Research Article: Methyl 4-{[6-(4-bromo­phen­yl)-3-oxo-2,3,4,5-tetra­hydro­pyridazin-4-yl]methyl}benzoate

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 [10] direction.

Partial Text

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 ▶)




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