N-(Ferrocenecarbonyl)-N'-(quinolin-8-yl)thio­urea

In the title compound, [Fe(C₅H₅)(C₁₆H₁₂N₃OS)], the 8-am­inoquinoline and acyl­thio­urea moieties are almost planar. There are two perpendicular arrangements of the mol­ecules in the crystal with slightly different conformations. The two cyclo­penta­dienyl rings in each mol­ecule are parallel and eclipsed.

S1. Comment

Ferrocene derivatives have received much interest recently as redox-active entities, with potential applications in areas such as materials for electronics (Nguyen et al., 1999; Creager & Yu, 1999; Bildstein et al., 2000), electrochemical molecular recognition (Beer et al., 1999), nonlinear optical (NLO) materials (Long, 1995; Tian et al., 1999; Roberto et al., 2000), and as biologically active compounds (Li et al., 1997; Kraatz et al., 1997). A variety of ferrocene derivatives have been investigated in this respect. Ligand design is a key factor for developing an efficient system for molecular recognition and catalysis. We herein report the crystal structure of a novel ferrocene derivative containing a N-heterocyclic and acylthiourea coordination site.

The title compound is an amino-substituted ferrocenoyl thiourea. There are two perpendicular arrangements of the molecules in the crystal with slightly different conformations (Fig. 1). Bond lengths and angles in the two molecules (A and B) are similar and the C=S bond distances are similar to those reported in the literature [1.671 (3) and 1.664 (3) Å (Fun et al., 1995) and 1.680 (3) Å (Tian et al., 1996)]. Each molecule can be described as consisting of ferrocenyl, N-heterocyclic and acylthiourea fragments. For molecule A, the Fe—C_ring distances are as expected for a ferrocene derivative, ranging from 2.031 (3) to 2.053 (3) Å, with an average of 2.045 (3) Å, which agree with the values found in acetylferrocene (2.046 Å; Palenik, 1970) and ferrocene (2.058 Å; Haaland & Silson, 1968). The dimensions of the cyclopentadienyl (Cp) rings [C—C distance 1.400 (4)–1.435 (3) Å, average value 1.414 (3) Å and C—C—C angles 107.3 (3)–108.9 (3)°, average value 108.0°] are also normal. The conformation of the Cp ring is close to eclipsed, which is common for ferrocene derivatives. The two Cp rings are planar and nearly parallel, the tilt between the two rings being 1.2 (2)°. Molecule B is similar.

The N-heterocyclic and acylthiourea fragments for each molecule almost lie in one plane. For molecule A, the N-heterocyclic fragment is planar with a maximum deviation of 0.023 (3) Å for C13A and the acylthiourea fragment is planar with a maximum deviation of 0.103 (1) Å for O1A. The mean planes through the N-heterocyclic and the acylthiourea fragments form a dihedral angle of 14.2 (2)°. However, for molecule B, the N-heterocyclic fragment is planar with a maximum deviation of 0.040 (3) Å for C20B and the acylthiourea fragment is planar with a maximum deviation of 0.045 (1) Å for O1B. The mean planes through the two fragments of molecule B form a dihedral angle of 1.9 (2)°, indicating that the two fragments in molecule B are more planar than those in molecule A.

There are intramolecular and intermolecular hydrogen bonds (Table 2), weak N2A—H2AB···N3A [2.638 (3) Å], N2B—H2BB···N3B [2.632 (3) Å], C14A—H14A···S1A [3.204 (3) Å] and C14B—H14B···S1B [3.225 (3) Å] intramolecular interactions and a weak C6A—H6AA···O1B(-1/2 + x, 1/2 - y, 1/2 + z) [3.214 (3) Å] intermolecular interaction.

S2. Experimental

The title compound was prepared by treating the product from the reaction of chlorocarbonylferrocene and potassium isothiocyanate with 8-aminoquinoline (Yuan et al., 1997; Wang et al., 1994; 1996). Single crystals were grown by slow evaporation from a dichloromathane/2-propanol solution.

S3. Refinement

The structure was solved by direct methods and refined by full-matrix least-squares techniques. After checking their presence in the difference map, all H atoms were geometrically fixed and allowed to ride on their attached atoms with U_iso = 1.2U_eq for the attached atoms.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli,1995) and PLATON (Spek, 1990).

Figures

Fig. 1. The title complex drawn with 50% probability displacement ellipsoids. H atoms are not shown.

(I)

Crystal data

C21H17FeN3OS	F(000) = 1712
Mr = 415.29	Dx = 1.510 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.9519 (1) Å	Cell parameters from 6038 reflections
b = 18.1406 (1) Å	θ = 1.7–28.4°
c = 15.6117 (2) Å	µ = 0.96 mm^−1
β = 95.230 (1)°	T = 293 K
V = 3652.78 (6) Å^3	Slab, dark brown
Z = 8	0.36 × 0.34 × 0.28 mm

