We have obtained previously known and new 4,8-C-substituted hexahydroquinazolincyanamides by two-component condensation of 2,6-diaryl(heteroaryl)methylidenecyclohexanones with the same or different terminal substituents with N-cyanoguanidine according to a modified procedure under conditions of basic catalysis. We have grown a singlecrystal of one of the representatives of the series –N-(8-benzylidene-4-phenylhexahydroquinazolin-2(1H)-ylidene)cyanamideby crystallization from a saturated solution of acetonitrile and carried out its X-ray diffraction study. The structure of N-(8-benzylidene-4-phenylhexahydroquinazolin-2(1H)-ylidene)cyanamide, C₂₂H₂₀N₄, has orthorhombic (P2₁2₁2₁) symmetry. The molecule is built from fused non-planar cyclohexene and tetrahydropyrimidine rings. The cyclohexene ring is in the half-chair conformation, while the tetrahydropyrimidine ring adopts the ‘C-envelope’ conformation. The crystal packing of the compound is an alternating layered structure. The mutual arrangement of molecules promotes the formation of intermolecular hydrogen bonds (IMH) between the H1 hydrogen atoms of the quinazoline ring and the N4 nitrogen atoms of the nitrile group. Non-planar C–H···π interactions are observed in the crystal as well. The compound is in the E,E-configuration. The calculation and analysis of Hirschfeld surfaces demonstrated the presence of hydrogen bonds, different in energy, and C–H···π interactions between benzene rings and protons of other benzene rings of neighbouring molecules in both the benzylidene and phenyl substituents.

Graphical Abstract

X-ray diffraction analysis of hexahydroquinazolincyanamide showed that there are intermolecular hydrogen bonds with the hydrogen atoms of the quinazoline ring and the nitrogen atoms of the nitrile and imine groups. An assessment of the intermolecular stacking interaction is given.

中文翻译：

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N-(8-亚苄基-4-苯基六氢喹唑啉-2(1H)-亚基)氰酰胺的分子和晶体结构

我们通过具有相同或不同末端取代基的2,6-二芳基(杂芳基)亚甲基环己酮与N-氰基胍按照改进的方法在碱性条件下进行双组分缩合，获得了先前已知的新型4,8-C-取代的六氢喹唑啉氰酰胺。催化。我们通过从饱和乙腈溶液中结晶，生长出了该系列的代表之一——N-(8-亚苄基-4-苯基六氢喹唑啉-2(1H)-亚基)氰胺的单晶，并进行了X射线衍射研究。N- (8-亚苄基-4-苯基六氢喹唑啉-2(1 H )-亚基)氰酰胺的结构，C ₂₂ H ₂₀ N ₄，具有斜方( P 2 ₁ 2 ₁ 2 ₁ )对称性。该分子由稠合的非平面环己烯和四氢嘧啶环构成。环己烯环呈半椅式构象，而四氢嘧啶环采用“C-包络”构象。该化合物的晶体堆积为交替层状结构。分子的相互排列促进喹唑啉环的H1氢原子和腈基的N4氮原子之间形成分子间氢键(IMH)。在晶体中也观察到非平面的 C–H…π 相互作用。该化合物呈E,E构型。赫希菲尔德面的计算和分析表明，苯亚甲基和苯基取代基中均存在不同能量的氢键，以及苯环与相邻分子其他苯环质子之间的C-H·π相互作用。

图形概要

六氢喹唑啉氰胺的X射线衍射分析表明，喹唑啉环的氢原子和腈基、亚胺基的氮原子之间存在分子间氢键。给出了分子间堆积相互作用的评估。