Abstract
The synthesis and detailed description of the crystal structure and energetic features of the 1:1 cocrystal of carbamazepine (5H-dibenzo[b,f]azepine-5-carboxamide, CBZ) with 3,5-dinitrobenzoic acid (35DNBA), i.e. C15H12N2O·C7H4N2O6, are reported. The CBZ and 35DNBA molecules are packed in alternately arranged layers. Two characteristic R 2 2(8) and R 2 2(16) hydrogen-bond ring motifs have been found. The supramolecular architecture, besides the network of hydrogen bonds, is also stabilized by numerous C-H⋯π, C=O⋯π, N-O⋯π, N-O⋯C and C=O⋯N weak intermolecular contacts involving neighbouring molecules in the crystal network. Identified interactions have been discussed in detail on the basis of a structural and energetic analysis. The latter approach, performed using the Pixel and CrystalExplorer programs, yielded additional information about the lattice energy and energetic landscape of the respective interactions in the crystal of CBZ·3DNBA with the evaluation of electrostatic, polarization, repulsion and dispersion terms.
Original language | English |
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Pages (from-to) | 1150-1156 |
Number of pages | 7 |
Journal | Acta Crystallographica Section C: Structural Chemistry |
Volume | 75 |
DOIs | |
State | Published - Aug 1 2019 |
Externally published | Yes |
Funding
Theoretical calculations were performed using the resources of WCSS (grant number 115). The data collection was carried out at the Core Facility for crystallographic and biophysical research to support the development of medicinal products sponsored by the Foundation for Polish Science (FNP). The research was carried out at the Biological and Chemical Research Centre, University of Warsaw, established within the project co-financed by European Union from the European Regional Development Fund under the Operational Programme Innovative Economy, 2007–2013. Funding for this research was provided by: National Science Centre Poland (MAESTRO grant No. DEC-2012/04/A/ST5/ 00609 to KW, SP and DT).
Keywords
- carbamazepine
- cocrystal
- crystal engineering
- crystal structure
- energy calculations
- energy frameworks
- hydrogen bonds
- nitro group interactions