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

Tan, Ming Yueh and Crouse, Karen A. and Ravoof, Thahira Begum S. A. and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2018) 3-{(E)-[4-(4-Hydroxy-3-methoxyphenyl)butan-2-ylidene]amino}-1-phenylurea: crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E Crystallographic Communications, 74 (1). pp. 21-27. ISSN 2056-9890

Tiekink Acta Cryst (2018) E74 21.pdf

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Official URL: http://dx.doi.org/10.1107/S2056989017017273


Two independent mol­ecules (A and B) comprise the asymmetric unit of the title compound, C18H21N3O3. The urea moiety is disubstituted with one amine being linked to a phenyl ring, which is twisted out of the plane of the CN2O 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.

Item Type: Article
Uncontrolled Keywords: crystal structure; urea derivative; hydrogen bonding; Hirshfeld surface analysis
Subjects: Q Science > QD Chemistry
Divisions: Sunway University > School of Engineering and Technology [formerly School of Science and Technology until 2020] > Research Centre for Crystalline Materials moved to SMLS wef 2021
Depositing User: Dr Janaki Sinnasamy
Related URLs:
Date Deposited: 13 Dec 2017 07:43
Last Modified: 07 Oct 2020 09:16
URI: http://eprints.sunway.edu.my/id/eprint/703

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