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Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P

  • Chongning Jiang ORCID logo EMAIL logo and Pengfei Zhao
Published/Copyright: June 18, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 4

Abstract

C26H23ClNO2P, triclinic, P1̄ (no. 2), a = 9.6023(16) Å, b = 9.9881(17) Å, c = 13.406(2) Å, α = 77.627(2)°, β = 70.524(2)°, γ = 73.294(2)°, V = 1151.0(3) Å3, Z = 2, Rgt (F) = 0.0439, wRref (F 2) = 0.1452, T = 296(2) K.

CCDC no.: 2359339

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: 0.18 × 0.16 × 0.15 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.26 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 27.5°, 98 %
N(hkl)measured, N(hkl)unique, R int: 7135, 5115, 0.016
Criterion for I obs, N(hkl) gt: I obs > 2σ(I obs), 4111
N(param) refined: 282
Programs: Bruker, 1 Shelx, 2 Olex2 3
Table 2:

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

Atom x y z U iso*/U eq
Cl1 −0.10246 (6) 0.76094 (7) 1.03705 (4) 0.0703 (2)
P1 0.57650 (4) 0.59577 (4) 0.63445 (3) 0.03109 (14)
O1 0.53561 (13) 0.47042 (12) 0.61974 (9) 0.0404 (3)
O2 0.29989 (13) 0.69874 (13) 0.53227 (10) 0.0385 (3)
H2A 0.3416 (16) 0.649 (2) 0.4897 (17) 0.058*
N1 0.39598 (14) 0.78660 (14) 0.52993 (10) 0.0322 (3)
C1 0.1807 (3) 1.0073 (2) 0.35981 (19) 0.0592 (6)
H1 0.090535 1.037650 0.411849 0.071*
C2 0.1804 (4) 1.0202 (3) 0.2550 (2) 0.0809 (8)
H2 0.090143 1.059573 0.237136 0.097*
C3 0.3105 (4) 0.9760 (3) 0.1780 (2) 0.0851 (9)
H3 0.309052 0.984248 0.107939 0.102*
C4 0.4457 (4) 0.9185 (3) 0.20395 (18) 0.0745 (7)
H4 0.535468 0.888513 0.151450 0.089*
C5 0.4458 (3) 0.9061 (2) 0.30867 (16) 0.0569 (5)
H5 0.536363 0.867793 0.326180 0.068*
C6 0.3135 (2) 0.94974 (18) 0.38769 (15) 0.0423 (4)
C7 0.3146 (2) 0.93141 (18) 0.50237 (14) 0.0412 (4)
H7A 0.364764 0.997899 0.511083 0.049*
H7B 0.211288 0.949121 0.549139 0.049*
C8 0.42427 (17) 0.75950 (17) 0.63511 (12) 0.0312 (3)
H8 0.468452 0.835673 0.636993 0.037*
C9 0.28843 (17) 0.75968 (17) 0.73380 (12) 0.0336 (3)
C10 0.20667 (19) 0.65554 (19) 0.76436 (14) 0.0407 (4)
H10 0.233639 0.584006 0.722272 0.049*
C11 0.0859 (2) 0.6570 (2) 0.85646 (14) 0.0453 (4)
H11 0.030933 0.587842 0.875699 0.054*
C12 0.04792 (19) 0.7617 (2) 0.91924 (13) 0.0435 (4)
C13 0.1268 (2) 0.8647 (2) 0.89190 (16) 0.0547 (5)
H13 0.100767 0.934389 0.935434 0.066*
C14 0.2457 (2) 0.8640 (2) 0.79896 (15) 0.0477 (4)
H14 0.298173 0.935077 0.779633 0.057*
C15 0.61857 (18) 0.57075 (18) 0.75926 (13) 0.0366 (4)
C16 0.6447 (2) 0.4334 (2) 0.81103 (15) 0.0492 (5)
H16 0.636038 0.360165 0.782470 0.059*
C17 0.6837 (3) 0.4062 (3) 0.90572 (18) 0.0675 (7)
H17 0.702053 0.314430 0.940288 0.081*
C18 0.6953 (3) 0.5149 (3) 0.94817 (17) 0.0689 (7)
H18 0.721639 0.496077 1.011380 0.083*
C19 0.6684 (3) 0.6499 (3) 0.89851 (17) 0.0619 (6)
H19 0.675878 0.722669 0.928190 0.074*
C20 0.6300 (2) 0.6789 (2) 0.80369 (15) 0.0491 (5)
H20 0.611979 0.771150 0.769935 0.059*
C21 0.73832 (17) 0.63833 (17) 0.52914 (13) 0.0346 (4)
C22 0.7438 (2) 0.6349 (2) 0.42395 (14) 0.0457 (4)
H22 0.666586 0.609445 0.410435 0.055*
C23 0.8636 (2) 0.6691 (3) 0.34069 (17) 0.0611 (6)
H23 0.867053 0.666763 0.270906 0.073*
C24 0.9790 (2) 0.7071 (3) 0.36017 (19) 0.0638 (6)
H24 1.057773 0.733145 0.303272 0.077*
C25 0.9781 (2) 0.7064 (2) 0.46271 (19) 0.0588 (6)
H25 1.057681 0.728770 0.475445 0.071*
C26 0.85775 (19) 0.6722 (2) 0.54756 (16) 0.0457 (4)
H26 0.856949 0.672022 0.617162 0.055*

