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Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-3-yl)methylene)-3, 4-dihydronaphthalen-1(2H)-one, C17H15NO3

  • Sheng-Nan Zhang ORCID logo , Feng-Lan Zhao and Qing-Guo Meng EMAIL logo
Published/Copyright: November 3, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 1

Abstract

C17H15NO3, monoclinic, P21/n (no. 14), a = 4.3970(3) Å, b = 13.8942(8) Å, c = 22.0484(14) Å, β = 91.099(6)°, V = 1346.75(15), Z = 4, R gt (F) = 0.0412, wRref (F2) = 0.1003, T = 150 K.

CCDC no.: 2078244

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: 0.14 × 0.12 × 0.11 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: SuperNova, CCD plate scans
θmax, completeness: 25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint: 6179, 2512, 0.024
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2118
N(param)refined: 192
Programs: CrysAlisPRO [1], SHELX [2,3]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.4103 (3) 0.59130 (11) 0.32499 (7) 0.0209 (3)
C2 0.2800 (3) 0.62282 (11) 0.38360 (7) 0.0208 (3)
C3 0.2984 (4) 0.55204 (11) 0.43536 (7) 0.0230 (4)
H3A 0.160627 0.571695 0.466893 0.028*
H3B 0.503212 0.551673 0.452488 0.028*
C4 0.2146 (3) 0.45095 (11) 0.41360 (7) 0.0222 (3)
H4A 0.242599 0.405774 0.446782 0.027*
H4B 0.001897 0.449622 0.401130 0.027*
C5 0.4936 (3) 0.32575 (11) 0.35329 (7) 0.0226 (4)
H5 0.429679 0.279271 0.380596 0.027*
C6 0.6726 (4) 0.29884 (11) 0.30550 (7) 0.0240 (4)
H6 0.725640 0.234559 0.300547 0.029*
C7 0.7744 (3) 0.36760 (11) 0.26460 (7) 0.0209 (3)
C8 0.6895 (3) 0.46246 (11) 0.27141 (7) 0.0206 (3)
H8 0.755823 0.508562 0.244088 0.025*
C9 0.5041 (3) 0.48944 (11) 0.31927 (7) 0.0188 (3)
C10 0.4070 (3) 0.42076 (11) 0.36142 (7) 0.0185 (3)
C11 0.1545 (3) 0.71073 (11) 0.38609 (7) 0.0222 (4)
H11 0.138271 0.742258 0.348966 0.027*
C12 0.0392 (3) 0.76505 (10) 0.43746 (7) 0.0205 (3)
C13 0.1408 (4) 0.75574 (11) 0.49728 (7) 0.0260 (4)
H13 0.283352 0.707946 0.505846 0.031*
C14 −0.1518 (4) 0.87792 (11) 0.53065 (7) 0.0239 (4)
C15 −0.2689 (4) 0.89500 (12) 0.47248 (8) 0.0334 (4)
H15 −0.410710 0.943597 0.465416 0.040*
C16 −0.1707 (4) 0.83881 (11) 0.42625 (7) 0.0261 (4)
H16 −0.243654 0.849544 0.386960 0.031*
C17 −0.1111 (4) 0.92834 (13) 0.63415 (8) 0.0343 (4)
H17A −0.161393 0.867427 0.651909 0.051*
H17B −0.182775 0.979394 0.659500 0.051*
H17C 0.105531 0.933248 0.630514 0.051*
N1 0.0488 (3) 0.81053 (9) 0.54364 (6) 0.0250 (3)
O1 0.9577 (3) 0.34428 (8) 0.21739 (5) 0.0277 (3)
H1 0.994506 0.286436 0.218249 0.042*
O2 0.4448 (3) 0.64764 (8) 0.28244 (5) 0.0302 (3)
O3 −0.2526 (3) 0.93570 (9) 0.57523 (5) 0.0348 (3)

