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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m940.
Published online 2010 July 17. doi:  10.1107/S1600536810027418
PMCID: PMC3007483

Diacetato­(N,N-diethyl­ethylenediamine)­zinc(II)

Abstract

In the title compound, [Zn(CH3COO)2(C6H16N2)], the ZnII atom is coordinated by two N atoms of one bidentate diethyl­ethylenediamine ligand and two O atoms of two acetate anions in a distorted tetra­hedral geometry. The acetate ligands are asymmetrically coordinated to the Zn atom with two different C—O distances of 1.234 (4) and 1.275 (4) Å. The dihedral angle between the N/Zn/N and O/Zn/O planes is 83.11 (8)°. There are two independent mol­ecules in the asymmetric unit. N—H(...)O hydrogen bonding links mol­ecules into a three-dimensional network.

Related literature

For general background to luminescent compounds, see: Xu et al. (2008 [triangle]); Son et al. (2008 [triangle]). For the synthesis and structures of ZnII metal complexes, see: Kim et al. (2007a [triangle],b [triangle]); Seo et al. (2009 [triangle]); Das et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m940-scheme1.jpg

Experimental

Crystal data

  • [Zn(C2H3O2)2(C6H16N2)]
  • M r = 299.67
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m940-efi1.jpg
  • a = 7.5495 (1) Å
  • b = 13.3244 (2) Å
  • c = 27.5543 (4) Å
  • β = 94.617 (1)°
  • V = 2762.76 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.78 mm−1
  • T = 173 K
  • 0.18 × 0.10 × 0.1 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.722, T max = 0.834
  • 27467 measured reflections
  • 6837 independent reflections
  • 5523 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.126
  • S = 1.04
  • 6837 reflections
  • 309 parameters
  • H-atom parameters constrained
  • Δρmax = 1.74 e Å−3
  • Δρmin = −0.95 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027418/jh2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027418/jh2180Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported for two years by Pusan National University Research Grant. The X-ray data were collected at the Center for Research Facilities at Chungnam National University.

supplementary crystallographic information

Comment

Luminescent metal coordination compounds have attracted considerable attention for their potential applications in electroluminescent displays (Xu, et al. 2008). Among many coordination compounds, ZnII metal complexes are of great interest due to their facile synthesis, tunable emission color and good electroluminescent (EL) properties (Son, et al. 2008). Recently, we reported blue fluorescent zinc(II) complexes with nitrogen-containing ligand to develop luminescent materials (Seo, et al. 2009; Kim et al., 2007a; Kim et al., 2007b). In an extension of this study, here we prepared novel zinc(II) complex with N,N-diethylethylenediamine and structurally studied. In the title compound, the ZnII atom is coordinated by two N atoms of one bidentate diethylethylenediamine ligand and two O atoms of two acetate anions in a distorted tetrahedral geometry. The acetate ligands are asymmetrically coordinated to Zn atom with two different C—O distances of 1.234 (4) and 1.275 (4) Å. The dihedral angle between the N1/Zn1/N4 plane and O9/Zn1/O13 plane is 83.11 (8) °. N—H···O hydrogen bonding links molecules into a three-dimensional network.

The title compound shows an intense deep-blue emission at 402 nm attributed to 1(π - π*) intraligand charge transfer(ILCT) transition in CHCl3 upon 300 nm excitation and exhibits increased quantum yield of 5.47% compared with that of free ligand of 0.45%. The chelation of the ligand to ZnII increased the rigidity of the ligand and thus reduced the loss of energy by thermal vibrational decay, resulting in enhancing the quantum yield in the title coordination compound (Das, et al. 2006).

Experimental

A solution of zinc acetate (2.195 g, 10.0 mmol) and N,N-diethylethylenediamine (1.14 g, 10.0 mmol) in absolute ethanol (50 ml) was stirred for 8 h at room temperature under a nitrogen atmosphere. The resulting colourless solution was allowed to stand at room temperature for two weeks to produce colorless crystals (yield 65.0%) suitable for X-ray diffraction. Anal. calcd. for C10H22N2O4Zn: C, 40.08; H, 7.40; N, 8.57. Found: C, 38.69; H, 7.18; N, 8.57.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with N—H = 0.90 Å, and with Uiso(H) = 1.2Ueq(N) for NH2, C—H = 0.96 - 0.97 Å, and with Uiso(H) = 1.2Ueq(C) for methylene and 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
Molecular structure of (l), showing the atom-numbering scheme and 30% probability ellipsoids.

