We have identified two polymorphs of the molecular complex [(TPA)Fe(III)(TCC)]PF6 [TPA = tris(2-pyridylmethyl)amine and TCC = 3,4,5,6-tetrachlorocatecholate dianion]: one is monoclinic and the other is orthorhombic. By lowering the temperature both undergo a thermal spin-crossover between a high-spin (S = 5/2) and a low-spin (S = 1/2) state, which we detected by magnetic, optical and X-ray diffraction measurements. The thermal crossover is only slightly shifted between the polymorphs. Their crystalline structures consist of similar cation layers alternating with PF6 anion layers, packed differently in the two polymorphs. The magnetic and optical properties of the polymorphs are presented.
Supporting information
CCDC references: 719405; 746148; 746149; 746150
For all compounds, data collection: CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.26; cell refinement: CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26; data reduction: CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26; program(s) used to solve structure: SIR97_(Altomare & al., 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON_(Spek, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Crystal data top
C24H18Cl4F6FeN4O2P | Z = 4 |
Mr = 737.04 | F(000) = 1476 |
Monoclinic, P21/a | Dx = 1.784 Mg m−3 |
a = 8.4250 (2) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 35.9730 (8) Å | µ = 1.07 mm−1 |
c = 9.0586 (2) Å | T = 80 K |
β = 91.942 (2)° | Needle, dark |
V = 2743.84 (11) Å3 | 0.25 × 0.05 × 0.05 mm |
Data collection top
CCD Saphire 3 Xcalibur diffractometer | 4967 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 27.0°, θmin = 2.7° |
Detector resolution: 19.64 pixels mm-1 | h = −10→10 |
ω scan | k = −45→45 |
36645 measured reflections | l = −11→11 |
5983 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.20 | w = 1/[σ2(Fo2) + (0.P)2 + 14.3117P] where P = (Fo2 + 2Fc2)/3 |
5983 reflections | (Δ/σ)max < 0.001 |
379 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.76 e Å−3 |
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 | Uiso*/Ueq | |
P1 | 0.30900 (14) | 0.47926 (3) | 0.22510 (14) | 0.0241 (3) | |
F1 | 0.3095 (4) | 0.47638 (12) | 0.4004 (4) | 0.0651 (12) | |
F2 | 0.3054 (4) | 0.48280 (13) | 0.0515 (4) | 0.0694 (12) | |
F3 | 0.3265 (3) | 0.52318 (7) | 0.2385 (3) | 0.0315 (6) | |
F4 | 0.1179 (3) | 0.48382 (7) | 0.2231 (4) | 0.0384 (7) | |
F5 | 0.2890 (4) | 0.43575 (9) | 0.2130 (7) | 0.0914 (18) | |
F6 | 0.4967 (3) | 0.47492 (8) | 0.2289 (4) | 0.0439 (8) | |
Fe1 | 0.07215 (6) | 0.367346 (14) | 0.70442 (6) | 0.01038 (12) | |
Cl1 | 0.01283 (12) | 0.23462 (2) | 0.63995 (10) | 0.0180 (2) | |
Cl2 | 0.14156 (12) | 0.20919 (2) | 0.33382 (11) | 0.0188 (2) | |
Cl3 | 0.28784 (12) | 0.26774 (3) | 0.12244 (10) | 0.0195 (2) | |
Cl4 | 0.31469 (11) | 0.35191 (2) | 0.22529 (10) | 0.01446 (18) | |
N4 | 0.2860 (4) | 0.36730 (9) | 0.7950 (3) | 0.0126 (6) | |
N2 | 0.0897 (4) | 0.42244 (8) | 0.7261 (3) | 0.0118 (6) | |
N3 | −0.0078 (3) | 0.36756 (9) | 0.9038 (3) | 0.0102 (6) | |
N1 | −0.1370 (4) | 0.38074 (8) | 0.6171 (3) | 0.0121 (6) | |
O1 | 0.0458 (3) | 0.31620 (7) | 0.6895 (3) | 0.0125 (5) | |
O2 | 0.1633 (3) | 0.36544 (7) | 0.5122 (3) | 0.0124 (5) | |
C1 | −0.2622 (5) | 0.35792 (11) | 0.5987 (4) | 0.0145 (8) | |
H1 | −0.2557 | 0.3333 | 0.6366 | 0.017* | |
C2 | −0.4004 (5) | 0.36948 (12) | 0.5259 (4) | 0.0178 (8) | |
H2 | −0.4877 | 0.3530 | 0.5131 | 0.021* | |
C3 | −0.4098 (5) | 0.40543 (11) | 0.4721 (4) | 0.0190 (8) | |
H3 | −0.5032 | 0.4137 | 0.4203 | 0.023* | |
C4 | −0.2815 (5) | 0.42944 (11) | 0.4942 (4) | 0.0179 (8) | |
H4 | −0.2869 | 0.4544 | 0.4598 | 0.021* | |
C5 | −0.1459 (5) | 0.41619 (10) | 0.5674 (4) | 0.0143 (7) | |
C6 | 0.0032 (5) | 0.43854 (10) | 0.5937 (4) | 0.0156 (8) | |
H6A | 0.0704 | 0.4372 | 0.5063 | 0.019* | |
H6B | −0.0235 | 0.4649 | 0.6117 | 0.019* | |
C7 | 0.0123 (5) | 0.43390 (10) | 0.8668 (4) | 0.0156 (8) | |
H7A | 0.0805 | 0.4524 | 0.9192 | 0.019* | |
H7B | −0.0909 | 0.4459 | 0.8420 | 0.019* | |
C8 | −0.0142 (4) | 0.40138 (10) | 0.9673 (4) | 0.0126 (7) | |
C9 | −0.0500 (4) | 0.40532 (11) | 1.1151 (4) | 0.0149 (8) | |
H9 | −0.0525 | 0.4292 | 1.1594 | 0.018* | |
C10 | −0.0821 (5) | 0.37385 (11) | 1.1968 (4) | 0.0167 (8) | |
H10 | −0.1068 | 0.3760 | 1.2980 | 0.020* | |
C11 | −0.0781 (4) | 0.33918 (11) | 1.1297 (4) | 0.0147 (8) | |
H11 | −0.1016 | 0.3174 | 1.1839 | 0.018* | |
C12 | −0.0397 (4) | 0.33686 (10) | 0.9838 (4) | 0.0134 (7) | |
H12 | −0.0353 | 0.3131 | 0.9380 | 0.016* | |
C13 | 0.2622 (5) | 0.43189 (11) | 0.7297 (4) | 0.0165 (8) | |
H13A | 0.2801 | 0.4559 | 0.7811 | 0.020* | |
H13B | 0.2998 | 0.4343 | 0.6277 | 0.020* | |
C14 | 0.3523 (5) | 0.40142 (11) | 0.8099 (4) | 0.0139 (8) | |
C15 | 0.4948 (5) | 0.40649 (12) | 0.8876 (4) | 0.0185 (8) | |
H15 | 0.5376 | 0.4307 | 0.9022 | 0.022* | |
C16 | 0.5736 (5) | 0.37566 (12) | 0.9435 (4) | 0.0200 (8) | |
H16 | 0.6717 | 0.3785 | 0.9972 | 0.024* | |
C17 | 0.5098 (5) | 0.34060 (11) | 0.9211 (4) | 0.0178 (8) | |
H17 | 0.5658 | 0.3191 | 0.9542 | 0.021* | |
C18 | 0.3633 (5) | 0.33754 (11) | 0.8496 (4) | 0.0160 (8) | |
H18 | 0.3159 | 0.3137 | 0.8387 | 0.019* | |
C19 | 0.0987 (4) | 0.30353 (10) | 0.5620 (4) | 0.0119 (7) | |
C20 | 0.0923 (4) | 0.26642 (10) | 0.5183 (4) | 0.0129 (7) | |
C21 | 0.1509 (5) | 0.25549 (10) | 0.3841 (4) | 0.0136 (7) | |
C22 | 0.2188 (5) | 0.28146 (10) | 0.2925 (4) | 0.0134 (7) | |
C23 | 0.2277 (4) | 0.31898 (10) | 0.3345 (4) | 0.0120 (7) | |
C24 | 0.1645 (4) | 0.33058 (10) | 0.4666 (4) | 0.0114 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0245 (6) | 0.0136 (5) | 0.0335 (6) | 0.0014 (4) | −0.0069 (5) | −0.0018 (4) |
F1 | 0.062 (2) | 0.097 (3) | 0.0355 (19) | −0.020 (2) | −0.0020 (17) | 0.043 (2) |
F2 | 0.057 (2) | 0.114 (3) | 0.036 (2) | 0.009 (2) | −0.0147 (17) | −0.035 (2) |
F3 | 0.0316 (15) | 0.0173 (12) | 0.0456 (17) | −0.0025 (11) | 0.0017 (12) | 0.0001 (11) |
F4 | 0.0236 (14) | 0.0197 (13) | 0.071 (2) | −0.0001 (11) | −0.0039 (14) | −0.0006 (13) |
F5 | 0.043 (2) | 0.0156 (15) | 0.213 (6) | 0.0038 (14) | −0.034 (3) | −0.016 (2) |
F6 | 0.0242 (15) | 0.0348 (16) | 0.072 (2) | 0.0055 (12) | −0.0083 (15) | −0.0052 (15) |
Fe1 | 0.0127 (3) | 0.0108 (2) | 0.0077 (2) | 0.0001 (2) | 0.00076 (19) | −0.00007 (19) |
Cl1 | 0.0241 (5) | 0.0139 (4) | 0.0165 (5) | −0.0019 (4) | 0.0081 (4) | 0.0018 (3) |
Cl2 | 0.0253 (5) | 0.0122 (4) | 0.0193 (5) | −0.0011 (4) | 0.0070 (4) | −0.0032 (3) |
Cl3 | 0.0290 (5) | 0.0183 (4) | 0.0117 (4) | −0.0005 (4) | 0.0086 (4) | −0.0028 (3) |
Cl4 | 0.0180 (5) | 0.0154 (4) | 0.0101 (4) | −0.0017 (3) | 0.0035 (3) | 0.0017 (3) |
N4 | 0.0163 (16) | 0.0175 (15) | 0.0041 (14) | 0.0003 (13) | 0.0025 (11) | −0.0002 (12) |
N2 | 0.0150 (16) | 0.0131 (14) | 0.0073 (15) | 0.0008 (12) | 0.0001 (12) | 0.0006 (11) |
N3 | 0.0079 (14) | 0.0157 (14) | 0.0070 (14) | 0.0005 (12) | 0.0012 (11) | 0.0003 (12) |
N1 | 0.0155 (16) | 0.0149 (15) | 0.0061 (14) | −0.0007 (12) | 0.0021 (12) | −0.0010 (11) |
O1 | 0.0152 (14) | 0.0137 (12) | 0.0087 (12) | −0.0001 (10) | 0.0039 (10) | −0.0004 (10) |
O2 | 0.0171 (14) | 0.0111 (12) | 0.0093 (12) | −0.0007 (10) | 0.0042 (10) | −0.0001 (10) |
C1 | 0.0151 (19) | 0.0179 (18) | 0.0107 (18) | 0.0006 (15) | 0.0034 (14) | −0.0020 (14) |
C2 | 0.015 (2) | 0.025 (2) | 0.0139 (19) | 0.0005 (16) | 0.0015 (15) | −0.0068 (16) |
C3 | 0.019 (2) | 0.026 (2) | 0.0117 (19) | 0.0061 (16) | −0.0035 (15) | −0.0047 (15) |
C4 | 0.024 (2) | 0.021 (2) | 0.0079 (18) | 0.0054 (16) | −0.0009 (15) | −0.0010 (14) |
C5 | 0.020 (2) | 0.0152 (17) | 0.0078 (17) | 0.0006 (15) | −0.0005 (14) | −0.0019 (14) |
C6 | 0.022 (2) | 0.0150 (17) | 0.0093 (18) | 0.0023 (15) | −0.0015 (15) | 0.0018 (14) |
C7 | 0.018 (2) | 0.0157 (18) | 0.0132 (19) | 0.0009 (15) | 0.0002 (15) | −0.0015 (14) |
C8 | 0.0091 (18) | 0.0136 (17) | 0.0149 (19) | 0.0018 (14) | −0.0021 (14) | −0.0005 (14) |
C9 | 0.0129 (19) | 0.0193 (19) | 0.0125 (18) | 0.0020 (14) | −0.0005 (14) | −0.0055 (14) |
C10 | 0.0162 (19) | 0.027 (2) | 0.0074 (17) | 0.0022 (16) | 0.0009 (14) | −0.0017 (15) |
C11 | 0.0123 (19) | 0.0194 (18) | 0.0126 (18) | 0.0006 (15) | 0.0020 (14) | 0.0045 (14) |
