8-Methyl-4-morpholinoethyl-1-thia-4-aza-spiro-[4.5]decan-3-one.

In the title compound, C(15)H(26)N(2)O(2)S, the cyclo-hexane and morpholine rings adopt chair conformations, while the thia-zole ring has a twist conformation. An intra-molecular C-H⋯S hydrogen-bond inter-action forms a five-membered ring. The crystal packing involves C-H⋯O=C inter-molecular inter-actions where carbonyl O atoms act as double acceptors to two symmetrically related H atoms.

Related literature

For general background, see: Andres et al. (2000 ▶); Vicini et al. (2006 ▶); Küçükgüzel et al. (2002 ▶); Barreca et al. (2001 ▶); Rao et al. (2004 ▶); Gududuru et al. (2004 ▶). For related literature, see: Akkurt et al. (2007 ▶, 2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H26N2O2S

M = 298.45

Triclinic,

a = 7.8629 (4) Å

b = 10.5239 (6) Å

c = 10.8252 (6) Å

α = 94.974 (5)°

β = 106.378 (5)°

γ = 107.169 (4)°

V = 806.89 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.72 × 0.64 × 0.58 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.867, T max = 0.891

17959 measured reflections

3253 independent reflections

2948 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.07

3253 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.18 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022459/kp2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022459/kp2183Isup2.hkl

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

C15H26N2O2S	Z = 2
Mr = 298.45	F000 = 324
Triclinic, P1	Dx = 1.228 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.8629 (4) Å	Cell parameters from 29201 reflections
b = 10.5239 (6) Å	θ = 2.0–28.0º
c = 10.8252 (6) Å	µ = 0.20 mm−1
α = 94.974 (5)º	T = 296 K
β = 106.378 (5)º	Block, colourless
γ = 107.169 (4)º	0.72 × 0.64 × 0.58 mm
V = 806.89 (8) Å3

Stoe IPDS-2 diffractometer	3253 independent reflections
Monochromator: plane graphite	2948 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.034
T = 296 K	θmax = 26.5º
ω scans	θmin = 2.9º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.867, Tmax = 0.891	k = −13→13
17959 measured reflections	l = −13→13

