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Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8

  • Wang Xin , Liu Qingyun , Yang Liguo EMAIL logo , Liu Nana , Niu Yongsheng and Wei Aimin
Published/Copyright: August 23, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 233 Issue 6

Abstract

C98H84Cl6N8O8, triclinic, P1̄ (no. 2), a = 8.3431(3) Å, b = 16.1109(6) Å, c = 18.1405(7) Å, α = 109.242(4)°, β = 95.119(3)°, γ = 103.798(3)°, V = 2197.92(16) Å3, Z = 1, Rgt(F) = 0.0595, wRref(F2) = 0.1689, T = 293(2) K.

CCDC no.: 1841802

The crystal structure is shown in the figure. The non-hydrogen atoms of the asymmetric unit are labeled. 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:Green block
Size:0.10 × 0.08 × 0.06 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:2.28 mm−1
Diffractometer, scan mode:APEX, ω and ϕ scans
θmax, completeness:63.5°, 98%
N(hkl)measured, N(hkl)unique, Rint:14028, 7069, 0.022
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5641
N(param)refined:554
Programs:Bruker [1, 3] , SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
O1−0.1555(2)0.29448(12)0.72314(11)0.0247(4)
N10.5431(3)0.60934(16)0.60052(15)0.0235(5)
C10.4743(3)0.60477(18)0.66491(16)0.0221(6)
H10.522(4)0.570(2)0.558(2)0.031(9)*
O2−0.2205(2)0.15334(13)0.59084(11)0.0282(5)
N20.3595(3)0.53648(15)0.67115(13)0.0230(5)
C20.2965(3)0.45500(18)0.61243(16)0.0214(6)
O30.1971(3)0.04385(13)0.12218(11)0.0287(5)
N30.3465(3)0.42391(15)0.54137(13)0.0223(5)
C30.1606(3)0.38431(18)0.61993(16)0.0220(6)
O40.3897(3)0.14863(13)0.06637(11)0.0294(5)
N40.2539(3)0.27817(15)0.43062(13)0.0233(5)
C40.0650(3)0.38415(18)0.67917(16)0.0228(6)
H40.08350.43590.72480.027*
C5−0.0576(3)0.30472(19)0.66749(16)0.0218(6)
C6−0.0888(3)0.22660(18)0.59694(16)0.0233(6)
C70.0069(3)0.22754(18)0.53856(16)0.0236(6)
H7−0.01220.17640.49240.028*
C80.1330(3)0.30782(18)0.55144(16)0.0216(6)
C90.2500(3)0.33499(18)0.50298(16)0.0219(6)
C100.3475(3)0.30574(18)0.38343(16)0.0212(6)
C110.3473(3)0.25114(18)0.30185(16)0.0218(6)
C120.2582(4)0.16098(18)0.25422(16)0.0238(6)
H120.18800.12310.27440.029*
C130.2783(4)0.13045(18)0.17634(17)0.0248(6)
C140.3835(4)0.18815(19)0.14503(16)0.0229(6)
C150.4729(3)0.27647(18)0.19220(16)0.0229(6)
H150.54340.31430.17210.028*
C160.4535(3)0.30713(18)0.27161(16)0.0226(6)
C17−0.1900(4)0.37306(19)0.77348(17)0.0268(6)
C18−0.3363(4)0.3907(2)0.7497(2)0.0354(7)
C19−0.3789(5)0.4641(2)0.8012(2)0.0469(9)
H19−0.47740.47710.78690.056*
