Home Physical Sciences Crystal structure of 6-methoxy-3-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4H-chromen-4-one-methanol (1/1), C20H18N2O6
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Crystal structure of 6-methoxy-3-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4H-chromen-4-one-methanol (1/1), C20H18N2O6

  • Soon Young Shin , Miri Yoo and Dongsoo Koh ORCID logo EMAIL logo
Published/Copyright: July 2, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 5

Abstract

C19H14N2O5 ⋅ CH3OH, monoclinic, P21/c (no. 14), a = 7.9074(3) Å, b = 20.4341(7) Å, c = 11.0406(4) Å, β = 92.6004(16)°, V = 1783.85(11) Å3, Z = 4, Rgt(F) = 0.0467, wRref(F2) = 0.1260, T = 223(2) K.

CCDC no.: 2012186

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:0.22 × 0.12 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.11 mm−1
Diffractometer, scan mode:PHOTON 100 CMOS, φ and ω
θmax, completeness:28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint:86382, 4456, 0.080
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3129
N(param)refined:257
Programs:Bruker [1], SHELX [2], [3], Olex2 [4], PublCIF [5]
Table 2:

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

AtomxyzUiso*/Ueq
O10.00874(17)0.49997(6)0.81048(11)0.0448(3)
O20.09386(15)0.66757(5)0.61913(10)0.0349(3)
O3−0.24451(16)0.69350(6)1.04774(10)0.0403(3)
O40.27408(13)0.49629(5)0.47887(9)0.0289(3)
N10.2503(2)0.39338(7)0.53418(13)0.0397(4)
N20.1644(2)0.43265(7)0.61833(13)0.0383(4)
C10.0344(2)0.55012(7)0.75304(14)0.0291(3)
C2−0.01964(19)0.61465(7)0.79644(14)0.0265(3)
C3−0.10580(19)0.62065(8)0.90656(14)0.0291(3)
H3−0.12810.58350.95390.035*
C4−0.1571(2)0.68166(8)0.94426(14)0.0314(3)
C5−0.1210(2)0.73722(8)0.87532(16)0.0360(4)
H5−0.15470.77870.90300.043*
C6−0.0370(2)0.73192(8)0.76803(16)0.0348(4)
H6−0.01290.76930.72170.042*
C70.0118(2)0.67026(8)0.72887(14)0.0288(3)
C80.1427(2)0.60923(8)0.57777(15)0.0323(4)
H80.19700.60780.50250.039*
C90.11949(19)0.55233(7)0.63650(13)0.0268(3)
C10−0.2790(2)0.63973(10)1.12483(16)0.0434(4)
H10A−0.35060.60861.08230.065*
H10B−0.33630.65521.19660.065*
H10C−0.17370.61871.14820.065*
C110.18235(19)0.49228(7)0.58259(13)0.0271(3)
C120.31094(19)0.43227(7)0.45487(14)0.0284(3)
C130.40607(19)0.41612(8)0.34670(14)0.0275(3)
C140.4379(2)0.35047(8)0.32287(14)0.0316(3)
H140.40000.31800.37640.038*
C150.5258(2)0.33311(8)0.21997(15)0.0343(4)
C160.5819(2)0.38110(9)0.14121(15)0.0386(4)
H160.64220.36950.07160.046*
C170.5484(2)0.44623(9)0.16571(16)0.0400(4)
H170.58640.47860.11200.048*
C180.4604(2)0.46445(8)0.26759(15)0.0345(4)
H180.43750.50880.28320.041*
O50.54987(18)0.26761(6)0.20448(12)0.0499(4)
C190.6158(3)0.24590(11)0.09180(18)0.0574(6)
H19A0.54790.26370.02590.086*
H19B0.61260.19850.08860.086*
H19C0.73170.26070.08410.086*
C200.2343(3)0.62376(11)0.16812(19)0.0535(5)
H20A0.15180.64340.11360.080*
H20B0.26470.58070.13840.080*
H20C0.33440.65110.17220.080*
O60.1652(2)0.61801(7)0.28324(12)0.0571(4)
H6A0.08910.59000.28190.086*

