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The title compound, aquachloro{4,4′-dibromo-2,2′-[
o-phenylenebis(nitrilomethylidyne)]diphenolato-
O,
N,
N′,
O′}iron(III)–chloro{4,4′-dibromo-2,2′-[
o-phenylenebis(nitrilomethyli-dyne)]diphenolato-
O,
N,
N′,
O′}iron(III)–dimethylformamide (1/1/1), [FeCl(C
20H
12Br
2N
2O
2)][FeCl(C
20H
12Br
2N
2O
2)(H
2O)]·C
3H
7NO, contains one independent five-coordinate [FeCl(C
20H
12Br
2N
2O
2)] monomer, one six-coordinate [FeCl(C
20H
12Br
2N
2O
2)(H
2O)] monomer and a non-coordinating dimethylformamide solvent molecule in the asymmetric unit. In the five-coordinate monomer, the Fe atom shows distorted square-pyramidal geometry, with the N and O atoms of the ligand at the base and the Cl atom at the apex of the pyramid. In the six-coordinate monomer, the Fe atom is in a distorted octahedral geometry and coordinated by the donor atoms of the tetrafunctional ligand in the horizontal plane, and the coordination sphere is completed by the O atom of the water molecule and the Cl atom at the axial positions. The title compound contains intermolecular O—H
O hydrogen bonds. Apart from these hydrogen bonds, there are also intermolecular C—H
Cl and C—H
O contacts.
Supporting information
CCDC reference: 150770
Data collection: CAD-4 Diffractometer Control Software (Enraf-Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: REDU4 (Stoe & Cie, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON92 (Spek, 1992); software used to prepare material for publication: SHELXL97.
Crystal data top
[FeCl(C20H12N2O2)][FeCl(C20H12N2O2)H2O]·C3H7NO | Z = 2 |
Mr = 1218.01 | F(000) = 1188 |
Triclinic, P1 | Dx = 1.885 Mg m−3 |
a = 11.623 (2) Å | Mo Kα radiation, λ = 0.71093 Å |
b = 13.426 (3) Å | Cell parameters from 25 reflections |
c = 15.156 (2) Å | θ = 3.0–13.3° |
α = 76.44 (1)° | µ = 4.60 mm−1 |
β = 71.30 (1)° | T = 303 K |
γ = 75.16 (2)° | Needle, black |
V = 2135.4 (7) Å3 | 0.40 × 0.10 × 0.05 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 7911 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.5°, θmin = 1.4° |
θ/2θ scans | h = −13→14 |
Absorption correction: empirical (using intensity measurements) via ψ scans (north et al., 1968) | k = −15→16 |
Tmin = 0.156, Tmax = 0.794 | l = 0→18 |
9150 measured reflections | 3 standard reflections every 90 min |
7926 independent reflections | intensity decay: 3.6% |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.01 | Calculated w = 1/[σ2(Fo2) + (0.0126P)2 + 1.3469P] where P = (Fo2 + 2Fc2)/3 |
7926 reflections | (Δ/σ)max = 0.002 |
540 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −1.34 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 | |
C1 | 0.5895 (2) | 0.8416 (2) | −0.19648 (17) | 0.0376 (5) | |
C2 | 0.5618 (3) | 0.8369 (2) | −0.27935 (19) | 0.0450 (6) | |
H2 | 0.5529 | 0.7739 | −0.2893 | 0.054* | |
C3 | 0.5480 (3) | 0.9249 (2) | −0.34462 (19) | 0.0504 (7) | |
H3 | 0.5321 | 0.9213 | −0.4000 | 0.060* | |
C4 | 0.5578 (3) | 1.0209 (2) | −0.32857 (19) | 0.0468 (6) | |
C5 | 0.5909 (2) | 1.0276 (2) | −0.25424 (19) | 0.0428 (6) | |
H5 | 0.6046 | 1.0907 | −0.2485 | 0.051* | |
