Home Crystal structure of photochromic 1-(2-methyl-5-phenyl-3-thienyl-2-[2-methyl-5-(4-ethoxylphenyl)-3-thienyl] 3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H22F6OS2
Article Open Access

Crystal structure of photochromic 1-(2-methyl-5-phenyl-3-thienyl-2-[2-methyl-5-(4-ethoxylphenyl)-3-thienyl] 3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H22F6OS2

  • Congbin Fan EMAIL logo , Yinglong Fu and Shouzhi Pu
Published/Copyright: January 12, 2016

Abstract

C29H22F6OS2, monoclinic, P21/c, a = 6.4504(2) Å, b = 16.9752(4) Å, c = 22.8762(6) Å, β = 91.7790(10)°, V = 2503.66(12) Å3, Z = 4, Rgt(F) = 0.0377, wRref(F2) = 0.1156, T = 100(2) K.

CCDC no.:: 1060703
Figure: Molecular view of the title compound. Ellipsoids are drawn at 30% probability level.
Figure:

Molecular view of the title compound. Ellipsoids are drawn at 30% probability level.

The crystal structure is shown in the figure, Tables 13 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Colorless, block, size 0.26×0.28×0.42 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.80 cm−1
Diffractometer, scan mode:CCD area detector, φ and ω scans
2θmax:55°
N(hkl)measured, N(hkl)unique:21976, 5746
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4806
N(param)refined:346
Programs:SHELX [16]
Table 2

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

AtomSitexyzUiso
H(1A)4e1.65340.61560.82910.053
H(1B)4e1.80220.68370.81070.053
H(1C)4e1.80970.60190.77890.053
H(2A)4e1.47770.71000.76880.029
H(2B)4e1.62620.68800.71800.029
H(4)4e1.31220.73110.67990.024
H(5)4e1.02310.74560.61940.024
H(7)4e0.86370.52130.64860.027
H(8)4e1.15060.50650.71020.027
H(10)4e0.74880.76020.55930.024
H(13A)4e0.10310.64370.49420.031
H(13B)4e0.14290.56190.52440.031
H(13C)4e0.22910.57840.46230.031
H(21A)4e0.75370.69640.42560.038
H(21B)4e0.81070.62500.38580.038
H(21C)4e0.68740.61090.44280.038
H(22)4e0.07080.73170.33620.022
H(25)4e−0.14830.68420.26330.026
H(26)4e−0.34420.64860.18090.031
H(27)4e−0.20820.56300.11310.035
H(28)4e0.12290.51420.12750.035
H(29)4e0.32030.54970.20940.029
Table 3

Atomic displacement parameters (Å2).

