Crystal structure of 2-tert-butyl-1,3-thia-zolo[4,5-b]pyridine.

The title compound, C10H12N2S, does not contain any strong hydrogen-bond donors but two long C-H⋯N contacts are observed in the crystal structure, with the most linear inter-action linking mol-ecules along [010]. The ellipsoids of the tert-butyl group indicate large librational motion.

Related literature

For the synthesis of substituted thiazolopyridines, see: Smith et al. (1994 ▶, 1995 ▶); El-Hiti (2003 ▶); Johnson et al. (2006 ▶); Rao et al. (2009 ▶); Sahasrabudhe et al. (2009 ▶); Lee et al. (2010 ▶); Chaban et al. (2013 ▶). For the crystal structure of a related compound, see: Yu et al. (2007 ▶).

Experimental

Crystal data

C10H12N2S

M = 192.28

Orthorhombic,

a = 9.4606 (3) Å

b = 9.7999 (3) Å

c = 11.1155 (4) Å

V = 1030.55 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.42 mm−1

T = 296 K

0.40 × 0.29 × 0.14 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▶) T min = 0.721, T max = 1.000

3395 measured reflections

1996 independent reflections

1951 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.12

1996 reflections

121 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013 ▶).

Absolute structure parameter: 0.027 (7)

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, 2008 ▶); molecular graphics: CHEMDRAW ultra (Cambridge Soft, 2001 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, shelx. DOI: 10.1107/S160053681401633X/zs2307sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401633X/zs2307Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401633X/zs2307Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S160053681401633X/zs2307fig1.tif

A mol­ecule of the title compound showing atom labels and 50% probability displacement ellipsoids for non-H atoms.

Click here for additional data file.

. DOI: 10.1107/S160053681401633X/zs2307fig2.tif

Crystal structure packing with the long linear C—H⋯N contacts shown as dashed lines.

CCDC reference: 1013859

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

C10H12N2S	Dx = 1.239 Mg m−3
Mr = 192.28	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 1951 reflections
a = 9.4606 (3) Å	θ = 6.0–73.4°
b = 9.7999 (3) Å	µ = 2.42 mm−1
c = 11.1155 (4) Å	T = 296 K
V = 1030.55 (6) Å3	Plate, colourless
Z = 4	0.40 × 0.29 × 0.14 mm
F(000) = 408

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	1951 reflections with I > 2σ(I)
Radiation source: SuperNova (Cu) X-ray Source	Rint = 0.016
ω scans	θmax = 73.4°, θmin = 6.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −7→11
Tmin = 0.721, Tmax = 1.000	k = −11→12
3395 measured reflections	l = −13→10
1996 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.0815P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 0.16 e Å−3
1996 reflections	Δρmin = −0.22 e Å−3
121 parameters	Absolute structure: Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).
0 restraints	Absolute structure parameter: 0.027 (7)

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	0.8245 (2)	0.2846 (2)	0.37042 (19)	0.0458 (5)
C2	0.6967 (2)	0.4685 (2)	0.33748 (19)	0.0435 (5)
C3	0.7716 (2)	0.5154 (3)	0.4378 (2)	0.0483 (5)
C4	0.7455 (3)	0.6454 (3)	0.4822 (3)	0.0645 (6)
H4	0.7924	0.6789	0.5496	0.077*
C5	0.6470 (3)	0.7218 (3)	0.4218 (3)	0.0677 (7)
H5	0.6260	0.8097	0.4477	0.081*
C6	0.5791 (3)	0.6682 (3)	0.3225 (3)	0.0656 (7)
H6	0.5138	0.7234	0.2833	0.079*
C7	0.8831 (3)	0.1417 (2)	0.3577 (2)	0.0556 (6)
C8	0.8599 (5)	0.0641 (4)	0.4747 (3)	0.0938 (11)
H8A	0.9096	0.1090	0.5387	0.141*
H8B	0.8948	−0.0274	0.4662	0.141*
H8C	0.7608	0.0617	0.4929	0.141*
C9	1.0411 (4)	0.1506 (5)	0.3319 (5)	0.1151 (16)
H9A	1.0560	0.1983	0.2575	0.173*
H9B	1.0798	0.0603	0.3260	0.173*
H9C	1.0871	0.1990	0.3961	0.173*
C10	0.8067 (6)	0.0657 (4)	0.2577 (4)	0.124 (2)
H10A	0.7076	0.0614	0.2758	0.186*
H10B	0.8440	−0.0251	0.2513	0.186*
H10C	0.8203	0.1129	0.1829	0.186*
N1	0.72864 (19)	0.3364 (2)	0.30173 (16)	0.0453 (4)
N2	0.6004 (2)	0.5424 (2)	0.2787 (2)	0.0576 (5)
S1	0.88585 (7)	0.39028 (7)	0.48644 (5)	0.0607 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0431 (10)	0.0571 (12)	0.0371 (10)	0.0007 (10)	−0.0013 (8)	0.0016 (9)
C2	0.0423 (10)	0.0483 (11)	0.0398 (10)	−0.0043 (9)	0.0022 (8)	0.0053 (9)
C3	0.0443 (11)	0.0550 (12)	0.0457 (11)	−0.0048 (9)	0.0022 (9)	−0.0035 (9)
C4	0.0664 (15)	0.0611 (14)	0.0661 (15)	−0.0075 (11)	0.0034 (13)	−0.0160 (13)
C5	0.0707 (17)	0.0500 (13)	0.0823 (19)	−0.0008 (12)	0.0129 (15)	−0.0023 (13)
C6	0.0686 (16)	0.0542 (13)	0.0740 (17)	0.0102 (12)	0.0041 (14)	0.0157 (13)
C7	0.0564 (12)	0.0560 (13)	0.0544 (12)	0.0118 (11)	−0.0010 (11)	0.0012 (10)
C8	0.122 (3)	0.078 (2)	0.081 (2)	0.0248 (19)	0.009 (2)	0.0219 (17)
C9	0.074 (2)	0.097 (3)	0.174 (5)	0.0241 (19)	0.044 (3)	−0.007 (3)
C10	0.187 (5)	0.073 (2)	0.112 (3)	0.052 (3)	−0.072 (3)	−0.034 (2)
N1	0.0468 (9)	0.0492 (9)	0.0401 (9)	0.0001 (8)	−0.0045 (8)	0.0005 (8)
N2	0.0588 (11)	0.0570 (11)	0.0570 (12)	0.0070 (10)	−0.0078 (10)	0.0101 (9)
S1	0.0568 (3)	0.0761 (4)	0.0493 (3)	0.0096 (3)	−0.0161 (3)	−0.0112 (3)

