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Acta Cryst. (2007). E63, m2445    [ doi:10.1107/S1600536807042122 ]

catena-Poly[[(2,2'-bipyridine-[kappa]2N,N')iron(II)]-[mu]-5-carboxy-4-carboxylatoimidazol-1-ido-[kappa]4N3,O4:N1,O5]

Z.-F. Li, S.-W. Wang, Q. Zhang and X.-J. Yu

Abstract top

The title compound, [Fe(C5H2N2O4)(C10H8N2)]n, was prepared by hydrothermal synthesis. The structure contains two crystallographically independent monomer units which exhibit similar geometry. The coordination environment of the FeII atom is octahedral, comprising two O atoms and four N atoms. Each FeII atom is chelated by one 2,2'-bipyridine ligand, and is linked to two neighbouring FeII atoms through bridging 5-carboxy-4-carboxylatoimidazol-1-ide ligands, forming zigzag chains parallel to the b axis. Intramolecular O-H...O hydrogen bonds are formed between the carboxy and carboxylate groups of each 5-carboxy-4-carboxylatoimidazol-1-ide ligand.

Comment top

Complexes containing carboxylic acids are of interest to chemists on account of their potential applications, such as catalysis, optics, information storage, medicine, molecular electrochemistry, biochemistry and biological pharmaceutics (Li et al., 1993; Go et al., 2004). Thus far, N-containing aromatic carboxylic acids, for example adipiodone and acetrizoic acid, have been widely used in organic synthesis, as dye intermediates, sensitization materials and functional pigments (An et al., 2000). Pyridine carboxylic acid is also used extensively in coordination chemistry due to its strong coordinating ability and versatile coordination modes (Baroni et al. (1996); Hundal et al. (2002)).

In the title compound, the asymetric unit contains two crystallographically independent monomer units. As shown in Fig. 1, FeII atoms have a distorted octahedral geometry formed by two carboxylate O atoms and four N atoms, two of which belong to the 2,2'-bipyridine ligand and the other two to the imidazole ring. The Fe—O and Fe—N bond lengths are in the range 2.110 (2)–2.216 (2) and 2.071 (2)–2.296 (2) Å, respectively. The carboxy and carboxylate groups of the 5-carboxy-4-carboxylatoimidazol-1-ide ligand coordinate in a monodentate fashion to two FeII atoms, giving rise to one-dimensional zigzag chains along [010] (Fig. 2). The 2,2'-bipyridine ligands are situated between these chains.

Related literature top

For related literature, see: Li et al. (1993); Go et al. (2004); An et al. (2000); Baroni et al. (1996); Hundal et al. (2002).

Experimental top

A mixture of FeSO4 (0.1 mmol), imidazole-4,5-dicarboxylic acid (0.1 mmol) and 2,2'-bipyridine (0.1 mmol) in 10 ml of a mixed ethanol/water solvent (1:1) was placed in a 25 ml Teflon-lined stainless steel autoclave and kept at 473 K for 10 d. Green crystals of the title compound were obtained after cooling to room temperature with a yield of 5%. Elemental analysis calculated: C 49.18, H 2.73, N 7.65%; found: C 49.12, H 2.77, N 7.61%.

