Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102011605/sk1557sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102011605/sk1557Isup2.hkl |
CCDC reference: 193403
The title compound was prepared from the trifluoromethanesulfonate complex of iron(III) porphyrin and three equivalents of L-valine methyl ester, as previously reported for the L-leucine methyl ester ligands (Morice et al., 1998). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a CH2Cl2-hexane solution in the presence of a small excess of the amino ester.
The title compound crystallized in triclinic space group P1 with two molecules in the asymmetric unit. The structure showed a pseudo I centring. Previous studies at room temperature showed a rather high thermal motion, disordered trifluoromethanesulfonate anions and a large thermal motion for the two dichloromethane molecules, the consequence of which was a ratio of reflections to parameters which was too low. The use of the CCD technique at low temperature enabled the reduction of this thermal motion and a very significant increase of the reflections to parameters ratio. Furthermore, the trifluoromethanesulfonate anions were no longer disordered. After anisotropic refinement (cations, anions and solvent molecules), most of the H atoms were found in a difference Fourier map and treated as riding, with C—H = 0.93–0.98 Å and N—H = 0.90 Å. Are these the correct constraints? It was also possible to confirm the absolute configuration unambiguously using the Friedel pairs.
Data collection: KappaCCD Server Software (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97.
[Fe(C44H28N4)(C6H13NO2)2]CF3O3S·CH2Cl2 | Z = 2 |
Mr = 1164.90 | F(000) = 1210 |
Triclinic, P1 | Dx = 1.408 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 11.3660 (2) Å | Cell parameters from 16340 reflections |
b = 14.4438 (2) Å | θ = 1.0–32.0° |
c = 17.6675 (2) Å | µ = 0.48 mm−1 |
α = 78.148 (1)° | T = 120 K |
β = 87.016 (1)° | Prism, black |
γ = 75.485 (1)° | 0.24 × 0.18 × 0.11 mm |
V = 2748.01 (7) Å3 |
Nonius KappaCCD area-detector diffractometer | 23226 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 32.0°, θmin = 1.5° |
Detector resolution: 19.24 pixels mm-1 | h = −16→16 |
33368 measured reflections | k = −21→21 |
33368 independent reflections | l = −26→26 |
Refinement on F2 | Hydrogen site location: difmap and geom |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.0588P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.133 | (Δ/σ)max = 0.001 |
S = 0.99 | Δρmax = 0.76 e Å−3 |
33368 reflections | Δρmin = −0.59 e Å−3 |
1406 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0012 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.008 (8) |
[Fe(C44H28N4)(C6H13NO2)2]CF3O3S·CH2Cl2 | γ = 75.485 (1)° |
Mr = 1164.90 | V = 2748.01 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.3660 (2) Å | Mo Kα radiation |
b = 14.4438 (2) Å | µ = 0.48 mm−1 |
c = 17.6675 (2) Å | T = 120 K |
α = 78.148 (1)° | 0.24 × 0.18 × 0.11 mm |
β = 87.016 (1)° |
Nonius KappaCCD area-detector diffractometer | 23226 reflections with I > 2σ(I) |
33368 measured reflections | Rint = 0.000 |
33368 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.133 | Δρmax = 0.76 e Å−3 |
S = 0.99 | Δρmin = −0.59 e Å−3 |
33368 reflections | Absolute structure: Flack (1983) |
1406 parameters | Absolute structure parameter: −0.008 (8) |
3 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.10460 (7) | 0.26075 (5) | 0.49321 (4) | 0.02943 (16) | |
S2 | 0.60857 (8) | 0.75677 (5) | −0.05624 (5) | 0.03372 (17) | |
O9 | 0.0724 (3) | 0.28711 (17) | 0.56682 (13) | 0.0511 (7) | |
O10 | 0.0924 (2) | 0.16627 (14) | 0.48557 (13) | 0.0449 (6) | |
O11 | 0.21169 (19) | 0.28634 (17) | 0.45824 (13) | 0.0359 (5) | |
O12 | 0.6113 (3) | 0.65631 (15) | −0.02635 (15) | 0.0651 (9) | |
O13 | 0.5637 (2) | 0.79608 (16) | −0.13396 (13) | 0.0471 (6) | |
O14 | 0.7146 (2) | 0.7867 (2) | −0.03975 (17) | 0.0562 (7) | |
C117 | −0.0137 (3) | 0.3443 (2) | 0.4302 (2) | 0.0412 (8) | |
C118 | 0.4940 (3) | 0.8226 (2) | 0.0014 (2) | 0.0372 (7) | |
F1 | −0.12462 (19) | 0.33607 (18) | 0.45227 (19) | 0.0773 (8) | |
F2 | 0.0020 (2) | 0.32956 (15) | 0.35693 (13) | 0.0637 (7) | |
F3 | −0.01169 (18) | 0.43663 (12) | 0.42765 (13) | 0.0490 (5) | |
F4 | 0.3847 (2) | 0.80757 (18) | −0.00734 (18) | 0.0740 (8) | |
F5 | 0.5224 (2) | 0.79712 (16) | 0.07635 (12) | 0.0610 (6) | |
F6 | 0.48325 (17) | 0.91824 (12) | −0.01999 (12) | 0.0444 (5) | |
Cl1 | 0.33337 (8) | 0.35856 (5) | 0.20240 (4) | 0.03885 (18) | |
Cl2 | 0.43929 (8) | 0.42109 (6) | 0.32392 (5) | 0.0447 (2) | |
Cl3 | 0.83333 (7) | 0.84265 (5) | −0.30816 (4) | 0.03554 (17) | |
Cl4 | 0.92633 (9) | 0.90497 (6) | −0.18110 (5) | 0.0445 (2) | |
C119 | 0.3522 (3) | 0.3455 (3) | 0.30319 (18) | 0.0433 (8) | |
H11A | 0.2730 | 0.3614 | 0.3273 | 0.052* | |
H11B | 0.3914 | 0.2781 | 0.3250 | 0.052* | |
C120 | 0.8441 (3) | 0.8282 (2) | −0.20670 (18) | 0.0391 (7) | |
H12A | 0.7630 | 0.8425 | −0.1849 | 0.047* | |
H12B | 0.8837 | 0.7609 | −0.1849 | 0.047* | |
Fe1 | 0.16886 (3) | −0.13878 (2) | 0.51745 (2) | 0.01256 (7) | |
Fe61 | 0.66800 (3) | 0.35721 (2) | 0.01667 (2) | 0.01247 (7) | |
O1 | 0.11604 (18) | −0.40445 (14) | 0.53629 (12) | 0.0298 (4) | |
O2 | 0.29694 (19) | −0.48981 (14) | 0.58880 (13) | 0.0343 (5) | |
O3 | 0.44295 (17) | −0.07664 (15) | 0.38572 (12) | 0.0304 (4) | |
O4 | 0.3736 (2) | −0.11334 (15) | 0.28053 (12) | 0.0354 (5) | |
O61 | 0.60789 (18) | 0.09221 (14) | 0.05646 (12) | 0.0313 (4) | |
O62 | 0.79407 (18) | 0.01155 (14) | 0.10214 (12) | 0.0316 (4) | |
O63 | 0.93745 (18) | 0.39906 (15) | −0.12863 (12) | 0.0317 (4) | |
O64 | 0.8561 (2) | 0.36407 (16) | −0.23024 (12) | 0.0380 (5) | |
N1 | 0.27236 (18) | −0.23745 (14) | 0.46221 (11) | 0.0143 (4) | |
N2 | 0.02541 (19) | −0.13033 (14) | 0.45264 (12) | 0.0145 (4) | |
N3 | 0.06455 (19) | −0.04180 (15) | 0.57338 (11) | 0.0150 (4) | |
N4 | 0.31181 (19) | −0.14755 (15) | 0.58249 (11) | 0.0147 (4) | |
N5 | 0.12005 (19) | −0.24685 (15) | 0.59548 (12) | 0.0173 (4) | |
H5A | 0.0883 | −0.2212 | 0.6366 | 0.021* | |
H5B | 0.0595 | −0.2627 | 0.5741 | 0.021* | |
N6 | 0.21365 (19) | −0.02718 (15) | 0.44201 (11) | 0.0156 (4) | |
H6A | 0.1566 | 0.0277 | 0.4454 | 0.019* | |
H6B | 0.2843 | −0.0200 | 0.4578 | 0.019* | |
N61 | 0.77127 (18) | 0.25143 (14) | −0.03099 (12) | 0.0138 (4) | |
N62 | 0.52430 (18) | 0.35733 (14) | −0.04450 (11) | 0.0141 (4) | |
N63 | 0.56270 (18) | 0.46111 (15) | 0.06621 (11) | 0.0137 (4) | |
N64 | 0.81057 (19) | 0.35711 (15) | 0.07877 (12) | 0.0159 (4) | |
N65 | 0.62030 (19) | 0.25658 (15) | 0.10285 (12) | 0.0166 (4) | |
H65A | 0.5924 | 0.2867 | 0.1424 | 0.020* | |
H65B | 0.5572 | 0.2395 | 0.0856 | 0.020* | |
N66 | 0.71416 (19) | 0.45989 (15) | −0.06684 (11) | 0.0158 (4) | |
H66A | 0.6606 | 0.5171 | −0.0651 | 0.019* | |
H66B | 0.7874 | 0.4659 | −0.0546 | 0.019* | |
C1 | 0.3940 (2) | −0.28405 (17) | 0.47522 (14) | 0.0153 (5) | |
C2 | 0.4350 (3) | −0.34940 (19) | 0.42258 (15) | 0.0210 (6) | |
H2 | 0.5130 | −0.3887 | 0.4195 | 0.025* | |
C3 | 0.3381 (2) | −0.34272 (19) | 0.37831 (15) | 0.0215 (6) | |
