N-Ferrocenoyl-labelled glutamate diethyl ester

Kraatz, H.-B.; Sutherland, T.C.; Appoh, F.E.

doi:10.1107/S1600536803026187

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N-Ferrocenoyl-labelled glutamate diethyl ester

H.-B. Kraatz, T. C. Sutherland and F. E. Appoh

Diethyl N-(ferrocenylcarbonyl)glutamate or N-ferrocenoyl-glutamate-(OEt)₂, [Fe(C₅H₅)(C₁₅H₂₀O₅N)], (I), is a derivative of N-ferrocenoylglutamate-(OBz)₂, the corresponding benzyl ester derivative published previously [Kraatz, Lusztyk & Enright (1997). Inorg. Chem. 36, 2400-2405]. These redox-labeled amino acid structures exhibit intermolecular hydrogen bonding that leads to extended networks in the solid state and exhibit typical ferrocene one-electron reversible electrochemical responses. The asymmetric unit of the structure contains two independent molecules, in which the most notable difference is in the conformations of the diethyl ester groups.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026187/lh6135sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026187/lh6135Isup2.hkl Contains datablock I

CCDC reference: 227761

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.005 Å
R factor = 0.038
wR factor = 0.095
Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       1.00 mm
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.51 Ratio
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.20 Ratio

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.16 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.74 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10      =       5.34 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C22    -   C23      =       5.70 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C8
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C28

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.37
           From the CIF: _reflns_number_total               8093
           Count of symmetry unique reflns         4140
           Completeness (_total/calc)            195.48%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3953
           Fraction of Friedel pairs measured     0.955
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(I) top

Crystal data top

[Fe(C₅H₅)(C₁₅H₂₀NO₅)]	D_x = 1.370 Mg m⁻³
M_r = 415.26	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3₁	Cell parameters from 4477 reflections
Hall symbol: P 31	θ = 2.2–25.7°
a = 11.4140 (3) Å	µ = 0.78 mm⁻¹
c = 26.7688 (17) Å	T = 193 K
V = 3020.2 (2) Å³	Prism, orange
Z = 6	1.00 × 0.23 × 0.22 mm
F(000) = 1308

