8-Ethyl-2-hydr-oxy-2-methyl-4-morpholinoethyl-1-thia-4-aza-spiro-[4.5]decan-3-one.

Mol-ecules of the title spiro-[4.5]decane derivative, C(17)H(30)N(2)O(3)S, are linked by paired O-H⋯N hydrogen bonds into centrosymmetric R(2) (2)(16) dimers and these dimers are linked into a three-dimensional framework structure by C-H⋯O interactions.

Related literature

For background on the applications of thia­zolidines, see: Babaoğlu et al. (2003 ▶); Pfahl et al. (2003 ▶); Sayyed et al. (2006 ▶); Sharma et al. (2006 ▶). For related structures, see: Akkurt et al. (2007 ▶); Akkurt et al. (2008a ▶,b ▶,c ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H30N2O3S

M = 342.50

Triclinic,

a = 8.1878 (4) Å

b = 10.2241 (5) Å

c = 12.2188 (6) Å

α = 79.901 (4)°

β = 73.796 (4)°

γ = 67.674 (4)°

V = 905.83 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.55 × 0.38 × 0.27 mm

Data collection

STOE IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.900, T max = 0.949

18506 measured reflections

3717 independent reflections

3297 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.03

3717 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.16 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/S1600536808029097/hb2794sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029097/hb2794Isup2.hkl

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

C17H30N2O3S	Z = 2
Mr = 342.50	F(000) = 372
Triclinic, P1	Dx = 1.256 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1878 (4) Å	Cell parameters from 28660 reflections
b = 10.2241 (5) Å	θ = 2.2–27.4°
c = 12.2188 (6) Å	µ = 0.20 mm−1
α = 79.901 (4)°	T = 296 K
β = 73.796 (4)°	Block, colourless
γ = 67.674 (4)°	0.55 × 0.38 × 0.27 mm
V = 905.83 (8) Å3

STOE IPDS II diffractometer	3717 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3297 reflections with I > 2σ(I)
plane graphite	Rint = 0.055
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.7°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.900, Tmax = 0.949	l = −15→15
18506 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.1334P] where P = (Fo2 + 2Fc2)/3
3717 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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	0.35630 (5)	0.26913 (4)	0.21446 (3)	0.0484 (1)
O1	0.18488 (14)	0.24461 (12)	0.54122 (9)	0.0578 (4)
O2	0.74392 (17)	0.18404 (13)	0.83355 (9)	0.0631 (4)
O3	0.08914 (13)	0.18609 (10)	0.34973 (9)	0.0505 (3)
N1	0.43113 (15)	0.26810 (11)	0.40883 (9)	0.0402 (3)
N2	0.68062 (14)	0.09805 (10)	0.64605 (9)	0.0379 (3)
C1	0.17113 (18)	0.28560 (13)	0.34309 (12)	0.0432 (4)
C2	0.26212 (18)	0.26248 (13)	0.44208 (11)	0.0421 (4)
C3	0.51348 (17)	0.28899 (13)	0.28697 (10)	0.0380 (3)
C4	0.5285 (2)	0.43629 (13)	0.25620 (12)	0.0453 (4)
C5	0.6216 (2)	0.45605 (14)	0.13129 (12)	0.0492 (4)
C6	0.80738 (19)	0.34126 (15)	0.09591 (12)	0.0459 (4)
C7	0.78779 (19)	0.19575 (14)	0.12536 (12)	0.0461 (4)
C8	0.70039 (18)	0.17493 (13)	0.25161 (11)	0.0425 (4)
C9	0.8933 (2)	0.36576 (18)	−0.02995 (13)	0.0564 (5)
C10	1.0855 (3)	0.2653 (2)	−0.06975 (18)	0.0795 (7)
C11	0.52301 (19)	0.26419 (13)	0.49686 (11)	0.0433 (4)
C12	0.61041 (19)	0.11222 (13)	0.54526 (11)	0.0422 (4)
C13	0.53767 (18)	0.14089 (15)	0.74933 (11)	0.0463 (4)
C14	0.6216 (2)	0.11142 (18)	0.85005 (12)	0.0582 (5)
C15	0.8845 (2)	0.14204 (18)	0.73395 (14)	0.0568 (5)
C16	0.80961 (18)	0.17138 (14)	0.62963 (12)	0.0440 (4)
C17	0.0219 (2)	0.43050 (16)	0.34677 (16)	0.0596 (5)
H3	0.16610	0.10620	0.34800	0.0760*
H4A	0.40790	0.50770	0.27160	0.0540*
H4B	0.59660	0.44980	0.30410	0.0540*
H5A	0.63620	0.54780	0.11730	0.0590*
H5B	0.54430	0.45600	0.08390	0.0590*
H6	0.88630	0.34690	0.14080	0.0550*
H7A	0.71400	0.18630	0.07950	0.0550*
H7B	0.90660	0.12260	0.10690	0.0550*
H8A	0.77890	0.17740	0.29720	0.0510*
H8B	0.68810	0.08240	0.26710	0.0510*
H9A	0.81850	0.35680	−0.07540	0.0680*
H9B	0.89310	0.46220	−0.04430	0.0680*
H10A	1.08690	0.16960	−0.05860	0.0950*
H10B	1.16160	0.27450	−0.02650	0.0950*
H10C	1.13010	0.28800	−0.14940	0.0950*
H11A	0.43600	0.32010	0.55830	0.0520*
H11B	0.61590	0.30620	0.46440	0.0520*
H12A	0.52110	0.06600	0.56460	0.0510*
H12B	0.70950	0.06160	0.48560	0.0510*
H13A	0.45590	0.08870	0.76210	0.0560*
H13B	0.46810	0.24120	0.74030	0.0560*
H14A	0.52660	0.14080	0.91840	0.0700*
H14B	0.68560	0.01030	0.86120	0.0700*
H15A	0.95260	0.04150	0.74380	0.0680*
H15B	0.96720	0.19290	0.72350	0.0680*
H16A	0.74900	0.27260	0.61620	0.0530*
H16B	0.90790	0.13880	0.56340	0.0530*
H17A	−0.03000	0.44790	0.28190	0.0720*
H17B	0.07200	0.50210	0.34490	0.0720*
H17C	−0.07050	0.43310	0.41580	0.0720*