H3 | 0.3373 | −0.3766 | 0.3390 | 0.026* | |
C4 | 0.2372 (2) | −0.27388 (18) | 0.40312 (14) | 0.0165 (5) | |
C5 | 0.1220 (2) | −0.24666 (19) | 0.36997 (15) | 0.0187 (5) | |
C6 | 0.0246 (2) | −0.17904 (18) | 0.39332 (14) | 0.0167 (5) | |
C7 | −0.0926 (2) | −0.14993 (19) | 0.35779 (15) | 0.0202 (5) | |
H7 | −0.1155 | −0.1726 | 0.3166 | 0.024* | |
C8 | −0.1645 (2) | −0.08300 (19) | 0.39519 (14) | 0.0193 (5) | |
H8 | −0.2455 | −0.0512 | 0.3848 | 0.023* | |
C9 | −0.0897 (2) | −0.07131 (18) | 0.45428 (14) | 0.0158 (5) | |
C10 | −0.1308 (2) | −0.00625 (17) | 0.50504 (14) | 0.0145 (5) | |
C11 | −0.0560 (2) | 0.00575 (18) | 0.56071 (14) | 0.0152 (5) | |
C12 | −0.0977 (2) | 0.06956 (18) | 0.61423 (15) | 0.0175 (5) | |
H12 | −0.1760 | 0.1081 | 0.6177 | 0.021* | |
C13 | −0.0015 (2) | 0.06296 (19) | 0.65861 (15) | 0.0188 (5) | |
H13 | −0.0008 | 0.0967 | 0.6981 | 0.023* | |
C14 | 0.1001 (2) | −0.00634 (18) | 0.63318 (14) | 0.0175 (5) | |
C15 | 0.2152 (2) | −0.0311 (2) | 0.66561 (15) | 0.0197 (5) | |
C16 | 0.3128 (2) | −0.09822 (19) | 0.64110 (14) | 0.0180 (5) | |
C17 | 0.4317 (2) | −0.1256 (2) | 0.67524 (15) | 0.0222 (6) | |
H17 | 0.4555 | −0.1025 | 0.7159 | 0.027* | |
C18 | 0.5024 (2) | −0.1913 (2) | 0.63692 (15) | 0.0205 (5) | |
H18 | 0.5840 | −0.2222 | 0.6466 | 0.025* | |
C19 | 0.4284 (2) | −0.20439 (18) | 0.57862 (13) | 0.0145 (5) | |
C20 | 0.4693 (2) | −0.26931 (18) | 0.52963 (14) | 0.0165 (5) | |
C21 | 0.1039 (2) | −0.2943 (2) | 0.30539 (16) | 0.0233 (6) | |
C22 | 0.1001 (3) | −0.2430 (2) | 0.22867 (16) | 0.0331 (7) | |
H22 | 0.1058 | −0.1785 | 0.2178 | 0.040* | |
C23 | 0.0876 (3) | −0.2897 (3) | 0.16838 (18) | 0.0445 (9) | |
H23 | 0.0854 | −0.2560 | 0.1174 | 0.053* | |
C24 | 0.0787 (3) | −0.3846 (3) | 0.1841 (2) | 0.0455 (10) | |
H24 | 0.0709 | −0.4154 | 0.1440 | 0.055* | |
C25 | 0.0813 (3) | −0.4342 (3) | 0.2598 (2) | 0.0440 (9) | |
H25 | 0.0745 | −0.4984 | 0.2702 | 0.053* | |
C26 | 0.0940 (3) | −0.3901 (2) | 0.32090 (19) | 0.0322 (7) | |
H26 | 0.0959 | −0.4246 | 0.3716 | 0.039* | |
C27 | −0.2588 (2) | 0.0538 (2) | 0.49792 (14) | 0.0188 (5) | |
C28 | −0.3565 (3) | 0.0106 (3) | 0.51213 (17) | 0.0300 (7) | |
H28 | −0.3421 | −0.0569 | 0.5267 | 0.036* | |
C29 | −0.4753 (3) | 0.0674 (3) | 0.5048 (2) | 0.0454 (10) | |
H29 | −0.5401 | 0.0381 | 0.5144 | 0.054* | |
C30 | −0.4969 (3) | 0.1683 (3) | 0.48304 (19) | 0.0503 (11) | |
H30 | −0.5763 | 0.2065 | 0.4775 | 0.060* | |
C31 | −0.4009 (3) | 0.2115 (3) | 0.46966 (17) | 0.0450 (9) | |
H31 | −0.4156 | 0.2790 | 0.4558 | 0.054* | |
C32 | −0.2818 (3) | 0.1547 (2) | 0.47677 (15) | 0.0268 (6) | |
H32 | −0.2174 | 0.1845 | 0.4673 | 0.032* | |
C33 | 0.2352 (2) | 0.0194 (2) | 0.72786 (17) | 0.0278 (7) | |
C34 | 0.2387 (3) | −0.0247 (3) | 0.80485 (18) | 0.0416 (8) | |
H34 | 0.2319 | −0.0887 | 0.8199 | 0.050* | |
C35 | 0.2530 (3) | 0.0296 (4) | 0.8609 (2) | 0.0567 (12) | |
H35 | 0.2542 | 0.0015 | 0.9132 | 0.068* | |
C36 | 0.2652 (3) | 0.1243 (3) | 0.8377 (3) | 0.0590 (13) | |
H36 | 0.2757 | 0.1588 | 0.8748 | 0.071* | |
C37 | 0.2622 (3) | 0.1671 (3) | 0.7625 (3) | 0.0549 (12) | |
H37 | 0.2704 | 0.2308 | 0.7479 | 0.066* | |
C38 | 0.2468 (3) | 0.1162 (2) | 0.7063 (2) | 0.0396 (8) | |
H38 | 0.2442 | 0.1462 | 0.6543 | 0.048* | |
C39 | 0.5979 (2) | −0.32912 (19) | 0.53677 (14) | 0.0181 (5) | |
C40 | 0.6937 (2) | −0.2862 (2) | 0.51069 (16) | 0.0236 (6) | |
H40 | 0.6778 | −0.2205 | 0.4873 | 0.028* | |
C41 | 0.8128 (3) | −0.3420 (2) | 0.51979 (18) | 0.0316 (7) | |
H41 | 0.8764 | −0.3129 | 0.5029 | 0.038* | |
C42 | 0.8382 (3) | −0.4398 (2) | 0.55346 (18) | 0.0342 (7) | |
H42 | 0.9183 | −0.4764 | 0.5593 | 0.041* | |
C43 | 0.7433 (3) | −0.4831 (2) | 0.57856 (18) | 0.0332 (7) | |
H43 | 0.7597 | −0.5491 | 0.6011 | 0.040* | |
C44 | 0.6234 (3) | −0.4278 (2) | 0.57001 (16) | 0.0262 (6) | |
H44 | 0.5601 | −0.4573 | 0.5867 | 0.031* | |
C45 | 0.2109 (2) | −0.33925 (17) | 0.62553 (14) | 0.0175 (5) | |
H45 | 0.2918 | −0.3267 | 0.6172 | 0.021* | |
C46 | 0.1977 (2) | −0.3794 (2) | 0.71213 (15) | 0.0263 (6) | |
H46 | 0.2646 | −0.4375 | 0.7265 | 0.032* | |
C47 | 0.0785 (3) | −0.4115 (2) | 0.7305 (2) | 0.0423 (8) | |
H47A | 0.0741 | −0.4368 | 0.7849 | 0.051* | |
H47B | 0.0761 | −0.4614 | 0.7024 | 0.051* | |
H47C | 0.0107 | −0.3566 | 0.7155 | 0.051* | |
C48 | 0.2114 (3) | −0.3061 (2) | 0.75978 (16) | 0.0365 (7) | |
H48A | 0.2033 | −0.3326 | 0.8137 | 0.044* | |
H48B | 0.1495 | −0.2468 | 0.7452 | 0.044* | |
H48C | 0.2900 | −0.2927 | 0.7505 | 0.044* | |
C49 | 0.2015 (2) | −0.41309 (18) | 0.57750 (15) | 0.0228 (5) | |
C50 | 0.2923 (4) | −0.5676 (2) | 0.5487 (2) | 0.0512 (9) | |
H50A | 0.3644 | −0.6195 | 0.5602 | 0.061* | |
H50B | 0.2873 | −0.5424 | 0.4940 | 0.061* | |
H50C | 0.2222 | −0.5920 | 0.5656 | 0.061* | |
C51 | 0.2270 (2) | −0.03422 (17) | 0.35948 (13) | 0.0191 (5) | |
H51 | 0.1814 | −0.0803 | 0.3506 | 0.023* | |
C52 | 0.1795 (2) | 0.06307 (18) | 0.30258 (14) | 0.0226 (5) | |
H52 | 0.1964 | 0.0501 | 0.2503 | 0.027* | |
C53 | 0.0418 (3) | 0.0978 (2) | 0.30982 (18) | 0.0318 (6) | |
H53A | 0.0048 | 0.0466 | 0.3044 | 0.038* | |
H53B | 0.0121 | 0.1541 | 0.2700 | 0.038* | |
H53C | 0.0219 | 0.1145 | 0.3596 | 0.038* | |
C54 | 0.2437 (3) | 0.14126 (19) | 0.31074 (17) | 0.0268 (6) | |
H54A | 0.3298 | 0.1168 | 0.3056 | 0.032* | |
H54B | 0.2261 | 0.1581 | 0.3606 | 0.032* | |
H54C | 0.2156 | 0.1981 | 0.2712 | 0.032* | |
C55 | 0.3606 (3) | −0.07699 (18) | 0.34505 (15) | 0.0246 (5) | |
C56 | 0.4962 (3) | −0.1604 (2) | 0.2619 (2) | 0.0474 (9) | |
H56A | 0.4960 | −0.1842 | 0.2150 | 0.057* | |
H56B | 0.5285 | −0.2140 | 0.3033 | 0.057* | |
H56C | 0.5457 | −0.1143 | 0.2550 | 0.057* | |
C61 | 0.8937 (2) | 0.20689 (18) | −0.01715 (14) | 0.0156 (5) | |
C62 | 0.9354 (2) | 0.13577 (19) | −0.06506 (15) | 0.0197 (5) | |
H62 | 1.0135 | 0.0962 | −0.0663 | 0.024* | |
C63 | 0.8390 (2) | 0.13722 (19) | −0.10825 (15) | 0.0197 (5) | |
H63 | 0.8388 | 0.0995 | −0.1450 | 0.024* | |
C64 | 0.7381 (2) | 0.20820 (17) | −0.08610 (14) | 0.0160 (5) | |
C65 | 0.6216 (2) | 0.22976 (18) | −0.11829 (14) | 0.0171 (5) | |
C66 | 0.5242 (2) | 0.30049 (18) | −0.09890 (14) | 0.0165 (5) | |
C67 | 0.4066 (2) | 0.32688 (19) | −0.13466 (15) | 0.0202 (5) | |
H67 | 0.3834 | 0.2997 | −0.1731 | 0.024* | |
C68 | 0.3356 (2) | 0.39888 (19) | −0.10203 (14) | 0.0190 (5) | |
H68 | 0.2547 | 0.4302 | −0.1138 | 0.023* | |
C69 | 0.4094 (2) | 0.41768 (18) | −0.04562 (14) | 0.0157 (5) | |
C70 | 0.3671 (2) | 0.48740 (18) | 0.00032 (14) | 0.0151 (5) | |
C71 | 0.4419 (2) | 0.50563 (17) | 0.05326 (13) | 0.0145 (5) | |
C72 | 0.3989 (2) | 0.57427 (18) | 0.10325 (14) | 0.0166 (5) | |
H72 | 0.3199 | 0.6118 | 0.1063 | 0.020* | |
C73 | 0.4958 (2) | 0.57353 (19) | 0.14490 (15) | 0.0188 (5) | |
H73 | 0.4962 | 0.6112 | 0.1816 | 0.023* | |
C74 | 0.5979 (2) | 0.50374 (18) | 0.12187 (14) | 0.0162 (5) | |
C75 | 0.7137 (2) | 0.48490 (18) | 0.15233 (14) | 0.0174 (5) | |
C76 | 0.8121 (2) | 0.41484 (19) | 0.13133 (14) | 0.0174 (5) | |
C77 | 0.9304 (2) | 0.3920 (2) | 0.16497 (15) | 0.0216 (6) | |
H77 | 0.9544 | 0.4218 | 0.2014 | 0.026* | |
C78 | 1.0007 (2) | 0.3188 (2) | 0.13356 (15) | 0.0209 (5) | |
H78 | 1.0816 | 0.2877 | 0.1453 | 0.025* | |
