Ferrocene compounds. XXXIV. 1′-(tert-Butoxycarbonylamino)ferrocene-1-carboxylic acid

Heteroannularly substituted ferrocene derivatives can act as model systems for various hydrogen-bonded assemblies of biomol­ecules formed, for instance, by means of O—H...O and N—H...O hydrogen bonding. The crystal structure analysis of 1′-(tert-butoxy­carbonyl­amino)­ferrocene-1-carbox­ylic acid, [Fe(C₁₀H₁₄NO₂)(C₆H₅O₂)] or (C₅H₄COOH)Fe(C₅­H₄NHCOOC(CH₃)₃, reveals two independent mol­ecules within the asymmetric unit, and these are joined into discrete dimers by two types of intermolecular hydrogen bonds, viz. O—H...O and N—H...O. The –COOH and –NHCOOR groups are archetypes for dimer formation via two eight-membered rings. The O—H...O hydrogen bonds [2.656 (3) and 2.663 (3) Å] form a cyclic carboxylic acid dimer motif. Another eight-membered ring is formed by N—H...O hydrogen bonds [2.827 (3) and 2.854 (3) Å] between the N—H group and an O atom of another carbamoyl moiety. The dimers are assembled in a herring-bone fashion in the bc plane.

S1. Comment

Conjugates of metallocenes with natural amino acids and peptides are of great interest in the field of bioorganometallic chemistry. Over the past five decades, many N– and C-ferrocenylamino acids and their derived peptides have been synthesized and studied. Current investigations have concentrated on 1,1'-ferrocenylenebis(amino acids) and the corresponding peptides, especially as chemical models of β-sheet and α-helix arrays, having interesting electrochemical and chelating properties (Oberhoff et al., 1996; Kraatz et al., 1997; Saweczko et al., 2001; Metzler-Nolte, 2001; Moriuchi et al., 2001; Pal et al., 2001).

Our investigations are directed towards the synthesis and characterization of a series of synthetic amino acids containing a skeletally bonded 1,1'-ferrocenylene unit. The first homologue of this class of heteroannularly substituted ferrocene compounds is 1'-aminoferrocene-1-carboxylic acid. The C– and/or N-protected derivatives of this compound, as well as its conjugates with natural amino acids (Barišić et al., 2002; Rapić et al., 2002; Barišić et al., 2003), can reveal various types of hydrogen bonds, such as N—H···O═C, O—H···O and C—H···O bonds, and a range of hydrogen-bonding patterns (infinite chains, discrete dimers, etc.; Pavlović et al., 2000; Pavlović, Barišić, Rapić & Leban, 2002; Pavlović, Barišić, Lapić & Rapić, 2002; Rapić et al., 2002), which act as models for the study of hydrogen bonding in biological environments. Therefore, such carboxy derivatives can be used as organometallic building blocks for crystal engineering (Braga et al., 2001), where R₂²(8) rings are the most frequent supramolecular synthons formed by carboxyl groups. In this context, the crystal structure of the title compound, (I), is presented here. \sch

Compound (I) crystallizes with Z' = 2 (Fig. 1). The two molecules have different conformations adjacent to the tert-Bu groups. The other parts of the molecules differ slightly. Both molecules exhibit disorder of the carboxylic acid group, with H atoms occurring statistically with equal probability (see Experimental).

Within the ferrocenyl moieties, the mean Fe—C bond distances for substituted and unsubstituted C atoms do not exhibit significant differences, according to the 3σ crystallographic criterion, with mean values for Fe—C(unsubstituted) of 2.044 (3) Å and Fe—C(substituted) of 2.054 (3) Å. The Cp rings are twisted away from the fully eclipsed conformation. The dihedral angles between the corresponding planes calculated through two C atoms and the centroids Cg1, Cg2, Cg3 and Cg4 Please define each of these are in the ranges 11.7 (6)–12.6 (3)° and 12.7 (3)–13.2 (3)° for molecules 1 and 2, containing Fe1 and Fe2, respectively. The distances between the Fe atoms and the centroids are Cg1—Fe1 1.6633 (4), Cg2—Fe1 1.6490 (4), Cg3—Fe2 1.6618 (6) and Cg4—Fe2 1.6487 Å, and the angles are Cg1—Fe1—Cg2 179.15 (3) and Cg3—Fe2—Cg4 179.72 (4)°.

The carboxylic acid moieties are coplanar with the ferrocenyl moieties to which they belong, and the planarity is slightly more pronounced in one molecule than in the other; the dihedral angle between the planes defined by atoms C16—C110 and C116, O3 and O4 is 2.4 (5)°, and the dihedral angle between the planes defined by atoms C26—C210 and C216, O7 and O8 is 4.2 (5)°. The C_ring—C_carboxyl bond distances (C16—C116 and C26—C216) of 1.469 (5) and 1.464 (4) Å, respectively, have significant π character, due to the coupling of the π electrons of the Cp ring and the carboxyl moiety. These bonds are comparable with the analogous value of 1.466 (2) Å in the structure of ferrocene-1,1'-dicarboxylic acid (FDAH; neutron study at 78 K; Takusagawa & Koetzle, 1979), but noticeably longer than the value of 1.407 (15) Å in the structure of ferrocenecarboxylic acid (FCAH; Cotton & Reid, 1985). A later, more precise study of FCAH at low temperature gave a value of 1.462 (2) Å (Reference?), consistent with the calculated value of 1.460 Å for the C_ring—C_carboxyl bond distance (Lin et al., 1998).

The NHCOO⁻ groups are inclined towards the Cp rings by 16.7 (2) and 6.9 (2)°, which is more twisted than the carboxyl groups. This is in accordance with the bulkiness of the ^tBu substituents. π-Delocalization through the NHCOO⁻ groups and Cp rings is indicated by the N1—C111 and N2—C211 bond distances of 1.344 (4) and 1.356 (4) Å, respectively, which are in between values for single and double bonds. The other geometric parameters within the carboxyl and Boc [NHCOOC(CH₃)₃] moieties are normal (Allen et al., 1987).

The two independent molecules in (I) are hydrogen bonded into discrete dimers (Fig. 2). In a similar manner, FCAH (Cotton & Reid, 1985) and FDAH (Takusagawa & Koetzle, 1979) are dimerized in the solid state into units containing O—H···O hydrogen bonds [2.714 (14) Å in FCAH and 2.5997–2.6597 Å for the two independent molecules in FDAH], as is found in most structures of carboxylic acid derivatives (Leiserowitz, 1976). The dimers in (I) are formed by two eight-membered rings. One ring resembles carboxylic acid dimers, with O—H···O intermolecular hydrogen bonds (Table 2) of 2.656 (3) Å for O4···O7 and 2.663 (3) Å for O8···O3. The other ring is formed by N—H···O intermolecular hydrogen bonds between the NHCOO⁻ group and an O atom from the carbamoyl moiety. This N—H···O hydrogen bond is longer, as expected, being 2.827 (3) and 2.854 (3) Å for N1···O6 and N2···O2, respectively. The two eight-membered rings are twisted with respect to each other by 5.9 (6)°.

S2. Experimental

The synthesis of compound (I) was published recently by Barišić et al. (2002) Is this ref. 2 or 3?. Diffraction quality crystals of (I) were obtained from solution in dichloromethane-n-pentane (Ratio?).

S3. Refinement

The statistical disorder (Leiserowitz, 1976) of the H atoms belonging to the carboxylic acid groups was established due to the possible rotation around the C16—C116 and C26—C216 single bonds. The relatively large displacement parameters of carboxylic acid atoms O3, O4, O7 and O8 [U_eq = 0.0617 (7)–0.0730 (9)] are also an indication of the presence of disorder, along with the C116—O3 and C116—O4, and C216—O7 and C216—O8 bonds, which are all longer than typical C═O bonds in C_ar—C(═O)-OH and shorter than typical C_ar—O bonds (Allen et al., 1987). H atoms were treated as riding, with O—H distances of 0.82 Å, N—H distances of 0.86 Å and C—H distances in the range 0.93–0.96 Å.

