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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, Stoeckli-Evans H - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: Monatsh.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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Affiliation: Debiopharm International S.A., Chemin Messidor 5-7, CP 5911, CH-1002 Lausanne, Switzerland.

ABSTRACT
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.

No MeSH data available.


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A partial view along the a axis of the crystal packing of compound HL1. The N—H⋯N, C—H⋯O and C-H⋯N hydrogen bonds are shown as dashed lines (see Table 1 ▶ for details).
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fig3: A partial view along the a axis of the crystal packing of compound HL1. The N—H⋯N, C—H⋯O and C-H⋯N hydrogen bonds are shown as dashed lines (see Table 1 ▶ for details).

Mentions: In the crystal of HL1, mol­ecules are linked by N—H⋯N hydrogen bonds, forming inversion dimers with an (10) ring motif. The dimers are linked via bifurcated-acceptor C—H⋯O hydrogen bonds, forming sheets lying parallel to (102) (see Table 1 ▶ and Fig. 3 ▶). The sheets are linked via C—H⋯N hydrogen bonds, forming a three-dimensional structure (Table 1 ▶ and Fig. 4 ▶).


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

Cati DS, Stoeckli-Evans H - Acta Crystallogr Sect E Struct Rep Online (2014)

A partial view along the a axis of the crystal packing of compound HL1. The N—H⋯N, C—H⋯O and C-H⋯N hydrogen bonds are shown as dashed lines (see Table 1 ▶ for details).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4120586&req=5

fig3: A partial view along the a axis of the crystal packing of compound HL1. The N—H⋯N, C—H⋯O and C-H⋯N hydrogen bonds are shown as dashed lines (see Table 1 ▶ for details).
Mentions: In the crystal of HL1, mol­ecules are linked by N—H⋯N hydrogen bonds, forming inversion dimers with an (10) ring motif. The dimers are linked via bifurcated-acceptor C—H⋯O hydrogen bonds, forming sheets lying parallel to (102) (see Table 1 ▶ and Fig. 3 ▶). The sheets are linked via C—H⋯N hydrogen bonds, forming a three-dimensional structure (Table 1 ▶ and Fig. 4 ▶).

Bottom Line: Monatsh.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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Debiopharm International S.A., Chemin Messidor 5-7, CP 5911, CH-1002 Lausanne, Switzerland.

ABSTRACT
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.

No MeSH data available.


Related in: MedlinePlus