supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers buy article online

Acta Cryst. (2007). E63, m2921    [ doi:10.1107/S1600536807055468 ]

Piperazinediium bis[bis(pyridine-2,6-dicarboxylato)ferrate(III)] monohydrate

H. Aghabozorg, A. Nemati, Z. Derikvand and M. Ghadermazi

Abstract top

The asymmetric unit of the title compound, (C4H12N2)[Fe(C7H3NO4)2]2·H2O or (pipzH2)2+·2[Fe(pydc)2]-·H2O (pipz is piperazine and pydcH2 is pyridine-2,6-dicarboxylic acid), contains one dication, two anions and one uncoordinated water molecule. In the anions, each FeIII ion is hexacoordinated by four O [Fe-O = 2.005 (2)-2.044 (2) Å] and two N [Fe-N = 2.050 (2)-2.075 (2) Å] atoms in a distorted octahedral geometry. An extensive three-dimensional network formed by classical O-H...O and N-H...O and weak C-H...O intermolecular hydrogen bonds stabilizes the crystal packing, which also exhibits [pi]-[pi] [centroid-centroid distances 3.500 (2)-3.533 (2) Å] and C-H...[pi] interactions.

Comment top

Recent interest of our research group has focused on self-assembling synthesis and characterization of novel metal complexes of proton transfer compounds (Aghabozorg, Sadrkhanlou et al., 2007; Aghabozorg, Motyeian et al., 2007; Aghabozorg, Attar Gharamaleki et al., 2007a,b). The pyridine-2,6-dicarboxylate ion is an effective tridentate chelating ligand forming stable complexes with most metal ions (Sheshmani et al., 2006). This compound has not been crystallized until now but its metal-organic derivatives can be obtained as suitable crystals. We have recently reported the crystal structures of new compounds synthesized using this ligand and piperazinediium as counter-ion. In this report, the crystal structure of the title iron(III) derivative, (I), is described.

The Fe1III and Fe2III ions are located at the centers of a distorted octahedrons (Fig.1). The angles N1—Fe1—N2 [169.31 (10)°], O1—Fe1—O3 [151.57 (9)°], O5—Fe1—O7 [151.57 (8)°], N3—Fe2—N4 [170.52 (10)°], O9—Fe2—O11 [151.29 (8)°] and O13—Fe2—O15 [151.16 (8)°] indicate some difference in Fe1III and Fe2III coordination geometries.

The torsion angles C7—O3—Fe1—O5 [86.8 (2)°] and C6— O1—Fe1—O5 [−91.3 (2)°] indicate that two dianionic pydc2– units connecting to Fe1III ion,are almost perpendicular to each other. The same is valid for Fe2 center, proved by torsion angles C27— O13—Fe2—O9 [92.4 (2)°] and C28— O15—Fe2—O9 [−90.1 (2)°]

In this work we use Fe2+ ions as starting material. Most probably, during the synthesis, Fe2+ ions oxidize into Fe3+ ions and in our crystalline product we obtain FeIII complexes.

There are π-π stacking interactions between the anions, proved by short distances Cg1···Cg2i, Cg1···Cg2ii and Cg3···Cg3iii of 3.500 (2), 3.533 (2) and 3.724 (2) Å, respectively [Cg1, Cg2 and Cg3 are centroids of N2/C8—C12, N3/C15—C19 and N4/C22—C26 rings, respectively. Symmetry codes: (i) 1/2 − x, −1/2 + y, 1/2-z ; (ii) 3/2 − x, −1/2 + y, 1/2 − z; (iii) −x, 1 − y, −z]. Also C—H···π interactions exist in the crystal, with C23···Cg4iv distance of 3.591 (4) Å (Fig. 2) [symmetry code: (iv) −1 + x, y, z]. The extensive O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1) between [Fe1(pydc)2]−, [Fe2(pydc)2]−, (pipzH2)2+ and uncoordinated water molecules play an important role in stabilization of the crystal packing (Fig. 3).

Related literature top

For related crystal structures, see: Aghabozorg, Attar Gharamaleki et al. (2007a,b); Aghabozorg, Motyeian et al. (2007); Aghabozorg, Sadrkhanlou et al. (2007); Sheshmani et al. (2006).

Experimental top

The proton transfer compound (pipzH2)(pydcH)2·3H2O, was prepared by the reaction of pyridine-2,6-dicarboxylic acid (pydcH2) with piperazine (pipz), (Sheshmani et al., 2006). The reaction between FeSO4·7H2O (139 mg, 0.5 mmol) in water (25 ml) and the proton transfer compound (pipzH2)(pydcH)2·3H2O (253 mg, 1.0 mmol) in water (25 ml), in a 1:2 molar ratio was carried by slow evaporation of the solvent at room temperature.

Refinement top

The C– and N-bound H atoms were geometrically positioned (C—H 0.93–0.97 Å, N—H 0.90 Å). Hydrogen atoms of water molecule were found in difference Fourier map and placed in idealized positions with O—H = 0.85, 0.87 Å. All hydrogen atoms were refined in riding model, with Uiso(H) = 1.2 Ueq of the parent atom.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998).

