Hydro­gen-bonded adducts of ferrocene-1,1′-diyl­bis­(di­phenyl­methanol): monomeric and dimeric 1:1 adducts with 1,2-bis(4-pyridyl)­ethane and 1,2-­diamino­ethane

In ferrocene-1,1′-diyl­bis­(di­phenyl­methanol)–4,4′-ethyl­enedi­pyridine (1/1), [Fe(C₁₈H₁₅O)₂]·C₁₂H₁₂N₂, there is an intra­molecular O—H...O hydrogen bond in the ferrocenediol component and a single O—H...N hydrogen bond linking the two components into a finite monomeric adduct. Ferrocene-1,1′-diyl­bis­(di­phenyl­methanol)–ethyl­enedi­amine (1/1), [Fe(C₁₈H₁₅O)₂]·C₂H₈N₂, crystallizes with Z′ = 2 in space group P, and there are two independent four-component aggregates in the structure, both of which are centrosymmetric. In the first type of aggregate, the molecular components are linked by O—H...N and N—H...O hydrogen bonds, in which both di­amine N atoms participate; in the second type of aggregate, the di­amine component is disordered over two sets of sites, but only one N atom is involved in the hydrogen bonding.

S1. Comment

The organometallic diol ferrocene-1,1'-diylbis(diphenylmethanol), [Fe(C₅H₄CPh₂OH)₂], forms hydrogen-bonded adducts with a wide range of hydrogen-bond acceptors, particularly cyclic and cage amines (Ferguson et al., 1993, 1995; Glidewell et al., 1994). Thus with piperazine, HN(CH₂CH₂)₂NH, an adduct of 1:1 stoichiometry is formed in which the supramolecular aggregation consists of spiral C²₂(13) chains of alternating diol and diamine units containing two distinct O—H···N hydrogen bonds (Glidewell et al., 1994); by contrast, in the 1:1 adduct formed with 4,4'-bipyridyl, only half of the bipyridyl molecules are involved in the supramolecular aggregation, which takes the form of the centrosymmetric three-component aggregate (diol)-(diamine)-(diol), while the remainder of the bipyridyl molecules simply occupy isolated sites in the structure (Glidewell et al., 1994). While a wide range of supramolecular structures has been observed in adducts formed by this ferrocenediol (Ferguson et al., 1993, 1995; Glidewell et al., 1994), no one structure type is predictable from knowledge of the remainder: in particular the hydrogen-bond donor and acceptor behaviour of the non-ferrocenediol components is not yet readily predictable. However, a frequently-observed pattern, found in the adducts formed with 4,4'-bipyridyl, 1,4-dioxan, dimethylformamide and hexamethylenetetramine, is that of a single intramolecular O—H···O hydrogen bond in the ferrocenediol component forming an S(8) ring, together with a single O—H···A hydrogen bond to the acceptor atom A, which may be N or O, in the second component.

In the adduct with 1,2-bis(4-pyridyl)ethane, (I) (Fig. 1), there is an intramolecular O—H···O hydrogen bond (Table 2) and, in addition O1 acts as hydrogen-bond donor to N71; N81, on the other hand, does not act as a hydrogen-bond acceptor, even of soft C—H···N hydrogen bonds, so that (I) is a simple finite adduct, whose hydrogen bonding can be characterized by the graph-set descriptor S(8)D, precisely as for the 1:1 adduct formed by the ferrocenediol with dimethylformamide (Glidewell et al., 1994). The constitution of (I) is thus entirely different from that of the analogous 1:1 adduct formed with 4,4'-bipyridyl itself. \sch

The 1,2-diaminoethane adduct (II) also exhibits 1:1 stoichiometry but in this case the diamine component is potentially a fourfold donor of hydrogen bonds as well as potentially a twofold acceptor; adduct (II) crystallizes with Z' = 2 and there are two distinct finite centrosymmetric aggregates in the structure which exhibit different patterns of hydrogen-bonding behaviour. In the aggregate of type 1, which contains ferrocenediol 1, based on Fe1, and diamine 1, containing N1 and N4, the neutral molecular components are all fully ordered. In addition to the intramolecular O—H···O hydrogen bond in the ferrocenediol, which generates the usual S(8) motif, the individual molecular components are linked by both O—H···N and N—H···O hydrogen bonds, but there are no N—H···N hydrogen bonds present. Hydroxyl O11 acts as a hydrogen-bond donor to N1 within the asymmetric unit (Fig. 2); N1 in the diamine at (x, y, z) acts as a hydrogen-bond donor, via H1A and H1B, O11 and O12, respectively, in the ferrocenediol at (-x, 1 - y, 1 - z), and N4 at (x, y, z) also acts as donor, via H4A, to O12 at (-x, 1 - y, 1 - z) but H4B plays no part in the hydrogen bonding. In this manner, a four-component aggregate is formed, centred at (0, 1/2, 1/2) (Fig. 3) and containing a central R⁴₄(8) ring and pairs of both R²₃(6) and R¹₂(7) rings, in which O11 and O12, respectively, are the double acceptors.

The aggregate of type 2 contains the fully ordered ferrocenediol 2, based on Fe2, and the disordered diamine 2 (Fig. 2): in both of the orientations of this diamine, only one N atom participates in the hydrogen bonding, so that the rest of the chain, untethered at the distal end, is free to adopt more than one conformation. By contrast, in the type 1 aggregate both N atoms are engaged in ring formation, so locking the diamine component into a single conformation. The two amine conformers in the type 2 aggregate have refined site-occupation factors of 0.756 (5) and 0.244 (5), respectively. In addition, in the minor conformer, there is rotational disorder of the terminal NH₂ group based on N82: the partial H atoms on N82 could not be unambiguously located from difference maps, and hence they were omitted from the refinements. This type 2 aggregate contains the same O—H···O hydrogen bond as in the type 1 aggregate, and O21 in the ferrocenediol acts as hydrogen bond donor to N51 within the asymmetric unit: N51 at (x, y, z) in turn acts as hydrogen-bond donor, via H51A, to O21 in the ferrocenediol at (1 - x, -y, -z), so generating an R⁴₄(8) ring centred at (1/2, 0, 0) (Fig. 4). None of the other N—H bonds in this aggregate participates in hydrogen bonding, and there are no interactions between aggregates of the two types. The hydrogen-bonding patterns within these two types of aggregate (Figs. 3 and 4) may be contrasted with the very simple R⁶₆(12) ring in the four-component aggregate formed by the ferrocenediol in its adduct with methanol (Ferguson et al., 1993). Equally, the behaviour of the diamine component in (II) may be contrasted with that of piperazine in its adduct with the ferrocenediol (Glidewell et al., 1994), where the diamine acts only as a hydrogen-bond acceptor, and the ferrocenediol only as a hydrogen-bond donor.

In the ferrocenediol components of (I) and (II) the cyclopentadienyl rings are nearly eclipsed. A convenient measure of the relative twist of the rings in (I) is the torsion angle C11—Cg1—Cg2—C21, where Cg1 and Cg2 are the centroids of the two rings: to allow for the fact that the rings do not have local C₅ rotational symmetry, because of the variations in the C—C bond distances, the mean value of the torsion angles C1n—Cg1—Cg2—C2n (n = 1 - 5) provides a better measure. For (II), the relevant values are those of C11n—Cg1—Cg2—C12n and C21n—Cg3—Cg4—C22n (n =1 - 5). For perfect eclipsing, this mean value should be (72 x n)° (n = zero or integer): the observed values are 65.4 (4)° in (I) and 53.7 (4)° and -60.0 (4)° in (II), indicating that each independent ferrocenediol adopts a conformation which is close to eclipsed, with the substituents on the two rings offset from one another by one-fifth of a turn.

The orientation of the exocyclic CPh₂OH substituents relative to the adjacent rings (Table 1 and 3) is largely determined by the formation of the intramolecular O—H···O hydrogen bonds. In adduct (I), the central aliphatic portion of the diamine has an almost planar skeleton, but the rings are significantly twisted out of this plane (Table 1, Fig. 1). In adduct (II), the synclinal conformation of the diamine component in the type 1 aggregate is most readily ascribed to the hydrogen bonding, but such a simple explanation cannot be valid for the diamine in the type 2 aggregate, where the major and minor components of the amine adopt synclinal and antiperiplanar conformations respectively (Tables 3 and 4).

Related literature

For related literature, see: Ferguson et al. (1993, 1995); Glidewell et al. (1994).

S2. Experimental

For each adduct, stoichiometric quantities of the ferrocenediol and the appropriate amine were separately dissolved in methanol: the component solutions were mixed and the mixtures were set aside to crystallize producing analytically pure (I) and (II), respectively. Analyses: compound (I), found C 78.5, H 5.9, N 3.7%; C₄₈H₄₂FeN₂O₂ requires C 78.5, H 5.8, N 3.8%; compound (II), found C 74.2, H 6.3, N 4.6%; C₃₈H₃₈FeN₂O₂ requires C 74.7, H 6.3, N 4.6%. Crystals suitable for single-crystal X-ray diffraction were selected directly from the analytical samples.

S3. Refinement

Compounds (I) and (II) both crystallize in the triclinic system; for each, space group P1 was assumed and confirmed by the analysis. In (II), the hydrogen-bonded N atoms of the two conformers of amine 2, N51 and N52, were constrained to have identical coordinates and identical anisotropic displacement parameters. H atoms were treated as riding atoms with C—H 0.95 Å (aryl and cyclopentadienyl) or 0.99 Å (aliphatic), N—H 0.91 Å and O—H 0.84 Å.

Computing details

For both compounds, data collection: Collect (Nonius, 1997-2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. The molecular aggregate in (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular components of (II) showing the atom-labelling scheme, (a) ferrocenediol 1 and diamine 1; (b) ferrocenediol 2 and diamine 2. Displacement ellipsoids are drawn at the 30% probability level, but in (b) the minor conformer N52—N82 of the diamine is omitted for clarity.
	Fig. 3. Part of the crystal structure of (II) showing formation of a type 1 aggregate. For clarity, H atoms bonded to C are omitted: the atoms marked with a star (*) are at the symmetry position (-x, 1 - y, 1 - z).
	Fig. 4. Part of the crystal structure of (II) showing formation of a type 2 aggregate. For clarity, H atoms bonded to C are omitted, and only the major conformer of the diamine is shown. The atoms marked with a hash (#) are at the symmetry position (1 - x, -y, -z).

