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In the title compound, [Zn(C2H3O2)2(C2H8N2)], the ZnII atom is coordinated by two N atoms of one bidentate ethyl­enediamine ligand and two O atoms of two acetate anions in a distorted tetra­hedral geometry. The compound displays [4+2] coordination, the `4' representing the distorted tetra­hedral coordination, while the `2' refers to the two much longer Zn...O(uncoordinated) distances of 2.594 (2) Å. The asymmetry of the acetate coordination is reflected in the different C—O distances of 1.229 (2) and 1.280 (2) Å. The Zn atom lies on a crystallographic twofold rotation axis. The dihedral angles between the N/Zn/N′ plane and the two O/Zn/O′ planes are 85.54 (7) and 29.96 (7)°, where the prime denotes the atom related by operation of the twofold axis. N—H...O hydrogen bonding links the mol­ecules into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036616/bm3031sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036616/bm3031Isup2.hkl
Contains datablock I

CCDC reference: 657642

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.026
  • wR factor = 0.067
  • Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 1.87
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Luminescent coordination compounds have been investigated extensively due to their various potential applications in material sciences (Amendola et al. 2006). Many Zn(II) complexes are known to exhibit an intense fluorescence at room temperature (Yang, et al. 2000; Xu, et al. 2006), and they are proposed as candidates for the fluorescent based organic light-emitting diods (OLED) devices (Evans, et al. 2006). The title compound displays distorted tetrahedral coordination, with two N atoms from ethylenediamine and two O atoms from two acetate ligands. The title compound displays [4 + 2] coordination: the "4" represnets the distorted tetrahedral coordination, while the "2" means the two much longer Zn1—O5 distances of 2.594 (2) Å. The asymmetry of the acetate coordination is reflected in the different C—O distances of 1.229 (2) and 1.280 (2) Å. The Zn1 lies on a crystallographic twofold axis. The dihedral angle between N1—Zn1—N1' and O3—Zn1—O3' planes is 85.54 (7) °, where the prime denotes the symetry operation about the twofold axis. While the dihedral angle between N1—Zn1—N1' and O5—Zn1—O5' planes is 29.96 (7) °. N—H···O hydrogen bonding links molecules into a three-dimensional network. The title compound exhibits an intense blue emission at 444 nm in CHCl3 upon 368 nm excitation.

Related literature top

For general background see: Amendola et al. (2006); Yang et al. (2000); Xu et al. (2006); Evans et al. (2006).

Experimental top

A solution of zinc acetate (2.195 g, 10.0 mmol) and ethylenediamine (0.601 g, 10.0 mmol) in absolute ethanol (50 ml) was stirred for 8 hrs at room temperature under a nitrogen atmosphere. The resulting colorless solution was allowed to stand at room temperature for two weeks to produce colorless crystals (yield 65.0%) suitable for X-ray diffraction.

Refinement top

Apart from those of sp2-bound methyl groups, which were located in ΔF syntheses, H atoms were positioned geometrically. Thereafter they were constrained to ride on their carrier atoms, with N—H = 0.90 Å and Uiso(H) = 1.2Uiso(N) for NH2, C—H = 0.97 Å and Uiso(H) = 1.2Uiso(C) for CH2, and C—H = 0.96 Å and Uiso(H) = 1.5Uiso(C) for CH3 groups.

Structure description top

Luminescent coordination compounds have been investigated extensively due to their various potential applications in material sciences (Amendola et al. 2006). Many Zn(II) complexes are known to exhibit an intense fluorescence at room temperature (Yang, et al. 2000; Xu, et al. 2006), and they are proposed as candidates for the fluorescent based organic light-emitting diods (OLED) devices (Evans, et al. 2006). The title compound displays distorted tetrahedral coordination, with two N atoms from ethylenediamine and two O atoms from two acetate ligands. The title compound displays [4 + 2] coordination: the "4" represnets the distorted tetrahedral coordination, while the "2" means the two much longer Zn1—O5 distances of 2.594 (2) Å. The asymmetry of the acetate coordination is reflected in the different C—O distances of 1.229 (2) and 1.280 (2) Å. The Zn1 lies on a crystallographic twofold axis. The dihedral angle between N1—Zn1—N1' and O3—Zn1—O3' planes is 85.54 (7) °, where the prime denotes the symetry operation about the twofold axis. While the dihedral angle between N1—Zn1—N1' and O5—Zn1—O5' planes is 29.96 (7) °. N—H···O hydrogen bonding links molecules into a three-dimensional network. The title compound exhibits an intense blue emission at 444 nm in CHCl3 upon 368 nm excitation.

