Home Crystal structure of (8R,10R,14R, Z)-2-((3–Fluoropyridin-4-yl) methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6, 6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a] phenanthren-3-one, C36H52FNO3
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Crystal structure of (8R,10R,14R, Z)-2-((3–Fluoropyridin-4-yl) methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6, 6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a] phenanthren-3-one, C36H52FNO3

  • Mei Zhang , Qing-Guo Meng , Gui-Ge Hou , Sheng Jiang , Yong-Sheng Jin and Yue Gao EMAIL logo
Published/Copyright: July 30, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 6

Abstract

C36H52FNO3, orthorhombic, P212121 (no. 19), a = 7.8016(7) Å, b = 13.1609(10) Å, c = 30.536(2) Å, V = 3135.3(4) Å3, Z = 4, R gt (F) = 0.0657, wR ref (F2) = 0.1435, T = 100 K.

CCDC no.: 2087492

The molecular structure is shown in the figure. Displacement ellipsoids are drawn at the 30% probability level. 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 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: SuperNova,
θmax, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint: 14226, 5509, 0.095
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 3824
N(param)refined: 379
Programs: CrysAlisPRO [1], SHELX [2], [3], [4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.2876 (6) 0.7168 (3) 0.60218 (14) 0.0267 (11)
H1A 0.391895 0.711210 0.585065 0.032*
H1B 0.201292 0.674928 0.588127 0.032*
C2 0.2280 (6) 0.8262 (3) 0.60106 (14) 0.0271 (11)
C3 0.1648 (6) 0.8737 (3) 0.64248 (15) 0.0270 (11)
C4 0.1101 (6) 0.8075 (3) 0.68105 (13) 0.0245 (11)
C5 0.1568 (6) 0.6943 (3) 0.67499 (13) 0.0241 (10)
H5 0.063715 0.666078 0.657200 0.029*
C6 0.1523 (7) 0.6339 (4) 0.71757 (15) 0.0344 (12)
H6A 0.247982 0.654206 0.735862 0.041*
H6B 0.047317 0.649423 0.733223 0.041*
C7 0.1616 (7) 0.5208 (4) 0.70934 (15) 0.0367 (13)
H7A 0.061956 0.500185 0.692562 0.044*
H7B 0.157977 0.485487 0.737197 0.044*
C8 0.3249 (6) 0.4888 (3) 0.68446 (14) 0.0275 (11)
C9 0.3439 (6) 0.5559 (3) 0.64300 (14) 0.0237 (10)
H9 0.248135 0.535487 0.624201 0.028*
C10 0.3222 (6) 0.6738 (3) 0.64821 (14) 0.0234 (10)
C11 0.5050 (6) 0.5247 (3) 0.61719 (17) 0.0342 (12)
H11A 0.512165 0.565863 0.590916 0.041*
H11B 0.605323 0.539177 0.634859 0.041*
C12 0.5085 (7) 0.4125 (4) 0.60404 (16) 0.0360 (13)
H12 0.420024 0.400024 0.581915 0.043*
C13 0.4765 (6) 0.3444 (3) 0.64334 (15) 0.0272 (11)
H13 0.572895 0.354512 0.663464 0.033*
C14 0.3121 (6) 0.3757 (3) 0.66842 (14) 0.0262 (11)
C15 0.3062 (8) 0.2928 (4) 0.70371 (16) 0.0412 (14)
H15A 0.381189 0.309854 0.727964 0.049*
H15B 0.190522 0.284310 0.714747 0.049*
C16 0.3676 (6) 0.1958 (4) 0.68072 (15) 0.0355 (13)
H16A 0.271161 0.151548 0.674560 0.043*
