Structure of a benzamide derivative

Abstract

Amino-5-chloro-2-methoxy-N- { 2-(N- (p- ro ethoxybenzyl)methylamino )- 1,1 -dimethylethyl } benz- amide, C21H28CIN303, M r = 405.93, monoclinic, P21/c, a = 6.144 (I), b = 26.512 (2), c = 13.741 (2) A, fl=94.76(1) °, V= 2230.5 (5) A3, Z=4, D_= 1.21, D x = 1.209 gcm -3, /),(Mo Ka) = 0.71073 ~, It = 1.92cm -I, F(000)=864, room temperature, R= 0.076 for 3926 observed reflections. The benzamide moiety adopts a conformation and intramolecular hydrogen bond similar to those of a potent analogue, while the distance between the tertiary N atom and the center of the benzene ring is different. An inter- molecular hydrogen bond of 3.019 (3) A exists between the amino group N and the carbonyl O. Introduction. The crystal-structure determination of the title compound (1) was undertaken as a part of continuous studies to find new potent neuroleptic drugs in benzamide derivatives in order to establish the three-dimensional structure-activity relationships. The crystal structure of a most potent compound, YM- 09151-2 (2) (Furuya, Iwanami, Takenaka & Sasada, 1982), has been determined previously. Even though the present compound is not an active one contrary to expectation, the comparison of the structural features of