Crystal data

[Zn(C2H3O2)2(C6H16N2)]F(000) = 1264
Mr = 299.67Dx = 1.441 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8610 reflections
a = 7.5495 (1) Åθ = 2.8–28.0°
b = 13.3244 (2) ŵ = 1.78 mm1
c = 27.5543 (4) ÅT = 173 K
β = 94.617 (1)°Block, colourless
V = 2762.76 (7) Å30.18 × 0.1 × 0.1 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer5523 reflections with I > 2σ(I)
[var phi] and ω scansRint = 0.033
Absorption correction: multi-scan (SADABS; Bruker, 2002)θmax = 28.3°, θmin = 1.5°
Tmin = 0.722, Tmax = 0.834h = −10→10
27467 measured reflectionsk = −17→17
6837 independent reflectionsl = −35→36

Refinement

Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047w = 1/[σ2(Fo2) + (0.059P)2 + 4.8891P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.126(Δ/σ)max = 0.001
S = 1.04Δρmax = 1.74 e Å3
6837 reflectionsΔρmin = −0.95 e Å3
309 parameters

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

xyzUiso*/Ueq
Zn10.16918 (4)0.56462 (3)0.137611 (12)0.02318 (10)
N1−0.0915 (4)0.5126 (2)0.11436 (10)0.0288 (6)
C2−0.2078 (5)0.5939 (4)0.13401 (16)0.0501 (11)
H2A−0.21840.64910.1110.06*
H2B−0.32590.5670.1370.06*
C3−0.1366 (5)0.6315 (3)0.18130 (15)0.0401 (9)
H3A−0.14370.57920.20560.048*
H3B−0.20780.68780.19070.048*
N40.0500 (3)0.6638 (2)0.18003 (9)0.0263 (6)
H4A0.10470.66420.21030.032*
H4B0.0550.72610.16750.032*
C5−0.1389 (5)0.4146 (3)0.13401 (18)0.0493 (10)
H5A−0.12160.41650.16930.059*
H5B−0.26360.40130.12510.059*
C6−0.0318 (7)0.3335 (4)0.1158 (2)0.0727 (16)
H6A−0.0670.27070.12920.109*
H6B0.09160.34550.12530.109*
H6C−0.04950.33090.08090.109*
C7−0.1186 (6)0.5195 (4)0.06090 (15)0.0519 (11)
H7A−0.0320.47670.0470.062*
H7B−0.09460.5880.05140.062*
C8−0.3044 (6)0.4902 (5)0.03852 (18)0.0662 (15)
H8A−0.30850.49660.00370.099*
H8B−0.39150.53380.05090.099*
H8C−0.32930.42210.04690.099*
O90.2504 (3)0.62175 (18)0.07728 (8)0.0315 (5)
C100.3632 (4)0.6901 (3)0.08970 (13)0.0295 (7)
O110.4063 (3)0.71228 (19)0.13251 (10)0.0374 (6)
C120.4416 (5)0.7456 (3)0.04874 (16)0.0451 (10)
H12A0.38340.80930.0440.068*
H12B0.42490.70680.01940.068*
H12C0.56630.7560.05680.068*
O130.3570 (3)0.47619 (19)0.16413 (9)0.0331 (5)
C140.3221 (4)0.4350 (2)0.20440 (12)0.0281 (7)
O150.1721 (3)0.4354 (2)0.21913 (9)0.0367 (6)
C160.4745 (5)0.3854 (3)0.23375 (14)0.0402 (9)
H16A0.47350.40490.26730.06*
H16B0.58450.40590.22160.06*
H16C0.46270.31380.23110.06*
Zn20.26193 (4)0.00571 (3)0.136874 (12)0.02231 (10)
N170.5069 (4)0.0707 (2)0.12031 (10)0.0323 (6)
C180.6250 (5)0.0412 (3)0.16251 (16)0.0449 (8)
H18A0.60340.08430.18980.054*
H18B0.74730.05080.15510.054*
C190.5986 (5)−0.0656 (4)0.17656 (18)0.0527 (11)
H19A0.6471−0.1090.15270.063*
H19B0.6637−0.07820.20780.063*
N200.4078 (3)−0.0914 (2)0.18006 (10)0.0281 (6)
H20A0.3795−0.08580.21110.034*
H20B0.3865−0.15490.17010.034*
C210.4946 (6)0.1876 (4)0.12071 (18)0.0593 (13)
H21A0.45380.20920.15150.071*
H21B0.61220.21540.11820.071*
C220.3713 (8)0.2277 (4)0.0800 (2)0.0807 (19)
H22A0.36890.29970.08170.121*
H22B0.25380.20190.08290.121*
H22C0.41190.20730.04940.121*
C230.5562 (5)0.0365 (3)0.07219 (14)0.0371 (8)
H23A0.4610.05470.04810.045*
