5-Chloro-4'-ethyl-3H-spiro-[1,3-benzo-thia-zole-2,1'-cyclo-hexa-ne].

In the title compound, C(14)H(18)ClNS, the 2,3-dihydro-1,3-thia-zole ring adopts an envelope with the S,N-bound C atom at the flap and the cyclo-hexane ring adopts a chair conformation. In the crystal, N-H⋯S hydrogen bonds with C(5) motifs connect the mol-ecules into chains parallel to the c axis.

Related literature

For the pharmacological activity of benzothia­zole derivatives, see: Coudert et al. (1988 ▶); Karalı et al. (2010 ▶); Palmer et al. (1971 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶). For ring-puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H18ClNS

M = 267.81

Orthorhombic,

a = 8.989 (3) Å

b = 11.163 (4) Å

c = 13.722 (4) Å

V = 1376.9 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 296 K

0.35 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.872, T max = 0.903

7077 measured reflections

3203 independent reflections

2724 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.03

3203 reflections

159 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 1320 Freidel pairs

Flack parameter: 0.02 (8)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016479/hg5210sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016479/hg5210Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016479/hg5210Isup3.cml

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

C14H18ClNS	F(000) = 568
Mr = 267.81	Dx = 1.292 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 859 reflections
a = 8.989 (3) Å	θ = 3.5–20°
b = 11.163 (4) Å	µ = 0.41 mm−1
c = 13.722 (4) Å	T = 296 K
V = 1376.9 (8) Å3	Prism, light yellow
Z = 4	0.35 × 0.28 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	3203 independent reflections
Radiation source: fine-focus sealed tube	2724 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 27.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→8
Tmin = 0.872, Tmax = 0.903	k = −14→10
7077 measured reflections	l = −18→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.2606P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3203 reflections	Δρmax = 0.32 e Å−3
159 parameters	Δρmin = −0.35 e Å−3
1 restraint	Absolute structure: Flack (1983), 1320 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (8)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.49813 (9)	0.45066 (8)	−0.35059 (4)	0.0819 (3)
S1	0.37029 (6)	0.40096 (5)	0.09263 (4)	0.0481 (2)
N1	0.5350 (2)	0.25670 (18)	−0.01023 (14)	0.0529 (6)
C1	0.3980 (2)	0.43112 (18)	−0.03208 (14)	0.0430 (7)
C2	0.3365 (2)	0.5213 (2)	−0.08691 (16)	0.0540 (7)
C3	0.3676 (3)	0.5274 (2)	−0.18623 (17)	0.0597 (8)
C4	0.4593 (3)	0.4430 (2)	−0.22640 (16)	0.0547 (8)
C5	0.5230 (3)	0.3517 (2)	−0.17270 (16)	0.0527 (7)
C6	0.4912 (2)	0.34542 (18)	−0.07400 (14)	0.0437 (6)
C7	0.5242 (2)	0.29047 (17)	0.09277 (15)	0.0437 (6)
C8	0.4828 (3)	0.18328 (18)	0.15561 (16)	0.0534 (7)
C9	0.4758 (3)	0.21449 (19)	0.26303 (16)	0.0541 (7)
C10	0.6208 (3)	0.26917 (19)	0.30042 (15)	0.0470 (6)
C11	0.6605 (2)	0.3776 (2)	0.23844 (15)	0.0506 (7)
C12	0.6673 (2)	0.3484 (2)	0.12979 (15)	0.0495 (7)
C13	0.6130 (3)	0.2992 (2)	0.40837 (16)	0.0602 (8)
C14	0.7593 (3)	0.3396 (3)	0.4523 (2)	0.0791 (10)
H1N	0.611 (2)	0.214 (2)	−0.0203 (19)	0.078 (9)*
H2	0.27450	0.57770	−0.05800	0.0650*
H3	0.32680	0.58780	−0.22450	0.0720*
H5	0.58560	0.29600	−0.20200	0.0630*
H8A	0.38670	0.15290	0.13500	0.0640*
H8B	0.55560	0.12030	0.14590	0.0640*
H9A	0.45400	0.14260	0.30000	0.0650*
H9B	0.39520	0.27080	0.27370	0.0650*
H10	0.69960	0.20940	0.29160	0.0560*
H11A	0.75630	0.40850	0.25920	0.0610*
H11B	0.58700	0.43990	0.24900	0.0610*
H12A	0.68540	0.42150	0.09350	0.0590*
H12B	0.75000	0.29450	0.11790	0.0590*
H13A	0.53990	0.36200	0.41780	0.0720*
H13B	0.57860	0.22900	0.44340	0.0720*
H14A	0.83630	0.28400	0.43480	0.1190*
H14B	0.75030	0.34280	0.52190	0.1190*
H14C	0.78410	0.41770	0.42790	0.1190*