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.07P)2 + 0.1465P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3253 reflections	Δρmax = 0.72 e Å−3
181 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S1	0.34108 (6)	0.16629 (5)	0.79000 (5)	0.0644 (2)
O1	0.4404 (2)	0.54993 (14)	0.84353 (15)	0.0737 (5)
O2	1.1634 (2)	0.77257 (19)	0.54682 (15)	0.0857 (6)
N1	0.58740 (18)	0.40139 (13)	0.80741 (13)	0.0476 (4)
N2	0.88645 (18)	0.65537 (12)	0.66493 (12)	0.0465 (4)
C1	0.2920 (3)	0.3148 (2)	0.8397 (2)	0.0649 (6)
C2	0.4460 (2)	0.43541 (18)	0.83066 (16)	0.0545 (5)
C3	0.5878 (2)	0.26243 (15)	0.81122 (14)	0.0444 (4)
C4	0.6416 (3)	0.20501 (17)	0.69912 (16)	0.0541 (5)
C5	0.6455 (3)	0.06167 (18)	0.70696 (18)	0.0623 (6)
C6	0.7743 (3)	0.05266 (18)	0.83773 (19)	0.0592 (6)
C7	0.7230 (3)	0.11180 (19)	0.94940 (18)	0.0587 (6)
C8	0.7174 (2)	0.25365 (17)	0.94280 (15)	0.0522 (5)
C9	0.7691 (4)	−0.0928 (2)	0.8470 (3)	0.0830 (8)
C10	0.7529 (2)	0.50806 (16)	0.80326 (15)	0.0506 (5)
C11	0.7251 (2)	0.54594 (17)	0.66860 (16)	0.0530 (5)
C12	0.8409 (3)	0.7076 (2)	0.54383 (18)	0.0651 (6)
C13	1.0103 (3)	0.8188 (2)	0.5390 (2)	0.0794 (7)
C14	1.2124 (3)	0.7255 (3)	0.6657 (2)	0.0766 (7)
C15	1.0497 (2)	0.61291 (18)	0.67652 (17)	0.0557 (5)
H1A	0.17090	0.31270	0.78280	0.0780*
H1B	0.28890	0.31960	0.92890	0.0780*
H4A	0.76460	0.26320	0.70210	0.0650*
H4B	0.55170	0.20400	0.61620	0.0650*
H5A	0.51890	0.00160	0.69320	0.0750*
H5B	0.68720	0.03110	0.63730	0.0750*
H6	0.90330	0.10710	0.84630	0.0710*
H7A	0.60070	0.05350	0.94770	0.0700*
H7B	0.81400	0.11330	1.03190	0.0700*
H8A	0.84370	0.31460	0.95710	0.0630*
H8B	0.67450	0.28300	1.01240	0.0630*
H9A	0.80140	−0.12910	0.77570	0.1240*
H9B	0.64500	−0.14730	0.84260	0.1240*
H9C	0.85780	−0.09330	0.92860	0.1240*
H10A	0.86080	0.47760	0.82650	0.0610*
H10B	0.77880	0.58750	0.86740	0.0610*
H11A	0.70360	0.46730	0.60500	0.0640*
H11B	0.61440	0.57310	0.64400	0.0640*
H12A	0.73840	0.74250	0.53870	0.0780*
H12B	0.80040	0.63490	0.46930	0.0780*
H13A	0.97770	0.85230	0.45800	0.0950*
H13B	1.04670	0.89310	0.61120	0.0950*
H14A	1.25230	0.79980	0.73860	0.0920*
H14B	1.31720	0.69320	0.67090	0.0920*
H15A	1.01660	0.53560	0.60800	0.0670*
H15B	1.08690	0.58510	0.76030	0.0670*

	U11	U22	U33	U12	U13	U23
S1	0.0449 (2)	0.0547 (3)	0.0893 (4)	0.0085 (2)	0.0219 (2)	0.0200 (2)
O1	0.0760 (9)	0.0646 (8)	0.0894 (10)	0.0368 (7)	0.0264 (7)	0.0132 (7)
O2	0.0795 (10)	0.1059 (12)	0.0718 (9)	0.0147 (9)	0.0356 (7)	0.0365 (8)
N1	0.0443 (6)	0.0453 (7)	0.0529 (7)	0.0129 (5)	0.0164 (5)	0.0124 (5)
N2	0.0477 (7)	0.0418 (6)	0.0465 (6)	0.0119 (5)	0.0119 (5)	0.0127 (5)
C1	0.0485 (9)	0.0746 (12)	0.0754 (11)	0.0193 (8)	0.0279 (8)	0.0109 (9)
C2	0.0518 (9)	0.0593 (9)	0.0547 (9)	0.0230 (7)	0.0163 (7)	0.0099 (7)
C3	0.0415 (7)	0.0446 (7)	0.0468 (7)	0.0117 (6)	0.0157 (6)	0.0125 (6)
C4	0.0645 (10)	0.0536 (9)	0.0460 (8)	0.0185 (7)	0.0209 (7)	0.0120 (6)
C5	0.0723 (11)	0.0540 (9)	0.0631 (10)	0.0207 (8)	0.0271 (8)	0.0071 (8)
C6	0.0532 (9)	0.0524 (9)	0.0770 (11)	0.0196 (7)	0.0253 (8)	0.0165 (8)
C7	0.0599 (10)	0.0663 (10)	0.0602 (9)	0.0279 (8)	0.0232 (8)	0.0271 (8)
C8	0.0536 (8)	0.0607 (9)	0.0441 (8)	0.0218 (7)	0.0148 (6)	0.0120 (6)
C9	0.0817 (14)	0.0599 (11)	0.1133 (18)	0.0334 (10)	0.0288 (13)	0.0205 (11)
C10	0.0473 (8)	0.0470 (8)	0.0501 (8)	0.0080 (6)	0.0123 (6)	0.0111 (6)
C11	0.0459 (8)	0.0524 (8)	0.0527 (8)	0.0094 (7)	0.0093 (6)	0.0161 (7)
C12	0.0649 (10)	0.0618 (10)	0.0595 (10)	0.0137 (8)	0.0098 (8)	0.0269 (8)
C13	0.0898 (15)	0.0634 (11)	0.0663 (11)	0.0041 (10)	0.0140 (10)	0.0316 (9)
C14	0.0559 (10)	0.0968 (15)	0.0778 (13)	0.0158 (10)	0.0280 (9)	0.0329 (11)
C15	0.0560 (9)	0.0602 (9)	0.0552 (9)	0.0210 (7)	0.0214 (7)	0.0161 (7)

