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Two new CoII complexes, namely bis{N-[(6-bromopyridin-2-yl)methylidene]-2-[6-ethylamino-3-(ethyliminiumyl)-2,7-dimethyl-3H-xanthen-9-yl]benzene-1-carbohydrazonate}cobalt(II) bis(perchlorate)–dichloromethane–methanol (1/1/2), [Co(C32H30BrN5O2)2](ClO4)2·CH2Cl2·2CH3OH or [CoII(L)2](ClO4)2·CH2Cl2·2CH3OH, (1), and the bis(tetrafluoridoborate) salt, [Co(C32H30BrN5O2)2](BF4)2·CH2Cl2·2CH3OH or [CoII(L)2](BF4)2·CH2Cl2·2CH3OH, (2) (L is commonly 6-bromopyridine-2-carbaldehyde rhodamine 6G hydrazone), have been successfully constructed and characterized. The crystal structure analysis revealed that complexes (1) and (2) are mononuclear and have a CoIIN4O2 distorted octahedral structure. The large π-conjugated xanthene moiety of the L ligand causes strong intermolecular π–π stacking interactions, yielding a supramolecular one-dimensional chain. Complexes (1) and (2) display an obvious fluorescence emission near 560 nm in the solid state. Magnetic investigations show that both (1) and (2) are paramagnetic, dominated by the structural distortion and spin-orbit coupling of CoII.
Supporting information
CCDC references: 1876890; 1876889
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2017); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Bis{
N-[(6-bromopyridin-2-yl)methylidene]-2-[6-ethylamino-3-(ethyliminiumyl)-2,7-dimethyl-3
H-xanthen-9-yl]benzene-1-carbohydrazonate}cobalt(II) bis(perchlorate)–dichloromethane –methanol
(1/1/2) (1)
top
Crystal data top
[Co(C32H30BrN5O2)2](ClO4)2·CH2Cl2·2CH4O | Z = 2 |
Mr = 1599.88 | F(000) = 1638 |
Triclinic, P1 | Dx = 1.522 Mg m−3 |
a = 13.2358 (5) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 16.3228 (5) Å | Cell parameters from 11414 reflections |
c = 17.8925 (5) Å | θ = 4.2–76.2° |
α = 95.741 (2)° | µ = 5.27 mm−1 |
β = 107.412 (3)° | T = 100 K |
γ = 105.197 (3)° | Block, clear orange |
V = 3492.0 (2) Å3 | 0.3 × 0.2 × 0.1 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an AtlasS2 detector | 14225 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 12089 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.049 |
Detector resolution: 5.2137 pixels mm-1 | θmax = 76.7°, θmin = 3.5° |
ω scans | h = −13→16 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017) | k = −19→20 |
