Home Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
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Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9

  • Hai-Lin Chen ORCID logo , Xian Li , Dong-Mei Yao EMAIL logo , Ze-Ping Luo , Yan-Ping Wang and Jian-Jing Lan
Published/Copyright: November 1, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 6

Abstract

C22H22N2O9, monoclinic, P21/c (no. 14), a = 7.7374(3) Å, b = 29.1082(11) Å, c = 8.7595(3) Å, β =  96.853 ( 3 ) ∘ , V = 1958.74(13) Å3, Z = 4, Rgt(F) = 0.0520, wRref (F2) = 0.1501, T = 100 K.

CCDC no.: 2302388

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: Red block
Size: 0.13 × 0.12 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.12 mm−1
Diffractometer, scan mode: ROD, Synergy Custom DW system, ω
θmax, completeness: 29.3°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 14766, 4372, 0.028
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 3383
N(param)refined: 318
Programs: CrysAlisPRO [1], Diamond [2], SHELX [3, 4]
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.72325 (18) 0.70755 (5) 0.94430 (15) 0.0302 (3)
H1 0.803283 0.721655 0.907218 0.045*
O2 0.41933 (19) 0.58657 (5) 0.37145 (15) 0.0312 (3)
O3 0.40939 (19) 0.57135 (5) 0.83217 (15) 0.0304 (3)
O4 0.0145 (2) 0.39433 (5) 0.22159 (16) 0.0334 (4)
H4 −0.011104 0.372950 0.279297 0.050*
O7 −0.03272 (19) 0.75635 (5) 1.31442 (16) 0.0327 (3)
O8 −0.11739 (19) 0.68461 (5) 1.34302 (17) 0.0363 (4)
N1 0.1660 (3) 0.46773 (6) 0.0737 (2) 0.0410 (5)
N2 0.4231 (2) 0.64722 (5) 1.13785 (17) 0.0226 (3)
H2 0.432622 0.632606 1.241837 0.027*
C1 0.6465 (2) 0.67838 (7) 0.8397 (2) 0.0243 (4)
C2 0.6499 (2) 0.68551 (7) 0.6804 (2) 0.0259 (4)
H2A 0.702946 0.712403 0.645884 0.031*
C3 0.5784 (2) 0.65445 (7) 0.5765 (2) 0.0254 (4)
H3 0.586891 0.659318 0.470431 0.031*
C4 0.4914 (2) 0.61496 (6) 0.6218 (2) 0.0224 (4)
C5 0.4873 (2) 0.60924 (6) 0.7792 (2) 0.0229 (4)
C6 0.5627 (2) 0.63967 (6) 0.8910 (2) 0.0233 (4)
C7 0.4152 (2) 0.58126 (6) 0.5124 (2) 0.0230 (4)
C8 0.3358 (2) 0.54101 (6) 0.5772 (2) 0.0225 (4)
C9 0.3394 (3) 0.53978 (7) 0.7309 (2) 0.0310 (5)
H9 0.289 (4) 0.5194 (10) 0.790 (3) 0.055 (8)*
C10 0.2544 (2) 0.50264 (6) 0.4835 (2) 0.0225 (4)
C11 0.2428 (3) 0.50196 (7) 0.3246 (2) 0.0288 (4)
H11 0.290664 0.526699 0.272712 0.035*
C12 0.1626 (3) 0.46591 (7) 0.2390 (2) 0.0291 (4)
C13 0.0898 (2) 0.42847 (6) 0.3068 (2) 0.0259 (4)
C14 0.1054 (3) 0.42864 (7) 0.4681 (2) 0.0273 (4)
H14 0.060505 0.403487 0.520180 0.033*
C15 0.1839 (3) 0.46423 (7) 0.5524 (2) 0.0263 (4)
H15 0.192 (3) 0.4620 (8) 0.664 (3) 0.037 (6)*
C16 0.5716 (2) 0.62845 (7) 1.0600 (2) 0.0254 (4)
H16A 0.574308 0.594636 1.072184 0.031*
H16B 0.682111 0.640710 1.113133 0.031*
C17 0.2475 (2) 0.63375 (7) 1.0573 (2) 0.0271 (4)
H17A 0.243384 0.600068 1.041725 0.033*
H17B 0.228892 0.648679 0.955154 0.033*
C18 0.1055 (3) 0.64802 (7) 1.1511 (2) 0.0288 (4)
H18A 0.118402 0.630865 1.249356 0.035*
H18B −0.009066 0.640030 1.094522 0.035*
C19 0.1110 (2) 0.69905 (7) 1.1843 (2) 0.0255 (4)
H19 0.086793 0.715777 1.084340 0.031*
C20 0.2929 (3) 0.71344 (7) 1.2601 (2) 0.0277 (4)
H20A 0.297033 0.747265 1.271701 0.033*
H20B 0.314549 0.699651 1.363923 0.033*
C21 0.4343 (3) 0.69811 (6) 1.1647 (2) 0.0258 (4)
H21A 0.420425 0.714404 1.064811 0.031*
H21B 0.550000 0.705980 1.219211 0.031*
C22 −0.0265 (2) 0.71368 (7) 1.2880 (2) 0.0267 (4)
O5a 0.2909 (3) 0.48698 (8) 0.0261 (2) 0.0538 (6)
O6a 0.0492 (4) 0.44931 (7) −0.0124 (2) 0.0544 (7)
O5Ab 0.184 (4) 0.5090 (7) 0.019 (3) 0.0538 (6)
O6Ab 0.166 (5) 0.4382 (7) −0.017 (2) 0.0544 (7)
O9 −0.0796 (2) 0.32321 (5) 0.36681 (18) 0.0378 (4)
H9A −0.058854 0.300415 0.307328 0.057*
H9B −0.019356 0.316840 0.454620 0.057*

