Home Crystal structure of (E)-2-((2-methoxy-3-pyridyl)methylene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
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Crystal structure of (E)-2-((2-methoxy-3-pyridyl)methylene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2

  • Xiao-Fan Zhang ORCID logo and Qing-Guo Meng
Published/Copyright: January 28, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 3

Abstract

C17H14FNO2, monoclinic, P21/c (no. 14), a = 14.0279(13) Å, b = 7.0527(5) Å, c = 14.4150(16) Å, β = 113.165(12)°, V = 1311.2(2) Å3, Z = 4, Rgt(F) = 0.0524, wRref(F2) = 0.1358, T = 100 K.

CCDC no.: 2039247

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:0.15 × 0.13 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.10 mm−1
Diffractometer, scan mode:SuperNova
θmax, completeness:25.5°, 99%
N(hkl)measured, N(hkl)unique, Rint:4957, 2438, 0.031
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1910
N(param)refined:191
Programs:CrysAlisPRO [1], SHELX [2], [,3]
Table 2:

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

xyzUiso*/Ueq
C10.47372 (16)0.5363 (3)0.60726 (15)0.0216 (5)
C20.52721 (16)0.7232 (3)0.64029 (15)0.0206 (5)
C30.46085 (16)0.8992 (3)0.62279 (16)0.0229 (5)
H3A0.4474390.9485260.5559910.027*
H3B0.4987720.9952430.6715250.027*
C40.35743 (16)0.8621 (3)0.63186 (17)0.0244 (5)
H4A0.3699260.8424880.7022990.029*
H4B0.3134850.9728750.6085100.029*
C50.19429 (16)0.6850 (3)0.52630 (16)0.0252 (5)
H50.1559410.7910730.5287010.030*
C60.14291 (17)0.5233 (3)0.47724 (17)0.0277 (5)
H60.0709190.5200370.4464110.033*
C70.20129 (17)0.3674 (3)0.47532 (16)0.0250 (5)
C80.30745 (16)0.3677 (3)0.51677 (16)0.0228 (5)
H80.3447350.2608620.5132130.027*
C90.35843 (16)0.5333 (3)0.56472 (15)0.0201 (5)
C100.30175 (16)0.6922 (3)0.57194 (15)0.0213 (5)
C110.63138 (16)0.7192 (3)0.68050 (15)0.0220 (5)
H110.6598740.5980550.6916360.026*
C120.70752 (16)0.8725 (3)0.70972 (16)0.0216 (5)
C130.81155 (16)0.8328 (3)0.77370 (16)0.0225 (5)
C140.86833 (17)1.1292 (3)0.75901 (17)0.0270 (5)
H140.9224331.2158670.7748600.032*
C150.77038 (17)1.1868 (3)0.69688 (16)0.0254 (5)
H150.7584121.3100060.6720160.031*
C160.69004 (17)1.0579 (3)0.67206 (16)0.0243 (5)
H160.6234031.0948340.6297620.029*
C170.93629 (16)0.6116 (4)0.87542 (18)0.0304 (6)
H17A0.9800480.6371500.8397710.046*
H17B0.9423230.4803710.8946410.046*
H17C0.9572010.6894830.9347250.046*
F10.15087 (10)0.2050 (2)0.42968 (10)0.0362 (4)
N10.88976 (14)0.9528 (3)0.79815 (13)0.0254 (5)
O10.52231 (11)0.3891 (2)0.61177 (12)0.0296 (4)
O20.83063 (11)0.6529 (2)0.81134 (11)0.0279 (4)

Source of material

7-Fluoro-3,4-dihydro-1(2H)-naphthalenone (0.7 g, 4.26 mmol) and 2-fluoro-3-formylpyridine (0.53 g, 4.26 mmol) were dissolved in 10 mL methanol. A sodium hydroxide aqueous solution (25%) was added to the mixture and stirred for 3 h at room temperature. The response endpoint was detected by thin layer chromatography (TLC, 254 nm). When 7-fluoro-3,4-dihydro-1(2H)-naphthalenone 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). Single crystal was obtained under ambient conditions via solvent evaporation in the mixed solvents of dichloromethane and methanol (1:1, v/v) and drying under vacuo at 333 K 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) = 0.96 Å (methyl), Uiso(H) = 1.5Ueq(C), and 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