Tmin = 0.500, Tmax = 1.000 | l = −18→22 |
25181 measured reflections | |
Refinement top
Refinement on F2 | 12 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.193 | w = 1/[σ2(Fo2) + (0.1212P)2 + 3.469P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
14225 reflections | Δρmax = 1.78 e Å−3 |
895 parameters | Δρmin = −1.14 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br2 | 0.14066 (4) | 0.57606 (3) | 0.51810 (2) | 0.02860 (12) | |
Br1 | 0.51541 (4) | 0.53924 (3) | 0.59296 (4) | 0.04488 (16) | |
Co1 | 0.26263 (5) | 0.41997 (4) | 0.61822 (3) | 0.01808 (14) | |
Cl2 | −0.21369 (12) | 0.28710 (8) | 0.08614 (6) | 0.0439 (3) | |
Cl1 | 0.73900 (10) | −0.10611 (8) | 0.73138 (8) | 0.0442 (3) | |
Cl3 | 0.69813 (14) | 0.38377 (10) | 0.65157 (13) | 0.0707 (5) | |
Cl4 | 0.63309 (18) | 0.22925 (14) | 0.52976 (13) | 0.0800 (5) | |
O1 | 0.1241 (2) | 0.31703 (17) | 0.60352 (15) | 0.0237 (5) | |
O2 | 0.3755 (2) | 0.39020 (17) | 0.70893 (15) | 0.0239 (5) | |
O3 | 0.1278 (2) | 0.08515 (17) | 0.47006 (15) | 0.0233 (5) | |
O4 | 0.4141 (2) | 0.54204 (17) | 0.92365 (16) | 0.0270 (6) | |
N2 | 0.1840 (3) | 0.4661 (2) | 0.68726 (17) | 0.0202 (6) | |
N5 | 0.3182 (3) | 0.3346 (2) | 0.56242 (18) | 0.0208 (6) | |
N4 | 0.2023 (3) | 0.4303 (2) | 0.49141 (17) | 0.0210 (6) | |
N1 | 0.3657 (3) | 0.5546 (2) | 0.66741 (18) | 0.0215 (6) | |
N6 | 0.3823 (3) | 0.2922 (2) | 0.60836 (18) | 0.0232 (6) | |
N3 | 0.0930 (3) | 0.4102 (2) | 0.69559 (18) | 0.0210 (6) | |
O14 | −0.1518 (4) | 0.3107 (3) | 0.1706 (2) | 0.0553 (11) | |
N8 | 0.3628 (3) | −0.0082 (2) | 0.6749 (2) | 0.0275 (7) | |
H8 | 0.3872 | −0.0094 | 0.7250 | 0.033* | |
O10 | 0.8443 (3) | −0.0422 (2) | 0.7537 (3) | 0.0472 (9) | |
N10 | 0.0722 (3) | 0.3576 (2) | 0.9200 (2) | 0.0332 (8) | |
H10 | 0.0324 | 0.3054 | 0.9161 | 0.040* | |
C7 | 0.0720 (3) | 0.3330 (2) | 0.6495 (2) | 0.0202 (7) | |
C14 | 0.0303 (3) | 0.1482 (2) | 0.5732 (2) | 0.0205 (7) | |
C39 | 0.4063 (3) | 0.3281 (2) | 0.6847 (2) | 0.0212 (7) | |
C5 | 0.3284 (3) | 0.5946 (2) | 0.7194 (2) | 0.0213 (7) | |
C8 | −0.0170 (3) | 0.2604 (2) | 0.6570 (2) | 0.0204 (7) | |
N7 | −0.0881 (4) | 0.1730 (3) | 0.2503 (2) | 0.0365 (8) | |
H7 | −0.1443 | 0.1909 | 0.2306 | 0.044* | |
C58 | 0.3711 (3) | 0.3889 (2) | 0.8758 (2) | 0.0226 (7) | |
