Home Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
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Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS

  • Xiaoqin Huang , Chunhong Zheng EMAIL logo and Shouzhi Pu
Published/Copyright: October 20, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 1

Abstract

C19H14F6N2OS, monclinic, P21/c (no. 14), a = 16.534(2) Å, b = 9.3008(12) Å, c = 12.7681(16) Å, β = 95.095(2)°, V = 1955.7(4) Å3, Z = 4, Rgt(F) = 0.0466, wRref(F2) = 0.1471, T = 296(2) K.

CCDC no.: 1871994

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:Colorless block
Size:0.26 × 0.22 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.23 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:26°, >99%
N(hkl)measured, N(hkl)unique, Rint:10436, 3842, 0.024
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2672
N(param)refined:317
Programs:Bruker programs [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
N10.51758(17)0.3460(4)0.2589(2)0.1059(11)
N20.40689(10)0.3740(2)0.47608(15)0.0469(5)
O1−0.00864(14)0.2361(3)0.7137(2)0.1059(9)
S10.07414(4)0.32641(7)0.51696(5)0.0575(2)
F1a0.3078(5)0.8874(8)0.3844(6)0.127(3)
F2a0.3678(3)0.8793(6)0.5749(5)0.0914(15)
F3a0.1920(2)0.9700(4)0.4174(3)0.0995(14)
F4a0.2459(5)1.0575(6)0.5634(6)0.102(3)
F5a0.1002(2)0.8529(4)0.5496(6)0.0930(15)
F6a0.1952(3)0.8453(5)0.6758(4)0.0952(14)
F1′b0.3461(5)0.8829(10)0.4172(9)0.070(3)
F2′b0.3794(6)0.8795(9)0.5144(10)0.092(3)
F3′b0.2302(11)1.0631(14)0.5088(12)0.135(7)
F4′b0.2823(4)0.9628(10)0.6449(6)0.112(3)
F5′b0.1138(4)0.8736(8)0.4785(8)0.097(3)
F6′b0.1426(7)0.8555(8)0.6442(9)0.104(3)
C10.47553(16)0.3934(3)0.3148(2)0.0720(8)
C20.42253(14)0.4505(3)0.38700(19)0.0519(6)
C30.38041(14)0.5768(3)0.38358(18)0.0499(6)
H3A0.3807910.6473120.3320080.060*
C40.33615(12)0.5802(2)0.47306(17)0.0414(5)
C50.35401(13)0.4548(2)0.52990(17)0.0432(5)
C60.32766(16)0.4065(3)0.6329(2)0.0620(7)
H6A0.2911660.4761490.6581210.093*
H6B0.3005420.3154420.6242090.093*
H6C0.3743070.3967480.6828400.093*
C70.43742(17)0.2321(3)0.5043(3)0.0753(8)
H7A0.4177300.2033330.5696620.113*
H7B0.4190840.1649550.4502750.113*
H7C0.4957010.2339700.5118270.113*
C80.28117(13)0.6942(2)0.50030(17)0.0426(5)
C90.30608(17)0.8490(3)0.4920(2)0.0624(7)
C100.2358(2)0.9353(3)0.5222(3)0.0893(12)
C110.17726(17)0.8324(3)0.5635(2)0.0650(7)
C120.20701(13)0.6856(2)0.53568(17)0.0426(5)
C130.15538(12)0.5595(2)0.54905(16)0.0407(5)
C140.13631(12)0.4571(2)0.47266(17)0.0418(5)
C150.15750(15)0.4524(3)0.36133(17)0.0518(6)
H15A0.1889480.5375270.3480730.062*
H15B0.1076320.4567400.3152840.062*
C160.20495(17)0.3215(3)0.3324(2)0.0674(7)
H16A0.2158090.3275160.2599510.101*
H16B0.2553290.3173340.3759480.101*
H16C0.1738450.2363810.3430910.101*
C170.11698(13)0.5320(3)0.64223(18)0.0489(6)
H17A0.1218090.5919270.7007640.059*
C180.07225(13)0.4085(3)0.6369(2)0.0532(6)
C190.02688(17)0.3477(4)0.7188(3)0.0753(9)
H19A0.0255130.4004240.7805240.090*

  1. Occupancy: a = 0.639, b = 0.361.

Source of material

The title compound was prepared following previously reported literatures [4]. The title compound was crystallized from hexane at room temperature and the colorless crystals was obtained.

