Startseite The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
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The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3

  • Zhi-Qiang Lu EMAIL logo
Veröffentlicht/Copyright: 6. April 2022

Abstract

C18H14N2O3, monoclinic, P21/n (no. 14), a = 8.1644(3) Å, b = 14.5766(6) Å, c = 12.9462(4) Å, β = 91.902(3)°, V = 1539.87(10) Å3, Z = 4, R gt (F) = 0.0456, ωRref(F2) = 0.1400, T = 293(2) K.

CCDC no.: 2162952

The crystal 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: 0.25 × 0.22 × 0.16 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker SMART, φ and ω-scans
θmax, completeness: 29.6°, >99%
N(hkl)measured, N(hkl)unique, Rint: 11,916, 3825, 0.027
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2796
N(param)refined: 208
Programs: SHELX [1, 2], OLEX2 [3]
Table 2:

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

x y z Uiso*/Ueq
O1 0.22413 (12) 0.34883 (7) 0.70184 (7) 0.0457 (3)
O2 −0.0318 (3) 0.19323 (19) 0.49957 (14) 0.1493 (10)
O3 0.1047 (2) 0.31363 (16) 0.51760 (10) 0.1089 (7)
N1 0.08023 (17) 0.28975 (9) 0.83617 (9) 0.0503 (3)
N2 0.0288 (2) 0.25240 (13) 0.55302 (11) 0.0702 (5)
C1 0.1894 (2) 0.54946 (11) 0.72630 (12) 0.0515 (4)
H1 0.212180 0.536690 0.657881 0.062*
C2 0.1072 (2) 0.62952 (13) 0.75029 (15) 0.0616 (4)
H2 0.074514 0.670071 0.698113 0.074*
C3 0.0740 (2) 0.64882 (13) 0.85182 (17) 0.0686 (5)
H3 0.018591 0.702364 0.868110 0.082*
C4 0.1226 (3) 0.58936 (14) 0.92843 (15) 0.0709 (5)
H4 0.101048 0.602974 0.996837 0.085*
C5 0.2035 (2) 0.50909 (12) 0.90499 (11) 0.0572 (4)
H5 0.235152 0.468795 0.957659 0.069*
C6 0.23792 (17) 0.48823 (10) 0.80342 (10) 0.0414 (3)
C7 0.32383 (17) 0.39987 (10) 0.77740 (9) 0.0410 (3)
H7 0.339421 0.362967 0.840231 0.049*
C8 0.48808 (17) 0.41507 (10) 0.72895 (11) 0.0438 (3)
C9 0.5069 (2) 0.41189 (12) 0.62327 (12) 0.0565 (4)
H9 0.417345 0.399296 0.579276 0.068*
C10 0.6607 (2) 0.42764 (14) 0.58288 (15) 0.0686 (5)
H10 0.673387 0.424743 0.511830 0.082*
C11 0.7935 (2) 0.44736 (13) 0.64680 (17) 0.0668 (5)
H11 0.895335 0.458300 0.619117 0.080*
C12 0.7755 (2) 0.45088 (13) 0.75159 (16) 0.0636 (5)
H12 0.865197 0.464389 0.795059 0.076*
C13 0.6237 (2) 0.43433 (12) 0.79300 (13) 0.0539 (4)
H13 0.612638 0.436143 0.864237 0.065*
C14 0.10411 (17) 0.29552 (10) 0.73592 (10) 0.0407 (3)
C15 0.00814 (19) 0.24509 (11) 0.66414 (12) 0.0506 (4)
C16 −0.1113 (2) 0.18736 (14) 0.69954 (17) 0.0719 (5)
H16 −0.174327 0.152218 0.653296 0.086*
C17 −0.1365 (3) 0.18224 (14) 0.80361 (18) 0.0793 (6)
H17 −0.217925 0.144893 0.829401 0.095*
C18 −0.0382 (3) 0.23360 (12) 0.86785 (14) 0.0658 (5)
H18 −0.054295 0.229518 0.938483 0.079*

Source of materials

The title compound was prepared according to the synthetic method reported in the previous literature [4]. The crude product was recrystallized from ethanol to afford crystals suitable for single crystal X-ray diffraction.

Experimental details

The hydrogen atoms were assigned with common isotropic displacement factors Uiso(H) = 1.2 times Ueq(C, aromatic ring), Uiso(H) = 1.2 times Ueq(CH). The final refinement was performed using geometrical restraints, with C–H = 0.93 Å (aromatic ring), C–H = 0.98 Å (CH).

Comment

Both O-alkylation and N-alkylation of 2-pyridone are all an important molecular scaffold for there biological and pharmaceutical properties [57]. However, based on the Hard–Soft Acid–Base theory, the softer nitrogen atom will tends to bond the softer carbon atom than oxygen. And, the N-alkylation compound is more thermodynamic stable than O-alkylation products. Thus, there are many methods for the N-alkylation of the 2-pyridone moiety, but the absolute selective synthesis of O-alkylated products is even rarer. We have reported the syntheses and the structures of some related compounds [4, 8]. In this paper, we reported the synthesis and structure of the compound 2-(benzhydryloxy)-3-nitropyridine.

The asymmetric unit of the title structure contains one molecule (see the figure). All bond lengths and angles are in the expected ranges. The dihedral angle between the phenyl ring (C1/C2/C3/C4/C5/C6), the phenyl ring (C8/C9/C10/C11/C12/C13) and the pyridine ring (C14/C15/C16/C17/C18/N2) are 73.8 °, 77.2 °, and 29.1 °, respectively.


Corresponding author: Zhi-Qiang Lu, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan 471022, P. R. China, E-mail:

Funding source: Natural Science Foundation of Henan Province

Award Identifier / Grant number: No. 212300410374

  1. Author contributions: The author has accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: We thank financial support from Natural Science Foundation of Henan Province No. 212300410374.

  3. Conflict of interest statement: The author declares no conflicts of interest regarding this article.

References

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Received: 2022-03-02
Accepted: 2022-03-29
Published Online: 2022-04-06
Published in Print: 2022-06-27

© 2022 Zhi-Qiang Lu, 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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