Figures top
[Figure 1] Fig. 1. The content of asymmetric unit of compound (I) showing the atomic numbering and displacement ellipsoids at the 50% proability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Intermolecular π-π and C—H···π interactions (dashed lines) between anionic fragments in (I).
[Figure 3] Fig. 3. A portion of the crystal packing viewed approximately down the a axis. Hydrogen bonds are shown as dashed lines.
Piperazinediium bis[bis(pyridine-2,6-dicarboxylato)ferrate(III)] monohydrate top
Crystal data top
(C4H12N2)·[Fe(C7H3NO4)2]2·H2OF(000) = 1792
Mr = 878.29Dx = 1.743 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.016 (3) ÅCell parameters from 3260 reflections
b = 24.855 (9) Åθ = 3–25°
c = 19.422 (7) ŵ = 0.96 mm−1
β = 98.697 (14)°T = 100 K
V = 3348 (2) Å3Prism, light yellow
Z = 40.23 × 0.15 × 0.14 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		7296 independent reflections
Radiation source: fine-focus sealed tube5113 reflections with I > 2u(I)
graphiteRint = 0.090
phi and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan
(APEX2; Bruker, 2005)		h = −8→8
Tmin = 0.795, Tmax = 0.878k = −31→31
34715 measured reflectionsl = −24→24
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)] = 0.042Hydrogen site location: mixed
wR(F2) = 0.081H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.01P)2 + 5.P]
where P = (Fo2 + 2Fc2)/3
7296 reflections(Δ/σ)max < 0.001
514 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
(C4H12N2)·[Fe(C7H3NO4)2]2·H2OV = 3348 (2) Å3
Mr = 878.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.016 (3) ŵ = 0.96 mm−1
b = 24.855 (9) ÅT = 100 K
c = 19.422 (7) Å0.23 × 0.15 × 0.14 mm
β = 98.697 (14)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		7296 independent reflections
Absorption correction: multi-scan
(APEX2; Bruker, 2005)		5113 reflections with I > 2u(I)
Tmin = 0.795, Tmax = 0.878Rint = 0.090
34715 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.081Δρmax = 0.43 e Å−3
S = 1.00Δρmin = −0.38 e Å−3
7296 reflectionsAbsolute structure: ?
514 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Fe10.71620 (6)0.207066 (17)0.04276 (2)0.01291 (11)
O10.4764 (3)0.24328 (8)0.06569 (11)0.0166 (5)
O20.2727 (3)0.31326 (9)0.04273 (12)0.0211 (5)
O30.9642 (3)0.20780 (8)0.00102 (11)0.0165 (5)
O41.1158 (3)0.24126 (9)−0.08327 (11)0.0207 (5)
O50.5842 (3)0.15623 (8)−0.02932 (11)0.0163 (5)
O60.5183 (3)0.06986 (8)−0.05937 (11)0.0174 (5)
O70.8526 (3)0.22327 (8)0.14032 (10)0.0156 (5)
O80.9823 (3)0.19068 (8)0.24467 (11)0.0175 (5)
N10.6895 (4)0.27400 (9)−0.01967 (13)0.0121 (5)
N20.7583 (3)0.13279 (10)0.08960 (12)0.0116 (5)
C10.5311 (4)0.30378 (12)−0.02266 (15)0.0137 (7)
C20.4961 (5)0.34517 (12)−0.07039 (16)0.0171 (7)
H2A0.38610.3664−0.07270.021*
C30.6304 (5)0.35402 (12)−0.11464 (16)0.0176 (7)
H3A0.60950.3814−0.14760.021*
C40.7966 (5)0.32254 (12)−0.11064 (16)0.0174 (7)
H4A0.88750.3287−0.14000.021*
C50.8212 (4)0.28188 (12)−0.06154 (15)0.0133 (7)
C60.4107 (4)0.28637 (12)0.03254 (15)0.0141 (7)
