Retracted: catena-Poly[[(2,2′-bipyridine-κ²N,N′)iron(II)]-μ-5-carboxy-4-carboxylatoimidazol-1-ido-κ⁴N³,O⁴:N¹,O⁵]

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 Fe^II atom is octa­hedral, comprising two O atoms and four N atoms. Each Fe^II atom is chelated by one 2,2′-bipyridine ligand, and is linked to two neighbouring Fe^II 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.100
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1         (2)       2.13
PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe2         (2)       2.15
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

S1. Comment

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, Fe^II 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 Fe^II atoms, giving rise to one-dimensional zigzag chains along [010] (Fig. 2). The 2,2'-bipyridine ligands are situated between these chains.

Related literature

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

S2. Experimental

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%.

S3. Refinement

H atoms bound to C atoms were placed geometrically and refined as riding atoms with C—H= 0.93 Å and with U_iso(H) = 1.2U_eq(C). The H atom on O1 was also placed geometrically and refined as riding atom with O—H = 0.82 Å and with U_iso(H) = 1.5U_eq(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 U_iso(H) = 1.5U_eq(O).

Computing details

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

	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.
	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]

Crystal data

[Fe(C5H2N2O4)(C10H8N2)]	F(000) = 1488
Mr = 366.12	Dx = 1.743 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5866 reflections
a = 19.9862 (10) Å	θ = 2.3–26.7°
b = 9.8828 (5) Å	µ = 1.11 mm^−1
c = 14.4351 (7) Å	T = 293 K
β = 101.806 (1)°	Block, green
V = 2790.9 (2) Å^3	0.43 × 0.35 × 0.28 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer	5866 independent reflections
Radiation source: fine-focus sealed tube	4863 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 26.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −25→20
Tmin = 0.647, Tmax = 0.746	k = −11→10
15091 measured reflections	l = −17→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 2.1242P] where P = (Fo^2 + 2Fc^2)/3
