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The title compound, (C10H10N2)2[Fe(C2O4)2(H2O)2](C2HO4)2, appears to be a modular associate consisting of a complex anion containing bivalent Fe as the central atom, a bridging hydrogen oxalate anion and a diprotonated 4,4-bipyridine acting as the counter-cation. The FeII ion in the complex anion occupies a position on a centre of inversion. Its coordination environment is formed by six O atoms from two bidentate oxalate ligands, forming a basal plane, and two water mol­ecules approximately perpendicular to the plane, representing a distorted octa­hedral geometry. These three kinds of ions are connected by strong hydrogen bonds, with donor-acceptor distances (N...O and O...O) lying in the range 2.54-2.98 Å, and [pi]-[pi] stacking inter­actions between the 4,4'-bipyridinium cations, thus forming a three-dimensional supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107006440/sf3025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107006440/sf3025Isup2.hkl
Contains datablock I

CCDC reference: 645522

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

bis(4,4'-bipyridinium) diaquadioxalatoferrate(II) bis(hydrogen oxalate) top
Crystal data top
(C10H10N2)2[Fe(C2O4)2(H2O)2](C2HO4)2Z = 1
Mr = 762.38F(000) = 392
Triclinic, P1Dx = 1.734 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0927 (14) ÅCell parameters from 3878 reflections
b = 10.092 (2) Åθ = 2.0–27.1°
c = 10.633 (2) ŵ = 0.62 mm1
α = 101.76 (3)°T = 293 K
β = 96.29 (3)°Prism, brown
γ = 98.09 (3)°0.16 × 0.08 × 0.08 mm
V = 730.2 (3) Å3
Data collection top
Bruker P4
diffractometer
1934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ω scansh = 88
3600 measured reflectionsk = 1111
2474 independent reflectionsl = 1112
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0477P)2 + 0.6889P]
where P = (Fo2 + 2Fc2)/3
2474 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.29 e Å3
4 restraintsΔρmin = 0.37 e Å3
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.