C6 | 0.60558 (17) | 0.93825 (17) | −0.18335 (16) | 0.0281 (4) | |
C7 | 0.63854 (19) | 0.94838 (18) | −0.10442 (18) | 0.0344 (5) | |
H7 | 0.6556 | 1.0125 | −0.1048 | 0.041* | |
C8 | 0.68269 (17) | 0.89416 (17) | 0.04428 (16) | 0.0279 (4) | |
C9 | 0.6976 (2) | 0.99065 (19) | 0.05379 (18) | 0.0358 (5) | |
H9 | 0.6843 | 1.0493 | 0.0086 | 0.043* | |
C10 | 0.7318 (3) | 0.9985 (2) | 0.1299 (2) | 0.0461 (6) | |
H10 | 0.7438 | 1.0625 | 0.1351 | 0.055* | |
C11 | 0.7487 (3) | 0.9145 (2) | 0.1982 (2) | 0.0456 (6) | |
H11 | 0.7690 | 0.9222 | 0.2504 | 0.055* | |
C12 | 0.7356 (3) | 0.8167 (2) | 0.19018 (19) | 0.0414 (5) | |
H12 | 0.7479 | 0.7589 | 0.2364 | 0.050* | |
C13 | 0.70375 (19) | 0.80717 (18) | 0.11170 (16) | 0.0306 (4) | |
C14 | 0.7230 (2) | 0.62402 (19) | 0.14430 (18) | 0.0363 (5) | |
H14 | 0.7615 | 0.6250 | 0.1892 | 0.044* | |
C15 | 0.70860 (18) | 0.52477 (17) | 0.13592 (17) | 0.0313 (4) | |
C16 | 0.7342 (2) | 0.43837 (19) | 0.2038 (2) | 0.0429 (6) | |
H16 | 0.7646 | 0.4467 | 0.2509 | 0.052* | |
C17 | 0.7163 (2) | 0.34372 (19) | 0.20309 (19) | 0.0396 (5) | |
C18 | 0.6785 (3) | 0.3274 (2) | 0.1314 (2) | 0.0451 (6) | |
H18 | 0.6678 | 0.2614 | 0.1303 | 0.054* | |
C19 | 0.6568 (2) | 0.4097 (2) | 0.06121 (19) | 0.0430 (5) | |
H19 | 0.6324 | 0.3986 | 0.0122 | 0.052* | |
C20 | 0.6706 (2) | 0.50897 (18) | 0.06226 (17) | 0.0338 (5) | |
C21 | 0.0220 (2) | 0.64206 (17) | 0.06125 (15) | 0.0293 (4) | |
C22 | −0.0131 (2) | 0.64577 (17) | −0.01937 (16) | 0.0308 (4) | |
H22 | −0.0280 | 0.5851 | −0.0295 | 0.037* | |
C23 | −0.0264 (2) | 0.73486 (19) | −0.08421 (16) | 0.0338 (5) | |
H23 | −0.0497 | 0.7348 | −0.1375 | 0.041* | |
C24 | −0.0046 (2) | 0.82493 (17) | −0.06884 (15) | 0.0337 (5) | |
C25 | 0.0305 (2) | 0.82683 (18) | 0.00808 (16) | 0.0332 (5) | |
H25 | 0.0453 | 0.8885 | 0.0164 | 0.040* | |
C26 | 0.04462 (18) | 0.73498 (16) | 0.07551 (14) | 0.0258 (4) | |
C27 | 0.0795 (2) | 0.74462 (15) | 0.15439 (16) | 0.0319 (5) | |
H27 | 0.0941 | 0.8094 | 0.1549 | 0.038* | |
C28 | 0.12707 (17) | 0.69104 (16) | 0.30157 (14) | 0.0265 (4) | |
C29 | 0.1448 (3) | 0.7876 (2) | 0.30986 (18) | 0.0414 (5) | |
H29 | 0.1355 | 0.8450 | 0.2627 | 0.050* | |
C30 | 0.1753 (3) | 0.7983 (2) | 0.3861 (2) | 0.0457 (6) | |
H30 | 0.1904 | 0.8618 | 0.3896 | 0.055* | |
C31 | 0.1838 (2) | 0.7150 (2) | 0.45773 (16) | 0.0394 (5) | |
H31 | 0.2013 | 0.7236 | 0.5109 | 0.047* | |
C32 | 0.1670 (2) | 0.61966 (19) | 0.45266 (18) | 0.0373 (5) | |
H32 | 0.1755 | 0.5635 | 0.5010 | 0.045* | |
C33 | 0.13706 (18) | 0.60717 (16) | 0.37444 (15) | 0.0274 (4) | |
C34 | 0.1392 (2) | 0.42479 (18) | 0.41978 (16) | 0.0328 (5) | |
H34 | 0.1658 | 0.4289 | 0.4703 | 0.039* | |
C35 | 0.1263 (2) | 0.32462 (16) | 0.41260 (15) | 0.0298 (4) | |
C36 | 0.1529 (3) | 0.2424 (2) | 0.48497 (18) | 0.0432 (6) | |
H36 | 0.1779 | 0.2557 | 0.5328 | 0.052* | |
C37 | 0.1420 (3) | 0.14210 (19) | 0.48525 (18) | 0.0421 (6) | |
C38 | 0.1010 (3) | 0.1223 (2) | 0.4157 (2) | 0.0493 (7) | |
H38 | 0.0923 | 0.0550 | 0.4167 | 0.059* | |
C39 | 0.0732 (3) | 0.20162 (19) | 0.34563 (19) | 0.0415 (5) | |
H39 | 0.0463 | 0.1872 | 0.2993 | 0.050* | |
