Startseite Crystal structure of (1aS,1a1S,2S)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl-4-nitrobenzoate, C22H25NO5
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Crystal structure of (1aS,1a1S,2S)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl-4-nitrobenzoate, C22H25NO5

  • Jiahuan Luo ORCID logo , Shengxian Zhai ORCID logo EMAIL logo , Chuchu Han und Hanwen Zhao
Veröffentlicht/Copyright: 16. November 2020
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 236 Heft 1

Abstract

C22H25NO5, monoclinic, P21/c (no. 14), a = 15.7241(13) Å, b = 7.0223(5) Å, c = 18.4613(14) Å, β = 100.329(4)°, V = 2005.4(3) Å3, Z = 4, Rgt(F) = 0.0495, wRref(F2) = 0.1564, T = 296(2) K.

CCDC no.: 2039767

The asymmetric unit of the molecular structure is shown in the Figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colorless block
Size:0.17 × 0.14 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint:21,787, 4985, 0.022
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3644
N(param)refined:254
Programs:Bruker [1], Olex2 [2]
Table 2:

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

AtomxyzUiso*/Ueq
C10.53113 (10)0.7800 (3)0.58806 (9)0.0644 (4)
H10.51820.90930.58440.077*
C20.60067 (10)0.7077 (3)0.56136 (8)0.0619 (4)
C30.62117 (11)0.5176 (3)0.56502 (10)0.0708 (5)
H30.66810.47210.54590.085*
C40.57076 (10)0.3958 (3)0.59766 (10)0.0694 (4)
H40.58360.26640.60050.083*
C50.50123 (9)0.4643 (2)0.62621 (9)0.0587 (4)
C60.48103 (9)0.6559 (2)0.62037 (9)0.0621 (4)
H60.43330.70160.63840.074*
C70.45188 (10)0.3257 (3)0.66396 (10)0.0663 (4)
C80.33374 (9)0.2845 (2)0.72671 (8)0.0553 (3)
H80.37480.21230.76270.066*
C90.27728 (9)0.1439 (2)0.67672 (8)0.0527 (3)
H90.28600.14840.62550.063*
C100.18052 (9)0.14880 (19)0.68438 (8)0.0507 (3)
H100.14390.10120.63940.061*
C110.28185 (11)−0.0622 (2)0.70937 (10)0.0667 (4)
H11A0.2727−0.16240.67260.080*
H11B0.3327−0.08670.74650.080*
C120.20238 (10)−0.0100 (2)0.74007 (9)0.0575 (4)
C130.17531 (11)−0.0233 (2)0.80304 (10)0.0642 (4)
H130.1977−0.11730.83660.077*
C140.10874 (11)0.1113 (3)0.82123 (10)0.0668 (4)
H14A0.13460.18970.86260.080*
H14B0.06230.03870.83610.080*
C150.07105 (10)0.2403 (2)0.75681 (10)0.0645 (4)
H15A0.04190.34660.77540.077*
H15B0.02810.16930.72310.077*
C160.13886 (9)0.3179 (2)0.71436 (8)0.0522 (3)
C170.20441 (11)0.4376 (2)0.76263 (9)0.0576 (4)
H170.18400.52880.79180.069*
C180.28846 (11)0.4244 (2)0.76721 (9)0.0596 (4)
H180.32260.50950.79830.072*
C190.13871 (11)0.4979 (3)0.60296 (10)0.0674 (4)
H19A0.14290.39400.56910.081*
H19B0.19680.53430.62590.081*
C200.09433 (11)0.6627 (2)0.56185 (9)0.0655 (4)
H20A0.09120.76660.59590.079*
H20B0.03570.62640.54050.079*
C210.14050 (16)0.7310 (3)0.50107 (11)0.0887 (6)
H21A0.19810.77320.52320.106*
H21B0.14680.62420.46920.106*
C220.0959 (2)0.8894 (4)0.45509 (14)0.1190 (9)
H22A0.04040.84640.43000.178*
H22B0.13020.92790.41960.178*
H22C0.08830.99540.48620.178*
N10.65651 (10)0.8387 (3)0.52871 (9)0.0807 (5)
O10.63772 (13)1.0053 (3)0.52389 (13)0.1229 (7)
O20.71968 (11)0.7727 (3)0.50842 (10)0.1181 (6)
O30.47294 (9)0.1625 (2)0.67558 (10)0.0951 (5)
O40.38273 (6)0.40487 (16)0.68382 (7)0.0630 (3)
O50.09169 (7)0.43701 (16)0.65788 (7)0.0653 (3)

Source of material

All of these reactions were executed in argon atmosphere with dry solvents, unless otherwise noted. All the commercially chemicals were purchased and used without any further purification.

