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

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.

Keywords: crystal structure; disorder; hydrogen bonding; mol­ecular conformation.

Figure 1

The mol­ecular structure of compound (I) showing the atom-labelling scheme and the disorder. Displacement ellipsoids are drawn at the 30% probability level, and the minor disorder component is drawn with broken lines.

Figure 2

The ionic components of compound (II) showing the atom-labelling scheme and the disorder. Displacement ellipsoids are drawn at the 30% probability level, and the minor disorder component is drawn with broken lines.

Figure 3

Part of the crystal structure of compound (II) showing the formation of a hydrogen-bonded chain running parallel to [100]. For the sake of clarity, only the major disorder component of the cation is shown and the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) and a hash (#) are at the symmetry positions (−1 + x, y, z) and (1 + x, y, z), respectively.

Figure 4

Part of the crystal structure of compound (II) showing the formation of a hydrogen-bonded chain of rings running parallel to [10]. For the sake of clarity, only the major disorder component of the cation is shown and the H atoms bonded to the C atoms which are not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) and a hash (#)are at the symmetry positions (1 + x, −1 + y, z) and (−1 + x, 1 + y, z), respectively.

Figure 5

Part of the crystal structure of compound (III) showing the formation of a hydrogen-bonded sheet of anions parallel to (001). The original atomic coordinates (Glidewell et al., 2017 ▸) have been used and, for the sake of clarity, the H atoms bonded to C atoms have been omitted.

Figure 6

A projection down [100] of part of the crystal structure of compound (III) showing the disposition of the cations bonded to both faces of the anion sheet. For the sake of clarity, the H atoms bonded to C atoms have been omitted.