Bis[4-(4-pyridyl)pyridinium] (4-carboxy-pyridine-2,6-dicarboxyl-ato-κO,N,O)(pyridine-2,4,6-tricarboxyl-ato-κO,N,O)ferrate(III) trihydrate.

In the title salt, (C(10)H(9)N(2))(2)[Fe(C(8)H(2)NO(6))(C(8)H(3)NO(6))]·3H(2)O, the Fe(III) atom is O,N,O'-chelated by dianionic and trianionic ligands in a slightly distorted octa-hedral coordination geometry. The cations and ferrate anions are linked into a layered structure; the layers are connected through the uncoordinated water mol-ecules into a hydrogen-bonded three-dimensional supra-molecular structure. One of the uncoordinated water molecules is disordered around an inversion centre and was refined with half-occupancy for each position.

Related literature

For the design and synthesis of coordination polymer complexes and their potential applications, see: Kaneko et al. (2007 ▶); Li et al. (2008 ▶); Lin et al. (2009 ▶). For the H3ptc ligand, see: Ghosh & Bharadwaj (2006 ▶); Lin et al. (2007 ▶); Syper et al. (1980 ▶).

Experimental

Crystal data

(C10H9N2)2[Fe(C8H2NO6)(C8H3NO6)]·3H2O

M = 841.50

Triclinic,

a = 10.568 (2) Å

b = 12.386 (3) Å

c = 14.344 (3) Å

α = 77.13 (3)°

β = 79.82 (3)°

γ = 76.15 (3)°

V = 1761.9 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.51 mm−1

T = 293 K

0.35 × 0.24 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.860, T max = 0.913

17019 measured reflections

7934 independent reflections

5458 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.138

S = 1.06

7934 reflections

526 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.41 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010514/ng2562sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010514/ng2562Isup2.hkl

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

(C10H9N2)2[Fe(C8H2NO6)(C8H3NO6)]·3H2O	Z = 2
Mr = 841.50	F(000) = 866
Triclinic, P1	Dx = 1.586 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.568 (2) Å	Cell parameters from 17019 reflections
b = 12.386 (3) Å	θ = 3.2–27.5°
c = 14.344 (3) Å	µ = 0.51 mm−1
α = 77.13 (3)°	T = 293 K
β = 79.82 (3)°	Block, brown
γ = 76.15 (3)°	0.35 × 0.24 × 0.17 mm
V = 1761.9 (6) Å3