C12 | 0.0106 (18) | 0.0150 (17) | 0.0144 (18) | −0.0001 (14) | −0.0031 (14) | 0.0010 (14) |
C13 | 0.016 (2) | 0.0164 (18) | 0.0169 (19) | −0.0028 (15) | 0.0023 (15) | 0.0020 (15) |
C14 | 0.016 (2) | 0.0176 (18) | 0.0083 (17) | 0.0000 (15) | 0.0041 (14) | −0.0010 (14) |
C15 | 0.015 (2) | 0.024 (2) | 0.016 (2) | −0.0053 (16) | 0.0014 (15) | 0.0005 (16) |
C16 | 0.013 (2) | 0.031 (2) | 0.016 (2) | 0.0001 (16) | 0.0006 (15) | 0.0014 (16) |
C17 | 0.016 (2) | 0.025 (2) | 0.0126 (19) | 0.0036 (16) | 0.0026 (15) | 0.0032 (15) |
C18 | 0.018 (2) | 0.0175 (18) | 0.0129 (19) | 0.0010 (15) | 0.0040 (15) | 0.0014 (14) |
C19 | 0.0105 (18) | 0.0133 (17) | 0.0118 (18) | 0.0001 (14) | −0.0016 (14) | −0.0004 (14) |
C20 | 0.0113 (18) | 0.0131 (17) | 0.0146 (18) | −0.0003 (14) | 0.0020 (14) | 0.0024 (14) |
C21 | 0.0148 (18) | 0.0134 (17) | 0.0126 (18) | −0.0006 (14) | 0.0023 (14) | −0.0012 (14) |
C22 | 0.0153 (19) | 0.0163 (18) | 0.0085 (17) | 0.0015 (14) | 0.0012 (14) | −0.0005 (13) |
C23 | 0.0121 (18) | 0.0136 (17) | 0.0104 (17) | 0.0016 (14) | 0.0010 (14) | 0.0008 (13) |
C24 | 0.0114 (18) | 0.0120 (16) | 0.0106 (17) | 0.0000 (13) | −0.0023 (14) | 0.0011 (13) |
Geometric parameters (Å, º) top
P1—F2 | 1.577 (4) | C4—C5 | 1.386 (5) |
P1—F5 | 1.578 (3) | C4—H4 | 0.9500 |
P1—F6 | 1.588 (3) | C5—C6 | 1.504 (5) |
P1—F1 | 1.591 (3) | C6—H6A | 0.9900 |
P1—F3 | 1.591 (3) | C6—H6B | 0.9900 |
P1—F4 | 1.618 (3) | C7—C8 | 1.504 (5) |
Fe1—O1 | 1.857 (3) | C7—H7A | 0.9900 |
Fe1—O2 | 1.928 (3) | C7—H7B | 0.9900 |
Fe1—N3 | 1.949 (3) | C8—C9 | 1.389 (5) |
Fe1—N4 | 1.954 (3) | C9—C10 | 1.384 (5) |
Fe1—N1 | 1.967 (3) | C9—H9 | 0.9500 |
Fe1—N2 | 1.996 (3) | C10—C11 | 1.388 (5) |
Cl1—C20 | 1.739 (4) | C10—H10 | 0.9500 |
Cl2—C21 | 1.728 (4) | C11—C12 | 1.374 (5) |
Cl3—C22 | 1.737 (4) | C11—H11 | 0.9500 |
Cl4—C23 | 1.723 (4) | C12—H12 | 0.9500 |
N4—C18 | 1.339 (5) | C13—C14 | 1.506 (5) |
N4—C14 | 1.353 (5) | C13—H13A | 0.9900 |
N2—C13 | 1.492 (5) | C13—H13B | 0.9900 |
N2—C6 | 1.499 (4) | C14—C15 | 1.384 (5) |
N2—C7 | 1.509 (5) | C15—C16 | 1.380 (6) |
N3—C8 | 1.348 (5) | C15—H15 | 0.9500 |
N3—C12 | 1.353 (5) | C16—C17 | 1.383 (6) |
N1—C1 | 1.343 (5) | C16—H16 | 0.9500 |
N1—C5 | 1.353 (5) | C17—C18 | 1.379 (6) |
O1—C19 | 1.333 (4) | C17—H17 | 0.9500 |
O2—C24 | 1.320 (4) | C18—H18 | 0.9500 |
C1—C2 | 1.382 (5) | C19—C20 | 1.393 (5) |
C1—H1 | 0.9500 | C19—C24 | 1.426 (5) |
C2—C3 | 1.384 (6) | C20—C21 | 1.385 (5) |
C2—H2 | 0.9500 | C21—C22 | 1.386 (5) |
C3—C4 | 1.392 (6) | C22—C23 | 1.404 (5) |
C3—H3 | 0.9500 | C23—C24 | 1.390 (5) |
| | | |
F2—P1—F5 | 90.7 (3) | C5—C6—H6A | 110.2 |
F2—P1—F6 | 90.9 (2) | N2—C6—H6B | 110.2 |
F5—P1—F6 | 90.46 (18) | C5—C6—H6B | 110.2 |
F2—P1—F1 | 178.7 (2) | H6A—C6—H6B | 108.5 |
F5—P1—F1 | 90.1 (3) | C8—C7—N2 | 112.1 (3) |
F6—P1—F1 | 90.1 (2) | C8—C7—H7A | 109.2 |
F2—P1—F3 | 89.7 (2) | N2—C7—H7A | 109.2 |
F5—P1—F3 | 179.1 (2) | C8—C7—H7B | 109.2 |
F6—P1—F3 | 90.34 (16) | N2—C7—H7B | 109.2 |
F1—P1—F3 | 89.5 (2) | H7A—C7—H7B | 107.9 |
F2—P1—F4 | 89.71 (19) | N3—C8—C9 | 121.1 (3) |
F5—P1—F4 | 89.78 (17) | N3—C8—C7 | 115.8 (3) |
F6—P1—F4 | 179.4 (2) | C9—C8—C7 | 123.1 (3) |
F1—P1—F4 | 89.3 (2) | C10—C9—C8 | 119.0 (3) |
F3—P1—F4 | 89.41 (15) | C10—C9—H9 | 120.5 |
O1—Fe1—O2 | 87.10 (11) | C8—C9—H9 | 120.5 |
O1—Fe1—N3 | 91.56 (12) | C9—C10—C11 | 119.5 (3) |
O2—Fe1—N3 | 176.26 (12) | C9—C10—H10 | 120.2 |
O1—Fe1—N4 | 97.80 (12) | C11—C10—H10 | 120.2 |
O2—Fe1—N4 | 89.39 (12) | C12—C11—C10 | 119.1 (4) |
N3—Fe1—N4 | 87.34 (12) | C12—C11—H11 | 120.5 |
O1—Fe1—N1 | 96.33 (12) | C10—C11—H11 | 120.5 |
O2—Fe1—N1 | 91.40 (12) | N3—C12—C11 | 121.6 (3) |
N3—Fe1—N1 | 92.22 (13) | N3—C12—H12 | 119.2 |
N4—Fe1—N1 | 165.87 (13) | C11—C12—H12 | 119.2 |
O1—Fe1—N2 | 176.97 (13) | N2—C13—C14 | 108.6 (3) |
O2—Fe1—N2 | 95.38 (12) | N2—C13—H13A | 110.0 |
N3—Fe1—N2 | 86.08 (13) | C14—C13—H13A | 110.0 |
N4—Fe1—N2 | 83.99 (13) | N2—C13—H13B | 110.0 |
N1—Fe1—N2 | 81.89 (13) | C14—C13—H13B | 110.0 |
C18—N4—C14 | 119.6 (3) | H13A—C13—H13B | 108.4 |
C18—N4—Fe1 | 125.9 (3) | N4—C14—C15 | 121.2 (4) |
C14—N4—Fe1 | 114.4 (3) | N4—C14—C13 | 114.4 (3) |
C13—N2—C6 | 112.1 (3) | C15—C14—C13 | 124.3 (4) |
C13—N2—C7 | 111.6 (3) | C16—C15—C14 | 118.6 (4) |
C6—N2—C7 | 111.0 (3) | C16—C15—H15 | 120.7 |
C13—N2—Fe1 | 107.3 (2) | C14—C15—H15 | 120.7 |
C6—N2—Fe1 | 105.8 (2) | C15—C16—C17 | 119.9 (4) |
C7—N2—Fe1 | 108.8 (2) | C15—C16—H16 | 120.0 |
C8—N3—C12 | 119.8 (3) | C17—C16—H16 | 120.0 |
C8—N3—Fe1 | 114.8 (2) | C18—C17—C16 | 118.6 (4) |
C12—N3—Fe1 | 125.0 (3) | C18—C17—H17 | 120.7 |
C1—N1—C5 | 120.0 (3) | C16—C17—H17 | 120.7 |
C1—N1—Fe1 | 126.1 (3) | N4—C18—C17 | 121.7 (4) |
C5—N1—Fe1 | 113.8 (3) | N4—C18—H18 | 119.1 |
C19—O1—Fe1 | 111.0 (2) | C17—C18—H18 | 119.1 |
C24—O2—Fe1 | 108.9 (2) | O1—C19—C20 | 124.3 (3) |
N1—C1—C2 | 121.4 (4) | O1—C19—C24 | 116.1 (3) |
N1—C1—H1 | 119.3 | C20—C19—C24 | 119.6 (3) |
C2—C1—H1 | 119.3 | C21—C20—C19 | 120.7 (3) |
C1—C2—C3 | 119.1 (4) | C21—C20—Cl1 | 121.7 (3) |
C1—C2—H2 | 120.4 | C19—C20—Cl1 | 117.6 (3) |
C3—C2—H2 | 120.4 | C20—C21—C22 | 120.0 (3) |
C2—C3—C4 | 119.6 (4) | C20—C21—Cl2 | 119.4 (3) |
C2—C3—H3 | 120.2 | C22—C21—Cl2 | 120.6 (3) |
C4—C3—H3 | 120.2 | C21—C22—C23 | 120.4 (3) |
C5—C4—C3 | 118.6 (4) | C21—C22—Cl3 | 119.8 (3) |
C5—C4—H4 | 120.7 | C23—C22—Cl3 | 119.8 (3) |
C3—C4—H4 | 120.7 | C24—C23—C22 | 120.2 (3) |
N1—C5—C4 | 121.2 (4) | C24—C23—Cl4 | 118.1 (3) |
N1—C5—C6 | 114.5 (3) | C22—C23—Cl4 | 121.7 (3) |
C4—C5—C6 | 124.2 (3) | O2—C24—C23 | 124.2 (3) |
N2—C6—C5 | 107.5 (3) | O2—C24—C19 | 116.8 (3) |
N2—C6—H6A | 110.2 | C23—C24—C19 | 119.0 (3) |
| | | |
O1—Fe1—N4—C18 | −10.6 (3) | C13—N2—C6—C5 | 158.2 (3) |
O2—Fe1—N4—C18 | −97.6 (3) | C7—N2—C6—C5 | −76.3 (4) |
N3—Fe1—N4—C18 | 80.6 (3) | Fe1—N2—C6—C5 | 41.5 (3) |
N1—Fe1—N4—C18 | 169.1 (4) | N1—C5—C6—N2 | −26.8 (4) |
N2—Fe1—N4—C18 | 166.9 (3) | C4—C5—C6—N2 | 155.5 (4) |
O1—Fe1—N4—C14 | 173.9 (2) | C13—N2—C7—C8 | −102.8 (4) |
O2—Fe1—N4—C14 | 86.9 (3) | C6—N2—C7—C8 | 131.4 (3) |
N3—Fe1—N4—C14 | −94.9 (3) | Fe1—N2—C7—C8 | 15.4 (4) |
N1—Fe1—N4—C14 | −6.4 (7) | C12—N3—C8—C9 | 1.3 (5) |
N2—Fe1—N4—C14 | −8.6 (3) | Fe1—N3—C8—C9 | −172.0 (3) |
O1—Fe1—N2—C13 | 151 (2) | C12—N3—C8—C7 | −176.1 (3) |
O2—Fe1—N2—C13 | −63.9 (2) | Fe1—N3—C8—C7 | 10.6 (4) |
N3—Fe1—N2—C13 | 112.6 (2) | N2—C7—C8—N3 | −17.5 (5) |
N4—Fe1—N2—C13 | 24.9 (2) | N2—C7—C8—C9 | 165.2 (3) |
N1—Fe1—N2—C13 | −154.6 (2) | N3—C8—C9—C10 | −1.1 (6) |
O1—Fe1—N2—C6 | −89 (2) | C7—C8—C9—C10 | 176.1 (4) |
O2—Fe1—N2—C6 | 55.9 (2) | C8—C9—C10—C11 | −0.1 (6) |
N3—Fe1—N2—C6 | −127.5 (2) | C9—C10—C11—C12 | 1.1 (6) |
N4—Fe1—N2—C6 | 144.8 (2) | C8—N3—C12—C11 | −0.3 (5) |
N1—Fe1—N2—C6 | −34.7 (2) | Fe1—N3—C12—C11 | 172.3 (3) |
O1—Fe1—N2—C7 | 30 (2) | C10—C11—C12—N3 | −0.9 (6) |
O2—Fe1—N2—C7 | 175.2 (2) | C6—N2—C13—C14 | −151.4 (3) |
N3—Fe1—N2—C7 | −8.2 (2) | C7—N2—C13—C14 | 83.4 (4) |
N4—Fe1—N2—C7 | −96.0 (2) | Fe1—N2—C13—C14 | −35.6 (3) |
N1—Fe1—N2—C7 | 84.6 (2) | C18—N4—C14—C15 | −3.6 (5) |
O1—Fe1—N3—C8 | −179.2 (3) | Fe1—N4—C14—C15 | 172.2 (3) |
O2—Fe1—N3—C8 | 111.9 (19) | C18—N4—C14—C13 | 173.6 (3) |
N4—Fe1—N3—C8 | 83.1 (3) | Fe1—N4—C14—C13 | −10.6 (4) |
N1—Fe1—N3—C8 | −82.8 (3) | N2—C13—C14—N4 | 31.1 (4) |
N2—Fe1—N3—C8 | −1.1 (3) | N2—C13—C14—C15 | −151.7 (4) |
O1—Fe1—N3—C12 | 7.9 (3) | N4—C14—C15—C16 | 3.6 (6) |
O2—Fe1—N3—C12 | −61 (2) | C13—C14—C15—C16 | −173.4 (4) |
N4—Fe1—N3—C12 | −89.8 (3) | C14—C15—C16—C17 | 0.0 (6) |
N1—Fe1—N3—C12 | 104.3 (3) | C15—C16—C17—C18 | −3.5 (6) |
N2—Fe1—N3—C12 | −174.0 (3) | C14—N4—C18—C17 | 0.0 (6) |
O1—Fe1—N1—C1 | 16.2 (3) | Fe1—N4—C18—C17 | −175.3 (3) |
O2—Fe1—N1—C1 | 103.4 (3) | C16—C17—C18—N4 | 3.5 (6) |
N3—Fe1—N1—C1 | −75.6 (3) | Fe1—O1—C19—C20 | −178.9 (3) |
N4—Fe1—N1—C1 | −163.5 (4) | Fe1—O1—C19—C24 | 0.8 (4) |
N2—Fe1—N1—C1 | −161.3 (3) | O1—C19—C20—C21 | −179.6 (3) |
O1—Fe1—N1—C5 | −160.9 (3) | C24—C19—C20—C21 | 0.7 (5) |
O2—Fe1—N1—C5 | −73.7 (3) | O1—C19—C20—Cl1 | −1.0 (5) |
N3—Fe1—N1—C5 | 107.3 (3) | C24—C19—C20—Cl1 | 179.3 (3) |
N4—Fe1—N1—C5 | 19.4 (7) | C19—C20—C21—C22 | 0.9 (6) |
N2—Fe1—N1—C5 | 21.5 (3) | Cl1—C20—C21—C22 | −177.5 (3) |
O2—Fe1—O1—C19 | −0.1 (2) | C19—C20—C21—Cl2 | 179.8 (3) |
N3—Fe1—O1—C19 | −176.6 (2) | Cl1—C20—C21—Cl2 | 1.3 (5) |
N4—Fe1—O1—C19 | −89.1 (2) | C20—C21—C22—C23 | −0.5 (6) |
N1—Fe1—O1—C19 | 91.0 (2) | Cl2—C21—C22—C23 | −179.3 (3) |
N2—Fe1—O1—C19 | 145 (2) | C20—C21—C22—Cl3 | −178.5 (3) |
O1—Fe1—O2—C24 | −0.7 (2) | Cl2—C21—C22—Cl3 | 2.7 (5) |
N3—Fe1—O2—C24 | 68.3 (19) | C21—C22—C23—C24 | −1.7 (6) |
N4—Fe1—O2—C24 | 97.1 (2) | Cl3—C22—C23—C24 | 176.3 (3) |
N1—Fe1—O2—C24 | −97.0 (2) | C21—C22—C23—Cl4 | 178.8 (3) |
N2—Fe1—O2—C24 | −179.0 (2) | Cl3—C22—C23—Cl4 | −3.2 (5) |
C5—N1—C1—C2 | 1.8 (5) | Fe1—O2—C24—C23 | −177.5 (3) |
Fe1—N1—C1—C2 | −175.1 (3) | Fe1—O2—C24—C19 | 1.4 (4) |
N1—C1—C2—C3 | −0.5 (6) | C22—C23—C24—O2 | −177.8 (3) |
C1—C2—C3—C4 | −1.1 (6) | Cl4—C23—C24—O2 | 1.7 (5) |
C2—C3—C4—C5 | 1.4 (6) | C22—C23—C24—C19 | 3.4 (5) |
C1—N1—C5—C4 | −1.5 (5) | Cl4—C23—C24—C19 | −177.1 (3) |
Fe1—N1—C5—C4 | 175.8 (3) | O1—C19—C24—O2 | −1.5 (5) |
C1—N1—C5—C6 | −179.4 (3) | C20—C19—C24—O2 | 178.2 (3) |
Fe1—N1—C5—C6 | −2.1 (4) | O1—C19—C24—C23 | 177.4 (3) |
C3—C4—C5—N1 | −0.1 (6) | C20—C19—C24—C23 | −2.9 (5) |
C3—C4—C5—C6 | 177.6 (4) | | |
Crystal data top
C24H18Cl4F6FeN4O2P | F(000) = 1476 |
Mr = 737.04 | Dx = 1.772 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.3086 (2) Å | µ = 1.06 mm−1 |
b = 36.1529 (8) Å | T = 80 K |
c = 9.1975 (2) Å | Plate, blue |
V = 2762.74 (11) Å3 | 0.20 × 0.20 × 0.05 mm |
Z = 4 | |
Data collection top
CCD Saphire 3 Xcalibur diffractometer | 4026 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.091 |
Graphite monochromator | θmax = 27.0°, θmin = 2.7° |
Detector resolution: 19.64 pixels mm-1 | h = −10→9 |
ω scan | k = −46→46 |
34420 measured reflections | l = −11→11 |
5992 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0271P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.80 | (Δ/σ)max = 0.001 |
5992 reflections | Δρmax = 0.71 e Å−3 |
379 parameters | Δρmin = −0.45 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.088 (18) |
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 | Uiso*/Ueq | |
Fe1 | −0.08472 (7) | 0.132572 (14) | 0.31075 (7) | 0.01344 (13) | |
Cl1 | −0.02351 (13) | 0.26470 (3) | 0.24926 (12) | 0.0215 (3) | |
Cl2 | −0.15399 (14) | 0.28998 (3) | −0.05720 (12) | 0.0224 (3) | |
Cl3 | −0.30156 (14) | 0.23168 (3) | −0.26869 (12) | 0.0237 (3) | |
Cl4 | −0.33150 (13) | 0.14818 (2) | −0.16718 (12) | 0.0179 (2) | |
P1 | −0.3177 (2) | 0.02188 (3) | −0.15669 (19) | 0.0457 (4) | |
F1 | −0.3379 (6) | 0.02447 (12) | 0.0122 (4) | 0.1057 (17) | |
F2 | −0.2968 (5) | 0.01982 (10) | −0.3270 (4) | 0.0876 (14) | |
F3 | −0.3351 (4) | −0.02161 (7) | −0.1496 (4) | 0.0597 (9) | |
F4 | −0.1237 (4) | 0.01668 (8) | −0.1399 (5) | 0.0832 (14) | |
F5 | −0.2924 (4) | 0.06450 (7) | −0.1619 (7) | 0.130 (2) | |
F6 | −0.5026 (4) | 0.02640 (9) | −0.1703 (5) | 0.0860 (12) | |
O1 | −0.0597 (3) | 0.18367 (6) | 0.2985 (3) | 0.0137 (6) | |
O2 | −0.1802 (3) | 0.13472 (7) | 0.1212 (3) | 0.0166 (7) | |
N1 | −0.2988 (4) | 0.13235 (9) | 0.3987 (3) | 0.0144 (8) | |
N2 | −0.1006 (4) | 0.07765 (8) | 0.3304 (4) | 0.0125 (7) | |
N3 | −0.0020 (4) | 0.13196 (8) | 0.5071 (3) | 0.0119 (8) | |
N4 | 0.1245 (4) | 0.11987 (8) | 0.2249 (4) | 0.0139 (8) | |
C1 | −0.3755 (5) | 0.16184 (11) | 0.4544 (4) | 0.0165 (10) | |
H1 | −0.3293 | 0.1857 | 0.4438 | 0.020* | |
C2 | −0.5200 (5) | 0.15806 (12) | 0.5264 (4) | 0.0180 (11) | |
H2 | −0.5757 | 0.1792 | 0.5612 | 0.022* | |
C3 | −0.5825 (6) | 0.12324 (13) | 0.5475 (5) | 0.0220 (12) | |
H3 | −0.6786 | 0.1202 | 0.6022 | 0.026* | |
C4 | −0.5060 (6) | 0.09275 (11) | 0.4891 (5) | 0.0206 (11) | |
H4 | −0.5502 | 0.0687 | 0.5012 | 0.025* | |
C5 | −0.3645 (5) | 0.09768 (11) | 0.4129 (4) | 0.0138 (10) | |
C6 | −0.2747 (5) | 0.06828 (10) | 0.3339 (5) | 0.0194 (10) | |
H6A | −0.2903 | 0.0442 | 0.3833 | 0.023* | |
H6B | −0.3163 | 0.0661 | 0.2334 | 0.023* | |
C7 | −0.0179 (6) | 0.06655 (11) | 0.4677 (4) | 0.0203 (11) | |
H7A | −0.0826 | 0.0472 | 0.5166 | 0.024* | |
H7B | 0.0880 | 0.0557 | 0.4433 | 0.024* | |
C8 | 0.0068 (5) | 0.09805 (10) | 0.5706 (5) | 0.0142 (10) | |
C9 | 0.0394 (5) | 0.09393 (11) | 0.7168 (5) | 0.0189 (10) | |
H9 | 0.0415 | 0.0700 | 0.7597 | 0.023* | |
C10 | 0.0689 (5) | 0.12492 (10) | 0.7999 (6) | 0.0197 (9) | |
H10 | 0.0920 | 0.1226 | 0.9007 | 0.024* | |
C11 | 0.0645 (5) | 0.15963 (10) | 0.7353 (5) | 0.0171 (10) | |
H11 | 0.0866 | 0.1812 | 0.7906 | 0.021* | |
C12 | 0.0276 (5) | 0.16222 (11) | 0.5893 (5) | 0.0154 (10) | |
H12 | 0.0229 | 0.1860 | 0.5453 | 0.019* | |
C13 | −0.0165 (6) | 0.06244 (11) | 0.1985 (5) | 0.0203 (11) | |
H13A | 0.0113 | 0.0361 | 0.2142 | 0.024* | |
H13B | −0.0880 | 0.0641 | 0.1126 | 0.024* | |
C14 | 0.1331 (5) | 0.08453 (11) | 0.1731 (4) | 0.0143 (10) | |
C15 | 0.2682 (6) | 0.07226 (11) | 0.1001 (4) | 0.0189 (11) | |
H15 | 0.2735 | 0.0476 | 0.0647 | 0.023* | |
C16 | 0.3944 (6) | 0.09612 (12) | 0.0794 (5) | 0.0198 (11) | |
H16 | 0.4872 | 0.0882 | 0.0276 | 0.024* | |
C17 | 0.3863 (5) | 0.13162 (12) | 0.1340 (4) | 0.0183 (11) | |
H17 | 0.4742 | 0.1482 | 0.1224 | 0.022* | |
C18 | 0.2500 (5) | 0.14258 (11) | 0.2049 (4) | 0.0151 (10) | |
H18 | 0.2439 | 0.1671 | 0.2413 | 0.018* | |
C19 | −0.1125 (5) | 0.19592 (10) | 0.1684 (4) | 0.0127 (10) | |
C20 | −0.1043 (5) | 0.23287 (11) | 0.1273 (4) | 0.0148 (10) | |
C21 | −0.1635 (6) | 0.24373 (10) | −0.0072 (4) | 0.0157 (10) | |
C22 | −0.2325 (5) | 0.21811 (11) | −0.0994 (4) | 0.0140 (10) | |
C23 | −0.2407 (5) | 0.18065 (11) | −0.0578 (5) | 0.0158 (10) | |
C24 | −0.1788 (5) | 0.16950 (10) | 0.0756 (4) | 0.0124 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0161 (3) | 0.0115 (2) | 0.0127 (3) | −0.0004 (3) | −0.0007 (3) | 0.0010 (3) |
Cl1 | 0.0277 (7) | 0.0148 (5) | 0.0219 (6) | −0.0021 (5) | −0.0093 (6) | −0.0015 (4) |
Cl2 | 0.0291 (7) | 0.0136 (5) | 0.0245 (6) | −0.0015 (5) | −0.0067 (6) | 0.0044 (5) |
Cl3 | 0.0357 (8) | 0.0198 (5) | 0.0158 (6) | −0.0006 (5) | −0.0099 (6) | 0.0041 (5) |
Cl4 | 0.0219 (6) | 0.0156 (4) | 0.0161 (6) | −0.0015 (4) | −0.0051 (6) | −0.0028 (5) |
P1 | 0.0527 (11) | 0.0183 (6) | 0.0662 (12) | −0.0113 (7) | 0.0307 (9) | −0.0127 (7) |
F1 | 0.122 (4) | 0.127 (4) | 0.068 (3) | −0.016 (3) | 0.021 (3) | −0.066 (3) |
F2 | 0.112 (4) | 0.085 (3) | 0.066 (3) | 0.004 (2) | 0.042 (3) | 0.035 (2) |
F3 | 0.096 (3) | 0.0255 (14) | 0.057 (2) | −0.0168 (16) | 0.024 (2) | −0.0064 (15) |
F4 | 0.056 (2) | 0.0452 (19) | 0.148 (4) | 0.0054 (16) | 0.028 (3) | 0.002 (2) |
F5 | 0.068 (3) | 0.0207 (15) | 0.302 (6) | −0.0115 (16) | 0.071 (4) | −0.036 (3) |
F6 | 0.047 (2) | 0.076 (2) | 0.135 (3) | −0.0138 (17) | 0.027 (3) | −0.031 (3) |
O1 | 0.0136 (17) | 0.0132 (12) | 0.0144 (17) | 0.0002 (11) | −0.0048 (15) | −0.0027 (13) |
O2 | 0.0214 (19) | 0.0091 (14) | 0.0193 (16) | 0.0014 (14) | 0.0001 (15) | 0.0002 (12) |
N1 | 0.018 (2) | 0.0128 (16) | 0.0125 (19) | 0.0005 (17) | −0.0060 (16) | −0.0013 (15) |
N2 | 0.0137 (18) | 0.0181 (16) | 0.0059 (18) | −0.0032 (14) | −0.0043 (19) | 0.0017 (16) |
N3 | 0.010 (2) | 0.0124 (17) | 0.0130 (19) | −0.0008 (16) | −0.0003 (16) | −0.0018 (15) |
N4 | 0.017 (2) | 0.0155 (16) | 0.0091 (18) | −0.0017 (15) | −0.0044 (16) | 0.0024 (15) |
C1 | 0.015 (3) | 0.020 (2) | 0.014 (2) | −0.0001 (19) | −0.005 (2) | 0.0006 (19) |
C2 | 0.012 (3) | 0.030 (3) | 0.012 (3) | 0.008 (2) | −0.005 (2) | −0.0069 (19) |
C3 | 0.014 (3) | 0.035 (3) | 0.017 (3) | −0.004 (2) | 0.006 (2) | −0.001 (2) |
C4 | 0.023 (3) | 0.021 (2) | 0.019 (3) | −0.005 (2) | −0.010 (2) | −0.0003 (19) |
C5 | 0.009 (3) | 0.026 (2) | 0.007 (2) | −0.0020 (19) | −0.0024 (18) | −0.0005 (18) |
C6 | 0.019 (3) | 0.0159 (19) | 0.023 (3) | −0.0034 (17) | 0.002 (3) | −0.003 (2) |
C7 | 0.021 (3) | 0.015 (2) | 0.025 (3) | −0.002 (2) | −0.003 (2) | 0.0022 (19) |
C8 | 0.011 (3) | 0.015 (2) | 0.016 (2) | 0.0044 (19) | −0.002 (2) | 0.0055 (18) |
C9 | 0.020 (3) | 0.019 (2) | 0.018 (3) | 0.0043 (19) | 0.003 (2) | 0.0063 (19) |
C10 | 0.014 (2) | 0.031 (2) | 0.015 (2) | 0.0057 (19) | 0.002 (2) | 0.002 (2) |
C11 | 0.017 (3) | 0.022 (2) | 0.012 (2) | 0.0032 (19) | 0.000 (2) | −0.0016 (19) |
C12 | 0.009 (3) | 0.019 (2) | 0.018 (3) | −0.0026 (19) | 0.003 (2) | −0.0058 (19) |
C13 | 0.028 (3) | 0.014 (2) | 0.019 (3) | 0.003 (2) | 0.000 (2) | −0.0025 (18) |