Source of material

Five milliliters (25%) of sodium hydroxide aqueous solution was added dropwise to the mixture of 7-hydroxy-3, 4-dihydronaphthalen-1(2H)-one and 6-methoxynicotinaldehyde in 10 mL methanol and stirred at room temperature for 3 h. The in process-control was monitored by silica gel thin layer chromatography (TLC, 254 nm). When the reaction was stopped, the precipitate was filtered from the reaction mixture and dissolved with ethyl acetate. The organic phase was washed successively with water and brine, and dried over anhydrous sodium sulfate. After filtration, the ethyl acetate solution was condensed in vacuo to yield a white solid, which was purified by silica-gel column chromatography (petroleum ether: ethyl acetate = 1:2, v/v). Crystals of the title compound were obtained by recrystallization in dichloromethane and methanol (1:1, v/v) system and dried under vacuo at 65 °C for 3 h.

Experimentaldetails

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

Existing studies have used 3,4-dihydronaphthalen-1(2H)-one (DHN) derivatives that showed anti-tumor and anti-inflammatory activities as novel allergic and inflammatory responses modifiers [4–7] and as potential retinoic acid (RA)-metabolizing enzymes inhibitors to treat skin diseases and cancer. However, DHN derivatives are rarely developed as anti-neuroinflammatory drugs, so the synthesis and crystal structure of novel benzylidene-substituted DHN derivatives with anti-neuroinflammatory activities are of great significance. Our group synthesized some of these compounds and studied their anti-neuroinflammatory activity [8–12].

Single crystal structure analysis revealed that the title compound crystallized in the monoclinic space group P21/n. The ORTEP diagram is presented in the Figure. Bond lengths and angles are all in the expected ranges. There is only one drug molecule in the asymmetric unit. The C(2)=C(11) olefinic bond adopts the E stereochemistry [13, 14]. Because of the sterical effect of 3,4-dihydronaphthalen-1(2H)-1, 7-hydroxyphenyl and 6-methoxypyridin-3-yl groups both are not coplanar with each other, showing a dihedral angle of approximately 52°. This twisted configuration may increase likelihood of interactions with bioactive molecules [15].

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: 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. Wang, F. L., Zhang, R. X., Cui, Y., Sheng, L. P., Sun, Y. P., Tian, W., Liu, X., Liang, S. Z. Design, synthesis and biological evaluation of 3,4-dihydronaphthalen-1(2H)-one derivatives as Bcl-2 inhibitors. Res. Chem. Intermed. 2017, 43, 5933–5942; https://doi.org/10.1007/s11164-017-2972-x.Search in Google Scholar

5. 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

6. 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

7. Kirby, A. J., Le, L. 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. Enzym. Inhib. Med. Chem. 2003, 18, 27–33; https://doi.org/10.1080/1475636021000049221.Search in Google Scholar

8. Zhang, X. F., Meng, Q. G. Crystal structure of (E)-2-((2-methoxy-3-pyridyl) methylene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 507–509; https://doi.org/10.1515/ncrs-2020-0603.Search in Google Scholar

9. Luan, M. Z., Meng, Q. G. Crystal structure of (E)-7-methoxy-2((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 387–389; https://doi.org/10.1515/ncrs-2020-0602.Search in Google Scholar

10. 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. C Struct. Chem. 2019, 75, 1157–1165; https://doi.org/10.1107/s2053229619010118.Search in Google Scholar

11. Sun, Y., Zhou, Y. Q., Liu, Y. K., Zhang, H. Q., Hou, G. G., Meng, Q. G., Hou, Y. Potential anti-neuroinflammatory NF-0̆01082B inhibitors based on 3,4-dihydronaphthalen-1(2H)-one derivatives. J. Enzym. Inhib. Med. Chem. 2020, 35, 1631–1640; https://doi.org/10.1080/14756366.2020.1804899.Search in Google Scholar

12. Wang, L., Meng, Q. G., Jiang, N., Wei, L., Wang, C. H. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 1069–1071; https://doi.org/10.1515/ncrs-2021-0222.Search in Google Scholar

