Home 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
Article Open Access

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

  • Fangfang Liu , Hui Li EMAIL logo and Shouzhi Pu
Published/Copyright: September 11, 2018
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 1

Abstract

C27H16ClF6S2, monclinic, P21/c (no. 14), a = 24.1193(5) Å, b = 9.2419(2) Å, c = 10.8343(2) Å, β = 96.1260(10)°, V = 2401.26(8) Å3, Z = 4, Rgt(F) = 0.0292, wRref(F2) = 0.0878, T = 100(2) K.

CCDC no.: 1863567

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.

Source of material

The title compound was prepared according to the literature method [3] in 47% yield. The title compound crystallized from n-hexane at room temperature and produced the suitable colorless crystals for X-ray analysis.

Table 1:

Data collection and handling.

Crystal:Colorless block
Size:0.20 × 0.18 × 0.14 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.40 mm−1
Diffractometer, scan mode:CCD area detector, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:29699, 4217, 0.024
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3900
N(param)refined:331
Programs:Bruker [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
S10.37308(2)0.71339(5)0.25566(4)0.02337(12)
S20.12011(2)0.68287(5)0.13666(4)0.02242(12)
F10.32629(5)0.17687(11)0.36073(10)0.0313(3)
F20.34570(4)0.18805(12)0.16997(11)0.0333(3)
F30.23206(4)0.05698(12)0.30340(10)0.0310(3)
F40.27113(5)−0.01149(11)0.14093(11)0.0329(3)
F50.16042(4)0.16134(11)0.13688(10)0.0258(2)
F60.22032(4)0.18347(11)0.00180(9)0.0254(2)
C1Aa0.52048(8)0.7049(2)0.66298(17)0.0294(4)
H1Ab0.5507870.7257780.7237590.035*
C1Ba0.52048(8)0.7049(2)0.66298(17)0.0294(4)
Cl1Bc0.5597(3)0.7097(9)0.7815(7)0.02855(14)
C20.49086(7)0.5782(2)0.66926(16)0.0259(4)
H2A0.5011010.5114300.7344330.031*
C30.44647(7)0.54685(19)0.58206(15)0.0215(4)
H3A0.4264370.4590730.5880190.026*
C40.43069(7)0.64346(18)0.48472(15)0.0191(3)
C50.46112(8)0.7715(2)0.47953(17)0.0275(4)
H5A0.4512050.8391630.4149530.033*
C60.50591(9)0.8008(2)0.56820(18)0.0318(4)
H6A0.5265130.8878100.5630780.038*
C70.38576(7)0.60683(18)0.38729(15)0.0184(3)
C80.35210(7)0.48766(18)0.37712(15)0.0181(3)
H8A0.3527200.4152310.4394730.022*
C90.31584(7)0.48211(18)0.26385(15)0.0181(3)
C100.32261(7)0.59844(19)0.18772(15)0.0207(4)
C110.29521(8)0.6321(2)0.06037(16)0.0276(4)
H11A0.3206410.6895170.0153090.041*
H11B0.2609170.6871050.0669810.041*
H11C0.2861330.5416330.0154870.041*
C120.27970(7)0.35784(18)0.22747(14)0.0170(3)
C130.30385(7)0.20797(19)0.24387(16)0.0214(4)
C140.25558(7)0.10461(18)0.20313(16)0.0215(4)
C150.21355(7)0.20163(18)0.12480(15)0.0189(3)
C160.22780(7)0.35367(17)0.16719(14)0.0167(3)
C170.18632(6)0.46728(17)0.13401(15)0.0171(3)
C180.17557(7)0.58444(18)0.20637(15)0.0198(3)
C190.20263(8)0.6322(2)0.33027(16)0.0250(4)
H19A0.1750430.6811210.3757860.038*
H19B0.2331740.6990790.3186950.038*
H19C0.2173970.5476640.3775280.038*
C200.14904(6)0.45925(17)0.02259(15)0.0174(3)
H20A0.1508270.384775−0.0372930.021*
C210.11062(7)0.56814(18)0.00982(15)0.0191(3)
C220.06448(7)0.58663(18)−0.08859(15)0.0188(3)
C230.06762(7)0.52516(19)−0.20523(16)0.0225(4)
H23A0.1007670.476694−0.2218030.027*
C240.02325(7)0.53359(19)−0.29729(16)0.0237(4)
H24A0.0258490.491380−0.3764200.028*
C25Aa−0.02487(7)0.60417(19)−0.27259(16)0.0228(4)
Cl1Ab−0.08077(2)0.61294(6)−0.38711(4)0.02855(14)
C25Ba−0.02487(7)0.60417(19)−0.27259(16)0.0228(4)
H25Bc−0.0555080.609410−0.3352640.027*
C26−0.02922(7)0.66724(19)−0.15845(17)0.0238(4)
H26A−0.0624630.715819−0.1427850.029*
C270.01537(7)0.65887(19)−0.06725(16)0.0224(4)
H27A0.0126360.7028350.0111260.027*

  1. aOccupancy: 0.5, bOccupancy: 0.9412(11), cOccupancy: 0.0588(11).

Experimental details

The hydrogen atoms were located by geometrically calculations, and their positions and isotropic displacement parameters were fixed during the structure refinement. The Cl1, C1 and C25 atom at the end of aromatic ring are disorder. The occupancies of the disorder components refined to a 0.9412(11):0.0588(11) ratio for Cl1A:Cl1B and a 0.5:0.5 ratio was set for C1A:C1B and C25A:C25B. All H atoms attached to C were fixed geometrically and treated as riding with C¨CH = 0.96 Å(methyl) or 0.93 Å (aromatic) with Uiso(H) = 1.2 Ueq (aromatic) or Uiso(H) = 1.5 Ueq (methyl).

Comment

Photochromic compounds have attracted considerable interest in the fields of optial storage, fluorescence switch and sensors. Their molecular structures can change by appropriate light irradiation and their skeleton can be derivated by the other functional group [4], [5], [6], [7], [8]. Among various types of photochromic compounds, diarylethene derivatives are the most promising compounds for application because of their excellent fatigue resistance and thermal stability in both isomeric forms [4]. In addition, the photochromic properties of diarylethene can be predictably improved by structure variation to meet a special functional requirement. An important improvement of the photochromic properties of diarylethene is attributed to the terminal aryl moieties. There are a number of reports on the effect of different substituents at the terminal groups in the aryl moieties [9], [10], [11].

Among the substituents, the properties of chlorine substituents have aroused great interest, because the some unique natures differing from the other electron-donating and electron-withdrawing substituents, for their resonance effect and inductive effect acting on the terminal benzene ring. The chlorine substituent has an electron-donating character in resonance effect, but is working as an electron-withdrawing character in the inductive effect.

In this paper, we reported a diarylethene with a chlorine atom at one terminal phenyl ring, the structure of this diarylethene named 1-[2-methyl-5-phenyl-3-thienyl]-2-[2-methyl-5-(4-chlorophenyl)-3-thienyl]3,3,4,4,5,5-hexafluorocyclopent-1-ene (cf. the figure) was analyzed in detail.

In the perfluorocyclopentene ring, the two thiophene rings are linked by the C12 = C16 double bond 1.353(3) Å, which is shorter than the other single bond (such as C12—C13, 1.507(3) Å and C16—C17, 1.468(3) Å). The dihedral angles between the perfluorocyclopentene ring and the two thiophene rings were 138.2° for S1/C7—C10 and 140.6° for S2/C17, C18, C20, C21. The dihedral angle between the thiophene ring and its attached phenyl ring is 171.1°, and the dihedral angle between the thiophene ring and its attached chlorophenyl ring is 25.2°. The perfluorocyclopentene unit with two thiophene rings is antiparallel in the solid state with the two methyl groups on the thiophene rings in a trans position to each other, reflected in the torsion angles −38.53(5)° for C12—C16—C17—C18 and −43.11(3)° for C16—C12—C9—C10. This conformation is crucial to its photochromic properties [3]. The intramolecular distance between the two reactive C atoms (C10 and C18) that comprise the cyclisation termini is 3.582 Å. This distance is less than 4.2 Å and indicates that the compound can be expected to exhibit photochromism in the solid crystalline phase [12, 13] .

