The X-ray structure of 2-(dibromomethyl)benzonitrile, featuring unexpectedly short CN⋯Br halogen bond distances between a nitrile group and a C(sp³)-linked bromine atom, is presented. Despite the weak Lewis base nature of the nitrile N atom and absence of strong electron-withdrawing groups on the Br atom, π-stacking significantly enhances both the electron donor and acceptor capability of the interacting partners. As such, and beyond trivial (hetero)aromatic systems, the rationale of CN⋯Br halogen bonding can also be employed in purely aliphatic systems.

中文翻译：

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通过π堆积缩短CN⋯Br–Csp3卤素键

提出了2-(二溴甲基)苯甲腈的 X 射线结构，其特征是腈基团和 C(sp ³ ) 连接的溴原子之间具有出人意料的短 C N⋯Br 卤素键距离。尽管腈 N 原子的路易斯碱性质较弱且 Br 原子上不存在强吸电子基团，但 π 堆积显着增强了相互作用伙伴的电子供体和受体能力。因此，除了普通（杂）芳香族系统之外，C N⋯B r 卤素键合的基本原理也可以用于纯脂肪族系统。