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Crystal structures of N-(pyridin-2-ylmeth-yl)pyrazine-2-carboxamide (monoclinic polymorph) and N-(pyridin-4-ylmeth-yl)pyrazine-2-carboxamide.

  • Cati DS Debiopharm International S.A., Chemin Messidor 5-7, CP 5911, CH-1002 Lausanne, Switzerland.
  • Stoeckli-Evans H Institute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland.
  • 2014-08-28
Published in:
  • Acta crystallographica. Section E, Structure reports online. - 2014
carboxamide
crystal structure
pyrazine
pyridine
English The title compounds, C11H10N4O (HL1) and C11H10N4O (HL2), are pyridine 2-ylmethyl and 4-ylmethyl derivatives, respectively, of pyrazine-2-carboxamide. HL1 was measured at 153 K and crystallized in the monoclinic space group P21/c with Z = 4. There has been a report of the same structure measured at room temperature but assumed to crystallize in the triclinic space group P-1 with Z = 4 [Sasan et al. (2008 ▶). Monatsh. Chem. 139, 773-780]. In HL1, the pyridine ring is inclined to the pyrazine ring by 61.34 (6)°, while in HL2 this dihedral angle is 84.33 (12)°. In both mol-ecules, there is a short N-H⋯N inter-action involving the pyrazine carboxamide unit. In the crystal of HL1, mol-ecules are linked by N-H⋯N hydrogen bonds, forming inversion dimers with an R 2 (2)(10) ring motif. The dimers are linked via bifurcated-acceptor C-H⋯O hydrogen bonds, forming sheets lying parallel to (102). The sheets are linked via C-H⋯N hydrogen bonds, forming a three-dimensional structure. In the crystal of HL2, mol-ecules are linked by N-H⋯N and C-H⋯N hydrogen bonds to form chains propagating along [010]. The chains are linked via C-H⋯O hydrogen bonds, forming sheets lying parallel to (100). Within the sheets there are π-π inter-actions involving neighbouring pyrazine rings [inter-centroid distance = 3.711 (15) Å]. Adjacent sheets are linked via parallel slipped π-π inter-actions involving inversion-related pyridine rings [inter-centroid distance = 3.6395 (17) Å], forming a three-dimensional structure.
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https://sonar.rero.ch/global/documents/83147
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