Microglia become activated under brain injury and immunological stimuli and undergo several alterations from a resting state to an active state. This activation and consequent neuroinflammation are substantially involved in the pathological development of inflammatory neurodegenerative diseases in the central nervous system (CNS) [4], [, 5]. It has been reported that pro-inflammatory cytokines [tumor necrosis factor (TNF-α), interleukin (IL)-6, IL-1β] secreted from M1 microglia increase blood-brain barrier (BBB) permeability by activating the nuclear factor kappa B (NF-κB) signaling pathway during inflammatory neurodegenerative diseases in CNS [6], [7], [8]. Concomitantly, the disruption of the blood-brain barrier can result in severe inflammatory response that aggravates the brain injury [9]. In addition, activated microglia can produce reactive oxygen species (ROS), which may indirectly induce neuroinflammation by activating NF-κB [10], [, 11]. Therefore, NF-κB inhibitor with anti-neuroinflammatory activity may represent a therapeutic option for the treatment of inflammatory neurodegenerative diseases [12], [13], [14].

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 [15], [, 16]. Our interests lie in developing these derivatives as anti-neuroinflammatory drugs. In this study, we designed and synthesized a new DHN derivative through Claisen–Schmidt condensation reaction.

Single crystals of the title compound were prepared under ambient conditions, with crystallization obtained via solvent evaporation in the mixed solvents of methanol and dichloromethane. Single-crystal structure analysis revealed that the title compound, here termed XF-1-4-2, crystallized in the monoclinic space group P21/c. The ORTEP diagram is presented in the Figure. There is only a drug molecule in the asymmetric unit. With respect to the C(12) = C(11) olefinic bonds, 2-methoxyphenyl and carbonyl groups adopt the E stereochemistry [17]. Because of the distorting effect of 3,4-dihydrobenzo[b]oxepin-5(2H)-one, the 7-fluorophenyl and 2-methoxyphenyl groups are not coplanar with each other, with a dihedral angle of approximately 37.8(3)°. This twisted configuration may increase the likelihood of interactions with bioactive molecules or the purposes of creating more potent biological activity [18], [, 19]. All geometric parameters are in the expected ranges [20]. Displacement ellipsoids are drawn at the 50% probability level.

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, P. R. China, E-mail:

Funding source: Science and Technology Innovation Development Plan of Yantai

Award Identifier / Grant number: 2020XDRH105

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 81473104

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

  2. Research funding: 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 PubMed

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. Goldmann, T., Prinz, M. Role of microglia in CNS autoimmunity. Clin. Dev. Immunol. 2013, 2013, 208093; https://doi.org/10.1155/2013/208093.Search in Google Scholar PubMed PubMed Central

5. 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 PubMed

6. Correale, J. The role of microglial activation in disease progression. Mult. Scler. J. 2014, 20, 1288–1295; https://doi.org/10.1177/1352458514533230.Search in Google Scholar PubMed

7. 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 vivo 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 PubMed

8. 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 PubMed PubMed Central

9. 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 PubMed

10. Bi, Y., Yang, J., Ma, C., Liu, Z. Y., Zhang, T. T., Zhang, X. C., Lu, J., Meng, Q. G. Design, synthesis and in vitro NO-releasing activities of ocotillol-type furoxans. Pharmazie 2015, 70, 213–218.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 PubMed PubMed Central

12. 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 PubMed PubMed Central

13. Zeng, K. W., Wang, S., Dong, X., Jiang, Y., Tu, P. F. Sesquiterpene dimer (DSF-52) from Artemisia argyi inhibits microglia-mediated neuroinflammation via suppression of NF-κB, JNK/p38 MAPKs and Jak2/Stat3 signaling pathways. Phytomedicine 2014, 21, 298–306; https://doi.org/10.1016/j.phymed.2013.08.016.Search in Google Scholar PubMed

14. Sun, Y., Gao, Z. F., Yan, W. B., Yao, B. R., Xin, W. Y., Wang, C. H., Meng, Q. G., Hou, G. G. Discovery of novel NF-κB inhibitor based on scaffold hopping: 1,4,5,6,7,8-hexahydropyrido[4,3-d] pyrimidine. Eur. J. Med. Chem. 2020, 198, 112366; https://doi.org/10.1016/j.ejmech.2020.112366.Search in Google Scholar PubMed

