Crystal structure of methyl (E)-3-(4-(2-ethoxy-2-oxoethoxy)phenyl) acrylate, C14H16O5

Guo Chun-Mei; Yi Lu-Yao; Pan Lei; You Yuan; Nie Xu-Liang

doi:10.1515/ncrs-2020-0634

Open Access Published by De Gruyter (O) February 1, 2021

Crystal structure of methyl (E)-3-(4-(2-ethoxy-2-oxoethoxy)phenyl) acrylate, C₁₄H₁₆O₅

Guo Chun-Mei , Yi Lu-Yao , Pan Lei , You Yuan and Nie Xu-Liang

From the journal Zeitschrift für Kristallographie - New Crystal Structures

https://doi.org/10.1515/ncrs-2020-0634

Abstract

C₁₄H₁₆O₅, triclinic, P1‾ (no. 2), a = 8.5293(8) Å, b = 11.5626(11) Å, c = 14.2196(13) Å, α = 88.888(10)°, β = 74.988(10)°, γ = 87.556(10)°, V = 1353.2(2) Å³, Z = 4, R_gt(F) = 0.0430, wR_ref(F²) = 0.1202, T = 296(2) K.

CCDC no.: 2056369

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:	Colorless block
Size:	0.20 × 0.17 × 0.15 mm
Wavelength:	Mo Kα radiation (0.71073 Å)
μ:	0.10 mm⁻¹
Diffractometer, scan mode:	Bruker APEX-II, φ and ω
θ_max, completeness:	25.5°, 99%
N(hkl)_measured, N(hkl)_unique, R_int:	10,485, 5000, 0.021
Criterion for I_obs, N(hkl)_gt:	I_obs > 2 σ(I_obs), 3803
N(param)_refined:	348
Programs:	Bruker [1], SHELX [2], [, 3], Diamond [4]

Table 2:

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

Atom	x	y	z	U_iso*/U_eq
C1	0.5279 (2)	−0.03036 (15)	0.83500 (13)	0.0583 (5)
H1	0.5195	−0.0209	0.9009	0.070*
C2	0.4461 (2)	0.04737 (15)	0.78830 (13)	0.0591 (5)
H2	0.3840	0.1086	0.8223	0.071*
C3	0.4571 (2)	0.03348 (14)	0.69001 (12)	0.0488 (4)
C4	0.5508 (2)	−0.05755 (14)	0.63956 (12)	0.0524 (4)
H4	0.5586	−0.0670	0.5737	0.063*
C5	0.6323 (2)	−0.13374 (14)	0.68744 (12)	0.0523 (4)
H5	0.6954	−0.1943	0.6530	0.063*
C6	0.6226 (2)	−0.12251 (14)	0.78623 (12)	0.0498 (4)
C7	0.7077 (2)	−0.20735 (15)	0.83439 (13)	0.0545 (4)
H7	0.7680	−0.2651	0.7946	0.065*
C8	0.7106 (2)	−0.21326 (16)	0.92638 (14)	0.0587 (5)
H8	0.6561	−0.1561	0.9690	0.070*
C9	0.7981 (2)	−0.30808 (15)	0.96279 (13)	0.0544 (4)
C10	0.8606 (3)	−0.39440 (18)	1.10074 (14)	0.0696 (5)
H10A	0.9752	−0.3823	1.0833	0.104*
H10B	0.8408	−0.4679	1.0767	0.104*
H10C	0.8202	−0.3933	1.1703	0.104*
C11	0.2865 (2)	0.19980 (14)	0.68563 (13)	0.0568 (4)
H11A	0.3556	0.2497	0.7099	0.068*
H11B	0.2027	0.1727	0.7406	0.068*
C12	0.2107 (2)	0.26569 (14)	0.61603 (12)	0.0512 (4)
C13	0.0553 (3)	0.43844 (16)	0.60416 (15)	0.0674 (5)
H13A	−0.0353	0.3993	0.5914	0.081*
H13B	0.1279	0.4600	0.5423	0.081*
C14	−0.0044 (3)	0.54338 (17)	0.66396 (16)	0.0737 (6)
H14A	0.0864	0.5834	0.6736	0.111*
H14B	−0.0726	0.5208	0.7260	0.111*
H14C	−0.0657	0.5936	0.6309	0.111*
C15	0.8044 (2)	0.18059 (16)	0.86747 (13)	0.0598 (5)
H15	0.8318	0.1430	0.8079	0.072*
C16	0.8569 (2)	0.13283 (15)	0.94355 (13)	0.0583 (5)
H16	0.9198	0.0642	0.9351	0.070*
C17	0.8157 (2)	0.18734 (14)	1.03318 (12)	0.0507 (4)
C18	0.7214 (2)	0.28931 (15)	1.04514 (13)	0.0574 (5)
H18	0.6922	0.3258	1.1052	0.069*
C19	0.6711 (2)	0.33635 (16)	0.96771 (13)	0.0587 (5)
H19	0.6086	0.4051	0.9763	0.070*
C20	0.7111 (2)	0.28407 (15)	0.87698 (12)	0.0529 (4)
C21	0.6633 (2)	0.33272 (16)	0.79310 (13)	0.0590 (5)
H21	0.6886	0.2865	0.7380	0.071*
C22	0.5891 (2)	0.43337 (16)	0.78423 (13)	0.0601 (5)
H22	0.5563	0.4818	0.8378	0.072*
C23	0.5575 (2)	0.46999 (16)	0.69200 (14)	0.0585 (5)
C24	0.4518 (3)	0.61708 (17)	0.60725 (15)	0.0704 (5)
H24A	0.5530	0.6258	0.5592	0.106*
H24B	0.3943	0.6908	0.6187	0.106*
H24C	0.3874	0.5635	0.5843	0.106*
C25	0.8304 (2)	0.18562 (15)	1.19728 (12)	0.0534 (4)
H25A	0.7132	0.1962	1.2191	0.064*
H25B	0.8775	0.2610	1.1938	0.064*
C26	0.8909 (2)	0.10903 (15)	1.26773 (12)	0.0516 (4)
C27	0.8913 (3)	0.09761 (17)	1.43497 (13)	0.0647 (5)
H27A	1.0080	0.0890	1.4249	0.078*
H27B	0.8469	0.0212	1.4408	0.078*
C28	0.8182 (3)	0.16530 (18)	1.52402 (15)	0.0772 (6)
H28A	0.8626	0.2408	1.5172	0.116*
H28B	0.8420	0.1263	1.5792	0.116*
H28C	0.7027	0.1727	1.5334	0.116*
O1	0.8814 (2)	−0.38141 (13)	0.91315 (11)	0.0909 (5)
O2	0.77875 (17)	−0.30365 (12)	1.05856 (9)	0.0685 (4)
O3	0.37976 (15)	0.10434 (10)	0.63651 (8)	0.0579 (3)
O4	0.21016 (19)	0.23713 (12)	0.53647 (10)	0.0748 (4)
O5	0.14039 (17)	0.36314 (11)	0.65826 (9)	0.0675 (4)
O6	0.5950 (3)	0.41540 (14)	0.61845 (11)	0.1085 (7)
O7	0.48292 (18)	0.57381 (11)	0.69658 (9)	0.0696 (4)
O8	0.87424 (16)	0.13399 (10)	1.10454 (8)	0.0593 (3)
O9	0.95911 (18)	0.01679 (11)	1.25174 (9)	0.0709 (4)
O10	0.85264 (17)	0.16062 (10)	1.35406 (9)	0.0624 (3)