Data collection top

Bruker PLATFORM diffractometer/SMART 1000 CCD area-detector	8093 independent reflections
Radiation source: fine-focus sealed tube	7430 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 8.192 pixels mm^-1	θ_max = 26.4°, θ_min = 2.1°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→14
T_min = 0.510, T_max = 0.847	l = −33→32
16410 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0498P)² + 0.5792P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
8093 reflections	Δρ_max = 0.46 e Å⁻³
487 parameters	Δρ_min = −0.37 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 4131 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.010 (12)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.12524 (4)	0.28445 (4)	−0.059761 (15)	0.03641 (12)
O1	0.1920 (2)	0.5992 (2)	0.01099 (7)	0.0393 (5)
O2	0.3444 (3)	0.8930 (3)	−0.07892 (11)	0.0670 (8)
O3	0.5209 (2)	1.0158 (2)	−0.02838 (10)	0.0487 (6)
O4	0.8334 (3)	0.8275 (3)	−0.02178 (12)	0.0707 (8)
O5	0.7618 (3)	0.6198 (3)	−0.04844 (15)	0.0803 (10)
N1	0.3352 (2)	0.6584 (2)	−0.05465 (9)	0.0341 (5)
H1N	0.3481	0.6353	−0.0846	0.041*
C1	0.2180 (3)	0.5780 (3)	−0.03170 (10)	0.0279 (5)
C2	0.4418 (3)	0.7813 (3)	−0.03278 (10)	0.0326 (6)
H2	0.4330	0.7741	0.0044	0.039*
C3	0.4274 (3)	0.9022 (3)	−0.05020 (13)	0.0384 (7)
C4	0.5177 (4)	1.1382 (4)	−0.0438 (2)	0.0652 (11)
H4A	0.5473	1.1604	−0.0790	0.078*
H4B	0.4244	1.1225	−0.0411	0.078*
C5	0.6067 (5)	1.2479 (4)	−0.0118 (2)	0.0866 (16)
H5A	0.6042	1.3297	−0.0212	0.104*
H5B	0.6992	1.2644	−0.0154	0.104*
H5C	0.5774	1.2246	0.0230	0.104*
C6	0.5816 (3)	0.8045 (3)	−0.04749 (12)	0.0380 (7)
H6A	0.5961	0.8256	−0.0836	0.046*
H6B	0.6517	0.8837	−0.0290	0.046*
C7	0.5984 (3)	0.6832 (3)	−0.03674 (13)	0.0430 (7)
H7A	0.5542	0.6426	−0.0045	0.052*
H7B	0.5519	0.6145	−0.0631	0.052*
C8	0.7431 (3)	0.7185 (4)	−0.03443 (12)	0.0449 (7)
C9	0.9044 (5)	0.6451 (5)	−0.0448 (3)	0.0974 (19)
H9A	0.9479	0.6983	−0.0143	0.117*
H9B	0.9025	0.5577	−0.0421	0.117*
C10	0.9837 (5)	0.7193 (6)	−0.0889 (2)	0.0908 (17)
H10A	1.0759	0.7346	−0.0858	0.109*
H10B	0.9868	0.8065	−0.0912	0.109*
H10C	0.9413	0.6661	−0.1190	0.109*
C11	0.1180 (3)	0.4575 (3)	−0.05989 (10)	0.0296 (6)
C12	0.1272 (3)	0.4193 (3)	−0.10954 (10)	0.0328 (6)
H12	0.2011	0.4739	−0.1339	0.039*
C13	0.0130 (3)	0.2905 (3)	−0.11858 (12)	0.0390 (7)
H13	−0.0066	0.2374	−0.1503	0.047*
C14	−0.0667 (3)	0.2478 (3)	−0.07464 (13)	0.0423 (7)
H14	−0.1524	0.1597	−0.0699	0.051*
C15	−0.0021 (3)	0.3519 (3)	−0.03806 (12)	0.0369 (6)
H15	−0.0349	0.3504	−0.0033	0.044*
C16	0.2834 (4)	0.3158 (4)	−0.01574 (16)	0.0583 (10)
H16	0.3408	0.3993	0.0042	0.070*
C17	0.3080 (4)	0.2948 (4)	−0.06535 (18)	0.0625 (11)
H17	0.3858	0.3599	−0.0865	0.075*
C18	0.2022 (5)	0.1640 (4)	−0.08035 (18)	0.0653 (12)
H18	0.1927	0.1216	−0.1139	0.078*
C19	0.1141 (5)	0.1065 (4)	−0.04005 (17)	0.0657 (13)
H19	0.0301	0.0157	−0.0398	0.079*
C20	0.1634 (4)	0.2018 (4)	0.00118 (16)	0.0607 (11)
H20	0.1217	0.1886	0.0351	0.073*
Fe2	0.14628 (4)	0.90014 (4)	0.116305 (14)	0.03207 (10)
O6	0.3622 (2)	0.7834 (2)	0.18188 (7)	0.0399 (5)
O7	0.4902 (3)	0.6275 (3)	0.08030 (11)	0.0716 (8)
O8	0.4480 (2)	0.4626 (2)	0.13470 (9)	0.0465 (5)
O9	−0.1745 (4)	0.3099 (5)	0.09276 (19)	0.1251 (17)
O10	−0.0892 (3)	0.1776 (3)	0.09732 (15)	0.0906 (11)
N2	0.2802 (3)	0.6550 (2)	0.11266 (9)	0.0344 (5)
H2N	0.2459	0.6494	0.0827	0.041*
C21	0.3198 (3)	0.7681 (3)	0.13887 (10)	0.0283 (5)
C22	0.2904 (3)	0.5405 (3)	0.13086 (10)	0.0316 (6)
H22	0.2919	0.5420	0.1682	0.038*
C23	0.4196 (4)	0.5505 (3)	0.11192 (12)	0.0393 (7)
C24	0.5717 (4)	0.4656 (4)	0.11968 (18)	0.0635 (11)
H24A	0.6458	0.5605	0.1162	0.076*
H24B	0.5584	0.4202	0.0870	0.076*
C25	0.6075 (4)	0.3954 (4)	0.1580 (2)	0.0763 (13)
H25A	0.6895	0.3948	0.1477	0.092*
H25B	0.5330	0.3022	0.1616	0.092*
H25C	0.6236	0.4428	0.1900	0.092*
C26	0.1676 (3)	0.4076 (3)	0.11301 (12)	0.0379 (7)
H26A	0.1646	0.4069	0.0760	0.046*
H26B	0.1781	0.3305	0.1239	0.046*
C27	0.0353 (3)	0.3897 (4)	0.13332 (14)	0.0542 (9)
H27A	0.0276	0.3624	0.1688	0.065*
H27B	0.0400	0.4787	0.1323	0.065*
C28	−0.0880 (4)	0.2914 (5)	0.10747 (18)	0.0647 (11)
C29	−0.2124 (5)	0.0706 (5)	0.0713 (2)	0.0917 (16)
H29A	−0.1884	0.0115	0.0520	0.110*
H29B	−0.2458	0.1137	0.0475	0.110*
C30	−0.3222 (5)	−0.0134 (6)	0.1078 (3)	0.119 (2)
H30A	−0.4005	−0.0841	0.0899	0.142*
H30B	−0.3488	0.0442	0.1259	0.142*
H30C	−0.2890	−0.0555	0.1316	0.142*
C31	0.3113 (3)	0.8790 (3)	0.11318 (11)	0.0308 (6)
C32	0.2619 (3)	0.8783 (3)	0.06410 (11)	0.0378 (6)
H32	0.2306	0.8034	0.0391	0.045*
C33	0.2664 (3)	1.0023 (4)	0.05725 (13)	0.0464 (8)
H33	0.2362	1.0297	0.0266	0.056*