AtomSitexyzU11U22U33U12U13U23
C(1)4e1.7209(3)0.6397(1)0.7968(1)0.030(1)0.029(1)0.045(1)−0.0018(9)−0.0200(9)0.0005(9)
C(2)4e1.5597(3)0.6680(1)0.75242(8)0.0218(9)0.0212(9)0.0278(9)0.0013(7)−0.0082(7)−0.0043(7)
C(3)4e1.2625(3)0.6171(1)0.70114(7)0.0143(8)0.0209(8)0.0147(8)0.0032(6)−0.0004(6)−0.0012(6)
C(4)4e1.2223(3)0.6889(1)0.67380(8)0.0210(9)0.0155(8)0.0243(9)−0.0007(7)−0.0029(7)−0.0023(7)
C(5)4e1.0483(3)0.6973(1)0.63743(8)0.0234(9)0.0149(8)0.0205(8)0.0021(7)−0.0027(7)0.0012(6)
C(6)4e0.9098(3)0.6356(1)0.62697(7)0.0171(8)0.0186(8)0.0145(8)0.0018(7)0.0005(6)0.0007(6)
C(7)4e0.9529(3)0.5637(1)0.65490(8)0.0197(9)0.0207(9)0.0277(9)−0.0042(7)−0.0050(7)0.0070(7)
C(8)4e1.1258(3)0.5546(1)0.69172(8)0.0201(9)0.0208(9)0.0271(9)−0.0006(7)−0.0032(7)0.0088(7)
C(9)4e0.7273(3)0.6473(1)0.58768(7)0.0185(8)0.0170(8)0.0156(8)−0.0006(7)−0.0007(6)−0.0006(6)
C(10)4e0.6724(3)0.7138(1)0.55731(7)0.0238(9)0.0178(8)0.0176(8)−0.0019(7)−0.0049(7)0.0005(6)
C(11)4e0.4860(3)0.7053(1)0.52219(7)0.0221(9)0.0174(8)0.0147(8)0.0022(7)−0.0044(6)−0.0018(6)
C(12)4e0.3972(3)0.6323(1)0.52718(7)0.0175(8)0.0182(8)0.0143(8)0.0036(6)−0.0010(6)−0.0016(6)
C(13)4e0.2004(3)0.6013(1)0.49955(8)0.0189(9)0.0219(9)0.0205(9)0.0005(7)−0.0019(7)−0.0011(7)
C(14)4e0.3992(3)0.7692(1)0.48575(8)0.0241(9)0.0158(8)0.0201(8)−0.0002(7)−0.0054(7)−0.0010(7)
C(15)4e0.3562(4)0.8480(1)0.51352(8)0.045(1)0.0185(9)0.0205(9)0.0039(8)−0.0116(8)−0.0023(7)
C(16)4e0.3013(3)0.9027(1)0.46203(8)0.036(1)0.0169(9)0.025(1)0.0044(8)−0.0066(8)−0.0003(7)
C(17)4e0.2230(3)0.8453(1)0.41457(8)0.028(1)0.0216(9)0.0194(9)0.0050(8)−0.0061(7)0.0008(7)
C(18)4e0.3323(3)0.7685(1)0.42914(8)0.0201(8)0.0166(8)0.0197(8)−0.0002(7)−0.0047(7)0.0012(7)
C(19)4e0.3463(3)0.7082(1)0.38379(7)0.0201(8)0.0158(8)0.0161(8)−0.0020(7)−0.0032(6)0.0018(6)
C(20)4e0.5082(3)0.6564(1)0.37674(7)0.0178(8)0.0209(9)0.0152(8)−0.0030(7)−0.0001(6)0.0015(6)
C(21)4e0.7078(3)0.6463(1)0.41078(8)0.0175(9)0.037(1)0.0221(9)0.0026(8)−0.0015(7)−0.0012(8)
C(22)4e0.1895(3)0.7006(1)0.33824(7)0.0183(8)0.0185(8)0.0185(8)0.0007(7)−0.0032(7)0.0012(6)
C(23)4e0.2302(3)0.6435(1)0.29816(7)0.0172(8)0.0165(8)0.0165(8)−0.0022(6)−0.0004(6)0.0040(6)
C(24)4e0.1068(3)0.6209(1)0.24539(7)0.0238(9)0.0148(8)0.0150(8)−0.0057(7)−0.0017(6)0.0024(6)
C(25)4e−0.0929(3)0.6500(1)0.23613(8)0.0230(9)0.0217(9)0.0196(8)−0.0029(7)−0.0021(7)−0.0006(7)
C(26)4e−0.2108(3)0.6286(1)0.18672(8)0.026(1)0.025(1)0.025(1)−0.0030(8)−0.0078(8)0.0027(7)
C(27)4e−0.1294(3)0.5776(1)0.14615(8)0.042(1)0.023(1)0.0201(9)−0.0070(9)−0.0115(8)0.0007(7)
C(28)4e0.0683(3)0.5484(1)0.15478(8)0.042(1)0.024(1)0.0200(9)−0.0004(9)−0.0036(8)−0.0055(7)
C(29)4e0.1868(3)0.5697(1)0.20398(8)0.028(1)0.0209(9)0.0227(9)0.0001(8)−0.0020(7)−0.0017(7)
F(1)4e0.5140(3)0.87658(8)0.54642(7)0.087(1)0.0205(6)0.0556(9)0.0058(7)−0.0519(8)−0.0095(6)
F(2)4e0.1909(3)0.84331(8)0.54884(6)0.085(1)0.0314(7)0.0271(7)0.0181(7)0.0163(7)0.0015(5)
F(3)4e0.4734(2)0.93884(7)0.44376(6)0.0466(8)0.0244(6)0.0406(7)−0.0071(6)−0.0054(6)−0.0008(5)
F(4)4e0.1643(2)0.95866(7)0.47495(5)0.0546(8)0.0234(6)0.0281(6)0.0155(6)−0.0060(5)−0.0036(5)
F(5)4e0.0124(2)0.83709(7)0.41781(5)0.0269(6)0.0312(6)0.0341(6)0.0089(5)−0.0091(5)−0.0060(5)
F(6)4e0.2567(2)0.87300(7)0.36040(5)0.0511(8)0.0240(6)0.0208(6)0.0062(5)−0.0045(5)0.0055(4)
O(1)4e1.4302(2)0.60236(7)0.73724(5)0.0176(6)0.0200(6)0.0232(6)0.0009(5)−0.0061(5)−0.0002(5)
S(1)4e0.54413(7)0.57411(2)0.57437(2)0.0179(2)0.0155(2)0.0176(2)0.0007(2)−0.0014(2)0.0012(2)
S(2)4e0.46363(7)0.59855(3)0.31584(2)0.0181(2)0.0236(2)0.0174(2)0.0014(2)0.0007(2)−0.0017(2)

