Structure of (+/-)-(1S*,3S*)-3-hydroxy-8,11,11-trimethyl-9-oxobicyclo[5.3.1]undec-7- en-1-yl benzoate.
C21H26O4, Mr = 342.43, monoclinic, P2(1)/n, a = 7.211 (2), b = 19.521 (6), c = 12.674 (3) A, beta = 95.04 (2) degrees, V = 1777.2 (8) A3, Z = 4, Dx = 1.28 g cm-3, Mo K alpha radiation, lambda = 0.7107 A, mu = 0.8152 cm-1, F(000) = 736, T = 163 K, R = 0.0632 for 3754 reflections [Fo greater than or equal to 4 sigma(Fo)]. The molecules exist as hydrogen-bonded dimers [O14-H14...O16 (related by -x, 1-y, 1-z), O14...O16 2.775 (2), H14...O16 1.93 (2) A, O14-H14...O16 175 (2) degrees] which stack in columns along b. Distortion at the bridgehead double bond is observed. Deviations from ideal values for the torsion angles around the double bond, C7-C8, are as large as 17.8 (2) degrees. The dihedral angle between planes through C6-C7-C8-C11 and C7-C8-C9-C15, the planar portions of the alkene moiety, is 13.4 (9) degrees. The Csp2--Csp3 bond lengths involving C7 are asymmetric with C7-C6 1.501 (2) and C7-C11 1.538 (2) A. The bond length C7-C8 is elongated [1.352 (3) A] for a C-C double bond. The enone system is also non-planar [max. deviation -0.404 (2) A for C10].
Lynch
V M
VM
Department of Chemistry, University of Texas, Austin 78712.
Fishpaugh
J R
JR
Martin
S F
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Davis
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D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004224:Diterpenes; D006860:Hydrogen Bonding; D015394:Molecular Structure; D014961:X-Ray Diffraction
C066150:3-hydroxy-8,11,11-trimethyl-9-oxabicyclo(5.3.1)undec-7-en-1-yl benzoate; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004224:Diterpenes