Startseite Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
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Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2

  • Haiyan Yu ORCID logo EMAIL logo und Jihong Li
Veröffentlicht/Copyright: 14. Dezember 2021

Abstract

C21H21BrO2, monoclinic, P21/c (no. 14), a = 22.175(2) Å, b = 5.8375(6) Å, c = 14.8729(14) Å, β = 100.936(1)°, V = 1890.3(3) Å3, Z = 4, R gt (F) = 0.0343, wRref(F2) = 0.0839, T = 296(2) K.

CCDC no.: 2125836

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 × 0.18 × 0.16 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 2.19 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint: 13,804, 3862, 0.026
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2606
N(param)refined: 246
Programs: Bruker [1], SHELX [2]
Table 2:

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

Atom x y z Uiso*/Ueq
Br1 0.19913 (2) 0.11721 (5) 0.58231 (2) 0.07259 (13)
O1 0.25684 (8) 0.8688 (3) 0.29775 (13) 0.0648 (5)
O2 −0.01240 (10) 0.6470 (4) 0.09392 (14) 0.0846 (6)
C1 0.21593 (11) 0.7301 (4) 0.33181 (19) 0.0576 (7)
C2 0.24030 (12) 0.6690 (4) 0.4188 (2) 0.0583 (7)
C3 0.29994 (12) 0.7735 (4) 0.4413 (2) 0.0642 (7)
C4 0.30784 (12) 0.8922 (4) 0.3659 (2) 0.0670 (7)
C5 0.15738 (12) 0.6980 (4) 0.27012 (18) 0.0560 (6)
C6 0.11978 (12) 0.5091 (5) 0.27505 (19) 0.0647 (7)
H6 0.133117 0.395143 0.317935 0.078*
C7 0.06316 (13) 0.4864 (5) 0.21787 (19) 0.0676 (7)
H7 0.038800 0.359235 0.223124 0.081*
C8 0.04278 (13) 0.6513 (5) 0.15330 (19) 0.0655 (7)
C9 0.08002 (14) 0.8386 (5) 0.1461 (2) 0.0708 (8)
H9 0.066937 0.950232 0.102090 0.085*
C10 0.13588 (13) 0.8607 (4) 0.20323 (19) 0.0655 (7)
H10 0.160118 0.987725 0.197201 0.079*
C11 −0.05025 (14) 0.4501 (6) 0.0955 (2) 0.0943 (10)
H11A −0.027821 0.315260 0.084901 0.142*
H11B −0.086290 0.463583 0.048487 0.142*
H11C −0.062121 0.438954 0.154141 0.142*
C12 0.35502 (13) 1.0473 (5) 0.3453 (2) 0.0705 (8)
C13 0.41696 (13) 1.0052 (5) 0.3779 (3) 0.0924 (10)
H13 0.428885 0.873088 0.411497 0.111*
C14 0.46111 (16) 1.1584 (7) 0.3608 (3) 0.1053 (12)
H14 0.502426 1.129507 0.383561 0.126*
C15 0.44432 (18) 1.3508 (7) 0.3108 (3) 0.1068 (12)
H15 0.474182 1.452939 0.299420 0.128*
C16 0.38348 (18) 1.3948 (6) 0.2770 (3) 0.0995 (11)
H16 0.372265 1.526487 0.242665 0.119*
C17 0.33849 (14) 1.2433 (5) 0.2937 (2) 0.0797 (8)
H17 0.297312 1.273365 0.270412 0.096*
C18 0.21078 (11) 0.5314 (4) 0.48488 (18) 0.0589 (6)
H18A 0.221628 0.597685 0.545610 0.071*
H18B 0.166466 0.538227 0.466192 0.071*
C19 0.23132 (12) 0.2853 (4) 0.4880 (2) 0.0658 (7)
H19A 0.275841 0.278759 0.500898 0.079*
H19B 0.216926 0.214340 0.428813 0.079*
C20 0.34128 (14) 0.7729 (5) 0.5333 (3) 0.0919 (10)
H20Aa 0.317788 0.756748 0.581689 0.110*
H20Ba 0.365073 0.913174 0.543041 0.110*
H20Cb 0.314614 0.815673 0.575217 0.110*
H20Db 0.368077 0.903453 0.531420 0.110*
C21a 0.3836 (3) 0.5629 (12) 0.5304 (5) 0.075 (3)
H21Aa 0.398778 0.533492 0.477423 0.090*
C22a 0.3982 (4) 0.4288 (15) 0.5994 (6) 0.112 (3)
H22Aa 0.383296 0.456453 0.652781 0.134*
H22Ba 0.423678 0.303759 0.596059 0.134*
C21Bb 0.3832 (4) 0.5905 (12) 0.5848 (6) 0.072 (3)
H21Bb 0.394940 0.588107 0.648282 0.087*
C22Bb 0.4008 (4) 0.4407 (16) 0.5325 (7) 0.081 (3)
H22Cb 0.387837 0.450450 0.469410 0.097*
H22Eb 0.426607 0.322024 0.557629 0.097*
  1. aOccupancy: 0.539(11), bOccupancy: 0.461(11).

