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

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Abstract

The structure of the Diels-Alder cycloadduct formed from 2-(1,2,3-1-H-benzotriazol-1-yl)-2-(p-tolyl)-2-H-isoindole and dimethyl acetylenedicarboxylate was proved as 11-aza-1-(1,2,3-1H-benzotriazol-1-yl)-11-(4-methylphenyl)-tricyclo- [5.2.1.02,7T]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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Authors and Affiliations

  1. Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Fukui University, 3-9-1 Bunkyo, Fukui, 910-8507, Japan

    Ichiro Takahashi, Mikio Tsuzuki, Hidehiko Kitajima, Minoru Hatanaka & Shiro Maeda

  2. X-ray Research Laboratory, Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima, Tokyo, 196-8666, Japan

    Shinzo Hosoi

  3. Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa, 920-0934, Japan

    Akihito Yamano & Tomihisa Ohta

Authors
  1. Ichiro Takahashi
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  2. Mikio Tsuzuki
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  3. Hidehiko Kitajima
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  4. Minoru Hatanaka
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  5. Shiro Maeda
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  6. Akihito Yamano
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  7. Tomihisa Ohta
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  8. Shinzo Hosoi
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Correspondence to Ichiro Takahashi.

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Takahashi, I., Tsuzuki, M., Kitajima, H. et al. Crystal Structure of Diels-Alder Cycloadduct Formed from 1-(1,2,3-IH- Benzotriazol-1-yl)-2-(4-methylphenyl)-2H-isoindole and Dimethyl Acetylenedicarboxylate. ANAL. SCI. 19, 973–974 (2003). https://doi.org/10.2116/analsci.19.973

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  • DOI: https://doi.org/10.2116/analsci.19.973

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