Startseite Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
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Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4

  • Shuai Fan , Qian Zhang , Xu-Dong Lv , Yuan-Yuan Jin und Zhao-Yong Yang EMAIL logo
Veröffentlicht/Copyright: 4. April 2022

Abstract

C42H42N2O4, triclinic, P 1 (no. 2), a = 9.309(3) Å, b = 14.191(5) Å, c = 14.918(5) Å, α = 69.221(4)°, β = 82.384(5)°, γ = 72.805(4)°, V = 1759.3(10) Å3, Z = 2, R gt (F) = 0.0699, wR ref (F2) = 0.1806, T = 296 K.

CCDC no.: 2142413

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: Colorless block
Size: 0.18 × 0.16 × 0.14 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.0°, 99%
N(hkl)measured, N(hkl)unique, Rint: 13,612, 6153, 0.055
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 3035
N(param)refined: 436
Programs: Bruker [1], SHELX [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.1743 (3) 0.16745 (18) 0.29691 (16) 0.0652 (7)
O2 0.3072 (3) 0.0507 (2) 0.42235 (18) 0.0711 (8)
O3 0.1796 (3) 0.4520 (2) 0.14238 (17) 0.0687 (7)
O4 0.1552 (3) 0.5808 (2) 0.20067 (18) 0.0799 (8)
N1 0.3176 (3) 0.2735 (2) 0.52951 (18) 0.0493 (7)
N2 0.5155 (3) 0.2589 (2) 0.31320 (17) 0.0487 (7)
C1 0.4964 (7) 0.1597 (4) 0.9162 (3) 0.124 (2)
H1A 0.577354 0.096735 0.932153 0.186*
H1B 0.411031 0.148420 0.958220 0.186*
H1C 0.527715 0.215206 0.923377 0.186*
C2 0.4537 (5) 0.1892 (4) 0.8132 (3) 0.0767 (12)
C3 0.3774 (6) 0.2900 (4) 0.7626 (3) 0.0906 (14)
H3 0.353746 0.341019 0.791663 0.109*
C4 0.3354 (5) 0.3167 (3) 0.6701 (3) 0.0816 (13)
H4 0.282848 0.385422 0.638491 0.098*
C5 0.3687 (4) 0.2446 (3) 0.6220 (2) 0.0498 (9)
C6 0.4447 (4) 0.1445 (3) 0.6726 (2) 0.0596 (10)
H6 0.471096 0.093660 0.643180 0.072*
C7 0.4829 (5) 0.1178 (3) 0.7663 (3) 0.0745 (12)
H7 0.530535 0.048294 0.799115 0.089*
C8 0.3874 (4) 0.2111 (3) 0.4670 (2) 0.0479 (9)
H8 0.422024 0.136128 0.502876 0.057*
C9 0.5177 (4) 0.2575 (3) 0.4105 (2) 0.0491 (9)
H9 0.615509 0.219238 0.439910 0.059*
C10 0.4647 (4) 0.3726 (3) 0.4099 (2) 0.0527 (9)
H10 0.535268 0.388956 0.441691 0.063*
C11 0.3098 (4) 0.3795 (3) 0.4627 (2) 0.0525 (9)
H11 0.285327 0.431272 0.495607 0.063*
C12 0.2975 (4) 0.4145 (3) 0.2903 (2) 0.0468 (8)
C13 0.3561 (3) 0.2975 (2) 0.2937 (2) 0.0455 (8)
H13 0.333428 0.288174 0.235570 0.055*
C14 0.2766 (3) 0.2353 (2) 0.3863 (2) 0.0442 (8)
C15 0.1292 (3) 0.3177 (2) 0.3946 (2) 0.0468 (8)
H15 0.074925 0.337666 0.335826 0.056*
C16 0.1969 (4) 0.4076 (2) 0.3833 (2) 0.0472 (8)
H16 0.119324 0.473270 0.377833 0.057*
C17 0.4303 (4) 0.4507 (3) 0.3082 (2) 0.0516 (9)
H17 0.387605 0.520296 0.314144 0.062*
C18 0.5571 (4) 0.4585 (3) 0.2347 (2) 0.0517 (9)
C19 0.5300 (4) 0.5154 (3) 0.1395 (3) 0.0688 (11)
H19 0.431058 0.547224 0.120503 0.083*
C20 0.6453 (5) 0.5267 (4) 0.0711 (3) 0.0790 (13)
H20 0.622849 0.565644 0.007318 0.095*
C21 0.7907 (5) 0.4815 (4) 0.0964 (3) 0.0819 (13)
H21 0.868710 0.488925 0.050829 0.098*
C22 0.8199 (5) 0.4247 (4) 0.1907 (3) 0.0919 (15)
H22 0.919019 0.392211 0.209000 0.110*
C23 0.7059 (4) 0.4147 (3) 0.2586 (3) 0.0779 (12)
H23 0.729540 0.377389 0.322446 0.094*
C24 0.6047 (4) 0.1771 (3) 0.2812 (2) 0.0467 (8)
C25 0.6063 (4) 0.1875 (3) 0.1855 (2) 0.0646 (10)
H25 0.546384 0.247837 0.143641 0.078*
C26 0.6947 (5) 0.1106 (3) 0.1508 (3) 0.0762 (12)
H26 0.690659 0.119259 0.086344 0.091*
C27 0.7887 (4) 0.0215 (3) 0.2087 (3) 0.0730 (11)
C28 0.7883 (4) 0.0113 (3) 0.3044 (3) 0.0714 (11)
H28 0.849949 −0.048464 0.345850 0.086*
C29 0.6982 (4) 0.0878 (3) 0.3401 (2) 0.0583 (10)
H29 0.700890 0.078689 0.404744 0.070*
C30 0.8856 (5) −0.0645 (4) 0.1719 (4) 0.1103 (17)
H30A 0.834515 −0.117846 0.184472 0.165*
H30B 0.979670 −0.094354 0.203792 0.165*
H30C 0.903803 −0.035847 0.104042 0.165*
C31 0.0198 (4) 0.2882 (3) 0.4772 (2) 0.0488 (9)
C32 −0.0508 (4) 0.2123 (3) 0.4833 (2) 0.0598 (10)
H32 −0.026867 0.178851 0.437616 0.072*
C33 −0.1563 (4) 0.1850 (3) 0.5561 (3) 0.0665 (11)
H33 −0.200474 0.132921 0.559442 0.080*
C34 −0.1948 (4) 0.2347 (3) 0.6222 (3) 0.0717 (11)
H34 −0.266248 0.217505 0.670477 0.086*
C35 −0.1275 (5) 0.3102 (3) 0.6172 (3) 0.0766 (12)
H35 −0.152676 0.343645 0.662846 0.092*
C36 −0.0228 (4) 0.3372 (3) 0.5451 (3) 0.0650 (10)
H36 0.020124 0.389617 0.542378 0.078*
C37 0.2069 (4) 0.4821 (3) 0.2022 (3) 0.0562 (10)
C38 0.0502 (7) 0.6556 (4) 0.1239 (4) 0.124 (2)
H38A 0.022017 0.618379 0.088661 0.149*
H38B −0.040399 0.690633 0.152062 0.149*
C39 0.1196 (8) 0.7268 (6) 0.0640 (5) 0.188 (3)
H39A 0.052789 0.775482 0.014123 0.281*
H39B 0.146477 0.763653 0.099262 0.281*
H39C 0.208690 0.691633 0.036067 0.281*
C40 0.2572 (4) 0.1387 (3) 0.3739 (2) 0.0511 (9)
C41 0.1492 (5) 0.0863 (3) 0.268 (3) 0.0815 (13)
H41A 0.062347 0.064452 0.303055 0.098*
H41B 0.236245 0.025956 0.282049 0.098*
C42 0.1235 (8) 0.1309 (4) 0.1649 (3) 0.150 (2)
H42A 0.210756 0.151239 0.131389 0.225*
H42B 0.037974 0.190999 0.152275 0.225*
H42C 0.104965 0.079459 0.143257 0.225*