Computing details

Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A view of the two independent molecules in the structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The dimerization of the two crystallographically independent molecules of (I) in the unit cell. Two eight-membered rings are formed by intermolecular hydrogen bonds between the two molecules. The hydrogen bonds are indicated by dashed lines.

1'-(tert-butoxycarbonylamino)ferrocene-1-carboxylic acid

Crystal data

[Fe(C10H14NO2)(C6H5O2)]	F(000) = 1440
Mr = 345.17	Dx = 1.438 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 72 reflections
a = 10.1876 (7) Å	θ = 10.0–18.3°
b = 18.8055 (15) Å	µ = 0.96 mm^−1
c = 16.7034 (13) Å	T = 293 K
β = 94.590 (7)°	Prism, orange
V = 3189.8 (4) Å^3	0.53 × 0.26 × 0.13 mm
Z = 8

Data collection

Philips PW1100 updated by Stoe diffractometer	3237 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 30.0°, θmin = 2.7°
ω scans	h = −14→14
Absorption correction: ψ scan (X-RED; Stoe & Cie, 1995)	k = 0→26
Tmin = 0.630, Tmax = 0.885	l = 0→23
11087 measured reflections	4 standard reflections every 120 min
9280 independent reflections	intensity decay: 3.6%

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0359P)^2] where P = (Fo^2 + 2Fc^2)/3
9280 reflections	(Δ/σ)max = 0.001
405 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.66432 (4)	0.16259 (2)	0.06101 (3)	0.04336 (14)
Fe2	−0.01794 (4)	0.06189 (3)	0.34206 (3)	0.04249 (14)
O1	0.2667 (2)	0.13330 (13)	−0.03557 (13)	0.0553 (6)
O2	0.1729 (2)	0.10278 (13)	0.07927 (13)	0.0606 (7)
O3	0.3923 (2)	0.23525 (14)	0.18130 (16)	0.0709 (8)
O4	0.5245 (2)	0.16575 (15)	0.26132 (16)	0.0659 (7)
H4	0.4578	0.1624	0.2855	0.099*
O5	0.3095 (2)	−0.04774 (12)	0.31080 (13)	0.0550 (6)
O6	0.4067 (2)	0.01075 (12)	0.21271 (13)	0.0544 (6)
O7	0.3276 (2)	0.13808 (13)	0.35166 (14)	0.0617 (7)
O8	0.1933 (2)	0.20503 (15)	0.26969 (17)	0.0724 (8)
H8	0.2599	0.2082	0.2454	0.109*
N1	0.3910 (3)	0.08910 (14)	0.06783 (15)	0.0492 (7)
H1	0.3973	0.0720	0.1157	0.059*
N2	0.1871 (2)	0.01609 (14)	0.21996 (14)	0.0438 (7)
H2	0.1827	0.0407	0.1764	0.053*
C11	0.5104 (3)	0.09262 (18)	0.03092 (19)	0.0461 (9)
C12	0.5422 (3)	0.1326 (2)	−0.03701 (19)	0.0572 (10)
H12	0.4861	0.1628	−0.0677	0.069*
C13	0.6753 (4)	0.1178 (2)	−0.0493 (2)	0.0667 (11)
H13	0.7216	0.1362	−0.0904	0.080*
C14	0.7258 (4)	0.0708 (2)	0.0109 (2)	0.0654 (11)
H14	0.8110	0.0527	0.0168	0.079*
C15	0.6240 (3)	0.05593 (18)	0.0607 (2)	0.0549 (9)
H15	0.6308	0.0267	0.1058	0.066*
C16	0.6171 (3)	0.22240 (17)	0.1559 (2)	0.0439 (8)
C17	0.6202 (3)	0.26541 (18)	0.0859 (2)	0.0554 (10)
H17	0.5505	0.2914	0.0614	0.067*
C18	0.7490 (4)	0.26122 (18)	0.0605 (2)	0.0589 (10)
H18	0.7788	0.2843	0.0162	0.071*
C19	0.8248 (3)	0.21614 (19)	0.1135 (2)	0.0543 (10)
H19	0.9130	0.2046	0.1104	0.065*
C110	0.7436 (3)	0.19171 (18)	0.1718 (2)	0.0509 (9)
H110	0.7686	0.1607	0.2136	0.061*
C111	0.2686 (4)	0.10834 (18)	0.0399 (2)	0.0473 (9)
C112	0.1456 (3)	0.15861 (19)	−0.07908 (19)	0.0488 (9)
C113	0.1905 (4)	0.1731 (2)	−0.1615 (2)	0.0708 (12)
H3A	0.2592	0.2082	−0.1576	0.106*
H3B	0.1176	0.1904	−0.1961	0.106*
H3C	0.2232	0.1300	−0.1833	0.106*
C114	0.0411 (4)	0.1014 (2)	−0.0827 (2)	0.0807 (13)
H4A	0.0777	0.0576	−0.1002	0.121*
H4B	−0.0311	0.1153	−0.1199	0.121*
H4C	0.0103	0.0951	−0.0304	0.121*
C115	0.1009 (5)	0.2256 (2)	−0.0397 (3)	0.1020 (16)
H5A	0.0729	0.2144	0.0123	0.153*
H5B	0.0288	0.2462	−0.0723	0.153*
H5C	0.1725	0.2589	−0.0341	0.153*
C116	0.5027 (4)	0.20754 (18)	0.2015 (2)	0.0478 (9)
C21	0.0657 (3)	0.00471 (16)	0.25280 (18)	0.0390 (8)
C22	0.0334 (3)	−0.04169 (17)	0.31572 (19)	0.0454 (9)
H22	0.0914	−0.0706	0.3467	0.054*
C23	−0.1046 (3)	−0.03538 (18)	0.3221 (2)	0.0526 (9)
H23	−0.1528	−0.0602	0.3580	0.063*
C24	−0.1556 (3)	0.01435 (19)	0.2655 (2)	0.0524 (9)
H24	−0.2433	0.0282	0.2574	0.063*
C25	−0.0510 (3)	0.03981 (18)	0.22282 (18)	0.0461 (9)
H25	−0.0577	0.0737	0.1821	0.055*
C26	0.1017 (3)	0.14532 (18)	0.37412 (19)	0.0457 (9)
C27	0.0999 (4)	0.09524 (18)	0.43880 (18)	0.0505 (9)
H27	0.1720	0.0706	0.4626	0.061*
