Home Physical Sciences The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
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The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3

  • Mengdan Wang ORCID logo EMAIL logo , Jianyue Li , Yinhai Zhou , Zhenquan Han , Guoda Wang and Jun-Ying Ma
Published/Copyright: July 8, 2024

Abstract

C25H18O3, triclinic, P1̄ (no. 2), a = 9.0717(14) Å, b = 10.2237(15) Å, c = 10.9385(18) Å, α = 101.415(4)°, β = 91.524(4)°, γ = 112.807(3)°, V = 910.7(2) Å3, Z = 2, Rgt(F) = 0.0517, wRref(F2) = 0.1427, T = 293(2) K.

CCDC no.: 2349960

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless prismatic
Size: 0.20 × 0.17 × 0.13 mm
Wavelength:

μ:
Mo Kα radiation (0.71073 Å)

0.09 mm−1
Diffractometer, scan mode:

θmax, completeness:
Bruker APEX-II, φ and ω

25.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 5283, 3379, 0.018
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2684
N(param)refined: 254
Programs: Olex2, 1 , 2 SHELX 3
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z Uiso*/Ueq
O1 0.01764 (19) 0.19589 (15) 0.43624 (13) 0.0630 (4)
O2 0.13215 (14) 0.38766 (12) 0.58854 (10) 0.0412 (3)
O3 0.2791 (2) 0.88463 (17) 0.9162 (2) 0.0998 (7)
C1 0.0441 (2) 0.24307 (19) 0.54698 (17) 0.0425 (4)
C2 −0.0106 (2) 0.15182 (19) 0.64104 (17) 0.0446 (4)
H2A −0.0107 0.0567 0.6070 0.054*
H2B −0.1206 0.1381 0.6536 0.054*
C3 0.0899 (2) 0.21388 (18) 0.76556 (17) 0.0401 (4)
C4 0.0977 (2) 0.1230 (2) 0.84276 (19) 0.0502 (5)
H4 0.0397 0.0229 0.8165 0.060*
C5 0.1895 (3) 0.1793 (2) 0.9566 (2) 0.0586 (6)
H5 0.1930 0.1177 1.0077 0.070*
C6 0.2768 (3) 0.3274 (2) 0.99551 (19) 0.0555 (5)
H6 0.3389 0.3658 1.0732 0.067*
C7 0.2723 (2) 0.4185 (2) 0.91978 (17) 0.0455 (4)
H7 0.3318 0.5183 0.9463 0.055*
C8 0.1797 (2) 0.36234 (18) 0.80402 (15) 0.0360 (4)
C9 0.1733 (2) 0.46345 (17) 0.72083 (15) 0.0375 (4)
C10 0.3378 (2) 0.58367 (19) 0.72460 (16) 0.0412 (4)
C11 0.4573 (2) 0.5498 (2) 0.66833 (18) 0.0493 (5)
H11 0.4351 0.4541 0.6281 0.059*
C12 0.6082 (2) 0.6559 (3) 0.6713 (2) 0.0589 (6)
H12 0.6870 0.6324 0.6317 0.071*
C13 0.6427 (3) 0.7979 (3) 0.7332 (2) 0.0646 (6)
H13 0.7445 0.8702 0.7346 0.077*
C14 0.5280 (3) 0.8322 (2) 0.7921 (2) 0.0629 (6)
H14 0.5530 0.9275 0.8355 0.076*
C15 0.3733 (2) 0.7262 (2) 0.78830 (18) 0.0494 (5)
C16 0.2474 (3) 0.7649 (2) 0.8490 (2) 0.0621 (6)
C17 0.0835 (3) 0.6558 (2) 0.8215 (2) 0.0563 (5)
H17 0.0011 0.6830 0.8488 0.068*
C18 0.0444 (2) 0.51912 (19) 0.75934 (16) 0.0425 (4)
C19 −0.1256 (2) 0.41213 (19) 0.72996 (18) 0.0434 (4)
C20 −0.2060 (2) 0.3782 (2) 0.6113 (2) 0.0546 (5)
H20 −0.1544 0.4258 0.5505 0.065*
C21 −0.3608 (3) 0.2752 (2) 0.5822 (2) 0.0581 (5)
H21 −0.4121 0.2538 0.5016 0.070*
C22 −0.4424 (2) 0.2026 (2) 0.6694 (2) 0.0566 (5)
C23 −0.3630 (3) 0.2388 (2) 0.7891 (2) 0.0595 (6)
H23 −0.4159 0.1930 0.8503 0.071*
C24 −0.2076 (3) 0.3412 (2) 0.81879 (19) 0.0533 (5)
H24 −0.1566 0.3632 0.8996 0.064*
C25 −0.6102 (3) 0.0867 (3) 0.6339 (3) 0.0836 (8)
H25A −0.6721 0.1193 0.5842 0.125*
H25B −0.6598 0.0678 0.7085 0.125*
H25C −0.6057 −0.0010 0.5861 0.125*

1 Source of material

In a Schlenk tube 2-(2-(4-hydroxy-2-(p-tolyl)naphthalen-1-yl)-phenyl)acetic acid (0.20 mmol, 73.7 mg), (diacetoxyiodo)-benzene (0.4 mmol, 128.8 mg), copper(II) trifluoromethanesulfonate (0.02 mmol, 7.2 mg) and DCM (2.0 mL) were stirred at room temperature for 5 h in air. Then, the residue was purified by chromatography on basic silica gel (PE : EA = 5 : 1) to afford the desired compound (white solid, 71.8 mg, 98 %). Single crystals were obtained by crystallization from a mixture of dichloromethane (10 mL) and petroleum ether (2 mL).

2 Experimental details

Using Olex2, 1 the structure was solved with the SHELXT 2 structure solution program and refined with the SHELXL 3 refinement package.

3 Comment

Cyclohexenone and indole scaffolds are widely present in many natural products and drug molecules. 4 7 In this paper we report the synthesis and crystal structure of a cyclohexenone compound. There is one ketone carbonyl and one ester carbonyl in this structure. The bond lengths of the two carbonyl groups are almost the same (1.218 Å and 1.192 Å). These values agree with literature values. 8 , 9

The complete set of X-ray diffraction data for the title compound was deposited to the Cambridge Crystallographic Data Centre (CCDC entry no. 2349960).


Corresponding author: Mengdan Wang, School of Chemistry and Chemical Engineering Henan University of Science and Technology, Luoyang, Henan 471003, P.R. China, E-mail:

Acknowledgements

This work was supported by the Doctor Start-up Funds of Henan University of Science and Technology (No. 13480078).

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Competing interests: The authors declare no conflicts of interest regarding this article.

  3. Research funding: Doctor Start-up Funds of Henan University of Science and Technology (No. 13480078).

References

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Received: 2024-04-22
Accepted: 2024-05-30
Published Online: 2024-07-08
Published in Print: 2024-10-28

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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