Startseite Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
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Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3

  • Yahong Chen EMAIL logo , Jing Wang und Ruoya Wang
Veröffentlicht/Copyright: 13. Januar 2025
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 240 Heft 2

Abstract

C20H19NO3, orthorhombic, P212121 (no. 19), a = 8.2965(7) Å, b = 12.5111(11) Å, c = 16.2899(15) Å, V = 1,690.9(3) Å3, Z = 4, Rgt(F) = 0.0582, wRref(F2) = 0.1257, T = 298.8(6) K.

CCDC no.: 2394920

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters (Figure 1).

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.40 × 0.33 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 28.8°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 7,335, 3,613, 0.028
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2,547
N(param)refined: 239
Programs: CrysAlisPRO, 1 Olex, 2 SHELX 3 , 4
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.5960 (3) 0.30724 (17) 0.30668 (15) 0.0554 (6)
O2 0.6893 (3) 0.2786 (2) 0.18312 (16) 0.0675 (7)
O3 0.5977 (4) 0.5845 (2) 0.11298 (18) 0.0821 (9)
N1 0.4405 (5) 0.3510 (3) 0.5843 (2) 0.0825 (11)
C1 0.6165 (4) 0.3402 (3) 0.2263 (2) 0.0497 (8)
C2 0.5563 (4) 0.4453 (2) 0.2051 (2) 0.0474 (8)
C3 0.4900 (4) 0.5076 (2) 0.2649 (2) 0.0510 (9)
H3 0.456502 0.576282 0.251262 0.061*
C4 0.4700 (4) 0.4731 (2) 0.3456 (2) 0.0484 (8)
C5 0.5268 (4) 0.3707 (2) 0.3661 (2) 0.0487 (8)
C6 0.5195 (4) 0.3292 (3) 0.4435 (2) 0.0574 (9)
H6 0.559808 0.261226 0.454081 0.069*
C7 0.4510 (4) 0.3894 (3) 0.5070 (2) 0.0571 (9)
C8 0.3900 (4) 0.4921 (3) 0.4876 (2) 0.0591 (10)
H8 0.341653 0.532927 0.528428 0.071*
C9 0.4011 (4) 0.5320 (3) 0.4098 (2) 0.0599 (10)
H9 0.361872 0.600237 0.399162 0.072*
C10 0.3706 (5) 0.4111 (4) 0.6518 (2) 0.0754 (12)
H10A 0.338839 0.361474 0.694580 0.090*
H10B 0.274020 0.446713 0.632396 0.090*
C11 0.4816 (6) 0.4928 (4) 0.6879 (3) 0.0980 (15)
H11A 0.515043 0.541796 0.645826 0.147*
H11B 0.574463 0.457868 0.710561 0.147*
H11C 0.426425 0.531311 0.730440 0.147*
C12a 0.4570 (10) 0.2334 (6) 0.6001 (5) 0.063 (2)
H12Aa 0.443710 0.193083 0.549713 0.076*
H12Ba 0.377357 0.209421 0.639633 0.076*
C13b 0.6248 (11) 0.2202 (9) 0.6337 (7) 0.104 (3)
H13Ab 0.700954 0.250836 0.596006 0.156*
H13Bb 0.647760 0.145596 0.640664 0.156*
H13Cb 0.632781 0.255902 0.685676 0.156*
C14 0.5767 (4) 0.4884 (3) 0.1210 (2) 0.0556 (9)
C15 0.5654 (4) 0.4200 (3) 0.0470 (2) 0.0486 (8)
C16 0.6523 (4) 0.4483 (3) −0.0221 (2) 0.0621 (10)
H16 0.722248 0.506287 −0.020369 0.074*
C17 0.6351 (5) 0.3904 (4) −0.0938 (3) 0.0774 (12)
H17 0.696314 0.408329 −0.139612 0.093*
C18 0.5285 (6) 0.3066 (4) −0.0980 (3) 0.0801 (12)
H18 0.515150 0.269261 −0.146857 0.096*
C19 0.4420 (5) 0.2785 (3) −0.0298 (3) 0.0681 (11)
H19 0.369893 0.221632 −0.032354 0.082*
C20 0.4613 (4) 0.3342 (3) 0.0430 (2) 0.0573 (9)
H20 0.403858 0.313629 0.089428 0.069*
C12Ac 0.5790 (16) 0.2675 (8) 0.6114 (6) 0.076 (3)
H12Cc 0.668820 0.269977 0.573305 0.091*
H12Dc 0.618231 0.283890 0.666004 0.091*
C13Ad 0.5018 (17) 0.1616 (8) 0.6098 (8) 0.107 (4)
H13Dd 0.444283 0.152874 0.559126 0.161*
H13Ed 0.428068 0.155701 0.654982 0.161*
H13Fd 0.582868 0.107132 0.614311 0.161*