5866 reflections	(Δ/σ)max < 0.001
437 parameters	Δρmax = 0.44 e Å^−3
1 restraint	Δρmin = −0.49 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.25412 (13)	−0.1015 (3)	0.11260 (18)	0.0286 (6)
C2	0.18886 (14)	−0.1492 (3)	0.09414 (19)	0.0336 (6)
H2	0.1524	−0.0904	0.0745	0.040*
C3	0.17701 (14)	−0.2887 (3)	0.1050 (2)	0.0357 (6)
H3	0.1325	−0.3220	0.0911	0.043*
C4	0.23018 (15)	−0.3752 (3)	0.13573 (19)	0.0335 (6)
H4	0.2231	−0.4671	0.1437	0.040*
C5	0.29390 (14)	−0.3204 (3)	0.15413 (19)	0.0318 (6)
H5	0.3310	−0.3771	0.1754	0.038*
C6	0.27142 (13)	0.0457 (3)	0.09936 (18)	0.0287 (6)
C7	0.22341 (14)	0.1449 (3)	0.06224 (19)	0.0338 (6)
H7	0.1774	0.1219	0.0452	0.041*
C8	0.24383 (15)	0.2782 (3)	0.0504 (2)	0.0365 (6)
H8	0.2116	0.3439	0.0266	0.044*
C9	0.31112 (15)	0.3106 (3)	0.0741 (2)	0.0371 (6)
H9	0.3266	0.3978	0.0665	0.045*
C10	0.35557 (14)	0.2074 (3)	0.1101 (2)	0.0355 (6)
H10	0.4019	0.2281	0.1267	0.043*
C11	0.52108 (13)	0.1314 (3)	0.22142 (18)	0.0281 (5)
H11	0.5347	0.1320	0.1635	0.034*
C12	0.51363 (13)	0.1848 (3)	0.35977 (18)	0.0270 (5)
C13	0.47003 (13)	0.0770 (3)	0.32962 (18)	0.0265 (5)
C14	0.41974 (13)	0.0067 (3)	0.37172 (19)	0.0289 (6)
C15	0.52678 (13)	0.2659 (3)	0.44617 (18)	0.0286 (6)
C16	0.24864 (14)	−0.0084 (3)	0.85456 (18)	0.0305 (6)
C17	0.31616 (15)	0.0270 (3)	0.8779 (2)	0.0417 (7)
H17	0.3489	−0.0364	0.9043	0.050*
C18	0.33542 (16)	0.1596 (4)	0.8615 (2)	0.0486 (8)
H18	0.3814	0.1833	0.8768	0.058*
C19	0.28792 (15)	0.2557 (3)	0.8235 (2)	0.0424 (7)
H19	0.3004	0.3435	0.8115	0.051*
C20	0.22184 (14)	0.2149 (3)	0.80465 (19)	0.0342 (6)
H20	0.1882	0.2775	0.7799	0.041*
C21	0.22464 (13)	−0.1523 (3)	0.86056 (18)	0.0305 (6)
C22	0.26600 (16)	−0.2602 (3)	0.8977 (2)	0.0392 (7)
H22	0.3119	−0.2446	0.9239	0.047*
C23	0.24014 (18)	−0.3919 (3)	0.8965 (2)	0.0468 (8)
H23	0.2684	−0.4631	0.9221	0.056*
C24	0.17451 (17)	−0.4144 (3)	0.8583 (2)	0.0445 (8)
H24	0.1555	−0.5004	0.8568	0.053*
C25	0.13582 (16)	−0.3022 (3)	0.8205 (2)	0.0377 (7)
H25	0.0902	−0.3166	0.7924	0.045*
C26	0.06717 (13)	0.1530 (3)	0.60594 (17)	0.0280 (5)
C27	0.04097 (12)	0.2468 (3)	0.66939 (17)	0.0251 (5)
C28	−0.00283 (13)	0.3567 (3)	0.65276 (17)	0.0254 (5)
C29	0.02308 (13)	0.3216 (3)	0.79865 (17)	0.0267 (5)
H29	0.0255	0.3308	0.8634	0.032*
C30	−0.04275 (12)	0.4138 (3)	0.56638 (17)	0.0248 (5)