Source of material

The oxadiazole compound was obtained by hypervalent iodine catalyzed oxidative cyclization reaction of corresponding chromenonyl-benzohydrazide (I), which was described in the literature [6]. 6-Methoxy–3–formylchromone (100 mg, 0.5 mmol), prepared by previously reported methods [7], was treated with 3-methoxybenzohydrazide (80 mg, 0.5 mmol) in ethanol (20 mL) and the mixture was refluxed for 5 h in the presence of catalytic amounts of glacial acetic acid. After cooling, the solvent was removed under vacuum and the product 3-methoxy-N′-((6-methoxy-4-oxo-4H-chromen-3-yl)methylene) benzohydrazide (I) was used for next step. To a solution of I, (70 mg, 0.2 mmol) in methylene chloride (20 mL), 1.5 equivalents of diacetoxyiodobenzene (97 mg, 0.3 mmol) [8] were added portion–wise over 30 min. The mixture was stirred at room temperature for 18 h and poured into water (40 mL). After extraction with methylene chloride (25 mL × 2), the combined organic layers were dried over MgSO4. Filtration and evaporation of the organic solvent gave a solid, which was recrystallized in methanol to afford crystals used in this X-ray diffraction study.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Comment

Flavonoids are well known secondary metabolites in plants and play important role in various biological processes [9], [10]. The characteristic skeletal structure of flavonoids are chromenons. Oxadiazole derivatives have attracted considerable interests due to their wide application as medicinal pharmacophore [11]. According to recent research, the 1,3,4-oxadiazole units were introduced as potential linkers to meet ‘the 5-atoms role’ to generate potent pharmacophores [12]. As a continuation of our research program to expand the use of novel synthetic flavones [13], [14], we designed a new flavone which has oxadiazole linker between chromenon and benzene ring.

The title compound crystallized as a methanol solvate (see the Figure). In the title molecule, the whole molecule is approximately planar and dihedral angles formed by central oxadiazole ring with substituated phenyl ring and chromenon moiety are 2.29(2)°, 4.75(1)° respectively. The methoxy group at the phenyl ring is coplanar with the ring [C3—C4—O3—C10 torsion angle = 2.8(2)°], whereas the methoxy group at the chromenonyl moiety is slightly twisted from the corresponding ring [C16—C15—O5—C19 torsion angle = −9.3(3)°]. In the crystal methanol acts as a hydrogen bond donor and an acceptor to form tetramers which are composed of two title molecules and two molecules of methanol. The hydrogen atom of methanol solvent interacts with carbonyl oxygen (O1) and one of nitrogen atom (N2) in the oxadiazole ring through a bifurcated O6—H6A—O1 and O6—H6A—N2 hydrogen bonds to form a six-membered ring. Additional weak intermolecular hydrogen bonds, C8—H8—O6, formed between solvated methanol and the title molecule generates inversion dimers of title compounds, which are intercalated by two molecules of methanol. Another nitrogen atoms (N1) in the oxadiazole ring forms intermolecular hydrogen bond interactions C5—H5—N1 which link the tetramers into chains propagating along the b-axis.

Acknowledgements

The authors acknowledge financial support from the Basic Science Research Program (award No. NRF- 2019R1F1A1058747). S.Y. Shin was supported by the KU Research Professor Program of Konkuk University.

References

1. Bruker. SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, WI, USA (2012).Search in Google Scholar

2. Sheldrick, G. M.: SHELXT – integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

4. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H.: OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 42 (2009) 339–341.10.1107/S0021889808042726Search in Google Scholar

5. Westrip, S. P.: publCIF: software for editing, validating and formatting crystallographic information files. J. Appl. Crystallogr. 43 (2010) 920–925.10.1107/S0021889810022120Search in Google Scholar

6. Kim, B. S.; Koh, D.; Cho, S. K.; Song, Y. W.; Sung, J.; Lim, Y.: 1H and 13C NMR characterization of 1,3,4–oxadiazole derivatives. Magn. Reson. Chem. 56 (2018) 782–791.10.1002/mrc.4718Search in Google Scholar PubMed

7. Koh, D.; Jung, Y.; Ahn, S.; Mok, K. H.; Shin, S. Y.; Lim, Y.: Synthesis and structure elucidation of polyphenols containing the N′–methyleneformohydrazide scaffold as aurora kinase inhibitors. Magn. Reson. Chem. 55 (2017) 864–876.10.1002/mrc.4611Search in Google Scholar PubMed

