Home Synthesis and crystal structure of 3-N-acetyl-5-(pyridin-3-yl)-2-(quinolin-2-yl)-1,3,4-oxadiazoline, C18H14N4O2
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Synthesis and crystal structure of 3-N-acetyl-5-(pyridin-3-yl)-2-(quinolin-2-yl)-1,3,4-oxadiazoline, C18H14N4O2

  • Xiang Yu ORCID logo , Lu Peng , Xin Wang and Ya-Fang Chen EMAIL logo
Published/Copyright: July 10, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 5

Abstract

C18H14N4O2, triclinic, P1̄ (no. 2), a = 7.6557(7) Å, b = 11.0905(8) Å, c = 11.3544(9) Å, α = 61.6430(10)°, β = 73.600(2)°, γ = 75.397(2)°, V = 805.86(11) Å3, Z = 2, Rgt(F) = 0.0609, wRref(F2) = 0.1633, T = 298 K.

CCDC no.: 1997954

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:Colourless block
Size:0.45 × 0.44 × 0.40 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Oxford Diffraction Gemini, omega scans
θmax, completeness:25.0°, 96%
N(hkl)measured, N(hkl)unique, Rint:3916, 2736, 0.029
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1688
N(param)refined:218
Programs:CrysAlisPRO [1], Olex2 [2], SHELX [3], [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.9068(2)0.39481(18)0.3208(2)0.0422(5)
O20.7590(3)0.0015(2)0.5539(2)0.0575(6)
N10.7505(3)0.2260(2)0.4974(2)0.0416(6)
N20.7144(3)0.3405(2)0.5279(3)0.0418(6)
N30.9516(3)0.7840(2)0.2686(3)0.0514(7)
N40.6239(3)0.3030(2)0.2498(2)0.0383(6)
C10.8080(3)0.4322(3)0.4232(3)0.0344(7)
C20.8777(4)0.2529(3)0.3643(3)0.0384(7)
H20.99370.19000.37800.046*
C30.9303(4)0.6579(3)0.2907(3)0.0432(8)
H30.99380.62670.22530.052*
C40.8186(4)0.5703(3)0.4059(3)0.0338(7)
C50.7217(4)0.6185(3)0.5040(3)0.0384(7)
H50.64510.56420.58150.046*
C60.7420(4)0.7481(3)0.4833(3)0.0418(7)
H60.68000.78220.54690.050*
C70.8572(4)0.8263(3)0.3656(3)0.0470(8)
H70.87000.91310.35280.056*
C80.8000(4)0.2477(3)0.2575(3)0.0358(7)
C90.9168(4)0.1899(3)0.1694(3)0.0419(7)
H91.03720.15110.18040.050*
C100.8507(4)0.1919(3)0.0687(3)0.0488(8)
H100.92550.15400.01080.059*
C110.6653(4)0.2529(3)0.0529(3)0.0432(8)
C120.5560(4)0.3057(3)0.1471(3)0.0382(7)
C130.3697(4)0.3666(3)0.1346(3)0.0507(8)
H130.29640.39970.19670.061*
C140.2982(5)0.3765(4)0.0314(4)0.0668(10)
H140.17710.41650.02380.080*
C150.4085(6)0.3259(4)−0.0633(4)0.0757(11)
H150.35920.3341−0.13320.091*
C160.5878(6)0.2649(4)−0.0537(4)0.0655(10)
H160.65810.2315−0.11640.079*
C170.7078(4)0.0961(3)0.5885(3)0.0422(8)
C180.6002(5)0.0792(3)0.7292(3)0.0604(9)
H18A0.5387−0.00100.77150.091*
H18B0.51100.15980.72060.091*
H18C0.68310.06820.78430.091*

Source of material

In a representative experiment 3-methylquinolin (1.0 mmol) reacted with SeO2 (1.1 mmol) in dioxane (10 mL) at 80 °C to afford the aldehyde, and then the mixture was reacted with nicotinohydrazide (1.0 mmol) in acetic anhydride (5 mL). The reaction mixture was refluxed and the title compound was purified by preparative thin-layer chromatography (PTLC) and recrystallised from dichloromethane. 1H NMR (400 MHz, Chloroform-d) δ [ppm]: 9.14 (d, J = 2.8 Hz, 1H), 8.73 (dd, J = 4.9, 1.2 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 8.13–8.18 (m, 2H), 7.84 (d, J = 8.4 Hz, 1H), 7.74 (t, J = 7.2 Hz, 1H), 7.54–7.60 (m, 2H), 7.36–7.40 (m, 1H), 7.26 (m, 1H), 2.42 (s, 3H).

