Crystal structures of four indole derivatives with a phenyl substituent at the 2-position and a carbonyl group at the 3-position: the C(6) N—H⋯O chain remains the same, but the weak reinforcing inter­actions are different

Acta Crystallographica Section E: Crystallographic Communications

Kerr, J.R.²  Trembleau, L.²  Wardell, J.L.²  Storey, J.M.D.²  Harrison, W.T.A.³ 

[1] ãDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland;Fundaço Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil

关键词: CRYSTAL STRUCTURE;    INDOLE;    N-H...O HYDROGEN BOND;    C(6) CHAIN;    WEAK INTERACTIONS;   

DOI  :  10.1107/S2056989016002620

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

We describe the crystal structures of four indole derivatives with a phenyl ring at the 2-position and different carbonyl-linked substituents at the 3-position, namely 1-(2-phenyl-1H-indol-3-yl)ethanone, C16H13NO, (I), 2-cyclo­hexyl-1-(2-phenyl-1H-indol-3-yl)ethanone, C22H23NO, (II), 3,3-dimethyl-1-(2-phenyl-1H-indol-3-yl)butan-1-one, C20H21NO, (III), and 3-benzoyl-2-phenyl-1H-indole, C21H15NO, (IV). In each case, the carbonyl-group O atom lies close to the indole-ring plane and points towards the benzene ring. The dihedral angles between the indole ring system and 2-phenyl ring for these structures are clustered in a narrow range around 65°. The dominant inter­molecular inter­action in each case is an N—H⋯O hydrogen bond, which generates a C(6) chain, although each structure possesses a different crystal symmetry. The C(6) chains are consolidated by different (C—H⋯O, C—H⋯π and π–π stacking) weak inter­actions, with little consistency between the structures.

【 授权许可】

CC BY