Crystal structures of N,N-dimethyl-(2-(2,2-diphen-yl)-2-prop-2-yn-yloxy)acet-oxy)ethyl-amine and N,N-dimethyl-(2-(2,2-diphen-yl)-2-prop-2-yn-yl--oxy)acet-oxy)ethyl-ammonium 2,4,6-tri-nitro-phenolate.

Mohammed A E Shaibah,Christopher Glidewell,Kullaiah Byrappa,S Madan Kumar,Hemmige S Yathirajan

doi:10.1107/s2056989017012968

Abstract

The N,N-di-methyl-ethylamminium unit in N,N-dimethyl-[2-(2,2-diphen-yl)-2-prop-2-ynyloxyacet-oxy]ethyl-amine, C21H23NO3 (I), is disordered over two sets of atomic sites having occupancies of 0.880 (3) and 0. 120 (3), but there are no direction-specific inter-actions between the mol-ecules of (I). The cation in N,N-dimethyl-[2-(2,2-diphen-yl)-2-prop-2-ynyloxyacet-oxy]ethyl-ammonium 2,4,6-tri-nitro-phenolate (picrate), C21H24NO3+·C6H2N3O7- (II), shows a similar type of disorder, with occupancies of 0.654 (11) and 0.346 (11), although the overall conformation of the cation in (II) is different from that in the neutral (I). The component ions are are linked by an almost planar three-centre N-H⋯(O)2 hydrogen bond, and the ion pairs are further linked by a combination of three C-H⋯O hydrogen bonds to form sheets. Comparisons are made with some related structures.

Highlights

The N,N-dimethylethylamminium unit in N,N-dimethyl-[2-(2,2-diphenyl)-2prop-2-ynyloxyacetoxy]ethylamine, C21H23NO3 (I), is disordered over two sets of atomic sites having occupancies of 0.880 (3) and 0. 120 (3), but there are no direction-specific interactions between the molecules of (I)
The component ions are are linked by an almost planar three-centre N—HÁ Á Á(O)2 hydrogen bond, and the ion pairs are further linked by a combination of three C—HÁ Á ÁO hydrogen bonds to form sheets
In the neutral compound (I) (Fig. 1) the methylaminoethyl fragment is disordered over two sets of atomic sites with occupancies of 0.880 (3) for the major disorder component comprising the atomic sites C2,C1,N1,C111 and C112, and 0.120 (3) for the minor component, comprising the atomic sites C22,C21,N21,C211 and C212

Summary

Chemical context

N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylamine (pargeverine) is an established anti-spasmodic drug (Mishra et al, 2010). Crystal structures have been reported (Bindya et al, 2007; Harrison, Bindya et al, 2007; Harrison, Sreevidya et al, 2007; Swamy et al, 2007; Yathirajan et al, 2007; Jasinski et al, 2009) for a number of related compounds that exhibit a range of pharmacological activities Matsushima et al, 1997), the structure of pargeverine itself has not yet been reported. We report the structure of the neutral compound (I) and its 2,4,6-trinitrophenolate (picrate) salt (II)

Structural commentary

Supramolecular features

Database survey

Refinement

C14 C15 C16 C121 C122 C123 C124 C125 C126 C131 C132 C133 C134 C135 C136