Home The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
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The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4

  • Bingcui Yang , Yuzhou Wang and Hao Cui ORCID logo EMAIL logo
Published/Copyright: July 6, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 5

Abstract

C50H32Cl6F4N4O4, triclinic, P 1 ‾ (no. 2), a = 6.6447(6) Å, b = 12.5839(11) Å, c = 14.3335(11) Å, α = 85.845(7)°, β = 85.679(7)°, γ = 85.679(7)°, V = 1188.89(18) Å3, Z = 1, R gt (F) = 0.0605, wR ref (F 2) = 0.1740, T = 200 K.

CCDC no.: 2265016

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: Red block
Size: 0.10 × 0.05 × 0.05 mm
Wavelength: CuKα radiation (1.54184 Å)
μ: 3.86 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 66.0°, 99 %
N(hkl)measured, N(hkl)unique, R int: 6205, 4076, 0.043
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3205
N(param)refined: 308
Programs: CrysAlis Pro [1], Olex2 [2], Shelx [3, 4]
Table 2:

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

Atom x y z U iso*/U eq
C1 −0.3442 (4) 0.3524 (2) 0.05240 (19) 0.0254 (6)
C1S 1.4212 (7) 0.9357 (4) 0.3317 (3) 0.0616 (10)
H1S 1.343549 0.927057 0.277662 0.074*
C2 −0.4452 (4) 0.2958 (2) 0.1329 (2) 0.0318 (6)
H2A −0.555455 0.254554 0.132063 0.038*
C3 −0.3487 (4) 0.3144 (2) 0.2085 (2) 0.0321 (6)
H3 −0.380183 0.289548 0.270166 0.039*
C4 −0.1856 (4) 0.3808 (2) 0.17473 (19) 0.0247 (5)
C5 −0.0438 (4) 0.4141 (2) 0.23223 (18) 0.0254 (6)
C6 0.1139 (4) 0.4784 (2) 0.20376 (18) 0.0259 (6)
C7 0.2443 (4) 0.5209 (2) 0.2642 (2) 0.0322 (6)
H7 0.244723 0.505999 0.328732 0.039*
C8 0.3678 (4) 0.5869 (2) 0.2116 (2) 0.0315 (6)
H8 0.465833 0.625575 0.233778 0.038*
C9 0.3204 (4) 0.5862 (2) 0.11598 (19) 0.0247 (5)
C10 0.4038 (4) 0.6469 (2) 0.0393 (2) 0.0248 (6)
C11 −0.0628 (4) 0.3789 (2) 0.33453 (19) 0.0291 (6)
C12 0.0653 (5) 0.2986 (3) 0.3724 (2) 0.0376 (7)
C13 0.0558 (6) 0.2646 (3) 0.4663 (2) 0.0518 (9)
H13 0.146584 0.210811 0.489029 0.062*
C14 −0.0919 (6) 0.3125 (4) 0.5256 (2) 0.0575 (10)
H14 −0.101712 0.290211 0.588984 0.069*
C15 −0.2244 (6) 0.3925 (4) 0.4920 (2) 0.0580 (11)
H15 −0.324219 0.424608 0.531937 0.070*
C16 −0.2063 (5) 0.4242 (3) 0.3976 (2) 0.0439 (8)
C17 0.5556 (4) 0.7224 (2) 0.06003 (19) 0.0262 (6)
C18 0.5063 (4) 0.8320 (2) 0.0507 (2) 0.0302 (6)
H18 0.383290 0.857421 0.027781 0.036*
C19 0.6380 (4) 0.9035 (2) 0.0753 (2) 0.0322 (6)
H19 0.603267 0.976493 0.069042 0.039*
C20 0.8220 (4) 0.8663 (2) 0.1091 (2) 0.0300 (6)
C21 0.8721 (4) 0.7572 (2) 0.1191 (2) 0.0340 (7)
H21 0.994457 0.732004 0.142749 0.041*
C22 0.7406 (4) 0.6860 (2) 0.0939 (2) 0.0341 (7)
H22 0.776252 0.613033 0.099701 0.041*
C23 0.9665 (4) 0.9407 (3) 0.1392 (2) 0.0373 (7)
C24 1.0484 (5) 1.1182 (3) 0.1414 (3) 0.0504 (9)
H24A 1.020229 1.186677 0.109154 0.076*
H24B 1.188083 1.095033 0.128417 0.076*
H24C 1.021009 1.123777 0.207632 0.076*
Cl1S 1.5749 (2) 1.04093 (11) 0.30153 (11) 0.0888 (5)
Cl2S 1.5640 (2) 0.81582 (11) 0.35393 (10) 0.0836 (4)
Cl3S 1.2493 (3) 0.96599 (15) 0.42467 (16) 0.1309 (8)
F1 0.2097 (3) 0.25112 (18) 0.31402 (15) 0.0544 (6)
F2 −0.3335 (4) 0.5046 (2) 0.36539 (15) 0.0695 (8)
N1 −0.1869 (3) 0.40386 (18) 0.07987 (16) 0.0244 (5)
N2 0.1683 (3) 0.51828 (18) 0.11461 (15) 0.0237 (5)
H2 0.114938 0.502963 0.064918 0.028*
O1 0.9218 (3) 1.04173 (17) 0.10955 (17) 0.0403 (5)
O2 1.1075 (4) 0.9118 (2) 0.1845 (2) 0.0600 (8)

