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Structure of an anti-aldol addition product of benzaldehyde and a pseudoephedrine-derived O-silyl ketene N,O-acetal

Marsh, Richard E. and Schaefer, William P. and Widdowson, Katherine L. and Myers, Andrew G. (1992) Structure of an anti-aldol addition product of benzaldehyde and a pseudoephedrine-derived O-silyl ketene N,O-acetal. Acta Crystallographica Section C, 48 (11). pp. 1948-1951. ISSN 0108-2701. doi:10.1107/S0108270192002233.

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[4S-(4R*,5R*,8R*,9S*)]-2,2,5,6,8-Pentamethyl-4,9-diphenyl-1,3-dioxa-6-aza-2-silacyclononan-7-one, C_(22)H_(29)NO_3Si, M_r = 383.56, monoclinic, P2_1, a = 6.550 (3), b = 17.318 (6), c = 20.129 (6) Å, β = 98.83 (3)°, V = 2256.2 (14) Å^3, Z = 4, D_x = 1.13 g cm^(-3), λ(Mo Kα) = 0.71073 Å, µ = 1.18 cm^(-1), F(000) = 824, room temperature, R on F = 0.039 for 4305 reflections with F_o^2 > 3σ(F_o^2). The two independent molecules in this structure have nearly the same configuration and geometry, with average Si-C bond distances of 1.842 (3) Å and average Si-O bond distances of 1.636 (7) Å; angles at Si differ from 109.5° by an average of 3.5°. The nine-membered rings are fully extended and the planes of the phenyl groups are approximate perpendicular to the nine-membered ring.

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Additional Information:© 1992 International Union of Crystallography. Received 30 September 1991; accepted 18 February 1992. Generous financial support from the National Science Foundation is gratefully acknowledged.
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Caltech Division of Chemistry and Chemical Engineering8513
Issue or Number:11
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ID Code:73574
Deposited By: Tony Diaz
Deposited On:21 Jan 2017 02:02
Last Modified:11 Nov 2021 05:18

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