Research Article: 1,1′-[(5-Hy­droxy­methyl-1,3-phenyl­ene)bis­(methyl­ene)]dipyridin-4(1H)-one monohydrate

Date Published: July 01, 2011

Publisher: International Union of Crystallography

Author(s): José A. Fernandes, Manuela E. L. Lago, Sandrina Silva, João P. C. Tomé, José A. S. Cavaleiro, Filipe A. Almeida Paz.


The asymmetric unit of the title compound, C19H18N2O3, comprises a whole organic dipyridinone mol­ecule plus a water mol­ecule of crystallization. The planes of the pyridinone rings are approximately perpendicular with the plane of the central aromatic ring [dihedral angles = 80.68 (8) and 83.65 (8)°]. The C—O bond of the hy­droxy group subtends an angle of 31.71 (10)° with the plane through the central aromatic ring. The crystal packing is mediated by the presence of several O—H⋯O hydrogen-bonding inter­actions and while the water mol­ecules form a C21(4) chain parallel to the c axis of the unit cell, the pendant hy­droxy groups are engaged in O—H⋯O=C hydrogen bonds described by a C11(12) graph-set motif which runs parallel to the a axis.

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For previous reports on the design and synthesis of mol­ecules based on a mesitylene core, see: Reger et al. (2010 ▶); Podyachev et al. (2006 ▶); Spiccia et al.(1997 ▶); Newkome et al. (1986 ▶); Berl et al., (2002 ▶). For the crystal structure and vibrational features of the precursor, 1,3,5-tris­(bromo­meth­yl)benzene, see: Fernandes et al. (2011 ▶). For a systematization of the graph-set notation for hydrogen-bonded aggregates, see: Grell et al. (1999 ▶).




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