C79 | 0.9263 (2) | 0.29806 (18) | 0.07853 (14) | 0.0151 (5) | |
C80 | 0.9673 (2) | 0.22677 (18) | 0.03517 (14) | 0.0162 (5) | |
C81 | 0.6032 (2) | 0.17568 (19) | −0.17786 (15) | 0.0188 (5) | |
C82 | 0.6025 (3) | 0.2181 (2) | −0.25672 (16) | 0.0271 (6) | |
H82 | 0.6133 | 0.2810 | −0.2721 | 0.033* | |
C83 | 0.5856 (3) | 0.1669 (2) | −0.31201 (17) | 0.0331 (7) | |
H83 | 0.5841 | 0.1960 | −0.3642 | 0.040* | |
C84 | 0.5713 (3) | 0.0736 (2) | −0.29014 (18) | 0.0333 (7) | |
H84 | 0.5615 | 0.0391 | −0.3274 | 0.040* | |
C85 | 0.5716 (3) | 0.0307 (2) | −0.21217 (18) | 0.0309 (7) | |
H85 | 0.5607 | −0.0322 | −0.1973 | 0.037* | |
C86 | 0.5880 (3) | 0.0812 (2) | −0.15647 (16) | 0.0247 (6) | |
H86 | 0.5889 | 0.0517 | −0.1044 | 0.030* | |
C87 | 0.2391 (2) | 0.5465 (2) | −0.00858 (14) | 0.0190 (5) | |
C88 | 0.1411 (3) | 0.5025 (2) | 0.00565 (17) | 0.0280 (6) | |
H88 | 0.1557 | 0.4352 | 0.0217 | 0.034* | |
C89 | 0.0230 (3) | 0.5588 (3) | −0.00403 (19) | 0.0416 (9) | |
H89 | −0.0414 | 0.5290 | 0.0045 | 0.050* | |
C90 | 0.0000 (3) | 0.6597 (3) | −0.02640 (19) | 0.0519 (11) | |
H90 | −0.0795 | 0.6975 | −0.0322 | 0.062* | |
C91 | 0.0953 (3) | 0.7030 (3) | −0.03985 (17) | 0.0409 (9) | |
H91 | 0.0798 | 0.7706 | −0.0547 | 0.049* | |
C92 | 0.2151 (3) | 0.6477 (2) | −0.03163 (15) | 0.0261 (6) | |
H92 | 0.2789 | 0.6781 | −0.0415 | 0.031* | |
C93 | 0.7335 (2) | 0.5442 (2) | 0.20835 (16) | 0.0207 (5) | |
C94 | 0.7303 (2) | 0.5085 (2) | 0.28788 (16) | 0.0246 (6) | |
H94 | 0.7169 | 0.4469 | 0.3064 | 0.029* | |
C95 | 0.7470 (3) | 0.5647 (2) | 0.33942 (16) | 0.0277 (6) | |
H95 | 0.7448 | 0.5408 | 0.3924 | 0.033* | |
C96 | 0.7670 (3) | 0.6565 (2) | 0.31190 (18) | 0.0296 (6) | |
H96 | 0.7777 | 0.6942 | 0.3466 | 0.035* | |
C97 | 0.7711 (3) | 0.6923 (2) | 0.23319 (18) | 0.0325 (7) | |
H97 | 0.7856 | 0.7536 | 0.2150 | 0.039* | |
C98 | 0.7534 (3) | 0.6364 (2) | 0.18127 (17) | 0.0249 (6) | |
H98 | 0.7550 | 0.6608 | 0.1283 | 0.030* | |
C99 | 1.0952 (2) | 0.16666 (19) | 0.04690 (15) | 0.0193 (5) | |
C100 | 1.1925 (2) | 0.2084 (2) | 0.02247 (16) | 0.0246 (6) | |
H100 | 1.1779 | 0.2725 | −0.0047 | 0.029* | |
C101 | 1.3117 (3) | 0.1541 (2) | 0.03882 (18) | 0.0302 (7) | |
H101 | 1.3763 | 0.1824 | 0.0234 | 0.036* | |
C102 | 1.3337 (3) | 0.0580 (2) | 0.07804 (17) | 0.0322 (7) | |
H102 | 1.4130 | 0.0223 | 0.0897 | 0.039* | |
C103 | 1.2386 (3) | 0.0154 (2) | 0.09985 (17) | 0.0296 (6) | |
H103 | 1.2539 | −0.0496 | 0.1251 | 0.036* | |
C104 | 1.1191 (2) | 0.0692 (2) | 0.08421 (15) | 0.0234 (5) | |
H104 | 1.0552 | 0.0399 | 0.0988 | 0.028* | |
C105 | 0.7113 (2) | 0.16478 (17) | 0.13523 (13) | 0.0179 (5) | |
H105 | 0.7925 | 0.1759 | 0.1239 | 0.022* | |
C106 | 0.7005 (3) | 0.1323 (2) | 0.22361 (15) | 0.0284 (6) | |
H106 | 0.7659 | 0.0735 | 0.2399 | 0.034* | |
C107 | 0.5802 (3) | 0.1054 (3) | 0.2472 (2) | 0.0434 (9) | |
H10A | 0.5708 | 0.0560 | 0.2207 | 0.052* | |
H10B | 0.5143 | 0.1623 | 0.2337 | 0.052* | |
H10C | 0.5798 | 0.0812 | 0.3020 | 0.052* | |
C108 | 0.7199 (3) | 0.2101 (2) | 0.26472 (16) | 0.0377 (7) | |
H10D | 0.7961 | 0.2252 | 0.2488 | 0.045* | |
H10E | 0.7206 | 0.1862 | 0.3196 | 0.045* | |
H10F | 0.6551 | 0.2678 | 0.2516 | 0.045* | |
C109 | 0.6968 (2) | 0.08659 (18) | 0.09266 (16) | 0.0242 (5) | |
C110 | 0.7883 (3) | −0.0670 (2) | 0.0632 (2) | 0.0426 (8) | |
H11C | 0.8618 | −0.1178 | 0.0731 | 0.051* | |
H11D | 0.7793 | −0.0421 | 0.0086 | 0.051* | |
H11E | 0.7201 | −0.0928 | 0.0825 | 0.051* | |
C111 | 0.7203 (2) | 0.44604 (17) | −0.14860 (13) | 0.0180 (5) | |
H111 | 0.6718 | 0.3999 | −0.1525 | 0.022* | |
C112 | 0.6717 (2) | 0.53999 (19) | −0.20848 (15) | 0.0243 (5) | |
H112 | 0.6789 | 0.5218 | −0.2593 | 0.029* | |
C113 | 0.5364 (3) | 0.5832 (2) | −0.19544 (19) | 0.0375 (7) | |
H11F | 0.5082 | 0.6413 | −0.2338 | 0.045* | |
H11G | 0.5251 | 0.5988 | −0.1449 | 0.045* | |
H11H | 0.4913 | 0.5364 | −0.1995 | 0.045* | |
C114 | 0.7473 (3) | 0.6150 (2) | −0.21143 (17) | 0.0299 (6) | |
H11I | 0.7138 | 0.6723 | −0.2494 | 0.036* | |
H11J | 0.8297 | 0.5873 | −0.2250 | 0.036* | |
H11K | 0.7459 | 0.6322 | −0.1617 | 0.036* | |
C115 | 0.8505 (3) | 0.40005 (19) | −0.16578 (15) | 0.0246 (5) | |
C116 | 0.9776 (3) | 0.3184 (3) | −0.2545 (2) | 0.0514 (10) | |
H11L | 0.9721 | 0.2950 | −0.3010 | 0.062* | |
H11M | 1.0147 | 0.2647 | −0.2145 | 0.062* | |
H11N | 1.0259 | 0.3653 | −0.2641 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0382 (4) | 0.0213 (3) | 0.0252 (3) | −0.0018 (3) | 0.0078 (3) | −0.0051 (3) |
S2 | 0.0429 (5) | 0.0197 (3) | 0.0319 (4) | 0.0013 (3) | 0.0116 (3) | −0.0040 (3) |
O9 | 0.086 (2) | 0.0358 (12) | 0.0294 (11) | −0.0090 (13) | 0.0191 (12) | −0.0143 (10) |
O10 | 0.0728 (18) | 0.0185 (10) | 0.0400 (12) | −0.0094 (10) | 0.0227 (12) | −0.0061 (9) |
O11 | 0.0227 (11) | 0.0462 (13) | 0.0381 (11) | −0.0043 (9) | 0.0048 (9) | −0.0136 (10) |
O12 | 0.123 (3) | 0.0154 (10) | 0.0461 (14) | −0.0067 (13) | 0.0425 (15) | −0.0040 (10) |
O13 | 0.0794 (19) | 0.0294 (11) | 0.0307 (11) | −0.0099 (12) | −0.0014 (11) | −0.0061 (9) |
O14 | 0.0237 (13) | 0.0732 (18) | 0.0666 (17) | 0.0002 (12) | 0.0029 (11) | −0.0177 (15) |
C117 | 0.0317 (18) | 0.0269 (15) | 0.066 (2) | −0.0029 (12) | −0.0048 (15) | −0.0165 (15) |
C118 | 0.0375 (18) | 0.0240 (13) | 0.0521 (19) | −0.0084 (12) | 0.0172 (14) | −0.0155 (13) |
F1 | 0.0286 (12) | 0.0603 (15) | 0.150 (3) | −0.0141 (10) | 0.0046 (13) | −0.0335 (16) |
F2 | 0.0882 (18) | 0.0464 (12) | 0.0520 (13) | 0.0045 (11) | −0.0330 (12) | −0.0172 (10) |
F3 | 0.0516 (12) | 0.0208 (8) | 0.0704 (14) | 0.0013 (8) | −0.0091 (10) | −0.0097 (9) |
F4 | 0.0369 (13) | 0.0658 (15) | 0.133 (2) | −0.0277 (11) | 0.0299 (13) | −0.0397 (16) |
F5 | 0.0987 (19) | 0.0452 (11) | 0.0374 (11) | −0.0136 (12) | 0.0247 (11) | −0.0158 (9) |
F6 | 0.0471 (12) | 0.0214 (8) | 0.0638 (13) | −0.0038 (8) | 0.0132 (9) | −0.0156 (9) |
Cl1 | 0.0523 (5) | 0.0322 (4) | 0.0313 (4) | −0.0153 (3) | 0.0063 (3) | −0.0004 (3) |
Cl2 | 0.0583 (6) | 0.0273 (4) | 0.0465 (4) | −0.0086 (4) | −0.0098 (4) | −0.0028 (3) |
Cl3 | 0.0396 (4) | 0.0321 (4) | 0.0323 (4) | −0.0103 (3) | 0.0050 (3) | 0.0002 (3) |
Cl4 | 0.0603 (6) | 0.0270 (4) | 0.0423 (4) | −0.0060 (4) | −0.0095 (4) | −0.0013 (3) |
C119 | 0.057 (2) | 0.0477 (19) | 0.0297 (15) | −0.0271 (17) | 0.0065 (15) | −0.0021 (14) |
C120 | 0.0418 (19) | 0.0414 (18) | 0.0310 (15) | −0.0109 (15) | 0.0086 (13) | −0.0014 (13) |
Fe1 | 0.01207 (15) | 0.01352 (14) | 0.01239 (13) | −0.00264 (11) | −0.00061 (10) | −0.00371 (11) |
Fe61 | 0.01193 (14) | 0.01382 (14) | 0.01171 (12) | −0.00245 (11) | −0.00018 (10) | −0.00349 (11) |
O1 | 0.0302 (11) | 0.0263 (10) | 0.0370 (11) | −0.0123 (8) | −0.0059 (9) | −0.0077 (8) |
O2 | 0.0338 (12) | 0.0199 (9) | 0.0477 (12) | 0.0019 (8) | −0.0037 (9) | −0.0128 (9) |
O3 | 0.0208 (10) | 0.0321 (10) | 0.0365 (11) | −0.0055 (8) | 0.0040 (8) | −0.0051 (9) |
O4 | 0.0391 (13) | 0.0334 (11) | 0.0289 (10) | 0.0022 (9) | 0.0109 (9) | −0.0122 (9) |
O61 | 0.0251 (11) | 0.0270 (10) | 0.0440 (12) | −0.0094 (8) | −0.0057 (9) | −0.0072 (9) |
O62 | 0.0270 (11) | 0.0210 (9) | 0.0444 (12) | 0.0012 (8) | −0.0025 (9) | −0.0088 (9) |
