Startseite Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
Artikel Open Access

Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2

  • Juan Yuan EMAIL logo und Di Cheng
Veröffentlicht/Copyright: 27. September 2018

Abstract

C32H31N5O2, triclinic, P1̄ (no. 2), a = 9.9226(4) Å, b = 11.1446(7) Å, c = 12.6719(6) Å, α = 90.693(4)°, β = 109.858(4)°, γ = 95.382(4)°, Z = 2, V = 1310.72(12) Å3, Rgt(F) = 0.0497, wRref(F2) = 0.1419, T = 173(10) K.

CCDC no.: 1865970

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colorless rod-like
Size:0.40 × 0.30 × 0.10 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.67 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:76.8°, >99%
N(hkl)measured, N(hkl)unique, Rint:8793, 5295, 0.024
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4778
N(param)refined:356
Programs:OLEX2 [1], SHELX [2], [3], CrysAlisPRO [4]
Table 2:

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

AtomxyzUiso*/Ueq
O20.62952(11)0.42340(9)0.52425(8)0.0301(2)
O10.64105(13)0.19506(11)0.99411(9)0.0408(3)
N30.66350(12)0.26114(10)0.82731(9)0.0257(2)
N20.78010(12)0.19989(11)0.84103(10)0.0280(3)
N40.30616(14)0.09943(13)0.30566(11)0.0367(3)
H40.24680.03720.30310.044*
N51.00517(15)0.72836(13)0.71075(12)0.0399(3)
H51.06480.76130.77280.048*
N11.03909(15)0.16870(14)0.71182(12)0.0423(3)
C260.53032(13)0.27276(12)0.62230(11)0.0241(3)
C200.71318(14)0.47944(12)0.62597(11)0.0257(3)
C150.70087(14)0.44633(12)0.72746(11)0.0251(3)
C130.47804(14)0.38260(12)0.77614(11)0.0255(3)
C250.44520(14)0.16212(12)0.60991(11)0.0264(3)
H250.43720.12750.67420.032*
C210.54415(14)0.31894(12)0.52489(11)0.0248(3)
C140.59497(14)0.34197(12)0.73478(11)0.0241(3)
C220.47296(15)0.26201(13)0.41981(11)0.0278(3)
H220.48460.29580.35630.033*
C230.38425(14)0.15456(13)0.40892(12)0.0279(3)
C190.81302(15)0.57225(13)0.61875(12)0.0290(3)
H190.81820.59190.54900.035*
C240.37278(14)0.10188(13)0.50770(12)0.0277(3)
C160.79453(15)0.51148(13)0.82389(11)0.0286(3)
H160.78790.49160.89320.034*
C70.60180(15)0.25416(13)0.91108(11)0.0289(3)
C170.89611(15)0.60368(13)0.82101(12)0.0307(3)
C180.90547(15)0.63610(13)0.71564(12)0.0299(3)
C50.97640(15)0.14832(13)0.78891(12)0.0307(3)
C80.48382(15)0.33203(13)0.87663(11)0.0285(3)
C60.84644(15)0.21117(13)0.77075(11)0.0286(3)
H60.81340.25830.70890.034*
C120.37338(16)0.45832(14)0.72485(12)0.0312(3)
H120.36880.49270.65740.037*
C41.02854(17)0.07489(15)0.87850(13)0.0365(3)
H4A0.98130.06280.93010.044*
C270.28226(16)−0.01633(14)0.49949(13)0.0336(3)
H27A0.2895−0.04050.57350.050*
H27B0.3159−0.07670.46280.050*
H27C0.1836−0.00720.45690.050*
C290.31836(17)0.14032(14)0.20117(12)0.0350(3)
H29A0.32090.22750.20170.042*
H29B0.23320.10760.13980.042*
C110.27577(18)0.48093(16)0.77781(14)0.0399(4)
H110.20460.53110.74490.048*
C31.15248(18)0.01975(16)0.88987(15)0.0425(4)
H31.1895−0.03040.94870.051*
C90.38677(18)0.35506(16)0.93018(13)0.0388(4)
H90.39210.32120.99800.047*
C280.99480(18)0.67037(16)0.92720(14)0.0409(4)
H28A0.97570.75330.92570.061*
H28B1.09310.66590.93280.061*
H28C0.97850.63440.99080.061*
C100.28229(19)0.42992(17)0.87916(15)0.0431(4)
H100.21560.44650.91270.052*
C311.01471(18)0.77284(14)0.60603(15)0.0406(4)
H31A1.05840.85570.61910.049*
H31B0.91810.77260.55200.049*
C300.4508(2)0.10433(16)0.17964(14)0.0425(4)
H30A0.45400.13650.11050.064*
H30B0.44650.01800.17460.064*
H30C0.53580.13580.24030.064*
C21.21884(18)0.04142(19)0.81171(17)0.0498(4)
H21.30240.00680.81690.060*
C321.1013(2)0.69960(18)0.55593(16)0.0485(4)
H32A1.09650.72940.48410.073*
H32B1.06230.61640.54680.073*
H32C1.19980.70660.60520.073*
C11.1587(2)0.1158(2)0.72517(17)0.0531(5)
11.20460.12990.67290.064*

