Two-dimensional hydrogen-bond network in bis­[(ferrocenylmethyl)­dimethyl­ammonium] sulfate penta­hydrate

In the title compound, [Fe(C₅H₅)(C₈H₁₃N)]₂(SO₄)·5H₂O, the Fe-C bond lengths lie in the range 2.021 (3)-2.047 (2) Å. Inter­molecular N-H...O and O-H...O hydrogen bonds link the cations, sulfate anions and water mol­ecules into a two-dimensional hydrogen-bonded network, which stabilizes the crystal packing.

S1. Comment

The hydrogen bond is the most versatile intermolecular interaction responsible for molecular aggregation in biological and material science (Sowerby et al., 1996). Conventionally strong hydrogen bonds such as N—H···O, N—H···N and O—H···O have been extensively used in the area of supramolecular chemistry and crystal engineering. Ferrocenylmethyldimethylamine, serving as an intermediate, plays an important role in the syntheses of many ferrocene derivatives (Rainer & Gotthelf, 1998). With this background and with our previous studies of the N—H···O(NO₃⁻) hydrogen bond in the ferrocenylmethyldimethylammonium chloride salt (Guo et al.., 2006), we have now studied the N—H···O(SO₄²⁻) hydrogen bond in the supramolecular system of the title ammonium salt, (I), and present the results here.

As shown in Fig. 1, the asymmetric unit of (I) consists of two mono-protonated ammonium ions, [(C₅H₅)Fe1(C₈H₁₃N]⁺ and [(C₅H₅)Fe2(C₈H₁₃N]⁺, one sulfate anion and five uncoordinated water molecules. The two Fe atoms are bonded to the two five-membered carbon rings, with Fe1—C and Fe2—C bond lengths in the ranges 2.021 (2)–2.044 (2) and 2.015 (2)–2.047 (2) Å, respectively (Table 1). The rings C11–C15 and C31–C35 in [(C₅H₅)Fe1(C₈H₁₃N]⁺ are nearly parallel, with a dihedral angle between their mean planes of 1.42°, while the two rings C21–C25 and C41–C45 in [(C₅H₅)Fe2(C₈H₁₃N]⁺ have a dihedral angle of 3.17°. The two carbon rings in the two cations exhibit nearly eclipsed conformations, as is usually found in other ferrocene derivatives (Ye et al., 2005; Todd et al., 2006). In the structure of the SO₄²⁻ anion, the S—O bond distances [1.462 (1)–1.483 (1) Å] and O—S—O angles [108.23 (8)–110.96 (9)°] are close to the respective values for an ideal tetrahedral S-atom environment.

In the crystal structure of (I), classical intermolecular N—H···O and O—H···O hydrogen bonds are observed (Table 2, Fig.2), which link the two ammonium cations, one sulfate anion and five uncoordinated water molecules into a two-dimensional hydrogen-bonded network and stabilize the crystal packing (Fig. 3). It is noted that both cations [(C₅H₅)Fe1(C₈H₁₃N]⁺ and [(C₅H₅)Fe2(C₈H₁₃N]⁺ bond to the same SO₄²⁻ anion, which in turn bonds to the water molecules. The D···A distances and D—H···A angles in the N—H···O hydrogen bonds lie in the ranges 2.745 (2)–3.174 (2) Å and 124.9–168.4°, respectively, while those in O—H···O(SO₄²⁻) hydrogen bonds lie in the ranges 2.754 (2)–2.884 (3) Å and 150–176°, respectively. Additionally, there is extensive hydrogen bonding between the water molecules, with O···O interatomic distances ranging from 2.697 (3) to 2.853 (3) Å (Table 2).

S2. Experimental

A solution of CuSO₄·5H₂O (0.1248 g, 0.5 mmol) in methanol (10 ml) was added to a solution of (ferrocenylmethyl)dimethylamine (0.1213 g, 0.5 mmol) in methanol (10 ml). To this solution, dichloromethane (1.6 ml) was addded dropwise, and the mixture was stirred for 2 h and then concentrated under vacuum to a volume of 10 ml. Red block crystals of (I) were obtained by slow evaporation of the solvent in air. Analysis, found: C 46.8, H 7.2, N 4.7%; C₂₆H₄₆Fe₂N₂O₉S requires: C 46.3, H 6.8, N 4.2%. FT—IR (KBr, ν, cm⁻¹): 3438 (vw), 2942 (w), 2645 (s), 2472 (w), 1707.9 (w), 1472.8 (vs), 1416.4 (w), 1381.2 (w), 1416.4 (w), 1116.3 (s), 1012.9 (w), 945.1 (w), 920.9 (w), 824.3 (w), 707.2 (w), 619.3 (vs), 501.2 (w), 486.4 (w).

S3. Refinement

The C-bound H atoms were positioned geometrically, with C—H = 0.98, 0.97 and 0.96 Å for those on cyclopentadienyl, methylene and methyl C atoms, respectively, and they were refined as riding, with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C). Atom H1N was positioned geometrically and allowed to ride on N1, with N—H = 0.91 Å and U_iso(H) = 1.2U_eq(N). Water H atoms were located in a difference map and refined with O—H and H···H distance restraints of 0.85 (1) and 1.39 (1) Å, respectively, and with U_iso(H) = 1.5U_eq(O).

Computing details

Data collection: TEXRAY in TEXSAN? (Molecular Structure Corporation, 1999).; cell refinement: RAPID-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A view of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The structure of (I). Dashed lines indicate hydrogen bonds.
	Fig. 3. The two-dimensional hydrogen-bond network structure in (I). Intermolecular N—H···O and O—H···O hydrogen bonds are shown as dashed lines.

