3-{(E)-[4-(4-Hy-droxy-3-meth-oxy-phen-yl)butan-2-yl-idene]amino}-1-phenyl-urea: crystal structure and Hirshfeld surface analysis

Ming Yueh Tan; Karen A Crouse; Thahira B S A Ravoof; Mukesh M Jotani; Edward R T Tiekink

doi:10.1107/S2056989017017273

3-{(E)-[4-(4-Hy-droxy-3-meth-oxy-phen-yl)butan-2-yl-idene]amino}-1-phenyl-urea: crystal structure and Hirshfeld surface analysis

Acta Crystallogr E Crystallogr Commun. 2018 Jan 1;74(Pt 1):21-27. doi: 10.1107/S2056989017017273.

Authors

Ming Yueh Tan¹, Karen A Crouse^{2

3}, Thahira B S A Ravoof², Mukesh M Jotani⁴, Edward R T Tiekink⁵

Affiliations

¹ Department of Physical Science, Faculty of Applied Sciences, Tunku Abdul Rahman, University College, 50932 Setapak, Kuala Lumpur, Malaysia.
² Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400, UPM Serdang, Selangor Darul Ehsan, Malaysia.
³ Department of Chemistry, St. Francis Xavier University, PO Box 5000, Antigonish, NS B2G 2W5, Canada.
⁴ Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India.
⁵ Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia.

Abstract

Two independent mol-ecules (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. Intra-molecular amine-N-H⋯N(imine) and hydroxyl-O-H⋯O(meth-oxy) hydrogen bonds close S(5) loops in each case. The mol-ecules 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 mol-ecules A and B via an eight-membered {⋯HNCO}₂ synthon. Further associations between mol-ecules, leading to supra-molecular layers in the ac plane, are hydrogen bonds of the type hydroxyl-O-H⋯N(imine) and phenyl-amine-N-H⋯O(meth-oxy). Connections between layers, leading to a three-dimensional architecture, comprise benzene-C-H⋯O(hy-droxy) inter-actions. A detailed analysis of the calculated Hirshfeld surfaces shows mol-ecules A and B participate in very similar inter-molecular inter-actions and that any variations relate to conformational differences between the mol-ecules.

Keywords: Hirshfeld surface analysis; crystal structure; hydrogen bonding; urea derivative.

Grants and funding

This work was funded by Sunway University grant INT-PRO-2017–096. Universiti Putra Malaysia grants RUGS 9199834 and RUGS 9174000. Kementerian Sains, Teknologi dan Inovasi grant 09–02–04–0752-EA001.