H23B0.5635−0.03620.07270.045*
C240.7298 (5)0.0772 (3)0.05540 (15)0.0408 (9)
H24A0.74850.05030.02390.061*
H24B0.82660.0580.07820.061*
H24C0.72380.14910.05350.061*
O250.0876 (3)0.08852 (18)0.16648 (8)0.0311 (5)
C260.1454 (4)0.1347 (2)0.20555 (11)0.0263 (6)
O270.3035 (3)0.1405 (2)0.21990 (8)0.0350 (6)
C280.0083 (5)0.1842 (3)0.23464 (15)0.0424 (9)
H28A0.02920.16560.26830.064*
H28B−0.10830.16270.22250.064*
H28C0.0170.25580.23160.064*
O290.1591 (3)−0.04624 (18)0.07437 (8)0.0291 (5)
C300.0457 (4)−0.1155 (3)0.08104 (12)0.0265 (6)
O310.0095 (3)−0.1432 (2)0.12188 (9)0.0390 (6)
C32−0.0414 (5)−0.1633 (3)0.03550 (14)0.0404 (9)
H32A0.0242−0.22210.02770.061*
H32B−0.0426−0.11640.0090.061*
H32C−0.1611−0.18190.04090.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.02171 (17)0.0258 (2)0.02222 (18)−0.00040 (14)0.00278 (12)0.00037 (14)
N10.0260 (13)0.0326 (16)0.0278 (13)−0.0040 (11)0.0014 (10)−0.0028 (12)
C20.0320 (18)0.061 (3)0.057 (3)0.0071 (19)0.0044 (17)−0.010 (2)
C30.0305 (17)0.042 (2)0.050 (2)0.0040 (16)0.0134 (15)−0.0109 (18)
N40.0319 (13)0.0245 (14)0.0229 (12)0.0010 (11)0.0041 (10)0.0007 (11)
C50.038 (2)0.042 (2)0.066 (3)−0.0063 (18)−0.0084 (19)0.008 (2)
C60.052 (3)0.066 (4)0.098 (4)−0.007 (2)−0.007 (3)−0.018 (3)
C70.041 (2)0.073 (3)0.039 (2)−0.015 (2)−0.0125 (17)0.010 (2)
C80.047 (2)0.093 (4)0.054 (3)−0.011 (3)−0.023 (2)−0.003 (3)
O90.0339 (12)0.0335 (13)0.0282 (11)−0.0064 (10)0.0091 (9)0.0018 (10)
C100.0259 (15)0.0251 (17)0.0385 (18)0.0060 (13)0.0090 (13)0.0050 (14)
O110.0331 (12)0.0341 (14)0.0445 (15)0.0012 (11)−0.0006 (10)−0.0050 (11)
C120.045 (2)0.038 (2)0.056 (2)−0.0040 (17)0.0204 (18)0.0119 (19)
O130.0303 (11)0.0348 (14)0.0346 (13)0.0048 (10)0.0050 (10)0.0088 (11)
C140.0330 (16)0.0201 (16)0.0303 (16)−0.0008 (13)−0.0024 (13)0.0002 (13)
O150.0337 (12)0.0468 (16)0.0300 (12)0.0006 (11)0.0049 (10)0.0037 (11)
C160.0408 (19)0.038 (2)0.041 (2)0.0070 (16)−0.0059 (15)0.0058 (17)
Zn20.02020 (17)0.0247 (2)0.02207 (18)−0.00164 (13)0.00178 (12)−0.00151 (14)
N170.0293 (13)0.0405 (17)0.0274 (14)−0.0142 (13)0.0038 (11)−0.0009 (12)
C180.0407 (19)0.040.054 (2)−0.0093 (17)0.0030 (18)−0.0051 (19)
C190.0283 (18)0.060 (3)0.067 (3)0.0067 (18)−0.0128 (18)0.011 (2)
N200.0304 (13)0.0291 (15)0.0246 (13)0.0020 (11)0.0014 (10)0.0001 (11)
C210.040.076 (3)0.066 (3)−0.033 (2)0.0304 (19)−0.026 (3)
C220.079 (4)0.054 (3)0.116 (5)0.017 (3)0.053 (4)0.020 (3)
C230.0349 (17)0.038 (2)0.0410 (19)−0.0088 (15)0.0162 (15)−0.0122 (16)
C240.0322 (17)0.046 (2)0.046 (2)0.0000 (16)0.0165 (15)−0.0023 (18)
O250.0262 (11)0.0336 (13)0.0335 (12)0.0022 (10)0.0019 (9)−0.0097 (10)
C260.0290 (15)0.0232 (16)0.0271 (15)−0.0001 (13)0.0048 (12)0.0016 (12)
O270.0296 (12)0.0475 (16)0.0278 (11)−0.0012 (11)0.0015 (9)−0.0052 (11)
C280.0360 (18)0.049 (2)0.043 (2)0.0029 (17)0.0077 (16)−0.0154 (18)
O290.0261 (11)0.0342 (13)0.0267 (11)−0.0065 (10)0.0008 (9)−0.0048 (10)
C300.0211 (13)0.0266 (17)0.0319 (16)0.0024 (12)0.0030 (12)−0.0031 (13)
O310.0446 (14)0.0352 (14)0.0381 (14)0.0001 (12)0.0085 (11)0.0066 (11)
C320.0325 (17)0.043 (2)0.045 (2)−0.0111 (16)0.0002 (15)−0.0105 (17)

