4′-tert-Butyl-5-chloro-3H-spiro­[1,3-benzothia­zole-2,1′-cyclo­hexa­ne]

Mehmet Akkurt; Gökçe Cihan-Üstündağ; Gültaze Çapan; Yılmaz Dağdemir; Muhammad Nawaz Tahir

doi:10.1107/S1600536812017539

. 2012 Apr 28;68(Pt 5):o1542. doi: 10.1107/S1600536812017539

4′-tert-Butyl-5-chloro-3H-spiro[1,3-benzothiazole-2,1′-cyclohexane]

Mehmet Akkurt ^a,^*, Gökçe Cihan-Üstündağ ^b, Gültaze Çapan ^b, Yılmaz Dağdemir ^a, Muhammad Nawaz Tahir ^c

PMCID: PMC3344643 PMID: 22590405

Abstract

In the title compound, C₁₆H₂₂ClNS, the nine-membered 2,3-dihydro-1,3-benzothiazole ring system is essentially planar, with a maximum deviation of 0.025 (2) Å for the N atom. Its plane is almost perpendicular to the main plane of the substituted cyclohexane ring, which adopts a chair conformation. In the crystal, the molecules are linked by C—H⋯π interactions.

Related literature

For the pharmacological activity of benzothiazole derivatives, see: Coudert et al. (1988 ▶); Karalı et al. (2010 ▶); Palmer et al. (1971 ▶). For the crystal structures of similar compounds, see, for example: Akkurt et al. (2010 ▶); Aryai et al. (1976 ▶); Karalı et al. (2010 ▶). For standard values of bond lengths, see: Allen et al. (1987 ▶). For details of ring-puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₆H₂₂ClNS
M _r = 295.87
Monoclinic,
a = 15.2810 (18) Å
b = 8.9830 (8) Å
c = 11.8750 (13) Å
β = 109.580 (3)°
V = 1535.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 296 K
0.27 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.915, T _max = 0.935
14074 measured reflections
3849 independent reflections
2330 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.128
S = 1.02
3849 reflections
179 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017539/su2411sup1.cif

e-68-o1542-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017539/su2411Isup2.hkl

e-68-o1542-Isup2.hkl^{(188.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812017539/su2411Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cg1ⁱ	0.97	2.84	3.796 (2)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The condensation of aldehydes and ketones with 2-aminothiophenoles lead to benzothiazolines and spirobenzothiazolines which are reported to exhibit antitubercular (Palmer et al., 1971), analgesic (Coudert et al., 1988) and antioxidant (Karalı et al., 2010) properties. The reactivity of cyclic ketones towards 2-aminothiophenoles has also been examined and the structure of the end products has been discussed (Aryai et al., 1976; Coudert et al., 1988; Akkurt et al., 2010; Karalı et al., 2010). Prompted by the above observations, we report here the synthesis, spectroscopic and crystal structure of the title compound.

As shown in Fig. 1, the C7—C12 cyclohexane ring of the title compound adopts a chair conformation [puckering parameters (Cremer & Pople, 1975): Q_T = 0.564 (2) Å, θ = 176.5 (2) ° and φ = 4(4) °]. The mean plane of the 2,3-dihydro-1,3-benzothiazole ring system [max. deviation: -0.025 (2) Å for N1] is almost perpendicular with a dihedral angle of 89.39 (5) ° to the main plane formed by the C8,C9, C11 and C12 atoms of the cyclohexane ring. The bond lengths (Allen et al., 1987) and bond angles are within the expected values.

The crystal packing is stabilized by C—H···π interactions (Table 1 and Fig. 2).

Experimental

A mixture of 2-amino-4-chlorothiophenol (0.01 mol) and 4-tert-butylcyclohexanone (0.01 mol) in absolute ethanol (50 ml) was refluxed on a water bath for 8 h. The solvent was evaporated in a crystallizing dish at room temperature and the residue was recrystallized twice from ethanol, giving X-ray quality crystals [Yield: 24.3%, m.p.: 453–455 K]. Analysis calculated for C₁₆H₂₂ClNS: C 64.95, H 7.49, N 4.73%. Found: C 64.91, H 7.47, N 4.64%. Spectroscopic data for the title compound are given in the archive CIF.