Home 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
Article Open Access

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

  • Thomas Henneberger , Wilhelm Klein and Thomas F. Fässler EMAIL logo
Published/Copyright: September 27, 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

C22H41N2O4Rb, monoclinic, P21/n (no. 14), a = 10.8160(9) Å, b = 17.7253(16) Å, c = 13.2179(12) Å, β = 93.961(8)°, V = 2528.0(4) Å3, Z = 4, Rgt(F) = 0.0376, wRref(F2) = 0.0694, T = 120(2) K.

CCDC no.: 1866601

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:Yellow block
Size:0.20 × 0.15 × 0.15 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.99 mm−1
Diffractometer, scan mode:Oxford Xcalibur 3, ω and π
θmax, completeness:26.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:26792, 4963, 0.100
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2435
N(param)refined:272
Programs:CrysAlis [1], SHELX [2, 3] , Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
Rb0.44660(3)0.33795(2)0.34703(3)0.03586(11)
O10.7034(2)0.30542(13)0.30666(16)0.0386(6)
C10.7869(3)0.3673(2)0.3013(3)0.0477(11)
H1A0.86070.35150.26640.057*
H1B0.81470.38410.37060.057*
C20.7224(3)0.4307(2)0.2443(3)0.0465(11)
H2A0.78280.47070.23040.056*
H2B0.68470.41210.17860.056*
O20.6287(2)0.46052(12)0.30345(16)0.0404(6)
C30.5591(4)0.5184(2)0.2503(3)0.0531(12)
H3A0.51140.49680.19060.064*
H3B0.61590.55730.22620.064*
C40.4717(4)0.5537(2)0.3211(3)0.0531(11)
H4A0.51960.57270.38230.064*
H4B0.42880.59710.28700.064*
N10.3790(3)0.49846(17)0.3511(2)0.0430(9)
H10.329(3)0.4852(19)0.295(2)0.052*
C50.3108(4)0.5236(2)0.4372(3)0.0581(12)
H5A0.26610.57090.41850.070*
H5B0.37060.53470.49540.070*
C60.2197(4)0.4658(2)0.4685(3)0.0576(12)
H6A0.17240.48630.52390.069*
H6B0.16030.45380.41050.069*
O30.2834(2)0.39923(13)0.50214(17)0.0406(6)
C70.2026(3)0.3442(2)0.5399(2)0.0475(10)
H7A0.14130.32800.48520.057*
H7B0.15720.36610.59540.057*
C80.2770(3)0.2783(2)0.5783(3)0.0445(10)
H8A0.34140.29530.63020.053*
H8B0.22250.24190.61060.053*
O40.3341(2)0.24242(13)0.49762(16)0.0392(6)
C90.3971(3)0.1748(2)0.5307(3)0.0437(10)
H9A0.33590.13470.54230.052*
H9B0.44630.18430.59540.052*
C100.4814(3)0.14978(19)0.4509(2)0.0411(9)
H10A0.51490.09910.46810.049*
H10B0.43360.14650.38430.049*
N20.5828(3)0.20283(17)0.4444(2)0.0366(8)
H20.625(3)0.2010(18)0.500(2)0.044*
C110.6684(3)0.18081(19)0.3684(2)0.0402(10)
H11A0.62150.17180.30260.048*
H11B0.71090.13330.38960.048*
C120.7631(3)0.2419(2)0.3565(3)0.0412(10)
H12A0.80040.25720.42390.049*
H12B0.83010.22290.31590.049*
C130.3113(3)0.29258(19)0.1439(3)0.0360(9)
C140.3567(3)0.3535(2)0.0906(2)0.0366(9)
C150.2813(3)0.4169(2)0.1046(3)0.0364(9)
C160.1884(3)0.39450(19)0.1681(3)0.0353(9)
C170.2064(3)0.31836(19)0.1926(2)0.0350(9)
C180.3655(3)0.21497(19)0.1515(3)0.0477(10)
H18A0.31950.18500.19630.072*
H18B0.36120.19210.08550.072*
H18C0.45040.21800.17750.072*
C190.4695(3)0.3515(2)0.0262(3)0.0499(10)
H19A0.50000.29960.02240.075*
H19B0.53510.38380.05740.075*
H19C0.44540.3699−0.04230.075*
C200.2902(3)0.4927(2)0.0539(3)0.0535(11)
H20A0.29110.53260.10530.080*
H20B0.21860.49970.00530.080*
H20C0.36660.49500.01830.080*
C210.0851(3)0.44569(19)0.1991(3)0.0496(11)
H21A0.11980.49470.22060.074*
H21B0.04440.42260.25550.074*
H21C0.02440.45290.14140.074*
C220.1287(3)0.27075(19)0.2596(3)0.0434(10)
H22A0.07920.30380.30040.065*
H22B0.18330.23950.30460.065*
H22C0.07340.23820.21710.065*

