Startseite Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
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Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2

  • Zhong-Yan Li , Lin Yuan EMAIL logo , Xian-You Yuan und Min Zhang
Veröffentlicht/Copyright: 8. August 2018

Abstract

C16H16O2, monoclinic, P21/c (no. 14), a = 13.685(10) Å, b = 6.461(5) Å, c = 15.717(12) Å, β = 112.262(8)°, V = 1286.1(17) Å3, Z = 4, Rgt(F) = 0.0417, wRref(F2) = 0.1200, T = 296(2) K.

CCDC no.: 1856734

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Block
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.08 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:9781, 2255, 0.025
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1868
N(param)refined:164
Programs:Bruker programs [1], SHELX [2, 3]
Table 2:

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

AtomxyzUiso*/Ueq
O1−0.42245(7)−0.19677(16)−0.04820(8)0.0671(3)
O20.04188(7)0.12518(17)0.14809(7)0.0652(3)
C1−0.51736(10)−0.2717(2)−0.10817(9)0.0516(4)
C2−0.60281(11)−0.1406(3)−0.12712(11)0.0640(4)
H2−0.5940−0.0121−0.09850.077*
C3−0.70096(12)−0.2000(3)−0.18823(11)0.0687(5)
H3−0.7584−0.1118−0.20070.082*
C4−0.71392(13)−0.3899(3)−0.23078(11)0.0697(5)
H4−0.7798−0.4301−0.27270.084*
C5−0.62857(12)−0.5195(3)−0.21080(10)0.0657(4)
H5−0.6381−0.6479−0.23960.079*
C6−0.52851(11)−0.4658(2)−0.14916(9)0.0531(4)
C7−0.43445(12)−0.6064(2)−0.12749(11)0.0645(4)
H7A−0.4375−0.6765−0.18300.077*
H7B−0.4356−0.7105−0.08340.077*
C8−0.33305(11)−0.4818(2)−0.08810(11)0.0600(4)
H8A−0.2735−0.5754−0.06360.072*
H8B−0.3241−0.4012−0.13670.072*
C9−0.33509(10)−0.3388(2)−0.01291(10)0.0552(4)
H9−0.3440−0.42210.03570.066*
C10−0.23688(10)−0.2092(2)0.02891(9)0.0505(3)
C11−0.15729(11)−0.2684(2)0.11056(10)0.0595(4)
H11−0.1659−0.38670.14070.071*
C12−0.06555(11)−0.1550(3)0.14793(10)0.0598(4)
H12−0.0128−0.19830.20250.072*
C13−0.05135(10)0.0223(2)0.10492(9)0.0501(3)
C14−0.12953(11)0.0837(2)0.02302(10)0.0570(4)
H14−0.12060.2018−0.00710.068*
C15−0.22127(11)−0.0323(2)−0.01388(10)0.0569(4)
H15−0.27370.0100−0.06880.068*
C160.05811(13)0.3144(3)0.10910(13)0.0756(5)
H16A0.05680.28900.04850.113*
H16B0.12530.37160.14690.113*
H16C0.00310.41040.10560.113*

Source of material

2-(4-methoxyphenyl)chromenylium perchlorate (2.19 g, 6.5 mmol) was added to dichloromethane (15 mL), and then sodium borohydride (0.25 g, 6.5 mmol) was added to the solution group by group. The color of solution changed from red to colorless. After the reaction finished, the solvent was removed to give the white product (1.41 g, 90%). Colorless crystals were obtained by recrystallization from 95% ethanol.

Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The Uiso values of the hydrogen atoms of methyl groups were set to 1.5Ueq(C) and the Uiso values of all other hydrogen atons were set to 1.2Ueq(C).

Discussion

The benzopyran core structure is a very important basic frame in organic compounds, because some derivatives are antioxidants or anti cancer drugs. The benzopyran core has a pivotal position in the total synthesis of natural products [4, 5] . Moreover, the corresponding positive ions of these derivatives have very important functions and are widely used in many fields [6].

Here, a new benzopyran derivative was synthesized and characterized by single-crystal X-ray diffraction [2, 3] . There is one molecule in the asymmetric unit. Bond lengths and angles are as expected [7]. In its structure, the bond angles of O(1)—C(9)—C(10), O(1)—C(9)—C(8) and C(10)—C(9)—C(8) are 106.68(13), 110.33(12) and 113.83(12) in turn, which indicates the sp3 hybridization state of C(9) atom.

Acknowledgements

This work was financially supported by the Natural Science Foundation of Hunan Province of China (2017JJ3093).

References

Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA (2012).Suche in Google Scholar

Sheldrick, G. M.: SHELXS-97: Program for the Solution of Crystal Structures. University of Göttingen, Germany, (1997).Suche in Google Scholar

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar PubMed

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Received: 2018-05-25
Accepted: 2018-07-19
Published Online: 2018-08-08
Published in Print: 2018-11-27

©2018 Zhong-Yan Li et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
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  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
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  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
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  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
  16. The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
  17. Crystal structure of catena-poly[bis(4,4′-dipyridylaminium-kN)-(μ2-germanowolframato-κ2O:O′)-(2,2′-bipyridine-κ2N,N′)copper(II)] with a Keggin-type heteropolyoxoanion, [Cu(C10H8N2)(C10H10N3)2][GeW12O40] ⋅ H2O
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  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
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  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
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  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
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