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Crystal structures, Hirsfeld surface analysis and a computational study of four ethyl 2-oxo-2H-chromene-3-carboxylate derivatives: a survey of organyl 2-oxo-2H-chromene-3-carboxylate structures

  • Ligia R. Gomes , John N. Low EMAIL logo , Tanja van Mourik , Ligia S. da Silveira Pinto , Marcus V.N. de Souza and Jámes L. Wardell EMAIL logo
Published/Copyright: January 24, 2019
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 234 Issue 2

Abstract

Crystal structures, Hirshfeld surface analysis and a computational study have been carried out on 2-oxo-2H-chromene-3-carboxylates. Crystal structures are reported for ethyl R-2-oxo-2H-chromene-3-carboxylate derivatives, 2a: R=6-Me, 2b: 7-Me, 2c: 7-Me, 2d: R=7-MeO. In contrast to 2-oxo-2H-chromene-3-carboxamides, 1, in which classical intramolecular N–H···O hydrogen bonds stabilize planar structures and hinder rotation of the amido group out of the coumarin plane in 2, without an equivalent hydrogen bond, there is a greater rotational freedom of the carboxylate group. The interplanar angles between the coumarin core and its attached –C(O)–R substituent in crystalline 2a, 2b, 2c and 2d are 10.41(6), 36.65(6), 10.4(2) and 5.64(6)°, respectively, with distances between the carbonyl oxygen atoms of 2.8255(16), 2.9278(16), 4.226(2) and 2.8328(14) Å, respectively. A theoretical study of molecular conformations was carried out at the M06-2X density level with the 6-31+G(d) and aug-cc-pVTZ basis sets, in methanol solution modeled by PCM, indicated that the most stable conformations had the carbonyl group of the ester in the plane of the coumarin core: the s-cis arrangement of the ester carbonyl and the 2-oxo moieties being the slightly more stable than the s-trans form by less than 0.5 kcal/mol. The experimental conformations of 2a and 2d match well the low energy s-cis arrangement, and 2c matches the slightly lesser stable s-trans arrangement found in the theoretical study. A survey of the molecular conformations of more than 50 2H-chromene-3-carboxylates derivatives in the CCDC data base indicated two distinct groupings of conformations, s-cis and s-trans, each with interplanar angles <30°.

Keywords: 2-oxo-2H-chromene-3-carboxylate derivatives; crystal structures; density functional theory; Hirshfeld surface analysis; molecular conformation

Acknowledgements

The authors thank the National Crystallographic Service, University of Southampton, UK, for the data collection, and for their help and advice. LRG thanks the Portuguese Foundation for Science and Technology (FCT) UID/Multi/04546/2013 for support. TvM is grateful to EaStCHEM for computational support via the EaStCHEM Research Computing Facility. JLW thanks CNPq, Brazil for support.

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Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2018-2117).

Received: 2018-07-08
Accepted: 2018-09-02
Published Online: 2019-01-24
Published in Print: 2019-02-25

©2019 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic
  4. Temperature induced twinning in aragonite: transmission electron microscopy experiments and ab initio calculations
  5. Organic
  6. Crystal structures, Hirsfeld surface analysis and a computational study of four ethyl 2-oxo-2H-chromene-3-carboxylate derivatives: a survey of organyl 2-oxo-2H-chromene-3-carboxylate structures
  7. Non-covalent interactions observed in nevirapinium pentaiodide hydrate which include the rare I4–I−···O=C halogen bonding
  8. Open-framework sodium uranyl selenate and sodium uranyl sulfate with protonated morpholino-N-acetic acid
  9. Competition between coordination bonds and hydrogen bonding interactions in solvatomorphs of copper(II), cadmium(II) and cobalt(II) complexes with 2,2′-bipyridyl and acetate
  10. Crystallographic Computing
  11. Stress, strain and Raman shifts
https://doi.org/10.1515/zkri-2018-2117
Keywords for this article
2-oxo-2H-chromene-3-carboxylate derivatives; crystal structures; density functional theory; Hirshfeld surface analysis; molecular conformation

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic
  4. Temperature induced twinning in aragonite: transmission electron microscopy experiments and ab initio calculations
  5. Organic
  6. Crystal structures, Hirsfeld surface analysis and a computational study of four ethyl 2-oxo-2H-chromene-3-carboxylate derivatives: a survey of organyl 2-oxo-2H-chromene-3-carboxylate structures
  7. Non-covalent interactions observed in nevirapinium pentaiodide hydrate which include the rare I4–I−···O=C halogen bonding
  8. Open-framework sodium uranyl selenate and sodium uranyl sulfate with protonated morpholino-N-acetic acid
  9. Competition between coordination bonds and hydrogen bonding interactions in solvatomorphs of copper(II), cadmium(II) and cobalt(II) complexes with 2,2′-bipyridyl and acetate
  10. Crystallographic Computing
  11. Stress, strain and Raman shifts
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