meso-4,4´-Difluoro-2,2´-{[(3aR,7aS )-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylene)}diphenol

0391700 - FZÚ 2014 RIV DK eng J - Journal Article
Rivera, A. - Quiroga, D. - Ríos-Motta, J. - Kučeráková, Monika - Dušek, Michal
meso-4,4´-Difluoro-2,2´-{[(3aR,7aS )-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylene)}diphenol.
Acta Crystallographica Section E-Structure Reports Online. Roč. 69, Part 2 (2013), , "o217"-"sub-8". ISSN 1600-5368. E-ISSN 2056-9890
Grant - others:AV ČR(CZ) AP0701
Program: Akademická prémie - Praemium Academiae
Institutional support: RVO:68378271
Keywords : single-crystal X-ray study * T = 120 K * mean sigma(C–C) = 0.002 A * R factor = 0.030 * wR factor = 0.077 * data-to-parameter ratio = 12.7
Subject RIV: BM - Solid Matter Physics ; Magnetism
Impact factor: 0.347, year: 2011

In the crystal structure of the title compound, C21H24F2N2O2, there are two intramolecular O-H...N hydrogen bonds involving the N atoms of the imidazolidine ring and the hydroxy groups. The crystal studied was a meso compound obtained by the reaction of the aminal (2S,7R,11S,16R)- 1,8,10,17-tetraazapentacyclo[8.8.1.1^(8,17).0^(2,7).0^(11,16)]cosane with 4-fluorophenol. The imidazolidine ring has a twisted conformation with a CH-CH-N-CH2 torsion angle of 44.99 (14) and, surprisingly, the lone pairs of the N atoms are disposed in a syn isomerism, making the title compound an exception to the typical ‘rabbit-ear effect’ in 1,2-diamines. In the crystal, molecules are linked via C-H...F hydrogen bonds, forming chains along the c-axis direction. These chains are linked via another C-H...F hydrogen bond, forming a three-dimensional network.
Permanent Link: http://hdl.handle.net/11104/0220680