Experimental details

Crystal structure determination of C18H14N4O2 by X-ray diffractions was carried on a Oxford Diffraction Gemini with the crystal kept at 298 K during data collection. The structure was solved with the Olex2 program [2] as an interface together with the SHELXT and SHELXL programs [3], [4]. Hydrogen atoms were treated using a riding model.

Comment

Recent studies show that introduction of active fragments into quinolin could increase biological activity [5]. Oxazoline is a group of heterocyclic compounds with nitrogen and oxygen atoms, which showed bioactivities such as anti-HIV [6] and antibacterial [7] activities. To further study the structure-activity relationship of quinolin, here we introduced oxazoline ring and prepared an quinolin-based derivative to find compounds with potential activity.

The asymmetric unit of the title structure consists of one cystallographically independent molecule (shown in the figure). One 1,3,4-oxadiazolyl group, one 3-pyridinyl ring and one quinolinyl moiety form the title molecule. All bond lengths are in normal ranges and they are similar with the known compound [8]. The short C—N bond length of 1.303(3) Å (N2-C1) suggests a localized double bond, and the C—N bond lengths of 1.486(3) Å (N1-C2) suggests a localized single bond. The bond distance of C17-O2 is 1.227(3) Å, which is typical for a carbonyl group.

Acknowledgements

This work was supported by the Science and Technology Fund of Guizhou [QKH-PTRC(2017)5735-22], Guizhou Provincial Natural Science Foundation [QKH-J(2020)1Y070] and the Youth Talent Development Project of Guizhou Provincial Department of Education [2017]169.

References

1. Oxford Diffraction: CrysAlisPro, 1.171.39.46, SCALE3 ABSPACK. Oxford Diffraction Ltd, Yarnton, England (2018).Search in Google Scholar

2. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H.: OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 42 (2009) 339–341.10.1107/S0021889808042726Search in Google Scholar

3. 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

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

5. Yu, X.; Feng, G.; Huang, J. L.; Xu, H.: Evaluation of some quinoline-based hydrazone derivatives as insecticidal agents. RSC Adv. 6 (2016) 30405–30411.10.1039/C6RA00993JSearch in Google Scholar

6. Che, Z. P.; Huang, N.; Yu, X.; Yang, L. M.; Ran, J. Q.; Zhi, X. Y.; Xu, H.; Zheng, Y. T.: Microwave-assisted combinatorial synthesis of 2-alkyl-2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-aryl-1,3,4-oxadiazolines as anti-HIV-1 agents. Comb. Chem. High Throughput Screen. 16 (2013) 400–407.10.2174/1386207311316050005Search in Google Scholar PubMed

7. Naveena, C. S.; Boja, P.; Manjunath, K.; Arulmoli, T.; Shalini, S.: Synthesis, characterization and antimicrobial activity of some 2,5-disubstituted-3-acetyl-[1,3,4]-oxadiazoles carrying 2-(aryloxymethyl) phenyl moiety. Der Pharma Chem. 3 (2011) 247–257.Search in Google Scholar

8. Grishko, V. V.; Tolmacheva, I. A.; Galaiko, N. V.; Pereslavceva, A. V.; Anikina, L. V.; Volkova, L. V.; Bachmetyev, B. A.; Slepukhin, P. A.: Synthesis, transformation and biological evaluation of 2,3-secotriterpene acetylhydrazones and their derivatives. Eur. J. Med. Chem. 68 (2013) 203–211.10.1016/j.ejmech.2013.07.016Search in Google Scholar PubMed

Received: 2020-04-05
Accepted: 2020-04-20
Published Online: 2020-07-10
Published in Print: 2020-08-26