C28	−0.0319 (4)	0.0903 (2)	0.4597 (2)	0.0614 (10)
H28	−0.0614	0.0620	0.5002	0.074*
C29	−0.1108 (4)	0.1357 (2)	0.4086 (2)	0.0613 (11)
H29	−0.2011	0.1422	0.4095	0.074*
C210	−0.0290 (3)	0.16926 (18)	0.3562 (2)	0.0527 (9)
H210	−0.0563	0.2018	0.3163	0.063*
C211	0.3099 (4)	−0.00579 (18)	0.2465 (2)	0.0466 (9)
C212	0.4340 (3)	−0.0781 (2)	0.3477 (2)	0.0632 (11)
C213	0.5222 (4)	−0.0177 (2)	0.3791 (2)	0.0812 (13)
H23A	0.5546	0.0075	0.3348	0.122*
H23B	0.5950	−0.0365	0.4126	0.122*
H23C	0.4727	0.0143	0.4100	0.122*
C214	0.3854 (4)	−0.1208 (3)	0.4167 (3)	0.1153 (19)
H24A	0.3435	−0.0896	0.4523	0.173*
H24B	0.4586	−0.1441	0.4455	0.173*
H24C	0.3232	−0.1559	0.3958	0.173*
C215	0.4977 (4)	−0.1252 (2)	0.2884 (3)	0.1001 (16)
H25A	0.4380	−0.1627	0.2709	0.150*
H25B	0.5770	−0.1455	0.3137	0.150*
H25C	0.5185	−0.0975	0.2429	0.150*
C216	0.2153 (4)	0.16327 (19)	0.3296 (2)	0.0481 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0392 (3)	0.0473 (3)	0.0430 (3)	−0.0046 (3)	−0.0008 (2)	0.0027 (2)
Fe2	0.0416 (3)	0.0463 (3)	0.0398 (3)	0.0009 (2)	0.0048 (2)	−0.0021 (3)
O1	0.0421 (14)	0.0829 (18)	0.0409 (14)	−0.0047 (12)	0.0030 (11)	0.0164 (13)
O2	0.0470 (14)	0.091 (2)	0.0458 (15)	−0.0045 (14)	0.0130 (12)	0.0150 (13)
O3	0.0544 (16)	0.0726 (19)	0.087 (2)	0.0167 (14)	0.0121 (15)	0.0134 (16)
O4	0.0600 (16)	0.0730 (19)	0.0653 (18)	−0.0088 (15)	0.0090 (13)	0.0099 (16)
O5	0.0442 (14)	0.0630 (17)	0.0579 (15)	0.0054 (12)	0.0043 (11)	0.0293 (13)
O6	0.0461 (14)	0.0683 (17)	0.0504 (15)	0.0037 (12)	0.0132 (12)	0.0123 (13)
O7	0.0456 (14)	0.0710 (18)	0.0675 (17)	−0.0002 (13)	−0.0013 (12)	0.0102 (14)
O8	0.0576 (17)	0.079 (2)	0.083 (2)	0.0132 (15)	0.0217 (15)	0.0288 (17)
N1	0.0419 (17)	0.071 (2)	0.0345 (16)	−0.0122 (15)	−0.0014 (13)	0.0109 (14)
N2	0.0461 (18)	0.0515 (18)	0.0346 (16)	0.0095 (14)	0.0084 (13)	0.0128 (13)
C11	0.043 (2)	0.059 (2)	0.036 (2)	−0.0135 (18)	−0.0010 (16)	−0.0086 (18)
C12	0.046 (2)	0.089 (3)	0.036 (2)	−0.017 (2)	−0.0022 (17)	0.006 (2)
C13	0.054 (3)	0.099 (3)	0.049 (2)	−0.015 (2)	0.0130 (19)	−0.010 (2)
C14	0.053 (2)	0.064 (3)	0.081 (3)	−0.002 (2)	0.015 (2)	−0.019 (2)
C15	0.057 (2)	0.046 (2)	0.061 (2)	−0.0026 (19)	0.002 (2)	0.001 (2)
C16	0.045 (2)	0.034 (2)	0.052 (2)	−0.0071 (17)	−0.0006 (17)	−0.0006 (17)
C17	0.055 (2)	0.041 (2)	0.070 (3)	0.0023 (18)	−0.001 (2)	0.014 (2)
C18	0.060 (3)	0.051 (2)	0.066 (3)	−0.015 (2)	0.009 (2)	0.008 (2)
C19	0.043 (2)	0.057 (2)	0.062 (3)	−0.0124 (19)	−0.0028 (19)	−0.002 (2)
C110	0.046 (2)	0.055 (2)	0.049 (2)	−0.0095 (19)	−0.0104 (18)	0.0031 (18)
C111	0.056 (2)	0.049 (2)	0.036 (2)	−0.0104 (19)	−0.0014 (18)	0.0001 (18)
C112	0.050 (2)	0.052 (2)	0.044 (2)	0.0055 (19)	0.0033 (16)	0.0028 (18)
C113	0.076 (3)	0.090 (3)	0.046 (2)	0.015 (2)	0.003 (2)	0.018 (2)
C114	0.061 (3)	0.107 (4)	0.072 (3)	−0.014 (3)	−0.008 (2)	0.002 (3)
C115	0.156 (5)	0.065 (3)	0.092 (4)	0.026 (3)	0.050 (3)	0.005 (3)
C116	0.059 (2)	0.035 (2)	0.049 (2)	−0.0054 (19)	−0.0007 (19)	−0.0067 (18)
C21	0.0400 (19)	0.041 (2)	0.0359 (19)	−0.0005 (16)	0.0030 (15)	−0.0052 (16)
C22	0.050 (2)	0.042 (2)	0.044 (2)	−0.0017 (17)	0.0045 (17)	0.0029 (17)
C23	0.050 (2)	0.056 (2)	0.052 (2)	−0.0116 (19)	0.0072 (18)	−0.002 (2)
C24	0.035 (2)	0.065 (3)	0.057 (2)	−0.0049 (19)	0.0048 (17)	−0.007 (2)
C25	0.050 (2)	0.050 (2)	0.0369 (19)	0.0023 (18)	−0.0048 (17)	−0.0001 (16)
C26	0.050 (2)	0.045 (2)	0.042 (2)	0.0007 (17)	0.0037 (17)	−0.0023 (17)
C27	0.062 (2)	0.053 (2)	0.036 (2)	−0.0043 (19)	−0.0010 (17)	−0.0074 (17)
C28	0.073 (3)	0.069 (3)	0.044 (2)	−0.007 (2)	0.021 (2)	−0.014 (2)
C29	0.056 (2)	0.061 (3)	0.069 (3)	0.000 (2)	0.019 (2)	−0.014 (2)
C210	0.057 (2)	0.044 (2)	0.058 (2)	0.0075 (19)	0.0108 (19)	−0.0002 (19)
C211	0.053 (2)	0.046 (2)	0.041 (2)	0.0067 (19)	0.0053 (18)	0.0017 (18)
C212	0.049 (2)	0.073 (3)	0.067 (3)	0.013 (2)	0.005 (2)	0.032 (2)
C213	0.057 (2)	0.118 (4)	0.067 (3)	0.002 (3)	−0.006 (2)	0.013 (3)
C214	0.086 (3)	0.143 (5)	0.116 (4)	0.004 (3)	0.006 (3)	0.096 (4)
C215	0.094 (3)	0.075 (3)	0.131 (4)	0.035 (3)	0.013 (3)	0.009 (3)
C216	0.060 (2)	0.040 (2)	0.044 (2)	−0.009 (2)	0.0058 (18)	−0.0053 (19)