Source of material

The title compound was prepared according to the literature method [1, 2] in 35.45% yield. Elemental analysis for C29H22F6OS2: calcd: C 61.69, H 3.93%; found: C 61.71, H 3.95%. The title compound crystallized from hexane at room temperature.

Upon irradiation with 297 nm light, the colorless single-crystals of the title structure turn blue quickly. When the blue crystals were dissolved in hexane, the colorless solution also showed a blue color, with an absorption maximum at 575 nm, accompanied with the formation of the closed-ring isomer. Upon irradiation with visible light (≥510 nm), blue crystals return to their colorless state. The absorption spectrum of a hexane solution of such colorless crystals is the same as that of the open-ring form, with an absorption maximum at 292 nm.

Experimental details

The hydrogen atoms were located by geometrically calculations, and their positions and thermal parameters were fixed during the structure refinement.

Discussion

Photochromism is defined as the phenomenon that a compound can be switched between two distinct states with its corresponding isomers by external light-triggered reversible reaction with chemical bond rearrangement which induces electronic as well as geometrical structure changes of the molecules (see the Scheme). Photochormic compounds have been attracted interest due to their promising wide applications in photonic devices, such as optical memory media, full-color display and various photoswitching devices [3]. Among various photochromic compounds, diarylethenes are promising candidates for such applications due to their excellent thermal stability of both isomers, fatigue-resistant property, high sensitivity, rapid response, and reactivity in solid state [4]. On one hand, the photochromic properties of diarylethene is strongly influenced by the substituents at the terminal groups at the aryl moieties [4]. Recently we have reported the photochromic diarylethene bearing different group, such as fluorine, chlorine, methoxy and methyl [5–7]. On the other hand, the application of the light responsive compounds need the solid state – especial crystal-based state – for their easily using [8]. In general, photochromic reactions rarely occur in crystals, [9, 10] because the photochromic reactions require large geometrical structural changes to form the closed-ring isomer. In our previous crystallographic studies of photochromic diarylethene, we have found that the diarylethenes can exhibite the photochromism in crystal states when they are bearing some special heterocyclic groups [11–13]. On the basis of these considerations, we have designed an assymmetrical photochromic diarylethene bearing an ethoxy group.

Scheme: Left: ground state as found in the crystal structure, right: excited state as found in the structure.
Scheme:

Left: ground state as found in the crystal structure, right: excited state as found in the structure.

The title molecule adopts a photo-active antiparallel conformation (see the Figure). In the cyclopentene ring, the two thiophene rings are linked by the C14=C18 double bond 1.352(2) Å. The two methyl groups are located on different sides of the C14=C18 double bond and this configuration is crucial to allow the compound to exhibit photochromic and photoinduced properties [4]. This geometry allows the breaking of the central hexafluorocyclopentene C=C double bond to form a new C—C single bond and the molecule thus can undergo a phototransition. The dihedral angles between the least-square planes of the cyclopentene (C14, C15, C17, C18) and the adjacent phenyl thienyl ring, ethoxylphenyl thienyl ring are 32.3(5)° and 126.9(6), respectively. The dihedral angle between the least-square planes of phenyl, ethoxylphenyl and their adjacent thienyl rings are 32.3(5)° and 1.9(7)°, respectively. The angle between the thienyl rings is 118.6(4)°.