©2020 Xiang Yu et al., published by De Gruyter, Berlin/Boston

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

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  72. Crystal structure of dichlorido-bis(dimethyl sulphoxide-κO)-bis(4-methylbenzyl-κC1)tin(IV), C20H30Cl2O2S2Sn
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  74. Crystal structure of chloridotris(4-chlorophenyl)(dimethyl sulfoxide-κO)tin(IV), C20H18Cl4OSSn
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  77. Crystal structure of 6-methoxy-3-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4H-chromen-4-one-methanol (1/1), C20H18N2O6
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  79. Crystal structure of tert-butyl 2-(hydroxymethyl)-5-{4-[(methoxycarbonyl)amino]phenyl}-2,5-dihydro-1H-pyrrole-1-carboxylate, C18H24N2O5
  80. Crystal structure of [(Z)-O-isopropyl N-(4-nitrophenyl)thiocarbamato-κS]-(triphenylphosphine-κP)-gold(I), C28H26AuN2O3PS
  81. Crystal structure of [O-ethyl N-(4-nitrophenyl)thiocarbamato-κS](tri-4-tolylphosphine-κP)gold(I) tetrahydrofuran solvate, C30H30AuN2O3PS, C4H8O
https://doi.org/10.1515/ncrs-2020-0174
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of isopimara-7,15-dien-3-one, C20H30O
  3. Crystal structure of bis(6-aminopyridine-2-carboxylato-κ2O,N)-copper(II), C12H10O6N4Cu
  4. Crystal structure of 5,6-diphenyldibenzo[c, g]chrysene, C38H24
  5. Poly[bis(dimethylformamide-κO)-(μ8-5,5′′-dicarboxy-[1,1′:4′,1′′-terphenyl]-2′,3,3′′,5′-tetracarboxylato-κ8O:O1:O2:O3:O4:O5:O6:O7)dizinc(II)] — dimethylformamide (1/2), C18H19N2O8Zn
  6. The crystal structure of poly[bis(N,N-dimethylformamide-κ1O)(μ4- 2′,5,5′,5′′-tetracarboxy-[1,1′:4′,1′′-terphenyl]-3,3′′-dicarboxylato-κ4O:O′:O′′:O′′′)manganese(II)] — N,N-dimethylformamide (1/2), C36H40N4O16Mn
  7. Crystal structure of N,N-dimethyl-4-((7-nitrobenzo[c][1,2,5]thiadiazol-4-yl)ethynyl)aniline, C16H12N4O2S
  8. The crystal structure of 8a-methoxy 8a-methoxy-1,5,8a,9a-tetrahydro-4H-8,9-dioxa-3a1λ4-aza-8aλ4, C18H14BNO3
  9. Crystal structure of poly[diaqua-(μ2-5-isopropoxyisophthalato-κ2O:O′)-(μ2-(1,3-bis(3,5-di(1H-imidazol-1-yl)pyridine))-κ2N:N′)cobalt(II)] monohydrate, C22H25N5O8Co
  10. The crystal structure of acetoximium 1′-hydroxy-1H,1H′-5,5′-bitetrazole-1-olate monohydrate, C5H11N9O4
  11. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-vinyl-1H-imidazol-3-ium hexafluoridophosphate(V), C9H13F6N2O2P
  12. The crystal structure of catena-poly[(μ2-4-(benzo[d]imidazol-2-yl)benzenecarboxylato-κ2N,O)-(μ2-4-(benzo[d]imidazol-2-yl)benzenecarboxylato-κ3N,O:O′)cadmium(II)]dihydrate, C28H22CdN4O6
  13. Enzyme-mediated synthesis and crystal structure of (2R,4S)-hydroxyketamine, C13H16ClNO2
  14. The crystal structure of bis(isothiocyanato-κ1N)-(methanol-κ1O)-[2-morpholine-4-yl-4,6-di(pyrazol-1-yl)-1,3,5-triazine-κ3N,N′,N′′] manganese(II), C16H18MnN10O2S2
  15. Crystal structure of bis{5-chloro-2-(((4-trifluoromethyl)imino)methyl)phenolato-κ2N,O}copper(II), C28H16Cl2CuF6N2O2
