4′-(3,4-Dimethoxyphenyl)-2,2′:6′,2′′-terpyridine

• Main Authors: Tsugiko Takase, Yuka Soga, Dai Oyama
• Format: Article
• Language: English
• Published: International Union of Crystallography 2016-06-01
• Series: IUCrData
• Subjects: crystal structure; terpyridine; dimethoxyphenyl substituent; hydrogen bonds; π–π contacts
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2414314616009500

In the title compound, C23H19N3O2, the terpyridine unit has a dimethoxyphenyl substituent at the 4-position of the central pyridyl ring. The three pyridyl rings are in a transoid conformation with respect to the interannular C—C bonds. In addition, the pendant dimethoxyphenyl substituent is almost coplanar with the terpyridyl unit; the dihedral angle between the central pyridyl ring and the benzene ring is 7.14 (11)°, which is much smaller than that found in the structural isomer with a 2,5-dimethoxyphenyl substituent. The C—C and C—N bond lengths within the aromatic rings are normal. One of the terminal pyridyl rings is disordered over two sets of sites with an occupancy ratio of 0.744 (7):0.256 (7). The orientation of the two methoxy groups at the 3- and 4-positions is such that the methyl groups point away from each other in opposite directions. In the crystal structure, C–H...N hydrogen bonds form chains along b while C—H...O contacts form inversion dimers, creating double chains. These combine with C—H...π contacts and π...π interactions, with a centroid-centroid distance of 3.858 (4) Å, to stack molecules along the b-axis direction.