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Crystal structures of three 4-substituted-2,2 ′ -bipyridines synthesized by Sonogashira and Suzuki – Miyaura cross-coupling reactions

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ABSTRACT

71: Facile synthetic routes for three 4-substituted 2,2′-bi­pyridine derivatives, 4-[2-(4-methyl­phenyl)­ethyn­yl]-2,2′-bi­pyridine, C19H14N2, (I), 4-[2-(pyridin-3-yl)ethyn­yl]-2,2′-bi­pyridine, C17H11N3, (II), and 4-(indol-4-yl)-2,2′-bi­pyridine, C18H13N3, (III), via Sonogashira and Suzuki–Miyaura cross-coupling reactions, respect­ively, are described. As indicated by X-ray analysis, the 2,2′-bi­pyridine core, the ethyl­ene linkage and the substituents of (I) and (II) are almost planar [dihedral angles between the two ring systems: 8.98 (5) and 9.90 (6)° for the two mol­ecules of (I) in the asymmetric unit and 2.66 (14)° for (II)], allowing π-conjugation. On the contrary, in (III), the indole substituent ring is rotated significantly out of the bi­pyridine plane [dihedral angle = 55.82 (3)°], due to steric hindrance. The crystal packings of (I) and (II) are dominated by π–π inter­actions, resulting in layers of mol­ecules parallel to (30-2) in (I) and columns of mol­ecules along the a axis in (II). The packing of (III) exhibits zigzag chains of mol­ecules along the c axis inter­acting through N—H⋯N hydrogen bonds and π–π inter­actions. The contributions of unknown disordered solvent mol­ecules to the diffraction intensities in (II) were removed with the SQUEEZE [Spek (2015 ▸). Acta Cryst. C, 9–18] algorithm of PLATON. The given chemical formula and other crystal data do not take into account these solvent mol­ecules.

No MeSH data available.


View of the asymmetric unit of (a) (I), (b) (II), and (c) (III) showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 50% probability level.
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fig1: View of the asymmetric unit of (a) (I), (b) (II), and (c) (III) showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 50% probability level.

Mentions: The mol­ecular conformations of the compounds (I), (II) and (III) determined in the X-ray structural analysis are shown in Fig. 1 ▸. The asymmetric unit of (I) (Fig. 1 ▸a) consists of two mol­ecules with similar conformational features (r.m.s deviation = 0.120 Å) and are linked by a C—H⋯N hydrogen bond (Table 1 ▸). As expected, the aromatic substituents introduced via an ethyl­ene bridge in (I) (Fig. 1 ▸a) and (II) (Fig. 1 ▸b) are essentially coplanar with the 2,2′-bi­pyridine core, as indicated by the dihedral angles between the aromatic moieties, viz. 8.98 (5) and 9.90 (6)° in (I) and 2.66 (14)° in (II). On the other hand, the indole moiety and the bipyridyl ring are out of plane in (III) (Fig. 1 ▸c) in order to reduce the van de Waals repulsion between H5 with H19 and H3 with H17, the dihedral angle between the mean planes of the bi­pyridine core and indole ring being 55.82 (3)°.


Crystal structures of three 4-substituted-2,2 ′ -bipyridines synthesized by Sonogashira and Suzuki – Miyaura cross-coupling reactions
View of the asymmetric unit of (a) (I), (b) (II), and (c) (III) showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 50% probability level.
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Related In: Results  -  Collection

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getmorefigures.php?uid=PMC5382633&req=5

fig1: View of the asymmetric unit of (a) (I), (b) (II), and (c) (III) showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 50% probability level.
Mentions: The mol­ecular conformations of the compounds (I), (II) and (III) determined in the X-ray structural analysis are shown in Fig. 1 ▸. The asymmetric unit of (I) (Fig. 1 ▸a) consists of two mol­ecules with similar conformational features (r.m.s deviation = 0.120 Å) and are linked by a C—H⋯N hydrogen bond (Table 1 ▸). As expected, the aromatic substituents introduced via an ethyl­ene bridge in (I) (Fig. 1 ▸a) and (II) (Fig. 1 ▸b) are essentially coplanar with the 2,2′-bi­pyridine core, as indicated by the dihedral angles between the aromatic moieties, viz. 8.98 (5) and 9.90 (6)° in (I) and 2.66 (14)° in (II). On the other hand, the indole moiety and the bipyridyl ring are out of plane in (III) (Fig. 1 ▸c) in order to reduce the van de Waals repulsion between H5 with H19 and H3 with H17, the dihedral angle between the mean planes of the bi­pyridine core and indole ring being 55.82 (3)°.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

71: Facile synthetic routes for three 4-substituted 2,2′-bi­pyridine derivatives, 4-[2-(4-methyl­phenyl)­ethyn­yl]-2,2′-bi­pyridine, C19H14N2, (I), 4-[2-(pyridin-3-yl)ethyn­yl]-2,2′-bi­pyridine, C17H11N3, (II), and 4-(indol-4-yl)-2,2′-bi­pyridine, C18H13N3, (III), via Sonogashira and Suzuki–Miyaura cross-coupling reactions, respect­ively, are described. As indicated by X-ray analysis, the 2,2′-bi­pyridine core, the ethyl­ene linkage and the substituents of (I) and (II) are almost planar [dihedral angles between the two ring systems: 8.98 (5) and 9.90 (6)° for the two mol­ecules of (I) in the asymmetric unit and 2.66 (14)° for (II)], allowing π-conjugation. On the contrary, in (III), the indole substituent ring is rotated significantly out of the bi­pyridine plane [dihedral angle = 55.82 (3)°], due to steric hindrance. The crystal packings of (I) and (II) are dominated by π–π inter­actions, resulting in layers of mol­ecules parallel to (30-2) in (I) and columns of mol­ecules along the a axis in (II). The packing of (III) exhibits zigzag chains of mol­ecules along the c axis inter­acting through N—H⋯N hydrogen bonds and π–π inter­actions. The contributions of unknown disordered solvent mol­ecules to the diffraction intensities in (II) were removed with the SQUEEZE [Spek (2015 ▸). Acta Cryst. C, 9–18] algorithm of PLATON. The given chemical formula and other crystal data do not take into account these solvent mol­ecules.

No MeSH data available.