13. 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-kappaB pathway activation. Eur. J. Med. Chem. 2019, 167, 187–199; https://doi.org/10.1016/j.ejmech.2019.02.020.Search in Google Scholar

14. 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

15. 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. C 2017, C73, 1003–1009; https://doi.org/10.1107/s2053229617015145.Search in Google Scholar
Received: 2021-10-04
Accepted: 2021-10-22
Published Online: 2021-11-03
Published in Print: 2022-02-23

© 2021 Sheng-Nan Zhang et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-3-yl)methylene)-3, 4-dihydronaphthalen-1(2H)-one, C17H15NO3
  4. Crystal structure of (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1 (2H)-one, C18H17NO3
  5. The crystal structure of N 6,N 6′-di(pyridin-2-yl)-[2,2′-bipyridine]-6,6′-diamine, C20H16N6
  6. The crystal structure of {N 1,N 2-bis[2,4-dimethyl-6-(4-(tert-butyl)phenyl)(phenyl)methyl]acenaphthylene-1,2-diimino-κ2 N, N′}-dibromido-nickel(II) – dichloromethane(1/2), C64H64Br2Cl4N2Ni
  7. Synthesis and crystal structure of nonacarbonyltris[(2-thia-1,3,5-triaza-7-phosphatricylco[3.3.1.1]decane-κ1 P)-2,2-dioxide]triruthenium(0) – acetonitrile (7/6), C25.71H32.57N9.86O15P3S3Ru3
  8. A new polymorph of 1-(4-nitrophenyl)-1H-benzimidazole (C13H9N3O2)
  9. The crystal structure of 2,2′-((1E,1′E)-(naphthalene-2,3 diylbis(azanylylidene)) bis(methanylylidene))bis(4-methylphenol), C26H22N2O2
  10. The crystal structure of bis(μ2-iodido)-bis(η6-benzene)-bis(iodido)-diosmium(II), C12H12I4Os2
  11. Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12
  12. Crystal structure of (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
  13. Crystal structure of 2,2′-(p-tolylazanediyl)bis(1-phenylethan-1-one), C23H21NO2
  14. Redetermination of the crystal structure of the crystal sponge the poly[tetrakis(μ3-2,4,6-tris(pyridin-4-yl)-1,3,5-triazine)-dodecaiodidohexazinc(II) nitrobenzene solvate], C72H48I12N24Zn6⋅10(C6H5NO2)
  15. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C44H45N5O2
  16. Crystal structure of (E)-7-fluoro-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O1
  17. Crystal structure of tetrabutylammonium sulfanilate – 1-(diaminomethylene)thiourea (1/2)
  18. Crystal structure of [2,2′-{azanediyl)bis[(propane-3,1-diyl)(azanylylidene)methylylidene]} bis(3,5-dichlorophenolato)-κ2O,O′]-isothiocyanato-κN-iron(III), C21H19Cl4FeN4O2S
  19. Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2
  20. Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2
  21. Chlorido-(2,2′-(ethane-bis(5-methoxyphenolato))-κ4 N,N′,O,O′)manganese(III) monohydrate, C19H18Cl2CuN2O2
  22. Crystal structure of 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one, C22H28O2
  23. Crystal structure of [6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato)-κ4N,N′,O,O′]copper(II)
  24. Crystal structure of 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione, C30H20O4N2Cl2S2
  25. Crystal structure of bis{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl)borato-κN 3}manganese(II), C30H26B2F18MnN12
  26. Crystal structure of 1-(2-methylphenyl)-2-(2-methylbenzo[b]thienyl)-3,3,4,4,5,5-hexafluorocyclopent-ene, C21H14F6S
  27. Crystal structure of 2-(3-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  28. Crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium chloride – chloroform (1/1), C21H23Cl4I2N3
  29. Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3
  30. The crystal structure of 2-(4-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  31. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C9H14F12N4P2
  32. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(pyren-1-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C54H48N4O2