8. Dobrota, C.; Paraschivescu, C. C.; Dumitru, I.; Matache, M.; Baciu, I.; Ruţă, L. L.: Convenient preparation of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles promoted by Dess–Martin reagent. Tetrahedron Lett. 50 (2009) 1886–1888.10.1016/j.tetlet.2009.02.054Search in Google Scholar

9. Zhao, L.; Yuan, X.; Wang, J.; Feng, Y.; Ji, F.; Li, Z.; Bian, J.: Review on flavones targeting serine/threonine protein kinases for potential anticancer drugs. Bioorg. Med. Chem. 27 (2019) 677–68510.1016/j.bmc.2019.01.027Search in Google Scholar PubMed

10. Singh, M.; Kaur, M.; Silakari, O.: Flavones: an important scaffold for medicinal chemistry. Eur. J. Med. Chem. 84 (2014) 206–239.10.1016/j.ejmech.2014.07.013Search in Google Scholar PubMed

11. Bajaj, S.; Asati, V.; Singh, J.; Roy, P. P.: 1,3,4-Oxadiazoles: an emerging scaffold to target growth factors, enzymes and kinases as anticancer agents. Eur. J. Med. Chem. 97 (2015) 124–141.10.1016/j.ejmech.2015.04.051Search in Google Scholar PubMed

12. Xu, C.; Han, Y.; Xu, S.; Wang, R.; Yue, M.; Tian, Y.; Li, X.; Zhao, Y.; Gong, P.: Design, synthesis and biological evaluation of new Axl kinase inhibitors containing 1,3,4-oxadiazole acetamide moiety as novel linker. Eur. J. Med. Chem. 186 (2020) 111867.10.1016/j.ejmech.2019.111867Search in Google Scholar PubMed

13. Shin, S. Y.; Lee, Y.; Kim, B. S.; Lee, J.; Ahn, S.; Koh, D.; Lim, Y.; Lee, Y.: Inhibitory effect of synthetic flavone derivatives on pan-aurora kinases: induction of G2/M cell-cycle arrest and apoptosis in HCT116 human colon cancer cells. Int. J. Mol. Sci. 19 (2018) 4086.10.3390/ijms19124086Search in Google Scholar PubMed PubMed Central

14. Ahn, S.; Sung, J.; Lee, J. H.; Yoo, M.; Lim, Y.; Shin, S. Y.; Koh, D.: Synthesis, single crystal X-ray structure, Hirshfeld surface analysis, DFT computations, docking studies on aurora kinases and an anticancer property of 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6,7-dimethoxy-4H-chromen-4-one. Crystals 10 (2020) 413.10.3390/cryst10050413Search in Google Scholar

Received: 2020-06-17
Accepted: 2020-06-25
Published Online: 2020-07-02
Published in Print: 2020-08-26

