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Crystal structure of 1-[(2,3-dihydro-1H-naphtho-[1,2-e][1,3]oxazin-2-yl)meth-yl]naphthalen-2-ol: a possible candidate for new polynaphthoxazine materials.

Rivera A, Rojas JJ, Ríos-Motta J, Bolte M - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: In the title compound, C23H19NO2, an oxazine Mannich base derivative, the oxazine ring has a half-chair conformation.The 2-hy-droxy-naphthalen-1-yl substituent is placed in an axial position.The dimers are linked by a π-π inter-action [centroid-centroid distance = 3.6268 (17) Å], consolidating a column along the a axis.

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Affiliation: Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia.

ABSTRACT
In the title compound, C23H19NO2, an oxazine Mannich base derivative, the oxazine ring has a half-chair conformation. The 2-hy-droxy-naphthalen-1-yl substituent is placed in an axial position. There is an intra-molecular O-H⋯N hydrogen bond, forming an S(6) graph-set motif. In the crystal, mol-ecules are connected by a pair of C-H⋯π inter-actions into an inversion dimer, which is reinforced by another pair of weak C-H⋯π inter-actions. The dimers are linked by a π-π inter-action [centroid-centroid distance = 3.6268 (17) Å], consolidating a column along the a axis. Furthermore, the columns inter-act with each other by a weak C-H⋯π inter-action, generating a three-dimensional network.

No MeSH data available.


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The view of the column structure along the a axis, showing the π–π stacking inter­actions (dashed lines).
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fig3: The view of the column structure along the a axis, showing the π–π stacking inter­actions (dashed lines).

Mentions: The crystal packing organization is essentially the result of two different types of inter­actions involving inversion-related mol­ecules. Based on the distance criteria employed in PLATON (Spek, 2009 ▸), the most notable inter­molecular contact is a C—H⋯π inter­action (C1—H1A⋯Cg3i; Table 1 ▸), so that an inversion dimer is formed (Fig. 2 ▸). In addition, there is another C—H⋯π inter­action (C2—H2B⋯Cg2i; Table 1 ▸) in the dimer. A column of alternating inversion dimers extending along the a axis results from a π–π stacking inter­action (Fig. 3 ▸) between adjacent 2,3-di­hydro-1H-naphtho­[1,2-e][1,3]oxazine ring systems with a centroid–centroid distance of 3.6268 (17) Å [Cg3⋯Cg3iii; symmetry code: (iii) = −x, −y + 1, −z + 1]. Neighboring columns are connected by a weak C—H⋯π inter­action (C14—H14A⋯Cg5ii; Table 1 ▸), generating a three-dimensional network. The unit-cell packing is shown in Fig. 4 ▸.


Crystal structure of 1-[(2,3-dihydro-1H-naphtho-[1,2-e][1,3]oxazin-2-yl)meth-yl]naphthalen-2-ol: a possible candidate for new polynaphthoxazine materials.

Rivera A, Rojas JJ, Ríos-Motta J, Bolte M - Acta Crystallogr E Crystallogr Commun (2015)

The view of the column structure along the a axis, showing the π–π stacking inter­actions (dashed lines).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4555368&req=5

fig3: The view of the column structure along the a axis, showing the π–π stacking inter­actions (dashed lines).
Mentions: The crystal packing organization is essentially the result of two different types of inter­actions involving inversion-related mol­ecules. Based on the distance criteria employed in PLATON (Spek, 2009 ▸), the most notable inter­molecular contact is a C—H⋯π inter­action (C1—H1A⋯Cg3i; Table 1 ▸), so that an inversion dimer is formed (Fig. 2 ▸). In addition, there is another C—H⋯π inter­action (C2—H2B⋯Cg2i; Table 1 ▸) in the dimer. A column of alternating inversion dimers extending along the a axis results from a π–π stacking inter­action (Fig. 3 ▸) between adjacent 2,3-di­hydro-1H-naphtho­[1,2-e][1,3]oxazine ring systems with a centroid–centroid distance of 3.6268 (17) Å [Cg3⋯Cg3iii; symmetry code: (iii) = −x, −y + 1, −z + 1]. Neighboring columns are connected by a weak C—H⋯π inter­action (C14—H14A⋯Cg5ii; Table 1 ▸), generating a three-dimensional network. The unit-cell packing is shown in Fig. 4 ▸.

Bottom Line: In the title compound, C23H19NO2, an oxazine Mannich base derivative, the oxazine ring has a half-chair conformation.The 2-hy-droxy-naphthalen-1-yl substituent is placed in an axial position.The dimers are linked by a π-π inter-action [centroid-centroid distance = 3.6268 (17) Å], consolidating a column along the a axis.

View Article: PubMed Central - HTML - PubMed

Affiliation: Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia.

ABSTRACT
In the title compound, C23H19NO2, an oxazine Mannich base derivative, the oxazine ring has a half-chair conformation. The 2-hy-droxy-naphthalen-1-yl substituent is placed in an axial position. There is an intra-molecular O-H⋯N hydrogen bond, forming an S(6) graph-set motif. In the crystal, mol-ecules are connected by a pair of C-H⋯π inter-actions into an inversion dimer, which is reinforced by another pair of weak C-H⋯π inter-actions. The dimers are linked by a π-π inter-action [centroid-centroid distance = 3.6268 (17) Å], consolidating a column along the a axis. Furthermore, the columns inter-act with each other by a weak C-H⋯π inter-action, generating a three-dimensional network.

No MeSH data available.


Related in: MedlinePlus