Home The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
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The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5

  • Xiao Guo , Tiejun Li , Xueli Cao ORCID logo EMAIL logo and Wenhao Zhang
Published/Copyright: August 12, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 5

Abstract

C26H26N4O5, triclinic, P 1 ‾ (no. 2), a = 7.245(2) Å, b = 12.522(3) Å, c = 13.789(3) Å, α = 75.420(1)°, β = 79.628(1)°, γ = 83.226(1)°, V = 1,187.5(5) Å3, Z = 2, R gt (F) = 0.0467, wR ref (F2) = 0.1399, T = 298 K.

CCDC no.: 2363039

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: Yellow block
Size: 0.22 × 0.18 × 0.14 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 0.77 mm−1
Diffractometer, scan mode: Bruker D8 VENTURE, φ and ω
θmax, completeness: 68.4°, 99 %
N(hkl)measured, N(hkl)unique, Rint: 16,092, 4,309, 0.049
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 3,634
N(param)refined: 323
Programs: Bruker 1 , SHELX 2 , 3 , Diamond 4
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.0628 (2) 0.05022 (12) 0.34557 (11) 0.0532 (4)
C2 −0.0894 (2) 0.10910 (12) 0.40441 (10) 0.0492 (3)
C3 −0.2746 (2) 0.08385 (13) 0.41119 (12) 0.0588 (4)
H3A −0.300764 0.032705 0.377887 0.071*
C4 −0.4182 (2) 0.13485 (14) 0.46728 (13) 0.0615 (4)
H4 −0.541692 0.118607 0.471199 0.074*
C5 −0.3805 (2) 0.20991 (13) 0.51778 (12) 0.0555 (4)
H5 −0.478693 0.242776 0.556440 0.067*
C6 −0.19585 (19) 0.23731 (12) 0.51157 (10) 0.0471 (3)
C7 −0.05201 (18) 0.18627 (12) 0.45365 (10) 0.0471 (3)
H7 0.071176 0.204086 0.447816 0.057*
C8 −0.16012 (18) 0.32311 (12) 0.56156 (10) 0.0467 (3)
C9 −0.2761 (2) 0.42146 (13) 0.55180 (12) 0.0537 (3)
H9 −0.378371 0.429541 0.517684 0.064*
C10 −0.2429 (2) 0.50653 (13) 0.59127 (12) 0.0574 (4)
H10 −0.322353 0.571059 0.583379 0.069*
C11 −0.0925 (2) 0.49695 (12) 0.64254 (12) 0.0537 (3)
H11 −0.069373 0.554704 0.668816 0.064*
C12 0.02352 (19) 0.39959 (12) 0.65419 (10) 0.0471 (3)
C13 −0.00921 (18) 0.31256 (11) 0.61493 (10) 0.0447 (3)
C14 0.3813 (2) 0.44718 (13) 0.77778 (11) 0.0530 (3)
C15 0.4638 (3) 0.52909 (14) 0.80971 (13) 0.0617 (4)
C16 0.4120 (4) 0.65026 (17) 0.78853 (19) 0.0897 (7)
H16A 0.476097 0.683314 0.827434 0.134*
H16B 0.278525 0.663358 0.806902 0.134*
H16C 0.447953 0.682353 0.717575 0.134*
C17 0.4940 (2) 0.34317 (13) 0.80869 (11) 0.0514 (3)
C18 0.7731 (2) 0.30618 (15) 0.90186 (12) 0.0599 (4)
C19 0.8359 (3) 0.20495 (18) 0.88273 (14) 0.0720 (5)
H19 0.779069 0.175850 0.840744 0.086*
C20 0.9854 (3) 0.1470 (2) 0.92714 (16) 0.0860 (6)
H20 1.027418 0.077700 0.915137 0.103*
C21 1.0758 (3) 0.1888 (2) 0.98951 (14) 0.0822 (6)
C22 1.0108 (3) 0.2902 (2) 1.00826 (17) 0.0864 (6)
C23 0.8605 (3) 0.34794 (18) 0.96455 (17) 0.0819 (6)
H23 0.816693 0.416652 0.977437 0.098*
C24 1.1018 (5) 0.3387 (3) 1.0762 (3) 0.1404 (14)
H24A 1.101275 0.287380 1.141021 0.211*
H24B 1.032754 0.406767 1.085157 0.211*
H24C 1.229210 0.352845 1.045675 0.211*
C25 1.2407 (4) 0.1226 (3) 1.0352 (2) 0.1106 (9)
H25A 1.341939 0.169446 1.024480 0.166*
H25B 1.281988 0.062100 1.003519 0.166*
H25C 1.202998 0.094405 1.106702 0.166*
C26 0.6304 (3) 0.0380 (3) 0.17458 (19) 0.1040 (8)
H26A 0.618332 0.035096 0.107121 0.156*
H26B 0.755745 0.011378 0.187136 0.156*
H26C 0.606080 0.113060 0.181320 0.156*
N1 0.17966 (17) 0.38416 (10) 0.70430 (9) 0.0511 (3)
H1 0.238477 0.319766 0.718465 0.061*
N2 0.23656 (18) 0.46707 (10) 0.72969 (9) 0.0519 (3)
N3 0.6224 (2) 0.37131 (11) 0.85751 (10) 0.0585 (3)
N4 0.6026 (2) 0.48493 (12) 0.85682 (11) 0.0668 (4)
O1 0.03772 (19) −0.02442 (10) 0.30888 (9) 0.0695 (3)
O2 0.23019 (16) 0.08517 (12) 0.33573 (11) 0.0712 (4)
H2 0.307229 0.049123 0.302925 0.107*
O3 0.11747 (13) 0.22214 (8) 0.62915 (9) 0.0544 (3)
H3 0.063056 0.165804 0.638128 0.082*
O4 0.47475 (16) 0.25184 (9) 0.79389 (9) 0.0604 (3)
O5 0.5027 (2) −0.02735 (13) 0.24382 (14) 0.0929 (5)
H5A 0.490608 −0.081728 0.223226 0.139*