C70.9836 (4)0.24122 (12)−0.04780 (15)0.0142 (7)
C80.6869 (4)0.08948 (12)0.05390 (15)0.0125 (6)
C90.6972 (4)0.03904 (12)0.08467 (16)0.0138 (7)
H9A0.64930.00870.06000.017*
C100.7826 (4)0.03575 (12)0.15446 (16)0.0146 (7)
H10A0.78990.00260.17690.018*
C110.8566 (4)0.08114 (12)0.19087 (16)0.0135 (7)
H11A0.91320.07890.23730.016*
C120.8435 (4)0.12969 (12)0.15588 (15)0.0123 (6)
C130.5878 (4)0.10475 (12)−0.01869 (15)0.0129 (7)
C140.9016 (4)0.18461 (12)0.18457 (16)0.0139 (7)
Fe20.13045 (6)0.498478 (18)0.22775 (2)0.01192 (10)
O90.0081 (3)0.57045 (8)0.19928 (10)0.0158 (5)
O10−0.0516 (3)0.65490 (8)0.23228 (11)0.0192 (5)
O110.2693 (3)0.44742 (8)0.30124 (10)0.0139 (5)
O120.4383 (3)0.43939 (9)0.40847 (11)0.0174 (5)
O13−0.1175 (3)0.45562 (8)0.22040 (10)0.0155 (5)
O14−0.3321 (3)0.40362 (8)0.15340 (11)0.0171 (5)
O150.3776 (3)0.51753 (8)0.19324 (10)0.0161 (5)
O160.5341 (3)0.52268 (8)0.10081 (11)0.0180 (5)
N30.1764 (3)0.54382 (10)0.31847 (12)0.0110 (5)
N40.1015 (4)0.46452 (10)0.13012 (13)0.0126 (5)
C150.1258 (4)0.59589 (12)0.31464 (16)0.0132 (7)
C160.1758 (4)0.62933 (12)0.37140 (16)0.0152 (7)
H16A0.14310.66560.36890.018*
C170.2763 (4)0.60755 (13)0.43247 (16)0.0153 (7)
H17A0.31190.62940.47110.018*
C180.3234 (4)0.55302 (12)0.43571 (15)0.0137 (7)
H18A0.38600.53770.47670.016*
C190.2742 (4)0.52220 (12)0.37614 (15)0.0123 (6)
C200.0167 (4)0.60987 (12)0.24339 (16)0.0150 (7)
C210.3333 (4)0.46497 (12)0.36450 (15)0.0124 (6)
C22−0.0591 (4)0.43742 (12)0.10654 (15)0.0124 (6)
C23−0.0907 (4)0.41764 (12)0.03954 (16)0.0157 (7)
H23A−0.20260.39870.02290.019*
C240.0505 (5)0.42688 (12)−0.00249 (16)0.0173 (7)
H24A0.03240.4142−0.04810.021*
C250.2179 (5)0.45485 (12)0.02302 (15)0.0145 (7)
H25A0.31340.4607−0.00450.017*
C260.2377 (4)0.47350 (12)0.09018 (16)0.0129 (6)
C27−0.1845 (4)0.43116 (12)0.16316 (16)0.0140 (7)
C280.4009 (4)0.50685 (12)0.12910 (15)0.0129 (6)
N50.7543 (4)0.27251 (11)0.29327 (13)0.0203 (6)
H5A0.83240.24780.27840.024*
H5B0.71750.26020.33280.024*
N60.5561 (4)0.37357 (10)0.27689 (13)0.0166 (6)
H6A0.47760.39820.29180.020*
H6B0.59130.38580.23700.020*
C290.5805 (5)0.28004 (13)0.23931 (17)0.0209 (8)
H29A0.51150.24620.23140.025*
H29B0.62000.29120.19580.025*
C300.4504 (5)0.32196 (12)0.26320 (17)0.0185 (7)
H30A0.33910.32730.22770.022*
H30B0.40520.30980.30540.022*
C310.7309 (5)0.36691 (13)0.33023 (16)0.0189 (7)
H31A0.69250.35680.37440.023*
H31B0.79970.40080.33670.023*
C320.8625 (5)0.32418 (13)0.30800 (17)0.0209 (7)
H32A0.91220.33600.26650.025*
H32B0.97100.31860.34460.025*
O1W0.0582 (3)0.32196 (9)0.15291 (11)0.0226 (5)
H1W0.11880.31970.11810.027*
H2W0.01810.28920.15680.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0157 (2)0.0105 (2)0.0122 (2)0.00008 (19)0.00130 (18)0.00209 (18)
O10.0188 (12)0.0156 (12)0.0168 (12)0.0003 (10)0.0070 (9)0.0033 (9)
O20.0193 (13)0.0191 (12)0.0262 (13)0.0045 (10)0.0079 (10)−0.0017 (10)
O30.0163 (12)0.0166 (11)0.0167 (11)0.0039 (10)0.0033 (9)0.0028 (10)
O40.0174 (12)0.0284 (13)0.0176 (12)0.0019 (10)0.0073 (10)−0.0019 (10)
