Exo conformers of N-(pyridin-2-yl)- and N-(pyridin-3-yl)norbornene-5,6-dicarboximide crystals.
Two isomeric pyridine-substituted norbornenedicarboximide derivatives, namely N-(pyridin-2-yl)-exo-norbornene-5,6-dicarboximide, (I), and N-(pyridin-3-yl)-exo-norbornene-5,6-dicarboximide, (II), both C(14)H(12)N(2)O(4), have been crystallized and their structures unequivocally determined by single-crystal X-ray diffraction. The molecules consist of norbornene moieties fused to a dicarboximide ring substituted at the N atom by either pyridin-2-yl or pyridin-3-yl in an anti configuration with respect to the double bond, thus affording exo isomers. In both compounds, the asymmetric unit consists of two independent molecules (Z' = 2). In compound (I), the pyridine rings of the two independent molecules adopt different conformations, i.e. syn and anti, with respect to the methylene bridge. The intermolecular contacts of (I) are dominated by C-H...O interactions. In contrast, in compound (II), the pyridine rings of both molecules have an anti conformation and the two independent molecules are linked by carbonyl-carbonyl interactions, as well as by C-H...O and C-H...N contacts.
Facultad de Ciencias Químicas, Universidad de Colima, Km 9 Carretera, Colima-Coquimatlán s/n, CP 28400, Coquimatlán, Colima, Mexico.
Oscar F
OF
Vazquez-Vuelvas
Facultad de Ciencias Químicas, Universidad de Colima, Km 9 Carretera, Colima-Coquimatlán s/n, CP 28400, Coquimatlán, Colima, Mexico.
Julia V
JV
Hernández-Madrigal
Facultad de Ciencias Químicas, Universidad de Colima, Km 9 Carretera, Colima-Coquimatlán s/n, CP 28400, Coquimatlán, Colima, Mexico.
Armando
A
Pineda-Contreras
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México DF 04510, Mexico.
Simón
S
Hernández-Ortega
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México DF 04510, Mexico.
Reyna
R
Reyes-Martínez
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México DF 04510, Mexico.
David
D
Morales-Morales
crystal structure; dicarboximide; dipole–dipole contact; exo isomers; norbornene; pyridin-2-yl; pyridin-3-yl