Fe1	0.100575 (14)	0.02478 (3)	0.78559 (2)	0.01296 (10)
Fe2	0.402091 (15)	−0.09584 (3)	0.18027 (2)	0.01510 (10)
N1	0.47565 (11)	0.0429 (2)	0.24137 (15)	0.0275 (5)
N2	0.05700 (11)	0.2242 (2)	0.76226 (14)	0.0265 (5)
N3	0.33654 (11)	0.0779 (2)	0.12307 (16)	0.0298 (5)
N4	0.30592 (11)	−0.1867 (2)	0.14295 (15)	0.0296 (5)
N5	0.20255 (11)	0.0867 (2)	0.82027 (15)	0.0295 (5)
N6	0.15995 (11)	−0.1735 (2)	0.82203 (16)	0.0316 (5)
N7	−0.01405 (11)	0.4035 (2)	0.73571 (14)	0.0263 (5)
N8	0.54562 (11)	0.2190 (2)	0.29037 (15)	0.0282 (5)
O1	0.41577 (10)	0.0408 (2)	0.45503 (14)	0.0355 (5)
H1	0.4462	0.0953	0.4756	0.053*
O2	0.38175 (10)	−0.0777 (2)	0.32461 (14)	0.0343 (4)
O3	0.56775 (10)	0.3637 (2)	0.45259 (13)	0.0344 (4)
O4	0.49475 (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)
O7	0.05428 (11)	0.1818 (2)	0.52042 (13)	0.0394 (5)
O8	0.10133 (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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0262 (13)	0.0346 (15)	0.0241 (12)	0.0017 (11)	0.0032 (10)	0.0001 (10)
C2	0.0277 (14)	0.0376 (16)	0.0337 (14)	−0.0009 (12)	0.0019 (11)	0.0051 (12)
C3	0.0272 (14)	0.0438 (17)	0.0343 (14)	−0.0068 (12)	0.0021 (11)	0.0025 (13)
C4	0.0366 (15)	0.0313 (15)	0.0321 (13)	−0.0073 (12)	0.0058 (11)	0.0017 (12)
C5	0.0311 (14)	0.0298 (15)	0.0337 (13)	0.0003 (11)	0.0045 (11)	0.0017 (11)
C6	0.0253 (13)	0.0333 (15)	0.0264 (12)	−0.0007 (11)	0.0029 (10)	−0.0005 (11)
C7	0.0269 (14)	0.0398 (16)	0.0326 (14)	0.0028 (12)	0.0014 (11)	0.0001 (12)
C8	0.0363 (15)	0.0330 (16)	0.0376 (15)	0.0077 (12)	0.0012 (12)	0.0046 (12)
C9	0.0390 (16)	0.0301 (15)	0.0416 (15)	−0.0019 (12)	0.0066 (13)	0.0039 (12)
C10	0.0288 (14)	0.0375 (16)	0.0393 (15)	−0.0041 (12)	0.0049 (11)	0.0021 (13)
C11	0.0240 (12)	0.0339 (15)	0.0259 (12)	−0.0025 (11)	0.0037 (10)	−0.0004 (11)
C12	0.0220 (12)	0.0312 (14)	0.0269 (12)	0.0020 (10)	0.0029 (10)	0.0012 (11)
C13	0.0232 (12)	0.0297 (14)	0.0255 (12)	0.0040 (10)	0.0025 (10)	0.0005 (10)
C14	0.0244 (13)	0.0310 (14)	0.0306 (13)	0.0036 (11)	0.0042 (10)	−0.0001 (11)
C15	0.0239 (12)	0.0309 (14)	0.0290 (13)	0.0030 (11)	0.0010 (10)	0.0001 (11)
C16	0.0258 (13)	0.0412 (16)	0.0234 (12)	0.0041 (12)	0.0028 (10)	−0.0005 (11)
C17	0.0256 (14)	0.054 (2)	0.0430 (16)	0.0045 (13)	0.0014 (12)	−0.0012 (14)
C18	0.0258 (15)	0.062 (2)	0.0547 (19)	−0.0096 (15)	0.0009 (13)	−0.0088 (17)
