Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one
Abstract
:Introduction
Results and Discussion
Empirical formula | C12H12O4 |
Formula weight | 220.22 |
Temperature, T (K) | 183(2) |
Wavelength, λ (Å) | 0.71073 |
Crystal system | orthorhombic |
Space group | P212121 |
Unit cell dimensions (Å) | a = 5.7069(1) |
b = 8.4010(1) | |
c = 21.2427(4) | |
Unit cell volume, V (Å3) | 1018.45(3) |
Formula units per unit cell Z | 4 |
Dcalcd (g/cm3) | 1.436 |
Absorption coefficient, μ (mm-1) | 0.108 |
F(000) | 464 |
Crystal size (mm) | 0.70 × 0.54 × 0.44 |
Diffractometer | Siemens SMART CCD |
θ Range (°) | 2.61–28.25 |
Range of h | –7→7 |
Range of k | –11→11 |
Range of l | –27→27 |
Reflections | 11525 |
Independent reflections | 2371 (Rint = 0.0328) |
Completeness to θ = 28.25 (%) | 95.7 |
Absorption correction | multi-scan |
Max. and min. transmission | 0.9539 and 0.9281 |
Refinement method | Full-matrix least-squares on F2 |
Data / restraints / parameters | 2371 / 0 / 158 |
Goodness-of-fit on F2 | 1.002 |
Final R indices [I>2σ(I)] | R1 = 0.0336, wR2 = 0.0798 |
R indices (all data) | R1 = 0.0400, wR2 = 0.0846 |
Largest difference peak and hole (e/Å3) | 0.195 and –0.209 |
O(1)-C(3) | 1.2065(17) | C(5)-C(1)-C(8) | 104.37(11) | |
O(2)-C(3) | 1.3533(18) | O(1)-C(3)-O(2) | 120.39(15) | |
O(2)-C(1) | 1.4474(16) | O(1)-C(3)-C(4) | 128.97(14) | |
O(3)-C(8) | 1.4211(15) | O(2)-C(3)-C(4) | 110.63(12) | |
O(6)-C(7) | 1.4379(17) | C(3)-C(4)-C(5) | 105.48(12) | |
O(6)-C(5) | 1.4382(17) | O(6)-C(5)-C(1) | 106.39(11) | |
C(1)-C(5) | 1.540(2) | O(6)-C(5)-C(4) | 112.97(13) | |
C(1)-C(8) | 1.5206(18) | C(1)-C(5)-C(4) | 103.71(12) | |
C(3)-C(4) | 1.499(2) | O(6)-C(7)-C(9) | 112.15(12) | |
C(4)-C(5) | 1.524(2) | O(6)-C(7)-C(8) | 104.29(11) | |
C(7)-C(9) | 1.5076(19) | C(9)-C(7)-C(8) | 114.36(11) | |
C(7)-C(8) | 1.5315(19) | O(3)-C(8)-C(1) | 105.62(11) | |
C(3)-O(2)-C(1) | 111.22(11) | O(3)-C(8)-C(7) | 112.58(12) | |
C(7)-O(6)-C(5) | 108.55(11) | C(1)-C(8)-C(7) | 101.00(11) | |
O(2)-C(1)-C(5) | 106.51(11) | C(10)-C(9)-C(7) | 123.04(13) | |
O(2)-C(1)-C(8) | 109.74(11) | C(14)-C(9)-C(7) | 117.78(13) |
O(2)-C(1)-C(5)-C(4) | 15.69(14) | O(2)-C(1)-C(5)-O(6) | –103.68(12) | |
C(1)-C(5)-C(4)-C(3) | –12.53(15) | C(8)-C(1)-C(5)-C(4) | 131.77(11) | |
C(5)-C(4)-C(3)-O(2) | 5.14(16) | C(3)-C(4)-C(5)-O(6) | 102.24(14) | |
C(4)-C(3)-O(2)-C(1) | 5.32(16) | C(5)-O(6)-C(7)-C(9) | –157.52(11) | |
C(3)-O(2)-C(1)-C(5) | –13.49(14) | O(2)-C(1)-C(8)-O(3) | –159.61(11) | |
O(6)-C(5)-C(1)-C(8) | 12.40(15) | C(5)-C(1)-C(8)-O(3) | 86.59(13) | |
C(5)-C(1)-C(8)-C(7) | –30.83(13) | O(2)-C(1)-C(8)-C(7) | 82.97(13) | |
C(1)-C(8)-C(7)-O(6) | 39.33(13) | O(6)-C(7)-C(8)-O(3) | –72.88(14) | |
C(8)-C(7)-O(6)-C(5) | –33.23(15) | C(9)-C(7)-C(8)-O(3) | 49.98(16) | |
C(7)-O(6)-C(5)-C(1) | 13.00(15) | C(9)-C(7)-C(8)-C(1) | 162.18(12) | |
C(3)-O(2)-C(1)-C(8) | –125.91(12) | C(8)-C(7)-C(9)-C(10) | –106.15(16) | |
C(7)-O(6)-C(5)-C(4) | –100.14(14) | O(6)-C(7)-C(9)-C(14) | –168.01(12) |
X–H…Y | Symmetry code | X–H(Å) | H…Y(Å) | X…Y(Å) | X–H…Y(°) |
O(3)–H(3)…O(1) | x, y+1, z | 0.84 | 2.12 | 2.8885(14) | 151.2 |
C(1)–H(1)…O(1) | –x, y+0.5, –z+0.5 | 1.00 | 2.55 | 3.4976(19) | 157.3 |
Experimental
General
X-ray techniques
(1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one (2).
Acknowledgements
References and Notes
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Langer, V.; Gyepesová, D.; Koman, M.; Kapitán, P.; Babjak, M.; Gracza, T.; Koóš, M. Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one. Molecules 2003, 8, 599-606. https://doi.org/10.3390/80700599
Langer V, Gyepesová D, Koman M, Kapitán P, Babjak M, Gracza T, Koóš M. Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one. Molecules. 2003; 8(7):599-606. https://doi.org/10.3390/80700599
Chicago/Turabian StyleLanger, Vratislav, Dalma Gyepesová, Marian Koman, Peter Kapitán, Matej Babjak, Tibor Gracza, and Miroslav Koóš. 2003. "Preparation and Crystal Structure of (1S, 5S, 7S, 8R)-8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one" Molecules 8, no. 7: 599-606. https://doi.org/10.3390/80700599