4-Aza-1-azoniabicyclo-[2.2.2]octa-ne-2-amino-benzoate-2-amino-benzoic acid (1/1/1)

Abstract

A 4-aza-1-azoniabicyclo-[2.2.2]octane cation, a 2-amino-benzoate anion and a neutral 2-amino-benzoic acid mol-ecule comprise the asymmetric unit of the title compound, C(6)H(13)N(2) (+)·C(7)H(6)NO(2) (-)·C(7)H(7)NO(2). An intra-molecular N-H⋯O hydrogen bond occurs in the anion and in the neutral 2-amino-benzoic acid mol-ecule. The cation provides a charge-assisted N-H⋯O hydrogen bond to the anion, and the 2-amino-benzoic acid mol-ecule forms an O-H⋯N hydrogen bond to the unprotonated amino N atom in the cation. In this way, a three-component aggregate is formed. These are connected into a three-dimensional network by amino-carboxyl-ate N-H⋯O hydrogen bonds. N-H⋯N hydrogen bonds are also observed.

Fig. 1.

Molecular structure of the 4-aza-1-azoniabicyclo(2.2.2)octane cation in (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Fig. 2.

Molecular structure of the 2-aminobenzoate anion in (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Fig. 3.

Molecular structure of the neutral 2-aminobenzoic acid molecule in (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Fig. 4.

Three component aggregate in (I) held together by O—H···N and N—H···O hydrogen bonds shown as orange and blue dashed lines, respectively.

Fig. 5.

View in projection down the a axis of the unit-cell contents of (I). The O—H···N and N—H···O hydrogen bonds are shown as orange and blue dashed lines, respectively.