Source of material

The Zintl phase Rb12Si17 [5] was prepared from stoichiometric mixtures of the elements in sealed tantalum containers, which were encapsulated in an evacuated fused silica tube. The mixture was heated to 800 °C for 15 h and slowly cooled to room temperature with a rate of 0.5 °C/min. Bis(pentamethylcyclopentadienyl)zinc (ZnCp*2) was prepared as described in literature [6]. 113 mg Rb12Si17, 35 mg 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane (diaza-18-crown-6; Merck, p. a.), and 25 mg Zn2Cp*2 were placed in into a dry Schlenk vessel and ca 2 mL NH3 (Westfalen, 99.999%, stored over elemental Na) were condensed on this. The obtained light yellow solution was stored at −70 °C for 11 months, after this time yellow crystals of the title compound were found. An appropriate crystal was selected under perfluoroalkylether in a stream of cold nitrogen gas.

Experimental details

The methylene and methyl H atoms have been refined using a riding model with Uiso set to 1.2 and 1.5 Ueq(C), respectively. The H atoms bound to N Atoms have been located from the difference Fourier map and refined with free atomic coordinates and an Uiso of 1.2 Ueq(N) [3].

Comment

During our investigations of the behaviour and reactivity of Si containing Zintl compounds in solution with the goal to synthesize transition metal complexes with Si clusters as ligands analogously to the known Ge compounds [7], liquid ammonia has been found to be a highly suitable solvent [8, 9] . For supporting the dissolution of the solid Zintl compounds often sequestering agents like crown ethers or cryptands are necessary. In the present experiment, diaza-18-crown-6 has been used to dissolve Rb12Si17 in liquid ammonia in presence of ZnCp*2. The title compound has been obtained as a crystallized product of a partial metathesis reaction, while the remaining ingredients, Zn2+ cations as well as [Si4]4− and [Si9]4− cluster anions, were not found as parts of crystalline phases after this experiment.

[Rb(diaza-18-crown-6)]Cp* crystallizes in space group P21/c with all atoms at general positions. The Rb+ cation is coordinated by one diaza-18-crown-6 molecule and one Cp* anion. While pure RbCp* is found to crystallize in polymeric “multidecker” strands [10], here the presence of the crown ether causes the formation of molecular units, similar to the effect of 18-crown-6 on RbCp* in THF [11]. The Rb+ cation is situated near the centre of the diaza-18-crown-6 molecule but apart from the ring plane shifted in direction of the Cp* anion as previously found for [Rb(diaza-18-crown-6)] complexes in Fulleride salts [12]. Rb is bound to the Cp* ligand via two short Rb—C bonds of 3.075(3) Å and 3.210(3) Å which are in the same range as those observed for the η5 coordination in [Rb(18-crown-6)]Cp* [11]. All atoms of the Cp* ligand are in plane and the cyclopentadienyl ring is a nearly perfect pentagon (C—C bond lengths between 1.398(4) Å and 1.418(4) Å, C—C—C angles between 107.3(3)° and 108.8(3)°) which differs clearly from the shape of the neutral Cp*–H molecule [13], suggesting that the negative charge is located at Cp*. Confirming the neutral nature of the diaza-18-crown-6 molecule, one H atom close to each N atom could have been located from the Fourier map. In contrast to the structure of the free diaza-18-crown-6 molecule [14], where the N—H bonds are parallel, both the N—H bonds of the [Rb(diaza-18-crown-6)] complex are directed almost perpendicular to the ring plane. Probably the orthogonal N—H bond hampers the formation of the symmetric η5 coordination, possibly by forming N—H⋯C hydrogen bonds instead.