bis[(ferrocenylmethyl)dimethylammonium] sulfate pentahydrate

Crystal data

[Fe(C5H5)(C8H13N)]2(SO4)·5H2O	F(000) = 1424
Mr = 674.42	Dx = 1.413 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7626 reflections
a = 20.2187 (14) Å	θ = 2.0–27.5°
b = 11.5943 (6) Å	µ = 1.03 mm^−1
c = 13.5435 (9) Å	T = 293 K
β = 93.106 (3)°	Block, red
V = 3170.2 (3) Å^3	0.23 × 0.16 × 0.12 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	7269 independent reflections
Radiation source: fine-focus sealed tube	4691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998)	h = −26→26
Tmin = 0.820, Tmax = 0.884	k = −15→0
7626 measured reflections	l = 0→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0198P)^2] where P = (Fo^2 + 2Fc^2)/3
7256 reflections	(Δ/σ)max = 0.001
401 parameters	Δρmax = 0.32 e Å^−3
15 restraints	Δρmin = −0.43 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
Fe1	0.147438 (13)	0.75031 (2)	0.02195 (2)	0.04199 (8)
Fe2	0.121569 (13)	0.22656 (3)	0.24814 (2)	0.04209 (8)
S1	0.35137 (2)	0.41714 (4)	−0.04176 (4)	0.03993 (13)
O1	0.40710 (7)	0.34596 (13)	−0.07011 (12)	0.0605 (4)
O2	0.37557 (6)	0.50587 (12)	0.03030 (10)	0.0488 (4)
O3	0.32017 (7)	0.47572 (13)	−0.12783 (10)	0.0553 (4)
O4	0.30257 (6)	0.34451 (12)	0.00596 (10)	0.0514 (4)
C1	0.28634 (9)	0.75151 (18)	−0.07248 (16)	0.0526 (6)
H1A	0.2831	0.8320	−0.0918	0.063*
H1B	0.2680	0.7054	−0.1271	0.063*
C2	0.39489 (12)	0.7242 (2)	−0.1448 (2)	0.0742 (8)
H2A	0.4403	0.7038	−0.1298	0.111*
H2B	0.3927	0.8007	−0.1719	0.111*
H2C	0.3755	0.6707	−0.1921	0.111*
C3	0.39080 (12)	0.7924 (2)	0.0261 (2)	0.0793 (8)
H3A	0.4361	0.7687	0.0367	0.119*
H3B	0.3683	0.7831	0.0863	0.119*
H3C	0.3892	0.8719	0.0064	0.119*
C4	0.27104 (9)	0.28081 (17)	0.24655 (15)	0.0413 (5)
H4A	0.2738	0.2073	0.2128	0.050*
H4B	0.2809	0.2674	0.3165	0.050*
C5	0.32299 (11)	0.47489 (18)	0.25890 (16)	0.0547 (6)
H5A	0.3560	0.5232	0.2318	0.082*
H5B	0.3332	0.4642	0.3283	0.082*
H5C	0.2803	0.5107	0.2492	0.082*
C6	0.38858 (9)	0.30531 (19)	0.21534 (16)	0.0516 (6)
H6A	0.4209	0.3571	0.1908	0.077*
H6B	0.3873	0.2360	0.1765	0.077*
H6C	0.4003	0.2867	0.2831	0.077*
C11	0.24668 (9)	0.73224 (17)	0.01575 (15)	0.0433 (5)
C12	0.21797 (9)	0.62564 (18)	0.04326 (16)	0.0477 (5)
H12A	0.2200	0.5528	0.0068	0.057*
C13	0.18494 (10)	0.64371 (19)	0.13048 (17)	0.0535 (6)
H13A	0.1599	0.5855	0.1654	0.064*
C14	0.19350 (11)	0.7608 (2)	0.15904 (16)	0.0564 (6)
H14A	0.1757	0.7974	0.2172	0.068*
C15	0.23169 (10)	0.8152 (2)	0.08848 (16)	0.0525 (6)
H15A	0.2452	0.8964	0.0891	0.063*
C21	0.20192 (9)	0.32652 (17)	0.23195 (15)	0.0409 (5)
C22	0.16302 (10)	0.37388 (17)	0.30581 (17)	0.0498 (5)
H22A	0.1773	0.3869	0.3752	0.060*
C23	0.09916 (10)	0.39790 (19)	0.26123 (19)	0.0593 (6)
H23A	0.0615	0.4298	0.2948	0.071*
C24	0.09925 (11)	0.3666 (2)	0.16135 (18)	0.0601 (6)
H24A	0.0615	0.3728	0.1131	0.072*
C25	0.16271 (10)	0.32321 (19)	0.14176 (16)	0.0509 (6)
H25A	0.1768	0.2954	0.0779	0.061*
C31	0.10969 (12)	0.8202 (2)	−0.10769 (17)	0.0634 (7)
H31A	0.1356	0.8495	−0.1614	0.076*
C32	0.08688 (11)	0.7058 (2)	−0.09780 (18)	0.0633 (7)
H32A	0.0937	0.6419	−0.1435	0.076*
C33	0.05256 (10)	0.7006 (3)	−0.00993 (19)	0.0690 (7)
H33A	0.0312	0.6320	0.0161	0.083*
C34	0.05382 (11)	0.8115 (3)	0.0338 (2)	0.0730 (8)
H34A	0.0335	0.8336	0.0951	0.088*
C35	0.08943 (12)	0.8843 (2)	−0.02711 (18)	0.0672 (7)
H35A	0.0987	0.9662	−0.0150	0.081*
C41	0.15325 (12)	0.0769 (2)	0.3099 (3)	0.0868 (10)
H41A	0.1974	0.0614	0.3403	0.104*
C42	0.09730 (14)	0.1185 (2)	0.3590 (2)	0.0770 (8)
H42A	0.0959	0.1379	0.4292	0.092*
C43	0.04471 (12)	0.1246 (2)	0.2879 (2)	0.0642 (7)
H43A	−0.0001	0.1517	0.2997	0.077*
C44	0.06638 (13)	0.0892 (2)	0.1977 (2)	0.0712 (7)
H44A	0.0395	0.0861	0.1354	0.085*
C45	0.13252 (15)	0.0593 (2)	0.2105 (3)	0.0818 (9)
H45A	0.1603	0.0304	0.1587	0.098*
N1	0.35790 (8)	0.72042 (15)	−0.05275 (13)	0.0507 (5)
HN1	0.3591	0.6462	−0.0309	0.061*
N2	0.32212 (7)	0.36149 (13)	0.20847 (11)	0.0384 (4)