Source of material

The title compound was synthesized according to our previous reported method, only the (4-methoxyphenyl) (1-(p-tolylethynyl) cyclopropyl)methanone was replaced by (4-methoxyphenyl) (1-(phenylethynyl)cyclopropyl) methanone [3]. The crystal suitable for single crystal structure determination was obtained by recrystallization from tetrahydrofuran at room temperature.

Experimental details

All H atoms were included in calculated positions and refined as riding atoms with C–H = 0.93–0.97 Å, with Uiso = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for the remaining H atoms. Some atoms are disordered over two positions. The two parts overlapped each other with site occupation factors of 0.539 and 0.461. The disorder is omitted in the figure for clarity.

Comment

Furan derivatives have attracted more and more attention due to their wide variety of biological and pharmacological activities [3], [4], [5], [6], [7], [8], [9], [10], [11], [12]. Recently we have reported the structure of the structurally related 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-(p-tolyl)furan [3]. In continuation of our research on furan derivatives, the molecular and crystal structure of the title compound were determined.

In the crystal structure, the asymmetric unit of the title compound consists of one formula unit (cf. Figure). The bond lengths are comparable with those found in our previous work [3] and that of others [12, 13]. The dihedral angle formed by the two aromatic rings is 22.319(1) Å. The furan ring and the two aromatic rings form dihedral angles of 26.389(1)° and 37.263(1)°, respectively. In the crystal, weak intermolecular C–H…Br hydrogen bonds link the molecules into one dimensional chains along the b axis.


Corresponding author: Haiyan Yu, Henan Key Laboratory of Industrial Microbial Resources and Fermentation Technology, Nanyang Institute of Technology, 473004, Nanyang, Henan, P. R. China; and School of Biological and Chemical Engineering, Nanyang Institute of Technology, 473004, Nanyang, Henan, People’s Republic of China, E-mail:

  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 financial supported by Nanyang Institute of Technology.

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

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Received: 2021-10-24
Accepted: 2021-12-02
Published Online: 2021-12-14
Published in Print: 2022-02-23

