Poly[bis-(4,4'-bipyridine)(μ(3)-4,4'-dicarboxybiphenyl-3,3'-di-carboxyl-ato)iron(II)].

In the polymeric title complex, [Fe(C(16)H(8)O(8))(C(10)H(8)N(2))(2)](n), the iron(II) cation is coordinated by four O atoms from three different 4,4'-dicarboxybiphenyl-3,3'-di-carboxyl-ate ligands and two N atoms from two 4,4'-bipyridine ligands in a distorted octa-hedral geometry. The 4,4'-dicarboxybiphenyl-3,3'-di-carboxyl-ate ligands bridge adjacent cations, forming chains parallel to the c axis. The chains are further connected by inter-molecular O-H⋯N hydrogen bonds, forming two-dimensional supra-molecular layers parallel to (010).

Related literature

For general background to self-assembling coordination polymers, see: Li et al. (2008 ▶); Yaghi et al. (2003 ▶). For related structures, see: Li et al. (2009 ▶); Liu et al. (2009 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

[Fe(C16H8O8)(C10H8N2)2]

M = 696.44

Monoclinic,

a = 11.9569 (13) Å

b = 24.114 (3) Å

c = 10.7232 (12) Å

β = 105.855 (1)°

V = 2974.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.57 mm−1

T = 296 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.880, T max = 0.899

15189 measured reflections

5363 independent reflections

4293 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.03

5363 reflections

444 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046273/rz2381sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046273/rz2381Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C16H8O8)(C10H8N2)2]	F(000) = 1432
Mr = 696.44	Dx = 1.555 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4905 reflections
a = 11.9569 (13) Å	θ = 2.4–27.0°
b = 24.114 (3) Å	µ = 0.57 mm−1
c = 10.7232 (12) Å	T = 296 K
β = 105.855 (1)°	Block, red
V = 2974.2 (6) Å3	0.23 × 0.21 × 0.19 mm
Z = 4