Refinement top

H atoms bound to C atoms were placed geometrically and refined as riding atoms with C—H= 0.93 Å and with Uiso(H) = 1.2Ueq(C). The H atom on O1 was also placed geometrically and refined as riding atom with O—H = 0.82 Å and with Uiso(H) = 1.5Ueq(O). The H atom on O6 was located in a difference Fourier map and refined with O—H restrained to be 0.82 (1) Å and with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); 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 (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing displacement ellipsoids at 30% probability for non-H atoms. The suffixes I and II denote atoms generated by the symmetry operators (−x, y − 1/2, −z + 3/2) and (1 − x, y − 1/2, −z + 1/2), respectively.
[Figure 2] Fig. 2. Packing diagram showing zigzag chains extending palallel to [010]. H atoms have been omitted.
catena-Poly[[(2,2'-bipyridine-κ2N,N')iron(II)]-µ- 5-carboxy-4-carboxylatoimidazol-1-ido- κ4N3,O4:N1,O5] top
Crystal data top
[Fe(C5H2N2O4)(C10H8N2)]F000 = 1488
Mr = 366.12Dx = 1.743 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5866 reflections
a = 19.9862 (10) Åθ = 2.3–26.7º
b = 9.8828 (5) ŵ = 1.11 mm−1
c = 14.4351 (7) ÅT = 293 (2) K
β = 101.806 (1)ºBlock, green
V = 2790.9 (2) Å30.43 × 0.35 × 0.28 mm
Z = 8
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5866 independent reflections
Radiation source: fine-focus sealed tube4863 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 293(2) Kθmax = 26.7º
φ and ω scansθmin = 2.3º
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −25→20
Tmin = 0.647, Tmax = 0.746k = −11→10
15091 measured reflectionsl = −17→18
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)] = 0.036H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.100  w = 1/[σ2(Fo2) + (0.061P)2 + 2.1242P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
5866 reflectionsΔρmax = 0.44 e Å−3
437 parametersΔρmin = −0.49 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Fe(C5H2N2O4)(C10H8N2)]V = 2790.9 (2) Å3
Mr = 366.12Z = 8
Monoclinic, P21/cMo Kα
a = 19.9862 (10) ŵ = 1.11 mm−1
b = 9.8828 (5) ÅT = 293 (2) K
c = 14.4351 (7) Å0.43 × 0.35 × 0.28 mm
β = 101.806 (1)º
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5866 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		4863 reflections with I > 2σ(I)
Tmin = 0.647, Tmax = 0.746Rint = 0.027
15091 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0361 restraint
wR(F2) = 0.100H atoms treated by a mixture of
independent and constrained refinement
S = 1.00Δρmax = 0.44 e Å−3
5866 reflectionsΔρmin = −0.49 e Å−3
437 parameters
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
C10.25412 (13)−0.1015 (3)0.11260 (18)0.0286 (6)