©2020 Soon Young Shin et al., published by De Gruyter, Berlin/Boston

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

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  64. Crystal structure of poly[diaqua-bis(μ2-4-(3-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)benzoato-κ2N:O)nickel(II)], C28H22O6N8Ni
  65. Crystal structure of 4,4′-bis(pyridin-1-ium-4-yl)biphenyl poly[bis(μ2-4,4′-bis(pyrid-4-yl)biphenyl-K2N:N′)-tetrakis(μ4-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-K4O,O′:O′′:O′′′)-bis[[μ2-1,1′-biphenyl]-3-carboxyl-5-carboxylato-K2O:O′]tetracobalt(II)]— [1,1′-biphenyl]-3,5-dicarboxylic acid (1/2), C93H68N3O16Co2
  66. The crystal structure of 4a-formyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-1-2-6a,6b,9,9,12a-heptamethylpicen-10-yl acetate, C32H50O3
  67. Crystal structure of 3,3′-(1,2-phenylenebis(methylene))bis(1-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C16H20F12N4P2
  68. Crystal structure of catena-poly[diaqua-(μ2-tartrato-κ4O,O′:O′′,O′′′)zinc(II)], C4H8O8Zn
  69. The crystal structure of (6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-10-(4-acetoxy-3-methylbutyl)-6a,8a,9-trimethyl-3,4,5,6,6a,6b,7,8,8a,8b,9,10,11a,12,12a,12b-hexadecahydro-1H-naphtho[2′,1′:4,5]indeno[2,1-b]furan-4-yl acetate, C31H48O5
  70. Crystal structure of 4,4′-(oxybis(methylene))bis(bromobenzene), C14H12Br2O
  71. Crystal structure of (N,N-dimethylsulphoxide)-[N-(3-ethoxy-2-(oxide)benzylidene)-3-methoxybenzenecarbohydrazonato-κ3N,O,O′]-dioxo-molybdenum(VI), C19H22MoN2O7S
  72. Crystal structure of dichlorido-bis(dimethyl sulphoxide-κO)-bis(4-methylbenzyl-κC1)tin(IV), C20H30Cl2O2S2Sn
  73. Crystal structure of (E)-2-amino-N′-(2-hydroxy-4-(2-(piperidin-1-yl)ethoxy)benzylidene)benzohydrazide monohydrate, C21H26N4O3 ⋅ H2O
  74. Crystal structure of chloridotris(4-chlorophenyl)(dimethyl sulfoxide-κO)tin(IV), C20H18Cl4OSSn
  75. Crystal structure of catena{di-aqua-sodium-[N-(hydroxyethyl), N-isopropyl-dithiocarbamato]}n, [C6H16NNaO2S2]n
  76. Crystal structure of 2,2,4,4,6,6-hexakis(4-chlorophenyl)-1,3,5,2,4,6-trithiatristanninane, C36H24Cl6S3Sn3
  77. Crystal structure of 6-methoxy-3-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4H-chromen-4-one-methanol (1/1), C20H18N2O6
  78. Crystal structure of hexanedihydrazide, C6H14N4O2
  79. Crystal structure of tert-butyl 2-(hydroxymethyl)-5-{4-[(methoxycarbonyl)amino]phenyl}-2,5-dihydro-1H-pyrrole-1-carboxylate, C18H24N2O5
  80. Crystal structure of [(Z)-O-isopropyl N-(4-nitrophenyl)thiocarbamato-κS]-(triphenylphosphine-κP)-gold(I), C28H26AuN2O3PS
  81. Crystal structure of [O-ethyl N-(4-nitrophenyl)thiocarbamato-κS](tri-4-tolylphosphine-κP)gold(I) tetrahydrofuran solvate, C30H30AuN2O3PS, C4H8O
https://doi.org/10.1515/ncrs-2020-0298
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of isopimara-7,15-dien-3-one, C20H30O
  3. Crystal structure of bis(6-aminopyridine-2-carboxylato-κ2O,N)-copper(II), C12H10O6N4Cu
  4. Crystal structure of 5,6-diphenyldibenzo[c, g]chrysene, C38H24
  5. Poly[bis(dimethylformamide-κO)-(μ8-5,5′′-dicarboxy-[1,1′:4′,1′′-terphenyl]-2′,3,3′′,5′-tetracarboxylato-κ8O:O1:O2:O3:O4:O5:O6:O7)dizinc(II)] — dimethylformamide (1/2), C18H19N2O8Zn
  6. The crystal structure of poly[bis(N,N-dimethylformamide-κ1O)(μ4- 2′,5,5′,5′′-tetracarboxy-[1,1′:4′,1′′-terphenyl]-3,3′′-dicarboxylato-κ4O:O′:O′′:O′′′)manganese(II)] — N,N-dimethylformamide (1/2), C36H40N4O16Mn