C34	0.3176 (3)	1.0814 (3)	0.10123 (14)	0.0468 (8)
H34	0.3302	1.1736	0.1070	0.056*
C35	0.3450 (3)	1.0043 (3)	0.13580 (12)	0.0379 (6)
H35	0.3811	1.0329	0.1704	0.045*
C36	0.0070 (3)	0.7500 (3)	0.16092 (12)	0.0433 (7)
H36	0.0204	0.6815	0.1794	0.052*
C37	−0.0447 (3)	0.7358 (4)	0.11175 (14)	0.0513 (9)
H37	−0.0740	0.6556	0.0894	0.062*
C38	−0.0452 (4)	0.8565 (4)	0.09965 (14)	0.0544 (10)
H38	−0.0755	0.8761	0.0672	0.065*
C39	0.0031 (4)	0.9435 (4)	0.14116 (14)	0.0494 (8)
H39	0.0133	1.0357	0.1433	0.059*
C40	0.0362 (3)	0.8782 (3)	0.17928 (12)	0.0428 (7)
H40	0.0736	0.9161	0.2130	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0377 (2)	0.0263 (2)	0.0467 (3)	0.01702 (19)	−0.01176 (19)	−0.00115 (18)
O1	0.0379 (11)	0.0414 (11)	0.0299 (10)	0.0133 (9)	0.0018 (8)	−0.0040 (8)
O2	0.0684 (18)	0.0561 (16)	0.0768 (18)	0.0313 (14)	−0.0309 (15)	−0.0016 (14)
O3	0.0378 (12)	0.0300 (11)	0.0770 (16)	0.0160 (10)	−0.0102 (11)	−0.0044 (11)
O4	0.0439 (14)	0.0677 (18)	0.096 (2)	0.0250 (14)	−0.0204 (14)	−0.0279 (16)
O5	0.0551 (18)	0.0512 (17)	0.142 (3)	0.0326 (15)	0.0075 (18)	0.0070 (19)
N1	0.0330 (12)	0.0332 (13)	0.0282 (12)	0.0107 (10)	−0.0001 (10)	−0.0038 (9)
C1	0.0297 (13)	0.0295 (13)	0.0278 (13)	0.0173 (11)	−0.0005 (10)	0.0023 (10)
C2	0.0318 (15)	0.0297 (14)	0.0305 (14)	0.0110 (12)	0.0001 (11)	0.0014 (11)
C3	0.0328 (16)	0.0344 (16)	0.0462 (17)	0.0154 (13)	−0.0027 (13)	−0.0044 (13)
C4	0.053 (2)	0.0364 (19)	0.109 (3)	0.0252 (17)	−0.002 (2)	0.008 (2)
C5	0.067 (3)	0.044 (2)	0.151 (5)	0.029 (2)	−0.013 (3)	−0.008 (3)
C6	0.0296 (15)	0.0354 (15)	0.0406 (16)	0.0101 (13)	0.0018 (12)	0.0052 (13)
C7	0.0334 (15)	0.0374 (16)	0.0550 (19)	0.0152 (13)	0.0073 (14)	0.0033 (14)
C8	0.0411 (18)	0.0501 (19)	0.0438 (18)	0.0231 (16)	0.0043 (14)	0.0094 (15)
C9	0.062 (3)	0.069 (3)	0.183 (6)	0.048 (3)	0.001 (3)	0.014 (4)
C10	0.057 (3)	0.100 (4)	0.117 (4)	0.040 (3)	0.011 (3)	−0.025 (3)
C11	0.0298 (13)	0.0289 (13)	0.0348 (15)	0.0182 (11)	−0.0028 (11)	0.0017 (11)
C12	0.0386 (15)	0.0279 (13)	0.0329 (14)	0.0174 (12)	−0.0038 (12)	0.0013 (11)
C13	0.0432 (17)	0.0331 (15)	0.0409 (16)	0.0192 (14)	−0.0149 (13)	−0.0049 (12)
C14	0.0332 (16)	0.0330 (16)	0.055 (2)	0.0124 (13)	−0.0140 (14)	0.0021 (14)
C15	0.0318 (15)	0.0358 (15)	0.0408 (16)	0.0151 (13)	−0.0013 (12)	0.0046 (12)
C16	0.056 (2)	0.0430 (19)	0.084 (3)	0.0307 (17)	−0.038 (2)	−0.0131 (19)
C17	0.051 (2)	0.057 (2)	0.093 (3)	0.0371 (19)	−0.016 (2)	−0.012 (2)
C18	0.076 (3)	0.060 (2)	0.084 (3)	0.052 (2)	−0.026 (2)	−0.018 (2)
C19	0.077 (3)	0.0274 (17)	0.093 (3)	0.0269 (18)	−0.041 (3)	−0.0061 (19)
C20	0.079 (3)	0.0412 (19)	0.070 (2)	0.0357 (19)	−0.028 (2)	0.0017 (17)
Fe2	0.0309 (2)	0.0363 (2)	0.0331 (2)	0.01991 (19)	0.00006 (17)	0.00118 (17)
O6	0.0538 (13)	0.0378 (11)	0.0327 (11)	0.0263 (10)	−0.0096 (9)	−0.0024 (8)
O7	0.0625 (18)	0.087 (2)	0.0684 (19)	0.0398 (16)	0.0284 (14)	0.0346 (16)
O8	0.0391 (12)	0.0390 (12)	0.0636 (14)	0.0211 (10)	0.0028 (11)	0.0024 (11)
O9	0.086 (3)	0.152 (4)	0.165 (4)	0.079 (3)	−0.054 (3)	−0.070 (3)
O10	0.067 (2)	0.0524 (18)	0.131 (3)	0.0144 (15)	−0.042 (2)	0.0034 (18)
N2	0.0429 (14)	0.0312 (13)	0.0299 (12)	0.0191 (11)	−0.0053 (10)	0.0026 (9)
C21	0.0259 (12)	0.0301 (13)	0.0291 (13)	0.0142 (11)	0.0023 (10)	0.0043 (10)
C22	0.0368 (15)	0.0269 (13)	0.0295 (14)	0.0148 (12)	0.0004 (11)	0.0016 (11)
C23	0.0472 (17)	0.0340 (15)	0.0347 (15)	0.0189 (13)	−0.0041 (13)	−0.0031 (12)
C24	0.044 (2)	0.054 (2)	0.098 (3)	0.0283 (19)	0.005 (2)	−0.017 (2)
C25	0.054 (2)	0.057 (2)	0.128 (4)	0.035 (2)	−0.020 (2)	−0.024 (3)
C26	0.0382 (17)	0.0283 (14)	0.0423 (16)	0.0129 (13)	−0.0006 (13)	0.0012 (12)
C27	0.0423 (18)	0.050 (2)	0.063 (2)	0.0170 (16)	0.0002 (16)	−0.0045 (17)
C28	0.047 (2)	0.062 (3)	0.075 (3)	0.020 (2)	0.001 (2)	0.001 (2)
C29	0.083 (4)	0.073 (3)	0.108 (4)	0.031 (3)	−0.020 (3)	−0.009 (3)
C30	0.047 (3)	0.106 (5)	0.155 (6)	0.002 (3)	−0.006 (3)	−0.003 (4)
C31	0.0245 (13)	0.0331 (14)	0.0359 (15)	0.0154 (12)	0.0066 (11)	0.0090 (12)
C32	0.0444 (17)	0.0512 (18)	0.0300 (14)	0.0331 (15)	0.0089 (12)	0.0095 (12)
C33	0.0497 (19)	0.055 (2)	0.0458 (18)	0.0350 (17)	0.0115 (15)	0.0190 (15)
C34	0.0433 (18)	0.0334 (16)	0.064 (2)	0.0196 (15)	0.0083 (16)	0.0113 (15)
C35	0.0287 (14)	0.0336 (15)	0.0504 (18)	0.0147 (12)	0.0007 (13)	0.0032 (13)
C36	0.0341 (15)	0.0495 (18)	0.0445 (18)	0.0195 (14)	0.0062 (13)	0.0074 (14)
C37	0.0321 (17)	0.060 (2)	0.053 (2)	0.0164 (16)	−0.0032 (15)	−0.0116 (17)
C38	0.0429 (19)	0.083 (3)	0.049 (2)	0.040 (2)	−0.0034 (15)	0.0075 (19)
C39	0.0455 (19)	0.061 (2)	0.057 (2)	0.0386 (18)	0.0080 (16)	0.0033 (17)
C40	0.0411 (16)	0.0527 (19)	0.0407 (16)	0.0281 (15)	0.0050 (13)	−0.0018 (14)