C20.18886 (14)−0.1492 (3)0.09414 (19)0.0336 (6)
H20.1524−0.09040.07450.040*
C30.17701 (14)−0.2887 (3)0.1050 (2)0.0357 (6)
H30.1325−0.32200.09110.043*
C40.23018 (15)−0.3752 (3)0.13573 (19)0.0335 (6)
H40.2231−0.46710.14370.040*
C50.29390 (14)−0.3204 (3)0.15413 (19)0.0318 (6)
H50.3310−0.37710.17540.038*
C60.27142 (13)0.0457 (3)0.09936 (18)0.0287 (6)
C70.22341 (14)0.1449 (3)0.06224 (19)0.0338 (6)
H70.17740.12190.04520.041*
C80.24383 (15)0.2782 (3)0.0504 (2)0.0365 (6)
H80.21160.34390.02660.044*
C90.31112 (15)0.3106 (3)0.0741 (2)0.0371 (6)
H90.32660.39780.06650.045*
C100.35557 (14)0.2074 (3)0.1101 (2)0.0355 (6)
H100.40190.22810.12670.043*
C110.52108 (13)0.1314 (3)0.22142 (18)0.0281 (5)
H110.53470.13200.16350.034*
C120.51363 (13)0.1848 (3)0.35977 (18)0.0270 (5)
C130.47003 (13)0.0770 (3)0.32962 (18)0.0265 (5)
C140.41974 (13)0.0067 (3)0.37172 (19)0.0289 (6)
C150.52678 (13)0.2659 (3)0.44617 (18)0.0286 (6)
C160.24864 (14)−0.0084 (3)0.85456 (18)0.0305 (6)
C170.31616 (15)0.0270 (3)0.8779 (2)0.0417 (7)
H170.3489−0.03640.90430.050*
C180.33542 (16)0.1596 (4)0.8615 (2)0.0486 (8)
H180.38140.18330.87680.058*
C190.28792 (15)0.2557 (3)0.8235 (2)0.0424 (7)
H190.30040.34350.81150.051*
C200.22184 (14)0.2149 (3)0.80465 (19)0.0342 (6)
H200.18820.27750.77990.041*
C210.22464 (13)−0.1523 (3)0.86056 (18)0.0305 (6)
C220.26600 (16)−0.2602 (3)0.8977 (2)0.0392 (7)
H220.3119−0.24460.92390.047*
C230.24014 (18)−0.3919 (3)0.8965 (2)0.0468 (8)
H230.2684−0.46310.92210.056*
C240.17451 (17)−0.4144 (3)0.8583 (2)0.0445 (8)
H240.1555−0.50040.85680.053*
C250.13582 (16)−0.3022 (3)0.8205 (2)0.0377 (7)
H250.0902−0.31660.79240.045*
C260.06717 (13)0.1530 (3)0.60594 (17)0.0280 (5)
C270.04097 (12)0.2468 (3)0.66939 (17)0.0251 (5)
C28−0.00283 (13)0.3567 (3)0.65276 (17)0.0254 (5)
C290.02308 (13)0.3216 (3)0.79865 (17)0.0267 (5)
H290.02550.33080.86340.032*
C30−0.04275 (12)0.4138 (3)0.56638 (17)0.0248 (5)
Fe10.100575 (14)0.02478 (3)0.78559 (2)0.01296 (10)
Fe20.402091 (15)−0.09584 (3)0.18027 (2)0.01510 (10)
N10.47565 (11)0.0429 (2)0.24137 (15)0.0275 (5)
N20.05700 (11)0.2242 (2)0.76226 (14)0.0265 (5)
N30.33654 (11)0.0779 (2)0.12307 (16)0.0298 (5)
N40.30592 (11)−0.1867 (2)0.14295 (15)0.0296 (5)
N50.20255 (11)0.0867 (2)0.82027 (15)0.0295 (5)
N60.15995 (11)−0.1735 (2)0.82203 (16)0.0316 (5)
N7−0.01405 (11)0.4035 (2)0.73571 (14)0.0263 (5)
N80.54562 (11)0.2190 (2)0.29037 (15)0.0282 (5)
O10.41577 (10)0.0408 (2)0.45503 (14)0.0355 (5)
H10.44620.09530.47560.053*
O20.38175 (10)−0.0777 (2)0.32461 (14)0.0343 (4)
O30.56775 (10)0.3637 (2)0.45259 (13)0.0344 (4)
O40.49475 (10)0.2334 (2)0.50895 (13)0.0364 (5)
O5−0.08546 (9)0.50345 (19)0.57110 (12)0.0285 (4)
O6−0.03321 (9)0.3645 (2)0.48931 (12)0.0310 (4)