1 Source of materials

The title compound was synthesized according to the literature method. 4 N-benzyl-1-(4-chlorophenyl)methanimine oxide (0.01 mol, 2.45 g) and diphenylphosphine oxide (0.012 mol, 2.42 g) were mixed in water (20 ml). The mixture was stirred for 3 h at reflux temperature. The crude product was obtained under vacuum. The crystals were recrystallized in hexane and ethyl acetate (4/1, v/v) with yield = 90 %. 1 H NMR (400 MHz, CDCl3) δ (ppm): 7.87–7.81 (m, 2H), 7.59 (td, J = 7.3, 1.5 Hz, 1H), 7.53–7.41 (m, 6H), 7.36 (td, J = 7.3, 1.4 Hz, 1H), 7.30–7.22 (m, 7H), 7.13–7.04 (m, 2H), 6.69 (s, 1H), 4.61 (d, J = 7.6 Hz, 1H), 4.08 (d, J = 13.1 Hz, 1H), 3.60 (d, J = 13.1 Hz, 1H). 13 C NMR (101 MHz, CDCl3) δ (ppm): 136.5, 134.5, 133.10, 131.90, 131.81, 131.6, 131.2, 128.6, 128.4, 128.0, 68.2, 61.5.

2 Experimental details

The obtained diffraction data were processed using the Shelxt software 1 , 2 to solve the crystal structure. The resulting crystal structure was visually represented using the OLEX2 software. 3

3 Comment

Hydroxylamine aryl phosphine oxides have not been synthesized in large quantities, may have unique biological activities and medicinal value, and can serve as important intermediates for the synthesis of α-aminophosphonic acids. α-Aminophosphonic acids and their phosphonic acid derivatives, 5 as an important surrogate for natural and unnatural α-amino acids, are known to have antitumor, 6 antibiotic, 7 pharmacogenetic and pharmacological properties. 8 Over the years, with the improvement of people’s environmental awareness, 9 how to build P–C–N bonds more green and efficiently has always been the goal 10 . In the prior technology, a radical addition method for adding P(O)–H bonds to alkenes or alkynes without adding solvent or catalyst has been studied. However, because nitrone is the N-oxide of imine, it has a unique C=N double bond in the structure, which shows its chemical properties different from C=C double bond, the method of adding P(O)–H bond to the unsaturated C=N double bond of nitrone has not been studied in depth. Nitrone is a weak electrophile, because it contains a polarized C=N double bond, so it is speculated that nitrone can effectively undergo nucleophilic addition reaction with the nucleophile to obtain the hydroxylamine derivative. The molecule forming the title crystal structure is shown in the figure. The important bond distances data are 1.4834(12) Å (P1–O1), 1.8533(16) Å (P1–C8), 1.7997(17) Å (P1–C15), 1.4341(17) Å (O2–N1), 1.467(2)(12) Å (N1–C7), 1.4782(19) Å (N1–C8), 1.8022(16) Å (P1–C21), respectively. Several important bond angle data are involved as follows O1–P1–C8 = 113.82(7)°, O1–P1–C15 = 111.47(7)°, O1–P1–C21 = 112.61(7)°. The other bond distances and angles are in their normal ranges.

Corresponding author: Chongning Jiang, College of Pharmacy, North China University of Science and Technology, 063210, Caofeidian District, Tangshan, P.R. China, E-mail:

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

  2. Research funding: None declared.

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

References

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Received: 2024-04-29
Accepted: 2024-05-30
Published Online: 2024-06-18
Published in Print: 2024-08-27

© 2024 the author(s), 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. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
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  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
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  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
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  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
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  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
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https://doi.org/10.1515/ncrs-2024-0192
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]−} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 −)
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
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