	U11	U22	U33	U12	U13	U23
Cl1	0.0729 (4)	0.1232 (6)	0.0495 (3)	−0.0171 (5)	0.0012 (3)	0.0056 (3)
S1	0.0423 (3)	0.0527 (3)	0.0492 (3)	0.0097 (3)	0.0031 (2)	−0.0056 (2)
N1	0.0541 (12)	0.0517 (11)	0.0528 (10)	0.0153 (10)	0.0027 (9)	−0.0101 (8)
C1	0.0378 (11)	0.0448 (12)	0.0464 (11)	−0.0016 (9)	−0.0028 (8)	−0.0087 (8)
C2	0.0495 (12)	0.0538 (13)	0.0586 (13)	0.0064 (10)	−0.0104 (11)	−0.0055 (11)
C3	0.0562 (13)	0.0646 (15)	0.0582 (13)	−0.0029 (13)	−0.0128 (12)	0.0067 (11)
C4	0.0476 (13)	0.0704 (15)	0.0462 (11)	−0.0142 (12)	−0.0063 (9)	−0.0003 (11)
C5	0.0423 (11)	0.0642 (14)	0.0517 (12)	−0.0016 (11)	0.0036 (10)	−0.0130 (11)
C6	0.0356 (10)	0.0465 (11)	0.0489 (11)	−0.0031 (9)	−0.0018 (9)	−0.0076 (9)
C7	0.0421 (11)	0.0398 (10)	0.0492 (11)	0.0056 (9)	0.0007 (10)	−0.0034 (9)
C8	0.0575 (13)	0.0375 (11)	0.0653 (14)	−0.0031 (10)	−0.0026 (12)	−0.0005 (9)
C9	0.0580 (14)	0.0426 (11)	0.0618 (13)	−0.0060 (11)	0.0061 (11)	0.0093 (10)
C10	0.0444 (11)	0.0463 (11)	0.0502 (11)	0.0066 (10)	0.0034 (10)	0.0035 (9)
C11	0.0450 (12)	0.0530 (13)	0.0537 (12)	−0.0103 (10)	−0.0018 (9)	0.0023 (10)
C12	0.0386 (11)	0.0559 (13)	0.0540 (12)	−0.0016 (10)	0.0030 (9)	0.0083 (10)
C13	0.0590 (14)	0.0690 (15)	0.0525 (13)	0.0078 (13)	0.0031 (12)	0.0082 (12)
C14	0.0742 (18)	0.104 (2)	0.0591 (15)	0.0009 (18)	−0.0082 (14)	−0.0086 (16)

