Z. Kristallogr.
NCS 2017; 232(1): 13–14
Iván Brito*, Mario Simirgiotis, Rubén Muñoz, Julio Benites, Leyla Pasten, Jorge Bórquez
and Alejandro Cárdenas
Crystal structure of 11-(p-coumaroyloxy)-
tremetone, C22H20O5
DOI 10.1515/ncrs-2016-0105
Received June 28, 2016; accepted September 14, 2016; available
online October 1, 2016
Abstract
C22 H20 O5 , orthorhombic, P21 21 21 (no. 19), a = 6.2039(3) Å,
b = 13.1634(8) Å, c = 22.8258(12) Å, V = 1864.06(17) Å3 , Z = 4,
Rgt (F) = 0.053, wRref (F 2 ) = 0.117, T = 297(2) K.
CCDC no.: 1504400
The title crystal structure (sytematic name: 2-(5-acetyl-
2,3-dihydrobenzofuran-2-yl)allyl (E)-3-(4-hydroxyphenyl)
acrylate) is shown in the figure. Tables 1 and 2 contain details
of the measurement method and a list of the atoms including
atomic coordinates and displacement parameters.
Source of material
The title compound C22 H20 O5 was isolated using medium
pressure column chromatography. Dried aerial parts of Paras-
trephia quadrangularis (1622 g) collected in april 2015 in El
Tatio, Atacama Desert, Northern Chile were defatted with
*Corresponding author: Iván Brito, Departamento de Química,
Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla
170, Antofagasta, Chile, e-mail: ivanbritob@yahoo.com
Mario Simirgiotis, Rubén Muñoz, Leyla Pasten and Jorge
Bórquez: Departamento de Química, Facultad de Ciencias Básicas,
Universidad de Antofagasta, Casilla 170, Antofagasta, Chile
Julio Benites: Facultad de Ciencia de la Salud, Universidad Arturo
Prat, Casilla 121, Iquique-Chile
Alejandro Cárdenas: Departamento de Física, Facultad de Ciencias
Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta,
Chile
© 2016 Iván Brito et al., published by De Gruyter.
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.
Open Access
Table 1: Data collection and handling.
Crystal: Colorless block
Size 0.16 × 0.12 × 0.05 mm
Wavelength: Cu Kα radiation (1.54178 Å)
µ: 7.5 cm−1
Diffractometer, scan mode: Bruker AXS, φ and ω
2θmax , completeness: 117.2°, >99%
N(hkl)measured , N(hkl)unique , Rint : 15024, 2635, 0.141
Criterion for Iobs , N(hkl)gt : Iobs > 2 σ(Iobs ), 1638
N(param)refined : 247
Programs: SHELX [4], Bruker programs [5],
OLEX2 [6]
hexane (3 liters, 3 times in the dark, 24 Hr each time)
and 54.82 g were obtained after evaporation of the solvent.
Then the plant material was extracted with ethyl acetate (3
liters, 3 times in the dark, 24 Hr each time. After evapora-
tion of the solvent under vacuo at 35 o C, 485 g of a dark
gummy extract was obtained. A portion of the extract (16 g)
was filtered and submitted to a medium pressure column
chromatography system composed of an 2.5 cm x 48 cm
medium pressure column (Aceglass inc, Vineland, NY, USA)
packed with silicagel (Kieselgel 60 H, Merck, Darmstadt, Ger-
many) using an isocratic solvent system of hexane-ethyl ac-
etate (8:2 v:v) pumped with a medium pressure pump (FMI
lab pump, Syosset, NY, USA) with a flow rate of 10 mL-
minute. The fractions were collected using a Gilson FC 203B
fraction collector (Gilson, Middleton, MI, USA) and the vol-
ume of each fraction was 5 mL·The collected fractions (140)
were combined according to TLC analysis (Kieselgel F254
plates, developed with CHCl3 : EtOAc 18:2 v/v, and spots
visualized by spraying with vanillin: sulfuric acid 2% in
ethanol and heating) and 17 combined fractions were ob-
tained. Fraction eight (1.5 g) was re-chromatographed us-
ing the same system and 22 mg of umbelliferone [1] were
isolated. Fraction 11 (3.5 g) was chromatographed using
the mentioned system and the title compound [2] was iso-
lated (525 mg). Suitable crystals for a crystallographic study
were obtained after re-crystallization from hexane: ethyl
acetate 9:1 v/v. The structure was already reported, how-
ever, we have revised and corrected NMR data [1] with the
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14 | Brito et al.: C22 H20 O5

Table 2: Fractional atomic coordinates and isotropic or equivalent 125 o C (Stuart Scientific SMP3 melting point apparatus,
isotropic displacement parameters (Å2 ). Bibby Scientific Ltd, Staffordshire, UK), HRESIMS− (Q exac-
tive focus, Thermo Fischer inc, Bremen, Germany), Found:
Atom x y z Uiso */Ueq
363.1308 [M—H]− calculated for C22 H19 O5 − : 363.1310.
