3-Chloro-6-[4-(2-pyrid­yl)piperazin-1-yl]pyridazine

Arslan, H.; Utku, S.; Hardcastle, K.I.; Gökçe, M.; Lense, S.

doi:10.1107/S1600536809050727

Volume 66
Part 1
Page o35
January 2010

Received 23 November 2009
Accepted 25 November 2009
Online 4 December 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.095
Data-to-parameter ratio = 19.0
Details

3-Chloro-6-[4-(2-pyridyl)piperazin-1-yl]pyridazine

Hakan Arslan,^a,^b ^* Semra Utku,^c Kenneth I. Hardcastle,^a Mehtap Gökçe ^d and Sheri Lense ^a

^aDepartment of Chemistry, Emory University, Atlanta, GA-30322, USA,^bDepartment of Chemistry, Faculty of Pharmacy, Mersin University, Mersin TR-33169, Turkey,^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin TR-33169, Turkey, and ^dDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, Ankara TR-06330, Turkey
Correspondence e-mail: hakan.arslan.acad@gmail.com

In the title compound, C₁₃H₁₄ClN₅, the piperazine ring adopts a chair conformation and the dihedral angle between the aromatic rings is 13.91 (7)°. The crystal structure is stabilized by weak intermolecular C-HN hydrogen-bond interactions.

Related literature

For the synthesis, structures and analgesic and anti-inflammatory activity of substituted pyridazine derivatives, see: Boissier et al. (1963); Gokce et al. (2001, 2004, 2005, 2009); Sahin et al. (2004); Dundar et al. (2007). For general background to non-opioid analgesic derivatives, see: Sato et al. (1981); Banoglu et al. (2004); Giovannoni et al. (2003)·For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₃H₁₄ClN₅
M_r = 275.74
Triclinic, $[P \overline 1]$
a = 5.912 (3) Å
b = 8.088 (5) Å
c = 13.689 (8) Å
= 83.359 (9)°
= 83.019 (9)°
= 75.168 (9)°
V = 625.5 (6) Å³
Z = 2
Mo K radiation
= 0.30 mm^-1
T = 296 K
0.16 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.954, T_max = 0.959
11395 measured reflections
3275 independent reflections
2264 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.095
S = 0.95
3275 reflections
172 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N1ⁱ	0.93	2.58	3.346 (3)	140
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker (2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2610 ).

References

Banoglu, E., Akoglu, C., Unlu, S., Kupeli, E., Yesilada, E. & Sahin, M. F. (2004). Arch. Pharm. 337, 7-14.
Boissier, J. R., Ratouis, R. & Dumont, C. (1963). J. Med. Chem. 6, 541-544.
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Dundar, Y., Gokce, M., Kupeli, E. & Sahin, M. F. (2007). Arzneim. Forsch. 57, 777-781.
Giovannoni, M. P., Vergelli, C., Chelardini, C., Nicoletta, G., Bartolini, A. & Dal Piaz, V. (2003). J. Med. Chem. 46, 1055-1059.
Gokce, M., Bakir, G., Sahin, M. F., Kupeli, E. & Yesilada, E. (2005). Arzneim. Forsch. 55, 318-325.
Gokce, M., Dogruer, D. S. & Sahin, M. F. (2001). Il Farmaco, 56, 233-237.
Gokce, M., Sahin, M. F., Kupeli, E. & Yesilada, E. (2004). Arzneim. Forsch. 54, 396-401.
Gokce, M., Utku, S. & Kupeli, E. (2009). Eur. J. Med. Chem. 44, 3760-3764.
Sahin, M. F., Badicoglu, B., Gokce, M., Kupeli, E. & Yesilada, E. (2004). Arch. Pharm. 337, 445-452.
Sato, M., Ishizuka, Y. & Yamagucci, A. (1981). Arzneim. Forsch. 31, 1738-1745.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds