Home Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
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Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2

  • Junfei Lv , Hui Li EMAIL logo and Shouzhi Pu
Published/Copyright: July 28, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 233 Issue 6

Abstract

C33H20F6N2S2, monoclinic, P21/c (no. 14), a = 13.418(4) Å, b = 13.876(4) Å, c = 15.182(4) Å, β = 98.211(3)°, V = 2797.6(14) Å3, Z = 4, Rgt(F) = 0.0500, wRref(F2) = 0.1456, T = 296(2) K.

CCDC no.: 1854559

The crystal structure is shown in the figure. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. 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:Colourless block
Size:0.30 × 0.28 × 0.22 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.26 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:27.7°, >99%
N(hkl)measured, N(hkl)unique, Rint:22123, 6188, 0.034
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4311
N(param)refined:388
Programs:SHELX [21, 23, 25], Bruker [24]
Table 2:

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

AtomxyzUiso*/Ueq
C10.8257(2)1.4518(2)0.0286(2)0.0672(8)
H1B0.8035771.5110610.0046500.081*
C20.8835(3)1.4481(2)0.1125(2)0.0682(8)
H2B0.8986661.5045580.1446480.082*
C30.9177(2)1.3620(2)0.1475(2)0.0572(7)
H3A0.9567541.3602540.2033000.069*
C40.89493(18)1.27581(18)0.10078(16)0.0423(6)
C50.83498(18)1.27935(18)0.01671(16)0.0444(6)
C60.8015(2)1.3701(2)−0.0184(2)0.0577(7)
H6A0.7625481.373655−0.0741360.069*
C70.93032(17)1.18466(18)0.13317(15)0.0408(5)
H7A0.9694371.1798830.1887350.049*
C80.90744(16)1.10379(17)0.08343(15)0.0370(5)
C90.84477(19)1.11633(19)0.00025(16)0.0464(6)
H9A0.8276151.061386−0.0336250.056*
C100.94495(16)1.00813(17)0.11188(14)0.0368(5)
C111.01844(16)0.98376(16)0.17998(14)0.0366(5)
H11A1.0550871.0290590.2164010.044*
C121.03381(16)0.88258(16)0.19007(14)0.0343(5)
C130.97212(17)0.83021(17)0.12775(15)0.0369(5)
C140.9649(2)0.72408(18)0.11277(17)0.0499(6)
H14A0.9136950.7107330.0633680.075*
H14B1.0284220.7000470.1001170.075*
H14C0.9479030.6931330.1651990.075*
C151.11248(16)0.84064(15)0.25627(14)0.0349(5)
C161.21254(18)0.89093(18)0.27607(16)0.0420(5)
C171.28391(18)0.8153(2)0.32182(17)0.0491(6)
C181.2147(2)0.74233(19)0.35749(18)0.0512(6)
C191.11151(17)0.76119(16)0.30741(15)0.0368(5)
C201.02755(17)0.70042(16)0.32513(15)0.0385(5)
C210.93598(18)0.73606(17)0.34088(16)0.0420(6)
C220.9010(2)0.83792(18)0.3440(2)0.0549(7)
H22A0.8328560.8389590.3565300.082*
H22B0.9435330.8720930.3898050.082*
H22C0.9040050.8682360.2875790.082*
C231.03231(18)0.59813(17)0.33298(17)0.0438(6)
H23A1.0892320.5627210.3251190.053*
C240.94671(19)0.55691(18)0.35288(16)0.0448(6)
C250.92384(19)0.45447(17)0.36248(17)0.0454(6)
C260.9960(2)0.38782(18)0.38927(16)0.0479(6)
H26A1.0621750.4072870.4069810.058*
C270.9708(2)0.28895(18)0.39028(16)0.0468(6)
C280.8692(2)0.26373(18)0.36444(19)0.0523(7)
C290.8236(2)0.4206(2)0.3385(2)0.0608(8)
H29A0.7738010.4661990.3215110.073*
C301.0420(2)0.2160(2)0.4144(2)0.0624(8)
H30A1.1092890.2321080.4312830.075*
C311.0132(3)0.1219(2)0.4133(2)0.0733(9)
H31A1.0608710.0739830.4289090.088*
C320.9118(3)0.0972(2)0.3887(2)0.0751(10)
H32A0.8926700.0328390.3891070.090*
C330.8419(3)0.1651(2)0.3647(2)0.0702(9)
H33A0.7750960.1472000.3480120.084*
F11.20590(12)0.96585(11)0.33317(11)0.0641(5)
F21.24704(11)0.92995(12)0.20530(10)0.0615(4)
F31.35332(13)0.85147(13)0.38502(12)0.0760(5)
F41.33382(13)0.77348(13)0.26126(12)0.0740(5)
F51.21721(14)0.75595(17)0.44626(12)0.0917(7)
F61.24768(13)0.65216(12)0.34869(17)0.0922(7)
N10.80931(16)1.19873(17)−0.03249(14)0.0519(5)
N20.79606(17)0.33001(17)0.3386(2)0.0662(7)
S10.89640(4)0.90533(5)0.05810(4)0.04218(18)
S20.85755(5)0.64476(5)0.36332(5)0.0518(2)

Source of material

The title compound was prepared according to a known synthetic protocol. 2.4 M n-BuLi in hexane solution (4.17 mL, 10.0 mmol) was slowly added to anhydrous THF (50 mL) of 3-bromo-2-methyl-5-(3-quinolyl)thiophene [1] (3.04 g, 10.0 mmol) with stirring at 195 K under an argon atmosphere. After 30 min at 195 K, C5F8 (0.68 mL, 5.0 mmol) was slowly added to the reaction mixture, and the mixture was stirred for 2 h at this low temperature. The reaction was quenched by water. The product was extracted with ethyl acetate, and washed with saturated aqueous NaCl and water. The crude product was purified by column chromatography on silica gel using petroleum ether and ethyl acetate (v/v = 6/1) as the eluent to afford 1.43 g of the title compound as a blue solid in 46% yield. M.p. 447 K–448 K. The title compound crystallized from hexane at room temperature and produced colorless crystals.

Experimental details

The hydrogen atoms were located by geometrical calculations, and their positions and thermal parameters were fixed during the structure refinement. All H atoms attached to C were fixed geometrically and treated as riding with C—H = 0.96 Å (methyl) or 0.93 Å (aromatic) with Uiso(H) = 1.2 Ueq (aromatic) or Uiso(H) = 1.5 Ueq (methyl).

Comment

Molecular switches can be triggered by light which is natures most abundant and powerful energy source. Organic photochromic compounds is a widely studied class of molecular switch, which are capable of undergoing efficient and reversible transformations between two states with distinctive physical and chemical properties upon photoirradiation [2], [3], [4], [5]. Among organic photochromic compounds, diarylethenes have been extensively studied for their two isomers that are both thermodynamically stable and their cyclization/cycloreversion reaction occurs fast on the piscosecond time scale [6], [7], [8]. Owing to these excellent characteristics, diarylethene materials have potential applications in the fields of optical memory media and optical switching devices [7]. In the past decades, a significant progress on design and synthesis of diarylethene compounds by the introduction of specific functional groups has enabled diarylethenes to respond not only to UV and visible lights but also to other special external stimuli [9]. Thus, functionalized photochromic diarylethenes with multi-responsive characteristics could be extended to colorimetric and fluorometric sensing, bioimaging, construction of logic gates [10], [11], and control of biological activity [12]. Based on the development of diarylethene, Feringa et al. forecast that the photochromic diarylethene can be used in the field of photopharmacology [13]. The quinoline scaffold is well known to have diverse bioactive units through acting on organisms [14], [15]. Certain quinoline compounds with such response characteristics as pharmacophore have been developed into marketed drugs [16]. On the other hand, the nitrogen atom of quinoline is the same as that of pyridine, which can be easily protonated by external acid stimuli [17], [18], [19]. The protonation of nitrogen atom may affect the photochromism of the diarylethenes, such as their absorptions, photoisomerizations, and other physical characteristics. Thus, the photochromic diarylethene bearing a quinolone unit can be functionalized as multi-respond to UV/Vis and acid/alkali in solution, thereby providing the second dimensional control of their optical properties [1]. In this paper, we have explored a new symmetrical diarylethene with quinolone units and investigated its multi-responsive properties.

In the crystal of diarylethene title compound distances of C15—C19, C15—C16 and C19—C20 in the central cyclopentene ring are 1.349(3), 1.505(3) and 1.463(3) Å, respectively. These data clearly indicate that the C15, C19 bond is a double bond due to its length shorter than the other carbon-carbon single bonds. The two thiophene moieties are linked on the C15=C19 double bond. The angle between the planes of the thiophene ring and the adjacent quinolyl ring are 167.6° and 29.6°, respectively. The dihedral angles between the corresponding thiophene rings and central cyclopentene ring are 45.0° and 40.6°, respectively. The perfluorocyclopentene unit is antiparallel in the crystal state with the two methyl groups on the thiophene rings in a trans disposition to each other, as reflected in the torsion angles −42.8(4)° for C19—C15—C12—C13 and −42.0(4)° for C15—C19—C20—C21. This kind of conformation is crucial to its photochromic and photoinduced properties [6]. The intramolecular distance between the two reactive C atoms (C13 and C21) that comprise the cyclisation termini is 3.586 Å. This distance is less than 4.2 Å and indicates that the compound can be expected to exhibit photochromism in the crystalline phase [7, 20] .