HN2	0.3113	0.3742	0.1433	0.046*
O1W	0.44185 (11)	0.1194 (2)	−0.03300 (15)	0.0821 (6)
H1WA	0.4318 (15)	0.1906 (16)	−0.040 (2)	0.129 (14)*
H1WB	0.4550 (13)	0.109 (2)	0.0259 (13)	0.097 (11)*
O2W	0.27295 (12)	0.1012 (2)	0.00822 (16)	0.0876 (6)
H2WA	0.3017 (12)	0.076 (2)	0.0483 (18)	0.106 (12)*
H2WB	0.2787 (13)	0.1714 (15)	−0.002 (2)	0.102 (12)*
O3W	0.48668 (11)	0.5506 (3)	0.15337 (15)	0.1153 (10)
H3WA	0.5140 (12)	0.596 (2)	0.133 (2)	0.134 (14)*
H3WB	0.4642 (12)	0.523 (2)	0.1061 (16)	0.106 (11)*
O4W	0.34744 (10)	0.48963 (17)	−0.32453 (13)	0.0696 (5)
H4WB	0.3898 (8)	0.496 (2)	−0.3274 (18)	0.092 (11)*
H4WA	0.3389 (12)	0.483 (3)	−0.2656 (13)	0.106 (12)*
O5W	0.48659 (11)	0.0205 (2)	0.15110 (17)	0.0924 (7)
H5WB	0.4970 (13)	0.035 (2)	0.2081 (13)	0.100 (12)*
H5WA	0.5123 (12)	−0.018 (2)	0.1218 (17)	0.101 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.04362 (16)	0.03893 (17)	0.04392 (17)	0.00069 (13)	0.00697 (13)	0.00180 (14)
Fe2	0.03966 (16)	0.03937 (17)	0.04760 (18)	−0.00209 (13)	0.00560 (13)	0.00040 (15)
S1	0.0450 (3)	0.0374 (3)	0.0377 (3)	−0.0053 (2)	0.0052 (2)	−0.0002 (2)
O1	0.0595 (9)	0.0483 (9)	0.0757 (11)	0.0044 (8)	0.0228 (8)	−0.0037 (8)
O2	0.0553 (9)	0.0422 (9)	0.0480 (8)	−0.0054 (7)	−0.0047 (7)	−0.0068 (7)
O3	0.0698 (10)	0.0566 (10)	0.0390 (8)	−0.0056 (8)	−0.0023 (7)	0.0105 (8)
O4	0.0564 (8)	0.0541 (9)	0.0441 (8)	−0.0183 (7)	0.0064 (7)	0.0057 (7)
C1	0.0465 (12)	0.0532 (15)	0.0587 (14)	0.0039 (11)	0.0090 (10)	0.0084 (12)
C2	0.0701 (16)	0.0640 (17)	0.092 (2)	−0.0020 (13)	0.0386 (15)	0.0063 (15)
C3	0.0591 (15)	0.0710 (19)	0.107 (2)	−0.0160 (14)	−0.0015 (15)	−0.0220 (17)
C4	0.0405 (10)	0.0396 (12)	0.0439 (11)	−0.0035 (9)	0.0044 (9)	0.0043 (10)
C5	0.0625 (14)	0.0456 (14)	0.0560 (14)	−0.0071 (11)	0.0036 (11)	−0.0081 (12)
C6	0.0387 (11)	0.0574 (14)	0.0586 (14)	0.0012 (10)	0.0020 (10)	0.0055 (12)
C11	0.0420 (11)	0.0405 (12)	0.0476 (12)	−0.0032 (9)	0.0035 (9)	0.0016 (10)
C12	0.0495 (12)	0.0353 (12)	0.0583 (14)	−0.0002 (10)	0.0024 (10)	0.0017 (11)
C13	0.0552 (13)	0.0496 (14)	0.0561 (14)	0.0010 (11)	0.0075 (11)	0.0178 (12)
C14	0.0626 (14)	0.0615 (16)	0.0453 (13)	−0.0004 (12)	0.0053 (11)	−0.0039 (12)
C15	0.0537 (13)	0.0446 (13)	0.0593 (14)	−0.0092 (11)	0.0040 (11)	−0.0051 (12)
C21	0.0401 (11)	0.0373 (11)	0.0453 (12)	−0.0031 (9)	0.0028 (9)	0.0026 (10)
C22	0.0497 (12)	0.0443 (13)	0.0555 (13)	−0.0019 (10)	0.0041 (10)	−0.0069 (11)
C23	0.0467 (13)	0.0414 (13)	0.0906 (19)	0.0042 (11)	0.0110 (12)	−0.0003 (14)
C24	0.0471 (13)	0.0597 (16)	0.0720 (17)	−0.0008 (12)	−0.0114 (11)	0.0199 (14)
C25	0.0499 (12)	0.0604 (15)	0.0421 (12)	−0.0075 (11)	0.0009 (10)	0.0118 (11)
C31	0.0706 (15)	0.0730 (18)	0.0471 (14)	0.0187 (14)	0.0059 (12)	0.0067 (14)
C32	0.0555 (14)	0.0732 (19)	0.0600 (16)	0.0070 (13)	−0.0082 (12)	−0.0129 (14)
C33	0.0417 (13)	0.090 (2)	0.0746 (18)	−0.0072 (13)	0.0011 (12)	0.0094 (17)
C34	0.0521 (14)	0.107 (2)	0.0613 (16)	0.0238 (15)	0.0118 (12)	−0.0024 (17)
C35	0.0794 (17)	0.0614 (16)	0.0606 (16)	0.0273 (14)	0.0034 (13)	0.0013 (14)
C41	0.0484 (15)	0.0540 (17)	0.156 (3)	−0.0097 (13)	−0.0167 (18)	0.051 (2)
C42	0.0860 (19)	0.082 (2)	0.0625 (16)	−0.0306 (17)	0.0023 (15)	0.0269 (15)
C43	0.0501 (13)	0.0575 (16)	0.0861 (18)	−0.0128 (12)	0.0143 (13)	−0.0001 (15)
C44	0.0694 (17)	0.0535 (16)	0.090 (2)	−0.0164 (13)	0.0021 (15)	−0.0153 (15)
C45	0.082 (2)	0.0405 (15)	0.126 (3)	0.0031 (14)	0.0290 (19)	−0.0063 (17)
N1	0.0491 (10)	0.0362 (10)	0.0682 (12)	−0.0038 (8)	0.0144 (9)	0.0012 (9)
N2	0.0389 (9)	0.0426 (10)	0.0336 (9)	−0.0046 (8)	0.0006 (7)	0.0023 (8)
O1W	0.1065 (15)	0.0746 (15)	0.0651 (13)	0.0320 (12)	0.0037 (11)	0.0039 (11)
O2W	0.1073 (17)	0.0699 (15)	0.0824 (15)	−0.0193 (13)	−0.0244 (12)	0.0068 (13)
O3W	0.0739 (14)	0.203 (3)	0.0666 (13)	−0.0671 (16)	−0.0189 (11)	0.0442 (16)
O4W	0.0780 (14)	0.0801 (13)	0.0502 (11)	0.0037 (11)	0.0001 (9)	0.0083 (10)
O5W	0.0934 (15)	0.123 (2)	0.0596 (13)	0.0447 (14)	−0.0058 (12)	−0.0068 (14)