Rigaku R-AXIS RAPID diffractometer	7934 independent reflections
Radiation source: fine-focus sealed tube	5458 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→16
Tmin = 0.860, Tmax = 0.913	l = −17→18
17019 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.2949P] where P = (Fo2 + 2Fc2)/3
7934 reflections	(Δ/σ)max = 0.018
526 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe	0.48489 (4)	0.50845 (4)	0.74947 (3)	0.02949 (13)
N1	0.3459 (2)	0.51476 (19)	0.86945 (15)	0.0271 (5)
N2	0.6260 (2)	0.52164 (19)	0.63117 (14)	0.0253 (5)
C1	0.3767 (3)	0.4481 (2)	0.95274 (18)	0.0272 (6)
C2	0.2896 (3)	0.4545 (2)	1.03624 (18)	0.0299 (6)
H2	0.3096	0.4081	1.0945	0.036*
C3	0.1708 (3)	0.5328 (2)	1.03055 (18)	0.0300 (6)
C4	0.1416 (3)	0.6013 (2)	0.94256 (19)	0.0310 (6)
H4	0.0624	0.6535	0.9381	0.037*
C5	0.2338 (3)	0.5894 (2)	0.86208 (18)	0.0286 (6)
C6	0.5121 (3)	0.3728 (2)	0.94093 (19)	0.0308 (6)
O1	0.57272 (18)	0.39221 (17)	0.85399 (13)	0.0358 (5)
O2	0.5550 (2)	0.30376 (19)	1.00811 (15)	0.0450 (5)
C7	0.0695 (3)	0.5450 (3)	1.1186 (2)	0.0335 (6)
O3	0.1080 (2)	0.4852 (2)	1.19749 (14)	0.0525 (6)
H3	0.0457	0.4873	1.2407	0.079*
O4	−0.0370 (2)	0.6083 (2)	1.10993 (15)	0.0529 (6)
C8	0.2268 (3)	0.6545 (2)	0.75967 (19)	0.0311 (6)
O5	0.1333 (2)	0.73086 (19)	0.73936 (14)	0.0436 (5)
O6	0.32849 (19)	0.62091 (18)	0.70084 (12)	0.0352 (5)
C9	0.6408 (2)	0.4532 (2)	0.56858 (18)	0.0266 (6)
C10	0.7329 (3)	0.4614 (2)	0.48723 (18)	0.0294 (6)
H10	0.7429	0.4149	0.4426	0.035*
C11	0.8105 (3)	0.5417 (2)	0.47426 (18)	0.0299 (6)
C12	0.7941 (3)	0.6101 (2)	0.54191 (18)	0.0301 (6)
H12	0.8464	0.6629	0.5345	0.036*
C13	0.6987 (2)	0.5981 (2)	0.62030 (18)	0.0271 (6)
C14	0.5477 (3)	0.3726 (2)	0.60007 (19)	0.0317 (6)
O7	0.47146 (19)	0.38846 (18)	0.67958 (14)	0.0379 (5)
O8	0.5477 (2)	0.3013 (2)	0.55424 (17)	0.0524 (6)
C15	0.9150 (3)	0.5546 (3)	0.38788 (19)	0.0356 (7)
O9	0.9347 (2)	0.4803 (2)	0.33614 (16)	0.0558 (7)
O10	0.9727 (2)	0.6326 (2)	0.37478 (17)	0.0595 (7)
C16	0.6609 (3)	0.6649 (2)	0.70080 (19)	0.0305 (6)
O11	0.7138 (2)	0.74272 (19)	0.69996 (15)	0.0441 (5)
O12	0.56886 (19)	0.63358 (17)	0.76424 (13)	0.0360 (5)
N3	0.9300 (3)	0.0772 (3)	0.6608 (2)	0.0529 (8)
H3A	0.9740	0.0865	0.7025	0.079*
C17	0.8781 (4)	−0.0123 (4)	0.6781 (2)	0.0579 (10)
H17	0.8887	−0.0644	0.7354	0.069*
C18	0.8083 (4)	−0.0307 (3)	0.6131 (2)	0.0556 (10)
H18	0.7717	−0.0945	0.6263	0.067*
C19	0.7928 (3)	0.0467 (3)	0.5278 (2)	0.0373 (7)
C20	0.8491 (3)	0.1404 (3)	0.5113 (2)	0.0422 (7)
H20	0.8415	0.1932	0.4542	0.051*
C21	0.9160 (3)	0.1548 (3)	0.5797 (3)	0.0512 (9)
H21	0.9519	0.2187	0.5697	0.061*
N4	0.5820 (3)	−0.0089 (3)	0.3213 (2)	0.0502 (7)
C22	0.7179 (3)	0.0271 (3)	0.4566 (2)	0.0380 (7)
C23	0.6505 (3)	0.1171 (3)	0.3962 (2)	0.0430 (7)
H23	0.6490	0.1913	0.4003	0.052*
C24	0.5854 (3)	0.0946 (3)	0.3297 (2)	0.0476 (8)
H24	0.5414	0.1555	0.2886	0.057*
C25	0.6459 (5)	−0.0947 (4)	0.3793 (3)	0.0829 (15)
H25	0.6458	−0.1680	0.3735	0.100*
C26	0.7133 (5)	−0.0797 (3)	0.4485 (3)	0.0783 (15)
H26	0.7552	−0.1423	0.4893	0.094*
N5	0.9437 (3)	0.9490 (3)	1.1818 (2)	0.0495 (7)
C27	0.8663 (3)	1.0491 (3)	1.1540 (2)	0.0491 (9)
H27	0.8631	1.1076	1.1858	0.059*
C28	0.7908 (3)	1.0700 (3)	1.0802 (2)	0.0443 (8)
H28	0.7390	1.1414	1.0619	0.053*
C29	0.7940 (3)	0.9821 (2)	1.0337 (2)	0.0320 (6)
C30	0.8776 (3)	0.8807 (3)	1.0597 (2)	0.0418 (7)
H30	0.8854	0.8217	1.0273	0.050*
C31	0.9503 (3)	0.8665 (3)	1.1342 (3)	0.0509 (9)
H31	1.0059	0.7969	1.1518	0.061*
N6	0.5522 (3)	1.0162 (2)	0.81949 (19)	0.0445 (7)
H6A	0.5044	1.0219	0.7753	0.067*
C32	0.7079 (3)	0.9959 (3)	0.9582 (2)	0.0324 (6)
C33	0.6801 (3)	1.0959 (3)	0.8931 (2)	0.0403 (7)
H33	0.7144	1.1574	0.8958	0.048*
C34	0.6010 (3)	1.1043 (3)	0.8238 (2)	0.0452 (8)
H34	0.5817	1.1718	0.7799	0.054*
C35	0.5763 (3)	0.9191 (3)	0.8826 (2)	0.0433 (8)
H35	0.5400	0.8592	0.8786	0.052*
C36	0.6533 (3)	0.9062 (3)	0.9529 (2)	0.0394 (7)
H36	0.6690	0.8383	0.9967	0.047*
O14	0.8797 (3)	0.7658 (3)	0.8387 (2)	0.0770 (9)
H14A	0.8215	0.7521	0.8116	0.116*
H14B	0.9524	0.7531	0.8024	0.116*
O15	1.1872 (2)	0.7054 (2)	0.25415 (18)	0.0571 (7)
H15A	1.1225	0.6765	0.2841	0.086*
H15B	1.2405	0.6626	0.2191	0.086*
O13A	−0.299 (4)	0.735 (3)	1.201 (2)	0.087 (5)	0.50
O13B	−0.293 (4)	0.719 (3)	1.174 (2)	0.087 (5)	0.50
H13A	−0.3480	0.6982	1.2502	0.131*
H13B	−0.2432	0.6654	1.1609	0.131*