  7. Crystal structure of N,N-dimethyl-4-((7-nitrobenzo[c][1,2,5]thiadiazol-4-yl)ethynyl)aniline, C16H12N4O2S
  8. The crystal structure of 8a-methoxy 8a-methoxy-1,5,8a,9a-tetrahydro-4H-8,9-dioxa-3a1λ4-aza-8aλ4, C18H14BNO3
  9. Crystal structure of poly[diaqua-(μ2-5-isopropoxyisophthalato-κ2O:O′)-(μ2-(1,3-bis(3,5-di(1H-imidazol-1-yl)pyridine))-κ2N:N′)cobalt(II)] monohydrate, C22H25N5O8Co
  10. The crystal structure of acetoximium 1′-hydroxy-1H,1H′-5,5′-bitetrazole-1-olate monohydrate, C5H11N9O4
  11. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-vinyl-1H-imidazol-3-ium hexafluoridophosphate(V), C9H13F6N2O2P
  12. The crystal structure of catena-poly[(μ2-4-(benzo[d]imidazol-2-yl)benzenecarboxylato-κ2N,O)-(μ2-4-(benzo[d]imidazol-2-yl)benzenecarboxylato-κ3N,O:O′)cadmium(II)]dihydrate, C28H22CdN4O6
  13. Enzyme-mediated synthesis and crystal structure of (2R,4S)-hydroxyketamine, C13H16ClNO2
  14. The crystal structure of bis(isothiocyanato-κ1N)-(methanol-κ1O)-[2-morpholine-4-yl-4,6-di(pyrazol-1-yl)-1,3,5-triazine-κ3N,N′,N′′] manganese(II), C16H18MnN10O2S2
  15. Crystal structure of bis{5-chloro-2-(((4-trifluoromethyl)imino)methyl)phenolato-κ2N,O}copper(II), C28H16Cl2CuF6N2O2
  16. Crystal structure of bis(1,3-phenylenedimethanaminium) bis(triiodide) tetraiodide – water (1/2) , C8H16I5N2O
  17. Crystal structure and anti-inflammatory activity of (3E,5E)-3,5-bis(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one, C25H18F3NO3S
  18. The crystal structure of bis{3-(diphenylphosphaneyl)propanoato-κ2O,P}platinum(II) dihydrate, C30H28O6P2Pt
  19. The crystal structure of (E)-2-(4-((4-fluorobenzyl)oxy)styryl)-4,6-dimethoxybenzaldehyde, C24H21FO4
  20. Crystal structure of bis[3-methoxy-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-κ3O,N,N′]nickel(II), C28H26N8O4Ni
  21. Crystal structure of 1-(2-(pyridin-2-yl)-5-(pyridin-3-yl)-1,3,4-oxadiazol-3(2H)-yl)ethan-1-one, C14H12N4O2
  22. Synthesis and crystal structure of 3-N-acetyl-5-(pyridin-3-yl)-2-(quinolin-2-yl)-1,3,4-oxadiazoline, C18H14N4O2
  23. Crystal structure of 2-methyl-1H-perimidine, C12H10N2
  24. Crystal structure of (E)-2-(5,5-dimethyl-3-(4-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)oxy)styryl)cyclohex-2-en-1-ylidene)malononitrile, C25H19N5O4
  25. Structural elucidation of 1-(3-acetyl-2,6-dihydroxy-4-methoxyphenyl)-4,5-dihydroxy-2-methylanthracene-9,10-dione isolated from Bulbine latifolia (L.) Wild, C24H18O8
  26. Crystal structure of 3-cinnamoyl-4-hydroxybenzoic acid, C16H12O4
  27. The crystal structure of poly[bis(μ4-2,3-pyridinedicarboxylato)-(μ2-oxalyl dihydrazide)-dicadmium(II) dihydrate], C16H16O12N6Cd2
  28. Synthesis and crystal structure of 1-{4-[(3-bromo-2-hydroxy-benzylidene)amino]phenyl}ethanone, C15H12BrNO2
  29. Synthesis and crystal structure of 1-{4-[(2-bromo-6-hydroxy-benzylidene)amino]phenyl}ethanone, C15H12BrNO2
  30. Crystal structure of (4-aminobenzoato-κ2O,O′)-[5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′]nickel(II) perchlorate monohydrate, C23H44ClN5NiO7
  31. Crystal structure of 1-{4-[(4-fluoro-2-hydroxy-benzylidene)amino]phenyl}ethanone, C15H12FNO2
  32. Preparation and crystal structure of a non-symmetrical vanadium(II) dimer: tri-μ2-bromido-(hydrogen-tris(3-isopropyl-4-bromopyrazol-1-yl)borato-κ3N,N′,N′′)-tris(tetrahydrofuran-κO)divanadium(II) – tetrahydrofuran (1/1), C34H57BBr6N6O4V2
