Home Crystal structure of (3R,3aS,6R,6aR)-6-hexyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione, C13H20O4
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Crystal structure of (3R,3aS,6R,6aR)-6-hexyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione, C13H20O4

  • Yu-Xi Huang , Zan-Hong Chen , Yu-Ting Liao , Jia-Yi Li , Mei-Ying Huang , Bo Ding , Hong-Bo Huang ORCID logo EMAIL logo and Yi-Wen Tao ORCID logo EMAIL logo
Published/Copyright: May 15, 2023

Abstract

C13H20O4, monoclinic, P21 (no. 4), a = 9.7071(4) Å, b = 7.9026(4) Å, c = 17.3139(7) Å, β = 101.617(4)°, V = 1300.97(10) Å3, Z = 4, Rgt(F) = 0.0428, wRref (F 2) = 0.1145, T = 170 K.

CCDC no.: 2254006

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 block
Size: 0.14 × 0.12 × 0.11 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.74 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 74.0°, 99 %
N(hkl) measured , N(hkl) unique, R int: 8682, 4658, 0.031
Criterion for I obs, N(hkl) gt: I obs > 2σ(I obs), 4401
N(param) refined: 330
Programs: CrysAlisPRO [1], SHELX [2], Olex2 [3]
Table 2:

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

Atom x y z U iso*/U eq
O1 1.08725 (18) 0.6835 (3) 0.34645 (12) 0.0402 (5)
O2 1.23020 (19) 0.6143 (3) 0.45897 (14) 0.0482 (5)
O3 0.7475 (2) 0.6760 (3) 0.45438 (12) 0.0424 (5)
O5 0.77090 (17) 0.6169 (3) 0.33230 (11) 0.0345 (4)
C2 1.1334 (3) 0.6989 (4) 0.42452 (18) 0.0367 (6)
C3 1.0489 (3) 0.8307 (3) 0.45787 (17) 0.0344 (6)
H3 1.097399 0.938915 0.456026 0.041*
C3A 0.9141 (3) 0.8384 (3) 0.39415 (17) 0.0338 (6)
H3A 0.873584 0.952424 0.389899 0.041*
C4 0.8033 (2) 0.7056 (3) 0.39990 (16) 0.0326 (6)
C6 0.8451 (3) 0.6806 (4) 0.27301 (16) 0.0361 (6)
H6 0.781295 0.752913 0.236034 0.043*
C6A 0.9629 (3) 0.7889 (4) 0.31918 (18) 0.0376 (6)
H6A 0.983450 0.887528 0.289118 0.045*
C7 1.0405 (3) 0.8008 (4) 0.54343 (18) 0.0437 (7)
H7A 0.987753 0.890421 0.561122 0.066*
H7B 1.133762 0.798425 0.575231 0.066*
H7C 0.994856 0.694583 0.548029 0.066*
C8 0.8901 (3) 0.5330 (5) 0.22822 (18) 0.0439 (7)
H8A 0.951944 0.460366 0.264992 0.053*
H8B 0.943210 0.575643 0.190532 0.053*
C9 0.7672 (3) 0.4282 (4) 0.18453 (18) 0.0432 (7)
H9A 0.705407 0.401556 0.220419 0.052*
H9B 0.714098 0.495523 0.141862 0.052*
C10 0.8119 (3) 0.2655 (5) 0.15098 (19) 0.0486 (8)
H10A 0.872638 0.203010 0.192670 0.058*
H10B 0.865895 0.292244 0.111142 0.058*
C11 0.6885 (3) 0.1544 (5) 0.1146 (2) 0.0518 (8)
H11A 0.634095 0.129873 0.154518 0.062*
H11B 0.628370 0.217646 0.072922 0.062*
C12 0.7276 (4) −0.0112 (5) 0.0808 (2) 0.0574 (9)
H12A 0.778439 0.012370 0.039119 0.069*
H12B 0.789984 −0.073802 0.121725 0.069*
C13 0.6008 (5) −0.1197 (6) 0.0479 (4) 0.0876 (15)
H13A 0.554580 −0.151567 0.089786 0.131*
H13B 0.630697 −0.219613 0.024309 0.131*
H13C 0.536855 −0.056858 0.008823 0.131*
O4 0.1561 (2) 0.1287 (3) 0.32783 (13) 0.0481 (5)
O6 0.2361 (2) 0.3473 (3) 0.26830 (12) 0.0422 (5)
O7 0.5501 (2) 0.2728 (3) 0.30764 (14) 0.0455 (5)
O8 0.6249 (2) 0.0060 (3) 0.31465 (15) 0.0570 (6)
C14 0.3813 (3) 0.2592 (4) 0.38767 (16) 0.0338 (6)
H14 0.362513 0.308640 0.436421 0.041*
C15 0.2457 (3) 0.2329 (4) 0.32715 (16) 0.0358 (6)
C16 0.4784 (3) 0.1061 (4) 0.40498 (16) 0.0352 (6)
H16 0.545704 0.130226 0.453994 0.042*
C17 0.5590 (3) 0.1143 (4) 0.33837 (18) 0.0402 (6)
C18 0.4631 (3) 0.3814 (4) 0.34591 (17) 0.0376 (6)
H18 0.519115 0.461850 0.382405 0.045*
C19 0.3524 (3) 0.4685 (4) 0.28470 (17) 0.0399 (6)
H19 0.320368 0.570034 0.308398 0.048*
C20 0.4169 (3) −0.0673 (4) 0.41417 (19) 0.0446 (7)
H20A 0.348318 −0.094214 0.367646 0.067*
H20B 0.372917 −0.067236 0.459103 0.067*
H20C 0.490630 −0.150319 0.421587 0.067*
C21 0.3955 (4) 0.5180 (5) 0.2087 (2) 0.0540 (9)
H21A 0.413329 0.415882 0.181238 0.065*
H21B 0.483006 0.580861 0.221367 0.065*
C22 0.2878 (4) 0.6241 (6) 0.1537 (2) 0.0609 (9)
H22A 0.316736 0.633139 0.103431 0.073*
H22B 0.198424 0.564967 0.144620 0.073*
C23 0.2659 (5) 0.8010 (6) 0.1830 (3) 0.0735 (12)
H23Ca 0.355969 0.858279 0.190662 0.088*
H23Da 0.242708 0.789112 0.234634 0.088*
H23Ab 0.353616 0.856551 0.206012 0.088*
H23Bb 0.202486 0.802948 0.219697 0.088*
C24b 0.1956 (13) 0.8769 (15) 0.0985 (7) 0.061 (3)
H24Ab 0.252059 0.850390 0.059764 0.074*
H24Bb 0.101793 0.831474 0.080472 0.074*
C25b 0.1903 (14) 1.0610 (16) 0.1107 (9) 0.076 (4)
H25Ab 0.283775 1.109544 0.124839 0.092*
H25Bb 0.137347 1.089139 0.150889 0.092*
C26 0.1068 (5) 1.1238 (8) 0.0210 (3) 0.102 (2)
H26Da 0.115877 1.225394 0.052051 0.153*
H26Ea 0.012026 1.082753 0.013740 0.153*
H26Fa 0.129269 1.147557 −0.029395 0.153*
H26Ab 0.074868 1.238173 0.023818 0.153*
H26Bb 0.027667 1.051231 0.002810 0.153*
H26Cb 0.170201 1.117994 −0.014901 0.153*
C27a 0.1559 (6) 0.9217 (8) 0.1350 (4) 0.0460 (17)
H27Aa 0.067861 0.861813 0.117569 0.055*
H27Ba 0.138825 1.015419 0.168004 0.055*
C28a 0.2084 (6) 0.9887 (10) 0.0639 (4) 0.053 (2)
H28Aa 0.215640 0.896346 0.027991 0.064*
H28Ba 0.301225 1.037608 0.080847 0.064*
  1. aOccupancy: 0.590 (12), boccupancy: 0.410 (12)