C19	0.0357 (16)	0.0442 (18)	0.0468 (17)	−0.0089 (14)	0.0073 (13)	−0.0026 (14)
C20	0.0318 (14)	0.0337 (16)	0.0356 (14)	−0.0034 (12)	0.0033 (11)	−0.0003 (12)
C21	0.0268 (13)	0.0417 (16)	0.0239 (12)	0.0055 (12)	0.0072 (10)	0.0032 (11)
C22	0.0341 (15)	0.0472 (19)	0.0364 (15)	0.0117 (13)	0.0076 (12)	0.0069 (13)
C23	0.0469 (19)	0.045 (2)	0.0507 (18)	0.0204 (15)	0.0159 (15)	0.0115 (15)
C24	0.0488 (19)	0.0328 (17)	0.0558 (19)	0.0067 (14)	0.0194 (16)	0.0039 (14)
C25	0.0383 (16)	0.0338 (16)	0.0441 (16)	0.0028 (13)	0.0157 (13)	0.0014 (13)
C26	0.0256 (13)	0.0311 (14)	0.0267 (12)	0.0015 (11)	0.0041 (10)	0.0007 (11)
C27	0.0220 (12)	0.0289 (14)	0.0239 (11)	−0.0013 (10)	0.0036 (9)	0.0015 (10)
C28	0.0239 (12)	0.0278 (13)	0.0243 (11)	−0.0019 (10)	0.0042 (9)	−0.0007 (10)
C29	0.0272 (13)	0.0320 (14)	0.0205 (11)	0.0009 (11)	0.0041 (9)	0.0005 (10)
C30	0.0220 (12)	0.0274 (14)	0.0247 (12)	−0.0016 (10)	0.0045 (10)	−0.0007 (10)
Fe1	0.00936 (16)	0.01382 (18)	0.01510 (16)	0.00017 (11)	0.00110 (11)	0.00294 (11)
Fe2	0.00912 (16)	0.01409 (18)	0.01998 (17)	0.00012 (11)	−0.00194 (12)	−0.00090 (12)
N1	0.0225 (11)	0.0331 (13)	0.0258 (10)	0.0005 (9)	0.0022 (8)	−0.0010 (9)
N2	0.0255 (11)	0.0296 (12)	0.0237 (10)	0.0010 (9)	0.0036 (8)	0.0018 (9)
N3	0.0246 (11)	0.0315 (12)	0.0322 (11)	−0.0007 (9)	0.0034 (9)	0.0022 (10)
N4	0.0253 (11)	0.0337 (13)	0.0282 (11)	−0.0011 (9)	0.0018 (9)	0.0008 (9)
N5	0.0233 (11)	0.0382 (14)	0.0270 (11)	0.0002 (9)	0.0049 (9)	0.0010 (9)
N6	0.0287 (12)	0.0343 (13)	0.0323 (11)	0.0042 (10)	0.0075 (9)	0.0014 (10)
N7	0.0258 (11)	0.0298 (12)	0.0227 (10)	0.0009 (9)	0.0031 (8)	−0.0003 (9)
N8	0.0251 (11)	0.0325 (12)	0.0263 (11)	−0.0008 (9)	0.0035 (8)	0.0009 (9)
O1	0.0325 (11)	0.0430 (13)	0.0332 (10)	−0.0032 (9)	0.0116 (8)	−0.0016 (9)
O2	0.0266 (10)	0.0404 (11)	0.0366 (10)	−0.0060 (8)	0.0078 (8)	−0.0017 (9)
O3	0.0307 (10)	0.0383 (11)	0.0321 (10)	−0.0033 (9)	0.0015 (8)	−0.0053 (8)
O4	0.0373 (11)	0.0437 (12)	0.0287 (10)	−0.0003 (9)	0.0078 (8)	−0.0035 (9)
O5	0.0247 (9)	0.0341 (10)	0.0259 (9)	0.0044 (8)	0.0034 (7)	0.0022 (8)
O6	0.0297 (10)	0.0377 (11)	0.0243 (9)	0.0053 (8)	0.0026 (7)	0.0014 (8)
O7	0.0485 (12)	0.0471 (13)	0.0234 (9)	0.0151 (10)	0.0089 (8)	0.0011 (9)
O8	0.0323 (10)	0.0328 (10)	0.0293 (9)	0.0077 (8)	0.0077 (8)	0.0016 (8)