Data collection

Siemens SMART CCD area detector diffractometer	8936 independent reflections
Radiation source: fine-focus sealed tube	5352 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 1.7°
ω scans	h = −15→16
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −18→24
Tmin = 0.725, Tmax = 0.776	l = −20→15
25618 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters not refined
S = 0.97	w = 1/[σ^2(Fo^2) + (0.015P)^2] where P = (Fo^2 + 2Fc^2)/3
8936 reflections	(Δ/σ)max = 0.001
487 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.71 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0,88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4.023 cm and the detector swing angle was -35°. Coverage of the unit set is 98.4% complete. Crystal decay was monitored by SAINT (Siemens, 1996) and was found to be negligible.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Fe1A	0.07154 (3)	0.13145 (2)	0.73841 (2)	0.03455 (11)
S1A	−0.21583 (7)	0.25926 (4)	1.01218 (5)	0.0503 (2)
O1A	−0.14797 (15)	0.06482 (9)	0.84572 (11)	0.0367 (4)
C1A	0.1979 (2)	0.0648 (2)	0.7283 (2)	0.0611 (9)
H1AA	0.2097	0.0330	0.6794	0.073*
C2A	0.1463 (2)	0.0447 (2)	0.7998 (2)	0.0578 (9)
H2AA	0.1158	−0.0038	0.8092	0.069*
C3A	0.1454 (2)	0.1053 (2)	0.8559 (2)	0.0553 (9)
H3AA	0.1153	0.1065	0.9112	0.066*
C4A	0.1972 (2)	0.1640 (2)	0.8179 (2)	0.0603 (9)
H4AA	0.2086	0.2134	0.8424	0.072*
C5A	0.2292 (2)	0.1393 (2)	0.7390 (2)	0.0642 (10)
H5AA	0.2670	0.1683	0.6990	0.077*
C6A	−0.0328 (2)	0.21580 (16)	0.72682 (18)	0.0414 (7)
H6AA	−0.0282	0.2616	0.7602	0.050*
C7A	0.0078 (2)	0.20468 (18)	0.64825 (19)	0.0512 (8)
H7AA	0.0463	0.2412	0.6176	0.061*
C8A	−0.0128 (2)	0.13100 (19)	0.62120 (17)	0.0487 (8)
H8AA	0.0077	0.1081	0.5684	0.058*
C9A	−0.0686 (2)	0.09621 (16)	0.68482 (16)	0.0366 (7)
H9AA	−0.0938	0.0453	0.6834	0.044*
C10A	−0.08150 (19)	0.14936 (14)	0.75106 (15)	0.0288 (6)
C11A	−0.13174 (18)	0.12963 (14)	0.82826 (15)	0.0268 (5)
N1A	−0.15927 (16)	0.18599 (11)	0.87969 (12)	0.0301 (5)
H1AB	−0.1455	0.2297	0.8626	0.036*
N2A	−0.24065 (17)	0.11482 (11)	0.97640 (13)	0.0343 (5)
H2AB	−0.2259	0.0805	0.9415	0.041*
N3A	−0.31497 (18)	−0.02042 (12)	0.96117 (14)	0.0382 (6)
C12A	−0.2066 (2)	0.18200 (14)	0.95613 (16)	0.0301 (6)
C13A	−0.2960 (2)	0.09047 (14)	1.04434 (16)	0.0312 (6)
C14A	−0.3133 (2)	0.12853 (16)	1.11695 (17)	0.0419 (7)
H14A	−0.2862	0.1757	1.1252	0.050*
C15A	−0.3716 (2)	0.09740 (18)	1.17953 (18)	0.0490 (8)
H15A	−0.3823	0.1242	1.2287	0.059*
C16A	−0.4126 (2)	0.02860 (18)	1.16891 (18)	0.0474 (8)
H16A	−0.4518	0.0090	1.2104	0.057*
C17A	−0.3959 (2)	−0.01300 (16)	1.09556 (16)	0.0356 (6)
C18A	−0.4355 (2)	−0.08471 (17)	1.08074 (18)	0.0450 (8)
H18A	−0.4760	−0.1065	1.1200	0.054*
C19A	−0.4143 (2)	−0.12149 (16)	1.00960 (19)	0.0481 (8)
H19A	−0.4397	−0.1689	0.9993	0.058*
C20A	−0.3535 (2)	−0.08746 (16)	0.95128 (18)	0.0462 (8)
H20A	−0.3395	−0.1138	0.9026	0.055*
C21A	−0.33637 (19)	0.01694 (14)	1.03281 (15)	0.0298 (6)
Fe1B	0.02835 (3)	0.16034 (2)	0.27483 (3)	0.03815 (12)
S1B	0.37739 (6)	−0.08294 (4)	0.28157 (6)	0.0504 (2)
O1B	0.31735 (15)	0.16302 (9)	0.30050 (12)	0.0426 (5)
C1B	−0.0280 (3)	0.0926 (2)	0.3643 (2)	0.0657 (10)
H1BA	−0.0313	0.0386	0.3618	0.079*
C2B	0.0561 (3)	0.1352 (2)	0.40215 (19)	0.0612 (10)
H2BA	0.1212	0.1159	0.4305	0.073*
C3B	0.0298 (3)	0.2100 (2)	0.3919 (2)	0.0667 (10)
H3BA	0.0729	0.2521	0.4119	0.080*
C4B	−0.0704 (3)	0.2138 (2)	0.3488 (2)	0.0676 (10)
H4BA	−0.1084	0.2592	0.3329	0.081*
C5B	−0.1062 (3)	0.1419 (2)	0.3307 (2)	0.0689 (11)
H5BA	−0.1733	0.1284	0.3008	0.083*
C6B	0.1306 (2)	0.21790 (15)	0.20936 (18)	0.0451 (7)
H6BA	0.1724	0.2600	0.2315	0.054*
C7B	0.0309 (3)	0.22163 (17)	0.16506 (19)	0.0553 (9)
H7BA	−0.0089	0.2667	0.1515	0.066*
C8B	−0.0017 (2)	0.14896 (16)	0.14341 (17)	0.0472 (8)
H8BA	−0.0685	0.1352	0.1132	0.057*
C9B	0.0767 (2)	0.09905 (15)	0.17597 (16)	0.0386 (7)
H9BA	0.0745	0.0452	0.1710	0.046*
C10B	0.1602 (2)	0.14187 (14)	0.21652 (16)	0.0320 (6)
C11B	0.2579 (2)	0.11820 (13)	0.26322 (16)	0.0298 (6)
N1B	0.28071 (16)	0.04413 (11)	0.26193 (13)	0.0322 (5)
H1BB	0.2348	0.0168	0.2343	0.039*
N2B	0.43615 (16)	0.04981 (11)	0.34568 (13)	0.0327 (5)
H2BB	0.4186	0.0955	0.3462	0.039*
N3B	0.53416 (18)	0.16409 (13)	0.41807 (15)	0.0426 (6)
C12B	0.3689 (2)	0.00699 (13)	0.29968 (16)	0.0310 (6)
C13B	0.5314 (2)	0.03408 (14)	0.39398 (16)	0.0324 (6)
C14B	0.5750 (2)	−0.03417 (16)	0.40962 (18)	0.0447 (7)
H14B	0.5420	−0.0763	0.3869	0.054*
C15B	0.6704 (3)	−0.03951 (19)	0.4606 (2)	0.0574 (9)
H15B	0.6994	−0.0859	0.4715	0.069*
C16B	0.7209 (3)	0.02014 (19)	0.49405 (19)	0.0564 (9)