The intramolecular distance between the two reactive C atoms (C20—C12) is 3.560(2) Å. This distance indicates that the crystal can be expected to undergo photochromism to form the closed ring isomer because photochromic reactivity usually appears when the distance between the reactive C atoms is less than 4.2 Å [14, 15].


Corresponding author: Congbin Fan, Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People's Republic of China, e-mail:

Acknowledgements:

This work was supported by the National Natural Science Foundation of China (21363009, 21362013), and the Project of Natural Science Foundation of Jiangxi Province (20132BAB203005, 20142BAB203005) and the Program for the Top Young Innovative Talents in University (2013QNBJRC002).

References

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Received: 2015-5-10
Accepted: 2015-12-16
Published Online: 2016-1-12
Published in Print: 2016-3-1

©2016 Congbin Fan et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  34. Crystal structure of 3′,4′,5-trihydroxy-3,7-dimethoxyflavone, C17H14O7
  35. Crystal structure of n-butyl-chlorido-bis[N-sec-butyl,N-n-propyl-carbamodithioato κ2S,S′]-tin(IV), C20H41ClN2S4Sn
  36. Crystal structure of poly[bis(μ4-4,4′-(1,2-phenylenebis(oxy))dibenzoato-κ4O:O′:O′′:O′′′)bis(μ3-4,4′-(1,2-phenylenebis(oxy))dibenzoato–κ3O:O′:O′′)(μ2-1-(4-((1H-imidazol-1-yl)methyl)benzyl)-1H-imidazole-κ2N:N′)tetracobalt(II)], C94H62O24N4Co4
  37. Crystal structure of catenapoly[diaqua-(μ24,4′-bipyridine)-κ2N:N′)-bis(2,6-difluorobenzoate)-κO)nickel(II)] ethanol monosolvate, C28H30F4N2O8Ni
  38. Crystal structure of 2-(9H-fluoren-9-ylidene)hydrazine-1-carbothioamide, C14H11N3S
  39. Crystal structure of 2-(4-methoxyphenyl)-2,3-dihydro-1H-perimidine, C18H16N2O
  40. Crystal structure of catena-poly[diaquabis(μ2-3-carboxybenzene-1,2-dicarboxylato-1:2κ2O:O′)-(μ2-1,4-bis(2-ethylbenzimidazol-1-ylmethyl)-benzene-1:1′κ2N:N′)dizinc(II)], [Zn2(C26H26N4)(C9H4O6)2(H2O)2]
  41. Crystal structure of diaquabis(phenoxyacetato-κ2O,O′)-zinc(II), C16H18O8Zn
  42. Crystal structure of 4-(1H-imidazol-1-yl)-6-pyrimidinylferrocene, C17H14FeN4
  43. Crystal structure of [2-(4-methoxyphenyl)pyrazine-κ2C,N) chlorido[N,N′-bis-(2,6-diisopropyl-phenyl)imidazol-2-ylidene-κC)] palladium(II), C38H45ClN4OPd
  44. Crystal structure of 2-(4-acetyl-2,6-dimethyl-phenyl)-5,6-dichloro-isoindole-1,3-dione, C18H13Cl2NO3
  45. Crystal structure of 4,4′-bipyridin-1-ium 3,3′,5′-tricarboxy-[1,1′-biphenyl]-2-carboxylate, (C26H18N2O8)
  46. Crystal structure of catena-poly[diaqua-μ2-4,4′-biphenyl-4,4′-diyldipyridine-κ2N:N′-bis(5-carboxy-2,6-dimethylpyridine-3-carboxylato-κO)nickel(II)] dihydrate, C40H40N4O12Ni
  47. Crystal structure of poly-[μ2-4,4′-bipyridine-κ2N:N′−μ3-thiophene-2,3-di-carboxylato-κ4O,O′, O′′:O′′′ -cadmium(II)]
  48. Crystal structure of hexaaquamanganese(II) bis(3-carboxythiophene-2-carboxylate) C12H18MnO14S2
  49. Crystal structure of 4-(3-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)benzoic acid, C14H10N4O2
  50. Crystal structure of (E)-2-(benzo[d]thiazol-2-yl)-3-(pyridin-3-yl)acrylonitrile)