  1. aOccupancy: 0.527(9), boccupancy: 0.55, coccupancy: 0.437(9), doccupancy: 0.45.

1 Source of material

The title compound, 7-(diethylamino)-3-(benzoyl)-2H-chromen-2-one was synthesized according to the literature methodology with slight modification. 5 , 6 Ethanol was selected as the solvent for the condensation between 4-diethylaminosalicylaldehyde and ethyl benzoylacetate. The synthetic efficiency is dependend on the reaction temperature. In a 100 mL round bottom flask, 4-diethylaminosalicylaldehyde (580 mg, 3 mmol) and ethyl benzoylacetate (635 mg, 3.3 mmol) were mixed with 50 mL anhydrous ethanol. Subsequently, piperidine (0.02 mmol) was added and the reaction mixture was refluxed for about 1 h. The reaction was monitored with the methodology of thin layer chromatography (TLC). Once one of the starting 4-diethylaminosalicylaldehyde disappeared completely on the TLC plate, the reaction was quenched by adding distilled water 20 mL. The obtained mixture was extracted with dichloromethane (30 mL × 3) and washed with distilled water (30 mL × 3). Then, the organic phase was dried over MgSO4. The volatile components was evaporated on the rotary evaporating equipment. The residue was purified by column chromatography on silica gel (dichloromethane/ethyl acetate). The crystal cultivation was carried in saturated ethanol solution into a NMR tube. After slow evaporation, suitable crystal was selected for X-ray diffraction and data was collected.

2 Experimental details

Hydrogen atoms attached to C atoms were placed geometrically and refined using a riding model approximation, with d(C–H) = 0.93 Å, 0.97 Å, or 0.96 Å (–CH, –CH2, –CH3). Uiso(H) = 1.2 Ueq(C) for CH or Uiso(H) = 1.5 Ueq(C) for CH3 and CH2 groups. 3 One of the ethyl groups attached to nitrogen atom is positionally disordered and rotates around the nitrogen atom. Therefore, it was split to parts with 53 and 47 %, separately. SADI command was used to refine with identical bond length. The anisotropic refinement of C13 was restricted by ISOR command due to its larger thermal ellipsoids.

3 Comment

7-(Diethylamino)-3-(benzoyl)-2H-chromen-2-one is attractive due to coumarin-containing configuration and strong fluorescencing character. Therefore, many fluorescent probes, bio-markers, solar cells, etc. were developed based on the coumarin core structure. 7 , 8 , 9 , 10 , 11 The title compound with a build in electron donor (diethylamino) and electron acceptor (carbonyl) configured the strong intramolecular electron push-pull system. Together with the specifically π system of coumarin, an easily modifiable fluorescence emission could be developed. Based on this strategy, the fluorescence emission maximum can be shifted to longer wavelength (red region). 12 , 13 Bright emitting devices were fabricated by doping fluorescent derivatives.