C46 | 0.4673 (3) | 0.4035 (2) | 0.8561 (2) | 0.0224 (7) | |
C13 | −0.0304 (3) | 0.1744 (2) | 0.6250 (2) | 0.0195 (6) | |
C21 | 0.1636 (3) | 0.0805 (2) | 0.5488 (2) | 0.0218 (7) | |
C6 | 0.2283 (3) | 0.5429 (2) | 0.7303 (2) | 0.0220 (7) | |
H6 | 0.1981 | 0.5638 | 0.7660 | 0.026* | |
C26 | 0.1168 (3) | 0.1125 (2) | 0.6023 (2) | 0.0197 (6) | |
O5 | −0.0996 (4) | 0.2136 (3) | 0.9305 (3) | 0.0642 (13) | |
H5 | −0.1299 | 0.2327 | 0.9589 | 0.096* | |
C47 | 0.5392 (3) | 0.4900 (2) | 0.8710 (2) | 0.0243 (7) | |
N9 | 0.7355 (4) | 0.7490 (3) | 0.9192 (3) | 0.0417 (9) | |
H9 | 0.7969 | 0.7599 | 0.9093 | 0.050* | |
C15 | −0.0069 (3) | 0.1513 (2) | 0.4911 (2) | 0.0205 (7) | |
C54 | 0.2454 (4) | 0.4517 (3) | 0.9208 (2) | 0.0269 (7) | |
H54 | 0.2303 | 0.5006 | 0.9402 | 0.032* | |
C37 | 0.2100 (3) | 0.3622 (2) | 0.4443 (2) | 0.0239 (7) | |
C53 | 0.3423 (3) | 0.4600 (2) | 0.9064 (2) | 0.0227 (7) | |
C45 | 0.5034 (3) | 0.3304 (2) | 0.8281 (2) | 0.0222 (7) | |
C24 | 0.2464 (3) | 0.0694 (2) | 0.7086 (2) | 0.0237 (7) | |
C23 | 0.2871 (3) | 0.0333 (2) | 0.6512 (2) | 0.0243 (7) | |
C19 | 0.0173 (3) | 0.1239 (2) | 0.3608 (2) | 0.0261 (7) | |
H19 | 0.0527 | 0.1017 | 0.3297 | 0.031* | |
C40 | 0.4754 (3) | 0.2929 (2) | 0.7474 (2) | 0.0220 (7) | |
C4 | 0.3850 (3) | 0.6792 (2) | 0.7605 (2) | 0.0241 (7) | |
H4 | 0.3596 | 0.7047 | 0.7971 | 0.029* | |
C57 | 0.2915 (3) | 0.3055 (2) | 0.8630 (2) | 0.0222 (7) | |
H57 | 0.3068 | 0.2569 | 0.8435 | 0.027* | |
C52 | 0.5097 (3) | 0.5573 (2) | 0.9060 (2) | 0.0246 (7) | |
C25 | 0.1639 (3) | 0.1063 (2) | 0.6836 (2) | 0.0225 (7) | |
H25 | 0.1372 | 0.1284 | 0.7211 | 0.027* | |
C38 | 0.2785 (3) | 0.3121 (2) | 0.4858 (2) | 0.0224 (7) | |
H38 | 0.2924 | 0.2670 | 0.4585 | 0.027* | |
C33 | 0.1418 (3) | 0.4765 (2) | 0.4546 (2) | 0.0237 (7) | |
C20 | 0.0448 (3) | 0.1200 (2) | 0.4409 (2) | 0.0226 (7) | |
C1 | 0.4583 (3) | 0.5992 (3) | 0.6582 (2) | 0.0273 (8) | |
O6 | 0.4925 (5) | −0.0476 (4) | 0.8219 (3) | 0.0765 (17) | |
H6A | 0.5493 | −0.0229 | 0.8134 | 0.115* | |
C55 | 0.1677 (3) | 0.3692 (3) | 0.9066 (2) | 0.0258 (7) | |
C17 | −0.1218 (3) | 0.1917 (2) | 0.3751 (2) | 0.0246 (7) | |
C9 | −0.0847 (3) | 0.2773 (3) | 0.6991 (2) | 0.0256 (7) | |
H9A | −0.0762 | 0.3342 | 0.7197 | 0.031* | |
C22 | 0.2452 (3) | 0.0411 (2) | 0.5707 (2) | 0.0231 (7) | |
