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In the crystal structure of the title compound, {[Zn(C2O4)(C2H8N2)]·2H2O}n, the ZnII atom adopts an octahedral geometry, formed by two N atoms of an ethyl­enedi­amine ligand [Zn—N = 2.112 (4)–2.124 (4)) Å] and four O atoms of two bridging oxalate ligands [Zn—O = 2.105 (3)–2.154 (3) Å]. The asymmetric unit consists of one and one-half formula units.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401668X/ci6390sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680401668X/ci6390Isup2.hkl
Contains datablock I

CCDC reference: 248748

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.060
  • wR factor = 0.163
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.33 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.56 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C6 - C6_b ... 1.56 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O8 .. C1 .. 3.01 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O10 .. C2 .. 3.01 Ang.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C4 H12 N2 O6 Zn1 Atom count from _chemical_formula_moiety:C4 H12 N6 O6 Zn1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: COLLECT; data reduction: COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

catena-Poly[[[(ethylenediamine-κ2N,N')zinc(II)]-µ-oxalato] dihydrate] top
Crystal data top
[Zn(C2O4)(C2H8N2)]·2H2OF(000) = 1536
Mr = 249.53Dx = 1.837 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 20214 reflections
a = 25.757 (5) Åθ = 2.9–27.6°
b = 9.053 (3) ŵ = 2.73 mm1
c = 11.623 (2) ÅT = 173 K
β = 93.05 (3)°Prism, colorless
V = 2706.4 (11) Å30.20 × 0.12 × 0.10 mm
Z = 12
Data collection top
Nonius KappaCCD area-detector
diffractometer
3121 independent reflections
Radiation source: fine-focus sealed tube2425 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 27.6°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3333
Tmin = 0.606, Tmax = 0.764k = 1111
20214 measured reflectionsl = 1415
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.23 w = 1/[σ2(Fo2) + (0.0528P)2 + 25.3123P]
where P = (Fo2 + 2Fc2)/3
3121 reflections(Δ/σ)max = 0.001
196 parametersΔρmax = 1.47 e Å3
66 restraintsΔρmin = 2.17 e Å3
Special details top

Experimental. A crystal was selected for the X–ray measurements and mounted to the glass fiber using the oil drop method (Kottke & Stalke, 1993) and data were collected at 193 K. The intensity data were corrected for Lorentz and polarization effects and for absorption. one of the ethylenediamine ligands was found to be disordered and was refined in two positions with population parameter 0.5. The positional and atomic displacement factors of nitrogen N1A and N1B and N2A and N2B, respectively, of the disordered ethylenediammine ligand were fixed to be the same. N1A and N1B, as well as, N2A and N2B, effectively act as single nitrogen atom. The reason for this model is to model the hydrogen atoms at these N atoms correctly.

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.33312 (2)0.07555 (6)0.57783 (4)0.01721 (19)
Zn20.50000.41017 (7)0.75000.0166 (2)
O10.35169 (12)0.2426 (3)0.7054 (3)0.0177 (7)
O20.41333 (13)0.1046 (4)0.5592 (3)0.0223 (7)
C10.39860 (17)0.2815 (4)0.7083 (4)0.0140 (8)
C20.43456 (17)0.2014 (5)0.6244 (4)0.0153 (8)
O30.41929 (12)0.3791 (3)0.7723 (3)0.0187 (7)
O40.48126 (12)0.2378 (3)0.6277 (3)0.0172 (6)
N10.34208 (16)0.1042 (4)0.6935 (3)0.0192 (8)
H11A0.37030.09190.74460.023*0.50
H12A0.31270.11970.73340.023*0.50
H11B0.37660.11240.71720.023*0.50
H12B0.32370.08490.75750.023*0.50
C3A0.3121 (4)0.2192 (10)0.5056 (7)0.0154 (17)0.50
H31A0.31540.30470.45330.019*0.50
H32A0.27630.21670.53220.019*0.50
C4A0.3510 (4)0.2300 (9)0.6062 (8)0.0143 (16)0.50
H41A0.38660.22300.57880.017*0.50
H42A0.34740.32680.64460.017*0.50
N20.32348 (18)0.0895 (4)0.4501 (4)0.0249 (9)
H21A0.29680.06470.39790.030*0.50
H22A0.35350.09980.41120.030*0.50
H21B0.28930.09700.42350.030*0.50
H22B0.34380.07090.38900.030*0.50
C3B0.3246 (4)0.2433 (9)0.6441 (7)0.0154 (17)0.50
H31B0.28630.25100.64330.018*0.50
H32B0.34000.32730.68850.018*0.50
C4B0.3432 (4)0.2425 (9)0.5217 (7)0.0156 (17)0.50
H41B0.32940.33070.48000.019*0.50
H42B0.38160.24790.52450.019*0.50
O50.25265 (12)0.1034 (4)0.5992 (3)0.0206 (7)
N30.51433 (18)0.5843 (5)0.8701 (4)0.0309 (10)
H310.54320.56510.90120.037*
H320.48920.59920.92330.037*
C50.5211 (2)0.7224 (6)0.7996 (5)0.0293 (11)
H5A0.55610.72380.76820.035*
H5B0.51750.81110.84840.035*
O60.31469 (12)0.2532 (4)0.4600 (3)0.0235 (7)
C60.26805 (18)0.2933 (5)0.4599 (4)0.0189 (9)
O80.43549 (12)0.0229 (3)0.8530 (3)0.0186 (7)
H810.46260.07410.85210.028*
H820.43320.02120.91900.028*
O90.26722 (17)0.4462 (6)0.7070 (4)0.0626 (17)
H910.26740.49620.76760.094*
H920.29590.40470.69740.094*
O100.09839 (15)0.0553 (5)0.5403 (4)0.0466 (12)
H1020.12700.10030.54090.070*
H1010.10350.00960.60310.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0135 (3)0.0204 (3)0.0175 (3)0.00060 (18)0.00122 (19)0.00589 (19)
Zn20.0127 (4)0.0087 (3)0.0280 (4)0.0000.0011 (3)0.000
O10.0154 (16)0.0143 (14)0.0232 (16)0.0014 (12)0.0002 (12)0.0041 (12)
O20.0166 (16)0.0294 (17)0.0207 (17)0.0019 (13)0.0004 (13)0.0146 (14)
C10.0140 (11)0.0135 (11)0.0145 (11)0.0004 (9)0.0006 (9)0.0000 (9)
C20.0153 (12)0.0152 (11)0.0155 (11)0.0008 (9)0.0003 (9)0.0002 (9)
O30.0155 (15)0.0134 (14)0.0272 (17)0.0012 (12)0.0016 (13)0.0065 (13)
O40.0122 (15)0.0193 (15)0.0200 (16)0.0008 (12)0.0007 (12)0.0041 (12)
N10.0196 (10)0.0186 (10)0.0193 (10)0.0000 (7)0.0016 (7)0.0020 (7)
C3A0.0163 (19)0.0157 (19)0.0143 (19)0.0003 (10)0.0001 (10)0.0001 (10)
C4A0.0151 (18)0.0143 (18)0.0136 (18)0.0003 (10)0.0004 (10)0.0008 (10)
N20.0257 (12)0.0272 (12)0.0222 (12)0.0029 (9)0.0033 (9)0.0020 (9)
C3B0.016 (2)0.015 (2)0.015 (2)0.0015 (18)0.0026 (18)0.0012 (18)
C4B0.018 (5)0.012 (4)0.017 (4)0.005 (3)0.000 (3)0.003 (3)
O50.0152 (16)0.0262 (16)0.0205 (16)0.0002 (13)0.0017 (13)0.0009 (13)
N30.0283 (13)0.0298 (13)0.0346 (13)0.0021 (9)0.0020 (9)0.0055 (9)
C50.0270 (14)0.0267 (14)0.0344 (14)0.0005 (9)0.0023 (10)0.0021 (9)
O60.0122 (16)0.0351 (19)0.0233 (17)0.0011 (14)0.0009 (13)0.0049 (15)
C60.0184 (12)0.0202 (12)0.0182 (12)0.0005 (9)0.0007 (9)0.0005 (9)
O80.0227 (17)0.0204 (16)0.0126 (15)0.0054 (13)0.0000 (12)0.0007 (12)
O90.032 (2)0.087 (4)0.066 (3)0.029 (2)0.022 (2)0.057 (3)
