Home The crystal structure of catena-poly[bis(1-ethylimidazole-k1 N)-(μ 2-benzene-1-carboxyl-3,5-dicarboxylato-κ 2 O, O′)zinc(II)], C19H20N4O6Zn
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The crystal structure of catena-poly[bis(1-ethylimidazole-k1 N)-(μ 2-benzene-1-carboxyl-3,5-dicarboxylato-κ 2 O, O′)zinc(II)], C19H20N4O6Zn

  • Ya-Fei Guo and Bao-Kuan Chen ORCID logo EMAIL logo
Published/Copyright: May 15, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 4

Abstract

C19H20N4O6Zn, monoclinic, P21/n (no. 14), a = 11.7411(7) Å, b = 13.7831(9) Å, c = 13.5425(10) Å, β =  97.564 ( 2 ) ∘ , V = 2172.5(3) Å3, Z = 4, R gt (F) = 0.0645, wR ref (F 2) = 0.1643, T = 298 K.

CCDC no.: 2256328

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: Colourless block
Size: 0.24 × 0.22 × 0.20 mm
Wavelength:

μ: 		Mo Kα radiation (0.71073 Å)

1.17 mm−1
Diffractometer, scan mode:

θ max, completeness:		 Bruker APEX-II, φ and ω

25.1°, 99 %
N(hkl) measured , N(hkl) unique, R int: 18959, 3838, 0.083
Criterion for I obs, N(hkl) gt: I obs > 2 σ(I obs), 2571
N(param) refined: 311
Programs: Bruker [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
Zn1 0.48561 (5) 0.76440 (4) 0.72839 (6) 0.0398 (3)
O1 0.1588 (3) 0.4217 (3) 0.7613 (3) 0.0527 (12)
O2 0.5654 (3) 0.1140 (3) 0.7721 (4) 0.0703 (15)
O3 0.7102 (3) 0.2117 (3) 0.7568 (4) 0.0672 (15)
H3 0.744914 0.160348 0.753970 0.101*
O4 0.1813 (3) 0.2632 (3) 0.7803 (3) 0.0481 (11)
O5 0.4964 (3) 0.6236 (3) 0.7240 (4) 0.0700 (15)
O6 0.6692 (3) 0.5602 (3) 0.7541 (4) 0.0621 (14)
N1 0.5453 (4) 0.8227 (4) 0.6124 (4) 0.0552 (12)
N2 0.6529 (6) 0.9137 (5) 0.9665 (5) 0.0820 (16)
N3 0.6419 (6) 0.9141 (5) 0.5213 (5) 0.0802 (15)
N4 0.5711 (4) 0.8132 (4) 0.8536 (4) 0.0528 (12)
C1 0.5111 (4) 0.4561 (3) 0.7488 (4) 0.0286 (10)
C2 0.8053 (9) 1.0279 (9) 1.0019 (8) 0.147 (4)
H2A 0.850073 0.971592 1.023284 0.220*
H2B 0.834403 1.082993 1.040569 0.220*
H2C 0.810204 1.039872 0.932728 0.220*
C3 0.6292 (7) 0.7631 (6) 0.9315 (6) 0.0791 (18)
H3A 0.632487 0.695816 0.936403 0.095*
C4 0.5787 (4) 0.3738 (3) 0.7507 (4) 0.0308 (11)
H4 0.656485 0.379486 0.745073 0.037*
C5a 0.7086 (8) 1.0023 (7) 0.4988 (8) 0.0886 (19)
H5Aa 0.672104 1.033846 0.438834 0.106*
H5Ba 0.712891 1.048108 0.553492 0.106*
C6 0.5317 (4) 0.2832 (3) 0.7609 (4) 0.0305 (10)
C7 0.6839 (8) 1.0111 (7) 1.0158 (7) 0.101 (2)
H7A 0.635134 1.062153 0.984323 0.121*
H7B 0.675526 1.008960 1.086059 0.121*
C8 0.5638 (4) 0.5539 (3) 0.7414 (4) 0.0352 (12)
C9b 0.848 (2) 0.8928 (18) 0.4688 (18) 0.081 (4)
H9Ab 0.895165 0.884089 0.531771 0.121*
H9Bb 0.890698 0.928014 0.424551 0.121*
H9Cb 0.826798 0.830517 0.440451 0.121*
C10 0.3948 (4) 0.4470 (3) 0.7543 (4) 0.0298 (11)
H10 0.348828 0.502201 0.751113 0.036*
C11c 0.5090 (13) 0.8150 (11) 0.5091 (11) 0.080 (2)
H11c 0.451016 0.773716 0.480848 0.096*
C12 0.3459 (4) 0.3564 (3) 0.7644 (4) 0.0289 (10)
C13d 0.6226 (18) 0.8296 (16) 0.4773 (17) 0.078 (2)
H13d 0.648673 0.810779 0.418256 0.093*
C14 0.6027 (4) 0.1938 (4) 0.7644 (4) 0.0364 (12)
C15e 0.752 (2) 0.944 (3) 0.482 (3) 0.076 (2)
H15Ae 0.726067 0.971546 0.417557 0.091*
H15Be 0.780108 0.997631 0.524457 0.091*
C16 0.2200 (4) 0.3484 (4) 0.7692 (4) 0.0344 (11)
C17d 0.5564 (19) 0.7726 (17) 0.5337 (16) 0.078 (2)
H17d 0.526591 0.711176 0.517726 0.093*
C18 0.4156 (4) 0.2751 (3) 0.7684 (4) 0.0314 (11)
H18 0.384013 0.214188 0.776215 0.038*
C19f 0.8243 (9) 0.9682 (10) 0.4849 (10) 0.090 (3)
H19Af 0.863716 0.946090 0.547457 0.135*
H19Bf 0.866675 1.020516 0.460297 0.135*
H19Cf 0.818060 0.915759 0.437806 0.135*
C20 0.5870 (7) 0.9045 (5) 0.8788 (6) 0.0723 (16)
H20 0.556285 0.956452 0.840302 0.087*
C21c 0.5688 (12) 0.8745 (10) 0.4568 (11) 0.076 (2)
H21c 0.558672 0.884483 0.388245 0.092*
C22 0.6800 (7) 0.8236 (6) 0.9987 (6) 0.0814 (18)
H22 0.726074 0.806948 1.057510 0.098*
C23 0.6114 (7) 0.8972 (6) 0.6127 (6) 0.0771 (15)
H23 0.635292 0.934674 0.668686 0.093*