1 Source of material

The title compound was isolated and purified from the secondary metabolites of Hypomontagnella monticulosa YX702. Colorless crystals were obtained by slow-evaporative solution of the methanol at room temperature.

2 Experimental details

All hydrogen atoms were placed in calculated positions and refined using a riding model with the relative isotropic parameters. U iso values of hydrogen atoms were set to 1.2 U eq of the parent atoms.

2.1 Comment

The endophytic fungus YX702 was isolated from mangrove tree Sonneratia apetala in Dongzhai harbor, Hainan Province, and identified as Hypomontagnella monticulosa by 18S DNA gene sequence [4]. The specimen was stored at Guangzhou Medical University, Guangzhou, P. R. China. YX702 was fermented statically by using modified rice medium (100 g rice, 0.4 g sea salts, 0.5 g glucose, 0.5 g yeast extract, and 200 mL distilled water) in a 1 L Erlenmeyer flask at 28 °C for 40 days. The culture was repetitively extracted with MeOH solvent, then the extract was further fractionated by silica gel chromatography using a stepwise isocratic solvent system according to the increasing polarity starting from 80 % petroleum/20 % ethyl acetate to 100 % methanol. Eight fractions (Fr. B–I) were obtained. The title compound was isolated and purified from Fraction D (50 % petroleum/50 % ethyl acetate) through silica gel column chromatography [5].

The structure of title compound was elucidated by MS and NMR data [6], [7], [8], [9], [10], and confirmed by X-ray crystallography. The X-ray crystallography data of the title compound was reported here for the first time. Bond lengths and angles are in the expected ranges.


Corresponding authors: Hong-Bo Huang and Yi-Wen Tao, Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou 511436, P.R. China, E-mail: ,
Corresponding authors: Yi-Wen Tao and Hong-Bo Huang, Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou 511436, P.R. China, E-mail: ,
Yu-Xi Huang and Zan-Hong Chen are Co-first authors.
  1. Author contributions: Yu-Xi Huang and Zan-Hong Chen are Co-first authors, and contributed equally to this work. All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The Guangdong Natural Science Foundation (2023A1515010968), Guangzhou Education Bureau Yangcheng Scholars Project (202032774), the Undergraduate Improving Programs of Scientific Research and Innovation Ability in Guangzhou Medical University (02–408–2203–2026) and the High-level University Construction Fund of Guangdong Province (02–410–2206304, 02–410–2206272, 02–410–2206307).

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

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Received: 2023-04-06
Accepted: 2023-05-01
Published Online: 2023-05-15
Published in Print: 2023-08-28

© 2023 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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  63. Synthesis and crystal structure of 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
  64. Crystal structure of 2-(thiazol-2-yl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C11H10N2O3S
  65. Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
  66. Crystal structure of poly[(μ3-3, 5-dichloro-2-hydroxy-benzoato-κ4 Cl,O:O′:O″) silver(I)], C7H3AgCl2O3
  67. The crystal structure of tetrakis(1-isopropylimidazole-κ1 N)-[μ2- imidazole-4,5-dicarboxylato-κ4 O,N,O′,N′)]- trioxido-divanadium, C29H41N10O7V2
  68. Crystal structure of catena-[(μ3-bromido)-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N)copper(I)], C9H7BrCuN3O2
  69. The crystal structure of (E)-4-fluoro-N′-(1-(2-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
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