C40 | 0.0845 (2) | 0.30354 (19) | 0.34234 (16) | 0.0348 (5) | |
C41 | 0.4249 (7) | 0.5011 (6) | 0.2856 (5) | 0.133 (2)* | |
H41 | 0.3963 | 0.5598 | 0.2459 | 0.159* | |
C42 | 0.4987 (7) | 0.6138 (6) | 0.3465 (6) | 0.134 (2)* | |
C43 | 0.4802 (7) | 0.4209 (6) | 0.4389 (6) | 0.130 (2)* | |
N1 | 0.64745 (16) | 0.87646 (14) | −0.03096 (14) | 0.0297 (4) | |
N2 | 0.68773 (16) | 0.71265 (14) | 0.09546 (13) | 0.0293 (4) | |
N3 | 0.09279 (17) | 0.67244 (14) | 0.22516 (13) | 0.0310 (4) | |
N4 | 0.11733 (15) | 0.51043 (13) | 0.36256 (12) | 0.0262 (3) | |
N5 | 0.4683 (5) | 0.5056 (5) | 0.3613 (4) | 0.1257 (17)* | |
O1 | 0.6001 (2) | 0.75622 (14) | −0.13398 (13) | 0.0483 (4) | |
O2 | 0.64845 (17) | 0.58715 (13) | −0.00673 (12) | 0.0391 (4) | |
O3 | 0.02901 (18) | 0.55553 (13) | 0.12256 (12) | 0.0398 (4) | |
O4 | 0.0512 (2) | 0.37665 (14) | 0.27579 (14) | 0.0476 (5) | |
O6 | 0.4290 (2) | 0.41346 (19) | 0.27824 (16) | 0.0650 (6) | |
Cl1 | 0.40113 (5) | 0.75915 (5) | 0.08624 (5) | 0.04839 (17) | |
Cl2 | −0.14784 (5) | 0.57896 (5) | 0.33544 (4) | 0.04354 (16) | |
Br1 | 0.53132 (4) | 1.14127 (3) | −0.42098 (3) | 0.07280 (14) | |
Br2 | 0.74309 (4) | 0.22994 (2) | 0.30045 (3) | 0.06775 (13) | |
Br3 | −0.02725 (3) | 0.94973 (2) | −0.15805 (2) | 0.04942 (11) | |
Br4 | 0.17305 (5) | 0.03356 (2) | 0.58348 (3) | 0.07630 (15) | |
Fe1 | 0.59591 (3) | 0.73188 (2) | −0.00593 (2) | 0.03104 (11) | |
Fe2 | 0.05840 (3) | 0.52017 (2) | 0.24315 (2) | 0.03298 (11) | |
O5 | 0.25313 (18) | 0.48039 (16) | 0.17702 (14) | 0.0520 (5) | |
HO51 | 0.2901 | 0.5394 | 0.1502 | 0.062* | |
HO52 | 0.2756 | 0.4450 | 0.1374 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0539 (13) | 0.0325 (12) | 0.0307 (11) | −0.0120 (10) | −0.0152 (10) | −0.0049 (10) |
C2 | 0.0670 (16) | 0.0353 (13) | 0.0367 (13) | −0.0124 (11) | −0.0214 (11) | −0.0011 (10) |
C3 | 0.0792 (19) | 0.0444 (16) | 0.0335 (13) | −0.0177 (14) | −0.0224 (12) | −0.0019 (11) |
C4 | 0.0576 (15) | 0.0356 (14) | 0.0392 (13) | −0.0092 (11) | −0.0135 (11) | 0.0087 (11) |
C5 | 0.0526 (13) | 0.0356 (13) | 0.0433 (13) | −0.0176 (11) | −0.0187 (11) | 0.0051 (11) |
C6 | 0.0249 (9) | 0.0223 (10) | 0.0366 (11) | −0.0034 (7) | −0.0060 (8) | −0.0086 (8) |
C7 | 0.0313 (10) | 0.0264 (11) | 0.0433 (12) | −0.0051 (8) | −0.0115 (9) | −0.0007 (9) |
C8 | 0.0242 (9) | 0.0219 (10) | 0.0384 (11) | −0.0019 (7) | −0.0118 (8) | −0.0054 (8) |
C9 | 0.0418 (11) | 0.0234 (11) | 0.0401 (12) | −0.0048 (9) | −0.0088 (9) | −0.0069 (9) |
C10 | 0.0561 (14) | 0.0311 (13) | 0.0565 (16) | −0.0138 (11) | −0.0150 (12) | −0.0128 (12) |
C11 | 0.0580 (15) | 0.0392 (14) | 0.0470 (14) | −0.0069 (11) | −0.0255 (12) | −0.0088 (12) |
C12 | 0.0602 (14) | 0.0300 (13) | 0.0368 (12) | −0.0040 (10) | −0.0197 (11) | −0.0079 (10) |
C13 | 0.0327 (10) | 0.0283 (11) | 0.0325 (11) | −0.0081 (8) | −0.0122 (8) | −0.0015 (9) |
C14 | 0.0374 (11) | 0.0354 (12) | 0.0446 (13) | −0.0102 (9) | −0.0195 (9) | −0.0081 (10) |
C15 | 0.0263 (9) | 0.0216 (10) | 0.0444 (12) | −0.0031 (7) | −0.0117 (8) | −0.0017 (9) |
C16 | 0.0542 (14) | 0.0241 (11) | 0.0607 (16) | −0.0138 (10) | −0.0339 (12) | 0.0056 (11) |
C17 | 0.0333 (10) | 0.0255 (12) | 0.0535 (15) | −0.0019 (9) | −0.0126 (10) | 0.0021 (10) |
C18 | 0.0597 (15) | 0.0247 (12) | 0.0500 (15) | −0.0081 (10) | −0.0116 (12) | −0.0097 (10) |
C19 | 0.0563 (14) | 0.0296 (12) | 0.0434 (13) | −0.0093 (10) | −0.0114 (11) | −0.0091 (10) |
C20 | 0.0348 (10) | 0.0253 (11) | 0.0355 (11) | 0.0017 (8) | −0.0073 (8) | −0.0058 (9) |
C21 | 0.0421 (11) | 0.0196 (10) | 0.0222 (9) | −0.0033 (8) | −0.0073 (8) | −0.0009 (8) |
C22 | 0.0411 (11) | 0.0185 (10) | 0.0354 (11) | −0.0004 (8) | −0.0194 (9) | −0.0034 (8) |
C23 | 0.0407 (11) | 0.0309 (12) | 0.0303 (11) | −0.0099 (9) | −0.0111 (9) | −0.0010 (9) |
C24 | 0.0492 (12) | 0.0219 (11) | 0.0262 (10) | −0.0029 (9) | −0.0118 (9) | 0.0004 (8) |
C25 | 0.0452 (11) | 0.0205 (10) | 0.0311 (11) | −0.0060 (8) | −0.0063 (9) | −0.0053 (8) |
C26 | 0.0297 (9) | 0.0226 (10) | 0.0241 (9) | −0.0059 (7) | −0.0078 (7) | −0.0005 (8) |
C27 | 0.0437 (11) | 0.0118 (9) | 0.0399 (12) | −0.0076 (8) | −0.0094 (9) | −0.0043 (8) |
C28 | 0.0262 (9) | 0.0229 (10) | 0.0278 (10) | 0.0005 (7) | −0.0018 (7) | −0.0130 (8) |
C29 | 0.0646 (15) | 0.0284 (12) | 0.0373 (12) | −0.0170 (11) | −0.0162 (11) | −0.0054 (10) |
C30 | 0.0615 (15) | 0.0324 (13) | 0.0498 (15) | −0.0073 (11) | −0.0193 (12) | −0.0161 (11) |
C31 | 0.0568 (13) | 0.0422 (14) | 0.0259 (10) | −0.0109 (11) | −0.0146 (10) | −0.0127 (10) |
C32 | 0.0508 (12) | 0.0233 (11) | 0.0380 (12) | −0.0068 (9) | −0.0171 (10) | 0.0007 (9) |
C33 | 0.0332 (9) | 0.0189 (10) | 0.0285 (10) | −0.0001 (7) | −0.0070 (8) | −0.0086 (8) |
C34 | 0.0381 (11) | 0.0299 (12) | 0.0345 (11) | −0.0052 (8) | −0.0171 (9) | −0.0047 (9) |
C35 | 0.0401 (10) | 0.0194 (10) | 0.0284 (10) | −0.0020 (8) | −0.0088 (8) | −0.0065 (8) |
C36 | 0.0674 (16) | 0.0337 (13) | 0.0307 (12) | −0.0095 (11) | −0.0200 (11) | −0.0012 (10) |
C37 | 0.0634 (15) | 0.0233 (12) | 0.0350 (12) | 0.0021 (10) | −0.0195 (11) | 0.0006 (9) |
C38 | 0.0843 (19) | 0.0198 (12) | 0.0445 (14) | −0.0139 (12) | −0.0194 (13) | −0.0003 (10) |
C39 | 0.0642 (15) | 0.0232 (11) | 0.0452 (13) | −0.0080 (10) | −0.0248 (11) | −0.0081 (10) |
C40 | 0.0465 (12) | 0.0275 (11) | 0.0293 (11) | −0.0066 (9) | −0.0129 (9) | −0.0001 (9) |
N1 | 0.0345 (8) | 0.0207 (8) | 0.0367 (10) | −0.0052 (7) | −0.0143 (7) | −0.0040 (7) |
N2 | 0.0319 (8) | 0.0230 (9) | 0.0331 (9) | −0.0065 (7) | −0.0077 (7) | −0.0053 (7) |
N3 | 0.0394 (9) | 0.0231 (9) | 0.0317 (9) | −0.0078 (7) | −0.0095 (7) | −0.0057 (7) |
N4 | 0.0329 (8) | 0.0189 (8) | 0.0251 (8) | −0.0014 (6) | −0.0104 (6) | −0.0011 (6) |
O1 | 0.0863 (13) | 0.0273 (9) | 0.0369 (9) | −0.0142 (9) | −0.0251 (9) | −0.0016 (7) |
O2 | 0.0618 (10) | 0.0232 (8) | 0.0306 (8) | −0.0011 (7) | −0.0137 (7) | −0.0081 (6) |
O3 | 0.0711 (11) | 0.0228 (8) | 0.0325 (8) | −0.0144 (7) | −0.0210 (8) | −0.0027 (6) |
O4 | 0.0853 (13) | 0.0262 (8) | 0.0483 (10) | −0.0171 (8) | −0.0444 (10) | 0.0047 (7) |
O6 | 0.0713 (13) | 0.0618 (14) | 0.0563 (12) | −0.0114 (11) | 0.0125 (10) | −0.0432 (11) |
Cl1 | 0.0367 (3) | 0.0357 (3) | 0.0686 (4) | −0.0056 (2) | −0.0101 (3) | −0.0086 (3) |
Cl2 | 0.0448 (3) | 0.0468 (4) | 0.0390 (3) | −0.0073 (2) | −0.0180 (2) | 0.0001 (3) |