C14 | 0.018 (3) | 0.014 (2) | 0.011 (2) | 0.0084 (19) | −0.006 (2) | 0.0007 (17) |
C15 | 0.029 (3) | 0.015 (2) | 0.013 (3) | 0.009 (2) | 0.000 (2) | −0.0014 (18) |
C16 | 0.017 (3) | 0.026 (3) | 0.017 (3) | 0.009 (2) | 0.004 (2) | 0.006 (2) |
C17 | 0.017 (3) | 0.026 (2) | 0.012 (2) | −0.005 (2) | −0.002 (2) | 0.006 (2) |
C18 | 0.016 (3) | 0.019 (2) | 0.010 (2) | 0.0020 (19) | 0.000 (2) | 0.0049 (17) |
C19 | 0.011 (3) | 0.013 (2) | 0.013 (2) | 0.0047 (18) | −0.001 (2) | −0.0019 (17) |
C20 | 0.013 (3) | 0.018 (2) | 0.014 (2) | −0.003 (2) | 0.001 (2) | −0.0039 (18) |
C21 | 0.017 (3) | 0.012 (2) | 0.017 (2) | −0.0056 (19) | −0.006 (2) | 0.0046 (17) |
C22 | 0.014 (3) | 0.018 (2) | 0.010 (2) | 0.0010 (18) | 0.0007 (19) | 0.0027 (17) |
C23 | 0.013 (3) | 0.016 (2) | 0.018 (2) | −0.0011 (18) | 0.005 (2) | −0.0059 (19) |
C24 | 0.013 (3) | 0.013 (2) | 0.011 (2) | 0.0010 (19) | 0.001 (2) | 0.0008 (17) |
Geometric parameters (Å, º) top
Fe1—O1 | 1.862 (2) | C4—C5 | 1.380 (6) |
Fe1—O2 | 1.917 (3) | C4—H4 | 0.9500 |
Fe1—N3 | 1.933 (3) | C5—C6 | 1.488 (5) |
Fe1—N1 | 1.954 (3) | C6—H6A | 0.9900 |
Fe1—N4 | 1.964 (3) | C6—H6B | 0.9900 |
Fe1—N2 | 1.998 (3) | C7—C8 | 1.495 (5) |
Cl1—C20 | 1.741 (4) | C7—H7A | 0.9900 |
Cl2—C21 | 1.736 (4) | C7—H7B | 0.9900 |
Cl3—C22 | 1.731 (4) | C8—C9 | 1.381 (6) |
Cl4—C23 | 1.720 (4) | C9—C10 | 1.378 (5) |
P1—F6 | 1.549 (3) | C9—H9 | 0.9500 |
P1—F5 | 1.556 (3) | C10—C11 | 1.389 (5) |
P1—F1 | 1.566 (4) | C10—H10 | 0.9500 |
P1—F2 | 1.577 (4) | C11—C12 | 1.380 (5) |
P1—F3 | 1.580 (3) | C11—H11 | 0.9500 |
P1—F4 | 1.630 (4) | C12—H12 | 0.9500 |
O1—C19 | 1.350 (4) | C13—C14 | 1.496 (6) |
O2—C24 | 1.326 (4) | C13—H13A | 0.9900 |
N1—C1 | 1.343 (5) | C13—H13B | 0.9900 |
N1—C5 | 1.373 (5) | C14—C15 | 1.381 (5) |
N2—C6 | 1.486 (5) | C15—C16 | 1.371 (6) |
N2—C7 | 1.493 (5) | C15—H15 | 0.9500 |
N2—C13 | 1.504 (5) | C16—C17 | 1.380 (6) |
N3—C12 | 1.352 (5) | C16—H16 | 0.9500 |
N3—C8 | 1.359 (4) | C17—C18 | 1.366 (6) |
N4—C18 | 1.339 (5) | C17—H17 | 0.9500 |
N4—C14 | 1.365 (5) | C18—H18 | 0.9500 |
C1—C2 | 1.378 (6) | C19—C20 | 1.390 (5) |
C1—H1 | 0.9500 | C19—C24 | 1.394 (5) |
C2—C3 | 1.376 (6) | C20—C21 | 1.388 (5) |
C2—H2 | 0.9500 | C21—C22 | 1.380 (5) |
C3—C4 | 1.381 (6) | C22—C23 | 1.409 (5) |
C3—H3 | 0.9500 | C23—C24 | 1.390 (6) |
| | | |
O1—Fe1—O2 | 87.20 (12) | C5—C6—H6A | 109.7 |
O1—Fe1—N3 | 91.61 (13) | N2—C6—H6B | 109.7 |
O2—Fe1—N3 | 176.00 (14) | C5—C6—H6B | 109.7 |
O1—Fe1—N1 | 97.51 (12) | H6A—C6—H6B | 108.2 |
O2—Fe1—N1 | 90.00 (13) | C8—C7—N2 | 113.2 (3) |
N3—Fe1—N1 | 86.37 (13) | C8—C7—H7A | 108.9 |
O1—Fe1—N4 | 96.25 (12) | N2—C7—H7A | 108.9 |
O2—Fe1—N4 | 90.59 (13) | C8—C7—H7B | 108.9 |
N3—Fe1—N4 | 93.33 (15) | N2—C7—H7B | 108.9 |
N1—Fe1—N4 | 166.24 (13) | H7A—C7—H7B | 107.8 |
O1—Fe1—N2 | 176.88 (14) | N3—C8—C9 | 121.7 (4) |
O2—Fe1—N2 | 95.45 (13) | N3—C8—C7 | 114.1 (3) |
N3—Fe1—N2 | 85.86 (14) | C9—C8—C7 | 124.2 (3) |
N1—Fe1—N2 | 84.16 (13) | C10—C9—C8 | 119.2 (4) |
N4—Fe1—N2 | 82.10 (13) | C10—C9—H9 | 120.4 |
F6—P1—F5 | 91.6 (2) | C8—C9—H9 | 120.4 |
F6—P1—F1 | 88.2 (3) | C9—C10—C11 | 119.5 (4) |
F5—P1—F1 | 89.2 (3) | C9—C10—H10 | 120.3 |
F6—P1—F2 | 91.9 (3) | C11—C10—H10 | 120.3 |
F5—P1—F2 | 90.1 (3) | C12—C11—C10 | 118.9 (4) |
F1—P1—F2 | 179.3 (2) | C12—C11—H11 | 120.5 |
F6—P1—F3 | 91.02 (19) | C10—C11—H11 | 120.5 |
F5—P1—F3 | 177.4 (2) | N3—C12—C11 | 121.9 (4) |
F1—P1—F3 | 90.5 (2) | N3—C12—H12 | 119.0 |
F2—P1—F3 | 90.22 (19) | C11—C12—H12 | 119.0 |
F6—P1—F4 | 179.0 (3) | C14—C13—N2 | 108.5 (3) |
F5—P1—F4 | 89.03 (18) | C14—C13—H13A | 110.0 |
F1—P1—F4 | 91.1 (3) | N2—C13—H13A | 110.0 |
F2—P1—F4 | 88.8 (2) | C14—C13—H13B | 110.0 |
F3—P1—F4 | 88.37 (18) | N2—C13—H13B | 110.0 |
C19—O1—Fe1 | 110.1 (2) | H13A—C13—H13B | 108.4 |
C24—O2—Fe1 | 108.8 (2) | N4—C14—C15 | 120.8 (4) |
C1—N1—C5 | 120.0 (4) | N4—C14—C13 | 113.7 (3) |
C1—N1—Fe1 | 125.9 (3) | C15—C14—C13 | 125.4 (4) |
C5—N1—Fe1 | 113.9 (3) | C16—C15—C14 | 119.1 (4) |
C6—N2—C7 | 111.6 (3) | C16—C15—H15 | 120.4 |
C6—N2—C13 | 112.8 (3) | C14—C15—H15 | 120.4 |
C7—N2—C13 | 111.7 (3) | C17—C16—C15 | 119.8 (4) |
C6—N2—Fe1 | 107.0 (2) | C17—C16—H16 | 120.1 |
C7—N2—Fe1 | 108.2 (2) | C15—C16—H16 | 120.1 |
C13—N2—Fe1 | 105.1 (2) | C18—C17—C16 | 118.9 (4) |
C12—N3—C8 | 118.7 (3) | C18—C17—H17 | 120.5 |
C12—N3—Fe1 | 125.3 (3) | C16—C17—H17 | 120.5 |
C8—N3—Fe1 | 115.5 (3) | N4—C18—C17 | 122.2 (4) |
C18—N4—C14 | 119.0 (4) | N4—C18—H18 | 118.9 |
C18—N4—Fe1 | 126.9 (3) | C17—C18—H18 | 118.9 |
C14—N4—Fe1 | 113.9 (3) | O1—C19—C20 | 122.7 (4) |
N1—C1—C2 | 121.2 (4) | O1—C19—C24 | 116.5 (3) |
N1—C1—H1 | 119.4 | C20—C19—C24 | 120.8 (4) |
C2—C1—H1 | 119.4 | C21—C20—C19 | 119.8 (4) |
C3—C2—C1 | 119.2 (4) | C21—C20—Cl1 | 121.6 (3) |
C3—C2—H2 | 120.4 | C19—C20—Cl1 | 118.6 (3) |
C1—C2—H2 | 120.4 | C20—C21—C22 | 120.3 (3) |
C2—C3—C4 | 120.1 (4) | C20—C21—Cl2 | 119.5 (3) |
C2—C3—H3 | 119.9 | C22—C21—Cl2 | 120.2 (3) |
C4—C3—H3 | 119.9 | C21—C22—C23 | 119.9 (4) |
C3—C4—C5 | 119.1 (4) | C21—C22—Cl3 | 120.0 (3) |
C3—C4—H4 | 120.5 | C23—C22—Cl3 | 120.0 (3) |
C5—C4—H4 | 120.5 | C24—C23—C22 | 120.0 (4) |
N1—C5—C4 | 120.3 (4) | C24—C23—Cl4 | 118.7 (3) |
N1—C5—C6 | 114.0 (4) | C22—C23—Cl4 | 121.2 (3) |
C4—C5—C6 | 125.6 (4) | O2—C24—C23 | 123.4 (4) |
N2—C6—C5 | 109.6 (3) | O2—C24—C19 | 117.4 (4) |
N2—C6—H6A | 109.7 | C23—C24—C19 | 119.2 (4) |
| | | |
O2—Fe1—O1—C19 | −2.1 (2) | C7—N2—C6—C5 | 82.5 (4) |
N3—Fe1—O1—C19 | −178.3 (3) | C13—N2—C6—C5 | −150.8 (3) |
N1—Fe1—O1—C19 | −91.7 (3) | Fe1—N2—C6—C5 | −35.7 (4) |
N4—Fe1—O1—C19 | 88.2 (3) | N1—C5—C6—N2 | 31.6 (5) |
N2—Fe1—O1—C19 | 146 (2) | C4—C5—C6—N2 | −151.7 (4) |
O1—Fe1—O2—C24 | 1.2 (3) | C6—N2—C7—C8 | −100.0 (4) |
N3—Fe1—O2—C24 | 73.9 (19) | C13—N2—C7—C8 | 132.7 (4) |
N1—Fe1—O2—C24 | 98.7 (3) | Fe1—N2—C7—C8 | 17.6 (4) |
N4—Fe1—O2—C24 | −95.0 (3) | C12—N3—C8—C9 | 2.3 (6) |
N2—Fe1—O2—C24 | −177.2 (3) | Fe1—N3—C8—C9 | −169.8 (3) |
O1—Fe1—N1—C1 | −11.2 (3) | C12—N3—C8—C7 | −176.3 (4) |
O2—Fe1—N1—C1 | −98.4 (3) | Fe1—N3—C8—C7 | 11.6 (5) |
N3—Fe1—N1—C1 | 80.0 (3) | N2—C7—C8—N3 | −19.6 (5) |
N4—Fe1—N1—C1 | 169.1 (5) | N2—C7—C8—C9 | 161.9 (4) |
N2—Fe1—N1—C1 | 166.2 (3) | N3—C8—C9—C10 | −2.1 (6) |
O1—Fe1—N1—C5 | 174.6 (3) | C7—C8—C9—C10 | 176.4 (4) |
O2—Fe1—N1—C5 | 87.4 (3) | C8—C9—C10—C11 | 0.3 (6) |
N3—Fe1—N1—C5 | −94.3 (3) | C9—C10—C11—C12 | 1.2 (6) |
N4—Fe1—N1—C5 | −5.1 (8) | C8—N3—C12—C11 | −0.7 (6) |
N2—Fe1—N1—C5 | −8.1 (3) | Fe1—N3—C12—C11 | 170.5 (3) |
O1—Fe1—N2—C6 | 147 (2) | C10—C11—C12—N3 | −1.0 (6) |
O2—Fe1—N2—C6 | −65.0 (3) | C6—N2—C13—C14 | 158.1 (3) |
N3—Fe1—N2—C6 | 111.2 (3) | C7—N2—C13—C14 | −75.3 (4) |
N1—Fe1—N2—C6 | 24.4 (3) | Fe1—N2—C13—C14 | 41.9 (4) |
N4—Fe1—N2—C6 | −154.9 (3) | C18—N4—C14—C15 | −0.5 (6) |
O1—Fe1—N2—C7 | 26 (3) | Fe1—N4—C14—C15 | 175.2 (3) |
O2—Fe1—N2—C7 | 174.5 (3) | C18—N4—C14—C13 | −178.2 (4) |
N3—Fe1—N2—C7 | −9.3 (3) | Fe1—N4—C14—C13 | −2.5 (4) |
N1—Fe1—N2—C7 | −96.0 (3) | N2—C13—C14—N4 | −26.8 (5) |
N4—Fe1—N2—C7 | 84.7 (3) | N2—C13—C14—C15 | 155.6 (4) |
O1—Fe1—N2—C13 | −93 (3) | N4—C14—C15—C16 | −0.2 (6) |
O2—Fe1—N2—C13 | 55.0 (3) | C13—C14—C15—C16 | 177.2 (4) |
N3—Fe1—N2—C13 | −128.8 (3) | C14—C15—C16—C17 | 1.3 (6) |
N1—Fe1—N2—C13 | 144.5 (3) | C15—C16—C17—C18 | −1.6 (6) |
N4—Fe1—N2—C13 | −34.8 (3) | C14—N4—C18—C17 | 0.2 (6) |
O1—Fe1—N3—C12 | 9.2 (3) | Fe1—N4—C18—C17 | −174.9 (3) |
O2—Fe1—N3—C12 | −63 (2) | C16—C17—C18—N4 | 0.9 (6) |
N1—Fe1—N3—C12 | −88.2 (3) | Fe1—O1—C19—C20 | −178.1 (3) |
N4—Fe1—N3—C12 | 105.6 (3) | Fe1—O1—C19—C24 | 2.6 (4) |
N2—Fe1—N3—C12 | −172.6 (3) | O1—C19—C20—C21 | −178.8 (4) |
O1—Fe1—N3—C8 | −179.3 (3) | C24—C19—C20—C21 | 0.4 (6) |
O2—Fe1—N3—C8 | 108.1 (18) | O1—C19—C20—Cl1 | −0.4 (6) |
N1—Fe1—N3—C8 | 83.3 (3) | C24—C19—C20—Cl1 | 178.9 (3) |
N4—Fe1—N3—C8 | −82.9 (3) | C19—C20—C21—C22 | 0.9 (6) |
N2—Fe1—N3—C8 | −1.1 (3) | Cl1—C20—C21—C22 | −177.5 (3) |
O1—Fe1—N4—C18 | 14.8 (3) | C19—C20—C21—Cl2 | 179.6 (3) |
O2—Fe1—N4—C18 | 102.0 (3) | Cl1—C20—C21—Cl2 | 1.2 (5) |
N3—Fe1—N4—C18 | −77.2 (3) | C20—C21—C22—C23 | −0.9 (6) |
N1—Fe1—N4—C18 | −165.6 (5) | Cl2—C21—C22—C23 | −179.6 (3) |
N2—Fe1—N4—C18 | −162.6 (4) | C20—C21—C22—Cl3 | −178.4 (3) |
O1—Fe1—N4—C14 | −160.6 (3) | Cl2—C21—C22—Cl3 | 2.9 (5) |