O50.0185 (12)0.0131 (11)0.0160 (11)0.0004 (9)−0.0018 (9)0.0015 (9)
O60.0177 (12)0.0165 (12)0.0180 (12)−0.0033 (10)0.0023 (9)−0.0029 (10)
O70.0211 (12)0.0109 (11)0.0142 (11)0.0005 (9)0.0010 (9)0.0014 (9)
O80.0178 (12)0.0189 (12)0.0148 (12)0.0027 (10)−0.0004 (9)−0.0017 (9)
N10.0132 (13)0.0103 (13)0.0125 (13)−0.0005 (11)0.0005 (10)−0.0016 (11)
N20.0108 (13)0.0119 (13)0.0129 (13)0.0017 (10)0.0042 (10)0.0007 (11)
C10.0137 (16)0.0122 (16)0.0139 (16)−0.0014 (13)−0.0016 (13)−0.0035 (12)
C20.0228 (18)0.0126 (16)0.0146 (16)0.0010 (14)−0.0017 (14)−0.0013 (13)
C30.0299 (19)0.0080 (15)0.0137 (16)−0.0013 (14)0.0000 (14)−0.0001 (13)
C40.0249 (18)0.0159 (16)0.0123 (16)−0.0038 (14)0.0061 (14)−0.0020 (13)
C50.0140 (16)0.0146 (16)0.0107 (15)−0.0030 (13)0.0000 (12)−0.0033 (12)
C60.0143 (16)0.0154 (16)0.0125 (16)−0.0007 (14)0.0014 (12)−0.0010 (13)
C70.0160 (17)0.0146 (16)0.0110 (15)−0.0023 (13)−0.0009 (13)−0.0042 (13)
C80.0090 (15)0.0135 (16)0.0161 (16)0.0024 (13)0.0051 (12)−0.0005 (13)
C90.0120 (16)0.0097 (15)0.0209 (17)0.0007 (13)0.0065 (13)−0.0010 (13)
C100.0138 (16)0.0108 (15)0.0205 (17)0.0036 (13)0.0064 (13)0.0050 (13)
C110.0135 (16)0.0150 (16)0.0130 (16)0.0059 (13)0.0052 (13)0.0029 (13)
C120.0087 (15)0.0173 (16)0.0116 (15)0.0031 (13)0.0035 (12)0.0005 (13)
C130.0095 (15)0.0173 (17)0.0130 (16)−0.0001 (13)0.0055 (12)−0.0024 (13)
C140.0122 (16)0.0155 (16)0.0150 (17)0.0027 (13)0.0055 (13)0.0001 (13)
Fe20.0134 (2)0.0123 (2)0.0103 (2)−0.00072 (19)0.00259 (17)−0.00144 (18)
O90.0195 (12)0.0147 (11)0.0124 (11)−0.0005 (10)0.0002 (9)0.0002 (9)
O100.0218 (13)0.0143 (12)0.0228 (12)0.0033 (10)0.0082 (10)0.0048 (10)
O110.0163 (12)0.0135 (11)0.0123 (11)0.0023 (9)0.0034 (9)−0.0015 (9)
O120.0169 (12)0.0194 (12)0.0152 (12)0.0041 (10)0.0000 (9)0.0025 (10)
O130.0166 (12)0.0159 (12)0.0144 (11)−0.0004 (9)0.0041 (9)−0.0024 (9)
O140.0158 (12)0.0179 (12)0.0172 (12)−0.0049 (10)0.0014 (9)−0.0005 (9)
O150.0154 (12)0.0208 (12)0.0130 (11)−0.0039 (9)0.0046 (9)−0.0034 (9)
O160.0170 (12)0.0188 (12)0.0193 (12)−0.0035 (10)0.0065 (10)−0.0004 (10)
N30.0088 (13)0.0121 (13)0.0131 (13)−0.0005 (10)0.0046 (10)−0.0021 (10)
N40.0148 (14)0.0109 (13)0.0128 (13)0.0019 (11)0.0044 (11)0.0005 (11)
C150.0122 (16)0.0134 (16)0.0160 (16)−0.0003 (13)0.0086 (13)0.0004 (13)
C160.0138 (16)0.0139 (16)0.0203 (17)−0.0014 (13)0.0109 (13)−0.0030 (13)
C170.0105 (16)0.0205 (17)0.0159 (16)−0.0043 (13)0.0059 (13)−0.0085 (13)
C180.0103 (16)0.0205 (17)0.0109 (15)−0.0020 (13)0.0038 (12)−0.0003 (13)
C190.0097 (15)0.0157 (16)0.0125 (15)−0.0010 (13)0.0047 (12)0.0013 (13)
C200.0119 (16)0.0160 (17)0.0189 (17)−0.0028 (13)0.0078 (13)0.0027 (14)
C210.0108 (15)0.0150 (16)0.0127 (16)−0.0023 (13)0.0056 (12)−0.0005 (13)
C220.0147 (16)0.0089 (15)0.0127 (15)0.0001 (13)−0.0006 (12)0.0009 (12)
C230.0152 (17)0.0142 (16)0.0166 (16)−0.0008 (13)−0.0007 (13)−0.0013 (13)
C240.0289 (19)0.0122 (16)0.0104 (15)0.0011 (14)0.0022 (14)−0.0021 (13)
C250.0205 (17)0.0121 (16)0.0119 (16)0.0016 (13)0.0055 (13)0.0007 (13)
C260.0155 (16)0.0076 (15)0.0159 (16)0.0007 (13)0.0038 (13)0.0019 (12)
