Home The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
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The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7

  • Soon Young Shin , Ha-Jin Lee and Dongsoo Koh ORCID logo EMAIL logo
Published/Copyright: December 14, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 1

Abstract

C28H28O7, triclinic, P 1 ‾ (no. 2), a = 11.0746(18) Å, b = 11.4312(17) Å, c = 11.552(2) Å, α = 77.148(8)°, β = 62.164(8)°, γ = 67.858(8)°, V = 1195.9(4) Å3, Z = 2, R gt (F) = 0.0522, wRref (F 2) = 0.1862, T = 223(2) K.

CCDC no.: 2224186

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: 0.20 × 0.15 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: PHOTON 100 CMOS, φ and ω
θ max, completeness: 26.2°, 99%
N(hkl)measured, N(hkl)unique, R int: 29,975, 4697, 0.065
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2951
N(param)refined: 321
Programs: Bruker [1], SHELX [2, 3], Olex2 [4]
Table 2:

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

Atom x y z U iso*/U eq
C1 −0.0681 (2) 0.3211 (2) 0.4174 (2) 0.0449 (6)
O1 −0.10339 (17) 0.21218 (14) 0.46434 (19) 0.0589 (5)
H1 −0.1865 0.2285 0.5235 0.088*
C2 −0.1724 (2) 0.4390 (2) 0.4501 (2) 0.0482 (6)
H2 −0.2694 0.4457 0.5045 0.058*
C3 −0.1303 (2) 0.5454 (2) 0.4009 (2) 0.0488 (6)
C4 0.0126 (3) 0.5373 (2) 0.3221 (3) 0.0523 (6)
H4 0.0396 0.6110 0.2898 0.063*
C5 0.1145 (2) 0.4194 (2) 0.2918 (2) 0.0464 (6)
C6 0.0757 (2) 0.3082 (2) 0.3372 (2) 0.0418 (5)
O2 −0.22372 (19) 0.66599 (15) 0.4240 (2) 0.0678 (6)
C7 −0.3696 (3) 0.6821 (3) 0.5072 (3) 0.0687 (8)
H7A −0.4061 0.6384 0.4740 0.103*
H7B −0.4240 0.7715 0.5104 0.103*
H7C −0.3794 0.6474 0.5946 0.103*
O3 0.25865 (17) 0.40044 (16) 0.21597 (19) 0.0626 (5)
C8 0.3042 (3) 0.5099 (3) 0.1669 (4) 0.0809 (10)
H8A 0.2573 0.5628 0.1117 0.121*
H8B 0.4077 0.4842 0.1158 0.121*
H8C 0.2784 0.5570 0.2396 0.121*
C9 0.1814 (2) 0.1795 (2) 0.3038 (2) 0.0426 (6)
C10 0.2742 (2) 0.1251 (2) 0.3574 (3) 0.0511 (6)
H10 0.2735 0.1705 0.4164 0.061*
C11 0.3768 (2) −0.0017 (2) 0.3291 (3) 0.0505 (6)
O4 0.4554 (2) −0.05331 (19) 0.3844 (2) 0.0796 (7)
C12 0.3837 (2) −0.0686 (2) 0.2244 (2) 0.0429 (6)
H12 0.4482 −0.0409 0.1373 0.051*
C13 0.2331 (2) −0.0325 (2) 0.2282 (2) 0.0400 (5)
H13 0.1688 −0.0568 0.3172 0.048*
C14 0.1765 (2) 0.1120 (2) 0.2085 (2) 0.0446 (6)
H14A 0.2344 0.1381 0.1188 0.054*
H14B 0.0769 0.1371 0.2196 0.054*
C15 0.4474 (2) −0.2094 (2) 0.2457 (2) 0.0463 (6)
O5 0.38290 (17) −0.27433 (16) 0.33133 (19) 0.0634 (5)
O6 0.58315 (15) −0.25410 (15) 0.16003 (17) 0.0535 (5)
C16 0.6520 (3) −0.3910 (2) 0.1711 (3) 0.0701 (8)
H16A 0.6061 −0.4360 0.1494 0.084*
H16B 0.6417 −0.4174 0.2611 0.084*
C17 0.8053 (3) −0.4213 (3) 0.0799 (4) 0.0863 (11)
H17A 0.8146 −0.3911 −0.0083 0.129*
H17B 0.8512 −0.5122 0.0825 0.129*
H17C 0.8512 −0.3806 0.1054 0.129*
C18 0.2266 (2) −0.0975 (2) 0.1310 (2) 0.0427 (6)
C19 0.3440 (2) −0.1423 (2) 0.0176 (3) 0.0499 (6)
H19 0.4333 −0.1379 0.0025 0.060*
C20 0.3364 (3) −0.1950 (2) −0.0775 (3) 0.0548 (7)
H20 0.4196 −0.2258 −0.1537 0.066*
C21 0.2073 (3) −0.2008 (2) −0.0580 (3) 0.0524 (6)
C22 0.0818 (2) −0.1570 (2) 0.0572 (2) 0.0458 (6)
C23 −0.0532 (3) −0.1617 (2) 0.0778 (3) 0.0544 (7)
H23 −0.0588 −0.1956 0.0141 0.065*
C24 −0.1733 (3) −0.1185 (2) 0.1867 (3) 0.0580 (7)
H24 −0.2619 −0.1214 0.1979 0.070*
C25 −0.1662 (2) −0.0693 (2) 0.2830 (3) 0.0550 (7)
H25 −0.2501 −0.0403 0.3593 0.066*
C26 −0.0380 (2) −0.0630 (2) 0.2672 (3) 0.0488 (6)
H26 −0.0354 −0.0297 0.3331 0.059*
C27 0.0905 (2) −0.1057 (2) 0.1534 (2) 0.0423 (5)
O7 0.1851 (2) −0.24807 (19) −0.14345 (19) 0.0702 (6)
C28 0.2999 (3) −0.2770 (3) −0.2688 (3) 0.0792 (9)
H28A 0.3298 −0.2028 −0.3106 0.119*
H28B 0.2685 −0.3024 −0.3221 0.119*
H28C 0.3803 −0.3454 −0.2597 0.119*

