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In the title compound, [Fe(C10H7NO3)2(H2O)2]2·C10H7NO3·2H2O, two cis-di­aqua­bis­(quinoline-2-carboxyl­ato)­iron(II) mol­ecules, one free quinoline-2-carboxyl­ic acid mol­ecule and two water mol­ecules are present in the asymmetric unit. In the complex, the central FeII ion has a distorted octahedral coordination geometry, involving two N and two O atoms of the two bidentate organic ligands, together with two aqua O atoms in a cis configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006603/cf6248sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006603/cf6248Isup2.hkl
Contains datablock I

CCDC reference: 214553

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.045
  • wR factor = 0.174
  • Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_725 Alert C D-H Calc 0.81909, Rep 0.83000, Dev. 0.01 Ang. O14 -H14 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Quinoline-2-carboxylic acid is a tryptophan metabolite (Martell & Smith, 1974). Crystal structures of its metal complexes have been determined with CuII (Haendler, 1986), MnII (Haendler, 1996; Okabe & Koizumi, 1997), FeII, CoII (Okabe & Makino, 1998, 1999), NiII (Odoko et al., 2001) and VIV (Okabe & Muranishi, 2002). The iron complex improves the Fenton oxidation reaction by Fenton's reagent (FeSO4·7H2O and H2O2) (Shul'pin, 2002), acting as a co-catalyst. Although the FeII complex has already been structurally characterized as trans-diaquabis(2-quinolinecarboxylato-N,O)iron(II)–ethanol–water (1/2/2) (Okabe & Makino, 1998), the structure of the FeII complex in a cis configuration has now also been determined as the title mixed solvate, (I).

The structure of the complex is shown in Fig. 1, and selected geometric parameters are listed in Table 1. Two cis-diaquabis(quinoline-2-carboxylato)iron(II) molecules, one free quinoline-2-carboxylic acid molecule and two water molecules are present in the asymmetric unit. The structures of the two independent complex molecules are almost the same. The bidentate organic ligands in each complex are nearly perpendicular to each other [N1—Fe1—N2 = 93.5 (1)° and N3—Fe2—N4 = 95.7 (1)°]. In each complex, the central FeII ion is coordinated by two N and two O atoms of the two organic ligands and by two aqua O atoms, in a distorted octahedral geometry. The ligand atoms are coordinated in a cis configuration. This cis configuration is quite different from trans-diaquabis(2-quinolinecarboxylato)iron(II) (Okabe & Makino, 1998), in which the quinoline rings of the two ligands lie in the same plane. The carboxyl groups of the ligands are ionized. The organic ligands and the central FeII ion form five-membered rings in a slightly distorted manner, as reflected by the torsion angles [O1—C10—C1—N1 = −1.5 (5), O3—C20—C11—N2 = −16.1 (8), O7—C30—C21—N3 = −13.3 (5) and O9—C40—C31—N4 − 10.1 (7)°]. Five-membered ring formation is usually observed in the metal complexes of quinoline-2-carboxylic acid (Okabe & Makino, 1999). The ligand–Fe distances are a little different from each other: Fe—O(carboxylate) = 2.025 (3)–2.080 (4) Å, Fe—N = 2.209 (3)–2.290 (3) Å and Fe—O(water) = 2.122 (5)–2.190 (3) Å. These values are somewhat different from those in the trans complex: Fe—O(carboxylate, trans) = 2.087 (1) Å, Fe—N(trans) = 2.270 (1) Å and Fe—O(water, trans) = 2.131 (1) Å. These cis and trans configurations of FeII complexes of quinoline-2-carboxylic acid should influence differently the metal–H2O2 binding interaction in the Fenton reaction (Shul'pin, 2002).

In the crystal packing, shown in Fig. 2, quinoline rings of the complex and the free quinoline-2-carboxylic acid stack alternately. The FeII complex, the free quinoline-2-carboxylic acid and the water molecule are linked to each other by a hydrogen-bonding network, as shown in Table 2.

Experimental top

Purple plate-shaped crystals were obtained by slow evapolation from a mixture of quinoline-2-carboxylic acid and Fe(NH4)2(SO4)2·6H2O (4:1) dissolved in water.

Refinement top

All H atoms were located in a difference Fourier map. Those of the quinoline rings were then positioned geometrically and refined as riding, while those of the water molecules were fixed at the positions found in the map.

Computing details top

Data collection: MSC/AFC (Molecular Structure Corporation & Rigaku Corporation, 1999); cell refinement: MSC/AFC; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of the title compound with the atomic numbering scheme. Ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. A stereoview of the molecular packing of (I).
