Home Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6
Article Open Access

Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6

  • Jaeun Kang , Kang Min Ok and Junghwan Do EMAIL logo
Published/Copyright: August 13, 2018

Abstract

C10H18O6Zn, monoclinic, P2/c (no. 13), a = 11.0730(2) Å, b = 5.52600(10) Å, c = 10.8410(2) Å, β = 100.350(1)°, V = 652.56(2) Å3, Z = 2, Rgt(F) = 0.0318, wRref(F2) = 0.0842, T = 293(2) K.

CCDC no.: 1859435

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:

Crystal collection and handling.

Crystal:Rod, colorless
Size:0.10 × 0.02 × 0.01 mm
Wavelength:Mo Kα radiation (λ = 0.71073 Å)
μ:1.894 mm−1
Diffractometer, scan mode:Bruker APEX, Φ and ω-scans
2θmax, completeness:28.32°, >99%
N(hkl)measured, N(hkl)unique, Rint:7022, 1629, 0.0288
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 1473
N(param)refined:88
Programs:Bruker programs [1], SHELX [2, 3] , Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
Zn10.5000000.09597(5)0.7500000.01995(13)
O10.36077(15)0.4042(2)0.72855(13)0.0240(3)
O20.41494(15)0.2101(2)0.57131(12)0.0258(3)
C10.35581(19)0.3818(3)0.61192(18)0.0220(4)
C20.2879(2)0.5540(4)0.52047(18)0.0255(4)
H10.3174910.5753420.4461890.031
C30.1888(2)0.6820(4)0.53298(18)0.0258(4)
C40.1357(2)0.8566(4)0.4313(2)0.0371(5)
H2A0.1813430.8476330.3640510.056
H2B0.1403031.0180010.4645430.056
H2C0.0514310.8156770.4002670.056
C50.1225(2)0.6683(5)0.6419(2)0.0366(5)
H3A0.1522610.5322120.6935890.055
H3B0.0361020.6498450.6115020.055
H3C0.1367810.8142560.6904270.055
OW10.39298(16)−0.1401(3)0.82073(14)0.0266(3)
H4A0.401(3)−0.156(5)0.894(3)0.045(8)
H4B0.381(3)−0.266(6)0.794(3)0.040(8)

Source of material

The title complex was synthesized from a mixture of ZnCl2 (0.123 g, 0.9 mmol), 3,3-dimethylacrylic acid (3-methylcrotonic acid) (0.09 g, 0.9 mmol), 1,3-diaminopropane (0.025 mL, 0.3 mmol), and ethanol (1.0 mL), which was sealed in a Pyrex tube and heated to 70 °C for 68 h, then cooled to room temperature at 20 °C/h. The solution pH values before and after the reaction were ∼6 and ∼5, respectively. The solid products were recovered by vacuum filtration. Colorless rod crystals were obtained with unidentified colorless chunk. The product was stable in air. The yield of the compound was about 30% based on zinc. EDX analysis confirmed the presence of Zn.

Experimental detail

All hydrogen atoms of 3,3-diemthylacrylate were placed in calculated positions and refined as riding model. The Uiso value of the methyl group was set to 1.5Ueq and the Uiso values of the other hydrogen atoms were set to 1.2Ueq. The hydrogen atoms in water molecules were located in difference Fourier maps, and their positions and isotropic displacement parameters were refined.

Comment

Metal complexes containing carboxylate are one of the most important classes in coordination chemistry. Although limited in number, however, Zn(II) carboxylates have been studied due to their importance in supramolecular chemistry and in biological system [5], [6], [7], [8], [9], [10], [11]. In this study we report a new zinc(II) complex containing 3,3-dimthylacrylate. The crystal structure of the title compound simply comprises discrete zinc(II) complex moieties. The crystallographically unique Zn atom, located on a 2-fold axis, is coordinated by four oxygen atoms from two symmetry related 3,3-dimethylacrylate ligands [d(Zn—O) = 2.0934(13) Å and 2.2810(14) Å] in a κ2,O,O′ mode (see the figure). Two water molecules [d(Zn—O) = 2.0051(15) Å] in cis-configuration complete the distorted octahedral environment of Zn1. The bond valence sum (BVS) calculation for Zn gives a value of +2.00 indicating an oxidation state of +2 [12]. The crystal packing of the title compound is stabilized by the presence of hydrogen bonds between the coordinated water molecules and the carboxylate oxygen atoms [d(OH⋅ ⋅ ⋅ O) = 1.9271(1) Å and 1.9538(1) Å] in adjacent zinc(II) complex moieties, which results in the formation of layers on the ac-plane. The hydrogen bonded layers stack along the a-axis and interact through van der Waals forces between the methyl groups. The interlayer distance between the methyl groups is >3.86 Å.