	U11	U22	U33	U12	U13	U23
S1	0.0492 (2)	0.0609 (2)	0.0430 (2)	−0.0225 (2)	−0.0195 (1)	−0.0021 (1)
O1	0.0516 (6)	0.0715 (7)	0.0478 (6)	−0.0221 (5)	−0.0079 (5)	−0.0035 (5)
O2	0.0749 (7)	0.0766 (7)	0.0507 (6)	−0.0302 (6)	−0.0222 (5)	−0.0163 (5)
O3	0.0399 (5)	0.0454 (5)	0.0692 (6)	−0.0137 (4)	−0.0166 (5)	−0.0089 (4)
N1	0.0419 (5)	0.0422 (5)	0.0398 (5)	−0.0146 (4)	−0.0161 (4)	−0.0012 (4)
N2	0.0394 (5)	0.0387 (5)	0.0373 (5)	−0.0119 (4)	−0.0133 (4)	−0.0046 (4)
C1	0.0391 (6)	0.0411 (6)	0.0511 (7)	−0.0110 (5)	−0.0166 (5)	−0.0048 (5)
C2	0.0411 (6)	0.0375 (6)	0.0459 (7)	−0.0094 (5)	−0.0131 (5)	−0.0042 (5)
C3	0.0402 (6)	0.0366 (6)	0.0392 (6)	−0.0115 (5)	−0.0158 (5)	−0.0019 (5)
C4	0.0513 (7)	0.0353 (6)	0.0488 (7)	−0.0124 (5)	−0.0145 (6)	−0.0040 (5)
C5	0.0584 (8)	0.0385 (7)	0.0504 (7)	−0.0177 (6)	−0.0146 (6)	0.0020 (5)
C6	0.0472 (7)	0.0516 (7)	0.0448 (7)	−0.0209 (6)	−0.0153 (6)	−0.0028 (5)
C7	0.0462 (7)	0.0424 (7)	0.0467 (7)	−0.0100 (6)	−0.0131 (6)	−0.0051 (5)
C8	0.0428 (7)	0.0362 (6)	0.0467 (7)	−0.0097 (5)	−0.0150 (5)	−0.0009 (5)
C9	0.0596 (9)	0.0649 (9)	0.0487 (8)	−0.0294 (8)	−0.0101 (7)	−0.0015 (7)
C10	0.0607 (10)	0.0973 (14)	0.0711 (12)	−0.0298 (10)	0.0037 (9)	−0.0090 (10)
C11	0.0521 (7)	0.0410 (6)	0.0429 (7)	−0.0155 (6)	−0.0216 (6)	−0.0030 (5)
C12	0.0495 (7)	0.0392 (6)	0.0417 (6)	−0.0123 (5)	−0.0192 (6)	−0.0059 (5)
C13	0.0437 (7)	0.0516 (7)	0.0431 (7)	−0.0171 (6)	−0.0075 (6)	−0.0058 (5)
C14	0.0662 (9)	0.0691 (10)	0.0389 (7)	−0.0239 (8)	−0.0104 (7)	−0.0058 (6)
C15	0.0512 (8)	0.0691 (10)	0.0597 (9)	−0.0224 (7)	−0.0249 (7)	−0.0069 (7)
C16	0.0411 (6)	0.0489 (7)	0.0451 (7)	−0.0175 (6)	−0.0114 (5)	−0.0050 (5)
C17	0.0541 (8)	0.0448 (8)	0.0783 (11)	−0.0033 (6)	−0.0299 (8)	−0.0094 (7)

