Synthesis, crystal structure and Hirshfeld surface analysis of 1-(3,4-dichlorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications Pub Date : 2026-08-01 Epub Date: 2026-08-12 DOI:10.1107/S2056989026007231

Sharatha Kumar, Tuncer Hökelek

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引用次数: 0

Abstract

The title compound, C₁₃H₁₄Cl₂N₂S, consists of dichlorophenyl and dihydropyrimidinethione rings, where the pyrimidine ring is in a flattened-boat conformation. In the crystal, N—H⋯S hydrogen bonds link the molecules, enclosing R²₂(8) ring motifs, into centrosymmetric dimers. Neither π–π stacking nor C—H⋯π(ring) interactions are observed. Hirshfeld surface analysis revealed that the most important contributions for crystal packing are from H⋯H (40.8%), H⋯Cl/Cl⋯H (28.7%) and H⋯S/S⋯H (15.5%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 135.01 Å³ and 17.99%, showing the crystal packing is not compact. Computational methods indicated an N—H⋯S hydrogen-bonding energy of −58.2 kJ mol⁻¹. Evaluations of the electrostatic, dispersion and total energy frameworks indicate that the crystal cohesion is dominated by electrostatic energy contributions.

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1-（3,4-二氯苯基）-4,4,6-三甲基-3,4-二氢嘧啶-2(1H)-硫酮的合成、晶体结构和Hirshfeld表面分析。

标题化合物C13H14Cl2N2S由二氯苯基环和二氢嘧啶硫酮环组成，其中嘧啶环呈扁船状构象。在晶体中，N-H⋯S氢键连接分子，将r22(8)环基序包裹成中心对称的二聚体。既没有观察到π-π堆叠，也没有观察到C-H⋯π（环）相互作用。Hirshfeld表面分析显示，对晶体堆积最重要的贡献是H⋯H (40.8%), H⋯Cl/Cl⋯H（28.7%）和H⋯S/S⋯H（15.5%）相互作用。计算得到晶体孔洞体积为135.01 Å3，自由空间百分比为17.99%，表明晶体堆积不致密。计算方法表明，N-H⋯S氢键能为-58.2 kJ mol-1。对静电、色散和总能量框架的评价表明，晶体内聚主要受静电能量贡献的影响。

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, crystal structure and Hirshfeld surface analysis of 1-(3,4-di­chloro­phen­yl)-4,4,6-trimethyl-3,4-di­hydro­pyrimidine-2(1H)-thione

Abstract

Synthesis, crystal structure and Hirshfeld surface analysis of 1-(3,4-dichlorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione