Home Crystal structure of (E)-2-(4-fluoro-3-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
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Crystal structure of (E)-2-(4-fluoro-3-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2

  • Xiao-Fan Zhang ORCID logo , Hui-yun Wang , Sheng-Nan Zhao , Sheng-Nan Zhang , Feng-Lan Zhao and Qing-Guo Meng EMAIL logo
Published/Copyright: October 12, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 1

Abstract

C19H14F4O2, triclinic, P1‾ (no. 2), a = 8.1539(7) Å, b = 8.8584(6) Å, c = 11.8025(9) Å, α = 73.186(7)°, β = 76.184(7)°, γ = 69.512(7)°, V = 755.39(11) Å3, Z = 2, Rgt(F) = 0.0436, wRref(F2) = 0.0965, T = 100 K.

CCDC no.: 2016724

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:0.13 × 0.12 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.13 mm−1
Diffractometer, scan mode:SuperNova,
θmax, completeness:25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:4729, 2802, 0.044
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2165
N(param)refined:227
Programs:CrysAlisPRO [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.2988 (2)0.3305 (2)0.48684 (17)0.0133 (4)
C20.1929 (2)0.3765 (2)0.60124 (16)0.0131 (4)
C30.0556 (2)0.2900 (2)0.66472 (17)0.0154 (4)
H3A−0.0460550.3364180.6227690.018*
H3B0.0160910.3081120.7453520.018*
C40.1307 (2)0.1037 (2)0.67046 (17)0.0162 (4)
H4A0.2184740.0543040.7240990.019*
H4B0.0360670.0534690.7029840.019*
C50.2153 (2)−0.0733 (2)0.51930 (18)0.0173 (4)
H50.158663−0.1450040.5746910.021*
C60.2978 (2)−0.1103 (2)0.40935 (18)0.0187 (5)
H60.296071−0.2053230.3915270.022*
C70.3833 (2)−0.0044 (2)0.32589 (17)0.0164 (4)
C80.3838 (2)0.1365 (2)0.35360 (17)0.0144 (4)
H80.4413050.2072560.2978620.017*
C90.2997 (2)0.1742 (2)0.46359 (16)0.0126 (4)
C100.2144 (2)0.0675 (2)0.54957 (17)0.0144 (4)
C110.2330 (2)0.4869 (2)0.63856 (16)0.0148 (4)
H110.3285920.5215490.5926440.018*
C120.1455 (2)0.5600 (2)0.74244 (16)0.0140 (4)
C130.2469 (2)0.6008 (2)0.80319 (17)0.0146 (4)
H130.3684960.5778840.7783240.017*
C140.1689 (2)0.6745 (2)0.89955 (16)0.0125 (4)
C15−0.0127 (2)0.7119 (2)0.93335 (17)0.0152 (4)
C16−0.1169 (2)0.6785 (2)0.87378 (17)0.0160 (4)
H16−0.2391400.7066030.8967250.019*
C17−0.0369 (2)0.6024 (2)0.77918 (17)0.0150 (4)
H17−0.1068610.5788520.7389100.018*
C180.2747 (2)0.7185 (2)0.96570 (17)0.0165 (4)
C190.4475 (3)−0.1562 (3)0.17480 (19)0.0276 (5)
H19A0.496952−0.2609260.2262630.041*
H19B0.507533−0.1556960.0941910.041*
H19C0.323735−0.1386340.1773940.041*
F1−0.09011 (13)0.78448 (14)1.02701 (10)0.0217 (3)
F20.26292 (14)0.64104 (13)1.08269 (9)0.0209 (3)
F30.22247 (14)0.88031 (13)0.96210 (10)0.0243 (3)
F40.44808 (13)0.67637 (14)0.92155 (10)0.0219 (3)
O10.37797 (17)0.42131 (16)0.41329 (12)0.0189 (3)
O20.46868 (17)−0.02713 (17)0.21432 (12)0.0220 (3)

Source of material

7–Methoxy-1-tetralone and 4-fluoro-3-(trifluoromethyl)benzaldehyde were dissolved in 10 mL methanol. Sodium hydroxide (aqueous solution, 25%) was added to the mixture and stirred for 3 h at room temperature. The in process-control was monitored by silica gel thin layer chromatography (TLC, 254 nm). When 7-methoxy-1-tetralone was disappeared, the precipitate was filtered from the reaction mixture and dissolved with dichloromethane. The organic phase was washed respectively with deionized water and brine, dried over anhydrous sodium sulfate and condensed under vacuum. The crude product was purified by silica-gel column chromatography (petroleum ether: ethyl acetate = 10:1, v/v). Crystals were obtained under ambient conditions via solvent evaporation in the mixed solvents of dichloromethane and methanol (1:1, v/v) and drying under vacuo at 60 °C for 3 h.