S1—C1	1.791 (2)	C4—H4A	0.9700
S1—C3	1.8410 (17)	C4—H4B	0.9700
O1—C2	1.216 (2)	C5—H5A	0.9700
O2—C13	1.410 (3)	C5—H5B	0.9700
O2—C14	1.412 (3)	C6—H6	0.9800
N1—C2	1.343 (2)	C7—H7A	0.9700
N1—C3	1.468 (2)	C7—H7B	0.9700
N1—C10	1.461 (2)	C8—H8A	0.9700
N2—C11	1.453 (2)	C8—H8B	0.9700
N2—C12	1.458 (2)	C9—H9A	0.9600
N2—C15	1.456 (2)	C9—H9B	0.9600
C1—C2	1.506 (3)	C9—H9C	0.9600
C3—C4	1.526 (3)	C10—H10A	0.9700
C3—C8	1.528 (2)	C10—H10B	0.9700
C4—C5	1.527 (3)	C11—H11A	0.9700
C5—C6	1.520 (3)	C11—H11B	0.9700
C6—C7	1.518 (3)	C12—H12A	0.9700
C6—C9	1.532 (3)	C12—H12B	0.9700
C7—C8	1.514 (3)	C13—H13A	0.9700
C10—C11	1.518 (2)	C13—H13B	0.9700
C12—C13	1.509 (3)	C14—H14A	0.9700
C14—C15	1.506 (3)	C14—H14B	0.9700
C1—H1A	0.9700	C15—H15A	0.9700
C1—H1B	0.9700	C15—H15B	0.9700
S1···N1	2.6062 (15)	H5B···H9A	2.5400
S1···H5A	2.8300	H7A···S1	2.8800
S1···H7A	2.8800	H7A···H9B	2.4700
S1···H13Bi	3.1500	H7A···H7Aviii	2.2900
S1···H13Aii	3.0600	H7B···H9C	2.5200
O1···C11	3.321 (2)	H7B···H9Cix	2.5700
O1···C14iii	3.311 (3)	H8A···C10	2.8600
O1···C15iii	3.380 (2)	H8A···H10A	2.3100
O1···C1iv	3.395 (3)	H8B···O1iv	2.7600
O1···C2iv	3.363 (2)	H9A···N2x	2.8100
O2···N2	2.856 (2)	H9A···C12x	3.0600
O2···C4v	3.419 (3)	H9A···H5B	2.5400
O1···H10B	2.5100	H9B···H5A	2.5500
O1···H15Biii	2.8200	H9B···H7A	2.4700
O1···H1Biv	2.6900	H9C···H7B	2.5200
O1···H8Biv	2.7600	H9C···H7Bix	2.5700
O1···H11B	2.8600	H9C···H9Cix	2.4900
O1···H14Biii	2.6500	H10A···C4	2.8600
N1···S1	2.6062 (15)	H10A···C8	2.8600
N2···O2	2.856 (2)	H10A···C15	2.7200
N2···H9Avi	2.8100	H10A···H4A	2.3200
C1···O1iv	3.395 (3)	H10A···H8A	2.3100
C2···O1iv	3.363 (2)	H10A···H15B	2.1500
C2···C2iv	3.565 (2)	H10B···O1	2.5100
C4···C11	3.514 (2)	H10B···H1Biv	2.5900
C4···O2v	3.419 (3)	H11A···C4	2.9800
C11···O1	3.321 (2)	H11A···H4A	2.5800
C11···C4	3.514 (2)	H11A···H12B	2.4800
C14···O1vii	3.311 (3)	H11A···H15A	2.3400
C15···O1vii	3.380 (2)	H11B···O1	2.8600