(I) top
Crystal data top
[Fe(C8H8NO2)2(H2O)2]2·C10H7NO2·2H2OZ = 2
Mr = 1081.59F(000) = 1116
Triclinic, P1Dx = 1.544 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 12.662 (3) ÅCell parameters from 25 reflections
b = 13.438 (3) Åθ = 12.7–14.3°
c = 16.340 (3) ŵ = 0.71 mm1
α = 97.20 (2)°T = 296 K
β = 101.94 (2)°Plate, purple
γ = 117.79 (1)°0.30 × 0.20 × 0.10 mm
V = 2326.0 (10) Å3
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.054
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 1614
Tmin = 0.844, Tmax = 0.932k = 017
11146 measured reflectionsl = 2121
10701 independent reflections3 standard reflections every 150 reflections
4869 reflections with I > 2σ(I) intensity decay: 0.3%
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.174(Δ/σ)max < 0.001
S = 0.84Δρmax = 0.37 e Å3
10701 reflectionsΔρmin = 0.48 e Å3
658 parameters
Crystal data top
[Fe(C8H8NO2)2(H2O)2]2·C10H7NO2·2H2Oγ = 117.79 (1)°
Mr = 1081.59V = 2326.0 (10) Å3
Triclinic, P1Z = 2
a = 12.662 (3) ÅMo Kα radiation
b = 13.438 (3) ŵ = 0.71 mm1
c = 16.340 (3) ÅT = 296 K
α = 97.20 (2)°0.30 × 0.20 × 0.10 mm
β = 101.94 (2)°
Data collection top
Rigaku AFC-5R
diffractometer
4869 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.054
Tmin = 0.844, Tmax = 0.9323 standard reflections every 150 reflections
11146 measured reflections intensity decay: 0.3%
10701 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045658 parameters
wR(F2) = 0.174H-atom parameters constrained
S = 0.84Δρmax = 0.37 e Å3
10701 reflectionsΔρmin = 0.48 e Å3
Special details top

Refinement. Refinement using reflections with F2 > −10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.10728 (5)0.42207 (5)0.90227 (4)0.0294 (2)
Fe20.10239 (5)0.39937 (5)0.36371 (4)0.0302 (2)
O10.1752 (3)0.4706 (3)0.8033 (2)0.0372 (7)
O20.3132 (3)0.4862 (3)0.7335 (2)0.0530 (9)
O30.0265 (3)0.3717 (3)0.9983 (2)0.0400 (7)
O40.1469 (4)0.2446 (3)1.0225 (3)0.061 (1)
O50.0217 (3)0.4812 (3)0.8575 (2)0.0408 (7)
O60.2286 (3)0.5980 (3)0.9848 (2)0.0399 (7)
O70.1857 (3)0.4532 (3)0.2707 (2)0.0375 (7)
O80.3663 (3)0.5305 (3)0.2411 (2)0.0467 (8)
O90.0231 (3)0.3686 (3)0.4640 (2)0.0371 (7)
O100.1416 (3)0.2477 (3)0.4994 (2)0.0542 (10)
O110.2069 (3)0.5821 (3)0.4372 (2)0.0538 (9)
O120.0410 (3)0.4195 (4)0.2885 (3)0.061 (1)
O130.2722 (4)0.2478 (3)0.3397 (3)0.076 (1)
O140.3135 (3)0.0957 (3)0.4398 (2)0.0570 (10)
O150.7226 (3)0.3480 (3)0.8397 (2)0.0460 (8)
O160.1872 (3)0.5523 (3)0.6177 (2)0.0562 (10)
N10.2694 (3)0.3910 (3)0.9211 (2)0.0290 (8)
N20.0390 (3)0.2291 (3)0.8430 (2)0.0350 (8)
N30.2764 (3)0.3850 (3)0.4003 (2)0.0282 (8)
N40.0319 (3)0.2101 (3)0.3240 (2)0.0287 (8)
N50.4168 (3)0.1022 (3)0.2567 (3)0.0375 (9)
C10.3217 (4)0.4151 (4)0.8585 (3)0.0284 (9)
C20.4228 (4)0.4009 (4)0.8508 (3)0.036 (1)
C30.4724 (4)0.3613 (4)0.9119 (3)0.040 (1)
C40.4217 (4)0.3358 (4)0.9810 (3)0.0319 (10)
C50.4702 (4)0.2965 (4)1.0474 (3)0.042 (1)
C60.4182 (5)0.2737 (4)1.1124 (3)0.048 (1)
C70.3171 (4)0.2906 (4)1.1156 (3)0.040 (1)
C80.2689 (4)0.3290 (4)1.0528 (3)0.036 (1)
C90.3186 (4)0.3520 (3)0.9838 (3)0.0289 (9)
C100.2670 (4)0.4619 (4)0.7926 (3)0.034 (1)
C110.1009 (4)0.1862 (4)0.8986 (3)0.040 (1)
C120.1893 (5)0.0675 (5)0.8838 (4)0.055 (1)
C130.2104 (5)0.0073 (5)0.8112 (4)0.058 (2)
C140.1473 (4)0.0322 (4)0.7505 (4)0.047 (1)
C150.1647 (5)0.0425 (5)0.6731 (4)0.063 (2)
C160.1066 (6)0.0006 (5)0.6151 (4)0.066 (2)
C170.0284 (5)0.1192 (5)0.6305 (4)0.058 (1)
C180.0064 (5)0.1964 (5)0.7045 (3)0.047 (1)
C190.0642 (4)0.1526 (4)0.7674 (3)0.038 (1)
C200.0732 (5)0.2724 (5)0.9802 (3)0.043 (1)
C210.3450 (4)0.4241 (4)0.3478 (3)0.0303 (9)
C220.4561 (4)0.4227 (4)0.3516 (3)0.038 (1)