  1. aOccupancy: 0.8, bOccupancy: 0.35, cOccupancy: 0.6, dOccupancy: 0.4, eOccupancy: 0.2, fOccupancy: 0.65.

1 Source of materials

The title compound was obtained by a reaction of zinc sulfate heptahydrate (0.287 g, 1 mmol), 1,3,5-benzenetricarboxylic acid (0.42 g, 2 mmol), 1-ethylimidazole (0.6 mL), in mixture solution of 5 mL N, N ′ -dimethylformamide and 2.5 mL dimethyl sulfoxide, which was heated in a 25 mL steel autoclave and then was heated to 423 K for 6 h. After the mixture solutions were cooled to room temperature, colorless block crystals were collected from the mother liquor.

2 Experimental details

The structure was solved by Direct Methods with the SHELXS-2018 program. All H-atoms from C and N atoms were positioned with idealized geometry and refined isotropically (U iso (H) = 1.2U eq (C)) using a riding model. The four C atoms of 1-ethylimidazole are processed with part instruction to model the disorder.

3 Comment

Considerable effort has been devoted to the assembly of zinc-1,3,5-benzenetricarboxylic acid-based coordination polymers and many crystal structures are reported [5], [6], [7], [8]. Although zinc-1,3,5-benzenetricarboxylic acid and different imidazole-containing ligands have been used as co-ligands to construct zinc coordination polymers [9], [10], [11], [12], [13], [14], [15], to the best of our knowledge, there has not been reported any result of zinc-1,3,5-benzenetricarboxylic acid and neutral N-containing ligand 1-ethylimidazole.