H16B 0.447942 0.159411 0.699215 0.043*
C17 0.4566 (6) 0.2288 (3) 0.63713 (14) 0.0248 (11)
H17 0.373820 0.218237 0.613419 0.030*
C18 0.4772 (7) 0.5014 (4) 0.71648 (16) 0.0406 (14)
H18A 0.484252 0.570963 0.725801 0.061*
H18B 0.581699 0.482664 0.701979 0.061*
H18C 0.460133 0.458459 0.741503 0.061*
C19 0.4816 (6) 0.7281 (4) 0.66655 (17) 0.0336 (12)
H19A 0.581300 0.706522 0.650655 0.050*
H19B 0.494925 0.711423 0.696960 0.050*
H19C 0.467863 0.800246 0.663459 0.050*
C20 0.6169 (6) 0.1648 (3) 0.62624 (14) 0.0259 (11)
C21 0.7709 (6) 0.1363 (3) 0.55358 (14) 0.0278 (11)
C22 0.7212 (7) 0.0240 (3) 0.55536 (15) 0.0334 (12)
H22A 0.614124 0.014163 0.539798 0.040*
H22B 0.808645 −0.015991 0.540749 0.040*
C23 0.7014 (7) −0.0131 (3) 0.60216 (17) 0.0370 (13)
H23A 0.664489 −0.083511 0.602121 0.044*
H23B 0.810835 −0.009248 0.617123 0.044*
C24 0.5703 (6) 0.0516 (3) 0.62608 (16) 0.0314 (12)
H24A 0.560877 0.027979 0.656078 0.038*
H24B 0.459356 0.042988 0.612253 0.038*
C25 0.7660 (6) 0.1871 (4) 0.65689 (15) 0.0360 (13)
H25A 0.852674 0.136031 0.653322 0.054*
H25B 0.726081 0.186868 0.686630 0.054*
H25C 0.813223 0.252583 0.650055 0.054*
C26 0.7344 (7) 0.1796 (4) 0.50828 (15) 0.0427 (14)
H26A 0.614838 0.171870 0.501664 0.064*
H26B 0.801332 0.143779 0.486873 0.064*
H26C 0.764126 0.250339 0.507754 0.064*
C27 0.9583 (6) 0.1531 (4) 0.56523 (16) 0.0371 (13)
H27A 0.981809 0.224626 0.566207 0.056*
H27B 1.029718 0.121637 0.543501 0.056*
H27C 0.981740 0.123517 0.593348 0.056*
C28 0.1773 (7) 0.8549 (4) 0.72367 (15) 0.0385 (13)
H28A 0.299030 0.844937 0.725551 0.058*
H28B 0.122654 0.822938 0.748248 0.058*
H28C 0.152381 0.926278 0.723871 0.058*
C29 −0.0879 (6) 0.8160 (4) 0.68132 (15) 0.0298 (11)
H29A −0.120492 0.884406 0.688456 0.045*
H29B −0.134178 0.770291 0.702755 0.045*
H29C −0.131715 0.798728 0.652905 0.045*
C30 0.1515 (6) 0.3583 (4) 0.63932 (18) 0.0409 (13)
H30A 0.138679 0.287031 0.633559 0.061*
H30B 0.165081 0.394166 0.612156 0.061*
H30C 0.051609 0.383047 0.654253 0.061*
C31 0.2241 (6) 0.8849 (4) 0.56523 (16) 0.0308 (12)
H31 0.183236 0.950435 0.569761 0.037*
C32 0.2741 (6) 0.8621 (3) 0.52005 (14) 0.0264 (11)
C33 0.3199 (6) 0.9395 (3) 0.49219 (16) 0.0283 (11)
C34 0.3694 (6) 0.9244 (4) 0.44913 (16) 0.0331 (12)
H34 0.399698 0.980146 0.432114 0.040*
C35 0.3272 (8) 0.7547 (4) 0.45781 (16) 0.0429 (14)
H35 0.328042 0.689437 0.446141 0.051*
C36 0.2773 (7) 0.7658 (4) 0.50100 (16) 0.0366 (12)
H36 0.245824 0.709137 0.517320 0.044*
F1 0.3172 (4) 1.03671 (18) 0.50736 (9) 0.0384 (7)
N1 0.3748 (5) 0.8318 (3) 0.43148 (13) 0.0357 (10)
O1 0.1510 (4) 0.9668 (2) 0.64495 (11) 0.0365 (8)
O2 0.6732 (6) 0.3964 (3) 0.58506 (16) 0.0782 (16)
H2 0.692325 0.335271 0.583501 0.117*
O3 0.6564 (4) 0.1952 (2) 0.58156 (9) 0.0262 (7)