C270.0154 (17)0.0113 (16)0.0146 (16)0.0012 (13)0.0004 (13)0.0030 (13)
C280.0138 (16)0.0112 (16)0.0144 (15)0.0041 (13)0.0042 (12)0.0020 (13)
N50.0276 (16)0.0215 (15)0.0125 (14)0.0096 (13)0.0055 (12)0.0026 (12)
N60.0182 (15)0.0155 (14)0.0171 (14)0.0019 (12)0.0058 (11)−0.0023 (11)
C290.027 (2)0.0171 (18)0.0182 (17)−0.0006 (14)0.0004 (15)−0.0008 (14)
C300.0163 (17)0.0156 (17)0.0238 (18)−0.0012 (14)0.0037 (14)0.0015 (14)
C310.0204 (18)0.0203 (18)0.0158 (17)−0.0035 (14)0.0018 (14)−0.0036 (14)
C320.0147 (17)0.030 (2)0.0180 (17)0.0030 (15)0.0021 (14)0.0005 (15)
O1W0.0269 (14)0.0192 (12)0.0228 (13)−0.0035 (10)0.0077 (10)−0.0009 (10)
Geometric parameters (Å, °) top
Fe1—O52.005 (2)O13—C271.292 (3)
Fe1—O12.017 (2)O14—C271.232 (4)
Fe1—O32.028 (2)O15—C281.308 (3)
Fe1—O72.030 (2)O16—C281.219 (3)
Fe1—N12.050 (2)N3—C191.335 (4)
Fe1—N22.060 (3)N3—C151.341 (4)
O1—C61.297 (4)N4—C221.333 (4)
O2—C61.217 (4)N4—C261.338 (4)
O3—C71.283 (4)C15—C161.383 (4)
O4—C71.236 (3)C15—C201.517 (4)
O5—C131.296 (4)C16—C171.394 (4)
O6—C131.224 (3)C16—H16A0.9300
O7—C141.300 (3)C17—C181.394 (4)
O8—C141.227 (4)C17—H17A0.9300
N1—C11.329 (4)C18—C191.387 (4)
N1—C51.335 (4)C18—H18A0.9300
N2—C81.336 (4)C19—C211.508 (4)
N2—C121.337 (4)C22—C231.377 (4)
C1—C21.382 (4)C22—C271.517 (4)
C1—C61.524 (4)C23—C241.395 (4)
C2—C31.385 (4)C23—H23A0.9300
C2—H2A0.9300C24—C251.390 (4)
C3—C41.397 (4)C24—H24A0.9300
C3—H3A0.9300C25—C261.371 (4)
C4—C51.382 (4)C25—H25A0.9300
C4—H4A0.9300C26—C281.519 (4)
C5—C71.516 (4)N5—C291.494 (4)
C8—C91.386 (4)N5—C321.497 (4)
C8—C131.523 (4)N5—H5A0.9000
C9—C101.399 (4)N5—H5B0.9000
C9—H9A0.9300N6—C301.485 (4)
C10—C111.390 (4)N6—C311.490 (4)
C10—H10A0.9300N6—H6A0.9000
C11—C121.381 (4)N6—H6B0.9000
C11—H11A0.9300C29—C301.504 (4)
C12—C141.507 (4)C29—H29A0.9700
Fe2—O152.008 (2)C29—H29B0.9700
Fe2—O92.025 (2)C30—H30A0.9700
Fe2—O132.026 (2)C30—H30B0.9700
Fe2—O112.044 (2)C31—C321.512 (4)
Fe2—N42.057 (3)C31—H31A0.9700
Fe2—N32.075 (2)C31—H31B0.9700
O9—C201.297 (4)C32—H32A0.9700
O10—C201.224 (4)C32—H32B0.9700
O11—C211.317 (3)O1W—H1W0.8540
O12—C211.219 (3)O1W—H2W0.8677
O5—Fe1—O197.06 (9)C19—N3—C15122.2 (3)
O5—Fe1—O393.44 (9)C19—N3—Fe2119.2 (2)
O1—Fe1—O3151.57 (9)C15—N3—Fe2118.1 (2)
O5—Fe1—O7151.57 (8)C22—N4—C26121.7 (3)
O1—Fe1—O789.81 (9)C22—N4—Fe2119.0 (2)
O3—Fe1—O793.41 (9)C26—N4—Fe2119.1 (2)
O5—Fe1—N196.14 (9)N3—C15—C16120.2 (3)
O1—Fe1—N176.33 (9)N3—C15—C20111.4 (3)
O3—Fe1—N176.32 (9)C16—C15—C20128.4 (3)
O7—Fe1—N1112.28 (9)C15—C16—C17118.6 (3)
O5—Fe1—N276.34 (9)C15—C16—H16A120.7
O1—Fe1—N2111.80 (9)C17—C16—H16A120.7
O3—Fe1—N296.32 (9)C18—C17—C16120.1 (3)
O7—Fe1—N275.50 (9)C18—C17—H17A119.9
N1—Fe1—N2169.31 (10)C16—C17—H17A119.9
C6—O1—Fe1120.28 (19)C19—C18—C17118.2 (3)
C7—O3—Fe1119.63 (19)C19—C18—H18A120.9
C13—O5—Fe1121.01 (19)C17—C18—H18A120.9
C14—O7—Fe1120.71 (19)N3—C19—C18120.6 (3)
C1—N1—C5122.9 (3)N3—C19—C21111.8 (3)
C1—N1—Fe1118.6 (2)C18—C19—C21127.3 (3)
C5—N1—Fe1118.0 (2)O10—C20—O9126.6 (3)
C8—N2—C12122.1 (3)O10—C20—C15120.0 (3)
C8—N2—Fe1118.4 (2)O9—C20—C15113.4 (3)
