Analytical Sciences

Crystal Structure of Diels-Alder Cycloadduct Formed from 1-(1,2,3-1H-Benzotriazol-1-yl)-2-(4-methylphenyl)-2H-isoindole and Dimethyl Acetylenedicarboxylate

Ichiro TAKAHASHI,*  Mikio TSUZUKI,* Hidehiko KITAJIMA,* Minoru HATANAKA,* Shiro MAEDA,* Akihito YAMANO,** Tomihisa OHTA,*** and Shinzo HOSOI*** 

*Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Fukui University, 3-9-1 Bunkyo, Fukui 910-8507, Japan
**X-ray Research Laboratory, Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima, Tokyo 196-8666, Japan
***Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920 - 0934, Japan

The structure of the Diels-Alder cycloadduct formed from 2-(1,2,3-1H-benzotriazol-1-yl)-2-(p-tolyl)-2H-isoindole and dimethyl acetylenedicarboxylate was proved as 11-aza-1-(1,2,3-1H-benzotriazol-1-yl)-11-(4-methylphenyl)-tricyclo-[5.2.1.0^2,7]undeca-2,4,6,9-tetraene-9,10-dioic acid dimethyl ester. The benzotriazole moiety was located as its 1-yl form, analogous to previous reports. The benzotriazole and the benzene (of tricyclo framework) planes were twisted with an angle of 115.83°. Intramolecular close contacts between benzotriazole and ester are characteristic [N(3)···C(26), 2.754(3)Å; N(3)···H(22), 3.26(4)Å]. The shortest contact of N(3)···H(22) accounting for the rotation of the methyl group is estimated to be 3.10 Å, which might be reasonable as C-H···N-type hydrogen bonding.

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