Br1 | 0.1178 (3) | 0.0486 (2) | 0.0620 (2) | −0.02256 (19) | −0.0529 (2) | 0.01801 (16) |
Br2 | 0.0942 (3) | 0.03172 (18) | 0.0806 (3) | −0.01445 (15) | −0.0456 (2) | 0.01674 (15) |
Br3 | 0.0762 (2) | 0.02706 (16) | 0.04694 (18) | −0.01038 (13) | −0.03038 (14) | 0.00904 (12) |
Br4 | 0.1405 (4) | 0.03148 (18) | 0.0678 (2) | −0.01640 (18) | −0.0608 (2) | 0.01534 (15) |
Fe1 | 0.04282 (19) | 0.01812 (17) | 0.03405 (19) | −0.00424 (12) | −0.01543 (14) | −0.00315 (13) |
Fe2 | 0.0534 (2) | 0.01874 (17) | 0.03040 (18) | −0.00679 (13) | −0.01992 (14) | 0.00041 (13) |
O5 | 0.0582 (11) | 0.0463 (11) | 0.0461 (10) | 0.0063 (8) | −0.0086 (8) | −0.0235 (9) |
Geometric parameters (Å, º) top
C1—O1 | 1.312 (3) | C25—C26 | 1.416 (3) |
C1—C2 | 1.412 (3) | C25—H25 | 0.9300 |
C1—C6 | 1.423 (3) | C26—C27 | 1.421 (3) |
C2—C3 | 1.362 (4) | C27—N3 | 1.287 (3) |
C2—H2 | 0.9300 | C27—H27 | 0.9300 |
C3—C4 | 1.404 (4) | C28—C33 | 1.390 (3) |
C3—H3 | 0.9300 | C28—C29 | 1.403 (3) |
C4—C5 | 1.330 (4) | C28—N3 | 1.430 (3) |
C4—Br1 | 1.905 (3) | C29—C30 | 1.359 (4) |
C5—C6 | 1.425 (4) | C29—H29 | 0.9300 |
C5—H5 | 0.9300 | C30—C31 | 1.372 (4) |
C6—C7 | 1.412 (3) | C30—H30 | 0.9300 |
C7—N1 | 1.304 (3) | C31—C32 | 1.366 (4) |
C7—H7 | 0.9300 | C31—H31 | 0.9300 |
C8—C13 | 1.387 (3) | C32—C33 | 1.394 (3) |
C8—C9 | 1.395 (3) | C32—H32 | 0.9300 |
C8—N1 | 1.415 (3) | C33—N4 | 1.436 (3) |
C9—C10 | 1.368 (4) | C34—N4 | 1.290 (3) |
C9—H9 | 0.9300 | C34—C35 | 1.423 (3) |
C10—C11 | 1.360 (4) | C34—H34 | 0.9300 |
C10—H10 | 0.9300 | C35—C36 | 1.412 (3) |
C11—C12 | 1.397 (4) | C35—C40 | 1.412 (3) |
C11—H11 | 0.9300 | C36—C37 | 1.383 (4) |
C12—C13 | 1.395 (3) | C36—H36 | 0.9300 |
C12—H12 | 0.9300 | C37—C38 | 1.388 (4) |
C13—N2 | 1.415 (3) | C37—Br4 | 1.878 (2) |
C14—N2 | 1.290 (3) | C38—C39 | 1.371 (4) |
C14—C15 | 1.424 (3) | C38—H38 | 0.9300 |
C14—H14 | 0.9300 | C39—C40 | 1.396 (3) |
C15—C16 | 1.398 (3) | C39—H39 | 0.9300 |
C15—C20 | 1.400 (3) | C40—O4 | 1.312 (3) |
C16—C17 | 1.342 (4) | C41—O6 | 1.195 (8) |
C16—H16 | 0.9300 | C41—N5 | 1.413 (9) |
C17—C18 | 1.374 (4) | C41—H41 | 0.9300 |
C17—Br2 | 1.898 (3) | C42—N5 | 1.532 (9) |
C18—C19 | 1.377 (4) | C43—N5 | 1.446 (9) |
C18—H18 | 0.9300 | N1—Fe1 | 2.0918 (19) |
C19—C20 | 1.386 (3) | N2—Fe1 | 2.0715 (19) |
C19—H19 | 0.9300 | N3—Fe2 | 2.1215 (19) |
C20—O2 | 1.335 (3) | N4—Fe2 | 2.0974 (17) |
C21—O3 | 1.309 (3) | O1—Fe1 | 1.8775 (18) |
C21—C22 | 1.393 (3) | O2—Fe1 | 1.8834 (17) |
C21—C26 | 1.415 (3) | O3—Fe2 | 1.8956 (17) |
C22—C23 | 1.368 (3) | O4—Fe2 | 1.8904 (18) |
C22—H22 | 0.9300 | Cl1—Fe1 | 2.2356 (8) |
C23—C24 | 1.382 (3) | Cl2—Fe2 | 2.3926 (8) |
C23—H23 | 0.9300 | Fe2—O5 | 2.142 (2) |
C24—C25 | 1.360 (3) | O5—HO51 | 0.943 (2) |
C24—Br3 | 1.909 (2) | O5—HO52 | 0.7897 (17) |
| | | |
O1—C1—C2 | 118.7 (2) | C30—C29—H29 | 119.6 |
O1—C1—C6 | 122.1 (2) | C28—C29—H29 | 119.6 |
C2—C1—C6 | 119.3 (2) | C29—C30—C31 | 119.7 (2) |
C3—C2—C1 | 119.9 (3) | C29—C30—H30 | 120.1 |
C3—C2—H2 | 120.1 | C31—C30—H30 | 120.1 |
C1—C2—H2 | 120.1 | C32—C31—C30 | 121.4 (2) |
C2—C3—C4 | 120.3 (3) | C32—C31—H31 | 119.3 |
C2—C3—H3 | 119.9 | C30—C31—H31 | 119.3 |