  33. Crystal structure of bis{2-(((4-(1-(hydroxyl-imino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C30H26CoN4O4
  34. Crystal structure of 3-((3-nitrophenyl)sulfonamido)propanoic acid — 4,4′-bipyridine (1/1), C19H18N4O6S
  35. Crystal structure of cyclo[diaqua-bis(μ2-3′,5-dicarboxy-[1,1′-biphenyl]-3,4′-dicarboxylato-κ4O,O′:O′′,O′′′)-bis(4,4′-bis(pyrid-4-yl)biphenyl-K1N)dicadmium(II)], C76H52Cd2N4O18
  36. Crystal structure of 1-(adamantan-1-yl)-3-aminothiourea, C11H19N3S
  37. Crystal structure of catena-poly[triaqua-(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(3′,5-dicarboxy-[1,1′-biphenyl]-3,4′-dicarboxylato-κO)nickel(II)], C32H26N2O11Ni
  38. Crystal structure of catena-poly[aqua-(μ4-4,4′-(pyridine-3,5-diyl)dibenzoato-κ4O,O′:O′′:O′′′)zinc(II)], C19H13NO5Zn
  39. Crystal structure of 4-(4′-(pyridin-4-yl)-[1,1′-biphenyl]-4-yl)pyridin-1-ium 2-carboxy-4-(3,5-dicarboxyphenoxy)benzoate hydrate, C38H28N2O10
  40. Crystal structure of 3-[(triisopropylsilanyl)-ethynyl]-6a,12a-dihydro-1H-1,4-diaza-benzo[α]anthracene-2,7,12-trione, C27H28N2O3Si
  41. Crystal structure of [(bis(1,10-phenanthroline-κ2N,N′)-(2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ2O:O′))nickel(II) monohydrate, (1,10-phenanthroline-κ2N:N′)-(μ2-(5-(3′,4′-dicarboxylphenoxy)-isophthalate-κ2O:O′))nickel(II)], C40H24N4O9Ni ⋅ H2O
  42. Crystal structure of 4-(3-(pyridin-3-yl)ureido)benzoic acid — adipic acid (2/1), C16H16N3O5
  43. Crystal structure of poly[bis{μ2-5-carboxy-4′-methyl-[1,1′-biphenyl]-3-carboxylato-κ2O:O′}-{μ2-4,4′-bipyridine-κ2N:N′}]cobalt(II), C40H30N2O8Co
  44. Crystal structure of aqua-(2,2′-bipyridine-κ2N,N′)(((3-nitrophenyl)sulfonyl)glycine-κ2N,O)copper(II) dihydrate, C18H20CuN4O9S
  45. Crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}copper(II), C32H28Br2CuN4O4
  46. Crystal structure of bis(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κ2O,O′)-(1,10-phenanthroline-κ2N,N′)zinc(II), C40H28Cl4N4O4Zn
  47. Crystal structure of 2-(3,6-dimethyl-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)-2-oxoethyl acetate, C14H17NO4
  48. Crystal structure of poly[dibromido-bis(μ2-1,6-di(1H-imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C24H36Br2N8Cd
  49. Synthesis and crystal structure of ((6R,7S)-3-ethyl-6-phenyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)(phenyl)methanone hemihydrate, 2(C19H18N4OS) ⋅ H2O
  50. Crystal structure of 2-(5-(pyridin-3-yl)-4-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)pyridine, C17H12N6
  51. The crystal structure of N-((1E,2E)-1,3-bis(4-fluorophenyl)but-2-en-1-ylidene)-4-methylbenzenesulfonamide, C23H19F2NO2S
  52. Crystal structure of diacetato-κ1O-diethanol-κ1O-bis(μ2-2-(((2-hydroxyethyl)imino)methyl)-5-methoxyphenolato-κ4O,N,O′:O′′)dinickel(II), C28H42Ni2N2O12
  53. The crystal structure of catena-poly[chlorido-(μ2-1,4-bis(pyridin-3-yl-methoxy)benzene-κ2N:N′)copper(II)], C18H16ClN2O2Cu
  54. N′,N′′′-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(methaneylylidene))bis(2-hydroxybenzohydrazide)nickel(II), C30H24N4NiO6
  55. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-(2-((quinolin-2-ylmethylene)amino)ethyl)spiro[isoindoline-1,9′-xanthen]-3-one, C38H37N5O2
  56. Crystal structure of 4,4′-di(1H-imidazol-1-yl)-1,1′-biphenyl-1-ium 5,3′,5′-tricarboxy-[1,10-biphenyl]-2-carboxylate, C25H17N2O8