C230.4974 (4)0.3790 (4)0.4131 (3)0.041 (1)
C240.4303 (4)0.3370 (4)0.4716 (3)0.036 (1)
C250.4701 (5)0.2927 (4)0.5379 (3)0.043 (1)
C260.4051 (5)0.2585 (4)0.5953 (3)0.049 (1)
C270.2963 (5)0.2672 (4)0.5886 (3)0.047 (1)
C280.2541 (4)0.3077 (4)0.5249 (3)0.039 (1)
C290.3193 (4)0.3427 (4)0.4641 (3)0.0317 (9)
C300.2964 (4)0.4738 (4)0.2812 (3)0.0330 (10)
C310.0977 (4)0.1749 (4)0.3784 (3)0.0337 (10)
C320.1883 (4)0.0574 (4)0.3678 (3)0.045 (1)
C330.2092 (5)0.0230 (4)0.2985 (4)0.048 (1)
C340.1446 (4)0.0102 (4)0.2370 (3)0.039 (1)
C350.1648 (5)0.0693 (5)0.1626 (3)0.051 (1)
C360.1049 (5)0.0314 (5)0.1031 (4)0.057 (1)
C370.0203 (5)0.0871 (5)0.1160 (3)0.052 (1)
C380.0036 (4)0.1671 (4)0.1885 (3)0.041 (1)
C390.0571 (4)0.1293 (4)0.2513 (3)0.0325 (10)
C400.0707 (4)0.2700 (4)0.4537 (3)0.036 (1)
C410.4117 (4)0.0573 (4)0.3309 (3)0.038 (1)
C420.4803 (5)0.0618 (4)0.3726 (3)0.048 (1)
C430.5604 (5)0.1363 (4)0.3345 (4)0.051 (1)
C440.5695 (4)0.0928 (4)0.2560 (3)0.044 (1)
C450.6517 (5)0.1634 (5)0.2128 (4)0.061 (2)
C460.6582 (5)0.1160 (6)0.1376 (4)0.068 (2)
C470.5823 (6)0.0040 (6)0.0995 (4)0.065 (2)
C480.5020 (5)0.0746 (5)0.1381 (3)0.052 (1)
C490.4945 (4)0.0288 (4)0.2177 (3)0.038 (1)
C500.3253 (5)0.1441 (5)0.3705 (3)0.043 (1)
H20.45520.41820.80500.0432*
H30.53920.35120.90810.0476*
H50.53780.28641.04650.0510*
H5A0.09710.43170.84000.0488*
H5B0.00940.53470.89600.0488*
H60.44950.24651.15520.0574*
H6A0.21600.64950.97080.0476*
H6B0.25170.61081.03780.0476*
H70.28310.27541.16100.0484*
H80.20250.34011.05590.0432*
H11A0.21710.62740.39840.0645*
H11B0.19090.63850.45840.0645*
H120.23220.04130.92350.0663*
H12A0.03160.45310.24970.0728*
H12B0.09000.42740.31090.0728*
H130.26750.08610.80110.0698*
H140.26640.14630.45910.0855*
H150.21770.12230.66240.0750*
H15A0.68900.38400.81810.0573*
H15B0.67820.27100.80800.0573*
H160.11820.05080.56510.0787*
H16A0.19200.56230.56380.0700*
H16B0.22820.52950.65500.0700*
H170.01010.14790.58930.0694*
H180.04570.27600.71310.0564*
H220.50030.45100.31290.0451*
H230.57050.37680.41650.0488*
H250.54130.28690.54220.0510*
H260.43170.22950.63890.0594*
H270.25290.24470.62860.0567*
H280.18230.31220.52150.0467*
H320.23240.03600.40760.0539*
H330.26680.10100.29120.0580*
H350.21960.14830.15400.0607*
H360.12020.08460.05360.0685*
H370.02020.11190.07490.0629*
H380.05930.24580.19630.0497*
H420.47200.08960.42450.0571*
H430.60840.21570.36110.0616*
H450.70160.24330.23680.0726*
H460.71340.16310.11080.0819*
H470.58700.03550.04730.0780*
H480.45160.15380.11160.0625*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0298 (3)0.0359 (4)0.0295 (3)0.0191 (3)0.0146 (3)0.0110 (3)
Fe20.0292 (3)0.0304 (4)0.0328 (4)0.0136 (3)0.0152 (3)0.0111 (3)
O10.041 (2)0.050 (2)0.037 (2)0.030 (2)0.021 (1)0.020 (2)
O20.049 (2)0.089 (3)0.044 (2)0.043 (2)0.028 (2)0.033 (2)
O30.048 (2)0.046 (2)0.037 (2)0.027 (2)0.022 (2)0.014 (2)
O40.074 (3)0.067 (3)0.082 (3)0.046 (2)0.060 (2)0.045 (2)
O50.033 (2)0.045 (2)0.044 (2)0.021 (2)0.009 (1)0.010 (2)
O60.042 (2)0.042 (2)0.038 (2)0.023 (2)0.012 (1)0.007 (1)
O70.035 (2)0.048 (2)0.039 (2)0.022 (2)0.019 (1)0.021 (2)
O80.048 (2)0.063 (2)0.051 (2)0.033 (2)0.033 (2)0.034 (2)
O90.037 (2)0.038 (2)0.035 (2)0.016 (2)0.017 (1)0.009 (1)
O100.061 (2)0.057 (2)0.061 (2)0.029 (2)0.045 (2)0.026 (2)
O110.061 (2)0.036 (2)0.066 (2)0.022 (2)0.031 (2)0.008 (2)
O120.056 (2)0.081 (3)0.074 (3)0.046 (2)0.031 (2)0.048 (2)
O130.111 (4)0.044 (2)0.090 (3)0.033 (2)0.071 (3)0.029 (2)
O140.064 (2)0.059 (2)0.050 (2)0.026 (2)0.035 (2)0.016 (2)
O150.051 (2)0.039 (2)0.043 (2)0.020 (2)0.009 (2)0.012 (2)
O160.067 (2)0.072 (3)0.044 (2)0.044 (2)0.020 (2)0.024 (2)
N10.029 (2)0.027 (2)0.031 (2)0.014 (2)0.011 (2)0.007 (2)