O63 | 0.0217 (11) | 0.0316 (11) | 0.0360 (11) | −0.0026 (8) | 0.0068 (8) | −0.0002 (9) |
O64 | 0.0468 (14) | 0.0354 (11) | 0.0289 (10) | −0.0033 (10) | 0.0159 (9) | −0.0124 (9) |
N1 | 0.0142 (11) | 0.0145 (9) | 0.0152 (10) | −0.0040 (8) | −0.0006 (8) | −0.0043 (8) |
N2 | 0.0143 (11) | 0.0152 (10) | 0.0151 (9) | −0.0037 (8) | −0.0002 (8) | −0.0055 (8) |
N3 | 0.0145 (11) | 0.0169 (10) | 0.0136 (10) | −0.0037 (8) | −0.0012 (8) | −0.0029 (8) |
N4 | 0.0141 (11) | 0.0154 (10) | 0.0152 (10) | −0.0028 (8) | −0.0011 (8) | −0.0054 (8) |
N5 | 0.0145 (11) | 0.0173 (10) | 0.0189 (10) | −0.0028 (8) | 0.0012 (8) | −0.0024 (8) |
N6 | 0.0181 (11) | 0.0143 (9) | 0.0148 (9) | −0.0049 (8) | −0.0006 (8) | −0.0029 (8) |
N61 | 0.0118 (11) | 0.0125 (9) | 0.0170 (10) | −0.0018 (8) | −0.0012 (8) | −0.0041 (8) |
N62 | 0.0115 (11) | 0.0163 (10) | 0.0143 (9) | −0.0019 (8) | −0.0005 (8) | −0.0045 (8) |
N63 | 0.0144 (11) | 0.0153 (9) | 0.0116 (9) | −0.0037 (8) | −0.0009 (8) | −0.0032 (8) |
N64 | 0.0145 (11) | 0.0178 (10) | 0.0171 (10) | −0.0041 (8) | −0.0008 (8) | −0.0071 (8) |
N65 | 0.0166 (11) | 0.0154 (9) | 0.0169 (10) | −0.0046 (8) | 0.0009 (8) | −0.0006 (8) |
N66 | 0.0183 (11) | 0.0154 (9) | 0.0140 (9) | −0.0052 (8) | 0.0021 (8) | −0.0028 (8) |
C1 | 0.0144 (13) | 0.0154 (11) | 0.0151 (11) | −0.0011 (9) | 0.0002 (9) | −0.0041 (9) |
C2 | 0.0196 (14) | 0.0220 (13) | 0.0217 (12) | −0.0005 (11) | 0.0012 (10) | −0.0110 (11) |
C3 | 0.0213 (14) | 0.0227 (13) | 0.0234 (13) | −0.0032 (11) | 0.0012 (10) | −0.0136 (11) |
C4 | 0.0167 (13) | 0.0179 (11) | 0.0170 (11) | −0.0054 (10) | −0.0006 (9) | −0.0067 (10) |
C5 | 0.0214 (14) | 0.0195 (12) | 0.0177 (11) | −0.0069 (10) | −0.0014 (10) | −0.0068 (10) |
C6 | 0.0191 (13) | 0.0187 (12) | 0.0148 (11) | −0.0070 (10) | −0.0030 (10) | −0.0053 (9) |
C7 | 0.0172 (14) | 0.0255 (13) | 0.0192 (12) | −0.0028 (10) | −0.0051 (10) | −0.0091 (10) |
C8 | 0.0179 (13) | 0.0249 (13) | 0.0162 (11) | −0.0038 (10) | −0.0040 (10) | −0.0077 (10) |
C9 | 0.0164 (13) | 0.0166 (11) | 0.0149 (11) | −0.0043 (10) | −0.0007 (9) | −0.0037 (9) |
C10 | 0.0125 (12) | 0.0143 (11) | 0.0151 (11) | −0.0003 (9) | −0.0016 (9) | −0.0023 (9) |
C11 | 0.0135 (12) | 0.0170 (11) | 0.0151 (11) | −0.0045 (9) | 0.0015 (9) | −0.0027 (9) |
C12 | 0.0138 (13) | 0.0185 (12) | 0.0212 (12) | −0.0028 (10) | 0.0017 (10) | −0.0082 (10) |
C13 | 0.0146 (13) | 0.0216 (12) | 0.0213 (12) | −0.0018 (10) | 0.0002 (10) | −0.0106 (10) |
C14 | 0.0147 (13) | 0.0197 (12) | 0.0183 (11) | −0.0019 (10) | 0.0007 (10) | −0.0076 (10) |
C15 | 0.0180 (13) | 0.0263 (13) | 0.0177 (12) | −0.0049 (10) | −0.0023 (10) | −0.0111 (10) |
C16 | 0.0146 (13) | 0.0233 (13) | 0.0170 (11) | −0.0023 (10) | −0.0042 (10) | −0.0079 (10) |
C17 | 0.0162 (14) | 0.0319 (14) | 0.0217 (13) | −0.0044 (11) | −0.0014 (10) | −0.0140 (11) |
C18 | 0.0128 (13) | 0.0243 (13) | 0.0240 (13) | −0.0016 (10) | −0.0030 (10) | −0.0068 (11) |
C19 | 0.0101 (12) | 0.0175 (11) | 0.0152 (11) | −0.0031 (9) | −0.0010 (9) | −0.0017 (9) |
C20 | 0.0136 (13) | 0.0178 (11) | 0.0176 (11) | −0.0037 (9) | −0.0008 (9) | −0.0022 (9) |
C21 | 0.0155 (13) | 0.0316 (14) | 0.0250 (13) | −0.0002 (11) | −0.0035 (10) | −0.0165 (12) |
C22 | 0.0321 (17) | 0.0441 (17) | 0.0243 (14) | −0.0021 (14) | −0.0038 (12) | −0.0176 (13) |
C23 | 0.0322 (18) | 0.076 (3) | 0.0253 (15) | 0.0038 (16) | −0.0056 (13) | −0.0300 (17) |
C24 | 0.0275 (17) | 0.070 (3) | 0.049 (2) | 0.0015 (16) | −0.0064 (14) | −0.049 (2) |
C25 | 0.0313 (18) | 0.048 (2) | 0.066 (2) | −0.0053 (15) | −0.0072 (16) | −0.0439 (19) |
C26 | 0.0262 (16) | 0.0330 (16) | 0.0437 (17) | −0.0048 (12) | −0.0064 (13) | −0.0236 (14) |
C27 | 0.0142 (13) | 0.0258 (13) | 0.0156 (11) | −0.0006 (10) | −0.0013 (9) | −0.0076 (10) |
C28 | 0.0161 (14) | 0.0482 (18) | 0.0292 (14) | −0.0062 (12) | 0.0013 (11) | −0.0180 (13) |
C29 | 0.0143 (16) | 0.087 (3) | 0.0378 (18) | −0.0054 (17) | −0.0043 (13) | −0.0268 (19) |
C30 | 0.0245 (18) | 0.084 (3) | 0.0274 (16) | 0.0223 (18) | −0.0058 (13) | −0.0202 (18) |
C31 | 0.047 (2) | 0.048 (2) | 0.0230 (14) | 0.0235 (16) | −0.0082 (14) | −0.0098 (14) |
C32 | 0.0269 (15) | 0.0288 (14) | 0.0183 (12) | 0.0065 (11) | −0.0048 (10) | −0.0054 (11) |
C33 | 0.0136 (14) | 0.0423 (17) | 0.0301 (15) | 0.0020 (12) | −0.0033 (11) | −0.0234 (13) |
C34 | 0.0260 (17) | 0.072 (2) | 0.0275 (15) | −0.0039 (16) | −0.0055 (13) | −0.0202 (16) |
C35 | 0.0223 (18) | 0.116 (4) | 0.0335 (18) | −0.005 (2) | 0.0024 (14) | −0.035 (2) |
C36 | 0.029 (2) | 0.086 (3) | 0.074 (3) | 0.0003 (19) | −0.0066 (18) | −0.060 (3) |
C37 | 0.039 (2) | 0.060 (2) | 0.078 (3) | 0.0038 (17) | −0.0219 (19) | −0.053 (2) |
C38 | 0.0319 (18) | 0.0379 (17) | 0.054 (2) | 0.0014 (14) | −0.0107 (15) | −0.0300 (16) |
C39 | 0.0143 (13) | 0.0222 (12) | 0.0178 (12) | −0.0021 (10) | −0.0016 (10) | −0.0068 (10) |
C40 | 0.0183 (14) | 0.0280 (13) | 0.0265 (13) | −0.0064 (11) | −0.0012 (10) | −0.0086 (11) |
C41 | 0.0151 (14) | 0.0465 (18) | 0.0367 (16) | −0.0068 (13) | 0.0047 (12) | −0.0186 (14) |
C42 | 0.0166 (15) | 0.0471 (19) | 0.0351 (16) | 0.0068 (13) | −0.0068 (12) | −0.0161 (14) |
C43 | 0.0233 (16) | 0.0339 (16) | 0.0330 (15) | 0.0099 (12) | −0.0039 (12) | −0.0056 (13) |
C44 | 0.0215 (15) | 0.0247 (13) | 0.0273 (13) | 0.0020 (11) | 0.0011 (11) | −0.0039 (11) |
C45 | 0.0138 (12) | 0.0165 (10) | 0.0203 (11) | −0.0027 (9) | 0.0010 (9) | −0.0011 (9) |
C46 | 0.0215 (14) | 0.0257 (13) | 0.0215 (12) | 0.0028 (10) | 0.0041 (10) | 0.0060 (10) |
C47 | 0.0335 (19) | 0.0384 (17) | 0.0441 (19) | −0.0077 (14) | 0.0122 (14) | 0.0118 (15) |
C48 | 0.0409 (18) | 0.0461 (18) | 0.0170 (12) | 0.0009 (14) | −0.0010 (12) | −0.0078 (12) |
C49 | 0.0230 (14) | 0.0170 (11) | 0.0279 (13) | −0.0066 (10) | 0.0032 (10) | −0.0024 (10) |
C50 | 0.061 (2) | 0.0234 (15) | 0.073 (3) | −0.0038 (15) | 0.0013 (19) | −0.0259 (17) |
C51 | 0.0217 (13) | 0.0197 (11) | 0.0150 (10) | −0.0046 (9) | 0.0028 (9) | −0.0026 (9) |
C52 | 0.0246 (14) | 0.0225 (12) | 0.0167 (11) | −0.0039 (10) | −0.0003 (10) | 0.0030 (9) |
C53 | 0.0212 (15) | 0.0307 (14) | 0.0372 (15) | −0.0021 (11) | −0.0047 (12) | 0.0034 (12) |
C54 | 0.0254 (15) | 0.0203 (12) | 0.0312 (14) | −0.0058 (11) | 0.0033 (11) | 0.0021 (11) |
C55 | 0.0287 (15) | 0.0195 (12) | 0.0215 (12) | −0.0024 (10) | 0.0070 (11) | −0.0009 (10) |
C56 | 0.051 (2) | 0.0334 (16) | 0.051 (2) | −0.0003 (15) | 0.0304 (17) | −0.0118 (15) |
C61 | 0.0128 (12) | 0.0169 (11) | 0.0170 (11) | −0.0024 (9) | −0.0003 (9) | −0.0045 (9) |
C62 | 0.0152 (13) | 0.0193 (12) | 0.0245 (13) | −0.0003 (10) | 0.0005 (10) | −0.0091 (10) |
C63 | 0.0192 (14) | 0.0197 (12) | 0.0213 (12) | −0.0017 (10) | 0.0015 (10) | −0.0110 (10) |
C64 | 0.0190 (13) | 0.0149 (11) | 0.0156 (11) | −0.0044 (10) | −0.0001 (9) | −0.0060 (9) |
C65 | 0.0205 (13) | 0.0178 (11) | 0.0158 (11) | −0.0058 (10) | −0.0013 (10) | −0.0076 (9) |
C66 | 0.0162 (13) | 0.0173 (11) | 0.0186 (11) | −0.0063 (10) | −0.0008 (10) | −0.0064 (10) |
C67 | 0.0176 (14) | 0.0265 (13) | 0.0190 (12) | −0.0037 (11) | −0.0041 (10) | −0.0109 (11) |
C68 | 0.0165 (13) | 0.0244 (13) | 0.0173 (11) | −0.0036 (10) | −0.0039 (10) | −0.0075 (10) |