Experimental details

The hydrogen atoms were located by geometrically calculations, and their positions and thermal parameters were fixed. The occupancies of the disordered fluorine atoms at the central cyclopentene ring are refined to a 0.639(6):0.361(6) ratio for F1 and F1′, F2 and F2′, F3 and F3′, F4 and F4′, F5 and F5′, F6 and F6′, respectively. All H atoms attached to C were fixed geometrically and treated as riding with C—CH = 0.96 Å (methyl) or 0.93 Å (ethyl and thienyl) with Uiso(H) = 1.2Ueq (ethyl and thienyl) or Uiso(H) = 1.5Ueq (methyl).

Discussion

Photochromic compounds which exhibit different absorption and emission behaviors triggered by light, have received continuous attention [5]. They have potential application in the fields of optical memory devices [6], molecular sensors [7], and light-responsive gas separation switch [8]. Among photochromic compounds, diarylethenes are regarded as the canditates in practical application for their excellent thermal stablility and high sensitivity [9], [10], [11]. The photochromic properties of diarylethenes are mainly depended on the aspects of substituents [12], the nature of the heterocyclic ring [13], and the groups at the active atoms [14]. Here, we reported a diarylethene with an ethyl chain at 2-postion on the thiophene ring.

In the crystal of title compound, the distance of C8—C12, in central cyclopentene ring is 1.346(3) Å, which clearly indicates that the this distance bond is a double bond due to its length shorter than the other carbon-carbon single bonds, such as 1.504(3) Å of C8—C9. The thiophene and pyrryl moieties are linked at the C8=C12 double bond. The dihedral angle between the plane of the thiophene ring and the plane of the central cyclopentene ring is 51.5°. The angle between the plane of the pyrrolyl ring and the plane of the central cyclopentene ring is 42.6°. The title diarylethene is an antiparallel structure in the crystal state with the two methyl groups on the thiophene rings in a trans position to each other, as reflected in the torsion angles 135.3(8)° for C9—C8—C4—C5 and 129.4(4)° for C14—C13—C12—C11. This kind of conformation is crucial to its photochromic and photoinduced properties [9]. The distance between the two reactive C atoms (C5 and C14) is 3.609 Å, which is less than 4.2 Å. Thus, the compound can be expected to exhibit photochromism in the crystalline phase [8], [15]. Bond lengths and other geometric parameters are in the expected ranges [14], [16].

The title compound is packed in an unit cell with antiparallel and crisscross neighbouring molecules each other. Intermolecular weak hydrogen bonds C—CH⋯π connect molecules of the title compound with each other. These molecular interactions together with hydrogen bonding may strengthen the stability of the framework structure.

The absorption spectrum of open-ring form of the title compound centered at 253 nm in acetonitrile solution. Upon irradiation with 297 nm, the absorbance at 253 nm decreased along with a new peak appearing at 665 nm, corresponding to the closed-ring form of the title compound. And upon visible light irradiation, the absorption spectrum returned to its original state, regenerating the original ring-open conformation. And this cycle can be repeated 100 times without any change.

Acknowledgements

This work was supported by the Project of Jiangxi Advantage Sci-Tech Innovative Team (20142BCB24012). We thank the editor for providing the figure.