H22 | 0.2723 | 0.0199 | 0.5331 | 0.028* | |
C56 | 0.1952 (3) | 0.2945 (2) | 0.8782 (2) | 0.0242 (7) | |
C36 | 0.1561 (3) | 0.3417 (3) | 0.3621 (2) | 0.0286 (8) | |
H36 | 0.1644 | 0.2962 | 0.3313 | 0.034* | |
C18 | −0.0641 (3) | 0.1615 (3) | 0.3272 (2) | 0.0269 (8) | |
C48 | 0.6363 (3) | 0.5138 (3) | 0.8508 (2) | 0.0281 (8) | |
H48 | 0.6577 | 0.4708 | 0.8273 | 0.034* | |
C16 | −0.0924 (3) | 0.1862 (2) | 0.4540 (2) | 0.0230 (7) | |
H16 | −0.1300 | 0.2062 | 0.4846 | 0.028* | |
C2 | 0.5189 (4) | 0.6850 (3) | 0.6944 (3) | 0.0326 (9) | |
H2 | 0.5824 | 0.7137 | 0.6841 | 0.039* | |
C3 | 0.4797 (4) | 0.7252 (3) | 0.7466 (2) | 0.0304 (8) | |
H3 | 0.5165 | 0.7826 | 0.7721 | 0.036* | |
C27 | −0.2118 (3) | 0.2303 (3) | 0.3381 (2) | 0.0294 (8) | |
H27A | −0.1810 | 0.2805 | 0.3189 | 0.044* | |
H27B | −0.2426 | 0.2466 | 0.3774 | 0.044* | |
H27C | −0.2693 | 0.1884 | 0.2944 | 0.044* | |
C44 | 0.5696 (3) | 0.2985 (3) | 0.8875 (2) | 0.0291 (8) | |
H44 | 0.5881 | 0.3227 | 0.9410 | 0.035* | |
C62 | 0.1129 (3) | 0.2068 (3) | 0.8657 (2) | 0.0268 (7) | |
H62A | 0.0467 | 0.2010 | 0.8220 | 0.040* | |
H62B | 0.0946 | 0.2005 | 0.9133 | 0.040* | |
H62C | 0.1450 | 0.1628 | 0.8540 | 0.040* | |
C41 | 0.5132 (3) | 0.2244 (2) | 0.7280 (2) | 0.0247 (7) | |
H41 | 0.4940 | 0.1991 | 0.6747 | 0.030* | |
C10 | −0.1647 (3) | 0.2105 (3) | 0.7108 (3) | 0.0285 (8) | |
H10A | −0.2098 | 0.2227 | 0.7387 | 0.034* | |
C12 | −0.1101 (3) | 0.1073 (2) | 0.6385 (2) | 0.0249 (7) | |
H12 | −0.1183 | 0.0501 | 0.6189 | 0.030* | |
C49 | 0.7005 (4) | 0.5989 (3) | 0.8646 (3) | 0.0326 (9) | |
C34 | 0.0815 (3) | 0.4596 (3) | 0.3733 (2) | 0.0283 (8) | |
H34 | 0.0377 | 0.4932 | 0.3514 | 0.034* | |
C50 | 0.6698 (4) | 0.6643 (3) | 0.9032 (3) | 0.0334 (9) | |
O11 | −0.2185 (5) | 0.2024 (3) | 0.0560 (3) | 0.0781 (17) | |
C35 | 0.0897 (4) | 0.3902 (3) | 0.3264 (2) | 0.0303 (8) | |
H35 | 0.0512 | 0.3763 | 0.2717 | 0.036* | |
C30 | 0.2965 (3) | 0.0646 (3) | 0.7946 (2) | 0.0293 (8) | |
H30A | 0.2830 | 0.0051 | 0.7998 | 0.044* | |
H30B | 0.2632 | 0.0925 | 0.8261 | 0.044* | |
H30C | 0.3752 | 0.0933 | 0.8127 | 0.044* | |
C51 | 0.5744 (4) | 0.6433 (3) | 0.9234 (2) | 0.0301 (8) | |
H51 | 0.5541 | 0.6861 | 0.9483 | 0.036* | |
C11 | −0.1768 (3) | 0.1253 (3) | 0.6806 (2) | 0.0274 (8) | |
