In this paper we report on the crystal structure of 4-methyl-4′,5′-dihydropyrrolocoumarin (MDPC, see Figs. 1 and 2). The tricyclic chromophore is formed on ring-closure by bridging amino nitrogen (N(1)) and ring carbon (C(6)) with two methylene groups (C(7) and C(8)). The tricyclic compound is regarded as a coumarin-indoline hybrid in which a pyrrolidine moiety is condensed with a coumarin skeleton.A previous spectroscopic study 1 suggests that the methylene bridge makes the amino moiety more pyramidal than simple Nalkylation without ring formation. Pyramidalization at the nitrogen atom may be responsible for the observed blue shift and the slight decrease in the molar extinction coefficient or oscillator strength in comparison with the more planar Nalkylaminocoumarin. 1 MDPC was synthesized according to a procedure described by Quanten et al.
X-ray Structure Analysis Online
Crystal Structure of a Coumarin-Indoline Hybrid DyeNoriko KITAMURA,* Yoshiharu TORIUMI,** Shigeru KOHTANI,* , *** and Ryoichi NAKAGAKI* , *** † *Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan **Toray Research Center, Inc, 3-3-7 Sonoyama, Otsu 520-8567, Japan ***Faculty of Pharmaceutical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan The crystal structure of 4-methyl-4′,5′-dihydropyrrolocoumarin (MDPC) has been determined by X-ray diffraction. The crystal, C12H11NO2, belongs to space group P21/c with cell dimensions of a = 7.539(2)Å, b = 19.230(2)Å, c = 6.9395(9)Å, β = 103.89(1)˚. The final R value is 0.036. The methylene bridge in the indoline moiety makes the amino moiety more pyramidal than simple N-alkylation.