S1—C1	1.8347 (15)	C5—H5A	0.9700
S1—C3	1.8386 (15)	C5—H5B	0.9700
O1—C2	1.2179 (17)	C6—H6	0.9800
O2—C14	1.412 (2)	C7—H7A	0.9700
O2—C15	1.420 (2)	C7—H7B	0.9700
O3—C1	1.3971 (18)	C8—H8A	0.9700
O3—H3	0.8200	C8—H8B	0.9700
N1—C2	1.350 (2)	C9—H9A	0.9700
N1—C11	1.4623 (19)	C9—H9B	0.9700
N1—C3	1.4680 (16)	C10—H10A	0.9600
N2—C12	1.4620 (18)	C10—H10B	0.9600
N2—C16	1.466 (2)	C10—H10C	0.9600
N2—C13	1.4609 (18)	C11—H11A	0.9700
C1—C17	1.519 (2)	C11—H11B	0.9700
C1—C2	1.531 (2)	C12—H12A	0.9700
C3—C4	1.5300 (18)	C12—H12B	0.9700
C3—C8	1.5299 (19)	C13—H13A	0.9700
C4—C5	1.520 (2)	C13—H13B	0.9700
C5—C6	1.527 (2)	C14—H14A	0.9700
C6—C9	1.522 (2)	C14—H14B	0.9700
C6—C7	1.526 (2)	C15—H15A	0.9700
C7—C8	1.5237 (19)	C15—H15B	0.9700
C9—C10	1.513 (3)	C16—H16A	0.9700
C11—C12	1.5314 (18)	C16—H16B	0.9700
C13—C14	1.504 (2)	C17—H17A	0.9600
C15—C16	1.501 (2)	C17—H17B	0.9600
C4—H4A	0.9700	C17—H17C	0.9600
C4—H4B	0.9700
C1—S1—C3	94.89 (6)	C8—C7—H7B	109.00
C14—O2—C15	110.20 (12)	H7A—C7—H7B	108.00
C1—O3—H3	109.00	C3—C8—H8A	109.00
C2—N1—C3	120.17 (12)	C3—C8—H8B	109.00
C3—N1—C11	121.19 (12)	C7—C8—H8A	109.00
C2—N1—C11	118.47 (11)	C7—C8—H8B	109.00
C12—N2—C13	113.18 (12)	H8A—C8—H8B	108.00
C13—N2—C16	109.95 (11)	C6—C9—H9A	109.00
C12—N2—C16	113.51 (11)	C6—C9—H9B	109.00
S1—C1—C2	104.46 (10)	C10—C9—H9A	109.00
S1—C1—C17	113.16 (10)	C10—C9—H9B	109.00
O3—C1—C2	112.49 (11)	H9A—C9—H9B	108.00
O3—C1—C17	106.76 (13)	C9—C10—H10A	109.00
C2—C1—C17	109.29 (12)	C9—C10—H10B	109.00
S1—C1—O3	110.80 (9)	C9—C10—H10C	109.00
O1—C2—N1	124.16 (14)	H10A—C10—H10B	109.00
N1—C2—C1	113.68 (11)	H10A—C10—H10C	109.00
O1—C2—C1	122.14 (14)	H10B—C10—H10C	109.00
S1—C3—N1	103.71 (10)	N1—C11—H11A	109.00
S1—C3—C4	110.66 (10)	N1—C11—H11B	109.00
N1—C3—C4	111.72 (10)	C12—C11—H11A	109.00
N1—C3—C8	111.49 (10)	C12—C11—H11B	109.00
S1—C3—C8	109.19 (9)	H11A—C11—H11B	108.00
C4—C3—C8	109.91 (12)	N2—C12—H12A	108.00
C3—C4—C5	111.93 (11)	N2—C12—H12B	108.00
C4—C5—C6	113.29 (12)	C11—C12—H12A	108.00
C5—C6—C7	109.26 (13)	C11—C12—H12B	108.00
C5—C6—C9	110.96 (12)	H12A—C12—H12B	107.00
C7—C6—C9	112.66 (12)	N2—C13—H13A	110.00
C6—C7—C8	111.36 (11)	N2—C13—H13B	110.00
C3—C8—C7	112.03 (11)	C14—C13—H13A	110.00
C6—C9—C10	114.58 (14)	C14—C13—H13B	110.00
N1—C11—C12	111.58 (11)	H13A—C13—H13B	108.00
N2—C12—C11	115.86 (11)	O2—C14—H14A	109.00
N2—C13—C14	109.49 (13)	O2—C14—H14B	109.00