The molecules of the title structure are packed with antiparallel and crisscross arrangement. Intermolecular C—F⋯π halogen bond, hydrogen bonds C—H⋯π, C—H⋯F, C—H⋯S and C—H⋯N connect molecules with each other. These molecular interactions together with halogen and hydrogen bonding may strengthen the stability of the framework structure.

The absorption spectrum of open-form of the title compound exhibited an intense band centered at 272 nm in acetonitrile solution. Upon irradiation with 365 nm, the absorbance at 272 nm decreased along with a new peak appearing at 602 nm, corresponding to the closed-form. 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 hundreds times without any change. And this diarylethene could also exhibit photochromic behavior in crystal state.

The multi-response photoswitching characteristic of diarylethene title compound was investigated by stimulation of acid/base and light. Gradual addition of HCl in acetonitrile solution, the diarylethene can form the N-protonated form and it can be transformed back by neutralization with NaOH solution. Coupling with the protonated process, its intensity of fluorescence enhanced by a factor of 8, the emission peak showed a notable red-shift from 400 nm to 550 nm. The increase of emission intensity may be attributed to the formation of the N-protonated open-ring isomer. Furthermore, the diarylethene title compound exhibited photoisomerization by light irradiation. Upon irradiation with UV light, the colorless solution turned blue to form the formation of N-protonated ring-closed isomer. Its absorption maximum was redshifted from 603 to 612 nm. At the same time, the fluorescence emission intensity at 550 nm decreased as irradiation time increases, and reduced to about 2% of the starting value in photostationary state.

Acknowledgements

This work was supported by the Project of the Science Funds of Jiangxi Education Office (GJJ170670). We thank the editor for providing the figure.

References

Xu, H. Y.; Wang, R. J.; Fan, C. B.; Liu, G.; Pu, S. Z.: Synthesis and photochromism of new asymmetrical diarylethenes with a variable heteroaryl ring and a quinoline unit. Turk. J. Chem. 40 (2016) 38–53.10.3906/kim-1502-11Search in Google Scholar

Irie, M.: Phororeactive Materials for Ultrahigh-density Optical Memory. Elsevier, Amsterdam (1993).Search in Google Scholar

Tian, H.; Yang, S. J.: Recent progresses on diarylethene based photochromic switches. Chem. Soc. Rev. 33 (2004) 85–97.10.1039/b302356gSearch in Google Scholar

Wang, J. C.; Liu, G.; Fan, C. B.; Pu, S. Z.: Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2. Z. Kristallogr. NCS. 232 (2017) 359–361.10.1515/ncrs-2016-0264Search in Google Scholar

Fan, C. B.; Fu, Y. L.; Pu, S. Z.: 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. Z. Kristallogr. NCS 231 (2016) 215–217.10.1515/ncrs-2015-0095Search in Google Scholar

Miyasaka, H.; Nobuto, T.; Itaya, A.; Tamai, N.; Irie, M.: Picosecond laser photolysis studies on a photochromic dithienylethene in solution and in crystalline phases. Chem. Phys. Lett. 269 (1997) 281–285.10.1016/S0009-2614(97)00282-0Search in Google Scholar

Irie, M.; Fukaminato, T.; Matsuda, K.; Kobatake, S.: Photochromism of diarylethene molecules and crystals: memories, switches, and actuators. Chem. Rev. 114 (2014) 12174–12277.10.1021/cr500249pSearch in Google Scholar PubMed

Sara, B.; Mohamed, El G.; Artur, C.; Martin, H.; Simone, C.; Marco, C.; Stefan, H.; Paolo, S.: Surface-induced selection during in situ photoswitching at the solid/liquid interface. Angew. Chem. 54 (2015) 4865–4869.10.1002/anie.201412215Search in Google Scholar PubMed

Pu, S. Z.; Sun, Q.; Fan, C. B.; Wang, R. J.; Liu, G.: Recent advances in diarylethene-based multi-responsive molecular switches. J. Mater. Chem. C4 (2016) 3075–3093.10.1039/C6TC00110FSearch in Google Scholar