C20−0.2756(5)0.5178(2)0.8733(2)0.0515(10)
H20−0.30470.56700.90740.062*
C21−0.1293(5)0.4991(2)0.8950(2)0.0431(9)
H21−0.06030.53660.94350.052*
C22−0.0826(4)0.4253(2)0.84595(17)0.0318(7)
C230.0716(5)0.4022(2)0.87151(19)0.0419(8)
H23A0.14520.45450.91390.063*
H23B0.12820.38530.82740.063*
H23C0.04010.35180.88950.063*
C24−0.4450(5)0.3325(3)0.6696(2)0.0513(10)
H24A−0.55930.33300.67180.077*
H24B−0.43810.27070.65550.077*
H24C−0.40660.35660.63040.077*
C25−0.2718(4)0.0798(2)0.51717(18)0.0288(7)
C26−0.2391(4)−0.0020(2)0.51448(19)0.0316(7)
C27−0.2946(4)−0.0757(2)0.4425(2)0.0402(8)
H27−0.2753−0.13140.43840.048*
C28−0.3779(4)−0.0676(2)0.3771(2)0.0451(9)
H28−0.4121−0.11730.32920.054*
C29−0.4102(4)0.0138(2)0.3826(2)0.0419(8)
H29−0.46790.01820.33840.050*
C30−0.3583(4)0.0899(2)0.45322(19)0.0343(7)
C31−0.3983(5)0.1777(2)0.4590(2)0.0447(8)
H31A−0.44250.19970.50650.067*
H31B−0.48000.16680.41360.067*
H31C−0.29790.22280.46060.067*
C32−0.1521(4)−0.0109(2)0.5857(2)0.0406(8)
H4A1−0.20480.01150.63020.061*
H4A2−0.03630.02420.59760.061*
H4A3−0.1592−0.07420.57520.061*
C330.1221(4)−0.02066(18)0.15373(16)0.0260(6)
C340.2211(4)−0.0691(2)0.17681(17)0.0305(7)
C350.1459(5)−0.1343(2)0.2065(2)0.0426(8)
H350.2080−0.16860.22190.051*
C36−0.0207(5)−0.1488(2)0.2134(2)0.0461(9)
H36−0.0689−0.19200.23450.055*
C37−0.1170(4)−0.1007(2)0.1897(2)0.0430(9)
H37−0.2294−0.11200.19470.052*
C38−0.0472(4)−0.0348(2)0.15812(19)0.0332(7)
C39−0.1476(5)0.0175(3)0.1289(2)0.0507(10)
H39A−0.25750.00440.14200.076*
H39B−0.1571−0.00040.07240.076*
H39C−0.09230.08210.15370.076*
C400.4037(4)−0.0495(2)0.1696(2)0.0436(8)
H5A10.4507−0.09240.18350.065*
H5A20.46310.01170.20470.065*
H5A30.4135−0.05540.11590.065*
C410.4579(4)0.20785(19)0.02816(16)0.0247(6)
C420.6239(4)0.2188(2)0.01890(17)0.0318(7)
C430.6856(4)0.2739(2)−0.0232(2)0.0424(8)
H430.79630.2828−0.03070.051*
C440.5850(5)0.3156(2)−0.0540(2)0.0440(9)
H440.62810.3522−0.08200.053*
C450.4200(4)0.3030(2)−0.04332(19)0.0382(8)
H450.35290.3311−0.06460.046*
C460.3529(4)0.2492(2)−0.00138(17)0.0294(7)
C470.1736(4)0.2340(2)0.0111(2)0.0397(8)
H47A0.11290.2557−0.02250.059*
H47B0.17140.26680.06560.059*
H47C0.12220.1697−0.00180.059*
C480.7296(5)0.1712(3)0.0518(2)0.0532(10)
H48A0.83730.18220.03610.080*
H48B0.67490.10640.03160.080*
H48C0.74430.19440.10870.080*
C490.9318(6)0.3612(3)0.3093(3)0.0631(12)
H490.83320.37910.29420.076*
Cl11.0711(2)0.37556(13)0.24635(12)0.1074(6)
Cl21.0213(3)0.42992(13)0.40712(9)0.1453(10)
Cl30.86685(17)0.24623(10)0.29942(9)0.0835(4)

