Two closely related 2-(benzo­furan-2-yl)-2-oxoethyl benzoates: structural differences and C—H⋯O hydrogen-bonded supra­molecular assemblies

Acta Crystallographica Section E: Crystallographic Communications

Kwong, H.C.¹  Mah, S.H.²  Chidan Kumar, C.S.⁴  Warad, I.⁵  Quah, C.K.⁶  Win, Y.-F.⁷  Naveen, S.⁸  Then, L.Y.⁸ 

[1] Technology, Visvesvaraya Technological University, Alanahally, Mysuru 570 028, Karnataka, India;Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Perak Campus, Jalan Universiti, Bandar Barat, Perak, Malaysia;Department of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories;Department of Engineering Chemistry, Vidya Vikas Institute of Engineering &Institution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India;School of Biosciences, Taylor's University, Lakeside Campus, 47500 Subang Jaya, Selangor, Malaysia;School of Chemical Sciences, Universiti Sains Malaysia, Penang 11800 USM, Malaysia;X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

关键词: CRYSTAL STRUCTURE;    BENZOFURAN;    INTRAMOLECULAR INTERACTION;    INTERMOLECULAR INTERACTION;    FUNCTIONAL GROUP;   

DOI  :  10.1107/S2056989017009422

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

The compounds 2-(1-benzo­furan-2-yl)-2-oxoethyl 2-nitro­benzoate, C17H11NO6 (I), and 2-(1-benzo­furan-2-yl)-2-oxoethyl 2-amino­benzoate, C17H13NO4 (II), were synthesized under mild conditions. Their mol­ecular structures were characterized by both spectroscopic and single-crystal X-ray diffraction analysis. The mol­ecular conformations of both title compounds are generally similar. However, different ortho-substituted moieties at the phenyl ring of the two compounds cause deviations in the torsion angles between the carbonyl group and the attached phenyl ring. In compound (I), the ortho-nitro­phenyl ring is twisted away from the adjacent carbonyl group whereas in compound (II), the ortho-amino­phenyl ring is almost co-planar with the carbonyl group. In the crystal of compound (I), two C—H⋯O hydrogen bonds link the mol­ecules into chains propagating along the c-axis direction and the chains are inter­digitated, forming sheets parallel to [20-1]. Conversely, pairs of N—H⋯O hydrogen bonds in compound (II) link inversion-related mol­ecules into dimers, which are further extended by C—H⋯O hydrogen bonds into dimer chains. These chains are inter­connected by π–π inter­actions involving the furan rings, forming sheets parallel to the ac plane.

【 授权许可】

CC BY