Geometric parameters (Å, º)

C1—N4	1.337 (3)	C20—N5	1.357 (4)
C1—C2	1.361 (4)	C20—H20	0.930
C1—C6	1.517 (4)	C21—N6	1.316 (3)
C2—C3	1.413 (4)	C21—C22	1.388 (4)
C2—H2	0.930	C22—C23	1.400 (5)
C3—C4	1.365 (4)	C22—H22	0.930
C3—H3	0.930	C23—C24	1.333 (5)
C4—C5	1.359 (4)	C23—H23	0.930
C4—H4	0.930	C24—C25	1.397 (4)
C5—N4	1.358 (4)	C24—H24	0.930
C5—H5	0.930	C25—N6	1.358 (4)
C6—N3	1.315 (3)	C25—H25	0.930
C6—C7	1.399 (4)	C26—O7	1.241 (3)
C7—C8	1.400 (4)	C26—O8	1.259 (3)
C7—H7	0.930	C26—C27	1.473 (4)
C8—C9	1.357 (4)	C27—N2	1.332 (3)
C8—H8	0.930	C27—C28	1.384 (4)
C9—C10	1.382 (4)	C28—N7	1.345 (3)
C9—H9	0.930	C28—C30	1.450 (3)
C10—N3	1.359 (4)	C29—N7	1.325 (3)
C10—H10	0.930	C29—N2	1.345 (3)
C11—N1	1.334 (3)	C29—H29	0.930
C11—N8	1.334 (3)	C30—O5	1.242 (3)
C11—H11	0.930	C30—O6	1.264 (3)
C12—N8	1.337 (3)	Fe1—N7^i	2.074 (2)
C12—C13	1.389 (4)	Fe1—N5	2.088 (2)
C12—C15	1.460 (4)	Fe1—O8	2.1102 (18)
C13—N1	1.344 (3)	Fe1—N2	2.153 (2)
C13—C14	1.453 (4)	Fe1—O5^i	2.1613 (18)
C14—O2	1.234 (3)	Fe1—N6	2.296 (2)
C14—O1	1.267 (3)	Fe2—N1	2.071 (2)
C15—O4	1.254 (3)	Fe2—N4	2.090 (2)
C15—O3	1.258 (3)	Fe2—N8^ii	2.107 (2)
C16—N5	1.338 (4)	Fe2—O3^ii	2.162 (2)
C16—C17	1.368 (4)	Fe2—O2	2.210 (2)
C16—C21	1.509 (4)	Fe2—N3	2.215 (2)
C17—C18	1.399 (5)	N7—Fe1^iii	2.074 (2)
C17—H17	0.930	N8—Fe2^iv	2.107 (2)
C18—C19	1.375 (5)	O1—H1	0.820
C18—H18	0.930	O3—Fe2^iv	2.162 (2)
C19—C20	1.354 (4)	O5—Fe1^iii	2.1613 (18)
C19—H19	0.930	O6—H6	0.82 (3)
N4—C1—C2	119.5 (3)	O7—C26—O8	124.4 (2)
N4—C1—C6	117.7 (2)	O7—C26—C27	116.5 (2)
C2—C1—C6	122.8 (2)	O8—C26—C27	119.1 (2)
C1—C2—C3	119.5 (3)	N2—C27—C28	108.6 (2)
C1—C2—H2	120.3	N2—C27—C26	118.5 (2)
C3—C2—H2	120.3	C28—C27—C26	132.7 (2)
C4—C3—C2	120.7 (3)	N7—C28—C27	109.3 (2)
C4—C3—H3	119.7	N7—C28—C30	118.0 (2)
C2—C3—H3	119.7	C27—C28—C30	132.2 (2)
C5—C4—C3	116.8 (3)	N7—C29—N2	115.2 (2)
C5—C4—H4	121.6	N7—C29—H29	122.4
C3—C4—H4	121.6	N2—C29—H29	122.4
N4—C5—C4	123.1 (3)	O5—C30—O6	123.5 (2)
N4—C5—H5	118.5	O5—C30—C28	119.6 (2)
C4—C5—H5	118.5	O6—C30—C28	116.8 (2)
N3—C6—C7	119.7 (3)	N7^i—Fe1—N5	161.40 (9)
N3—C6—C1	116.0 (2)	N7^i—Fe1—O8	95.75 (8)
C7—C6—C1	124.3 (2)	N5—Fe1—O8	89.80 (8)
C6—C7—C8	120.8 (3)	N7^i—Fe1—N2	101.96 (8)
C6—C7—H7	119.6	N5—Fe1—N2	96.50 (9)
C8—C7—H7	119.6	O8—Fe1—N2	79.36 (8)
C9—C8—C7	119.4 (3)	N7^i—Fe1—O5^i	79.05 (7)
C9—C8—H8	120.3	N5—Fe1—O5^i	96.88 (8)
C7—C8—H8	120.3	O8—Fe1—O5^i	172.39 (7)