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Received: 2018-07-30
Accepted: 2018-10-08
Published Online: 2018-10-20
Published in Print: 2018-12-19

©2018 Xiaoqin Huang et al., published by De Gruyter, Berlin/Boston

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

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  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
https://doi.org/10.1515/ncrs-2018-0276
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of bis(6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2,4-diiodophenolato)-κ4N,N′,O,O′)cer(IV), C32H20CeI8N4O4
  3. Crystal structure of (6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato-κ2N,O))copper(II), C16H12Cl2CuN2O2
  4. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)samarium(III)], C26H18N2O9Sm
  5. Crystal structure of 1-{4-[(2-hydroxy-5-nitrobenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15N3O4
  6. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis(μ2-1-(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)trizinc(II), C44H38Zn3N4O12
  7. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)–bis(μ2–(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)tricobalt(II), C44H38Co3N4O12
  8. Crystal structure of poly[aqua(μ4-2,2′,2′′-nitrilotriacetato-κ6O1,O3,O5:O2:O4:O6)-yttrium(III)], C6H8NO7Y
  9. Crystal structure of catena-poly[bromido-(μ2-pyrazine-2-carboxylato-κ3N:N′,O)copper(II)], C10H6N4Cu2O4Br
  10. Crystal structure of poly[dodekais(μ2-2,6-difluorobenzoato-κ2O:O′)-bis((μ3-hexamethylenetetramine-κ3N:N′:N′′)hexacopper(II)], C48H30N4O12F12Cu3
  11. Crystal structure of methyl 4-(4-hydroxy-3-nitrophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H18N2O6
  12. Crystal structure of N-phenyl-2-(propan-2-ylidene)hydrazine-1-carbothioamide, C10H13N3S
  13. Crystal structure of sodium caesium zinc phosphate, NaCsZnP2O7
  14. Crystal structure of methyl 4-(4-isopropylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C23H29NO3
  15. Crystal structure of catena-poly[bis(μ2-1,3-di(4H-1,2,4-triazol-4-yl)benzene-κ2N:N′)-bis(thiocyanato-κ1N)cobalt(II), C22H16CoN14S2
  16. Crystal structure of catena-poly[(μ2-2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ2N:N′)-bis(2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ1N)-bis(thiocyanato-κ1N)cobalt(II)], C38H24CoN14S5
  17. Crystal structure of bis(2,5-di(pyridin-2-yl)-1,3,4-thiadiazole-κ2N,N′)-bis(thiocyanato-κ1N)cobalt(II), C26H16CoN10S4
  18. Crystal structure of (bis((1H-benzo[d]imidazol2-yl)methyl)amine-κ3N,N′,N′′)-(pyridine-2,6-dicarboxylato-κ3N,O,O′)zinc(II) — methanol — water (1/2/1), C25H28N6O7Zn
  19. Crystal structure of catena-poly[triaqua-(μ2-5-methoxy-isophthalato-κ2O:O′)copper(II)], C9H12CuO8
  20. Structure and photochromism of 1-[2-methyl-5-phenyl-3-thienyl]-2-[2-methyl-5-(4-chlorophenyl)-3-thienyl]3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16ClF6S2
  21. Crystal structure of methyl 4-(3-phenoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C26H27NO4
  22. Crystal structure of poly[diaqua-di-μ2-hydroxido-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ4O:O′:O′′:O′′′)-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ5O,O:O′:O′′:O′′′)disamarium(III)] – bipyridine (2/1), C21H11NF16O12Sm2
  23. Crystal structural of diethyl 4-(3,5-dibromo-4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C19H21Br2NO5
  24. Crystal structure of catena-poly[tetraaqua(μ2-4-(1H-imidazol-1-yl)pyridine-κ2N:N′))zinc(II)] thiophene-2,5-dicarboxylate, C14H17N3O8ZnS
  25. Crystal structure of (20S)-20-(dimethylamino)-3-(tigloylamino)-5α-pregn-2,16-dien-4-one, C28H42N2O2
  26. Crystal structure of rac-trans-N,N′-bis(3,5-diiodosalicylidene)-1,2-cyclohexanediamine, C20H18I4N2O2
  27. Crystal structure of 2-bromo-7-(4-(dimethylamino)phenyl)-10-methylacridin-9 (10H)-one, C22H19BrN2O