  57. The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C14H19N2O2Cl
  58. The crystal structure of 5-bromo-2-fluoronicotinic acid monohydrate, C6H5BrFNO3
  59. Crystal structure of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C7H7F3N2O2
  60. Crystal structure of tetrakis(1H-benzo[d]imidazol-3-ium) bis(μ5-phenylphosphonato)-pentakis(μ2-oxido)-decaoxo-penta-molybdenum dihydrate, C40H42Mo5N8O23P2
  61. Structure of 7-(3,3,4,4,5,5-hexafluoro-2-(2-methylbenzo[b]thiophen-3-yl)cyclopent-1-en-1-yl)-8-methylquinoline, C24H15F6NS
  62. Crystal structure of monocarbonyl[2-((cyclopentylmethylene)amino)-5-methylphenolato-κ2N,O] (tricyclohexylphosphine)rhodium(I), C32H48NO2PRh
  63. The crystal structure of fac-tricarbonyl(1,10-phenanthroline-κ2N,N′)-(pyrazole-κN)rhenium(I)nitrate, C18H12O3N4Re
  64. Crystal structure of poly[diaqua-bis(μ2-4-(3-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)benzoato-κ2N:O)nickel(II)], C28H22O6N8Ni
  65. Crystal structure of 4,4′-bis(pyridin-1-ium-4-yl)biphenyl poly[bis(μ2-4,4′-bis(pyrid-4-yl)biphenyl-K2N:N′)-tetrakis(μ4-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-K4O,O′:O′′:O′′′)-bis[[μ2-1,1′-biphenyl]-3-carboxyl-5-carboxylato-K2O:O′]tetracobalt(II)]— [1,1′-biphenyl]-3,5-dicarboxylic acid (1/2), C93H68N3O16Co2
  66. The crystal structure of 4a-formyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-1-2-6a,6b,9,9,12a-heptamethylpicen-10-yl acetate, C32H50O3
  67. Crystal structure of 3,3′-(1,2-phenylenebis(methylene))bis(1-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C16H20F12N4P2
  68. Crystal structure of catena-poly[diaqua-(μ2-tartrato-κ4O,O′:O′′,O′′′)zinc(II)], C4H8O8Zn
  69. The crystal structure of (6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-10-(4-acetoxy-3-methylbutyl)-6a,8a,9-trimethyl-3,4,5,6,6a,6b,7,8,8a,8b,9,10,11a,12,12a,12b-hexadecahydro-1H-naphtho[2′,1′:4,5]indeno[2,1-b]furan-4-yl acetate, C31H48O5
  70. Crystal structure of 4,4′-(oxybis(methylene))bis(bromobenzene), C14H12Br2O
  71. Crystal structure of (N,N-dimethylsulphoxide)-[N-(3-ethoxy-2-(oxide)benzylidene)-3-methoxybenzenecarbohydrazonato-κ3N,O,O′]-dioxo-molybdenum(VI), C19H22MoN2O7S
  72. Crystal structure of dichlorido-bis(dimethyl sulphoxide-κO)-bis(4-methylbenzyl-κC1)tin(IV), C20H30Cl2O2S2Sn
  73. Crystal structure of (E)-2-amino-N′-(2-hydroxy-4-(2-(piperidin-1-yl)ethoxy)benzylidene)benzohydrazide monohydrate, C21H26N4O3 ⋅ H2O
  74. Crystal structure of chloridotris(4-chlorophenyl)(dimethyl sulfoxide-κO)tin(IV), C20H18Cl4OSSn
  75. Crystal structure of catena{di-aqua-sodium-[N-(hydroxyethyl), N-isopropyl-dithiocarbamato]}n, [C6H16NNaO2S2]n
  76. Crystal structure of 2,2,4,4,6,6-hexakis(4-chlorophenyl)-1,3,5,2,4,6-trithiatristanninane, C36H24Cl6S3Sn3
  77. Crystal structure of 6-methoxy-3-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4H-chromen-4-one-methanol (1/1), C20H18N2O6
  78. Crystal structure of hexanedihydrazide, C6H14N4O2
  79. Crystal structure of tert-butyl 2-(hydroxymethyl)-5-{4-[(methoxycarbonyl)amino]phenyl}-2,5-dihydro-1H-pyrrole-1-carboxylate, C18H24N2O5
  80. Crystal structure of [(Z)-O-isopropyl N-(4-nitrophenyl)thiocarbamato-κS]-(triphenylphosphine-κP)-gold(I), C28H26AuN2O3PS
  81. Crystal structure of [O-ethyl N-(4-nitrophenyl)thiocarbamato-κS](tri-4-tolylphosphine-κP)gold(I) tetrahydrofuran solvate, C30H30AuN2O3PS, C4H8O
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