C8—C9—C10	116.6 (3)	N2—Fe1—O5^i	96.18 (7)
C8—C9—H9	121.7	N7^i—Fe1—N6	85.24 (8)
C10—C9—H9	121.7	N5—Fe1—N6	76.21 (9)
N3—C10—C9	124.7 (3)	O8—Fe1—N6	103.04 (8)
N3—C10—H10	117.6	N2—Fe1—N6	172.23 (8)
C9—C10—H10	117.6	O5^i—Fe1—N6	82.20 (8)
N1—C11—N8	115.3 (2)	N1—Fe2—N4	158.38 (9)
N1—C11—H11	122.4	N1—Fe2—N8^ii	102.12 (8)
N8—C11—H11	122.4	N4—Fe2—N8^ii	94.04 (9)
N8—C12—C13	108.9 (2)	N1—Fe2—O3^ii	101.41 (8)
N8—C12—C15	118.1 (2)	N4—Fe2—O3^ii	95.76 (8)
C13—C12—C15	132.9 (2)	N8^ii—Fe2—O3^ii	78.51 (8)
N1—C13—C12	108.7 (2)	N1—Fe2—O2	78.24 (8)
N1—C13—C14	118.4 (2)	N4—Fe2—O2	86.62 (8)
C12—C13—C14	132.8 (2)	N8^ii—Fe2—O2	93.45 (8)
O2—C14—O1	123.5 (3)	O3^ii—Fe2—O2	171.74 (7)
O2—C14—C13	119.5 (2)	N1—Fe2—N3	87.68 (8)
O1—C14—C13	116.9 (2)	N4—Fe2—N3	78.15 (9)
O4—C15—O3	124.4 (2)	N8^ii—Fe2—N3	168.44 (8)
O4—C15—C12	116.6 (2)	O3^ii—Fe2—N3	93.66 (8)
O3—C15—C12	119.0 (2)	O2—Fe2—N3	94.57 (8)
N5—C16—C17	118.8 (3)	C11—N1—C13	103.5 (2)
N5—C16—C21	118.7 (2)	C11—N1—Fe2	142.88 (18)
C17—C16—C21	122.4 (3)	C13—N1—Fe2	112.30 (17)
C16—C17—C18	119.3 (3)	C27—N2—C29	103.7 (2)
C16—C17—H17	120.3	C27—N2—Fe1	108.53 (17)
C18—C17—H17	120.3	C29—N2—Fe1	144.53 (17)
C19—C18—C17	121.5 (3)	C6—N3—C10	118.8 (2)
C19—C18—H18	119.2	C6—N3—Fe2	112.81 (18)
C17—C18—H18	119.2	C10—N3—Fe2	128.37 (18)
C20—C19—C18	116.1 (3)	C1—N4—C5	120.5 (2)
C20—C19—H19	122.0	C1—N4—Fe2	115.04 (18)
C18—C19—H19	122.0	C5—N4—Fe2	124.28 (18)
C19—C20—N5	122.9 (3)	C16—N5—C20	121.3 (2)
C19—C20—H20	118.5	C16—N5—Fe1	116.59 (19)
N5—C20—H20	118.5	C20—N5—Fe1	122.02 (18)
N6—C21—C22	119.8 (3)	C21—N6—C25	118.1 (2)
N6—C21—C16	115.0 (2)	C21—N6—Fe1	112.18 (19)
C22—C21—C16	125.1 (3)	C25—N6—Fe1	129.06 (19)
C21—C22—C23	121.4 (3)	C29—N7—C28	103.2 (2)
C21—C22—H22	119.3	C29—N7—Fe1^iii	141.96 (18)
C23—C22—H22	119.3	C28—N7—Fe1^iii	110.65 (16)
C24—C23—C22	119.3 (3)	C11—N8—C12	103.6 (2)
C24—C23—H23	120.3	C11—N8—Fe2^iv	143.60 (18)
C22—C23—H23	120.3	C12—N8—Fe2^iv	111.23 (17)
C23—C24—C25	116.6 (3)	C14—O1—H1	109.5
C23—C24—H24	121.7	C14—O2—Fe2	111.30 (17)
C25—C24—H24	121.7	C15—O3—Fe2^iv	111.86 (16)
N6—C25—C24	124.8 (3)	C30—O5—Fe1^iii	110.75 (15)
N6—C25—H25	117.6	C30—O6—H6	110 (3)
C24—C25—H25	117.6	C26—O8—Fe1	112.45 (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, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.82	1.69	2.493 (3)	167
O6—H6···O7	0.82 (3)	1.69 (2)	2.489 (2)	167 (2)