Different N-H center dot center dot center dot pi interactions in two indole derivatives

被引:4
|
作者
Kerr, Jamie R. [1 ]
Trembleau, Laurent [1 ]
Storey, John M. D. [1 ]
Wardell, James L. [1 ,2 ]
Harrison, William T. A. [1 ]
机构
[1] Univ Aberdeen, Dept Chem, Meston Walk, Aberdeen AB24 3UE, Scotland
[2] Fundacao Oswaldo Cruz, Inst Tecnol Farmacos Far Manguinhos, BR-21041250 Rio De Janeiro, RJ, Brazil
关键词
crystal structure; indole; N-H center dot center dot center dot pi interaction; chains; inversion dimers;
D O I
10.1107/S2056989016006162
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
We describe the syntheses and crystal structures of two indole derivatives, namely 6-isopropyl-3-(2-nitro-1-phenylethyl)-1H-indole, C19H20N2O2, (I), and 2-(4-methoxyphenyl)-3-(2-nitro-1-phenylethyl)-1H-indole, C23H20N2O3, (II); the latter crystallizes with two molecules (A and B) with similar conformations (r.m.s. overlay fit = 0.139 angstrom) in the asymmetric unit. Despite the presence of O atoms as potential acceptors for classical hydrogen bonds, the dominant intermolecular interaction in each crystal is an N-H center dot center dot center dot pi bond, which generates chains in (I) and A+A and B+B inversion dimers in (II). A different aromatic ring acts as the acceptor in each case. The packing is consolidated by C-H center dot center dot center dot pi interactions in each case but aromatic pi-pi stacking interactions are absent.
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页码:699 / +
页数:19
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