Source of material

The title compound was synthesized by three-step chemical reactions in turn. First, ginsenoside of stems and leaves (GSL) was degraded by 10% sulfuric acid ethanol solution and purified by silica gel column chromatography. After recrystallization in ethyl acetate and CH2Cl2, the pure white crystalline product panaxadiol (PD; systematic name: (3S, 5R,8R,9R,10R,12R,13R,14R,17S)-4,4,8,10,14-pentamethyl-17 -((R)-2,6,6-trimethyltetra-hydro-2H-pyran-2-yl) hexadecahydro-1H-cyclopenta[a] phen-anthrene-3,12-diol)-was obtained. Second, panaxadiol and PCC were dissolved in 25 ml dichloromethane(methylene chloride) solution and stirred for 4 h at room temperature. The product 3-oxo-panaxadiol was purified by silica gel column chromatography. Finally, in a representative experiment 0.72 mL (25%) of sodium hydroxide aqueous solution was added dropwise to the mixture of 3-oxo-panaxadiol (100 mg; 0.218 mmol) and 3-fluoropyridine-4-formaldehyde (0.022 ml; 0.218 mmol) in 1.4 mL methanol and stirred at room temperature for 2.5 h. The in process-control was monitored by silica gel thin layer chromatography (TLC, 254 nm), the developing solvent is petroleum ether and ethyl acetate. When the reaction was finished, the reaction system was extracted twice with appropriate amount of water and ethyl acetate, and the third time with brine and ethyl acetate. The crude yellow oil was obtained by vacuum distillation of the organic phase and the title compound was purified by silica gel column chromatography. Suitable crystals of the title compound were obtained by recrystallization in ethyl acetate system and dried under vacuo at 65 °C for 5 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), d(C–H) = 0.98 Å (aromatic), d(C–H) = 0.96 Å (methyl), d(C–H) = 0.93 Å (alkenyl) and d(O–H) = 0.82 Å (–OH). The absolute configuration was derived from the synthesis and the configuration of the educts.

Comment

Ginsenoside are divided into two groups according to their glycosidic structures: dammarane and oleanane. There are two types of dammaranes: protopanaxadiol type [5, 6] and protopanaxatriol type sharing a tetrahydrofuran ring and a dammarane skeleton. Because these ginsenosides and their derivatives have a wide range of biological activities, such as anticancer, enhancing myocardial function [7], anti-inflammatory [8] and analgesic, their synthesis and biological activities have attracted extensive attention. At the same time the conformation of the compound will have a certain influence on the biological activity [9]. Our laboratory has done a lot of research work on panaxadiol derivatives [10, 11] and panaxatriol derivatives [12], and obtained crystal structures [13] with good data. The title compound is a PD derivative. It is possible to modify the structure of ginsenoside which is an important saponin in ginsenoside [14].

Single crystal X-ray structure analysis of the title compound revealed that the substituents are at on C(2), the structure of the title compound is similar to that of panaxadiol. In the crystal structure, the pyridine ring is planar, and the other six membered rings except the ring with the keto group have chair conformation. The bond lengths and angles are all in the expected ranges [12].

Corresponding author: Yue Gao, Department of Lab Teaching, School of Pharmacy, Naval Medical University, Shanghai, 200433, P. R. China, E-mail:

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 81473104, 81773563, 81573585

Funding source: Science Foundation

Award Identifier / Grant number: 13ZJZ06

  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 the National Natural Science Foundation of China (No. 81473104, 81773563). Meanwhile, this work was also supported by National Natural Science Foundation of China (Grant no. 81573585) and other Science Foundation (No. 13ZJZ06).

