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

Adailton J Bortoluzzi; Luciana B P Souza; Antônio C Joussef; Emerson Meyer

doi:10.1107/S160053681101467X

. 2011 Apr 29;67(Pt 5):o1230–o1231. doi: 10.1107/S160053681101467X

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

Adailton J Bortoluzzi ^a,^*, Luciana B P Souza ^a, Antônio C Joussef ^a, Emerson Meyer ^b

PMCID: PMC3089372 PMID: 21754527

Abstract

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 [1 Inline graphic 0] direction.

Related literature

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 ▶)

Experimental

Crystal data

C₁₉H₁₇BrN₂O₃
M _r = 401.26
Triclinic,
a = 5.991 (1) Å
b = 8.958 (1) Å
c = 17.531 (2) Å
α = 99.502 (11)°
β = 95.241 (12)°
γ = 105.499 (10)°
V = 885.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.34 mm⁻¹
T = 293 K
0.50 × 0.33 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan [North et al. (1968 ▶) and PLATON (Spek, 2009 ▶)] T _min = 0.567, T _max = 0.978
3368 measured reflections
3151 independent reflections
2033 reflections with I > 2σ(I)
R _int = 0.024
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.098
S = 1.03
3151 reflections
237 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101467X/lw2061sup1.cif

e-67-o1230-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101467X/lw2061Isup2.hkl

e-67-o1230-Isup2.hkl^{(151.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681101467X/lw2061Isup3.mol

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.86	2.08	2.910 (4)	162

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and the Financiadora de Estudos e Projetos (FINEP) for financial support.

supplementary crystallographic information

Comment

Heterocyclic compounds containing 3-(2H)-pyridazinone moiety in their structures have attracted a great deal of attention due to their wide spectrum of biological activity such as antimicrobial (Sayed et al., 2002; Katrusiak & Baloniak, 1994), anti-inflammatory (Dogruer et al., 2003; Pieretti et al., 2006), antifeedant (Cao et al., 2003), herbicidal (Piaz et al., 1994; Xu et al., 2008), antiplatelet (Giovannoni et al., 2007; Coelho et al., 2007), anticancer (Malinka et al., 2003), antihypertensive (Wexler et al., 1996; Barbaro et al., 2001), antinociceptive agent (Giovannoni et al., 2007; Vergelli et al., 2007) and other biological and pharmacological properties (Abudshait, 2007). In our study toward the synthesis of dihydropyridazinones as potential candidates for antihypertensive activity the structure of methyl 4-[6-(4-bromophenyl)-3-oxo-2,3,4,5-dihydropyridazin-4-ylmethyl]benzoate has been determined.

The structure of the title compound consists of two cyclic moieties, 4-(methoxycarbonyl)phenyl and 6-(4-bromophenyl)-3-oxo-2,3,4,5-dihydropyridazin-4-yl, which are linked by methylene spacer (Fig. 1). The pyridazinyl ring is twisted, the greatest deviation is observed for carbon atoms C5 and the disordered C6A and C6B atoms, which are -0.0674 (8), 0.479 (5) and -0.415 (12) Å, respectively, out of the mean plane of all atoms in the ring. The dihedral angle between the mean plane of this ring and that of the bromophenyl mean plane is 17.2 (2)°. The 4-(Methoxycarbonyl)phenyl moiety shows quasi-planar conformation, where the dihedral angle between the mean planes of the phenyl ring and carboxylate ester group is 7.9 (4)°. Intermolecular N3—H3N···O1 hydrogen bonds form centrosymmetric dimers (Fig. 2). Each dimer is linked to two neighboring dimers through C4═O1···Br—C14 interactions (Voronina et al., 2009) forming an one-dimensional polymeric structure along [120] direction (Fig. 3). In addition, packing analysis shows that the molecules are perfectly stacked along [100] direction (Fig. 4).

Experimental

The title compound was synthesized according to a previously described method (Meyer et al., 2004). A careful crystallization from methanol/water (1:1 v/v) provided colorless crystals suitable for X-ray analysis.