Preis Jasmin, Schollmeyer Dieter, Detert Heiner
University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany.
Acta Crystallogr Sect E Struct Rep Online. 2011 Oct 1;67(Pt 10):o2551. doi: 10.1107/S1600536811035288. Epub 2011 Sep 3.
The title compound, C(12)H(9)ClN(4), was prepared from dichloro-pyridazine and tolyl-tetra-zole in a nucleophilic biaryl coupling followed by thermal ring transformation. The mol-ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.036 Å) and an intra-molecular C-H⋯N hydrogen bond occurs. In the crystal, the mol-ecules form dimers connected via π-π inter-actions [centroid-centroid distance = 3.699 (2) Å], which are further connected to neighbouring mol-ecules via C-H-N bonds. The bond lengths in the pyridazine ring system indicate a strong localization of the double bonds and there is a weak C-Cl bond [1.732 (3) Å].
标题化合物C₁₂H₉ClN₄是由二氯哒嗪和甲苯基四唑通过亲核联芳基偶联反应，随后进行热环转化反应制备而成。该分子基本呈平面结构（所有非H原子的均方根偏差 = 0.036 Å），且存在分子内C—H⋯N氢键。在晶体中，分子通过π-π相互作用形成二聚体[质心-质心距离 = 3.699 (2) Å]，这些二聚体又通过C—H—N键与相邻分子相连。哒嗪环系中的键长表明双键有很强的定域性，并且存在一个较弱的C—Cl键[1.732 (3) Å]。
