Abstract
The crystal and molecular structure oftrans-4-t-butylcyclohexanol parabromobenzoate has been studied by X-ray crystallographic methods. Crystals of this compound are triclinic, space groupP¯1, with unit cell constantsa = 9·813(2),b = 13·451(3),c = 6·564(3) Å, α = 102·99(3), β = 98·88(3), γ = 89·99(3) ° andZ = 2. Using a GE XRD-6 diffractometer equipped with a scintillation detector, 3165 reflexions were measured to the limit 2θ = 140 ° for the Cu sphere. The structure was refined by least-squares methods toR (conventional) = 0·058. The main results of this study are:
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(i)
no flattening is induced into the cyclohexane ring and there is no elongation of the C(t-bu)-C(cyclohexane) bond;
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(ii)
the steric strain introduced by thet-butyl group is minimized by a flattening of the C(4), C(3), C(7), C(5) pyramid;
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(iii)
the axial hydrogen atom on C(1) nearly eclipses the carbonyl oxygen, as found in the earlier studies of the acetates and esters of cyclohexanols.
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We are grateful to Professor H. Kagan for bringing this problem to our attention and for the crystals of PBTB, to Dr D. Harker for his interest and valuable suggestions and to Dr C. Altona for sending a preprint of his paper. We are thankful to Mrs. Winiewicz for her excellent technical assistance. Partial financial assistance by NIH-GM-15787 is gratefully acknowledged.
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Ohrt, J., Parthasarathy, R. Crystal and molecular structure of trans-4-t-butylcyclohexanol parabromobenzoate. Journal of Crystal and Molecular Structure 2, 213–223 (1972). https://doi.org/10.1007/BF01246638
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DOI: https://doi.org/10.1007/BF01246638