H11 | −0.2297 | 0.0802 | 0.6887 | 0.033* | |
C43 | 0.6079 (4) | 0.2310 (3) | 0.8671 (3) | 0.0319 (8) | |
H43 | 0.6528 | 0.2108 | 0.9068 | 0.038* | |
C42 | 0.5789 (4) | 0.1936 (3) | 0.7871 (3) | 0.0312 (8) | |
H42 | 0.6038 | 0.1478 | 0.7735 | 0.037* | |
O8 | 0.7534 (4) | −0.1792 (3) | 0.7687 (3) | 0.0751 (16) | |
C31 | 0.4071 (4) | −0.0513 (3) | 0.6229 (3) | 0.0317 (8) | |
H31A | 0.3478 | −0.0795 | 0.5727 | 0.038* | |
H31B | 0.4329 | −0.0958 | 0.6475 | 0.038* | |
O7 | 0.6661 (4) | −0.0731 (5) | 0.7615 (4) | 0.0877 (19) | |
O9 | 0.6895 (7) | −0.1313 (5) | 0.6492 (4) | 0.105 (2) | |
O12 | −0.1699 (6) | 0.3437 (5) | 0.0432 (3) | 0.101 (2) | |
C63 | 0.0299 (4) | 0.4276 (3) | 0.9409 (3) | 0.0372 (10) | |
H63A | 0.0911 | 0.4748 | 0.9781 | 0.045* | |
H63B | −0.0232 | 0.4069 | 0.9675 | 0.045* | |
C32 | 0.5024 (4) | 0.0098 (3) | 0.6060 (3) | 0.0412 (10) | |
H32A | 0.5296 | −0.0225 | 0.5729 | 0.062* | |
H32B | 0.5613 | 0.0384 | 0.6554 | 0.062* | |
H32C | 0.4765 | 0.0522 | 0.5790 | 0.062* | |
O13 | −0.3258 (5) | 0.2876 (5) | 0.0733 (3) | 0.0926 (19) | |
C28 | −0.0253 (4) | 0.1569 (3) | 0.1985 (3) | 0.0385 (10) | |
H28A | 0.0510 | 0.1651 | 0.2312 | 0.046* | |
H28B | −0.0244 | 0.1988 | 0.1637 | 0.046* | |
C59 | 0.8007 (4) | 0.6235 (3) | 0.8398 (3) | 0.0448 (11) | |
H59A | 0.8662 | 0.6473 | 0.8864 | 0.067* | |
H59B | 0.7944 | 0.6659 | 0.8066 | 0.067* | |
H59C | 0.8061 | 0.5732 | 0.8105 | 0.067* | |
C60 | 0.7063 (5) | 0.8204 (3) | 0.9519 (3) | 0.0476 (13) | |
H60A | 0.6966 | 0.8120 | 1.0025 | 0.057* | |
H60B | 0.6366 | 0.8230 | 0.9157 | 0.057* | |
C65 | −0.1473 (5) | 0.1242 (3) | 0.9075 (4) | 0.0483 (12) | |
H65A | −0.1200 | 0.1029 | 0.8679 | 0.072* | |
H65B | −0.2267 | 0.1104 | 0.8855 | 0.072* | |
H65C | −0.1280 | 0.0978 | 0.9531 | 0.072* | |
C64 | −0.0253 (5) | 0.4606 (4) | 0.8692 (3) | 0.0523 (14) | |
H64A | −0.0927 | 0.4167 | 0.8362 | 0.078* | |
H64B | 0.0240 | 0.4748 | 0.8393 | 0.078* | |
H64C | −0.0426 | 0.5113 | 0.8863 | 0.078* | |
C29 | −0.0738 (5) | 0.0671 (4) | 0.1483 (3) | 0.0512 (13) | |
H29A | −0.0347 | 0.0616 | 0.1116 | 0.077* | |
H29B | −0.1511 | 0.0570 | 0.1189 | 0.077* | |
H29C | −0.0665 | 0.0255 | 0.1822 | 0.077* | |
C61 | 0.7981 (6) | 0.9050 (3) | 0.9641 (4) | 0.0630 (19) | |
H61A | 0.8041 | 0.9149 | 0.9135 | 0.095* | |