Geometric parameters (Å, º)

Fe—C(av.)(unsubst.)	2.044 (3)	C16—C116	1.469 (5)
Fe—C(av.)(subst.)	2.054 (3)	C17—C18	1.412 (5)
Fe1—C16	2.033 (3)	C17—H17	0.9300
Fe1—C110	2.034 (3)	C18—C19	1.411 (5)
Fe1—C17	2.035 (3)	C18—H18	0.9300
Fe1—C13	2.037 (4)	C19—C110	1.403 (4)
Fe1—C14	2.040 (4)	C19—H19	0.9300
Fe1—C18	2.046 (3)	C110—H110	0.9300
Fe1—C15	2.047 (3)	C112—C115	1.509 (5)
Fe1—C12	2.054 (3)	C112—C113	1.510 (4)
Fe1—C19	2.056 (3)	C112—C114	1.511 (5)
Fe1—C11	2.077 (3)	C113—H3A	0.9600
Fe2—C24	2.028 (3)	C113—H3B	0.9600
Fe2—C26	2.032 (3)	C113—H3C	0.9600
Fe2—C27	2.034 (3)	C114—H4A	0.9600
Fe2—C25	2.036 (3)	C114—H4B	0.9600
Fe2—C210	2.037 (3)	C114—H4C	0.9600
Fe2—C23	2.047 (3)	C115—H5A	0.9600
Fe2—C28	2.052 (3)	C115—H5B	0.9600
Fe2—C29	2.055 (3)	C115—H5C	0.9600
Fe2—C22	2.073 (3)	C21—C25	1.416 (4)
Fe2—C21	2.076 (3)	C21—C22	1.425 (4)
O1—C111	1.344 (4)	C22—C23	1.423 (4)
O1—C112	1.460 (4)	C22—H22	0.9300
O2—C111	1.223 (4)	C23—C24	1.400 (4)
O3—C116	1.260 (4)	C23—H23	0.9300
O4—C116	1.276 (4)	C24—C25	1.412 (4)
O4—H4	0.8200	C24—H24	0.9300
O5—C211	1.332 (4)	C25—H25	0.9300
O5—C212	1.480 (4)	C26—C210	1.415 (4)
O6—C211	1.216 (4)	C26—C27	1.434 (4)
O7—C216	1.266 (4)	C26—C216	1.464 (4)
O8—C216	1.278 (4)	C27—C28	1.417 (5)
O8—H8	0.8200	C27—H27	0.9300
N1—C111	1.346 (4)	C28—C29	1.412 (5)
N1—C11	1.409 (4)	C28—H28	0.9300
N1—H1	0.8600	C29—C210	1.406 (4)
N2—C211	1.357 (4)	C29—H29	0.9300
N2—C21	1.409 (4)	C210—H210	0.9300
N2—H2	0.8600	C212—C215	1.514 (5)
C11—C15	1.403 (4)	C212—C213	1.516 (5)
C11—C12	1.420 (4)	C212—C214	1.519 (5)
C12—C13	1.415 (4)	C213—H23A	0.9600
C12—H12	0.9300	C213—H23B	0.9600
C13—C14	1.406 (5)	C213—H23C	0.9600
C13—H13	0.9300	C214—H24A	0.9600
C14—C15	1.409 (5)	C214—H24B	0.9600
C14—H14	0.9300	C214—H24C	0.9600
C15—H15	0.9300	C215—H25A	0.9600
C16—C110	1.418 (4)	C215—H25B	0.9600
C16—C17	1.425 (4)	C215—H25C	0.9600
C16—Fe1—C110	40.80 (12)	C16—C17—H17	126.4
C16—Fe1—C17	41.02 (12)	Fe1—C17—H17	125.7
C110—Fe1—C17	68.70 (14)	C19—C18—C17	108.7 (3)
C16—Fe1—C13	165.40 (15)	C19—C18—Fe1	70.3 (2)
C110—Fe1—C13	152.57 (15)	C17—C18—Fe1	69.4 (2)
C17—Fe1—C13	127.30 (16)	C19—C18—H18	125.7
C16—Fe1—C14	152.65 (15)	C17—C18—H18	125.7
C110—Fe1—C14	119.25 (16)	Fe1—C18—H18	126.3
C17—Fe1—C14	165.50 (16)	C110—C19—C18	108.0 (3)
C13—Fe1—C14	40.36 (14)	C110—C19—Fe1	69.11 (18)
C16—Fe1—C18	68.14 (13)	C18—C19—Fe1	69.50 (19)
C110—Fe1—C18	67.84 (14)	C110—C19—H19	126.0
C17—Fe1—C18	40.48 (13)	C18—C19—H19	126.0
C13—Fe1—C18	108.50 (16)	Fe1—C19—H19	127.0
C14—Fe1—C18	128.50 (15)	C19—C110—C16	108.3 (3)
C16—Fe1—C15	118.94 (13)	C19—C110—Fe1	70.76 (19)
C110—Fe1—C15	109.33 (14)	C16—C110—Fe1	69.55 (18)
C17—Fe1—C15	152.09 (14)	C19—C110—H110	125.8
C13—Fe1—C15	67.58 (15)	C16—C110—H110	125.8
C14—Fe1—C15	40.34 (13)	Fe1—C110—H110	125.4
C18—Fe1—C15	166.61 (14)	O2—C111—O1	125.6 (3)
C16—Fe1—C12	127.42 (14)	O2—C111—N1	123.1 (3)
C110—Fe1—C12	165.95 (14)	O1—C111—N1	111.3 (3)
C17—Fe1—C12	107.10 (15)	O1—C112—C115	109.2 (3)
C13—Fe1—C12	40.46 (13)	O1—C112—C113	102.0 (3)
C14—Fe1—C12	68.08 (15)	C115—C112—C113	111.8 (3)
C18—Fe1—C12	118.32 (15)	O1—C112—C114	110.6 (3)
C15—Fe1—C12	67.69 (14)	C115—C112—C114	112.0 (3)
C16—Fe1—C19	68.02 (13)	C113—C112—C114	110.8 (3)
C110—Fe1—C19	40.13 (12)	C112—C113—H3A	109.5
C17—Fe1—C19	68.18 (14)	C112—C113—H3B	109.5
C13—Fe1—C19	119.29 (14)	H3A—C113—H3B	109.5
C14—Fe1—C19	109.27 (15)	C112—C113—H3C	109.5
C18—Fe1—C19	40.23 (13)	H3A—C113—H3C	109.5
C15—Fe1—C19	129.31 (14)	H3B—C113—H3C	109.5
C12—Fe1—C19	152.22 (14)	C112—C114—H4A	109.5
C16—Fe1—C11	108.55 (13)	C112—C114—H4B	109.5
C110—Fe1—C11	128.89 (13)	H4A—C114—H4B	109.5
C17—Fe1—C11	118.46 (14)	C112—C114—H4C	109.5
C13—Fe1—C11	67.32 (14)	H4A—C114—H4C	109.5
C14—Fe1—C11	67.36 (14)	H4B—C114—H4C	109.5
C18—Fe1—C11	152.06 (15)	C112—C115—H5A	109.5
C15—Fe1—C11	39.77 (12)	C112—C115—H5B	109.5
C12—Fe1—C11	40.19 (11)	H5A—C115—H5B	109.5
C19—Fe1—C11	166.51 (14)	C112—C115—H5C	109.5
C24—Fe2—C26	151.20 (14)	H5A—C115—H5C	109.5
C24—Fe2—C27	166.25 (14)	H5B—C115—H5C	109.5
C26—Fe2—C27	41.32 (12)	O3—C116—O4	124.1 (3)
C24—Fe2—C25	40.66 (12)	O3—C116—C16	120.7 (3)
C26—Fe2—C25	117.65 (13)	O4—C116—C16	115.3 (3)