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

References

1. Rigaku OD. CrysAlisP̂RO; 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 PubMed PubMed Central

4. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar PubMed PubMed Central

5. 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

6. Zhang, S. N., Zhao, Y. Q. Crystallization separation of anti-tumor constituent 20(R) 25–OCH3–PPD. Chin. Tradit. Herb. Drugs 2014, 45, 770–773.Search in Google Scholar

7. Wang, J. Z., Wang, H. Y., Mou, X. D., Luan, M. Z., Zhang, X. F., He, X. T., Zhao, F. L., Meng, Q. G. The advances on the protective effects of ginsenosides on myocardial ischemia and ischemia-reperfusion injury. Mini Rev. Med. Chem. 2020, 20, 1610–1618; https://doi.org/10.2174/1389557520666200619115444.Search in Google Scholar PubMed

8. 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 PubMed

9. 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, 152889; https://doi.org/10.1016/j.phymed.2019.152899.Search in Google Scholar PubMed

10. Deng, J. Q., Mu, X. D., Zhao, R. L., Liu, Z., Tang, H. J., He, M., Meng, Q. G. Crystal structure of (20R)-20,25-epoxydammaran-3,12- dione, C30H48O3. Z. Kristallogr. N. Cryst. Struct 2019, 234, 145–147.10.1515/ncrs-2018-0237Search in Google Scholar

11. Wang, J. Z., Weng, W. Z., Ma, Y., He, X. T., Meng, Q. G. Crystal structure of (1S, 3aR, 3bR, 10aR, 10bR, 12aR)-8-amino-3a, 3b, 6, 6, 10a-pentamethyl-1- ((S)-2, 6, 6-trimethyltetrahydro-2H-pyran-2-yl)-2, 3, 3a, 3b, 4, 5, 5a, 6, 10, 10a, 10b, 11, 12, 12a-tetradecahydro-1H- cyclopenta[7, 8] phenanthro[2, 3-d]thiazol-12-ol a panaxadiol dervative, C31H50N2O2S. Z. Kristallogr. N. Cryst. Struct 2019, 234, 397–400; https://doi.org/10.1515/ncrs-2018-0238.Search in Google Scholar

12. Sun, K. W., Wang, X. H., Ma, G. Q., Luo, Q., Wang, Y. H., Meng, Q. G. 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. Z. Kristallogr. N. Cryst. Struct 2021, 236, 17–20; https://doi.org/10.1515/ncrs-2020-0459.Search in Google Scholar

13. Liu, J., Xu, Y. R., An, X. S., Hou, G. G., Meng, Q. G. Synthesis and crystal structures of a 3-acetylated (20S,24S)-ocotillol-type saponin and its C-24 epimer. Acta Crystallogr. 2017, C73, 464–469; https://doi.org/10.1107/s2053229617006507.Search in Google Scholar

14. 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

Received: 2021-06-17
Accepted: 2021-07-19
Published Online: 2021-07-30
Published in Print: 2021-12-20

