Home The crystal structure of 3,3′-[1,4-phenylenebis(methylene)]bis(1-ethenyl-1H-imidazol-3-ium) dichloride – dichloromethane – water (1/1/1), C19H24Cl4N4O1
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The crystal structure of 3,3′-[1,4-phenylenebis(methylene)]bis(1-ethenyl-1H-imidazol-3-ium) dichloride – dichloromethane – water (1/1/1), C19H24Cl4N4O1

  • Wenqi Song ORCID logo , Miaoxiu Yang , Liwei Qian and Zongcheng Miao EMAIL logo
Published/Copyright: August 13, 2021

Abstract

C19H24Cl4N4O1, triclinic, P 1 (no. 2), a = 8.5930(4) Å, b = 12.0814(5) Å, c = 12.2430(5) Å, α = 69.805(2)°, β = 75.2820(10)°, γ = 86.733(2)°, V = 1153.07(9) Å3, Z = 2, R gt (F) = 0.0411, wR ref (F2) = 0.1053, T = 296 K.

CCDC no.: 2081427

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: Colorless block
Size: 0.12 × 0.10 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.53 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 28.3°, 98%
N(hkl)measuredN(hkl)uniqueRint: 11,517, 5737, 0.036
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4737
N(param)refined: 291
Programs: Bruker [1], Olex2 [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
Cl1 0.97060 (5) −0.25898 (4) 0.12781 (4) 0.03941 (12)
Cl2 0.50058 (4) −0.23901 (3) 0.43371 (3) 0.03151 (10)
Cl3Aa 0.3697 (8) 0.3632 (2) 0.0889 (5) 0.0973 (13)
Cl3Bb 0.4272 (4) 0.3379 (5) 0.0575 (3) 0.0767 (10)
Cl4Ab 0.1332 (3) 0.2234 (6) 0.22311 (19) 0.0824 (10)
Cl4Ba 0.1476 (3) 0.1619 (5) 0.2064 (3) 0.0858 (13)
C19 0.2855 (3) 0.2352 (2) 0.0845 (2) 0.0585 (5)
H19Ab 0.334704 0.159534 0.091698 0.070*
H19Bb 0.235082 0.256389 0.017862 0.070*
H19Ca 0.237698 0.257800 0.016443 0.070*
H19Da 0.371714 0.182430 0.070633 0.070*
O1 0.68048 (16) −0.42479 (12) 0.32114 (15) 0.0505 (4)
H1A 0.619093 −0.382545 0.355709 0.076*
H1B 0.745280 −0.375520 0.262148 0.076*
N1 0.70313 (16) 0.08316 (12) 0.18770 (11) 0.0297 (3)
N2 0.69578 (18) 0.24761 (13) 0.21964 (13) 0.0362 (3)
C1 0.3657 (2) −0.07543 (15) 0.05513 (14) 0.0345 (4)
H1 0.275706 −0.126266 0.092243 0.041*
C2 0.4838 (2) −0.08022 (14) 0.11491 (14) 0.0349 (4)
H2 0.472536 −0.134124 0.192244 0.042*
C3 0.6189 (2) −0.00525 (13) 0.06044 (13) 0.0293 (3)
C4 0.7429 (2) −0.00531 (15) 0.12783 (16) 0.0357 (4)
H4A 0.744816 −0.082873 0.187228 0.043*
H4B 0.848726 0.013116 0.072507 0.043*
C5 0.5816 (2) 0.07082 (17) 0.28992 (14) 0.0384 (4)
H5 0.515330 0.004282 0.336127 0.046*
C6 0.5777 (2) 0.17362 (17) 0.30959 (15) 0.0419 (4)
H6 0.508069 0.191633 0.372461 0.050*
C7 0.76951 (19) 0.19010 (15) 0.14643 (15) 0.0324 (3)
H7 0.853296 0.220253 0.078061 0.039*
C8 0.7289 (3) 0.36615 (18) 0.2077 (2) 0.0503 (5)
H8 0.676987 0.393225 0.269655 0.060*
C9 0.8251 (5) 0.4362 (3) 0.1172 (3) 0.0855 (10)
H9A 0.854 (4) 0.511 (3) 0.115 (3) 0.105 (11)*
H9B 0.875 (4) 0.424 (3) 0.040 (3) 0.093 (10)*
N3 0.16449 (15) 0.43687 (11) 0.39404 (12) 0.0296 (3)
N4 −0.00547 (15) 0.29811 (11) 0.51798 (12) 0.0276 (3)
C10 −0.11256 (19) −0.03180 (14) 0.45203 (15) 0.0315 (3)
H10 −0.188520 −0.053076 0.419985 0.038*
C11 −0.14664 (19) 0.05456 (13) 0.50454 (14) 0.0315 (3)
H11 −0.245111 0.091061 0.507283 0.038*
C12 −0.03437 (18) 0.08688 (13) 0.55312 (13) 0.0278 (3)
C13 −0.0702 (2) 0.18327 (13) 0.60786 (14) 0.0324 (3)
H13A −0.185692 0.187065 0.637262 0.039*
H13B −0.022283 0.165158 0.675481 0.039*
C14 −0.08828 (19) 0.37833 (14) 0.44444 (14) 0.0312 (3)
H14 −0.197048 0.373253 0.447691 0.037*
C15 0.01741 (19) 0.46533 (14) 0.36707 (15) 0.0319 (3)
H15 −0.004362 0.531778 0.307053 0.038*
C16 0.14719 (19) 0.33517 (13) 0.48595 (14) 0.0301 (3)
H16 0.228148 0.296868 0.521437 0.036*
C17 0.3128 (2) 0.50344 (15) 0.33711 (17) 0.0389 (4)
H17 0.399823 0.479423 0.371019 0.047*
C18 0.3324 (3) 0.5957 (2) 0.2405 (2) 0.0550 (5)
H18A 0.254 (3) 0.622 (2) 0.198 (2) 0.066 (7)*
H18B 0.438 (3) 0.633 (2) 0.207 (2) 0.064 (7)*
  1. aOccupancy: 0.552 (9), bOccupancy: 0.448 (9).

