Literature DB >> 26090185

Crystal structure of 3-(3,4,5-tri-meth-oxy-phen-yl)-1,2,3,4-tetra-hydro-cyclo-penta[b]indole-2-carb-oxy-lic acid.

Daniara Fernandes1, Deborah de Alencar Simoni2, Manoel T Rodrigues1, Marilia S Santos1, Fernando Coelho1.   

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 carb-oxy-lic acid substituent deviating by 0.237 (1) Å from the mean plane of the other four atoms (r.m.s. deviation = 0.007 Å). The dihedral angle between the fused ring system (all atoms; r.m.s. deviation = 0.057 Å) and the pendant trimeth-oxy benzene ring is 66.65 (3)°. The C atoms of the meta-meth-oxy groups lie close to the plane of the benzene ring [deviations = 0.052 (1) and -0.083 (1) Å], whereas the C atom of the para-meth-oxy group is significantly displaced [deviation = -1.289 (1) Å]. In the crystal, carb-oxy-lic acid inversion dimers generate R 2 (2)(8) loops. The dimers are connected by N-H⋯O hydrogen bonds, forming [011] chains. A C-H⋯O inter-action is also observed.

Entities:  

Keywords:  Morita–Baylis–Hillman adduct; crystal strycture; hydrogen bonding; indole skeleton

Year:  2015        PMID: 26090185      PMCID: PMC4459319          DOI: 10.1107/S2056989015008786

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


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