Geometric parameters (Å, º) top

Fe1—C11	2.018 (3)	Fe2—C31	2.017 (3)
Fe1—C12	2.027 (3)	Fe2—C32	2.021 (3)
Fe1—C16	2.032 (3)	Fe2—C35	2.033 (3)
Fe1—C17	2.035 (4)	Fe2—C38	2.034 (3)
Fe1—C20	2.038 (3)	Fe2—C33	2.034 (3)
Fe1—C15	2.039 (3)	Fe2—C36	2.041 (3)
Fe1—C19	2.040 (3)	Fe2—C40	2.041 (3)
Fe1—C18	2.043 (4)	Fe2—C39	2.042 (3)
Fe1—C13	2.052 (3)	Fe2—C37	2.048 (4)
Fe1—C14	2.053 (3)	Fe2—C34	2.054 (3)
O1—C1	1.234 (3)	O6—C21	1.227 (3)
O2—C3	1.183 (4)	O7—C23	1.196 (4)
O3—C3	1.333 (4)	O8—C23	1.345 (4)
O3—C4	1.475 (4)	O8—C24	1.451 (4)
O4—C8	1.201 (4)	O9—C28	1.176 (6)
O5—C8	1.302 (4)	O10—C28	1.320 (6)
O5—C9	1.507 (5)	O10—C29	1.495 (5)
N1—C1	1.334 (4)	N2—C21	1.334 (4)
N1—C2	1.444 (4)	N2—C22	1.453 (3)
N1—H1N	0.8800	N2—H2N	0.8800
C1—C11	1.481 (4)	C21—C31	1.485 (4)
C2—C6	1.532 (4)	C22—C23	1.508 (5)
C2—C3	1.542 (4)	C22—C26	1.539 (4)
C2—H2	1.0000	C22—H22	1.0000
C4—C5	1.436 (6)	C24—C25	1.479 (6)
C4—H4A	0.9900	C24—H24A	0.9900
C4—H4B	0.9900	C24—H24B	0.9900
C5—H5A	0.9800	C25—H25A	0.9800
C5—H5B	0.9800	C25—H25B	0.9800
C5—H5C	0.9800	C25—H25C	0.9800
C6—C7	1.517 (4)	C26—C27	1.519 (5)
C6—H6A	0.9900	C26—H26A	0.9900
C6—H6B	0.9900	C26—H26B	0.9900
C7—C8	1.493 (4)	C27—C28	1.463 (5)
C7—H7A	0.9900	C27—H27A	0.9900
C7—H7B	0.9900	C27—H27B	0.9900
C9—C10	1.471 (8)	C29—C30	1.498 (8)
C9—H9A	0.9900	C29—H29A	0.9900
C9—H9B	0.9900	C29—H29B	0.9900
C10—H10A	0.9800	C30—H30A	0.9800
C10—H10B	0.9800	C30—H30B	0.9800
C10—H10C	0.9800	C30—H30C	0.9800
C11—C12	1.419 (4)	C31—C35	1.417 (4)
C11—C15	1.422 (4)	C31—C32	1.428 (4)
C12—C13	1.415 (4)	C32—C33	1.403 (4)
C12—H12	1.0000	C32—H32	1.0000
C13—C14	1.416 (5)	C33—C34	1.419 (5)
C13—H13	1.0000	C33—H33	1.0000
C14—C15	1.428 (5)	C34—C35	1.416 (5)
C14—H14	1.0000	C34—H34	1.0000
C15—H15	1.0000	C35—H35	1.0000
C16—C17	1.402 (6)	C36—C40	1.417 (5)
C16—C20	1.411 (6)	C36—C37	1.418 (5)
C16—H16	1.0000	C36—H36	1.0000
C17—C18	1.431 (6)	C37—C38	1.419 (5)
C17—H17	1.0000	C37—H37	1.0000
C18—C19	1.395 (6)	C38—C39	1.406 (5)
C18—H18	1.0000	C38—H38	1.0000
C19—C20	1.451 (5)	C39—C40	1.422 (5)
C19—H19	1.0000	C39—H39	1.0000
C20—H20	1.0000	C40—H40	1.0000