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*/Ueq
Fe10.00000.00000.00000.0299 (3)
O10.4358 (4)1.5647 (3)0.6837 (3)0.0426 (7)
O20.3026 (5)1.4917 (3)0.8857 (3)0.0404 (7)
O30.3562 (5)1.7086 (3)0.9973 (3)0.0452 (8)
O40.4985 (4)1.7842 (3)0.7880 (3)0.0458 (8)
O50.1688 (4)0.4186 (2)0.0784 (2)0.0404 (7)
O60.0415 (5)0.3428 (3)0.2880 (2)0.0442 (8)
O70.0075 (4)0.1243 (2)0.1827 (2)0.0333 (6)
O80.2922 (4)0.0179 (3)0.0597 (4)0.0536 (9)
O90.0999 (4)0.1993 (2)0.0298 (2)0.0326 (6)
C10.1588 (7)0.7030 (4)0.2554 (4)0.0500 (12)
H1A0.14470.67680.16540.060*
C20.1916 (7)0.8391 (4)0.3154 (4)0.0495 (12)
H2B0.19740.90480.26540.059*
C30.2924 (7)1.1294 (4)0.4491 (4)0.0411 (11)
H30.28661.10640.35930.049*
C40.3346 (6)1.2635 (4)0.5133 (4)0.0410 (10)
H40.35951.33130.46690.049*
C50.3076 (7)1.2047 (4)0.7096 (4)0.0502 (12)
H50.31181.23120.79910.060*
C60.2671 (7)1.0680 (4)0.6493 (4)0.0440 (11)
H60.24551.00240.69840.053*
C70.2582 (5)1.0272 (3)0.5168 (3)0.0243 (8)
C80.2162 (5)0.8808 (3)0.4489 (3)0.0239 (8)
C90.1999 (7)0.7784 (4)0.5176 (4)0.0465 (12)
H90.21140.80100.60770.056*
C100.1666 (7)0.6438 (4)0.4529 (4)0.0500 (12)
H100.15760.57540.49980.060*
C110.3614 (5)1.6229 (4)0.9004 (4)0.0291 (9)
C120.4401 (6)1.6608 (4)0.7805 (4)0.0318 (9)
C130.1105 (5)0.2936 (3)0.0692 (3)0.0281 (9)
C140.0426 (5)0.2510 (3)0.1907 (3)0.0288 (9)
N10.1471 (5)0.6094 (3)0.3249 (3)0.0347 (8)
H10.12640.52390.28640.042*
N20.3408 (5)1.2992 (3)0.6407 (3)0.0328 (8)
H2A0.36671.38460.67930.039*
H70.341 (6)0.083 (3)0.025 (5)0.08 (2)*
H80.378 (5)0.051 (3)0.082 (5)0.080 (19)*
H20.256 (7)1.472 (5)0.949 (3)0.070 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0422 (5)0.0190 (4)0.0261 (4)0.0027 (3)0.0055 (3)0.0007 (3)
O10.068 (2)0.0280 (14)0.0294 (15)0.0028 (13)0.0142 (14)0.0038 (12)
O20.070 (2)0.0219 (14)0.0299 (16)0.0005 (13)0.0203 (15)0.0049 (12)
O30.078 (2)0.0242 (14)0.0338 (16)0.0093 (14)0.0178 (15)0.0012 (13)
O40.068 (2)0.0263 (15)0.0357 (16)0.0104 (14)0.0035 (14)0.0052 (12)
O50.070 (2)0.0201 (14)0.0317 (16)0.0019 (13)0.0174 (14)0.0064 (11)
O60.081 (2)0.0232 (14)0.0268 (15)0.0020 (14)0.0201 (14)0.0008 (12)
O70.0536 (18)0.0196 (13)0.0262 (14)0.0007 (12)0.0120 (12)0.0050 (11)
O80.044 (2)0.0274 (16)0.079 (2)0.0052 (15)0.0020 (17)0.0066 (16)
O90.0532 (18)0.0219 (13)0.0221 (13)0.0027 (12)0.0118 (12)0.0024 (11)
C10.087 (4)0.034 (2)0.025 (2)0.009 (2)0.009 (2)0.0024 (19)
C20.094 (4)0.028 (2)0.025 (2)0.008 (2)0.011 (2)0.0035 (17)
C30.069 (3)0.029 (2)0.024 (2)0.003 (2)0.005 (2)0.0066 (17)
C40.061 (3)0.026 (2)0.037 (2)0.0042 (19)0.010 (2)0.0089 (18)
C50.085 (4)0.035 (2)0.027 (2)0.002 (2)0.017 (2)0.0011 (19)
C60.082 (3)0.023 (2)0.030 (2)0.006 (2)0.022 (2)0.0077 (17)
C70.0247 (19)0.0250 (18)0.0235 (19)0.0053 (15)0.0064 (15)0.0040 (15)
C80.026 (2)0.0228 (18)0.0232 (18)0.0046 (15)0.0053 (15)0.0051 (15)