C2···H11B	2.9700	H11B···C2	2.9700
C4···H11A	2.9800	H11B···H12A	2.3200
C4···H10A	2.8600	H12A···H11B	2.3200
C8···H10A	2.8600	H12B···H11A	2.4800
C10···H15B	2.7000	H12B···H15A	2.4700
C10···H8A	2.8600	H13A···S1ii	3.0600
C10···H4A	2.7500	H13B···S1xi	3.1500
C12···H9Avi	3.0600	H13B···C15	3.1000
C15···H10A	2.7200	H13B···H14A	2.3200
C15···H13B	3.1000	H14A···H13B	2.3200
H1B···O1iv	2.6900	H14B···O1vii	2.6500
H1B···H10Biv	2.5900	H15A···H11A	2.3400
H4A···C10	2.7500	H15A···H12B	2.4700
H4A···H10A	2.3200	H15A···H15Av	2.3100
H4A···H11A	2.5800	H15B···O1vii	2.8200
H5A···S1	2.8300	H15B···C10	2.7000
H5A···H9B	2.5500	H15B···H10A	2.1500
C1—S1—C3	92.98 (9)	C9—C6—H6	108.00
C13—O2—C14	109.27 (17)	C6—C7—H7A	109.00
C2—N1—C3	118.93 (14)	C6—C7—H7B	109.00
C2—N1—C10	119.11 (14)	C8—C7—H7A	109.00
C3—N1—C10	120.98 (14)	C8—C7—H7B	109.00
C11—N2—C12	110.57 (14)	H7A—C7—H7B	108.00
C11—N2—C15	112.08 (13)	C3—C8—H8A	109.00
C12—N2—C15	109.11 (15)	C3—C8—H8B	109.00
S1—C1—C2	107.46 (16)	C7—C8—H8A	109.00
O1—C2—N1	124.77 (17)	C7—C8—H8B	109.00
O1—C2—C1	122.89 (18)	H8A—C8—H8B	108.00
N1—C2—C1	112.34 (16)	C6—C9—H9A	110.00
S1—C3—N1	103.37 (11)	C6—C9—H9B	109.00
S1—C3—C4	108.79 (12)	C6—C9—H9C	109.00
S1—C3—C8	110.62 (11)	H9A—C9—H9B	109.00
N1—C3—C4	112.65 (13)	H9A—C9—H9C	109.00
N1—C3—C8	111.03 (12)	H9B—C9—H9C	109.00
C4—C3—C8	110.18 (14)	N1—C10—H10A	109.00
C3—C4—C5	111.69 (15)	N1—C10—H10B	109.00
C4—C5—C6	112.69 (15)	C11—C10—H10A	109.00
C5—C6—C7	110.18 (19)	C11—C10—H10B	109.00
C5—C6—C9	112.17 (18)	H10A—C10—H10B	108.00
C7—C6—C9	110.37 (18)	N2—C11—H11A	109.00
C6—C7—C8	113.08 (15)	N2—C11—H11B	109.00
C3—C8—C7	112.40 (14)	C10—C11—H11A	109.00
N1—C10—C11	111.79 (13)	C10—C11—H11B	109.00
N2—C11—C10	112.12 (13)	H11A—C11—H11B	108.00
N2—C12—C13	110.35 (17)	N2—C12—H12A	110.00
O2—C13—C12	111.52 (18)	N2—C12—H12B	110.00
O2—C14—C15	111.56 (18)	C13—C12—H12A	110.00
N2—C15—C14	111.32 (17)	C13—C12—H12B	110.00