H16B	0.7845	0.0145	0.5262	0.068*
C17B	0.6788 (2)	0.09048 (17)	0.48089 (17)	0.0414 (7)
C18B	0.7238 (3)	0.15560 (19)	0.51682 (19)	0.0537 (9)
H18B	0.7875	0.1534	0.5494	0.064*
C19B	0.6753 (3)	0.22077 (19)	0.50436 (19)	0.0563 (9)
H19B	0.7048	0.2638	0.5279	0.068*
C20B	0.5798 (2)	0.22241 (17)	0.45529 (19)	0.0522 (8)
H20B	0.5460	0.2675	0.4483	0.063*
C21B	0.5830 (2)	0.09777 (15)	0.43094 (16)	0.0340 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1A	0.0236 (2)	0.0438 (2)	0.0368 (2)	−0.00398 (18)	0.00555 (16)	0.00292 (19)
S1A	0.0734 (6)	0.0270 (4)	0.0511 (5)	0.0042 (4)	0.0090 (4)	−0.0086 (3)
O1A	0.0466 (12)	0.0226 (10)	0.0439 (11)	−0.0062 (8)	0.0201 (9)	−0.0036 (8)
C1A	0.0313 (18)	0.081 (3)	0.071 (2)	0.0119 (18)	0.0059 (16)	−0.014 (2)
C2A	0.0376 (19)	0.065 (2)	0.070 (2)	0.0147 (17)	0.0007 (17)	0.015 (2)
C3A	0.0342 (18)	0.088 (3)	0.0422 (18)	0.0052 (18)	−0.0032 (14)	0.0057 (19)
C4A	0.0295 (18)	0.088 (3)	0.062 (2)	−0.0118 (18)	−0.0040 (15)	−0.018 (2)
C5A	0.0244 (17)	0.096 (3)	0.073 (2)	−0.0124 (18)	0.0094 (15)	0.000 (2)
C6A	0.0354 (17)	0.0365 (16)	0.0525 (18)	−0.0021 (13)	0.0049 (13)	0.0116 (14)
C7A	0.0457 (19)	0.060 (2)	0.0494 (19)	−0.0017 (16)	0.0114 (15)	0.0256 (17)
C8A	0.0433 (19)	0.076 (2)	0.0271 (15)	−0.0024 (17)	0.0050 (13)	0.0050 (16)
C9A	0.0291 (15)	0.0502 (17)	0.0308 (15)	−0.0058 (13)	0.0040 (11)	−0.0005 (13)
C10A	0.0231 (14)	0.0309 (14)	0.0321 (14)	−0.0017 (11)	0.0009 (11)	0.0049 (11)
C11A	0.0206 (13)	0.0262 (14)	0.0337 (14)	−0.0022 (11)	0.0027 (10)	−0.0013 (12)
N1A	0.0343 (13)	0.0186 (10)	0.0382 (12)	−0.0023 (9)	0.0079 (10)	0.0024 (10)
N2A	0.0426 (14)	0.0243 (12)	0.0382 (13)	−0.0026 (10)	0.0161 (10)	−0.0059 (10)
N3A	0.0452 (15)	0.0307 (13)	0.0403 (13)	−0.0050 (11)	0.0123 (11)	0.0004 (11)
C12A	0.0272 (14)	0.0265 (14)	0.0362 (15)	0.0030 (11)	0.0000 (11)	−0.0006 (12)
C13A	0.0267 (14)	0.0362 (15)	0.0316 (14)	0.0028 (12)	0.0071 (11)	0.0002 (12)
C14A	0.0412 (17)	0.0433 (17)	0.0428 (17)	−0.0012 (14)	0.0123 (13)	−0.0081 (14)
C15A	0.049 (2)	0.063 (2)	0.0373 (17)	0.0053 (17)	0.0159 (14)	−0.0077 (15)
C16A	0.0412 (18)	0.063 (2)	0.0403 (17)	0.0021 (16)	0.0185 (13)	0.0064 (16)
C17A	0.0305 (15)	0.0435 (17)	0.0332 (15)	0.0036 (13)	0.0055 (11)	0.0079 (13)
C18A	0.0409 (18)	0.0508 (19)	0.0448 (18)	−0.0058 (15)	0.0110 (14)	0.0180 (15)
C19A	0.056 (2)	0.0381 (17)	0.0513 (19)	−0.0128 (15)	0.0080 (15)	0.0097 (15)
C20A	0.063 (2)	0.0344 (16)	0.0431 (17)	−0.0061 (15)	0.0126 (15)	−0.0019 (14)
C21A	0.0264 (14)	0.0346 (15)	0.0290 (14)	0.0027 (12)	0.0059 (11)	0.0039 (12)
Fe1B	0.0317 (2)	0.0339 (2)	0.0478 (3)	0.00886 (18)	−0.00152 (18)	−0.00772 (19)
S1B	0.0477 (5)	0.0216 (4)	0.0821 (6)	0.0001 (3)	0.0063 (4)	−0.0045 (4)
O1B	0.0356 (12)	0.0244 (10)	0.0662 (13)	0.0005 (9)	−0.0033 (10)	−0.0110 (9)
C1B	0.075 (3)	0.059 (2)	0.068 (2)	−0.002 (2)	0.032 (2)	−0.0057 (19)
C2B	0.056 (2)	0.090 (3)	0.0391 (18)	0.021 (2)	0.0133 (16)	−0.0046 (19)
C3B	0.045 (2)	0.085 (3)	0.070 (2)	0.008 (2)	0.0071 (17)	−0.036 (2)
C4B	0.048 (2)	0.069 (2)	0.087 (3)	0.0245 (19)	0.0088 (19)	−0.029 (2)
C5B	0.036 (2)	0.093 (3)	0.079 (3)	−0.005 (2)	0.0170 (17)	−0.030 (2)
C6B	0.050 (2)	0.0267 (15)	0.0566 (19)	0.0005 (14)	−0.0053 (15)	0.0054 (14)
C7B	0.057 (2)	0.0409 (18)	0.065 (2)	0.0108 (16)	−0.0118 (17)	0.0067 (16)
C8B	0.048 (2)	0.0461 (19)	0.0446 (17)	0.0026 (15)	−0.0135 (14)	−0.0020 (14)
C9B	0.0421 (18)	0.0319 (15)	0.0413 (16)	0.0009 (13)	0.0009 (13)	−0.0057 (13)
C10B	0.0370 (16)	0.0266 (14)	0.0330 (14)	0.0011 (12)	0.0053 (12)	−0.0007 (12)
C11B	0.0304 (15)	0.0248 (14)	0.0356 (15)	−0.0005 (11)	0.0105 (11)	−0.0032 (12)
N1B	0.0272 (12)	0.0226 (11)	0.0471 (13)	−0.0034 (9)	0.0053 (10)	−0.0077 (10)
N2B	0.0322 (13)	0.0221 (11)	0.0445 (13)	0.0041 (10)	0.0064 (10)	−0.0004 (10)
N3B	0.0383 (15)	0.0364 (13)	0.0517 (15)	0.0021 (12)	−0.0038 (11)	−0.0023 (12)
C12B	0.0309 (15)	0.0217 (13)	0.0426 (15)	−0.0010 (11)	0.0151 (12)	0.0009 (12)
C13B	0.0330 (15)	0.0358 (15)	0.0301 (14)	0.0061 (12)	0.0123 (11)	0.0055 (12)
C14B	0.053 (2)	0.0352 (16)	0.0469 (17)	0.0071 (14)	0.0094 (14)	0.0034 (14)
C15B	0.065 (2)	0.048 (2)	0.058 (2)	0.0276 (18)	−0.0006 (18)	0.0108 (17)
C16B	0.052 (2)	0.064 (2)	0.051 (2)	0.0185 (18)	−0.0087 (16)	0.0085 (18)
C17B	0.0374 (17)	0.0515 (19)	0.0351 (15)	0.0056 (15)	0.0018 (13)	0.0089 (14)
C18B	0.043 (2)	0.067 (2)	0.0479 (19)	−0.0023 (17)	−0.0126 (15)	0.0056 (17)
C19B	0.055 (2)	0.051 (2)	0.059 (2)	−0.0090 (17)	−0.0146 (17)	−0.0029 (17)
C20B	0.050 (2)	0.0398 (18)	0.064 (2)	0.0003 (15)	−0.0103 (16)	−0.0034 (16)
C21B	0.0328 (16)	0.0408 (16)	0.0292 (14)	0.0028 (13)	0.0079 (12)	0.0026 (12)