Source of material

All of the starting materials and solvents were reagent grade and were used without purification. The title compound was obtained from Rhodamine 6G by a two-step reaction. Rhodamine 6G hydrozone is prepared according to the literature method [5]. To a 50 mL flask, Rhodamine 6G (1 mmol, 0.479 g) was dissolved in 20 mL ethanol. 2.0 mL (excess) hydrazine monohydrate (80%) was then added dropwise under stirring at room temperature. After the addition, the stirred mixture was refluxed for 3 h, during which the pink precipitate appeared. The precipitate was filtered, washed 3 times with methanol/water (1:1). Yield: ca 80%.

The synthesis of the title compound. Rhodamine 6G hydrozone (0.5 mmol, 0.214 g) was dissolved in boiling methanol, and 2-pyridinecarbaldehyde (0.5 mmol, 0.5 mL) was dropped to the above solution under stirring. Then, the mixture was refluxed for 5 h with vigorous stirring, and white precipitates appeared. The precipitate was filtered, washed 3 times with methanol/water (1:1) and dried over P2O5 under vacuum to obtain white powder. Yield: ca 85%. The white powder (0.05 mmol, 25.9 mg) was dissolved in methanol/dichloromethane (1:1) (10 mL) under stirring to give a colorless solution. Afterwards, ether (20 mL) was slowly diffused to the above solution in a sealed monotube. After 3 days, colourless rod-like crystals were obtained.

Experimental details

The H atoms were added using riding models. Their Uiso values were set to 1.2Ueq of the parent atoms.

Comment

Rhodamine derivatives have attracted great attention in the field of material and analytical chemistry [6], [7], [8], because of the excellent spectroscopic properties such as high fluorescence quantum yield and long wavelength emission. Rhodamine derivatives have been widely investigated as fluorescent probe and fluorescence chemosensors [9], [10], [11].

In this paper, we report a rhodamine 6G pyridyl aroylhydrozone compound. The asymmetric unit contains a neutral molecule in a ring-closed form. The amide C=O bond distance is 1.2162(18) Å, indicative of the keto form. The aroylhydrozone plane and the pyridyl plane are nearly coplanar with the dihedral angle of 4.8°. The dihedral angle between the xanthene plane and pyridyl aroylhydrozone group is 84.8°.

Award Identifier / Grant number: 21571113

Funding statement: This work was supported by the National Natural Science Foundation of China (Project No. 21571113) and the project of scientific and technological in Henan Province (Project No. 172102310433).

References

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Cheng, D.; Pan, Y.; Wang, L.; Zeng, Z. B.; Yuan, L.; Zhang, X. B.; Chang, Y.-T.: Selective visualization of the endogenous peroxynitrite in an inflamed mouse model by a mitochondria-targetable two-photon ratiometric fluorescent probe. J. Am. Chem. Soc. 139 (2017) 285–292.10.1021/jacs.6b10508Suche in Google Scholar PubMed

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Received: 2018-07-13
Accepted: 2018-09-05
Published Online: 2018-09-27
Published in Print: 2018-12-19