Source of material

About 8.5 g of vinyl imidazole and 5 g of α,α-Dichloro-p-xylene were dissolved in 30 mL of DMSO. Then, the mixture was stirred at 50 °C for 24 h under nitrogen atmosphere. After the reaction was completed, the crude product was washed with ether for several times, and then filtered and dried in vacuum at room temperature to constant weight. The final colorless crystals were obtained by slowly evaporating the solution of the title compound at room temperature.

Experimental details

All the H atoms on the benzene rings were placed geometrically and included with fixed Uiso parameters.

Comment

The diverse applications of polymerized ionic liquids (PILs), in polymer electrolytes, electrochemical devices, smart materials, catalyst support the construction of porous polymers, and antibacterial materials, require different PIL structures and properties [4]. The design and synthesis of PIL relies on the direct continuous chain growth polymerization of ionic liquid (IL) monomers [5]. Here, a novel vinylimidazolium-based IL was synthesized, which can be used as a cross-linking agent as well as a functional monomer for the preparation of adsorbents.

Single-crystal X-ray diffraction reveals that the title compound crystallizes in the triclinic space group P 1 and each asymmetric unit contains two crystallographically independent halves of 3,3′-(1,4-phenylenebis(methylene)) bis(1-vinyl-1H-imidazol-3-ium) cations located on inversion centers, two chloride anions as the counterions, one dichloromethane (DCM) and one water molecule (see the left part of the Figure). The DCM molecules are found to be disordered over two positions with the occupancies of 0.552(9):0.448(9). The C–C and C–N bond lengths in the organic cations are all in the expected ranges [6], [7], [8]. The organic cations in the crystal structure use their conformational flexibility by a rotation about the C3–C4–N1 and C12–C13–N4 single bonds, respectively and the corresponding dihedral angles between the imidazole rings and the phenyl rings are 75.8(3) and 78.6(2)°, respectively, which are comparable to some analogs of the organic cations [9, 10]. The imidazole rings in the same organic cation are perfectly parallel (forced by the space group symmetry and the position of the cation) and located on the opposite sides of the benzene rings, which resulted in the formation of the lightning shape of the organic cations. Furthermore, the vinyl groups (C8–C9, C17–C18) are nearly coplanar with the imidazole rings.