Zhang, J.; Zou, Q.; Tian, H.: Photochromic materials: more than meets the eye. Adv. Mater. 25 (2013) 378–399.10.1002/adma.201201521Search in Google Scholar PubMed

Rameshbabu, K.; Zou, L.; Kim, C.; Urbas, A.; Li, Q.: Self-organized photochromic dithienylcyclopentene organogels. J. Mater. Chem. 21 (2011) 15673–15677.10.1039/c1jm13342jSearch in Google Scholar

Oleg, B.; Sergii, A.; Marina, B.; Sabine, R.; Pavel, K. M.; Vladimir, S. K.; Thomas, S.; Anne, S. U.; Igor, V. K.: Controlling biological activity with light: diarylethene-containing cyclic peptidomimetics. Angew. Chem. Int. Ed. 53 (2014) 3392–3395.10.1002/anie.201310019Search in Google Scholar PubMed

Velema, W. A.; Szymanski, W.; Feringa, B. L.: Photopharmacology: beyond proof of principle. J. Am. Chem. Soc. 136 (2014) 2178–2191.10.1021/ja413063eSearch in Google Scholar PubMed

Solomon, V. R.; Lee, H.: Quinoline as a privileged scaffold in cancer drug discovery. Curr. Med. Chem. 18 (2011) 1488–1508.10.2174/092986711795328382Search in Google Scholar PubMed

Elisei, R.; Schlumberger, M. J.; Muller, S. P.; Schoffski, P.; Brose, M. S.; Shah, M. H.; Licitra, L.; Jarzab, B.; Medvedev, V.; Kreissl, M. C.; Niederle, B.; Cohen, E. E.; Wirth, L. J.; Ali, H.; Hessel, C.; Yaron, Y.; Ball, D.; Nelkin, B.; Sherman, S. I.: Cabozantinib in progressive medullary thyroid cancer. J. Clin. Oncol. 31 (2013) 3639–3646.10.1200/JCO.2012.48.4659Search in Google Scholar PubMed PubMed Central

Li, K.; Li, Y.; Zhou, D.; Fan, Y.; Guo, H.; Ma, T.; Wen, J.; Liu, D.; Zhao, L.: Synthesis and biological evaluation of quinoline derivatives as potential anti-prostate cancer agents and Pim-1 kinase inhibitors. Bioorg. Med. Chem. 24 (2016) 1889–1897.10.1016/j.bmc.2016.03.016Search in Google Scholar PubMed

Yumoto, K.; Irie, M.; Matsuda, K.: Control of the photoreactivity of diarylethene derivatives by quaternarization of the pyridylethynyl group. Org. Lett. 10 (2008) 2051–2054.10.1021/ol8005216Search in Google Scholar PubMed

Liu, G.; Liu, M.; Pu, S. Z.; Fan, C. B.; Cui, S. Q.: Synthesis and photochromic properties of novel pyridine-containing diarylethenes. Dyes Pigments 95 (2012) 553–562.10.1016/j.dyepig.2012.05.016Search in Google Scholar

Fan, C. B.; Pu, S. Z.; Liu, G.: Effects of solvents on the growth of an asymmetrical photochromic diarylethene crystal. Dyes Pigments 113 (2015) 61–69.10.1016/j.dyepig.2014.07.023Search in Google Scholar

Ramamurthy, V.; Venkatesan, K.: Photochemical reactions of organic crystals. Chem. Rev. 87 (1987) 433–481.10.1021/cr00078a009Search in Google Scholar

Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

Sheldrick, G. M.: SHELXT-integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

Sheldrick, G. M.: SADABS. University of Göttingen, Germany (2014).Search in Google Scholar

Bruker. APEX2, SADABS, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA (2009).Search in Google Scholar

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

Received: 2018-05-28
Accepted: 2018-07-09
Published Online: 2018-07-28
Published in Print: 2018-11-27

©2018 Junfei Lv 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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  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
https://doi.org/10.1515/ncrs-2018-0116
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of di-μ2-aqua-tetraaqua-bis(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)disodium(I) C18H24N6Na2O10
  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
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  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
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  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
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)pyridin-1-ium-4-carbohydrazonate-κ3N,N′,O)-tris[nitrato-κ2O,O′)lanthanum(III), C12H15N8O12La
  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
  21. Crystal structure of (Z)-2-bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H27BrO2
  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
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
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