Open AccessSterically shielded pyramidal amino groups in two 4,4′‐(arylmethylene)bis(6‐allyl‐3‐chloro‐2‐methylaniline) derivatives
Author(s) -
Blanco Maria C.,
Palma Alirio,
Bahsas Ali,
Hursthouse Michael B.,
Cobo Justo,
Glidewell Christopher
Publication year - 2009
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270109031175
Subject(s) - chemistry , steric effects , hydrogen bond , molecule , stereochemistry , crystallography , double bond , medicinal chemistry , polymer chemistry , organic chemistry
4,4′‐(Phenylmethylene)bis(6‐allyl‐3‐chloro‐2‐methylaniline), C 27 H 28 Cl 2 N 2 , (I), and 4,4′‐(2‐thienylmethylene)bis(6‐allyl‐3‐chloro‐2‐methylaniline), C 25 H 26 Cl 2 N 2 S, (II), adopt similar molecular conformations, although the thienyl group in (II) exhibits orientational disorder over two sets of sites with occupancies of 0.614 (3) and 0.386 (3). The amino groups in both compounds are pyramidal. A single N—H...N hydrogen bond links the molecules of (I) into cyclic centrosymmetric dimers. Molecules of (II) are linked by an ordered C—H...π(arene) hydrogen bond to form cyclic centrosymmetric dimers, and these dimers are linked into statistically interrupted chains by a second C—H...π(arene) hydrogen bond involving a donor in the minor component of the disordered thienyl unit.