Home Crystal structure of 7-hydroxy-6-(2-hydroxyethyl)-2H-chromen-2-one, C11H10O4
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Crystal structure of 7-hydroxy-6-(2-hydroxyethyl)-2H-chromen-2-one, C11H10O4

  • Hua Huang ORCID logo , Jing Yang , Yi-chun Sun , Jiang-Hai Ye , Kang He EMAIL logo and Juan Zou EMAIL logo
Published/Copyright: January 20, 2023

Abstract

C11H10O4, monoclinic, Pn (no. 7), a = 4.8622(5) Å, b = 6.7853(7) Å, c = 14.3349(17) Å, β = 96.556(3)°, V = 469.84(9) Å3, Z = 2, Rgt(F) = 0.0512, wRref(F2) = 0.1249, T = 273(2) K.

CCDC no.: 2216262

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 needle
Size: 0.24 × 0.21 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 33.8°, 98%
N(hkl)measured, N(hkl)unique, Rint: 6201, 3524, 0.034
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2326
N(param)refined: 138
Programs: Olex2 [1], Bruker [2], SHELX [3], Diamond [4]
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.2775 (4) 0.7890 (3) 0.42205 (14) 0.0433 (5)
C10 0.4188 (5) 0.4502 (3) 0.41359 (16) 0.0328 (5)
O2 −0.0633 (5) 0.9135 (3) 0.32840 (15) 0.0614 (6)
C2 0.0707 (5) 0.7668 (4) 0.34965 (17) 0.0421 (6)
O3 1.0292 (4) 0.5629 (3) 0.63293 (15) 0.0466 (5)
H3A 1.031978 0.680003 0.647234 0.070*
C3 0.0386 (6) 0.5755 (4) 0.30776 (19) 0.0445 (6)
H1 −0.099541 0.555650 0.258215 0.053*
C4 0.2018 (6) 0.4249 (4) 0.33791 (19) 0.0421 (6)
H2 0.174409 0.302096 0.309536 0.050*
C7 0.8266 (5) 0.5311 (3) 0.56179 (17) 0.0345 (5)
C6 0.8060 (5) 0.3394 (3) 0.52394 (17) 0.0329 (5)
C5 0.6010 (5) 0.3031 (4) 0.45071 (16) 0.0352 (5)
H8 0.583872 0.176855 0.425401 0.042*
C8 0.6476 (5) 0.6777 (4) 0.52696 (19) 0.0395 (6)
H3 0.661442 0.803571 0.552708 0.047*
C9 0.4489 (5) 0.6360 (3) 0.45402 (18) 0.0344 (5)
C1_1 0.9953 (5) 0.1789 (4) 0.56577 (18) 0.0389 (5)
H4_1 1.183119 0.228874 0.576348 0.047*
H5_1 0.992991 0.070034 0.521811 0.047*
O4_1 1.0647 (5) −0.0623 (3) 0.69174 (16) 0.0602 (6)
H4A_1 1.186171 −0.027943 0.732945 0.090*
C2_1 0.9087 (6) 0.1056 (4) 0.65727 (19) 0.0411 (6)
H6_1 0.933348 0.210302 0.703557 0.049*
H7_1 0.713723 0.071597 0.648306 0.049*

Source of material

The whole plant of Lysimachia pariformis var. stenophylla (35.58 kg) was purchased from Yuqing County, Guizhou Province, was air-dried and crushed, and extracted twice at room temperature with 95, 90 and 70% methanol water, respectively, within one month. After evaporation of solvent in vacuo, the concentrated extract was suspended in water and extracted successively with petroleum ether, ethyl acetate and n-butanol. The ethyl acetate soluble fraction (328 g) was treated by MCI column with methanol/water (volume ratio 50–100%) to obtain six fractions A–F. The title compound was further purified and isolated from A by silica gel column chromatography. The colorless needle crystal of the title compound (12 mg) was obtained after recrystallization with ethyl acetate for three days.

Experimental details

The carbon-bound hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms with d(C–H) = 0.82–0.97 Å, Uiso(H) = 1.5 times Ueq(C) and 1.2 times Ueq(O).

Comment

Lysimachia pariformis var. stenophylla, which is a member of the family of Lysimachia genus in Primulaceae, are used as a traditional Chinese herbal medicine for the treatment of rheumatism, limb spasm, hemiplegia, convulsions in children, and fracture [5], [6], [7], [8]. L. pariformis var. stenophylla is an important composition of Hei–Gu–Teng Zhuifenghuoluo granule [Sinopharm Group Tongjitang (Guizhou) Pharmaceutical Co., Ltd., China]. This product has become a representative Chinese patent medicine for the treatment of Rheumatoid arthritis in China due to its good effect of removing wind and dampness, dredging collaterals and relieving pain [9], [10], [11]. In order to clarify its pharmacodynamic substances and improve its quality control level, the chemical constituents of L. pariformis var. stenophylla were studied and the title compound was obtained.

The title compound consisted of a benzo α-pyrone, a hydroxyl group and a propan-1-ol moiety. The bond lengths and angles which were derived from the title structure are within normal ranges. The ketone bond was determined at the distance of 1.210(3) Å (C2–O2). The hydroxyl group was confirmed by the distance of 1.352(3) Å (C7–O3), and the alcohol hydroxyl group was identified by the distance of 1.425(3) Å (C′2–O′4), respectively.


Corresponding authors: Juan Zou and Kang He, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, P. R. China, E-mail: ,

Acknowledgments

The authors gratefully acknowledge support from the Sinopharm Group Tongjitang (Guizhou) Pharmaceutical Co., Ltd. (Project Contract No. JS-YF-KY-201912015), and the Key Projects of Guizhou Basic Research Program [grant number Qiankehejichu-ZK (2022) key 046].

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

  2. Research funding: Sinopharm Group Tongjitang (Guizhou) Pharmaceutical Co., Ltd. (Project Contract No. JS-YF-KY-201912015), and the Key Projects of Guizhou Basic Research Program [grant number Qiankehejichu-ZK (2022) key 046].

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2022-11-16
Accepted: 2023-01-10
Published Online: 2023-01-20
Published in Print: 2023-04-25

© 2022 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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