TY - JOUR

T1 - A cocrystal of L-ascorbic acid with picolinic acid

T2 - the role of O-H...O, N-H...O and C-H...O hydrogen bonds and L-ascorbic acid conformation in structure stabilization

AU - Evtushenko, Diana N.

AU - Arkhipov, Sergey G.

AU - Fateev, Alexander V.

AU - Izaak, Tatyana I.

AU - Egorova, Lidia A.

AU - Skorik, Nina A.

AU - Vodyankina, Olga V.

AU - Boldyreva, Elena V.

N1 - Publisher Copyright: © 2020 International Union of Crystallography. All rights reserved.

PY - 2020/12/1

Y1 - 2020/12/1

N2 - A new 1:1 cocrystal (L-Asc-Pic) of L-ascorbic acid (vitamin C) with picolinic acid was prepared as a powder and as single crystals. The crystal structure was solved and refined from single-crystal X-ray diffraction (SCXRD) data collected at 293 (2) and 100 (2) K. The samples of the L-Asc-Pic cocrystal were characterized by elemental (HCNS) analysis and titrimetric methods, TG/DTG/DSC, and IR and Raman spectroscopy. The asymmetric unit comprises a picolinic acid zwitterion and an L-ascorbic acid molecule. The stabilization energy of intermolecular interactions involving hydrogen bonds, the vibrational spectrum and the energies of the frontier molecular orbitals were calculated using the GAUSSIAN09 and the CrystalExplorer17 programs. The charge distribution on the atoms of the L-Asc-Pic cocrystal, L-ascorbic acid itself and its 12 known cocrystals (structures from Version 5.40 of the Cambridge Structural Database) were calculated by the methods of Mulliken, Voronoi and Hirshfeld charge analyses (ADF) at the bp86/TZ2P+ level of theory. The total effective charges and conformations of the L-ascorbic acid molecules in the new and previously reported cocrystals were compared with those of the two symmetry-independent molecules in the crystals of L-ascorbic acid. A correlation between molecular conformation and its effective charge is discussed.

AB - A new 1:1 cocrystal (L-Asc-Pic) of L-ascorbic acid (vitamin C) with picolinic acid was prepared as a powder and as single crystals. The crystal structure was solved and refined from single-crystal X-ray diffraction (SCXRD) data collected at 293 (2) and 100 (2) K. The samples of the L-Asc-Pic cocrystal were characterized by elemental (HCNS) analysis and titrimetric methods, TG/DTG/DSC, and IR and Raman spectroscopy. The asymmetric unit comprises a picolinic acid zwitterion and an L-ascorbic acid molecule. The stabilization energy of intermolecular interactions involving hydrogen bonds, the vibrational spectrum and the energies of the frontier molecular orbitals were calculated using the GAUSSIAN09 and the CrystalExplorer17 programs. The charge distribution on the atoms of the L-Asc-Pic cocrystal, L-ascorbic acid itself and its 12 known cocrystals (structures from Version 5.40 of the Cambridge Structural Database) were calculated by the methods of Mulliken, Voronoi and Hirshfeld charge analyses (ADF) at the bp86/TZ2P+ level of theory. The total effective charges and conformations of the L-ascorbic acid molecules in the new and previously reported cocrystals were compared with those of the two symmetry-independent molecules in the crystals of L-ascorbic acid. A correlation between molecular conformation and its effective charge is discussed.

KW - cocrystal

KW - conformations of molecules

KW - DFT

KW - energy of hydrogen bond

KW - Hirshfeld charge

KW - IR and Raman spectroscopy

KW - l-ascorbic acid

KW - Mulliken populations

KW - picolinic acid

KW - root-mean-square deviation of atomic positions (RMSD)

KW - vitamin C

KW - Voronoi charge

KW - L-ascorbic acid

KW - GRAPH-SET ANALYSIS

KW - PATTERNS

KW - CRYSTAL

KW - AMINO-ACIDS

KW - X-RAY

UR - http://www.scopus.com/inward/record.url?scp=85097578100&partnerID=8YFLogxK

U2 - 10.1107/S2052520620012421

DO - 10.1107/S2052520620012421

M3 - Article

C2 - 33289709

AN - SCOPUS:85097578100

VL - 76

SP - 967

EP - 978

JO - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

JF - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

SN - 2052-5192

IS - Pt 6

ER -