	U11	U22	U33	U12	U13	U23
Fe	0.0310 (2)	0.0340 (2)	0.0201 (2)	−0.00864 (17)	0.00912 (14)	−0.00606 (16)
N1	0.0288 (12)	0.0288 (12)	0.0202 (10)	−0.0050 (10)	0.0050 (8)	−0.0047 (9)
N2	0.0270 (11)	0.0293 (12)	0.0175 (10)	−0.0071 (9)	0.0045 (8)	−0.0043 (9)
C1	0.0317 (14)	0.0284 (15)	0.0196 (12)	−0.0071 (11)	0.0038 (10)	−0.0052 (11)
C2	0.0357 (15)	0.0335 (16)	0.0178 (12)	−0.0097 (12)	0.0040 (10)	−0.0026 (11)
C3	0.0340 (15)	0.0350 (16)	0.0213 (13)	−0.0107 (12)	0.0070 (10)	−0.0106 (12)
C4	0.0275 (14)	0.0339 (16)	0.0296 (14)	−0.0021 (12)	0.0021 (11)	−0.0111 (12)
C5	0.0312 (14)	0.0297 (15)	0.0228 (13)	−0.0055 (12)	0.0025 (10)	−0.0061 (11)
C6	0.0355 (15)	0.0304 (16)	0.0254 (13)	−0.0082 (12)	0.0027 (11)	−0.0066 (12)
O1	0.0309 (10)	0.0404 (12)	0.0280 (10)	−0.0012 (9)	0.0100 (8)	−0.0074 (9)
O2	0.0454 (13)	0.0424 (13)	0.0325 (11)	0.0073 (10)	0.0005 (9)	0.0016 (10)
C7	0.0355 (16)	0.0363 (17)	0.0270 (14)	−0.0091 (13)	0.0094 (11)	−0.0113 (12)
O3	0.0432 (13)	0.0707 (17)	0.0273 (11)	−0.0002 (12)	0.0159 (9)	−0.0045 (11)
O4	0.0406 (13)	0.0621 (16)	0.0411 (12)	0.0063 (12)	0.0118 (10)	−0.0107 (12)
C8	0.0367 (16)	0.0336 (16)	0.0223 (13)	−0.0077 (13)	−0.0017 (11)	−0.0050 (12)
O5	0.0447 (13)	0.0442 (14)	0.0337 (11)	0.0016 (11)	−0.0047 (9)	−0.0022 (10)
O6	0.0388 (11)	0.0427 (12)	0.0196 (9)	−0.0065 (9)	0.0032 (8)	−0.0046 (8)
C9	0.0289 (14)	0.0282 (15)	0.0208 (12)	−0.0066 (11)	0.0033 (10)	−0.0054 (11)
C10	0.0287 (14)	0.0369 (16)	0.0207 (12)	−0.0055 (12)	0.0031 (10)	−0.0078 (11)
C11	0.0278 (14)	0.0339 (16)	0.0225 (13)	−0.0061 (12)	0.0054 (10)	−0.0013 (11)
C12	0.0326 (15)	0.0305 (15)	0.0251 (13)	−0.0118 (12)	0.0032 (11)	−0.0009 (11)
C13	0.0278 (14)	0.0290 (15)	0.0219 (13)	−0.0071 (11)	0.0015 (10)	−0.0016 (11)
C14	0.0342 (15)	0.0342 (16)	0.0267 (14)	−0.0121 (13)	0.0047 (11)	−0.0070 (12)
O7	0.0385 (11)	0.0427 (13)	0.0330 (10)	−0.0194 (10)	0.0127 (8)	−0.0104 (9)
O8	0.0595 (15)	0.0541 (15)	0.0543 (14)	−0.0294 (12)	0.0149 (11)	−0.0308 (12)
C15	0.0340 (15)	0.0437 (18)	0.0253 (14)	−0.0104 (14)	0.0064 (11)	−0.0043 (13)
O9	0.0602 (15)	0.0702 (17)	0.0390 (13)	−0.0285 (13)	0.0272 (11)	−0.0246 (12)
O10	0.0616 (15)	0.0712 (18)	0.0495 (14)	−0.0384 (14)	0.0268 (12)	−0.0193 (13)
C16	0.0352 (15)	0.0272 (15)	0.0279 (14)	−0.0060 (12)	−0.0013 (11)	−0.0056 (12)