1 Source of materials

All chemicals were purchased from commercial sources and used as received without further purification. Procedures for the preperation of trimethyl dimethyl4,4′-[10,20- bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate were adapted from the reported papers [5, 6]. Under N2 atmosphere, trifluoroacetic acid (0.3 ml) was added to a stirred solution of 20 g (122 mmol)methyl p-formylbenzoate and 100 ml pyrrole under nitrogen gas atmosphere. The reaction mixture was stirred at room temperature for 0.5 h. After that, TLC analysis (dichloromethane/hexane 3:1) showed the complete consumption of methy-lp-formylbenzoate. The excessive pyrrole was removed to afford the crude product. Then, the crude product was purified by column chromatography on silica gel eluted with (CH2Cl2/PE 3:1) to give the corresponding compound (15.62 g, 78 %) as a white solid. 1H NMR (400 MHz, DCCl3) δ 10.62 (s, 2H), 7.88 (d, J = 7.6 Hz, 2H), 7.29 (d, J = 7.6 Hz, 2H), 6.63 (s, 2H), 5.91 (s, 2H), 5.66 (s, 2H), 5.44 (s, 3H). Under N2 atmosphere, 4-(di(1H-pyrrole-2-yl)methyl)benzoate (1.12 g, 4 mmol) and 2,6-difluorobenzaldehyde (4 mmol) were dissolved in 500 ml dichloromethane, and then boron (tri) fluoride etherate (50 μL) was added. Subsequently, the reaction was stirred at room temperature for 1 h. After that, DDQ (2,3–dichloro-5,6- dicyano-p-benzoquinone) (4 mmol, 908 mg) was added, and the mixture was stirred at room temperature 2 h. The reaction mixture was evaporated to dryness, and the crude product was purified by chromatography (silica gel) with dichloromethane, dichloromethane/PE (3:1, by vol.) and dichloromethane successively, finally with pure green product obtained (140 mg, 20.6 % yield). 1H NMR (400 MHz, DCCl3) δ 8.84 (8H, d, J = 5.6), 8.43 (4H, d, J = 8.0), 8.29 (4H, d, J = 8.0), 7.78 (2 H, s), 7.37 (4 H, m), 4.10 (6 H, s), −2.80 (2 H, s). MALDI–TOF–MS (m/z): [M]+ calcd. for C48H30F4N4O4, 803.2237; found, 803.2275. Single crystals were obtained from solution of the title compound in DCCl3 at room temperature for two days.

