2-Benzyl-6-benz­yloxypyridazin-3(2H)-one

Zhi-Yu Ju; Wan-Xiang Jiang; Feng-Ling Yang

doi:10.1107/S1600536811011597

. 2011 Apr 7;67(Pt 5):o1042. doi: 10.1107/S1600536811011597

2-Benzyl-6-benzyloxypyridazin-3(2H)-one

Zhi-Yu Ju ^a, Wan-Xiang Jiang ^b, Feng-Ling Yang ^a,^*

PMCID: PMC3089324 PMID: 21754369

Abstract

In the title compound, C₁₈H₁₆N₂O₂, the central pyridazine ring forms dihedral angles of 77.08 (5)° and 84.62 (5)° with the two benzene rings. The dihedral angle between the two benzene rings is 68.18 (4)°. A very weak intramolecular C—H⋯N hydrogen bond and an intramolecular C—H⋯π interaction occur. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds and weak C—H⋯π and π–π stacking interactions [centroid–centroid distance = 3.6867 (10) Å].

Related literature

For applications of pyridazinone analogues as highly selective anti-HIV agents, see: Loksha et al. (2007 ▶). For applications as pesticide agents, see: Li et al. (2005 ▶); Selby et al. (2002 ▶). For applications as herbicides, see: Xu et al. (2006 ▶). For related structures, see: Liu et al. (2005 ▶).

Experimental

Crystal data

C₁₈H₁₆N₂O₂
M _r = 292.33
Monoclinic,
a = 32.741 (4) Å
b = 10.9198 (14) Å
c = 8.1228 (10) Å
β = 95.92 (2)°
V = 2888.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009 ▶) T _min = 0.982, T _max = 0.989
18031 measured reflections
3448 independent reflections
2142 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.116
S = 0.95
3448 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2009 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku/MSC, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011597/fj2404sup1.cif

e-67-o1042-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011597/fj2404Isup2.hkl

e-67-o1042-Isup2.hkl^{(169.2KB, hkl)}

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

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

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.38	3.2906 (19)	161 (19)
C11—H11⋯N2	0.95	2.49	3.126 (2)	124
C11—H11⋯Cg3	0.95	2.98	3.7103 (17)	135
C17—H17⋯Cg3ⁱⁱ	0.95	2.98	3.6991 (17)	133

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant No. 20972143), the Natural Science Foundation of Henan Province Educational Committee, China (grant Nos. 2010 A150021 and 2007150036) and the High-level Talents Foundation of Xuchang University (grant No. 2010 GC033).

supplementary crystallographic information

Comment

Pyridazinone analogues have been reported to have a variety of biological activities, such as highly-selective anti-HIV agents (Loksha et al., 2007), pesticide(Li et al., 2005), highly herbicidal activity (Xu et al., 2006). In order to discover further biologically active Pyridazinone analogues, the title compound, (I), was synthesized and its crystal structure determined (Fig. 1).

In a continuation of our studies on the crystal structures of Pyridazinone analogues (Liu et al., 2005), we report here the synthesis and crystal structure of the title molecule, the central pyridazine ring forms dihedral angles of 77.08 (5)° and 84.62 (5)° with the two benzene rings, The dihedral angle between two benzene rings is 68.18 (4)°. The Crystal structure is stabilized by a weak intramolecular C—H···N hydrogen bond (Table 1), a weak intermolecular C—H···O hydrogen bond (Table 1), C—H···Cgπ—ring (Table 1) and π-π stacking interactions where Cg(1)—Cg(1) (1/2 - x, 1/2 - y, 1 - z) is 3.6867 (10) Å [Cg(1) is the centroid of the N1,N2, C1—C4 ring] (Table 2).

Experimental

Maleic hydrazide(0.56 g, 5 mmol), Benzyl chloride(1.52 g, 12 mmol) and K₂CO₃ (1.66 g, 12 mmol) were added to absolute ethanol(30 ml). The mixture was stirred in the room temperature for 6 h. The suspension was filtered and the residue was washed with absolute ethanol. The title compound was recrystallized from the mother solution and single crystals of (I) were obtained by slow evaporation.