Structure of (+-)-6-methyl-6,12-methano-6H,12H,13H-[1]benzopyran[4,3-d] [1,3]benzodioxocin-13-one.
A derivative of warfarin, racemic C19H14O4, Mr = 306.32, monoclinic, Cc, a = 9.594 (2), b = 20.437 (4), c = 7.793 (2) A, beta = 109.94 (3) degree, V = 1436.4 (11) A3, Z = 4, Dx = 1.416 g cm-3, lambda(CuK alpha) = 1.5418 A, mu = 7.742 cm-1, F(000) = 640, T = 293 K, final R = 0.053 for 1224 observations. The title molecule, formed by spontaneous dehydration of 2'-hydroxy-warfarin, is a cyclic ketal in which the side-chain phenyl is disposed pseudoaxially and is linked through a 2'-oxygen to the ketal carbon in a fixed cis 1,3-diaxial configuration. Two dihydropyran rings are formed; one fused with the benzopyran ring adopts an e,f-diplanar conformation, the other is a chroman and is in a similar conformation.
Ruggiero
G
G
Department of Chemistry, Mississippi College, Clinton 39058.
Valente
E J
EJ
Eggleston
D S
DS
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003460:Crystallization; D003461:Crystallography; D008968:Molecular Conformation; D015394:Molecular Structure; D014859:Warfarin / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D014859:Warfarin; C062169:6-methyl-6,12-methano-6H,12H,13H-benzopyran(4,3-d)benzodioxocin-13-one