Source of material

The preparation of 1,4-diaryl-1,4-dihydropyridine-3-carboxylic acid photoreactive raw materials was performed by a literature method [4]. Starting from aniline (0.5 mmol), ethyl propiolate (0.5 mmol) and 4-methylcinnamaldehyde (0.5 mmol); piperazine (0.25 mmol) and p-toluenesulfonic acid (0.02 mmol) were used as catalysts, 1,2-dichloroethane (20 mL) was used as solvent. The mixture was heated to reflux for 12 h to obtain 1-phenyl-4-(4-methyl-phenyl)-1,4-dihydroethylpyridine-3-carboxylate. The 1-phenyl-4-(4-methyl-phenyl)-1,4-dihydroethylpyridine-3-carboxylate (0.5 mmol) obtained in the first step of the reaction was placed on a blue LED (410 nm) for a photoreaction for 3 h [5]. The product was obtained by column chromatography eluting with petroleum ether and n-hexane 10:1. The resulting solution was evaporated to dryness to get some crystals.

Experimental details

All hydrogen atoms were placed in the calculated positions and all the non-hydrogen atoms were refined anisotropically.

Comment

Cage dimers based on 4-aryl-1,4-dihydropyridines have a wide range of biological activities, such as anti-HIV drug and as an antimultidrug resistance modulator [6], [7], [8]. The caged dimeric compounds similar to the title compound has also been obtained by a dimerization by photoreaction. However, the two pyridine rings in the title compound present a special angle, which is of interest for the study of new functional caged compounds. The bond lengths and angles are in the expected ranges.


Corresponding author: Zhao-Yong Yang, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantanxili, 100050 Beijing, P. R. China, E-mail:

Funding source: National Key Research and Development Program of China 10.13039/501100012166

Award Identifier / Grant number: 2018YFA0901800

  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 Key Research and Development Program of China (No. 2018YFA0901800).

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

References

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Received: 2022-01-18
Accepted: 2022-03-07
Published Online: 2022-04-04
Published in Print: 2022-06-27

© 2022 Shuai Fan et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
  48. Crystal structure of 5-nitroquinazolin-4(3H)-one, C8H5N3O3
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