Geometric parameters (Å, º)

Fe1—C11	2.0238 (19)	C11—C12	1.424 (3)
Fe1—C33	2.027 (2)	C12—C13	1.404 (3)
Fe1—C15	2.028 (2)	C12—H12A	0.9800
Fe1—C14	2.035 (2)	C13—C14	1.419 (3)
Fe1—C13	2.035 (2)	C13—H13A	0.9800
Fe1—C34	2.036 (2)	C14—C15	1.410 (3)
Fe1—C35	2.036 (2)	C14—H14A	0.9800
Fe1—C12	2.040 (2)	C15—H15A	0.9800
Fe1—C31	2.044 (2)	C21—C22	1.416 (3)
Fe1—C32	2.045 (2)	C21—C25	1.420 (3)
Fe2—C41	2.015 (2)	C22—C23	1.423 (3)
Fe2—C21	2.0173 (18)	C22—H22A	0.9800
Fe2—C45	2.021 (3)	C23—C24	1.401 (3)
Fe2—C42	2.035 (2)	C23—H23A	0.9800
Fe2—C25	2.038 (2)	C24—C25	1.416 (3)
Fe2—C22	2.039 (2)	C24—H24A	0.9800
Fe2—C24	2.040 (2)	C25—H25A	0.9800
Fe2—C44	2.041 (2)	C31—C35	1.400 (3)
Fe2—C23	2.047 (2)	C31—C32	1.413 (3)
Fe2—C43	2.048 (2)	C31—H31A	0.9800
S1—O3	1.4623 (14)	C32—C33	1.411 (3)
S1—O1	1.4646 (14)	C32—H32A	0.9800
S1—O4	1.4729 (13)	C33—C34	1.416 (4)
S1—O2	1.4828 (14)	C33—H33A	0.9800
C1—C11	1.491 (3)	C34—C35	1.406 (3)
C1—N1	1.501 (2)	C34—H34A	0.9800
C1—H1A	0.9700	C35—H35A	0.9800
C1—H1B	0.9700	C41—C45	1.403 (4)
C2—N1	1.489 (3)	C41—C42	1.427 (4)
C2—H2A	0.9600	C41—H41A	0.9800
C2—H2B	0.9600	C42—C43	1.397 (3)
C2—H2C	0.9600	C42—H42A	0.9800
C3—N1	1.484 (3)	C43—C44	1.382 (3)
C3—H3A	0.9600	C43—H43A	0.9800
C3—H3B	0.9600	C44—C45	1.383 (3)
C3—H3C	0.9600	C44—H44A	0.9800
C4—C21	1.498 (2)	C45—H45A	0.9800
C4—N2	1.505 (2)	N1—HN1	0.9100
C4—H4A	0.9700	N2—HN2	0.9100
C4—H4B	0.9700	O1W—H1WA	0.853 (17)
C5—N2	1.481 (2)	O1W—H1WB	0.835 (16)
C5—H5A	0.9600	O2W—H2WA	0.829 (16)
C5—H5B	0.9600	O2W—H2WB	0.834 (16)
C5—H5C	0.9600	O3W—H3WA	0.826 (16)
C6—N2	1.492 (2)	O3W—H3WB	0.828 (16)
C6—H6A	0.9600	O4W—H4WB	0.864 (15)
C6—H6B	0.9600	O4W—H4WA	0.830 (16)
C6—H6C	0.9600	O5W—H5WB	0.808 (15)
C11—C15	1.421 (3)	O5W—H5WA	0.808 (15)
C11—Fe1—C33	152.96 (10)	C15—C11—Fe1	69.63 (11)
C11—Fe1—C15	41.06 (8)	C12—C11—Fe1	70.11 (11)
C33—Fe1—C15	164.27 (10)	C1—C11—Fe1	126.51 (14)
C11—Fe1—C14	68.80 (8)	C13—C12—C11	108.05 (19)
C33—Fe1—C14	126.31 (10)	C13—C12—Fe1	69.67 (12)
C15—Fe1—C14	40.61 (8)	C11—C12—Fe1	68.88 (11)
C11—Fe1—C13	68.63 (8)	C13—C12—H12A	126.0
C33—Fe1—C13	106.99 (10)	C11—C12—H12A	126.0
C15—Fe1—C13	68.48 (9)	Fe1—C12—H12A	126.0
C14—Fe1—C13	40.81 (8)	C12—C13—C14	108.40 (19)
C11—Fe1—C34	165.35 (11)	C12—C13—Fe1	70.03 (12)
C33—Fe1—C34	40.79 (10)	C14—C13—Fe1	69.59 (13)
C15—Fe1—C34	126.71 (11)	C12—C13—H13A	125.8
C14—Fe1—C34	106.78 (10)	C14—C13—H13A	125.8
C13—Fe1—C34	117.80 (10)	Fe1—C13—H13A	125.8
C11—Fe1—C35	128.34 (10)	C15—C14—C13	107.84 (19)
C33—Fe1—C35	68.04 (11)	C15—C14—Fe1	69.43 (13)
C15—Fe1—C35	108.48 (10)	C13—C14—Fe1	69.60 (13)
C14—Fe1—C35	118.64 (10)	C15—C14—H14A	126.1
C13—Fe1—C35	152.19 (9)	C13—C14—H14A	126.1
C34—Fe1—C35	40.38 (10)	Fe1—C14—H14A	126.1
C11—Fe1—C12	41.01 (7)	C14—C15—C11	108.19 (19)
C33—Fe1—C12	118.34 (10)	C14—C15—Fe1	69.97 (12)
C15—Fe1—C12	68.66 (8)	C11—C15—Fe1	69.30 (12)
C14—Fe1—C12	68.37 (9)	C14—C15—H15A	125.9
C13—Fe1—C12	40.30 (8)	C11—C15—H15A	125.9
C34—Fe1—C12	151.84 (10)	Fe1—C15—H15A	125.9
C35—Fe1—C12	166.56 (9)	C22—C21—C25	108.20 (18)
C11—Fe1—C31	109.29 (9)	C22—C21—C4	126.44 (18)
C33—Fe1—C31	67.97 (10)	C25—C21—C4	125.27 (18)
C15—Fe1—C31	120.01 (10)	C22—C21—Fe2	70.40 (11)
C14—Fe1—C31	153.04 (10)	C25—C21—Fe2	70.28 (11)
C13—Fe1—C31	165.57 (10)	C4—C21—Fe2	122.25 (14)
C34—Fe1—C31	67.91 (10)	C21—C22—C23	107.6 (2)
C35—Fe1—C31	40.13 (9)	C21—C22—Fe2	68.73 (11)
C12—Fe1—C31	128.91 (9)	C23—C22—Fe2	69.93 (12)
C11—Fe1—C32	119.57 (9)	C21—C22—H22A	126.2
C33—Fe1—C32	40.55 (9)	C23—C22—H22A	126.2
C15—Fe1—C32	153.95 (10)	Fe2—C22—H22A	126.2
C14—Fe1—C32	164.46 (10)	C24—C23—C22	108.07 (19)
C13—Fe1—C32	127.12 (10)	C24—C23—Fe2	69.69 (13)
C34—Fe1—C32	68.36 (10)	C22—C23—Fe2	69.32 (12)
C35—Fe1—C32	67.92 (10)	C24—C23—H23A	126.0
C12—Fe1—C32	108.51 (9)	C22—C23—H23A	126.0
C31—Fe1—C32	40.43 (9)	Fe2—C23—H23A	126.0
C41—Fe2—C21	107.45 (9)	C23—C24—C25	108.8 (2)
C41—Fe2—C45	40.69 (11)	C23—C24—Fe2	70.23 (13)
C21—Fe2—C45	115.09 (10)	C25—C24—Fe2	69.59 (12)
C41—Fe2—C42	41.24 (11)	C23—C24—H24A	125.6