C11—Fe1—C12	41.07 (11)	C31—Fe2—C32	41.43 (11)
C11—Fe1—C16	107.23 (12)	C31—Fe2—C35	40.96 (12)
C12—Fe1—C16	125.17 (14)	C32—Fe2—C35	69.10 (13)
C11—Fe1—C17	119.02 (14)	C31—Fe2—C38	156.26 (14)
C12—Fe1—C17	106.59 (16)	C32—Fe2—C38	120.42 (14)
C16—Fe1—C17	40.33 (18)	C35—Fe2—C38	161.39 (15)
C11—Fe1—C20	125.27 (14)	C31—Fe2—C33	68.56 (11)
C12—Fe1—C20	162.54 (13)	C32—Fe2—C33	40.47 (12)
C16—Fe1—C20	40.57 (16)	C35—Fe2—C33	68.24 (13)
C17—Fe1—C20	68.62 (19)	C38—Fe2—C33	107.68 (15)
C11—Fe1—C15	41.03 (11)	C31—Fe2—C36	107.80 (12)
C12—Fe1—C15	68.92 (12)	C32—Fe2—C36	125.68 (13)
C16—Fe1—C15	120.42 (15)	C35—Fe2—C36	120.90 (13)
C17—Fe1—C15	154.42 (14)	C38—Fe2—C36	68.42 (15)
C20—Fe1—C15	107.72 (15)	C33—Fe2—C36	162.66 (14)
C11—Fe1—C19	164.25 (17)	C31—Fe2—C40	125.02 (12)
C12—Fe1—C19	153.80 (15)	C32—Fe2—C40	162.82 (12)
C16—Fe1—C19	68.46 (15)	C35—Fe2—C40	107.34 (13)
C17—Fe1—C19	68.21 (19)	C38—Fe2—C40	68.34 (14)
C20—Fe1—C19	41.70 (15)	C33—Fe2—C40	155.33 (13)
C15—Fe1—C19	126.91 (17)	C36—Fe2—C40	40.61 (13)
C11—Fe1—C18	154.17 (17)	C31—Fe2—C39	162.05 (14)
C12—Fe1—C18	119.23 (16)	C32—Fe2—C39	155.01 (13)
C16—Fe1—C18	68.38 (16)	C35—Fe2—C39	124.68 (14)
C17—Fe1—C18	41.07 (16)	C38—Fe2—C39	40.36 (15)
C20—Fe1—C18	68.95 (18)	C33—Fe2—C39	120.38 (14)
C15—Fe1—C18	163.34 (16)	C36—Fe2—C39	68.36 (14)
C19—Fe1—C18	39.95 (18)	C40—Fe2—C39	40.76 (13)
C11—Fe1—C13	68.56 (11)	C31—Fe2—C37	121.18 (14)
C12—Fe1—C13	40.59 (11)	C32—Fe2—C37	107.88 (14)
C16—Fe1—C13	162.41 (16)	C35—Fe2—C37	156.32 (14)
C17—Fe1—C13	125.48 (17)	C38—Fe2—C37	40.68 (15)
C20—Fe1—C13	155.67 (14)	C33—Fe2—C37	125.59 (15)
C15—Fe1—C13	68.39 (12)	C36—Fe2—C37	40.59 (14)
C19—Fe1—C13	120.16 (14)	C40—Fe2—C37	68.24 (14)
C18—Fe1—C13	107.52 (15)	C39—Fe2—C37	68.12 (16)
C11—Fe1—C14	68.76 (12)	C31—Fe2—C34	68.69 (12)
C12—Fe1—C14	68.47 (12)	C32—Fe2—C34	68.72 (14)
C16—Fe1—C14	155.75 (16)	C35—Fe2—C34	40.52 (13)
C17—Fe1—C14	162.90 (16)	C38—Fe2—C34	124.66 (15)
C20—Fe1—C14	120.95 (16)	C33—Fe2—C34	40.62 (15)
C15—Fe1—C14	40.83 (13)	C36—Fe2—C34	155.50 (14)
C19—Fe1—C14	108.55 (15)	C40—Fe2—C34	120.20 (14)
C18—Fe1—C14	125.77 (15)	C39—Fe2—C34	107.10 (14)
C13—Fe1—C14	40.36 (13)	C37—Fe2—C34	162.11 (15)
C3—O3—C4	114.3 (3)	C23—O8—C24	116.8 (3)
C8—O5—C9	116.3 (3)	C28—O10—C29	116.3 (4)
C1—N1—C2	123.3 (2)	C21—N2—C22	123.6 (2)
C1—N1—H1N	118.3	C21—N2—H2N	118.2
C2—N1—H1N	118.3	C22—N2—H2N	118.2
O1—C1—N1	123.2 (2)	O6—C21—N2	123.3 (2)
O1—C1—C11	120.3 (2)	O6—C21—C31	120.2 (3)
N1—C1—C11	116.5 (2)	N2—C21—C31	116.5 (2)
N1—C2—C6	111.3 (2)	N2—C22—C23	109.5 (2)
N1—C2—C3	109.4 (2)	N2—C22—C26	109.8 (2)
C6—C2—C3	109.6 (2)	C23—C22—C26	110.2 (2)
N1—C2—H2	108.8	N2—C22—H22	109.1
C6—C2—H2	108.8	C23—C22—H22	109.1
C3—C2—H2	108.8	C26—C22—H22	109.1
O2—C3—O3	126.0 (3)	O7—C23—O8	122.9 (4)
O2—C3—C2	123.8 (3)	O7—C23—C22	124.6 (3)
O3—C3—C2	110.3 (3)	O8—C23—C22	112.5 (3)
C5—C4—O3	108.5 (4)	O8—C24—C25	108.9 (4)
C5—C4—H4A	110.0	O8—C24—H24A	109.9
O3—C4—H4A	110.0	C25—C24—H24A	109.9
C5—C4—H4B	110.0	O8—C24—H24B	109.9
O3—C4—H4B	110.0	C25—C24—H24B	109.9
H4A—C4—H4B	108.4	H24A—C24—H24B	108.3
C4—C5—H5A	109.5	C24—C25—H25A	109.5
C4—C5—H5B	109.5	C24—C25—H25B	109.5
H5A—C5—H5B	109.5	H25A—C25—H25B	109.5
C4—C5—H5C	109.5	C24—C25—H25C	109.5
H5A—C5—H5C	109.5	H25A—C25—H25C	109.5
H5B—C5—H5C	109.5	H25B—C25—H25C	109.5
C7—C6—C2	112.9 (2)	C27—C26—C22	112.1 (3)
C7—C6—H6A	109.0	C27—C26—H26A	109.2
C2—C6—H6A	109.0	C22—C26—H26A	109.2
C7—C6—H6B	109.0	C27—C26—H26B	109.2
C2—C6—H6B	109.0	C22—C26—H26B	109.2
H6A—C6—H6B	107.8	H26A—C26—H26B	107.9
C8—C7—C6	112.9 (3)	C28—C27—C26	116.4 (3)
C8—C7—H7A	109.0	C28—C27—H27A	108.2
C6—C7—H7A	109.0	C26—C27—H27A	108.2
C8—C7—H7B	109.0	C28—C27—H27B	108.2
C6—C7—H7B	109.0	C26—C27—H27B	108.2
H7A—C7—H7B	107.8	H27A—C27—H27B	107.3
O4—C8—O5	123.4 (3)	O9—C28—O10	120.7 (5)
O4—C8—C7	123.5 (3)	O9—C28—C27	126.4 (5)
O5—C8—C7	113.1 (3)	O10—C28—C27	112.7 (4)
C10—C9—O5	110.7 (5)	O10—C29—C30	111.3 (5)
C10—C9—H9A	109.5	O10—C29—H29A	109.4
O5—C9—H9A	109.5	C30—C29—H29A	109.4
C10—C9—H9B	109.5	O10—C29—H29B	109.4
O5—C9—H9B	109.5	C30—C29—H29B	109.4
H9A—C9—H9B	108.1	H29A—C29—H29B	108.0
C9—C10—H10A	109.5	C29—C30—H30A	109.5
C9—C10—H10B	109.5	C29—C30—H30B	109.5
H10A—C10—H10B	109.5	H30A—C30—H30B	109.5
C9—C10—H10C	109.5	C29—C30—H30C	109.5
H10A—C10—H10C	109.5	H30A—C30—H30C	109.5
H10B—C10—H10C	109.5	H30B—C30—H30C	109.5
C12—C11—C15	108.2 (2)	C35—C31—C32	107.8 (3)
C12—C11—C1	128.5 (2)	C35—C31—C21	124.2 (3)
C15—C11—C1	123.1 (3)	C32—C31—C21	127.9 (3)
C12—C11—Fe1	69.82 (15)	C35—C31—Fe2	70.14 (16)
C15—C11—Fe1	70.30 (16)	C32—C31—Fe2	69.46 (16)
C1—C11—Fe1	121.23 (18)	C21—C31—Fe2	123.04 (18)
C13—C12—C11	108.0 (3)	C33—C32—C31	107.4 (3)
C13—C12—Fe1	70.66 (16)	C33—C32—Fe2	70.26 (18)
C11—C12—Fe1	69.11 (15)	C31—C32—Fe2	69.12 (16)
C13—C12—H12	126.0	C33—C32—H32	126.3
C11—C12—H12	126.0	C31—C32—H32	126.3
Fe1—C12—H12	126.0	Fe2—C32—H32	126.3
C12—C13—C14	108.4 (3)	C32—C33—C34	109.2 (3)
C12—C13—Fe1	68.75 (16)	C32—C33—Fe2	69.27 (17)
C14—C13—Fe1	69.87 (17)	C34—C33—Fe2	70.44 (19)
C12—C13—H13	125.8	C32—C33—H33	125.4
C14—C13—H13	125.8	C34—C33—H33	125.4
Fe1—C13—H13	125.8	Fe2—C33—H33	125.4
C13—C14—C15	107.9 (3)	C35—C34—C33	107.2 (3)
C13—C14—Fe1	69.77 (17)	C35—C34—Fe2	68.95 (17)
C15—C14—Fe1	69.05 (17)	C33—C34—Fe2	68.93 (19)
C13—C14—H14	126.0	C35—C34—H34	126.4
C15—C14—H14	126.0	C33—C34—H34	126.4
Fe1—C14—H14	126.0	Fe2—C34—H34	126.4
C11—C15—C14	107.6 (3)	C34—C35—C31	108.4 (3)
C11—C15—Fe1	68.66 (16)	C34—C35—Fe2	70.53 (18)
C14—C15—Fe1	70.12 (18)	C31—C35—Fe2	68.90 (16)
C11—C15—H15	126.2	C34—C35—H35	125.8
C14—C15—H15	126.2	C31—C35—H35	125.8
Fe1—C15—H15	126.2	Fe2—C35—H35	125.8
C17—C16—C20	109.4 (3)	C40—C36—C37	108.0 (3)
C17—C16—Fe1	69.9 (2)	C40—C36—Fe2	69.72 (18)
C20—C16—Fe1	69.92 (19)	C37—C36—Fe2	70.0 (2)
C17—C16—H16	125.3	C40—C36—H36	126.0
C20—C16—H16	125.3	C37—C36—H36	126.0
Fe1—C16—H16	125.3	Fe2—C36—H36	126.0
C16—C17—C18	107.9 (4)	C36—C37—C38	107.7 (3)
C16—C17—Fe1	69.7 (2)	C36—C37—Fe2	69.42 (19)
C18—C17—Fe1	69.8 (2)	C38—C37—Fe2	69.1 (2)
C16—C17—H17	126.0	C36—C37—H37	126.1
C18—C17—H17	126.0	C38—C37—H37	126.1
Fe1—C17—H17	126.0	Fe2—C37—H37	126.1
C19—C18—C17	107.9 (4)	C39—C38—C37	108.4 (3)
C19—C18—Fe1	69.9 (2)	C39—C38—Fe2	70.1 (2)
C17—C18—Fe1	69.1 (2)	C37—C38—Fe2	70.22 (19)
C19—C18—H18	126.0	C39—C38—H38	125.8
C17—C18—H18	126.0	C37—C38—H38	125.8
Fe1—C18—H18	126.0	Fe2—C38—H38	125.8
C18—C19—C20	108.5 (4)	C38—C39—C40	108.1 (3)
C18—C19—Fe1	70.2 (2)	C38—C39—Fe2	69.51 (19)
C20—C19—Fe1	69.07 (19)	C40—C39—Fe2	69.61 (17)
C18—C19—H19	125.7	C38—C39—H39	126.0
C20—C19—H19	125.7	C40—C39—H39	126.0
Fe1—C19—H19	125.7	Fe2—C39—H39	126.0
C16—C20—C19	106.3 (4)	C36—C40—C39	107.8 (3)
C16—C20—Fe1	69.5 (2)	C36—C40—Fe2	69.67 (18)
C19—C20—Fe1	69.2 (2)	C39—C40—Fe2	69.63 (18)
C16—C20—H20	126.8	C36—C40—H40	126.1
C19—C20—H20	126.8	C39—C40—H40	126.1
Fe1—C20—H20	126.8	Fe2—C40—H40	126.1