Geometric parameters (Å, º)

Fe1A—C9A	2.031 (3)	Fe1B—C6B	2.034 (3)
Fe1A—C10A	2.036 (3)	Fe1B—C10B	2.035 (3)
Fe1A—C6A	2.038 (3)	Fe1B—C3B	2.036 (3)
Fe1A—C2A	2.041 (3)	Fe1B—C2B	2.039 (3)
Fe1A—C4A	2.042 (3)	Fe1B—C4B	2.045 (3)
Fe1A—C8A	2.044 (3)	Fe1B—C7B	2.046 (3)
Fe1A—C3A	2.045 (3)	Fe1B—C9B	2.046 (3)
Fe1A—C5A	2.046 (3)	Fe1B—C5B	2.046 (3)
Fe1A—C1A	2.053 (3)	Fe1B—C1B	2.045 (3)
Fe1A—C7A	2.053 (3)	Fe1B—C8B	2.063 (3)
S1A—C12A	1.662 (3)	S1B—C12B	1.661 (3)
O1A—C11A	1.229 (3)	O1B—C11B	1.229 (3)
C1A—C2A	1.400 (4)	C1B—C5B	1.416 (5)
C1A—C5A	1.417 (5)	C1B—C2B	1.421 (5)
C1A—H1AA	0.9800	C1B—H1BA	0.9800
C2A—C3A	1.406 (4)	C2B—C3B	1.404 (5)
C2A—H2AA	0.9800	C2B—H2BA	0.9800
C3A—C4A	1.416 (5)	C3B—C4B	1.407 (5)
C3A—H3AA	0.9800	C3B—H3BA	0.9800
C4A—C5A	1.409 (4)	C4B—C5B	1.404 (5)
C4A—H4AA	0.9800	C4B—H4BA	0.9800
C5A—H5AA	0.9800	C5B—H5BA	0.9800
C6A—C7A	1.392 (4)	C6B—C7B	1.410 (4)
C6A—C10A	1.427 (3)	C6B—C10B	1.433 (4)
C6A—H6AA	0.9800	C6B—H6BA	0.9800
C7A—C8A	1.420 (4)	C7B—C8B	1.416 (4)
C7A—H7AA	0.9800	C7B—H7BA	0.9800
C8A—C9A	1.428 (4)	C8B—C9B	1.420 (4)
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C9A—C10A	1.435 (3)	C9B—C10B	1.431 (4)
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C10A—C11A	1.465 (3)	C10B—C11B	1.466 (4)
C11A—N1A	1.367 (3)	C11B—N1B	1.376 (3)
N1A—C12A	1.393 (3)	N1B—C12B	1.408 (3)
N1A—H1AB	0.8600	N1B—H1BB	0.8600
N2A—C12A	1.343 (3)	N2B—C12B	1.328 (3)
N2A—C13A	1.404 (3)	N2B—C13B	1.415 (3)
N2A—H2AB	0.8600	N2B—H2BB	0.8600
N3A—C20A	1.318 (3)	N3B—C20B	1.320 (3)
N3A—C21A	1.358 (3)	N3B—C21B	1.365 (3)
C13A—C14A	1.363 (3)	C13B—C14B	1.373 (4)
C13A—C21A	1.438 (4)	C13B—C21B	1.430 (4)
C14A—C15A	1.407 (4)	C14B—C15B	1.411 (4)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.360 (4)	C15B—C16B	1.345 (4)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.405 (4)	C16B—C17B	1.396 (4)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.410 (4)	C17B—C21B	1.411 (4)
C17A—C21A	1.409 (3)	C17B—C18B	1.411 (4)
C18A—C19A	1.345 (4)	C18B—C19B	1.345 (4)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.400 (4)	C19B—C20B	1.395 (4)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—H20A	0.9300	C20B—H20B	0.9300
C9A—Fe1A—C10A	41.31 (10)	C6B—Fe1B—C10B	41.25 (10)
C9A—Fe1A—C6A	68.87 (12)	C6B—Fe1B—C3B	105.71 (14)
C10A—Fe1A—C6A	41.02 (10)	C10B—Fe1B—C3B	122.35 (12)
C9A—Fe1A—C2A	108.56 (13)	C6B—Fe1B—C2B	122.64 (14)
C10A—Fe1A—C2A	120.12 (12)	C10B—Fe1B—C2B	108.57 (12)
C6A—Fe1A—C2A	154.55 (13)	C3B—Fe1B—C2B	40.32 (14)
C9A—Fe1A—C4A	166.92 (12)	C6B—Fe1B—C4B	120.67 (14)
C10A—Fe1A—C4A	128.61 (12)	C10B—Fe1B—C4B	157.62 (13)
C6A—Fe1A—C4A	108.79 (13)	C3B—Fe1B—C4B	40.35 (13)
C2A—Fe1A—C4A	67.66 (14)	C2B—Fe1B—C4B	67.61 (14)
C9A—Fe1A—C8A	41.02 (11)	C6B—Fe1B—C7B	40.44 (11)
C10A—Fe1A—C8A	69.02 (11)	C10B—Fe1B—C7B	68.68 (12)
C6A—Fe1A—C8A	68.14 (12)	C3B—Fe1B—C7B	120.78 (15)
C2A—Fe1A—C8A	127.53 (14)	C2B—Fe1B—C7B	157.39 (15)
C4A—Fe1A—C8A	151.25 (14)	C4B—Fe1B—C7B	105.92 (14)
C9A—Fe1A—C3A	128.59 (12)	C6B—Fe1B—C9B	69.00 (11)
C10A—Fe1A—C3A	109.29 (12)	C10B—Fe1B—C9B	41.06 (10)
C6A—Fe1A—C3A	120.41 (13)	C3B—Fe1B—C9B	159.90 (13)
C2A—Fe1A—C3A	40.25 (12)	C2B—Fe1B—C9B	125.10 (12)
C4A—Fe1A—C3A	40.55 (13)	C4B—Fe1B—C9B	159.10 (13)
C8A—Fe1A—C3A	165.91 (14)	C7B—Fe1B—C9B	68.53 (12)
C9A—Fe1A—C5A	151.35 (13)	C6B—Fe1B—C5B	156.50 (15)
C10A—Fe1A—C5A	165.59 (13)	C10B—Fe1B—C5B	161.08 (14)
C6A—Fe1A—C5A	126.95 (14)	C3B—Fe1B—C5B	68.16 (14)
C2A—Fe1A—C5A	67.75 (15)	C2B—Fe1B—C5B	68.26 (15)
C4A—Fe1A—C5A	40.32 (12)	C4B—Fe1B—C5B	40.14 (14)
C8A—Fe1A—C5A	117.11 (13)	C7B—Fe1B—C5B	121.69 (15)
C3A—Fe1A—C5A	68.10 (14)	C9B—Fe1B—C5B	124.34 (13)
C9A—Fe1A—C1A	118.14 (13)	C6B—Fe1B—C1B	160.29 (14)
C10A—Fe1A—C1A	153.07 (13)	C10B—Fe1B—C1B	124.96 (13)
C6A—Fe1A—C1A	164.20 (13)	C3B—Fe1B—C1B	68.13 (15)
C2A—Fe1A—C1A	40.01 (13)	C2B—Fe1B—C1B	40.72 (14)
C4A—Fe1A—C1A	67.68 (14)	C4B—Fe1B—C1B	67.57 (15)
C8A—Fe1A—C1A	107.08 (13)	C7B—Fe1B—C1B	158.93 (15)
C3A—Fe1A—C1A	67.71 (13)	C9B—Fe1B—C1B	109.97 (13)
C5A—Fe1A—C1A	40.46 (13)	C5B—Fe1B—C1B	40.51 (14)
C9A—Fe1A—C7A	68.45 (12)	C6B—Fe1B—C8B	67.91 (12)
C10A—Fe1A—C7A	68.22 (11)	C10B—Fe1B—C8B	68.19 (11)
C6A—Fe1A—C7A	39.78 (11)	C3B—Fe1B—C8B	157.23 (14)
C2A—Fe1A—C7A	164.78 (14)	C2B—Fe1B—C8B	161.35 (14)
C4A—Fe1A—C7A	118.57 (14)	C4B—Fe1B—C8B	122.57 (13)
C8A—Fe1A—C7A	40.54 (12)	C7B—Fe1B—C8B	40.30 (11)
C3A—Fe1A—C7A	152.98 (14)	C9B—Fe1B—C8B	40.41 (11)
C5A—Fe1A—C7A	107.26 (14)	C5B—Fe1B—C8B	108.48 (14)
C1A—Fe1A—C7A	127.04 (14)	C1B—Fe1B—C8B	124.93 (14)
C2A—C1A—C5A	107.9 (3)	C5B—C1B—C2B	107.8 (3)
C2A—C1A—Fe1A	69.54 (18)	C5B—C1B—Fe1B	69.8 (2)
C5A—C1A—Fe1A	69.52 (19)	C2B—C1B—Fe1B	69.4 (2)