C1—N1	1.290 (3)	C6—H6	0.9300
C1—C7	1.512 (3)	C7—C10	1.521 (4)
C1—S1	1.753 (2)	C7—C8	1.522 (4)
C2—N2	1.335 (3)	C7—C9	1.524 (4)
C2—N1	1.387 (3)	C8—H8A	0.9600
C2—C3	1.399 (3)	C8—H8B	0.9600
C3—C4	1.389 (4)	C8—H8C	0.9600
C3—S1	1.722 (3)	C9—H9A	0.9600
C4—C5	1.371 (4)	C9—H9B	0.9600
C4—H4	0.9300	C9—H9C	0.9600
C5—C6	1.380 (4)	C10—H10A	0.9600
C5—H5	0.9300	C10—H10B	0.9600
C6—N2	1.341 (4)	C10—H10C	0.9600
N1—C1—C7	124.6 (2)	C8—C7—C9	109.3 (3)
N1—C1—S1	115.80 (18)	C7—C8—H8A	109.5
C7—C1—S1	119.64 (17)	C7—C8—H8B	109.5
N2—C2—N1	121.0 (2)	H8A—C8—H8B	109.5
N2—C2—C3	123.9 (2)	C7—C8—H8C	109.5
N1—C2—C3	115.1 (2)	H8A—C8—H8C	109.5
C4—C3—C2	119.7 (2)	H8B—C8—H8C	109.5
C4—C3—S1	130.8 (2)	C7—C9—H9A	109.5
C2—C3—S1	109.55 (18)	C7—C9—H9B	109.5
C5—C4—C3	116.6 (3)	H9A—C9—H9B	109.5
C5—C4—H4	121.7	C7—C9—H9C	109.5
C3—C4—H4	121.7	H9A—C9—H9C	109.5
C4—C5—C6	120.0 (3)	H9B—C9—H9C	109.5
C4—C5—H5	120.0	C7—C10—H10A	109.5
C6—C5—H5	120.0	C7—C10—H10B	109.5
N2—C6—C5	124.8 (3)	H10A—C10—H10B	109.5
N2—C6—H6	117.6	C7—C10—H10C	109.5
C5—C6—H6	117.6	H10A—C10—H10C	109.5
C1—C7—C10	110.3 (2)	H10B—C10—H10C	109.5
C1—C7—C8	109.3 (2)	C1—N1—C2	110.6 (2)
C10—C7—C8	108.1 (3)	C2—N2—C6	115.0 (2)
C1—C7—C9	108.9 (3)	C3—S1—C1	88.96 (11)
C10—C7—C9	110.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N1i	0.93	2.81	3.564 (3)	138
C6—H6···N1ii	0.93	2.72	3.620 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N1i	0.93	2.81	3.564 (3)	138
C6—H6⋯N1ii	0.93	2.72	3.620 (3)	164

Symmetry codes: (i) ; (ii) .