O2—Fe1—N4—C14 | −73.4 (3) | C21—C22—C23—C24 | −0.3 (6) |
N3—Fe1—N4—C14 | 107.4 (3) | Cl3—C22—C23—C24 | 177.2 (3) |
N1—Fe1—N4—C14 | 19.1 (8) | C21—C22—C23—Cl4 | 177.9 (3) |
N2—Fe1—N4—C14 | 22.1 (3) | Cl3—C22—C23—Cl4 | −4.6 (5) |
C5—N1—C1—C2 | 0.2 (6) | Fe1—O2—C24—C23 | −179.4 (3) |
Fe1—N1—C1—C2 | −173.7 (3) | Fe1—O2—C24—C19 | 0.0 (5) |
N1—C1—C2—C3 | 3.1 (6) | C22—C23—C24—O2 | −179.0 (4) |
C1—C2—C3—C4 | −3.9 (6) | Cl4—C23—C24—O2 | 2.7 (6) |
C2—C3—C4—C5 | 1.6 (6) | C22—C23—C24—C19 | 1.6 (6) |
C1—N1—C5—C4 | −2.5 (6) | Cl4—C23—C24—C19 | −176.7 (3) |
Fe1—N1—C5—C4 | 172.0 (3) | O1—C19—C24—O2 | −1.8 (6) |
C1—N1—C5—C6 | 174.4 (4) | C20—C19—C24—O2 | 179.0 (4) |
Fe1—N1—C5—C6 | −11.0 (4) | O1—C19—C24—C23 | 177.6 (4) |
C3—C4—C5—N1 | 1.7 (6) | C20—C19—C24—C23 | −1.7 (6) |
C3—C4—C5—C6 | −174.9 (4) | | |
Crystal data top
C24H18Cl4F6FeN4O2P | Z = 4 |
Mr = 737.04 | F(000) = 1476 |
Monoclinic, P21/a | Dx = 1.642 Mg m−3 |
a = 8.6788 (6) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 37.001 (2) Å | µ = 0.99 mm−1 |
c = 9.2881 (5) Å | T = 400 K |
β = 91.255 (2)° | Needle, orange |
V = 2981.9 (3) Å3 | 0.25 × 0.05 × 0.05 mm |
Data collection top
CCD Saphire 3 Xcalibur diffractometer | 1817 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.123 |
Graphite monochromator | θmax = 27.0°, θmin = 2.6° |
Detector resolution: 19.64 pixels mm-1 | h = −11→11 |
ω scan | k = −47→47 |
38192 measured reflections | l = −11→11 |
5982 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 0.71 | w = 1/[σ2(Fo2) + (0.0588P)2] where P = (Fo2 + 2Fc2)/3 |
5982 reflections | (Δ/σ)max < 0.001 |
379 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
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 | Uiso*/Ueq | |
P1 | 0.2047 (3) | 0.02064 (4) | 0.7802 (2) | 0.1023 (6) | |
F1 | 0.1785 (7) | 0.02239 (19) | 0.6191 (6) | 0.258 (3) | |
F2 | 0.2359 (7) | 0.0193 (2) | 0.9329 (5) | 0.300 (4) | |
F3 | 0.3857 (5) | 0.01908 (11) | 0.7567 (6) | 0.1846 (19) | |
F4 | 0.2010 (5) | −0.02037 (11) | 0.7676 (6) | 0.204 (2) | |
F5 | 0.0309 (5) | 0.02113 (13) | 0.7990 (6) | 0.197 (2) | |
F6 | 0.2144 (6) | 0.06065 (12) | 0.7727 (11) | 0.302 (4) | |
Fe1 | 0.40809 (8) | 0.134889 (17) | 0.33376 (7) | 0.0644 (3) | |
Cl1 | 0.46039 (19) | 0.26577 (4) | 0.39357 (18) | 0.1117 (6) | |
Cl2 | 0.3353 (2) | 0.29066 (4) | 0.69243 (19) | 0.1211 (6) | |
Cl3 | 0.1965 (2) | 0.23370 (4) | 0.90136 (16) | 0.1215 (6) | |
Cl4 | 0.17306 (17) | 0.15192 (4) | 0.80391 (14) | 0.0882 (5) | |
O1 | 0.4315 (3) | 0.18649 (7) | 0.3476 (3) | 0.0686 (9) | |
O2 | 0.3167 (3) | 0.13887 (8) | 0.5204 (3) | 0.0698 (9) | |
N4 | 0.6223 (5) | 0.11667 (14) | 0.4195 (4) | 0.0708 (12) | |
N2 | 0.4005 (6) | 0.07688 (10) | 0.2967 (4) | 0.0705 (11) | |
N3 | 0.4954 (4) | 0.13384 (12) | 0.1241 (4) | 0.0629 (10) | |
N1 | 0.1894 (5) | 0.12800 (15) | 0.2334 (4) | 0.0761 (12) | |
C1 | 0.1038 (9) | 0.15572 (18) | 0.1789 (6) | 0.0989 (19) | |
H1 | 0.1385 | 0.1793 | 0.1919 | 0.119* | |
C2 | −0.0324 (10) | 0.1499 (3) | 0.1052 (8) | 0.130 (3) | |
H2 | −0.0919 | 0.1693 | 0.0728 | 0.156* | |
C3 | −0.0793 (11) | 0.1153 (4) | 0.0799 (10) | 0.153 (4) | |
H3 | −0.1692 | 0.1109 | 0.0265 | 0.184* | |
C4 | 0.0073 (10) | 0.0870 (3) | 0.1341 (9) | 0.130 (3) | |
H4 | −0.0243 | 0.0633 | 0.1178 | 0.156* | |
C5 | 0.1442 (8) | 0.0940 (2) | 0.2142 (6) | 0.0875 (18) | |
C6 | 0.2365 (8) | 0.06595 (15) | 0.2901 (6) | 0.0958 (18) | |
H6A | 0.1990 | 0.0628 | 0.3869 | 0.115* | |
H6B | 0.2261 | 0.0431 | 0.2396 | 0.115* | |
C7 | 0.4805 (6) | 0.06855 (13) | 0.1597 (5) | 0.0815 (16) | |
H7A | 0.4213 | 0.0505 | 0.1069 | 0.098* | |
H7B | 0.5806 | 0.0582 | 0.1831 | 0.098* | |
C8 | 0.5025 (5) | 0.10100 (14) | 0.0637 (6) | 0.0629 (13) | |
C9 | 0.5376 (6) | 0.09709 (17) | −0.0801 (6) | 0.0859 (17) | |
H9 | 0.5394 | 0.0743 | −0.1221 | 0.103* | |
C10 | 0.5698 (7) | 0.1272 (2) | −0.1599 (6) | 0.102 (2) | |
H10 | 0.5964 | 0.1248 | −0.2559 | 0.122* | |
C11 | 0.5627 (6) | 0.16082 (18) | −0.0982 (7) | 0.0959 (18) | |
H11 | 0.5831 | 0.1815 | −0.1513 | 0.115* | |
C12 | 0.5251 (5) | 0.16296 (14) | 0.0429 (6) | 0.0722 (14) | |
H12 | 0.5196 | 0.1857 | 0.0852 | 0.087* | |
C13 | 0.4874 (8) | 0.06035 (14) | 0.4216 (6) | 0.0939 (18) | |
H13A | 0.4223 | 0.0599 | 0.5052 | 0.113* | |
H13B | 0.5148 | 0.0356 | 0.3984 | 0.113* | |
C14 | 0.6288 (8) | 0.08133 (17) | 0.4552 (6) | 0.0827 (16) | |
C15 | 0.7577 (11) | 0.0673 (2) | 0.5229 (7) | 0.121 (3) | |
H15 | 0.7621 | 0.0430 | 0.5481 | 0.145* | |
C16 | 0.8792 (11) | 0.0897 (3) | 0.5524 (8) | 0.139 (3) | |
H16 | 0.9664 | 0.0806 | 0.5996 | 0.167* | |
C17 | 0.8751 (9) | 0.1255 (2) | 0.5137 (7) | 0.117 (2) | |
H17 | 0.9585 | 0.1406 | 0.5326 | 0.141* | |
C18 | 0.7444 (8) | 0.13805 (17) | 0.4465 (6) | 0.0908 (18) | |
H18 | 0.7398 | 0.1622 | 0.4187 | 0.109* | |
C19 | 0.3792 (5) | 0.19872 (13) | 0.4725 (5) | 0.0607 (13) | |
C20 | 0.3845 (5) | 0.23509 (13) | 0.5111 (6) | 0.0686 (14) | |
C21 | 0.3283 (6) | 0.24545 (13) | 0.6439 (6) | 0.0738 (15) | |
C22 | 0.2634 (6) | 0.22063 (16) | 0.7357 (5) | 0.0760 (15) | |
C23 | 0.2552 (5) | 0.18405 (14) | 0.6956 (5) | 0.0652 (14) | |
C24 | 0.3154 (5) | 0.17308 (14) | 0.5667 (5) | 0.0568 (12) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.129 (2) | 0.0680 (13) | 0.1096 (17) | 0.0000 (11) | −0.0002 (12) | −0.0021 (10) |
F1 | 0.309 (7) | 0.313 (9) | 0.153 (5) | −0.056 (5) | −0.008 (4) | 0.057 (5) |
F2 | 0.295 (7) | 0.515 (13) | 0.088 (4) | 0.010 (7) | −0.026 (4) | −0.030 (5) |
F3 | 0.125 (4) | 0.134 (4) | 0.296 (6) | 0.015 (3) | 0.030 (4) | 0.012 (3) |
F4 | 0.199 (4) | 0.083 (3) | 0.330 (7) | −0.004 (3) | 0.035 (4) | 0.002 (4) |
F5 | 0.095 (4) | 0.214 (5) | 0.283 (6) | −0.001 (3) | 0.026 (3) | 0.013 (4) |
F6 | 0.218 (5) | 0.066 (3) | 0.619 (14) | 0.000 (3) | −0.027 (6) | −0.022 (5) |
Fe1 | 0.0818 (6) | 0.0500 (4) | 0.0616 (5) | 0.0024 (4) | 0.0032 (4) | −0.0005 (4) |
Cl1 | 0.1459 (14) | 0.0581 (9) | 0.1329 (13) | −0.0127 (9) | 0.0417 (11) | 0.0098 (9) |
Cl2 | 0.1558 (15) | 0.0581 (10) | 0.1509 (15) | −0.0013 (10) | 0.0347 (12) | −0.0279 (10) |
Cl3 | 0.1751 (17) | 0.0950 (12) | 0.0960 (12) | 0.0035 (11) | 0.0389 (11) | −0.0275 (9) |
Cl4 | 0.1109 (11) | 0.0811 (10) | 0.0732 (9) | −0.0051 (8) | 0.0168 (8) | 0.0084 (7) |
O1 | 0.091 (3) | 0.0471 (19) | 0.068 (2) | 0.0036 (17) | 0.0168 (19) | 0.0056 (18) |
O2 | 0.096 (3) | 0.044 (2) | 0.070 (2) | −0.0039 (18) | 0.0132 (18) | 0.0012 (17) |
N4 | 0.076 (4) | 0.076 (3) | 0.061 (3) | 0.005 (3) | 0.007 (2) | −0.006 (2) |
N2 | 0.090 (4) | 0.052 (3) | 0.070 (3) | −0.006 (3) | 0.013 (3) | 0.003 (2) |
N3 | 0.068 (3) | 0.055 (3) | 0.065 (3) | −0.008 (2) | 0.000 (2) | 0.002 (2) |
N1 | 0.076 (4) | 0.080 (4) | 0.074 (3) | −0.001 (3) | 0.015 (3) | −0.003 (3) |
C1 | 0.095 (6) | 0.120 (6) | 0.082 (4) | 0.029 (5) | 0.017 (4) | 0.009 (4) |
C2 | 0.065 (6) | 0.220 (11) | 0.105 (6) | 0.020 (6) | −0.002 (5) | 0.020 (6) |
C3 | 0.078 (7) | 0.257 (14) | 0.124 (7) | −0.033 (8) | −0.010 (5) | 0.000 (9) |
C4 | 0.090 (7) | 0.175 (9) | 0.125 (6) | −0.044 (6) | 0.011 (5) | −0.005 (6) |
C5 | 0.081 (5) | 0.105 (6) | 0.077 (4) | −0.020 (4) | 0.014 (4) | −0.003 (4) |
C6 | 0.119 (6) | 0.065 (4) | 0.104 (5) | −0.025 (4) | 0.013 (4) | 0.006 (3) |
C7 | 0.120 (5) | 0.051 (3) | 0.074 (4) | 0.007 (3) | 0.006 (3) | −0.006 (3) |
C8 | 0.060 (4) | 0.067 (4) | 0.062 (4) | −0.001 (3) | −0.001 (3) | −0.009 (3) |
C9 | 0.088 (4) | 0.099 (5) | 0.070 (4) | −0.004 (3) | 0.002 (3) | −0.019 (4) |
C10 | 0.118 (5) | 0.129 (6) | 0.058 (4) | −0.005 (5) | 0.014 (3) | 0.001 (4) |
C11 | 0.115 (5) | 0.101 (5) | 0.072 (4) | −0.005 (4) | 0.012 (4) | 0.027 (4) |
C12 | 0.068 (4) | 0.072 (4) | 0.077 (4) | −0.009 (3) | 0.011 (3) | 0.013 (3) |
C13 | 0.147 (6) | 0.058 (4) | 0.078 (4) | 0.017 (4) | 0.019 (4) | 0.011 (3) |
C14 | 0.113 (6) | 0.069 (4) | 0.066 (4) | 0.022 (4) | −0.002 (4) | −0.001 (3) |
C15 | 0.155 (7) | 0.110 (6) | 0.097 (5) | 0.056 (6) | −0.035 (5) | −0.012 (4) |
C16 | 0.133 (7) | 0.181 (10) | 0.102 (6) | 0.085 (7) | −0.047 (5) | −0.044 (6) |
C17 | 0.092 (6) | 0.153 (8) | 0.106 (5) | 0.021 (6) | −0.016 (4) | −0.029 (5) |
C18 | 0.086 (5) | 0.107 (5) | 0.078 (4) | 0.003 (5) | −0.011 (4) | −0.006 (4) |
