TY - JOUR AU - Zhu, Xiao-Yu AU - Liang, Zu-Pei AU - Li, Jian AU - Gao, Jun AU - Zhang, Zhi-Shan PY - 2013/11/11 Y2 - 2024/03/29 TI - Synthesis and Structural Characterization of N-(2-Carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide JF - Asian Journal of Chemistry JA - ajc VL - 25 IS - 17 SE - Articles DO - 10.14233/ajchem.2013.15030 UR - https://asianpubs.org/index.php/ajchem/article/view/25_18_12 SP - 9478-9480 AB - <p style="text-align: justify;">The compound N-(2-carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide (C<sub>15</sub>H<sub>11</sub>NO<sub>5</sub>, M<sub>r</sub> = 285.25) was synthesized and characterized by elemental analysis, <sup>1</sup>H NMR spectra, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n, with a = 8.4994(8), b = 14.6499(15), c = 10.2880(10) Å, <span style="font-family: Symbol;">b</span>&nbsp;= 101.5890(10)º, V = 1254.9(2) Å<sup>3</sup>, Z = 4, D<sub>c</sub> = 1.510 g/cm<sup>3</sup>,&nbsp;<span style="font-family: Symbol;">l</span> = 0.71073 Å, (MoK<sub><span style="font-family: Symbol;">a</span></sub>) = 0.115 mm<sup>-1</sup>, F<sub>(000)</sub> = 592. The final refinement gave R = 0.0374, wR(F<sup>2</sup>) = 0.0856 for 2,201 observed reflections with I &gt; 2<span style="font-family: Symbol;">s</span>(I). The structure of the compound comprises a racemic mixture of chiral molecules containing four stereogenic centres. X-Ray diffraction analysis reveals that the cyclohexane ring tends towards a boat conformation, the tetrahydrofuran ring and the dihydrofuran ring adopt envelope conformations. The dihedral angle between the pyrrolidine-2,5-dione plane and the aromatic ring is 65.0 (1)º. The crystal structure is stabilized by O-H···O and C-H···O hydrogen bonds.</p> ER -