C12—N2—Fe1119.4 (2)O12—C21—O11124.4 (3)
N1—C1—C2120.4 (3)O12—C21—C19122.5 (3)
N1—C1—C6111.1 (3)O11—C21—C19112.9 (3)
C2—C1—C6128.5 (3)N4—C22—C23120.8 (3)
C1—C2—C3117.8 (3)N4—C22—C27110.8 (3)
C1—C2—H2A121.1C23—C22—C27128.3 (3)
C3—C2—H2A121.1C22—C23—C24117.8 (3)
C2—C3—C4121.1 (3)C22—C23—H23A121.1
C2—C3—H3A119.4C24—C23—H23A121.1
C4—C3—H3A119.4C25—C24—C23120.7 (3)
C5—C4—C3117.6 (3)C25—C24—H24A119.7
C5—C4—H4A121.2C23—C24—H24A119.7
C3—C4—H4A121.2C26—C25—C24117.8 (3)
N1—C5—C4120.1 (3)C26—C25—H25A121.1
N1—C5—C7111.5 (3)C24—C25—H25A121.1
C4—C5—C7128.4 (3)N4—C26—C25121.1 (3)
O2—C6—O1127.1 (3)N4—C26—C28110.7 (3)
O2—C6—C1119.8 (3)C25—C26—C28128.2 (3)
O1—C6—C1113.0 (3)O14—C27—O13125.6 (3)
O4—C7—O3125.8 (3)O14—C27—C22120.8 (3)
O4—C7—C5120.6 (3)O13—C27—C22113.6 (3)
O3—C7—C5113.6 (3)O16—C28—O15125.4 (3)
N2—C8—C9120.9 (3)O16—C28—C26121.6 (3)
N2—C8—C13111.3 (3)O15—C28—C26113.0 (2)
C9—C8—C13127.7 (3)C29—N5—C32111.3 (2)
C8—C9—C10117.2 (3)C29—N5—H5A109.4
C8—C9—H9A121.4C32—N5—H5A109.4
C10—C9—H9A121.4C29—N5—H5B109.4
C11—C10—C9121.2 (3)C32—N5—H5B109.4
C11—C10—H10A119.4H5A—N5—H5B108.0
C9—C10—H10A119.4C30—N6—C31111.4 (2)
C12—C11—C10117.8 (3)C30—N6—H6A109.4
C12—C11—H11A121.1C31—N6—H6A109.4
C10—C11—H11A121.1C30—N6—H6B109.4
N2—C12—C11120.7 (3)C31—N6—H6B109.4
N2—C12—C14111.1 (3)H6A—N6—H6B108.0
C11—C12—C14128.0 (3)N5—C29—C30109.8 (3)
O6—C13—O5126.9 (3)N5—C29—H29A109.7
O6—C13—C8120.2 (3)C30—C29—H29A109.7
O5—C13—C8112.9 (3)N5—C29—H29B109.7
O8—C14—O7125.2 (3)C30—C29—H29B109.7
O8—C14—C12121.5 (3)H29A—C29—H29B108.2
O7—C14—C12113.3 (3)N6—C30—C29110.1 (3)
O15—Fe2—O993.01 (9)N6—C30—H30A109.6
O15—Fe2—O13151.16 (8)C29—C30—H30A109.6
O9—Fe2—O1396.96 (9)N6—C30—H30B109.6
O15—Fe2—O1192.01 (9)C29—C30—H30B109.6
O9—Fe2—O11151.29 (8)H30A—C30—H30B108.2
O13—Fe2—O1192.08 (9)N6—C31—C32110.7 (3)
O15—Fe2—N476.05 (9)N6—C31—H31A109.5
O9—Fe2—N497.59 (9)C32—C31—H31A109.5
O13—Fe2—N475.84 (9)N6—C31—H31B109.5
O11—Fe2—N4111.05 (9)C32—C31—H31B109.5
O15—Fe2—N397.14 (9)H31A—C31—H31B108.1
O9—Fe2—N375.94 (9)N5—C32—C31110.1 (3)
O13—Fe2—N3111.51 (9)N5—C32—H32A109.6
O11—Fe2—N375.39 (9)C31—C32—H32A109.6
N4—Fe2—N3170.52 (10)N5—C32—H32B109.6
C20—O9—Fe2120.76 (19)C31—C32—H32B109.6
C21—O11—Fe2120.34 (18)H32A—C32—H32B108.2
C27—O13—Fe2120.33 (19)H1W—O1W—H2W102.4
C28—O15—Fe2120.59 (19)
O5—Fe1—O1—C6−91.3 (2)O13—Fe2—O9—C20113.2 (2)
O3—Fe1—O1—C619.5 (3)O11—Fe2—O9—C205.8 (3)
O7—Fe1—O1—C6116.3 (2)N4—Fe2—O9—C20−170.2 (2)
N1—Fe1—O1—C63.3 (2)N3—Fe2—O9—C202.7 (2)
N2—Fe1—O1—C6−169.4 (2)O15—Fe2—O11—C2191.7 (2)
O5—Fe1—O3—C786.8 (2)O9—Fe2—O11—C21−8.3 (3)
O1—Fe1—O3—C7−24.9 (3)O13—Fe2—O11—C21−116.8 (2)
O7—Fe1—O3—C7−120.8 (2)N4—Fe2—O11—C21167.5 (2)
N1—Fe1—O3—C7−8.7 (2)N3—Fe2—O11—C21−5.2 (2)
N2—Fe1—O3—C7163.4 (2)O15—Fe2—O13—C27−17.0 (3)
O1—Fe1—O5—C13−113.5 (2)O9—Fe2—O13—C2792.4 (2)
O3—Fe1—O5—C1393.0 (2)O11—Fe2—O13—C27−114.9 (2)
O7—Fe1—O5—C13−10.7 (3)N4—Fe2—O13—C27−3.7 (2)
N1—Fe1—O5—C13169.6 (2)N3—Fe2—O13—C27170.0 (2)
N2—Fe1—O5—C13−2.7 (2)O9—Fe2—O15—C28−90.1 (2)
O5—Fe1—O7—C148.1 (3)O13—Fe2—O15—C2820.2 (3)