(I) Ferrocene-1,1'-diylbis(diphenylmethanol)–1,2-bis(4-pyridyl)ethane (1/1)

Crystal data

[Fe(C18H15O)]·C12H12N2	Z = 2
Mr = 734.69	F(000) = 772
Triclinic, P1	Dx = 1.328 Mg m^−3
a = 9.7191 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3281 (4) Å	Cell parameters from 7609 reflections
c = 17.5549 (7) Å	θ = 2.7–27.2°
α = 78.6970 (16)°	µ = 0.45 mm^−1
β = 87.8100 (15)°	T = 150 K
γ = 75.772 (2)°	Block, orange
V = 1837.05 (11) Å^3	0.20 × 0.18 × 0.18 mm

Data collection

Kappa-CCD diffractometer	8061 independent reflections
Radiation source: fine-focus sealed X-ray tube	4882 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
ϕ scans, and ω scans with κ offsets	θmax = 27.2°, θmin = 2.7°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = 0→12
Tmin = 0.915, Tmax = 0.923	k = −13→14
23051 measured reflections	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0442P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
8061 reflections	Δρmax = 0.29 e Å^−3
481 parameters	Δρmin = −0.40 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (7)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
Fe1	0.58246 (4)	0.21972 (4)	0.32690 (2)	0.02559 (13)
O1	0.32627 (19)	0.16989 (16)	0.19879 (10)	0.0290 (4)
O2	0.56163 (17)	−0.03784 (17)	0.23881 (11)	0.0299 (5)
C1	0.2769 (3)	0.2694 (2)	0.24043 (15)	0.0246 (6)
C11	0.4045 (3)	0.3133 (2)	0.26100 (15)	0.0239 (6)
C12	0.4206 (3)	0.3742 (2)	0.32287 (16)	0.0297 (6)
C13	0.5531 (3)	0.4061 (2)	0.31567 (17)	0.0323 (7)
C14	0.6213 (3)	0.3653 (3)	0.24918 (17)	0.0332 (7)
C15	0.5307 (3)	0.3092 (2)	0.21527 (16)	0.0282 (6)
C31	0.1701 (3)	0.3750 (2)	0.18831 (15)	0.0258 (6)
C32	0.0514 (3)	0.3485 (3)	0.16009 (16)	0.0319 (7)
C33	−0.0465 (3)	0.4381 (3)	0.11088 (17)	0.0373 (7)
C34	−0.0283 (3)	0.5576 (3)	0.08990 (17)	0.0410 (8)
C35	0.0869 (3)	0.5865 (3)	0.11831 (18)	0.0416 (8)
C36	0.1853 (3)	0.4951 (3)	0.16740 (16)	0.0326 (7)
C41	0.2034 (3)	0.2184 (2)	0.31337 (15)	0.0249 (6)
C42	0.2149 (3)	0.0909 (3)	0.33677 (16)	0.0299 (7)
C43	0.1574 (3)	0.0451 (3)	0.40611 (16)	0.0333 (7)
C44	0.0866 (3)	0.1241 (3)	0.45359 (17)	0.0382 (8)
C45	0.0697 (3)	0.2510 (3)	0.42915 (16)	0.0344 (7)
C46	0.1264 (3)	0.2976 (3)	0.35983 (16)	0.0310 (7)
C2	0.6992 (3)	−0.0417 (2)	0.26858 (16)	0.0266 (6)
C21	0.6802 (3)	0.0371 (2)	0.33112 (15)	0.0255 (6)
C22	0.5638 (3)	0.0488 (2)	0.38325 (16)	0.0293 (6)
C23	0.5875 (3)	0.1191 (3)	0.43750 (16)	0.0307 (7)
C24	0.7189 (3)	0.1516 (3)	0.41922 (16)	0.0312 (7)
C25	0.7762 (3)	0.1011 (3)	0.35407 (16)	0.0296 (6)
C51	0.7569 (3)	−0.1809 (3)	0.30422 (17)	0.0282 (6)
C52	0.7502 (3)	−0.2266 (3)	0.38375 (18)	0.0352 (7)
C53	0.7810 (3)	−0.3543 (3)	0.41295 (19)	0.0381 (8)
C54	0.8226 (3)	−0.4368 (3)	0.3628 (2)	0.0407 (8)
C55	0.8358 (3)	−0.3925 (3)	0.2847 (2)	0.0384 (8)
C56	0.8026 (3)	−0.2649 (3)	0.25523 (18)	0.0332 (7)
C61	0.7930 (3)	0.0025 (2)	0.20233 (16)	0.0300 (7)
C62	0.9381 (3)	−0.0143 (3)	0.21361 (18)	0.0352 (7)
C63	1.0223 (3)	0.0288 (3)	0.1544 (2)	0.0441 (8)
C64	0.9633 (4)	0.0887 (3)	0.0825 (2)	0.0498 (9)
C65	0.8202 (4)	0.1052 (3)	0.06977 (19)	0.0478 (9)
C66	0.7355 (3)	0.0629 (3)	0.12927 (17)	0.0353 (7)
N71	0.3644 (3)	0.2404 (2)	0.04191 (14)	0.0379 (6)
C72	0.3967 (3)	0.3484 (3)	0.01159 (17)	0.0431 (8)
C73	0.4498 (3)	0.3756 (3)	−0.06233 (17)	0.0387 (7)
C74	0.4717 (3)	0.2889 (3)	−0.10968 (16)	0.0290 (6)
C75	0.4363 (3)	0.1766 (3)	−0.07936 (17)	0.0368 (7)
C76	0.3853 (3)	0.1572 (3)	−0.00449 (17)	0.0393 (8)
C77	0.5239 (3)	0.3180 (3)	−0.19106 (16)	0.0332 (7)
N81	0.7512 (3)	0.3633 (3)	−0.45181 (15)	0.0462 (7)
C82	0.6315 (3)	0.3259 (3)	−0.43182 (18)	0.0429 (8)
C83	0.5999 (3)	0.2765 (3)	−0.35746 (17)	0.0364 (7)
C84	0.6924 (3)	0.2661 (3)	−0.29630 (17)	0.0314 (7)
C85	0.8146 (3)	0.3056 (3)	−0.31637 (19)	0.0384 (8)
C86	0.8398 (3)	0.3509 (3)	−0.3932 (2)	0.0468 (9)
C87	0.6532 (3)	0.2231 (3)	−0.21328 (17)	0.0346 (7)
H1	0.3299	0.1993	0.1512	0.044*
H2	0.5094	0.0342	0.2351	0.045*
H12	0.3533	0.3906	0.3625	0.036*
H13	0.5898	0.4474	0.3493	0.039*
H14	0.7121	0.3742	0.2307	0.040*
H15	0.5500	0.2746	0.1698	0.034*
H32	0.0371	0.2671	0.1749	0.038*
H33	−0.1259	0.4175	0.0916	0.045*
H34	−0.0948	0.6193	0.0561	0.049*
H35	0.0995	0.6685	0.1046	0.050*
H36	0.2642	0.5161	0.1868	0.039*
H42	0.2628	0.0355	0.3047	0.036*
H43	0.1664	−0.0418	0.4214	0.040*
H44	0.0503	0.0919	0.5021	0.046*
H45	0.0186	0.3064	0.4605	0.041*
H46	0.1127	0.3848	0.3436	0.037*
H22	0.4838	0.0151	0.3818	0.035*
H23	0.5266	0.1407	0.4788	0.037*
H24	0.7609	0.1992	0.4461	0.037*
H25	0.8635	0.1084	0.3298	0.036*
H52	0.7245	−0.1703	0.4184	0.042*
H53	0.7734	−0.3844	0.4670	0.046*
H54	0.8419	−0.5237	0.3823	0.049*
H55	0.8677	−0.4491	0.2506	0.046*
H56	0.8115	−0.2354	0.2012	0.040*
H62	0.9801	−0.0558	0.2626	0.042*
H63	1.1210	0.0171	0.1632	0.053*