For general background see: Amendola et al. (2006); Yang et al. (2000); Xu et al. (2006); Evans et al. (2006).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom-numbering scheme and 30% probability ellipsoids.
Diacetato(ethylenediamine)zinc(II) top
Crystal data top
[Zn(C2H3O2)2(C2H8N2)]F(000) = 504
Mr = 243.56Dx = 1.645 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 1923 reflections
a = 12.1335 (4) Åθ = 3.1–26.9°
b = 7.7866 (2) ŵ = 2.48 mm1
c = 10.4078 (3) ÅT = 295 K
V = 983.32 (5) Å3Block, colourless
Z = 40.12 × 0.12 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
867 reflections with I > 2σ(I)
φ and ω scansRint = 0.028
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
θmax = 28.3°, θmin = 3.1°
Tmin = 0.745, Tmax = 0.758h = 1611
5391 measured reflectionsk = 710
1221 independent reflectionsl = 913
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026 w = 1/[σ2(Fo2) + (0.03P)2 + 0.232P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.067(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.28 e Å3
1221 reflectionsΔρmin = 0.34 e Å3
61 parameters
Crystal data top
[Zn(C2H3O2)2(C2H8N2)]V = 983.32 (5) Å3
Mr = 243.56Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 12.1335 (4) ŵ = 2.48 mm1
b = 7.7866 (2) ÅT = 295 K
c = 10.4078 (3) Å0.12 × 0.12 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1221 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
867 reflections with I > 2σ(I)
Tmin = 0.745, Tmax = 0.758Rint = 0.028
5391 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.067H-atom parameters constrained
S = 0.99Δρmax = 0.28 e Å3
1221 reflectionsΔρmin = 0.34 e Å3
61 parameters
Special details top

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) top
xyzUiso*/Ueq
Zn10.50.61106 (4)0.750.03233 (13)
N10.39968 (13)0.4143 (2)0.68272 (16)0.0361 (4)
H1A0.32860.43520.70170.043*
H1B0.40640.40280.5970.043*
C20.43883 (19)0.2582 (3)0.7493 (2)0.0531 (7)
H2A0.4120.15680.70510.064*
H2B0.41090.25620.83660.064*
O30.56408 (11)0.71701 (18)0.59300 (13)0.0405 (4)
C40.63853 (17)0.8189 (3)0.6350 (2)0.0364 (5)
O50.66115 (15)0.8299 (2)0.74983 (13)0.0513 (4)
C60.6980 (2)0.9260 (3)0.5362 (2)0.0526 (6)
H6A0.75070.99840.57830.079*
H6B0.64530.99620.49120.079*
H6C0.73480.85230.47630.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0364 (2)0.0318 (2)0.02885 (18)00.00367 (14)0
N10.0369 (10)0.0397 (11)0.0316 (9)0.0031 (8)0.0019 (8)0.0034 (7)
C20.0726 (17)0.0370 (13)0.0495 (13)0.0147 (12)0.0162 (14)0.0061 (11)
O30.0420 (9)0.0408 (9)0.0386 (8)0.0132 (7)0.0047 (7)0.0014 (6)
C40.0424 (13)0.0280 (11)0.0386 (11)0.0004 (10)0.0077 (10)0.0027 (9)
O50.0634 (11)0.0538 (10)0.0367 (8)0.0129 (9)0.0037 (7)0.0030 (8)
C60.0665 (16)0.0486 (14)0.0427 (12)0.0260 (13)0.0051 (12)0.0027 (11)
Geometric parameters (Å, º) top
Zn1—N12.0784 (16)C2—H2B0.97
Zn1—O31.9887 (13)O3—C41.280 (2)
N1—C21.477 (3)C4—O51.229 (2)
N1—H1A0.90C4—C61.508 (3)
N1—H1B0.90C6—H6A0.96
C2—C2i1.485 (5)C6—H6B0.96
C2—H2A0.97C6—H6C0.96
N1—Zn1—N1i85.01 (9)C2i—C2—H2B109.9
N1—Zn1—O3104.95 (6)H2A—C2—H2B108.3
N1i—Zn1—O3110.71 (6)C4—O3—Zn1104.61 (12)
C2—N1—Zn1105.09 (12)O5—C4—O3122.23 (19)
C2—N1—H1A110.7O5—C4—C6121.2 (2)
Zn1—N1—H1A110.7O3—C4—C6116.56 (18)
C2—N1—H1B110.7C4—C6—H6A109.5
Zn1—N1—H1B110.7C4—C6—H6B109.5
H1A—N1—H1B108.8H6A—C6—H6B109.5
N1—C2—C2i109.05 (16)C4—C6—H6C109.5
N1—C2—H2A109.9H6A—C6—H6C109.5
C2i—C2—H2A109.9H6B—C6—H6C109.5
N1—C2—H2B109.9
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O3ii0.902.223.078 (2)160
N1—H1A···O5iii0.902.253.050 (2)148
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x1/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Zn(C2H3O2)2(C2H8N2)]
Mr243.56
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)295
a, b, c (Å)12.1335 (4), 7.7866 (2), 10.4078 (3)
V3)983.32 (5)
Z4
Radiation typeMo Kα
µ (mm1)2.48
Crystal size (mm)0.12 × 0.12 × 0.11
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.745, 0.758
No. of measured, independent and
observed [I > 2σ(I)] reflections
5391, 1221, 867
Rint0.028
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.067, 0.99
No. of reflections1221
No. of parameters61
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.34

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Zn1—N12.0784 (16)O3—C41.280 (2)
Zn1—O31.9887 (13)C4—O51.229 (2)
N1—C21.477 (3)
N1—Zn1—N1i85.01 (9)N1i—Zn1—O3110.71 (6)
N1—Zn1—O3104.95 (6)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O3ii0.902.223.078 (2)160
N1—H1A···O5iii0.902.253.050 (2)148
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x1/2, y1/2, z+3/2.
 

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