15. 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 PubMed

16. Kirby, A. J., Le Lain, R., Maharlouie, F., Mason, P., Nicholls, P. J., Smith, H. J., Simons, C. Inhibition of retinoic acid metabolising enzymes by 2-(4-aminophenylmethyl)-6-hydroxy-3,4-dihydronaphthalen-1(2H)-one and related compounds. J. Enzyme Inhib. Med. Chem. 2003, 18, 27–33; https://doi.org/10.1080/1475636021000049221.Search in Google Scholar PubMed

17. 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 PubMed

18. Yang, Q. W., Wang, N., Zhang, J., Chen, G., Xu, H., Meng, Q. G., Du, Y., Yang, X., Fan, H. Y. In vitro and in silico evaluation of stereoselective effect of ginsenosideisomers on platelet P2Y12 receptor. Phytomedicine 2019, 64, 152899; https://doi.org/10.1016/j.phymed.2019.152899.Search in Google Scholar PubMed

19. 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

20. Sun, Y., Gao, Z., Wang, C., Hou, 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 PubMed

Received: 2020-11-18
Accepted: 2020-12-30
Published Online: 2021-01-28
Published in Print: 2021-05-26

© 2020 Xiao-Fan Zhang and Qing-Guo Meng, published by De Gruyter, Berlin/Boston

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

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  56. Crystal structure of (R)-6-(benzo[b]thiophen-5-yl)-2-methyl-2,6-dihydrobenzo [5,6] silino[4,3,2-cd]indole, C23H17NSSi
  57. Crystal structure of catena-poly[bis(μ2-thiocyanato-κ2N:S)-(2-(5-methyl-1H-pyrazol-3-yl)pyridine-κ2N,N′)cadmium(II)]–dioxane (1/1), C15H17CdN5O2S2
  58. Crystal structure of poly[aqua-(μ2-1,4-bis(2′-carboxylatophenoxy)benzene-κ2O:O′)-(μ2-4,4′-bipyridione-κ2N:N′)cadmium(II)] monhydrate, C30H22CdN2O7⋅H2O
  59. Crystal structure of catena-poly[tetraaqua-(μ2-4,4′-bipyridine-k2N:N′)-bis(μ2-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-k4O,O′:O″,O′″)dicadmium(II)] dihydrate, C20H20NO7Cd
  60. Crystal structure of 1‐tert‐butyl‐3‐(2,6‐diisopropyl‐4‐phenoxyphenyl)‐2-methylisothiourea, C24H34N2OS
  61. Crystal structure of catena-poly[triaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ1O)cobalt(II)] — N,N′-dimethylformamide (1/1), C28H34N8O8Co
  62. Crystal structure of tetraaqua-bis(1,4-di(1H-imidazol-1-yl)benzene-κ1N)manganese(II) 2,3-dihydroxyterephthalate, C32H32MnN8O10
https://doi.org/10.1515/ncrs-2020-0603
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxidoethylidene)benzohydrazonato-κ5N,O,O′:N′,O′′)hexkis(pyridine-κ1N)trinickel(II) - pyridine (1/1), C63H57Cl2N13Ni3O6
  4. Crystal structure of [(μ2-succinato κ3O,O′:O′′)-bis-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)]dinickel(II)] diperchlorate, dihydrate C36H82Cl2N8Ni2O15
  5. Crystal structure of catena-poly[aquabis(3-nitrobenzoato-κ2O:O′)-(μ2-pyrazine-N: N′)cadmium(II)], C18H14N4O9Cd
  6. Crystal structure of 4-(2,2-difluoroethyl)-2,4,6-trimethylisoquinoline-1,3(2H,4H)-dione, C14H15F2NO2
  7. The crystal structure of thioxanthen-9-one-10,10-dioxide, C13H8O3S – a second polymorph
  8. Crystal structure of (E)-2-((2-methoxy-3-pyridyl)methylene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  9. The crystal structure of diaquahydrogen 2,5-dimethylbenzenesulphonate, C8H14O5S
  10. The crystal structure of N-(4-(cyclohexylimino)pent-2-en-2-yl)cyclohexanamine, C17H30N2