C2A—C1A—H1AA	126.1	C5B—C1B—H1BA	126.1
C5A—C1A—H1AA	126.1	C2B—C1B—H1BA	126.1
Fe1A—C1A—H1AA	126.1	Fe1B—C1B—H1BA	126.1
C1A—C2A—C3A	108.9 (3)	C3B—C2B—C1B	108.0 (3)
C1A—C2A—Fe1A	70.45 (19)	C3B—C2B—Fe1B	69.72 (19)
C3A—C2A—Fe1A	70.04 (18)	C1B—C2B—Fe1B	69.87 (19)
C1A—C2A—H2AA	125.6	C3B—C2B—H2BA	126.0
C3A—C2A—H2AA	125.6	C1B—C2B—H2BA	126.0
Fe1A—C2A—H2AA	125.6	Fe1B—C2B—H2BA	126.0
C2A—C3A—C4A	107.3 (3)	C2B—C3B—C4B	107.8 (3)
C2A—C3A—Fe1A	69.71 (17)	C2B—C3B—Fe1B	69.95 (18)
C4A—C3A—Fe1A	69.59 (17)	C4B—C3B—Fe1B	70.15 (19)
C2A—C3A—H3AA	126.4	C2B—C3B—H3BA	126.1
C4A—C3A—H3AA	126.4	C4B—C3B—H3BA	126.1
Fe1A—C3A—H3AA	126.4	Fe1B—C3B—H3BA	126.1
C5A—C4A—C3A	108.4 (3)	C5B—C4B—C3B	108.9 (3)
C5A—C4A—Fe1A	70.00 (17)	C5B—C4B—Fe1B	69.97 (18)
C3A—C4A—Fe1A	69.86 (18)	C3B—C4B—Fe1B	69.49 (18)
C5A—C4A—H4AA	125.8	C5B—C4B—H4BA	125.5
C3A—C4A—H4AA	125.8	C3B—C4B—H4BA	125.5
Fe1A—C4A—H4AA	125.8	Fe1B—C4B—H4BA	125.5
C4A—C5A—C1A	107.6 (3)	C4B—C5B—C1B	107.5 (3)
C4A—C5A—Fe1A	69.68 (18)	C4B—C5B—Fe1B	69.9 (2)
C1A—C5A—Fe1A	70.02 (18)	C1B—C5B—Fe1B	69.7 (2)
C4A—C5A—H5AA	126.2	C4B—C5B—H5BA	126.2
C1A—C5A—H5AA	126.2	C1B—C5B—H5BA	126.2
Fe1A—C5A—H5AA	126.2	Fe1B—C5B—H5BA	126.2
C7A—C6A—C10A	108.8 (3)	C7B—C6B—C10B	108.1 (3)
C7A—C6A—Fe1A	70.69 (18)	C7B—C6B—Fe1B	70.23 (19)
C10A—C6A—Fe1A	69.40 (15)	C10B—C6B—Fe1B	69.42 (16)
C7A—C6A—H6AA	125.6	C7B—C6B—H6BA	125.9
C10A—C6A—H6AA	125.6	C10B—C6B—H6BA	125.9
Fe1A—C6A—H6AA	125.6	Fe1B—C6B—H6BA	125.9
C6A—C7A—C8A	108.8 (3)	C6B—C7B—C8B	108.2 (3)
C6A—C7A—Fe1A	69.53 (16)	C6B—C7B—Fe1B	69.33 (17)
C8A—C7A—Fe1A	69.36 (17)	C8B—C7B—Fe1B	70.53 (17)
C6A—C7A—H7AA	125.6	C6B—C7B—H7BA	125.9
C8A—C7A—H7AA	125.6	C8B—C7B—H7BA	125.9
Fe1A—C7A—H7AA	125.6	Fe1B—C7B—H7BA	125.9
C7A—C8A—C9A	107.6 (3)	C7B—C8B—C9B	108.7 (3)
C7A—C8A—Fe1A	70.09 (16)	C7B—C8B—Fe1B	69.17 (16)
C9A—C8A—Fe1A	69.03 (14)	C9B—C8B—Fe1B	69.14 (15)
C7A—C8A—H8AA	126.2	C7B—C8B—H8BA	125.6
C9A—C8A—H8AA	126.2	C9B—C8B—H8BA	125.6
Fe1A—C8A—H8AA	126.2	Fe1B—C8B—H8BA	125.6
C8A—C9A—C10A	107.7 (3)	C8B—C9B—C10B	107.4 (2)
C8A—C9A—Fe1A	69.95 (16)	C8B—C9B—Fe1B	70.44 (16)
C10A—C9A—Fe1A	69.51 (14)	C10B—C9B—Fe1B	69.04 (15)
C8A—C9A—H9AA	126.2	C8B—C9B—H9BA	126.3
C10A—C9A—H9AA	126.2	C10B—C9B—H9BA	126.3
Fe1A—C9A—H9AA	126.2	Fe1B—C9B—H9BA	126.3
C6A—C10A—C9A	107.0 (2)	C9B—C10B—C6B	107.6 (2)
C6A—C10A—C11A	131.6 (2)	C9B—C10B—C11B	130.1 (2)
C9A—C10A—C11A	121.2 (2)	C6B—C10B—C11B	122.2 (2)
C6A—C10A—Fe1A	69.58 (15)	C9B—C10B—Fe1B	69.90 (16)
C9A—C10A—Fe1A	69.18 (15)	C6B—C10B—Fe1B	69.33 (16)
C11A—C10A—Fe1A	123.37 (17)	C11B—C10B—Fe1B	123.20 (18)
O1A—C11A—N1A	121.7 (2)	O1B—C11B—N1B	121.8 (2)
O1A—C11A—C10A	120.9 (2)	O1B—C11B—C10B	121.1 (2)
N1A—C11A—C10A	117.4 (2)	N1B—C11B—C10B	117.1 (2)
C11A—N1A—C12A	128.6 (2)	C11B—N1B—C12B	128.9 (2)
C11A—N1A—H1AB	115.7	C11B—N1B—H1BB	115.6
C12A—N1A—H1AB	115.7	C12B—N1B—H1BB	115.6
C12A—N2A—C13A	131.6 (2)	C12B—N2B—C13B	131.9 (2)
C12A—N2A—H2AB	114.2	C12B—N2B—H2BB	114.1
C13A—N2A—H2AB	114.2	C13B—N2B—H2BB	114.1
C20A—N3A—C21A	117.0 (2)	C20B—N3B—C21B	117.3 (2)
N2A—C12A—N1A	115.4 (2)	N2B—C12B—N1B	114.4 (2)
N2A—C12A—S1A	126.9 (2)	N2B—C12B—S1B	128.0 (2)
N1A—C12A—S1A	117.75 (19)	N1B—C12B—S1B	117.56 (19)
C14A—C13A—N2A	127.1 (2)	C14B—C13B—N2B	126.9 (3)
C14A—C13A—C21A	119.2 (2)	C14B—C13B—C21B	119.2 (2)
N2A—C13A—C21A	113.7 (2)	N2B—C13B—C21B	113.9 (2)
C13A—C14A—C15A	120.9 (3)	C13B—C14B—C15B	119.1 (3)
C13A—C14A—H14A	119.5	C13B—C14B—H14B	120.4
C15A—C14A—H14A	119.5	C15B—C14B—H14B	120.4
C16A—C15A—C14A	120.8 (3)	C16B—C15B—C14B	122.3 (3)
C16A—C15A—H15A	119.6	C16B—C15B—H15B	118.9
C14A—C15A—H15A	119.6	C14B—C15B—H15B	118.9
C15A—C16A—C17A	120.3 (3)	C15B—C16B—C17B	120.6 (3)
C15A—C16A—H16A	119.8	C15B—C16B—H16B	119.7
C17A—C16A—H16A	119.8	C17B—C16B—H16B	119.7
C16A—C17A—C18A	123.3 (3)	C16B—C17B—C21B	118.7 (3)
C16A—C17A—C21A	119.6 (3)	C16B—C17B—C18B	124.4 (3)
C18A—C17A—C21A	117.1 (2)	C21B—C17B—C18B	116.9 (3)
C19A—C18A—C17A	119.6 (3)	C19B—C18B—C17B	120.5 (3)
C19A—C18A—H18A	120.2	C19B—C18B—H18B	119.7
C17A—C18A—H18A	120.2	C17B—C18B—H18B	119.7
C18A—C19A—C20A	119.2 (3)	C18B—C19B—C20B	118.5 (3)
C18A—C19A—H19A	120.4	C18B—C19B—H19B	120.7
C20A—C19A—H19A	120.4	C20B—C19B—H19B	120.7
N3A—C20A—C19A	124.1 (3)	N3B—C20B—C19B	124.3 (3)
N3A—C20A—H20A	118.0	N3B—C20B—H20B	117.9
C19A—C20A—H20A	118.0	C19B—C20B—H20B	117.9
N3A—C21A—C17A	123.1 (2)	N3B—C21B—C17B	122.4 (3)
N3A—C21A—C13A	117.8 (2)	N3B—C21B—C13B	117.4 (2)
C17A—C21A—C13A	119.1 (2)	C17B—C21B—C13B	120.2 (2)
C9A—Fe1A—C1A—C2A	−85.7 (2)	C6B—Fe1B—C1B—C5B	156.7 (3)
C10A—Fe1A—C1A—C2A	−51.6 (3)	C10B—Fe1B—C1B—C5B	−163.45 (19)
C6A—Fe1A—C1A—C2A	161.5 (4)	C3B—Fe1B—C1B—C5B	81.5 (2)