C69 | 0.0141 (13) | 0.0192 (12) | 0.0144 (11) | −0.0054 (10) | −0.0011 (9) | −0.0026 (9) |
C70 | 0.0118 (12) | 0.0175 (11) | 0.0153 (11) | −0.0029 (9) | 0.0013 (9) | −0.0026 (9) |
C71 | 0.0137 (12) | 0.0145 (11) | 0.0149 (11) | −0.0024 (9) | 0.0028 (9) | −0.0041 (9) |
C72 | 0.0155 (13) | 0.0187 (11) | 0.0157 (11) | −0.0018 (10) | −0.0009 (9) | −0.0065 (9) |
C73 | 0.0159 (13) | 0.0206 (12) | 0.0209 (12) | −0.0030 (10) | −0.0011 (10) | −0.0080 (10) |
C74 | 0.0141 (13) | 0.0195 (12) | 0.0160 (11) | −0.0032 (9) | 0.0007 (9) | −0.0072 (9) |
C75 | 0.0147 (13) | 0.0196 (12) | 0.0198 (12) | −0.0029 (10) | −0.0019 (9) | −0.0092 (10) |
C76 | 0.0146 (13) | 0.0238 (12) | 0.0158 (11) | −0.0053 (10) | −0.0010 (9) | −0.0075 (10) |
C77 | 0.0131 (13) | 0.0331 (14) | 0.0228 (13) | −0.0057 (11) | −0.0014 (10) | −0.0149 (11) |
C78 | 0.0130 (13) | 0.0291 (14) | 0.0217 (12) | −0.0028 (11) | −0.0022 (10) | −0.0101 (11) |
C79 | 0.0097 (12) | 0.0204 (12) | 0.0150 (11) | −0.0022 (9) | −0.0021 (9) | −0.0045 (9) |
C80 | 0.0120 (12) | 0.0178 (11) | 0.0178 (11) | −0.0019 (9) | 0.0012 (9) | −0.0037 (9) |
C81 | 0.0161 (13) | 0.0231 (12) | 0.0201 (12) | −0.0037 (10) | −0.0005 (10) | −0.0122 (10) |
C82 | 0.0329 (16) | 0.0287 (14) | 0.0229 (13) | −0.0088 (12) | −0.0001 (11) | −0.0110 (11) |
C83 | 0.0317 (17) | 0.0479 (18) | 0.0218 (13) | −0.0067 (14) | 0.0018 (12) | −0.0160 (13) |
C84 | 0.0286 (16) | 0.0417 (17) | 0.0362 (16) | −0.0034 (13) | −0.0018 (12) | −0.0288 (14) |
C85 | 0.0315 (17) | 0.0266 (14) | 0.0396 (17) | −0.0063 (12) | −0.0060 (13) | −0.0173 (13) |
C86 | 0.0250 (15) | 0.0237 (13) | 0.0265 (13) | −0.0030 (11) | −0.0068 (11) | −0.0097 (11) |
C87 | 0.0147 (13) | 0.0260 (13) | 0.0145 (11) | 0.0021 (10) | −0.0038 (9) | −0.0076 (10) |
C88 | 0.0178 (14) | 0.0411 (16) | 0.0288 (14) | −0.0043 (12) | −0.0011 (11) | −0.0182 (13) |
C89 | 0.0145 (15) | 0.080 (3) | 0.0347 (16) | −0.0026 (16) | −0.0020 (12) | −0.0327 (18) |
C90 | 0.0237 (18) | 0.089 (3) | 0.0300 (16) | 0.0239 (18) | −0.0093 (13) | −0.0264 (18) |
C91 | 0.041 (2) | 0.0453 (18) | 0.0209 (13) | 0.0233 (15) | −0.0098 (13) | −0.0118 (13) |
C92 | 0.0284 (15) | 0.0271 (14) | 0.0169 (12) | 0.0066 (11) | −0.0083 (10) | −0.0058 (10) |
C93 | 0.0111 (13) | 0.0269 (13) | 0.0271 (13) | −0.0008 (10) | 0.0000 (10) | −0.0171 (11) |
C94 | 0.0198 (14) | 0.0299 (14) | 0.0252 (13) | −0.0031 (11) | −0.0033 (10) | −0.0107 (11) |
C95 | 0.0224 (15) | 0.0402 (16) | 0.0225 (13) | −0.0027 (12) | −0.0037 (11) | −0.0158 (12) |
C96 | 0.0234 (15) | 0.0378 (16) | 0.0358 (15) | −0.0067 (12) | −0.0013 (12) | −0.0268 (14) |
C97 | 0.0315 (17) | 0.0325 (15) | 0.0403 (17) | −0.0102 (13) | 0.0003 (13) | −0.0201 (14) |
C98 | 0.0227 (14) | 0.0282 (14) | 0.0279 (13) | −0.0080 (11) | −0.0008 (11) | −0.0125 (11) |
C99 | 0.0136 (13) | 0.0233 (13) | 0.0203 (12) | −0.0002 (10) | −0.0006 (10) | −0.0081 (10) |
C100 | 0.0170 (14) | 0.0288 (14) | 0.0301 (14) | −0.0065 (11) | 0.0028 (11) | −0.0105 (12) |
C101 | 0.0141 (14) | 0.0409 (17) | 0.0385 (16) | −0.0049 (12) | 0.0028 (12) | −0.0172 (14) |
C102 | 0.0185 (15) | 0.0405 (17) | 0.0336 (15) | 0.0081 (12) | −0.0055 (12) | −0.0158 (13) |
C103 | 0.0223 (15) | 0.0276 (14) | 0.0326 (15) | 0.0058 (11) | −0.0048 (11) | −0.0053 (12) |
C104 | 0.0188 (13) | 0.0258 (13) | 0.0240 (13) | −0.0011 (10) | 0.0001 (10) | −0.0064 (11) |
C105 | 0.0139 (12) | 0.0173 (10) | 0.0191 (11) | −0.0015 (9) | 0.0004 (9) | 0.0013 (9) |
C106 | 0.0236 (15) | 0.0296 (14) | 0.0216 (12) | 0.0035 (11) | 0.0043 (10) | 0.0053 (11) |
C107 | 0.0355 (19) | 0.0409 (18) | 0.0400 (18) | −0.0037 (15) | 0.0172 (14) | 0.0117 (15) |
C108 | 0.0371 (18) | 0.0520 (19) | 0.0177 (12) | −0.0004 (14) | −0.0017 (11) | −0.0054 (13) |
C109 | 0.0216 (14) | 0.0178 (11) | 0.0310 (14) | −0.0058 (10) | 0.0044 (11) | 0.0002 (10) |
C110 | 0.047 (2) | 0.0213 (14) | 0.060 (2) | −0.0027 (13) | 0.0015 (16) | −0.0159 (14) |
C111 | 0.0201 (12) | 0.0192 (11) | 0.0142 (10) | −0.0049 (9) | 0.0037 (9) | −0.0032 (9) |
C112 | 0.0233 (14) | 0.0263 (13) | 0.0196 (12) | −0.0059 (11) | −0.0012 (10) | 0.0040 (10) |
C113 | 0.0247 (16) | 0.0329 (15) | 0.0447 (18) | −0.0056 (12) | −0.0057 (13) | 0.0152 (13) |
C114 | 0.0244 (16) | 0.0223 (13) | 0.0365 (16) | −0.0049 (11) | 0.0033 (12) | 0.0073 (12) |
C115 | 0.0261 (15) | 0.0205 (12) | 0.0233 (12) | −0.0019 (10) | 0.0075 (11) | −0.0021 (10) |
C116 | 0.062 (2) | 0.0354 (17) | 0.053 (2) | −0.0057 (16) | 0.0367 (19) | −0.0190 (16) |
S1—O11 | 1.433 (2) | C41—C42 | 1.378 (5) |
S1—O9 | 1.433 (2) | C41—H41 | 0.9300 |
S1—O10 | 1.440 (2) | C42—C43 | 1.388 (5) |
S1—C117 | 1.815 (3) | C42—H42 | 0.9300 |
S2—O12 | 1.432 (2) | C43—C44 | 1.394 (4) |
S2—O14 | 1.440 (3) | C43—H43 | 0.9300 |
S2—O13 | 1.440 (2) | C44—H44 | 0.9300 |
S2—C118 | 1.810 (3) | C45—C49 | 1.519 (3) |
C117—F1 | 1.327 (4) | C45—C46 | 1.535 (3) |
C117—F3 | 1.331 (3) | C45—H45 | 0.9800 |
C117—F2 | 1.350 (4) | C46—C48 | 1.522 (4) |
C118—F6 | 1.331 (3) | C46—C47 | 1.538 (4) |
C118—F5 | 1.333 (4) | C46—H46 | 0.9800 |
C118—F4 | 1.336 (4) | C47—H47A | 0.9600 |
Cl1—C119 | 1.770 (3) | C47—H47B | 0.9600 |
Cl2—C119 | 1.746 (3) | C47—H47C | 0.9600 |
Cl3—C120 | 1.769 (3) | C48—H48A | 0.9600 |
Cl4—C120 | 1.754 (3) | C48—H48B | 0.9600 |
C119—H11A | 0.9700 | C48—H48C | 0.9600 |
C119—H11B | 0.9700 | C50—H50A | 0.9600 |
C120—H12A | 0.9700 | C50—H50B | 0.9600 |
C120—H12B | 0.9700 | C50—H50C | 0.9600 |
Fe1—N3 | 1.990 (2) | C51—C55 | 1.518 (4) |
Fe1—N1 | 1.995 (2) | C51—C52 | 1.540 (3) |
Fe1—N4 | 2.002 (2) | C51—H51 | 0.9800 |
Fe1—N2 | 2.005 (2) | C52—C54 | 1.523 (4) |
Fe1—N6 | 2.023 (2) | C52—C53 | 1.526 (4) |
Fe1—N5 | 2.029 (2) | C52—H52 | 0.9800 |
Fe61—N61 | 1.987 (2) | C53—H53A | 0.9600 |
Fe61—N63 | 1.995 (2) | C53—H53B | 0.9600 |
Fe61—N64 | 2.003 (2) | C53—H53C | 0.9600 |
Fe61—N62 | 2.004 (2) | C54—H54A | 0.9600 |
Fe61—N66 | 2.016 (2) | C54—H54B | 0.9600 |
Fe61—N65 | 2.031 (2) | C54—H54C | 0.9600 |
O1—C49 | 1.210 (3) | C56—H56A | 0.9600 |
O2—C49 | 1.332 (3) | C56—H56B | 0.9600 |
O2—C50 | 1.458 (4) | C56—H56C | 0.9600 |
O3—C55 | 1.211 (3) | C61—C80 | 1.395 (3) |
O4—C55 | 1.337 (3) | C61—C62 | 1.438 (3) |
O4—C56 | 1.443 (4) | C62—C63 | 1.360 (4) |
O61—C109 | 1.201 (3) | C62—H62 | 0.9300 |
O62—C109 | 1.330 (3) | C63—C64 | 1.432 (3) |
O62—C110 | 1.458 (4) | C63—H63 | 0.9300 |
O63—C115 | 1.210 (3) | C64—C65 | 1.404 (4) |
O64—C115 | 1.338 (3) | C65—C66 | 1.387 (4) |
O64—C116 | 1.458 (4) | C65—C81 | 1.485 (3) |
N1—C4 | 1.379 (3) | C66—C67 | 1.436 (4) |
N1—C1 | 1.385 (3) | C67—C68 | 1.357 (4) |
N2—C9 | 1.373 (3) | C67—H67 | 0.9300 |
N2—C6 | 1.379 (3) | C68—C69 | 1.443 (3) |
N3—C11 | 1.377 (3) | C68—H68 | 0.9300 |
N3—C14 | 1.383 (3) | C69—C70 | 1.399 (3) |
N4—C16 | 1.374 (3) | C70—C71 | 1.401 (3) |
N4—C19 | 1.379 (3) | C70—C87 | 1.488 (3) |
N5—C45 | 1.485 (3) | C71—C72 | 1.440 (3) |
N5—H5A | 0.9000 | C72—C73 | 1.353 (4) |
N5—H5B | 0.9000 | C72—H72 | 0.9300 |
N6—C51 | 1.480 (3) | C73—C74 | 1.436 (4) |
N6—H6A | 0.9000 | C73—H73 | 0.9300 |
N6—H6B | 0.9000 | C74—C75 | 1.389 (4) |
N61—C64 | 1.373 (3) | C75—C76 | 1.398 (4) |
N61—C61 | 1.390 (3) | C75—C93 | 1.494 (3) |
N62—C69 | 1.375 (3) | C76—C77 | 1.432 (4) |
N62—C66 | 1.387 (3) | C77—C78 | 1.355 (4) |