Single X-ray diffraction study shows that the title compound crystallizes in the monoclinic space group P21/n (no. 14). The asymmetrical unit in title compound contains one Zn(II) cation, one benzene-1-carboxyl-3,5-dicarboxylate dianion (bcd) and two coordinated 1-ethylimidazole ligands. The Zn cation is tetrahedrally coordinated by two O atoms of bcd and two N atoms from two 1-ethylimidazole ligands, which is common in such zinc complexes [9], [10], [11], [12], [13], [14], [15].

The Zn-O, Zn-N bond distances are 1.9426–1.9478 Å and 1.9716–1.9733 Å, respectively. The bond angles around the central Zn vary from 93.4∘ to 116.7 ∘ , indicating that the tetrahedron is slightly distorted. All the bond lengths and angles are comparable with that observed in related zinc(II) complexes [9], [10], [11], [12], [13], [14], [15]. The results show that two protons of 1,3,5-benzenetricarboxylic acid are removed for the balance charge and bridged two Zn cation, which leads to the formation of 1D chains. It is worth noting that the 1D chains are different from the previous reports of zinc-1,3,5-benzenetricarboxylic acid-based chains [8], [9], [10]. A 2D layered structure is constructed by intermolecular hydrogen bond of oxygen atoms of the carboxyl groups between chains.

Corresponding author: Bao-Kuan Chen, School of Petrochemical Engineering Liaoning Petrochemical University, Fushun, Liaoning Province 113001, P. R. China, E-mail:

Acknowledgements

This work was supported by Talent Scientific Research Fund of Liaoning Petrochemical University (2016XJJL-019).

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

  2. Research funding: Talent Scientific Research Fund of Liaoning Petrochemical University (2016XJJL-019).

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

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Received: 2023-03-20
Accepted: 2023-04-14
Published Online: 2023-05-15
Published in Print: 2023-08-28