In the title crystal structure, the asymmetric unit contains one molecule. Both the bond lengths and the angles are in the expected ranges. The core coumarin part is coplanar with the root mean square error (RMSD) in distance estimated to be 0.020 Å. Other groups, ethyl, carbonyl, and benzene, are twisted out of the plane of coumarin. The distance of C2–C14 is determined to be 1.482(5) Å and shorter than that of the saturated carbons. However, the carbonyl is not coplanar with the coumarin and therefore the two parts are not conjugated. Vice versa, the distance of N1–C7 is estimated to be 1.351(5) Å, which is shorter than the distance of N1–C10 (1.453 Å) and N1–C12 (1.500 Å). It demonstrates that the N1 conjugated with the coumarin framework, which can effectively donate the electron toward the coumarin moiety. Therefore, the donor (NEt2) and carbonyl group generates a strong intramolecular “push-pull” effect. Based on this “push-pull” electronic effect, the emission performance could be modified effectively. 14 , 15 , 16 , 17 , 18 Additionally, the amino structure (N1/C7/C10/C12 or N1/C7/C10/C12A) does not construct the ideal trigonal pyramid geometry but complanar with the RMSD in distance 0.053 Å for N1/C7/C10/C12 and 0.093 Å for N1/C7/C10/C12A, respectively. It indicates that there exists the electron donation character of N1 in some degree. The adjacent parallel molecules are fixed by the C–H⋯π interactions. The hydrogen atoms (H13A/H13B/H13F, H16, and H8/H9) are located directly above the benzene ring (C4/C5/C6/C7/C8/C9 and C15/C16/C17/C18/C19/C20). The H⋯centroid distance ranges from 2.97 to 3.95 Å, which is well inside the interval classified to 2.65 to 4.0 Å. 19 The C–H bonds point to the ring carbon rings center and corresponds to a type III, VI, and V geometry. Besides the C–H⋯π interactions mentioned above, typical C–H⋯O interactions also found in the adjacent nonparallel molecules. The distances of C⋯O distances are 3.260–3.396 Å (C12⋯O1 and C13⋯O3), which is well inside the interval of 3.0–4.0 Å quoted by Desiraju. 20 The angles between C12–H12B⋯O1 and C13–H13A⋯O3 are 153.3 and 130.8°, which is also in agreement with the above mentioned survey. 20 , 21 The hydrogen bond investigation is beneficial to analyse the solid emission behavior of fluorescent dye molecules. 22 , 23 , 24 , 25 The introduction of oxygen atoms is the key factor for the configuration of inter- or intra-molecular hydrogen bonds. The excited state of dye molecules is highly dependend on the intermolecular interactions, which determines the ration between radiative and nonradiative channels. 26 When there exist highly stronger intramolecular interactions, the significant fluorescence quench will not be avoided. 27 , 28 , 29 , 30

The crystal lattices were mainly stabilized by the hydrogen bonds and C–H⋯π interactions. Only two hydrogens (H12B and H13A) were involved in the establishment of hydrogen bonds, which jointed the adjacent molecules side by side. It should be noted that there are no π⋯π interactions established in the crystal lattice. Both the hydrogen bonds and C–H⋯π interactions analyzed above are weak intramolecular interactions, which facilitate the emission performance in solid state. 31 Without the establishment of π⋯π interaction, parallel-displaced conformation also was not observed, which may lead to regular tight packing model and quench the fluorescence emission. 32 , 33 , 34 , 35 , 36 The non-radiative channel can be enhanced owing to the regular parallel packing model. 37 , 38 To the crystal of 7-(diethylamino)-3-(benzoyl)-2H-chromen-2-one, the weak interaction, together with the intramolecular electron “push-pull” effect, leads to the character of strong emission. 39 , 40 , 41 In conclusion, the molecules are staggered layer by layer along the axis b, and H⋯O contact joints the layers. Both the bond lengths and the angles are in the expected ranges. 42 , 43 , 44

Corresponding author: Yahong Chen, College of Chemistry and Chemical Engineering, Zhoukou Normal University, Zhoukou, 466000, P.R. China, E-mail:

Acknowledgments

We gratefully thank Prof. Xiaochuan Li (Henan Normal University) for provding lab facilities and supporting the X-ray diffraction data acquisition and structure solving.

  1. Author contributions: 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: The authors declare no conflicts of interest regarding this article.