N20.030 (2)0.036 (2)0.044 (2)0.019 (2)0.013 (2)0.015 (2)
N30.027 (2)0.029 (2)0.029 (2)0.013 (2)0.012 (1)0.008 (2)
N40.030 (2)0.032 (2)0.028 (2)0.016 (2)0.011 (1)0.011 (2)
N50.038 (2)0.034 (2)0.043 (2)0.017 (2)0.017 (2)0.012 (2)
C10.027 (2)0.029 (2)0.031 (2)0.013 (2)0.013 (2)0.008 (2)
C20.027 (2)0.040 (3)0.040 (3)0.016 (2)0.012 (2)0.008 (2)
C30.028 (2)0.042 (3)0.055 (3)0.020 (2)0.018 (2)0.013 (2)
C40.025 (2)0.029 (2)0.037 (2)0.012 (2)0.006 (2)0.006 (2)
C50.031 (2)0.039 (3)0.056 (3)0.022 (2)0.004 (2)0.010 (2)
C60.049 (3)0.053 (3)0.047 (3)0.028 (3)0.010 (2)0.027 (3)
C70.041 (3)0.043 (3)0.040 (3)0.021 (2)0.013 (2)0.017 (2)
C80.035 (2)0.039 (3)0.034 (2)0.018 (2)0.012 (2)0.010 (2)
C90.026 (2)0.023 (2)0.031 (2)0.010 (2)0.006 (2)0.001 (2)
C100.033 (2)0.039 (3)0.032 (2)0.017 (2)0.015 (2)0.010 (2)
C110.034 (2)0.044 (3)0.051 (3)0.024 (2)0.015 (2)0.020 (2)
C120.039 (3)0.053 (3)0.083 (4)0.022 (3)0.027 (3)0.039 (3)
C130.041 (3)0.036 (3)0.080 (4)0.012 (3)0.005 (3)0.013 (3)
C140.035 (3)0.041 (3)0.062 (3)0.022 (2)0.005 (2)0.011 (3)
C150.057 (4)0.041 (3)0.067 (4)0.024 (3)0.010 (3)0.007 (3)
C160.068 (4)0.058 (4)0.055 (4)0.034 (3)0.004 (3)0.007 (3)
C170.055 (3)0.071 (4)0.044 (3)0.034 (3)0.010 (3)0.002 (3)
C180.046 (3)0.047 (3)0.040 (3)0.020 (3)0.011 (2)0.004 (2)
C190.027 (2)0.034 (3)0.044 (3)0.015 (2)0.001 (2)0.001 (2)
C200.049 (3)0.053 (3)0.056 (3)0.036 (3)0.031 (3)0.036 (3)
C210.031 (2)0.024 (2)0.031 (2)0.012 (2)0.009 (2)0.001 (2)
C220.031 (2)0.042 (3)0.043 (3)0.020 (2)0.016 (2)0.009 (2)
C230.032 (2)0.040 (3)0.054 (3)0.021 (2)0.014 (2)0.010 (2)
C240.031 (2)0.031 (2)0.038 (3)0.014 (2)0.004 (2)0.001 (2)
C250.040 (3)0.039 (3)0.048 (3)0.023 (2)0.006 (2)0.014 (2)
C260.050 (3)0.049 (3)0.046 (3)0.024 (3)0.007 (2)0.020 (3)
C270.046 (3)0.048 (3)0.049 (3)0.022 (3)0.015 (2)0.024 (3)
C280.041 (3)0.042 (3)0.039 (3)0.022 (2)0.018 (2)0.016 (2)
C290.032 (2)0.030 (2)0.032 (2)0.016 (2)0.007 (2)0.005 (2)
C300.033 (2)0.036 (3)0.032 (2)0.017 (2)0.016 (2)0.004 (2)
C310.029 (2)0.036 (2)0.040 (3)0.016 (2)0.015 (2)0.015 (2)
C320.043 (3)0.043 (3)0.053 (3)0.019 (2)0.025 (2)0.022 (3)
C330.043 (3)0.031 (3)0.065 (4)0.010 (2)0.020 (3)0.023 (3)
C340.039 (3)0.028 (2)0.048 (3)0.017 (2)0.008 (2)0.006 (2)
C350.052 (3)0.036 (3)0.056 (3)0.020 (3)0.010 (3)0.003 (2)
C360.059 (3)0.048 (3)0.049 (3)0.027 (3)0.001 (3)0.013 (3)
C370.064 (3)0.055 (3)0.037 (3)0.031 (3)0.017 (3)0.000 (2)
C380.047 (3)0.038 (3)0.039 (3)0.020 (2)0.017 (2)0.012 (2)
C390.031 (2)0.034 (2)0.037 (2)0.020 (2)0.008 (2)0.010 (2)
C400.044 (3)0.047 (3)0.033 (2)0.030 (2)0.021 (2)0.019 (2)
C410.036 (2)0.040 (3)0.042 (3)0.022 (2)0.013 (2)0.016 (2)
C420.050 (3)0.043 (3)0.047 (3)0.022 (3)0.017 (2)0.005 (2)
C430.046 (3)0.027 (3)0.065 (4)0.010 (2)0.014 (3)0.004 (2)
C440.034 (3)0.045 (3)0.056 (3)0.020 (2)0.015 (2)0.021 (3)
C450.043 (3)0.045 (3)0.089 (5)0.012 (3)0.025 (3)0.034 (3)
C460.058 (4)0.079 (5)0.086 (5)0.034 (4)0.045 (4)0.048 (4)
C470.069 (4)0.086 (5)0.055 (4)0.041 (4)0.035 (3)0.033 (3)
C480.057 (3)0.053 (3)0.052 (3)0.026 (3)0.027 (3)0.020 (3)
C490.031 (2)0.038 (3)0.046 (3)0.018 (2)0.012 (2)0.016 (2)
C500.048 (3)0.049 (3)0.042 (3)0.028 (3)0.021 (2)0.019 (2)
Geometric parameters (Å, º) top
Fe1—O12.025 (3)C12—C131.345 (9)
Fe1—O32.061 (4)C12—H120.930
Fe1—O52.166 (4)C13—C141.402 (9)
Fe1—O62.173 (3)C13—H130.930
Fe1—N12.248 (5)C14—C151.420 (9)
Fe1—N22.290 (3)C14—C191.408 (6)
Fe2—O72.043 (3)C15—C161.338 (10)
Fe2—O92.080 (4)C15—H150.930
Fe2—O112.190 (3)C16—C171.395 (8)
Fe2—O122.122 (5)C16—H160.930
Fe2—N32.265 (4)C17—C181.376 (8)
Fe2—N42.209 (3)C17—H170.930
O1—C101.264 (7)C18—C191.414 (8)
O2—C101.231 (6)C18—H180.930
O3—C201.280 (5)C21—C221.404 (8)