Crystals of the title compound show photochromism in accordance with the expected ring closure. Upon irradiation with 313 nm light, the colorless single-crystals of the title compound turn blue quickly. When the blue crystals were dissolved in n-hexane, the solution also showed a blue color, with an absorption maximum at 577 nm, consistent with the presence of the closed-ring isomer. Upon irradiation with visible light with a wavelength greater than 510 nm, the blue crystals return to their initial colorless state, and the absorption spectrum of a hexane solution of such colorless crystals is the same as that of a solution of the open-ring form, with an absorption maximum at 289 nm. The photochromism was highly consistent in crystalline phase even after 100 repeat cycles, indicating that it is favorable for applications in a certain optoelectronic device [14]. The photoconversion ratio from the open- to closed-ring isomer was analysed by HPLC in hexane. The photoconversion ratio from open- to closed-ring isomer in the photostationary state was 61.4%.

Acknowledgements

The authors are grateful for the financial support from the Project of the Science Funds of Jiangxi Education Office (GJJ170670). We thank the editor for providing the figure and refining crystal structure.

References

BRUKER. SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, WI, USA (2009).Search 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

Fan, C. B.; Pu, S. Z.; Liu, G.; Yang, T. S.: Substituent position effect on the properties of new unsymmetrical isomeric diarylethenes having a chlorine atom. J. Photochem. Photobiol. A 197 (2008) 415–425.10.1016/j.jphotochem.2008.02.004Search in Google Scholar

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

Tsuruoka, T.; Hayakawa, R.; Kobashi, K.; Higashiguchi, K.; Matsuda, K.; Wakayama, Y.: Laser patterning of optically reconfigurable transistor channels in a photochromic diarylethene layer. Nano Lett. 16 (2016) 7474–7480.10.1021/acs.nanolett.6b03162Search in Google Scholar PubMed

Fu, Y. L.; Fan, C. B.; Liu, G.; Pu, S. Z.: A colorimetric and fluorescent sensor for Cu2+ and F− based on a diarylethene with a 1,8-naphthalimide Schiff base unit. Sens. Actuators. B 239 (2017) 295–303.10.1016/j.snb.2016.08.020Search in Google Scholar

Kashihara, R.; Morimoto, M.; Ito, S.; Miyasaka, H.; Irie, M.: Fluorescence photoswitching of a diarylethene by irradiation with single-wavelength visible light. J. Am. Chem. Soc. 139 (2017) 16498–16501.10.1021/jacs.7b10697Search in Google Scholar PubMed

Chai, X. Z.; Fu, Y. X.; James, T. D.; Zhang, J. J.; He, X. P.; Tian, H.: Photochromism and molecular logic gate operation of a water-compatible bis-glycosyl diarylethene. Chem. Commun. 53 (2017) 9494–9497.10.1039/C7CC04427ESearch in Google Scholar PubMed

Fan, C. B.; Fu, Y. L.; Pu, S. Z.: Crystal structure of phtotochromic 1-(2-methyl-5-phenyl-3-thienyl-2-[2-methyl-5-(4-ethoxylphenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C29H22F6OS2. Z. Kristallogr. NCS 231 (2016) 215–217.10.1515/ncrs-2015-0095Search 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

Wang, R. J.; Zhang, X. X.; Pu, S. Z.; Liu, G.; Dai, Y. F.: Substituent effect in the photochromism of two isomeric asymmetric diarylethenes having pyrrole and thiophene units. Spectrochim. Acta A 173 (2017) 257–263.10.1016/j.saa.2016.09.029Search in Google Scholar PubMed

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

Kobatake, S.; Irie, M.: Singe-crystalline photochromism of diarylethenes. Bull. Chem. Soc. Jpn. 77 (2004) 195–210.10.1246/bcsj.77.195Search in Google Scholar

Cheng, H. B.; Zhang, H. Y.; Liu, Y.: Dual-stimulus luminescent lanthanide molecular switch based on an unsymmetrical diarylperfluorocyclopentene. J. Am. Chem. Soc. 135 (2013) 10190–10193.10.1021/ja4018804Search in Google Scholar PubMed

Received: 2018-05-15
Accepted: 2018-08-23
Published Online: 2018-09-11
Published in Print: 2018-12-19

©2018 Fangfang Liu et al., published by De Gruyter, Berlin/Boston

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

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
https://doi.org/10.1515/ncrs-2018-0129
Creative Commons
BY-NC-ND 4.0

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
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 21.11.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0129/html
Scroll to top button