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The title compound, [Fe(C2O4)(C5H5N)2], was synthesized via unexpected oxidation of (S,S)-tartaric acid under solvothermal conditions. The FeII atom reveals octa­hedral coordination involving two N atoms of pyridine and two oxalate groups acting as tetra­dentate bridging ligands between two FeII centres. The FeII coordination polyhedra are connected into one-dimensional zigzag chains linked by exo-tetra­dentate oxalate groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016789/kp2094sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016789/kp2094Isup2.hkl
Contains datablock I

CCDC reference: 632130

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.094
  • Data-to-parameter ratio = 24.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C1_b ... 1.55 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C2 - C2_a ... 1.55 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

catena-poly[[bis(pyridine)iron(II)]-µ-oxalato-κ2O,O':κ2O'',O'''] top
Crystal data top
[Fe(C2O4)(C5H5N)2]F(000) = 616
Mr = 302.07Dx = 1.513 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.714 (6) ÅCell parameters from 4154 reflections
b = 8.895 (6) Åθ = 3.1–29.6°
c = 15.359 (10) ŵ = 1.15 mm1
β = 91.688 (7)°T = 273 K
V = 1326.5 (14) Å3Block, yellow
Z = 40.30 × 0.22 × 0.19 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
3281 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 31.6°, θmin = 3.1°
φ and ω scansh = 1414
12351 measured reflectionsk = 1213
4354 independent reflectionsl = 2022
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0519P)2 + 0.1013P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4354 reflectionsΔρmax = 0.33 e Å3
172 parametersΔρmin = 0.29 e Å3
0 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.002 (7)
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
Fe10.753633 (19)0.42019 (2)0.074891 (14)0.03556 (8)
C11.02045 (14)0.41575 (16)0.00009 (10)0.0338 (3)
O40.93429 (10)0.32524 (12)0.03015 (7)0.0410 (2)
O30.63518 (11)0.40632 (13)0.04807 (7)0.0434 (3)
O20.57087 (10)0.53056 (13)0.10435 (7)0.0390 (2)
O10.86576 (10)0.61682 (12)0.02993 (8)0.0425 (3)
C20.51957 (13)0.46417 (16)0.04397 (9)0.0329 (3)
N20.68163 (13)0.19369 (15)0.10675 (9)0.0438 (3)
N10.82529 (14)0.46773 (17)0.20942 (9)0.0459 (3)
C30.9001 (2)0.3726 (3)0.25699 (15)0.0699 (6)
H3A0.92060.27900.23360.084*
C40.9494 (3)0.4068 (3)0.34071 (17)0.0909 (9)
H4A1.00290.33750.37200.109*
C50.9192 (3)0.5402 (3)0.37595 (15)0.0810 (8)
H5A0.95180.56520.43160.097*
C60.8405 (3)0.6372 (3)0.32908 (17)0.0785 (7)
H6A0.81660.72970.35240.094*
C70.7960 (2)0.5980 (2)0.24637 (16)0.0675 (6)
H7A0.74240.66660.21470.081*
C80.6973 (2)0.0829 (2)0.04999 (13)0.0557 (5)
H8A0.74330.10320.00090.067*
C90.6488 (3)0.0606 (2)0.06281 (15)0.0659 (6)
H9A0.66350.13550.02190.079*
C100.5790 (2)0.0912 (2)0.13650 (15)0.0623 (5)
H10A0.54280.18640.14580.075*
C110.5632 (3)0.0200 (3)0.19593 (15)0.0750 (6)
H11A0.51730.00170.24720.090*
C120.6164 (2)0.1606 (2)0.17906 (14)0.0670 (6)