O4—C201.223 (8)C21—C301.516 (7)
O5—H5A0.826C22—C231.359 (8)
O5—H5B0.824C22—H220.930
O6—H6A0.827C23—C241.406 (7)
O6—H6B0.822C23—H230.930
O7—C301.264 (6)C24—C251.414 (8)
O8—C301.236 (6)C24—C291.423 (8)
O9—C401.260 (5)C25—C261.358 (8)
O10—C401.240 (7)C25—H250.930
O11—H11A0.921C26—C271.418 (10)
O11—H11B0.917C26—H260.930
O12—H12A0.820C27—C281.359 (8)
O12—H12B0.822C27—H270.930
O13—C501.208 (7)C28—C291.410 (7)
O14—C501.306 (7)C28—H280.930
O14—H140.819C31—C321.414 (6)
O15—H15A0.845C31—C401.512 (7)
O15—H15B0.927C32—C331.350 (8)
O16—H16A0.918C32—H320.930
O16—H16B0.894C33—C341.411 (8)
N1—C11.324 (6)C33—H330.930
N1—C91.375 (6)C34—C351.404 (8)
N2—C111.332 (7)C34—C391.411 (6)
N2—C191.377 (6)C35—C361.360 (9)
N3—C211.327 (6)C35—H350.930
N3—C291.381 (7)C36—C371.400 (7)
N4—C311.323 (6)C36—H360.930
N4—C391.374 (6)C37—C381.372 (8)
N5—C411.314 (7)C37—H370.930
N5—C491.362 (6)C38—C391.412 (7)
C1—C21.407 (8)C38—H380.930
C1—C101.517 (7)C41—C421.402 (6)
C2—C31.364 (8)C41—C501.505 (7)
C2—H20.930C42—C431.375 (8)
C3—C41.412 (7)C42—H420.930
C3—H30.930C43—C441.391 (9)
C4—C51.416 (8)C43—H430.930
C4—C91.429 (8)C44—C451.426 (8)
C5—C61.355 (8)C44—C491.420 (6)
C5—H50.930C45—C461.35 (1)
C6—C71.411 (9)C45—H450.930
C6—H60.930C46—C471.402 (9)
C7—C81.364 (8)C46—H460.930
C7—H70.930C47—C481.358 (9)
C8—C91.401 (7)C47—H470.930
C8—H80.930C48—C491.409 (8)
C11—C121.408 (7)C48—H480.930
C11—C201.511 (8)
O1···O12i3.026 (7)O12···O16i2.757 (7)
O2···C22ii3.277 (6)O13···O15xi3.096 (6)
O2···C6iii3.537 (5)O14···C17x3.402 (8)
O3···O5iv2.910 (5)O14···C42xi3.413 (7)
O3···O6iv3.500 (6)O14···C16x3.438 (10)
O4···O6iv2.760 (7)O15···N5xi2.936 (5)
O4···O5iv3.332 (4)O15···C30ii3.350 (7)
O4···C46v3.372 (8)O15···C48xi3.570 (6)
O4···C37vi3.513 (9)O16···C40i3.537 (8)
O4···C38vi3.534 (7)N5···C12x3.546 (8)
O5···O15vii2.801 (4)C1···C5iii3.411 (5)
O5···O12i2.949 (6)C1···C4iii3.574 (4)
O5···O7i3.139 (5)C2···C4iii3.575 (6)
O5···C20iv3.494 (6)C3···C9iii3.425 (5)
O6···O15iii2.731 (4)C4···C35x3.576 (5)
O6···C20iv3.263 (8)C5···C10iii3.555 (5)
O6···C3iii3.560 (6)C7···C30vi3.559 (8)
O6···C5iii3.578 (6)C9···C35x3.584 (6)
O7···O15ii3.305 (5)C13···C41x3.572 (9)
O7···O13viii3.587 (6)C13···C37x3.59 (1)
O8···O15ii2.704 (6)C14···C41x3.523 (9)
O8···C2ii3.154 (6)C14···C36x3.577 (9)
O8···C26ii3.287 (5)C15···C39x3.572 (10)
O8···C7ix3.306 (7)C19···C50x3.538 (8)
O8···C8ix3.397 (6)C19···C35x3.599 (9)
O8···C3ii3.576 (7)C21···C25ii3.399 (6)
O9···O16i3.395 (6)C21···C24ii3.570 (5)
O10···O14x2.675 (5)C22···C24ii3.529 (6)
O10···O11i2.917 (7)C22···C29ii3.579 (5)
O10···O13x3.382 (7)C23···C29ii3.391 (6)
O10···C50x3.411 (7)C25···C30ii3.568 (5)
O11···O13viii2.854 (6)C32···C44vii3.497 (9)
O11···C25ii3.529 (7)C47···C47xii3.52 (1)
O1—Fe1—O3176.0 (2)C16—C15—H15119.3
O1—Fe1—O586.4 (2)C15—C16—C17119.3 (6)
O1—Fe1—O691.2 (1)C15—C16—H16120.3
O1—Fe1—N176.5 (2)C17—C16—H16120.3
O1—Fe1—N2102.6 (1)C16—C17—C18122.2 (6)
O3—Fe1—O589.9 (2)C16—C17—H17118.9
O3—Fe1—O690.1 (1)C18—C17—H17118.9
O3—Fe1—N1107.3 (2)C17—C18—C19118.8 (5)
O3—Fe1—N276.1 (1)C17—C18—H18120.6
O5—Fe1—O685.3 (1)C19—C18—H18120.6
O5—Fe1—N1162.4 (1)N2—C19—C14121.8 (5)
O5—Fe1—N294.2 (1)N2—C19—C18119.1 (4)
O6—Fe1—N190.9 (1)C14—C19—C18119.1 (5)
O6—Fe1—N2166.2 (1)O3—C20—O4125.0 (5)
N1—Fe1—N293.5 (1)O3—C20—C11116.0 (5)
O7—Fe2—O9171.9 (1)O4—C20—C11119.0 (4)
O7—Fe2—O1187.4 (1)N3—C21—C22124.5 (5)
O7—Fe2—O1283.5 (2)N3—C21—C30115.3 (5)
O7—Fe2—N376.2 (1)C22—C21—C30120.2 (4)
O7—Fe2—N4111.3 (1)C21—C22—C23118.3 (5)
O9—Fe2—O1185.1 (1)C21—C22—H22120.8
O9—Fe2—O1293.7 (2)C23—C22—H22120.8
O9—Fe2—N3106.9 (1)C22—C23—C24120.4 (5)
O9—Fe2—N476.0 (1)C22—C23—H23119.8
O11—Fe2—O1292.2 (2)C24—C23—H23119.8
O11—Fe2—N391.3 (1)C23—C24—C25122.9 (5)
