Ayoub El-Mrabet, Amal Haoudi, Frederic Capet, Tuncer Hökelek, Mazzah Ahmed
{"title":"2-[(4-氰基-苯基)甲基-氧]喹啉-4-羧酸甲酯的晶体结构和赫希菲尔德表面分析、相互作用能计算和能量框架。","authors":"Ayoub El-Mrabet, Amal Haoudi, Frederic Capet, Tuncer Hökelek, Mazzah Ahmed","doi":"10.1107/S2056989025005547","DOIUrl":null,"url":null,"abstract":"<p><p>The title compound, C<sub>19</sub>H<sub>14</sub>N<sub>2</sub>O<sub>3</sub>, features competition and inter-play of a range of weak inter-actions, which actualize under the absence of conventional hydrogen-bond donors. Two kinds of stacking inter-actions, namely slipped anti-parallel inter-actions of cyano-phenyl groups as well as quinoline and carb-oxy groups, are primarily important. In combination with relatively short tetrel OCH<sub>3</sub>⋯N≡C bonds [C⋯N = 3.146 (3) Å] they are responsible for the generation of the layers, while the inter-layer bonding occurs <i>via</i> C-H⋯O and C-H⋯N weak hydrogen bonds. These findings are consistent with the results of Hirshfeld surface analysis and calculated inter-action energies. Contributions of the C⋯C, C⋯N/N⋯C and C⋯O/O⋯C contacts originating in the stacking inter-actions account for 17.0% to the surface area. The largest inter-actions energies are associated with the two kinds of stacks (-45.8 and -24.3 kJ mol<sup>-1</sup>) and they are superior to the energies of weak hydrogen bond and tetrel inter-actions (-12.4 to -22.4 kJ mol<sup>-1</sup>). Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the consolidation is dominated <i>via</i> the dispersion energy contributions.</p>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 Pt 7","pages":"650-656"},"PeriodicalIF":0.5000,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12230613/pdf/","citationCount":"0","resultStr":"{\"title\":\"Crystal structure and Hirshfeld surface analyses, inter-action energy calculations and energy frameworks of methyl 2-[(4-cyano-phen-yl)meth-oxy]quinoline-4-carboxyl-ate.\",\"authors\":\"Ayoub El-Mrabet, Amal Haoudi, Frederic Capet, Tuncer Hökelek, Mazzah Ahmed\",\"doi\":\"10.1107/S2056989025005547\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>The title compound, C<sub>19</sub>H<sub>14</sub>N<sub>2</sub>O<sub>3</sub>, features competition and inter-play of a range of weak inter-actions, which actualize under the absence of conventional hydrogen-bond donors. Two kinds of stacking inter-actions, namely slipped anti-parallel inter-actions of cyano-phenyl groups as well as quinoline and carb-oxy groups, are primarily important. In combination with relatively short tetrel OCH<sub>3</sub>⋯N≡C bonds [C⋯N = 3.146 (3) Å] they are responsible for the generation of the layers, while the inter-layer bonding occurs <i>via</i> C-H⋯O and C-H⋯N weak hydrogen bonds. These findings are consistent with the results of Hirshfeld surface analysis and calculated inter-action energies. Contributions of the C⋯C, C⋯N/N⋯C and C⋯O/O⋯C contacts originating in the stacking inter-actions account for 17.0% to the surface area. The largest inter-actions energies are associated with the two kinds of stacks (-45.8 and -24.3 kJ mol<sup>-1</sup>) and they are superior to the energies of weak hydrogen bond and tetrel inter-actions (-12.4 to -22.4 kJ mol<sup>-1</sup>). Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the consolidation is dominated <i>via</i> the dispersion energy contributions.</p>\",\"PeriodicalId\":7367,\"journal\":{\"name\":\"Acta Crystallographica Section E: Crystallographic Communications\",\"volume\":\"81 Pt 7\",\"pages\":\"650-656\"},\"PeriodicalIF\":0.5000,\"publicationDate\":\"2025-06-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12230613/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Acta Crystallographica Section E: Crystallographic Communications\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1107/S2056989025005547\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/7/1 0:00:00\",\"PubModel\":\"eCollection\",\"JCR\":\"Q4\",\"JCRName\":\"CRYSTALLOGRAPHY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Crystallographica Section E: Crystallographic Communications","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1107/S2056989025005547","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/7/1 0:00:00","PubModel":"eCollection","JCR":"Q4","JCRName":"CRYSTALLOGRAPHY","Score":null,"Total":0}
Crystal structure and Hirshfeld surface analyses, inter-action energy calculations and energy frameworks of methyl 2-[(4-cyano-phen-yl)meth-oxy]quinoline-4-carboxyl-ate.
The title compound, C19H14N2O3, features competition and inter-play of a range of weak inter-actions, which actualize under the absence of conventional hydrogen-bond donors. Two kinds of stacking inter-actions, namely slipped anti-parallel inter-actions of cyano-phenyl groups as well as quinoline and carb-oxy groups, are primarily important. In combination with relatively short tetrel OCH3⋯N≡C bonds [C⋯N = 3.146 (3) Å] they are responsible for the generation of the layers, while the inter-layer bonding occurs via C-H⋯O and C-H⋯N weak hydrogen bonds. These findings are consistent with the results of Hirshfeld surface analysis and calculated inter-action energies. Contributions of the C⋯C, C⋯N/N⋯C and C⋯O/O⋯C contacts originating in the stacking inter-actions account for 17.0% to the surface area. The largest inter-actions energies are associated with the two kinds of stacks (-45.8 and -24.3 kJ mol-1) and they are superior to the energies of weak hydrogen bond and tetrel inter-actions (-12.4 to -22.4 kJ mol-1). Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the consolidation is dominated via the dispersion energy contributions.
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.