3-Chloro-6-{4-[3-(4-chloro­phen­oxy)prop­yl]piperazin-1-yl}pyridazine

Wang, H.; Xiao, J.; Zhang, X.; Sun, T.; Li, S.

doi:10.1107/S1600536810005337

Volume 66
Part 3
Page o716
March 2010

Received 3 February 2010
Accepted 9 February 2010
Online 27 February 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.005 Å
R = 0.050
wR = 0.159
Data-to-parameter ratio = 13.8
Details

3-Chloro-6-{4-[3-(4-chlorophenoxy)propyl]piperazin-1-yl}pyridazine

Hongliang Wang,^a Junhai Xiao,^b Xian Zhang,^a Tiemin Sun ^a ^* and Song Li ^b

^aSchool of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China, and ^bBeijing Institute of Pharmacology and Toxicology, Beijing 100850, People's Republic of China
Correspondence e-mail: xiaojunhai@139.com

In the title compound, C₁₇H₂₀Cl₂N₄O, the piperazine ring adopts a chair conformation and the dihedral angle between the pyridazine ring and the benzene ring is 36.3 (1)°. In the crystal, weak C-HO and C-H(N,N) interactions help to establish the packing, which also features short intermolecular ClCl contacts [3.331 (2) Å].

Related literature

For the biological properties of 3-(piperazin-1-yl)pyridazine derivatives, see: Monge et al. (1991); Tucker et al. (1998). For the synthesis, see: Fan et al. (2009).

Experimental

Crystal data

C₁₇H₂₀Cl₂N₄O
M_r = 367.27
Monoclinic, C 2/c
a = 39.774 (18) Å
b = 5.757 (3) Å
c = 14.924 (7) Å
= 93.107 (9)°
V = 3412 (3) Å³
Z = 8
Mo K radiation
= 0.39 mm^-1
T = 113 K
0.20 × 0.18 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.926, T_max = 0.969
11904 measured reflections
2996 independent reflections
2030 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.159
S = 1.09
2996 reflections
217 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N1ⁱ	0.95	2.53	3.247 (6)	133
C3-H3N2ⁱ	0.95	2.50	3.427 (6)	164
C13-H13O1ⁱⁱ	0.95	2.60	3.529 (5)	168
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5330 ).

Acknowledgements

The work was supported by National Natural Science Foundation of China (90813025).

References

Fan, S. Y., Zheng, Z. B., Mi, C. L., Zhou, X. B., Yan, H., Gong, Z. H. & Li, S. (2009). Bioorg. Med. Chem. 17, 621-624.
Monge, A., Aldana, I., Alvarez, T., Font, M., Santiago, E., Latre, J. A., Bermejillo, M. J. & Lopez-Unzu, M. J. (1991). J. Med. Chem. 34, 3023-3029.
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tucker, J. A., Allwine, D. A., Grega, K. C., Barbachyn, M. R., Klock, J. L., Adamski, J. L., Brickner, S. J., Hutchinson, D. K., Ford, C. W., Zurenko, G. E., Conradi, R. A., Burton, P. S. & Jensen, R. M. (1998). J. Med. Chem. 41, 3727-3725.

organic compounds