Experimental details

The H atoms were placed in idealized positions and treated as riding on their parent atoms, with d(C–H) = 0.97 Å (methylene), Uiso(H) = 1.2Ueq(C), and d(C–H) = 0.93 Å (aromatic), Uiso(H) = 1.2Ueq(C).

Comment

Inflammation is a very common and important basic pathological process [4]. This process can result in the excessive release of inflammatory mediators or cytokines such as NO, TNF-α, PGE2, and interleukin (IL)-6 [5], [6]. When stimulated in the brain, the body defenses by producing inflammation. Microglia is the resident immune competent cells of the CNS [7], [8]. Activated microglia-mediated inflammatory responses play a key role in the pathological development of inflammatory neurodegenerative diseases in the central nervous system (CNS) [4], [7], [8]. Despite distinct embryonic origins, microglia and resident tissue macrophages are related. Monocyte-derived macrophages are classified into phenotyopic subsets: M1, M2a, M2b and M2c. During inflammatory neurodegenerative diseases in CNS, the resident microglia become activated and polarized to a pro-inflammatory M1 phenotype [9]. It has been reported that the pro-inflammatory cytokines (tumor necrosis factor (TNF-α), interleukin (IL)-6, IL-1β) secreted from M1 microglia can compromise BBB functions by activating the nuclear factor κB (NF-κB) signaling pathway [4], [10], [11], leading to BBB disruption. Concomitantly, the BBB disruption can promote glial activation then boosts CNS inflammation [12]. Moreover, activated microglia can produce reactive oxygen species (ROS), which may indirectly trigger neuroinflammation by activating NF-κB [13]. Therefore, an NF-κB inhibitor may be a perspective drug for the treatment of inflammatory CNS neurodegenerative diseases.

3,4-Dihydronaphthalen-1(2H)-one (DHN)derivatives with antitumor and anti-inflammatory activities have been investigated as novel modulators of allergic and inflammatory responses [14]. But DHN derivatives have rarely been developed as anti-neuroinflammatory drugs [4]. We designed a series of new benzylidene-substituted DHN derivatives and synthesized them through Claisen–Schmidt condensation reactions.

The crystal structure analysis revealed that F1–2 crystallized in the triclinic space group P1‾. The ORTEP diagram is presented in the Figure. There is only one drug molecule in the asymmetric unit. Compared to the C(2)=C(11) olefinic bonds, 4-fluoro-3-(trifluoromethyl)phenyl and carbonyl groups adopt the Estereochemistry [15], [16]. Because of the sterical effects 3,4-dihydrobenzo[b]oxepin-5(2H)-one, the 7-methoxyphenyl and 4-fluoro-3-(trifluoromethyl)phenyl groups are not coplanar with each other. This twisted configuration may increase interactions with bioactive molecules, for the purposes of creating more potent biological activity [17]. Bond lengths and angles are all in the expected ranges [18].

Corresponding author: Qing-Guo Meng, School of Pharmacy, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Yantai University, Yantai, PR China, E-mail:

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 2020XDRH105

Funding source: Science and Technology Innovation Development Plan of Yantai

Award Identifier / Grant number: 2020XDRH105

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

  2. Funding information: This work was supported by Science and Technology Innovation Development Plan of Yantai (No. 2020XDRH105) and the National Natural Science Foundation of China (No. 81473104).

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

References

1. Rigaku OD. CrysAlispro; Rigaku Oxford Diffraction Ltd: Yarnton, Oxfordshire, England, 2017.Search in Google Scholar

2. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Sun, Y., Gao, Z. F., Wang, C. H., Hou, G. G. Synthesis, crystal structures and anti-inflammatory activity of fluorine-substituted 1,4,5,6-tetrahydrobenzo [h]quinazolin-2-amine derivatives. Acta Crystallogr. 2019, C75, 1157–1165; https://doi.org/10.1107/s2053229619010118.Search in Google Scholar

5. Zhang, J. Q., Zhang, Q., Xu, Y. R., Li, H. X., Zhao, F. L., Wang, C. M., Liu, Z., Liu, P., Liu, Y. N., Meng, Q. G., Zhao, F. Synthesis and in vitro anti-inflammatory activity of C20 epimeric ocotillol-type triterpenes and protopanaxadiol. Planta Med. 2019, 85, 292–301; https://doi.org/10.1055/a-0770-0994.Search in Google Scholar

6. Wang, C. M., Liu, J., Deng, J. Q., Wang, J. Z., Weng, W. Z., Chu, H. X., Meng, Q. G. Advances in the chemistry, pharmacological diversity, and metabolism of 20(R)-ginseng saponins. J. Ginseng Res. 2020, 44, 14–23; https://doi.org/10.1016/j.jgr.2019.01.005.Search in Google Scholar