O100.021 (2)0.066 (3)0.051 (3)0.0101 (19)0.0055 (18)0.039 (2)
Geometric parameters (Å, º) top
Zn1—O22.105 (3)C4A—H42A0.99
Zn1—N22.112 (4)N2—H21A0.92
Zn1—N12.116 (4)N2—H22A0.92
Zn1—O52.116 (3)C3B—C4B1.524 (12)
Zn1—O62.149 (3)C3B—H31B0.99
Zn1—O12.154 (3)C3B—H32B0.99
Zn2—N32.124 (4)C4B—H41B0.99
Zn2—N3i2.124 (4)C4B—H42B0.99
Zn2—O32.127 (3)O5—C6ii1.262 (6)
Zn2—O3i2.127 (3)N3—C51.510 (7)
Zn2—O42.148 (3)N3—H310.83
Zn2—O4i2.148 (3)N3—H320.93
O1—C11.257 (5)C5—C5i1.543 (10)
O2—C21.264 (5)C5—H5A0.99
C1—O31.255 (5)C5—H5B0.99
C1—C21.559 (6)O6—C61.255 (6)
C2—O41.246 (5)C6—O5ii1.262 (6)
N1—C4A1.549 (9)C6—C6ii1.562 (9)
N1—H11A0.92O8—H810.84
N1—H12A0.92O8—H820.87
C3A—N21.379 (9)O9—H910.84
C3A—C4A1.501 (12)O9—H920.84
C3A—H31A0.99O10—H1020.84
C3A—H32A0.99O10—H1010.84
C4A—H41A0.99
O2—Zn1—N295.48 (15)H11A—N1—H12A109.6
O2—Zn1—N195.00 (15)N2—C3A—C4A105.7 (7)
N2—Zn1—N184.68 (16)N2—C3A—H31A110.6
O2—Zn1—O5165.94 (14)C4A—C3A—H31A110.6
N2—Zn1—O595.03 (16)N2—C3A—H32A110.6
N1—Zn1—O595.25 (15)C4A—C3A—H32A110.6
O2—Zn1—O691.47 (13)H31A—C3A—H32A108.7
N2—Zn1—O693.88 (15)C3A—C4A—N1110.3 (7)
N1—Zn1—O6173.48 (14)C3A—C4A—H41A109.6
O5—Zn1—O678.53 (13)N1—C4A—H41A109.6
O2—Zn1—O178.45 (12)C3A—C4A—H42A109.6
N2—Zn1—O1173.90 (15)N1—C4A—H42A109.6
N1—Zn1—O195.17 (14)H41A—C4A—H42A108.1
O5—Zn1—O191.05 (13)C3A—N2—Zn1107.1 (4)
O6—Zn1—O186.94 (14)C3A—N2—H21A110.3
N3—Zn2—N3i84.2 (3)Zn1—N2—H21A110.3
N3—Zn2—O398.91 (15)C3A—N2—H22A110.3
N3i—Zn2—O392.36 (16)Zn1—N2—H22A110.3
N3—Zn2—O3i92.36 (16)H21A—N2—H22A108.6
N3i—Zn2—O3i98.91 (15)C4B—C3B—H31B110.7
O3—Zn2—O3i164.82 (17)C4B—C3B—H32B110.7
N3—Zn2—O4176.95 (15)H31B—C3B—H32B108.8
N3i—Zn2—O494.54 (16)C3B—C4B—H41B109.3
O3—Zn2—O478.34 (12)C3B—C4B—H42B109.3
O3i—Zn2—O490.58 (12)H41B—C4B—H42B108.0
N3—Zn2—O4i94.54 (16)C6ii—O5—Zn1114.4 (3)
N3i—Zn2—O4i176.95 (15)C5—N3—Zn2106.2 (3)
O3—Zn2—O4i90.58 (12)C5—N3—H31106.5
O3i—Zn2—O4i78.34 (12)Zn2—N3—H31104.6
O4—Zn2—O4i86.82 (17)C5—N3—H32110.2
C1—O1—Zn1113.2 (3)Zn2—N3—H32116.3
C2—O2—Zn1114.9 (3)H31—N3—H32112.4
O1—C1—O3126.2 (4)N3—C5—C5i107.9 (4)
O1—C1—C2117.0 (4)N3—C5—H5A110.1
O3—C1—C2116.8 (4)C5i—C5—H5A110.1
O4—C2—O2126.0 (4)N3—C5—H5B110.1
O4—C2—C1117.5 (4)C5i—C5—H5B110.1
O2—C2—C1116.4 (4)H5A—C5—H5B108.4
C1—O3—Zn2114.1 (3)C6—O6—Zn1113.3 (3)
C2—O4—Zn2113.3 (3)O6—C6—O5ii126.3 (4)
C4A—N1—Zn199.5 (4)O6—C6—C6ii117.0 (5)
C4A—N1—H11A111.9O5ii—C6—C6ii116.7 (5)
Zn1—N1—H11A111.9H81—O8—H82111.0
C4A—N1—H12A111.9H91—O9—H92112.8
Zn1—N1—H12A111.9H102—O10—H10197.7
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11A···O80.922.293.174 (5)160
N1—H11B···O80.922.463.174 (5)135
N1—H12A···O9iii0.922.293.133 (6)153
N1—H12B···O9iii0.922.423.133 (6)135
N2—H21A···O9ii0.922.273.166 (7)165
N2—H21B···O9ii0.922.463.166 (7)134
N2—H22A···O8iv0.922.363.210 (6)154
N2—H22B···O8iv0.922.463.210 (6)139
N3—H31···O10v0.832.363.121 (6)153
N3—H32···O10vi0.932.353.147 (6)144
O8—H81···O4i0.842.082.895 (4)166
O8—H82···O2vii0.871.892.747 (5)168
O9—H91···O5vi0.841.922.736 (6)164
O9—H92···O10.842.052.852 (6)159
O10—H101···O3iii0.841.982.757 (6)152
O10—H102···O6ii0.842.002.832 (5)167
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+1/2, y+1/2, z+1; (iii) x+1/2, y1/2, z+3/2; (iv) x, y, z1/2; (v) x+1/2, y+1/2, z+1/2; (vi) x+1/2, y+1/2, z+3/2; (vii) x, y, z+1/2.
 

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