6-Benz­yloxy-2-phenyl­pyridazin-3(2H)-one

Zhi-Yu Ju; Gong-Chun Li; Chao Li; Jie Wang; Feng-Ling Yang

doi:10.1107/S1600536812018776

. 2012 May 5;68(Pt 6):o1646. doi: 10.1107/S1600536812018776

6-Benzyloxy-2-phenylpyridazin-3(2H)-one

Zhi-Yu Ju ^a, Gong-Chun Li ^a, Chao Li ^b, Jie Wang ^b, Feng-Ling Yang ^a,^*

PMCID: PMC3379247 PMID: 22719445

Abstract

In the title compound, C₁₇H₁₄N₂O₂, the central pyridazine ring forms dihedral angles of 47.29 (5) and 88.54 (5)° with the benzene rings, while the dihedral angle between the benzene rings is 62.68 (6)°. In the crystal, molecules are linked by two weak C—H⋯O hydrogen bonds and three weak C—H⋯π interactions.

Related literature

For applications of pyridazinone analogues as highly selective anti-HIV agents, see: Loksha et al. (2007 ▶), as pesticides, see: Li et al. (2005 ▶) and as herbicides, see: Xu et al. (2006 ▶). For a related structure, see: Ju et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₁₄N₂O₂
M _r = 278.30
Triclinic,
a = 7.390 (4) Å
b = 9.385 (5) Å
c = 10.587 (6) Å
α = 106.618 (7)°
β = 97.489 (6)°
γ = 101.098 (9)°
V = 676.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.982, T _max = 0.987
7083 measured reflections
3167 independent reflections
2103 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.070
S = 1.02
3167 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018776/bg2457sup1.cif

e-68-o1646-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018776/bg2457Isup2.hkl

e-68-o1646-Isup2.hkl^{(155.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018776/bg2457Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C1–C6 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.95	2.54	3.389 (2)	149
C15—H15⋯O1ⁱⁱ	0.95	2.44	3.235 (2)	141
C4—H4⋯Cg2ⁱⁱⁱ	0.95	2.76	3.494 (2)	135
C9—H9⋯Cg2^iv	0.95	2.95	3.752 (2)	143
C13—H13⋯Cg1^v	0.95	2.63	3.456 (2)	145

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant Nos. 20972143 and 20972130), the Natural Science Foundation of Henan Province Education Committee, China (No. 2010 A150021) and the Natural Science Foundation of Xuchang University (grant No. 2012064).

supplementary crystallographic information

Comment

Pyridazinones represent an important class of biologically active compounds. Recently, a substantial number of pyridazinones have been reported to possess 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).

As a continuation of our studies on the crystal structures of Pyridazinone analogues (Ju et al., 2011), we report here the synthesis and crystal structure, an ellipsoid plot of which is shown in Fig. 1. The central pyridazine ring forms dihedral angles of 47.29 (5)° and 88.54 (5)° with the two benzene rings, while the dihedral angle between the two benzene rings is 62.68 (6)°. The structure is stabilized by two weak C—H···O and three C—H···Cg intermolecular hydrogen bonds (Cg's: centroids of the benzene rings) (Table 1).

Experimental

3-hydroxyl-1phenyl-6-pyridazone(0.94 g, 5 mmol), benzyl chloride(0.63 g, 5 mmol) and K₂CO₃ (0.69 g, 5 mmol) were added to absolute ethanol(30 ml). The mixture was stirred in the room temperature for 10 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.