The 4-(but-3-yn-1-yl)-4-butoxycyclohexa-2,5-dien-1-one was synthesized as following: To a well-stirred mixture of 4-(but-3-yn-1-yl)phenol (10 mmol) in butan-1-ol (15 mL) was added the phenyliodine(III) diacetate (15 mmol) at 0 °C in several portions. Then the mixture was warmed to room temperature and stirred overnight followed by quenching with the saturated aqueous NaHCO3 (40 mL) and the saturated aqueous Na2SO3 (20 mL) and extracted with ethyl acetate (30 mL) three times. The combined organic mixture was washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography using petroleum ether/ethyl acetate eluent to afford the 4-(but-3-yn-1-yl)-4-butoxycyclohexa-2,5-dien-1-one.

The 4-butoxy-4-(penta-3,4-dien-1-yl)cyclohexa-2,5-dien-1-one was synthesized: To a well-stirred solution of 4-(but-3-yn-1-yl)-4-butoxycyclohexa-2,5-dien-1-one (2 mmol) in dioxane (10 mL) was sequentially added paraformaldehyde (300 mg, 10.0 mmol) CuBr (114.8 mg, 0.8 mmol) and diisopropylamine (0.56 mL, 4.0 mmol) under argon atmosphere. The resulting mixture was stirred at 110 °C for about 1 h (traced by TLC). After cooling to room temperature, the reaction mixture was filtered through a plug of celite and followed by washing with DCM (10 mL × 3). The organic phase was concentrated under reduced pressure and the residue purified by flash column chromatography using PE/ethyl acetate eluent to afford 4-butoxy-4-(penta-3,4-dien-1-yl)cyclohexa-2,5-dien-1-one.

The (R)-4a-butoxy-1,4a,5,6-tetrahydro-2H-cyclobuta[de]naphthalen-2-one was synthesized: To a 25 mL Schlenk tube equipped with magnetic stirring bar was added the 4-butoxy-4-(penta-3,4-dien-1-yl) cyclohexa-2,5-dien-1-one (100.2 mg) and TFE (2.0 mL), The tube was sealed and the resulting mixture was stirred for 4 h at 100 °C, before being cooled down to rt, and the mixture was transferred to a round-bottom flask and followed by concentration under reduced pressure, and then the resulting sticky oil was purified by column chromatography on silica gel using the petroleum ether/ethyl acetate as the eluent to afford the (R)-4a-butoxy-1,4a,5,6-tetrahydro-2H-cyclobuta[de]naphthalen-2-one.

The (1aS,1a1S,2R,4aR)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-ol was synthesized: To a solution of (R)-4a-butoxy-1,4a,5,6-tetrahydro-2H-cyclobuta[de]naphthalen-2-one (151.8 mg, 0.474 mmol) in dry MeOH (5 mL) was added NaBH4 (36.05 mg, 2.0 equiv). The reaction mixture was stirred for another 1 h at room temperature, then concentrated under reduced pressure. The resulting residue was purified by flash column chromatography using PE/EA eluent to afford the (1aS,1a1S,2R,4aR)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-ol.