O1—Fe1—O7—C14112.7 (2)O11—Fe2—O15—C28118.2 (2)
O3—Fe1—O7—C14−95.6 (2)N4—Fe2—O15—C287.0 (2)
N1—Fe1—O7—C14−172.2 (2)N3—Fe2—O15—C28−166.3 (2)
N2—Fe1—O7—C140.1 (2)O15—Fe2—N3—C19−86.9 (2)
O5—Fe1—N1—C188.3 (2)O9—Fe2—N3—C19−178.3 (2)
O1—Fe1—N1—C1−7.5 (2)O13—Fe2—N3—C1989.7 (2)
O3—Fe1—N1—C1−179.6 (2)O11—Fe2—N3—C193.3 (2)
O7—Fe1—N1—C1−91.5 (2)O15—Fe2—N3—C1585.4 (2)
N2—Fe1—N1—C1133.1 (5)O9—Fe2—N3—C15−5.9 (2)
O5—Fe1—N1—C5−83.9 (2)O13—Fe2—N3—C15−98.0 (2)
O1—Fe1—N1—C5−179.7 (2)O11—Fe2—N3—C15175.6 (2)
O3—Fe1—N1—C58.2 (2)O15—Fe2—N4—C22179.6 (2)
O7—Fe1—N1—C596.3 (2)O9—Fe2—N4—C22−89.1 (2)
N2—Fe1—N1—C5−39.1 (6)O13—Fe2—N4—C226.2 (2)
O5—Fe1—N2—C80.4 (2)O11—Fe2—N4—C2292.9 (2)
O1—Fe1—N2—C892.6 (2)O15—Fe2—N4—C26−5.2 (2)
O3—Fe1—N2—C8−91.6 (2)O9—Fe2—N4—C2686.1 (2)
O7—Fe1—N2—C8176.5 (2)O13—Fe2—N4—C26−178.6 (2)
N1—Fe1—N2—C8−45.7 (6)O11—Fe2—N4—C26−91.9 (2)
O5—Fe1—N2—C12−175.0 (2)C19—N3—C15—C160.4 (4)
O1—Fe1—N2—C12−82.7 (2)Fe2—N3—C15—C16−171.7 (2)
O3—Fe1—N2—C1293.0 (2)C19—N3—C15—C20179.8 (3)
O7—Fe1—N2—C121.1 (2)Fe2—N3—C15—C207.7 (3)
N1—Fe1—N2—C12139.0 (5)N3—C15—C16—C17−1.0 (4)
C5—N1—C1—C2−0.1 (4)C20—C15—C16—C17179.6 (3)
Fe1—N1—C1—C2−171.9 (2)C15—C16—C17—C18−0.4 (4)
C5—N1—C1—C6−178.6 (3)C16—C17—C18—C192.5 (4)
Fe1—N1—C1—C69.7 (3)C15—N3—C19—C181.8 (4)
N1—C1—C2—C30.4 (4)Fe2—N3—C19—C18173.8 (2)
C6—C1—C2—C3178.5 (3)C15—N3—C19—C21−173.3 (3)
C1—C2—C3—C4−0.7 (5)Fe2—N3—C19—C21−1.3 (3)
C2—C3—C4—C50.7 (5)C17—C18—C19—N3−3.1 (4)
C1—N1—C5—C40.2 (4)C17—C18—C19—C21171.1 (3)
Fe1—N1—C5—C4172.0 (2)Fe2—O9—C20—O10−179.9 (2)
C1—N1—C5—C7−178.5 (3)Fe2—O9—C20—C150.5 (3)
Fe1—N1—C5—C7−6.7 (3)N3—C15—C20—O10175.1 (3)
C3—C4—C5—N1−0.5 (4)C16—C15—C20—O10−5.6 (5)
C3—C4—C5—C7178.0 (3)N3—C15—C20—O9−5.3 (4)
Fe1—O1—C6—O2−177.1 (2)C16—C15—C20—O9174.1 (3)
Fe1—O1—C6—C10.7 (3)Fe2—O11—C21—O12−170.2 (2)
N1—C1—C6—O2171.4 (3)Fe2—O11—C21—C196.0 (3)
C2—C1—C6—O2−6.9 (5)N3—C19—C21—O12173.4 (3)
N1—C1—C6—O1−6.6 (4)C18—C19—C21—O12−1.3 (5)
C2—C1—C6—O1175.1 (3)N3—C19—C21—O11−2.9 (3)
Fe1—O3—C7—O4−170.4 (2)C18—C19—C21—O11−177.5 (3)
Fe1—O3—C7—C57.7 (3)C26—N4—C22—C23−0.1 (4)
N1—C5—C7—O4177.7 (3)Fe2—N4—C22—C23175.0 (2)
C4—C5—C7—O4−0.9 (5)C26—N4—C22—C27177.7 (3)
N1—C5—C7—O3−0.5 (4)Fe2—N4—C22—C27−7.2 (3)
C4—C5—C7—O3−179.1 (3)N4—C22—C23—C240.0 (4)
C12—N2—C8—C90.5 (4)C27—C22—C23—C24−177.4 (3)
Fe1—N2—C8—C9−174.8 (2)C22—C23—C24—C250.5 (4)
C12—N2—C8—C13176.7 (2)C23—C24—C25—C26−0.9 (4)
Fe1—N2—C8—C131.4 (3)C22—N4—C26—C25−0.3 (4)
N2—C8—C9—C100.9 (4)Fe2—N4—C26—C25−175.4 (2)
C13—C8—C9—C10−174.7 (3)C22—N4—C26—C28178.0 (3)
C8—C9—C10—C11−1.0 (4)Fe2—N4—C26—C282.9 (3)
C9—C10—C11—C12−0.1 (4)C24—C25—C26—N40.8 (4)
C8—N2—C12—C11−1.7 (4)C24—C25—C26—C28−177.2 (3)
Fe1—N2—C12—C11173.5 (2)Fe2—O13—C27—O14179.1 (2)
C8—N2—C12—C14−177.1 (3)Fe2—O13—C27—C221.1 (3)
Fe1—N2—C12—C14−1.9 (3)N4—C22—C27—O14−174.2 (3)
C10—C11—C12—N21.5 (4)C23—C22—C27—O143.5 (5)
C10—C11—C12—C14176.1 (3)N4—C22—C27—O133.9 (4)
Fe1—O5—C13—O6−177.5 (2)C23—C22—C27—O13−178.5 (3)
Fe1—O5—C13—C84.2 (3)Fe2—O15—C28—O16170.3 (2)
N2—C8—C13—O6178.1 (3)Fe2—O15—C28—C26−7.4 (3)
C9—C8—C13—O6−6.0 (5)N4—C26—C28—O16−175.1 (3)