C4A—Fe1A—C1A—C2A	81.4 (2)	C2B—Fe1B—C1B—C5B	119.1 (3)
C8A—Fe1A—C1A—C2A	−128.7 (2)	C4B—Fe1B—C1B—C5B	37.8 (2)
C3A—Fe1A—C1A—C2A	37.4 (2)	C7B—Fe1B—C1B—C5B	−37.9 (5)
C5A—Fe1A—C1A—C2A	119.3 (3)	C9B—Fe1B—C1B—C5B	−119.9 (2)
C7A—Fe1A—C1A—C2A	−168.9 (2)	C8B—Fe1B—C1B—C5B	−77.2 (2)
C9A—Fe1A—C1A—C5A	155.04 (19)	C6B—Fe1B—C1B—C2B	37.7 (5)
C10A—Fe1A—C1A—C5A	−170.9 (2)	C10B—Fe1B—C1B—C2B	77.5 (2)
C6A—Fe1A—C1A—C5A	42.2 (6)	C3B—Fe1B—C1B—C2B	−37.5 (2)
C2A—Fe1A—C1A—C5A	−119.3 (3)	C4B—Fe1B—C1B—C2B	−81.3 (2)
C4A—Fe1A—C1A—C5A	−37.9 (2)	C7B—Fe1B—C1B—C2B	−157.0 (3)
C8A—Fe1A—C1A—C5A	112.0 (2)	C9B—Fe1B—C1B—C2B	121.0 (2)
C3A—Fe1A—C1A—C5A	−81.9 (2)	C5B—Fe1B—C1B—C2B	−119.1 (3)
C7A—Fe1A—C1A—C5A	71.8 (2)	C8B—Fe1B—C1B—C2B	163.78 (19)
C5A—C1A—C2A—C3A	−0.6 (4)	C5B—C1B—C2B—C3B	0.0 (4)
Fe1A—C1A—C2A—C3A	−59.7 (2)	Fe1B—C1B—C2B—C3B	59.5 (2)
C5A—C1A—C2A—Fe1A	59.1 (2)	C5B—C1B—C2B—Fe1B	−59.5 (2)
C9A—Fe1A—C2A—C1A	111.9 (2)	C6B—Fe1B—C2B—C3B	75.1 (2)
C10A—Fe1A—C2A—C1A	155.79 (19)	C10B—Fe1B—C2B—C3B	118.5 (2)
C6A—Fe1A—C2A—C1A	−168.4 (3)	C4B—Fe1B—C2B—C3B	−38.0 (2)
C4A—Fe1A—C2A—C1A	−81.4 (2)	C7B—Fe1B—C2B—C3B	39.5 (5)
C8A—Fe1A—C2A—C1A	70.2 (3)	C9B—Fe1B—C2B—C3B	161.1 (2)
C3A—Fe1A—C2A—C1A	−119.6 (3)	C5B—Fe1B—C2B—C3B	−81.4 (2)
C5A—Fe1A—C2A—C1A	−37.7 (2)	C1B—Fe1B—C2B—C3B	−119.1 (3)
C7A—Fe1A—C2A—C1A	35.9 (6)	C8B—Fe1B—C2B—C3B	−164.8 (4)
C9A—Fe1A—C2A—C3A	−128.44 (19)	C6B—Fe1B—C2B—C1B	−165.8 (2)
C10A—Fe1A—C2A—C3A	−84.6 (2)	C10B—Fe1B—C2B—C1B	−122.4 (2)
C6A—Fe1A—C2A—C3A	−48.8 (4)	C3B—Fe1B—C2B—C1B	119.1 (3)
C4A—Fe1A—C2A—C3A	38.2 (2)	C4B—Fe1B—C2B—C1B	81.1 (2)
C8A—Fe1A—C2A—C3A	−170.22 (19)	C7B—Fe1B—C2B—C1B	158.6 (3)
C5A—Fe1A—C2A—C3A	81.9 (2)	C9B—Fe1B—C2B—C1B	−79.8 (2)
C1A—Fe1A—C2A—C3A	119.6 (3)	C5B—Fe1B—C2B—C1B	37.7 (2)
C7A—Fe1A—C2A—C3A	155.5 (5)	C8B—Fe1B—C2B—C1B	−45.7 (5)
C1A—C2A—C3A—C4A	0.3 (4)	C1B—C2B—C3B—C4B	0.6 (4)
Fe1A—C2A—C3A—C4A	−59.7 (2)	Fe1B—C2B—C3B—C4B	60.2 (2)
C1A—C2A—C3A—Fe1A	60.0 (2)	C1B—C2B—C3B—Fe1B	−59.6 (2)
C9A—Fe1A—C3A—C2A	71.8 (2)	C6B—Fe1B—C3B—C2B	−122.3 (2)
C10A—Fe1A—C3A—C2A	114.2 (2)	C10B—Fe1B—C3B—C2B	−80.6 (2)
C6A—Fe1A—C3A—C2A	158.00 (19)	C4B—Fe1B—C3B—C2B	118.5 (3)
C4A—Fe1A—C3A—C2A	−118.4 (3)	C7B—Fe1B—C3B—C2B	−163.5 (2)
C8A—Fe1A—C3A—C2A	33.6 (6)	C9B—Fe1B—C3B—C2B	−50.6 (5)
C5A—Fe1A—C3A—C2A	−81.0 (2)	C5B—Fe1B—C3B—C2B	81.7 (2)
C1A—Fe1A—C3A—C2A	−37.2 (2)	C1B—Fe1B—C3B—C2B	37.9 (2)
C7A—Fe1A—C3A—C2A	−166.2 (3)	C8B—Fe1B—C3B—C2B	167.5 (3)
C9A—Fe1A—C3A—C4A	−169.79 (19)	C6B—Fe1B—C3B—C4B	119.2 (2)
C10A—Fe1A—C3A—C4A	−127.4 (2)	C10B—Fe1B—C3B—C4B	160.9 (2)
C6A—Fe1A—C3A—C4A	−83.6 (2)	C2B—Fe1B—C3B—C4B	−118.5 (3)
C2A—Fe1A—C3A—C4A	118.4 (3)	C7B—Fe1B—C3B—C4B	78.0 (3)
C8A—Fe1A—C3A—C4A	152.0 (5)	C9B—Fe1B—C3B—C4B	−169.2 (3)
C5A—Fe1A—C3A—C4A	37.4 (2)	C5B—Fe1B—C3B—C4B	−36.8 (2)
C1A—Fe1A—C3A—C4A	81.2 (2)	C1B—Fe1B—C3B—C4B	−80.6 (3)
C7A—Fe1A—C3A—C4A	−47.7 (4)	C8B—Fe1B—C3B—C4B	49.0 (5)
C2A—C3A—C4A—C5A	0.1 (4)	C2B—C3B—C4B—C5B	−1.1 (4)
Fe1A—C3A—C4A—C5A	−59.6 (2)	Fe1B—C3B—C4B—C5B	59.0 (2)
C2A—C3A—C4A—Fe1A	59.8 (2)	C2B—C3B—C4B—Fe1B	−60.1 (2)
C9A—Fe1A—C4A—C5A	157.1 (5)	C6B—Fe1B—C4B—C5B	161.9 (2)
C10A—Fe1A—C4A—C5A	−167.1 (2)	C10B—Fe1B—C4B—C5B	−166.9 (3)
C6A—Fe1A—C4A—C5A	−125.5 (2)	C3B—Fe1B—C4B—C5B	−120.3 (3)
C2A—Fe1A—C4A—C5A	81.5 (2)	C2B—Fe1B—C4B—C5B	−82.4 (2)
C8A—Fe1A—C4A—C5A	−46.9 (4)	C7B—Fe1B—C4B—C5B	120.6 (2)
C3A—Fe1A—C4A—C5A	119.4 (3)	C9B—Fe1B—C4B—C5B	49.3 (5)
C1A—Fe1A—C4A—C5A	38.1 (2)	C1B—Fe1B—C4B—C5B	−38.2 (2)
C7A—Fe1A—C4A—C5A	−83.1 (2)	C8B—Fe1B—C4B—C5B	80.0 (3)
C9A—Fe1A—C4A—C3A	37.7 (7)	C6B—Fe1B—C4B—C3B	−77.8 (3)
C10A—Fe1A—C4A—C3A	73.6 (2)	C10B—Fe1B—C4B—C3B	−46.6 (5)
C6A—Fe1A—C4A—C3A	115.1 (2)	C2B—Fe1B—C4B—C3B	37.9 (2)
C2A—Fe1A—C4A—C3A	−37.9 (2)	C7B—Fe1B—C4B—C3B	−119.1 (2)
C8A—Fe1A—C4A—C3A	−166.2 (3)	C9B—Fe1B—C4B—C3B	169.6 (3)
C5A—Fe1A—C4A—C3A	−119.4 (3)	C5B—Fe1B—C4B—C3B	120.3 (3)
C1A—Fe1A—C4A—C3A	−81.3 (2)	C1B—Fe1B—C4B—C3B	82.2 (3)
C7A—Fe1A—C4A—C3A	157.5 (2)	C8B—Fe1B—C4B—C3B	−159.7 (2)
C3A—C4A—C5A—C1A	−0.5 (4)	C3B—C4B—C5B—C1B	1.1 (4)
Fe1A—C4A—C5A—C1A	−60.0 (2)	Fe1B—C4B—C5B—C1B	59.8 (2)
C3A—C4A—C5A—Fe1A	59.5 (2)	C3B—C4B—C5B—Fe1B	−58.7 (3)
C2A—C1A—C5A—C4A	0.7 (4)	C2B—C1B—C5B—C4B	−0.7 (4)
Fe1A—C1A—C5A—C4A	59.8 (2)	Fe1B—C1B—C5B—C4B	−59.9 (2)
C2A—C1A—C5A—Fe1A	−59.2 (2)	C2B—C1B—C5B—Fe1B	59.2 (2)
C9A—Fe1A—C5A—C4A	−169.4 (2)	C6B—Fe1B—C5B—C4B	−42.0 (4)
C10A—Fe1A—C5A—C4A	44.7 (6)	C10B—Fe1B—C5B—C4B	164.5 (3)
C6A—Fe1A—C5A—C4A	74.7 (3)	C3B—Fe1B—C5B—C4B	37.0 (2)
C2A—Fe1A—C5A—C4A	−81.2 (2)	C2B—Fe1B—C5B—C4B	80.6 (2)
C8A—Fe1A—C5A—C4A	156.8 (2)	C7B—Fe1B—C5B—C4B	−76.6 (2)
C3A—Fe1A—C5A—C4A	−37.6 (2)	C9B—Fe1B—C5B—C4B	−160.89 (19)
C1A—Fe1A—C5A—C4A	−118.5 (3)	C1B—Fe1B—C5B—C4B	118.5 (3)
C7A—Fe1A—C5A—C4A	114.1 (2)	C8B—Fe1B—C5B—C4B	−119.0 (2)
C9A—Fe1A—C5A—C1A	−50.9 (4)	C6B—Fe1B—C5B—C1B	−160.5 (3)
C10A—Fe1A—C5A—C1A	163.2 (4)	C10B—Fe1B—C5B—C1B	46.1 (5)
C6A—Fe1A—C5A—C1A	−166.78 (19)	C3B—Fe1B—C5B—C1B	−81.4 (2)
C2A—Fe1A—C5A—C1A	37.3 (2)	C2B—Fe1B—C5B—C1B	−37.9 (2)
C4A—Fe1A—C5A—C1A	118.5 (3)	C4B—Fe1B—C5B—C1B	−118.5 (3)
C8A—Fe1A—C5A—C1A	−84.7 (2)	C7B—Fe1B—C5B—C1B	164.9 (2)
C3A—Fe1A—C5A—C1A	80.9 (2)	C9B—Fe1B—C5B—C1B	80.6 (2)
C7A—Fe1A—C5A—C1A	−127.4 (2)	C8B—Fe1B—C5B—C1B	122.6 (2)
C9A—Fe1A—C6A—C7A	−81.31 (19)	C10B—Fe1B—C6B—C7B	119.2 (2)
C10A—Fe1A—C6A—C7A	−119.8 (2)	C3B—Fe1B—C6B—C7B	−119.3 (2)
C2A—Fe1A—C6A—C7A	−170.3 (3)	C2B—Fe1B—C6B—C7B	−159.81 (19)
C4A—Fe1A—C6A—C7A	112.4 (2)	C4B—Fe1B—C6B—C7B	−78.2 (2)
C8A—Fe1A—C6A—C7A	−37.07 (18)	C9B—Fe1B—C6B—C7B	81.14 (19)
C3A—Fe1A—C6A—C7A	155.43 (19)	C5B—Fe1B—C6B—C7B	−48.1 (4)
C5A—Fe1A—C6A—C7A	71.1 (2)	C1B—Fe1B—C6B—C7B	171.9 (4)
C1A—Fe1A—C6A—C7A	38.1 (5)	C8B—Fe1B—C6B—C7B	37.56 (18)
C9A—Fe1A—C6A—C10A	38.49 (15)	C3B—Fe1B—C6B—C10B	121.49 (17)
C2A—Fe1A—C6A—C10A	−50.5 (4)	C2B—Fe1B—C6B—C10B	81.0 (2)
C4A—Fe1A—C6A—C10A	−127.81 (17)	C4B—Fe1B—C6B—C10B	162.59 (17)
C8A—Fe1A—C6A—C10A	82.72 (17)	C7B—Fe1B—C6B—C10B	−119.2 (2)
C3A—Fe1A—C6A—C10A	−84.78 (19)	C9B—Fe1B—C6B—C10B	−38.06 (15)
C5A—Fe1A—C6A—C10A	−169.06 (17)	C5B—Fe1B—C6B—C10B	−167.3 (3)
C1A—Fe1A—C6A—C10A	157.9 (4)	C1B—Fe1B—C6B—C10B	52.7 (4)
C7A—Fe1A—C6A—C10A	119.8 (2)	C8B—Fe1B—C6B—C10B	−81.65 (17)
C10A—C6A—C7A—C8A	−0.8 (3)	C10B—C6B—C7B—C8B	−0.8 (4)
Fe1A—C6A—C7A—C8A	58.3 (2)	Fe1B—C6B—C7B—C8B	−60.1 (2)
C10A—C6A—C7A—Fe1A	−59.11 (19)	C10B—C6B—C7B—Fe1B	59.3 (2)
C9A—Fe1A—C7A—C6A	82.44 (18)	C10B—Fe1B—C7B—C6B	−38.16 (17)
C10A—Fe1A—C7A—C6A	37.83 (17)	C3B—Fe1B—C7B—C6B	77.7 (2)
C2A—Fe1A—C7A—C6A	164.0 (5)	C2B—Fe1B—C7B—C6B	49.1 (4)
C4A—Fe1A—C7A—C6A	−85.4 (2)	C4B—Fe1B—C7B—C6B	118.9 (2)
C8A—Fe1A—C7A—C6A	120.6 (3)	C9B—Fe1B—C7B—C6B	−82.41 (19)
C3A—Fe1A—C7A—C6A	−52.1 (3)	C5B—Fe1B—C7B—C6B	159.59 (19)
C5A—Fe1A—C7A—C6A	−127.64 (19)	C1B—Fe1B—C7B—C6B	−172.4 (3)
C1A—Fe1A—C7A—C6A	−167.84 (19)	C8B—Fe1B—C7B—C6B	−119.2 (3)
C9A—Fe1A—C7A—C8A	−38.15 (17)	C6B—Fe1B—C7B—C8B	119.2 (3)
C10A—Fe1A—C7A—C8A	−82.76 (19)	C10B—Fe1B—C7B—C8B	81.00 (19)
C6A—Fe1A—C7A—C8A	−120.6 (3)	C3B—Fe1B—C7B—C8B	−163.14 (19)
C2A—Fe1A—C7A—C8A	43.4 (6)	C2B—Fe1B—C7B—C8B	168.3 (3)
C4A—Fe1A—C7A—C8A	154.04 (19)	C4B—Fe1B—C7B—C8B	−121.9 (2)
C3A—Fe1A—C7A—C8A	−172.7 (3)	C9B—Fe1B—C7B—C8B	36.75 (18)
C5A—Fe1A—C7A—C8A	111.8 (2)	C5B—Fe1B—C7B—C8B	−81.3 (2)
C1A—Fe1A—C7A—C8A	71.6 (2)	C1B—Fe1B—C7B—C8B	−53.3 (4)
C6A—C7A—C8A—C9A	0.6 (3)	C6B—C7B—C8B—C9B	1.4 (4)
Fe1A—C7A—C8A—C9A	59.06 (19)	Fe1B—C7B—C8B—C9B	−57.9 (2)
C6A—C7A—C8A—Fe1A	−58.4 (2)	C6B—C7B—C8B—Fe1B	59.3 (2)
C9A—Fe1A—C8A—C7A	118.9 (3)	C6B—Fe1B—C8B—C7B	−37.68 (19)
C10A—Fe1A—C8A—C7A	80.61 (19)	C10B—Fe1B—C8B—C7B	−82.3 (2)
C6A—Fe1A—C8A—C7A	36.40 (17)	C3B—Fe1B—C8B—C7B	40.1 (4)
C2A—Fe1A—C8A—C7A	−166.86 (19)	C2B—Fe1B—C8B—C7B	−165.8 (4)
C4A—Fe1A—C8A—C7A	−53.0 (4)	C4B—Fe1B—C8B—C7B	75.5 (2)
C3A—Fe1A—C8A—C7A	166.3 (5)	C9B—Fe1B—C8B—C7B	−120.8 (3)
C5A—Fe1A—C8A—C7A	−85.1 (2)	C5B—Fe1B—C8B—C7B	117.5 (2)
C1A—Fe1A—C8A—C7A	−127.6 (2)	C1B—Fe1B—C8B—C7B	159.4 (2)
C10A—Fe1A—C8A—C9A	−38.28 (17)	C6B—Fe1B—C8B—C9B	83.12 (19)
C6A—Fe1A—C8A—C9A	−82.49 (18)	C10B—Fe1B—C8B—C9B	38.48 (16)
C2A—Fe1A—C8A—C9A	74.2 (2)	C3B—Fe1B—C8B—C9B	160.9 (3)
C4A—Fe1A—C8A—C9A	−171.9 (3)	C2B—Fe1B—C8B—C9B	−45.0 (5)
C3A—Fe1A—C8A—C9A	47.5 (6)	C4B—Fe1B—C8B—C9B	−163.68 (19)
C5A—Fe1A—C8A—C9A	156.02 (19)	C7B—Fe1B—C8B—C9B	120.8 (3)
C1A—Fe1A—C8A—C9A	113.5 (2)	C5B—Fe1B—C8B—C9B	−121.7 (2)
C7A—Fe1A—C8A—C9A	−118.9 (3)	C1B—Fe1B—C8B—C9B	−79.8 (2)
C7A—C8A—C9A—C10A	−0.2 (3)	C7B—C8B—C9B—C10B	−1.5 (3)
Fe1A—C8A—C9A—C10A	59.50 (17)	Fe1B—C8B—C9B—C10B	−59.40 (18)
C7A—C8A—C9A—Fe1A	−59.7 (2)	C7B—C8B—C9B—Fe1B	57.9 (2)
C10A—Fe1A—C9A—C8A	118.8 (2)	C6B—Fe1B—C9B—C8B	−80.18 (18)
C6A—Fe1A—C9A—C8A	80.57 (19)	C10B—Fe1B—C9B—C8B	−118.4 (2)
C2A—Fe1A—C9A—C8A	−126.4 (2)	C3B—Fe1B—C9B—C8B	−158.4 (4)
C4A—Fe1A—C9A—C8A	162.7 (6)	C2B—Fe1B—C9B—C8B	163.9 (2)
C3A—Fe1A—C9A—C8A	−166.7 (2)	C4B—Fe1B—C9B—C8B	41.6 (4)
C5A—Fe1A—C9A—C8A	−49.0 (4)	C7B—Fe1B—C9B—C8B	−36.66 (18)
C1A—Fe1A—C9A—C8A	−83.8 (2)	C5B—Fe1B—C9B—C8B	77.9 (2)
C7A—Fe1A—C9A—C8A	37.72 (18)	C1B—Fe1B—C9B—C8B	120.9 (2)
C6A—Fe1A—C9A—C10A	−38.23 (15)	C6B—Fe1B—C9B—C10B	38.24 (15)
C2A—Fe1A—C9A—C10A	114.82 (17)	C3B—Fe1B—C9B—C10B	−39.9 (5)
C4A—Fe1A—C9A—C10A	43.9 (6)	C2B—Fe1B—C9B—C10B	−77.6 (2)
C8A—Fe1A—C9A—C10A	−118.8 (2)	C4B—Fe1B—C9B—C10B	160.0 (4)
C3A—Fe1A—C9A—C10A	74.5 (2)	C7B—Fe1B—C9B—C10B	81.76 (17)
C5A—Fe1A—C9A—C10A	−167.8 (3)	C5B—Fe1B—C9B—C10B	−163.73 (18)
