Cocrystallization of two tautomers: 4-(1-{[4-(dimethylamino)benzylidene]hydrazono}ethyl)benzene-1,3-diol and 6-[(E)-1-{[4-(dimethylamino)benzylidene]hydrazino}ethylidene]-3-hydroxycyclohexa-2,4-dien-1-one (1/1).
Two different tautomeric forms of a new Schiff base, C(17)H(19)N(3)O(2).C(17)H(19)N(3)O(2), are present in the crystal in a 1:1 ratio, namely the enol-imine form 4-(1-{[4-(dimethylamino)benzylidene]hydrazono}ethyl)benzene-1,3-diol and the keto-amine form 6-[(E)-1-{[4-(dimethylamino)benzylidene]hydrazino}ethylidene]-3-hydroxycyclohexa-2,4-dien-1-one. The tautomers are formed by proton transfer between the hydroxy O atom and the imine N atom and are hydrogen bonded to each other to form a one-dimensional zigzag chain along the crystallographic b axis via intermolecular hydrogen bonds.
Wu
Zhen-Hua
ZH
College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, People's Republic of China.
Ma
Jian-Ping
JP
Wu
Xiang-Wen
XW
Huang
Ru-Qi
RQ
Dong
Yu-Bin
YB