CRYSTAL AND MOLECULAR STRUCTURE OF AN ANTIINFLAMMATORY AGENT, INDOMETHACIN, 1-(PARA CHLOROBENZOYL)-5-METHOXY-2-METHYLINDOLE-3-ACETIC ACID
CRYSTAL AND MOLECULAR STRUCTURE OF AN ANTIINFLAMMATORY AGENT, INDOMETHACIN, 1-(PARA CHLOROBENZOYL)-5-METHOXY-2-METHYLINDOLE-3-ACETIC ACID
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DOI：
10.1021/ja00759a047
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发表时间：
1972-01-01
影响因子：
15
通讯作者：
MARSH, RE
中科院分区：
文献类型：
--
作者：
KISTENMA.TJ;MARSH, RE
用单晶X-射线衍射法测定了消炎痛的晶体和分子结构。从无水乙腈中生长吲哚美辛，1-（对氯苯甲酰基）-5-甲氧基-2-甲基吲哚-3-乙酸的晶体。晶体属三斜晶系，空间群PI，晶胞常数：a= 9.295（2）<$，B= 10.969（1）<$，c= 9.742（1），<$，a= 69.38（1），<$= 110.79（1），y= 92.78（1），Z = 2。计算密度为1。37 g/cm 3;观察值为1.38（1）g/cm 3。结构的解决方案是通过一个常规的应用程序的符号添加方法的直接符号测定。基于3678个计数器收集的X射线强度的全矩阵最小二乘细化给出了最终的R指数为0.059。吲哚、对氯苯基和羧酸基团各自几乎是平面的。对氯苯基和吲哚基的相对取向是不寻常的，可能在消炎痛的化学中发挥重要作用。晶体结构表现出预期的氢键的羧酸基团周围的反转中心，形成分子二聚体。
The crystal and molecular structure of the antiinflammatory agent indomethacin has been determined by single-crystal X-ray diffraction methods. Crystals of indomethacin, l-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid, were grown from anhydrous acetonitrile. The crystals are triclinic, space group PI, with cell constants: a= 9.295 (2) Á, b= 10.969 (1) Á, c= 9.742 (1), Á, a= 69.38 (1), ß= 110.79 (1), y= 92.78 (1), andZ= 2. The calculated density is1. 37 g/cm3; the observed value is 1.38 (1) g/cm3. The structural solution was obtained by a routine application of the symbolic-addition method of direct sign determination. Full-matrix least-squares refinement based on 3678 counter-collected X-ray intensities gave a final R index of 0.059. The indole, p-chlorophenyl, and carboxylic acid groups are each nearly planar. The relative orientation of the p-chlorophenyl and indole groups is unusual and may play an important role in the chemistry of indomethacin. The crystal structure exhibits the expected hydrogen bonding of the carboxylic acid groups about centers of inversion to form molecular dimers.