  28. Crystal structure of catena-poly[(μ2-pentane-1,5-dicarboxylato-κ2O:O′)-(μ2-2-[(1H-imidazol-1-yl)methyl]-6-methyl-1H-benzimidazole-κ2N:N′)zinc(II)] sesquihydrate, C17H21N4O5.5Zn
  29. Crystal structure of ethyl 2-amino-4-(3,4-difluorophenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C21H15F2NO5
  30. Crystal structure of 9-(5-methylthiophen-2-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione, C18H18O3S
  31. Crystal structure of [5,5′-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-2-ylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′]nickel(II), C23H30N4O4Ni
  32. Crystal structure of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl) terephthalic acid-dimethylsulfoxide (1/1), C18H15N3O6 ⋅ C2H6OS
  33. Crystal structure of (2E,4Z)-dimethyl 4-((phenylamino)methylene)pent-2-enedioate, C14H15N1O4
  34. Crystal structure of (2Z,2′Z)-1,1′-(pyridine-2,6-diyl) bis(3-hydroxy-3-phenylprop-2-en-1-one), C23H17NO4
  35. Crystal structure of ethyl 2-amino-4-(3-bromophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C21H16BrNO5
  36. Crystal structure of bis(μ2-3,5-dichloro-2-oxidobenzoato-κ4O,O′:O′,O′′)-hexakis(μ2-pivalato-κ2O:O′)-bis(pivalato-κ2O,O′)-tetrakis(1,10-phenanthroline-κ2N,N′)tetragadolinium(III), C102H108Cl4Gd4N8O22
  37. Crystal structure of catena-poly[aqua-bis(formato-κ1O)-(μ2-1,1′-(oxybis(1,4-phenylene))-bis(1H-1,2,4-triazole)-κ2N:N′)copper(II)]hydrate, C18H16CuN6O6
  38. Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN
  39. Crystal structure of N-(4-methoxybenzyl)pyridazin-3-amine- a rare Z′ = 4 structure, C12H13N3O
  40. Crystal structure of bis(perchlorato-κ1O)-bis(3,4,5-trimethoxy-N-(pyridin-2-yl)benzamide-κ2N,O)copper(II), C32H30Cl2CuN4O16
  41. Crystal structure of methyl 4-methyl-2,5-di(pyridin-4-yl)-1H-pyrrole-3-carboxylate monohydrate C17H15N3O2⋅H2O
  42. Crystal structure of dimethyl 5-(10-(methoxycarbonyl)anthracen-9-yl) isophthalate,C26H20O6
  43. Crystal structure of tert-butyl (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)carbamate, C16H24N2O4
  44. Crystal structure of aqua-bis(1,5-dimethyl-2-phenyl-4-(((E)-4-pyridylmethylene)amino)pyrazolidin-3-one-κN)-(nitrato-κO)-(nitrato-κ2O,O′)zinc(II), C34H34N10O9Zn
  45. Crystal structure of catena-poly[dichlorido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)cobalt(II)] – methanol (1/1), C18H20Cl2CoN4O2
  46. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)]bis(2-carboxybenzoate) dihydrate, MnC40H40N10O12
  47. The crystal structure of 4-((3,4-dichlorobenzylidene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, C18H15Cl2N3O
  48. Crystal structure of bis(2-methoxy-6-((2-(pyrimidin-2-yl)hydrazono)methyl)phenolato-κ3N,N′,O)iron(III) perchlorate, C24H22N8O8ClFe
  49. The crystal structure of 2-[4-hydroxy-3-methoxyphenyl]-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl, C14H19N2O4
  50. Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6
  51. Crystal structure of dichloro-tetrakis[(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol-κN]cadmium (II), C60H74CdCl6N12O4
  52. Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
  53. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
  54. The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
  55. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(tri(p-tolyl)phosphine-κP)copper(I) tetrafluoroborate – 4,4′-bipyridine (2/1), C57H54BCuF4N3P2
  56. The crystal structure of 2,6-dimethyl-3,5-dinitrocyclohexa-2,5-diene-1,4-dione, C8H6N2O6
  57. The crystal structure of 2,3-dimethyl-1,4-dinitrobenzene – a Z′ = 4 structure, C8H8N2O4
  58. Crystal structure of [(1,2-η)-1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl] (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-κ6N2,O4) rubidium (I), [Rb(diaza-18-crown-6)]Cp*, C22H41N2O4Rb
  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
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