C19 | 0.070 (4) | 0.052 (3) | 0.061 (3) | 0.006 (3) | 0.002 (3) | 0.001 (3) |
C20 | 0.071 (4) | 0.049 (3) | 0.086 (4) | 0.005 (3) | 0.009 (3) | 0.004 (3) |
C21 | 0.085 (4) | 0.048 (3) | 0.089 (4) | 0.005 (3) | 0.014 (3) | −0.016 (3) |
C22 | 0.082 (4) | 0.073 (4) | 0.074 (4) | 0.009 (3) | 0.011 (3) | −0.012 (3) |
C23 | 0.080 (4) | 0.060 (4) | 0.056 (3) | 0.004 (3) | 0.006 (3) | 0.003 (3) |
C24 | 0.064 (4) | 0.051 (3) | 0.056 (3) | 0.001 (3) | 0.005 (3) | 0.007 (3) |
Geometric parameters (Å, º) top
P1—F2 | 1.439 (5) | C4—C5 | 1.413 (8) |
P1—F6 | 1.484 (4) | C4—H4 | 0.9300 |
P1—F1 | 1.510 (5) | C5—C6 | 1.481 (7) |
P1—F5 | 1.522 (4) | C6—H6A | 0.9700 |
P1—F4 | 1.522 (4) | C6—H6B | 0.9700 |
P1—F3 | 1.592 (4) | C7—C8 | 1.511 (6) |
Fe1—O1 | 1.924 (3) | C7—H7A | 0.9700 |
Fe1—O2 | 1.928 (3) | C7—H7B | 0.9700 |
Fe1—N3 | 2.105 (4) | C8—C9 | 1.384 (6) |
Fe1—N1 | 2.111 (5) | C9—C10 | 1.370 (7) |
Fe1—N4 | 2.116 (4) | C9—H9 | 0.9300 |
Fe1—N2 | 2.175 (4) | C10—C11 | 1.372 (7) |
Cl1—C20 | 1.717 (5) | C10—H10 | 0.9300 |
Cl2—C21 | 1.733 (5) | C11—C12 | 1.360 (7) |
Cl3—C22 | 1.726 (5) | C11—H11 | 0.9300 |
Cl4—C23 | 1.722 (5) | C12—H12 | 0.9300 |
O1—C19 | 1.335 (5) | C13—C14 | 1.480 (7) |
O2—C24 | 1.337 (5) | C13—H13A | 0.9700 |
N4—C18 | 1.342 (6) | C13—H13B | 0.9700 |
N4—C14 | 1.350 (6) | C14—C15 | 1.374 (8) |
N2—C6 | 1.480 (6) | C15—C16 | 1.366 (10) |
N2—C7 | 1.494 (5) | C15—H15 | 0.9300 |
N2—C13 | 1.500 (6) | C16—C17 | 1.370 (9) |
N3—C8 | 1.340 (5) | C16—H16 | 0.9300 |
N3—C12 | 1.344 (5) | C17—C18 | 1.364 (8) |
N1—C5 | 1.328 (7) | C17—H17 | 0.9300 |
N1—C1 | 1.358 (7) | C18—H18 | 0.9300 |
C1—C2 | 1.370 (8) | C19—C20 | 1.393 (6) |
C1—H1 | 0.9300 | C19—C24 | 1.412 (6) |
C2—C3 | 1.360 (10) | C20—C21 | 1.390 (6) |
C2—H2 | 0.9300 | C21—C22 | 1.381 (7) |
C3—C4 | 1.380 (10) | C22—C23 | 1.405 (6) |
C3—H3 | 0.9300 | C23—C24 | 1.378 (6) |
| | | |
F2—P1—F6 | 94.1 (4) | C5—C6—H6A | 109.7 |
F2—P1—F1 | 177.8 (4) | N2—C6—H6B | 109.7 |
F6—P1—F1 | 85.3 (4) | C5—C6—H6B | 109.7 |
F2—P1—F5 | 93.0 (3) | H6A—C6—H6B | 108.2 |
F6—P1—F5 | 92.9 (3) | N2—C7—C8 | 113.9 (4) |
F1—P1—F5 | 89.2 (3) | N2—C7—H7A | 108.8 |
F2—P1—F4 | 92.5 (4) | C8—C7—H7A | 108.8 |
F6—P1—F4 | 172.6 (5) | N2—C7—H7B | 108.8 |
F1—P1—F4 | 87.9 (3) | C8—C7—H7B | 108.8 |
F5—P1—F4 | 90.1 (3) | H7A—C7—H7B | 107.7 |
F2—P1—F3 | 88.2 (3) | N3—C8—C9 | 120.8 (5) |
F6—P1—F3 | 88.4 (3) | N3—C8—C7 | 117.7 (5) |
F1—P1—F3 | 89.6 (3) | C9—C8—C7 | 121.3 (5) |
F5—P1—F3 | 178.1 (3) | C10—C9—C8 | 119.3 (6) |
F4—P1—F3 | 88.4 (3) | C10—C9—H9 | 120.4 |
O1—Fe1—O2 | 84.79 (13) | C8—C9—H9 | 120.4 |
O1—Fe1—N3 | 92.31 (15) | C9—C10—C11 | 120.0 (6) |
O2—Fe1—N3 | 175.36 (14) | C9—C10—H10 | 120.0 |
O1—Fe1—N1 | 104.00 (18) | C11—C10—H10 | 120.0 |
O2—Fe1—N1 | 91.31 (13) | C12—C11—C10 | 118.0 (6) |
N3—Fe1—N1 | 85.86 (14) | C12—C11—H11 | 121.0 |
O1—Fe1—N4 | 101.56 (16) | C10—C11—H11 | 121.0 |
O2—Fe1—N4 | 93.50 (13) | N3—C12—C11 | 123.2 (5) |
N3—Fe1—N4 | 90.63 (14) | N3—C12—H12 | 118.4 |
N1—Fe1—N4 | 154.3 (2) | C11—C12—H12 | 118.4 |
O1—Fe1—N2 | 173.11 (15) | C14—C13—N2 | 110.5 (5) |
O2—Fe1—N2 | 101.91 (14) | C14—C13—H13A | 109.6 |
N3—Fe1—N2 | 81.11 (16) | N2—C13—H13A | 109.6 |
N1—Fe1—N2 | 77.70 (19) | C14—C13—H13B | 109.6 |
N4—Fe1—N2 | 76.62 (19) | N2—C13—H13B | 109.6 |
C19—O1—Fe1 | 110.9 (3) | H13A—C13—H13B | 108.1 |
C24—O2—Fe1 | 111.6 (3) | N4—C14—C15 | 120.6 (6) |
C18—N4—C14 | 119.8 (5) | N4—C14—C13 | 115.3 (6) |
C18—N4—Fe1 | 124.5 (4) | C15—C14—C13 | 124.1 (7) |
C14—N4—Fe1 | 115.6 (4) | C16—C15—C14 | 118.6 (7) |
C6—N2—C7 | 111.9 (4) | C16—C15—H15 | 120.7 |
C6—N2—C13 | 112.8 (4) | C14—C15—H15 | 120.7 |
C7—N2—C13 | 109.8 (4) | C15—C16—C17 | 121.3 (8) |
C6—N2—Fe1 | 107.6 (3) | C15—C16—H16 | 119.4 |
C7—N2—Fe1 | 109.0 (3) | C17—C16—H16 | 119.4 |
C13—N2—Fe1 | 105.5 (3) | C18—C17—C16 | 117.8 (8) |
C8—N3—C12 | 118.7 (4) | C18—C17—H17 | 121.1 |
C8—N3—Fe1 | 115.2 (3) | C16—C17—H17 | 121.1 |
C12—N3—Fe1 | 125.6 (4) | N4—C18—C17 | 122.0 (6) |
C5—N1—C1 | 120.5 (6) | N4—C18—H18 | 119.0 |
C5—N1—Fe1 | 115.7 (5) | C17—C18—H18 | 119.0 |
C1—N1—Fe1 | 123.5 (5) | O1—C19—C20 | 122.8 (5) |
N1—C1—C2 | 121.8 (7) | O1—C19—C24 | 117.2 (4) |
N1—C1—H1 | 119.1 | C20—C19—C24 | 120.1 (5) |
C2—C1—H1 | 119.1 | C21—C20—C19 | 119.0 (4) |
C3—C2—C1 | 119.1 (9) | C21—C20—Cl1 | 121.9 (4) |
C3—C2—H2 | 120.4 | C19—C20—Cl1 | 119.1 (4) |
C1—C2—H2 | 120.4 | C22—C21—C20 | 121.3 (4) |
C2—C3—C4 | 119.6 (10) | C22—C21—Cl2 | 119.6 (4) |
C2—C3—H3 | 120.2 | C20—C21—Cl2 | 119.1 (4) |
C4—C3—H3 | 120.2 | C21—C22—C23 | 119.7 (4) |
C3—C4—C5 | 119.8 (9) | C21—C22—Cl3 | 120.9 (4) |
C3—C4—H4 | 120.1 | C23—C22—Cl3 | 119.3 (4) |
C5—C4—H4 | 120.1 | C24—C23—C22 | 119.7 (5) |
N1—C5—C4 | 119.3 (7) | C24—C23—Cl4 | 118.3 (4) |
N1—C5—C6 | 116.4 (6) | C22—C23—Cl4 | 122.0 (4) |
C4—C5—C6 | 124.1 (8) | O2—C24—C23 | 124.4 (4) |
N2—C6—C5 | 109.7 (5) | O2—C24—C19 | 115.5 (4) |
N2—C6—H6A | 109.7 | C23—C24—C19 | 120.1 (5) |
| | | |
O2—Fe1—O1—C19 | 1.1 (3) | C7—N2—C6—C5 | −81.5 (5) |
N3—Fe1—O1—C19 | 177.5 (3) | C13—N2—C6—C5 | 154.1 (4) |
N1—Fe1—O1—C19 | 91.2 (3) | Fe1—N2—C6—C5 | 38.2 (5) |
N4—Fe1—O1—C19 | −91.4 (3) | N1—C5—C6—N2 | −34.4 (7) |
N2—Fe1—O1—C19 | −165.4 (12) | C4—C5—C6—N2 | 150.8 (5) |
O1—Fe1—O2—C24 | −0.6 (3) | C6—N2—C7—C8 | 102.0 (5) |
N3—Fe1—O2—C24 | −52.1 (19) | C13—N2—C7—C8 | −132.0 (4) |
N1—Fe1—O2—C24 | −104.6 (3) | Fe1—N2—C7—C8 | −16.9 (5) |
N4—Fe1—O2—C24 | 100.7 (3) | C12—N3—C8—C9 | −0.8 (6) |
N2—Fe1—O2—C24 | 177.7 (3) | Fe1—N3—C8—C9 | 171.1 (3) |
O1—Fe1—N4—C18 | −10.9 (4) | C12—N3—C8—C7 | 175.5 (4) |
O2—Fe1—N4—C18 | −96.3 (4) | Fe1—N3—C8—C7 | −12.5 (5) |
N3—Fe1—N4—C18 | 81.6 (4) | N2—C7—C8—N3 | 20.3 (6) |
N1—Fe1—N4—C18 | 163.3 (4) | N2—C7—C8—C9 | −163.4 (4) |
N2—Fe1—N4—C18 | 162.3 (4) | N3—C8—C9—C10 | 1.9 (7) |
O1—Fe1—N4—C14 | 165.3 (3) | C7—C8—C9—C10 | −174.3 (5) |
O2—Fe1—N4—C14 | 79.9 (3) | C8—C9—C10—C11 | −1.8 (9) |
N3—Fe1—N4—C14 | −102.2 (4) | C9—C10—C11—C12 | 0.7 (9) |
N1—Fe1—N4—C14 | −20.5 (5) | C8—N3—C12—C11 | −0.3 (7) |
N2—Fe1—N4—C14 | −21.5 (3) | Fe1—N3—C12—C11 | −171.3 (4) |
O1—Fe1—N2—C6 | −130.4 (12) | C10—C11—C12—N3 | 0.3 (8) |
O2—Fe1—N2—C6 | 63.3 (3) | C6—N2—C13—C14 | −159.5 (4) |
N3—Fe1—N2—C6 | −113.1 (3) | C7—N2—C13—C14 | 74.9 (5) |
N1—Fe1—N2—C6 | −25.4 (3) | Fe1—N2—C13—C14 | −42.4 (5) |
N4—Fe1—N2—C6 | 154.1 (3) | C18—N4—C14—C15 | 1.9 (8) |
O1—Fe1—N2—C7 | −8.9 (15) | Fe1—N4—C14—C15 | −174.5 (4) |
O2—Fe1—N2—C7 | −175.1 (3) | C18—N4—C14—C13 | 179.5 (5) |
N3—Fe1—N2—C7 | 8.5 (3) | Fe1—N4—C14—C13 | 3.1 (6) |
N1—Fe1—N2—C7 | 96.1 (3) | N2—C13—C14—N4 | 27.5 (6) |
N4—Fe1—N2—C7 | −84.3 (3) | N2—C13—C14—C15 | −155.0 (5) |
O1—Fe1—N2—C13 | 109.0 (12) | N4—C14—C15—C16 | −0.4 (9) |
O2—Fe1—N2—C13 | −57.3 (3) | C13—C14—C15—C16 | −177.8 (6) |
N3—Fe1—N2—C13 | 126.3 (3) | C14—C15—C16—C17 | −1.1 (11) |
N1—Fe1—N2—C13 | −146.0 (4) | C15—C16—C17—C18 | 1.0 (11) |
N4—Fe1—N2—C13 | 33.5 (3) | C14—N4—C18—C17 | −2.1 (8) |
O1—Fe1—N3—C8 | 179.9 (3) | Fe1—N4—C18—C17 | 174.0 (4) |
O2—Fe1—N3—C8 | −128.8 (17) | C16—C17—C18—N4 | 0.6 (9) |
N1—Fe1—N3—C8 | −76.2 (3) | Fe1—O1—C19—C20 | 179.0 (4) |
N4—Fe1—N3—C8 | 78.3 (3) | Fe1—O1—C19—C24 | −1.5 (5) |
N2—Fe1—N3—C8 | 1.9 (3) | O1—C19—C20—C21 | −179.6 (4) |
O1—Fe1—N3—C12 | −8.8 (4) | C24—C19—C20—C21 | 0.9 (7) |
O2—Fe1—N3—C12 | 42.5 (19) | O1—C19—C20—Cl1 | 0.3 (6) |
N1—Fe1—N3—C12 | 95.1 (4) | C24—C19—C20—Cl1 | −179.2 (3) |
N4—Fe1—N3—C12 | −110.4 (4) | C19—C20—C21—C22 | −2.0 (7) |
N2—Fe1—N3—C12 | 173.3 (4) | Cl1—C20—C21—C22 | 178.1 (4) |
O1—Fe1—N1—C5 | −178.6 (4) | C19—C20—C21—Cl2 | 179.8 (4) |
O2—Fe1—N1—C5 | −93.6 (4) | Cl1—C20—C21—Cl2 | −0.1 (6) |
N3—Fe1—N1—C5 | 90.1 (4) | C20—C21—C22—C23 | 0.7 (8) |
N4—Fe1—N1—C5 | 7.2 (6) | Cl2—C21—C22—C23 | 178.9 (4) |
N2—Fe1—N1—C5 | 8.3 (4) | C20—C21—C22—Cl3 | 179.1 (4) |
O1—Fe1—N1—C1 | 7.3 (4) | Cl2—C21—C22—Cl3 | −2.7 (6) |
O2—Fe1—N1—C1 | 92.2 (4) | C21—C22—C23—C24 | 1.6 (7) |
N3—Fe1—N1—C1 | −84.1 (4) | Cl3—C22—C23—C24 | −176.8 (4) |
N4—Fe1—N1—C1 | −166.9 (4) | C21—C22—C23—Cl4 | −179.0 (4) |
N2—Fe1—N1—C1 | −165.9 (4) | Cl3—C22—C23—Cl4 | 2.7 (6) |
C5—N1—C1—C2 | 1.2 (8) | Fe1—O2—C24—C23 | 179.1 (3) |
Fe1—N1—C1—C2 | 175.1 (4) | Fe1—O2—C24—C19 | 0.0 (5) |
N1—C1—C2—C3 | −3.2 (11) | C22—C23—C24—O2 | 178.3 (4) |
C1—C2—C3—C4 | 2.7 (13) | Cl4—C23—C24—O2 | −1.1 (6) |
