Three closely related (2 E,2' E)-3,3'-(1,4-phenyl-ene)bis-[1-(meth-oxy-phen-yl)prop-2-en-1-ones]: supra-molecular assemblies in one dimension mediated by hydrogen bonding and C-H⋯π inter-actions

Aijia Sim; C S Chidan Kumar; Huey Chong Kwong; Li Yee Then; Yip-Foo Win; Ching Kheng Quah; S Naveen; S Chandraju; N K Lokanath; Ismail Warad

doi:10.1107/S2056989017007460

Three closely related (2 E,2' E)-3,3'-(1,4-phenyl-ene)bis-[1-(meth-oxy-phen-yl)prop-2-en-1-ones]: supra-molecular assemblies in one dimension mediated by hydrogen bonding and C-H⋯π inter-actions

Acta Crystallogr E Crystallogr Commun. 2017 May 26;73(Pt 6):896-900. doi: 10.1107/S2056989017007460. eCollection 2017 Jun 1.

Authors

Aijia Sim¹, C S Chidan Kumar², Huey Chong Kwong³, Li Yee Then¹, Yip-Foo Win⁴, Ching Kheng Quah¹, S Naveen⁵, S Chandraju⁶, N K Lokanath⁷, Ismail Warad⁸

Affiliations

¹ X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
² Department of Engineering Chemistry, Vidya Vikas Institute of Engineering &, Technology, Visvesvaraya Technological University, Alanahalli, Mysuru 570 028, Karnataka, India.
³ School of Chemical Sciences, Universiti Sains Malaysia, Penang 11800 USM, Malaysia.
⁴ Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul, Rahman, Perak Campus, Jalan Universiti, Bandar Barat, Perak, Malaysia.
⁵ Institution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India.
⁶ Department of Sugar Technology & Chemistry, University of Mysore, Sir M. Visvesvaraya PG Centre, Tubinakere, Mandya 571 402, India.
⁷ Department of Studies in Physics, University of Mysore, Manasagangotri, Mysuru, 570 006, India.
⁸ Department of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories.

Abstract

In the title compounds, (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(2-meth-oxy-phen-yl)prop-2-en-1-one], C₂₆H₂₂O₄ (I), (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(3-meth-oxy-phen-yl)prop-2-en-1-one], C₂₆H₂₂O₄ (II) and (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one], C₂₈H₂₆O₆ (III), the asymmetric unit consists of a half-mol-ecule, completed by crystallographic inversion symmetry. The dihedral angles between the central and terminal benzene rings are 56.98 (8), 7.74 (7) and 7.73 (7)° for (I), (II) and (III), respectively. In the crystal of (I), mol-ecules are linked by pairs of C-H⋯π inter-actions into chains running parallel to [101]. The packing for (II) and (III), features inversion dimers linked by pairs of C-H⋯O hydrogen bonds, forming R₂²(16) and R₂²(14) ring motifs, respectively, as parts of [201] and [101] chains, respectively.

Keywords: C—H⋯O hydrogen bond; C—H⋯π interactions; bischalcone; crystal structure; enone bridge; methoxyphenyl ring.