C27—Fe2—C25	151.78 (13)	N2—C21—C25	122.0 (3)
C24—Fe2—C210	117.90 (14)	N2—C21—C22	129.9 (3)
C26—Fe2—C210	40.70 (12)	C25—C21—C22	108.0 (3)
C27—Fe2—C210	68.72 (14)	N2—C21—Fe2	128.6 (2)
C25—Fe2—C210	107.99 (14)	C25—C21—Fe2	68.37 (17)
C24—Fe2—C23	40.20 (12)	C22—C21—Fe2	69.82 (17)
C26—Fe2—C23	167.07 (14)	C23—C22—C21	107.0 (3)
C27—Fe2—C23	128.63 (14)	C23—C22—Fe2	68.80 (19)
C25—Fe2—C23	67.87 (14)	C21—C22—Fe2	70.01 (18)
C210—Fe2—C23	151.34 (14)	C23—C22—H22	126.5
C24—Fe2—C28	128.39 (15)	C21—C22—H22	126.5
C26—Fe2—C28	68.45 (14)	Fe2—C22—H22	126.2
C27—Fe2—C28	40.59 (13)	C24—C23—C22	108.7 (3)
C25—Fe2—C28	166.17 (14)	C24—C23—Fe2	69.18 (19)
C210—Fe2—C28	67.82 (15)	C22—C23—Fe2	70.79 (19)
C23—Fe2—C28	109.05 (15)	C24—C23—H23	125.7
C24—Fe2—C29	108.28 (14)	C22—C23—H23	125.7
C26—Fe2—C29	68.19 (13)	Fe2—C23—H23	125.9
C27—Fe2—C29	68.29 (14)	C23—C24—C25	108.3 (3)
C25—Fe2—C29	128.28 (15)	C23—C24—Fe2	70.62 (19)
C210—Fe2—C29	40.18 (13)	C25—C24—Fe2	69.98 (18)
C23—Fe2—C29	118.70 (14)	C23—C24—H24	125.9
C28—Fe2—C29	40.20 (13)	C25—C24—H24	125.9
C24—Fe2—C22	68.00 (13)	Fe2—C24—H24	125.1
C26—Fe2—C22	128.70 (13)	C24—C25—C21	108.0 (3)
C27—Fe2—C22	108.39 (14)	C24—C25—Fe2	69.36 (19)
C25—Fe2—C22	68.02 (13)	C21—C25—Fe2	71.37 (17)
C210—Fe2—C22	166.69 (13)	C24—C25—H25	126.0
C23—Fe2—C22	40.40 (12)	C21—C25—H25	126.0
C28—Fe2—C22	119.06 (15)	Fe2—C25—H25	124.9
C29—Fe2—C22	152.12 (14)	C210—C26—C27	107.5 (3)
C24—Fe2—C21	67.76 (13)	C210—C26—C216	126.0 (3)
C26—Fe2—C21	108.50 (13)	C27—C26—C216	126.3 (3)
C27—Fe2—C21	118.71 (13)	C210—C26—Fe2	69.84 (19)
C25—Fe2—C21	40.27 (11)	C27—C26—Fe2	69.41 (18)
C210—Fe2—C21	128.78 (13)	C216—C26—Fe2	121.7 (2)
C23—Fe2—C21	67.46 (13)	C28—C27—C26	107.3 (3)
C28—Fe2—C21	152.44 (15)	C28—C27—Fe2	70.4 (2)
C29—Fe2—C21	166.26 (14)	C26—C27—Fe2	69.28 (18)
C22—Fe2—C21	40.17 (11)	C28—C27—H27	126.3
C111—O1—C112	122.0 (3)	C26—C27—H27	126.3
C116—O4—H4	109.5	Fe2—C27—H27	125.6
C211—O5—C212	120.4 (3)	C29—C28—C27	108.5 (3)
C216—O8—H8	109.5	C29—C28—Fe2	70.0 (2)
C111—N1—C11	130.1 (3)	C27—C28—Fe2	69.01 (19)
C111—N1—H1	114.9	C29—C28—H28	125.8
C11—N1—H1	114.9	C27—C28—H28	125.8
C211—N2—C21	129.9 (3)	Fe2—C28—H28	126.8
C211—N2—H2	115.0	C210—C29—C28	108.1 (3)
C21—N2—H2	115.0	C210—C29—Fe2	69.2 (2)
C15—C11—N1	122.5 (3)	C28—C29—Fe2	69.8 (2)
C15—C11—C12	108.0 (3)	C210—C29—H29	125.9
N1—C11—C12	129.4 (3)	C28—C29—H29	125.9
C15—C11—Fe1	68.96 (19)	Fe2—C29—H29	126.7
N1—C11—Fe1	125.8 (2)	C29—C210—C26	108.6 (3)
C12—C11—Fe1	69.03 (18)	C29—C210—Fe2	70.6 (2)
C13—C12—C11	107.1 (3)	C26—C210—Fe2	69.46 (19)
C13—C12—Fe1	69.11 (19)	C29—C210—H210	125.7
C11—C12—Fe1	70.78 (17)	C26—C210—H210	125.7
C13—C12—H12	126.4	Fe2—C210—H210	125.8
C11—C12—H12	126.4	O6—C211—O5	125.5 (3)
Fe1—C12—H12	125.3	O6—C211—N2	122.1 (3)
C14—C13—C12	108.7 (3)	O5—C211—N2	112.4 (3)
C14—C13—Fe1	69.9 (2)	O5—C212—C215	110.5 (3)
C12—C13—Fe1	70.4 (2)	O5—C212—C213	108.6 (3)
C14—C13—H13	125.7	C215—C212—C213	113.1 (3)
C12—C13—H13	125.7	O5—C212—C214	101.5 (3)
Fe1—C13—H13	125.6	C215—C212—C214	111.7 (4)
C13—C14—C15	107.6 (3)	C213—C212—C214	110.8 (3)
C13—C14—Fe1	69.7 (2)	C212—C213—H23A	109.5
C15—C14—Fe1	70.1 (2)	C212—C213—H23B	109.5
C13—C14—H14	126.2	H23A—C213—H23B	109.5
C15—C14—H14	126.2	C212—C213—H23C	109.5
Fe1—C14—H14	125.5	H23A—C213—H23C	109.5
C11—C15—C14	108.6 (3)	H23B—C213—H23C	109.5
C11—C15—Fe1	71.3 (2)	C212—C214—H24A	109.5
C14—C15—Fe1	69.5 (2)	C212—C214—H24B	109.5
C11—C15—H15	125.7	H24A—C214—H24B	109.5
C14—C15—H15	125.7	C212—C214—H24C	109.5
Fe1—C15—H15	125.1	H24A—C214—H24C	109.5
C110—C16—C17	107.7 (3)	H24B—C214—H24C	109.5
C110—C16—C116	125.0 (3)	C212—C215—H25A	109.5
C17—C16—C116	127.2 (3)	C212—C215—H25B	109.5
C110—C16—Fe1	69.65 (19)	H25A—C215—H25B	109.5
C17—C16—Fe1	69.58 (19)	C212—C215—H25C	109.5
C116—C16—Fe1	123.1 (2)	H25A—C215—H25C	109.5
C18—C17—C16	107.3 (3)	H25B—C215—H25C	109.5
C18—C17—Fe1	70.2 (2)	O7—C216—O8	123.7 (3)
C16—C17—Fe1	69.40 (19)	O7—C216—C26	119.9 (3)
C18—C17—H17	126.4	O8—C216—C26	116.3 (3)
C111—N1—C11—C15	−165.2 (3)	C211—N2—C21—C25	171.2 (3)
C111—N1—C11—C12	17.3 (6)	C211—N2—C21—C22	−10.9 (5)
C111—N1—C11—Fe1	108.5 (4)	C211—N2—C21—Fe2	84.4 (4)
C16—Fe1—C11—C15	−113.3 (2)	C24—Fe2—C21—N2	152.7 (3)
