Structural investigations of a tetracyclic endo-norborenyl derivative

Lloyd, B. A.; Arif, and Atta M.; Coots, R. J.; Allred, Evan L.

doi:10.1107/s0108270193012685

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2013

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(2 citation statements)

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“…The greatest difference between symmetry-related bond lengths is 0.011 (4) Å (for C1-C11 versus C8-C11, and between symmetry-related bond angles is 0.78 (20)° (between C2-C7-C6 and C3-C2-C7). Bonds C1-C2, C2-C7, C4-C5 and C7-C8 are somewhat longer than usual, similar to analogous bonds in 2- (Lloyd et al, 1995), isomeric 3- (Lloyd, et al, 1994), 4-, and 5-OPBB (Lloyd & Arif, 2012a,b). Less alkenic C pyramidalization is apparent in 1-OPBB…”

Section: Data Collectionmentioning

confidence: 68%

See 1 more Smart Citation

endo,endo-Tetracyclo[6.2.1.1^3,6.0^2,7]dodeca-9-en-anti-11-yl 4-bromobenzoate

Lloyd

Arif

Coots³

2013

Acta Cryst E

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The title compound 1-OPBB, C19H19BrO2, contains a dechlorinated and hydrogenated isodrin backbone with ananti-4-bromobenzoate substituent at one of the methano bridges. The dihedral angle between the CO2ester plane and the benzene ring plane is 8.5 (2)°. In the crystal, the ester groups stack over benzene rings: the molecules pack as conformational enantiomers, with nearest parallel benzene ring planes separated by a perpendicular distance of 3.339 (1) Å. The nearest benzene-ring centroids are 5.266 (1) Å apart. Possible structural correlation with enhanced solvolytic reactivity is investigated.

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Section: Data Collectionmentioning

confidence: 68%

“…For a structure containing the same tetracyclic framework, see: Lloyd et al (1995). For the isomeric endo,exo-structure, see: Lloyd et al (1994). For solvolysis rate information, see: Coots (1983); Chow & Jiang (2000).…”

Section: Related Literaturementioning

confidence: 99%