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

Ju, Z.-Y.; Li, G.-C.; Li, C.; Wang, J.; Yang, F.-L.

doi:10.1107/S1600536812018776

Volume 68
Part 6
Page o1646
June 2012

Received 11 April 2012
Accepted 26 April 2012
Online 5 May 2012

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.070
Data-to-parameter ratio = 16.7
Details

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

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

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China, and ^bCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan Province 450001, People's Republic of China
Correspondence e-mail: 374107445@qq.com

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-HO hydrogen bonds and three weak C-H [pi] 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, $[P \overline 1]$
a = 7.390 (4) Å
b = 9.385 (5) Å
c = 10.587 (6) Å
= 106.618 (7)°
= 97.489 (6)°
= 101.098 (9)°
V = 676.9 (6) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.070
S = 1.02
3167 reflections
190 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C8-H8O1ⁱ	0.95	2.54	3.389 (2)	149
C15-H15O1ⁱⁱ	0.95	2.44	3.235 (2)	141
C4-H4Cg2ⁱⁱⁱ	0.95	2.76	3.494 (2)	135
C9-H9Cg2^iv	0.95	2.95	3.752 (2)	143
C13-H13Cg1^v	0.95	2.63	3.456 (2)	145
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x+1, y-1, z; (iii) -x+1, -y+1, -z+2; (iv) -x+2, -y+1, -z+1; (v) x+1, y, z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: BG2457 ).

Acknowledgements

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).

References

Ju, Z.-Y., Jiang, W.-X. & Yang, F.-L. (2011). Acta Cryst. E67, o1042.
Li, H. S., Ling, Y., Guo, Y. L., Yang, X. L. & Chen, F. H. (2005). Chin. J. Org. Chem. 25, 204-207.
Loksha, Y. M., Pedersen, E. B., Colla, P. L. & Loddo, R. (2007). J. Heterocycl. Chem. 44, 1351-1356.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xu, H., Zou, X. M. & Yang, H. Z. (2006). Pest Manag. Sci. 62, 522-530.

organic compounds