Acta Cryst. (2008). E64, o1939-o1940 [ doi:10.1107/S1600536808029097 ]
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-HO interactions.
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).
All H atoms were placed geometrically (C—H = 0.96–0.98 Å, O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C, O).
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).
![[Figure 1]](./hb2794fig1thm.gif)
| Fig. 1. The molecular structure of (I). Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. |
![[Figure 2]](./hb2794fig2thm.gif)
| 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. |
| 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 |
| C17H30N2O3S | γ = 67.674 (4)° |
| Mr = 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)° |
| STOE IPDS II diffractometer | 3717 independent reflections |
| Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 3297 reflections with I > 2σ(I) |
| Tmin = 0.900, Tmax = 0.949 | Rint = 0.055 |
| 18506 measured reflections | θmax = 26.5° |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.092 | Δρmax = 0.25 e Å−3 |
| S = 1.03 | Δρmin = −0.16 e Å−3 |
| 3717 reflections | Absolute structure: ? |
| 208 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 |
| Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z−1; (iii) x+1, y, z. |
| 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. |
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).
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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: QT = 0.565 (2) Å, θ = 177.6 (2) °, φ = 73 (4) °, and QT = 0.570 (2) Å, θ = 0.40 (17) °, φ = 101 (16) °, respectively].