C21—Fe2—C42	131.42 (10)	C25—C24—H24A	125.6
C45—Fe2—C42	68.25 (12)	Fe2—C24—H24A	125.6
C41—Fe2—C25	129.34 (11)	C24—C25—C21	107.36 (19)
C21—Fe2—C25	41.00 (8)	C24—C25—Fe2	69.77 (12)
C45—Fe2—C25	107.15 (11)	C21—C25—Fe2	68.72 (11)
C42—Fe2—C25	169.64 (10)	C24—C25—H25A	126.3
C41—Fe2—C22	116.57 (11)	C21—C25—H25A	126.3
C21—Fe2—C22	40.87 (7)	Fe2—C25—H25A	126.3
C45—Fe2—C22	148.45 (11)	C35—C31—C32	108.3 (2)
C42—Fe2—C22	110.10 (10)	C35—C31—Fe1	69.65 (13)
C25—Fe2—C22	68.61 (9)	C32—C31—Fe1	69.81 (14)
C41—Fe2—C24	168.34 (13)	C35—C31—H31A	125.9
C21—Fe2—C24	68.56 (8)	C32—C31—H31A	125.9
C45—Fe2—C24	129.95 (12)	Fe1—C31—H31A	125.9
C42—Fe2—C24	149.31 (11)	C33—C32—C31	107.4 (2)
C25—Fe2—C24	40.64 (8)	C33—C32—Fe1	69.06 (13)
C22—Fe2—C24	68.14 (9)	C31—C32—Fe1	69.75 (14)
C41—Fe2—C44	67.84 (11)	C33—C32—H32A	126.3
C21—Fe2—C44	147.24 (9)	C31—C32—H32A	126.3
C45—Fe2—C44	39.82 (10)	Fe1—C32—H32A	126.3
C42—Fe2—C44	67.48 (11)	C32—C33—C34	108.3 (2)
C25—Fe2—C44	115.42 (10)	C32—C33—Fe1	70.39 (12)
C22—Fe2—C44	170.97 (9)	C34—C33—Fe1	69.94 (14)
C24—Fe2—C44	109.17 (11)	C32—C33—H33A	125.8
C41—Fe2—C23	150.02 (13)	C34—C33—H33A	125.8
C21—Fe2—C23	68.61 (8)	Fe1—C33—H33A	125.8
C45—Fe2—C23	168.80 (13)	C35—C34—C33	107.4 (2)
C42—Fe2—C23	118.04 (11)	C35—C34—Fe1	69.82 (13)
C25—Fe2—C23	68.19 (9)	C33—C34—Fe1	69.27 (13)
C22—Fe2—C23	40.75 (8)	C35—C34—H34A	126.3
C24—Fe2—C23	40.08 (9)	C33—C34—H34A	126.3
C44—Fe2—C23	131.80 (10)	Fe1—C34—H34A	126.3
C41—Fe2—C43	67.83 (10)	C31—C35—C34	108.6 (2)
C21—Fe2—C43	170.90 (10)	C31—C35—Fe1	70.22 (13)
C45—Fe2—C43	66.88 (10)	C34—C35—Fe1	69.80 (14)
C42—Fe2—C43	40.01 (10)	C31—C35—H35A	125.7
C25—Fe2—C43	147.99 (10)	C34—C35—H35A	125.7
C22—Fe2—C43	133.22 (9)	Fe1—C35—H35A	125.7
C24—Fe2—C43	117.61 (9)	C45—C41—C42	107.1 (2)
C44—Fe2—C43	39.50 (9)	C45—C41—Fe2	69.88 (15)
C23—Fe2—C43	111.27 (9)	C42—C41—Fe2	70.14 (14)
O3—S1—O1	110.95 (9)	C45—C41—H41A	126.5
O3—S1—O4	110.19 (8)	C42—C41—H41A	126.5
O1—S1—O4	109.64 (9)	Fe2—C41—H41A	126.5
O3—S1—O2	108.37 (8)	C43—C42—C41	106.8 (3)
O1—S1—O2	109.41 (9)	C43—C42—Fe2	70.46 (14)
O4—S1—O2	108.24 (8)	C41—C42—Fe2	68.62 (14)
C11—C1—N1	112.11 (17)	C43—C42—H42A	126.6
C11—C1—H1A	109.2	C41—C42—H42A	126.6
N1—C1—H1A	109.2	Fe2—C42—H42A	126.6
C11—C1—H1B	109.2	C44—C43—C42	109.1 (2)
N1—C1—H1B	109.2	C44—C43—Fe2	69.97 (13)
H1A—C1—H1B	107.9	C42—C43—Fe2	69.53 (13)
N1—C2—H2A	109.5	C44—C43—H43A	125.4
N1—C2—H2B	109.5	C42—C43—H43A	125.4
H2A—C2—H2B	109.5	Fe2—C43—H43A	125.4
N1—C2—H2C	109.5	C43—C44—C45	108.4 (3)
H2A—C2—H2C	109.5	C43—C44—Fe2	70.52 (14)
H2B—C2—H2C	109.5	C45—C44—Fe2	69.32 (15)
N1—C3—H3A	109.5	C43—C44—H44A	125.8
N1—C3—H3B	109.5	C45—C44—H44A	125.8
H3A—C3—H3B	109.5	Fe2—C44—H44A	125.8
N1—C3—H3C	109.5	C44—C45—C41	108.6 (3)
H3A—C3—H3C	109.5	C44—C45—Fe2	70.85 (15)
H3B—C3—H3C	109.5	C41—C45—Fe2	69.44 (16)
C21—C4—N2	112.80 (16)	C44—C45—H45A	125.7
C21—C4—H4A	109.0	C41—C45—H45A	125.7
N2—C4—H4A	109.0	Fe2—C45—H45A	125.7
C21—C4—H4B	109.0	C3—N1—C2	111.09 (18)
N2—C4—H4B	109.0	C3—N1—C1	112.53 (17)
H4A—C4—H4B	107.8	C2—N1—C1	111.53 (17)
N2—C5—H5A	109.5	C3—N1—HN1	107.1
N2—C5—H5B	109.5	C2—N1—HN1	107.1
H5A—C5—H5B	109.5	C1—N1—HN1	107.1
N2—C5—H5C	109.5	C5—N2—C6	111.76 (15)
H5A—C5—H5C	109.5	C5—N2—C4	112.64 (15)
H5B—C5—H5C	109.5	C6—N2—C4	109.86 (14)
N2—C6—H6A	109.5	C5—N2—HN2	107.4
N2—C6—H6B	109.5	C6—N2—HN2	107.4
H6A—C6—H6B	109.5	C4—N2—HN2	107.4
N2—C6—H6C	109.5	H1WA—O1W—H1WB	107 (2)
H6A—C6—H6C	109.5	H2WA—O2W—H2WB	111 (2)
H6B—C6—H6C	109.5	H3WA—O3W—H3WB	110 (2)
C15—C11—C12	107.51 (18)	H4WB—O4W—H4WA	108 (2)
C15—C11—C1	126.73 (19)	H5WB—O5W—H5WA	117 (2)
C12—C11—C1	125.75 (19)
N1—C1—C11—C15	94.2 (2)	C45—Fe2—C25—C24	132.24 (16)
N1—C1—C11—C12	−84.5 (3)	C42—Fe2—C25—C24	−165.7 (6)
N1—C1—C11—Fe1	−175.15 (14)	C22—Fe2—C25—C24	−80.94 (15)
C33—Fe1—C11—C15	−166.98 (19)	C44—Fe2—C25—C24	90.25 (16)
C14—Fe1—C11—C15	−37.40 (13)	C23—Fe2—C25—C24	−36.95 (14)
C13—Fe1—C11—C15	−81.35 (14)	C43—Fe2—C25—C24	58.6 (2)
C34—Fe1—C11—C15	37.5 (4)	C41—Fe2—C25—C21	−69.40 (19)