O11	0.0546 (14)	0.0407 (13)	0.0431 (12)	−0.0207 (11)	0.0018 (10)	−0.0153 (10)
O12	0.0451 (12)	0.0380 (12)	0.0260 (10)	−0.0130 (10)	0.0076 (8)	−0.0131 (9)
N3	0.0578 (18)	0.066 (2)	0.0462 (17)	−0.0192 (16)	−0.0176 (14)	−0.0182 (16)
C17	0.072 (3)	0.068 (3)	0.0364 (18)	−0.023 (2)	−0.0220 (17)	0.0058 (17)
C18	0.074 (3)	0.053 (2)	0.0473 (19)	−0.034 (2)	−0.0233 (17)	0.0104 (17)
C19	0.0395 (17)	0.0368 (18)	0.0388 (16)	−0.0089 (14)	−0.0146 (13)	−0.0047 (13)
C20	0.054 (2)	0.0351 (18)	0.0424 (17)	−0.0150 (15)	−0.0144 (14)	−0.0053 (14)
C21	0.055 (2)	0.053 (2)	0.056 (2)	−0.0212 (18)	−0.0125 (16)	−0.0168 (18)
N4	0.0571 (18)	0.0484 (18)	0.0533 (17)	−0.0110 (14)	−0.0291 (14)	−0.0092 (14)
C22	0.0448 (17)	0.0364 (18)	0.0375 (16)	−0.0154 (14)	−0.0135 (13)	−0.0028 (13)
C23	0.055 (2)	0.0358 (18)	0.0409 (17)	−0.0031 (15)	−0.0181 (14)	−0.0100 (14)
C24	0.049 (2)	0.044 (2)	0.0485 (19)	0.0038 (16)	−0.0258 (15)	−0.0067 (16)
C25	0.127 (4)	0.038 (2)	0.106 (4)	−0.024 (2)	−0.078 (3)	−0.004 (2)
C26	0.121 (4)	0.032 (2)	0.100 (3)	−0.018 (2)	−0.085 (3)	0.007 (2)
N5	0.0512 (17)	0.056 (2)	0.0476 (16)	−0.0099 (15)	−0.0234 (13)	−0.0100 (14)
C27	0.053 (2)	0.052 (2)	0.050 (2)	−0.0059 (17)	−0.0173 (16)	−0.0223 (17)
C28	0.0459 (18)	0.0380 (19)	0.053 (2)	−0.0032 (15)	−0.0188 (15)	−0.0139 (16)
C29	0.0312 (15)	0.0330 (16)	0.0317 (14)	−0.0065 (12)	−0.0058 (11)	−0.0047 (12)
C30	0.0453 (18)	0.0384 (18)	0.0449 (18)	−0.0040 (14)	−0.0157 (14)	−0.0119 (15)
C31	0.054 (2)	0.041 (2)	0.061 (2)	−0.0005 (16)	−0.0284 (17)	−0.0111 (17)
N6	0.0439 (15)	0.0547 (18)	0.0402 (14)	−0.0101 (13)	−0.0208 (12)	−0.0078 (13)
C32	0.0330 (15)	0.0345 (17)	0.0311 (14)	−0.0061 (12)	−0.0064 (11)	−0.0082 (12)
C33	0.0451 (18)	0.0387 (18)	0.0398 (17)	−0.0109 (14)	−0.0113 (13)	−0.0063 (14)
C34	0.051 (2)	0.044 (2)	0.0418 (18)	−0.0082 (16)	−0.0191 (14)	−0.0015 (15)
C35	0.0421 (18)	0.046 (2)	0.0494 (19)	−0.0134 (15)	−0.0148 (14)	−0.0123 (16)
C36	0.0435 (18)	0.0368 (18)	0.0397 (16)	−0.0118 (14)	−0.0124 (13)	−0.0018 (14)
O14	0.0659 (18)	0.091 (2)	0.0760 (19)	−0.0138 (17)	−0.0019 (15)	−0.0274 (18)
O15	0.0461 (14)	0.0489 (15)	0.0652 (15)	−0.0081 (12)	0.0163 (11)	−0.0084 (12)
O13A	0.075 (4)	0.063 (8)	0.101 (15)	−0.016 (5)	0.050 (8)	−0.016 (6)
O13B	0.075 (4)	0.063 (8)	0.101 (15)	−0.016 (5)	0.050 (8)	−0.016 (6)