C2—N1—C1—O1	−2.5 (4)	C22—N2—C21—O6	−3.9 (4)
C2—N1—C1—C11	178.5 (2)	C22—N2—C21—C31	175.7 (2)
C1—N1—C2—C6	144.9 (3)	C21—N2—C22—C23	−95.3 (3)
C1—N1—C2—C3	−93.9 (3)	C21—N2—C22—C26	143.6 (3)
C4—O3—C3—O2	−1.6 (5)	C24—O8—C23—O7	0.8 (5)
C4—O3—C3—C2	178.4 (3)	C24—O8—C23—C22	−179.1 (3)
N1—C2—C3—O2	−3.2 (4)	N2—C22—C23—O7	−11.5 (5)
C6—C2—C3—O2	119.0 (4)	C26—C22—C23—O7	109.4 (4)
N1—C2—C3—O3	176.8 (3)	N2—C22—C23—O8	168.3 (2)
C6—C2—C3—O3	−60.9 (3)	C26—C22—C23—O8	−70.8 (3)
C3—O3—C4—C5	170.4 (4)	C23—O8—C24—C25	163.0 (3)
N1—C2—C6—C7	−52.6 (3)	N2—C22—C26—C27	−62.1 (3)
C3—C2—C6—C7	−173.7 (3)	C23—C22—C26—C27	177.2 (3)
C2—C6—C7—C8	−160.6 (3)	C22—C26—C27—C28	161.9 (3)
C9—O5—C8—O4	4.1 (6)	C29—O10—C28—O9	−6.3 (8)
C9—O5—C8—C7	−177.1 (4)	C29—O10—C28—C27	179.4 (4)
C6—C7—C8—O4	29.0 (5)	C26—C27—C28—O9	−129.6 (6)
C6—C7—C8—O5	−149.8 (3)	C26—C27—C28—O10	44.3 (5)
C8—O5—C9—C10	−82.9 (6)	C28—O10—C29—C30	−85.1 (6)
O1—C1—C11—C12	177.3 (3)	O6—C21—C31—C35	−2.5 (4)
N1—C1—C11—C12	−3.7 (4)	N2—C21—C31—C35	177.9 (3)
O1—C1—C11—C15	−9.0 (4)	O6—C21—C31—C32	−178.3 (3)
N1—C1—C11—C15	170.1 (3)	N2—C21—C31—C32	2.1 (4)
O1—C1—C11—Fe1	−94.7 (3)	O6—C21—C31—Fe2	−89.7 (3)
N1—C1—C11—Fe1	84.4 (3)	N2—C21—C31—Fe2	90.7 (3)
C16—Fe1—C11—C12	124.2 (2)	C32—Fe2—C31—C35	118.9 (2)
C17—Fe1—C11—C12	82.0 (2)	C38—Fe2—C31—C35	166.3 (3)
C20—Fe1—C11—C12	165.2 (2)	C33—Fe2—C31—C35	81.1 (2)
C15—Fe1—C11—C12	−119.0 (2)	C36—Fe2—C31—C35	−116.93 (19)
C19—Fe1—C11—C12	−164.3 (5)	C40—Fe2—C31—C35	−75.4 (2)
C18—Fe1—C11—C12	48.3 (4)	C39—Fe2—C31—C35	−42.3 (5)
C13—Fe1—C11—C12	−37.70 (17)	C37—Fe2—C31—C35	−159.36 (19)
C14—Fe1—C11—C12	−81.18 (18)	C34—Fe2—C31—C35	37.31 (19)
C12—Fe1—C11—C15	119.0 (2)	C35—Fe2—C31—C32	−118.9 (2)
C16—Fe1—C11—C15	−116.8 (2)	C38—Fe2—C31—C32	47.5 (4)
C17—Fe1—C11—C15	−159.0 (2)	C33—Fe2—C31—C32	−37.79 (19)
C20—Fe1—C11—C15	−75.8 (2)	C36—Fe2—C31—C32	124.20 (19)
C19—Fe1—C11—C15	−45.3 (6)	C40—Fe2—C31—C32	165.72 (18)
C18—Fe1—C11—C15	167.3 (3)	C39—Fe2—C31—C32	−161.2 (4)
C13—Fe1—C11—C15	81.29 (19)	C37—Fe2—C31—C32	81.8 (2)
C14—Fe1—C11—C15	37.82 (19)	C34—Fe2—C31—C32	−81.6 (2)
C12—Fe1—C11—C1	−123.5 (3)	C32—Fe2—C31—C21	−122.6 (3)
C16—Fe1—C11—C1	0.7 (3)	C35—Fe2—C31—C21	118.5 (3)
C17—Fe1—C11—C1	−41.5 (3)	C38—Fe2—C31—C21	−75.2 (4)
C20—Fe1—C11—C1	41.7 (3)	C33—Fe2—C31—C21	−160.4 (3)
C15—Fe1—C11—C1	117.5 (3)	C36—Fe2—C31—C21	1.6 (3)
C19—Fe1—C11—C1	72.2 (6)	C40—Fe2—C31—C21	43.1 (3)
C18—Fe1—C11—C1	−75.2 (4)	C39—Fe2—C31—C21	76.2 (5)
C13—Fe1—C11—C1	−161.2 (3)	C37—Fe2—C31—C21	−40.9 (3)
C14—Fe1—C11—C1	155.3 (3)	C34—Fe2—C31—C21	155.8 (3)
C15—C11—C12—C13	0.1 (3)	C35—C31—C32—C33	0.2 (3)
C1—C11—C12—C13	174.7 (3)	C21—C31—C32—C33	176.6 (3)
Fe1—C11—C12—C13	60.23 (19)	Fe2—C31—C32—C33	60.1 (2)
C15—C11—C12—Fe1	−60.09 (19)	C35—C31—C32—Fe2	−59.90 (19)
C1—C11—C12—Fe1	114.4 (3)	C21—C31—C32—Fe2	116.5 (3)
C11—Fe1—C12—C13	−119.0 (2)	C31—Fe2—C32—C33	−118.5 (3)
C16—Fe1—C12—C13	165.9 (2)	C35—Fe2—C32—C33	−80.6 (2)
C17—Fe1—C12—C13	125.7 (2)	C38—Fe2—C32—C33	81.6 (2)
C20—Fe1—C12—C13	−163.0 (5)	C36—Fe2—C32—C33	165.7 (2)
C15—Fe1—C12—C13	−80.98 (19)	C40—Fe2—C32—C33	−161.6 (4)
C19—Fe1—C12—C13	51.4 (4)	C39—Fe2—C32—C33	47.9 (4)
C18—Fe1—C12—C13	82.9 (2)	C37—Fe2—C32—C33	124.3 (2)
C14—Fe1—C12—C13	−37.01 (19)	C34—Fe2—C32—C33	−37.0 (2)
C16—Fe1—C12—C11	−75.1 (2)	C35—Fe2—C32—C31	37.91 (17)
C17—Fe1—C12—C11	−115.38 (19)	C38—Fe2—C32—C31	−159.88 (19)
C20—Fe1—C12—C11	−44.1 (6)	C33—Fe2—C32—C31	118.5 (3)
C15—Fe1—C12—C11	37.98 (16)	C36—Fe2—C32—C31	−75.8 (2)
C19—Fe1—C12—C11	170.4 (3)	C40—Fe2—C32—C31	−43.1 (5)
C18—Fe1—C12—C11	−158.10 (19)	C39—Fe2—C32—C31	166.4 (3)
C13—Fe1—C12—C11	119.0 (2)	C37—Fe2—C32—C31	−117.2 (2)
C14—Fe1—C12—C11	81.95 (18)	C34—Fe2—C32—C31	81.49 (19)
C11—C12—C13—C14	−0.5 (3)	C31—C32—C33—C34	−0.1 (4)
Fe1—C12—C13—C14	58.8 (2)	Fe2—C32—C33—C34	59.3 (2)
C11—C12—C13—Fe1	−59.25 (19)	C31—C32—C33—Fe2	−59.38 (19)
C11—Fe1—C13—C12	38.14 (17)	C31—Fe2—C33—C32	38.66 (19)
C16—Fe1—C13—C12	−41.2 (5)	C35—Fe2—C33—C32	82.9 (2)
C17—Fe1—C13—C12	−73.0 (2)	C38—Fe2—C33—C32	−116.4 (2)
C20—Fe1—C13—C12	167.7 (3)	C36—Fe2—C33—C32	−42.4 (5)
C15—Fe1—C13—C12	82.41 (18)	C40—Fe2—C33—C32	167.1 (3)