C35—Fe1—C11—C15	73.00 (16)	C45—Fe2—C25—C21	−108.76 (15)
C12—Fe1—C11—C15	−118.40 (18)	C42—Fe2—C25—C21	−46.7 (6)
C31—Fe1—C11—C15	113.89 (14)	C22—Fe2—C25—C21	38.07 (12)
C32—Fe1—C11—C15	157.12 (14)	C24—Fe2—C25—C21	119.0 (2)
C33—Fe1—C11—C12	−48.6 (3)	C44—Fe2—C25—C21	−150.75 (13)
C15—Fe1—C11—C12	118.40 (18)	C23—Fe2—C25—C21	82.05 (14)
C14—Fe1—C11—C12	80.99 (13)	C43—Fe2—C25—C21	177.61 (16)
C13—Fe1—C11—C12	37.05 (12)	C11—Fe1—C31—C35	−127.18 (16)
C34—Fe1—C11—C12	155.9 (3)	C33—Fe1—C31—C35	81.61 (17)
C35—Fe1—C11—C12	−168.61 (13)	C15—Fe1—C31—C35	−83.27 (17)
C31—Fe1—C11—C12	−127.71 (14)	C14—Fe1—C31—C35	−46.2 (3)
C32—Fe1—C11—C12	−84.49 (15)	C13—Fe1—C31—C35	153.7 (3)
C33—Fe1—C11—C1	71.8 (3)	C34—Fe1—C31—C35	37.43 (16)
C15—Fe1—C11—C1	−121.3 (2)	C12—Fe1—C31—C35	−169.04 (14)
C14—Fe1—C11—C1	−158.7 (2)	C32—Fe1—C31—C35	119.5 (2)
C13—Fe1—C11—C1	157.4 (2)	C11—Fe1—C31—C32	113.28 (14)
C34—Fe1—C11—C1	−83.7 (4)	C33—Fe1—C31—C32	−37.92 (14)
C35—Fe1—C11—C1	−48.3 (2)	C15—Fe1—C31—C32	157.20 (13)
C12—Fe1—C11—C1	120.3 (2)	C14—Fe1—C31—C32	−165.75 (18)
C31—Fe1—C11—C1	−7.4 (2)	C13—Fe1—C31—C32	34.2 (4)
C32—Fe1—C11—C1	35.9 (2)	C34—Fe1—C31—C32	−82.10 (15)
C15—C11—C12—C13	1.0 (2)	C35—Fe1—C31—C32	−119.5 (2)
C1—C11—C12—C13	179.90 (18)	C12—Fe1—C31—C32	71.43 (17)
Fe1—C11—C12—C13	−58.82 (14)	C35—C31—C32—C33	−0.2 (3)
C15—C11—C12—Fe1	59.85 (14)	Fe1—C31—C32—C33	59.03 (16)
C1—C11—C12—Fe1	−121.3 (2)	C35—C31—C32—Fe1	−59.22 (16)
C11—Fe1—C12—C13	119.83 (18)	C11—Fe1—C32—C33	155.79 (15)
C33—Fe1—C12—C13	−82.96 (15)	C15—Fe1—C32—C33	−168.6 (2)
C15—Fe1—C12—C13	81.48 (13)	C14—Fe1—C32—C33	36.6 (4)
C14—Fe1—C12—C13	37.70 (13)	C13—Fe1—C32—C33	71.30 (18)
C34—Fe1—C12—C13	−47.6 (3)	C34—Fe1—C32—C33	−37.90 (16)
C35—Fe1—C12—C13	161.7 (4)	C35—Fe1—C32—C33	−81.57 (17)
C31—Fe1—C12—C13	−166.51 (14)	C12—Fe1—C32—C33	112.25 (16)
C32—Fe1—C12—C13	−126.09 (14)	C31—Fe1—C32—C33	−118.8 (2)
C33—Fe1—C12—C11	157.21 (13)	C11—Fe1—C32—C31	−85.40 (15)
C15—Fe1—C12—C11	−38.34 (12)	C33—Fe1—C32—C31	118.8 (2)
C14—Fe1—C12—C11	−82.13 (13)	C15—Fe1—C32—C31	−49.8 (3)
C13—Fe1—C12—C11	−119.83 (18)	C14—Fe1—C32—C31	155.4 (3)
C34—Fe1—C12—C11	−167.38 (19)	C13—Fe1—C32—C31	−169.89 (13)
C35—Fe1—C12—C11	41.8 (4)	C34—Fe1—C32—C31	80.91 (15)
C31—Fe1—C12—C11	73.66 (17)	C35—Fe1—C32—C31	37.24 (14)
C32—Fe1—C12—C11	114.08 (14)	C12—Fe1—C32—C31	−128.94 (13)
C11—C12—C13—C14	−0.9 (2)	C31—C32—C33—C34	0.4 (3)
Fe1—C12—C13—C14	−59.22 (15)	Fe1—C32—C33—C34	59.88 (16)
C11—C12—C13—Fe1	58.34 (14)	C31—C32—C33—Fe1	−59.47 (16)
C11—Fe1—C13—C12	−37.68 (12)	C11—Fe1—C33—C32	−51.7 (3)
C33—Fe1—C13—C12	114.02 (14)	C15—Fe1—C33—C32	161.4 (3)
C15—Fe1—C13—C12	−81.95 (13)	C14—Fe1—C33—C32	−168.58 (15)
C14—Fe1—C13—C12	−119.57 (18)	C13—Fe1—C33—C32	−127.83 (16)
C34—Fe1—C13—C12	156.81 (14)	C34—Fe1—C33—C32	119.1 (2)
C35—Fe1—C13—C12	−170.98 (19)	C35—Fe1—C33—C32	81.24 (16)
C31—Fe1—C13—C12	46.8 (4)	C12—Fe1—C33—C32	−85.67 (17)
C32—Fe1—C13—C12	73.93 (15)	C31—Fe1—C33—C32	37.81 (15)
C11—Fe1—C13—C14	81.89 (13)	C11—Fe1—C33—C34	−170.75 (18)
C33—Fe1—C13—C14	−126.41 (14)	C15—Fe1—C33—C34	42.3 (4)
C15—Fe1—C13—C14	37.62 (12)	C14—Fe1—C33—C34	72.35 (18)
C34—Fe1—C13—C14	−83.62 (16)	C13—Fe1—C33—C34	113.09 (16)
C35—Fe1—C13—C14	−51.4 (3)	C35—Fe1—C33—C34	−37.83 (15)
C12—Fe1—C13—C14	119.57 (18)	C12—Fe1—C33—C34	155.25 (15)
C31—Fe1—C13—C14	166.3 (3)	C31—Fe1—C33—C34	−81.26 (16)
C32—Fe1—C13—C14	−166.50 (13)	C32—Fe1—C33—C34	−119.1 (2)
C12—C13—C14—C15	0.4 (2)	C32—C33—C34—C35	−0.5 (3)
Fe1—C13—C14—C15	−59.10 (15)	Fe1—C33—C34—C35	59.69 (16)
C12—C13—C14—Fe1	59.49 (15)	C32—C33—C34—Fe1	−60.16 (16)
C11—Fe1—C14—C15	37.81 (12)	C11—Fe1—C34—C35	44.6 (4)
C33—Fe1—C14—C15	−167.97 (15)	C33—Fe1—C34—C35	−118.6 (2)
C13—Fe1—C14—C15	119.26 (18)	C15—Fe1—C34—C35	74.56 (18)
C34—Fe1—C14—C15	−127.41 (15)	C14—Fe1—C34—C35	114.71 (16)
C35—Fe1—C14—C15	−85.30 (15)	C13—Fe1—C34—C35	157.43 (15)
C12—Fe1—C14—C15	82.02 (13)	C12—Fe1—C34—C35	−169.92 (17)
C31—Fe1—C14—C15	−53.3 (2)	C31—Fe1—C34—C35	−37.21 (15)