Source of material

The mixtrue of methyl (E)-3-(4-hydroxyphenyl)acrylate (1.78 g, 0.01 mol), ethyl 2-bromoacetate (2.00 g, 0.012 mol), K₂CO₃ (2.76 g, 0.02 mol) and DMF (10 mL) was reacted at 80 °C for 2 h. After the reaction completed (monitored by TLC), the mixture was poured into 50 mL ice water and a large amount of white product was precipitated. The product was filtered and washed with water three times respectively. The yield was 86% (based on methyl (E)-3-(4-hydroxyphenyl)acrylate). Elemental Anal. Calcd. (%) for C₁₄H₁₆O₅(264.27): C, 63.63; H, 6.10. Found (%): C, 61.53; H, 6.27. The crystals were obtained after one week of slow volatilisation at room temperature.

Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.93 Å with U_iso(H) = 1.5 U_eq(C) for methyl H atoms and 1.2 U_eq(C) for all other H atoms.

Comment

The p-coumaric acid, (E)-3-(4-hydroxyphenyl) acrylic acid, is a natural phenolic acid of cinnamic acid core structure [5]. p-Coumaric acid is mainly found in fruits, vegetables, grains, and fungi, and is also abundant in Chinese herbal medicines [6], [7], [8], [9]. The pharmacological effects of p-coumaric acid has anti-oxidant, anti-inflammatory, antitumor effects, antiplatelet aggregation, and cardiovascular protection, while the anti-oxidant activities is the important basis of other pharmacological effects [10], [11], [12]. The synthesis and application of p-coumaric acid and its derivatives have attracted much attention [10], [11], [12], [13], [14], [15], [16]. We are committed to the detection and regulation of cosmetics. In order to establish a rapid and effective method for the determination of coumaric acid derivatives, a series of p-coumaric acid derivatives were synthesized.

There are two crystallographic independent molecules in the asymmetric unit (shown in the figure). In the molecules of the title structure bond lengths and angles are very similar to those given in the literature for p-coumaric acid derivatives [17], [, 18]. In the title structure, the parts of methyl p-coumaric acid of molecule A and B were approximately planar. The dihedral angles of molecule A formed by the C1–C6 plane, the carboxylate group O1–C9–O2 plane and the carboxylate group O4–C12–O5 plane were 5.0°, 10.1° and 14.6, respectively, while the dihedral angles of molecule B formed by the C15–C20 plane, the carboxylate group O6–C23–O7 plane and the carboxylate group O9–C26–O10 plane were 6.5°, 6.1° and 1.1°, respectively.

Corresponding author: Nie Xu-Liang, Department of Chemistry/Key Laboratory of Chemical Utilization of Plant Resources of Nanchang, Jiangxi Agricultural University, Nanchang330045, P. R. China, E-mail: niexuliang1981@163.com

Funding source: Jiangxi key R & D project

Award Identifier / Grant number: 20203BBGL73212

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

Award Identifier / Grant number: GJJ200386

Award Identifier / Grant number: GJJ160382

Funding source: Reform of Higher Education Foundation of Jiangxi Province

Award Identifier / Grant number: JXJG-17-3-18

Acknowledgements

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

Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: Jiangxi key R & D project (20203BBGL73212), the Key Research Foundation of Educational Department of Jiangxi Province of China (GJJ200386, GJJ160382) and the Reform of Higher Education Foundation of Jiangxi Province (No. JXJG-17-3-18).
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2020-12-17

Accepted: 2021-01-18

Published Online: 2021-02-01

Published in Print: 2021-05-26

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