Date Published: May 01, 2011
Publisher: International Union of Crystallography
Author(s): Adailton J. Bortoluzzi, Luciana B. P. Souza, Antônio C. Joussef, Emerson Meyer.
The structure of the title compound, C19H17BrN2O3, consists of two cyclic groups, viz. 4-(methoxycarbonyl)phenyl and 6-(4-bromophenyl)-3-oxo-2,3,4,5-dihydropyridazin-4-yl, which are linked by a methylene spacer. The pyridazine ring is twisted and the dihedral angle between its mean plane and that of the bromophenyl mean plane is 17.2 (2)°. The 4-(methoxycarbonyl)phenyl group shows a quasi-planar conformation, where the dihedral angle between the mean planes of the phenyl ring and carboxylate ester group is 7.9 (4)°. Centrosymmetric intermolecular N—H⋯O hydrogen bonds form dimers. These are linked by C—Br⋯O=C interactions [Br⋯O = 3.10 (1) Å] to form a one-dimensional polymeric structure running along the  direction.
For specific details concerning organic reactions and synthetic procedures for 4,5-diihydro-3(2H)-pyridazinone derivatives, see: Meyer et al. (2004 ▶). For the biological activity of heterocyclic compounds containing the 3(2H)-pyridazinone group, see: Sayed et al. (2002 ▶); Katrusiak & Baloniak (1994 ▶); Dogruer et al. (2003 ▶); Pieretti et al. (2006 ▶); Cao et al. (2003 ▶); Piaz et al. (1994 ▶); Xu et al. (2008 ▶); Giovannoni et al. (2007 ▶); Coelho et al. (2007 ▶); Malinka et al. (2003 ▶); Wexler et al. (1996 ▶); Barbaro et al., (2001 ▶); Vergelli et al. (2007 ▶); Abudshait (2007 ▶). For related structures, see: Zhang et al. (2006 ▶); Zhou & Zhou (2007 ▶). For C—Br⋯O interactions, see: Voronina et al. (2009 ▶)