Crystal structure of 2-cyclo­hexyl-1,3-thia­zolo[4,5-b]pyridine

In the title compound, C₁₂H₁₄N₂S, the cyclo­hexane ring adopts a chair conformation with the exocyclic C-C bond in an equatorial orientation. The mean plane through the cyclo­hexane ring (all atoms) is twisted from the thia­zolo­pyridine ring system (r.m.s. deviation = 0.013 Å) by 39.57 (6)°. In the crystal, mol­ecules form (100) sheets, although there are no specific directional inter­actions between them. The crystal stucture was refined as a two-component perfect twin.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.180
• Data-to-parameter ratio = 28.8

checkCIF/PLATON results

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Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         10 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) .          1 Check

Alert level G
PLAT021_ALERT_4_G Ratio Unique / Expected Reflections too High ...      1.718
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.13 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         41 Note
PLAT931_ALERT_5_G Found Twin Law ( 0 0  1)[       ] Estimated BASF       0.50 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Chemical context

Thia­zolo­pyridine derivatives have been reported to exhibit inter­esting biological activities (Leysen et al., 1984). As part of our ongoing studies in this area (El-Hiti et al., 2015), we now report the structure of the title compound.

S2. Structural commentary

The asymmetric unit comprises one molecule of C₁₂H₁₄N₂S (Fig. 1). The cyclo­hexane ring is in the chair conformation in the molecule. The least squares plane through the cyclo­hexane ring is twisted from the thia­zolo­pyridine group by 39.57 (6)°. In the crystal structure, the molecular axes are aligned along [001] (Fig. 2).

S3. Synthesis and crystallization

2-Cyclo­hexyl-1,3-thia­zolo[4,5-b]pyridine was obtained in qu­anti­tative yield from acid hydrolysis (HCl, 5 M) of 3-(diiso­propyl­amino­thio­carbonyl­thio)-2-(cyclo­hexyl­carbonyl­amino)­pyridine under reflux for 5 h (Smith et al., 1995). The compound may also be synthesized in 94% yield from acid hydrolysis (5 M HCl, 5 h reflux) of 3-(diiso­propyl­amino­thio­carbonyl­thio)-2-(bis(cyclo­hexyl­carbony)lamino) pyridine (Smith et al., 1995). Crystallization of the crude product from di­ethyl ether gave the title compound as colourless crystals. Spectroscopic and analytical data are consistent with those reported (Smith et al., 1995).

S4. Refinement details

The data were twinned and HKLF5 in Shelxl 2013 was used. 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.

Related literature

For background to the uses of thiazolopyridine derivatives, see: Leysen et al. (1984). For a related structure reported by us and further references, see: El-Hiti et al. (2015). For the first report of this compound and spectroscopic data, see: Smith et al. (1995).

Structure description

Thia­zolo­pyridine derivatives have been reported to exhibit inter­esting biological activities (Leysen et al., 1984). As part of our ongoing studies in this area (El-Hiti et al., 2015), we now report the structure of the title compound.

The asymmetric unit comprises one molecule of C₁₂H₁₄N₂S (Fig. 1). The cyclo­hexane ring is in the chair conformation in the molecule. The least squares plane through the cyclo­hexane ring is twisted from the thia­zolo­pyridine group by 39.57 (6)°. In the crystal structure, the molecular axes are aligned along [001] (Fig. 2).

For background to the uses of thiazolopyridine derivatives, see: Leysen et al. (1984). For a related structure reported by us and further references, see: El-Hiti et al. (2015). For the first report of this compound and spectroscopic data, see: Smith et al. (1995).

Synthesis and crystallization

2-Cyclo­hexyl-1,3-thia­zolo[4,5-b]pyridine was obtained in qu­anti­tative yield from acid hydrolysis (HCl, 5 M) of 3-(diiso­propyl­amino­thio­carbonyl­thio)-2-(cyclo­hexyl­carbonyl­amino)­pyridine under reflux for 5 h (Smith et al., 1995). The compound may also be synthesized in 94% yield from acid hydrolysis (5 M HCl, 5 h reflux) of 3-(diiso­propyl­amino­thio­carbonyl­thio)-2-(bis(cyclo­hexyl­carbony)lamino) pyridine (Smith et al., 1995). Crystallization of the crude product from di­ethyl ether gave the title compound as colourless crystals. Spectroscopic and analytical data are consistent with those reported (Smith et al., 1995).

Refinement details

The data were twinned and HKLF5 in Shelxl 2013 was used. 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.

Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (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).

Figures

	Fig. 1. The asymmetric unit of C12H14N2S with 50% probability displacement ellipsoids for nonhydrogen atoms.
	Fig. 2. Crystal packing viewed along the a axis.

2-Cyclohexyl-1,3-thiazolo[4,5-b]pyridine

Crystal data

C12H14N2S	F(000) = 464
Mr = 218.31	Dx = 1.297 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 7.8884 (5) Å	Cell parameters from 1721 reflections
b = 11.8079 (7) Å	θ = 6.2–73.9°
c = 12.2134 (6) Å	µ = 2.29 mm^−1
β = 100.589 (6)°	T = 293 K
V = 1118.25 (11) Å^3	Needle, colourless
Z = 4	0.27 × 0.17 × 0.14 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	3429 reflections with I > 2σ(I)
ω scans	Rint = 0.015
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	θmax = 74.2°, θmin = 5.3°
Tmin = 0.592, Tmax = 1.000	h = −9→9
7328 measured reflections	k = −14→14
3913 independent reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.180	w = 1/[σ^2(Fo^2) + (0.1345P)^2 + 0.113P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3913 reflections	Δρmax = 0.30 e Å^−3
136 parameters	Δρmin = −0.29 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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. Refined as a 2-component perfect twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2814 (3)	0.12366 (19)	0.54649 (18)	0.0467 (5)
C2	0.2459 (3)	0.20807 (19)	0.72356 (18)	0.0467 (5)
C3	0.2223 (4)	0.2609 (2)	0.8209 (2)	0.0561 (6)
H3	0.1818	0.3349	0.8212	0.067*
C4	0.2619 (4)	0.1982 (3)	0.9169 (2)	0.0634 (7)
H4	0.2461	0.2291	0.9844	0.076*
C5	0.3249 (4)	0.0897 (3)	0.9136 (2)	0.0659 (7)
H5	0.3505	0.0501	0.9805	0.079*
C6	0.3115 (3)	0.0972 (2)	0.72741 (18)	0.0472 (5)
C7	0.2823 (3)	0.0976 (2)	0.42621 (18)	0.0501 (5)
H7	0.3994	0.0741	0.4202	0.060*
C8	0.1612 (4)	−0.0018 (2)	0.3883 (2)	0.0616 (7)
H8A	0.1972	−0.0671	0.4350	0.074*
H8B	0.0450	0.0181	0.3967	0.074*
C9	0.1620 (4)	−0.0321 (2)	0.2671 (2)	0.0654 (7)
H9A	0.2758	−0.0588	0.2600	0.079*
H9B	0.0805	−0.0929	0.2443	0.079*
C10	0.1149 (4)	0.0680 (3)	0.1922 (2)	0.0706 (8)
H10A	−0.0030	0.0901	0.1937	0.085*
H10B	0.1218	0.0471	0.1163	0.085*
C11	0.2341 (5)	0.1671 (3)	0.2281 (2)	0.0856 (11)
H11A	0.1964	0.2320	0.1811	0.103*
H11B	0.3501	0.1478	0.2188	0.103*
C12	0.2352 (5)	0.1982 (2)	0.3501 (2)	0.0709 (8)
H12A	0.3176	0.2587	0.3723	0.085*
H12B	0.1220	0.2257	0.3577	0.085*
N1	0.3309 (3)	0.05196 (17)	0.62604 (16)	0.0529 (5)
N2	0.3519 (3)	0.0371 (2)	0.82184 (17)	0.0616 (6)
S1	0.20709 (8)	0.25440 (5)	0.58736 (5)	0.0545 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0509 (11)	0.0426 (11)	0.0457 (11)	−0.0033 (9)	0.0065 (9)	−0.0001 (8)
C2	0.0516 (11)	0.0423 (11)	0.0436 (11)	−0.0036 (9)	0.0021 (8)	−0.0008 (9)
C3	0.0664 (15)	0.0505 (13)	0.0496 (13)	−0.0023 (11)	0.0058 (11)	−0.0090 (10)
C4	0.0767 (17)	0.0704 (18)	0.0419 (12)	−0.0073 (13)	0.0076 (11)	−0.0079 (11)
C5	0.0794 (17)	0.0733 (18)	0.0425 (13)	0.0014 (13)	0.0047 (11)	0.0092 (11)
C6	0.0507 (12)	0.0475 (12)	0.0425 (11)	0.0013 (9)	0.0060 (8)	0.0012 (9)
C7	0.0547 (13)	0.0510 (13)	0.0453 (11)	−0.0017 (9)	0.0107 (9)	−0.0023 (9)
C8	0.0855 (18)	0.0504 (13)	0.0502 (13)	−0.0138 (13)	0.0160 (12)	−0.0044 (10)
C9	0.0846 (18)	0.0552 (15)	0.0563 (15)	−0.0118 (13)	0.0121 (12)	−0.0137 (11)
C10	0.0842 (19)	0.0764 (19)	0.0473 (13)	0.0011 (15)	0.0020 (12)	−0.0089 (13)
C11	0.145 (3)	0.0712 (19)	0.0416 (13)	−0.030 (2)	0.0189 (15)	0.0008 (12)
C12	0.116 (2)	0.0519 (15)	0.0442 (13)	−0.0148 (15)	0.0133 (13)	−0.0002 (11)
N1	0.0672 (12)	0.0472 (10)	0.0450 (10)	0.0074 (9)	0.0121 (8)	0.0036 (8)
N2	0.0795 (14)	0.0581 (13)	0.0467 (11)	0.0120 (11)	0.0104 (9)	0.0103 (9)
S1	0.0753 (5)	0.0424 (4)	0.0425 (4)	0.0053 (2)	0.0017 (3)	0.0013 (2)