© 2021 Mei 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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  36. Crystal structure of dichlorido-bis(4-chlorophenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C48H38As2Cl4O2Sn
  37. Crystal structure of (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane-κ 8 N 2, O 6) potassium cyclopentadienide, [K([2.2.2]crypt)]Cp, C23H41KN2O6
  38. The crystal structure of bis(2-oxidopyridin-1-ium-3-carboxylato-κ2O,O′)-(phenantroline-κ2N,N′)manganese(II) - methanol (1/3), C27H28N4O9Mn
  39. Crystal structure of 4-(dimethylamino)pyridinium dibromido-tris(4-chlorophenyl-κC)stannate(IV), C25H23Br2Cl3N2Sn
  40. Crystal structure of (3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis(3-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C27H20Cl2F2N2O3S
  41. Crystal structure of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-trifluoromethyl)benzenesulfonyl)piperidin-4-one, C26H18F5NO3S
  42. Crystal structure of chlorido-(4-methyl-2-((phenylimino)methyl)phenolato-κ2 N,O)-(pyridine-κ1 N)platinum(II), C19H17ClN2OPt
  43. Crystal structure of (4-methylbenzyl)(triphenyl)phosphonium chloride dihydrate, C26H28ClO2P
  44. The crystal structure of poly[μ2-chlorido-(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′silver(I)], C12H12AgClN2
  45. Crystal structure of poly[(μ4-benzene-1,2,4,5-tetracarboxylato)-bis(μ2-adipohydrazide)dicadmium], C11H15N4O6Cd
  46. The crystal structure of (E)-N′-(butan-2-ylidene)isonicotinohydrazide 0.5 hydrate C10H13N3O·0.5H2O
  47. The crystal structure of bis(6-phenylpyridine-2-carboxylate-κ2 N,O)-(2,2′-bipyridine-κ2 N,N′)zinc(II) monohydrate, C34H26N4O5Zn
  48. The crystal structure of (1R *,2S *)-1,2-bis(2-fluorophenyl)-3,8-dimethoxyacenaphthene-1,2-diol, C26H20F2O4
  49. Crystal structure of catena-poly[(μ2-1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzotriazole-κ2N:N′)-(nitrato-κ2O,O′)silver (I)], C13H15Ag1N6O3
  50. The crystal structure of [(phenantroline-κ2 N,N′)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)cobalt(II)]monohydrate, C36H26N4O5Co
  51. Crystal structure of (1E)-N′-[(1E)-1-(4-chlorophenyl)ethylidene]-2-[1-(4-chlorophenyl)ethylidene]hydrazine-1-carbohydrazonamide, C 17 H 17 Cl 2 N 5
  52. The crystal structure of (E)-2-((tert-butylimino)methyl)-4-chlorophenol, C11H14ClNO
  53. Crystal structure of all-cis-2,4,6-trihydroxycyclohexane- 1,3,5-triaminium chloride sulfate, C6H18ClN3O7S
  54. Crystal structure of dichlorido-bis(dimethyl sulfoxide-κO)bis(4-methylphenyl-κC 1)tin(IV), C18H26Cl2O2S2Sn
  55. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)(2,2′-bipyridyl-κ 2 N,N′)tin(IV), C22H16Cl4N2Sn
  56. Redetermination of the crystal structure of (E)-5-bromo-2-hydroxybenzaldehyde oxime, C 7 H 6 BrNO 2
  57. The crystal structure of (E)-amino(2-(4-methylbenzylidene)hydrazineyl)methaniminium 4-methylbenzoate, C9H13N4 + C8H7O2 −
  58. Crystal structure of 2-chloro-3-(isopentylamino)naphthalene-1,4-dione, C 15 H 16 ClNO 2
  59. The crystal structure of bis(2-acetyl-5-methoxyphenyl)carbonate 1.5 hydrate, C19H18O7
  60. The crystal structure of poly[(μ 4-4,4′-(azanediylbis(methylene))dibenzoato-κ 4 O:N:O′:Oʺ)zinc(II)], C16H13NO4Zn
  61. The crystal structure of catena-poly[(1,10-phenanthroline-k2N,N′)-(μ3-tetraoxidomoybdato(VI)-k3O:O′:O″)manganese(II)] C12H8N2O4MoMn