Bruker APEXII area-detector diffractometer	5363 independent reflections
Radiation source: fine-focus sealed tube	4293 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→10
Tmin = 0.880, Tmax = 0.899	k = −28→26
15189 measured reflections	l = −12→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0462P)2 + 1.5067P] where P = (Fo2 + 2Fc2)/3
5363 reflections	(Δ/σ)max = 0.002
444 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Fe1	0.58299 (3)	0.948957 (13)	0.88381 (3)	0.02617 (11)
C27	0.63026 (19)	0.80826 (9)	0.4436 (2)	0.0267 (5)
C11	0.4184 (2)	0.97360 (10)	0.5952 (2)	0.0331 (6)
H11	0.4542	1.0082	0.6064	0.040*
O3	0.88485 (15)	0.84329 (7)	0.88903 (16)	0.0417 (4)
H3	0.9409	0.8416	0.9532	0.063*
C29	0.5469 (2)	0.81316 (9)	0.3128 (2)	0.0277 (5)
N2	1.05946 (18)	0.88387 (10)	1.71537 (19)	0.0416 (5)
C3	0.8429 (2)	0.91461 (10)	1.3316 (2)	0.0322 (5)
O5	0.23281 (15)	0.87426 (7)	−0.06664 (16)	0.0414 (4)
H5	0.1792	0.8734	−0.1333	0.062*
C21	0.6846 (2)	0.88567 (9)	0.7580 (2)	0.0279 (5)
N1	0.70900 (17)	0.93693 (8)	1.07668 (18)	0.0327 (5)
N4	0.0513 (2)	0.85951 (11)	0.0994 (2)	0.0510 (6)
N3	0.44003 (17)	0.93946 (8)	0.69706 (18)	0.0304 (4)
C10	0.9865 (2)	0.85667 (11)	1.4936 (2)	0.0382 (6)
H10	0.9875	0.8309	1.4293	0.046*
C5	0.7413 (2)	0.88541 (11)	1.1179 (2)	0.0388 (6)
H5A	0.7179	0.8564	1.0593	0.047*
C2	0.8088 (2)	0.96780 (11)	1.2899 (2)	0.0435 (7)
H2	0.8296	0.9974	1.3471	0.052*
C6	0.9155 (2)	0.90314 (11)	1.4651 (2)	0.0332 (5)
C1	0.7440 (2)	0.97724 (11)	1.1640 (2)	0.0432 (7)
H1	0.7237	1.0136	1.1386	0.052*
C4	0.8068 (2)	0.87257 (11)	1.2414 (2)	0.0383 (6)
H4	0.8266	0.8359	1.2642	0.046*
C9	1.0557 (2)	0.84914 (12)	1.6183 (2)	0.0414 (6)
H9	1.1026	0.8177	1.6355	0.050*
C7	0.9158 (2)	0.93795 (12)	1.5675 (3)	0.0482 (7)
H7	0.8675	0.9689	1.5544	0.058*
C8	0.9880 (3)	0.92674 (13)	1.6896 (2)	0.0506 (7)
H8	0.9861	0.9506	1.7571	0.061*
C12	0.3463 (2)	0.96087 (10)	0.4744 (2)	0.0338 (6)
H12	0.3344	0.9864	0.4069	0.041*
C16	0.2130 (2)	0.89236 (11)	0.3283 (2)	0.0350 (6)
C14	0.3124 (2)	0.87458 (10)	0.5620 (2)	0.0358 (6)
H14	0.2764	0.8401	0.5547	0.043*
C17	0.1517 (3)	0.93092 (12)	0.2401 (3)	0.0519 (8)
H17	0.1640	0.9687	0.2559	0.062*
C13	0.2917 (2)	0.90935 (10)	0.4548 (2)	0.0313 (5)
C15	0.3853 (2)	0.89073 (10)	0.6785 (2)	0.0345 (6)
H15	0.3973	0.8664	0.7482	0.041*
C20	0.1939 (2)	0.83734 (12)	0.2949 (3)	0.0484 (7)
H20	0.2353	0.8100	0.3495	0.058*
C19	0.1136 (3)	0.82278 (13)	0.1808 (3)	0.0527 (8)
H19	0.1027	0.7854	0.1601	0.063*
C18	0.0727 (3)	0.91279 (14)	0.1290 (3)	0.0622 (9)
H18	0.0318	0.9392	0.0712	0.075*
C26	0.7131 (2)	0.76653 (10)	0.4723 (2)	0.0313 (5)
H26	0.7138	0.7393	0.4112	0.038*
C36	0.51638 (19)	0.86533 (9)	0.2589 (2)	0.0269 (5)
H36	0.5478	0.8966	0.3066	0.032*
C22	0.70735 (19)	0.84500 (9)	0.66113 (19)	0.0246 (5)
C25	0.7947 (2)	0.76543 (10)	0.5919 (2)	0.0305 (5)
H25	0.8516	0.7380	0.6087	0.037*
C34	0.44068 (19)	0.87230 (9)	0.1366 (2)	0.0250 (5)
C23	0.79408 (19)	0.80409 (9)	0.6875 (2)	0.0258 (5)
C33	0.2957 (2)	0.82910 (10)	−0.0585 (2)	0.0344 (6)
C28	0.62884 (19)	0.84684 (9)	0.5393 (2)	0.0284 (5)
H28	0.5733	0.8749	0.5210	0.034*
C30	0.5005 (2)	0.76689 (10)	0.2393 (2)	0.0394 (6)
H30	0.5216	0.7315	0.2717	0.047*
C24	0.8873 (2)	0.80139 (10)	0.8127 (2)	0.0296 (5)
C32	0.3894 (2)	0.82577 (10)	0.0668 (2)	0.0310 (5)
C31	0.4231 (2)	0.77351 (10)	0.1183 (2)	0.0415 (7)
H31	0.3929	0.7422	0.0700	0.050*
O2	0.62783 (14)	0.86750 (7)	0.83378 (14)	0.0317 (4)
O1	0.70685 (16)	0.93579 (7)	0.75185 (16)	0.0382 (4)
O4	0.95713 (16)	0.76380 (8)	0.83860 (17)	0.0479 (5)
O6	0.27834 (18)	0.79341 (8)	−0.14063 (18)	0.0575 (6)
C35	0.43099 (19)	0.92924 (9)	0.0796 (2)	0.0256 (5)
O7	0.45273 (14)	0.93505 (7)	−0.02766 (14)	0.0338 (4)
O8	0.40781 (15)	0.96848 (7)	0.14606 (15)	0.0355 (4)

