Molecular and crystal structure, lattice energy and DFT calculations of two 2′-(nitrobenzoyloxy)acetophenone isomers

• Main Authors: Georgii Bogdanov, Jenna Bustos, Viktor Glebov, Evgenii Oskolkov, John P. Tillotson, Tatiana V. Timofeeva
• Format: Article
• Language: English
• Published: International Union of Crystallography 2020-06-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: 2′-(nitrobenzoyloxy)acetophenone isomers; crystal structure; molecular conformation; dft calculations; lattice energy
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989020006295
• ISSN: 2056-9890

The two isomers 2′-(4-nitrobenzoyloxy)acetophenone (systematic name: 2-acetylphenyl 4-nitrobenzoate) (I) and 2′-(2-nitrobenzoyloxy)acetophenone (systematic name: 2-acetylphenyl 2-nitrobenzoate) (II), both C15H11NO5, with para and ortho positions of the nitro substituent have been crystallized and studied. It is evident that the variation in the position of the nitro group causes a significant difference in the molecular conformations: the dihedral angle between the aromatic fragments in the molecule of I is 84.80 (4)°, while that in the molecule of II is 6.12 (7)°. Diffraction analysis revealed the presence of a small amount of water in the crystal of I. DFT calculations of the molecular energy demonstrate that the ortho substituent causes a higher energy for isomer II, while crystal lattice energy calculations show that the values are almost equal for two isomers.