Fe—O6	2.008 (2)	C18—H18	0.9300
Fe—O7	2.012 (2)	C19—C20	1.384 (4)
Fe—O1	2.018 (2)	C19—C22	1.488 (4)
Fe—O12	2.026 (2)	C20—C21	1.371 (4)
Fe—N2	2.056 (2)	C20—H20	0.9300
Fe—N1	2.058 (2)	C21—H21	0.9300
N1—C5	1.321 (3)	N4—C25	1.318 (5)
N1—C1	1.336 (3)	N4—C24	1.323 (4)
N2—C13	1.324 (3)	C22—C26	1.367 (5)
N2—C9	1.332 (3)	C22—C23	1.381 (4)
C1—C2	1.380 (3)	C23—C24	1.380 (4)
C1—C6	1.514 (4)	C23—H23	0.9300
C2—C3	1.393 (4)	C24—H24	0.9300
C2—H2	0.9300	C25—C26	1.386 (5)
C3—C4	1.394 (4)	C25—H25	0.9300
C3—C7	1.515 (3)	C26—H26	0.9300
C4—C5	1.383 (3)	N5—C27	1.332 (4)
C4—H4	0.9300	N5—C31	1.332 (4)
C5—C8	1.515 (4)	C27—C28	1.379 (4)
C6—O2	1.212 (3)	C27—H27	0.9300
C6—O1	1.296 (3)	C28—C29	1.389 (4)
C7—O4	1.216 (4)	C28—H28	0.9300
C7—O3	1.281 (4)	C29—C30	1.369 (4)
O3—H3	0.8200	C29—C32	1.491 (4)
C8—O5	1.220 (3)	C30—C31	1.380 (4)
C8—O6	1.289 (3)	C30—H30	0.9300
C9—C10	1.383 (3)	C31—H31	0.9300
C9—C14	1.510 (4)	N6—C34	1.331 (4)
C10—C11	1.397 (4)	N6—C35	1.334 (4)
C10—H10	0.9300	N6—H6A	0.8600
C11—C12	1.388 (4)	C32—C33	1.379 (4)
C11—C15	1.514 (3)	C32—C36	1.390 (4)
C12—C13	1.378 (3)	C33—C34	1.379 (4)
C12—H12	0.9300	C33—H33	0.9300
C13—C16	1.510 (4)	C34—H34	0.9300
C14—O8	1.213 (3)	C35—C36	1.364 (4)
C14—O7	1.299 (3)	C35—H35	0.9300
C15—O10	1.225 (4)	C36—H36	0.9300
C15—O9	1.265 (4)	O14—H14A	0.8499
C16—O11	1.221 (3)	O14—H14B	0.8508
C16—O12	1.279 (3)	O15—H15A	0.8517
N3—C17	1.309 (5)	O15—H15B	0.8520
N3—C21	1.339 (5)	O13A—H13A	0.9035
N3—H3A	0.8600	O13A—H13B	1.1256
C17—C18	1.372 (5)	O13B—H13A	1.1455
C17—H17	0.9300	O13B—H13B	0.7764
C18—C19	1.383 (4)
O6—Fe—O7	95.18 (9)	C16—O12—Fe	120.48 (17)
O6—Fe—O1	151.77 (7)	C17—N3—C21	121.4 (3)
O7—Fe—O1	92.17 (9)	C17—N3—H3A	119.3
O6—Fe—O12	91.68 (9)	C21—N3—H3A	119.3
O7—Fe—O12	151.67 (8)	N3—C17—C18	121.1 (3)
O1—Fe—O12	94.66 (9)	N3—C17—H17	119.5
O6—Fe—N2	102.03 (9)	C18—C17—H17	119.5
O7—Fe—N2	75.81 (8)	C17—C18—C19	119.5 (3)
O1—Fe—N2	106.20 (8)	C17—C18—H18	120.3
O12—Fe—N2	75.88 (8)	C19—C18—H18	120.3
O6—Fe—N1	75.78 (9)	C18—C19—C20	118.3 (3)
O7—Fe—N1	110.98 (8)	C18—C19—C22	119.9 (3)
O1—Fe—N1	76.14 (8)	C20—C19—C22	121.9 (3)
O12—Fe—N1	97.35 (8)	C21—C20—C19	119.5 (3)
N2—Fe—N1	172.91 (9)	C21—C20—H20	120.2
C5—N1—C1	122.9 (2)	C19—C20—H20	120.2
C5—N1—Fe	118.62 (18)	N3—C21—C20	120.3 (3)