  16. Crystal structure of bis(1,3-phenylenedimethanaminium) bis(triiodide) tetraiodide – water (1/2) , C8H16I5N2O
  17. Crystal structure and anti-inflammatory activity of (3E,5E)-3,5-bis(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one, C25H18F3NO3S
  18. The crystal structure of bis{3-(diphenylphosphaneyl)propanoato-κ2O,P}platinum(II) dihydrate, C30H28O6P2Pt
  19. The crystal structure of (E)-2-(4-((4-fluorobenzyl)oxy)styryl)-4,6-dimethoxybenzaldehyde, C24H21FO4
  20. Crystal structure of bis[3-methoxy-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-κ3O,N,N′]nickel(II), C28H26N8O4Ni
  21. Crystal structure of 1-(2-(pyridin-2-yl)-5-(pyridin-3-yl)-1,3,4-oxadiazol-3(2H)-yl)ethan-1-one, C14H12N4O2
  22. Synthesis and crystal structure of 3-N-acetyl-5-(pyridin-3-yl)-2-(quinolin-2-yl)-1,3,4-oxadiazoline, C18H14N4O2
  23. Crystal structure of 2-methyl-1H-perimidine, C12H10N2
  24. Crystal structure of (E)-2-(5,5-dimethyl-3-(4-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)oxy)styryl)cyclohex-2-en-1-ylidene)malononitrile, C25H19N5O4
  25. Structural elucidation of 1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione isolated from Bulbine latifolia (L.) Wild, C24H18O8
  26. Crystal structure of 3-cinnamoyl-4-hydroxybenzoic acid, C16H12O4
  27. The crystal structure of poly[bis(μ4-2,3-pyridinedicarboxylato)-(μ2-oxalyl dihydrazide)-dicadmium(II) dihydrate], C16H16O12N6Cd2
  28. Synthesis and crystal structure of 1-{4-[(3-bromo-2-hydroxy-benzylidene)amino]phenyl}ethanone, C15H12BrNO2
  29. Synthesis and crystal structure of 1-{4-[(2-bromo-6-hydroxy-benzylidene)amino]phenyl}ethanone, C15H12BrNO2
  30. Crystal structure of (4-aminobenzoato-κ2O,O′)-[5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′]nickel(II) perchlorate monohydrate, C23H44ClN5NiO7
  31. Crystal structure of 1-{4-[(4-fluoro-2-hydroxy-benzylidene)amino]phenyl}ethanone, C15H12FNO2
  32. Preparation and crystal structure of a non-symmetrical vanadium(II) dimer: tri-μ2-bromido-(hydrogen-tris(3-isopropyl-4-bromopyrazol-1-yl)borato-κ3N,N′,N′′)-tris(tetrahydrofuran-κO)divanadium(II) – tetrahydrofuran (1/1), C34H57BBr6N6O4V2
  33. Crystal structure of bis{2-(((4-(1-(hydroxyl-imino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C30H26CoN4O4
  34. Crystal structure of 3-((3-nitrophenyl)sulfonamido)propanoic acid — 4,4′-bipyridine (1/1), C19H18N4O6S
  35. Crystal structure of cyclo[diaqua-bis(μ2-3′,5-dicarboxy-[1,1′-biphenyl]-3,4′-dicarboxylato-κ4O,O′:O′′,O′′′)-bis(4,4′-bis(pyrid-4-yl)biphenyl-K1N)dicadmium(II)], C76H52Cd2N4O18
  36. Crystal structure of 1-(adamantan-1-yl)-3-aminothiourea, C11H19N3S
  37. Crystal structure of catena-poly[triaqua-(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(3′,5-dicarboxy-[1,1′-biphenyl]-3,4′-dicarboxylato-κO)nickel(II)], C32H26N2O11Ni
  38. Crystal structure of catena-poly[aqua-(μ4-4,4′-(pyridine-3,5-diyl)dibenzoato-κ4O,O′:O′′:O′′′)zinc(II)], C19H13NO5Zn