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44. Liu, Y.; Sun, S.; Ji, G.; Li, X.; Son, Y. A. Crystal Structure of 2-Phenylethynyl-1,3,6,8-tetramethylBOPHY (BOPHY = Bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C22H20B2F4N4. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 749–752; https://doi.org/10.1515/ncrs-2021-0074.Suche in Google Scholar
Received: 2024-10-30
Accepted: 2024-12-22
Published Online: 2025-01-13
Published in Print: 2025-04-28

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
https://doi.org/10.1515/ncrs-2024-0426
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Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of N-(3-bromo-4-fluorophenyl)-N′-hydroxy-4-{[2-(4-methylphenyl)ethyl]amino}-1,2,5-oxadiazole-3-carboximidamide, C18H17BrFN5O2
  4. Synthesis and crystal structure of ethyl (2S,4aS,6aS,6bR,8aR,12aS,12bR,14bR,E)-10-(((3,4-dichlorobenzyl)oxy)imino)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
  5. The crystal structure of pyrazole nitrate
  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
  7. Crystal structure of catena-poly[μ3-iodido-(4-bromopyridine-κ1N)copper(I)], C5H4BrNCuI
  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
  9. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(phenylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C34H48N2O
  10. The crystal structure of (E)-3-((E)-3-(4-ethoxy-3-methoxyphenyl)-1-hydroxyallylidene) chroman-2,4-dione, C21H18O6
  11. The crystal structure of trans–L/D-[bis-(2-methyl-8-hydroxyquinoline-κ2 N,O) bis-(1,3,5-triaza-7-phosphaadamantane-κ2 P)cobalt(III)] tetrafluoroborate
  12. Crystal structure of 9-chloro-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C14H15ClN4
  13. Crystal structure of 7-(diethylamino)-3-(benzoyl)-2 H -chromen-2-one, C20H19NO3
  14. The crystal structure of 4–bromo-3,5-dinitropyrazole
  15. Crystal structure of 8-hydroxy-3,5,8a-trimethyl-7,8,8a,9-tetrahydronaphtho[2,3-b]furan-4,6-dione, C15H16O4
  16. Crystal structure of 5-hydroxy-3,5,8a-trimethyl-4a,5,6,7,8a,9-hexahydronaphtho[2,3-b]furan-4,8-dione, C15H18O4
  17. Synthesis and crystal structure of-(3S,10S,13S,17S)-N-(2-methoxyphenyl)-10,13-dimethyl-17-((R)-1-(p-tolylamino)ethyl)hexadecahydro-1H-cyclopenta[α]phenanthren-3-amine, C35H50N2O
  18. The crystal structure of catena-poly((μ2-1,3,5-tri(1H- imidazol-1-yl)benzene κ2N:N′)-bis(4-hydroxbenzoato-κ1O)-zinc(II) monohydrate), C29H24N6O7Zn
  19. Crystal structure of 2-(benzo[d]oxazol-2-yl)acetonitrile, C9H6N2O
  20. Crystal structure of 1,3-dihydroxy-6,8-dimethoxy-2-(6-methyltetrahydro-2Hpyran-2-yl)-4a,9a-dihydroanthracene-9,10-dione, C22H22O7
  21. The crystal structure of the double salt potassium 1-methylpiperazine-1,4-di-ium trinitrate, C5H14KN5O9
  22. Crystal structure of 5′-hydroxy-6′-methoxy-1′-methyl-2′,3′,8′,8a′-tetrahydro-1′H-spiro[cyclohexane-1,7′-cyclopenta[ij]isoquinoline]-2,5-dien-4-one, C18H19NO3
  23. The crystal structure of 1,1′-(2,3,5,6-tetramethylpyrazine-1,4-diyl)bis(ethan-1-one), C12H18N2O2
  24. Crystal structure of [μ2-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ2O:O′)] bis(μ2-4,4′-trimethylenedipyridyl-κ2N:N′)disilver(I), C18H24AgN3O4S
  25. Crystal structure of bis ((1-((E)-((4-methoxyphenyl)imino)methyl)naphthalen-2-yl)oxy) copper(II), C36H28CuN2O4
  26. Synthesis and crystal structure of 6,6′-((1E,11E)-5,8-dioxa-2,11-diazadodeca-1,11-diene-1,12-diyl) bis(2,4-di-tert-butylphenol), C36H56N2O4
  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