C4—C3—H3 | 119.9 | C31—C32—C33 | 119.5 (2) |
C5—C4—C3 | 121.6 (3) | C31—C32—H32 | 120.3 |
C5—C4—Br1 | 120.5 (2) | C33—C32—H32 | 120.3 |
C3—C4—Br1 | 117.8 (2) | C28—C33—C32 | 119.82 (19) |
C4—C5—C6 | 120.2 (2) | C28—C33—N4 | 116.40 (18) |
C4—C5—H5 | 119.9 | C32—C33—N4 | 123.8 (2) |
C6—C5—H5 | 119.9 | N4—C34—C35 | 125.9 (2) |
C7—C6—C1 | 122.7 (2) | N4—C34—H34 | 117.1 |
C7—C6—C5 | 118.9 (2) | C35—C34—H34 | 117.1 |
C1—C6—C5 | 118.4 (2) | C36—C35—C40 | 118.9 (2) |
N1—C7—C6 | 126.3 (2) | C36—C35—C34 | 115.8 (2) |
N1—C7—H7 | 116.8 | C40—C35—C34 | 125.2 (2) |
C6—C7—H7 | 116.8 | C37—C36—C35 | 120.5 (2) |
C13—C8—C9 | 119.6 (2) | C37—C36—H36 | 119.8 |
C13—C8—N1 | 115.64 (19) | C35—C36—H36 | 119.8 |
C9—C8—N1 | 124.8 (2) | C36—C37—C38 | 120.1 (2) |
C10—C9—C8 | 119.6 (2) | C36—C37—Br4 | 120.4 (2) |
C10—C9—H9 | 120.2 | C38—C37—Br4 | 119.45 (19) |
C8—C9—H9 | 120.2 | C39—C38—C37 | 120.2 (2) |
C11—C10—C9 | 121.4 (2) | C39—C38—H38 | 119.9 |
C11—C10—H10 | 119.3 | C37—C38—H38 | 119.9 |
C9—C10—H10 | 119.3 | C38—C39—C40 | 121.4 (2) |
C10—C11—C12 | 120.3 (3) | C38—C39—H39 | 119.3 |
C10—C11—H11 | 119.9 | C40—C39—H39 | 119.3 |
C12—C11—H11 | 119.9 | O4—C40—C39 | 118.3 (2) |
C13—C12—C11 | 118.8 (2) | O4—C40—C35 | 122.7 (2) |
C13—C12—H12 | 120.6 | C39—C40—C35 | 118.9 (2) |
C11—C12—H12 | 120.6 | O6—C41—N5 | 112.4 (7) |
C8—C13—C12 | 120.2 (2) | O6—C41—H41 | 123.8 |
C8—C13—N2 | 115.5 (2) | N5—C41—H41 | 123.8 |
C12—C13—N2 | 124.3 (2) | C7—N1—C8 | 121.9 (2) |
N2—C14—C15 | 126.1 (2) | C7—N1—Fe1 | 124.31 (16) |
N2—C14—H14 | 117.0 | C8—N1—Fe1 | 113.53 (14) |
C15—C14—H14 | 117.0 | C14—N2—C13 | 121.24 (19) |
C16—C15—C20 | 118.0 (2) | C14—N2—Fe1 | 124.46 (15) |
C16—C15—C14 | 118.8 (2) | C13—N2—Fe1 | 114.22 (14) |
C20—C15—C14 | 123.2 (2) | C27—N3—C28 | 121.71 (18) |
C17—C16—C15 | 121.9 (2) | C27—N3—Fe2 | 124.09 (15) |
C17—C16—H16 | 119.0 | C28—N3—Fe2 | 114.14 (14) |
C15—C16—H16 | 119.0 | C34—N4—C33 | 121.51 (18) |
C16—C17—C18 | 120.5 (2) | C34—N4—Fe2 | 123.88 (15) |
C16—C17—Br2 | 120.8 (2) | C33—N4—Fe2 | 114.56 (13) |
C18—C17—Br2 | 118.71 (19) | C41—N5—C43 | 124.5 (6) |
C17—C18—C19 | 119.3 (2) | C41—N5—C42 | 108.4 (6) |
C17—C18—H18 | 120.4 | C43—N5—C42 | 127.1 (6) |
C19—C18—H18 | 120.4 | C1—O1—Fe1 | 132.97 (16) |
C18—C19—C20 | 121.3 (3) | C20—O2—Fe1 | 130.20 (14) |
C18—C19—H19 | 119.4 | C21—O3—Fe2 | 133.71 (14) |
C20—C19—H19 | 119.4 | C40—O4—Fe2 | 131.79 (15) |
O2—C20—C19 | 119.7 (2) | O1—Fe1—O2 | 90.84 (8) |
O2—C20—C15 | 121.3 (2) | O1—Fe1—N2 | 148.96 (8) |
C19—C20—C15 | 119.0 (2) | O2—Fe1—N2 | 87.64 (8) |
O3—C21—C22 | 120.1 (2) | O1—Fe1—N1 | 87.32 (8) |
O3—C21—C26 | 122.0 (2) | O2—Fe1—N1 | 147.03 (8) |
C22—C21—C26 | 117.9 (2) | N2—Fe1—N1 | 77.55 (7) |
C23—C22—C21 | 122.8 (2) | O1—Fe1—Cl1 | 111.18 (7) |
C23—C22—H22 | 118.6 | O2—Fe1—Cl1 | 107.73 (6) |
C21—C22—H22 | 118.6 | N2—Fe1—Cl1 | 98.75 (5) |
C22—C23—C24 | 118.5 (2) | N1—Fe1—Cl1 | 103.58 (6) |
C22—C23—H23 | 120.7 | O4—Fe2—O3 | 102.19 (7) |
C24—C23—H23 | 120.7 | O4—Fe2—N4 | 90.25 (7) |
C25—C24—C23 | 121.8 (2) | O3—Fe2—N4 | 165.61 (7) |
C25—C24—Br3 | 119.87 (17) | O4—Fe2—N3 | 167.63 (8) |
C23—C24—Br3 | 118.29 (17) | O3—Fe2—N3 | 88.70 (7) |