H64	1.0212	0.1185	0.0421	0.060*
H65	0.7795	0.1455	0.0203	0.057*
H66	0.6368	0.0753	0.1201	0.042*
H72	0.3821	0.4100	0.0428	0.052*
H73	0.4711	0.4538	−0.0804	0.046*
H75	0.4473	0.1143	−0.1098	0.044*
H76	0.3636	0.0797	0.0153	0.047*
H77A	0.5477	0.3995	−0.1987	0.040*
H77B	0.4451	0.3263	−0.2274	0.040*
H82	0.5646	0.3343	−0.4718	0.051*
H83	0.5148	0.2492	−0.3475	0.044*
H85	0.8816	0.3015	−0.2773	0.046*
H86	0.9264	0.3749	−0.4050	0.056*
H87A	0.7342	0.2144	−0.1783	0.042*
H87B	0.6310	0.1411	−0.2075	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0260 (2)	0.0237 (2)	0.0258 (2)	−0.00525 (16)	−0.00004 (16)	−0.00246 (17)
O1	0.0327 (10)	0.0272 (11)	0.0249 (10)	−0.0037 (8)	0.0019 (9)	−0.0043 (8)
O2	0.0264 (10)	0.0247 (11)	0.0380 (12)	−0.0032 (8)	−0.0068 (9)	−0.0073 (9)
C1	0.0280 (14)	0.0220 (15)	0.0216 (14)	−0.0007 (11)	0.0007 (11)	−0.0063 (12)
C11	0.0255 (14)	0.0198 (15)	0.0235 (14)	−0.0037 (11)	0.0007 (11)	0.0006 (11)
C12	0.0316 (15)	0.0251 (16)	0.0303 (16)	−0.0029 (12)	0.0006 (12)	−0.0051 (13)
C13	0.0346 (16)	0.0216 (16)	0.0398 (18)	−0.0073 (12)	−0.0051 (13)	−0.0026 (13)
C14	0.0306 (16)	0.0278 (17)	0.0380 (18)	−0.0096 (13)	−0.0020 (13)	0.0046 (13)
C15	0.0301 (15)	0.0246 (16)	0.0263 (15)	−0.0040 (12)	−0.0001 (12)	0.0004 (12)
C31	0.0274 (15)	0.0254 (16)	0.0220 (14)	−0.0027 (12)	0.0012 (11)	−0.0035 (12)
C32	0.0342 (16)	0.0297 (17)	0.0320 (17)	−0.0092 (13)	−0.0017 (13)	−0.0044 (13)
C33	0.0337 (17)	0.041 (2)	0.0337 (18)	−0.0018 (14)	−0.0106 (13)	−0.0053 (15)
C34	0.0410 (18)	0.037 (2)	0.0349 (18)	0.0047 (14)	−0.0094 (14)	0.0009 (15)
C35	0.0471 (19)	0.0298 (18)	0.0420 (19)	−0.0038 (14)	−0.0076 (15)	0.0017 (15)
C36	0.0326 (16)	0.0293 (17)	0.0341 (17)	−0.0057 (13)	−0.0054 (13)	−0.0029 (13)
C41	0.0229 (14)	0.0278 (16)	0.0224 (14)	−0.0062 (11)	−0.0021 (11)	−0.0006 (12)
C42	0.0222 (14)	0.0314 (17)	0.0334 (17)	−0.0034 (12)	−0.0016 (12)	−0.0039 (13)
C43	0.0256 (15)	0.0341 (18)	0.0366 (17)	−0.0105 (13)	−0.0024 (13)	0.0063 (14)
C44	0.0308 (16)	0.052 (2)	0.0283 (17)	−0.0129 (15)	−0.0007 (13)	0.0047 (15)
C45	0.0299 (16)	0.044 (2)	0.0266 (16)	−0.0053 (14)	0.0035 (12)	−0.0049 (14)
C46	0.0290 (15)	0.0329 (17)	0.0278 (16)	−0.0039 (12)	0.0009 (12)	−0.0027 (13)
C2	0.0232 (14)	0.0228 (15)	0.0335 (16)	−0.0059 (11)	−0.0029 (12)	−0.0038 (12)
C21	0.0260 (14)	0.0214 (15)	0.0264 (15)	−0.0040 (11)	−0.0014 (11)	−0.0004 (12)
C22	0.0268 (15)	0.0265 (16)	0.0318 (16)	−0.0059 (12)	−0.0019 (12)	0.0010 (13)
C23	0.0339 (16)	0.0315 (17)	0.0248 (15)	−0.0056 (13)	0.0018 (12)	−0.0039 (13)
C24	0.0342 (16)	0.0300 (17)	0.0278 (16)	−0.0063 (13)	−0.0062 (12)	−0.0027 (13)
C25	0.0245 (14)	0.0304 (17)	0.0318 (16)	−0.0054 (12)	−0.0030 (12)	−0.0019 (13)
C51	0.0185 (13)	0.0243 (16)	0.0407 (17)	−0.0043 (11)	−0.0013 (12)	−0.0043 (13)
C52	0.0299 (16)	0.0308 (18)	0.0426 (19)	−0.0044 (13)	−0.0026 (13)	−0.0052 (14)
C53	0.0319 (16)	0.0293 (18)	0.0458 (19)	−0.0042 (13)	−0.0064 (14)	0.0070 (15)
C54	0.0317 (17)	0.0238 (17)	0.063 (2)	−0.0038 (13)	−0.0066 (15)	−0.0025 (16)
C55	0.0305 (16)	0.0257 (17)	0.060 (2)	−0.0045 (13)	−0.0033 (15)	−0.0134 (16)
C56	0.0300 (16)	0.0285 (17)	0.0425 (18)	−0.0062 (13)	−0.0021 (13)	−0.0107 (14)
C61	0.0339 (16)	0.0225 (16)	0.0340 (17)	−0.0048 (12)	0.0022 (13)	−0.0096 (13)
C62	0.0328 (16)	0.0280 (17)	0.0443 (19)	−0.0061 (13)	0.0024 (14)	−0.0079 (14)
C63	0.0360 (18)	0.038 (2)	0.061 (2)	−0.0107 (15)	0.0123 (16)	−0.0152 (17)
C64	0.060 (2)	0.042 (2)	0.050 (2)	−0.0173 (17)	0.0223 (18)	−0.0133 (17)
C65	0.062 (2)	0.047 (2)	0.0339 (19)	−0.0147 (17)	0.0068 (16)	−0.0077 (16)
C66	0.0425 (18)	0.0340 (18)	0.0326 (17)	−0.0107 (14)	0.0007 (14)	−0.0120 (14)
N71	0.0460 (15)	0.0362 (16)	0.0286 (14)	−0.0050 (12)	−0.0015 (11)	−0.0053 (12)
C72	0.062 (2)	0.041 (2)	0.0296 (18)	−0.0133 (16)	−0.0013 (15)	−0.0139 (15)
C73	0.0482 (19)	0.0355 (19)	0.0359 (18)	−0.0157 (15)	0.0010 (14)	−0.0079 (15)
C74	0.0282 (15)	0.0270 (16)	0.0291 (16)	−0.0024 (12)	−0.0047 (12)	−0.0038 (13)
C75	0.0534 (19)	0.0293 (17)	0.0293 (17)	−0.0114 (14)	0.0029 (14)	−0.0081 (13)
C76	0.054 (2)	0.0271 (17)	0.0338 (18)	−0.0080 (14)	0.0066 (15)	−0.0026 (14)
C77	0.0331 (16)	0.0315 (17)	0.0331 (17)	−0.0067 (13)	0.0017 (13)	−0.0035 (13)
N81	0.0501 (17)	0.0551 (19)	0.0402 (16)	−0.0214 (14)	0.0156 (13)	−0.0179 (14)
C82	0.0421 (19)	0.058 (2)	0.0355 (19)	−0.0170 (16)	0.0059 (14)	−0.0207 (17)
C83	0.0342 (17)	0.046 (2)	0.0353 (18)	−0.0183 (14)	0.0028 (13)	−0.0127 (15)
C84	0.0321 (16)	0.0272 (16)	0.0364 (17)	−0.0071 (13)	0.0070 (13)	−0.0109 (13)
C85	0.0254 (16)	0.0394 (19)	0.052 (2)	−0.0056 (13)	0.0034 (14)	−0.0166 (16)
C86	0.0370 (18)	0.057 (2)	0.058 (2)	−0.0238 (16)	0.0190 (17)	−0.0268 (19)
C87	0.0315 (16)	0.0313 (17)	0.0384 (18)	−0.0055 (13)	−0.0025 (13)	−0.0025 (14)

