Crystal structure of methyl 2-(2H-1,3-benzodioxol-5-yl)-7,9-dibromo-8-oxo1-oxaspiro[4.5]deca-2,6,9-triene-3-carboxylate

Author(s)

Martins, Lucimara Julio ; Simoni, Deborah de Alencar ; Aparicio, Ricardo ; Coelho, Fernando

• Document type: Journal article
• Source: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS; v. 70, p. 9-pg., 2014-12-01.

Abstract

The title compound, C18H12Br2O6, was synthesized from Morita-Baylis-Hillman adducts. It incorporates the brominated spiro-hexadienone moiety typically exhibited by compounds of this class that exhibit biological activity. Both the brominated cyclohexadienone and the central five-membered rings are nearly planar (r.m.s. deviations of 0.044 and 0.016 angstrom, respectively), being almost perpendicularly oriented [interplanar angle = 89.47 (5)degrees]. With respect to the central five-membered ring, the brominated cyclohexadienone ring, the benzodioxol ring and the carboxylate fragment make C-O-C-C, O-C-C-C and C-C-C-O dihedral angles of -122.11 (8), -27.20 (11) and -8.40 (12)degrees, respectively. An intramolecular C-H center dot center dot center dot O hydrogen bond occurs. In the crystal, molecules are linked by non-classical C-H center dot center dot center dot O and C-H center dot center dot center dot Br hydrogen bonds resulting in a molecular packing in which the brominated rings are in a head-to-head orientation, forming well marked planes parallel to the b axis. (AU)

• FAPESP's process: 09/51602-5 - Chemical biology: new natural and synthetic molecular targets against cancer, structural studies, biological evaluation and mode of action
• Grantee: Ronaldo Aloise Pilli
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 09/18390-4 - Morita-Baylis-Hillma in synthesis: structural diversity and biological evaluation of spirocyclohexadienones
• Grantee: Lucimara Júlio Martins
• Support Opportunities: Scholarships in Brazil - Doctorate