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BY 4.0 license Open Access Published online by De Gruyter (O) May 13, 2022

Crystal structure of 3-acetyl-6-hydroxy-2H-chromen-2-one monohydrate, C11H10O5

Zhi-Qiang Xiong, Ling Yang, Shu-Zhen Xiao, Chen-Yu Yang and Xu-Liang Nie ORCID logo

Abstract

[C11H10O5], monoclinic, P21/n, a = 7.041(3) Å, b = 9.339(4) Å, c = 15.614(6) Å, β = 103.03°, V = 1000.2(7) Å3, Z = 4, Rgt(F) = 0.0337, wR ref (F2) = 0.0994, T = 296(2) K.

CCDC no.: 2169855

The crystal 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: Colorless block
Size: 0.22 × 0.18 × 0.14 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.12 mm−1
Diffractometer, scan mode: Bruker APEX-2, φ and ω-scans
θmax, completeness: 25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint: 7350, 1863, 0.028
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1602
N(param)refined: 156
Programs: Bruker programs [1], SHELX [2, 3], DIAMOND [4]

Table 2:

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

x y z Uiso*/Ueq
O1 0.74949 (13) 0.34547 (9) 1.05587 (6) 0.0437 (3)
O2 0.67556 (17) 0.14944 (10) 0.97957 (7) 0.0582 (3)
O3 0.61438 (19) 0.16768 (11) 0.80055 (7) 0.0657 (3)
O4 0.91200 (18) 0.75279 (11) 1.23927 (6) 0.0580 (3)
H4A 0.9245 0.6911 1.2775 0.087*
O5 0.9441 (2) 0.56954 (13) 0.36617 (8) 0.0645 (4)
H1W 0.906 (3) 0.587 (2) 0.4106 (15) 0.084 (7)*
H2W 1.008 (3) 0.497 (3) 0.3737 (15) 0.101 (8)*
C1 0.78081 (17) 0.49077 (13) 1.06464 (8) 0.0366 (3)
C2 0.82995 (18) 0.54412 (14) 1.14887 (8) 0.0410 (3)
H2 0.8407 0.4840 1.1972 0.049*
C3 0.86312 (19) 0.69068 (15) 1.15975 (9) 0.0430 (3)
C4 0.8470 (2) 0.77999 (15) 1.08616 (10) 0.0488 (4)
H4 0.8702 0.8777 1.0938 0.059*
C5 0.7975 (2) 0.72383 (14) 1.00346 (9) 0.0469 (3)
H5 0.7869 0.7841 0.9552 0.056*
C6 0.76208 (17) 0.57637 (13) 0.98994 (8) 0.0386 (3)
C7 0.70984 (18) 0.50902 (14) 0.90658 (8) 0.0401 (3)
H7 0.6962 0.5652 0.8564 0.048*
C8 0.67881 (17) 0.36563 (14) 0.89704 (8) 0.0380 (3)
C9 0.62521 (19) 0.29659 (14) 0.80899 (9) 0.0425 (3)
C10 0.5842 (3) 0.39028 (16) 0.72915 (9) 0.0556 (4)
H10A 0.5380 0.3326 0.6778 0.083*
H10B 0.7015 0.4387 0.7243 0.083*
H10C 0.4866 0.4596 0.7342 0.083*
C11 0.69916 (18) 0.27724 (14) 0.97565 (8) 0.0412 (3)

Source of materials

2,4–Dihydroxybenzaldehyde (0.69 g, 5 mmol) and ethyl acetoacetate (2.61 g, 20 mmol) were dissolved ethanol (100 mL). Piperidine (0.043 g, 0.5 mmol) and acetic acid (0.018 g, 0.03 mmol) were added dropwise to the solution and refluxed (monitored by TLC). After completion of the reaction, the mixture was cooled to room temperature and then 10 mL water was added. The mixture was placed at 3 °C to crystallize. After suction filtration, the filter residue was washed with 50% ice–ethanol, and dried in vacuo to give the title compound. m.p. 234–236 °C. Elemental Anal. Calcd. (%) for C11H8O4 (204.18): C, 64.71; H, 3.95. Found (%): C, 63.59; H, 4.08. IR (KBr, cm−1): 3486, 3070.8, 2983.2, 1724.9, 1663.2, 1608.1, 1455.7, 1384.3, 1215.7, 927.03.

Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.90–0.97 Å with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms.

Comment

Coumarin derivatives are well-known natural heterocyclic compounds with a core structure of a benzo-a-pyranone. Coumarin is an important structural subunit of many drugs and bioactive compounds [5], [6], [7], [8]. There are many coumarin derivatives, such as dicoumarol, Osthole, warfarin, 8–Methoxypsoralen and Psoralen, etc. [9, 10]. Coumarin and its derivatives also have excellent antiviral, antioxidation antibacterial, many other physiological activities and optical properties [11], [12], [13], [14], [15], [16]. The synthesis of coumarin and its derivatives have attracted increasing attention, due to their extensive biological applications and their wide applications [12], [13], [14], [15], [16], [17], [18]. In this paper, we report the synthesis and crystal structure of 3-acetyl-6-hydroxy-2H-chromen-2-one as an important intermediate.

In the molecule of the title compound (Fig.), bond lengths and angles within coumarin are very similar to those given in the literature for coumarin derivatives [17], [18], [19]. The coumarin ring is approximately planar. The dihedral angles between the coumarin moiety and the plane of the acety group (C10–C9–O3) is 6.9(1)°. The torsion angles of C6–C7–C8–C9, C7–C8–C9–C10, C7–C8–C9–O3, and C7–C8–C11–O2 are −179.6(1)°, −6.5(2)°, 173.4(1)° and 179.3(1)°, respectively. Intermolecular O–H…O hydrogen bonds between water molecules and oxygen atoms (carboxyl oxygen atoms (O1, O2) and hydroxyl oxygen atoms (O4)) of title compound link the molecules into a two-dimensional hydrogen bonded network.


Corresponding author: Xu-Liang Nie, Key Laboratory of Chemical Utilization of Plant Resources of Nanchang/College of Chemistry and Materials, Jiangxi Agricultural University, Nanchang 330045, P. R. China, E-mail:

Funding source: Key Research Foundation of Education Department of Jiangxi Province of China

Award Identifier / Grant number: GJJ190181, GJJ200404

Funding source: National College Students Innovation and Entrepreneurship Training Program

Award Identifier / Grant number: S202110410095

Acknowledgments

X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, People’s Republic of China.

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

  2. Research funding: This work was supported by the Key Research Foundation of Education Department of Jiangxi Province of China [GJJ190181, GJJ200404] and National College Students Innovation and Entrepreneurship Training Program (No. S202110410095).

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

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Received: 2022-03-09
Accepted: 2022-05-02
Published Online: 2022-05-13

© 2022 Zhi-Qiang Xiong et al., published by De Gruyter, Berlin/Boston

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