© 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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  63. Synthesis and crystal structure of 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
  64. Crystal structure of 2-(thiazol-2-yl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C11H10N2O3S
  65. Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
  66. Crystal structure of poly[(μ3-3, 5-dichloro-2-hydroxy-benzoato-κ4 Cl,O:O′:O″) silver(I)], C7H3AgCl2O3
  67. The crystal structure of tetrakis(1-isopropylimidazole-κ1 N)-[μ2- imidazole-4,5-dicarboxylato-κ4 O,N,O′,N′)]- trioxido-divanadium, C29H41N10O7V2
  68. Crystal structure of catena-[(μ3-bromido)-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N)copper(I)], C9H7BrCuN3O2
  69. The crystal structure of (E)-4-fluoro-N′-(1-(2-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
https://doi.org/10.1515/ncrs-2023-0132
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of a polymorph of potassium picrate, C6H2KN3O7
  4. The crystal structure of (1E,2E)-1,2-bis(quinolin-2-ylmethylene)hydrazine, C20H14N4
  5. 5-Amino-2-chloro-4-fluoro-N-(N-isopropyl-N-methylsulfamoyl) benzamide, C11H15O3ClFN3S
  6. Crystal structure of trans-N 1,N 8-bis(2-cyanoethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H42N6
  7. The crystal structure of [N-{[2-(oxy)-4-methoxyphenyl](phenyl)methylidene}alaninato]-diphenyl-silicon(IV) – chloroform (1/1), C29H25NO4Si·CHCl3
  8. Crystal structure of tetracarbonyl-{μ-[N-(diphenylphosphanyl)-N,P,P-triphenylphosphinous amide]}-bis[μ-(phenylmethanethiolato)]diiron (Fe–Fe), C48H39Fe2NO4P2S2
  9. Crystal structure of baryte from Mine du Pradet (France)
  10. The crystal structure of [(2,2′-bipyridine-6-carboxylato-κ3 N,N,O)-(6-phenylpyridine-2-carboxylate-κ2 N,O)copper(II)] monohydrate, C23H17N3O5Cu
  11. Crystal structure of bis(μ-benzeneselenolato)-(μ-[N-benzyl-N-(diphenylphosphanyl)-P,P-diphenylphosphinous amide])-tetracarbonyl diiron (Fe–Fe), C47H37Fe2NO4P2Se2
  12. The crystal structure of diaqua-methanol-κ1 O- (3-thiophenecarboxylato-κO)-(2,2′-dipyridyl-κ2 N,N′)manganese(II) 3-thiophenecarboxylate, C21H22N2O7S2Mn
  13. Crystal structure of catena-poly[tetrakis(butyl)-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O:O,O′,N-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O,N,O′:N′-ditin(IV)], C34H50N6O6Sn2
  14. Crystal structure of 4-chloro-N′-[(1E)-(2-nitrophenyl)methylidene]benzohydrazide, C14H10ClN3O3
  15. The crystal structure of 3-(1′-deoxy-3′,5′-O-dibenzy-β-d-ribosyl)adenine dichloromethane solvate, C49H52Cl2N10O6
  16. The crystal structure of (Z)-4-amino-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H17N3O
  17. The co-crystal structure of etoricoxib–phthalic acid (1/1), C18H15ClN2O2S·C8H6O4
  18. Crystal structure of (glycinto-κ 2 O,N ′)-[5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ 4 N,N ′,N ″,N ‴]nickel(II) perchlorate monohydrate C18H42ClN5NiO7
  19. The crystal structure of catena-poly[bis(1-ethylimidazole-k1 N)-(μ 2-benzene-1-carboxyl-3,5-dicarboxylato-κ 2 O, O′)zinc(II)], C19H20N4O6Zn
  20. Crystal structure of 3-(thiazol-2-ylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C11H12N2O4S
  21. Rietveld structure analysis of keatite, a rare, metastable SiO2 polymorph
  22. Crystal structure of catena-poly[(μ2-isophthalato-k3 O,O′:O″)(4-(4-pyridyl)-2,5-dipyrazylpyridine-k3 N,N′,N″)cobalt(II)] trihydrate C26H22N6O7Co1
  23. Crystal structure of 3,5–di-O-benzoyl-1,2-O-isopropylidene-α–D-ribose, C22H22O7
  24. The crystal structure of fac-tricarbonyl(6-bromo-2,2-bipyridine-κ2 N,N)-(nitrato-κO)rhenium(I), C13H7BrN3O6Re
  25. The crystal structure of (E)-N′-(4-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide monohydrate, C19H18N2O4
  26. The crystal structure of 5,5′-diselanediyl-bis(2-hydroxybenzaldehyde), C14H10O4Se2
  27. The crystal structure of catena-poly[diaqua-m2-dicyanido-κ2 C:N-dicyanido-κ1 C-bis(4-(pyridin-4-yl)benzaldehyde-κ1N)iron(II)-platinum(II), C28H22N6O4PtFe
  28. Redetermination of the crystal structure of 5,14-dihydro-6,17-dimethyl-8,15-diphenyldibenzo(b,i)(1,4,8,11)tetra-azacyclotetradecine, C32H28N4
  29. Crystal structure of poly[(μ3-2-(3,5-dicarboxyphenyl) benzimidazole-6-carboxylato-κ4O:O:O′:O″)lead(II)] monohydrate, C16H10N2O7Pb
  30. The crystal structure of fac-tricarbonyl(2-pyridin-2-yl-quinoline-κ2 N,N′)-(pyrazole-κN)rhenium(I)nitrate, C20H14N4O3ReNO3
