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Solid state conformational parameters in dibenzo[b,f]heteroepin drugs: Crystal structures of 3-methoxy-10-methyl-11-phenyldibenzo[b, f]thiepine and 3-allyloxy-10-ethyl-11-phenyldibenzo[b, f]oxepine

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Abstract

The structures of 3-methoxy-10-methyl-11-phenyldibenzo[b, f]thiepine (I) [C22H18OS, tetragonal,I41/a, witha=33.81(1),c=6.065(5)Å,Z=16] and 3-allyloxy-10-ethyl-11-phenyldibenzo[b,f]oxepine (II) [C25H22O2, mono-clinic,P21/c,a=12.115(7),b=16.316(9),c=10.136(7)Å,β=105.05(9)°,Z=4] have been determined by the symbolic addition procedure and refined by least-squares method to anR of 0.090 for 784 diffractometer-measured reflections (I) and to anR of 0.083 for 442 reflections (II). The dihedral angle between the phenyl-ring mean planes is 111.3° in (I) and 121.1° in (II), the middle seven-membered ring has the “boat” conformation, and the tricyclic moiety has twist and skew values of 6° and 0.42 Å in (I) and 0.3° and 0.79 Å in (II). The overall conformational characteristic for the tricyclic (6, 7, 6)-dibenzo[b,f]heteroepin derivatives have been reviewed to gain a better understanding of what requirements may be important for interaction of drugs of this class at the receptor site.

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  1. Facoltá di Farmacia, Universitá degli Studi di Padova, Via Marzolo n. 5, 35100, Padova, Italy

    Giuliano Bandoli & Marino Nicolini

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  1. Giuliano Bandoli
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Bandoli, G., Nicolini, M. Solid state conformational parameters in dibenzo[b,f]heteroepin drugs: Crystal structures of 3-methoxy-10-methyl-11-phenyldibenzo[b, f]thiepine and 3-allyloxy-10-ethyl-11-phenyldibenzo[b, f]oxepine. Journal of Crystallographic and Spectroscopic Research 12, 425–447 (1982). https://doi.org/10.1007/BF01161405

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