C90.084 (4)0.031 (2)0.021 (2)0.003 (2)0.003 (2)0.0050 (17)
C100.086 (4)0.024 (2)0.037 (3)0.001 (2)0.003 (2)0.0093 (19)
C110.036 (2)0.0223 (19)0.030 (2)0.0065 (16)0.0036 (17)0.0060 (17)
C120.041 (2)0.022 (2)0.029 (2)0.0014 (17)0.0005 (17)0.0046 (16)
C130.039 (2)0.0208 (19)0.026 (2)0.0058 (16)0.0090 (17)0.0062 (16)
C140.039 (2)0.0212 (19)0.025 (2)0.0040 (16)0.0057 (16)0.0029 (16)
N10.046 (2)0.0197 (16)0.0338 (19)0.0038 (14)0.0049 (15)0.0034 (14)
N20.043 (2)0.0198 (15)0.0334 (19)0.0033 (14)0.0089 (15)0.0001 (14)
Geometric parameters (Å, º) top
Fe1—O7i2.097 (2)C2—H2B0.9300
Fe1—O72.097 (2)C3—C41.361 (5)
Fe1—O92.134 (2)C3—C71.383 (5)
Fe1—O9i2.134 (2)C3—H30.9300
Fe1—O82.143 (3)C4—N21.322 (5)
Fe1—O8i2.143 (3)C4—H40.9300
O1—C121.257 (4)C5—N21.328 (5)
O2—C111.303 (4)C5—C61.372 (5)
O2—H20.83 (2)C5—H50.9300
O3—C111.211 (4)C6—C71.377 (5)
O4—C121.239 (4)C6—H60.9300
O5—C131.251 (4)C7—C81.478 (5)
O6—C141.242 (4)C8—C91.381 (5)
O7—C141.261 (4)C9—C101.365 (5)
O8—H70.824 (19)C9—H90.9300
O8—H80.832 (19)C10—N11.321 (5)
O9—C131.255 (4)C10—H100.9300
C1—N11.313 (5)C11—C121.542 (5)
C1—C21.366 (5)C13—C141.546 (5)
C1—H1A0.9300N1—H10.8600
C2—C81.380 (5)N2—H2A0.8600
O7i—Fe1—O7180.00 (15)C6—C5—H5119.9
O7i—Fe1—O9101.47 (9)C5—C6—C7120.6 (4)
O7—Fe1—O978.53 (9)C5—C6—H6119.7
O7i—Fe1—O9i78.53 (9)C7—C6—H6119.7
O7—Fe1—O9i101.47 (9)C6—C7—C3117.0 (3)
O9—Fe1—O9i180.0 (2)C6—C7—C8122.0 (3)
O7i—Fe1—O890.03 (12)C3—C7—C8121.0 (3)
O7—Fe1—O889.97 (12)C2—C8—C9116.6 (3)
O9—Fe1—O888.92 (12)C2—C8—C7122.5 (3)
O9i—Fe1—O891.08 (12)C9—C8—C7120.9 (3)
O7i—Fe1—O8i89.97 (12)C10—C9—C8119.9 (4)
O7—Fe1—O8i90.03 (12)C10—C9—H9120.1
O9—Fe1—O8i91.08 (12)C8—C9—H9120.1
O9i—Fe1—O8i88.92 (12)N1—C10—C9121.1 (4)
O8—Fe1—O8i180.00 (16)N1—C10—H10119.5
C11—O2—H2113 (3)C9—C10—H10119.5
C14—O7—Fe1114.4 (2)O3—C11—O2124.6 (4)
Fe1—O8—H7122 (3)O3—C11—C12122.1 (3)
Fe1—O8—H8121 (3)O2—C11—C12113.3 (3)
H7—O8—H8108 (3)O4—C12—O1126.1 (4)
C13—O9—Fe1113.5 (2)O4—C12—C11116.6 (3)
N1—C1—C2120.0 (4)O1—C12—C11117.3 (3)
N1—C1—H1A120.0O5—C13—O9126.2 (3)
C2—C1—H1A120.0O5—C13—C14117.1 (3)
C1—C2—C8121.2 (4)O9—C13—C14116.7 (3)
C1—C2—H2B119.4O6—C14—O7125.0 (3)
C8—C2—H2B119.4O6—C14—C13118.2 (3)
C4—C3—C7120.2 (4)O7—C14—C13116.8 (3)
C4—C3—H3119.9C1—N1—C10121.2 (3)
C7—C3—H3119.9C1—N1—H1119.4
N2—C4—C3121.1 (4)C10—N1—H1119.4
N2—C4—H4119.4C4—N2—C5120.7 (3)
C3—C4—H4119.4C4—N2—H2A119.6
N2—C5—C6120.2 (4)C5—N2—H2A119.6
N2—C5—H5119.9
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O5ii0.83 (4)1.72 (2)2.548 (4)175 (5)
O8—H7···O3iii0.83 (4)2.09 (3)2.817 (4)148 (5)
O8—H8···O4iv0.83 (4)1.95 (3)2.705 (4)149 (5)
N1—H1···O50.862.322.952 (4)130
N1—H1···O60.861.852.625 (4)150
N2—H2A···O10.861.802.601 (4)153
N2—H2A···O20.862.362.979 (4)129
Symmetry codes: (ii) x, y+1, z+1; (iii) x, y2, z1; (iv) x+1, y+2, z+1.
 

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