C32—Fe1—C14—C15	163.3 (3)	C32—Fe1—C34—C35	−80.92 (16)
C11—Fe1—C14—C13	−81.45 (13)	C11—Fe1—C34—C33	163.2 (3)
C33—Fe1—C14—C13	72.77 (17)	C15—Fe1—C34—C33	−166.83 (14)
C15—Fe1—C14—C13	−119.26 (18)	C14—Fe1—C34—C33	−126.68 (15)
C34—Fe1—C14—C13	113.33 (15)	C13—Fe1—C34—C33	−83.96 (17)
C35—Fe1—C14—C13	155.45 (13)	C35—Fe1—C34—C33	118.6 (2)
C12—Fe1—C14—C13	−37.24 (12)	C12—Fe1—C34—C33	−51.3 (3)
C31—Fe1—C14—C13	−172.53 (18)	C31—Fe1—C34—C33	81.40 (16)
C32—Fe1—C14—C13	44.0 (4)	C32—Fe1—C34—C33	37.69 (15)
C13—C14—C15—C11	0.3 (2)	C32—C31—C35—C34	−0.1 (3)
Fe1—C14—C15—C11	−58.95 (15)	Fe1—C31—C35—C34	−59.43 (17)
C13—C14—C15—Fe1	59.21 (16)	C32—C31—C35—Fe1	59.33 (16)
C12—C11—C15—C14	−0.8 (2)	C33—C34—C35—C31	0.3 (3)
C1—C11—C15—C14	−179.65 (19)	Fe1—C34—C35—C31	59.69 (17)
Fe1—C11—C15—C14	59.36 (15)	C33—C34—C35—Fe1	−59.34 (16)
C12—C11—C15—Fe1	−60.15 (14)	C11—Fe1—C35—C31	73.47 (19)
C1—C11—C15—Fe1	121.0 (2)	C33—Fe1—C35—C31	−81.42 (17)
C11—Fe1—C15—C14	−119.54 (18)	C15—Fe1—C35—C31	114.94 (16)
C33—Fe1—C15—C14	38.3 (4)	C14—Fe1—C35—C31	158.10 (15)
C13—Fe1—C15—C14	−37.80 (13)	C13—Fe1—C35—C31	−166.31 (19)
C34—Fe1—C15—C14	71.55 (17)	C34—Fe1—C35—C31	−119.6 (2)
C35—Fe1—C15—C14	112.74 (14)	C12—Fe1—C35—C31	39.6 (5)
C12—Fe1—C15—C14	−81.24 (14)	C32—Fe1—C35—C31	−37.51 (15)
C31—Fe1—C15—C14	155.18 (13)	C11—Fe1—C35—C34	−166.91 (15)
C32—Fe1—C15—C14	−169.9 (2)	C33—Fe1—C35—C34	38.20 (15)
C33—Fe1—C15—C11	157.8 (3)	C15—Fe1—C35—C34	−125.43 (16)
C14—Fe1—C15—C11	119.54 (18)	C14—Fe1—C35—C34	−82.28 (18)
C13—Fe1—C15—C11	81.74 (13)	C13—Fe1—C35—C34	−46.7 (3)
C34—Fe1—C15—C11	−168.91 (14)	C12—Fe1—C35—C34	159.2 (4)
C35—Fe1—C15—C11	−127.73 (13)	C31—Fe1—C35—C34	119.6 (2)
C12—Fe1—C15—C11	38.30 (12)	C32—Fe1—C35—C34	82.11 (17)
C31—Fe1—C15—C11	−85.28 (15)	C21—Fe2—C41—C45	−108.44 (16)
C32—Fe1—C15—C11	−50.4 (3)	C42—Fe2—C41—C45	117.7 (2)
N2—C4—C21—C22	−104.7 (2)	C25—Fe2—C41—C45	−68.37 (19)
N2—C4—C21—C25	79.3 (2)	C22—Fe2—C41—C45	−151.63 (15)
N2—C4—C21—Fe2	166.83 (13)	C24—Fe2—C41—C45	−40.3 (5)
C41—Fe2—C21—C22	−110.69 (16)	C44—Fe2—C41—C45	37.03 (15)
C45—Fe2—C21—C22	−153.76 (15)	C23—Fe2—C41—C45	174.28 (17)
C42—Fe2—C21—C22	−71.38 (18)	C43—Fe2—C41—C45	79.83 (17)
C25—Fe2—C21—C22	118.67 (18)	C21—Fe2—C41—C42	133.90 (16)
C24—Fe2—C21—C22	80.94 (14)	C45—Fe2—C41—C42	−117.7 (2)
C44—Fe2—C21—C22	173.32 (17)	C25—Fe2—C41—C42	173.96 (15)
C23—Fe2—C21—C22	37.75 (13)	C22—Fe2—C41—C42	90.71 (17)
C43—Fe2—C21—C22	−53.3 (6)	C24—Fe2—C41—C42	−158.0 (4)
C41—Fe2—C21—C25	130.64 (16)	C44—Fe2—C41—C42	−80.64 (17)
C45—Fe2—C21—C25	87.57 (17)	C23—Fe2—C41—C42	56.6 (2)
C42—Fe2—C21—C25	169.94 (16)	C43—Fe2—C41—C42	−37.83 (16)
C22—Fe2—C21—C25	−118.67 (18)	C45—C41—C42—C43	0.0 (3)
C24—Fe2—C21—C25	−37.73 (13)	Fe2—C41—C42—C43	60.43 (18)
C44—Fe2—C21—C25	54.7 (2)	C45—C41—C42—Fe2	−60.44 (18)
C23—Fe2—C21—C25	−80.93 (14)	C41—Fe2—C42—C43	−117.9 (3)
C43—Fe2—C21—C25	−172.0 (6)	C21—Fe2—C42—C43	175.62 (14)
C41—Fe2—C21—C4	10.7 (2)	C45—Fe2—C42—C43	−79.50 (18)
C45—Fe2—C21—C4	−32.4 (2)	C25—Fe2—C42—C43	−144.8 (5)
C42—Fe2—C21—C4	50.0 (2)	C22—Fe2—C42—C43	134.30 (16)
C25—Fe2—C21—C4	−119.9 (2)	C24—Fe2—C42—C43	53.5 (3)
C22—Fe2—C21—C4	121.4 (2)	C44—Fe2—C42—C43	−36.36 (15)
C24—Fe2—C21—C4	−157.68 (19)	C23—Fe2—C42—C43	90.27 (17)
C44—Fe2—C21—C4	−65.3 (2)	C21—Fe2—C42—C41	−66.4 (2)
C23—Fe2—C21—C4	159.13 (19)	C45—Fe2—C42—C41	38.44 (16)
C43—Fe2—C21—C4	68.1 (6)	C25—Fe2—C42—C41	−26.9 (7)
C25—C21—C22—C23	1.0 (2)	C22—Fe2—C42—C41	−107.77 (18)
C4—C21—C22—C23	−175.54 (19)	C24—Fe2—C42—C41	171.5 (2)
Fe2—C21—C22—C23	−59.36 (15)	C44—Fe2—C42—C41	81.57 (18)
C25—C21—C22—Fe2	60.39 (14)	C23—Fe2—C42—C41	−151.79 (17)
C4—C21—C22—Fe2	−116.2 (2)	C43—Fe2—C42—C41	117.9 (3)
C41—Fe2—C22—C21	86.24 (16)	C41—C42—C43—C44	−0.3 (3)
C45—Fe2—C22—C21	49.9 (2)	Fe2—C42—C43—C44	58.90 (18)
C42—Fe2—C22—C21	130.82 (14)	C41—C42—C43—Fe2	−59.25 (16)
C25—Fe2—C22—C21	−38.18 (12)	C41—Fe2—C43—C44	−81.60 (18)
C24—Fe2—C22—C21	−82.06 (13)	C21—Fe2—C43—C44	−141.8 (5)