The (1aS,1a1S,2S,4aR)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta [de]naphthalen-2-yl 4-nitrobenzoate was synthesized: To a stirred solution of alcohol (1aS,1a1S,2R,4aR)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-ol (54 mg, 0.17 mmol), p-nitrobenzoic acid (142.05 mg, 0.85 mmol), and PPh3 (248.2 mg, 0.85 mmol) in THF (5.0 mL) was added DEAD (148.02 mg, 0.13 mL, 0.85 mmol) at 0 °C. The resulting mixture was stirred at room temperature overnight before it was quenched with saturated aq. NaHCO3 solution (10 mL) and extracted with EtOAc (3 × 10 mL). The combined organic phases were washed with brine (20 mL) and dried over anhydrous Na2SO4. After filtration and evaporation of the solvent, the residue so obtained was purified by flash column chromatography with petroleum ether/EtOAc (15:1 to 10:1) to give the (1aS,1a1S,2S,4aR)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl 4-nitrobenzoate.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Comment

The cyclobutane and the cyclobutene derivatives containing polycyclic compounds are very common in natural products and bioactive compounds [3], and there are numerous methods for the construction of the cyclobutane and the cyclobutene derivatives via the photochemistry initiation [4] and the transition metal catalyzed [5] and the Lewis acid promoted [6] and the thermal promoted fashion [7]. Recently, we disclosed a powerful, distinct, and atom-economical method for the synthesis of clobutane-fused oxygen containing tricyclic framework via a thermal promoted intramolecular [2+2] cycloaddition of cyclohexadienone-tethered allenes [8]. However, the method for the dicyclobutanes containing ring system remains rather rare reported to date. As our continuing efforts on the efficient synthetic methods for cyclic compounds synthesis associate with allenes [9], we herein report a useful method and the crystal structure of the titled compound.

There is one molecule in the asymmetric unit of the title structure (see the Figure). The single crystal structure verifies that all bond lengths are in normal ranges. Furthermore, the crystal packing doesn’t exhibit strong intramolecular or intermolecular hydrogen bond.

Corresponding author: Shengxian Zhai, College of Chemistry and Environmental Engineering, Anyang Institute of Technology Anyang, 455000Henan, P. R. China, e-mail: .

Funding source: Henan Postdoctoral Foundation

Funding source: Anyang Institute of Technology

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by Henan Postdoctoral Foundation and the Foundation of Postdoctoral innovation base of Anyang Institute of Technology.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2020-09-28
Accepted: 2020-10-21
Published Online: 2020-11-16
Published in Print: 2021-01-26

