Dataset Information

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.

SUBMITTER: Arman HD

PROVIDER: S-EPMC3247346 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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Publications

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

Arman Hadi D HD Kaulgud Trupta T Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20111012 Pt 11

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 ato ...[more]

PMID: 22219964

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Project description:In the structures of 1:1 and 1:2 adducts of phosphanetricarbo-nitrile (C3N3P) with 1,4-di-aza-bicyclo-[2.2.2]octane (C6H12N2), the 1:1 adduct crystallizes in the ortho-rhom-bic space group, Pbcm, with four formula units in the unit cell (Z' = 0.5). The P(CN)3 unit lies on a crystallographic mirror plane while the C6H12N2 unit lies on a crystallographic twofold axis passing through one of the C-C bonds. The P(CN)3 moiety has close to C 3v symmetry and is stabilized by forming adducts with two symmetry-related C6H12N2 units. The phospho-rus atom is in a five-coordinate environment. As a result of the symmetry, the two trans angles are equal so τ5 = 0.00 and thus the geometrical description could be considered to be square pyramidal. However, the electronic geometry is distorted octa-hedral with the lone pair on the phospho-rous occupying the sixth position. As would be expected from VSEPR considerations, the repulsion of the lone-pair electrons with the equatorial bonding electrons means that the trans angles for the latter are considerably reduced from 180° to 162.01 (4)°, so the best description of the overall geometry for phospho-rus is distorted square pyramidal. The 1:2 adduct crystallizes in the monoclinic space group, P21/m with two formula units in the asymmetric unit (i.e. Z' = 1/2). The P(CN)3 moiety lies on a mirror plane and one of the two C6H12N2 (dabco) mol-ecules also lies on a mirror plane. The symmetry of the P(CN)3 unit is close to C 3v. There are three P⋯N inter-actions and consequently the mol-ecular geometry of the phospho-rus atom is distorted octa-hedral. This must mean that the lone pair of electrons on the phospho-rus atom is not sterically active. For the 1:1 adduct, there are weak associations between the phospho-rus atom and one of the terminal nitro-gen atoms from the C≡ N moiety, forming chains in the a-axis direction. In addition there are weak C-H⋯N inter-actions between a terminal nitro-gen atoms from the C≡N moiety and the C6H12N2 mol-ecules, which form sheets perpendicular to the a axis.

Dataset Information

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

Publications

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

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