Three polymorphs of a new N,N′-dipropylated isoindigo derivative

A newly synthesized N , N ′-dipropyl-substituted isoindigo derivative, namely, 1-propyl-3-(1-propyl-1,2-dihydro-2-oxo-3 H -indol-3-ylidene)-1,3-dihydro-2 H -indol-2-one, C 22 H 22 N 2 O 2 , was found to have three polymorphic forms (denoted Forms I, II and III) under various crystallization conditions. Crystal structure analysis indicated that Form III had a significantly different molecular conformation from the other two polymorphs. Their different packing arrangements were correlated with differences in the intermolecular interactions. Thermal measurements revealed that Forms I and II are enantiotropically related, and Form II exhibits thermally dynamic behaviour.