Ezemobi Fortune, North Henry, Scott Kenneth R, Wutoh Anthohy K, Butcher Ray J
Department of Biology, College of Arts & Sciences, Howard University, 415 College Street NW, Washington, DC 20059, USA.
Department of Pharmaceutical Sciences, College of Pharmacy, Harding University, 915 E. Market Avenue, Box 12330, Searcy, Arkansas 72149, USA.
Acta Crystallogr Sect E Struct Rep Online. 2014 Nov 5;70(Pt 12):456-61. doi: 10.1107/S1600536814023769. eCollection 2014 Dec 1.
The title compounds, C9H7NO3, (1), C10H7NO5, (2), and C14H9NO5, (3), are three potentially anti-convulsant compounds. Compounds (1) and (2) are isoindoline derivatives and (3) is an iso-quinoline derivative. Compounds (2) and (3) crystallize with two independent mol-ecules (A and B) in their asymmetric units. In all three cases, the isoindoline and benzoiso-quinoline moieties are planar [r.m.s. deviations are 0.021 Å for (1), 0.04 and 0.018 Å for (2), and 0.033 and 0.041 Å for (3)]. The substituents attached to the N atom are almost perpendicular to the mean planes of the heterocycles, with dihedral angles of 89.7 (3)° for the N-O-Cmeth-yl group in (1), 71.01 (4) and 80.00 (4)° for the N-O-C(=O)O-Cmeth-yl groups in (2), and 75.62 (14) and 74.13 (4)° for the same groups in (3). In the crystal of (1), there are unusual inter-molecular C=O⋯C contacts of 2.794 (1) and 2.873 (1) Å present in mol-ecules A and B, respectively. There are also C-H⋯O hydrogen bonds and π-π inter-actions [inter-centroid distance = 3.407 (3) Å] present, forming slabs lying parallel to (001). In the crystal of (2), the A and B mol-ecules are linked by C-H⋯O hydrogen bonds, forming slabs parallel to (10-1), which are in turn linked via a number of π-π inter-actions [the most significant centroid-centroid distances are 3.4202 (7) and 3.5445 (7) Å], forming a three-dimensional structure. In the crystal of (3), the A and B mol-ecules are linked via C-H⋯O hydrogen bonds, forming a three-dimensional structure, which is consolidated by π-π inter-actions [the most significant inter-centroid distances are 3.575 (3) and 3.578 (3) Å].
标题化合物C₉H₇NO₃（1）、C₁₀H₇NO₅（2）和C₁₄H₉NO₅（3）是三种潜在的抗惊厥化合物。化合物（1）和（2）是异吲哚啉衍生物，（3）是异喹啉衍生物。化合物（2）和（3）在其不对称单元中与两个独立的分子（A和B）结晶。在所有三种情况下，异吲哚啉和苯并异喹啉部分都是平面的[（1）的均方根偏差为0.021 Å，（2）的为0.04和0.018 Å，（3）的为0.033和0.041 Å]。连接到N原子上的取代基几乎垂直于杂环的平均平面，（1）中N - O - C甲基基团的二面角为89.7（3）°，（2）中N - O - C(=O)O - C甲基基团的二面角为71.01（4）°和80.00（4）°，（3）中相同基团的二面角为75.62（14）°和74.13（4）°。在（1）的晶体中，分子A和B中分别存在不寻常的分子间C=O⋯C接触，距离为2.794（1）和2.873（1）Å。还存在C - H⋯O氢键和π - π相互作用[质心间距 = 3.407（3）Å]，形成平行于（001）的层板。在（2）的晶体中，A和B分子通过C - H⋯O氢键相连，形成平行于（10 - 1）的层板，这些层板又通过一些π - π相互作用[最显著的质心 - 质心距离为3.4202（7）和3.5445（7）Å]相连，形成三维结构。在（3）的晶体中，A和B分子通过C - H⋯O氢键相连，形成三维结构，该结构通过π - π相互作用[最显著的质心间距为3.575（3）和3.578（3）Å]得到巩固。