Source of material

To a solution of 4,6-dimethoxy-2-hydroxyacetophenone (20 mmol, 3.32 g) in 100 ml of ethanol was added 4-methoxy-1-naphthaldehyde (20 mmol, 3.72 g) and the temperature was adjusted to around 276–278 K in an ice-bath. To the reaction mixture was added 15 mL of 50% (w/v) aqueous KOH solution and the reaction mixture was stirred at room temperature for 24 h. At the end of the reaction, ice water was added to the mixture and it was acidified with 6N HCl (pH = 3–4). The resulting precipitate was filtered and washed with water and ethanol. The crude solid was purified by recrystallization from ethanol to give pure chalcone. An excess amount of ethylacetoacetate (2.6 g, 20 mmol) was added to a solution of the chalcone compound (5 mmol, 1.82 g) in 50 mL anhydrous ethanol, and 5 mL of aqueous NaOH solution was added to the reaction mixture and was refluxed at 360 K for 5 h. The reaction mixture was cooled to room temperature and was acidified with 3N HCl (pH = 3–4). The resulting precipitate was filtered and washed with water and ethanol. The crude solid product was purified by recrystallization from ethanol to afford the title compound (m.p.: 375–377 K; yield: 72%).

Experimental details

Data collections and reduction were carried out using the Bruker software Apex2 and Saint including Sadabs [1]. Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Comment

Compounds containing a cyclohexenone moiety have been reported to inhibit acetylcholinesterase (AChE) [5], attenuate heart failure in a zebra fish model [6] and show anticancer activities in HCT116 human colon cancer cells [7]. Since cyclohexenone derivatives exhibit various biological activities, the title compound was designed and synthesized according to a previous report [8].

The molecular structure of the title compound is shown in the Figure. The central cyclohexenone ring (C9–C14) has an envelope conformation with the atom C13 as the flap. The benzene ring (C1–C6) and the naphthalene ring system (C18–C27) are attached to the central cyclohexenone ring (C9–C14) at positions C9 and C13, respectively. The dihedral angle between the benzene and ring (C1–C6) and the naphthalene ring system (C18–C27) is 65.03(3)°. The hydrogen atom H13 attached to C13 forms a trans diaxial conformation with each one of H12 atom of the C12 (H12–C12–C13–H13 = −177.2°) and H14A atom of the C14 methylene group (H14A–C14–C13–H13 = −176.1°). The hydrogen atom H13 forms a gauche conformation with the other methylene hydrogen atom H14B (H14B–C14–C13–H13 = −58.4°). The methoxy group at the ortho and para position of the benzene ring are almost coplanar with the ring [C6–C5–O3–C8 = 179.8(2)°, C2–C3–O2–C7 = 3.0(4)°]. However, the methoxy group on the naphthalene ring is tilted from the ring [C20–C21–O7–C28 = 9.1(4)°]. In the crystal, molecules are linked by pairs of O1–H1⋯O5 interactions forming inversion dimers. There are also C–H⋯O interactions present and the dimers are linked via C7–H7B⋯O4 hydrogen bonds. All derived bond lengths and angles of the title structure are in the typical ranges [9, 10].

Corresponding author: Dongsoo Koh, Department of Applied Chemistry, Dongduk Women’s University, Seoul 02748, Republic of Korea, E-mail:

Funding source: Basic Science Research Program

Award Identifier / Grant number: NRF-2021R1F1A1052699

Acknowledgements

The authors acknowledge financial support from the Basic Science Research Program (award No. NRF-2021R1F1A1052699). S. Y. Shin was supported by the KU Research Professor Program of Konkuk University.

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

  2. Research funding: Basic Science Research Program (award No. NRF-2021R1F1A1052699).

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

References

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Received: 2022-11-08
Accepted: 2022-12-03
Published Online: 2022-12-14
Published in Print: 2023-01-27

© 2022 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. Crystal structure of undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
https://doi.org/10.1515/ncrs-2022-0517
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
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