	U11	U22	U33	U12	U13	U23
Fe1	0.0328 (2)	0.02408 (19)	0.01910 (18)	0.00295 (13)	0.00281 (13)	−0.00112 (12)
C27	0.0317 (13)	0.0253 (12)	0.0203 (11)	0.0002 (9)	0.0025 (10)	0.0004 (9)
C11	0.0381 (14)	0.0307 (13)	0.0265 (12)	−0.0020 (10)	0.0023 (10)	−0.0001 (10)
O3	0.0371 (11)	0.0483 (11)	0.0302 (9)	0.0044 (8)	−0.0070 (7)	−0.0103 (8)
C29	0.0330 (13)	0.0271 (12)	0.0209 (11)	0.0031 (10)	0.0036 (10)	0.0012 (9)
N2	0.0345 (12)	0.0527 (14)	0.0309 (12)	−0.0021 (10)	−0.0023 (9)	0.0060 (10)
C3	0.0269 (13)	0.0415 (15)	0.0247 (12)	0.0026 (10)	0.0010 (10)	−0.0004 (10)
O5	0.0370 (11)	0.0463 (11)	0.0307 (10)	0.0071 (8)	−0.0083 (8)	−0.0022 (8)
C21	0.0298 (13)	0.0275 (13)	0.0208 (11)	0.0054 (10)	−0.0024 (9)	−0.0008 (9)
N1	0.0348 (12)	0.0340 (12)	0.0251 (10)	0.0045 (9)	0.0012 (9)	−0.0007 (8)
N4	0.0408 (14)	0.0683 (18)	0.0352 (13)	−0.0011 (12)	−0.0041 (10)	−0.0144 (12)
N3	0.0311 (11)	0.0349 (12)	0.0235 (10)	0.0017 (8)	0.0047 (8)	−0.0001 (8)
C10	0.0369 (15)	0.0401 (15)	0.0328 (13)	0.0020 (11)	0.0014 (11)	0.0013 (11)
C5	0.0485 (16)	0.0371 (14)	0.0241 (12)	0.0025 (12)	−0.0013 (11)	−0.0029 (10)
C2	0.0490 (17)	0.0376 (15)	0.0335 (14)	0.0063 (12)	−0.0065 (12)	−0.0082 (11)
C6	0.0270 (13)	0.0425 (15)	0.0263 (12)	−0.0008 (10)	0.0008 (10)	0.0018 (10)
C1	0.0532 (17)	0.0352 (15)	0.0307 (14)	0.0117 (12)	−0.0062 (12)	0.0001 (11)
C4	0.0473 (16)	0.0349 (14)	0.0259 (12)	0.0050 (11)	−0.0013 (11)	0.0028 (10)
C9	0.0344 (15)	0.0457 (16)	0.0385 (15)	0.0047 (12)	0.0004 (11)	0.0098 (12)
C7	0.0495 (18)	0.0548 (18)	0.0308 (14)	0.0195 (13)	−0.0051 (12)	−0.0021 (12)
C8	0.0538 (18)	0.0607 (19)	0.0289 (14)	0.0114 (15)	−0.0031 (12)	−0.0048 (13)
C12	0.0372 (14)	0.0360 (14)	0.0239 (12)	−0.0020 (11)	0.0013 (10)	0.0044 (10)
C16	0.0298 (13)	0.0428 (15)	0.0279 (12)	−0.0010 (11)	0.0004 (10)	−0.0044 (11)
C14	0.0337 (14)	0.0323 (14)	0.0370 (14)	−0.0048 (10)	0.0020 (11)	0.0009 (11)