  51. Crystal structure of catena-poly[2,2′-bipyridinyl-6,6′-dicarboxylato-κ4N,N′,O,O′)-(μ2-2,2′-bipyridinyl-6′-carboxyl-6-carboxylato-κ5N,N′,O,O′:O′′)samarium(III)] monohydrate, C24H13N4O8Sm · H2O
  52. Crystal structure of catena-poly[bis(μ2-4-(3-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)benzoato)-κ2N:O)copper(II)] dihydrate, C28H22N8O6Cu
  53. Crystal structure of catena-poly[tetraaqua-(μ2-4,4′-bipyridine-k2N:N′)-zinc(II)] fumarate tetrahydrate, C14H26N2O12Zn
  54. Crystal structure of triaqua-(1,10-phenanthroline)-(dihydrogen-3,3′,3′′-(2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tripropanoato) cobalt(II)dihydrogen-3,3′,3′′-(2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tripropanoate, C72H82Co2N16O42
  55. Crystal structure of poly[dibromido-(μ2–4,4′-bis-(pyrid-4-yl)biphenyl-κ2N:N′)lead(II)], C22H16N2PbBr2
  56. Crystal structure of catena-poly[diaqua-bis(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:N)-cobalt(II)]dihydrate, C26H24N2O12Co
  57. Crystal structure of 5-(4-pyridyl)pyrimidine–4,4′-bipyridine–1,3,5-benzenetriol–water (1:1:1:1), C25H23N5O4
  58. Crystal structure of 5-hydroxy-4-((4-hydroxyphenyl)imino)naphthalen-1(4H)-one monohydrate, C16H11NO3 · 0.5H2O
  59. Crystal structure of 2-amino-N-(4-methoxyphenyl)benzamide, C14H14N2O2
  60. Crystal structure of (2,5-dihydroxyphenyl)-(4-hydroxy-3,5-dimethoxyphenyl)methanone, C15H14O6
  61. Crystal structure of dichlorido[bis(2-hydroxyethyl)5′-([2,2′:6′,2′′-terpyridin]-4′-yl)-[1,1′:3′,1′′-terphenyl]-4,4′′-dicarboxylato]zinc(II), C39H31Cl2N3O6Zn
  62. Crystal structure of bis[4-(3-carboxy-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium] benzene-1,4-dicarboxylate (C20H18F2N3O3)2(C8H4O4), C48H40F4N6O10
  63. Crystal structure of (2,5-dihydroxyphenyl)-(4-methoxyphenyl)methanone, C14H12O4
  64. Crystal structure of photochromic 1-(2-methyl-5-phenyl-3-thienyl-2-[2-methyl-5-(4-ethoxylphenyl)-3-thienyl] 3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H22F6OS2
  65. Crystal structure of poly[diaquabis(μ2-biphenyl-2,4′-dicarboxylato-κ2O:O′)tris(μ2-1,1′-biphenyl-4,4′-diylbis(1H-imidazole)-κ2N:N′)dicobalt(II)] monohydrat, C82H64N12O11Co2
  66. Crystal structure of 2-amino-4-(3,4-difluorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H12N2O2F2
  67. Crystal structure of poly[(di-μ2-aqua-κ2O:O)bis(μ5-oxalato-1:2κ2O1; 1κ1O2; 3:4:5κ3O3; 3κ1O4)(μ4-oxalato-1:2κ2O1; 2:3κ2O2; 3:4κ2O3; 4:1κ2O4)dizinc(II)disodium(I)]
  68. Crystal structure of tetraethylammonium hexachloridotantalate(V), C8H20Cl6NTa
  69. Crystal structure of (E)-2,4-dibromo-6-(((2-nitrophenyl)imino)methyl)phenol, C13H8Br2N2O3
  70. The crystal structure of 6-chloro-2,4-diphenylquinoline
  71. Crystal structure of (E)-2-(((1,10-phenanthrolin-5-yl)imino)methyl)-5-methylphenol monohydrate, C20H15N3O·H2O
  72. Crystal structure of tris(3-(2-pyridyl)pyrazole)zinc(II)tetrachlorido zincate(II), C24H21Cl4N9Zn2
  73. Crystal structure of 4-chloro-N,N-diethyl-6-(piperidin-1-yl)-1,3,5-triazin-2-amine, C12H20ClN5
  74. The crystal structure of 4-allyl-5-benzyl-2,4-dihydro-3H-1,2,4-triazol-3-one, C12H13N3O