  39. Crystal structure of 4-(4′-(pyridin-4-yl)-[1,1′-biphenyl]-4-yl)pyridin-1-ium 2-carboxy-4-(3,5-dicarboxyphenoxy)benzoate hydrate, C38H28N2O10
  40. Crystal structure of 3-[(triisopropylsilanyl)-ethynyl]-6a,12a-dihydro-1H-1,4-diaza-benzo[α]anthracene-2,7,12-trione, C27H28N2O3Si
  41. Crystal structure of [(bis(1,10-phenanthroline-κ2N,N′)-(2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ2O:O′))nickel(II) monohydrate, (1,10-phenanthroline-κ2N:N′)-(μ2-(5-(3′,4′-dicarboxylphenoxy)-isophthalate-κ2O:O′))nickel(II)], C40H24N4O9Ni ⋅ H2O
  42. Crystal structure of 4-(3-(pyridin-3-yl)ureido)benzoic acid — adipic acid (2/1), C16H16N3O5
  43. Crystal structure of poly[bis{μ2-5-carboxy-4′-methyl-[1,1′-biphenyl]-3-carboxylato-κ2O:O′}-{μ2-4,4′-bipyridine-κ2N:N′}]cobalt(II), C40H30N2O8Co
  44. Crystal structure of aqua-(2,2′-bipyridine-κ2N,N′)(((3-nitrophenyl)sulfonyl)glycine-κ2N,O)copper(II) dihydrate, C18H20CuN4O9S
  45. Crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}copper(II), C32H28Br2CuN4O4
  46. Crystal structure of bis(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κ2O,O′)-(1,10-phenanthroline-κ2N,N′)zinc(II), C40H28Cl4N4O4Zn
  47. Crystal structure of 2-(3,6-dimethyl-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)-2-oxoethyl acetate, C14H17NO4
  48. Crystal structure of poly[dibromido-bis(μ2-1,6-di(1H-imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C24H36Br2N8Cd
  49. Synthesis and crystal structure of ((6R,7S)-3-ethyl-6-phenyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)(phenyl)methanone hemihydrate, 2(C19H18N4OS) ⋅ H2O
  50. Crystal structure of 2-(5-(pyridin-3-yl)-4-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)pyridine, C17H12N6
  51. The crystal structure of N-((1E,2E)-1,3-bis(4-fluorophenyl)but-2-en-1-ylidene)-4-methylbenzenesulfonamide, C23H19F2NO2S
  52. Crystal structure of diacetato-κ1O-diethanol-κ1O-bis(μ2-2-(((2-hydroxyethyl)imino)methyl)-5-methoxyphenolato-κ4O,N,O′:O′′)dinickel(II), C28H42Ni2N2O12
  53. The crystal structure of catena-poly[chlorido-(μ2-1,4-bis(pyridin-3-yl-methoxy)benzene-κ2N:N′)copper(II)], C18H16ClN2O2Cu
  54. N′,N′′′-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(methaneylylidene))bis(2-hydroxybenzohydrazide)nickel(II), C30H24N4NiO6
  55. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-(2-((quinolin-2-ylmethylene)amino)ethyl)spiro[isoindoline-1,9′-xanthen]-3-one, C38H37N5O2
  56. Crystal structure of 4,4′-di(1H-imidazol-1-yl)-1,1′-biphenyl-1-ium 5,3′,5′-tricarboxy-[1,10-biphenyl]-2-carboxylate, C25H17N2O8
  57. The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C14H19N2O2Cl
  58. The crystal structure of 5-bromo-2-fluoronicotinic acid monohydrate, C6H5BrFNO3
  59. Crystal structure of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C7H7F3N2O2
  60. Crystal structure of tetrakis(1H-benzo[d]imidazol-3-ium) bis(μ5-phenylphosphonato)-pentakis(μ2-oxido)-decaoxo-penta-molybdenum dihydrate, C40H42Mo5N8O23P2