O1 0.5954(6) 0.8931(4) 0.45813(15) 0.0791(13)
H1 0.6889 0.8717 0.4360 0.119*
O2 1.0292(8) 0.8641(4) 0.80724(17) 0.0880(15) Experimental details
O3 0.6975(6) 0.8804(3) 0.84272(14) 0.0617(10) H atoms were located in the difference Fourier map, but
O4 0.7176(6) 0.6537(3) 0.89249(15) 0.0672(12) refined with fixed individual displacement parameters, using
O5 0.3260(8) 0.6486(3) 0.63958(16) 0.0854(14)
a riding model with C—H distances of 0.93 Å (for aromatic
C4′ 0.6638(11) 0.8836(4) 0.5149(2) 0.0615(15)
C3′ 0.8588(10) 0.8447(4) 0.5300(2) 0.0678(17) rings), 0.96 Å (for CH3 ), with U(H) values of 1.2U eq (C) (for
H2 0.9523 0.8209 0.5013 0.081* CH in aromatic moiety), and 1.5U eq (C) (for methyl), O—H
C2′ 0.9176(10) 0.8405(5) 0.5888(2) 0.0701(17) distances are 0.82 Å with U(H) = 1.5U eq (O).
H3 1.0524 0.8150 0.5988 0.084*
C1′ 0.7814(10) 0.8733(4) 0.6325(2) 0.0542(14)
C6′ 0.5837(11) 0.9113(4) 0.6158(3) 0.0678(17) Discussion
H5 0.4876 0.9336 0.6443 0.081* Due to exocyclic double bond, the p-cumaric acid and treme-
C5′ 0.5261(10) 0.9169(4) 0.5577(3) 0.0710(19)
tone fragments make angle of 11.33(16)°. The crystal packing
H6 0.3925 0.9435 0.5473 0.085*
is stabilized by intermolecular O—H· · · O hydrogen bonds,
C7′ 0.8508(10) 0.8678(4) 0.6933(2) 0.0592(16)
H7 0.9940 0.8492 0.6989 0.071* between hydroxyl and carbonyl groups O(1)—H(1)· · · O(5)i
C8′ 0.7404(10) 0.8855(4) 0.7417(2) 0.0597(15) [symmetry code: (i) 1/2 + x, 3/2 − y, 1 − z] which links the
H8 0.5962 0.9042 0.7392 0.072* molecules into chains with graph-set notation C(16) [3] run-
C9′ 0.8418(13) 0.8760(4) 0.7987(2) 0.0603(16) ning along the b axis [100]. All distances and angles are in
C11 0.7824(10) 0.8662(5) 0.90185(19) 0.0656(17)
the normal range. All proton NMR spectroscopic evidence was
H10A 0.8167 0.9316 0.9191 0.079*
H10B 0.9132 0.8260 0.9004 0.079* similar to that previously published [2].
C10 0.6163(9) 0.8133(4) 0.9381(2) 0.0557(16)
C12 0.5509(9) 0.8530(5) 0.9876(2) 0.0754(19) Acknowledgements: The authors thank fondecyt (Grant
H12A 0.6079 0.9145 1.0004 0.090* 1140178) and fondequip (EQM14002) for financial support. IB
H12B 0.4476 0.8197 1.0100 0.090* Thanks to fondequip (EQM13–0021).
C2 0.5377(9) 0.7112(4) 0.9176(2) 0.0611(16)
H13 0.4817 0.6738 0.9514 0.073*
References
C3 0.3616(9) 0.7145(5) 0.8699(2) 0.0681(18)
H14A 0.2394 0.6724 0.8804 0.082*
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H14B 0.3122 0.7834 0.8631 0.082*
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C3A 0.4764(10) 0.6730(4) 0.8169(2) 0.0535(15)
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C4 0.4174(10) 0.6657(4) 0.7592(2) 0.0579(15)
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H16 0.2832 0.6890 0.7469 0.069*
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H22B 0.6984 0.5038 0.6276 0.133*
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HMBC and HMQC). Analysis: colourless crystals, m.p.124– 339–341.

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