Crystal structure of 3-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydrocyclopenta[b]indole-2-carboxylic acid

Author(s)

Fernandes, Daniara C. ; Simoni, Deborah de Alencar ; Rodrigues, Manuel T., Jr. ; Santos, Marilia S. ; Coelho, Fernando

• Document type: Journal article
• Source: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS; v. 71, p. 9-pg., 2015-06-01.

Abstract

In the title compound, C21H21NO5, obtained from a Morita-Baylis-Hillman adduct, the hydrogenated five-membered ring adopts a shallow envelope conformation, with the C atom bearing the carboxylic acid substituent deviating by 0.237 (1) angstrom from the mean plane of the other four atoms (r.m.s. deviation = 0.007 angstrom). The dihedral angle between the fused ring system (all atoms; r.m.s. deviation = 0.057 angstrom) and the pendant trimethoxy benzene ring is 66.65 (3)degrees. The C atoms of the meta-methoxy groups lie close to the plane of the benzene ring [deviations = 0.052 (1) and -0.083 (1) angstrom], whereas the C atom of the para-methoxy group is significantly displaced [deviation = -1.289 (1) angstrom]. In the crystal, carboxylic acid inversion dimers generate R-2(2)(8) loops. The dimers are connected by N-H center dot center dot center dot O hydrogen bonds, forming [011] chains. A C-H center dot center dot center dot O interaction is also observed. (AU)

• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• 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