4-(6-Chloro­imidazo[1,2-b]pyridazin-3-yl)benzonitrile

Yiliang Zhao; Clarissa K L Ng

doi:10.1107/S1600536811037901

. 2011 Sep 30;67(Pt 10):o2710. doi: 10.1107/S1600536811037901

4-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)benzonitrile

Yiliang Zhao ^a,^*, Clarissa K L Ng ^a

PMCID: PMC3201438 PMID: 22065465

Abstract

In the title compound, C₁₃H₇ClN₄, the imidazopyridazine ring system is essentially planar [maximum deviation 0.015 (1) Å]. It is inclined to the benzene ring of the benzonitrile group by 11.31 (2)°. In the crystal, molecules are linked via C—H⋯Cl and C—H⋯N interactions.

Related literature

For related structures, see Kia et al. (2009 ▶); Khan et al. (2010 ▶); Xue (2010 ▶); Zhao et al. (2009 ▶).

Experimental

Crystal data

C₁₃H₇ClN₄
M _r = 254.68
Tetragonal,
a = 13.5513 (12) Å
c = 24.566 (3) Å
V = 4511.3 (7) Å³
Z = 16
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 150 K
0.25 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.659, T _max = 0.746
140841 measured reflections
18107 independent reflections
11833 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.141
S = 1.08
18107 reflections
191 parameters
7 restraints
All H-atom parameters refined
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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: ORTEP-3 for Windows (Farrugia, 1999 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811037901/ng5227sup1.cif

e-67-o2710-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037901/ng5227Isup2.hkl

e-67-o2710-Isup2.hkl^{(885.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037901/ng5227Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1ⁱ	1.08 (1)	2.60 (1)	3.3502 (7)	126 (1)
C3—H3⋯Cl1ⁱⁱ	1.08 (1)	2.70 (1)	3.7389 (6)	161 (1)
C5—H5⋯N4ⁱⁱⁱ	1.08 (1)	2.31 (1)	3.3341 (7)	157 (1)
C8—H8⋯N4ⁱⁱⁱ	1.08 (1)	2.52 (1)	3.6049 (8)	177 (1)
C12—H12⋯N2	1.08 (1)	2.25 (1)	2.9975 (6)	125 (1)

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

Acknowledgments

The authors would like to thank Professor Dai Hibbs from the Faculty of Pharmacy, the University of Sydney, for his kind and generous support of this research project.

supplementary crystallographic information

Comment

The title compound, C₁₃ H₇ C_l1 N₄, was newly synthesized, crystallized and analysed at high resolution sin theta/lambda 1.1. The bond lengths are as expected. The crystal packing reveals that in one unit cell, every four molecules stack in parallel position by a number of non-classical hydrogen bonds. Hydrogen atoms are fixed at 1.083 A as determined from neutron diffraction, and the temperature factors were refined isotropically.

Experimental

To a thick wall borosilicate glass vial were added 6-Chloro-3-iodo-imidazo[1,2-b]pyridazine (0.05 g, 1.0 equiv.), 4-cyanophenylboronic acid (0.032 g, 1.2 equiv.), Pd(PPh₃)₄ (0.02 g, 10 mol%), K₂CO₃ (0.037 g, 1.5 equiv.), and EtOH/H2O (4 : 1, 5 ml). The vial was sealed with a silicon septum and the reaction mixture was pre-stirred for 1 min. The reaction mixture was subjected to microwave irradiation at 90 °C for 14 min at the maximum power of 300 W with sufficient stirring. The reaction mixture was cooled to room temperature and solvent was removed under reduced pressure. The crude product was purified by flash column chromatography, eluting with ethyl acetate/hexane (1 : 1) to give the titled compound as a bright yellow solid (0.038 g, 83 %).