H12A0.60600.23580.22040.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.03141 (11)0.03744 (13)0.03775 (13)0.00017 (7)0.00051 (8)0.00024 (9)
C10.0342 (6)0.0314 (7)0.0356 (7)0.0017 (5)0.0040 (5)0.0023 (6)
O40.0371 (5)0.0328 (5)0.0533 (6)0.0002 (4)0.0048 (4)0.0056 (5)
O30.0366 (5)0.0570 (7)0.0367 (6)0.0086 (4)0.0001 (4)0.0085 (5)
O20.0375 (5)0.0479 (6)0.0314 (5)0.0030 (4)0.0033 (4)0.0066 (5)
O10.0360 (5)0.0349 (5)0.0569 (7)0.0044 (4)0.0060 (5)0.0026 (5)
C20.0345 (6)0.0330 (7)0.0311 (7)0.0034 (5)0.0011 (5)0.0020 (5)
N20.0483 (7)0.0377 (7)0.0458 (7)0.0022 (5)0.0088 (5)0.0004 (6)
N10.0461 (7)0.0496 (8)0.0416 (7)0.0008 (6)0.0075 (6)0.0004 (6)
C30.0876 (15)0.0618 (13)0.0589 (12)0.0091 (11)0.0221 (11)0.0034 (11)
C40.126 (2)0.0792 (18)0.0651 (15)0.0114 (15)0.0431 (15)0.0209 (13)
C50.1047 (19)0.0920 (18)0.0453 (11)0.0429 (15)0.0156 (12)0.0050 (12)
C60.0810 (14)0.0797 (16)0.0739 (15)0.0128 (12)0.0124 (12)0.0301 (14)
C70.0722 (13)0.0588 (13)0.0698 (14)0.0057 (9)0.0260 (11)0.0170 (10)
C80.0695 (11)0.0493 (10)0.0493 (10)0.0079 (8)0.0164 (9)0.0080 (8)
C90.0899 (15)0.0440 (11)0.0647 (13)0.0080 (9)0.0160 (11)0.0138 (9)
C100.0776 (13)0.0390 (10)0.0705 (13)0.0090 (8)0.0083 (10)0.0066 (9)
C110.1036 (16)0.0560 (13)0.0675 (14)0.0191 (11)0.0379 (12)0.0003 (11)
C120.0926 (14)0.0461 (11)0.0643 (12)0.0130 (9)0.0374 (11)0.0111 (9)
Geometric parameters (Å, º) top
Fe1—O42.0822 (14)C4—C31.392 (3)
Fe1—O22.0898 (14)C4—H4A0.930
Fe1—O12.1832 (15)C5—C61.347 (4)
Fe1—O32.1858 (15)C5—H5A0.930
Fe1—N22.1926 (18)C6—H6A0.930
Fe1—N12.2017 (19)C7—H7A0.930
C1—O1i1.2432 (18)C7—C61.375 (3)
C1—O41.2598 (18)N2—C81.327 (2)
C1—C1i1.550 (3)N2—C121.328 (2)
O3—C21.2385 (18)C8—C91.376 (3)
O2—C2ii1.2594 (18)C8—H8A0.930
O1—C1i1.2432 (18)C9—H9A0.930
C2—O2ii1.2594 (18)C10—H10A0.930
C2—C2ii1.551 (3)C10—C111.357 (3)
N1—C31.322 (3)C10—C91.364 (3)
C3—H3A0.930C11—H11A0.930
N1—C71.325 (3)C12—C111.381 (3)
C4—C51.340 (4)C12—H12A0.930
O4—Fe1—O2172.52 (4)N2—C8—C9123.24 (18)
O4—Fe1—O177.73 (6)C5—C4—C3119.5 (2)
O2—Fe1—O197.30 (6)C11—C10—C9118.78 (18)
O4—Fe1—O396.85 (6)N1—C7—C6123.5 (2)
O2—Fe1—O377.57 (5)N2—C12—C11123.26 (18)
O1—Fe1—O391.53 (5)C10—C9—C8118.97 (19)
O4—Fe1—N288.76 (6)N1—C3—C4122.6 (2)
O2—Fe1—N296.01 (6)C4—C5—C6118.6 (2)
O1—Fe1—N2166.42 (4)C5—C6—C7119.3 (2)
O3—Fe1—N288.72 (5)C10—C11—C12118.90 (19)
O4—Fe1—N198.13 (6)H3A—C3—N1118.67
O2—Fe1—N187.35 (5)H3A—C3—C4118.70
O1—Fe1—N189.78 (6)H4A—C4—C3120.25
O3—Fe1—N1164.90 (5)H4A—C4—C5120.22
N2—Fe1—N193.51 (6)H5A—C5—C4120.69
O1i—C1—O4126.48 (14)H5A—C5—C6120.71
O1i—C1—C1i117.16 (15)H6A—C6—C5120.35
O4—C1—C1i116.36 (15)H6A—C6—C7120.35
C1—O4—Fe1115.97 (10)H7A—C7—C6118.22
C2—O3—Fe1112.80 (9)H7A—C7—N1118.28
C2ii—O2—Fe1115.89 (10)H8A—C8—N2118.38
C1i—O1—Fe1112.78 (10)H8A—C8—C9118.39
O3—C2—O2ii126.29 (13)H9A—C9—C8120.51
O3—C2—C2ii117.45 (15)H9A—C9—C10120.52
O2ii—C2—C2ii116.26 (15)H10A—C10—C9120.59
C8—N2—C12116.83 (16)H10A—C10—C11120.64
C8—N2—Fe1119.48 (12)H11A—C11—C10120.53
C12—N2—Fe1123.62 (12)H11A—C11—C12120.57
C3—N1—C7116.42 (19)H12A—C12—C11118.34
C3—N1—Fe1123.32 (15)H12A—C12—N2118.41
C7—N1—Fe1120.25 (13)
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z.
 

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