Acknowledgements

This work was supported by the Deutsche Forschungsgesellschaft (DFG) and the Technische Universität München within the funding programme Open Access Publishing. We thank Kerstin Mayer for the preparation of ZnCp*2.

References

Rigaku Oxford Diffraction: CrysAlis CCD, CrysAlis RED Version 1.171.33.34d. Oxford Diffraction Ltd., Yarnton, Oxfordshire, UK (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

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

Brandenburg, K.: DIAMOND. Visual Crystal Structure Information System. Version 3.2i. Crystal Impact, Bonn, Germany (2012).Search in Google Scholar

Quéneau, V.; Todorov, E.; Sevov, S. C.: Synthesis and structure of isolated silicon clusters of nine atoms. J. Am. Chem. Soc. 120 (1998) 3263–3264.10.1021/ja980044wSearch in Google Scholar

Blom, R.; Boersma, J.; Budzelaar, P. H. M.; Fischer, B.; Haaland, A.; Volden, H. V.; Weidlein, J.: The preparation of bis(pentamethylcyclopentadienyl)zinc and bis(trimethylsilylcyclopentadienyl)zinc, and their molecular structures determined by gas electron diffraction. Acta Chem. Scand. A 40 (1986) 113–120.10.3891/acta.chem.scand.40a-0113Search in Google Scholar

Bentlohner, M. M.; Jantke, L.-A.; Henneberger, T.; Fischer, C.; Mayer, K.; Klein, W.; Fässler, T. F.: On the nature of cridging metal atoms in intermetalloid clusters: synthesis and structure of the metal-atom-bridged zintl clusters [Sn(Ge9)2]4− and [Zn(Ge9)2]6−. Chem. Eur. J. 22 (2016) 13946–13952.10.1002/chem.201601706Search in Google Scholar

Benda, C. B.; Henneberger, T.; Klein, W.; Fässler, T. F.: [Si4]4− and [Si9]4− clusters crystallized from liquid ammonia solution – synthesis and characterization of K8[Si4][Si9](NH3)14.6. Z. Anorg. Allg. Chem. 643 (2017) 146–148.10.1002/zaac.201600369Search in Google Scholar

Henneberger, T.; Klein, W.; Fässler, T. F.: Silicon containing nine atom clusters from liquid ammonia solution: crystal structures of the first protonated clusters [HSi9]3− and [H2{Si/Ge}9]2. Z. Anorg. Allg. Chem. 644 (2018) 1018–1027.10.1002/zaac.201800227Search in Google Scholar

Behrens, U.; Dinnebier, R. E.; Neander, S.; Olbrich, F.: Solid-state structures of base-free rubidium and cesium pentamethylcyclopentadienides. Determination by high-resolution powder diffraction. Organometallics 27 (2008) 5398–5400.10.1021/om800617gSearch in Google Scholar

Neander, S.; Behrens, U.; Olbrich, F.: Novel 18-crown-6 organometallic rubidium and cesium complexes containing cyclopentadienyl, indenyl, pentamethylcyclopentadienyl, and fluorenyl as carbanions. J. Organomet. Chem. 604 (2000) 59–67.10.1016/S0022-328X(00)00202-3Search in Google Scholar

Boeddinghaus, M. B.; Wahl, B.; Fässler, T. F.; Jakes, P.; Eichel, R.-A.: Three salts containing the fullerene tetra-anion C604− – synthesis, X-ray single-crystal structure determination and EPR investigation. Z. Anorg. Allg. Chem. 638 (2012) 2205–2212.10.1002/zaac.201200272Search in Google Scholar

Benda, C. B.; Klein, W.; Fässler, T. F.: Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16. Z. Kristallogr. NCS 232 (2017) 511–512.10.1515/ncrs-2016-0402Search in Google Scholar

Dokurno, P.; Trokowski, R.; Kościuszko-Panek, B.; Ossowski, T.; Konitz, A.; Blażejowski, J.: Crystal structure of three diaza-crowns-18. Z. Kristallogr. 212 (1997) 362–366.10.1524/zkri.1997.212.5.362Search in Google Scholar

Received: 2018-07-19
Accepted: 2018-09-09
Published Online: 2018-09-27
Published in Print: 2018-12-19

©2018 Thomas Henneberger 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-2018-0252
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 3.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0252/html?lang=en
Scroll to top button