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Crystal structures of N -[4-(tri-fluoro-meth-yl)phen-yl]benzamide and N -(4-meth-oxy-phen-yl)benz-amide at 173 K: a study of the energetics of conformational changes due to crystal packing.

  • Academic Journal
  • Pearson WH; Chemistry Department, United States Naval Academy, 572 Holloway Rd, Annapolis, MD 21402, USA.
    Urban JJ; Chemistry Department, United States Naval Academy, 572 Holloway Rd, Annapolis, MD 21402, USA.
    MacArthur AHR; Chemistry Department, United States Naval Academy, 572 Holloway Rd, Annapolis, MD 21402, USA.
    Lin S; Chemistry Department, United States Naval Academy, 572 Holloway Rd, Annapolis, MD 21402, USA.
    Cabrera DWL; Chemistry Department, United States Naval Academy, 572 Holloway Rd, Annapolis, MD 21402, USA.
  • Acta crystallographica. Section E, Crystallographic communications [Acta Crystallogr E Crystallogr Commun] 2022 Feb 08; Vol. 78 (Pt 3), pp. 297-305. Date of Electronic Publication: 2022 Feb 08 (Print Publication: 2022).
  • English
  • As a part of our study of the syntheses of aryl amides, the crystal structures of two benzamides were determined from single-crystal X-ray data at 173 K. Both crystal structures contain mol-ecular units as asymmetric units with no solvent in the unit cells. Crystal structure I, TFMP , is the result of the crystallization of N -[4-(tri-fluoro-meth-yl)phen-yl]benzamide, C 14 H 10 F 3 NO. Crystal structure II, MOP , is composed of N -(4-meth-oxy-phen-yl)benzamide, C 14 H 13 NO 2 , units. TFMP is triclinic, space group P , consisting of two mol-ecules in the unit cell related by the center of symmetry. MOP is monoclinic, space group P 2 1 / c , consisting of four mol-ecules in the unit cell. Both types of mol-ecules contain three planar regions; a phenyl ring, an amide planar region, and a para -substituted phenyl ring. The orientations of these planar regions within the asymmetric units are compared to their predicted orientations, in isolation, from DFT calculations. The aryl rings are tilted approximately 60° with respect to each other in both experimentally determined structures, as compared to 30° in the DFT results. These conformational changes result in more favorable environments for N-H⋯O hydrogen bonding and aryl ring π-stacking in the crystal structures. Inter-molecular inter-actions were examined by Hirshfeld surface analysis and qu-anti-fied by calculating mol-ecular inter-action energies. The results of this study demonstrate that both hydrogen bonding and dispersion are essential to the side-by-side stacking of mol-ecular units in these crystal structures. Weaker dispersion inter-actions along the axial directions of the mol-ecules reveal insight into the melting mechanisms of these crystals.
    (© Pearson et al. 2022.)
Additional Information
Publisher: John Wiley & Sons Ltd Country of Publication: England NLM ID: 101648987 Publication Model: eCollection Cited Medium: Print ISSN: 2056-9890 (Print) NLM ISO Abbreviation: Acta Crystallogr E Crystallogr Commun Subsets: PubMed not MEDLINE
Original Publication: West Sussex : John Wiley & Sons Ltd. [2015]-
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Keywords: DFT calculations; Hirshfeld surfaces; aryl amides; crystal structure; inter­molecular forces; mol­ecular inter­action energies
Date Created: 20220404 Latest Revision: 20220405
20220908
PMC8900516
10.1107/S2056989022000950
35371548

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