C17	0.0584 (19)	0.0431 (17)	0.0396 (16)	0.0095 (14)	−0.0115 (13)	−0.0097 (13)
C13	0.0262 (13)	0.0370 (14)	0.0273 (12)	0.0026 (10)	0.0015 (10)	−0.0040 (10)
C15	0.0354 (14)	0.0371 (14)	0.0283 (12)	−0.0022 (11)	0.0042 (10)	0.0060 (10)
C20	0.0502 (17)	0.0414 (16)	0.0422 (16)	−0.0034 (13)	−0.0067 (13)	−0.0029 (12)
C19	0.0542 (19)	0.0511 (18)	0.0448 (16)	−0.0116 (14)	0.0000 (14)	−0.0133 (14)
C18	0.062 (2)	0.065 (2)	0.0414 (17)	0.0152 (16)	−0.0162 (15)	−0.0066 (15)
C26	0.0390 (14)	0.0292 (13)	0.0233 (11)	0.0060 (10)	0.0048 (10)	−0.0049 (9)
C36	0.0336 (13)	0.0241 (12)	0.0200 (11)	0.0001 (9)	0.0022 (9)	−0.0040 (9)
C22	0.0300 (12)	0.0233 (12)	0.0196 (11)	−0.0002 (9)	0.0050 (9)	0.0009 (8)
C25	0.0345 (13)	0.0278 (12)	0.0271 (12)	0.0094 (10)	0.0048 (10)	0.0008 (9)
C34	0.0285 (12)	0.0258 (12)	0.0188 (11)	0.0029 (9)	0.0034 (9)	−0.0006 (9)
C23	0.0272 (12)	0.0263 (12)	0.0220 (11)	−0.0011 (9)	0.0036 (9)	0.0024 (9)
C33	0.0363 (14)	0.0338 (14)	0.0274 (12)	−0.0049 (11)	−0.0011 (10)	0.0018 (10)
C28	0.0304 (13)	0.0272 (12)	0.0247 (11)	0.0076 (9)	0.0027 (10)	0.0015 (9)
C30	0.0529 (17)	0.0250 (13)	0.0306 (13)	0.0028 (11)	−0.0049 (11)	0.0022 (10)
C24	0.0286 (13)	0.0348 (14)	0.0235 (11)	−0.0014 (10)	0.0039 (10)	0.0030 (10)
C32	0.0354 (13)	0.0296 (13)	0.0237 (11)	−0.0011 (10)	0.0011 (10)	−0.0013 (10)
C31	0.0551 (18)	0.0253 (13)	0.0331 (14)	−0.0048 (11)	−0.0068 (12)	−0.0038 (10)
O2	0.0383 (10)	0.0346 (9)	0.0204 (8)	0.0044 (7)	0.0049 (7)	−0.0013 (7)
O1	0.0517 (11)	0.0256 (9)	0.0346 (9)	0.0016 (8)	0.0076 (8)	−0.0032 (7)
O4	0.0446 (11)	0.0457 (12)	0.0422 (11)	0.0147 (9)	−0.0071 (8)	0.0026 (9)
O6	0.0701 (14)	0.0466 (12)	0.0369 (11)	0.0030 (10)	−0.0176 (9)	−0.0143 (9)
C35	0.0243 (12)	0.0267 (12)	0.0210 (11)	−0.0005 (9)	−0.0017 (9)	−0.0005 (9)
O7	0.0377 (10)	0.0395 (10)	0.0233 (8)	0.0002 (7)	0.0068 (7)	0.0056 (7)
O8	0.0532 (11)	0.0234 (9)	0.0284 (9)	0.0038 (7)	0.0084 (8)	−0.0023 (7)