C19—Fe1—C13—C12	−156.5 (2)	C39—Fe2—C33—C32	−158.7 (2)
C18—Fe1—C13—C12	−114.7 (2)	C37—Fe2—C33—C32	−75.1 (2)
C14—Fe1—C13—C12	120.2 (3)	C34—Fe2—C33—C32	120.5 (3)
C11—Fe1—C13—C14	−82.02 (19)	C31—Fe2—C33—C34	−81.9 (2)
C12—Fe1—C13—C14	−120.2 (3)	C32—Fe2—C33—C34	−120.5 (3)
C16—Fe1—C13—C14	−161.3 (4)	C35—Fe2—C33—C34	−37.64 (19)
C17—Fe1—C13—C14	166.9 (2)	C38—Fe2—C33—C34	123.0 (2)
C20—Fe1—C13—C14	47.6 (4)	C36—Fe2—C33—C34	−162.9 (4)
C15—Fe1—C13—C14	−37.75 (18)	C40—Fe2—C33—C34	46.6 (4)
C19—Fe1—C13—C14	83.4 (3)	C39—Fe2—C33—C34	80.8 (2)
C18—Fe1—C13—C14	125.1 (2)	C37—Fe2—C33—C34	164.4 (2)
C12—C13—C14—C15	0.6 (3)	C32—C33—C34—C35	0.0 (4)
Fe1—C13—C14—C15	58.7 (2)	Fe2—C33—C34—C35	58.5 (2)
C12—C13—C14—Fe1	−58.1 (2)	C32—C33—C34—Fe2	−58.6 (2)
C11—Fe1—C14—C13	81.47 (18)	C31—Fe2—C34—C35	−37.70 (19)
C12—Fe1—C14—C13	37.21 (17)	C32—Fe2—C34—C35	−82.3 (2)
C16—Fe1—C14—C13	166.4 (3)	C38—Fe2—C34—C35	164.6 (2)
C17—Fe1—C14—C13	−39.0 (6)	C33—Fe2—C34—C35	−119.2 (3)
C20—Fe1—C14—C13	−159.23 (19)	C36—Fe2—C34—C35	48.6 (4)
C15—Fe1—C14—C13	119.5 (2)	C40—Fe2—C34—C35	81.4 (2)
C19—Fe1—C14—C13	−115.0 (2)	C39—Fe2—C34—C35	123.8 (2)
C18—Fe1—C14—C13	−74.1 (3)	C37—Fe2—C34—C35	−164.6 (4)
C11—Fe1—C14—C15	−38.00 (18)	C31—Fe2—C34—C33	81.5 (2)
C12—Fe1—C14—C15	−82.26 (18)	C32—Fe2—C34—C33	36.87 (18)
C16—Fe1—C14—C15	46.9 (4)	C35—Fe2—C34—C33	119.2 (3)
C17—Fe1—C14—C15	−158.5 (5)	C38—Fe2—C34—C33	−76.2 (2)
C20—Fe1—C14—C15	81.3 (2)	C36—Fe2—C34—C33	167.8 (3)
C19—Fe1—C14—C15	125.5 (2)	C40—Fe2—C34—C33	−159.46 (18)
C18—Fe1—C14—C15	166.5 (2)	C39—Fe2—C34—C33	−117.0 (2)
C13—Fe1—C14—C15	−119.5 (2)	C37—Fe2—C34—C33	−45.4 (5)
C12—C11—C15—C14	0.2 (3)	C33—C34—C35—C31	0.2 (3)
C1—C11—C15—C14	−174.6 (2)	Fe2—C34—C35—C31	58.7 (2)
Fe1—C11—C15—C14	−59.6 (2)	C33—C34—C35—Fe2	−58.5 (2)
C12—C11—C15—Fe1	59.78 (19)	C32—C31—C35—C34	−0.2 (3)
C1—C11—C15—Fe1	−115.1 (3)	C21—C31—C35—C34	−176.8 (3)
C13—C14—C15—C11	−0.5 (3)	Fe2—C31—C35—C34	−59.7 (2)
Fe1—C14—C15—C11	58.6 (2)	C32—C31—C35—Fe2	59.47 (19)
C13—C14—C15—Fe1	−59.1 (2)	C21—C31—C35—Fe2	−117.1 (3)
C12—Fe1—C15—C11	−38.01 (17)	C31—Fe2—C35—C34	119.6 (3)
C16—Fe1—C15—C11	81.3 (2)	C32—Fe2—C35—C34	81.3 (2)
C17—Fe1—C15—C11	46.5 (4)	C38—Fe2—C35—C34	−43.0 (5)
C20—Fe1—C15—C11	123.80 (19)	C33—Fe2—C35—C34	37.7 (2)
C19—Fe1—C15—C11	166.04 (19)	C36—Fe2—C35—C34	−158.7 (2)
C18—Fe1—C15—C11	−160.5 (5)	C40—Fe2—C35—C34	−116.5 (2)
C13—Fe1—C15—C11	−81.73 (18)	C39—Fe2—C35—C34	−75.0 (3)
C14—Fe1—C15—C11	−119.1 (3)	C37—Fe2—C35—C34	168.3 (3)
C11—Fe1—C15—C14	119.1 (3)	C32—Fe2—C35—C31	−38.33 (17)
C12—Fe1—C15—C14	81.05 (19)	C38—Fe2—C35—C31	−162.7 (4)
C16—Fe1—C15—C14	−159.6 (2)	C33—Fe2—C35—C31	−81.91 (19)
C17—Fe1—C15—C14	165.5 (4)	C36—Fe2—C35—C31	81.6 (2)
C20—Fe1—C15—C14	−117.1 (2)	C40—Fe2—C35—C31	123.87 (18)
C19—Fe1—C15—C14	−74.9 (2)	C39—Fe2—C35—C31	165.38 (18)
C18—Fe1—C15—C14	−41.5 (6)	C37—Fe2—C35—C31	48.7 (4)
C13—Fe1—C15—C14	37.33 (18)	C34—Fe2—C35—C31	−119.6 (3)
C11—Fe1—C16—C17	−114.8 (2)	C31—Fe2—C36—C40	123.47 (19)
C12—Fe1—C16—C17	−73.1 (3)	C32—Fe2—C36—C40	165.82 (18)
C20—Fe1—C16—C17	120.6 (3)	C35—Fe2—C36—C40	80.5 (2)
C15—Fe1—C16—C17	−157.6 (2)	C38—Fe2—C36—C40	−81.4 (2)
C19—Fe1—C16—C17	81.3 (3)	C33—Fe2—C36—C40	−161.6 (4)
C18—Fe1—C16—C17	38.2 (3)	C39—Fe2—C36—C40	−37.9 (2)
C13—Fe1—C16—C17	−41.5 (6)	C37—Fe2—C36—C40	−119.1 (3)
C14—Fe1—C16—C17	168.8 (3)	C34—Fe2—C36—C40	45.9 (4)
C11—Fe1—C16—C20	124.6 (2)	C31—Fe2—C36—C37	−117.5 (2)
C12—Fe1—C16—C20	166.2 (2)	C32—Fe2—C36—C37	−75.1 (3)
C17—Fe1—C16—C20	−120.6 (3)	C35—Fe2—C36—C37	−160.4 (2)
C15—Fe1—C16—C20	81.8 (3)	C38—Fe2—C36—C37	37.6 (2)
C19—Fe1—C16—C20	−39.4 (3)	C33—Fe2—C36—C37	−42.5 (5)
C18—Fe1—C16—C20	−82.5 (3)	C40—Fe2—C36—C37	119.1 (3)
C13—Fe1—C16—C20	−162.2 (4)	C39—Fe2—C36—C37	81.2 (2)
C14—Fe1—C16—C20	48.1 (4)	C34—Fe2—C36—C37	165.0 (3)
C20—C16—C17—C18	−0.6 (4)	C40—C36—C37—C38	0.9 (4)
Fe1—C16—C17—C18	−59.6 (3)	Fe2—C36—C37—C38	−58.7 (2)
C20—C16—C17—Fe1	58.9 (2)	C40—C36—C37—Fe2	59.6 (2)
C11—Fe1—C17—C16	82.5 (3)	C31—Fe2—C37—C36	81.0 (2)
C12—Fe1—C17—C16	125.3 (2)	C32—Fe2—C37—C36	124.4 (2)
C20—Fe1—C17—C16	−36.9 (2)	C35—Fe2—C37—C36	45.8 (4)