©2018 Juan Yuan et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of bis(6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2,4-diiodophenolato)-κ4N,N′,O,O′)cer(IV), C32H20CeI8N4O4
  3. Crystal structure of (6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato-κ2N,O))copper(II), C16H12Cl2CuN2O2
  4. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)samarium(III)], C26H18N2O9Sm
  5. Crystal structure of 1-{4-[(2-hydroxy-5-nitrobenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15N3O4
  6. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis(μ2-1-(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)trizinc(II), C44H38Zn3N4O12
  7. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)–bis(μ2–(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)tricobalt(II), C44H38Co3N4O12
  8. Crystal structure of poly[aqua(μ4-2,2′,2′′-nitrilotriacetato-κ6O1,O3,O5:O2:O4:O6)-yttrium(III)], C6H8NO7Y
  9. Crystal structure of catena-poly[bromido-(μ2-pyrazine-2-carboxylato-κ3N:N′,O)copper(II)], C10H6N4Cu2O4Br
  10. Crystal structure of poly[dodekais(μ2-2,6-difluorobenzoato-κ2O:O′)-bis((μ3-hexamethylenetetramine-κ3N:N′:N′′)hexacopper(II)], C48H30N4O12F12Cu3
  11. Crystal structure of methyl 4-(4-hydroxy-3-nitrophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H18N2O6
  12. Crystal structure of N-phenyl-2-(propan-2-ylidene)hydrazine-1-carbothioamide, C10H13N3S
  13. Crystal structure of sodium caesium zinc phosphate, NaCsZnP2O7
  14. Crystal structure of methyl 4-(4-isopropylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C23H29NO3
  15. Crystal structure of catena-poly[bis(μ2-1,3-di(4H-1,2,4-triazol-4-yl)benzene-κ2N:N′)-bis(thiocyanato-κ1N)cobalt(II), C22H16CoN14S2
  16. Crystal structure of catena-poly[(μ2-2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ2N:N′)-bis(2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ1N)-bis(thiocyanato-κ1N)cobalt(II)], C38H24CoN14S5
  17. Crystal structure of bis(2,5-di(pyridin-2-yl)-1,3,4-thiadiazole-κ2N,N′)-bis(thiocyanato-κ1N)cobalt(II), C26H16CoN10S4
  18. Crystal structure of (bis((1H-benzo[d]imidazol2-yl)methyl)amine-κ3N,N′,N′′)-(pyridine-2,6-dicarboxylato-κ3N,O,O′)zinc(II) — methanol — water (1/2/1), C25H28N6O7Zn
  19. Crystal structure of catena-poly[triaqua-(μ2-5-methoxy-isophthalato-κ2O:O′)copper(II)], C9H12CuO8
  20. Structure and photochromism of 1-[2-methyl-5-phenyl-3-thienyl]-2-[2-methyl-5-(4-chlorophenyl)-3-thienyl]3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16ClF6S2
  21. Crystal structure of methyl 4-(3-phenoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C26H27NO4
  22. Crystal structure of poly[diaqua-di-μ2-hydroxido-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ4O:O′:O′′:O′′′)-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ5O,O:O′:O′′:O′′′)disamarium(III)] – bipyridine (2/1), C21H11NF16O12Sm2
  23. Crystal structural of diethyl 4-(3,5-dibromo-4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C19H21Br2NO5
  24. Crystal structure of catena-poly[tetraaqua(μ2-4-(1H-imidazol-1-yl)pyridine-κ2N:N′))zinc(II)] thiophene-2,5-dicarboxylate, C14H17N3O8ZnS
  25. Crystal structure of (20S)-20-(dimethylamino)-3-(tigloylamino)-5α-pregn-2,16-dien-4-one, C28H42N2O2
  26. Crystal structure of rac-trans-N,N′-bis(3,5-diiodosalicylidene)-1,2-cyclohexanediamine, C20H18I4N2O2
  27. Crystal structure of 2-bromo-7-(4-(dimethylamino)phenyl)-10-methylacridin-9 (10H)-one, C22H19BrN2O
  28. Crystal structure of catena-poly[(μ2-pentane-1,5-dicarboxylato-κ2O:O′)-(μ2-2-[(1H-imidazol-1-yl)methyl]-6-methyl-1H-benzimidazole-κ2N:N′)zinc(II)] sesquihydrate, C17H21N4O5.5Zn