© 2021 Haiyan Yu and Jihong Li, published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-3-yl)methylene)-3, 4-dihydronaphthalen-1(2H)-one, C17H15NO3
  4. Crystal structure of (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1 (2H)-one, C18H17NO3
  5. The crystal structure of N 6,N 6′-di(pyridin-2-yl)-[2,2′-bipyridine]-6,6′-diamine, C20H16N6
  6. The crystal structure of {N 1,N 2-bis[2,4-dimethyl-6-(4-(tert-butyl)phenyl)(phenyl)methyl]acenaphthylene-1,2-diimino-κ2 N, N′}-dibromido-nickel(II) – dichloromethane(1/2), C64H64Br2Cl4N2Ni
  7. Synthesis and crystal structure of nonacarbonyltris[(2-thia-1,3,5-triaza-7-phosphatricylco[3.3.1.1]decane-κ1 P)-2,2-dioxide]triruthenium(0) – acetonitrile (7/6), C25.71H32.57N9.86O15P3S3Ru3
  8. A new polymorph of 1-(4-nitrophenyl)-1H-benzimidazole (C13H9N3O2)
  9. The crystal structure of 2,2′-((1E,1′E)-(naphthalene-2,3 diylbis(azanylylidene)) bis(methanylylidene))bis(4-methylphenol), C26H22N2O2
  10. The crystal structure of bis(μ2-iodido)-bis(η6-benzene)-bis(iodido)-diosmium(II), C12H12I4Os2
  11. Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12
  12. Crystal structure of (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
  13. Crystal structure of 2,2′-(p-tolylazanediyl)bis(1-phenylethan-1-one), C23H21NO2
  14. Redetermination of the crystal structure of the crystal sponge the poly[tetrakis(μ3-2,4,6-tris(pyridin-4-yl)-1,3,5-triazine)-dodecaiodidohexazinc(II) nitrobenzene solvate], C72H48I12N24Zn6⋅10(C6H5NO2)
  15. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C44H45N5O2
  16. Crystal structure of (E)-7-fluoro-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O1
  17. Crystal structure of tetrabutylammonium sulfanilate – 1-(diaminomethylene)thiourea (1/2)
  18. Crystal structure of [2,2′-{azanediyl)bis[(propane-3,1-diyl)(azanylylidene)methylylidene]} bis(3,5-dichlorophenolato)-κ2O,O′]-isothiocyanato-κN-iron(III), C21H19Cl4FeN4O2S
  19. Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2
  20. Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2
  21. Chlorido-(2,2′-(ethane-bis(5-methoxyphenolato))-κ4 N,N,O,O′)manganese(III) monohydrate, C19H18Cl2CuN2O2
  22. Crystal structure of 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one, C22H28O2
  23. Crystal structure of [6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato)-κ4N,N′,O,O′]copper(II)
  24. Crystal structure of 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione, C30H20O4N2Cl2S2
  25. Crystal structure of bis{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl)borato-κN 3}manganese(II), C30H26B2F18MnN12
  26. Crystal structure of 1-(2-methylphenyl)-2-(2-methylbenzo[b]thienyl)-3,3,4,4,5,5-hexafluorocyclopent-ene, C21H14F6S
  27. Crystal structure of 2-(3-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  28. Crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium chloride – chloroform (1/1), C21H23Cl4I2N3
  29. Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3
  30. The crystal structure of 2-(4-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  31. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C9H14F12N4P2
  32. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(pyren-1-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C54H48N4O2
  33. Crystal structure of poly[bis(μ2-2,6-bis(1-imidazoly)pyridine-κ2 N,N′)-bis(thiocyanato-κ1 N)copper(II)] dithiocyanate, C24H18CuN12S2
  34. Cones with a three-fold symmetry constructed from three hydrogen bonded theophyllinium cations that coat [FeCl4] anions in the crystal structure of tris(theophyllinium) bis(tetrachloridoferrate(III)) chloride trihydrate, C21H33Cl9Fe2N12O9
  35. Crystal structure of 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin monohydrate, C32H49N3O6S
  36. The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
  37. The crystal structure of 4-phenyl-4-[2-(pyridine-4-carbonyl)hydrazinylidene]butanoic acid, C16H15N3O3
  38. The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3
  39. Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)
  40. Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene) hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
  41. Crystal structure of (E)-amino(2-((5-methylfuran-2-yl)methylene)hydrazinyl) methaniminium nitrate monohydrate, C14H26N10O10
  42. The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
  43. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)zinc(II)], C64H44Br4N8O8Zn2
  44. The crystal structure of catena-poly[(1-(4-carboxybenzyl)pyridin-1-ium-4-carboxylato-κ1O)-(μ2-oxalato-κ4 O:O′:O″:O‴)dioxidouranium(VI)], C16H11NO10U
  45. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
  46. Halogen bonds in the crystal structure of 4,3′:5′,4″-terpyridine — 1,3-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  47. Crystal structure of 2-(1H-indol-3-yl)ethan-1-aminium 2-(4-acetylphenoxy)acetate, C20H22N2O4
  48. Chalcogen bonds in the crystal structure of 4,7-dibromo-2,1,3-benzoselenadiazole, C6H2Br2N2Se
  49. The crystal structure of 1,4-bis((1H-benzimidazol-2-yl)methyl)-piperazine-2,5-dione dihydrate, C20H22N6O4
  50. The crystal structure of C19H20O8
  51. The crystal structure of KNa3Te8O18·5H2O exhibiting a 2[Te4O9]2− layer
  52. Erratum
  53. Erratum to: Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
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