Dataset Information

5-Amino-3-eth-oxy-1,8,8-trimethyl-2-aza-bicyclo-[2.2.2]octa-2,5-diene-4,6-dicarbo-nitrile.

ABSTRACT: The title 2-aza-bicyclo-[2.2.2]octa-2,5-diene derivative, C(14)H(18)N(4)O, crystallized out with two independent mol-ecules with similar conformations in the asymmetric unit. In each mol-ecule, the three six-membered rings adopt boat conformations. The mol-ecules exist in the enamine form. In the crystal, mol-ecules are linked by N-H?O and N-H?N hydrogen bonds into a two-dimensional network parallel to the ab plane.

SUBMITTER: Chantrapromma S

PROVIDER: S-EPMC3435638 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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Publications

5-Amino-3-eth-oxy-1,8,8-trimethyl-2-aza-bicyclo-[2.2.2]octa-2,5-diene-4,6-dicarbo-nitrile.

Chantrapromma Suchada S Suwunwong Thitipone T Ruanwas Pumsak P Boonnak Nawong N Fun Hoong-Kun HK

Acta crystallographica. Section E, Structure reports online 20120801 Pt 9

The title 2-aza-bicyclo-[2.2.2]octa-2,5-diene derivative, C(14)H(18)N(4)O, crystallized out with two independent mol-ecules with similar conformations in the asymmetric unit. In each mol-ecule, the three six-membered rings adopt boat conformations. The mol-ecules exist in the enamine form. In the crystal, mol-ecules are linked by N-H⋯O and N-H⋯N hydrogen bonds into a two-dimensional network parallel to the ab plane. ...[more]

PMID: 22969511

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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

5-Amino-3-eth-oxy-1,8,8-trimethyl-2-aza-bicyclo-[2.2.2]octa-2,5-diene-4,6-dicarbo-nitrile.

Publications

5-Amino-3-eth-oxy-1,8,8-trimethyl-2-aza-bicyclo-[2.2.2]octa-2,5-diene-4,6-dicarbo-nitrile.

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