Geometric parameters (Å, °)

Zn1—O131.941 (2)Zn2—O251.946 (2)
Zn1—O91.971 (2)Zn2—O291.958 (2)
Zn1—N42.023 (3)Zn2—N202.023 (3)
Zn1—N12.136 (3)Zn2—N172.124 (3)
N1—C51.468 (5)N17—C181.461 (5)
N1—C71.474 (5)N17—C231.478 (4)
N1—C21.522 (5)N17—C211.560 (6)
C2—C31.458 (6)C18—C191.493 (6)
C2—H2A0.97C18—H18A0.97
C2—H2B0.97C18—H18B0.97
C3—N41.476 (4)C19—N201.491 (5)
C3—H3A0.97C19—H19A0.97
C3—H3B0.97C19—H19B0.97
N4—H4A0.9N20—H20A0.9
N4—H4B0.9N20—H20B0.9
C5—C61.464 (7)C21—C221.497 (8)
C5—H5A0.97C21—H21A0.97
C5—H5B0.97C21—H21B0.97
C6—H6A0.96C22—H22A0.96
C6—H6B0.96C22—H22B0.96
C6—H6C0.96C22—H22C0.96
C7—C81.536 (5)C23—C241.524 (5)
C7—H7A0.97C23—H23A0.97
C7—H7B0.97C23—H23B0.97
C8—H8A0.96C24—H24A0.96
C8—H8B0.96C24—H24B0.96
C8—H8C0.96C24—H24C0.96
O9—C101.275 (4)O25—C261.285 (4)
C10—O111.234 (4)C26—O271.229 (4)
C10—C121.509 (5)C26—C281.510 (5)
C12—H12A0.96C28—H28A0.96
C12—H12B0.96C28—H28B0.96
C12—H12C0.96C28—H28C0.96
O13—C141.284 (4)O29—C301.282 (4)
C14—O151.233 (4)C30—O311.236 (4)
C14—C161.505 (5)C30—C321.510 (5)
C16—H16A0.96C32—H32A0.96
C16—H16B0.96C32—H32B0.96
C16—H16C0.96C32—H32C0.96
O13—Zn1—O9106.53 (10)O25—Zn2—O29109.61 (10)
O13—Zn1—N4121.65 (11)O25—Zn2—N20118.07 (11)
O9—Zn1—N4114.72 (11)O29—Zn2—N20116.73 (11)
O13—Zn1—N1122.93 (11)O25—Zn2—N17119.27 (11)
O9—Zn1—N1102.37 (10)O29—Zn2—N17104.20 (10)
N4—Zn1—N186.76 (11)N20—Zn2—N1786.84 (11)
C5—N1—C7114.0 (3)C18—N17—C23116.7 (3)
C5—N1—C2109.7 (3)C18—N17—C21107.2 (3)
C7—N1—C2105.9 (3)C23—N17—C21109.5 (3)
C5—N1—Zn1115.1 (2)C18—N17—Zn2101.9 (2)
C7—N1—Zn1109.3 (2)C23—N17—Zn2110.7 (2)
C2—N1—Zn1101.9 (2)C21—N17—Zn2110.6 (2)
C3—C2—N1112.4 (3)N17—C18—C19112.1 (3)
C3—C2—H2A109.1N17—C18—H18A109.2
N1—C2—H2A109.1C19—C18—H18A109.2
C3—C2—H2B109.1N17—C18—H18B109.2
N1—C2—H2B109.1C19—C18—H18B109.2
H2A—C2—H2B107.9H18A—C18—H18B107.9
C2—C3—N4111.3 (3)N20—C19—C18112.7 (3)
C2—C3—H3A109.4N20—C19—H19A109
N4—C3—H3A109.4C18—C19—H19A109
C2—C3—H3B109.4N20—C19—H19B109
N4—C3—H3B109.4C18—C19—H19B109
H3A—C3—H3B108H19A—C19—H19B107.8
C3—N4—Zn1107.0 (2)C19—N20—Zn2107.3 (2)
C3—N4—H4A110.3C19—N20—H20A110.3