  62. Crystal structure of catena-poly[(4-hydroxyl-5-(methoylcarbonyl)thiophene-2-carboxylato-κ1 O)-(μ2-piperazine-1,4-diylbis(pyridin-4-ylmethanone)-κ2 N:N′)silver(I)] monohydrate, C23H23AgN4O8S
  63. Crystal structure of bis(4-bromo-2-(((3-bromopropyl)imino)methyl)phenolato-κ2N,O)-oxido-vanadium(IV), C20H20Br4N2O3V
  64. The crystal structure of (2a′S,2a1′S,3R,5a′S,7′R)-5-(furan-3-yl)-2a′,2a1′-dihydroxy-7′-methyldecahydro-2H-spiro[furan-3,6′-naphtho[1,8-bc]furan]-2,2′(2a′H)-dione, C19H22O7
  65. The crystal structure of 3-bromopicolinic acid, C6H4BrNO2
  66. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S,S) platinum(II), C26H18N6PtS4
  67. Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
  68. The crystal structure of 3-amino-5-carboxypyridin-1-ium bromide, C6H7BrN2O2
  69. The crystal structure of (2-hydroxy-5-methyl-phenyl)-(1H-pyrazol-4-yl)-methanone hemihydrate, C11H10.5N2O2.5
  70. Crystal structure of tetraaqua-(2-(4-formylphenoxy)acetato-k1O)cadmium(II), C18H22O12Cd
  71. Crystal structure of diethyl 6,12-dimethyl-3,9-di-p-tolyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5-dicarboxylate, C32H38N2O4
  72. Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5
https://doi.org/10.1515/ncrs-2021-0248
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Redetermination of the crystal structure of 3-bromonitrobenzene at 200 K, C6H4BrNO2 – temperature effects on cell constants
  4. Crystal structure of (E)-ethyl 2-((4-oxo-4H-chromen-3-yl)methyleneaminooxy)acetate, C14H13NO5
  5. Crystal structure of (8R,10R,14R, Z)-2-((3–Fluoropyridin-4-yl) methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6, 6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a] phenanthren-3-one, C36H52FNO3
  6. Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-κ4N,N′,O,O′] copper(II), C17H14Cl2CuN2O2
  7. The crystal structure of 6-amino-2-carboxypyridin-1-ium bromide, C6H7BrN2O2
  8. Redetermination of the crystal structure of bis[N,N′-ethylenebis(acetylacetoniminato)nickel(II)] sodium perchlorate, C24H36ClN4NaNi2O8
  9. The crystal structure of 3-methyl-2,6-dinitrophenol, C7H6N2O5
  10. The crystal structure of 5-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  11. Crystal structure of trans-tetraaqua-bis{2-carboxy-4-((5-carboxypyridin-3-yl)oxy)benzoato-κ1 N}cobalt(II) dihydrate C28H28O20N2Co
  12. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-(p-tolyl)furan, C23H23BrO2
  13. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(benzo[d][1,3]dioxol-5-ol ato-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV)-dichloromethane(1/1), C27H25N3O10Ti
  14. Crystal structure of (((1E,1′E)-1,2-phenylenebis(methaneylylidene))bis(hydrazin-1-yl-2-ylidene))bis(aminomethaniminium) dinitrate C10H16N10O6
  15. Crystal structure of catena-poly[triaqua-(μ 2-1,3-di(1H-imidazol-1-yl)propane-κ 2 N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ 1 O)nickel(II)]N,N′-dimethylformamide (1/1), C28H35N8O8Ni
  16. The crystal structure of 3,3′-[1,4-phenylenebis(methylene)]bis(1-ethenyl-1H-imidazol-3-ium) dichloride – dichloromethane – water (1/1/1), C19H24Cl4N4O1
  17. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C13H22F12N4P2
  18. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)tin(IV), C12H8Cl4Sn
  19. Synthesis and crystal structure of 4-acetylpyrene, C18H12O