C24—C25—C26 | 120.0 (2) | N4—Fe2—N3 | 78.25 (7) |
C24—C25—H25 | 120.0 | O4—Fe2—O5 | 89.77 (9) |
C26—C25—H25 | 120.0 | O3—Fe2—O5 | 89.61 (8) |
C21—C26—C25 | 119.00 (19) | N4—Fe2—O5 | 83.17 (7) |
C21—C26—C27 | 124.85 (19) | N3—Fe2—O5 | 84.39 (8) |
C25—C26—C27 | 116.15 (19) | O4—Fe2—Cl2 | 95.34 (7) |
N3—C27—C26 | 126.34 (19) | O3—Fe2—Cl2 | 98.30 (6) |
N3—C27—H27 | 116.8 | N4—Fe2—Cl2 | 87.56 (5) |
C26—C27—H27 | 116.8 | N3—Fe2—Cl2 | 88.78 (6) |
C33—C28—C29 | 118.7 (2) | O5—Fe2—Cl2 | 169.44 (6) |
C33—C28—N3 | 116.27 (18) | Fe2—O5—HO51 | 112.99 (14) |
C29—C28—N3 | 124.9 (2) | Fe2—O5—HO52 | 118.32 (19) |
C30—C29—C28 | 120.8 (2) | HO51—O5—HO52 | 105.8 (2) |
| | | |
O1—C1—C2—C3 | 178.8 (3) | C9—C8—N1—C7 | 7.6 (3) |
C6—C1—C2—C3 | −1.4 (4) | C13—C8—N1—Fe1 | 13.5 (2) |
C1—C2—C3—C4 | −1.9 (5) | C9—C8—N1—Fe1 | −166.89 (17) |
C2—C3—C4—C5 | 5.9 (5) | C15—C14—N2—C13 | 178.2 (2) |
C2—C3—C4—Br1 | −177.7 (2) | C15—C14—N2—Fe1 | 1.8 (3) |
C3—C4—C5—C6 | −6.4 (4) | C8—C13—N2—C14 | 169.0 (2) |
Br1—C4—C5—C6 | 177.39 (18) | C12—C13—N2—C14 | −12.5 (3) |
O1—C1—C6—C7 | 2.5 (4) | C8—C13—N2—Fe1 | −14.3 (2) |
C2—C1—C6—C7 | −177.3 (2) | C12—C13—N2—Fe1 | 164.27 (19) |
O1—C1—C6—C5 | −179.2 (2) | C26—C27—N3—C28 | −179.32 (19) |
C2—C1—C6—C5 | 1.0 (3) | C26—C27—N3—Fe2 | −2.4 (3) |
C4—C5—C6—C7 | −178.8 (2) | C33—C28—N3—C27 | 179.25 (19) |
C4—C5—C6—C1 | 2.9 (4) | C29—C28—N3—C27 | 2.6 (3) |
C1—C6—C7—N1 | −6.6 (3) | C33—C28—N3—Fe2 | 2.1 (2) |
C5—C6—C7—N1 | 175.2 (2) | C29—C28—N3—Fe2 | −174.63 (18) |
C13—C8—C9—C10 | −0.5 (3) | C35—C34—N4—C33 | −178.0 (2) |
N1—C8—C9—C10 | 179.9 (2) | C35—C34—N4—Fe2 | −0.7 (3) |
C8—C9—C10—C11 | −1.7 (4) | C28—C33—N4—C34 | 171.31 (18) |
C9—C10—C11—C12 | 2.3 (4) | C32—C33—N4—C34 | −7.5 (3) |
C10—C11—C12—C13 | −0.7 (4) | C28—C33—N4—Fe2 | −6.3 (2) |
C9—C8—C13—C12 | 2.1 (3) | C32—C33—N4—Fe2 | 174.88 (17) |
N1—C8—C13—C12 | −178.2 (2) | O6—C41—N5—C43 | −18.1 (10) |
C9—C8—C13—N2 | −179.28 (18) | O6—C41—N5—C42 | 162.2 (6) |
N1—C8—C13—N2 | 0.4 (3) | C2—C1—O1—Fe1 | −162.2 (2) |
C11—C12—C13—C8 | −1.5 (4) | C6—C1—O1—Fe1 | 18.1 (4) |
C11—C12—C13—N2 | −180.0 (2) | C19—C20—O2—Fe1 | 152.41 (19) |
N2—C14—C15—C16 | −170.1 (2) | C15—C20—O2—Fe1 | −28.0 (3) |
N2—C14—C15—C20 | 10.4 (4) | C22—C21—O3—Fe2 | −173.87 (17) |
C20—C15—C16—C17 | −4.0 (4) | C26—C21—O3—Fe2 | 3.7 (3) |
C14—C15—C16—C17 | 176.4 (2) | C39—C40—O4—Fe2 | −176.7 (2) |
C15—C16—C17—C18 | 3.8 (4) | C35—C40—O4—Fe2 | 5.9 (4) |
C15—C16—C17—Br2 | −176.38 (19) | C1—O1—Fe1—O2 | −170.6 (3) |
C16—C17—C18—C19 | −1.3 (4) | C1—O1—Fe1—N2 | −83.8 (3) |
Br2—C17—C18—C19 | 178.92 (19) | C1—O1—Fe1—N1 | −23.5 (3) |
C17—C18—C19—C20 | −0.9 (4) | C1—O1—Fe1—Cl1 | 80.0 (3) |
C18—C19—C20—O2 | −179.8 (2) | C20—O2—Fe1—O1 | 179.5 (2) |
C18—C19—C20—C15 | 0.6 (4) | C20—O2—Fe1—N2 | 30.5 (2) |
C16—C15—C20—O2 | −177.8 (2) | C20—O2—Fe1—N1 | 93.1 (2) |
C14—C15—C20—O2 | 1.7 (3) | C20—O2—Fe1—Cl1 | −68.0 (2) |
C16—C15—C20—C19 | 1.8 (3) | C14—N2—Fe1—O1 | −104.5 (2) |
C14—C15—C20—C19 | −178.7 (2) | C13—N2—Fe1—O1 | 78.9 (2) |
O3—C21—C22—C23 | 177.6 (2) | C14—N2—Fe1—O2 | −16.76 (19) |
C26—C21—C22—C23 | −0.2 (3) | C13—N2—Fe1—O2 | 166.59 (15) |
C21—C22—C23—C24 | −0.2 (3) | C14—N2—Fe1—N1 | −167.10 (19) |