© 2020 Jiahuan Luo et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

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  2. New Crystal Structures
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  64. Crystal structure of (1aS,1a1S,2S)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl-4-nitrobenzoate, C22H25NO5
  65. Crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-k2O,O′)(triphenylarsine-κAs)rhodium(I), C24H19AsNO3Rh
  66. Crystal structure of catena-poly[triqua-bis(μ2-4-carboxy-2-(1H-tetrazol-1-yl)-1H-imidazole-5-carboxylato-k3N,O:O′)barium(II)] tetrahydrate, C14H14BaN12O15
  67. Crystal structure of (E)-3′,6′-bis(ethylamino)-2-((quinoxalin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C35H32N6O2
  68. Crystal structure of diaqua-bis(μ2-5-chloro-salicylato-κ3O,O′:O′)-bis(5-chloro-salicylato-κ2O,O′)-bis(1,10-phenanthroline-κ2N,N′) dilead(II) – water (1/2), C52H36C14N4O14Pb2·2(H2O)
  69. Crystal structure of (E)-2-(4-ethoxycarbonyl-3,5-dimethyl-2-(pyrrole-2-ylmethyleneamino)-3′,6′-dihydroxylspiro[isoindoline-1,9′-xanthen]-3-one-methanol (1/1), C31H29N3O7
  70. The crystal structure of 5H-dibenzo[b,e]azepine-6,11-dione, C14H9NO2
  71. Crystal structure of (E)-2-(4-fluoro-2-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  72. The crystal structure of N-(2-methoxy-4,5-bis[phenylselanyl]phenyl)picolinamide, C25H20N2O2Se2
  73. The crystal structure of (E)-2-(5-bromo-2-hydroxybenzylidene)-N-phenylhydrazine-1- carboxamide monohydrate, C14H14BrN3O3
  74. Crystal structure of fac-tricarbonyl-(nitrato-k1O)-bis(pyridine-κN)-rhenium, C13H10O6N3Re
  75. Crystal structure of (E)-2-(((1H-pyrrol-2-yl)methylene)amino)-3′,6′-dihydroxyspiro[isoindoline-1,9′-xanthen]-3-one — methanol (1/2), C27H25N3O6
  76. The crystal structure of 4-amino-N′-(4-aminobenzoyl)benzohydrazide monohydrate, C14H16N4O3
  77. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 5-hydroxyisophthalate monohydrate, C12H20N8O6S2
  78. The crystal structure of 2-(chloromethyl)pyridine, C6H6ClN
  79. The crystal structure of 1-bromo-4-iodo-benzene, C6H4BrI
  80. The crystal structure of 2,6-dimethyl-4-nitro-phenol, C8H9NO3
  81. The crystal structure of 3-chloropropionic acid, C3H5ClO2
  82. The crystal structure of 2-(2-methoxyphenyl)acetic acid, C9H10O3
https://doi.org/10.1515/ncrs-2020-0496
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Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 3-oxo-urs-12-en-28-oic acid, C30H46O3·1/6H2O
  4. The crystal structure of (3S,12R,20R,24R)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25–triol–ethyl acetate (4/1), C34H56O6⋅ 0.25(C4H8O2)
  5. A new polymorph of tetrakis(dimethylammonium) catena-poly[tetrakis(μ2-sulfato-κ2O:O′)dizinc(II)], Zn2C8H32N4O16S4
  6. Crystal structure of 10-oxysophoridine, C15H22N2O2
  7. The crystal structure of (5R,8R,9R,10R,12R,13R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)tetradecahydro-3H-cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O4
  8. Synthesis, crystal structure and optical property of 1,6-bis(p-tolylthio)pyrene, C30H22S2
  9. The crystal structure of hexakis(2-(pyridin-2-ylamino)pyridin-1-ium) decavanadate(V) dihydrate, C60H64N18O30V10
  10. Preparation and crystal structure of a cationic olefin polymerization precatalyst: (1,7-bis(2,6–dichlorophenyl)-1,7-di-aza-4-oxo-heptan-1,4,7-triyl)dimethyl zirconium(IV), C18H20Cl4N2OZr
  11. The crystal structure of fac-tricarbonyl(4,4-dimethyl-2,2-dipyridyl-κ2N,N′)- (pyrazole-κN)rhenium(I) nitrate, C18H16O3N4Re
  12. Synthesis and crystal structure of hexaaquacopper(II) 2,5-dicarboxyterephthalate, C10H16O14Cu
  13. The crystal structure of (8R,10R,12R,14R)- 12-hydroxy-16-(5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)- 4,4,8,10,14-pentamethyltetradecahydro-3H- cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O5
