Crystal structure of 4-(meth-oxy-carbon-yl)phenyl-boronic acid

Keith J Flanagan; Mathias O Senge

doi:10.1107/S2056989015015923

Crystal structure of 4-(meth-oxy-carbon-yl)phenyl-boronic acid

Acta Crystallogr E Crystallogr Commun. 2015 Sep 12;71(Pt 10):1151-4. doi: 10.1107/S2056989015015923. eCollection 2015 Oct 1.

Authors

Keith J Flanagan¹, Mathias O Senge¹

Affiliation

¹ School of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Trinity College Dublin, The University of Dublin, Dublin 2, Ireland.

Abstract

In the title compound, C8H9BO4, the meth-oxy-carbonyl group is rotated out of the plane of the benzene ring by 7.70 (6)°. In the crystal, mol-ecules are linked via pairs of O-H⋯O hydrogen bonds, involving the boronic acid OH groups, forming inversion dimers. The dimers are linked via O-H⋯O hydrogen bonds, involving a boronic acid OH group and the carbonyl O atom, forming undulating sheets parallel to (10-2). Within the sheets there are also C-H⋯O hydrogen bonds present, also involving the carbonyl O atom. The sheets are linked via C-H⋯π and offset face-to-face π-inter-actions between inversion-related mol-ecules [inter-centroid distance = 3.7843 (16) Å, inter-planar distance = 3.3427 (4) Å and offset = 1.744 Å], forming a three-dimensional structure.

Keywords: Suzuki coupling; boronic acid; crystal structure; ester; hydrogen bonding; inversion dimers; methoxycarbonyl; protecting groups; π–π interactions..