  20. Crystal structure of 2,2′-(butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(4-methoxyphenol), C20H24N2O4
  21. The crystal structure of (E)-2-(((5-((triphenylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C27H21N3OS2Sn
  22. Crystal structure of diaqua-bis(μ2-6-phenylpyridine-2-carboxylate-κ3N,O:O)-bis(6-phenylpyridine-2-carboxylato-κ2N,O)lead(II) – N,N-dimethylformamide – water (1/2/4), C54H58N6O16Pb2
  23. Crystal structure of methyl 4-acetoxy-3-methoxybenzoate, C11H12O5
  24. Crystal structure of 2,2′-(propane-1,3-dilylbis(azaneylylidene))bis(methanylylidene)bis(4-methylphenol), C19H22N2O2
  25. Crystal structure of dichlorido-bis(4-methylphenyl-κC1)tin(IV), C14H14Cl2Sn
  26. Crystal structure of methyl (E)-3-(4-acetoxyphenyl)acrylate, C12H12O4
  27. The crystal structure of bis(benzoato-κ2 O,O′)-(2,9-dimethyl-1,10-phenanthroline-κ2 N,N′)-copper(II), C28H22CuN2O4
  28. Crystal structure of (8R,10R,14R,Z)-12-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one–water (2/1), C37H56NO4.5
  29. Crystal structure of dimethyl-bis(4-bromophenyl-κC1)tin(IV), C14H14Br2Sn
  30. The crystal structure of the cocrystal di-μ2-chlorido-octamethyl-di-μ3-oxido-bis(2,3,4,5-tetrafluorobenzoato-κ2 O,O′)tetratin(IV) ─ octamethyl-di-μ3-oxido-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O′)-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O;O′)tetratin(IV) C58H54Cl2F24O16Sn8
  31. Crystal structure of 3-iodo-N 2-(2-methyl-1-(methylsulfonyl)propan-2-yl)-N 1-(2-methyl-4-(perfluoropropan-2-yl)phenyl)phthalamide, C23H22F7I1N2O4S1
  32. Crystal structure of 1-(2-(4-bromophenyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)-naphthalen-2-ol – dichloromethane – dimethyl sulfoxide (1/1/1), C28H18BrNO·CH2Cl2·C2H6SO
  33. Crystal structure of [meso-5,7,7,12,14,14,-hexamethyl-1,4,8,11-tetraazacyclotetradecane]nickel(II) diperchlorate – dimethylsulphoxide (1/2), C20H48Cl2N4NiO10S2
  34. Crystal structure of 1,1′-(1,3-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S) palladium(II), C26H18N6PdS4
  35. The crystal structure of bis(6-phenylpyridine-2-carboxylato-κ2 N,O)copper(II), C24H16N2O4Cu
  36. Crystal structure of dichlorido-bis(4-chlorophenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C48H38As2Cl4O2Sn
  37. Crystal structure of (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane-κ 8 N 2, O 6) potassium cyclopentadienide, [K([2.2.2]crypt)]Cp, C23H41KN2O6
  38. The crystal structure of bis(2-oxidopyridin-1-ium-3-carboxylato-κ2O,O′)-(phenantroline-κ2N,N′)manganese(II) - methanol (1/3), C27H28N4O9Mn
  39. Crystal structure of 4-(dimethylamino)pyridinium dibromido-tris(4-chlorophenyl-κC)stannate(IV), C25H23Br2Cl3N2Sn
  40. Crystal structure of (3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis(3-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C27H20Cl2F2N2O3S
  41. Crystal structure of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-trifluoromethyl)benzenesulfonyl)piperidin-4-one, C26H18F5NO3S
  42. Crystal structure of chlorido-(4-methyl-2-((phenylimino)methyl)phenolato-κ2 N,O)-(pyridine-κ1 N)platinum(II), C19H17ClN2OPt
  43. Crystal structure of (4-methylbenzyl)(triphenyl)phosphonium chloride dihydrate, C26H28ClO2P
  44. The crystal structure of poly[μ2-chlorido-(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′silver(I)], C12H12AgClN2