N63—C71 | 1.371 (3) | C77—H77 | 0.9300 |
N63—C74 | 1.386 (3) | C78—C79 | 1.443 (3) |
N64—C76 | 1.373 (3) | C78—H78 | 0.9300 |
N64—C79 | 1.377 (3) | C79—C80 | 1.382 (3) |
N65—C105 | 1.489 (3) | C80—C99 | 1.495 (4) |
N65—H65A | 0.9000 | C81—C86 | 1.391 (4) |
N65—H65B | 0.9000 | C81—C82 | 1.402 (4) |
N66—C111 | 1.494 (3) | C82—C83 | 1.387 (4) |
N66—H66A | 0.9000 | C82—H82 | 0.9300 |
N66—H66B | 0.9000 | C83—C84 | 1.372 (5) |
C1—C20 | 1.401 (3) | C83—H83 | 0.9300 |
C1—C2 | 1.438 (3) | C84—C85 | 1.390 (5) |
C2—C3 | 1.356 (4) | C84—H84 | 0.9300 |
C2—H2 | 0.9300 | C85—C86 | 1.385 (4) |
C3—C4 | 1.432 (4) | C85—H85 | 0.9300 |
C3—H3 | 0.9300 | C86—H86 | 0.9300 |
C4—C5 | 1.393 (4) | C87—C92 | 1.394 (4) |
C5—C6 | 1.387 (4) | C87—C88 | 1.403 (4) |
C5—C21 | 1.495 (3) | C88—C89 | 1.383 (4) |
C6—C7 | 1.430 (3) | C88—H88 | 0.9300 |
C7—C8 | 1.360 (4) | C89—C90 | 1.390 (6) |
C7—H7 | 0.9300 | C89—H89 | 0.9300 |
C8—C9 | 1.441 (3) | C90—C91 | 1.368 (6) |
C8—H8 | 0.9300 | C90—H90 | 0.9300 |
C9—C10 | 1.410 (3) | C91—C92 | 1.394 (4) |
C10—C11 | 1.397 (3) | C91—H91 | 0.9300 |
C10—C27 | 1.492 (3) | C92—H92 | 0.9300 |
C11—C12 | 1.435 (3) | C93—C98 | 1.390 (4) |
C12—C13 | 1.352 (4) | C93—C94 | 1.396 (4) |
C12—H12 | 0.9300 | C94—C95 | 1.386 (4) |
C13—C14 | 1.445 (3) | C94—H94 | 0.9300 |
C13—H13 | 0.9300 | C95—C96 | 1.386 (4) |
C14—C15 | 1.388 (4) | C95—H95 | 0.9300 |
C15—C16 | 1.393 (4) | C96—C97 | 1.383 (5) |
C15—C33 | 1.493 (4) | C96—H96 | 0.9300 |
C16—C17 | 1.437 (4) | C97—C98 | 1.393 (4) |
C17—C18 | 1.353 (4) | C97—H97 | 0.9300 |
C17—H17 | 0.9300 | C98—H98 | 0.9300 |
C18—C19 | 1.434 (4) | C99—C104 | 1.391 (4) |
C18—H18 | 0.9300 | C99—C100 | 1.397 (4) |
C19—C20 | 1.385 (3) | C100—C101 | 1.396 (4) |
C20—C39 | 1.497 (4) | C100—H100 | 0.9300 |
C21—C26 | 1.387 (4) | C101—C102 | 1.384 (5) |
C21—C22 | 1.402 (4) | C101—H101 | 0.9300 |
C22—C23 | 1.403 (4) | C102—C103 | 1.375 (4) |
C22—H22 | 0.9300 | C102—H102 | 0.9300 |
C23—C24 | 1.370 (5) | C103—C104 | 1.395 (4) |
C23—H23 | 0.9300 | C103—H103 | 0.9300 |
C24—C25 | 1.378 (6) | C104—H104 | 0.9300 |
C24—H24 | 0.9300 | C105—C109 | 1.524 (4) |
C25—C26 | 1.392 (4) | C105—C106 | 1.543 (3) |
C25—H25 | 0.9300 | C105—H105 | 0.9800 |
C26—H26 | 0.9300 | C106—C108 | 1.521 (4) |
C27—C32 | 1.389 (4) | C106—C107 | 1.528 (4) |
C27—C28 | 1.392 (4) | C106—H106 | 0.9800 |
C28—C29 | 1.390 (4) | C107—H10A | 0.9600 |
C28—H28 | 0.9300 | C107—H10B | 0.9600 |
C29—C30 | 1.389 (6) | C107—H10C | 0.9600 |
C29—H29 | 0.9300 | C108—H10D | 0.9600 |
C30—C31 | 1.375 (6) | C108—H10E | 0.9600 |
C30—H30 | 0.9300 | C108—H10F | 0.9600 |
C31—C32 | 1.393 (4) | C110—H11C | 0.9600 |
C31—H31 | 0.9300 | C110—H11D | 0.9600 |
C32—H32 | 0.9300 | C110—H11E | 0.9600 |
C33—C34 | 1.376 (4) | C111—C115 | 1.505 (4) |
C33—C38 | 1.409 (5) | C111—C112 | 1.537 (3) |
C34—C35 | 1.422 (5) | C111—H111 | 0.9800 |
C34—H34 | 0.9300 | C112—C113 | 1.531 (4) |
C35—C36 | 1.383 (6) | C112—C114 | 1.534 (4) |
C35—H35 | 0.9300 | C112—H112 | 0.9800 |
C36—C37 | 1.345 (6) | C113—H11F | 0.9600 |
C36—H36 | 0.9300 | C113—H11G | 0.9600 |
C37—C38 | 1.392 (5) | C113—H11H | 0.9600 |
C37—H37 | 0.9300 | C114—H11I | 0.9600 |
C38—H38 | 0.9300 | C114—H11J | 0.9600 |
C39—C44 | 1.389 (4) | C114—H11K | 0.9600 |
C39—C40 | 1.396 (4) | C116—H11L | 0.9600 |
C40—C41 | 1.390 (4) | C116—H11M | 0.9600 |
C40—H40 | 0.9300 | C116—H11N | 0.9600 |
O11—S1—O9 | 115.44 (15) | C48—C46—C47 | 111.9 (3) |
O11—S1—O10 | 114.65 (14) | C45—C46—C47 | 112.1 (2) |
O9—S1—O10 | 116.29 (14) | C48—C46—H46 | 107.3 |
O11—S1—C117 | 101.62 (15) | C45—C46—H46 | 107.3 |
O9—S1—C117 | 102.63 (16) | C47—C46—H46 | 107.3 |
O10—S1—C117 | 103.19 (15) | C46—C47—H47A | 109.5 |
O12—S2—O14 | 115.2 (2) | C46—C47—H47B | 109.5 |
O12—S2—O13 | 116.51 (17) | H47A—C47—H47B | 109.5 |
O14—S2—O13 | 113.72 (17) | C46—C47—H47C | 109.5 |
O12—S2—C118 | 104.19 (14) | H47A—C47—H47C | 109.5 |
O14—S2—C118 | 101.59 (15) | H47B—C47—H47C | 109.5 |
O13—S2—C118 | 102.97 (16) | C46—C48—H48A | 109.5 |
F1—C117—F3 | 107.0 (3) | C46—C48—H48B | 109.5 |
F1—C117—F2 | 107.5 (3) | H48A—C48—H48B | 109.5 |
F3—C117—F2 | 106.8 (3) | C46—C48—H48C | 109.5 |
F1—C117—S1 | 113.1 (3) | H48A—C48—H48C | 109.5 |
F3—C117—S1 | 111.2 (2) | H48B—C48—H48C | 109.5 |
F2—C117—S1 | 111.0 (2) | O1—C49—O2 | 124.5 (2) |
F6—C118—F5 | 107.5 (3) | O1—C49—C45 | 124.1 (2) |
F6—C118—F4 | 106.8 (3) | O2—C49—C45 | 111.4 (2) |
F5—C118—F4 | 108.5 (3) | O2—C50—H50A | 109.5 |
F6—C118—S2 | 110.4 (2) | O2—C50—H50B | 109.5 |
F5—C118—S2 | 111.5 (2) | H50A—C50—H50B | 109.5 |
F4—C118—S2 | 111.8 (2) | O2—C50—H50C | 109.5 |
Cl2—C119—Cl1 | 111.86 (17) | H50A—C50—H50C | 109.5 |
Cl2—C119—H11A | 109.2 | H50B—C50—H50C | 109.5 |
Cl1—C119—H11A | 109.2 | N6—C51—C55 | 107.51 (19) |
Cl2—C119—H11B | 109.2 | N6—C51—C52 | 114.39 (19) |
Cl1—C119—H11B | 109.2 | C55—C51—C52 | 110.8 (2) |
H11A—C119—H11B | 107.9 | N6—C51—H51 | 108.0 |
Cl4—C120—Cl3 | 111.91 (17) | C55—C51—H51 | 108.0 |
Cl4—C120—H12A | 109.2 | C52—C51—H51 | 108.0 |
Cl3—C120—H12A | 109.2 | C54—C52—C53 | 112.0 (2) |
Cl4—C120—H12B | 109.2 | C54—C52—C51 | 113.0 (2) |
Cl3—C120—H12B | 109.2 | C53—C52—C51 | 110.3 (2) |
H12A—C120—H12B | 107.9 | C54—C52—H52 | 107.1 |
N3—Fe1—N1 | 179.20 (10) | C53—C52—H52 | 107.1 |
N3—Fe1—N4 | 90.61 (8) | C51—C52—H52 | 107.1 |
N1—Fe1—N4 | 89.58 (8) | C52—C53—H53A | 109.5 |
N3—Fe1—N2 | 89.34 (8) | C52—C53—H53B | 109.5 |
N1—Fe1—N2 | 90.47 (8) | H53A—C53—H53B | 109.5 |
N4—Fe1—N2 | 179.78 (11) | C52—C53—H53C | 109.5 |
N3—Fe1—N6 | 88.74 (8) | H53A—C53—H53C | 109.5 |
N1—Fe1—N6 | 92.05 (8) | H53B—C53—H53C | 109.5 |
N4—Fe1—N6 | 89.08 (8) | C52—C54—H54A | 109.5 |
N2—Fe1—N6 | 91.13 (8) | C52—C54—H54B | 109.5 |
N3—Fe1—N5 | 89.02 (8) | H54A—C54—H54B | 109.5 |
N1—Fe1—N5 | 90.20 (8) | C52—C54—H54C | 109.5 |
N4—Fe1—N5 | 90.83 (8) | H54A—C54—H54C | 109.5 |
N2—Fe1—N5 | 88.95 (9) | H54B—C54—H54C | 109.5 |
N6—Fe1—N5 | 177.75 (9) | O3—C55—O4 | 125.3 (3) |
N61—Fe61—N63 | 178.66 (10) | O3—C55—C51 | 124.6 (2) |
N61—Fe61—N64 | 89.84 (8) | O4—C55—C51 | 110.1 (2) |
N63—Fe61—N64 | 90.40 (8) | O4—C56—H56A | 109.5 |
N61—Fe61—N62 | 90.56 (8) | O4—C56—H56B | 109.5 |
N63—Fe61—N62 | 89.19 (8) | H56A—C56—H56B | 109.5 |
N64—Fe61—N62 | 179.42 (9) | O4—C56—H56C | 109.5 |
N61—Fe61—N66 | 91.13 (8) | H56A—C56—H56C | 109.5 |
N63—Fe61—N66 | 90.20 (8) | H56B—C56—H56C | 109.5 |
N64—Fe61—N66 | 88.98 (9) | N61—C61—C80 | 126.0 (2) |
N62—Fe61—N66 | 91.43 (8) | N61—C61—C62 | 110.0 (2) |
N61—Fe61—N65 | 90.39 (8) | C80—C61—C62 | 124.0 (2) |
N63—Fe61—N65 | 88.29 (8) | C63—C62—C61 | 107.2 (2) |
N64—Fe61—N65 | 90.37 (8) | C63—C62—H62 | 126.4 |
N62—Fe61—N65 | 89.20 (8) | C61—C62—H62 | 126.4 |
N66—Fe61—N65 | 178.35 (9) | C62—C63—C64 | 106.6 (2) |
C49—O2—C50 | 115.3 (2) | C62—C63—H63 | 126.7 |
C55—O4—C56 | 115.8 (3) | C64—C63—H63 | 126.7 |
C109—O62—C110 | 115.0 (2) | N61—C64—C65 | 125.7 (2) |
C115—O64—C116 | 115.7 (3) | N61—C64—C63 | 111.2 (2) |
C4—N1—C1 | 105.6 (2) | C65—C64—C63 | 123.1 (2) |
C4—N1—Fe1 | 126.96 (17) | C66—C65—C64 | 123.5 (2) |
C1—N1—Fe1 | 127.44 (16) | C66—C65—C81 | 118.5 (2) |
C9—N2—C6 | 105.5 (2) | C64—C65—C81 | 118.0 (2) |
C9—N2—Fe1 | 127.88 (16) | N62—C66—C65 | 126.4 (2) |
C6—N2—Fe1 | 126.50 (17) | N62—C66—C67 | 109.6 (2) |
C11—N3—C14 | 105.2 (2) | C65—C66—C67 | 123.9 (2) |
C11—N3—Fe1 | 128.32 (16) | C68—C67—C66 | 107.4 (2) |
C14—N3—Fe1 | 126.47 (17) | C68—C67—H67 | 126.3 |
C16—N4—C19 | 105.9 (2) | C66—C67—H67 | 126.3 |
C16—N4—Fe1 | 126.53 (17) | C67—C68—C69 | 107.0 (2) |
C19—N4—Fe1 | 127.55 (16) | C67—C68—H68 | 126.5 |
C45—N5—Fe1 | 120.64 (16) | C69—C68—H68 | 126.5 |
C45—N5—H5A | 107.2 | N62—C69—C70 | 126.4 (2) |
Fe1—N5—H5A | 107.2 | N62—C69—C68 | 109.9 (2) |
C45—N5—H5B | 107.2 | C70—C69—C68 | 123.7 (2) |
Fe1—N5—H5B | 107.2 | C69—C70—C71 | 122.3 (2) |
H5A—N5—H5B | 106.8 | C69—C70—C87 | 119.1 (2) |
C51—N6—Fe1 | 117.91 (15) | C71—C70—C87 | 118.5 (2) |
C51—N6—H6A | 107.8 | N63—C71—C70 | 126.1 (2) |
Fe1—N6—H6A | 107.8 | N63—C71—C72 | 110.7 (2) |
C51—N6—H6B | 107.8 | C70—C71—C72 | 123.2 (2) |
Fe1—N6—H6B | 107.8 | C73—C72—C71 | 106.6 (2) |
H6A—N6—H6B | 107.2 | C73—C72—H72 | 126.7 |
C64—N61—C61 | 105.1 (2) | C71—C72—H72 | 126.7 |
C64—N61—Fe61 | 127.53 (17) | C72—C73—C74 | 107.3 (2) |
C61—N61—Fe61 | 127.38 (16) | C72—C73—H73 | 126.3 |
C69—N62—C66 | 106.1 (2) | C74—C73—H73 | 126.3 |
C69—N62—Fe61 | 127.56 (16) | N63—C74—C75 | 126.9 (2) |
C66—N62—Fe61 | 126.15 (17) | N63—C74—C73 | 110.0 (2) |
C71—N63—C74 | 105.3 (2) | C75—C74—C73 | 123.0 (2) |
C71—N63—Fe61 | 128.29 (16) | C74—C75—C76 | 122.8 (2) |
C74—N63—Fe61 | 126.44 (16) | C74—C75—C93 | 118.1 (2) |
C76—N64—C79 | 106.0 (2) | C76—C75—C93 | 119.1 (2) |
C76—N64—Fe61 | 126.88 (17) | N64—C76—C75 | 126.5 (2) |
C79—N64—Fe61 | 127.08 (16) | N64—C76—C77 | 110.3 (2) |
C105—N65—Fe61 | 120.20 (15) | C75—C76—C77 | 123.1 (2) |
C105—N65—H65A | 107.3 | C78—C77—C76 | 106.9 (2) |
Fe61—N65—H65A | 107.3 | C78—C77—H77 | 126.5 |
C105—N65—H65B | 107.3 | C76—C77—H77 | 126.5 |
Fe61—N65—H65B | 107.3 | C77—C78—C79 | 107.1 (2) |
H65A—N65—H65B | 106.9 | C77—C78—H78 | 126.5 |
C111—N66—Fe61 | 118.72 (15) | C79—C78—H78 | 126.5 |
C111—N66—H66A | 107.6 | N64—C79—C80 | 126.7 (2) |
Fe61—N66—H66A | 107.6 | N64—C79—C78 | 109.6 (2) |
C111—N66—H66B | 107.6 | C80—C79—C78 | 123.6 (2) |
Fe61—N66—H66B | 107.6 | C79—C80—C61 | 122.9 (2) |
H66A—N66—H66B | 107.1 | C79—C80—C99 | 118.2 (2) |
N1—C1—C20 | 126.2 (2) | C61—C80—C99 | 118.9 (2) |
N1—C1—C2 | 110.1 (2) | C86—C81—C82 | 118.6 (2) |
C20—C1—C2 | 123.7 (2) | C86—C81—C65 | 120.6 (2) |
C3—C2—C1 | 106.7 (2) | C82—C81—C65 | 120.8 (2) |
C3—C2—H2 | 126.6 | C83—C82—C81 | 120.4 (3) |
C1—C2—H2 | 126.6 | C83—C82—H82 | 119.8 |
C2—C3—C4 | 107.5 (2) | C81—C82—H82 | 119.8 |
C2—C3—H3 | 126.2 | C84—C83—C82 | 120.3 (3) |
C4—C3—H3 | 126.2 | C84—C83—H83 | 119.8 |
N1—C4—C5 | 125.8 (2) | C82—C83—H83 | 119.8 |
N1—C4—C3 | 110.1 (2) | C83—C84—C85 | 119.9 (3) |
C5—C4—C3 | 124.1 (2) | C83—C84—H84 | 120.1 |
C6—C5—C4 | 124.1 (2) | C85—C84—H84 | 120.1 |
C6—C5—C21 | 118.8 (2) | C86—C85—C84 | 120.3 (3) |
C4—C5—C21 | 117.1 (2) | C86—C85—H85 | 119.9 |
N2—C6—C5 | 126.1 (2) | C84—C85—H85 | 119.9 |
N2—C6—C7 | 110.2 (2) | C85—C86—C81 | 120.4 (3) |
C5—C6—C7 | 123.7 (2) | C85—C86—H86 | 119.8 |
C8—C7—C6 | 107.5 (2) | C81—C86—H86 | 119.8 |
C8—C7—H7 | 126.3 | C92—C87—C88 | 118.8 (3) |
C6—C7—H7 | 126.3 | C92—C87—C70 | 119.8 (3) |
C7—C8—C9 | 106.2 (2) | C88—C87—C70 | 121.3 (2) |
C7—C8—H8 | 126.9 | C89—C88—C87 | 120.3 (3) |
C9—C8—H8 | 126.9 | C89—C88—H88 | 119.9 |
N2—C9—C10 | 125.8 (2) | C87—C88—H88 | 119.9 |
N2—C9—C8 | 110.6 (2) | C88—C89—C90 | 120.4 (3) |
C10—C9—C8 | 123.6 (2) | C88—C89—H89 | 119.8 |
C11—C10—C9 | 122.7 (2) | C90—C89—H89 | 119.8 |
C11—C10—C27 | 118.6 (2) | C91—C90—C89 | 119.5 (3) |
C9—C10—C27 | 118.6 (2) | C91—C90—H90 | 120.3 |
N3—C11—C10 | 125.9 (2) | C89—C90—H90 | 120.3 |
N3—C11—C12 | 110.8 (2) | C90—C91—C92 | 121.1 (3) |
C10—C11—C12 | 123.2 (2) | C90—C91—H91 | 119.4 |
C13—C12—C11 | 106.8 (2) | C92—C91—H91 | 119.4 |
C13—C12—H12 | 126.6 | C91—C92—C87 | 119.8 (3) |
C11—C12—H12 | 126.6 | C91—C92—H92 | 120.1 |
C12—C13—C14 | 107.1 (2) | C87—C92—H92 | 120.1 |
C12—C13—H13 | 126.5 | C98—C93—C94 | 119.5 (2) |
C14—C13—H13 | 126.5 | C98—C93—C75 | 119.9 (2) |
N3—C14—C15 | 126.8 (2) | C94—C93—C75 | 120.6 (3) |
N3—C14—C13 | 110.0 (2) | C95—C94—C93 | 120.2 (3) |
C15—C14—C13 | 123.2 (2) | C95—C94—H94 | 119.9 |
C14—C15—C16 | 123.0 (2) | C93—C94—H94 | 119.9 |
C14—C15—C33 | 118.0 (2) | C96—C95—C94 | 119.9 (3) |
C16—C15—C33 | 119.0 (2) | C96—C95—H95 | 120.0 |
N4—C16—C15 | 126.6 (2) | C94—C95—H95 | 120.0 |
N4—C16—C17 | 110.0 (2) | C97—C96—C95 | 120.4 (3) |
C15—C16—C17 | 123.4 (2) | C97—C96—H96 | 119.8 |
C18—C17—C16 | 107.0 (2) | C95—C96—H96 | 119.8 |
C18—C17—H17 | 126.5 | C96—C97—C98 | 119.8 (3) |
C16—C17—H17 | 126.5 | C96—C97—H97 | 120.1 |
C17—C18—C19 | 107.3 (2) | C98—C97—H97 | 120.1 |
C17—C18—H18 | 126.4 | C93—C98—C97 | 120.2 (3) |
C19—C18—H18 | 126.4 | C93—C98—H98 | 119.9 |
N4—C19—C20 | 126.5 (2) | C97—C98—H98 | 119.9 |
N4—C19—C18 | 109.8 (2) | C104—C99—C100 | 119.1 (2) |
C20—C19—C18 | 123.6 (2) | C104—C99—C80 | 120.5 (2) |
C19—C20—C1 | 122.7 (2) | C100—C99—C80 | 120.4 (2) |
C19—C20—C39 | 118.9 (2) | C101—C100—C99 | 120.1 (3) |
C1—C20—C39 | 118.3 (2) | C101—C100—H100 | 119.9 |
C26—C21—C22 | 119.7 (3) | C99—C100—H100 | 119.9 |
C26—C21—C5 | 120.2 (3) | C102—C101—C100 | 120.0 (3) |
C22—C21—C5 | 120.1 (3) | C102—C101—H101 | 120.0 |
C21—C22—C23 | 119.5 (3) | C100—C101—H101 | 120.0 |
C21—C22—H22 | 120.2 | C103—C102—C101 | 120.2 (3) |
C23—C22—H22 | 120.2 | C103—C102—H102 | 119.9 |
C24—C23—C22 | 120.4 (3) | C101—C102—H102 | 119.9 |
C24—C23—H23 | 119.8 | C102—C103—C104 | 120.2 (3) |
C22—C23—H23 | 119.8 | C102—C103—H103 | 119.9 |
C23—C24—C25 | 119.7 (3) | C104—C103—H103 | 119.9 |
C23—C24—H24 | 120.2 | C99—C104—C103 | 120.3 (3) |
C25—C24—H24 | 120.2 | C99—C104—H104 | 119.8 |
C24—C25—C26 | 121.4 (3) | C103—C104—H104 | 119.8 |
C24—C25—H25 | 119.3 | N65—C105—C109 | 107.59 (19) |
C26—C25—H25 | 119.3 | N65—C105—C106 | 113.3 (2) |
C21—C26—C25 | 119.3 (3) | C109—C105—C106 | 111.7 (2) |
C21—C26—H26 | 120.3 | N65—C105—H105 | 108.0 |
C25—C26—H26 | 120.3 | C109—C105—H105 | 108.0 |
C32—C27—C28 | 119.0 (3) | C106—C105—H105 | 108.0 |
C32—C27—C10 | 119.7 (2) | C108—C106—C107 | 111.4 (3) |
C28—C27—C10 | 121.3 (2) | C108—C106—C105 | 110.5 (2) |
C29—C28—C27 | 120.6 (3) | C107—C106—C105 | 112.3 (2) |
C29—C28—H28 | 119.7 | C108—C106—H106 | 107.5 |
C27—C28—H28 | 119.7 | C107—C106—H106 | 107.5 |
C30—C29—C28 | 119.8 (3) | C105—C106—H106 | 107.5 |
C30—C29—H29 | 120.1 | C106—C107—H10A | 109.5 |
C28—C29—H29 | 120.1 | C106—C107—H10B | 109.5 |
C31—C30—C29 | 119.9 (3) | H10A—C107—H10B | 109.5 |
C31—C30—H30 | 120.0 | C106—C107—H10C | 109.5 |
C29—C30—H30 | 120.0 | H10A—C107—H10C | 109.5 |
C30—C31—C32 | 120.5 (3) | H10B—C107—H10C | 109.5 |
C30—C31—H31 | 119.8 | C106—C108—H10D | 109.5 |
C32—C31—H31 | 119.8 | C106—C108—H10E | 109.5 |
C27—C32—C31 | 120.2 (3) | H10D—C108—H10E | 109.5 |
C27—C32—H32 | 119.9 | C106—C108—H10F | 109.5 |
C31—C32—H32 | 119.9 | H10D—C108—H10F | 109.5 |
C34—C33—C38 | 119.7 (3) | H10E—C108—H10F | 109.5 |
C34—C33—C15 | 122.0 (3) | O61—C109—O62 | 125.0 (3) |
C38—C33—C15 | 118.2 (3) | O61—C109—C105 | 123.8 (2) |
C33—C34—C35 | 118.7 (4) | O62—C109—C105 | 111.2 (2) |
C33—C34—H34 | 120.7 | O62—C110—H11C | 109.5 |
C35—C34—H34 | 120.7 | O62—C110—H11D | 109.5 |