  33. Crystal structure of poly[bis(μ2-2,6-bis(1-imidazoly)pyridine-κ2 N,N′)-bis(thiocyanato-κ1 N)copper(II)] dithiocyanate, C24H18CuN12S2
  34. Cones with a three-fold symmetry constructed from three hydrogen bonded theophyllinium cations that coat [FeCl4]− anions in the crystal structure of tris(theophyllinium) bis(tetrachloridoferrate(III)) chloride trihydrate, C21H33Cl9Fe2N12O9
  35. Crystal structure of 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin monohydrate, C32H49N3O6S
  36. The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
  37. The crystal structure of 4-phenyl-4-[2-(pyridine-4-carbonyl)hydrazinylidene]butanoic acid, C16H15N3O3
  38. The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3
  39. Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)
  40. Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene) hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
  41. Crystal structure of (E)-amino(2-((5-methylfuran-2-yl)methylene)hydrazinyl) methaniminium nitrate monohydrate, C14H26N10O10
  42. The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
  43. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)zinc(II)], C64H44Br4N8O8Zn2
  44. The crystal structure of catena-poly[(1-(4-carboxybenzyl)pyridin-1-ium-4-carboxylato-κ1O)-(μ2-oxalato-κ4 O:O′:O″:O‴)dioxidouranium(VI)], C16H11NO10U
  45. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
  46. Halogen bonds in the crystal structure of 4,3′:5′,4″-terpyridine — 1,3-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  47. Crystal structure of 2-(1H-indol-3-yl)ethan-1-aminium 2-(4-acetylphenoxy)acetate, C20H22N2O4
  48. Chalcogen bonds in the crystal structure of 4,7-dibromo-2,1,3-benzoselenadiazole, C6H2Br2N2Se
  49. The crystal structure of 1,4-bis((1H-benzimidazol-2-yl)methyl)-piperazine-2,5-dione dihydrate, C20H22N6O4
  50. The crystal structure of C19H20O8
  51. The crystal structure of KNa3Te8O18·5H2O exhibiting a ∞2[Te4O9]2− layer
  52. Erratum
  53. Erratum to: Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
https://doi.org/10.1515/ncrs-2021-0382
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-3-yl)methylene)-3, 4-dihydronaphthalen-1(2H)-one, C17H15NO3
  4. Crystal structure of (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1 (2H)-one, C18H17NO3
  5. The crystal structure of N 6,N 6′-di(pyridin-2-yl)-[2,2′-bipyridine]-6,6′-diamine, C20H16N6
  6. The crystal structure of {N 1,N 2-bis[2,4-dimethyl-6-(4-(tert-butyl)phenyl)(phenyl)methyl]acenaphthylene-1,2-diimino-κ2 N, N′}-dibromido-nickel(II) – dichloromethane(1/2), C64H64Br2Cl4N2Ni
  7. Synthesis and crystal structure of nonacarbonyltris[(2-thia-1,3,5-triaza-7-phosphatricylco[3.3.1.1]decane-κ1 P)-2,2-dioxide]triruthenium(0) – acetonitrile (7/6), C25.71H32.57N9.86O15P3S3Ru3
  8. A new polymorph of 1-(4-nitrophenyl)-1H-benzimidazole (C13H9N3O2)
  9. The crystal structure of 2,2′-((1E,1′E)-(naphthalene-2,3 diylbis(azanylylidene)) bis(methanylylidene))bis(4-methylphenol), C26H22N2O2
  10. The crystal structure of bis(μ2-iodido)-bis(η6-benzene)-bis(iodido)-diosmium(II), C12H12I4Os2
  11. Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12
  12. Crystal structure of (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
  13. Crystal structure of 2,2′-(p-tolylazanediyl)bis(1-phenylethan-1-one), C23H21NO2
  14. Redetermination of the crystal structure of the crystal sponge the poly[tetrakis(μ3-2,4,6-tris(pyridin-4-yl)-1,3,5-triazine)-dodecaiodidohexazinc(II) nitrobenzene solvate], C72H48I12N24Zn6⋅10(C6H5NO2)
  15. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C44H45N5O2
  16. Crystal structure of (E)-7-fluoro-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O1