  29. Crystal structure of ethyl 2-amino-4-(3,4-difluorophenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C21H15F2NO5
  30. Crystal structure of 9-(5-methylthiophen-2-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione, C18H18O3S
  31. Crystal structure of [5,5′-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-2-ylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′]nickel(II), C23H30N4O4Ni
  32. Crystal structure of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl) terephthalic acid-dimethylsulfoxide (1/1), C18H15N3O6 ⋅ C2H6OS
  33. Crystal structure of (2E,4Z)-dimethyl 4-((phenylamino)methylene)pent-2-enedioate, C14H15N1O4
  34. Crystal structure of (2Z,2′Z)-1,1′-(pyridine-2,6-diyl) bis(3-hydroxy-3-phenylprop-2-en-1-one), C23H17NO4
  35. Crystal structure of ethyl 2-amino-4-(3-bromophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C21H16BrNO5
  36. Crystal structure of bis(μ2-3,5-dichloro-2-oxidobenzoato-κ4O,O′:O′,O′′)-hexakis(μ2-pivalato-κ2O:O′)-bis(pivalato-κ2O,O′)-tetrakis(1,10-phenanthroline-κ2N,N′)tetragadolinium(III), C102H108Cl4Gd4N8O22
  37. Crystal structure of catena-poly[aqua-bis(formato-κ1O)-(μ2-1,1′-(oxybis(1,4-phenylene))-bis(1H-1,2,4-triazole)-κ2N:N′)copper(II)]hydrate, C18H16CuN6O6
  38. Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN
  39. Crystal structure of N-(4-methoxybenzyl)pyridazin-3-amine- a rare Z′ = 4 structure, C12H13N3O
  40. Crystal structure of bis(perchlorato-κ1O)-bis(3,4,5-trimethoxy-N-(pyridin-2-yl)benzamide-κ2N,O)copper(II), C32H30Cl2CuN4O16
  41. Crystal structure of methyl 4-methyl-2,5-di(pyridin-4-yl)-1H-pyrrole-3-carboxylate monohydrate C17H15N3O2⋅H2O
  42. Crystal structure of dimethyl 5-(10-(methoxycarbonyl)anthracen-9-yl) isophthalate,C26H20O6
  43. Crystal structure of tert-butyl (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)carbamate, C16H24N2O4
  44. Crystal structure of aqua-bis(1,5-dimethyl-2-phenyl-4-(((E)-4-pyridylmethylene)amino)pyrazolidin-3-one-κN)-(nitrato-κO)-(nitrato-κ2O,O′)zinc(II), C34H34N10O9Zn
  45. Crystal structure of catena-poly[dichlorido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)cobalt(II)] – methanol (1/1), C18H20Cl2CoN4O2
  46. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)]bis(2-carboxybenzoate) dihydrate, MnC40H40N10O12
  47. The crystal structure of 4-((3,4-dichlorobenzylidene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, C18H15Cl2N3O
  48. Crystal structure of bis(2-methoxy-6-((2-(pyrimidin-2-yl)hydrazono)methyl)phenolato-κ3N,N′,O)iron(III) perchlorate, C24H22N8O8ClFe
  49. The crystal structure of 2-[4-hydroxy-3-methoxyphenyl]-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl, C14H19N2O4
  50. Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6
  51. Crystal structure of dichloro-tetrakis[(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol-κN]cadmium (II), C60H74CdCl6N12O4
  52. Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
  53. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
  54. The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
  55. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(tri(p-tolyl)phosphine-κP)copper(I) tetrafluoroborate – 4,4′-bipyridine (2/1), C57H54BCuF4N3P2
  56. The crystal structure of 2,6-dimethyl-3,5-dinitrocyclohexa-2,5-diene-1,4-dione, C8H6N2O6
  57. The crystal structure of 2,3-dimethyl-1,4-dinitrobenzene – a Z′ = 4 structure, C8H8N2O4
  58. Crystal structure of [(1,2-η)-1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl] (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-κ6N2,O4) rubidium (I), [Rb(diaza-18-crown-6)]Cp*, C22H41N2O4Rb
  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
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