Zn1—N4—H4A110.3Zn2—N20—H20A110.3
C3—N4—H4B110.3C19—N20—H20B110.3
Zn1—N4—H4B110.3Zn2—N20—H20B110.3
H4A—N4—H4B108.6H20A—N20—H20B108.5
C6—C5—N1111.9 (4)C22—C21—N17112.6 (4)
C6—C5—H5A109.2C22—C21—H21A109.1
N1—C5—H5A109.2N17—C21—H21A109.1
C6—C5—H5B109.2C22—C21—H21B109.1
N1—C5—H5B109.2N17—C21—H21B109.1
H5A—C5—H5B107.9H21A—C21—H21B107.8
C5—C6—H6A109.5C21—C22—H22A109.5
C5—C6—H6B109.5C21—C22—H22B109.5
H6A—C6—H6B109.5H22A—C22—H22B109.5
C5—C6—H6C109.5C21—C22—H22C109.5
H6A—C6—H6C109.5H22A—C22—H22C109.5
H6B—C6—H6C109.5H22B—C22—H22C109.5
N1—C7—C8115.7 (4)N17—C23—C24116.6 (3)
N1—C7—H7A108.3N17—C23—H23A108.1
C8—C7—H7A108.3C24—C23—H23A108.1
N1—C7—H7B108.3N17—C23—H23B108.1
C8—C7—H7B108.3C24—C23—H23B108.1
H7A—C7—H7B107.4H23A—C23—H23B107.3
C7—C8—H8A109.5C23—C24—H24A109.5
C7—C8—H8B109.5C23—C24—H24B109.5
H8A—C8—H8B109.5H24A—C24—H24B109.5
C7—C8—H8C109.5C23—C24—H24C109.5
H8A—C8—H8C109.5H24A—C24—H24C109.5
H8B—C8—H8C109.5H24B—C24—H24C109.5
C10—O9—Zn1107.2 (2)C26—O25—Zn2115.3 (2)
O11—C10—O9123.1 (3)O27—C26—O25123.7 (3)
O11—C10—C12120.6 (3)O27—C26—C28119.4 (3)
O9—C10—C12116.3 (3)O25—C26—C28116.9 (3)
C10—C12—H12A109.5C26—C28—H28A109.5
C10—C12—H12B109.5C26—C28—H28B109.5
H12A—C12—H12B109.5H28A—C28—H28B109.5
C10—C12—H12C109.5C26—C28—H28C109.5
H12A—C12—H12C109.5H28A—C28—H28C109.5
H12B—C12—H12C109.5H28B—C28—H28C109.5
C14—O13—Zn1112.9 (2)C30—O29—Zn2110.5 (2)
O15—C14—O13122.7 (3)O31—C30—O29123.0 (3)
O15—C14—C16120.5 (3)O31—C30—C32121.1 (3)
O13—C14—C16116.8 (3)O29—C30—C32115.8 (3)
C14—C16—H16A109.5C30—C32—H32A109.5
C14—C16—H16B109.5C30—C32—H32B109.5
H16A—C16—H16B109.5H32A—C32—H32B109.5
C14—C16—H16C109.5C30—C32—H32C109.5
H16A—C16—H16C109.5H32A—C32—H32C109.5
H16B—C16—H16C109.5H32B—C32—H32C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···O27i0.92.022.904 (3)168
N4—H4B···O31ii0.92.163.032 (4)163
N20—H20A···O15iii0.92.012.911 (4)176
N20—H20B···O11iv0.92.062.925 (4)160

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, y+1, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2180).

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