C2—C3—C4—C5 | −0.4 (13) | C22—C23—C24—C19 | −2.7 (7) |
C1—N1—C5—C4 | 1.2 (8) | Cl4—C23—C24—C19 | 177.9 (3) |
Fe1—N1—C5—C4 | −173.2 (4) | O1—C19—C24—O2 | 1.0 (6) |
C1—N1—C5—C6 | −174.0 (5) | C20—C19—C24—O2 | −179.5 (4) |
Fe1—N1—C5—C6 | 11.7 (6) | O1—C19—C24—C23 | −178.1 (4) |
C3—C4—C5—N1 | −1.6 (10) | C20—C19—C24—C23 | 1.4 (7) |
C3—C4—C5—C6 | 173.2 (7) | | |
Crystal data top
C24H18Cl4F6FeN4O2P | F(000) = 1476 |
Mr = 737.04 | Dx = 1.617 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.561 (2) Å | µ = 0.97 mm−1 |
b = 37.414 (9) Å | T = 400 K |
c = 9.452 (2) Å | Plate, purple |
V = 3027.5 (12) Å3 | 0.20 × 0.20 × 0.05 mm |
Z = 4 | |
Data collection top
CCD Saphire 3 Xcalibur diffractometer | 1760 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.121 |
Graphite monochromator | θmax = 27.0°, θmin = 2.6° |
Detector resolution: 19.64 pixels mm-1 | h = −10→10 |
ω scan | k = −47→47 |
35296 measured reflections | l = −12→12 |
6576 independent 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)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0651P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.53 | (Δ/σ)max = 0.001 |
6576 reflections | Δρmax = 0.31 e Å−3 |
379 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (2) |
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 | Uiso*/Ueq | |
Fe1 | −0.11014 (9) | 0.134605 (19) | 0.30104 (9) | 0.0674 (3) | |
Cl1 | −0.0628 (2) | 0.26489 (4) | 0.2470 (2) | 0.1136 (7) | |
Cl2 | −0.1908 (2) | 0.28983 (4) | −0.0491 (2) | 0.1245 (7) | |
Cl3 | −0.3304 (2) | 0.23345 (5) | −0.2597 (2) | 0.1268 (8) | |
Cl4 | −0.3511 (2) | 0.15210 (4) | −0.16513 (17) | 0.0916 (6) | |
P1 | −0.3106 (3) | 0.02133 (6) | −0.1360 (3) | 0.1083 (7) | |
F1 | −0.3540 (10) | 0.0207 (2) | 0.0191 (6) | 0.264 (4) | |
F2 | −0.2588 (9) | 0.02260 (16) | −0.2886 (6) | 0.223 (3) | |
F3 | −0.3061 (8) | −0.01968 (12) | −0.1393 (7) | 0.222 (3) | |
F4 | −0.1299 (8) | 0.01923 (18) | −0.1080 (9) | 0.239 (3) | |
F5 | −0.2948 (7) | 0.06003 (11) | −0.1188 (9) | 0.279 (5) | |
F6 | −0.4796 (7) | 0.0216 (2) | −0.1600 (9) | 0.268 (4) | |
O1 | −0.0884 (4) | 0.18584 (8) | 0.2914 (5) | 0.0692 (10) | |
O2 | −0.2057 (4) | 0.13884 (10) | 0.1151 (4) | 0.0685 (11) | |
N1 | −0.3307 (6) | 0.1279 (2) | 0.3989 (6) | 0.0798 (15) | |
N2 | −0.1149 (6) | 0.07686 (12) | 0.3342 (5) | 0.0665 (13) | |
N3 | −0.0190 (5) | 0.13392 (16) | 0.5103 (5) | 0.0633 (13) | |
N4 | 0.1066 (7) | 0.11749 (15) | 0.2180 (5) | 0.0691 (14) | |
C1 | −0.4191 (12) | 0.1548 (2) | 0.4566 (9) | 0.109 (2) | |
H1 | −0.3887 | 0.1784 | 0.4431 | 0.131* | |
C2 | −0.5506 (14) | 0.1476 (4) | 0.5333 (11) | 0.143 (4) | |
H2 | −0.6095 | 0.1665 | 0.5690 | 0.171* | |
C3 | −0.5958 (14) | 0.1144 (5) | 0.5577 (12) | 0.158 (5) | |
H3 | −0.6843 | 0.1101 | 0.6121 | 0.189* | |
C4 | −0.5099 (13) | 0.0855 (3) | 0.5013 (11) | 0.138 (4) | |
H4 | −0.5411 | 0.0620 | 0.5162 | 0.166* | |
C5 | −0.3739 (10) | 0.0936 (3) | 0.4210 (8) | 0.093 (2) | |
C6 | −0.2784 (9) | 0.06598 (19) | 0.3446 (8) | 0.101 (2) | |
H6A | −0.2851 | 0.0434 | 0.3947 | 0.121* | |
H6B | −0.3206 | 0.0625 | 0.2504 | 0.121* | |
C7 | −0.0283 (8) | 0.06904 (16) | 0.4742 (7) | 0.084 (2) | |
H7A | −0.0842 | 0.0505 | 0.5248 | 0.101* | |
H7B | 0.0750 | 0.0600 | 0.4524 | 0.101* | |
C8 | −0.0119 (6) | 0.1013 (2) | 0.5700 (7) | 0.0665 (17) | |
C9 | 0.0209 (7) | 0.0965 (2) | 0.7173 (9) | 0.091 (2) | |
H9 | 0.0252 | 0.0738 | 0.7571 | 0.109* | |
C10 | 0.0458 (8) | 0.1266 (3) | 0.7979 (9) | 0.113 (2) | |
H10 | 0.0644 | 0.1248 | 0.8946 | 0.136* | |
C11 | 0.0426 (8) | 0.1589 (3) | 0.7329 (9) | 0.104 (2) | |
H11 | 0.0662 | 0.1791 | 0.7860 | 0.125* | |
C12 | 0.0060 (6) | 0.16329 (18) | 0.5911 (8) | 0.0740 (18) | |
H12 | −0.0012 | 0.1860 | 0.5520 | 0.089* | |
C13 | −0.0298 (10) | 0.06153 (17) | 0.2117 (7) | 0.090 (2) | |
H13A | −0.0981 | 0.0613 | 0.1298 | 0.108* | |
H13B | −0.0007 | 0.0370 | 0.2327 | 0.108* | |
C14 | 0.1133 (10) | 0.0825 (2) | 0.1780 (7) | 0.0744 (18) | |
C15 | 0.2445 (13) | 0.0698 (2) | 0.1090 (7) | 0.098 (2) | |
H15 | 0.2497 | 0.0460 | 0.0812 | 0.118* | |
C16 | 0.3682 (12) | 0.0927 (4) | 0.0814 (10) | 0.128 (4) | |
H16 | 0.4575 | 0.0841 | 0.0368 | 0.154* | |
C17 | 0.3590 (12) | 0.1278 (3) | 0.1196 (9) | 0.113 (3) | |
H17 | 0.4402 | 0.1436 | 0.0998 | 0.136* | |
C18 | 0.2282 (11) | 0.13916 (19) | 0.1873 (7) | 0.085 (2) | |
H18 | 0.2220 | 0.1630 | 0.2139 | 0.101* | |
C19 | −0.1417 (6) | 0.19865 (16) | 0.1665 (7) | 0.0633 (16) | |
C20 | −0.1401 (7) | 0.23474 (16) | 0.1282 (7) | 0.0726 (18) | |
C21 | −0.1981 (7) | 0.24494 (16) | −0.0038 (8) | 0.0778 (19) | |
C22 | −0.2613 (7) | 0.22046 (19) | −0.0931 (7) | 0.0788 (19) | |
C23 | −0.2688 (6) | 0.18429 (17) | −0.0569 (7) | 0.0693 (16) | |
C24 | −0.2053 (7) | 0.17302 (18) | 0.0730 (7) | 0.0612 (16) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0756 (6) | 0.0658 (5) | 0.0610 (5) | 0.0019 (5) | −0.0058 (6) | −0.0011 (5) |
Cl1 | 0.1428 (16) | 0.0722 (11) | 0.1259 (18) | −0.0101 (10) | −0.0395 (13) | −0.0156 (10) |
Cl2 | 0.1563 (17) | 0.0759 (12) | 0.1412 (17) | 0.0026 (11) | −0.0307 (16) | 0.0291 (12) |
Cl3 | 0.176 (2) | 0.1144 (14) | 0.0905 (16) | 0.0008 (13) | −0.0413 (14) | 0.0308 (12) |
Cl4 | 0.1095 (14) | 0.0972 (11) | 0.0680 (12) | −0.0041 (9) | −0.0216 (10) | −0.0053 (9) |
P1 | 0.123 (2) | 0.0891 (18) | 0.113 (2) | −0.0113 (14) | 0.0262 (16) | −0.0192 (13) |
F1 | 0.364 (11) | 0.325 (9) | 0.103 (5) | −0.078 (7) | 0.073 (6) | −0.049 (5) |
F2 | 0.310 (9) | 0.224 (6) | 0.135 (5) | −0.056 (5) | 0.071 (6) | −0.006 (5) |
F3 | 0.313 (7) | 0.098 (4) | 0.255 (7) | −0.017 (4) | 0.137 (6) | −0.012 (4) |
F4 | 0.171 (6) | 0.264 (7) | 0.281 (9) | 0.032 (5) | −0.033 (6) | 0.006 (6) |
F5 | 0.306 (7) | 0.068 (3) | 0.462 (13) | −0.006 (4) | 0.174 (8) | −0.052 (5) |
F6 | 0.114 (5) | 0.379 (10) | 0.310 (11) | −0.037 (5) | −0.037 (6) | −0.044 (8) |
O1 | 0.081 (3) | 0.066 (2) | 0.061 (2) | 0.004 (2) | −0.019 (3) | −0.004 (3) |
O2 | 0.081 (3) | 0.065 (3) | 0.060 (3) | 0.005 (2) | −0.007 (2) | −0.003 (2) |
N1 | 0.065 (4) | 0.108 (5) | 0.067 (4) | 0.002 (4) | −0.014 (3) | −0.005 (4) |
N2 | 0.067 (4) | 0.073 (3) | 0.060 (4) | −0.012 (3) | −0.016 (3) | 0.000 (3) |
N3 | 0.061 (4) | 0.064 (3) | 0.065 (3) | −0.005 (3) | −0.002 (3) | 0.001 (4) |
N4 | 0.078 (4) | 0.068 (3) | 0.061 (3) | 0.004 (3) | −0.011 (3) | 0.002 (3) |
C1 | 0.100 (7) | 0.144 (7) | 0.083 (5) | 0.027 (7) | −0.022 (6) | −0.030 (6) |
C2 | 0.068 (8) | 0.258 (16) | 0.102 (8) | 0.001 (8) | −0.002 (6) | −0.040 (9) |
C3 | 0.102 (10) | 0.250 (17) | 0.120 (9) | −0.050 (10) | 0.028 (7) | −0.045 (10) |
C4 | 0.103 (9) | 0.211 (12) | 0.102 (8) | −0.064 (8) | −0.018 (7) | 0.005 (7) |
C5 | 0.071 (7) | 0.143 (8) | 0.065 (5) | −0.033 (6) | −0.007 (5) | −0.008 (5) |
C6 | 0.100 (6) | 0.095 (5) | 0.108 (6) | −0.027 (5) | −0.008 (5) | 0.003 (5) |
C7 | 0.093 (5) | 0.071 (5) | 0.088 (6) | −0.007 (4) | −0.004 (5) | 0.014 (4) |
C8 | 0.050 (4) | 0.086 (5) | 0.063 (5) | −0.007 (4) | −0.004 (3) | 0.005 (5) |
C9 | 0.086 (5) | 0.119 (6) | 0.067 (6) | −0.006 (4) | −0.018 (4) | 0.008 (5) |
C10 | 0.135 (6) | 0.141 (7) | 0.063 (5) | −0.009 (5) | −0.001 (6) | −0.023 (7) |
C11 | 0.097 (6) | 0.148 (8) | 0.067 (6) | −0.030 (6) | −0.002 (4) | −0.041 (6) |
C12 | 0.072 (5) | 0.076 (5) | 0.074 (6) | −0.004 (4) | 0.003 (4) | −0.017 (4) |
C13 | 0.124 (7) | 0.069 (4) | 0.077 (5) | 0.013 (5) | 0.001 (5) | −0.033 (4) |
C14 | 0.090 (6) | 0.079 (5) | 0.055 (4) | 0.013 (5) | −0.009 (4) | 0.005 (4) |
C15 | 0.115 (7) | 0.109 (6) | 0.071 (5) | 0.049 (6) | 0.019 (5) | −0.005 (4) |
C16 | 0.084 (8) | 0.175 (10) | 0.125 (8) | 0.064 (8) | 0.020 (6) | 0.063 (8) |
C17 | 0.098 (8) | 0.143 (9) | 0.100 (6) | 0.035 (7) | −0.005 (6) | 0.024 (6) |
C18 | 0.086 (6) | 0.095 (6) | 0.073 (5) | −0.003 (5) | 0.012 (5) | 0.005 (4) |
C19 | 0.067 (5) | 0.052 (4) | 0.070 (5) | 0.005 (4) | 0.004 (4) | 0.003 (4) |
C20 | 0.076 (5) | 0.057 (4) | 0.085 (5) | −0.004 (4) | −0.017 (4) | −0.009 (4) |
C21 | 0.079 (5) | 0.066 (5) | 0.089 (6) | 0.002 (4) | −0.008 (4) | 0.015 (4) |
C22 | 0.084 (5) | 0.075 (5) | 0.077 (5) | 0.008 (4) | 0.001 (4) | 0.008 (4) |
C23 | 0.073 (5) | 0.079 (5) | 0.056 (4) | 0.000 (4) | 0.005 (4) | −0.002 (4) |
