Isochroman derivatives and their tendency to crystallize in chiral space groups.
In methyl [5-methoxy-4-(4-methoxyphenyl)isochroman-3-yl]acetate, C(20)H(22)O(5), (I), and methyl [4-(2,5-dimethoxyphenyl)-8-methoxyisochroman-3-yl]acetate, C(21)H(24)O(6), (II), the heterocyclic rings adopt half-chair conformations. The substituents at the 3- and 4-positions are in a trans configuration in both (I) and (II), being in an axial conformation in (I) and in an equatorial conformation in (II). The crystal structure of (I) is stabilized by weak C-H.O hydrogen bonding, leading to the formation of an infinite three-dimensional network. Compound (II) crystallizes in a chiral space group. This feature, which was also found in previously investigated isochroman derivatives, is related to the arrangement of substituents attached to the isochroman moiety.
Palusiak
Marcin
M
Department of Crystallography and Crystal Chemistry, University of Lodz, Pomorska 149/153, 90236 Łódź, Poland. marcinp@uni.lodz.pl
Pfitzner
Arno
A
Zabel
Manfred
M
Grabowski S
Sławomir J
SJ
Epsztajn
Jan
J
Kowalska
Justyna A
JA