Crystal structure of a 1:1 salt of 4-amino-benzoic acid (vitamin B10) with pyrazinoic acid

K V Drozd; S G Arkhipov; E V Boldyreva; G L Perlovich

doi:10.1107/S2056989018016663

Crystal structure of a 1:1 salt of 4-amino-benzoic acid (vitamin B₁₀) with pyrazinoic acid

Acta Crystallogr E Crystallogr Commun. 2018 Nov 30;74(Pt 12):1923-1927. doi: 10.1107/S2056989018016663. eCollection 2018 Dec 1.

Authors

K V Drozd¹, S G Arkhipov^{2

3}, E V Boldyreva^{2

4}, G L Perlovich¹

Affiliations

¹ G. A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1, Academicheskaya, Ivanovo 153045, Russian Federation.
² Novosibirsk State University, Pirogova str. 2, Novosibirsk, 630090, Russian Federation.
³ Institute of Solid State Chemistry and Mechanochemistry SB RAS, Kutateladze str. 18, Novosibirsk 630128, Russian Federation.
⁴ G. K. Boreskov Institute of Catalysis SB RAS, Laverentiev Ave. 5, Novosibirsk 630090, Russian Federation.

Abstract

The title 1:1 salt, C₇H₈NO₂ ⁺·C₅H₃N₂O₂ ^- (systematic name: 4-carb-oxy-anilinium pyrazine-2-carboxyl-ate), was synthesized successfully by slow evaporation of a saturated solution from water-ethanol (1:1 v/v) mixture and characterized by X-ray diffraction (SCXRD, PXRD) and calorimetry (DSC). The crystal structure of the salt was solved and refined at 150 and 293 K. The salt crystallizes with one mol-ecule of 4-amino-benzoic acid (PABA) and one mol-ecule of pyrazinoic acid (POA) in the asymmetric unit. In the crystal, the PABA and POA mol-ecules are associated via COOH⋯N_arom heterosynthons, which are connected by N-H⋯O hydrogen bonds, creating zigzag chains. The chains are further linked by N-H⋯O hydrogen bonds and π-π stacking inter-actions along the b axis [centroid-to-centroid distances = 3.7377 (13) and 3.8034 (13) Å at 150 and 293 K, respectively] to form a layered three-dimensional structure.

Keywords: 4-aminobenzoic acid; crystal structure; hydrogen bonding; melting point; pyrazinoic acid; salt.

Grants and funding

This work was funded by RFBR grant 17-33-50073 mol_nr.