Steric repulsion and supra­molecular assemblies via a two-dimensional plate by C—H⋯O hydrogen bonds in two closely related 2-(benzo­furan-2-yl)-2-oxoethyl benzoates

Acta Crystallographica Section E: Crystallographic Communications

Win, Y.-F.¹  Warad, I.²  Chidan Kumar, C.S.³  Naveen, S.⁴  Mah, S.H.⁵  Kwong, H.C.⁶  Quah, C.K.⁷  Then, L.Y.⁷ 

[1] 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 & Technology, Visvesvaraya Technological University, Alanahally, Mysuru 570 028, Karnataka, India;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;    INTERMOLECULAR INTERACTION;    FUNCTIONAL GROUP;   

DOI  :  10.1107/S2056989017010556

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

2-(Benzo­furan-2-yl)-2-oxoethyl 2-chloro­benzoate, C17H11ClO4 (I), and 2-(benzo­furan-2-yl)-2-oxoethyl 2-meth­oxy­benzoate, C18H14O5 (II), were synthesized under mild conditions. Their chemical and mol­ecular structures were analyzed by spectroscopic and single-crystal X-ray diffraction studies, respectively. These compounds possess different ortho-substituted functional groups on their phenyl rings, thus experiencing extra steric repulsion force within their mol­ecules as the substituent changes from 2-chloro (I) to 2-meth­oxy (II). The crystal packing of compound (I) depends on weak inter­molecular hydrogen bonds and π–π inter­actions. Mol­ecules are related by inversion into centrosymmetric dimers via C—H⋯O hydrogen bonds, and further strengthened by π–π inter­actions between furan rings. Conversely, mol­ecules in compound (II) are linked into alternating dimeric chains propagating along the [101] direction, which develop into a two-dimensional plate through extensive inter­molecular hydrogen bonds. These plates are further stabilized by π–π and C—H⋯π inter­actions.

【 授权许可】

CC BY