Conformational control through co-operative nonconventional C—H...N hydrogen bonds
Conformational control through co-operative nonconventional C—H...N hydrogen bonds
复制标题
通过协同非常规 C–H...N 氢键进行构象控制
DOI：
10.1107/s2053229621007427
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Oburn, Shalisa M.
中科院分区：
文献类型：
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作者：
Bosch, Eric;Bowling, Nathan P.;Oburn, Shalisa M.
我们报道了一个共轭亚芳基乙炔基分子2-（2-{4，5-二甲氧基-2-[2-（2，3，4-三氟苯基）乙炔基]苯基}乙炔基）-6-[2-（吡啶-2-基）乙炔基]吡啶（C30 H17 F3 N2 O2）的设计、合成和晶体结构。该分子在空间群P\overline{1}中结晶，Z = 2，并且具有两个分子内sp2-C-H N氢键，这两个氢键协同地将芳基乙炔基分子保持在菱形构象中。由于H原子位于三氟苯基环上，H <$N距离为2.470（16）和2.646（16）<$，C-H <$N角分别为161.7（2）和164.7（2）°，因此H原子被活化成氢键。 分子静电势计算支持三氟苯基部分形成C-H N氢键。Hirshfeld表面分析确定了相邻的1，2-二甲氧基苯片段之间的自互补C-H-2 O二聚体相互作用，这在含有该部分的结构中是常见的。
We report the design, synthesis, and crystal structure of a conjugated aryleneethynyl molecule, 2-(2-{4,5-dimethoxy-2-[2-(2,3,4-trifluorophenyl)ethynyl]phenyl}ethynyl)-6-[2-(pyridin-2-yl)ethynyl]pyridine, C30H17F3N2O2, that adopts a planar rhombus conformation in the solid state. The molecule crystallizes in the space group P\overline{1}, with Z = 2, and features two intramolecular sp2-C—H⋯N hydrogen bonds that co-operatively hold the arylethynyl molecule in a rhombus conformation. The H atoms are activated towards hydrogen bonding since they are situated on a trifluorophenyl ring and the H⋯N distances are 2.470 (16) and 2.646 (16) Å, with C—H⋯N angles of 161.7 (2) and 164.7 (2)°, respectively. Molecular electrostatic potential calculations support the formation of C—H⋯N hydrogen bonds to the trifluorophenyl moiety. Hirshfeld surface analysis identifies a self-complementary C—H⋯O dimeric interaction between adjacent 1,2-dimethoxybenzene segments that is shown to be common in structures containing that moiety.