3-{( E )-[4-(4-Hydroxy-3-methoxyphenyl)butan-2-ylidene]amino}-1-phenylurea: crystal structure and Hirshfeld surface analysis

• Published in: Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2018-01, Vol.74 (1), p.21-27
• Main Authors: Tan, Ming Yueh, Crouse, Karen A., Ravoof, Thahira B. S. A., Jotani, Mukesh M., Tiekink, Edward R. T.
• Format: Article
• Language: English
• Subjects: crystal structure; Hirshfeld surface analysis; hydrogen bonding; urea derivative
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989017017273

Two independent molecules ( A and B ) comprise the asymmetric unit of the title compound, C 18 H 21 N 3 O 3 . The urea moiety is disubstituted with one amine being linked to a phenyl ring, which is twisted out of the plane of the CN 2 O urea core [dihedral angles = 25.57 (11) ( A ) and 29.13 (10)° ( B )]. The second amine is connected to an imine ( E conformation), which is linked in turn to an ethane bridge that links a disubstituted benzene ring. Intramolecular amine-N—H...N(imine) and hydroxyl-O—H...O(methoxy) hydrogen bonds close S (5) loops in each case. The molecules have twisted conformations with the dihedral angles between the outer rings being 38.64 (81) ( A ) and 48.55 (7)° ( B ). In the crystal, amide-N—H...O(amide) hydrogen bonds link the molecules A and B via an eight-membered {...HNCO} 2 synthon. Further associations between molecules, leading to supramolecular layers in the ac plane, are hydrogen bonds of the type hydroxyl-O—H...N(imine) and phenylamine-N—H...O(methoxy). Connections between layers, leading to a three-dimensional architecture, comprise benzene-C—H...O(hydroxy) interactions. A detailed analysis of the calculated Hirshfeld surfaces shows molecules A and B participate in very similar intermolecular interactions and that any variations relate to conformational differences between the molecules.