H61B | 0.8675 | 0.9012 | 0.9982 | 0.095* | |
H61C | 0.7802 | 0.9519 | 0.9885 | 0.095* | |
C67 | 0.6052 (6) | 0.3245 (6) | 0.5564 (5) | 0.071 (2) | |
H67A | 0.5295 | 0.3104 | 0.5569 | 0.086* | |
H67B | 0.6110 | 0.3602 | 0.5167 | 0.086* | |
C66 | 0.5106 (9) | −0.0302 (8) | 0.9036 (5) | 0.099 (3) | |
H66A | 0.4760 | 0.0122 | 0.9147 | 0.149* | |
H66B | 0.5891 | −0.0084 | 0.9324 | 0.149* | |
H66C | 0.4791 | −0.0824 | 0.9199 | 0.149* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br2 | 0.0388 (2) | 0.0231 (2) | 0.0288 (2) | 0.01534 (16) | 0.01248 (16) | 0.00771 (15) |
Br1 | 0.0478 (3) | 0.0309 (2) | 0.0653 (3) | 0.0051 (2) | 0.0410 (2) | 0.0016 (2) |
Co1 | 0.0244 (3) | 0.0153 (3) | 0.0178 (3) | 0.0071 (2) | 0.0103 (2) | 0.0052 (2) |
Cl2 | 0.0767 (8) | 0.0488 (6) | 0.0255 (5) | 0.0428 (6) | 0.0223 (5) | 0.0138 (4) |
Cl1 | 0.0394 (5) | 0.0312 (5) | 0.0589 (7) | 0.0082 (4) | 0.0110 (5) | 0.0200 (5) |
Cl3 | 0.0624 (8) | 0.0423 (7) | 0.1186 (14) | 0.0161 (6) | 0.0473 (9) | 0.0132 (8) |
Cl4 | 0.0805 (11) | 0.0738 (12) | 0.0841 (12) | 0.0232 (9) | 0.0309 (9) | 0.0007 (9) |
O1 | 0.0294 (12) | 0.0192 (12) | 0.0251 (12) | 0.0039 (10) | 0.0162 (10) | 0.0042 (10) |
O2 | 0.0328 (13) | 0.0213 (12) | 0.0209 (11) | 0.0130 (10) | 0.0093 (10) | 0.0055 (10) |
O3 | 0.0326 (13) | 0.0211 (12) | 0.0226 (12) | 0.0141 (10) | 0.0124 (10) | 0.0071 (10) |
O4 | 0.0399 (14) | 0.0175 (12) | 0.0257 (12) | 0.0111 (11) | 0.0121 (11) | 0.0038 (10) |
N2 | 0.0262 (14) | 0.0182 (14) | 0.0189 (13) | 0.0074 (11) | 0.0100 (11) | 0.0073 (11) |
N5 | 0.0247 (14) | 0.0172 (14) | 0.0226 (14) | 0.0061 (11) | 0.0108 (11) | 0.0055 (11) |
N4 | 0.0263 (14) | 0.0197 (14) | 0.0193 (13) | 0.0055 (11) | 0.0108 (11) | 0.0085 (11) |
N1 | 0.0282 (14) | 0.0180 (14) | 0.0236 (14) | 0.0106 (12) | 0.0124 (12) | 0.0068 (11) |
N6 | 0.0286 (15) | 0.0214 (15) | 0.0226 (14) | 0.0094 (12) | 0.0106 (12) | 0.0071 (12) |
N3 | 0.0259 (14) | 0.0175 (14) | 0.0248 (14) | 0.0078 (11) | 0.0141 (11) | 0.0075 (11) |
O14 | 0.092 (3) | 0.059 (2) | 0.0264 (16) | 0.054 (2) | 0.0106 (17) | 0.0059 (15) |
N8 | 0.0328 (16) | 0.0295 (17) | 0.0262 (15) | 0.0172 (14) | 0.0113 (13) | 0.0069 (13) |
O10 | 0.0456 (18) | 0.0279 (16) | 0.079 (3) | 0.0128 (14) | 0.0318 (18) | 0.0221 (17) |
N10 | 0.0433 (19) | 0.0249 (17) | 0.0421 (19) | 0.0152 (15) | 0.0255 (16) | 0.0067 (14) |
