Kozlov Leonid, Goldberg Israel
School of Chemistry, Sackler Faculty of Exact Sciences, Tel-Aviv University, Ramat-Aviv, 69978 Tel-Aviv, Israel.
Acta Crystallogr C. 2008 Sep;64(Pt 9):o498-501. doi: 10.1107/S0108270108025377. Epub 2008 Aug 13.
The solvent-free title compound, C(16)H(6)N(6), is an aromatic derivative of phenanthroline with an extended pi system. It exhibits a remarkable pi-pi columnar stacking in the crystal structure, with interplanar distances of 3.229 (3) and 3.380 (3) A, the shorter spacing being between the two molecules within the asymmetric unit. Adjacent units along the stacked arrays are rotated in-plane with respect to one another by approximately 120 degrees . The hydrochloride derivative, C(16)H(7)N(6)(+).Cl(-).2H(2)O, in which one of the phenanthroline N atoms has been protonated, crystallized as a dihydrate. The supramolecular organization in this compound is characterized by continuous hydrogen bonding between the component species, yielding two-dimensional hydrogen-bonded networks. This study demonstrates the high significance of the pi-pi stacking interactions in the solvent-free aromatic system and how they can be undermined by introducing hydrogen-bonding capacity into the ligand.
无溶剂标题化合物C(16)H(6)N(6)是具有扩展π体系的菲咯啉芳香衍生物。它在晶体结构中呈现出显著的π-π柱状堆积，平面间距为3.229(3)和3.380(3) Å，较短的间距存在于不对称单元内的两个分子之间。沿堆积阵列的相邻单元在平面内彼此相对旋转约120度。盐酸盐衍生物C(16)H(7)N(6)(+)·Cl(-)·2H(2)O中，菲咯啉的一个氮原子已被质子化，以二水合物形式结晶。该化合物中的超分子结构以组分物种之间连续的氢键为特征，形成二维氢键网络。本研究证明了无溶剂芳香体系中π-π堆积相互作用的高度重要性，以及如何通过在配体中引入氢键能力来破坏它们。