  14. Structure of the mixed crystal (S)-(6-(bromo/chloro)-2-methoxy-2,6-dihydroquinolin-3-yl)(phenyl)methanol, C17H14Br0.5Cl0.5NO2
  15. The crystal structure of trans-tetraaqua-bis(4-acetylphenoxyacetato-κ1O)manganese(II), C20H26O12Mn
  16. Crystal structure of (E)-2-(4-fluoro-3-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  17. Crystal structure of DL-α-(methylaminomethyl)benzyl alcohol, C9H13NO
  18. The crystal structure of dipentaerthritol hexanitrate, C10H16N6O19
  19. Crystal structure of N,N-diphenylformamide, C13H11NO
  20. Crystal structure of (E)-2-(3,5-bis(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen- 1(2H)-one, C20H14F6O2
  21. Crystal structure of ortho-methoxy benzaldehyde, C8H8O2 – a second polymorph and deposition of 3D coordinates
  22. Crystal structure of catena-poly[diaqua-bis(μ2-2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O:O')-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O,O')yttrium(III)], C51H79O11Y
  23. Crystal structure of benzylthiouronium chloride, C8H11ClN2S
  24. Synthesis and crystal structure of tert-butyl (2′R,3R,3′R,4a′R,9a′S)-1-acetyl-5-chloro-3″-methyl-2,5″,9′-trioxo-1″-phenyl-1″,4a′,5″,9a′-tetrahydro-1′H,3′H,9′H-dispiro[indoline-3,4′-xanthene-2′,4″-pyrazole]-3′-carboxylate, C36H32ClN3O7
  25. Crystal structure of 2-hydroxy-4-methoxy benzaldehyde, C8H8O3
  26. Crystal structure of poly[diaqua-(m3-3′,5′-dicarboxy-[1,1′-biphenyl]-3,4-dicarboxylato-K4O,O′:O″:O‴) cadmium(II)], C16H11O10Cd
  27. Crystal structure of {tetraaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)}-{triaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)} – water – acetone (1/1/8/2)
  28. Synthesis and crystal structure of bis{2-bromo-6-((E)-((4-((E)-1-(methoxy-imino)ethyl)phenyl)imino)methyl)phenolato- κ2N,O}zinc(II)-methanol(1/2), C65H60Br4N8O9Zn2
  29. Crystal structure of benzenesulphonic acid
  30. Crystal structure of N-benzyl-N-nicotinoyl-nicotine amide C19H15N3O2
  31. Crystal structure of poly[aqua(μ3-2,4-diamino-benzenesulfonato-κ4N:N′,O:O′)silver(I)], C12H18O8N4S2Ag2
  32. Crystal structure of 1,4-bis(methylpyridinium benzene) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C26H18N6NiS4
  33. Crystal structure of the Cu(II) complex chlorido-(6-oxo-2-phenyl-1,6-dihydropyrimidine-4-carboxylato-k2N,O)-(phenanthroline-k2N,N')copper(II), C23H15ClCuN4O3
  34. Crystal structure of phenarsazine chloride acetic acid solvate, C14H13AsClNO2
  35. Crystal structure of poly[aqua-(μ2-3,3′,4,5′-biphenyl tetracarboxylate- κ3O,O′:O′′) -(μ2-4,4′-bis(pyrid-4-yl)biphenyl-κ2N:N′)zinc(II)], C27H18NO9Zn
  36. Crystal structure of catena-poly[(μ2-3-amino-benzenedisulfonato-κ2N:O)-bis (3-methyl-isoquinoline-κN)silver(I)], C26H24N3O3SAg
  37. Crystal structure of 2-((4-Aminophenyl)thio)acetic acid, C8H9NO2S
  38. Crystal structure of phenarsazine chloride dimethylsulfoxide solvate, C14H15AsClNOS
  39. Synthesis and crystal structure of 2-azido-N-phenylacetamide, C8H8N4O
  40. Crystal structure of chlorido{hydridotris[3-phenyl-5-methylpyrazol-1-yl-κN3]borato}copper(II), C30H28BClCuN6
  41. Crystal structure of benzanthrone – a redetermination for correct molecular geometry and localization of hydrogen atoms
  42. Crystal structure of 4-bromobenzaldehyde – complete redetermination at 200 K, C7H5BrO
  43. Crystal structure and spectroscopic properties of chlorido{hydridotris[3-,5-dimethylpyrazol-1-yl-κN3]borato}(3-,5-dimethylpyrazol-1-yl-κN)copper(II), C20H30BClCuN8
  44. The crystal structure of 4-((2-hydroxynaphthalen-1-yl)(pyrrolidin-1-yl)methyl)benzonitrile, C22H20N2O
  45. Crystal structure of 4-ethyl-3-phenylisoquinolin-1(2H)-one, C17H15NO