Source of material

n-Pentanol and n-octanol were distilled from sodium under nitrogen. Column chromatography was carried out on silica gel columns (Merck, Kieselgel 60, 70–230 mesh) with the indicated eluents. All other reagents and solvents were used as received. 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyaninate was prepared according to the literature procedures with slight modification [4]. 4,5-Dichlorophthalonitrile (4.0 g, 20 mmol) and 2,6-dimethylphenol (14.6 g, 120 mmol) in dry DMSO (40 mL) were strirred under dry nitrogen at 95 °C. Dry potassium carbonate (60 g) was added (in 5 min) and the solution was stirred at 95 °C for an additional 1.5 h, then cooled and poured into ice-water (400 mL). The sticky precipitate was filtered, washed with cold water, ethanol, and then dissolved in trichloromethane and precipitated with ethanol with subsequent evaporation of dichloromethane. The precipitate was filtered and vacuum-dried to get the 4,5-bis(2,6-dimethylphenoxy)phthalonitrile. Then the bis(diiminoisoindoline) (prepared from the 101 mg (0.57 mmol) 1,2,4,5-tetra-cyanobenzene) and 4,5-bis(2,6-dimethylphenoxy)phthalonitrile (1.4 g, 4 mmol) were added to the n-BuOH (40 mL) solution and the mixture was heated under reflux for 48 h. After the reaction mixture had been cooled, methanol (200 mL) was added and the resulting mixture was stirred for 1 h. The precipitate was collected by the centrifugation, washed with methanol, dried and then extracted with toluene. After evaporation of toluene the solid was dissolved in trifluoroacetic acid (25 mL) and stirred in the dark for 1 h. The solution was poured into ice-water (100 mL) the precipitate collected, washed successively with water, 5% NaHCO3, water and methanol, then dried under vacumm, extracted with toluene/hexanes (4:1 v/v) and subjected to chromatography on silica gel eluting with toluene/hexanes gradually reducing the hexanes content from 20 to 50 vol%. From the first green fraction containing 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyaninate the solvents were evaporated and the resulting solid was recrystallised from the toluene and trichloromethane. (0.36 g, 24%). 1H NMR (200 MHz, CDCl3, 25 °C, TMS): δ = 8.18(s, 8H), 7.30−7.41(brm, 24H), 2.43(s, 48H) – 0.76 ppm(brs, 2H); IR(KBr): 3296(N—H), 3024, 2952, 2922, 2854, 1612, 1588, 1442, 1396, 1328, 1276, 1222, 1188, 1092, 1016, 920, 878, 834, 800, 762, 708, 696 cm−1.

Experimental details

Hydrogen atoms were added using a riding model implemented in the crystallographic software [2], [3].

Comment

Some of the most important applications of phthalocyanines (Pcs) are based on the interaction of visible light with the chromophores of these molecules: dyes and pigments, photoconductors in laser printers, photosensitisers in the photodynamic therapy of cancer and degradation of pollutants of waste and natural water [5], [6], [7], [8], [9], [10], [11], [12]. Pcs as thin films or adsorbed on inorganic semiconductors have potential applications in photovoltaic or dye-sensitised solar cells. Based on these applications and taking into account the increasing interest in near-infrared (NIR) absorbing systems, it is important to sythesize compounds with absorptions over a broad region of visible light down to the NIR region. The similar phthalocyanine 2,3,9,10,16,17,23,24-octakis(2-tetrahydropyran)phthalocyanine has been reported [13].

The figure depicts a perspective drawing of the compound showing the atom numbering. The atoms of the phthalocyaninate ring are in the same plane, the 2,6-dimethylphenoxy group is almost vertical to the phthalocyaninate ring.

Acknowledgements

This work was supported by Henan science and technology project (Nos. 172102210161, 172102210160) and the Research Fund of Anyang Institute of Technology (No. YJJ2016014).

References

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Received: 2018-05-12
Accepted: 2018-07-09
Published Online: 2018-08-23
Published in Print: 2018-11-27

©2018 Wang Xin et al., published by De Gruyter, Berlin/Boston

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

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  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
https://doi.org/10.1515/ncrs-2018-0005
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of di-μ2-aqua-tetraaqua-bis(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)disodium(I) C18H24N6Na2O10
  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
  16. The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
  17. Crystal structure of catena-poly[bis(4,4′-dipyridylaminium-kN)-(μ2-germanowolframato-κ2O:O′)-(2,2′-bipyridine-κ2N,N′)copper(II)] with a Keggin-type heteropolyoxoanion, [Cu(C10H8N2)(C10H10N3)2][GeW12O40] ⋅ H2O
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)pyridin-1-ium-4-carbohydrazonate-κ3N,N′,O)-tris[nitrato-κ2O,O′)lanthanum(III), C12H15N8O12La
  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
  21. Crystal structure of (Z)-2-bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H27BrO2
  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
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