Acknowledgements

This paper was supported by Konkuk University in 2017.

References

Bruker. SAINT, APEX2, Bruker Inc., Madison, WI, USA (2016).Search in Google Scholar

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

Hubschle, C. B.; Sheldrick, G. M.; Dittrich, B.: ShelXle: a Qt graphical user interface for SHELXL. J. Appl. Crystallogr. 44 (2011) 1281–1284.10.1107/S0021889811043202Search in Google Scholar PubMed PubMed Central

Brandenburg, K.: DIAMOND. Visual crystal structure information system. Version 4.2.2. Crystal Impact, Bonn, Germany (2016).Search in Google Scholar

Hafeez, S. T.; Ali, S.; Tahir, M. N.; Iqbal, M.; Munawar, K. S.: One-pot synthesis, structural elucidation, DNA binding and alkaline phosphatase inhibition studies of zinc(II) complexes with 4-nitrocinnamic acid and ethylenediamine. J. Coord. Chem. 67 (2014) 2479–2495.10.1080/00958972.2014.940922Search in Google Scholar

Zeleňák, V.; Sabo, M.; Massa, W.; Llewellyn, P.: Preparation, characterization and crystal structure of two zinc(II) benzoate complexes with pyridine-based ligands nicotinamide and methyl-3-pyridylcarbamate. Inorg. Chim. Acta 357 (2004) 2049–2059.10.1016/j.ica.2004.01.016Search in Google Scholar

Cunnane, S. C.: Zinc: Clinical and Biochemical Significance, CRC Press, Boca Raton, FL (1988).Search in Google Scholar

Burrows, A. D.; Chan, S.; Gee, W. J.; Mahon, M. F.; Richardson, C.; Sebestyen, V. M.; Turski, D.; Warren, M. R.: The impact of N,N′-ditopic ligand length and geometry on the structures of zinc-based mixed-linker metal–organic frameworks. CrystEngComm 19 (2017) 5549–5557.10.1039/C7CE01447CSearch in Google Scholar

Dybtsev, D. N.; Chun, H.; Kim, K.: Rigid and flexible: a highly porous metal-organic framework with unusual guest-dependent dynamic behavior. Angew. Chem. Int. Ed. 43 (2004) 5033–5036.10.1002/anie.200460712Search in Google Scholar PubMed

Chun, H.; Dybtsev, D. N.; Kim, H.; Kim, K.: Synthesis, X-ray crystal structures, and gas sorption properties of pillared square grid nets based on paddle-sheel motifs: implications for hydrogen storage in porous materials. Chem. Eur. J. 11 (2005) 3521–3529.10.1002/chem.200401201Search in Google Scholar PubMed

Chen, B.; Liang, C.; Yang, J.; Contreras, D. S.; Clancy, Y. L.; Lobkovsky, E. B.; Yaghi, O. M.; Dai, S.: A microporous metal-organic gramework for gas-chromatographic separation of alkanes. Angew. Chem. Int. Ed. 45 (2006) 1390–1393.10.1002/anie.200502844Search in Google Scholar PubMed

Brese, N. E.; O’Keeffe, M.: Bond-valence parameters for solids. Acta Crystallogr. B47 (1991) 192–197.10.1107/S0108768190011041Search in Google Scholar

Received: 2018-07-11
Accepted: 2018-07-31
Published Online: 2018-08-13
Published in Print: 2018-12-19

©2018 Jaeun Kang et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  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
Downloaded on 21.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0235/html
Scroll to top button