N2—C8—C13—O5−3.5 (4)C25—C26—C28—O163.1 (5)
C9—C8—C13—O5172.4 (3)N4—C26—C28—O152.7 (4)
Fe1—O7—C14—O8−179.2 (2)C25—C26—C28—O15−179.1 (3)
Fe1—O7—C14—C12−1.1 (3)C32—N5—C29—C30−58.2 (3)
N2—C12—C14—O8−180.0 (3)C31—N6—C30—C29−58.1 (3)
C11—C12—C14—O85.0 (5)N5—C29—C30—N658.1 (3)
N2—C12—C14—O71.9 (4)C30—N6—C31—C3256.8 (3)
C11—C12—C14—O7−173.1 (3)C29—N5—C32—C3156.7 (3)
O15—Fe2—O9—C20−93.9 (2)N6—C31—C32—N5−55.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O80.901.942.836 (4)175
N5—H5B···O4i0.901.882.742 (4)161
N6—H6A···O110.901.942.816 (4)165
N6—H6B···O14ii0.901.842.738 (4)174
O1W—H1W···O20.851.952.805 (4)176
O1W—H2W···O7iii0.872.012.837 (4)160
C4—H4A···O10iv0.932.313.221 (4)167
C9—H9A···O6v0.932.283.103 (4)148
C11—H11A···O15vi0.932.393.126 (4)136
C16—H16A···O1vii0.932.523.324 (4)144
C17—H17A···O3viii0.932.513.237 (4)135
C18—H18A···O12ix0.932.453.234 (4)142
C25—H25A···O16iv0.932.333.223 (4)162
C29—H29A···O10x0.972.383.171 (4)138
C30—H30A···O1W0.972.273.221 (4)167
C31—H31B···O6xi0.972.453.135 (4)127
C32—H32A···O1Wii0.972.593.495 (4)155
C32—H32B···O5xi0.972.543.340 (4)140
C23—H23A···Cg4(N1/C1-C5)iii0.932.813.591 (4)142
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z; (v) −x+1, −y, −z; (vi) −x+3/2, y−1/2, −z+1/2; (vii) −x+1/2, y+1/2, −z+1/2; (viii) −x+3/2, y+1/2, −z+1/2; (ix) −x+1, −y+1, −z+1; (x) −x+1/2, y−1/2, −z+1/2; (xi) x+1/2, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O80.901.942.836 (4)175
N5—H5B···O4i0.901.882.742 (4)161
N6—H6A···O110.901.942.816 (4)165
N6—H6B···O14ii0.901.842.738 (4)174
O1W—H1W···O20.851.952.805 (4)176
O1W—H2W···O7iii0.872.012.837 (4)160
C4—H4A···O10iv0.932.313.221 (4)167
C9—H9A···O6v0.932.283.103 (4)148
C11—H11A···O15vi0.932.393.126 (4)136
C16—H16A···O1vii0.932.523.324 (4)144
C17—H17A···O3viii0.932.513.237 (4)135
C18—H18A···O12ix0.932.453.234 (4)142
C25—H25A···O16iv0.932.333.223 (4)162
C29—H29A···O10x0.972.383.171 (4)138
C30—H30A···O1W0.972.273.221 (4)167
C31—H31B···O6xi0.972.453.135 (4)127
C32—H32A···O1Wii0.972.593.495 (4)155
C32—H32B···O5xi0.972.543.340 (4)140
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z; (v) −x+1, −y, −z; (vi) −x+3/2, y−1/2, −z+1/2; (vii) −x+1/2, y+1/2, −z+1/2; (viii) −x+3/2, y+1/2, −z+1/2; (ix) −x+1, −y+1, −z+1; (x) −x+1/2, y−1/2, −z+1/2; (xi) x+1/2, −y+1/2, z+1/2.
references
References top

Aghabozorg, H., Attar Gharamaleki, J., Ghadermazi, M., Ghasemikhah, P. & Soleimannejad, J. (2007a). Acta Cryst. E63, m1803–m1804.

Aghabozorg, H., Attar Gharamaleki, J., Ghasemikhah, P., Ghadermazi, M. & Soleimannejad, J. (2007b). Acta Cryst. E63, m1710–m1711.

Aghabozorg, H., Motyeian, E., Aghajani, Z., Ghadermazi, M. & Attar Gharamaleki, J. (2007). Acta Cryst. E63, m1754–m1755.

Aghabozorg, H., Sadrkhanlou, E., Soleimannejad, J. & Adams, H. (2007). Acta Cryst. E63, m1760–?.

Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1998). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheshmani, S., Ghadermazi, M. & Aghabozorg, H. (2006). Acta Cryst. E62, o3620–o3622.