S1—C1—H1A	110.00	H12A—C12—H12B	108.00
S1—C1—H1B	110.00	O2—C13—H13A	109.00
C2—C1—H1A	110.00	O2—C13—H13B	109.00
C2—C1—H1B	110.00	C12—C13—H13A	109.00
H1A—C1—H1B	109.00	C12—C13—H13B	109.00
C3—C4—H4A	109.00	H13A—C13—H13B	108.00
C3—C4—H4B	109.00	O2—C14—H14A	109.00
C5—C4—H4A	109.00	O2—C14—H14B	109.00
C5—C4—H4B	109.00	C15—C14—H14A	109.00
H4A—C4—H4B	108.00	C15—C14—H14B	109.00
C4—C5—H5A	109.00	H14A—C14—H14B	108.00
C4—C5—H5B	109.00	N2—C15—H15A	109.00
C6—C5—H5A	109.00	N2—C15—H15B	109.00
C6—C5—H5B	109.00	C14—C15—H15A	109.00
H5A—C5—H5B	108.00	C14—C15—H15B	109.00
C5—C6—H6	108.00	H15A—C15—H15B	108.00
C7—C6—H6	108.00
C3—S1—C1—C2	17.14 (14)	C12—N2—C15—C14	54.33 (18)
C1—S1—C3—C4	−140.08 (12)	C12—N2—C11—C10	−168.37 (15)
C1—S1—C3—C8	98.77 (13)	C15—N2—C12—C13	−54.9 (2)
C1—S1—C3—N1	−20.15 (11)	S1—C1—C2—O1	171.24 (15)
C13—O2—C14—C15	58.7 (2)	S1—C1—C2—N1	−8.90 (19)
C14—O2—C13—C12	−59.8 (2)	N1—C3—C8—C7	−179.28 (15)
C3—N1—C2—O1	172.02 (16)	C8—C3—C4—C5	54.1 (2)
C10—N1—C2—O1	3.3 (2)	S1—C3—C8—C7	66.56 (17)
C10—N1—C3—C8	69.70 (18)	N1—C3—C4—C5	178.67 (16)
C2—N1—C3—C4	137.07 (16)	C4—C3—C8—C7	−53.77 (19)
C2—N1—C3—S1	19.82 (16)	S1—C3—C4—C5	−67.33 (18)
C10—N1—C3—S1	−171.66 (11)	C3—C4—C5—C6	−55.4 (2)
C10—N1—C2—C1	−176.58 (14)	C4—C5—C6—C7	53.7 (2)
C10—N1—C3—C4	−54.41 (19)	C4—C5—C6—C9	177.0 (2)
C2—N1—C3—C8	−98.82 (17)	C5—C6—C7—C8	−53.1 (2)
C3—N1—C2—C1	−7.8 (2)	C9—C6—C7—C8	−177.6 (2)
C3—N1—C10—C11	106.22 (16)	C6—C7—C8—C3	54.4 (2)
C2—N1—C10—C11	−85.28 (18)	N1—C10—C11—N2	177.91 (13)
C11—N2—C15—C14	177.14 (14)	N2—C12—C13—O2	59.0 (2)
C11—N2—C12—C13	−178.59 (16)	O2—C14—C15—N2	−57.2 (2)
C15—N2—C11—C10	69.65 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···S1	0.97	2.83	3.217 (2)	105
C14—H14B···O1vii	0.97	2.65	3.311 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯S1	0.97	2.83	3.217 (2)	105
C14—H14B⋯O1i	0.97	2.65	3.311 (3)	126

Symmetry code: (i) .