (18)	0.56187 (17)	1.0365 (2)	0.0203 (3)
C4	0.2865 (2)	0.72261 (17)	1.2365 (3)	0.0257 (4)
H4	0.2483	0.7985	1.2829	0.031*
C5	0.39534 (19)	0.6532 (2)	1.3007 (3)	0.0279 (4)
H5	0.4342	0.6813	1.3931	0.034*
C6	0.44760 (19)	0.54145 (19)	1.2283 (3)	0.0273 (4)
H6	0.5220	0.4959	1.2752	0.033*
C7	0.05003 (18)	0.57871 (19)	0.7259 (3)	0.0271 (4)
H7	0.0177	0.4852	0.7251	0.033*
C8	−0.0783 (2)	0.6663 (2)	0.7204 (3)	0.0365 (5)
H8A	−0.1375	0.6475	0.8070	0.055*
H8B	−0.1299	0.6488	0.6279	0.055*
H8C	−0.0499	0.7589	0.7227	0.055*
C9	0.1411 (2)	0.5992 (3)	0.5875 (3)	0.0421 (6)
H9A	0.1666	0.6923	0.5796	0.063*
H9B	0.0897	0.5727	0.4977	0.063*
H9C	0.2253	0.5457	0.5966	0.063*
N1	0.23563 (16)	0.52156 (16)	0.9037 (2)	0.0241 (3)
N2	0.40055 (14)	0.49434 (16)	1.0985 (2)	0.0254 (4)
S1	0.10273 (4)	0.73079 (4)	0.98822 (7)	0.02515 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0205 (8)	0.0253 (8)	0.0224 (10)	−0.0013 (7)	0.0032 (7)	−0.0026 (8)
C2	0.0212 (8)	0.0210 (7)	0.0203 (9)	−0.0011 (6)	0.0033 (6)	−0.0004 (7)
C3	0.0199 (7)	0.0206 (7)	0.0204 (9)	−0.0026 (6)	0.0032 (6)	−0.0024 (7)
C4	0.0292 (9)	0.0258 (9)	0.0221 (9)	−0.0028 (7)	0.0018 (8)	−0.0061 (8)
C5	0.0302 (9)	0.0353 (11)	0.0184 (9)	−0.0058 (7)	−0.0024 (7)	0.0002 (9)
C6	0.0258 (8)	0.0303 (9)	0.0259 (9)	0.0005 (7)	−0.0035 (8)	0.0042 (8)
C7	0.0266 (8)	0.0293 (9)	0.0254 (9)	−0.0036 (7)	−0.0032 (8)	−0.0030 (8)
C8	0.0293 (9)	0.0428 (12)	0.0374 (13)	0.0037 (9)	−0.0127 (9)	−0.0071 (11)
C9	0.0351 (11)	0.0705 (16)	0.0207 (11)	−0.0072 (11)	−0.0024 (8)	−0.0025 (11)
N1	0.0231 (7)	0.0264 (8)	0.0229 (8)	0.0012 (6)	0.0001 (6)	−0.0067 (7)
N2	0.0238 (8)	0.0239 (7)	0.0284 (9)	0.0024 (6)	−0.0016 (6)	−0.0002 (7)
S1	0.0242 (2)	0.0266 (2)	0.0246 (2)	0.00703 (13)	−0.0007 (2)	−0.0048 (2)

C1—N1	1.291 (2)	C6—N2	1.334 (3)
C1—C7	1.508 (3)	C6—H6	0.9500
C1—S1	1.7585 (19)	C7—C8	1.524 (3)
C2—C4	1.383 (3)	C7—C9	1.530 (3)
C2—C3	1.411 (2)	C7—H7	1.0000
C2—S1	1.7325 (19)	C8—H8A	0.9800
C3—N2	1.342 (2)	C8—H8B	0.9800
C3—N1	1.380 (2)	C8—H8C	0.9800
C4—C5	1.388 (3)	C9—H9A	0.9800
C4—H4	0.9500	C9—H9B	0.9800
C5—C6	1.400 (3)	C9—H9C	0.9800
C5—H5	0.9500
N1—C1—C7	122.91 (17)	C8—C7—C9	111.1 (2)
N1—C1—S1	115.73 (15)	C1—C7—H7	107.6
C7—C1—S1	121.36 (14)	C8—C7—H7	107.6
C4—C2—C3	120.08 (17)	C9—C7—H7	107.6
C4—C2—S1	130.92 (14)	C7—C8—H8A	109.5
C3—C2—S1	108.98 (14)	C7—C8—H8B	109.5
N2—C3—N1	121.16 (16)	H8A—C8—H8B	109.5
N2—C3—C2	123.53 (18)	C7—C8—H8C	109.5
N1—C3—C2	115.30 (16)	H8A—C8—H8C	109.5
C2—C4—C5	116.51 (17)	H8B—C8—H8C	109.5
C2—C4—H4	121.7	C7—C9—H9A	109.5
C5—C4—H4	121.7	C7—C9—H9B	109.5
C4—C5—C6	119.6 (2)	H9A—C9—H9B	109.5
C4—C5—H5	120.2	C7—C9—H9C	109.5
C6—C5—H5	120.2	H9A—C9—H9C	109.5
N2—C6—C5	124.73 (18)	H9B—C9—H9C	109.5
N2—C6—H6	117.6	C1—N1—C3	110.99 (16)
C5—C6—H6	117.6	C6—N2—C3	115.54 (16)
C1—C7—C8	112.90 (18)	C2—S1—C1	89.00 (9)
C1—C7—C9	109.85 (15)
C4—C2—C3—N2	−0.3 (3)	C7—C1—N1—C3	−179.88 (16)
S1—C2—C3—N2	−179.06 (14)	S1—C1—N1—C3	0.6 (2)
C4—C2—C3—N1	178.46 (16)	N2—C3—N1—C1	178.62 (17)
S1—C2—C3—N1	−0.3 (2)	C2—C3—N1—C1	−0.1 (2)
C3—C2—C4—C5	0.4 (3)	C5—C6—N2—C3	0.0 (3)
S1—C2—C4—C5	178.89 (15)	N1—C3—N2—C6	−178.61 (17)
C2—C4—C5—C6	−0.4 (3)	C2—C3—N2—C6	0.1 (3)
C4—C5—C6—N2	0.2 (3)	C4—C2—S1—C1	−178.11 (19)
N1—C1—C7—C8	169.47 (19)	C3—C2—S1—C1	0.50 (14)
S1—C1—C7—C8	−11.0 (2)	N1—C1—S1—C2	−0.64 (15)
N1—C1—C7—C9	−65.9 (3)	C7—C1—S1—C2	179.79 (16)
S1—C1—C7—C9	113.64 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N1i	0.95	2.51	3.391 (2)	153

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C4H4N1i	0.95	2.51	3.391(2)	153

Symmetry code: (i) .