C22—C23—C24—C25 | 0.5 (4) | C13—N2—Fe1—N1 | 16.25 (14) |
C22—C23—C24—Br3 | −178.52 (17) | C14—N2—Fe1—Cl1 | 90.82 (18) |
C23—C24—C25—C26 | −0.5 (3) | C13—N2—Fe1—Cl1 | −85.83 (14) |
Br3—C24—C25—C26 | 178.52 (16) | C7—N1—Fe1—O1 | 17.02 (19) |
O3—C21—C26—C25 | −177.5 (2) | C8—N1—Fe1—O1 | −168.69 (15) |
C22—C21—C26—C25 | 0.2 (3) | C7—N1—Fe1—O2 | 104.4 (2) |
O3—C21—C26—C27 | 1.5 (3) | C8—N1—Fe1—O2 | −81.27 (19) |
C22—C21—C26—C27 | 179.2 (2) | C7—N1—Fe1—N2 | 169.74 (19) |
C24—C25—C26—C21 | 0.2 (3) | C8—N1—Fe1—N2 | −15.97 (13) |
C24—C25—C26—C27 | −179.0 (2) | C7—N1—Fe1—Cl1 | −94.13 (18) |
C21—C26—C27—N3 | −1.8 (3) | C8—N1—Fe1—Cl1 | 80.17 (13) |
C25—C26—C27—N3 | 177.3 (2) | C40—O4—Fe2—O3 | 166.6 (2) |
C33—C28—C29—C30 | 2.2 (4) | C40—O4—Fe2—N4 | −6.2 (2) |
N3—C28—C29—C30 | 178.9 (2) | C40—O4—Fe2—N3 | 15.3 (6) |
C28—C29—C30—C31 | −2.8 (4) | C40—O4—Fe2—O5 | 77.0 (2) |
C29—C30—C31—C32 | 2.7 (4) | C40—O4—Fe2—Cl2 | −93.7 (2) |
C30—C31—C32—C33 | −1.9 (4) | C21—O3—Fe2—O4 | −179.9 (2) |
C29—C28—C33—C32 | −1.5 (3) | C21—O3—Fe2—N4 | −30.5 (4) |
N3—C28—C33—C32 | −178.37 (19) | C21—O3—Fe2—N3 | −5.8 (2) |
C29—C28—C33—N4 | 179.63 (19) | C21—O3—Fe2—O5 | −90.2 (2) |
N3—C28—C33—N4 | 2.7 (3) | C21—O3—Fe2—Cl2 | 82.8 (2) |
C31—C32—C33—C28 | 1.3 (3) | C34—N4—Fe2—O4 | 3.41 (18) |
C31—C32—C33—N4 | −179.9 (2) | C33—N4—Fe2—O4 | −179.09 (14) |
N4—C34—C35—C36 | −178.6 (2) | C34—N4—Fe2—O3 | −146.7 (3) |
N4—C34—C35—C40 | −1.5 (4) | C33—N4—Fe2—O3 | 30.8 (4) |
C40—C35—C36—C37 | 2.1 (4) | C34—N4—Fe2—N3 | −172.00 (18) |
C34—C35—C36—C37 | 179.3 (2) | C33—N4—Fe2—N3 | 5.50 (13) |
C35—C36—C37—C38 | −2.0 (4) | C34—N4—Fe2—O5 | −86.34 (17) |
C35—C36—C37—Br4 | −178.25 (19) | C33—N4—Fe2—O5 | 91.16 (14) |
C36—C37—C38—C39 | 1.1 (5) | C34—N4—Fe2—Cl2 | 98.74 (17) |
Br4—C37—C38—C39 | 177.4 (2) | C33—N4—Fe2—Cl2 | −83.76 (13) |
C37—C38—C39—C40 | −0.4 (5) | C27—N3—Fe2—O4 | 156.8 (4) |
C38—C39—C40—O4 | −177.0 (3) | C28—N3—Fe2—O4 | −26.0 (5) |
C38—C39—C40—C35 | 0.5 (4) | C27—N3—Fe2—O3 | 4.88 (18) |
C36—C35—C40—O4 | 176.1 (2) | C28—N3—Fe2—O3 | −178.00 (14) |
C34—C35—C40—O4 | −0.9 (4) | C27—N3—Fe2—N4 | 178.78 (18) |
C36—C35—C40—C39 | −1.3 (3) | C28—N3—Fe2—N4 | −4.10 (13) |
C34—C35—C40—C39 | −178.2 (2) | C27—N3—Fe2—O5 | 94.61 (18) |
C6—C7—N1—C8 | 179.27 (18) | C28—N3—Fe2—O5 | −88.27 (14) |
C6—C7—N1—Fe1 | −6.9 (3) | C27—N3—Fe2—Cl2 | −93.45 (17) |
C13—C8—N1—C7 | −172.1 (2) | C28—N3—Fe2—Cl2 | 83.67 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Cl1i | 0.93 (1) | 2.75 (1) | 3.654 (2) | 165 (1) |
C12—H12···Cl2ii | 0.93 (1) | 2.74 (1) | 3.643 (3) | 163 (1) |
C14—H14···Cl2ii | 0.93 (1) | 2.63 (1) | 3.537 (3) | 165 (1) |
C16—H16···Cl2ii | 0.93 (1) | 2.94 (1) | 3.777 (4) | 150 (1) |
C32—H32···Cl2iii | 0.93 (1) | 2.74 (1) | 3.648 (2) | 167 (1) |
C34—H34···Cl2iii | 0.93 (1) | 2.86 (1) | 3.731 (3) | 156 (1) |
C2—H2···O6iv | 0.93 (1) | 2.44 (1) | 3.332 (4) | 161 (1) |
C14—H14···O3ii | 0.93 (1) | 2.92 (1) | 3.364 (3) | 111 (1) |
C41—H41···O5 | 0.93 (1) | 2.75 (1) | 3.062 (10) | 101 (1) |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z. |
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