Crystal structure of 9-(3-bromo-5-chloro-2-hydroxy-phen-yl)-10-(2-hy-droxy-eth-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione

Antar A Abdelhamid; Shaaban K Mohamed; Jim Simpson

doi:10.1107/S1600536814009556

Crystal structure of 9-(3-bromo-5-chloro-2-hydroxy-phen-yl)-10-(2-hy-droxy-eth-yl)-3,3,6,6-tetra-methyl-3,4,6,7,9,10-hexa-hydro-acridine-1,8(2H,5H)-dione

Acta Crystallogr Sect E Struct Rep Online. 2014 Jul 19;70(Pt 8):44-7. doi: 10.1107/S1600536814009556. eCollection 2014 Aug 1.

Authors

Antar A Abdelhamid¹, Shaaban K Mohamed², Jim Simpson³

Affiliations

¹ Chemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt.
² Chemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England.
³ Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.

Abstract

The title compound C25H29BrClNO4, comprises a 3,3,6,6-tetra-methyl-tetra-hydro-acridine-1,8-dione ring system that carries a hy-droxy-ethyl substituent on the acridine N atom and a 3-bromo-5-chloro-2-hy-droxy-phenyl ring on the central methine C atom of the di-hydro-pyridine ring. The benzene ring is inclined to the acridine ring system at an angle of 89.84 (6)° and this conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond between the hy-droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit. In the crystal, O-H⋯O, C-H⋯O and C-H⋯Br hydrogen bonds combine to stack mol-ecules in inter-connected columns propagating along the a-axis direction.

Keywords: acridine; crystal structure; hydroacridine.