Geometric parameters (Å, º)

Fe1—C14	2.027 (3)	C23—C24	1.422 (4)
Fe1—C13	2.030 (3)	C23—H23	0.95
Fe1—C12	2.036 (3)	C24—C25	1.413 (4)
Fe1—C24	2.037 (3)	C24—H24	0.95
Fe1—C25	2.038 (3)	C25—H25	0.95
Fe1—C22	2.041 (3)	C51—C56	1.388 (4)
Fe1—C21	2.042 (3)	C51—C52	1.396 (4)
Fe1—C15	2.041 (3)	C52—C53	1.397 (4)
Fe1—C23	2.045 (3)	C52—H52	0.95
Fe1—C11	2.055 (2)	C53—C54	1.386 (4)
O1—C1	1.437 (3)	C53—H53	0.95
O1—H1	0.8400	C54—C55	1.378 (4)
O2—C2	1.441 (3)	C54—H54	0.95
O2—H2	0.84	C55—C56	1.397 (4)
C1—C11	1.525 (4)	C55—H55	0.95
C1—C41	1.525 (3)	C56—H56	0.95
C1—C31	1.543 (3)	C61—C62	1.393 (4)
C11—C12	1.429 (4)	C61—C66	1.396 (4)
C11—C15	1.436 (3)	C62—C63	1.386 (4)
C12—C13	1.415 (4)	C62—H62	0.95
C12—H12	0.95	C63—C64	1.381 (4)
C13—C14	1.420 (4)	C63—H63	0.95
C13—H13	0.95	C64—C65	1.378 (4)
C14—C15	1.414 (4)	C64—H64	0.95
C14—H14	0.95	C65—C66	1.390 (4)
C15—H15	0.95	C65—H65	0.95
C31—C36	1.381 (4)	C66—H66	0.95
C31—C32	1.393 (4)	N71—C76	1.337 (4)
C32—C33	1.388 (4)	N71—C72	1.341 (4)
C32—H32	0.95	C72—C73	1.384 (4)
C33—C34	1.385 (4)	C72—H72	0.95
C33—H33	0.95	C73—C74	1.380 (4)
C34—C35	1.376 (4)	C73—H73	0.95
C34—H34	0.95	C74—C75	1.398 (4)
C35—C36	1.398 (4)	C74—C77	1.500 (4)
C35—H35	0.95	C75—C76	1.383 (4)
C36—H36	0.95	C75—H75	0.95
C41—C46	1.393 (4)	C76—H76	0.95
C41—C42	1.400 (4)	C77—C87	1.533 (4)
C42—C43	1.381 (4)	C77—H77A	0.99
C42—H42	0.95	C77—H77B	0.99
C43—C44	1.384 (4)	N81—C86	1.331 (4)
C43—H43	0.95	N81—C82	1.346 (4)
C44—C45	1.388 (4)	C82—C83	1.371 (4)
C44—H44	0.95	C82—H82	0.95
C45—C46	1.379 (4)	C83—C84	1.396 (4)
C45—H45	0.95	C83—H83	0.95
C46—H46	0.95	C84—C85	1.379 (4)
C2—C21	1.524 (4)	C84—C87	1.509 (4)
C2—C61	1.533 (4)	C85—C86	1.381 (4)
C2—C51	1.549 (4)	C85—H85	0.95
C21—C22	1.425 (4)	C86—H86	0.95
C21—C25	1.426 (4)	C87—H87A	0.99
C22—C23	1.413 (4)	C87—H87B	0.99
C22—H22	0.95
C1—O1—H1	109.5	C56—C51—C52	118.6 (3)
C2—O2—H2	109.5	C56—C51—C2	119.2 (3)
O1—C1—C11	108.4 (2)	C52—C51—C2	121.8 (2)
O1—C1—C41	107.4 (2)	C51—C52—C53	120.7 (3)
C11—C1—C41	111.1 (2)	C51—C52—H52	119.6
O1—C1—C31	108.6 (2)	C53—C52—H52	119.6
C11—C1—C31	111.1 (2)	C54—C53—C52	119.8 (3)
C41—C1—C31	110.0 (2)	C54—C53—H53	120.1
C12—C11—C15	106.3 (2)	C52—C53—H53	120.1
C12—C11—C1	128.9 (2)	C55—C54—C53	119.8 (3)
C15—C11—C1	124.6 (2)	C55—C54—H54	120.1
C13—C12—C11	109.0 (2)	C53—C54—H54	120.1
C13—C12—H12	125.5	C54—C55—C56	120.4 (3)
C11—C12—H12	125.5	C54—C55—H55	119.8
C12—C13—C14	107.8 (3)	C56—C55—H55	119.8
C12—C13—H13	126.1	C51—C56—C55	120.6 (3)
C14—C13—H13	126.1	C51—C56—H56	119.7
C15—C14—C13	108.1 (2)	C55—C56—H56	119.7
C15—C14—H14	125.9	C62—C61—C66	117.9 (3)
C13—C14—H14	125.9	C62—C61—C2	121.0 (3)
C14—C15—C11	108.7 (2)	C66—C61—C2	121.1 (2)
C14—C15—H15	125.7	C63—C62—C61	121.0 (3)
C11—C15—H15	125.7	C63—C62—H62	119.5
C36—C31—C32	117.6 (2)	C61—C62—H62	119.5
C36—C31—C1	123.9 (2)	C64—C63—C62	120.3 (3)
C32—C31—C1	118.5 (2)	C64—C63—H63	119.8
C33—C32—C31	121.5 (3)	C62—C63—H63	119.8
C33—C32—H32	119.2	C65—C64—C63	119.7 (3)
C31—C32—H32	119.2	C65—C64—H64	120.1
C34—C33—C32	119.8 (3)	C63—C64—H64	120.1
C34—C33—H33	120.1	C64—C65—C66	120.0 (3)
C32—C33—H33	120.1	C64—C65—H65	120.0
C35—C34—C33	119.6 (3)	C66—C65—H65	120.0
C35—C34—H34	120.2	C65—C66—C61	121.1 (3)
C33—C34—H34	120.2	C65—C66—H66	119.5
C34—C35—C36	120.0 (3)	C61—C66—H66	119.5
C34—C35—H35	120.0	C76—N71—C72	115.7 (3)
C36—C35—H35	120.0	N71—C72—C73	124.0 (3)
C31—C36—C35	121.4 (3)	N71—C72—H72	118.0
C31—C36—H36	119.3	C73—C72—H72	118.0
C35—C36—H36	119.3	C74—C73—C72	119.8 (3)
C46—C41—C42	118.2 (3)	C74—C73—H73	120.1
C46—C41—C1	120.7 (2)	C72—C73—H73	120.1
C42—C41—C1	121.1 (2)	C73—C74—C75	116.8 (3)
C43—C42—C41	120.5 (3)	C73—C74—C77	120.8 (3)
C43—C42—H42	119.7	C75—C74—C77	122.3 (3)
C41—C42—H42	119.7	C76—C75—C74	119.2 (3)
C42—C43—C44	120.8 (3)	C76—C75—H75	120.4
C42—C43—H43	119.6	C74—C75—H75	120.4
C44—C43—H43	119.6	N71—C76—C75	124.4 (3)
C43—C44—C45	118.9 (3)	N71—C76—H76	117.8
C43—C44—H44	120.5	C75—C76—H76	117.8
C45—C44—H44	120.5	C74—C77—C87	116.0 (2)
C46—C45—C44	120.6 (3)	C74—C77—H77A	108.3
C46—C45—H45	119.7	C87—C77—H77A	108.3
C44—C45—H45	119.7	C74—C77—H77B	108.3
C45—C46—C41	120.8 (3)	C87—C77—H77B	108.3
C45—C46—H46	119.6	H77A—C77—H77B	107.4
C41—C46—H46	119.6	C86—N81—C82	115.1 (3)
O2—C2—C21	109.1 (2)	N81—C82—C83	124.2 (3)
O2—C2—C61	110.2 (2)	N81—C82—H82	117.9
C21—C2—C61	111.9 (2)	C83—C82—H82	117.9
O2—C2—C51	102.9 (2)	C82—C83—C84	120.1 (3)
C21—C2—C51	110.9 (2)	C82—C83—H83	119.9
C61—C2—C51	111.6 (2)	C84—C83—H83	119.9
C22—C21—C25	107.3 (2)	C85—C84—C83	115.9 (3)
C22—C21—C2	124.0 (2)	C85—C84—C87	123.0 (3)
C25—C21—C2	128.4 (2)	C83—C84—C87	120.9 (2)
C23—C22—C21	108.5 (2)	C84—C85—C86	120.1 (3)
C23—C22—H22	125.8	C84—C85—H85	120.0
C21—C22—H22	125.8	C86—C85—H85	120.0
C22—C23—C24	107.8 (2)	N81—C86—C85	124.6 (3)
C22—C23—H23	126.1	N81—C86—H86	117.7
C24—C23—H23	126.1	C85—C86—H86	117.7
C25—C24—C23	108.2 (3)	C84—C87—C77	109.4 (2)
C25—C24—H24	125.9	C84—C87—H87A	109.8
C23—C24—H24	125.9	C77—C87—H87A	109.8
C24—C25—C21	108.2 (2)	C84—C87—H87B	109.8
C24—C25—H25	125.9	C77—C87—H87B	109.8
C21—C25—H25	125.9	H87A—C87—H87B	108.2
O1—C1—C11—C12	−155.0 (2)	C22—C23—C24—C25	−0.3 (3)
C31—C1—C11—C12	85.7 (3)	C23—C24—C25—C21	0.3 (3)
C41—C1—C11—C12	−37.2 (4)	C22—C21—C25—C24	−0.2 (3)
O1—C1—C11—C15	30.6 (3)	C2—C21—C25—C24	−174.4 (3)
C41—C1—C11—C15	148.5 (2)	O2—C2—C51—C56	73.9 (3)
C31—C1—C11—C15	−88.6 (3)	C21—C2—C51—C56	−169.7 (2)
C15—C11—C12—C13	−0.3 (3)	C61—C2—C51—C56	−44.3 (3)
C1—C11—C12—C13	−175.4 (2)	O2—C2—C51—C52	−99.2 (3)
C11—C12—C13—C14	−0.1 (3)	C21—C2—C51—C52	17.3 (3)
C12—C13—C14—C15	0.4 (3)	C61—C2—C51—C52	142.7 (2)
C13—C14—C15—C11	−0.6 (3)	C56—C51—C52—C53	−3.7 (4)
C12—C11—C15—C14	0.5 (3)	C2—C51—C52—C53	169.4 (2)
C1—C11—C15—C14	175.9 (2)	C51—C52—C53—C54	1.9 (4)
O1—C1—C31—C36	−122.8 (3)	C52—C53—C54—C55	1.1 (4)
C11—C1—C31—C36	−3.7 (4)	C53—C54—C55—C56	−2.3 (4)
C41—C1—C31—C36	119.9 (3)	C52—C51—C56—C55	2.5 (4)
O1—C1—C31—C32	56.9 (3)	C2—C51—C56—C55	−170.7 (2)
C11—C1—C31—C32	176.0 (2)	C54—C55—C56—C51	0.4 (4)
C41—C1—C31—C32	−60.4 (3)	O2—C2—C61—C62	−168.0 (2)
C36—C31—C32—C33	1.8 (4)	C21—C2—C61—C62	70.5 (3)
C1—C31—C32—C33	−177.9 (3)	C51—C2—C61—C62	−54.3 (3)
C31—C32—C33—C34	−1.1 (4)	O2—C2—C61—C66	13.2 (3)
C32—C33—C34—C35	−0.2 (5)	C21—C2—C61—C66	−108.3 (3)
C33—C34—C35—C36	0.6 (5)	C51—C2—C61—C66	126.9 (3)
C32—C31—C36—C35	−1.4 (4)	C66—C61—C62—C63	0.7 (4)
C1—C31—C36—C35	178.3 (3)	C2—C61—C62—C63	−178.2 (3)
C34—C35—C36—C31	0.2 (5)	C61—C62—C63—C64	−0.4 (5)
O1—C1—C41—C46	−170.6 (2)	C62—C63—C64—C65	−0.3 (5)
C11—C1—C41—C46	70.9 (3)	C63—C64—C65—C66	0.8 (5)
C31—C1—C41—C46	−52.6 (3)	C64—C65—C66—C61	−0.5 (5)
O1—C1—C41—C42	11.4 (3)	C62—C61—C66—C65	−0.2 (4)
C11—C1—C41—C42	−107.1 (3)	C2—C61—C66—C65	178.7 (3)
C31—C1—C41—C42	129.4 (2)	C76—N71—C72—C73	−0.7 (4)
C46—C41—C42—C43	−3.2 (4)	N71—C72—C73—C74	0.4 (5)
C1—C41—C42—C43	174.9 (2)	C72—C73—C74—C75	0.7 (4)
C41—C42—C43—C44	0.3 (4)	C72—C73—C74—C77	177.7 (2)
C42—C43—C44—C45	2.4 (4)	C73—C74—C75—C76	−1.4 (4)
C43—C44—C45—C46	−2.1 (4)	C77—C74—C75—C76	−178.3 (2)
C44—C45—C46—C41	−0.9 (4)	C72—N71—C76—C75	−0.1 (4)
C42—C41—C46—C45	3.5 (4)	C74—C75—C76—N71	1.1 (5)
C1—C41—C46—C45	−174.6 (2)	C75—C74—C77—C87	−54.6 (4)
C73—C74—C77—C87	128.6 (3)	C86—N81—C82—C83	−0.9 (5)
C83—C84—C87—C77	−64.3 (3)	N81—C82—C83—C84	2.2 (5)
O2—C2—C21—C22	34.4 (3)	C82—C83—C84—C85	−1.3 (4)
C51—C2—C21—C22	−78.2 (3)	C82—C83—C84—C87	174.3 (3)
C61—C2—C21—C22	156.6 (2)	C83—C84—C85—C86	−0.5 (4)
O2—C2—C21—C25	−152.2 (2)	C87—C84—C85—C86	−176.0 (3)
C61—C2—C21—C25	−30.0 (4)	C82—N81—C86—C85	−1.1 (5)
C51—C2—C21—C25	95.2 (3)	C84—C85—C86—N81	1.8 (5)
C25—C21—C22—C23	0.0 (3)	C85—C84—C87—C77	110.9 (3)
C2—C21—C22—C23	174.6 (2)	C74—C77—C87—C84	−179.8 (2)
C21—C22—C23—C24	0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N71	0.84	1.92	2.751 (3)	170
O2—H2···O1	0.84	2.07	2.845 (2)	153