C7 | 0.0283 (16) | 0.0154 (16) | 0.0208 (15) | 0.0092 (13) | 0.0106 (13) | 0.0074 (12) |
C14 | 0.0242 (16) | 0.0127 (15) | 0.0244 (16) | 0.0032 (12) | 0.0099 (13) | 0.0042 (12) |
C39 | 0.0269 (16) | 0.0151 (15) | 0.0252 (16) | 0.0085 (13) | 0.0115 (13) | 0.0061 (13) |
C5 | 0.0285 (17) | 0.0194 (16) | 0.0193 (15) | 0.0106 (14) | 0.0086 (13) | 0.0074 (13) |
C8 | 0.0261 (16) | 0.0165 (16) | 0.0235 (16) | 0.0103 (13) | 0.0103 (13) | 0.0095 (13) |
N7 | 0.053 (2) | 0.042 (2) | 0.0247 (16) | 0.0293 (18) | 0.0141 (15) | 0.0116 (15) |
C58 | 0.0336 (18) | 0.0186 (17) | 0.0188 (15) | 0.0107 (14) | 0.0106 (13) | 0.0052 (13) |
C46 | 0.0316 (18) | 0.0192 (16) | 0.0180 (15) | 0.0109 (14) | 0.0065 (13) | 0.0080 (12) |
C13 | 0.0238 (15) | 0.0166 (16) | 0.0233 (15) | 0.0090 (13) | 0.0111 (13) | 0.0098 (13) |
C21 | 0.0267 (16) | 0.0170 (16) | 0.0225 (16) | 0.0070 (13) | 0.0088 (13) | 0.0061 (13) |
C6 | 0.0309 (17) | 0.0185 (16) | 0.0213 (15) | 0.0119 (14) | 0.0114 (13) | 0.0049 (13) |
C26 | 0.0268 (16) | 0.0123 (14) | 0.0229 (16) | 0.0062 (13) | 0.0111 (13) | 0.0073 (12) |
O5 | 0.081 (3) | 0.036 (2) | 0.087 (3) | −0.0007 (19) | 0.067 (3) | −0.0036 (19) |
C47 | 0.0333 (18) | 0.0189 (17) | 0.0213 (16) | 0.0115 (15) | 0.0057 (14) | 0.0083 (13) |
N9 | 0.047 (2) | 0.0224 (18) | 0.053 (2) | 0.0060 (16) | 0.0134 (18) | 0.0168 (16) |
C15 | 0.0257 (16) | 0.0155 (15) | 0.0209 (16) | 0.0051 (13) | 0.0093 (13) | 0.0055 (12) |
C54 | 0.041 (2) | 0.0213 (17) | 0.0255 (17) | 0.0164 (16) | 0.0141 (15) | 0.0070 (14) |
C37 | 0.0300 (17) | 0.0217 (17) | 0.0199 (16) | 0.0037 (14) | 0.0118 (14) | 0.0045 (13) |
C53 | 0.0365 (19) | 0.0163 (16) | 0.0182 (15) | 0.0126 (14) | 0.0080 (14) | 0.0087 (12) |
C45 | 0.0255 (16) | 0.0192 (16) | 0.0250 (17) | 0.0086 (13) | 0.0103 (13) | 0.0078 (13) |
C24 | 0.0280 (17) | 0.0209 (17) | 0.0249 (17) | 0.0076 (14) | 0.0114 (14) | 0.0085 (13) |
C23 | 0.0284 (17) | 0.0183 (16) | 0.0256 (17) | 0.0066 (14) | 0.0087 (14) | 0.0046 (13) |
C19 | 0.039 (2) | 0.0218 (17) | 0.0236 (17) | 0.0148 (15) | 0.0130 (15) | 0.0066 (14) |
C40 | 0.0255 (16) | 0.0194 (16) | 0.0227 (16) | 0.0069 (13) | 0.0099 (13) | 0.0060 (13) |
C4 | 0.0348 (19) | 0.0183 (17) | 0.0216 (16) | 0.0109 (14) | 0.0098 (14) | 0.0063 (13) |