Fe1—O8i	2.0244 (17)	C7—C8	1.384 (4)
Fe1—O7ii	2.0609 (16)	C7—H7	0.9300
Fe1—O2	2.1426 (16)	C8—H8	0.9300
Fe1—N1	2.2201 (19)	C12—C13	1.392 (3)
Fe1—N3	2.2615 (19)	C12—H12	0.9300
Fe1—O1	2.3327 (18)	C16—C20	1.377 (4)
C27—C26	1.387 (3)	C16—C17	1.384 (4)
C27—C28	1.389 (3)	C16—C13	1.482 (3)
C27—C29	1.487 (3)	C14—C15	1.370 (3)
C11—N3	1.335 (3)	C14—C13	1.390 (3)
C11—C12	1.381 (3)	C14—H14	0.9300
C11—H11	0.9300	C17—C18	1.374 (4)
O3—C24	1.306 (3)	C17—H17	0.9300
O3—H3	0.8200	C15—H15	0.9300
C29—C36	1.391 (3)	C20—C19	1.379 (4)
C29—C30	1.391 (3)	C20—H20	0.9300
N2—C8	1.321 (4)	C19—H19	0.9300
N2—C9	1.327 (3)	C18—H18	0.9300
C3—C2	1.383 (4)	C26—C25	1.383 (3)
C3—C4	1.386 (3)	C26—H26	0.9300
C3—C6	1.483 (3)	C36—C34	1.385 (3)
O5—C33	1.313 (3)	C36—H36	0.9300
O5—H5	0.8200	C22—C28	1.386 (3)
C21—O1	1.243 (3)	C22—C23	1.403 (3)
C21—O2	1.271 (3)	C25—C23	1.387 (3)
C21—C22	1.506 (3)	C25—H25	0.9300
N1—C1	1.335 (3)	C34—C32	1.395 (3)
N1—C5	1.339 (3)	C34—C35	1.495 (3)
N4—C19	1.321 (4)	C23—C24	1.494 (3)
N4—C18	1.331 (4)	C33—O6	1.208 (3)
N3—C15	1.333 (3)	C33—C32	1.498 (3)
C10—C9	1.379 (3)	C28—H28	0.9300
C10—C6	1.389 (3)	C30—C31	1.382 (3)
C10—H10	0.9300	C30—H30	0.9300
C5—C4	1.378 (3)	C24—O4	1.212 (3)
C5—H5A	0.9300	C32—C31	1.391 (3)
C2—C1	1.380 (3)	C31—H31	0.9300
C2—H2	0.9300	C35—O7	1.254 (3)
C6—C7	1.382 (4)	C35—O8	1.260 (3)
C1—H1	0.9300	O7—Fe1iii	2.0609 (16)
C4—H4	0.9300	O8—Fe1i	2.0244 (17)
C9—H9	0.9300
O8i—Fe1—O7ii	108.27 (7)	C13—C12—H12	120.4
O8i—Fe1—O2	146.50 (7)	C20—C16—C17	116.8 (2)
O7ii—Fe1—O2	103.80 (7)	C20—C16—C13	121.5 (2)
O8i—Fe1—N1	102.91 (7)	C17—C16—C13	121.6 (2)
O7ii—Fe1—N1	87.46 (7)	C15—C14—C13	120.5 (2)
O2—Fe1—N1	87.76 (7)	C15—C14—H14	119.7
O8i—Fe1—N3	91.15 (7)	C13—C14—H14	119.7
O7ii—Fe1—N3	84.72 (7)	C18—C17—C16	119.2 (3)
O2—Fe1—N3	82.29 (6)	C18—C17—H17	120.4
N1—Fe1—N3	165.49 (8)	C16—C17—H17	120.4
O8i—Fe1—O1	88.10 (6)	C14—C13—C12	116.3 (2)
O7ii—Fe1—O1	160.43 (7)	C14—C13—C16	121.0 (2)
O2—Fe1—O1	58.64 (6)	C12—C13—C16	122.6 (2)
N1—Fe1—O1	99.53 (7)	N3—C15—C14	123.4 (2)
N3—Fe1—O1	84.29 (7)	N3—C15—H15	118.3
C26—C27—C28	118.3 (2)	C14—C15—H15	118.3
C26—C27—C29	121.45 (19)	C16—C20—C19	120.1 (3)
C28—C27—C29	120.2 (2)	C16—C20—H20	120.0
N3—C11—C12	124.2 (2)	C19—C20—H20	120.0