1 Source of materials

All reagents for the synthesis were commercially procured and used without further treatment. A solution of 3′-amino-2′-hydroxy-1,1′-biphenyl-3- carboxylic acid (1.0 g, 4.36 mmol) in methanol (20 mL) was stirred at 0–5 °C, 4 M hydrochloric acid (2.9 g, 10.73 mmol) was added. A solution of sodium nitrite (0.31 g, 4.36 mmol) in water (2 mL) was added over 20 min. The reaction was stirred at 0–5 °C for 1 h. Triethylamine (0.8 g, 7.85 mmol) was added to bring the pH to 8–9 and 2-(3,4-dimethylphenyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one (0.79 g, 3.93 mmol) was added in one portion. The mixture was stirred for 3 h at 15–25 °C maintaining the pH 8–9. After the reaction was over, 4 M hydrochloric acid was added dropwise to adjust the pH to 1.5–2. The temperature was kept for 1 h, the precipitate was filtered, washed with water and dried at 45 °C to yield (Z)-3′-(2-(1-(3,4- dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylic acid (1.70 g, 88 % yield) as a yellow solid. 0.5 g of (Z)-3′-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-5-pyrazol-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylic acid was dissolved in 20 mL of methanol. After filtration, the solution was left to evaporate slowly at room temperature with the cap being left only slightly open. After a period of 7 days, yellow crystals of the title compound were obtained.

2 Experimental details

Hydrogen atom were placed in their geometrically idealized positions and constrained to ride on their parent atoms with C–H = 0.96 Å (methyl) or 0.93 Å (methylene), N–H = 0.86 Å, O–H = 0.82 Å. For H atoms in methyl and hydroxyl groups, the uncertainty displacement parameter (Uiso(H)) was constrained to 1.5 times the equivalent isotropic displacement parameter (Ueq), and for all other H atoms, it was constrained to 1.2 times Ueq of the parent atoms.

3 Comment

Eltrombopag, chemically known as (Z)-3′-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylic acid is a small molecule agonist of the c-mpl (TpoR) receptor, which is the physiological target of the hormone thrombopoietin. 5 Eltrombopag has a catalytic effect on the differentiation and proliferation of bone marrow progenitor cells, so it has been developed to treat immune thrombocytopenia (ITP). 6 , 7 , 8 , 9 , 10 The structural integrity and stability of Eltrombopag are crucial for its pharmaceutical applications. The study of its crystal structure not only provides insights into its physicochemical properties but also aids in the optimization of its formulation for improved bioavailability and therapeutic outcomes. 11 The crystalline structure elucidates that the two phenyl rings are not coplanar. 12 , 13 The dihedral angle between the best planes of the benzene ring (C2/C3/C4/C5/C6/C7) and benzene ring (C8/C9/C10/C11/C12/C13) is 44.61°. The crystalline structure elucidates that hydrogen bonds are important in the crystal structure. The hydroxyl group of methanol forms an O–H–O hydrogen bond to a carbonyl group. The complete set of X-ray diffraction data for the title compound was deposited to the Cambridge Crystallographic Data Centre (CCDC entry no. 2363039).

Corresponding author: Xueli Cao, Department of Chemistry and Chemical Engineering, College of Taishan, Tai’an, 271000, 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: Major Special Projects of Science and Technology Innovation of Tai’an (2021ZDZX029), Key Research and Development Program of Shandong Province (2021CXGC010514), Science and Technology Innovation Development Project of Tai’an (2023GX076), Double Ten Project of Tai’an (2023JSGG12).

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

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Received: 2024-06-16
Accepted: 2024-07-30
Published Online: 2024-08-12
Published in Print: 2024-10-28

© 2024 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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  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2′-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
https://doi.org/10.1515/ncrs-2024-0251
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Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O′:O″)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
  28. Crystal structure of catena-poly[bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-k3-O,O′:O″)hexaqua-dicobalt tetrahydrate], C26H36N4O20Co2
  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
  34. The crystal structure of (E)-6-bromo-3,5-dimethyl-2-(1-phenylprop-1-en-2-yl)-3Himidazo[4,5b]pyridine, C17H16BrN3
  35. Crystal structure of (3S,3′S,4R,4′S)-3′-(furan-3-yl)-3-hydroxy-4′-methyl-3,5,6′,7′-tetrahydro-1H,3′H-4,5′-spirobi[isobenzofuran]-1,1′(4′H)-dione-methanol (1/1), C21H22O7
  36. Cocrystal structure of progesterone-isophthalic acid, C25H33O4
  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
  38. Crystal structure of S-(4-carboxybutyl)- l -cysteine
  39. The cocrystal of 2,2′-(hydrazine-1,1-diyl)bis(1H-imidazole-4,5-dicarbonitrile)– methanol (2/3)
  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
  45. Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
  46. Crystal structure of 1-(5-(benzo[d][1,3]dioxol-5-yl)-4-benzyl-1-(4-bromophenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethan-1-one, C24H20BrN3O3
  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
  48. Crystal structure of (S)-1-phenylpropan-1-aminium (S)-(1-phenylpropyl)carbamate C19H26N2O2
  49. Synthesis and crystal structure of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, C18H16BrN3O2S
  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N′)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2′-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
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