O2—C14—C13	111.30 (12)	C13—C14—H14A	109.00
O2—C15—C16	111.43 (14)	C13—C14—H14B	109.00
N2—C16—C15	109.68 (12)	H14A—C14—H14B	108.00
C3—C4—H4A	109.00	O2—C15—H15A	109.00
C3—C4—H4B	109.00	O2—C15—H15B	109.00
C5—C4—H4A	109.00	C16—C15—H15A	109.00
C5—C4—H4B	109.00	C16—C15—H15B	109.00
H4A—C4—H4B	108.00	H15A—C15—H15B	108.00
C4—C5—H5A	109.00	N2—C16—H16A	110.00
C4—C5—H5B	109.00	N2—C16—H16B	110.00
C6—C5—H5A	109.00	C15—C16—H16A	110.00
C6—C5—H5B	109.00	C15—C16—H16B	110.00
H5A—C5—H5B	108.00	H16A—C16—H16B	108.00
C5—C6—H6	108.00	C1—C17—H17A	109.00
C7—C6—H6	108.00	C1—C17—H17B	109.00
C9—C6—H6	108.00	C1—C17—H17C	109.00
C6—C7—H7A	109.00	H17A—C17—H17B	109.00
C6—C7—H7B	109.00	H17A—C17—H17C	110.00
C8—C7—H7A	109.00	H17B—C17—H17C	109.00
C3—S1—C1—O3	−137.43 (10)	C12—N2—C16—C15	−175.82 (11)
C3—S1—C1—C2	−16.07 (9)	C17—C1—C2—O1	70.12 (17)
C3—S1—C1—C17	102.70 (12)	C17—C1—C2—N1	−108.05 (14)
C1—S1—C3—N1	14.83 (9)	S1—C1—C2—N1	13.31 (13)
C1—S1—C3—C4	−105.10 (10)	S1—C1—C2—O1	−168.51 (11)
C1—S1—C3—C8	133.79 (9)	O3—C1—C2—N1	133.56 (12)
C14—O2—C15—C16	58.82 (17)	O3—C1—C2—O1	−48.27 (17)
C15—O2—C14—C13	−59.22 (17)	C4—C3—C8—C7	−55.31 (15)
C11—N1—C3—C4	−65.77 (16)	N1—C3—C8—C7	−179.75 (12)
C2—N1—C11—C12	81.87 (15)	S1—C3—C4—C5	−67.62 (15)
C11—N1—C2—O1	−5.22 (19)	N1—C3—C4—C5	177.37 (13)
C3—N1—C2—C1	−2.34 (16)	S1—C3—C8—C7	66.25 (13)
C2—N1—C3—C4	109.35 (14)	C8—C3—C4—C5	53.06 (16)
C3—N1—C11—C12	−102.93 (14)	C3—C4—C5—C6	−54.41 (18)
C11—N1—C3—C8	57.65 (15)	C4—C5—C6—C7	54.72 (17)
C11—N1—C2—C1	172.91 (10)	C4—C5—C6—C9	179.53 (13)
C3—N1—C2—O1	179.53 (12)	C5—C6—C7—C8	−55.82 (16)
C11—N1—C3—S1	175.01 (9)	C5—C6—C9—C10	174.32 (15)
C2—N1—C3—C8	−127.23 (13)	C7—C6—C9—C10	−62.8 (2)
C2—N1—C3—S1	−9.86 (13)	C9—C6—C7—C8	−179.64 (13)
C13—N2—C16—C15	56.27 (14)	C6—C7—C8—C3	57.90 (17)
C12—N2—C13—C14	175.30 (11)	N1—C11—C12—N2	−170.62 (12)
C16—N2—C13—C14	−56.60 (14)	N2—C13—C14—O2	58.47 (16)
C13—N2—C12—C11	71.56 (15)	O2—C15—C16—N2	−57.46 (16)
C16—N2—C12—C11	−54.67 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2i	0.82	1.99	2.7994 (14)	171
C9—H9A···O2ii	0.97	2.57	3.418 (2)	146
C15—H15B···O1iii	0.97	2.55	3.249 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2i	0.82	1.99	2.7994 (14)	171
C9—H9A⋯O2ii	0.97	2.57	3.418 (2)	146
C15—H15B⋯O1iii	0.97	2.55	3.249 (2)	129

Symmetry codes: (i) ; (ii) ; (iii) .