  11. The twinned crystal structure of 1,3-phenylenedimethanaminium dibromide, C8H14Br2N2
  12. Crystal structure of 2,4,7,9-tetranitro-10H-benzofuro[3,2-b]indole – dimethyl sulfoxide (1/1), C16H11N5O10S
  13. Crystal structure of 2,6-bis(2-(pyridin-3-yl)ethyl)pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone, C24H18N4O4
  14. The crystal structure of 3,4-dichlorobenzoic acid chloride, C7H3Cl3O
  15. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-k2S:S)zinc(II), C26H18N6ZnS4
  16. Crystal structure of tetrakis(μ-naphthalene-1-carboxylato-κ2O,O′)bis(methanol)copper(II), C46H36Cu2O10
  17. Crystal structure of 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one, C14H13NO
  18. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 3-nitrophthalate monohydrate, C12H19N9O7S2
  19. Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate), C18H24F12N4P2
  20. The crystal structure of 5-hydroxy-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one– rubrofusarin B, C16H14O5
  21. The crystal structure of bis(ethanol-kO)- bis(6-aminopicolinato-k2N,O)manganese(II), C16H22O6N4Mn
  22. The crystal structure of 3,3′-((carbonylbis(azanediyl))bis(ethane-2,1-diyl)) bis(1-methyl-1H-benzo[d]imidazol-3-ium) tetrafluoroborate monohydrate, C21H28N6O3B2F8
  23. Crystal structure of dimethanol-dichlorido-bis( μ2-2-(((1,5-dimethyl-3-oxo-2- phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato- κ4O:O,O′,N)dinickel (II), C20H24ClNiN3O4
  24. The crystal structure of methyl 5-(trifluoromethyl)-1H-pyrrole-2-carboxylate, C7H6F3NO2
  25. Crystal structure of (OC‐6‐13)‐aqua‐tris (3‐bromopyridine‐κ1N)‐bis(trifluoroacetato‐κ1O)cadmium(II) C19H14Br3CdF6N3O5
  26. Crystal structure of methyl (E)-3-(4-(2-ethoxy-2-oxoethoxy)phenyl) acrylate, C14H16O5
  27. Crystal structure of methyl 4-acetoxy-3,5-dimethoxybenzoate, C12H14O6
  28. The crystal structure of 2-(1H-benzimidazol-2-yl)-3-bromo-5-chlorophenol, C13H8BrClN2O
  29. The crystal structure of bis(μ2-5-chloro-N-(2-methyl-1-oxidopropylidene)-2-oxidobenzohydrazonate-κ5N,O,O′:N′,O′′)pentakis(pyridine-κ1N)tricopper(II), C47H45Cl2N9Cu3O6
  30. Synthesis and crystal structure of catena-poly[aqua-bis(nitrato-κ2O:O′)- (μ2-((1 H-imidazol-1-yl)methyl)benzene-κ2 N,N′)-H2O-κ2O]cadmium(II), C14H16N6O7Cd
  31. The crystal structure of pentakis(carbonyl)-{μ-[2,3-bis(sulfanyl)propan-1-olato]}-(triphenylphosphane)diiron (Fe–Fe)C26H21Fe2O6PS2
  32. Crystal structure of ethyl-2-(3-benzoylthioureido)propanoate, C13H16N2O3S
  33. Crystal structure of 2-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino[2′,1′:1,6] pyrazino[2,3-b]quinoxaline, C19H18N4O
  34. Crystal structure of 2,2′-[ethane-1,2-diylbis(azanylylidenemethylylidene)]bis(6-chlorophenol), C16H14Cl2N2O2
  35. The crystal structure of (Z)-3-((2-(2-(2-aminophenoxy)ethoxy)phenyl)amino)-1-phenylbut-2-en-1-one, C24H24N2O3
  36. The crystal structure of 10-(3,5-di(pyridin-4-yl)phenyl)-10H-phenoxazine dihydrate, C28H23N3O3
  37. Crystal structure of poly[dipoly[aqua-di(µ2-pyrazin-2-olato-κ2N:N′) zinc(II)], C8H8N4O3Zn
  38. Crystal structure of poly[tetra(μ2-cyanido-κ2N:O)-bis(N,N-dimethylformamide-κO)-manganese(II)-platinum(II)], C10H14MnN6O2Pt
  39. The crystal structure of aqua-chlorido-6,6′-((ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dichlorophenolato-κ4N,N′,O,O′)manganese(III), C16H12Cl5MnN2O3
