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- Title
Charge density analysis of metformin chloride, a biguanide anti-hyperglycemic agent.
- Authors
Devi, Rajendran Niranjana; Jelsch, Christian; Israel, Samuel; Aubert, Emmanuel; Anzline, Chellam; Hosamani, Amar A.
- Abstract
The experimental charge density analysis of the anti-hyperglycemic agent metformin chloride with high-resolution X-ray diffraction data at low temperature (100 K) has been performed and these experimental results were compared with that derived from the corresponding periodic theoretical calculations at the B3LYP/6-31G** level of theory. The experimental and theoretical multipolar charge-density analyses of metformin chloride have been accomplished in order to understand its structural and electronic properties. The C and N atoms of the molecular backbone adopt a near trigonal geometry due to the occurrence of extensive delocalization/resonance of C-N bonds, as confirmed by topological analysis and also found by Natural Resonance Theory calculations performed in the isolated metformin cation. The molecule contains six C-N bonds and the topological bond order analysis shows that four bonds have bond orders close to 4/3 and two bonds can be considered as single. The analysis of numerical parameters of the valence shell charge concentration reports that the N3 atom, which forms two bonds with C atoms, possesses one non-bonding valence-shell charge concentration (VSCC) in the direction of the electron lone pair. Among the intermolecular interactions of the chloride atom with the H-C and H-N atoms, eight have been found to be shorter than the sum of van der Waals radii. The analysis of contacts on the Hirshfeld surface reveals that the H-N…Cl hydrogen bonds are enriched (over-represented) and act as the driving force in the crystal packing formation. The metformin cations form favorable electrostatic interactions with the chloride anions which have globally a stronger energy than the unfavorable cation/cation interactions.
- Subjects
DENSITY; METFORMIN; BIGUANIDE
- Publication
Acta Crystallographica Section B: Structural Science, Crystal Engineering & Materials, 2017, Vol 73, Issue 1, p10
- ISSN
2052-5192
- Publication type
Article
- DOI
10.1107/S2052520616017844