(II) Ferrocene-1,1'-diylbis(diphenylmethanol)–1,2-diaminoethane (1/1)

Crystal data

[Fe(C18H15O)]·C2H8N2	Z = 4
Mr = 610.55	F(000) = 1288
Triclinic, P1	Dx = 1.338 Mg m^−3
a = 9.8551 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7183 (2) Å	Cell parameters from 12683 reflections
c = 27.6810 (5) Å	θ = 2.7–27.5°
α = 82.3495 (8)°	µ = 0.54 mm^−1
β = 84.4918 (8)°	T = 150 K
γ = 73.4846 (8)°	Block, orange
V = 3031.88 (10) Å^3	0.32 × 0.28 × 0.26 mm

Data collection

Kappa-CCD diffractometer	13826 independent reflections
Radiation source: fine-focus sealed X-ray tube	8093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = 0→12
Tmin = 0.848, Tmax = 0.873	k = −14→15
39122 measured reflections	l = −35→35

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.043P)^2] where P = (Fo^2 + 2Fc^2)/3
13826 reflections	(Δ/σ)max < 0.001
795 parameters	Δρmax = 0.38 e Å^−3
9 restraints	Δρmin = −0.42 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.40357 (4)	0.36346 (3)	0.347750 (14)	0.02290 (11)
O11	0.1126 (2)	0.37855 (14)	0.44166 (7)	0.0262 (4)
O12	0.0750 (2)	0.58204 (15)	0.38063 (7)	0.0294 (5)
C11	0.1845 (3)	0.2618 (2)	0.42763 (10)	0.0230 (6)
C12	0.1783 (3)	0.6316 (2)	0.35284 (10)	0.0245 (6)
C111	0.3327 (3)	0.2615 (2)	0.40629 (10)	0.0229 (6)
C112	0.4194 (3)	0.1877 (2)	0.37181 (10)	0.0257 (6)
C113	0.5558 (3)	0.2080 (2)	0.36650 (10)	0.0295 (7)
C114	0.5550 (3)	0.2953 (2)	0.39781 (10)	0.0308 (7)
C115	0.4179 (3)	0.3286 (2)	0.42184 (10)	0.0264 (6)
C121	0.2846 (3)	0.5360 (2)	0.32572 (10)	0.0239 (6)
C122	0.2445 (3)	0.4498 (2)	0.30225 (10)	0.0283 (7)
C123	0.3656 (3)	0.3851 (2)	0.27576 (10)	0.0321 (7)
C124	0.4803 (3)	0.4294 (2)	0.28212 (10)	0.0320 (7)
C125	0.4314 (3)	0.5225 (2)	0.31309 (10)	0.0258 (6)
C131	0.1894 (3)	0.1718 (2)	0.47375 (10)	0.0239 (6)
C132	0.0628 (3)	0.1550 (3)	0.49574 (11)	0.0319 (7)
C133	0.0578 (3)	0.0811 (3)	0.53873 (11)	0.0380 (8)
C134	0.1832 (3)	0.0213 (3)	0.56087 (11)	0.0377 (8)
C135	0.3093 (3)	0.0384 (3)	0.54034 (11)	0.0397 (8)
C136	0.3131 (3)	0.1133 (2)	0.49686 (10)	0.0317 (7)
C141	0.0981 (3)	0.2345 (2)	0.38947 (10)	0.0236 (6)
C142	−0.0079 (3)	0.3232 (2)	0.36603 (10)	0.0285 (7)
C143	−0.0818 (3)	0.2971 (3)	0.33056 (11)	0.0344 (7)
C144	−0.0497 (3)	0.1824 (3)	0.31768 (11)	0.0349 (7)
C145	0.0543 (3)	0.0924 (3)	0.34149 (11)	0.0325 (7)
C146	0.1253 (3)	0.1187 (2)	0.37717 (10)	0.0264 (6)
C151	0.0921 (3)	0.7293 (2)	0.31591 (10)	0.0258 (6)
C152	0.1340 (3)	0.7433 (2)	0.26762 (11)	0.0324 (7)
C153	0.0523 (3)	0.8327 (3)	0.23519 (12)	0.0406 (8)
C154	−0.0734 (3)	0.9083 (3)	0.25216 (13)	0.0412 (9)
C155	−0.1164 (3)	0.8951 (2)	0.30077 (13)	0.0389 (8)
C156	−0.0341 (3)	0.8072 (2)	0.33319 (11)	0.0323 (7)
C161	0.2509 (3)	0.6900 (2)	0.38555 (10)	0.0270 (7)
C162	0.3241 (3)	0.7719 (2)	0.36530 (11)	0.0309 (7)
C163	0.3839 (3)	0.8287 (2)	0.39506 (12)	0.0395 (8)
C164	0.3716 (3)	0.8046 (3)	0.44523 (13)	0.0414 (9)
C165	0.3025 (3)	0.7210 (3)	0.46562 (12)	0.0437 (9)
C166	0.2418 (3)	0.6637 (3)	0.43631 (11)	0.0340 (7)
Fe2	0.37640 (4)	0.06863 (3)	0.195217 (14)	0.02341 (11)
O21	0.4933 (2)	0.10212 (15)	0.06452 (6)	0.0254 (4)
O22	0.63074 (19)	−0.11735 (15)	0.11437 (6)	0.0271 (4)
C21	0.4444 (3)	0.2080 (2)	0.08943 (10)	0.0246 (6)
C22	0.5795 (3)	−0.1800 (2)	0.15691 (10)	0.0242 (6)
C211	0.3431 (3)	0.1848 (2)	0.13210 (10)	0.0244 (6)
C212	0.2990 (3)	0.2481 (2)	0.17409 (10)	0.0258 (6)
C213	0.1929 (3)	0.2028 (2)	0.20202 (11)	0.0313 (7)
C214	0.1700 (3)	0.1115 (2)	0.17777 (10)	0.0312 (7)
C215	0.2620 (3)	0.1007 (2)	0.13465 (10)	0.0272 (7)
C221	0.5254 (3)	−0.0952 (2)	0.19609 (10)	0.0243 (6)
C222	0.5892 (3)	−0.0050 (2)	0.20404 (10)	0.0267 (7)
C223	0.5210 (3)	0.0481 (2)	0.24620 (10)	0.0287 (7)
C224	0.4150 (3)	−0.0082 (2)	0.26501 (10)	0.0300 (7)
C225	0.4168 (3)	−0.0970 (2)	0.23399 (9)	0.0263 (6)
C231	0.3697 (3)	0.3136 (2)	0.05295 (10)	0.0270 (7)
C232	0.4432 (3)	0.3397 (3)	0.00960 (11)	0.0360 (8)
C233	0.3806 (4)	0.4317 (3)	−0.02505 (12)	0.0438 (9)
C234	0.2440 (4)	0.5009 (3)	−0.01618 (12)	0.0489 (10)
C235	0.1699 (4)	0.4762 (3)	0.02674 (12)	0.0522 (10)
C236	0.2314 (4)	0.3823 (3)	0.06141 (11)	0.0427 (9)
C241	0.5748 (3)	0.2350 (2)	0.10606 (10)	0.0251 (6)
C242	0.5609 (3)	0.3409 (2)	0.12663 (10)	0.0307 (7)
C243	0.6757 (3)	0.3632 (3)	0.14466 (11)	0.0377 (8)
C244	0.8093 (3)	0.2817 (3)	0.14131 (12)	0.0424 (8)
C245	0.8248 (3)	0.1795 (3)	0.11934 (12)	0.0388 (8)
C246	0.7093 (3)	0.1551 (2)	0.10208 (11)	0.0314 (7)
C251	0.7098 (3)	−0.2816 (2)	0.17373 (10)	0.0261 (6)
C252	0.7930 (3)	−0.3504 (2)	0.13907 (11)	0.0321 (7)
C253	0.9109 (3)	−0.4426 (2)	0.15229 (12)	0.0381 (8)
C254	0.9469 (3)	−0.4685 (3)	0.20033 (13)	0.0425 (9)
C255	0.8630 (4)	−0.4018 (3)	0.23542 (12)	0.0435 (9)
C256	0.7454 (3)	−0.3089 (2)	0.22204 (11)	0.0356 (8)
C261	0.4661 (3)	−0.2356 (2)	0.14416 (10)	0.0244 (6)
C262	0.3970 (3)	−0.1963 (3)	0.10060 (11)	0.0331 (7)
C263	0.2947 (3)	−0.2467 (3)	0.08924 (13)	0.0438 (9)
C264	0.2573 (3)	−0.3360 (3)	0.12106 (13)	0.0457 (9)
C265	0.3260 (3)	−0.3762 (3)	0.16431 (12)	0.0389 (8)
C266	0.4293 (3)	−0.3264 (2)	0.17523 (11)	0.0320 (7)
N1	0.1551 (2)	0.4189 (2)	0.53263 (8)	0.0315 (6)
C2	0.3019 (3)	0.4024 (3)	0.54452 (11)	0.0373 (8)
C3	0.3210 (3)	0.4354 (3)	0.59423 (10)	0.0355 (7)
N4	0.2705 (3)	0.3680 (3)	0.63668 (9)	0.0533 (8)
N51	0.2997 (3)	0.0977 (2)	0.00037 (9)	0.0405 (7)	0.744 (5)
C61	0.1492 (4)	0.1211 (16)	0.0148 (2)	0.0523 (10)	0.744 (5)
C71	0.0470 (5)	0.1870 (5)	−0.02434 (15)	0.0460 (14)	0.744 (5)
N81	0.0708 (4)	0.1159 (3)	−0.06569 (12)	0.0435 (12)	0.744 (5)
N52	0.2997 (3)	0.0977 (2)	0.00037 (9)	0.0405 (7)	0.256 (5)
C62	0.1520 (9)	0.120 (5)	0.0190 (6)	0.0523 (10)	0.256 (5)
C72	0.0533 (12)	0.1161 (14)	−0.0195 (5)	0.040*	0.256 (5)
N82	−0.0905 (12)	0.1385 (11)	0.0032 (4)	0.070 (4)*	0.256 (5)
H11	0.1359	0.3842	0.4695	0.039*
H12	0.1159	0.5172	0.3966	0.044*
H112	0.3906	0.1336	0.3551	0.031*
H113	0.6335	0.1701	0.3458	0.035*
H114	0.6323	0.3258	0.4019	0.037*
H115	0.3877	0.3862	0.4446	0.032*
H122	0.1525	0.4381	0.3041	0.034*
H123	0.3688	0.3223	0.2569	0.039*
H124	0.5741	0.4020	0.2682	0.038*
H125	0.4871	0.5678	0.3235	0.031*
H132	−0.0232	0.1956	0.4807	0.038*
H133	−0.0303	0.0712	0.5530	0.046*
H134	0.1816	−0.0311	0.5901	0.045*
H135	0.3947	−0.0010	0.5559	0.048*
H136	0.4012	0.1242	0.4830	0.038*
H142	−0.0301	0.4028	0.3743	0.034*
H143	−0.1548	0.3587	0.3151	0.041*
H144	−0.0983	0.1651	0.2928	0.042*
H145	0.0764	0.0128	0.3332	0.039*
H146	0.1947	0.0560	0.3938	0.032*
H152	0.2201	0.6914	0.2558	0.039*
H153	0.0831	0.8415	0.2017	0.049*
H154	−0.1295	0.9690	0.2303	0.049*
H155	−0.2032	0.9463	0.3124	0.047*
H156	−0.0635	0.8001	0.3669	0.039*
H162	0.3334	0.7893	0.3308	0.037*
H163	0.4337	0.8846	0.3808	0.047*
H164	0.4104	0.8452	0.4655	0.050*
H165	0.2962	0.7023	0.5001	0.052*
H166	0.1941	0.6065	0.4508	0.041*
H21	0.4326	0.1013	0.0453	0.038*
H22	0.5708	−0.0515	0.1074	0.041*
H212	0.3346	0.3102	0.1821	0.031*
H213	0.1456	0.2293	0.2317	0.038*
H214	0.1050	0.0657	0.1883	0.037*
H215	0.2682	0.0464	0.1114	0.033*
H222	0.6648	0.0161	0.1844	0.032*
H223	0.5428	0.1109	0.2596	0.034*
H224	0.3536	0.0097	0.2932	0.036*
H225	0.3562	−0.1482	0.2379	0.032*
H232	0.5382	0.2937	0.0035	0.043*
H233	0.4319	0.4471	−0.0549	0.053*
H234	0.2014	0.5650	−0.0395	0.059*
H235	0.0756	0.5236	0.0329	0.063*
H236	0.1787	0.3655	0.0907	0.051*
H242	0.4710	0.3985	0.1282	0.037*
H243	0.6634	0.4344	0.1594	0.045*
H244	0.8884	0.2963	0.1539	0.051*
H245	0.9162	0.1247	0.1159	0.047*
H246	0.7221	0.0836	0.0875	0.038*
H252	0.7688	−0.3341	0.1060	0.038*
H253	0.9676	−0.4885	0.1281	0.046*
H254	1.0284	−0.5315	0.2092	0.051*
H255	0.8860	−0.4196	0.2686	0.052*
H256	0.6884	−0.2634	0.2463	0.043*
H262	0.4206	−0.1344	0.0786	0.040*
H263	0.2496	−0.2198	0.0594	0.053*
H264	0.1857	−0.3694	0.1135	0.055*
H265	0.3019	−0.4379	0.1863	0.047*
H266	0.4761	−0.3551	0.2047	0.038*
H1A	0.1040	0.4960	0.5355	0.047*
H1B	0.1162	0.3684	0.5536	0.047*
H2A	0.3459	0.4511	0.5192	0.045*
H2B	0.3547	0.3174	0.5426	0.045*
H3A	0.4233	0.4254	0.5969	0.043*
H3B	0.2716	0.5213	0.5955	0.043*
H4B	0.3183	0.2890	0.6371	0.080*
H4A	0.1762	0.3771	0.6352	0.080*
H51B	0.3155	0.1626	−0.0188	0.061*
H51A	0.3276	0.0327	−0.0166	0.061*
H61A	0.1288	0.1685	0.0430	0.063*	0.744 (5)
H61B	0.1290	0.0434	0.0262	0.063*	0.744 (5)
H71A	−0.0520	0.1995	−0.0107	0.055*	0.744 (5)
H71B	0.0627	0.2663	−0.0355	0.055*	0.744 (5)
H81A	0.0096	0.1548	−0.0890	0.065*	0.744 (5)
H81B	0.0559	0.0432	−0.0553	0.065*	0.744 (5)
H62A	0.1208	0.1998	0.0312	0.063*	0.256 (5)
H62B	0.1448	0.0594	0.0469	0.063*	0.256 (5)
H72A	0.0572	0.1778	−0.0473	0.048*	0.256 (5)
H72B	0.0825	0.0366	−0.0318	0.048*	0.256 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0247 (2)	0.0207 (2)	0.0224 (2)	−0.00531 (17)	−0.00219 (17)	−0.00097 (16)
O11	0.0320 (11)	0.0202 (9)	0.0250 (11)	−0.0038 (8)	−0.0027 (9)	−0.0046 (8)
O12	0.0313 (11)	0.0211 (10)	0.0336 (12)	−0.0067 (9)	0.0018 (9)	0.0013 (8)
C11	0.0236 (15)	0.0201 (13)	0.0248 (15)	−0.0046 (11)	−0.0003 (12)	−0.0043 (11)
C12	0.0245 (15)	0.0220 (13)	0.0267 (15)	−0.0073 (12)	−0.0021 (12)	0.0009 (11)
C111	0.0238 (15)	0.0199 (13)	0.0230 (15)	−0.0038 (11)	−0.0016 (12)	0.0004 (11)
C112	0.0270 (16)	0.0206 (14)	0.0277 (16)	−0.0041 (12)	−0.0026 (13)	−0.0010 (12)
C113	0.0264 (16)	0.0237 (14)	0.0348 (17)	−0.0047 (12)	−0.0006 (13)	0.0040 (12)
C114	0.0294 (17)	0.0352 (16)	0.0290 (16)	−0.0136 (13)	−0.0080 (13)	0.0074 (13)
C115	0.0285 (16)	0.0293 (15)	0.0227 (15)	−0.0106 (13)	−0.0037 (12)	−0.0001 (12)
C121	0.0276 (16)	0.0203 (13)	0.0219 (15)	−0.0041 (12)	−0.0042 (12)	0.0004 (11)
C122	0.0297 (16)	0.0263 (15)	0.0272 (16)	−0.0052 (13)	−0.0061 (13)	0.0004 (12)
C123	0.0447 (19)	0.0230 (14)	0.0243 (16)	−0.0007 (14)	−0.0066 (14)	−0.0032 (12)
C124	0.0311 (17)	0.0305 (16)	0.0251 (16)	0.0010 (13)	0.0052 (13)	0.0041 (12)
C125	0.0294 (16)	0.0247 (14)	0.0230 (15)	−0.0090 (12)	−0.0006 (12)	0.0009 (11)
C131	0.0280 (16)	0.0210 (13)	0.0222 (15)	−0.0057 (12)	−0.0009 (12)	−0.0037 (11)
C132	0.0266 (16)	0.0348 (16)	0.0312 (17)	−0.0063 (13)	0.0001 (13)	0.0016 (13)
C133	0.0329 (18)	0.0414 (18)	0.0382 (19)	−0.0138 (15)	0.0034 (14)	0.0053 (14)
C134	0.046 (2)	0.0301 (16)	0.0286 (17)	−0.0037 (15)	0.0030 (15)	0.0059 (13)
C135	0.0358 (19)	0.0408 (18)	0.0314 (18)	0.0018 (15)	−0.0005 (15)	0.0070 (14)
C136	0.0250 (16)	0.0358 (16)	0.0323 (17)	−0.0068 (13)	0.0006 (13)	−0.0017 (13)
C141	0.0241 (15)	0.0228 (14)	0.0241 (15)	−0.0077 (12)	0.0017 (12)	−0.0029 (11)
C142	0.0253 (15)	0.0281 (15)	0.0325 (17)	−0.0072 (12)	−0.0009 (13)	−0.0059 (12)
C143	0.0298 (17)	0.0377 (17)	0.0362 (18)	−0.0118 (14)	−0.0055 (14)	0.0022 (14)
C144	0.0329 (17)	0.0451 (18)	0.0327 (17)	−0.0189 (15)	−0.0007 (14)	−0.0088 (14)
C145	0.0358 (18)	0.0325 (16)	0.0347 (17)	−0.0173 (14)	0.0059 (14)	−0.0114 (13)
C146	0.0243 (15)	0.0220 (14)	0.0316 (16)	−0.0062 (12)	0.0008 (13)	−0.0011 (12)
C151	0.0284 (16)	0.0183 (13)	0.0312 (16)	−0.0070 (12)	−0.0073 (13)	0.0006 (12)
C152	0.0351 (18)	0.0300 (15)	0.0314 (17)	−0.0104 (14)	−0.0026 (14)	0.0023 (13)
C153	0.044 (2)	0.0417 (18)	0.0360 (19)	−0.0150 (16)	−0.0123 (16)	0.0099 (14)
C154	0.0374 (19)	0.0318 (17)	0.055 (2)	−0.0103 (15)	−0.0253 (18)	0.0089 (15)
C155	0.0258 (17)	0.0267 (16)	0.064 (2)	−0.0043 (13)	−0.0135 (16)	−0.0025 (15)
C156	0.0315 (17)	0.0255 (15)	0.0394 (18)	−0.0075 (13)	−0.0021 (14)	−0.0021 (13)
C161	0.0246 (15)	0.0220 (14)	0.0305 (16)	0.0023 (12)	−0.0054 (13)	−0.0060 (12)
C162	0.0348 (17)	0.0233 (14)	0.0360 (18)	−0.0094 (13)	−0.0099 (14)	0.0003 (13)
C163	0.0374 (19)	0.0236 (15)	0.058 (2)	−0.0058 (14)	−0.0171 (17)	−0.0028 (15)
C164	0.0306 (18)	0.0359 (18)	0.057 (2)	0.0030 (15)	−0.0163 (17)	−0.0198 (16)
C165	0.041 (2)	0.056 (2)	0.0324 (19)	−0.0023 (17)	−0.0070 (16)	−0.0190 (16)
C166	0.0300 (17)	0.0379 (17)	0.0304 (17)	−0.0031 (14)	−0.0023 (13)	−0.0040 (13)
Fe2	0.0233 (2)	0.0227 (2)	0.0225 (2)	−0.00375 (17)	−0.00159 (17)	−0.00177 (16)
O21	0.0287 (11)	0.0230 (9)	0.0230 (10)	−0.0026 (8)	−0.0027 (8)	−0.0062 (8)
O22	0.0289 (11)	0.0237 (10)	0.0238 (10)	−0.0021 (8)	0.0013 (9)	0.0010 (8)
C21	0.0264 (15)	0.0215 (13)	0.0238 (15)	−0.0017 (12)	−0.0042 (12)	−0.0036 (11)
C22	0.0252 (15)	0.0228 (14)	0.0231 (15)	−0.0052 (12)	0.0004 (12)	−0.0012 (11)
C211	0.0221 (15)	0.0225 (14)	0.0260 (15)	−0.0003 (12)	−0.0064 (12)	−0.0028 (11)
C212	0.0279 (16)	0.0234 (14)	0.0233 (15)	−0.0026 (12)	−0.0023 (12)	−0.0019 (11)
C213	0.0269 (16)	0.0300 (15)	0.0289 (16)	0.0021 (13)	0.0023 (13)	0.0003 (13)
C214	0.0227 (16)	0.0334 (16)	0.0342 (18)	−0.0062 (13)	−0.0016 (13)	0.0042 (13)
C215	0.0234 (15)	0.0305 (15)	0.0263 (16)	−0.0050 (12)	−0.0063 (12)	0.0000 (12)
C221	0.0252 (15)	0.0212 (13)	0.0239 (15)	−0.0016 (12)	−0.0058 (12)	−0.0008 (11)
C222	0.0265 (16)	0.0264 (14)	0.0260 (16)	−0.0055 (12)	−0.0055 (12)	0.0007 (12)
C223	0.0302 (16)	0.0270 (15)	0.0281 (16)	−0.0027 (13)	−0.0104 (13)	−0.0057 (12)
C224	0.0351 (18)	0.0289 (15)	0.0212 (15)	−0.0018 (13)	−0.0042 (13)	0.0009 (12)
C225	0.0297 (16)	0.0250 (14)	0.0230 (15)	−0.0076 (12)	−0.0030 (12)	0.0027 (12)
C231	0.0344 (17)	0.0240 (14)	0.0228 (15)	−0.0071 (13)	−0.0061 (13)	−0.0023 (12)
C232	0.0340 (18)	0.0382 (17)	0.0331 (18)	−0.0079 (14)	−0.0032 (14)	0.0019 (14)
C233	0.058 (2)	0.0393 (18)	0.0306 (18)	−0.0120 (17)	−0.0072 (16)	0.0081 (14)
C234	0.072 (3)	0.0334 (18)	0.033 (2)	−0.0020 (18)	−0.0179 (19)	0.0073 (15)
C235	0.049 (2)	0.050 (2)	0.039 (2)	0.0146 (18)	−0.0098 (17)	0.0000 (16)
C236	0.047 (2)	0.0439 (19)	0.0239 (16)	0.0071 (16)	−0.0033 (15)	0.0000 (14)
C241	0.0250 (15)	0.0250 (14)	0.0246 (15)	−0.0070 (12)	−0.0024 (12)	0.0006 (11)
C242	0.0309 (17)	0.0274 (15)	0.0330 (17)	−0.0073 (13)	−0.0049 (14)	−0.0001 (13)
C243	0.043 (2)	0.0333 (17)	0.0397 (19)	−0.0140 (15)	−0.0078 (16)	−0.0028 (14)
C244	0.0380 (19)	0.0422 (19)	0.052 (2)	−0.0173 (16)	−0.0154 (17)	0.0012 (16)
C245	0.0234 (17)	0.0384 (18)	0.053 (2)	−0.0077 (14)	−0.0052 (15)	−0.0006 (16)
C246	0.0268 (16)	0.0290 (15)	0.0387 (18)	−0.0079 (13)	0.0001 (14)	−0.0055 (13)
C251	0.0235 (15)	0.0217 (14)	0.0329 (16)	−0.0061 (12)	−0.0041 (13)	−0.0006 (12)
C252	0.0294 (17)	0.0282 (15)	0.0364 (18)	−0.0051 (13)	0.0009 (14)	−0.0040 (13)
C253	0.0335 (18)	0.0250 (15)	0.052 (2)	−0.0026 (14)	0.0064 (15)	−0.0082 (14)
C254	0.0345 (19)	0.0259 (16)	0.060 (2)	0.0024 (14)	−0.0123 (17)	0.0020 (15)
C255	0.046 (2)	0.0357 (18)	0.045 (2)	−0.0033 (16)	−0.0171 (17)	−0.0012 (15)
C256	0.0402 (19)	0.0315 (16)	0.0319 (17)	−0.0030 (14)	−0.0063 (15)	−0.0051 (13)
C261	0.0215 (15)	0.0207 (13)	0.0286 (16)	−0.0015 (12)	0.0016 (12)	−0.0060 (12)
C262	0.0322 (17)	0.0344 (16)	0.0323 (17)	−0.0067 (14)	−0.0043 (14)	−0.0060 (13)
C263	0.039 (2)	0.048 (2)	0.047 (2)	−0.0107 (16)	−0.0160 (17)	−0.0109 (17)
C264	0.0334 (19)	0.047 (2)	0.063 (2)	−0.0142 (16)	−0.0018 (17)	−0.0199 (18)
C265	0.042 (2)	0.0335 (17)	0.044 (2)	−0.0140 (15)	0.0047 (16)	−0.0113 (15)
C266	0.0368 (18)	0.0269 (15)	0.0323 (17)	−0.0076 (14)	−0.0008 (14)	−0.0066 (13)
N1	0.0291 (14)	0.0323 (13)	0.0321 (14)	−0.0053 (11)	−0.0003 (11)	−0.0080 (11)
C2	0.0307 (18)	0.0469 (18)	0.0324 (18)	−0.0053 (15)	−0.0020 (14)	−0.0088 (14)
C3	0.0301 (17)	0.0407 (17)	0.0355 (18)	−0.0071 (14)	−0.0012 (14)	−0.0104 (14)
N4	0.056 (2)	0.069 (2)	0.0363 (17)	−0.0219 (17)	−0.0049 (15)	0.0027 (15)
N51	0.0376 (16)	0.0522 (16)	0.0322 (15)	−0.0103 (13)	−0.0037 (12)	−0.0103 (13)
C61	0.044 (2)	0.081 (3)	0.032 (2)	−0.016 (2)	−0.0002 (17)	−0.015 (2)
C71	0.040 (3)	0.052 (3)	0.040 (3)	0.001 (2)	−0.011 (2)	−0.010 (2)
N81	0.047 (2)	0.045 (2)	0.038 (2)	−0.0083 (18)	−0.0078 (18)	−0.0097 (17)
N52	0.0376 (16)	0.0522 (16)	0.0322 (15)	−0.0103 (13)	−0.0037 (12)	−0.0103 (13)
C62	0.044 (2)	0.081 (3)	0.032 (2)	−0.016 (2)	−0.0002 (17)	−0.015 (2)

Geometric parameters (Å, º)

Fe1—C123	2.032 (3)	C21—C211	1.519 (4)
Fe1—C124	2.041 (3)	C21—C241	1.532 (4)
Fe1—C113	2.045 (2)	C21—C231	1.544 (3)
Fe1—C112	2.046 (3)	C22—C221	1.524 (4)
Fe1—C115	2.047 (3)	C22—C261	1.532 (4)
Fe1—C122	2.051 (2)	C22—C251	1.544 (3)
Fe1—C114	2.052 (3)	C211—C215	1.427 (4)
Fe1—C125	2.057 (3)	C211—C212	1.428 (4)
Fe1—C111	2.069 (3)	C212—C213	1.423 (4)
Fe1—C121	2.073 (2)	C212—H212	0.95
O11—C11	1.436 (3)	C213—C214	1.415 (4)
O11—H11	0.84	C213—H213	0.95
O12—C12	1.425 (3)	C214—C215	1.425 (4)
O12—H12	0.84	C214—H214	0.95
C11—C111	1.522 (4)	C215—H215	0.95
C11—C141	1.536 (4)	C221—C222	1.425 (4)
C11—C131	1.539 (4)	C221—C225	1.428 (4)
C12—C121	1.523 (4)	C222—C223	1.416 (4)
C12—C161	1.539 (4)	C222—H222	0.95
C12—C151	1.543 (3)	C223—C224	1.412 (4)
C111—C112	1.426 (4)	C223—H223	0.95
C111—C115	1.429 (4)	C224—C225	1.430 (4)
C112—C113	1.422 (4)	C224—H224	0.95
C112—H112	0.95	C225—H225	0.95
C113—C114	1.424 (4)	C231—C232	1.386 (4)
C113—H113	0.95	C231—C236	1.388 (4)
C114—C115	1.420 (4)	C232—C233	1.387 (4)
C114—H114	0.95	C232—H232	0.95
C115—H115	0.95	C233—C234	1.378 (5)
C121—C125	1.424 (4)	C233—H233	0.95
C121—C122	1.431 (4)	C234—C235	1.375 (5)
C122—C123	1.415 (4)	C234—H234	0.95
C122—H122	0.95	C235—C236	1.396 (4)
C123—C124	1.405 (4)	C235—H235	0.95
C123—H123	0.95	C236—H236	0.95
C124—C125	1.424 (4)	C241—C246	1.392 (4)
C124—H124	0.95	C241—C242	1.400 (4)
C125—H125	0.95	C242—C243	1.381 (4)
C131—C136	1.387 (3)	C242—H242	0.95
C131—C132	1.389 (4)	C243—C244	1.393 (4)
C132—C133	1.381 (4)	C243—H243	0.95
C132—H132	0.95	C244—C245	1.378 (4)
C133—C134	1.390 (4)	C244—H244	0.95
C133—H133	0.95	C245—C246	1.390 (4)
C134—C135	1.373 (5)	C245—H245	0.95
C134—H134	0.95	C246—H246	0.95
C135—C136	1.396 (4)	C251—C252	1.386 (4)
C135—H135	0.95	C251—C256	1.388 (4)
C136—H136	0.95	C252—C253	1.383 (4)
C141—C142	1.387 (3)	C252—H252	0.95
C141—C146	1.389 (4)	C253—C254	1.382 (4)
C142—C143	1.390 (4)	C253—H253	0.95
C142—H142	0.95	C254—C255	1.386 (5)
C143—C144	1.378 (4)	C254—H254	0.95
C143—H143	0.95	C255—C256	1.386 (4)
C144—C145	1.388 (4)	C255—H255	0.95
C144—H144	0.95	C256—H256	0.95
C145—C146	1.377 (4)	C261—C266	1.386 (4)
C145—H145	0.95	C261—C262	1.401 (4)
C146—H146	0.95	C262—C263	1.383 (4)
C151—C152	1.363 (4)	C262—H262	0.95
C151—C156	1.402 (4)	C263—C264	1.385 (5)
C152—C153	1.400 (4)	C263—H263	0.95
C152—H152	0.95	C264—C265	1.392 (4)
C153—C154	1.384 (4)	C264—H264	0.95
C153—H153	0.95	C265—C266	1.383 (4)
C154—C155	1.374 (5)	C265—H265	0.95
C154—H154	0.95	C266—H266	0.95
C155—C156	1.394 (4)	N1—C2	1.468 (3)
C155—H155	0.95	N1—H1A	0.91
C156—H156	0.95	N1—H1B	0.91
C161—C162	1.390 (4)	C2—C3	1.520 (4)
C161—C166	1.398 (4)	C2—H2A	0.99
C162—C163	1.389 (4)	C2—H2B	0.99
C162—H162	0.95	C3—N4	1.455 (3)
C163—C164	1.381 (5)	C3—H3A	0.99
C163—H163	0.95	C3—H3B	0.99
C164—C165	1.379 (5)	N4—H4B	0.91
C164—H164	0.95	N4—H4A	0.91
C165—C166	1.391 (4)	N51—C61	1.456 (4)
C165—H165	0.95	N51—H51B	0.91
C166—H166	0.95	N51—H51A	0.91
Fe2—C225	2.041 (3)	C61—C71	1.526 (7)
Fe2—C214	2.041 (3)	C61—H61A	0.99
Fe2—C224	2.042 (3)	C61—H61B	0.99
Fe2—C213	2.044 (3)	C71—N81	1.466 (4)
Fe2—C215	2.044 (2)	C71—H71A	0.99
Fe2—C223	2.045 (3)	C71—H71B	0.99
Fe2—C212	2.048 (2)	N81—H81A	0.91
Fe2—C222	2.053 (3)	N81—H81B	0.91
Fe2—C221	2.058 (2)	C62—C72	1.524 (7)
Fe2—C211	2.059 (3)	C62—H62A	0.99
O21—C21	1.439 (3)	C62—H62B	0.99
O21—H21	0.84	C72—N82	1.461 (6)
O22—C22	1.431 (3)	C72—H72A	0.99
O22—H22	0.84	C72—H72B	0.99
C11—O11—H11	109.5	C214—C213—H213	126.0
C12—O12—H12	109.5	C212—C213—H213	126.0
O11—C11—C111	109.0 (2)	C213—C214—C215	107.7 (3)
O11—C11—C141	107.93 (19)	C213—C214—H214	126.1
C111—C11—C141	110.7 (2)	C215—C214—H214	126.1
O11—C11—C131	107.3 (2)	C214—C215—C211	108.8 (3)
C111—C11—C131	111.6 (2)	C214—C215—H215	125.6
C141—C11—C131	110.2 (2)	C211—C215—H215	125.6
O12—C12—C121	110.2 (2)	C222—C221—C225	107.2 (2)
O12—C12—C161	110.9 (2)	C222—C221—C22	123.8 (3)
C121—C12—C161	112.2 (2)	C225—C221—C22	128.7 (3)
O12—C12—C151	104.3 (2)	C223—C222—C221	108.5 (3)
C121—C12—C151	109.8 (2)	C223—C222—H222	125.7
C161—C12—C151	109.2 (2)	C221—C222—H222	125.7
C112—C111—C115	106.6 (2)	C224—C223—C222	108.4 (3)
C112—C111—C11	128.1 (2)	C224—C223—H223	125.8
C115—C111—C11	125.0 (2)	C222—C223—H223	125.8
C113—C112—C111	109.0 (2)	C223—C224—C225	107.8 (3)
C113—C112—H112	125.5	C223—C224—H224	126.1
C111—C112—H112	125.5	C225—C224—H224	126.1
C112—C113—C114	107.7 (3)	C221—C225—C224	108.1 (3)
C112—C113—H113	126.1	C221—C225—H225	126.0
C114—C113—H113	126.1	C224—C225—H225	126.0
C115—C114—C113	107.7 (3)	C232—C231—C236	118.6 (2)
C115—C114—H114	126.1	C232—C231—C21	118.6 (2)
C113—C114—H114	126.1	C236—C231—C21	122.8 (3)
C114—C115—C111	109.0 (3)	C231—C232—C233	121.2 (3)
C114—C115—H115	125.5	C231—C232—H232	119.4
C111—C115—H115	125.5	C233—C232—H232	119.4
C125—C121—C122	107.1 (2)	C234—C233—C232	120.0 (3)
C125—C121—C12	129.4 (2)	C234—C233—H233	120.0
C122—C121—C12	123.1 (2)	C232—C233—H233	120.0
C123—C122—C121	108.2 (3)	C235—C234—C233	119.4 (3)
C123—C122—H122	125.9	C235—C234—H234	120.3
C121—C122—H122	125.9	C233—C234—H234	120.3
C124—C123—C122	108.5 (2)	C234—C235—C236	120.9 (3)
C124—C123—H123	125.8	C234—C235—H235	119.6
C122—C123—H123	125.8	C236—C235—H235	119.6
C123—C124—C125	108.1 (3)	C231—C236—C235	119.9 (3)
C123—C124—H124	125.9	C231—C236—H236	120.1
C125—C124—H124	125.9	C235—C236—H236	120.1
C121—C125—C124	108.2 (3)	C246—C241—C242	118.1 (3)
C121—C125—H125	125.9	C246—C241—C21	121.6 (2)
C124—C125—H125	125.9	C242—C241—C21	120.4 (2)
C136—C131—C132	117.8 (3)	C243—C242—C241	121.1 (3)
C136—C131—C11	123.2 (3)	C243—C242—H242	119.4
C132—C131—C11	118.7 (2)	C241—C242—H242	119.4
C133—C132—C131	122.1 (3)	C242—C243—C244	120.3 (3)
C133—C132—H132	118.9	C242—C243—H243	119.8
C131—C132—H132	118.9	C244—C243—H243	119.8
C132—C133—C134	119.2 (3)	C245—C244—C243	118.8 (3)
C132—C133—H133	120.4	C245—C244—H244	120.6
C134—C133—H133	120.4	C243—C244—H244	120.6
C135—C134—C133	119.7 (3)	C244—C245—C246	121.2 (3)
C135—C134—H134	120.2	C244—C245—H245	119.4
C133—C134—H134	120.2	C246—C245—H245	119.4
C134—C135—C136	120.6 (3)	C245—C246—C241	120.4 (3)
C134—C135—H135	119.7	C245—C246—H246	119.8
C136—C135—H135	119.7	C241—C246—H246	119.8
C131—C136—C135	120.5 (3)	C252—C251—C256	118.7 (2)
C131—C136—H136	119.7	C252—C251—C22	118.3 (2)
C135—C136—H136	119.7	C256—C251—C22	123.0 (2)
C142—C141—C146	117.9 (2)	C253—C252—C251	120.5 (3)
C142—C141—C11	121.9 (2)	C253—C252—H252	119.7
C146—C141—C11	120.2 (2)	C251—C252—H252	119.7
C141—C142—C143	120.9 (3)	C254—C253—C252	120.6 (3)
C141—C142—H142	119.6	C254—C253—H253	119.7
C143—C142—H142	119.6	C252—C253—H253	119.7
C144—C143—C142	120.3 (3)	C253—C254—C255	119.3 (3)
C144—C143—H143	119.8	C253—C254—H254	120.3
C142—C143—H143	119.8	C255—C254—H254	120.3
C143—C144—C145	119.3 (3)	C256—C255—C254	120.0 (3)
C143—C144—H144	120.3	C256—C255—H255	120.0
C145—C144—H144	120.3	C254—C255—H255	120.0
C146—C145—C144	120.0 (3)	C255—C256—C251	120.9 (3)
C146—C145—H145	120.0	C255—C256—H256	119.6
C144—C145—H145	120.0	C251—C256—H256	119.6
C145—C146—C141	121.6 (2)	C266—C261—C262	118.0 (3)
C145—C146—H146	119.2	C266—C261—C22	121.1 (2)
C141—C146—H146	119.2	C262—C261—C22	120.9 (3)
C152—C151—C156	119.1 (2)	C263—C262—C261	120.7 (3)
C152—C151—C12	122.8 (3)	C263—C262—H262	119.6
C156—C151—C12	118.1 (3)	C261—C262—H262	119.6
C151—C152—C153	121.1 (3)	C262—C263—C264	120.6 (3)
C151—C152—H152	119.5	C262—C263—H263	119.7
C153—C152—H152	119.5	C264—C263—H263	119.7
C154—C153—C152	119.8 (3)	C263—C264—C265	119.2 (3)
C154—C153—H153	120.1	C263—C264—H264	120.4
C152—C153—H153	120.1	C265—C264—H264	120.4
C155—C154—C153	119.6 (3)	C266—C265—C264	120.0 (3)
C155—C154—H154	120.2	C266—C265—H265	120.0
C153—C154—H154	120.2	C264—C265—H265	120.0
C154—C155—C156	120.7 (3)	C265—C266—C261	121.5 (3)
C154—C155—H155	119.7	C265—C266—H266	119.2
C156—C155—H155	119.7	C261—C266—H266	119.2
C155—C156—C151	119.8 (3)	C2—N1—H1A	109.5
C155—C156—H156	120.1	C2—N1—H1B	109.5
C151—C156—H156	120.1	H1A—N1—H1B	109.5
C162—C161—C166	118.6 (3)	N1—C2—C3	116.0 (2)
C162—C161—C12	120.7 (3)	N1—C2—H2A	108.3
C166—C161—C12	120.6 (3)	C3—C2—H2A	108.3
C163—C162—C161	120.5 (3)	N1—C2—H2B	108.3
C163—C162—H162	119.7	C3—C2—H2B	108.3
C161—C162—H162	119.7	H2A—C2—H2B	107.4
C164—C163—C162	120.6 (3)	N4—C3—C2	116.7 (3)
C164—C163—H163	119.7	N4—C3—H3A	108.1
C162—C163—H163	119.7	C2—C3—H3A	108.1
C165—C164—C163	119.3 (3)	N4—C3—H3B	108.1
C165—C164—H164	120.3	C2—C3—H3B	108.1
C163—C164—H164	120.3	H3A—C3—H3B	107.3
C164—C165—C166	120.7 (3)	C3—N4—H4B	109.5
C164—C165—H165	119.6	C3—N4—H4A	109.5
C166—C165—H165	119.6	H4B—N4—H4A	109.5
C165—C166—C161	120.1 (3)	N51—C61—C71	116.3 (6)
C165—C166—H166	119.9	N51—C61—H61A	108.2
C161—C166—H166	119.9	C71—C61—H61A	108.2
C21—O21—H21	109.5	N51—C61—H61B	108.2
C22—O22—H22	109.5	C71—C61—H61B	108.2
O21—C21—C211	108.5 (2)	H61A—C61—H61B	107.4
O21—C21—C241	107.7 (2)	N81—C71—C61	109.3 (6)
C211—C21—C241	112.2 (2)	N81—C71—H71A	109.8
O21—C21—C231	108.6 (2)	C61—C71—H71A	109.8
C211—C21—C231	111.1 (2)	N81—C71—H71B	109.8
C241—C21—C231	108.7 (2)	C61—C71—H71B	109.8
O22—C22—C221	109.4 (2)	H71A—C71—H71B	108.3
O22—C22—C261	110.8 (2)	C71—N81—H81A	109.5
C221—C22—C261	112.4 (2)	C71—N81—H81B	109.5
O22—C22—C251	104.9 (2)	H81A—N81—H81B	109.5
C221—C22—C251	110.4 (2)	C72—C62—H62A	109.0
C261—C22—C251	108.8 (2)	C72—C62—H62B	109.0
C215—C211—C212	106.7 (3)	H62A—C62—H62B	107.8
C215—C211—C21	124.8 (2)	N82—C72—C62	108.0 (9)
C212—C211—C21	128.2 (3)	N82—C72—H72A	110.1
C213—C212—C211	108.7 (3)	C62—C72—H72A	110.1
C213—C212—H212	125.7	N82—C72—H72B	110.1
C211—C212—H212	125.7	C62—C72—H72B	110.1
C214—C213—C212	108.1 (3)	H72A—C72—H72B	108.4
O11—C11—C111—C112	−153.6 (2)	O21—C21—C211—C215	−25.6 (3)
C131—C11—C111—C112	88.1 (3)	C241—C21—C211—C215	−144.4 (2)
C141—C11—C111—C112	−35.0 (3)	C231—C21—C211—C215	93.7 (3)
O11—C11—C111—C115	33.8 (3)	O21—C21—C211—C212	161.3 (2)
C141—C11—C111—C115	152.4 (2)	C231—C21—C211—C212	−79.4 (3)
C131—C11—C111—C115	−84.5 (3)	C241—C21—C211—C212	42.5 (3)
C115—C111—C112—C113	0.5 (3)	C215—C211—C212—C213	0.3 (3)
C11—C111—C112—C113	−173.2 (2)	C21—C211—C212—C213	174.3 (2)
C111—C112—C113—C114	0.0 (3)	C211—C212—C213—C214	−0.1 (3)
C112—C113—C114—C115	−0.4 (3)	C212—C213—C214—C215	−0.2 (3)
C113—C114—C115—C111	0.7 (3)	C213—C214—C215—C211	0.4 (3)
C112—C111—C115—C114	−0.8 (3)	C212—C211—C215—C214	−0.4 (3)
C11—C111—C115—C114	173.2 (2)	C21—C211—C215—C214	−174.7 (2)
O12—C12—C121—C125	−147.8 (3)	O22—C22—C221—C222	−36.2 (3)
C161—C12—C121—C125	−23.8 (4)	C251—C22—C221—C222	78.7 (3)
C151—C12—C121—C125	97.8 (3)	C261—C22—C221—C222	−159.7 (2)
O12—C12—C121—C122	41.0 (3)	O22—C22—C221—C225	151.1 (2)
C151—C12—C121—C122	−73.4 (3)	C261—C22—C221—C225	27.6 (3)
C161—C12—C121—C122	165.0 (2)	C251—C22—C221—C225	−94.0 (3)
C125—C121—C122—C123	0.0 (3)	C225—C221—C222—C223	0.0 (3)
C12—C121—C122—C123	172.8 (2)	C22—C221—C222—C223	−174.0 (2)
C121—C122—C123—C124	−0.2 (3)	C221—C222—C223—C224	0.2 (3)
C122—C123—C124—C125	0.3 (3)	C222—C223—C224—C225	−0.3 (3)
C122—C121—C125—C124	0.2 (3)	C222—C221—C225—C224	−0.2 (3)
C12—C121—C125—C124	−172.1 (2)	C22—C221—C225—C224	173.4 (2)
C123—C124—C125—C121	−0.3 (3)	C223—C224—C225—C221	0.3 (3)
O11—C11—C131—C136	−109.6 (3)	O21—C21—C231—C232	−54.9 (3)
C111—C11—C131—C136	9.7 (4)	C211—C21—C231—C232	−174.1 (3)
C141—C11—C131—C136	133.1 (3)	C241—C21—C231—C232	62.0 (3)
O11—C11—C131—C132	65.1 (3)	O21—C21—C231—C236	124.1 (3)
C111—C11—C131—C132	−175.5 (2)	C211—C21—C231—C236	4.9 (4)
C141—C11—C131—C132	−52.1 (3)	C241—C21—C231—C236	−119.0 (3)
C136—C131—C132—C133	−1.2 (4)	C236—C231—C232—C233	−0.5 (5)
C11—C131—C132—C133	−176.2 (3)	C21—C231—C232—C233	178.6 (3)
C131—C132—C133—C134	0.0 (5)	C231—C232—C233—C234	1.5 (5)
C132—C133—C134—C135	1.3 (5)	C232—C233—C234—C235	−1.3 (5)
C133—C134—C135—C136	−1.4 (5)	C233—C234—C235—C236	0.1 (6)
C132—C131—C136—C135	1.1 (4)	C232—C231—C236—C235	−0.6 (5)
C11—C131—C136—C135	175.9 (3)	C21—C231—C236—C235	−179.7 (3)
C134—C135—C136—C131	0.1 (5)	C234—C235—C236—C231	0.8 (5)
O11—C11—C141—C142	14.3 (4)	O21—C21—C241—C246	−8.2 (3)
C111—C11—C141—C142	−104.9 (3)	C211—C21—C241—C246	111.1 (3)
C131—C11—C141—C142	131.2 (3)	C231—C21—C241—C246	−125.7 (3)
O11—C11—C141—C146	−166.2 (3)	O21—C21—C241—C242	172.9 (2)
C111—C11—C141—C146	74.6 (3)	C211—C21—C241—C242	−67.8 (3)
C131—C11—C141—C146	−49.3 (3)	C231—C21—C241—C242	55.4 (3)
C146—C141—C142—C143	−1.5 (4)	C246—C241—C242—C243	−3.1 (4)
C11—C141—C142—C143	178.0 (3)	C21—C241—C242—C243	175.8 (3)
C141—C142—C143—C144	−0.7 (5)	C241—C242—C243—C244	2.0 (5)
C142—C143—C144—C145	1.9 (5)	C242—C243—C244—C245	0.6 (5)
C143—C144—C145—C146	−0.8 (5)	C243—C244—C245—C246	−2.1 (5)
C144—C145—C146—C141	−1.5 (5)	C244—C245—C246—C241	0.9 (5)
C142—C141—C146—C145	2.6 (5)	C242—C241—C246—C245	1.7 (4)
C11—C141—C146—C145	−176.9 (3)	C21—C241—C246—C245	−177.3 (3)
O12—C12—C151—C152	−134.9 (3)	O22—C22—C251—C252	−47.4 (3)
C121—C12—C151—C152	−16.8 (4)	C221—C22—C251—C252	−165.1 (3)
C161—C12—C151—C152	106.5 (3)	C261—C22—C251—C252	71.1 (3)
O12—C12—C151—C156	45.5 (3)	O22—C22—C251—C256	134.2 (3)
C121—C12—C151—C156	163.6 (2)	C221—C22—C251—C256	16.5 (4)
C161—C12—C151—C156	−73.1 (3)	C261—C22—C251—C256	−107.3 (3)
C156—C151—C152—C153	−0.8 (4)	C256—C251—C252—C253	−1.5 (4)
C12—C151—C152—C153	179.6 (3)	C22—C251—C252—C253	−180.0 (3)
C151—C152—C153—C154	−0.2 (5)	C251—C252—C253—C254	0.7 (5)
C152—C153—C154—C155	0.3 (5)	C252—C253—C254—C255	0.5 (5)
C153—C154—C155—C156	0.7 (5)	C253—C254—C255—C256	−0.9 (5)
C154—C155—C156—C151	−1.7 (4)	C254—C255—C256—C251	0.1 (5)
C152—C151—C156—C155	1.7 (4)	C252—C251—C256—C255	1.0 (5)
C12—C151—C156—C155	−178.7 (3)	C22—C251—C256—C255	179.5 (3)
O12—C12—C161—C162	−161.7 (2)	O22—C22—C261—C266	161.9 (2)
C121—C12—C161—C162	74.7 (3)	C221—C22—C261—C266	−75.4 (3)
C151—C12—C161—C162	−47.3 (3)	C251—C22—C261—C266	47.2 (3)
O12—C12—C161—C166	16.9 (3)	O22—C22—C261—C262	−17.8 (3)
C121—C12—C161—C166	−106.7 (3)	C221—C22—C261—C262	104.9 (3)
C151—C12—C161—C166	131.3 (3)	C251—C22—C261—C262	−132.6 (3)
C166—C161—C162—C163	−1.6 (4)	C266—C261—C262—C263	0.3 (4)
C12—C161—C162—C163	177.0 (2)	C22—C261—C262—C263	−180.0 (3)
C161—C162—C163—C164	0.0 (4)	C261—C262—C263—C264	0.8 (5)
C162—C163—C164—C165	1.7 (4)	C262—C263—C264—C265	−1.2 (5)
C163—C164—C165—C166	−1.9 (5)	C263—C264—C265—C266	0.5 (5)
C164—C165—C166—C161	0.3 (4)	C264—C265—C266—C261	0.6 (4)
C162—C161—C166—C165	1.5 (4)	C262—C261—C266—C265	−1.0 (4)
C12—C161—C166—C165	−177.1 (2)	C22—C261—C266—C265	179.3 (3)
N1—C2—C3—N4	61.6 (4)	N52—C62—C72—N82	179.5 (4)
N51—C61—C71—N81	60.5 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···N1	0.84	1.89	2.715 (3)	169
O12—H12···O11	0.84	1.92	2.687 (2)	152
O21—H21···N51	0.84	1.90	2.743 (3)	178
O22—H22···O21	0.84	2.01	2.790 (2)	154
N1—H1A···O11^i	0.91	2.31	3.103 (3)	146
N1—H1B···O12^i	0.91	2.49	3.142 (3)	129
N4—H4A···O12^i	0.91	2.45	3.358 (3)	172
N51—H51A···O21^ii	0.91	2.43	3.252 (3)	151

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z.