C1—N1—Fe	118.31 (18)	N3—C21—H21	119.9
C13—N2—C9	122.6 (2)	C20—C21—H21	119.9
C13—N2—Fe	118.47 (16)	C25—N4—C24	117.7 (3)
C9—N2—Fe	118.94 (17)	C26—C22—C23	117.7 (3)
N1—C1—C2	120.3 (2)	C26—C22—C19	121.5 (3)
N1—C1—C6	111.8 (2)	C23—C22—C19	120.8 (3)
C2—C1—C6	127.9 (3)	C24—C23—C22	118.6 (3)
C1—C2—C3	118.0 (2)	C24—C23—H23	120.7
C1—C2—H2	121.0	C22—C23—H23	120.7
C3—C2—H2	121.0	N4—C24—C23	123.6 (3)
C2—C3—C4	120.4 (2)	N4—C24—H24	118.2
C2—C3—C7	121.4 (3)	C23—C24—H24	118.2
C4—C3—C7	118.2 (3)	N4—C25—C26	122.5 (4)
C5—C4—C3	118.1 (3)	N4—C25—H25	118.8
C5—C4—H4	120.9	C26—C25—H25	118.8
C3—C4—H4	120.9	C22—C26—C25	119.9 (4)
N1—C5—C4	120.3 (2)	C22—C26—H26	120.1
N1—C5—C8	111.4 (2)	C25—C26—H26	120.1
C4—C5—C8	128.3 (3)	C27—N5—C31	118.0 (3)
O2—C6—O1	126.0 (3)	N5—C27—C28	123.1 (3)
O2—C6—C1	121.2 (2)	N5—C27—H27	118.4
O1—C6—C1	112.7 (2)	C28—C27—H27	118.4
C6—O1—Fe	120.88 (18)	C27—C28—C29	118.4 (3)
O4—C7—O3	126.2 (2)	C27—C28—H28	120.8
O4—C7—C3	119.8 (3)	C29—C28—H28	120.8
O3—C7—C3	114.1 (3)	C30—C29—C28	118.4 (3)
C7—O3—H3	109.5	C30—C29—C32	120.1 (3)
O5—C8—O6	126.1 (3)	C28—C29—C32	121.5 (3)
O5—C8—C5	121.1 (2)	C29—C30—C31	119.6 (3)
O6—C8—C5	112.8 (2)	C29—C30—H30	120.2
C8—O6—Fe	120.84 (18)	C31—C30—H30	120.2
N2—C9—C10	120.4 (2)	N5—C31—C30	122.4 (3)
N2—C9—C14	111.4 (2)	N5—C31—H31	118.8
C10—C9—C14	128.2 (2)	C30—C31—H31	118.8
C9—C10—C11	117.9 (2)	C34—N6—C35	121.2 (3)
C9—C10—H10	121.0	C34—N6—H6A	119.4
C11—C10—H10	121.0	C35—N6—H6A	119.4
C12—C11—C10	120.1 (2)	C33—C32—C36	118.6 (3)
C12—C11—C15	118.8 (2)	C33—C32—C29	121.7 (3)
C10—C11—C15	121.1 (2)	C36—C32—C29	119.7 (3)
C13—C12—C11	118.6 (2)	C34—C33—C32	119.7 (3)
C13—C12—H12	120.7	C34—C33—H33	120.2
C11—C12—H12	120.7	C32—C33—H33	120.2
N2—C13—C12	120.4 (2)	N6—C34—C33	120.2 (3)
N2—C13—C16	111.8 (2)	N6—C34—H34	119.9
C12—C13—C16	127.8 (2)	C33—C34—H34	119.9
O8—C14—O7	125.4 (3)	N6—C35—C36	121.1 (3)
O8—C14—C9	121.8 (2)	N6—C35—H35	119.4
O7—C14—C9	112.8 (2)	C36—C35—H35	119.4
C14—O7—Fe	121.07 (17)	C35—C36—C32	119.2 (3)
O10—C15—O9	126.3 (3)	C35—C36—H36	120.4
O10—C15—C11	118.9 (3)	C32—C36—H36	120.4
O9—C15—C11	114.8 (3)	H14A—O14—H14B	107.2
O11—C16—O12	126.0 (2)	H15A—O15—H15B	112.8
O11—C16—C13	120.6 (2)	H13A—O13A—H13B	103.2
O12—C16—C13	113.4 (2)	H13A—O13B—H13B	110.8