C1A—Fe1A—C9A—C10A	157.37 (16)	C1B—Fe1B—C9B—C10B	−120.73 (18)
C7A—Fe1A—C9A—C10A	−81.07 (17)	C8B—Fe1B—C9B—C10B	118.4 (2)
C7A—C6A—C10A—C9A	0.6 (3)	C8B—C9B—C10B—C6B	1.0 (3)
Fe1A—C6A—C10A—C9A	−59.29 (17)	Fe1B—C9B—C10B—C6B	−59.33 (19)
C7A—C6A—C10A—C11A	176.9 (3)	C8B—C9B—C10B—C11B	177.3 (3)
Fe1A—C6A—C10A—C11A	117.0 (3)	Fe1B—C9B—C10B—C11B	117.0 (3)
C7A—C6A—C10A—Fe1A	59.9 (2)	C8B—C9B—C10B—Fe1B	60.3 (2)
C8A—C9A—C10A—C6A	−0.2 (3)	C7B—C6B—C10B—C9B	−0.1 (3)
Fe1A—C9A—C10A—C6A	59.54 (18)	Fe1B—C6B—C10B—C9B	59.69 (19)
C8A—C9A—C10A—C11A	−177.0 (2)	C7B—C6B—C10B—C11B	−176.8 (3)
Fe1A—C9A—C10A—C11A	−117.2 (2)	Fe1B—C6B—C10B—C11B	−117.0 (2)
C8A—C9A—C10A—Fe1A	−59.78 (19)	C7B—C6B—C10B—Fe1B	−59.8 (2)
C9A—Fe1A—C10A—C6A	−118.4 (2)	C6B—Fe1B—C10B—C9B	−118.8 (2)
C2A—Fe1A—C10A—C6A	157.46 (18)	C3B—Fe1B—C10B—C9B	164.86 (18)
C4A—Fe1A—C10A—C6A	73.2 (2)	C2B—Fe1B—C10B—C9B	122.53 (18)
C8A—Fe1A—C10A—C6A	−80.41 (18)	C4B—Fe1B—C10B—C9B	−161.3 (3)
C3A—Fe1A—C10A—C6A	114.50 (18)	C7B—Fe1B—C10B—C9B	−81.37 (17)
C5A—Fe1A—C10A—C6A	37.5 (5)	C5B—Fe1B—C10B—C9B	45.5 (4)
C1A—Fe1A—C10A—C6A	−166.9 (3)	C1B—Fe1B—C10B—C9B	80.3 (2)
C7A—Fe1A—C10A—C6A	−36.73 (16)	C8B—Fe1B—C10B—C9B	−37.89 (15)
C6A—Fe1A—C10A—C9A	118.4 (2)	C3B—Fe1B—C10B—C6B	−76.3 (2)
C2A—Fe1A—C10A—C9A	−84.11 (19)	C2B—Fe1B—C10B—C6B	−118.68 (19)
C4A—Fe1A—C10A—C9A	−168.42 (18)	C4B—Fe1B—C10B—C6B	−42.5 (4)
C8A—Fe1A—C10A—C9A	38.02 (16)	C7B—Fe1B—C10B—C6B	37.42 (16)
C3A—Fe1A—C10A—C9A	−127.07 (17)	C9B—Fe1B—C10B—C6B	118.8 (2)
C5A—Fe1A—C10A—C9A	156.0 (5)	C5B—Fe1B—C10B—C6B	164.3 (4)
C1A—Fe1A—C10A—C9A	−48.5 (3)	C1B—Fe1B—C10B—C6B	−160.88 (19)
C7A—Fe1A—C10A—C9A	81.70 (17)	C8B—Fe1B—C10B—C6B	80.91 (17)
C9A—Fe1A—C10A—C11A	114.4 (3)	C6B—Fe1B—C10B—C11B	115.7 (3)
C6A—Fe1A—C10A—C11A	−127.1 (3)	C3B—Fe1B—C10B—C11B	39.4 (3)
C2A—Fe1A—C10A—C11A	30.3 (3)	C2B—Fe1B—C10B—C11B	−2.9 (3)
C4A—Fe1A—C10A—C11A	−54.0 (3)	C4B—Fe1B—C10B—C11B	73.2 (4)
C8A—Fe1A—C10A—C11A	152.5 (2)	C7B—Fe1B—C10B—C11B	153.2 (2)
C3A—Fe1A—C10A—C11A	−12.6 (2)	C9B—Fe1B—C10B—C11B	−125.5 (3)
C5A—Fe1A—C10A—C11A	−89.6 (5)	C5B—Fe1B—C10B—C11B	−79.9 (5)
C1A—Fe1A—C10A—C11A	65.9 (3)	C1B—Fe1B—C10B—C11B	−45.1 (3)
C7A—Fe1A—C10A—C11A	−163.9 (2)	C8B—Fe1B—C10B—C11B	−163.3 (2)
C6A—C10A—C11A—O1A	−163.1 (3)	C9B—C10B—C11B—O1B	−173.7 (3)
C9A—C10A—C11A—O1A	12.7 (4)	C6B—C10B—C11B—O1B	2.2 (4)
Fe1A—C10A—C11A—O1A	−71.6 (3)	Fe1B—C10B—C11B—O1B	−82.9 (3)
C6A—C10A—C11A—N1A	16.7 (4)	C9B—C10B—C11B—N1B	7.5 (4)
C9A—C10A—C11A—N1A	−167.4 (2)	C6B—C10B—C11B—N1B	−176.6 (2)
Fe1A—C10A—C11A—N1A	108.2 (2)	Fe1B—C10B—C11B—N1B	98.3 (2)
O1A—C11A—N1A—C12A	0.4 (4)	O1B—C11B—N1B—C12B	0.1 (4)
C10A—C11A—N1A—C12A	−179.4 (2)	C10B—C11B—N1B—C12B	178.9 (2)
C13A—N2A—C12A—N1A	−176.2 (2)	C13B—N2B—C12B—N1B	178.8 (2)
C13A—N2A—C12A—S1A	3.6 (4)	C13B—N2B—C12B—S1B	−1.7 (4)
C11A—N1A—C12A—N2A	−8.7 (4)	C11B—N1B—C12B—N2B	3.3 (4)
C11A—N1A—C12A—S1A	171.5 (2)	C11B—N1B—C12B—S1B	−176.3 (2)
C12A—N2A—C13A—C14A	−12.9 (5)	C12B—N2B—C13B—C14B	−4.9 (5)
C12A—N2A—C13A—C21A	167.5 (3)	C12B—N2B—C13B—C21B	177.0 (2)
N2A—C13A—C14A—C15A	179.2 (3)	N2B—C13B—C14B—C15B	−179.0 (3)
C21A—C13A—C14A—C15A	−1.2 (4)	C21B—C13B—C14B—C15B	−1.1 (4)
C13A—C14A—C15A—C16A	−0.3 (5)	C13B—C14B—C15B—C16B	−0.5 (5)
C14A—C15A—C16A—C17A	0.9 (5)	C14B—C15B—C16B—C17B	1.5 (5)
C15A—C16A—C17A—C18A	179.6 (3)	C15B—C16B—C17B—C21B	−0.8 (5)
C15A—C16A—C17A—C21A	0.0 (4)	C15B—C16B—C17B—C18B	176.9 (3)
C16A—C17A—C18A—C19A	−178.7 (3)	C16B—C17B—C18B—C19B	−176.6 (3)
C21A—C17A—C18A—C19A	0.9 (4)	C21B—C17B—C18B—C19B	1.1 (5)
C17A—C18A—C19A—C20A	−0.3 (4)	C17B—C18B—C19B—C20B	0.0 (5)
C21A—N3A—C20A—C19A	0.1 (4)	C21B—N3B—C20B—C19B	2.0 (5)
C18A—C19A—C20A—N3A	−0.2 (5)	C18B—C19B—C20B—N3B	−1.7 (5)
C20A—N3A—C21A—C17A	0.6 (4)	C20B—N3B—C21B—C17B	−0.7 (4)
C20A—N3A—C21A—C13A	−179.3 (2)	C20B—N3B—C21B—C13B	177.2 (3)
C16A—C17A—C21A—N3A	178.5 (2)	C16B—C17B—C21B—N3B	177.1 (3)
C18A—C17A—C21A—N3A	−1.1 (4)	C18B—C17B—C21B—N3B	−0.8 (4)
C16A—C17A—C21A—C13A	−1.5 (4)	C16B—C17B—C21B—C13B	−0.8 (4)
C18A—C17A—C21A—C13A	178.9 (2)	C18B—C17B—C21B—C13B	−178.6 (2)
C14A—C13A—C21A—N3A	−177.9 (2)	C14B—C13B—C21B—N3B	−176.2 (2)
N2A—C13A—C21A—N3A	1.7 (3)	N2B—C13B—C21B—N3B	2.0 (3)
C14A—C13A—C21A—C17A	2.1 (4)	C14B—C13B—C21B—C17B	1.7 (4)
N2A—C13A—C21A—C17A	−178.2 (2)	N2B—C13B—C21B—C17B	179.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AB···O1B^i	0.86	2.21	3.009 (3)	155
N2A—H2AB···O1A	0.86	1.90	2.621 (3)	141
N1B—H1BB···O1A^ii	0.86	2.18	3.026 (3)	167
N2B—H2BB···O1B	0.86	1.89	2.625 (3)	143
C15B—H15B···S1A^iii	0.93	2.83	3.715 (3)	160
C9B—H9BA···O1A^ii	0.98	2.24	3.140 (3)	153

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x, −y, −z+1; (iii) −x+1/2, y−1/2, −z+3/2.