  17. Crystal structure of tetrabutylammonium sulfanilate – 1-(diaminomethylene)thiourea (1/2)
  18. Crystal structure of [2,2′-{azanediyl)bis[(propane-3,1-diyl)(azanylylidene)methylylidene]} bis(3,5-dichlorophenolato)-κ2O,O′]-isothiocyanato-κN-iron(III), C21H19Cl4FeN4O2S
  19. Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2
  20. Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2
  21. Chlorido-(2,2′-(ethane-bis(5-methoxyphenolato))-κ4 N,N′,O,O′)manganese(III) monohydrate, C19H18Cl2CuN2O2
  22. Crystal structure of 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one, C22H28O2
  23. Crystal structure of [6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato)-κ4N,N′,O,O′]copper(II)
  24. Crystal structure of 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione, C30H20O4N2Cl2S2
  25. Crystal structure of bis{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl)borato-κN 3}manganese(II), C30H26B2F18MnN12
  26. Crystal structure of 1-(2-methylphenyl)-2-(2-methylbenzo[b]thienyl)-3,3,4,4,5,5-hexafluorocyclopent-ene, C21H14F6S
  27. Crystal structure of 2-(3-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  28. Crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium chloride – chloroform (1/1), C21H23Cl4I2N3
  29. Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3
  30. The crystal structure of 2-(4-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  31. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C9H14F12N4P2
  32. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(pyren-1-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C54H48N4O2
  33. Crystal structure of poly[bis(μ2-2,6-bis(1-imidazoly)pyridine-κ2 N,N′)-bis(thiocyanato-κ1 N)copper(II)] dithiocyanate, C24H18CuN12S2
  34. Cones with a three-fold symmetry constructed from three hydrogen bonded theophyllinium cations that coat [FeCl4]− anions in the crystal structure of tris(theophyllinium) bis(tetrachloridoferrate(III)) chloride trihydrate, C21H33Cl9Fe2N12O9
  35. Crystal structure of 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin monohydrate, C32H49N3O6S
  36. The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
  37. The crystal structure of 4-phenyl-4-[2-(pyridine-4-carbonyl)hydrazinylidene]butanoic acid, C16H15N3O3
  38. The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3
  39. Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)
  40. Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene) hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
  41. Crystal structure of (E)-amino(2-((5-methylfuran-2-yl)methylene)hydrazinyl) methaniminium nitrate monohydrate, C14H26N10O10
  42. The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
  43. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)zinc(II)], C64H44Br4N8O8Zn2
  44. The crystal structure of catena-poly[(1-(4-carboxybenzyl)pyridin-1-ium-4-carboxylato-κ1O)-(μ2-oxalato-κ4 O:O′:O″:O‴)dioxidouranium(VI)], C16H11NO10U
  45. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
  46. Halogen bonds in the crystal structure of 4,3′:5′,4″-terpyridine — 1,3-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  47. Crystal structure of 2-(1H-indol-3-yl)ethan-1-aminium 2-(4-acetylphenoxy)acetate, C20H22N2O4
  48. Chalcogen bonds in the crystal structure of 4,7-dibromo-2,1,3-benzoselenadiazole, C6H2Br2N2Se
  49. The crystal structure of 1,4-bis((1H-benzimidazol-2-yl)methyl)-piperazine-2,5-dione dihydrate, C20H22N6O4
  50. The crystal structure of C19H20O8
  51. The crystal structure of KNa3Te8O18·5H2O exhibiting a ∞2[Te4O9]2− layer
  52. Erratum
  53. Erratum to: Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
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