O11—Fe2—N4161.1 (2)C23—C24—C29117.8 (5)
O12—Fe2—N3159.3 (2)C25—C24—C29119.3 (5)
O12—Fe2—N487.4 (2)C24—C25—C26120.5 (6)
N3—Fe2—N495.7 (1)C24—C25—H25119.7
Fe1—O1—C10120.8 (3)C26—C25—H25119.7
Fe1—O3—C20119.0 (3)C25—C26—C27119.7 (6)
Fe1—O5—H5A117.0C25—C26—H26120.2
Fe1—O5—H5B109.2C27—C26—H26120.2
H5A—O5—H5B109.5C26—C27—C28121.5 (5)
Fe1—O6—H6A117.5C26—C27—H27119.2
Fe1—O6—H6B121.6C28—C27—H27119.2
H6A—O6—H6B110.1C27—C28—C29119.9 (6)
Fe2—O7—C30119.0 (3)C27—C28—H28120.1
Fe2—O9—C40118.4 (3)C29—C28—H28120.1
Fe2—O11—H11A108.1N3—C29—C24121.5 (4)
Fe2—O11—H11B138.7N3—C29—C28119.4 (5)
H11A—O11—H11B74.5C24—C29—C28119.1 (5)
Fe2—O12—H12A122.5O7—C30—O8124.7 (5)
Fe2—O12—H12B119.4O7—C30—C21116.7 (4)
H12A—O12—H12B110.6O8—C30—C21118.6 (5)
C50—O14—H14109.5N4—C31—C32123.3 (5)
H15A—O15—H15B109.2N4—C31—C40115.3 (4)
H16A—O16—H16B129.9C32—C31—C40121.3 (5)
Fe1—N1—C1110.8 (3)C31—C32—C33118.4 (5)
Fe1—N1—C9131.2 (3)C31—C32—H32120.8
C1—N1—C9118.0 (5)C33—C32—H32120.8
Fe1—N2—C11109.9 (3)C32—C33—C34120.6 (4)
Fe1—N2—C19132.1 (3)C32—C33—H33119.7
C11—N2—C19117.7 (4)C34—C33—H33119.7
Fe2—N3—C21110.7 (3)C33—C34—C35123.1 (4)
Fe2—N3—C29131.9 (3)C33—C34—C39117.6 (5)
C21—N3—C29117.4 (4)C35—C34—C39119.3 (5)
Fe2—N4—C31112.6 (3)C34—C35—C36120.5 (5)
Fe2—N4—C39128.9 (3)C34—C35—H35119.8
C31—N4—C39118.4 (3)C36—C35—H35119.8
C41—N5—C49118.2 (4)C35—C36—C37120.4 (5)
N1—C1—C2124.3 (5)C35—C36—H36119.8
N1—C1—C10116.0 (5)C37—C36—H36119.8
C2—C1—C10119.7 (4)C36—C37—C38120.8 (5)
C1—C2—C3118.7 (5)C36—C37—H37119.6
C1—C2—H2120.7C38—C37—H37119.6
C3—C2—H2120.7C37—C38—C39119.6 (4)
C2—C3—C4119.6 (5)C37—C38—H38120.2
C2—C3—H3120.2C39—C38—H38120.2
C4—C3—H3120.2N4—C39—C34121.5 (4)
C3—C4—C5122.5 (5)N4—C39—C38119.1 (4)
C3—C4—C9118.2 (5)C34—C39—C38119.4 (4)
C5—C4—C9119.3 (5)O9—C40—O10124.6 (5)
C4—C5—C6120.1 (6)O9—C40—C31116.2 (5)
C4—C5—H5120.0O10—C40—C31119.2 (4)
C6—C5—H5120.0N5—C41—C42124.2 (5)
C5—C6—C7120.7 (6)N5—C41—C50115.0 (4)
C5—C6—H6119.6C42—C41—C50120.8 (5)
C7—C6—H6119.6C41—C42—C43118.1 (5)
C6—C7—C8120.6 (5)C41—C42—H42121.0
C6—C7—H7119.7C43—C42—H42121.0
C8—C7—H7119.7C42—C43—C44119.8 (4)
C7—C8—C9120.6 (5)C42—C43—H43120.1
C7—C8—H8119.7C44—C43—H43120.1
C9—C8—H8119.7C43—C44—C45123.6 (5)
N1—C9—C4121.2 (4)C43—C44—C49118.2 (5)
N1—C9—C8120.0 (5)C45—C44—C49118.2 (5)
C4—C9—C8118.8 (5)C44—C45—C46120.9 (5)
O1—C10—O2125.8 (5)C44—C45—H45119.5
O1—C10—C1115.9 (4)C46—C45—H45119.5
O2—C10—C1118.3 (5)C45—C46—C47120.4 (6)
N2—C11—C12123.3 (5)C45—C46—H46119.8
N2—C11—C20116.6 (4)C47—C46—H46119.8
C12—C11—C20120.2 (5)C46—C47—C48120.7 (6)
C11—C12—C13118.7 (6)C46—C47—H47119.6
C11—C12—H12120.7C48—C47—H47119.6
C13—C12—H12120.7C47—C48—C49120.6 (5)
C12—C13—C14120.8 (5)C47—C48—H48119.7
C12—C13—H13119.6C49—C48—H48119.7
C14—C13—H13119.6N5—C49—C44121.5 (5)
C13—C14—C15123.4 (5)N5—C49—C48119.5 (4)
C13—C14—C19117.6 (5)C44—C49—C48119.0 (5)
C15—C14—C19119.0 (5)O13—C50—O14124.2 (5)
C14—C15—C16121.5 (5)O13—C50—C41122.5 (5)
C14—C15—H15119.3O14—C50—C41113.3 (4)
Fe1—O1—C10—O2178.1 (3)N3—Fe2—O9—C40101.9 (4)
Fe1—O1—C10—C10.7 (4)N3—Fe2—N4—C31109.8 (4)
Fe1—O3—C20—O4160.2 (5)N3—Fe2—N4—C3972.8 (4)
Fe1—O3—C20—C1118.0 (7)N3—C21—C22—C230.3 (6)
Fe1—N1—C1—C2178.0 (3)N3—C29—C24—C231.7 (6)
Fe1—N1—C1—C102.6 (4)N3—C29—C24—C25179.8 (4)
Fe1—N1—C9—C4178.2 (2)N3—C29—C28—C27179.2 (4)
Fe1—N1—C9—C82.7 (5)N4—Fe2—O7—C30102.6 (3)
Fe1—N2—C11—C12174.3 (5)N4—Fe2—O9—C4010.0 (4)
Fe1—N2—C11—C206.4 (6)N4—Fe2—N3—C21114.3 (3)
Fe1—N2—C19—C14170.0 (4)N4—Fe2—N3—C2964.6 (3)
Fe1—N2—C19—C1810.9 (8)N4—C31—C32—C330.3 (9)
Fe2—O7—C30—O8162.9 (4)N4—C39—C34—C332.4 (8)
Fe2—O7—C30—C2117.4 (5)N4—C39—C34—C35178.4 (5)
Fe2—O9—C40—O10164.5 (5)N4—C39—C38—C37179.5 (6)
Fe2—O9—C40—C3114.0 (7)N5—C41—C42—C431.6 (9)
