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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 [sigma](C-C) = 0.005 Å
R = 0.050
wR = 0.159
Data-to-parameter ratio = 13.8
Details
Open access

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

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-H...O and C-H...(N,N) interactions help to establish the packing, which also features short intermolecular Cl...Cl contacts [3.331 (2) Å].

Related literature

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

[Scheme 1]

Experimental

Crystal data
  • C17H20Cl2N4O

  • Mr = 367.27

  • Monoclinic, C 2/c

  • a = 39.774 (18) Å

  • b = 5.757 (3) Å

  • c = 14.924 (7) Å

  • [beta] = 93.107 (9)°

  • V = 3412 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, USA.]) Tmin = 0.926, Tmax = 0.969

  • 11904 measured reflections

  • 2996 independent reflections

  • 2030 reflections with I > 2[sigma](I)

  • Rint = 0.061

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.159

  • S = 1.09

  • 2996 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...N1i 0.95 2.53 3.247 (6) 133
C3-H3...N2i 0.95 2.50 3.427 (6) 164
C13-H13...O1ii 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort] [ISI]
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2010). E66, o716  [ doi:10.1107/S1600536810005337 ]

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