Geometric parameters (Å, º)

C1—N1	1.294 (3)	C7—H7	0.9800
C1—C7	1.502 (3)	C8—C9	1.524 (4)
C1—S1	1.756 (2)	C8—H8A	0.9700
C2—C3	1.385 (3)	C8—H8B	0.9700
C2—C6	1.405 (3)	C9—C10	1.499 (4)
C2—S1	1.724 (2)	C9—H9A	0.9700
C3—C4	1.374 (4)	C9—H9B	0.9700
C3—H3	0.9300	C10—C11	1.515 (4)
C4—C5	1.378 (4)	C10—H10A	0.9700
C4—H4	0.9300	C10—H10B	0.9700
C5—N2	1.332 (3)	C11—C12	1.534 (4)
C5—H5	0.9300	C11—H11A	0.9700
C6—N2	1.342 (3)	C11—H11B	0.9700
C6—N1	1.383 (3)	C12—H12A	0.9700
C7—C12	1.512 (4)	C12—H12B	0.9700
C7—C8	1.530 (3)
N1—C1—C7	123.0 (2)	H8A—C8—H8B	108.0
N1—C1—S1	115.61 (17)	C10—C9—C8	111.3 (2)
C7—C1—S1	121.33 (17)	C10—C9—H9A	109.4
C3—C2—C6	119.8 (2)	C8—C9—H9A	109.4
C3—C2—S1	131.07 (19)	C10—C9—H9B	109.4
C6—C2—S1	109.08 (17)	C8—C9—H9B	109.4
C4—C3—C2	116.4 (2)	H9A—C9—H9B	108.0
C4—C3—H3	121.8	C9—C10—C11	111.2 (2)
C2—C3—H3	121.8	C9—C10—H10A	109.4
C3—C4—C5	120.2 (2)	C11—C10—H10A	109.4
C3—C4—H4	119.9	C9—C10—H10B	109.4
C5—C4—H4	119.9	C11—C10—H10B	109.4
N2—C5—C4	124.9 (2)	H10A—C10—H10B	108.0
N2—C5—H5	117.6	C10—C11—C12	111.0 (3)
C4—C5—H5	117.6	C10—C11—H11A	109.4
N2—C6—N1	121.2 (2)	C12—C11—H11A	109.4
N2—C6—C2	123.3 (2)	C10—C11—H11B	109.4
N1—C6—C2	115.5 (2)	C12—C11—H11B	109.4
C1—C7—C12	113.3 (2)	H11A—C11—H11B	108.0
C1—C7—C8	109.77 (19)	C7—C12—C11	111.5 (3)
C12—C7—C8	110.3 (2)	C7—C12—H12A	109.3
C1—C7—H7	107.8	C11—C12—H12A	109.3
C12—C7—H7	107.8	C7—C12—H12B	109.3
C8—C7—H7	107.8	C11—C12—H12B	109.3
C9—C8—C7	111.1 (2)	H12A—C12—H12B	108.0
C9—C8—H8A	109.4	C1—N1—C6	110.6 (2)
C7—C8—H8A	109.4	C5—N2—C6	115.3 (2)
C9—C8—H8B	109.4	C2—S1—C1	89.19 (10)
C7—C8—H8B	109.4