N3—C11—H11	117.9	N4—C19—C20	123.1 (3)
C12—C11—H11	117.9	N4—C19—H19	118.5
C24—O3—H3	109.5	C20—C19—H19	118.5
C36—C29—C30	118.1 (2)	N4—C18—C17	123.7 (3)
C36—C29—C27	119.7 (2)	N4—C18—H18	118.1
C30—C29—C27	122.1 (2)	C17—C18—H18	118.1
C8—N2—C9	116.6 (2)	C25—C26—C27	120.0 (2)
C2—C3—C4	116.4 (2)	C25—C26—H26	120.0
C2—C3—C6	121.9 (2)	C27—C26—H26	120.0
C4—C3—C6	121.7 (2)	C34—C36—C29	122.2 (2)
C33—O5—H5	109.5	C34—C36—H36	118.9
O1—C21—O2	121.9 (2)	C29—C36—H36	118.9
O1—C21—C22	121.0 (2)	C28—C22—C23	119.0 (2)
O2—C21—C22	116.4 (2)	C28—C22—C21	115.20 (19)
C1—N1—C5	115.9 (2)	C23—C22—C21	125.58 (19)
C1—N1—Fe1	124.13 (16)	C26—C25—C23	121.8 (2)
C5—N1—Fe1	119.29 (16)	C26—C25—H25	119.1
C19—N4—C18	116.9 (2)	C23—C25—H25	119.1
C15—N3—C11	116.3 (2)	C36—C34—C32	119.2 (2)
C15—N3—Fe1	116.29 (15)	C36—C34—C35	117.16 (19)
C11—N3—Fe1	126.34 (16)	C32—C34—C35	123.08 (19)
C9—C10—C6	119.2 (2)	C25—C23—C22	118.5 (2)
C9—C10—H10	120.4	C25—C23—C24	118.8 (2)
C6—C10—H10	120.4	C22—C23—C24	122.7 (2)
N1—C5—C4	124.2 (2)	O6—C33—O5	124.2 (2)
N1—C5—H5A	117.9	O6—C33—C32	123.6 (2)
C4—C5—H5A	117.9	O5—C33—C32	112.2 (2)
C1—C2—C3	120.4 (2)	C22—C28—C27	122.2 (2)
C1—C2—H2	119.8	C22—C28—H28	118.9
C3—C2—H2	119.8	C27—C28—H28	118.9
C7—C6—C10	116.5 (2)	C31—C30—C29	120.0 (2)
C7—C6—C3	121.9 (2)	C31—C30—H30	120.0
C10—C6—C3	121.6 (2)	C29—C30—H30	120.0
N1—C1—C2	123.4 (2)	O4—C24—O3	124.5 (2)
N1—C1—H1	118.3	O4—C24—C23	122.5 (2)
C2—C1—H1	118.3	O3—C24—C23	113.0 (2)
C5—C4—C3	119.6 (2)	C31—C32—C34	118.6 (2)
C5—C4—H4	120.2	C31—C32—C33	118.0 (2)
C3—C4—H4	120.2	C34—C32—C33	123.4 (2)
N2—C9—C10	124.1 (2)	C30—C31—C32	121.6 (2)
N2—C9—H9	117.9	C30—C31—H31	119.2
C10—C9—H9	117.9	C32—C31—H31	119.2
C6—C7—C8	119.9 (3)	C21—O2—Fe1	93.32 (13)
C6—C7—H7	120.0	C21—O1—Fe1	85.40 (14)
C8—C7—H7	120.0	O7—C35—O8	124.6 (2)
N2—C8—C7	123.5 (3)	O7—C35—C34	117.7 (2)
N2—C8—H8	118.3	O8—C35—C34	117.57 (19)
C7—C8—H8	118.3	C35—O7—Fe1iii	144.35 (15)
C11—C12—C13	119.1 (2)	C35—O8—Fe1i	128.26 (15)
C11—C12—H12	120.4

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2iv	0.82	1.86	2.677 (2)	171
O3—H3···N4v	0.82	1.81	2.598 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2i	0.82	1.86	2.677 (2)	171
O3—H3⋯N4ii	0.82	1.81	2.598 (3)	162

Symmetry codes: (i) ; (ii) .