Fe2—N3—C21—C22177.5 (3)N5—C49—C44—C431.0 (9)
Fe2—N3—C21—C303.2 (4)N5—C49—C44—C45177.8 (6)
Fe2—N3—C29—C24176.5 (3)N5—C49—C48—C47177.4 (6)
Fe2—N3—C29—C285.4 (5)C1—N1—C9—C41.1 (5)
Fe2—N4—C31—C32179.0 (4)C1—N1—C9—C8177.9 (3)
Fe2—N4—C31—C401.6 (6)C1—C2—C3—C40.1 (6)
Fe2—N4—C39—C34178.4 (4)C2—C1—N1—C91.5 (5)
Fe2—N4—C39—C383.2 (7)C2—C3—C4—C5178.8 (4)
O1—Fe1—N1—C12.3 (2)C2—C3—C4—C90.4 (5)
O1—Fe1—N1—C9178.3 (3)C3—C2—C1—C10178.4 (3)
O1—Fe1—N2—C11174.6 (4)C3—C4—C5—C6179.8 (4)
O1—Fe1—N2—C1911.8 (5)C3—C4—C9—C8178.8 (3)
O1—C10—C1—N11.5 (5)C4—C5—C6—C71.2 (6)
O1—C10—C1—C2179.0 (3)C4—C9—C8—C70.8 (5)
O2—C10—C1—N1179.6 (3)C5—C4—C9—C80.4 (5)
O2—C10—C1—C20.2 (5)C5—C6—C7—C80.8 (6)
O3—Fe1—N1—C1176.4 (2)C6—C5—C4—C90.6 (6)
O3—Fe1—N1—C93.0 (3)C6—C7—C8—C90.2 (6)
O3—Fe1—N2—C111.5 (4)C9—N1—C1—C10177.9 (3)
O3—Fe1—N2—C19172.1 (5)C11—N2—C19—C143.2 (8)
O3—C20—C11—N216.1 (8)C11—N2—C19—C18175.8 (5)
O3—C20—C11—C12164.6 (6)C11—C12—C13—C141 (1)
O4—C20—C11—N2162.3 (6)C12—C11—N2—C190.4 (9)
O4—C20—C11—C1217.0 (9)C12—C13—C14—C15179.4 (7)
O5—Fe1—O1—C10177.4 (3)C12—C13—C14—C191.6 (10)
O5—Fe1—O3—C2083.3 (5)C13—C12—C11—C20179.0 (6)
O5—Fe1—N1—C116.1 (5)C13—C14—C15—C16177.1 (7)
O5—Fe1—N1—C9164.5 (3)C13—C14—C19—C18175.2 (6)
O5—Fe1—N2—C1187.3 (4)C14—C15—C16—C170 (1)
O5—Fe1—N2—C1999.0 (5)C14—C19—C18—C173.2 (9)
O6—Fe1—O1—C1092.2 (3)C15—C14—C19—C183.8 (9)
O6—Fe1—O3—C20168.6 (5)C15—C16—C17—C181 (1)
O6—Fe1—N1—C193.3 (2)C16—C15—C14—C191 (1)
O6—Fe1—N1—C987.4 (3)C16—C17—C18—C190 (1)
O6—Fe1—N2—C110.2 (9)C19—N2—C11—C20178.9 (5)
O6—Fe1—N2—C19173.4 (6)C21—N3—C29—C242.3 (5)
O7—Fe2—N3—C213.7 (2)C21—N3—C29—C28175.7 (4)
O7—Fe2—N3—C29175.2 (4)C21—C22—C23—C240.4 (6)
O7—Fe2—N4—C31172.7 (3)C22—C21—N3—C291.6 (6)
O7—Fe2—N4—C394.6 (5)C22—C23—C24—C25178.7 (4)
O7—C30—C21—N313.3 (5)C22—C23—C24—C290.3 (6)
O7—C30—C21—C22167.4 (4)C23—C22—C21—C30179.0 (4)
O8—C30—C21—N3166.9 (4)C23—C24—C25—C26176.8 (4)
O8—C30—C21—C2212.4 (6)C23—C24—C29—C28176.3 (4)
O9—Fe2—N3—C21168.6 (2)C24—C25—C26—C270.1 (7)
O9—Fe2—N3—C2912.5 (4)C24—C29—C28—C271.2 (6)
O9—Fe2—N4—C313.8 (4)C25—C24—C29—C282.1 (6)
O9—Fe2—N4—C39178.9 (5)C25—C26—C27—C281.0 (7)
O9—C40—C31—N410.1 (7)C26—C25—C24—C291.6 (6)
O9—C40—C31—C32170.5 (5)C26—C27—C28—C290.4 (7)
O10—C40—C31—N4168.5 (5)C29—N3—C21—C30177.7 (3)
O10—C40—C31—C3210.9 (8)C31—N4—C39—C344.4 (8)
O11—Fe2—O7—C3080.2 (3)C31—N4—C39—C38174.0 (5)
O11—Fe2—O9—C40168.3 (4)C31—C32—C33—C341.8 (9)
O11—Fe2—N3—C2183.3 (3)C32—C31—N4—C393.3 (8)
O11—Fe2—N3—C2997.8 (3)C32—C33—C34—C35178.4 (6)
O11—Fe2—N4—C311.5 (7)C32—C33—C34—C390.8 (9)
O11—Fe2—N4—C39175.9 (5)C33—C32—C31—C40179.0 (5)
O12—Fe2—O7—C30172.7 (3)C33—C34—C35—C36176.3 (6)
O12—Fe2—O9—C4076.4 (4)C33—C34—C39—C38176.0 (5)
O12—Fe2—N3—C2116.3 (5)C34—C35—C36—C371 (1)
O12—Fe2—N3—C29162.6 (4)C34—C39—C38—C372.1 (9)
O12—Fe2—N4—C3190.7 (4)C35—C34—C39—C383.2 (8)
O12—Fe2—N4—C3986.6 (5)C35—C36—C37—C380 (1)
O13—C50—C41—N55.5 (9)C36—C35—C34—C392.8 (9)
O13—C50—C41—C42174.3 (6)C36—C37—C38—C390.6 (10)
O14—C50—C41—N5173.9 (5)C39—N4—C31—C40176.0 (5)
O14—C50—C41—C426.3 (8)C41—N5—C49—C440.7 (8)
N1—Fe1—O1—C101.6 (3)C41—N5—C49—C48179.9 (6)
N1—Fe1—O3—C20100.4 (5)C41—C42—C43—C441.2 (9)
N1—Fe1—N2—C11108.5 (4)C42—C41—N5—C490.6 (9)
N1—Fe1—N2—C1965.1 (5)C42—C43—C44—C45178.7 (6)
N1—C1—C2—C30.9 (6)C42—C43—C44—C490.0 (9)
N1—C9—C4—C30.2 (5)C43—C42—C41—C50178.1 (6)
N1—C9—C4—C5179.4 (3)C43—C44—C45—C46178.7 (7)
N1—C9—C8—C7179.8 (3)C43—C44—C49—C48179.8 (6)
N2—Fe1—O1—C1089.1 (3)C44—C45—C46—C471 (1)
N2—Fe1—O3—C2011.1 (5)C44—C49—C48—C471.8 (10)
N2—Fe1—N1—C199.8 (3)C45—C44—C49—C481.4 (9)
N2—Fe1—N1—C979.6 (3)C45—C46—C47—C480 (1)
N2—C11—C12—C131.8 (10)C46—C45—C44—C490.0 (10)
N2—C19—C14—C133.9 (9)C46—C47—C48—C490 (1)