O70.05428 (11)0.1818 (2)0.52042 (13)0.0394 (5)
O80.10133 (10)0.0515 (2)0.64077 (13)0.0313 (4)
H6−0.0001 (13)0.314 (2)0.499 (3)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0262 (13)0.0346 (15)0.0241 (12)0.0017 (11)0.0032 (10)0.0001 (10)
C20.0277 (14)0.0376 (16)0.0337 (14)−0.0009 (12)0.0019 (11)0.0051 (12)
C30.0272 (14)0.0438 (17)0.0343 (14)−0.0068 (12)0.0021 (11)0.0025 (13)
C40.0366 (15)0.0313 (15)0.0321 (13)−0.0073 (12)0.0058 (11)0.0017 (12)
C50.0311 (14)0.0298 (15)0.0337 (13)0.0003 (11)0.0045 (11)0.0017 (11)
C60.0253 (13)0.0333 (15)0.0264 (12)−0.0007 (11)0.0029 (10)−0.0005 (11)
C70.0269 (14)0.0398 (16)0.0326 (14)0.0028 (12)0.0014 (11)0.0001 (12)
C80.0363 (15)0.0330 (16)0.0376 (15)0.0077 (12)0.0012 (12)0.0046 (12)
C90.0390 (16)0.0301 (15)0.0416 (15)−0.0019 (12)0.0066 (13)0.0039 (12)
C100.0288 (14)0.0375 (16)0.0393 (15)−0.0041 (12)0.0049 (11)0.0021 (13)
C110.0240 (12)0.0339 (15)0.0259 (12)−0.0025 (11)0.0037 (10)−0.0004 (11)
C120.0220 (12)0.0312 (14)0.0269 (12)0.0020 (10)0.0029 (10)0.0012 (11)
C130.0232 (12)0.0297 (14)0.0255 (12)0.0040 (10)0.0025 (10)0.0005 (10)
C140.0244 (13)0.0310 (14)0.0306 (13)0.0036 (11)0.0042 (10)−0.0001 (11)
C150.0239 (12)0.0309 (14)0.0290 (13)0.0030 (11)0.0010 (10)0.0001 (11)
C160.0258 (13)0.0412 (16)0.0234 (12)0.0041 (12)0.0028 (10)−0.0005 (11)
C170.0256 (14)0.054 (2)0.0430 (16)0.0045 (13)0.0014 (12)−0.0012 (14)
C180.0258 (15)0.062 (2)0.0547 (19)−0.0096 (15)0.0009 (13)−0.0088 (17)
C190.0357 (16)0.0442 (18)0.0468 (17)−0.0089 (14)0.0073 (13)−0.0026 (14)
C200.0318 (14)0.0337 (16)0.0356 (14)−0.0034 (12)0.0033 (11)−0.0003 (12)
C210.0268 (13)0.0417 (16)0.0239 (12)0.0055 (12)0.0072 (10)0.0032 (11)
C220.0341 (15)0.0472 (19)0.0364 (15)0.0117 (13)0.0076 (12)0.0069 (13)
C230.0469 (19)0.045 (2)0.0507 (18)0.0204 (15)0.0159 (15)0.0115 (15)
C240.0488 (19)0.0328 (17)0.0558 (19)0.0067 (14)0.0194 (16)0.0039 (14)
C250.0383 (16)0.0338 (16)0.0441 (16)0.0028 (13)0.0157 (13)0.0014 (13)
C260.0256 (13)0.0311 (14)0.0267 (12)0.0015 (11)0.0041 (10)0.0007 (11)
C270.0220 (12)0.0289 (14)0.0239 (11)−0.0013 (10)0.0036 (9)0.0015 (10)
C280.0239 (12)0.0278 (13)0.0243 (11)−0.0019 (10)0.0042 (9)−0.0007 (10)
C290.0272 (13)0.0320 (14)0.0205 (11)0.0009 (11)0.0041 (9)0.0005 (10)
C300.0220 (12)0.0274 (14)0.0247 (12)−0.0016 (10)0.0045 (10)−0.0007 (10)
Fe10.00936 (16)0.01382 (18)0.01510 (16)0.00017 (11)0.00110 (11)0.00294 (11)
Fe20.00912 (16)0.01409 (18)0.01998 (17)0.00012 (11)−0.00194 (12)−0.00090 (12)
N10.0225 (11)0.0331 (13)0.0258 (10)0.0005 (9)0.0022 (8)−0.0010 (9)
N20.0255 (11)0.0296 (12)0.0237 (10)0.0010 (9)0.0036 (8)0.0018 (9)
N30.0246 (11)0.0315 (12)0.0322 (11)−0.0007 (9)0.0034 (9)0.0022 (10)
N40.0253 (11)0.0337 (13)0.0282 (11)−0.0011 (9)0.0018 (9)0.0008 (9)