C110—Fe1—C11—C15	−72.3 (3)	C26—Fe2—C21—N2	3.2 (3)
C17—Fe1—C11—C15	−156.9 (2)	C27—Fe2—C21—N2	−40.8 (3)
C13—Fe1—C11—C15	81.7 (2)	C25—Fe2—C21—N2	114.4 (4)
C14—Fe1—C11—C15	37.8 (2)	C210—Fe2—C21—N2	44.0 (3)
C18—Fe1—C11—C15	168.6 (3)	C23—Fe2—C21—N2	−163.7 (3)
C12—Fe1—C11—C15	120.2 (3)	C28—Fe2—C21—N2	−75.5 (4)
C19—Fe1—C11—C15	−40.3 (7)	C29—Fe2—C21—N2	76.8 (6)
C16—Fe1—C11—N1	2.4 (3)	C22—Fe2—C21—N2	−125.6 (4)
C110—Fe1—C11—N1	43.4 (4)	C24—Fe2—C21—C25	38.26 (19)
C17—Fe1—C11—N1	−41.3 (3)	C26—Fe2—C21—C25	−111.2 (2)
C13—Fe1—C11—N1	−162.6 (4)	C27—Fe2—C21—C25	−155.2 (2)
C14—Fe1—C11—N1	153.5 (3)	C210—Fe2—C21—C25	−70.4 (2)
C18—Fe1—C11—N1	−75.7 (4)	C23—Fe2—C21—C25	81.9 (2)
C15—Fe1—C11—N1	115.7 (4)	C28—Fe2—C21—C25	170.1 (3)
C12—Fe1—C11—N1	−124.2 (4)	C29—Fe2—C21—C25	−37.6 (6)
C19—Fe1—C11—N1	75.3 (7)	C22—Fe2—C21—C25	120.0 (3)
C16—Fe1—C11—C12	126.6 (2)	C24—Fe2—C21—C22	−81.8 (2)
C110—Fe1—C11—C12	167.5 (2)	C26—Fe2—C21—C22	128.74 (19)
C17—Fe1—C11—C12	82.9 (2)	C27—Fe2—C21—C22	84.8 (2)
C13—Fe1—C11—C12	−38.4 (2)	C25—Fe2—C21—C22	−120.0 (3)
C14—Fe1—C11—C12	−82.3 (2)	C210—Fe2—C21—C22	169.57 (19)
C18—Fe1—C11—C12	48.4 (4)	C23—Fe2—C21—C22	−38.14 (19)
C15—Fe1—C11—C12	−120.2 (3)	C28—Fe2—C21—C22	50.0 (4)
C19—Fe1—C11—C12	−160.5 (6)	C29—Fe2—C21—C22	−157.6 (5)
C15—C11—C12—C13	1.8 (4)	N2—C21—C22—C23	−176.8 (3)
N1—C11—C12—C13	179.6 (3)	C25—C21—C22—C23	1.3 (4)
Fe1—C11—C12—C13	59.8 (2)	Fe2—C21—C22—C23	59.1 (2)
C15—C11—C12—Fe1	−58.1 (2)	N2—C21—C22—Fe2	124.1 (3)
N1—C11—C12—Fe1	119.8 (3)	C25—C21—C22—Fe2	−57.8 (2)
C16—Fe1—C12—C13	168.7 (2)	C24—Fe2—C22—C23	−37.2 (2)
C110—Fe1—C12—C13	−161.6 (6)	C26—Fe2—C22—C23	170.2 (2)
C17—Fe1—C12—C13	128.0 (2)	C27—Fe2—C22—C23	128.6 (2)
C14—Fe1—C12—C13	−37.4 (2)	C25—Fe2—C22—C23	−81.2 (2)
C18—Fe1—C12—C13	85.6 (3)	C210—Fe2—C22—C23	−156.2 (5)
C15—Fe1—C12—C13	−81.1 (2)	C28—Fe2—C22—C23	85.6 (2)
C19—Fe1—C12—C13	52.5 (4)	C29—Fe2—C22—C23	50.5 (4)
C11—Fe1—C12—C13	−117.9 (3)	C21—Fe2—C22—C23	−118.3 (3)
C16—Fe1—C12—C11	−73.4 (3)	C24—Fe2—C22—C21	81.1 (2)
C110—Fe1—C12—C11	−43.7 (7)	C26—Fe2—C22—C21	−71.4 (2)
C17—Fe1—C12—C11	−114.1 (2)	C27—Fe2—C22—C21	−113.0 (2)
C13—Fe1—C12—C11	117.9 (3)	C25—Fe2—C22—C21	37.12 (18)
C14—Fe1—C12—C11	80.4 (2)	C210—Fe2—C22—C21	−37.8 (7)
C18—Fe1—C12—C11	−156.5 (2)	C23—Fe2—C22—C21	118.3 (3)
C15—Fe1—C12—C11	36.7 (2)	C28—Fe2—C22—C21	−156.06 (19)
C19—Fe1—C12—C11	170.4 (3)	C29—Fe2—C22—C21	168.8 (3)
C11—C12—C13—C14	−1.2 (4)	C21—C22—C23—C24	−0.9 (4)
Fe1—C12—C13—C14	59.7 (3)	Fe2—C22—C23—C24	59.0 (2)
C11—C12—C13—Fe1	−60.9 (2)	C21—C22—C23—Fe2	−59.9 (2)
C16—Fe1—C13—C14	−157.5 (5)	C26—Fe2—C23—C24	−155.9 (5)
C110—Fe1—C13—C14	51.0 (4)	C27—Fe2—C23—C24	168.7 (2)
C17—Fe1—C13—C14	169.4 (2)	C25—Fe2—C23—C24	−38.05 (19)
C18—Fe1—C13—C14	128.3 (2)	C210—Fe2—C23—C24	49.2 (4)
C15—Fe1—C13—C14	−38.0 (2)	C28—Fe2—C23—C24	127.5 (2)
C12—Fe1—C13—C14	−119.4 (3)	C29—Fe2—C23—C24	84.6 (2)
C19—Fe1—C13—C14	85.7 (3)	C22—Fe2—C23—C24	−119.7 (3)
C11—Fe1—C13—C14	−81.2 (2)	C21—Fe2—C23—C24	−81.7 (2)
C16—Fe1—C13—C12	−38.1 (7)	C24—Fe2—C23—C22	119.7 (3)
C110—Fe1—C13—C12	170.4 (3)	C26—Fe2—C23—C22	−36.3 (7)
C17—Fe1—C13—C12	−71.1 (3)	C27—Fe2—C23—C22	−71.6 (2)
C14—Fe1—C13—C12	119.4 (3)	C25—Fe2—C23—C22	81.6 (2)
C18—Fe1—C13—C12	−112.2 (2)	C210—Fe2—C23—C22	168.8 (3)
C15—Fe1—C13—C12	81.4 (2)	C28—Fe2—C23—C22	−112.8 (2)
C19—Fe1—C13—C12	−154.9 (2)	C29—Fe2—C23—C22	−155.7 (2)
C11—Fe1—C13—C12	38.2 (2)	C21—Fe2—C23—C22	37.93 (19)
C12—C13—C14—C15	0.2 (4)	C22—C23—C24—C25	0.1 (4)
Fe1—C13—C14—C15	60.2 (3)	Fe2—C23—C24—C25	60.1 (2)
C12—C13—C14—Fe1	−60.0 (3)	C22—C23—C24—Fe2	−60.0 (2)
C16—Fe1—C14—C13	167.9 (3)	C26—Fe2—C24—C23	169.1 (2)
C110—Fe1—C14—C13	−155.8 (2)	C27—Fe2—C24—C23	−39.9 (7)
C17—Fe1—C14—C13	−35.6 (7)	C25—Fe2—C24—C23	118.8 (3)
C18—Fe1—C14—C13	−71.9 (3)	C210—Fe2—C24—C23	−155.8 (2)
C15—Fe1—C14—C13	118.4 (3)	C28—Fe2—C24—C23	−73.0 (3)
C12—Fe1—C14—C13	37.5 (2)	C29—Fe2—C24—C23	−113.1 (2)
C19—Fe1—C14—C13	−112.9 (2)	C22—Fe2—C24—C23	37.40 (19)
C11—Fe1—C14—C13	81.1 (2)	C21—Fe2—C24—C23	80.9 (2)
C16—Fe1—C14—C15	49.5 (4)	C26—Fe2—C24—C25	50.3 (4)
C110—Fe1—C14—C15	85.8 (2)	C27—Fe2—C24—C25	−158.7 (5)
C17—Fe1—C14—C15	−154.0 (5)	C210—Fe2—C24—C25	85.4 (2)