  46. Crystal structure of (tricyclohexylphosphane-κP)-[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-k1S]gold(I), C26H40AuFNOPS
  47. Crystal structure of (3S,8R,10R,12R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H54O4
  48. The crystal structure of 2-[(S)-1-(naphthalen-1-yl)ethyl]-2,3,7,7a- tetrahydro-3a,6-epoxyisoindol-1(6H)-one, C19H20NO2
  49. Crystal structure of {hydridotris[3-(t-butyl)-5-isopropylpyrazol-1-yl-κN3]borato}thallium(I), C30H52BN6Tl
  50. Synthesis and crystal structure of 1-octyl-3-phenylquinoxalin-2(1H)-one, C22H26N2O
  51. The crystal structure of 2,6-difluorophenol, C6H4F2O
  52. 4-(9H-Fluoren-9-yl)-4-methylmorpholin-4-ium bromide, C18H20BrNO
  53. The crystal structure of 2,4-dimethylimidazole monohydrate, C5H10N2O
  54. The crystal structure of 1,2-dimethylimidazole, C5H8N2
  55. The crystal structure of 3-ammonio-4-aminobenzoate, C7H8N2O2 – a second polymorph
  56. The crystal structure of 4-hydroxy-2,5-bis(1-methyl-1H-imidazol-3-ium-2-ylthio)-3,6-dioxocyclohexa-1,4-dienolate chloride monohydrate, C14H15N4O5S2Cl
  57. The crystal structure of butyrylferrocene, C14H16FeO
  58. The crystal structure of bi-1,1′-cyclopentane-1,1′-diol, C10H18O2
  59. The crystal structure of 2-iso-propylimidazole, C6H10N2
  60. The crystal structure of aqua-tris (1,3-diphenylpropane-1,3-dionato-κ2O,O′)-lanthanum(III), C45H35LaO7
  61. Crystal structure of (3E,5E)-3,5-bis-4-methoxy-3-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  62. The crystal structure of 3,5-dichloro-6-diazo-2,4-dinitrocyclohexa-2,4-dien-1-one, C6Cl2N4O5
  63. Crystal structure of carbonyl(2-methylquinolin-8-olato-κ2N,O)(triphenylarsine-κAs)rhodium(I), C29H23AsNO2Rh
  64. Crystal structure of (1aS,1a1S,2S)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl-4-nitrobenzoate, C22H25NO5
  65. Crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-k2O,O′)(triphenylarsine-κAs)rhodium(I), C24H19AsNO3Rh
  66. Crystal structure of catena-poly[triqua-bis(μ2-4-carboxy-2-(1H-tetrazol-1-yl)-1H-imidazole-5-carboxylato-k3N,O:O′)barium(II)] tetrahydrate, C14H14BaN12O15
  67. Crystal structure of (E)-3′,6′-bis(ethylamino)-2-((quinoxalin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C35H32N6O2
  68. Crystal structure of diaqua-bis(μ2-5-chloro-salicylato-κ3O,O′:O′)-bis(5-chloro-salicylato-κ2O,O′)-bis(1,10-phenanthroline-κ2N,N′) dilead(II) – water (1/2), C52H36C14N4O14Pb2·2(H2O)
  69. Crystal structure of (E)-2-(4-ethoxycarbonyl-3,5-dimethyl-2-(pyrrole-2-ylmethyleneamino)-3′,6′-dihydroxylspiro[isoindoline-1,9′-xanthen]-3-one-methanol (1/1), C31H29N3O7
  70. The crystal structure of 5H-dibenzo[b,e]azepine-6,11-dione, C14H9NO2
  71. Crystal structure of (E)-2-(4-fluoro-2-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  72. The crystal structure of N-(2-methoxy-4,5-bis[phenylselanyl]phenyl)picolinamide, C25H20N2O2Se2
  73. The crystal structure of (E)-2-(5-bromo-2-hydroxybenzylidene)-N-phenylhydrazine-1- carboxamide monohydrate, C14H14BrN3O3
  74. Crystal structure of fac-tricarbonyl-(nitrato-k1O)-bis(pyridine-κN)-rhenium, C13H10O6N3Re
  75. Crystal structure of (E)-2-(((1H-pyrrol-2-yl)methylene)amino)-3′,6′-dihydroxyspiro[isoindoline-1,9′-xanthen]-3-one — methanol (1/2), C27H25N3O6
  76. The crystal structure of 4-amino-N′-(4-aminobenzoyl)benzohydrazide monohydrate, C14H16N4O3
  77. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 5-hydroxyisophthalate monohydrate, C12H20N8O6S2
  78. The crystal structure of 2-(chloromethyl)pyridine, C6H6ClN
  79. The crystal structure of 1-bromo-4-iodo-benzene, C6H4BrI
  80. The crystal structure of 2,6-dimethyl-4-nitro-phenol, C8H9NO3
  81. The crystal structure of 3-chloropropionic acid, C3H5ClO2
  82. The crystal structure of 2-(2-methoxyphenyl)acetic acid, C9H10O3
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