N50.0233 (11)0.0382 (14)0.0270 (11)0.0002 (9)0.0049 (9)0.0010 (9)
N60.0287 (12)0.0343 (13)0.0323 (11)0.0042 (10)0.0075 (9)0.0014 (10)
N70.0258 (11)0.0298 (12)0.0227 (10)0.0009 (9)0.0031 (8)−0.0003 (9)
N80.0251 (11)0.0325 (12)0.0263 (11)−0.0008 (9)0.0035 (8)0.0009 (9)
O10.0325 (11)0.0430 (13)0.0332 (10)−0.0032 (9)0.0116 (8)−0.0016 (9)
O20.0266 (10)0.0404 (11)0.0366 (10)−0.0060 (8)0.0078 (8)−0.0017 (9)
O30.0307 (10)0.0383 (11)0.0321 (10)−0.0033 (9)0.0015 (8)−0.0053 (8)
O40.0373 (11)0.0437 (12)0.0287 (10)−0.0003 (9)0.0078 (8)−0.0035 (9)
O50.0247 (9)0.0341 (10)0.0259 (9)0.0044 (8)0.0034 (7)0.0022 (8)
O60.0297 (10)0.0377 (11)0.0243 (9)0.0053 (8)0.0026 (7)0.0014 (8)
O70.0485 (12)0.0471 (13)0.0234 (9)0.0151 (10)0.0089 (8)0.0011 (9)
O80.0323 (10)0.0328 (10)0.0293 (9)0.0077 (8)0.0077 (8)0.0016 (8)
Geometric parameters (Å, °) top
C1—N41.337 (3)C20—N51.357 (4)
C1—C21.361 (4)C20—H200.930
C1—C61.517 (4)C21—N61.316 (3)
C2—C31.413 (4)C21—C221.388 (4)
C2—H20.930C22—C231.400 (5)
C3—C41.365 (4)C22—H220.930
C3—H30.930C23—C241.333 (5)
C4—C51.359 (4)C23—H230.930
C4—H40.930C24—C251.397 (4)
C5—N41.358 (4)C24—H240.930
C5—H50.930C25—N61.358 (4)
C6—N31.315 (3)C25—H250.930
C6—C71.399 (4)C26—O71.241 (3)
C7—C81.400 (4)C26—O81.259 (3)
C7—H70.930C26—C271.473 (4)
C8—C91.357 (4)C27—N21.332 (3)
C8—H80.930C27—C281.384 (4)
C9—C101.382 (4)C28—N71.345 (3)
C9—H90.930C28—C301.450 (3)
C10—N31.359 (4)C29—N71.325 (3)
C10—H100.930C29—N21.345 (3)
C11—N11.334 (3)C29—H290.930
C11—N81.334 (3)C30—O51.242 (3)
C11—H110.930C30—O61.264 (3)
C12—N81.337 (3)Fe1—N7i2.074 (2)
C12—C131.389 (4)Fe1—N52.088 (2)
C12—C151.460 (4)Fe1—O82.1102 (18)
C13—N11.344 (3)Fe1—N22.153 (2)
C13—C141.453 (4)Fe1—O5i2.1613 (18)
C14—O21.234 (3)Fe1—N62.296 (2)
C14—O11.267 (3)Fe2—N12.071 (2)
C15—O41.254 (3)Fe2—N42.090 (2)
C15—O31.258 (3)Fe2—N8ii2.107 (2)
C16—N51.338 (4)Fe2—O3ii2.162 (2)
C16—C171.368 (4)Fe2—O22.210 (2)
C16—C211.509 (4)Fe2—N32.215 (2)
C17—C181.399 (5)N7—Fe1iii2.074 (2)
C17—H170.930N8—Fe2iv2.107 (2)
C18—C191.375 (5)O1—H10.820
C18—H180.930O3—Fe2iv2.162 (2)
C19—C201.354 (4)O5—Fe1iii2.1613 (18)
C19—H190.930O6—H60.82 (3)
N4—C1—C2119.5 (3)O7—C26—O8124.4 (2)
N4—C1—C6117.7 (2)O7—C26—C27116.5 (2)
C2—C1—C6122.8 (2)O8—C26—C27119.1 (2)
C1—C2—C3119.5 (3)N2—C27—C28108.6 (2)
C1—C2—H2120.3N2—C27—C26118.5 (2)
C3—C2—H2120.3C28—C27—C26132.7 (2)
C4—C3—C2120.7 (3)N7—C28—C27109.3 (2)
C4—C3—H3119.7N7—C28—C30118.0 (2)
C2—C3—H3119.7C27—C28—C30132.2 (2)
C5—C4—C3116.8 (3)N7—C29—N2115.2 (2)
C5—C4—H4121.6N7—C29—H29122.4
C3—C4—H4121.6N2—C29—H29122.4
N4—C5—C4123.1 (3)O5—C30—O6123.5 (2)
N4—C5—H5118.5O5—C30—C28119.6 (2)
C4—C5—H5118.5O6—C30—C28116.8 (2)
N3—C6—C7119.7 (3)N7i—Fe1—N5161.40 (9)
N3—C6—C1116.0 (2)N7i—Fe1—O895.75 (8)