C13—Fe1—C14—C15	−118.4 (3)	C23—Fe2—C24—C25	−118.8 (3)
C18—Fe1—C14—C15	169.6 (2)	C28—Fe2—C24—C25	168.2 (2)
C12—Fe1—C14—C15	−80.9 (2)	C29—Fe2—C24—C25	128.1 (2)
C19—Fe1—C14—C15	128.7 (2)	C22—Fe2—C24—C25	−81.4 (2)
C11—Fe1—C14—C15	−37.3 (2)	C21—Fe2—C24—C25	−37.90 (19)
N1—C11—C15—C14	−179.7 (3)	C23—C24—C25—C21	0.7 (4)
C12—C11—C15—C14	−1.7 (4)	Fe2—C24—C25—C21	61.2 (2)
Fe1—C11—C15—C14	−59.8 (2)	C23—C24—C25—Fe2	−60.5 (2)
N1—C11—C15—Fe1	−119.9 (3)	N2—C21—C25—C24	177.1 (3)
C12—C11—C15—Fe1	58.1 (2)	C22—C21—C25—C24	−1.2 (4)
C13—C14—C15—C11	0.9 (4)	Fe2—C21—C25—C24	−59.9 (2)
Fe1—C14—C15—C11	60.9 (2)	N2—C21—C25—Fe2	−123.0 (3)
C13—C14—C15—Fe1	−59.9 (3)	C22—C21—C25—Fe2	58.7 (2)
C16—Fe1—C15—C11	84.5 (2)	C26—Fe2—C25—C24	−155.3 (2)
C110—Fe1—C15—C11	128.2 (2)	C27—Fe2—C25—C24	169.5 (3)
C17—Fe1—C15—C11	47.4 (4)	C210—Fe2—C25—C24	−112.1 (2)
C13—Fe1—C15—C11	−81.0 (2)	C23—Fe2—C25—C24	37.6 (2)
C14—Fe1—C15—C11	−119.0 (3)	C28—Fe2—C25—C24	−42.1 (7)
C18—Fe1—C15—C11	−156.4 (6)	C29—Fe2—C25—C24	−72.2 (3)
C12—Fe1—C15—C11	−37.09 (19)	C22—Fe2—C25—C24	81.4 (2)
C19—Fe1—C15—C11	168.7 (2)	C21—Fe2—C25—C24	118.4 (3)
C16—Fe1—C15—C14	−156.5 (2)	C24—Fe2—C25—C21	−118.4 (3)
C110—Fe1—C15—C14	−112.8 (2)	C26—Fe2—C25—C21	86.3 (2)
C17—Fe1—C15—C14	166.5 (3)	C27—Fe2—C25—C21	51.1 (4)
C13—Fe1—C15—C14	38.0 (2)	C210—Fe2—C25—C21	129.45 (19)
C18—Fe1—C15—C14	−37.4 (7)	C23—Fe2—C25—C21	−80.8 (2)
C12—Fe1—C15—C14	81.9 (2)	C28—Fe2—C25—C21	−160.5 (6)
C19—Fe1—C15—C14	−72.2 (3)	C29—Fe2—C25—C21	169.4 (2)
C11—Fe1—C15—C14	119.0 (3)	C22—Fe2—C25—C21	−37.03 (18)
C17—Fe1—C16—C110	−119.0 (3)	C24—Fe2—C26—C210	51.3 (4)
C13—Fe1—C16—C110	−160.3 (5)	C27—Fe2—C26—C210	−118.7 (3)
C14—Fe1—C16—C110	52.2 (4)	C25—Fe2—C26—C210	85.7 (2)
C18—Fe1—C16—C110	−81.0 (2)	C23—Fe2—C26—C210	−161.8 (5)
C15—Fe1—C16—C110	86.5 (2)	C28—Fe2—C26—C210	−80.6 (2)
C12—Fe1—C16—C110	169.4 (2)	C29—Fe2—C26—C210	−37.2 (2)
C19—Fe1—C16—C110	−37.43 (19)	C22—Fe2—C26—C210	168.74 (19)
C11—Fe1—C16—C110	128.7 (2)	C21—Fe2—C26—C210	128.6 (2)
C110—Fe1—C16—C17	119.0 (3)	C24—Fe2—C26—C27	169.9 (3)
C13—Fe1—C16—C17	−41.3 (6)	C25—Fe2—C26—C27	−155.60 (19)
C14—Fe1—C16—C17	171.2 (3)	C210—Fe2—C26—C27	118.7 (3)
C18—Fe1—C16—C17	38.05 (19)	C23—Fe2—C26—C27	−43.2 (7)
C15—Fe1—C16—C17	−154.54 (19)	C28—Fe2—C26—C27	38.1 (2)
C12—Fe1—C16—C17	−71.6 (2)	C29—Fe2—C26—C27	81.5 (2)
C19—Fe1—C16—C17	81.6 (2)	C22—Fe2—C26—C27	−72.6 (2)
C11—Fe1—C16—C17	−112.3 (2)	C21—Fe2—C26—C27	−112.7 (2)
C110—Fe1—C16—C116	−119.2 (4)	C24—Fe2—C26—C216	−69.3 (4)
C17—Fe1—C16—C116	121.8 (4)	C27—Fe2—C26—C216	120.7 (4)
C13—Fe1—C16—C116	80.5 (6)	C25—Fe2—C26—C216	−34.9 (3)
C14—Fe1—C16—C116	−66.9 (4)	C210—Fe2—C26—C216	−120.6 (4)
C18—Fe1—C16—C116	159.9 (3)	C23—Fe2—C26—C216	77.6 (7)
C15—Fe1—C16—C116	−32.7 (3)	C28—Fe2—C26—C216	158.8 (3)
C12—Fe1—C16—C116	50.2 (4)	C29—Fe2—C26—C216	−157.8 (3)
C19—Fe1—C16—C116	−156.6 (3)	C22—Fe2—C26—C216	48.1 (3)
C11—Fe1—C16—C116	9.5 (3)	C21—Fe2—C26—C216	8.0 (3)
C110—C16—C17—C18	−0.8 (4)	C210—C26—C27—C28	−0.7 (4)
C116—C16—C17—C18	−176.9 (3)	C216—C26—C27—C28	−175.3 (3)
Fe1—C16—C17—C18	−60.2 (2)	Fe2—C26—C27—C28	−60.4 (2)
C110—C16—C17—Fe1	59.4 (2)	C210—C26—C27—Fe2	59.7 (2)
C116—C16—C17—Fe1	−116.7 (3)	C216—C26—C27—Fe2	−114.9 (3)
C16—Fe1—C17—C18	118.2 (3)	C24—Fe2—C27—C28	−41.1 (7)
C110—Fe1—C17—C18	80.4 (2)	C26—Fe2—C27—C28	118.2 (3)
C13—Fe1—C17—C18	−73.9 (3)	C25—Fe2—C27—C28	168.9 (3)
C14—Fe1—C17—C18	−45.6 (7)	C210—Fe2—C27—C28	80.3 (2)
C15—Fe1—C17—C18	171.7 (3)	C23—Fe2—C27—C28	−73.1 (3)
C12—Fe1—C17—C18	−113.8 (2)	C29—Fe2—C27—C28	37.0 (2)
C19—Fe1—C17—C18	37.1 (2)	C22—Fe2—C27—C28	−113.5 (2)
C11—Fe1—C17—C18	−155.9 (2)	C21—Fe2—C27—C28	−156.1 (2)
C110—Fe1—C17—C16	−37.84 (18)	C24—Fe2—C27—C26	−159.3 (5)
C13—Fe1—C17—C16	167.9 (2)	C25—Fe2—C27—C26	50.7 (4)
C14—Fe1—C17—C16	−163.8 (5)	C210—Fe2—C27—C26	−37.88 (19)
C18—Fe1—C17—C16	−118.2 (3)	C23—Fe2—C27—C26	168.70 (19)
C15—Fe1—C17—C16	53.5 (4)	C28—Fe2—C27—C26	−118.2 (3)
C12—Fe1—C17—C16	127.95 (19)	C29—Fe2—C27—C26	−81.2 (2)
C19—Fe1—C17—C16	−81.1 (2)	C22—Fe2—C27—C26	128.30 (19)
C11—Fe1—C17—C16	85.9 (2)	C21—Fe2—C27—C26	85.7 (2)
C16—C17—C18—C19	0.3 (4)	C26—C27—C28—C29	0.6 (4)
Fe1—C17—C18—C19	−59.5 (3)	Fe2—C27—C28—C29	−59.1 (2)