  45. Crystal structure of poly[(μ4-benzene-1,2,4,5-tetracarboxylato)-bis(μ2-adipohydrazide)dicadmium], C11H15N4O6Cd
  46. The crystal structure of (E)-N′-(butan-2-ylidene)isonicotinohydrazide 0.5 hydrate C10H13N3O·0.5H2O
  47. The crystal structure of bis(6-phenylpyridine-2-carboxylate-κ2 N,O)-(2,2′-bipyridine-κ2 N,N′)zinc(II) monohydrate, C34H26N4O5Zn
  48. The crystal structure of (1R *,2S *)-1,2-bis(2-fluorophenyl)-3,8-dimethoxyacenaphthene-1,2-diol, C26H20F2O4
  49. Crystal structure of catena-poly[(μ2-1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzotriazole-κ2N:N′)-(nitrato-κ2O,O′)silver (I)], C13H15Ag1N6O3
  50. The crystal structure of [(phenantroline-κ2 N,N′)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)cobalt(II)]monohydrate, C36H26N4O5Co
  51. Crystal structure of (1E)-N′-[(1E)-1-(4-chlorophenyl)ethylidene]-2-[1-(4-chlorophenyl)ethylidene]hydrazine-1-carbohydrazonamide, C 17 H 17 Cl 2 N 5
  52. The crystal structure of (E)-2-((tert-butylimino)methyl)-4-chlorophenol, C11H14ClNO
  53. Crystal structure of all-cis-2,4,6-trihydroxycyclohexane- 1,3,5-triaminium chloride sulfate, C6H18ClN3O7S
  54. Crystal structure of dichlorido-bis(dimethyl sulfoxide-κO)bis(4-methylphenyl-κC 1)tin(IV), C18H26Cl2O2S2Sn
  55. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)(2,2′-bipyridyl-κ 2 N,N′)tin(IV), C22H16Cl4N2Sn
  56. Redetermination of the crystal structure of (E)-5-bromo-2-hydroxybenzaldehyde oxime, C 7 H 6 BrNO 2
  57. The crystal structure of (E)-amino(2-(4-methylbenzylidene)hydrazineyl)methaniminium 4-methylbenzoate, C9H13N4 + C8H7O2 −
  58. Crystal structure of 2-chloro-3-(isopentylamino)naphthalene-1,4-dione, C 15 H 16 ClNO 2
  59. The crystal structure of bis(2-acetyl-5-methoxyphenyl)carbonate 1.5 hydrate, C19H18O7
  60. The crystal structure of poly[(μ 4-4,4′-(azanediylbis(methylene))dibenzoato-κ 4 O:N:O′:Oʺ)zinc(II)], C16H13NO4Zn
  61. The crystal structure of catena-poly[(1,10-phenanthroline-k2N,N′)-(μ3-tetraoxidomoybdato(VI)-k3O:O′:O″)manganese(II)] C12H8N2O4MoMn
  62. Crystal structure of catena-poly[(4-hydroxyl-5-(methoylcarbonyl)thiophene-2-carboxylato-κ1 O)-(μ2-piperazine-1,4-diylbis(pyridin-4-ylmethanone)-κ2 N:N′)silver(I)] monohydrate, C23H23AgN4O8S
  63. Crystal structure of bis(4-bromo-2-(((3-bromopropyl)imino)methyl)phenolato-κ2N,O)-oxido-vanadium(IV), C20H20Br4N2O3V
  64. The crystal structure of (2a′S,2a1′S,3R,5a′S,7′R)-5-(furan-3-yl)-2a′,2a1′-dihydroxy-7′-methyldecahydro-2H-spiro[furan-3,6′-naphtho[1,8-bc]furan]-2,2′(2a′H)-dione, C19H22O7
  65. The crystal structure of 3-bromopicolinic acid, C6H4BrNO2
  66. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S,S) platinum(II), C26H18N6PtS4
  67. Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
  68. The crystal structure of 3-amino-5-carboxypyridin-1-ium bromide, C6H7BrN2O2
  69. The crystal structure of (2-hydroxy-5-methyl-phenyl)-(1H-pyrazol-4-yl)-methanone hemihydrate, C11H10.5N2O2.5
  70. Crystal structure of tetraaqua-(2-(4-formylphenoxy)acetato-k1O)cadmium(II), C18H22O12Cd
  71. Crystal structure of diethyl 6,12-dimethyl-3,9-di-p-tolyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5-dicarboxylate, C32H38N2O4
  72. Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5
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