2 Experimental details

Single-crystal X-ray diffraction data for the title structure was collected on SuperNova, Dual, Cu at home/near, AtlasS2 diffractometer by ‘CrysAlisPro 1.171.39.46’ [2]. A suitable crystal was selected and mounted on the diffractometer and the data was collected. The structure was solved with the Shelxt [3] structure solution program and refined with the xl [4] refinement package. The positions of the hydrogen atoms were generated geometrically. The cif-file of the title compound can be obtained free of charge from the Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif (2265016).

3 Comment

Fluorine, with the strong electrophilic properties and the unique properties of fluorine, can cause many interesting changes in the porphyrin ring when it is introduced. Fluoro-porphyrins are widely used in the fields of biology, biochemistry [7], catalysis [8], medicine [9] and materials [8] due to their unique structural characteristics. It is of great significance to design fluoro-porphyrin-containing compounds or porous materials. We have synthesized a fluoro-porphyrin-containing compound, which can be used for the synthesis of fluoro-porphyrin-containing metal-organic frameworks after hydrolysis. The crystal structure of the complex is shown in the figure. The symmetric unit contains the half porphyrin and one CHCl3 molecule. The substituent at the substitution positions of porphyrin 10,20 is 2,6-difluorophenyl and the substituent at position 5,10 is phenyl. The bond lengths and angles within molecule are in the expected ranges [10]. The distance of N1–C1, N1–C4, N2–C6, N2–C9 is 1.367(3), 1.370(4), 1.371(4), 1.374(3) Å, the distance of C1s–Clsl, C1s–Cls2, C1s–Cls3 is 1.743(4), 1.743(5), 1.732(5) Å, the distance of F1–C12, F2–C16 is 1.356(4), 1.347(4) Å. Void between porphyrin molecules in the structure are occupied by CHCl3 molecules.

Corresponding author: Hao Cui, School of Pharmaceutical Sciences, Guangxi University of Chinese Medicine, Nanning 530200, P.R. China, E-mail:

Funding source: Science and Technology Planning Project of Guangxi Zhuang Autonomous Region

Award Identifier / Grant number: Gui ke AD1924509

Funding source: Doctoral Scientific Research Foundation of Guangxi University of Chinese Medicine

Award Identifier / Grant number: XP018133

Funding source: College Student Innovation and Entrepreneurship Program Training Program

Award Identifier / Grant number: S2021110600117

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

  2. Research funding: This work was funded by Science and Technology Planning Project of Guangxi Zhuang Autonomous Region (Gui ke AD19245096), Doctoral Scientific Research Foundation of Guangxi University of Chinese Medicine (2018BS018), and College Student Innovation and Entrepreneurship Program Training Program (S2021110600117 and S202310600066).

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

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Received: 2023-05-27
Accepted: 2023-06-21
Published Online: 2023-07-06
Published in Print: 2023-10-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