C44—Fe2—C22—C21	−156.4 (6)	C45—Fe2—C43—C44	−37.36 (17)
C23—Fe2—C22—C21	−119.17 (19)	C42—Fe2—C43—C44	−120.6 (2)
C43—Fe2—C22—C21	169.98 (14)	C25—Fe2—C43—C44	48.2 (3)
C41—Fe2—C22—C23	−154.59 (16)	C22—Fe2—C43—C44	172.14 (15)
C21—Fe2—C22—C23	119.17 (19)	C24—Fe2—C43—C44	87.02 (18)
C45—Fe2—C22—C23	169.1 (2)	C23—Fe2—C43—C44	130.71 (16)
C42—Fe2—C22—C23	−110.01 (16)	C41—Fe2—C43—C42	38.97 (19)
C25—Fe2—C22—C23	80.99 (14)	C21—Fe2—C43—C42	−21.2 (7)
C24—Fe2—C22—C23	37.11 (13)	C45—Fe2—C43—C42	83.22 (19)
C44—Fe2—C22—C23	−37.2 (7)	C25—Fe2—C43—C42	168.73 (19)
C43—Fe2—C22—C23	−70.85 (18)	C22—Fe2—C43—C42	−67.3 (2)
C21—C22—C23—C24	−0.5 (2)	C24—Fe2—C43—C42	−152.41 (17)
Fe2—C22—C23—C24	−59.11 (16)	C44—Fe2—C43—C42	120.6 (2)
C21—C22—C23—Fe2	58.61 (14)	C23—Fe2—C43—C42	−108.72 (18)
C41—Fe2—C23—C24	169.74 (18)	C42—C43—C44—C45	0.6 (3)
C21—Fe2—C23—C24	81.71 (14)	Fe2—C43—C44—C45	59.20 (18)
C45—Fe2—C23—C24	−29.8 (6)	C42—C43—C44—Fe2	−58.63 (18)
C42—Fe2—C23—C24	−151.68 (14)	C41—Fe2—C44—C43	81.57 (18)
C25—Fe2—C23—C24	37.46 (13)	C21—Fe2—C44—C43	169.59 (16)
C22—Fe2—C23—C24	119.56 (19)	C45—Fe2—C44—C43	119.4 (2)
C44—Fe2—C23—C24	−67.75 (18)	C42—Fe2—C44—C43	36.81 (16)
C43—Fe2—C23—C24	−108.06 (15)	C25—Fe2—C44—C43	−154.07 (15)
C41—Fe2—C23—C22	50.2 (2)	C22—Fe2—C44—C43	−39.4 (7)
C21—Fe2—C23—C22	−37.85 (12)	C24—Fe2—C44—C43	−110.48 (16)
C45—Fe2—C23—C22	−149.4 (5)	C23—Fe2—C44—C43	−71.4 (2)
C42—Fe2—C23—C22	88.76 (15)	C41—Fe2—C44—C45	−37.81 (18)
C25—Fe2—C23—C22	−82.10 (13)	C21—Fe2—C44—C45	50.2 (3)
C24—Fe2—C23—C22	−119.56 (19)	C42—Fe2—C44—C45	−82.57 (19)
C44—Fe2—C23—C22	172.69 (14)	C25—Fe2—C44—C45	86.54 (19)
C43—Fe2—C23—C22	132.38 (14)	C22—Fe2—C44—C45	−158.8 (6)
C22—C23—C24—C25	−0.2 (3)	C24—Fe2—C44—C45	130.14 (18)
Fe2—C23—C24—C25	−59.10 (16)	C23—Fe2—C44—C45	169.26 (18)
C22—C23—C24—Fe2	58.87 (16)	C43—Fe2—C44—C45	−119.4 (2)
C41—Fe2—C24—C23	−153.9 (5)	C43—C44—C45—C41	−0.6 (3)
C21—Fe2—C24—C23	−81.84 (14)	Fe2—C44—C45—C41	59.37 (19)
C45—Fe2—C24—C23	172.76 (14)	C43—C44—C45—Fe2	−59.95 (18)
C42—Fe2—C24—C23	55.1 (2)	C42—C41—C45—C44	0.4 (3)
C25—Fe2—C24—C23	−119.9 (2)	Fe2—C41—C45—C44	−60.25 (18)
C22—Fe2—C24—C23	−37.72 (12)	C42—C41—C45—Fe2	60.61 (18)
C44—Fe2—C24—C23	133.07 (14)	C41—Fe2—C45—C44	119.4 (2)
C43—Fe2—C24—C23	90.81 (15)	C21—Fe2—C45—C44	−152.67 (16)
C41—Fe2—C24—C25	−34.0 (6)	C42—Fe2—C45—C44	80.49 (18)
C21—Fe2—C24—C25	38.05 (13)	C25—Fe2—C45—C44	−109.36 (17)
C45—Fe2—C24—C25	−67.34 (18)	C22—Fe2—C45—C44	173.76 (17)
C42—Fe2—C24—C25	175.02 (19)	C24—Fe2—C45—C44	−70.4 (2)
C22—Fe2—C24—C25	82.18 (14)	C23—Fe2—C45—C44	−45.7 (6)
C44—Fe2—C24—C25	−107.03 (15)	C43—Fe2—C45—C44	37.07 (16)
C23—Fe2—C24—C25	119.9 (2)	C21—Fe2—C45—C41	87.90 (17)
C43—Fe2—C24—C25	−149.29 (14)	C42—Fe2—C45—C41	−38.95 (15)
C23—C24—C25—C21	0.9 (3)	C25—Fe2—C45—C41	131.21 (16)
Fe2—C24—C25—C21	−58.63 (15)	C22—Fe2—C45—C41	54.3 (3)
C23—C24—C25—Fe2	59.50 (16)	C24—Fe2—C45—C41	170.18 (15)
C22—C21—C25—C24	−1.2 (2)	C44—Fe2—C45—C41	−119.4 (2)
C4—C21—C25—C24	175.45 (19)	C23—Fe2—C45—C41	−165.1 (5)
Fe2—C21—C25—C24	59.30 (15)	C43—Fe2—C45—C41	−82.37 (18)
C22—C21—C25—Fe2	−60.47 (14)	C11—C1—N1—C3	−62.4 (2)
C4—C21—C25—Fe2	116.2 (2)	C11—C1—N1—C2	172.01 (18)
C41—Fe2—C25—C24	171.60 (17)	C21—C4—N2—C5	60.8 (2)
C21—Fe2—C25—C24	−119.0 (2)	C21—C4—N2—C6	−173.88 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O2	0.91	1.85	2.745 (2)	168
N2—HN2···O4	0.91	1.89	2.757 (2)	158
O1W—H1WA···O1	0.85 (2)	1.91 (2)	2.758 (3)	174 (3)
O1W—H1WB···O5W	0.84 (2)	2.06 (2)	2.847 (3)	158 (3)
O2W—H2WA···O4W^i	0.83 (2)	2.05 (2)	2.853 (3)	162 (3)
O2W—H2WB···O4	0.83 (2)	2.07 (2)	2.884 (3)	167 (3)
O3W—H3WA···O1^ii	0.83 (2)	1.96 (2)	2.754 (2)	160 (3)
O3W—H3WB···O2	0.83 (2)	2.03 (2)	2.773 (2)	150 (3)
O4W—H4WB···O5W^iii	0.86 (2)	2.00 (2)	2.853 (3)	168 (3)
O4W—H4WA···O3	0.83 (2)	1.93 (2)	2.754 (2)	177 (3)
O5W—H5WB···O3W^iv	0.81 (2)	1.90 (2)	2.697 (3)	171 (3)
O5W—H5WA···O1W^v	0.81 (2)	1.95 (2)	2.745 (3)	168 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) −x+1, −y, −z.