The crystal structure of a chiral m-cyclophane

The crystal structure of a chiral m-cyclophane, the α-isomer of (S)-α-methoxy-α-(trifluoromethyl)phenylacetate ester of 13-(methoxycarbonyl)-14-hydroxy-17-methyl-[11]-m-cyclophane (C 30 H 37 O 5 F 3 , FW = 534.62) has been solved by direct methods and refined by a least-squares procedure to a final...

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Veröffentlicht in:Canadian journal of chemistry 1985-12, Vol.63 (12), p.3298-3304
Hauptverfasser: Chan, T. H, Kang, G. J, Belanger-Gariepy, F, Brisse, F, Steliou, K
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Sprache:eng
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Zusammenfassung:The crystal structure of a chiral m-cyclophane, the α-isomer of (S)-α-methoxy-α-(trifluoromethyl)phenylacetate ester of 13-(methoxycarbonyl)-14-hydroxy-17-methyl-[11]-m-cyclophane (C 30 H 37 O 5 F 3 , FW = 534.62) has been solved by direct methods and refined by a least-squares procedure to a final R = 0.048 for 2756 independent reflections. The crystals belong to the orthorhombic system, a = 10.8077(13), b = 13.676(3), c = 19.060(4) Å, V = 2817.2 Å 3 , Z = 4, and the space group is P2 1 2 1 2 1 . The absolute configuration of the chiral plane, using the S-configuration of the α-methoxy-α-(trifluoromethyl)phenylacetate ester as reference, is found to be S, in agreement with the X-ray result. The 14-membered ring has the slightly distorted rectangular conformation that has been described by Dale as the rectangular diamond-lattice conformation [3434]. The distortions, also observed in similar 14-membered rings, have been successfully approximated by molecular mechanics calculations.
ISSN:0008-4042
1480-3291
DOI:10.1139/v85-546