  40. Crystal structure of [di(µ2-cyanido)-dicyanido-bis(dimethyl sulfoxide-κO)- bis(2,2′-(ethane-1,2-diylbis(azanylylidenemethanylylidene))diphenolato-κ4,N,N′,O,O′)- dimanganese(III)-platinum(II)], C40H40Mn2N8O6PtS2
  41. The crystal structure of (azido)-κ1N-6,6′-((cyclohexane-1,2-diylbis(azanylylidene)) bis(methanylylidene))bis(3-bromophenolato-κ4N,N,O,O)-(methanol)-manganese(III)–methanol(1/1), C22H26Br2MnN5O4
  42. Crystal structure of 7-chloro-N-(4-iodobenzyl)-1,2,3,4-tetrahydroacridin-9-amine, C20H18ClIN2
  43. Crystal structure of catena-poly[(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N′′′)-bis(μ2-thiocyanato-κ2N:S)-bis(thiocyanato-κS)-nickel(II)palladium(II)], C14H24N8NiPdS4
  44. Crystal structure of 3-chloro-4-(4-ethylpiperazin-1-yl)aniline monohydrate, C12H20ClN3O
  45. Crystal structure of the 2D coordination polymer poly[diaqua-bis(μ2-3- methoxyisonicotinato-κ2N:O)cobalt(II)] — dimethylformamide (1/1), C20H30CoN4O10
  46. Crystal structure of 4-[(5-chloro-2-hydroxybenzylidene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione, C12H13ClN4OS
  47. Crystal structure of N-(5-(2-(benzyl(1-(4-methoxyphenyl)propan-2-yl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide, C33H36N2O4
  48. Crystal structure of 3-(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C9H12O5
  49. The crystal structure of 1-((dimethylamino)(3-nitrophenyl)methyl)naphthalen-2-ol, C19H18N2O3
  50. Crystal structure of catena-poly[di(μ2-cyanido-κ2C:N)-dicyanido-tetrakis(dimethyl sulfoxide-κO)-manganese(II)-platinum(II)], C12H24MnN4O4PtS4
  51. Crystal structure of 4-amino-N-(2-pyrimidinyl)benzenesulfonamide–1,4-dioxane (1/1), C14H18N4O4S
  52. Crystal structure of bis{1-[(benzotriazol-1-yl)methyl]-1H-1,3-(2-methyl-imidazol)}di-chloridomercury(II), [Hg(C11H11N5)2Cl2], C22H22N10Cl2Hg
  53. Crystal structure of 2, 3-bis((4-methylbenzoyl)oxy) succinic acid–N, N-dimethylformamide (1/1), C23H25NO9
  54. Crystal structure of catena-poly[bis(4-(4-carboxyphenoxy)benzoato-κ1O)-μ2-(1,4-bis(1-imidazolyl)benzene-κ2N:N′)cobalt(II)], C40H28N4O10Co
  55. Crystal structure of 1H-imidazol-3-ium poly[aqua-(μ4-glutarato-κ6O,O′:O′:O′′,O′′′:O′′′)-(nitrato-κ2O,O′)strontium(II)], C8H13N3O8Sr
  56. Crystal structure of (R)-6-(benzo[b]thiophen-5-yl)-2-methyl-2,6-dihydrobenzo [5,6] silino[4,3,2-cd]indole, C23H17NSSi
  57. Crystal structure of catena-poly[bis(μ2-thiocyanato-κ2N:S)-(2-(5-methyl-1H-pyrazol-3-yl)pyridine-κ2N,N′)cadmium(II)]–dioxane (1/1), C15H17CdN5O2S2
  58. Crystal structure of poly[aqua-(μ2-1,4-bis(2′-carboxylatophenoxy)benzene-κ2O:O′)-(μ2-4,4′-bipyridione-κ2N:N′)cadmium(II)] monhydrate, C30H22CdN2O7⋅H2O
  59. Crystal structure of catena-poly[tetraaqua-(μ2-4,4′-bipyridine-k2N:N′)-bis(μ2-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-k4O,O′:O″,O′″)dicadmium(II)] dihydrate, C20H20NO7Cd
  60. Crystal structure of 1‐tert‐butyl‐3‐(2,6‐diisopropyl‐4‐phenoxyphenyl)‐2-methylisothiourea, C24H34N2OS
  61. Crystal structure of catena-poly[triaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ1O)cobalt(II)] — N,N′-dimethylformamide (1/1), C28H34N8O8Co
  62. Crystal structure of tetraaqua-bis(1,4-di(1H-imidazol-1-yl)benzene-κ1N)manganese(II) 2,3-dihydroxyterephthalate, C32H32MnN8O10
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