C24 | 0.060 (4) | 0.057 (4) | 0.066 (4) | −0.002 (3) | −0.003 (4) | 0.008 (4) |
Geometric parameters (Å, º) top
Fe1—O1 | 1.928 (3) | C4—C5 | 1.423 (10) |
Fe1—O2 | 1.945 (4) | C4—H4 | 0.9300 |
Fe1—N4 | 2.114 (5) | C5—C6 | 1.502 (8) |
Fe1—N1 | 2.118 (6) | C6—H6A | 0.9700 |
Fe1—N3 | 2.127 (5) | C6—H6B | 0.9700 |
Fe1—N2 | 2.183 (4) | C7—C8 | 1.515 (8) |
Cl1—C20 | 1.724 (6) | C7—H7A | 0.9700 |
Cl2—C21 | 1.735 (6) | C7—H7B | 0.9700 |
Cl3—C22 | 1.750 (7) | C8—C9 | 1.432 (8) |
Cl4—C23 | 1.730 (6) | C9—C10 | 1.376 (9) |
P1—F5 | 1.463 (5) | C9—H9 | 0.9300 |
P1—F6 | 1.465 (6) | C10—C11 | 1.358 (9) |
P1—F2 | 1.510 (6) | C10—H10 | 0.9300 |
P1—F1 | 1.513 (6) | C11—C12 | 1.386 (9) |
P1—F3 | 1.535 (5) | C11—H11 | 0.9300 |
P1—F4 | 1.571 (6) | C12—H12 | 0.9300 |
O1—C19 | 1.353 (7) | C13—C14 | 1.490 (9) |
O2—C24 | 1.340 (6) | C13—H13A | 0.9700 |
N1—C5 | 1.350 (8) | C13—H13B | 0.9700 |
N1—C1 | 1.372 (8) | C14—C15 | 1.384 (8) |
N2—C6 | 1.461 (7) | C15—C16 | 1.387 (10) |
N2—C13 | 1.484 (7) | C15—H15 | 0.9300 |
N2—C7 | 1.545 (7) | C16—C17 | 1.366 (12) |
N3—C8 | 1.346 (6) | C16—H16 | 0.9300 |
N3—C12 | 1.355 (7) | C17—C18 | 1.357 (9) |
N4—C18 | 1.351 (7) | C17—H17 | 0.9300 |
N4—C14 | 1.363 (7) | C18—H18 | 0.9300 |
C1—C2 | 1.366 (11) | C19—C20 | 1.398 (7) |
C1—H1 | 0.9300 | C19—C24 | 1.413 (8) |
C2—C3 | 1.323 (14) | C20—C21 | 1.395 (8) |
C2—H2 | 0.9300 | C21—C22 | 1.358 (8) |
C3—C4 | 1.412 (14) | C22—C23 | 1.398 (7) |
C3—H3 | 0.9300 | C23—C24 | 1.407 (8) |
| | | |
O1—Fe1—O2 | 85.23 (17) | C5—C6—H6A | 109.4 |
O1—Fe1—N4 | 101.5 (2) | N2—C6—H6B | 109.4 |
O2—Fe1—N4 | 93.35 (17) | C5—C6—H6B | 109.4 |
O1—Fe1—N1 | 103.0 (2) | H6A—C6—H6B | 108.0 |
O2—Fe1—N1 | 91.67 (18) | C8—C7—N2 | 113.9 (5) |
N4—Fe1—N1 | 155.3 (3) | C8—C7—H7A | 108.8 |
O1—Fe1—N3 | 91.2 (2) | N2—C7—H7A | 108.8 |
O2—Fe1—N3 | 174.74 (19) | C8—C7—H7B | 108.8 |
N4—Fe1—N3 | 91.14 (17) | N2—C7—H7B | 108.8 |
N1—Fe1—N3 | 85.37 (17) | H7A—C7—H7B | 107.7 |
O1—Fe1—N2 | 172.90 (19) | N3—C8—C9 | 122.0 (6) |
O2—Fe1—N2 | 101.68 (17) | N3—C8—C7 | 117.9 (6) |
N4—Fe1—N2 | 76.7 (2) | C9—C8—C7 | 120.0 (6) |
N1—Fe1—N2 | 78.6 (2) | C10—C9—C8 | 117.8 (7) |
N3—Fe1—N2 | 82.0 (2) | C10—C9—H9 | 121.1 |
F5—P1—F6 | 95.9 (4) | C8—C9—H9 | 121.1 |
F5—P1—F2 | 92.7 (4) | C11—C10—C9 | 118.4 (8) |
F6—P1—F2 | 98.1 (5) | C11—C10—H10 | 120.8 |
F5—P1—F1 | 86.0 (4) | C9—C10—H10 | 120.8 |
F6—P1—F1 | 84.7 (5) | C10—C11—C12 | 123.2 (7) |
F2—P1—F1 | 177.0 (5) | C10—C11—H11 | 118.4 |
F5—P1—F3 | 171.5 (4) | C12—C11—H11 | 118.4 |
F6—P1—F3 | 91.6 (4) | N3—C12—C11 | 119.0 (6) |
F2—P1—F3 | 90.3 (3) | N3—C12—H12 | 120.5 |
F1—P1—F3 | 90.6 (4) | C11—C12—H12 | 120.5 |
F5—P1—F4 | 86.5 (4) | N2—C13—C14 | 111.5 (5) |
F6—P1—F4 | 177.4 (4) | N2—C13—H13A | 109.3 |
F2—P1—F4 | 82.7 (4) | C14—C13—H13A | 109.3 |
F1—P1—F4 | 94.5 (5) | N2—C13—H13B | 109.3 |
F3—P1—F4 | 85.9 (3) | C14—C13—H13B | 109.3 |
C19—O1—Fe1 | 111.2 (4) | H13A—C13—H13B | 108.0 |
C24—O2—Fe1 | 110.2 (4) | N4—C14—C15 | 119.7 (7) |
C5—N1—C1 | 119.0 (7) | N4—C14—C13 | 114.4 (7) |
C5—N1—Fe1 | 115.1 (6) | C15—C14—C13 | 125.9 (7) |
C1—N1—Fe1 | 125.3 (7) | C14—C15—C16 | 119.7 (8) |
C6—N2—C13 | 114.5 (6) | C14—C15—H15 | 120.1 |
C6—N2—C7 | 110.4 (5) | C16—C15—H15 | 120.1 |
C13—N2—C7 | 111.1 (5) | C17—C16—C15 | 120.1 (9) |
C6—N2—Fe1 | 107.6 (4) | C17—C16—H16 | 120.0 |
C13—N2—Fe1 | 105.2 (4) | C15—C16—H16 | 120.0 |
C7—N2—Fe1 | 107.5 (3) | C18—C17—C16 | 118.2 (10) |
C8—N3—C12 | 119.5 (5) | C18—C17—H17 | 120.9 |
C8—N3—Fe1 | 114.6 (4) | C16—C17—H17 | 120.9 |
C12—N3—Fe1 | 124.9 (5) | N4—C18—C17 | 123.3 (8) |
C18—N4—C14 | 118.9 (6) | N4—C18—H18 | 118.3 |
C18—N4—Fe1 | 125.1 (5) | C17—C18—H18 | 118.3 |
C14—N4—Fe1 | 115.5 (5) | O1—C19—C20 | 124.4 (6) |
C2—C1—N1 | 121.5 (9) | O1—C19—C24 | 115.8 (5) |
C2—C1—H1 | 119.2 | C20—C19—C24 | 119.8 (6) |
N1—C1—H1 | 119.2 | C21—C20—C19 | 119.5 (5) |
C3—C2—C1 | 121.1 (13) | C21—C20—Cl1 | 122.7 (5) |
C3—C2—H2 | 119.4 | C19—C20—Cl1 | 117.8 (5) |
C1—C2—H2 | 119.4 | C22—C21—C20 | 120.9 (5) |
C2—C3—C4 | 120.2 (13) | C22—C21—Cl2 | 120.9 (6) |
C2—C3—H3 | 119.9 | C20—C21—Cl2 | 118.2 (6) |
C4—C3—H3 | 119.9 | C21—C22—C23 | 121.2 (6) |
C3—C4—C5 | 117.6 (11) | C21—C22—Cl3 | 120.5 (5) |
C3—C4—H4 | 121.2 | C23—C22—Cl3 | 118.3 (6) |
C5—C4—H4 | 121.2 | C22—C23—C24 | 119.1 (6) |
N1—C5—C4 | 120.6 (8) | C22—C23—Cl4 | 123.2 (6) |
N1—C5—C6 | 115.5 (8) | C24—C23—Cl4 | 117.7 (5) |
C4—C5—C6 | 123.7 (10) | O2—C24—C23 | 123.0 (6) |
N2—C6—C5 | 111.2 (6) | O2—C24—C19 | 117.6 (6) |
N2—C6—H6A | 109.4 | C23—C24—C19 | 119.4 (6) |
| | | |
O2—Fe1—O1—C19 | −2.0 (3) | C13—N2—C6—C5 | −153.3 (6) |
N4—Fe1—O1—C19 | 90.5 (4) | C7—N2—C6—C5 | 80.3 (7) |
N1—Fe1—O1—C19 | −92.6 (4) | Fe1—N2—C6—C5 | −36.8 (6) |
N3—Fe1—O1—C19 | −178.1 (3) | N1—C5—C6—N2 | 34.6 (8) |
N2—Fe1—O1—C19 | 164.8 (14) | C4—C5—C6—N2 | −151.0 (6) |
O1—Fe1—O2—C24 | 1.6 (4) | C6—N2—C7—C8 | −98.6 (6) |
N4—Fe1—O2—C24 | −99.6 (4) | C13—N2—C7—C8 | 133.1 (6) |
N1—Fe1—O2—C24 | 104.6 (4) | Fe1—N2—C7—C8 | 18.6 (6) |
N3—Fe1—O2—C24 | 49 (2) | C12—N3—C8—C9 | 0.2 (8) |
N2—Fe1—O2—C24 | −176.7 (4) | Fe1—N3—C8—C9 | −169.2 (4) |
O1—Fe1—N1—C5 | −178.9 (4) | C12—N3—C8—C7 | −175.4 (5) |
O2—Fe1—N1—C5 | 95.7 (4) | Fe1—N3—C8—C7 | 15.2 (7) |
N4—Fe1—N1—C5 | −6.1 (8) | N2—C7—C8—N3 | −23.3 (8) |
N3—Fe1—N1—C5 | −88.7 (5) | N2—C7—C8—C9 | 160.9 (5) |
N2—Fe1—N1—C5 | −5.9 (4) | N3—C8—C9—C10 | −0.1 (9) |
O1—Fe1—N1—C1 | −8.0 (5) | C7—C8—C9—C10 | 175.4 (6) |
O2—Fe1—N1—C1 | −93.5 (5) | C8—C9—C10—C11 | −2.0 (10) |
N4—Fe1—N1—C1 | 164.7 (5) | C9—C10—C11—C12 | 4.1 (11) |
N3—Fe1—N1—C1 | 82.1 (5) | C8—N3—C12—C11 | 1.7 (8) |
N2—Fe1—N1—C1 | 164.9 (5) | Fe1—N3—C12—C11 | 170.0 (4) |
O1—Fe1—N2—C6 | 127.6 (14) | C10—C11—C12—N3 | −4.1 (10) |
O2—Fe1—N2—C6 | −65.9 (4) | C6—N2—C13—C14 | 160.3 (6) |
N4—Fe1—N2—C6 | −156.6 (5) | C7—N2—C13—C14 | −73.7 (6) |
N1—Fe1—N2—C6 | 23.5 (4) | Fe1—N2—C13—C14 | 42.4 (6) |
N3—Fe1—N2—C6 | 110.3 (4) | C18—N4—C14—C15 | 0.9 (8) |
O1—Fe1—N2—C13 | −109.9 (15) | Fe1—N4—C14—C15 | 173.3 (4) |
O2—Fe1—N2—C13 | 56.6 (4) | C18—N4—C14—C13 | −177.5 (5) |
N4—Fe1—N2—C13 | −34.1 (4) | Fe1—N4—C14—C13 | −5.1 (6) |
N1—Fe1—N2—C13 | 146.0 (4) | N2—C13—C14—N4 | −26.4 (7) |
N3—Fe1—N2—C13 | −127.2 (4) | N2—C13—C14—C15 | 155.3 (5) |
O1—Fe1—N2—C7 | 8.6 (17) | N4—C14—C15—C16 | 0.2 (10) |
O2—Fe1—N2—C7 | 175.1 (4) | C13—C14—C15—C16 | 178.4 (7) |
N4—Fe1—N2—C7 | 84.4 (4) | C14—C15—C16—C17 | −1.4 (12) |
N1—Fe1—N2—C7 | −95.6 (4) | C15—C16—C17—C18 | 1.5 (12) |
N3—Fe1—N2—C7 | −8.7 (4) | C14—N4—C18—C17 | −0.8 (9) |
O1—Fe1—N3—C8 | 179.1 (4) | Fe1—N4—C18—C17 | −172.4 (5) |
O2—Fe1—N3—C8 | 132 (2) | C16—C17—C18—N4 | −0.4 (11) |
N4—Fe1—N3—C8 | −79.4 (4) | Fe1—O1—C19—C20 | −179.4 (4) |
N1—Fe1—N3—C8 | 76.1 (4) | Fe1—O1—C19—C24 | 1.9 (6) |
N2—Fe1—N3—C8 | −3.0 (4) | O1—C19—C20—C21 | 179.9 (5) |
O1—Fe1—N3—C12 | 10.3 (4) | C24—C19—C20—C21 | −1.5 (8) |
O2—Fe1—N3—C12 | −37 (2) | O1—C19—C20—Cl1 | 0.8 (8) |
N4—Fe1—N3—C12 | 111.8 (5) | C24—C19—C20—Cl1 | 179.4 (4) |
N1—Fe1—N3—C12 | −92.7 (5) | C19—C20—C21—C22 | 2.4 (9) |
N2—Fe1—N3—C12 | −171.8 (5) | Cl1—C20—C21—C22 | −178.5 (5) |
O1—Fe1—N4—C18 | 7.6 (5) | C19—C20—C21—Cl2 | −178.8 (4) |
O2—Fe1—N4—C18 | 93.4 (5) | Cl1—C20—C21—Cl2 | 0.3 (8) |
N1—Fe1—N4—C18 | −165.3 (5) | C20—C21—C22—C23 | −0.8 (10) |
N3—Fe1—N4—C18 | −83.9 (5) | Cl2—C21—C22—C23 | −179.5 (4) |
N2—Fe1—N4—C18 | −165.4 (5) | C20—C21—C22—Cl3 | −178.8 (5) |
O1—Fe1—N4—C14 | −164.3 (4) | Cl2—C21—C22—Cl3 | 2.5 (8) |
O2—Fe1—N4—C14 | −78.5 (4) | C21—C22—C23—C24 | −1.8 (9) |
N1—Fe1—N4—C14 | 22.9 (7) | Cl3—C22—C23—C24 | 176.3 (4) |
N3—Fe1—N4—C14 | 104.3 (4) | C21—C22—C23—Cl4 | 178.8 (5) |
N2—Fe1—N4—C14 | 22.7 (4) | Cl3—C22—C23—Cl4 | −3.1 (7) |
C5—N1—C1—C2 | −1.1 (10) | Fe1—O2—C24—C23 | −179.2 (4) |
Fe1—N1—C1—C2 | −171.6 (6) | Fe1—O2—C24—C19 | −1.0 (6) |
N1—C1—C2—C3 | 1.6 (13) | C22—C23—C24—O2 | −179.1 (5) |
C1—C2—C3—C4 | −1.6 (17) | Cl4—C23—C24—O2 | 0.3 (8) |
C2—C3—C4—C5 | 1.1 (15) | C22—C23—C24—C19 | 2.7 (8) |
C1—N1—C5—C4 | 0.7 (9) | Cl4—C23—C24—C19 | −177.9 (4) |
Fe1—N1—C5—C4 | 172.2 (5) | O1—C19—C24—O2 | −0.6 (8) |
C1—N1—C5—C6 | 175.3 (5) | C20—C19—C24—O2 | −179.3 (5) |
Fe1—N1—C5—C6 | −13.3 (7) | O1—C19—C24—C23 | 177.7 (5) |
C3—C4—C5—N1 | −0.7 (11) | C20—C19—C24—C23 | −1.0 (8) |
C3—C4—C5—C6 | −174.8 (8) | | |