C16—C17—C18—Fe1	59.7 (2)	C26—C27—C28—Fe2	59.7 (2)
C16—Fe1—C18—C19	81.4 (2)	C24—Fe2—C28—C29	−71.5 (3)
C110—Fe1—C18—C19	37.2 (2)	C26—Fe2—C28—C29	81.3 (2)
C17—Fe1—C18—C19	119.9 (3)	C27—Fe2—C28—C29	120.0 (3)
C13—Fe1—C18—C19	−113.8 (2)	C25—Fe2—C28—C29	−37.6 (7)
C14—Fe1—C18—C19	−73.3 (3)	C210—Fe2—C28—C29	37.3 (2)
C15—Fe1—C18—C19	−43.1 (7)	C23—Fe2—C28—C29	−112.2 (2)
C12—Fe1—C18—C19	−156.8 (2)	C22—Fe2—C28—C29	−155.4 (2)
C11—Fe1—C18—C19	169.9 (3)	C21—Fe2—C28—C29	170.2 (3)
C16—Fe1—C18—C17	−38.5 (2)	C24—Fe2—C28—C27	168.5 (2)
C110—Fe1—C18—C17	−82.7 (2)	C26—Fe2—C28—C27	−38.7 (2)
C13—Fe1—C18—C17	126.3 (2)	C25—Fe2—C28—C27	−157.6 (5)
C14—Fe1—C18—C17	166.8 (2)	C210—Fe2—C28—C27	−82.7 (2)
C15—Fe1—C18—C17	−163.0 (6)	C23—Fe2—C28—C27	127.7 (2)
C12—Fe1—C18—C17	83.3 (2)	C29—Fe2—C28—C27	−120.0 (3)
C19—Fe1—C18—C17	−119.9 (3)	C22—Fe2—C28—C27	84.6 (2)
C11—Fe1—C18—C17	50.0 (4)	C21—Fe2—C28—C27	50.2 (4)
C17—C18—C19—C110	0.4 (4)	C27—C28—C29—C210	−0.3 (4)
Fe1—C18—C19—C110	−58.5 (2)	Fe2—C28—C29—C210	−58.8 (2)
C17—C18—C19—Fe1	58.9 (3)	C27—C28—C29—Fe2	58.5 (2)
C16—Fe1—C19—C110	38.0 (2)	C24—Fe2—C29—C210	−111.9 (2)
C17—Fe1—C19—C110	82.4 (2)	C26—Fe2—C29—C210	37.7 (2)
C13—Fe1—C19—C110	−156.0 (2)	C27—Fe2—C29—C210	82.3 (2)
C14—Fe1—C19—C110	−112.8 (2)	C25—Fe2—C29—C210	−71.1 (3)
C18—Fe1—C19—C110	119.7 (3)	C23—Fe2—C29—C210	−154.5 (2)
C15—Fe1—C19—C110	−72.1 (3)	C28—Fe2—C29—C210	119.6 (3)
C12—Fe1—C19—C110	167.8 (3)	C22—Fe2—C29—C210	170.8 (3)
C11—Fe1—C19—C110	−39.7 (7)	C21—Fe2—C29—C210	−40.9 (7)
C16—Fe1—C19—C18	−81.7 (2)	C24—Fe2—C29—C28	128.5 (2)
C110—Fe1—C19—C18	−119.7 (3)	C26—Fe2—C29—C28	−82.0 (2)
C17—Fe1—C19—C18	−37.3 (2)	C27—Fe2—C29—C28	−37.3 (2)
C13—Fe1—C19—C18	84.3 (3)	C25—Fe2—C29—C28	169.3 (2)
C14—Fe1—C19—C18	127.4 (2)	C210—Fe2—C29—C28	−119.6 (3)
C15—Fe1—C19—C18	168.2 (2)	C23—Fe2—C29—C28	85.9 (3)
C12—Fe1—C19—C18	48.1 (4)	C22—Fe2—C29—C28	51.1 (4)
C11—Fe1—C19—C18	−159.4 (5)	C21—Fe2—C29—C28	−160.6 (5)
C18—C19—C110—C16	−0.9 (4)	C28—C29—C210—C26	−0.2 (4)
Fe1—C19—C110—C16	−59.6 (2)	Fe2—C29—C210—C26	−59.3 (2)
C18—C19—C110—Fe1	58.8 (2)	C28—C29—C210—Fe2	59.1 (2)
C17—C16—C110—C19	1.0 (4)	C27—C26—C210—C29	0.5 (4)
C116—C16—C110—C19	177.2 (3)	C216—C26—C210—C29	175.2 (3)
Fe1—C16—C110—C19	60.4 (2)	Fe2—C26—C210—C29	60.0 (2)
C17—C16—C110—Fe1	−59.4 (2)	C27—C26—C210—Fe2	−59.4 (2)
C116—C16—C110—Fe1	116.8 (3)	C216—C26—C210—Fe2	115.2 (3)
C16—Fe1—C110—C19	−119.0 (3)	C24—Fe2—C210—C29	85.6 (2)
C17—Fe1—C110—C19	−81.0 (2)	C26—Fe2—C210—C29	−119.6 (3)
C13—Fe1—C110—C19	50.4 (4)	C27—Fe2—C210—C29	−81.1 (2)
C14—Fe1—C110—C19	85.6 (2)	C25—Fe2—C210—C29	128.7 (2)
C18—Fe1—C110—C19	−37.3 (2)	C23—Fe2—C210—C29	52.1 (4)
C15—Fe1—C110—C19	128.7 (2)	C28—Fe2—C210—C29	−37.3 (2)
C12—Fe1—C110—C19	−156.1 (6)	C22—Fe2—C210—C29	−161.0 (5)
C11—Fe1—C110—C19	169.0 (2)	C21—Fe2—C210—C29	168.5 (2)
C17—Fe1—C110—C16	38.03 (18)	C24—Fe2—C210—C26	−154.8 (2)
C13—Fe1—C110—C16	169.4 (3)	C27—Fe2—C210—C26	38.44 (19)
C14—Fe1—C110—C16	−155.4 (2)	C25—Fe2—C210—C26	−111.8 (2)
C18—Fe1—C110—C16	81.8 (2)	C23—Fe2—C210—C26	171.6 (3)
C15—Fe1—C110—C16	−112.2 (2)	C28—Fe2—C210—C26	82.3 (2)
C12—Fe1—C110—C16	−37.1 (7)	C29—Fe2—C210—C26	119.6 (3)
C19—Fe1—C110—C16	119.0 (3)	C22—Fe2—C210—C26	−41.5 (7)
C11—Fe1—C110—C16	−72.0 (2)	C21—Fe2—C210—C26	−72.0 (2)
C112—O1—C111—O2	1.3 (5)	C212—O5—C211—O6	0.6 (5)
C112—O1—C111—N1	−179.1 (3)	C212—O5—C211—N2	178.9 (3)
C11—N1—C111—O2	−179.3 (3)	C21—N2—C211—O6	−177.2 (3)
C11—N1—C111—O1	1.1 (5)	C21—N2—C211—O5	4.5 (5)
C111—O1—C112—C115	67.4 (4)	C211—O5—C212—C215	−61.3 (4)
C111—O1—C112—C113	−174.3 (3)	C211—O5—C212—C213	63.3 (4)
C111—O1—C112—C114	−56.3 (4)	C211—O5—C212—C214	−179.9 (3)
C110—C16—C116—O3	−177.3 (3)	C210—C26—C216—O7	−179.7 (3)
C17—C16—C116—O3	−1.8 (5)	C27—C26—C216—O7	−6.1 (5)
Fe1—C16—C116—O3	−90.2 (4)	Fe2—C26—C216—O7	−92.7 (4)
C110—C16—C116—O4	2.9 (5)	C210—C26—C216—O8	0.8 (5)
C17—C16—C116—O4	178.3 (3)	C27—C26—C216—O8	174.4 (3)
Fe1—C16—C116—O4	89.9 (3)	Fe2—C26—C216—O8	87.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.86	1.98	2.827 (3)	166
N2—H2···O2	0.86	1.99	2.854 (3)	177
O4—H4···O7	0.82	1.85	2.656 (3)	167
O8—H8···O3	0.82	1.86	2.663 (3)	167