Synthesis, structure and energy calculations of 4-{4-[(2,3-dioxoindol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}butyl acetate

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications Pub Date : 2026-08-01 Epub Date: 2026-08-12 DOI:10.1107/S2056989026006985

Sanaa Sabir, Nour El Hoda Mustaphi, Daouda Ballo, Olivier Blacque, Tuncer Hökelek, Nada Kheira Sebbar

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Abstract

The title compound, C₁₇H₁₈N₄O₄, consists of almost planar isatin and triazole rings inclined by 78.47 (5)°, as well as a butyl acetate moiety bonded to the N atom of the triazole ring. In the crystal, molecules link into a semicolon shape along the b-axis direction through bifurcated C—H⋯O hydrogen bonds. Aromatic π–π and C—H⋯π(ring) interactions also help to consolidate the crystal packing. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (40.6%), H⋯O/O⋯H (26.6%), H⋯N/N⋯H (13.8%) and H⋯C/C⋯H (8.9%) interactions. The volume of the crystal voids and the percentage of free space in the unit cell were calculated to be 82.1 Å³ and 10.0%, respectively, showing that there is no large cavity in the crystal packing. Computational methods revealed C—H⋯O hydrogen-bonding energy of −11.6 kJ mol⁻¹. The evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated via the dispersion energy contributions in the crystal structure.

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4-{4-[（2,3-二氧吲哚-1-基）甲基]- 1h -1,2,3-三唑-1-基}乙酸丁酯的合成、结构和能量计算

标题化合物C17H18N4O4由倾斜78.47(5)°的几乎平面的isatin和三唑环以及与三唑环N原子键合的乙酸丁酯部分组成。在晶体中，分子通过分叉的C-H⋯O氢键沿b轴方向连接成分号形状。芳香π-π和C-H⋯π（环）相互作用也有助于巩固晶体包装。晶体结构的Hirshfeld表面分析表明，对晶体堆积最重要的贡献是H⋯H (40.6%), H⋯O/O⋯H (26.6%), H⋯N/N⋯H（13.8%）和H⋯C/C⋯H（8.9%）相互作用。计算得到晶胞内的孔洞体积和自由空间百分比分别为82.1 Å3和10.0%，说明晶体填料中不存在大的孔洞。计算方法显示C-H⋯O氢键能为-11.6 kJ mol-1。对静电、色散和总能量框架的评价表明，晶体结构中的色散能对稳定性起主导作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Acta Crystallographica Section E: Crystallographic Communications Chemistry-Chemistry (all)

CiteScore

1.90

自引率

0.00%

发文量

351

审稿时长

3 weeks

期刊介绍： Acta Crystallographica Section E: Crystallographic Communications is the IUCr''s open-access structural communications journal. It provides a fast, simple and easily accessible publication mechanism for crystal structure determinations of inorganic, metal-organic and organic compounds. The electronic submission, validation, refereeing and publication facilities of the journal ensure rapid and high-quality publication of fully validated structures. The primary article category is Research Communications; these are peer-reviewed articles describing one or more structure determinations with appropriate discussion of the science.

Synthesis, structure and energy calculations of 4-{4-[(2,3-dioxoindol-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}butyl acetate

Abstract

Synthesis, structure and energy calculations of 4-{4-[(2,3-dioxoindol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}butyl acetate