  31. The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
  32. The crystal structure of 1,3,5-trichloro-2-nitrobenzene
  33. The crystal structure of tris(μ2-bromido)-bis(η6-p-cymene)-diosmium(II) tetrafluoroborate, C20H28BBr3F4Os2
  34. Crystal structure of new barium lithium manganese fluorides: Ba14Li1.87Mn14.13F68 with a Jarlite–related structure
  35. Crystal structure of (4-fluorobenzyl)triphenylphosphonium chloride, C25H21ClFP
  36. The crystal structure of calcitriol–chloroform (1/1), C27H44O3⋅CHCl3
  37. The crystal structure of (E)-1-((3)-nitrophenyl)pyren-3-(pyren-1-yl)prop-2-en-1-one, C25H15NO3
  38. Crystal structure of (E)-2-hydroxy-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H16N2O3
  39. Crystal structure of (E)-(3-(thiophen-2-yl)acryloyl)ferrocene, C17H14FeOS
  40. Crystal structure of (E)-(3-(furan-2-yl)acryloyl)ferrocene, C17H14FeO2
  41. Synthesis and crystal structure poly[diaqua(μ3-3-(((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl) methyl)ammonio)propanoate-κ3 O:O′:O″) sodium(I)] monohydrate, C20H24NNaO12S
  42. Crystal structure of 9-methoxy-4-(2-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine C19H18N4O2
  43. Synthesis and crystal structure of 4-(difluoromethyl)-1-methyl-N-(pyridin-3-yl)-1H-pyrazole-3-carboxamide hydrate, C11H12F2N4O2
  44. The crystal structure of caesalfurfuric acid B, C22H32O4
  45. The crystal structure of 2-bromo-2-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-1-phenylethanone, C12H9Br2N3O3
  46. The crystal structure of bis{chlorido-[μ2-(1-oxidopyridin-2-yl)(pyridin-2-yl)amido-κ3 O,N, N′]copper(II)}, C20H16Cl2Cu2N6O2
  47. The crystal structure of 3-amino-2-formyl-1-phenyl-9,10-dihydrophenanthrene-4-carbonitrile, C22H16N2O
  48. The crystal structure of 1,1′-(2,5-dimethylpyrazine-1,4-diyl)bis(ethan-1-one), C10H14N2O2
  49. Crystal structure of 5′-(9-phenyl-9H-carbazol-3-yl)-[2,2′-bithiophene]-5-carbaldehyde, C27H17NOS2
  50. The crystal structure of the double salt dipyridin-1-ium bromide tribromide
  51. Crystal structure of (E)-(3-(3-methylthiophen-2-yl)acryloyl)ferrocene, C18H16FeOS
  52. Crystal structure of (E)-(3-(4-phenoxyphenyl)acryloyl)ferrocene, C25H20FeO2
  53. Crystal structure of (E)-(3-(3,4-dimethylphenyl)acryloyl)ferrocene, C21H20FeO
  54. Crystal structure of [(1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N‴)tetracyanidodiplatinum(II)] dimethyl sulfoxide solvate, C18H36N8O2Pt2S2
  55. Crystal structure of (4-ethoxybenzyl)triphenylphosphonium bromide ethanol solvate, C29H32BrO2P
  56. Crystal structure of (1-naphthalen-1-yl-methyl)triphenylphosphonium chloride ethanol solvate, C31H30ClOP
  57. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)platinum(II) bis[tribromido(dimethyl sulfoxide-κS)platinate(II)], C14H36Br6N4O2Pt3S2
  58. Crystal structure of (2-methylbenzyl)triphenylphosphonium chloride ethanol solvate, C28H30ClOP
  59. Crystal structure of bis(η2, σ1-8-methoxycyclooct-4-enyl)(μ2-1,4,8,11-tetraazacyclotetradecane-κ4 N, N′, N″, N‴)diplatinum(II) dibromide, C28H54Br2N4O2Pt2
  60. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetrabromidopalladate(II), C10H24Br4N4Pd2
  61. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) bis[trichlorido(dimethyl sulfoxide-κS)platinate(II)], C14H36Cl6N4O2PdPt2S2
  62. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)palladium(II) tetraiodidopalladate(II), C10H24I4N4Pd2
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