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O9i	0.82	1.64	2.454 (3)	172
N3—H3A···N5ii	0.86	1.93	2.741 (4)	158
N6—H6A···N4iii	0.86	1.84	2.694 (4)	170
O13A—H13A···O7iv	0.90	1.90	2.766 (4)	161
O13B—H13B···O4	0.78	2.17	2.821 (4)	142
O14—H14A···O11	0.85	2.16	2.973 (4)	160
O14—H14B···O5v	0.85	1.95	2.788 (4)	169
O15—H15A···O10	0.85	1.97	2.801 (3)	166
O15—H15B···O1vi	0.85	2.10	2.877 (3)	152

Table 1

Selected geometric parameters (Å, °)

Fe—O6	2.008 (2)
Fe—O7	2.012 (2)
Fe—O1	2.018 (2)
Fe—O12	2.026 (2)
Fe—N2	2.056 (2)
Fe—N1	2.058 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O9i	0.82	1.64	2.454 (3)	172
N3—H3A⋯N5ii	0.86	1.93	2.741 (4)	158
N6—H6A⋯N4iii	0.86	1.84	2.694 (4)	170
O13A—H13A⋯O7iv	0.90	1.90	2.766 (4)	161
O13B—H13B⋯O4	0.78	2.17	2.821 (4)	142
O14—H14A⋯O11	0.85	2.16	2.973 (4)	160
O14—H14B⋯O5v	0.85	1.95	2.788 (4)	169
O15—H15A⋯O10	0.85	1.97	2.801 (3)	166
O15—H15B⋯O1vi	0.85	2.10	2.877 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .