Abstract
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 atransoidconformation 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 alongbwhile 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 theb-axis direction.
Highlights
In the title compound, C23H19N3O2, the terpyridine unit has a dimethoxyphenyl substituent at the 4-position of the central pyridyl ring
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
One of the terminal pyridyl rings is disordered over two sets of sites with an occupancy ratio of 0.744 (7):0.256 (7)
Summary
Symmetry codes: (i) x À 12; Ày þ 12; z; (ii) Àx þ 1; Ày þ 1; Àz þ 2; (iii) Àx þ 12; y À 12; Àz þ 2; (iv) x þ 12; Ày þ 12; z; (v) x; y þ 1; z. In the molecule (Fig. 1), the terpyridine unit has a dimethoxyphenyl substituent at the 4-position of the central pyridyl ring. 7.14 (11) between the N2/C6–C10 and C16–C21 ring planes This is comparable to that found for the related compound with a phenyl substituent (10.9; Constable et al, 1990) but distinct from that of the corresponding 2,5-dimethoxyphenyl structural isomer (50.2; Storrier et al, 1998). A – contact between Cg3 and Cg4, 3.858 (4) A , (Cg3 and Cg4 are the centroids of the N2/ C6–C10 and N3/C11–C15 rings respectively; symmetry operation x, À1 + y, z) stack molecules along the b-axis direction, Fig. 2. C23H19N3O2 369.42 Monoclinic, P21/a 93 18.280 (14), 5.493 (4), 18.298 (14) 96.020 (6) 1827 (3) 4 Mo K 0.09 0.20 Â 0.15 Â 0.08
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