  61. Structure of 7-(3,3,4,4,5,5-hexafluoro-2-(2-methylbenzo[b]thiophen-3-yl)cyclopent-1-en-1-yl)-8-methylquinoline, C24H15F6NS
  62. Crystal structure of monocarbonyl[2-((cyclopentylmethylene)amino)-5-methylphenolato-κ2N,O] (tricyclohexylphosphine)rhodium(I), C32H48NO2PRh
  63. The crystal structure of fac-tricarbonyl(1,10-phenanthroline-κ2N,N′)-(pyrazole-κN)rhenium(I)nitrate, C18H12O3N4Re
  64. Crystal structure of poly[diaqua-bis(μ2-4-(3-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)benzoato-κ2N:O)nickel(II)], C28H22O6N8Ni
  65. Crystal structure of 4,4′-bis(pyridin-1-ium-4-yl)biphenyl poly[bis(μ2-4,4′-bis(pyrid-4-yl)biphenyl-K2N:N′)-tetrakis(μ4-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-K4O,O′:O′′:O′′′)-bis[[μ2-1,1′-biphenyl]-3-carboxyl-5-carboxylato-K2O:O′]tetracobalt(II)]— [1,1′-biphenyl]-3,5-dicarboxylic acid (1/2), C93H68N3O16Co2
  66. The crystal structure of 4a-formyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-1-2-6a,6b,9,9,12a-heptamethylpicen-10-yl acetate, C32H50O3
  67. Crystal structure of 3,3′-(1,2-phenylenebis(methylene))bis(1-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C16H20F12N4P2
  68. Crystal structure of catena-poly[diaqua-(μ2-tartrato-κ4O,O′:O′′,O′′′)zinc(II)], C4H8O8Zn
  69. The crystal structure of (6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-10-(4-acetoxy-3-methylbutyl)-6a,8a,9-trimethyl-3,4,5,6,6a,6b,7,8,8a,8b,9,10,11a,12,12a,12b-hexadecahydro-1H-naphtho[2′,1′:4,5]indeno[2,1-b]furan-4-yl acetate, C31H48O5
  70. Crystal structure of 4,4′-(oxybis(methylene))bis(bromobenzene), C14H12Br2O
  71. Crystal structure of (N,N-dimethylsulphoxide)-[N-(3-ethoxy-2-(oxide)benzylidene)-3-methoxybenzenecarbohydrazonato-κ3N,O,O′]-dioxo-molybdenum(VI), C19H22MoN2O7S
  72. Crystal structure of dichlorido-bis(dimethyl sulphoxide-κO)-bis(4-methylbenzyl-κC1)tin(IV), C20H30Cl2O2S2Sn
  73. Crystal structure of (E)-2-amino-N′-(2-hydroxy-4-(2-(piperidin-1-yl)ethoxy)benzylidene)benzohydrazide monohydrate, C21H26N4O3 ⋅ H2O
  74. Crystal structure of chloridotris(4-chlorophenyl)(dimethyl sulfoxide-κO)tin(IV), C20H18Cl4OSSn
  75. Crystal structure of catena{di-aqua-sodium-[N-(hydroxyethyl), N-isopropyl-dithiocarbamato]}n, [C6H16NNaO2S2]n
  76. Crystal structure of 2,2,4,4,6,6-hexakis(4-chlorophenyl)-1,3,5,2,4,6-trithiatristanninane, C36H24Cl6S3Sn3
  77. Crystal structure of 6-methoxy-3-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4H-chromen-4-one-methanol (1/1), C20H18N2O6
  78. Crystal structure of hexanedihydrazide, C6H14N4O2
  79. Crystal structure of tert-butyl 2-(hydroxymethyl)-5-{4-[(methoxycarbonyl)amino]phenyl}-2,5-dihydro-1H-pyrrole-1-carboxylate, C18H24N2O5
  80. Crystal structure of [(Z)-O-isopropyl N-(4-nitrophenyl)thiocarbamato-κS]-(triphenylphosphine-κP)-gold(I), C28H26AuN2O3PS
  81. Crystal structure of [O-ethyl N-(4-nitrophenyl)thiocarbamato-κS](tri-4-tolylphosphine-κP)gold(I) tetrahydrofuran solvate, C30H30AuN2O3PS, C4H8O
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