  31. Crystal structure of dibromo-dicarbonyl-bis(tricyclohexylphosphine)-osmium(II) dichloromethane solvate, C38H66Br2O2OsP2
  32. Crystal structure of poly[bis(μ 2-2,6-bis(1-imidazoly)pyridine-κ 2 N:N′)copper(II)] diperchlorate dihydrate, C22H22Cl2CuN10O10
  33. The crystal structure of fac-tricarbonyl(N-benzoyl-N,N-cyclohexylmethylcarbamimidothioato-κ2 S,O)-(pyridine-κN)rhenium(I), C23H24N3O4ReS
  34. Crystal structure of (E)-7-fluoro-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O
  35. Synthesis and crystal structure of 1-((3R,10S,13S, 17S)-3-((2-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO2
  36. The crystal structure of fac-tricarbonyl((pyridin-2-yl)methanamino-κ2 N,N′)-((pyridin-2-yl)methanamino-κN)rhenium(I) nitrate, C15H16O3N4Re
  37. The crystal structure of (1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)-N-((1-(4-vinylbenzyl)-1H-benzo[d]imidazol-2-yl)methyl)methanamine-κ 4 N,N′,N″,N‴)tris(nitrato-kO,O′)-erbium(III), C29H27ErN8O9
  38. Crystal structure of tetracene-5,12-dione, C18H10O2
  39. Crystal structure of (3R,3aS,6R,6aR)-6-hexyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione, C13H20O4
  40. The crystal structure of N′1,N′3-bis((E)-thiophen-2-ylmethylene)isophthalohydrazide monohydrate, C18H16N4O3S2
  41. Crystal structure of methyl ((4-aminobenzyl)sulfonyl)-L-prolinate, C13H18N2O4S
  42. Crystal structure of (E)-3-(3-methoxybenzylidene)benzofuran-2(3H)-one, C16H12O3
  43. Synthesis and crystal structure (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C11H12BrNO2
  44. Synthesis and crystal structure of (S,E)-4-hydroxy-3-(2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C23H34O5
  45. The crystal structure of N,N′-(1,2-phenylene)bis (2-((2-oxopropyl)selanyl)benzamide), C26H24N2O4Se2
  46. The crystal structure of 1-ethyl-2-nitro-imidazole oxide, C5H7N3O3
  47. The crystal structure of 2-(2-fluorophenyl)naphtho[2,1-d]thiazole, C17H10FNS
  48. Crystal structure of (E)-2,4-di-tert-butyl-6-(((2-fluorophenyl)imino) methyl)phenol, C21H26FNO
  49. Synthesis and crystal structure of 3-methyl-2-(methylthio)-4H-chromen-4-one, C12H12O2S
  50. Crystal structure of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione, C14H4O2S4
  51. The crystal structure of dimethyl 2,2ʹ-((adamantane-1,3-diylbis(4,1-phenylene)) bis(oxy))diacetate, C28H32O6
  52. The crystal structure of N-(6-chloro-2-methyl-2H-indazol-5-yl)acetamide, C10H10ClN3O
  53. Crystal structure of triaqua-(5-bromoisophthalato-κ1 O)-(2,2′-bipyridine-κ2 N:N′)nickel(II) hydrate, C18H19BrN2NiO8
  54. The crystal structure of 2-amino-4-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  55. The crystal structure of catena-poly[5-aminonicotinic acid-k1 N-m2-bromido-copper(I)], Cu(C6N2H6O2)Br
  56. The crystal structure of 2,2-bis(3-methoxyphenyl)-1-tosyl-1,2-dihydro- 2λ4,3λ4  -[1,3,2]diazaborolo[4,5,1-ij]quinoline - dichloromethane (1/1)
  57. The crystal structure of catena-poly[bis(6-phenylpyridine-2-carboxylato-κ2 N,O)-(μ2-4,4′-bipyridne-κ2 N:N)cadmium(II)], C34H24N4O4Cd
  58. The crystal structure of 5,7-dinitropyrazolo[5,1-b]quinazolin-9(4H)-one, C10H5N5O5
  59. Crystal structure of rac-1,8-bis(2-carbamoylethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H46N6O2
  60. The crystal structure of (E)-N ′-(2-bromobenzylidene)-2-naphthohydrazide, C36H26Br2N4O2
  61. The crystal structure of 5-nitronaphthoquinone, C10H5NO4
  62. The crystal structure of (S, R p )-4–benzhydrylideneamino-12-(4-tert-butyl oxazolin-2-yl)[2.2]paracyclophane, C36H36N2O
  63. Synthesis and crystal structure of 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
  64. Crystal structure of 2-(thiazol-2-yl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C11H10N2O3S
  65. Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
  66. Crystal structure of poly[(μ3-3, 5-dichloro-2-hydroxy-benzoato-κ4 Cl,O:O′:O″) silver(I)], C7H3AgCl2O3
  67. The crystal structure of tetrakis(1-isopropylimidazole-κ1 N)-[μ2- imidazole-4,5-dicarboxylato-κ4 O,N,O′,N′)]- trioxido-divanadium, C29H41N10O7V2
  68. Crystal structure of catena-[(μ3-bromido)-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N)copper(I)], C9H7BrCuN3O2
  69. The crystal structure of (E)-4-fluoro-N′-(1-(2-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
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