C7—C6—C1124.3 (2)N5—Fe1—O889.80 (8)
C6—C7—C8120.8 (3)N7i—Fe1—N2101.96 (8)
C6—C7—H7119.6N5—Fe1—N296.50 (9)
C8—C7—H7119.6O8—Fe1—N279.36 (8)
C9—C8—C7119.4 (3)N7i—Fe1—O5i79.05 (7)
C9—C8—H8120.3N5—Fe1—O5i96.88 (8)
C7—C8—H8120.3O8—Fe1—O5i172.39 (7)
C8—C9—C10116.6 (3)N2—Fe1—O5i96.18 (7)
C8—C9—H9121.7N7i—Fe1—N685.24 (8)
C10—C9—H9121.7N5—Fe1—N676.21 (9)
N3—C10—C9124.7 (3)O8—Fe1—N6103.04 (8)
N3—C10—H10117.6N2—Fe1—N6172.23 (8)
C9—C10—H10117.6O5i—Fe1—N682.20 (8)
N1—C11—N8115.3 (2)N1—Fe2—N4158.38 (9)
N1—C11—H11122.4N1—Fe2—N8ii102.12 (8)
N8—C11—H11122.4N4—Fe2—N8ii94.04 (9)
N8—C12—C13108.9 (2)N1—Fe2—O3ii101.41 (8)
N8—C12—C15118.1 (2)N4—Fe2—O3ii95.76 (8)
C13—C12—C15132.9 (2)N8ii—Fe2—O3ii78.51 (8)
N1—C13—C12108.7 (2)N1—Fe2—O278.24 (8)
N1—C13—C14118.4 (2)N4—Fe2—O286.62 (8)
C12—C13—C14132.8 (2)N8ii—Fe2—O293.45 (8)
O2—C14—O1123.5 (3)O3ii—Fe2—O2171.74 (7)
O2—C14—C13119.5 (2)N1—Fe2—N387.68 (8)
O1—C14—C13116.9 (2)N4—Fe2—N378.15 (9)
O4—C15—O3124.4 (2)N8ii—Fe2—N3168.44 (8)
O4—C15—C12116.6 (2)O3ii—Fe2—N393.66 (8)
O3—C15—C12119.0 (2)O2—Fe2—N394.57 (8)
N5—C16—C17118.8 (3)C11—N1—C13103.5 (2)
N5—C16—C21118.7 (2)C11—N1—Fe2142.88 (18)
C17—C16—C21122.4 (3)C13—N1—Fe2112.30 (17)
C16—C17—C18119.3 (3)C27—N2—C29103.7 (2)
C16—C17—H17120.3C27—N2—Fe1108.53 (17)
C18—C17—H17120.3C29—N2—Fe1144.53 (17)
C19—C18—C17121.5 (3)C6—N3—C10118.8 (2)
C19—C18—H18119.2C6—N3—Fe2112.81 (18)
C17—C18—H18119.2C10—N3—Fe2128.37 (18)
C20—C19—C18116.1 (3)C1—N4—C5120.5 (2)
C20—C19—H19122.0C1—N4—Fe2115.04 (18)
C18—C19—H19122.0C5—N4—Fe2124.28 (18)
C19—C20—N5122.9 (3)C16—N5—C20121.3 (2)
C19—C20—H20118.5C16—N5—Fe1116.59 (19)
N5—C20—H20118.5C20—N5—Fe1122.02 (18)
N6—C21—C22119.8 (3)C21—N6—C25118.1 (2)
N6—C21—C16115.0 (2)C21—N6—Fe1112.18 (19)
C22—C21—C16125.1 (3)C25—N6—Fe1129.06 (19)
C21—C22—C23121.4 (3)C29—N7—C28103.2 (2)
C21—C22—H22119.3C29—N7—Fe1iii141.96 (18)
C23—C22—H22119.3C28—N7—Fe1iii110.65 (16)
C24—C23—C22119.3 (3)C11—N8—C12103.6 (2)
C24—C23—H23120.3C11—N8—Fe2iv143.60 (18)
C22—C23—H23120.3C12—N8—Fe2iv111.23 (17)
C23—C24—C25116.6 (3)C14—O1—H1109.5
C23—C24—H24121.7C14—O2—Fe2111.30 (17)
C25—C24—H24121.7C15—O3—Fe2iv111.86 (16)
N6—C25—C24124.8 (3)C30—O5—Fe1iii110.75 (15)
N6—C25—H25117.6C30—O6—H6110 (3)
C24—C25—H25117.6C26—O8—Fe1112.45 (16)
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+3/2; (iv) −x+1, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.821.692.493 (3)167
O6—H6···O70.82 (3)1.69 (2)2.489 (2)167 (2)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.821.692.493 (3)167
O6—H6···O70.82 (3)1.69 (2)2.489 (2)167 (2)
Acknowledgements top

The authors thank Shandong Institute of Light Industry for financial support.

references
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