Citation: CHEN Chao-Yue, HU Jin-Song, CHAI Fei-Fei, XIE Kai-Yun, ZHANG Xiao-Mei, SHI Jian-Jun. Synthesis, Crystal Structure and Properties of Ethyl 3,9-Dimethyl-7-phenyl-6H-dibenzo[b,d]pyran-6-one-8-carboxylate[J]. Chinese Journal of Structural Chemistry, ;2014, 33(3): 395-400. shu

Synthesis, Crystal Structure and Properties of Ethyl 3,9-Dimethyl-7-phenyl-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

1.
School of Chemical Engineering, Anhui University of Science and Technology, Huainan, Anhui 232001, China

Corresponding author: CHEN Chao-Yue,
Received Date: 6 November 2013
Available Online: 10 January 2014
Fund Project: the Doctoral Foundation of Anhui University of Science and Technology (No. 11117) (No. 20130911160)

Ethyl 3,9-dimethyl-7-phenyl-6H-dibenzo[b,d]pyran-6-one-8-carboxylate (C₂₄H₂₀O₄, M_r=372.40) has been synthesized and its structure was determined by ¹H and ¹³C NMR, ESI-MS, elemental analysis, and X-ray single-crystal diffraction. The crystal belongs to the monoclinic system, space group P2₁/n, with a=8.3674(11), b=10.6683(14), c=11.3817(15) Å, α=95.596(2), β=109.866(2), γ=94.495(2)°, V=944.2(2) Å³, Z=2, D_c=1.310 g/cm³, μ=0.089 mm^-1, F(000)=392, R=0.0482 and wR=0.1281 for 2916 observed reflections with I>2σ(I). In the crystal structure, the fused tricyclic nucleus of the title compound is not fully coplanar. Analysis of the crystal packing indicates aromatic π-π stacking interactions occurring between the fused tricyclic aromatic rings of neighboring molecules in which a maximum overlap of the π-electron systems was achieved. Fluorescence and thermal studies indicate that compound 3 has good optical properties and thermal stability.
- 6H-dibenzo[b,d]pyran-6-one,
- synthesis,
- crystal structure,
- π-π stacking interactions
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