N2—C19—C14—C15177.1 (6)C49—N5—C41—C50179.1 (5)
N2—C19—C18—C17177.7 (6)C49—N5—C41—C50179.1 (5)
N3—Fe2—O7—C3011.8 (3)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z+2; (iv) x, y+1, z+2; (v) x1, y, z+1; (vi) x, y, z+1; (vii) x1, y, z; (viii) x, y+1, z; (ix) x, y, z1; (x) x, y, z+1; (xi) x+1, y, z+1; (xii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O15vii0.832.022.801 (4)158
O6—H6B···O15iii0.821.922.731 (4)167
O5—H5B···O3iv0.822.122.910 (4)162
O6—H6A···O4iv0.831.992.760 (5)154
O11—H11A···O13viii0.921.952.854 (5)166
O11—H11B···O10i0.922.002.917 (5)175
O14—H14···O10x0.831.872.675 (5)169
O15—H15A···O8ii0.841.872.704 (5)170
O12—H12A···O5i0.822.152.949 (5)165
O15—H15B···N5xi0.932.012.936 (5)178
O12—H12B···O16i0.821.942.757 (5)170
O16—H16A···O110.922.153.071 (5)178
O16—H16B···O20.891.832.722 (5)178
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z+2; (iv) x, y+1, z+2; (vii) x1, y, z; (viii) x, y+1, z; (x) x, y, z+1; (xi) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula[Fe(C8H8NO2)2(H2O)2]2·C10H7NO2·2H2O
Mr1081.59
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)12.662 (3), 13.438 (3), 16.340 (3)
α, β, γ (°)97.20 (2), 101.94 (2), 117.79 (1)
V3)2326.0 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.71
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerRigaku AFC-5R
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.844, 0.932
No. of measured, independent and
observed [I > 2σ(I)] reflections
11146, 10701, 4869
Rint0.054
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.174, 0.84
No. of reflections10701
No. of parameters658
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.48

Computer programs: MSC/AFC (Molecular Structure Corporation & Rigaku Corporation, 1999), MSC/AFC, TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1999), SIR97 (Altomare et al., 1999) and DIRDIF94 (Beurskens et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) top
Fe1—O12.025 (3)Fe2—O72.043 (3)
Fe1—O32.061 (4)Fe2—O92.080 (4)
Fe1—O52.166 (4)Fe2—O112.190 (3)
Fe1—O62.173 (3)Fe2—O122.122 (5)
Fe1—N12.248 (5)Fe2—N32.265 (4)
Fe1—N22.290 (3)Fe2—N42.209 (3)
O1—Fe1—O3176.0 (2)O9—Fe2—O1293.7 (2)
O1—Fe1—O586.4 (2)O9—Fe2—N3106.9 (1)
O1—Fe1—O691.2 (1)O9—Fe2—N476.0 (1)
O1—Fe1—N176.5 (2)O11—Fe2—O1292.2 (2)
O1—Fe1—N2102.6 (1)O11—Fe2—N391.3 (1)
O3—Fe1—O589.9 (2)O11—Fe2—N4161.1 (2)
O3—Fe1—O690.1 (1)O12—Fe2—N3159.3 (2)
O3—Fe1—N1107.3 (2)O12—Fe2—N487.4 (2)
O3—Fe1—N276.1 (1)N3—Fe2—N495.7 (1)
O5—Fe1—O685.3 (1)Fe1—O1—C10120.8 (3)
O5—Fe1—N1162.4 (1)Fe1—O3—C20119.0 (3)
O5—Fe1—N294.2 (1)Fe2—O7—C30119.0 (3)
O6—Fe1—N190.9 (1)Fe2—O9—C40118.4 (3)
O6—Fe1—N2166.2 (1)Fe1—N1—C1110.8 (3)
N1—Fe1—N293.5 (1)Fe1—N1—C9131.2 (3)
O7—Fe2—O9171.9 (1)Fe1—N2—C11109.9 (3)
O7—Fe2—O1187.4 (1)Fe1—N2—C19132.1 (3)
O7—Fe2—O1283.5 (2)Fe2—N3—C21110.7 (3)
O7—Fe2—N376.2 (1)Fe2—N3—C29131.9 (3)
O7—Fe2—N4111.3 (1)Fe2—N4—C31112.6 (3)
O9—Fe2—O1185.1 (1)Fe2—N4—C39128.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O15i0.832.022.801 (4)158
O6—H6B···O15ii0.821.922.731 (4)167
O5—H5B···O3iii0.822.122.910 (4)162
O6—H6A···O4iii0.831.992.760 (5)154
O11—H11A···O13iv0.921.952.854 (5)166
O11—H11B···O10v0.922.002.917 (5)175
O14—H14···O10vi0.831.872.675 (5)169
O15—H15A···O8vii0.841.872.704 (5)170
O12—H12A···O5v0.822.152.949 (5)165
O15—H15B···N5viii0.932.012.936 (5)178
O12—H12B···O16v0.821.942.757 (5)170
O16—H16A···O110.922.153.071 (5)178
O16—H16B···O20.891.832.722 (5)178
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+2; (iii) x, y+1, z+2; (iv) x, y+1, z; (v) x, y+1, z+1; (vi) x, y, z+1; (vii) x+1, y+1, z+1; (viii) x+1, y, z+1.
 

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