Crystal structure of 2-oxo-2H-chromen-7-yl 4-fluorobenzoate

Acta Crystallographica Section E: Crystallographic Communications

Stéphane Coussan¹  Jules Yoda²  Abdoulaye Djandé²  T. Jérémie Zoueu³  Akoun Abou³ 

[1] CNRS, Aix-Marseille Université, UMR 7345, Laboratoire de Physique des Interactions Ioniques et Moléculaires, Centre St Jérôme, 13397 Marseille Cedex 20, France;Laboratoire de Chimie Moléculaire et de Matériaux (LCMM), Equipe de Chimie Organique et de Phytochimie, Université Ouaga I Pr Joseph KI-ZERBO, 03 BP 7021 Ouagadougou 03, Burkina Faso;Unité Mixte de Recherche et d'Innovation en Electronique et d'Electricité Appliqueés (UMRI EEA), Equipe de Recherche: Instrumentation Image et Spectroscopie (L2IS), DFR–GEE, Institut National Polytechnique Félix Houphouët-Boigny (INPHB), BP 1093 Yamoussoukro, Côte d'Ivoire;

关键词: coumarin ester;    C—H...O hydrogen bonds;    π–π stacking interactions;    Hirshfeld surface analysis;    quantum chemical calculations;    crystal structure;   

DOI  :  10.1107/S205698901800614X

来源: DOAJ

【 摘 要 】

In the title compound, C16H9FO4, (I), the benzene ring is oriented at an acute angle of 59.03 (15)° relative to the coumarin plane (r.m.s deviation = 0.009 Å). This conformation of (I) is stabilized by an intramolecular C—H...O hydrogen bond, which closes a five-membering ring. In the crystal, molecules of (I) form infinite zigzag chains along the b-axis direction, linked by C—H...O hydrogen bonds. Furthermore, the crystal structure is supported by π–π stacking interactions between neighbouring pyrone and benzene or coumarin rings [centroid–centroid distances in the range 3.5758 (18)–3.6115 (16) Å], as well as C=O...π interactions [O...centroid distances in the range 3.266 (3)–3.567 (3) Å]. The theoretical data for (I) obtained from quantum chemical calculations are in good agreement with the observed structure, although the calculated C—O—C—C torsion angle between the coumarin fragment and the benzene ring (73.7°) is somewhat larger than the experimental value [63.4 (4)°]. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions.

【 授权许可】

Unknown