  75. Crystal structure of diethyl 2-(((2-(pyridin-3-ylthio)phenyl)amino)methylene)malonate, C19H20N2O4S
  76. Crystal structure of fac-tricarbonyl(2-(isopropylimino)methyl-5-methylphenolatido-κ2N,O)(pyridine-κN)rhenium(I), C19H19N2O4Re
  77. Crystal structure of 1,3,6,8-tetrakis(p-tolylthio)pyrene, C44H34S4
  78. Crystal structure of catena-poly-(diaqua-(μ2-1,2-bis(4-pyridyl)ethene-κ2N:N′)-(4-methylphthalato-κ2O,O′)-cobalt(II)trihydrate, C21H26CoN2O9
  79. Crystal structure of tetraethylammonium fac-tricarbonyl(hexafluoroacetylacetonato-κ2O,O′)-(nitrato-κO)rhenium(I), C16H21O8N2F6Re
  80. Crystal structure of 3-(thiophen-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carboxamide
  81. Crystal structure of bis(1-ethyl-3-methylimidazolium) tetrabromidocadmate(II), [C6H11N2]2[CdBr4]
  82. Crystal structure of N′-(adamantan-2-ylidene)-isonicotinohydrazide, C16H19N3O
  83. Crystal structure of trans-tetraaquabis(4-(pyridin-4-ylsulfonyl)pyridine-κN)cobalt(II) diperchlorate dihydrate, C20H28Cl2CoN4O18S2
  84. Crystal structure of (Z)-4-(furan-2-yl(p-tolylamino)methylene)-3-methyl-1-p-tolyl-1H-pyrazol-5(4H)-one, C23H21N3O2
  85. Crystal structure of 2-[(4-fluorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile, C16H16FN3OS
  86. Crystal structure of poly[octaaqua-tris(benzene-1,2,4,5-tetracarboxylato)tetralanthanum(III)] hexahydrate, C30H34La4O38
  87. Crystal structure of trans-tetraaqua-bis(4,4′-sulfonyldipyridine-κN)zinc(II) diperchlorate dihydrate, C20H28Cl2ZnN4O18S2
  88. Crystal structure of 4-nitro-thiophene-2-carboxylic acid, a structure with a Z′ = 4, C5H3NO4S
  89. Crystal structure of dirubidium trimercury(II) tetraselenide, Rb2Hg3Se4
  90. Crystal structure of 5-(adamantan-1-yl)-3-[(4-chloroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C19H22ClN3OS
  91. Crystal structure of hexaaquamagnesium(II) 5,5′-bitetrazole-1,1′-diolate, C2H12N8O8Mg
  92. The crystal structure of catena-poly[(μ2-1,1′-benzene-1,4-diylbis(1H-benzimidazole-κ2N:N′)silver(I)] nitrate, C20H14N5AgO3
  93. The crystal structure of 1-(2-(4-chlorophenoxy)-4-chlorophenyl)ethanone, C14H10Cl2O2
  94. The crystal structure of 3,5-dinitro-1,3,5-oxadiazinane, C3H6N4O5
  95. Crystal structure of methyl 5-methoxy 1H-indole-2-carboxylate, C11H11NO3
  96. Crystal structure of (Z)-1-(((3-acetyl-2-hydroxyphenyl)amino)methylene)naphthalen-2(1H)-one, C19H15NO3
  97. Crystal structure of (Z)-5-(4-chlorobenzylidene)-2-thioxothiazolidin-4-one —dimethylsulfoxide (1:1), C12H12ClNO2S3
  98. Crystal structure of 5,5′-((4-(trifluoromethyl)phenyl)methylene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) – diethylamine – dichloromethane (1/1/1) C25H32Cl2F3N5O6
  99. Crystal structure of 2-(dimethylsulfanylidene)-N-(4-methoxyphenyl)-3-oxo-3-phenylpropanamide
  100. Crystal structure of (1,10-phenanthroline-κ2N,N′)bis(thiocyanato-κN)platinum(II), C14H8N4PtS2
  101. Crystal structure of di(μ2-chlorido)bis[2-(2-pyridyl)phenyl-κ2N,C1]dipalladium(II), C22H16Cl2N2Pd2
  102. Crystal structure of trans-dibromidodi(pyridine-κN)palladium(II), PdBr2(C5H5N)2
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