Organic cations, chloride anions, and water molecules are connected by C–H⃛Cl, O–H⃛Cl and C–H⃛O hydrogen bonds. Chloride anions all accept at least three hydrogen atoms and the oxygen atom from the water molecule accepts at least two hydrogen atoms from the organic cations. All Cl⃛H and O⃛H distances are obviously shorter than the typical van der Waals distances and similar hydrogen bonds have been observed in some reported crystals [11], [12], [13]. These hydrogen bonds joined these components together to generate a three-dimensional (3D) framework and the voids in this framework are further filled with the DCM molecules via the C–H⃛π and Cl⃛π interactions between the DCM molecules and organic cations (see the right part of the Figure). The distances between the hydrogen atoms of DCM molecules and the centroids of the benzene rings are shorter than 2.75 Å, while the distances between the Cl atoms of DCM and the centroids of the benzene or imidazole rings are in the range of 3.386(4)–3.793(6) Å.


Corresponding author: Zongcheng Miao, Xi'an Key Laboratory of Advanced Photo-Electronics Materials and Energy Conversion Device, School of Science, Xijing University, Xi'an, Shaanxi 710123, China, E-mail:

Funding source: Education Department of Shaanxi Provincial Government 10.13039/5011000091032

Award Identifier / Grant number: 21JK0955

Funding source: Xijing University 10.13039/501100016984

Award Identifier / Grant number: XJ18T03

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

  2. Research funding: This project was funded by the Education Department of Shaanxi Provincial Government (No: 21JK0955) and the Xijing University (No: XJ18T03). This work was supported by the Youth Innovation Team of Shaanxi Universities.

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

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Received: 2021-06-30
Accepted: 2021-07-29
Published Online: 2021-08-13
Published in Print: 2021-12-20

© 2021 Wenqi Song 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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  62. Crystal structure of catena-poly[(4-hydroxyl-5-(methoylcarbonyl)thiophene-2-carboxylato-κ1 O)-(μ2-piperazine-1,4-diylbis(pyridin-4-ylmethanone)-κ2 N:N′)silver(I)] monohydrate, C23H23AgN4O8S
  63. Crystal structure of bis(4-bromo-2-(((3-bromopropyl)imino)methyl)phenolato-κ2N,O)-oxido-vanadium(IV), C20H20Br4N2O3V
  64. The crystal structure of (2a′S,2a1′S,3R,5a′S,7′R)-5-(furan-3-yl)-2a′,2a1′-dihydroxy-7′-methyldecahydro-2H-spiro[furan-3,6′-naphtho[1,8-bc]furan]-2,2′(2a′H)-dione, C19H22O7
  65. The crystal structure of 3-bromopicolinic acid, C6H4BrNO2
  66. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S,S) platinum(II), C26H18N6PtS4
  67. Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
  68. The crystal structure of 3-amino-5-carboxypyridin-1-ium bromide, C6H7BrN2O2
  69. The crystal structure of (2-hydroxy-5-methyl-phenyl)-(1H-pyrazol-4-yl)-methanone hemihydrate, C11H10.5N2O2.5
  70. Crystal structure of tetraaqua-(2-(4-formylphenoxy)acetato-k1O)cadmium(II), C18H22O12Cd
  71. Crystal structure of diethyl 6,12-dimethyl-3,9-di-p-tolyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5-dicarboxylate, C32H38N2O4
  72. Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5
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