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  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
https://doi.org/10.1515/ncrs-2023-0254
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
  4. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2-chloro-4-methyl phenolate-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV), C27H27Cl2N3O6Ti
  5. N′-[(1E)-(4–Fluorophenyl)methylidene]adamantane-1-carbohydrazide, C18H21FN2O
  6. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid monohydrate, C4H2N3BrO4·H2O
  7. Crystal structure of dipyridine-k1N-tris(2,2,6,6-tetramethyl-5-oxohept-3-en-3-olato-k2O,O′)dysprosium(III), DyC43H67O6N2
  8. Crystal structure of cyclo[tetraiodido-bis{μ2-1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-isopropyl-imidazol)-k2N:N}dicadmiun(II)], C26H30N10Cd2I4
  9. The crystal structure of tert-butyl (E)-3-(2-(benzylideneamino)phenyl)-1H-indole-1-carboxylate, C26H24N2O2
  10. The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
  11. Crystal structure of (μ2-1-(4,4′-bipyridine-κ2N:N′)-bis[diaqua-(4-iodopyridine-2,6-dicarboxylato-κ3O,N,O′)–cobalt(II)], C24H20Co2I2N4O12
  12. The crystal structure of dimethyl 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane solvate, C49H36N4O4Cl2
  13. (E)-2-((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ylidene)hydrazine-1-carbothioamide C14H23N3S1
  14. The crystal structure of [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
  15. Crystal structure of (E)-2-amino-N′-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide – dimethylformamide – water (1/1/2), C15H16N4O3·C3H7NO·2H2O
  16. Crystal structure of 3-(4-bromophenyl)-5-methyl-1H-pyrazole, C10H9BrN2
  17. Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
  18. Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
  19. The crystal structure of nitroterephthalic acid, C8H5NO6
  20. Crystal structure of (2-((4-bromo-2,6-dichlorophenyl)amino)phenyl) (morpholino)methanone, C17H15BrCl2N2O2
  21. Crystal structure of tetraaqua-bis(ethanol-κO)-tetrakis(μ2-trifluoroacetate-κ2O:O′)-bis(trifluoroacetate-κ2O)digadolinium(III) Gd2C16H20O18F18
  22. The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
  23. The crystal structure of N,N′-((nitroazanediyl)bis(methylene))diacetamide, C6H12O4N4
  24. The crystal structure of [bis(2,2′-bipyridine-6-carboxylato-κ3N,N,O)magnesium(II)]dihydrate, C22H18N4O6Mg
  25. Crystal structure of poly[diaqua-(bis(μ2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′] cobalt(II)-tetraqua-bis(1,4-bis(imidazol-1-ylmethyl)benzene)-κ1N)-cobalt(II) di(2,5-thiophenedicarboxylate) dihydrate, C68H76Co2N16O16S2
  26. Crystal structure of poly[chlorido-μ2-chlorido-(μ2-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κN:N’)cadmium(II)], C13H15CdN5Cl2
  27. The crystal structure of (4-hydroxybenzenesulfonate)-k1O-6,6′-((1E,1′E)- (ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene)) bis(2-methoxyphenol)-κ2N,N,μ2O,O,κ2O, O)-(methanol)-cobalt(II) sodium(I), C25H27CoN2NaO9S
  28. Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
  29. Crystal structure of bis{[(cyclohexylimino)(phenylimino)-l5-(methyl)diethylazane-κ2N:N′]-(ethyl)-zinc(II)]}, C38H62N6Zn2
  30. Crystal structure of 2-[(4-bromobenzyl)thio]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C13H8Br2N2OS2
  31. Crystal structure of 10-methoxy-7,11b,12,13-tetrahydro-6H-pyrazino [2′,3′:5,6]pyrazino[2,1-a]isoquinoline, C15H16N4O
  32. The crystal structure of 1-propyl-2-nitro-imidazole oxide, C6H9N3O3
  33. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid–2-ethoxybenzamide (1/1), C17H16N2O8
  34. The structure of RUB-1, (C8H16N)6[B6Si48O108], a boron containing levyne-type zeolite, occluding N-methyl-quinuclidinium in the cage-like pores
  35. The crystal structure of diaqua-(naphthalene-4,5-dicarboxylate-1,8-dicarboxylic anhydride-κ1O)-(4′-(4-(1H-benzimidazolyl-1-yl)phenyl)-2,2′:6′,2″-terpyridine-κ3N,N′,N″)–manganese(II) dihydrate, C42H27MnN5O9·2H2O
  36. Crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (3-(3-bromopropoxy)phenol), C20H22Br2N2O4
  37. The crystal structure of 3-(2-hydroxyphenyl)-4-phenyl-6-(p-tolyl)-2H-pyran-2-one, C24H18O3
  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
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