7. Sun, Y., Zhou, Y. Q., Liu, Y. K., Zhang, H. Q., Hou, G. G., Meng, Q. G., Hou, Y. Potential anti-neuroinflammatory NF-κB inhibitors based on 3,4-dihydronaphthalen-1(2H)-one derivatives. J. Enzyme Inhib. Med. Chem. 2020, 35, 1631–1640; https://doi.org/10.1080/14756366.2020.1804899.Search in Google Scholar

8. Gao, C. L., Hou, G. G., Liu, J., Ru, T., Xu, Y. Z., Zhao, S. Y., Ye, H., Zhang, L. Y., Chen, K. X., Guo, Y. W., Pang, T., Li, X. W. Synthesis and target identification of benzoxepane derivatives as potential anti-neuroinflammatory agents for ischemic stroke. Angew. Chem. Int. Ed. 2020, 59, 2429–2439; https://doi.org/10.1002/anie.201912489.Search in Google Scholar

9. Streit, W. J., Xue, Q. S., Tischer, J., Bechmann, I. Microglial pathology. Acta Neuropathol. Commun. 2014, 2, 142; https://doi.org/10.1186/s40478-014-0142-6.Search in Google Scholar

10. Pisanu, A., Lecca, D., Mulas, G., Wardas, J., Simbula, G., Spiga, S., Carta, A. R. Dynamic changes in pro-and anti-inflammatory cytokines in microglia after PPAR-gamma agonist neuroprotective treatment in the MPTPp mouse model of progressive Parkinson’s disease. Neurobiol. Dis. 2014, 71, 280–291; https://doi.org/10.1016/j.nbd.2014.08.011.Search in Google Scholar

11. Liu, J., Xu, Y. R., Yang, J. J., Wang, W. Z., Zhang, J. Q., Zhang, R. M., Meng, Q. G. Discovery, semisynthesis, biological activities, and metabolism of ocotillol-type saponins. J. Ginseng Res. 2017, 41, 373–378; https://doi.org/10.1016/j.jgr.2017.01.001.Search in Google Scholar

12. Hou, Y., Ryu, C. H., Park, K. Y., Kim, S. M., Jeong, C. H., Jeun, S. S. Effective combination of human bone marrow mesenchymal stem cells and minocycline in experimental autoimmune encephalomyelitis mice. Stem Cell Res. Ther. 2013, 4, 77; https://doi.org/10.1186/scrt228.Search in Google Scholar

13. Yang, Y., Salayandia, V. M., Thompson, J. F., Yang, L. Y., Estrada, E. Y., Yang, Y. Attenuation of acute stroke injury in rat brain by minocycline promotes blood-brain barrier remodeling and alternative microglia/macrophage activation during recovery. J. Neuroinflammation, 2015, 12, Article 26; https://doi.org/10.1186/s12974-015-0245-4.Search in Google Scholar

14. Barlow, J. W., Zhang, T., Woods, O., Byrne, A. J., Walsh, J. J. Novel mast cell-stabilising amine derivatives of 3,4-dihydronaphthalen-1(2H)-one and 6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one. Med. Chem. 2011, 7, 213–223; https://doi.org/10.2174/157340611795564222.Search in Google Scholar

15. Li, N., Xin, W. Y., Yao, B. R., Wang, C. H., Cong, W., Zhao, F., Li, H. J., Hou, Y., Meng, Q. G., Hou, G. G. Novel dissymmetric 3,5-bis(arylidene)-4-piperidones as potential antitumor agents with biological evaluation in vitro and in vivo. Eur. J. Med. Chem. 2018, 147, 21–33; https://doi.org/10.1016/j.ejmech.2018.01.088.Search in Google Scholar

16. Yao, B. R., Sun, Y., Chen, S. L., Suo, H. D., Zhang, Y. L., Wei, H., Wang, C. H., Zhao, F., Cong, W., Xin, W. Y., Hou, G. G. Dissymmetric pyridyl-substituted 3,5-bis(arylidene)-4-piperidones as anti- hepatoma agents by inhibiting NF-kB pathway activation. Eur. J. Med. Chem. 2019, 167, 187–199; https://doi.org/10.1016/j.ejmech.2019.02.020.Search in Google Scholar

17. Li, N., Yao, B. Y., Wang, C. H., Meng, Q. G., Hou, G. G. Synthesis, crystal structure and activity evaluation of novel 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives as protein–tyrosine kinase (PTK) inhibitors. Acta Crystallogr. 2017, C73, 1003–1009; https://doi.org/10.1107/s2053229617015145.Search in Google Scholar

18. El-Sayed, N. E., Almaneai, N. M., Ghabbour, H. A., Alafeefy, A. M. Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H18O4, Z. Kristallogr. NCS 2017, 232, 203–205.10.1515/ncrs-2016-0195Search in Google Scholar

Received: 2020-08-19
Accepted: 2020-09-23
Published Online: 2020-10-12
Published in Print: 2021-01-26

© 2020 Xiao-Fan Zhang 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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  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
https://doi.org/10.1515/ncrs-2020-0448
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Articles in the same Issue

  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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