Cl1—C4	1.742 (2)	C13—C14	1.515 (4)
S1—C1	1.762 (2)	C2—H2	0.9300
S1—C7	1.854 (2)	C3—H3	0.9300
N1—C6	1.379 (3)	C5—H5	0.9300
N1—C7	1.466 (3)	C8—H8A	0.9700
N1—H1N	0.84 (2)	C8—H8B	0.9700
C1—C6	1.396 (3)	C9—H9A	0.9700
C1—C2	1.373 (3)	C9—H9B	0.9700
C2—C3	1.393 (3)	C10—H10	0.9800
C3—C4	1.368 (3)	C11—H11A	0.9700
C4—C5	1.382 (3)	C11—H11B	0.9700
C5—C6	1.386 (3)	C12—H12A	0.9700
C7—C8	1.521 (3)	C12—H12B	0.9700
C7—C12	1.527 (3)	C13—H13A	0.9700
C8—C9	1.516 (3)	C13—H13B	0.9700
C9—C10	1.528 (4)	C14—H14A	0.9600
C10—C11	1.522 (3)	C14—H14B	0.9600
C10—C13	1.520 (3)	C14—H14C	0.9600
C11—C12	1.527 (3)
C1—S1—C7	91.30 (9)	C6—C5—H5	121.00
C6—N1—C7	114.09 (17)	C7—C8—H8A	109.00
C6—N1—H1N	122.2 (17)	C7—C8—H8B	109.00
C7—N1—H1N	110.9 (18)	C9—C8—H8A	109.00
S1—C1—C2	127.99 (16)	C9—C8—H8B	109.00
S1—C1—C6	110.75 (14)	H8A—C8—H8B	108.00
C2—C1—C6	121.23 (18)	C8—C9—H9A	109.00
C1—C2—C3	119.4 (2)	C8—C9—H9B	109.00
C2—C3—C4	118.8 (2)	C10—C9—H9A	109.00
Cl1—C4—C5	118.36 (18)	C10—C9—H9B	109.00
C3—C4—C5	122.9 (2)	H9A—C9—H9B	108.00
Cl1—C4—C3	118.77 (18)	C9—C10—H10	108.00
C4—C5—C6	118.2 (2)	C11—C10—H10	108.00
N1—C6—C5	126.69 (19)	C13—C10—H10	108.00
N1—C6—C1	113.71 (17)	C10—C11—H11A	109.00
C1—C6—C5	119.46 (19)	C10—C11—H11B	109.00
S1—C7—C12	110.33 (14)	C12—C11—H11A	109.00
N1—C7—C8	111.13 (16)	C12—C11—H11B	109.00
S1—C7—C8	109.97 (14)	H11A—C11—H11B	108.00
C8—C7—C12	110.53 (17)	C7—C12—H12A	109.00
N1—C7—C12	111.96 (16)	C7—C12—H12B	109.00
S1—C7—N1	102.68 (13)	C11—C12—H12A	109.00
C7—C8—C9	112.37 (17)	C11—C12—H12B	109.00
C8—C9—C10	112.5 (2)	H12A—C12—H12B	108.00
C9—C10—C13	112.1 (2)	C10—C13—H13A	109.00
C11—C10—C13	112.33 (18)	C10—C13—H13B	109.00
C9—C10—C11	109.28 (18)	C14—C13—H13A	109.00
C10—C11—C12	112.66 (18)	C14—C13—H13B	109.00
C7—C12—C11	112.43 (16)	H13A—C13—H13B	108.00
C10—C13—C14	114.4 (2)	C13—C14—H14A	109.00
C1—C2—H2	120.00	C13—C14—H14B	110.00
C3—C2—H2	120.00	C13—C14—H14C	109.00
C2—C3—H3	121.00	H14A—C14—H14B	110.00
C4—C3—H3	121.00	H14A—C14—H14C	109.00
C4—C5—H5	121.00	H14B—C14—H14C	109.00
C7—S1—C1—C2	−169.63 (19)	Cl1—C4—C5—C6	−179.63 (18)
C7—S1—C1—C6	12.78 (15)	C3—C4—C5—C6	0.5 (4)
C1—S1—C7—N1	−22.42 (13)	C4—C5—C6—N1	175.0 (2)
C1—S1—C7—C8	−140.76 (15)	C4—C5—C6—C1	−0.6 (3)
C1—S1—C7—C12	97.06 (15)	S1—C7—C8—C9	−68.9 (2)
C6—N1—C7—S1	28.68 (19)	N1—C7—C8—C9	178.09 (19)
C6—N1—C7—C8	146.21 (18)	C12—C7—C8—C9	53.2 (3)
C6—N1—C7—C12	−89.7 (2)	S1—C7—C12—C11	69.5 (2)
C7—N1—C6—C1	−21.5 (2)	N1—C7—C12—C11	−176.80 (17)
C7—N1—C6—C5	162.7 (2)	C8—C7—C12—C11	−52.3 (2)
S1—C1—C2—C3	−177.34 (17)	C7—C8—C9—C10	−56.0 (3)
C6—C1—C2—C3	0.0 (3)	C8—C9—C10—C11	55.3 (2)
S1—C1—C6—N1	2.0 (2)	C8—C9—C10—C13	−179.54 (18)
S1—C1—C6—C5	178.12 (17)	C9—C10—C11—C12	−54.5 (2)
C2—C1—C6—N1	−175.77 (18)	C13—C10—C11—C12	−179.53 (19)
C2—C1—C6—C5	0.3 (3)	C9—C10—C13—C14	172.9 (2)
C1—C2—C3—C4	−0.1 (3)	C11—C10—C13—C14	−63.6 (3)
C2—C3—C4—C5	−0.1 (4)	C10—C11—C12—C7	54.5 (2)
C2—C3—C4—Cl1	179.98 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1i	0.84 (2)	2.84 (2)	3.669 (2)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1i	0.84 (2)	2.84 (2)	3.669 (2)	168 (2)

Symmetry code: (i) .