8-Ethyl-2-hydr­oxy-2-methyl-4-morpholinoethyl-1-thia-4-aza­spiro­[4.5]decan-3-one

Akkurt, M.; Yalçın, Ş.P.; Klip, N.T.; Büyükgüngör, O.

doi:10.1107/S1600536808029097

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages o1939-o1940

doi:10.1107/S1600536808029097

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8-Ethyl-2-hydroxy-2-methyl-4-morpholinoethyl-1-thia-4-azaspiro[4.5]decan-3-one

Mehmet Akkurt,^a ^* Şerife Pınar Yalçın,^a Nalan Terzioğlu Klip ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Pharmacetical Chemistry, Faculty of Pharmacy, stanbul University, Beyazıt 34116, Istanbul, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 9 September 2008; accepted 10 September 2008; online 13 September 2008)

Molecules of the title spiro[4.5]decane derivative, C₁₇H₃₀N₂O₃S, are linked by paired O—H⋯N hydrogen bonds into centrosymmetric R²₂(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_r = 342.50
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.092
S = 1.03
3717 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) -x+1, -y, -z+1; (ii) x, y, z-1; (iii) x+1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029097/hb2794sup1.cif

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

checkCIF report

Comment top

Thiazolidinone derivatives have been shown to possess antibacterial (Sayyed et al., 2006), antimicrobial (Sharma et al., 2006) and antimycobacterial (Babaoğlu et al., 2003) activities. There have also been several reports on the anticancer properties of compounds bearing this ring system (Pfahl et al., 2003). In view of above considerations, we have synthesized the title spiro[4.5]decane derivative, (I), and we report here its crystal structure. This molecule is chiral: in the arbitrarily chosen asymmetric molecule, C1 has R configuration, but crystal symmetry generates a racemic mixture.

The values of the geometric parameters of the molecule shown in Fig. 1 are in their normal ranges and similar to those in the related compounds, 8-methyl-4-morpholinoethyl-1-thia-4-azaspiro[4.5]decan-3-one (Akkurt et al., 2008b) and 2,8-dimethyl-4-morpholinoethyl-1-thia-4-azaspiro[4.5] decan-3-one (Akkurt et al., 2008c).

In the crystal, the molecules of (I) are linked by paired O—H···N hydrogen bonds into centrosymmetric R²₂(16) dimers and these dimers are linked into a three-dimensional framework structure by a combination of three independent C—H···O hydrogen bonds (Table 1). The thiazole ring (C1–C3/S1/N1) has an envelope conformation on S1 [puckering parameters (Cremer & Pople, 1975): Q(2) = 0.2032 (12) Å, ϕ(2) = 6.1 (4) °]. The cyclohexane ring (C3–C8) and morpholine ring (C13–C16/N2/O2) adopt chair conformations [puckering parameters: Q_T = 0.565 (2) Å, θ = 177.6 (2) °, ϕ = 73 (4) °, and Q_T = 0.570 (2) Å, θ = 0.40 (17) °, ϕ = 101 (16) °, respectively].

Related literature top

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 top

A mixture of morpholinoethylamin (5 mmol), 4-ethyl cyclohexanone (5 mmol) and α-mercaptopropionic acid (20 mmol) in dry benzene (20 ml) was refluxed for 18 h using a Dean–Starkwater separator. Excess solvent was evaporated in vacuo. The residue was taken up in chloroform. The chloroform layer was triturated with saturated NaHCO₃ solution (2×) before drying over sodium sulfate and concentrated under reduced pressure to dryness. The crude product was triturated with diethyl ether several times and recrystallized from ethanol to yield colourless prisms of (I).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the hydrogen-bonded dimer in (I), forming a intermolecular R₂²(16) ring. For clarity, H atoms not involved in hydrogen bonds have been omitted.

8-Ethyl-2-hydroxy-2-methyl-4-morpholinoethyl-1-thia- 4-azaspiro[4.5]decan-3-one top

Crystal data top

C₁₇H₃₀N₂O₃S	Z = 2
M_r = 342.50	F(000) = 372
Triclinic, P1	D_x = 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

Data collection top

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 monochromator	R_int = 0.055
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.7°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.900, T_max = 0.949	l = −15→15
18506 measured reflections

Refinement top

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(F_o²) + (0.0459P)² + 0.1334P] where P = (F_o² + 2F_c²)/3
3717 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₇H₃₀N₂O₃S	γ = 67.674 (4)°
M_r = 342.50	V = 905.83 (8) Å³
Triclinic, P1	Z = 2
a = 8.1878 (4) Å	Mo Kα radiation
b = 10.2241 (5) Å	µ = 0.20 mm⁻¹
c = 12.2188 (6) Å	T = 296 K
α = 79.901 (4)°	0.55 × 0.38 × 0.27 mm
β = 73.796 (4)°

Data collection top

STOE IPDS II diffractometer	3717 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3297 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.949	R_int = 0.055
18506 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
3717 reflections	Δρ_min = −0.16 e Å⁻³
208 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1; (ii) x, y, z−1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₃₀N₂O₃S
M_r	342.50
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.1878 (4), 10.2241 (5), 12.2188 (6)
α, β, γ (°)	79.901 (4), 73.796 (4), 67.674 (4)
V (Å³)	905.83 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.55 × 0.38 × 0.27

Data collection
Diffractometer	STOE IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.900, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	18506, 3717, 3297
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.092, 1.03
No. of reflections	3717
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.16

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1; (ii) x, y, z−1; (iii) x+1, y, z.

Acknowledgements

The authors thank the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund). This work was supported by The Research Fund of İstanbul University (project Nos 177/15012004 and UDP-730/05052006).

References

Akkurt, M., Yalçın, Ş. P., Gürsoy, E., Güzeldemirci, N. U. & Büyükgüngör, O. (2007). Acta Cryst. E63, o3103. Web of Science CSD CrossRef IUCr Journals Google Scholar
Akkurt, M., Yalçın, Ş. P., Güzeldemirci, N. U. & Büyükgüngör, O. (2008a). Acta Cryst. E64, o810–o811. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sayyed, M., Mokle, S., Bokhare, M., Mankar, A., Surwase, S., Bhusare, S. & Vilohute, Y. (2006). Arkivoc ii, 187–197. CrossRef Google Scholar
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Volume 64| Part 10| October 2008| Pages o1939-o1940

doi:10.1107/S1600536808029097

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

8-Ethyl-2-hydr­­oxy-2-methyl-4-morpholino­ethyl-1-thia-4-aza­spiro­[4.5]decan-3-one

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Experimental

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organic compounds

8-Ethyl-2-hydroxy-2-methyl-4-morpholinoethyl-1-thia-4-azaspiro[4.5]decan-3-one