TY - JOUR
T1 - Crystal structure of azilsartan methyl ester ethyl acetate hemisolvate
AU - Li, Zhengyi
AU - Liu, Rong
AU - Zhu, Meilan
AU - Chen, Liang
AU - Sun, Xiaoqiang
A2 - Harrison, W. T A
N1 - We gratefully acknowledge financial support from the NSFC (No. 21002009), the Scientific and Technological Project of Jiangsu Province (BY2014037–01), the Major Program for Natural Science Research of Jiangsu Colleges and Universities (12 K J A150002, 14 K J A150002) and the Qing Lan Project of Jiangsu Province.
PY - 2015/2/1
Y1 - 2015/2/1
N2 - The title compound, C26H22N4O5 (systematic name: methyl 2-ethoxy-1-{4-[2-(5-oxo-4, 5-dihydro-1, 2, 4-oxadiazol-3-yl)phen-yl]benzyl}-1 H-1, 3-benzodiazole-7-carboxylate ethyl acetate hemisolvate), was obtained via cyclization of methyl (Z)-2-ethoxy-1-{(2′-(N′-hydroxycarbamimidoyl)-[1, 1′-biphenyl]-4-yl)methyl}-1 H-benzo[d]imidazole-7-carboxylate with diphen-yl carbonate. There are two independent molecules (A and B) with different conformations and an ethyl acetate solvent molecule in the asymmetric unit. In molecule A, the dihedral angle between the benzene ring and its attached oxadiazole ring is 59.36 (17); the dihedral angle between the benzene rings is 43.89 (15) and that between the benzene ring and its attached imidazole ring system is 80.06 (11)°. The corresponding dihedral angles in molecule B are 58.45 (18), 50.73 (16) and 85.37 (10)°, respectively. The C - O - C - Cm (m = methyl) torsion angles for the ethoxy side chains attached to the imidazole rings in molecules A and B are 93.9 (3) and - 174.6 (3)°, respectively. In the crystal, the components are linked by N - H⋯N and C - H⋯O hydrogen bonds, generating a three-dimensional network. Aromatic π-π stacking interactions [shortest centroid-centroid separation = 3.536 (3)Å] are also observed.
AB - The title compound, C26H22N4O5 (systematic name: methyl 2-ethoxy-1-{4-[2-(5-oxo-4, 5-dihydro-1, 2, 4-oxadiazol-3-yl)phen-yl]benzyl}-1 H-1, 3-benzodiazole-7-carboxylate ethyl acetate hemisolvate), was obtained via cyclization of methyl (Z)-2-ethoxy-1-{(2′-(N′-hydroxycarbamimidoyl)-[1, 1′-biphenyl]-4-yl)methyl}-1 H-benzo[d]imidazole-7-carboxylate with diphen-yl carbonate. There are two independent molecules (A and B) with different conformations and an ethyl acetate solvent molecule in the asymmetric unit. In molecule A, the dihedral angle between the benzene ring and its attached oxadiazole ring is 59.36 (17); the dihedral angle between the benzene rings is 43.89 (15) and that between the benzene ring and its attached imidazole ring system is 80.06 (11)°. The corresponding dihedral angles in molecule B are 58.45 (18), 50.73 (16) and 85.37 (10)°, respectively. The C - O - C - Cm (m = methyl) torsion angles for the ethoxy side chains attached to the imidazole rings in molecules A and B are 93.9 (3) and - 174.6 (3)°, respectively. In the crystal, the components are linked by N - H⋯N and C - H⋯O hydrogen bonds, generating a three-dimensional network. Aromatic π-π stacking interactions [shortest centroid-centroid separation = 3.536 (3)Å] are also observed.
KW - Antihypertension
KW - Azilsartan
KW - Azilsartan methyl ester
KW - Crystal structure
UR - http://www.scopus.com/inward/record.url?scp=84928107849&partnerID=8YFLogxK
U2 - 10.1107/S2056989014028023
DO - 10.1107/S2056989014028023
M3 - Article
AN - SCOPUS:84928107849
VL - 71
SP - o84-o85
JO - Acta Crystallographica Section E: Structure Reports Online
JF - Acta Crystallographica Section E: Structure Reports Online
SN - 1600-5368
IS - 2
ER -