1 Source of materials

All reagents and chemicals were purchased from commercial sources and used without further purification. A mixture of 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one (0.013 g), sodium nitrite (0.035 g), 6 mol/L nitric acid (1.0 mL) and water (10 mL) was sealed in a 20 mL vial and stood for 10 min. The mixture was sonicated for 1 min. The mixture was heated at 363 K for 24 h. The mixture was filtered and the residue was washed with water. The residue was dried at 353 K. 7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4H-chromen-4-one (0.015 g) was obtained. A mixture of nitro compound described before (0.015 g), piperidine-4-carboxylic acid (0.026 g), N,N-dimethyl formamide (1 mL), methanol (3 mL) and formaldehyde solution (20 μL, 37 %) was sealed in a 20 mL vial and sonicated for 10 min. Then the mixture was heated at 363 K for 24 h. The mixture evaporated for one day at room temperature. Red block shape crystals of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl) methyl)piperidin-1-ium-4-carboxylate monohydrate were obtained. 1H NMR (400 MHz, DMSO-d6) δ:8.50 (s, 1H, H9), 8.16 (d, J = 2.1 Hz, 1H, H11), 7.92 (d, J = 8.8 Hz, 1H, H3), 7.73 (dd, J = 8.7, 2.1 Hz, 1H, H15), 7.16 (d, J = 8.7 Hz, 1H, H14), 6.91 (d, J = 8.8 Hz, 1H, H2) 3.97 (s, 2H, H16A and H16B), 2.92 (m, 3H, H17B, H21B, H19), 2.32 (m, 2H, H17A, H21A), 1.87 (m, 2H, H18B, H20A), 1.59 (m, 2H, H18A, H20B). 13C NMR (100 MHz, DMSO-d6) δ:175.74 (C7), 174.47 (C22), 163.45 (C1), 155.16 (C5), 153.67 (C9), 152.30 (C13), 136.57 (C12), 135.43 (C15), 125.77 (C3), 125.26 (C10), 122.68 (C8), 121.20 (C11), 119.14 (C14), 116.05 (C4), 115.34 (C6), 108.37 (C2), 52.05 (C16), 51.76 (C17 and C21), 39.73 (C19), 27.75 (C18 and C20). IR spectra (potassium bromide pellet) were recorded on a Nicolet 6700. IR (v/cm−1): 3005, 2856, 2704, 1625, 1573, 1525, 1445, 1423, 1396, 1373, 1343, 1308, 1265, 1244, 1211, 1183, 1644, 1094, 1077, 1041, 962, 926, 823, 802, 785, 764, 717, 687, 640, 551, 495, 456, 428.

2 Experimental details

Carbon-bound H atoms with the exception of H15 and H9 were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 Ueq(C). The oxygen-bound, nitrogen-bound H atoms, H15 and H9 were located on a difference Fourier map. The O5 and O6 atoms were disordered.

3 Comment

Numerous publications describe the nitrated derivatives and Mannich base derivatives of flavonoids [5, 6]. Some derivatives of flavonoids possess important biological activities. Our previous investigations showed that daizein Mannich base derivatives of amino acid or aliphatic amine react with nitrating agent [7], [8], [9]. To extend this research, we investigated a new synthetic route. Nitro group was first introduced on the 3'-position of ring B of daidzein. Then we used the intermediate to react with piperidine-4-carboxylic acid by Mannich reaction and got the title compound. The presence of several groups in daizein derivatives expands the capability of studying their biological activity.

The title structure contains one zwitterion and one water molecule in the asymmetric unit (cf. the figure). The bond distances and bond angles are in normal ranges [7], [8], [9]. The dihedral angle between planar rings B (C10–C15) and C (C7–C9/O3/C5/C4) is 1.59 ∘ . There are two π-π stacking interactions between phenyl rings from adjacent molecules. The centroid-centroid distance of C1–C6 phenyl rings and C10–C15 phenyl rings is 4.05 Å. The centroid-centroid distance of C10–C15 phenyl rings is 3.97 Å. The nitrogen atom N2 is protonated. There exist various O–H⋯O and N–H⋯O hydrogen bonds. Together with hydrogen bonds interactions and π-π stacking interactions a three dimensional network is obtained.

Corresponding author: Dong-Mei Yao, School of Chemical and Biological Engineering, Hechi University, Yizhou District, Hechi, Guangxi, 546300, 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: This work was financially supported by Guangxi Natural Science Foundation of China (No. 2020GXNSFBA297138) and 2021 High-level Talents Scientific Research Startup Fund of Hechi University (No. 2021GCC021).

  3. Competing interests: The authors declare no conflicts of interest regarding this article.

References

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Received: 2023-09-17
Accepted: 2023-10-20
Published Online: 2023-11-01
Published in Print: 2023-12-15

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

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  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-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
https://doi.org/10.1515/ncrs-2023-0412
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] – 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-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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