C36—C35—C34 | 120.2 (4) | H11C—C110—H11D | 109.5 |
C36—C35—H35 | 119.9 | O62—C110—H11E | 109.5 |
C34—C35—H35 | 119.9 | H11C—C110—H11E | 109.5 |
C37—C36—C35 | 121.1 (4) | H11D—C110—H11E | 109.5 |
C37—C36—H36 | 119.5 | N66—C111—C115 | 107.8 (2) |
C35—C36—H36 | 119.5 | N66—C111—C112 | 114.4 (2) |
C36—C37—C38 | 120.1 (4) | C115—C111—C112 | 110.7 (2) |
C36—C37—H37 | 119.9 | N66—C111—H111 | 107.9 |
C38—C37—H37 | 119.9 | C115—C111—H111 | 107.9 |
C37—C38—C33 | 120.3 (4) | C112—C111—H111 | 107.9 |
C37—C38—H38 | 119.9 | C113—C112—C114 | 112.1 (2) |
C33—C38—H38 | 119.9 | C113—C112—C111 | 111.2 (2) |
C44—C39—C40 | 119.2 (2) | C114—C112—C111 | 112.3 (2) |
C44—C39—C20 | 120.3 (2) | C113—C112—H112 | 107.0 |
C40—C39—C20 | 120.4 (2) | C114—C112—H112 | 107.0 |
C41—C40—C39 | 119.8 (3) | C111—C112—H112 | 107.0 |
C41—C40—H40 | 120.1 | C112—C113—H11F | 109.5 |
C39—C40—H40 | 120.1 | C112—C113—H11G | 109.5 |
C42—C41—C40 | 121.0 (3) | H11F—C113—H11G | 109.5 |
C42—C41—H41 | 119.5 | C112—C113—H11H | 109.5 |
C40—C41—H41 | 119.5 | H11F—C113—H11H | 109.5 |
C41—C42—C43 | 119.4 (3) | H11G—C113—H11H | 109.5 |
C41—C42—H42 | 120.3 | C112—C114—H11I | 109.5 |
C43—C42—H42 | 120.3 | C112—C114—H11J | 109.5 |
C42—C43—C44 | 120.1 (3) | H11I—C114—H11J | 109.5 |
C42—C43—H43 | 119.9 | C112—C114—H11K | 109.5 |
C44—C43—H43 | 119.9 | H11I—C114—H11K | 109.5 |
C39—C44—C43 | 120.4 (3) | H11J—C114—H11K | 109.5 |
C39—C44—H44 | 119.8 | O63—C115—O64 | 125.1 (3) |
C43—C44—H44 | 119.8 | O63—C115—C111 | 125.2 (2) |
N5—C45—C49 | 107.82 (19) | O64—C115—C111 | 109.7 (2) |
N5—C45—C46 | 114.0 (2) | O64—C116—H11L | 109.5 |
C49—C45—C46 | 111.2 (2) | O64—C116—H11M | 109.5 |
N5—C45—H45 | 107.9 | H11L—C116—H11M | 109.5 |
C49—C45—H45 | 107.9 | O64—C116—H11N | 109.5 |
C46—C45—H45 | 107.9 | H11L—C116—H11N | 109.5 |
C48—C46—C45 | 110.7 (2) | H11M—C116—H11N | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Fe(C44H28N4)(C6H13NO2)2]CF3O3S·CH2Cl2 |
Mr | 1164.90 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 11.3660 (2), 14.4438 (2), 17.6675 (2) |
α, β, γ (°) | 78.148 (1), 87.016 (1), 75.485 (1) |
V (Å3) | 2748.01 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.48 |
Crystal size (mm) | 0.24 × 0.18 × 0.11 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33368, 33368, 23226 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.746 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.133, 0.99 |
No. of reflections | 33368 |
No. of parameters | 1406 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.76, −0.59 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.008 (8) |
Computer programs: KappaCCD Server Software (Nonius, 1999), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR97 (Altomare et al., 1998), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1998), SHELXL97.
Fe1—N3 | 1.990 (2) | Fe61—N66 | 2.016 (2) |
Fe1—N1 | 1.995 (2) | Fe61—N65 | 2.031 (2) |
Fe1—N4 | 2.002 (2) | C2—C3 | 1.356 (4) |
Fe1—N2 | 2.005 (2) | C7—C8 | 1.360 (4) |
Fe1—N6 | 2.023 (2) | C12—C13 | 1.352 (4) |
Fe1—N5 | 2.029 (2) | C17—C18 | 1.353 (4) |
Fe61—N61 | 1.987 (2) | C62—C63 | 1.360 (4) |
Fe61—N63 | 1.995 (2) | C67—C68 | 1.357 (4) |
Fe61—N64 | 2.003 (2) | C72—C73 | 1.353 (4) |
Fe61—N62 | 2.004 (2) | C77—C78 | 1.355 (4) |
N3—Fe1—N1 | 179.20 (10) | N61—Fe61—N63 | 178.66 (10) |
N3—Fe1—N4 | 90.61 (8) | N61—Fe61—N64 | 89.84 (8) |
N1—Fe1—N4 | 89.58 (8) | N63—Fe61—N64 | 90.40 (8) |
N3—Fe1—N2 | 89.34 (8) | N61—Fe61—N62 | 90.56 (8) |
N1—Fe1—N2 | 90.47 (8) | N63—Fe61—N62 | 89.19 (8) |
N4—Fe1—N2 | 179.78 (11) | N64—Fe61—N62 | 179.42 (9) |
N3—Fe1—N6 | 88.74 (8) | N61—Fe61—N66 | 91.13 (8) |
N1—Fe1—N6 | 92.05 (8) | N63—Fe61—N66 | 90.20 (8) |
N4—Fe1—N6 | 89.08 (8) | N64—Fe61—N66 | 88.98 (9) |
N2—Fe1—N6 | 91.13 (8) | N62—Fe61—N66 | 91.43 (8) |
N3—Fe1—N5 | 89.02 (8) | N61—Fe61—N65 | 90.39 (8) |
N1—Fe1—N5 | 90.20 (8) | N63—Fe61—N65 | 88.29 (8) |
N4—Fe1—N5 | 90.83 (8) | N64—Fe61—N65 | 90.37 (8) |
N2—Fe1—N5 | 88.95 (9) | N62—Fe61—N65 | 89.20 (8) |
N6—Fe1—N5 | 177.75 (9) | N66—Fe61—N65 | 178.35 (9) |
Cytochrome f is one of the four redox centres in the cytochrome b6f complex of the thylakoid membrane in oxygenic photosynthetic organisms. Cytochrome f is also the electron donor to the Cu-containing protein plastocyanin in some eukariotic algae and cyanobacteria, when growing in a Cu-deficient environment. The protein consists predominantly of β-sheets and has a unique ligation of the heme by the α-amino N of the N-terminal residue. The structures of two truncated forms of the protein have been reported, one from turnip (Martinez et al., 1994, 1996) and the other from chlamydonas reinhardtii (Chi et al., 2000). The present study of the title compound, (I), seems to be the only reported structure of an amino ester complex of iron porphyrins. The crystal structures of primary amine complexes of iron(II) porphyrins are the only other examples involving NH2 groups and iron porphyrins that have been reported to date (Munro et al., 1999). \sch
The crystal structure of (I) is comprised of two independent ion pairs in the asymmetric unit. The iron porphyrin differs slightly in the orientation of the C—Hα bonds of the axial ligands with respect to the porphyrin plane. Thus, the orientation of the ligands with respect to the N1—Fe—N3 axis is not equivalent for the two independent molecules. The angle between the N—Fe—N axis and the projection of the ligand C—Hα bond normal onto the porphyrin plane is 139.5 (2)° for molecule A and 138 (1)° for molecule B. The structures of (Ia) and (Ib) are shown in Fig. 1, and selected bond distances and angles are given in Table 1.
The equatorial Fe—N distances average 1.998 (2) Å for (Ia) and 1.997 (2) Å for (Ib), which is quite expected for low-spin iron(III) porphyrinate derivatives (Scheidt & Reed, 1981). The axial Fe—N bonds average 2.026 (2) Å for (Ia) and 2.023 (2) Å in (Ib). In [(TPP)Fe(1-BuNH2)2], [(TPP)Fe(BzNH2)2] and [(TPP)Fe(PhCH2CH2NH2)2] (TPP is tetraphenylporphyrin Correct?; Munro et al., 1999), the axial Fe—N distances are 2.039 (3), 2.043 (3) and 2.028 (2) Å, respectively. These three values are longer than those observed for (I) and reflect the increase of the oxidation state, from the ferrous state for the alkyl amine complexes to the ferric state for (I). Accordingly, a better σ donation from the ligated N atoms is expected in the ferric state.
All these distances are significantly longer than the Fe—NH2 distance reported for the X-ray structure of turnip cytochrome f (1.94 Å; Martinez et al., 1996). This is unexpected and the result was previously discussed by Munro and coworkers (Munro et al., 1999).
Recently, a truncated form of cytochrome f from chlamydomonas reinhardtii has been crystallized and its structure determined to 2.0 Å resolution (Chi et al., 2000). The distance between the Fe atom and the N atom of the amino group of the N-terminus residue (Tyrosine) is 2.7 Å. Although the two protein structures display the same folding, the latter Fe—N distance is much longer. This situation will probably be solved with the structure determination of other cytochromes f.