C15—Fe1—C17—C16	49.6 (5)	C38—Fe2—C37—C36	−119.4 (3)
C19—Fe1—C17—C16	−81.9 (3)	C33—Fe2—C37—C36	165.66 (18)
C18—Fe1—C17—C16	−119.0 (4)	C40—Fe2—C37—C36	−37.8 (2)
C13—Fe1—C17—C16	165.8 (2)	C39—Fe2—C37—C36	−81.8 (2)
C14—Fe1—C17—C16	−164.2 (4)	C34—Fe2—C37—C36	−159.6 (4)
C11—Fe1—C17—C18	−158.5 (2)	C31—Fe2—C37—C38	−159.6 (2)
C12—Fe1—C17—C18	−115.7 (3)	C32—Fe2—C37—C38	−116.2 (2)
C16—Fe1—C17—C18	119.0 (4)	C35—Fe2—C37—C38	165.2 (3)
C20—Fe1—C17—C18	82.1 (3)	C33—Fe2—C37—C38	−74.9 (3)
C15—Fe1—C17—C18	168.6 (3)	C36—Fe2—C37—C38	119.4 (3)
C19—Fe1—C17—C18	37.1 (3)	C40—Fe2—C37—C38	81.6 (2)
C13—Fe1—C17—C18	−75.2 (3)	C39—Fe2—C37—C38	37.6 (2)
C14—Fe1—C17—C18	−45.2 (7)	C34—Fe2—C37—C38	−40.1 (6)
C16—C17—C18—C19	0.2 (4)	C36—C37—C38—C39	−1.1 (4)
Fe1—C17—C18—C19	−59.4 (3)	Fe2—C37—C38—C39	−60.0 (3)
C16—C17—C18—Fe1	59.6 (2)	C36—C37—C38—Fe2	58.9 (2)
C11—Fe1—C18—C19	166.8 (3)	C31—Fe2—C38—C39	166.8 (3)
C12—Fe1—C18—C19	−158.9 (2)	C32—Fe2—C38—C39	−158.8 (2)
C16—Fe1—C18—C19	81.8 (3)	C35—Fe2—C38—C39	−42.2 (6)
C17—Fe1—C18—C19	119.3 (4)	C33—Fe2—C38—C39	−116.4 (2)
C20—Fe1—C18—C19	38.1 (2)	C36—Fe2—C38—C39	81.5 (2)
C15—Fe1—C18—C19	−43.3 (6)	C40—Fe2—C38—C39	37.7 (2)
C13—Fe1—C18—C19	−116.3 (2)	C37—Fe2—C38—C39	119.1 (3)
C14—Fe1—C18—C19	−75.6 (3)	C34—Fe2—C38—C39	−74.8 (3)
C11—Fe1—C18—C17	47.5 (5)	C31—Fe2—C38—C37	47.7 (4)
C12—Fe1—C18—C17	81.7 (3)	C32—Fe2—C38—C37	82.1 (2)
C16—Fe1—C18—C17	−37.5 (3)	C35—Fe2—C38—C37	−161.3 (4)
C20—Fe1—C18—C17	−81.2 (3)	C33—Fe2—C38—C37	124.5 (2)
C15—Fe1—C18—C17	−162.6 (5)	C36—Fe2—C38—C37	−37.5 (2)
C19—Fe1—C18—C17	−119.3 (4)	C40—Fe2—C38—C37	−81.4 (2)
C13—Fe1—C18—C17	124.3 (3)	C39—Fe2—C38—C37	−119.1 (3)
C14—Fe1—C18—C17	165.1 (2)	C34—Fe2—C38—C37	166.1 (2)
C17—C18—C19—C20	0.3 (4)	C37—C38—C39—C40	0.9 (4)
Fe1—C18—C19—C20	−58.6 (2)	Fe2—C38—C39—C40	−59.1 (2)
C17—C18—C19—Fe1	58.9 (3)	C37—C38—C39—Fe2	60.0 (2)
C11—Fe1—C19—C18	−158.6 (5)	C31—Fe2—C39—C38	−162.6 (4)
C12—Fe1—C19—C18	45.3 (4)	C32—Fe2—C39—C38	47.6 (4)
C16—Fe1—C19—C18	−81.6 (3)	C35—Fe2—C39—C38	164.9 (2)
C17—Fe1—C19—C18	−38.1 (2)	C33—Fe2—C39—C38	81.6 (3)
C20—Fe1—C19—C18	−120.0 (4)	C36—Fe2—C39—C38	−81.7 (2)
C15—Fe1—C19—C18	165.8 (2)	C40—Fe2—C39—C38	−119.5 (3)
C13—Fe1—C19—C18	81.3 (3)	C37—Fe2—C39—C38	−37.9 (2)
C14—Fe1—C19—C18	124.0 (2)	C34—Fe2—C39—C38	123.8 (2)
C11—Fe1—C19—C20	−38.6 (7)	C31—Fe2—C39—C40	−43.2 (5)
C12—Fe1—C19—C20	165.2 (3)	C32—Fe2—C39—C40	167.1 (3)
C16—Fe1—C19—C20	38.3 (3)	C35—Fe2—C39—C40	−75.7 (2)
C17—Fe1—C19—C20	81.9 (3)	C38—Fe2—C39—C40	119.5 (3)
C15—Fe1—C19—C20	−74.3 (3)	C33—Fe2—C39—C40	−159.0 (2)
C18—Fe1—C19—C20	120.0 (4)	C36—Fe2—C39—C40	37.7 (2)
C13—Fe1—C19—C20	−158.8 (2)	C37—Fe2—C39—C40	81.6 (2)
C14—Fe1—C19—C20	−116.0 (3)	C34—Fe2—C39—C40	−116.7 (2)
C17—C16—C20—C19	0.8 (4)	C37—C36—C40—C39	−0.3 (4)
Fe1—C16—C20—C19	59.8 (2)	Fe2—C36—C40—C39	59.4 (2)
C17—C16—C20—Fe1	−58.9 (2)	C37—C36—C40—Fe2	−59.7 (2)
C18—C19—C20—C16	−0.7 (4)	C38—C39—C40—C36	−0.4 (4)
Fe1—C19—C20—C16	−59.9 (2)	Fe2—C39—C40—C36	−59.4 (2)
C18—C19—C20—Fe1	59.3 (3)	C38—C39—C40—Fe2	59.1 (2)
C11—Fe1—C20—C16	−74.4 (3)	C31—Fe2—C40—C36	−75.9 (2)
C12—Fe1—C20—C16	−40.4 (6)	C32—Fe2—C40—C36	−42.4 (5)
C17—Fe1—C20—C16	36.7 (2)	C35—Fe2—C40—C36	−117.54 (19)
C15—Fe1—C20—C16	−116.4 (2)	C38—Fe2—C40—C36	81.7 (2)
C19—Fe1—C20—C16	117.5 (4)	C33—Fe2—C40—C36	167.0 (3)
C18—Fe1—C20—C16	80.9 (3)	C39—Fe2—C40—C36	119.0 (3)
C13—Fe1—C20—C16	167.0 (3)	C37—Fe2—C40—C36	37.8 (2)
C14—Fe1—C20—C16	−159.1 (2)	C34—Fe2—C40—C36	−159.83 (19)
C11—Fe1—C20—C19	168.0 (2)	C31—Fe2—C40—C39	165.1 (2)
C12—Fe1—C20—C19	−157.9 (5)	C32—Fe2—C40—C39	−161.4 (4)
C16—Fe1—C20—C19	−117.5 (4)	C35—Fe2—C40—C39	123.4 (2)
C17—Fe1—C20—C19	−80.8 (3)	C38—Fe2—C40—C39	−37.4 (2)
C15—Fe1—C20—C19	126.1 (3)	C33—Fe2—C40—C39	47.9 (4)
C18—Fe1—C20—C19	−36.6 (3)	C36—Fe2—C40—C39	−119.0 (3)
C13—Fe1—C20—C19	49.5 (5)	C37—Fe2—C40—C39	−81.3 (2)
C14—Fe1—C20—C19	83.4 (3)	C34—Fe2—C40—C39	81.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6ⁱ	0.88	1.97	2.822 (3)	163
N2—H2N···O1	0.88	2.01	2.861 (3)	162

Symmetry code: (i) −x+y, −x+1, z−1/3.

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