C57 | 0.0339 (18) | 0.0174 (16) | 0.0219 (15) | 0.0128 (14) | 0.0134 (14) | 0.0086 (13) |
C52 | 0.0364 (19) | 0.0198 (17) | 0.0197 (16) | 0.0116 (15) | 0.0077 (14) | 0.0102 (13) |
C25 | 0.0281 (17) | 0.0192 (16) | 0.0232 (16) | 0.0078 (14) | 0.0118 (13) | 0.0071 (13) |
C38 | 0.0299 (17) | 0.0201 (16) | 0.0193 (15) | 0.0069 (14) | 0.0118 (13) | 0.0042 (13) |
C33 | 0.0299 (17) | 0.0207 (17) | 0.0239 (17) | 0.0069 (14) | 0.0136 (14) | 0.0081 (13) |
C20 | 0.0301 (17) | 0.0133 (15) | 0.0279 (17) | 0.0085 (13) | 0.0125 (14) | 0.0058 (13) |
C1 | 0.0304 (18) | 0.0209 (18) | 0.0326 (19) | 0.0063 (15) | 0.0153 (15) | 0.0033 (15) |
O6 | 0.117 (4) | 0.112 (4) | 0.043 (2) | 0.093 (4) | 0.033 (2) | 0.030 (2) |
C55 | 0.040 (2) | 0.0241 (18) | 0.0223 (16) | 0.0167 (16) | 0.0164 (15) | 0.0071 (14) |
C17 | 0.0310 (18) | 0.0171 (16) | 0.0267 (17) | 0.0090 (14) | 0.0094 (14) | 0.0056 (13) |
C9 | 0.0328 (18) | 0.0210 (17) | 0.0300 (18) | 0.0118 (15) | 0.0160 (15) | 0.0101 (14) |
C22 | 0.0301 (17) | 0.0196 (16) | 0.0254 (17) | 0.0129 (14) | 0.0126 (14) | 0.0064 (13) |
C56 | 0.0356 (19) | 0.0210 (17) | 0.0216 (16) | 0.0124 (15) | 0.0134 (14) | 0.0068 (13) |
C36 | 0.037 (2) | 0.0268 (19) | 0.0211 (17) | 0.0082 (16) | 0.0112 (15) | 0.0027 (14) |
C18 | 0.0364 (19) | 0.0222 (18) | 0.0232 (17) | 0.0100 (15) | 0.0106 (15) | 0.0055 (14) |
C48 | 0.0349 (19) | 0.0238 (19) | 0.0275 (18) | 0.0109 (16) | 0.0097 (15) | 0.0115 (15) |
C16 | 0.0280 (17) | 0.0189 (16) | 0.0243 (16) | 0.0077 (14) | 0.0114 (14) | 0.0053 (13) |
C2 | 0.034 (2) | 0.024 (2) | 0.039 (2) | 0.0025 (16) | 0.0168 (17) | 0.0056 (16) |
C3 | 0.038 (2) | 0.0184 (17) | 0.0296 (18) | 0.0028 (15) | 0.0090 (16) | 0.0042 (14) |
C27 | 0.036 (2) | 0.029 (2) | 0.0265 (18) | 0.0157 (16) | 0.0098 (15) | 0.0083 (15) |
C44 | 0.0349 (19) | 0.030 (2) | 0.0243 (17) | 0.0173 (16) | 0.0054 (15) | 0.0076 (15) |
C62 | 0.0350 (19) | 0.0215 (18) | 0.0298 (18) | 0.0111 (15) | 0.0163 (15) | 0.0089 (14) |
C41 | 0.0309 (18) | 0.0218 (17) | 0.0254 (17) | 0.0116 (14) | 0.0115 (14) | 0.0073 (14) |
C10 | 0.0317 (18) | 0.0271 (19) | 0.038 (2) | 0.0132 (16) | 0.0226 (16) | 0.0132 (16) |
C12 | 0.0301 (18) | 0.0173 (16) | 0.0311 (18) | 0.0081 (14) | 0.0136 (14) | 0.0094 (14) |
C49 | 0.040 (2) | 0.026 (2) | 0.037 (2) | 0.0116 (17) | 0.0148 (17) | 0.0175 (16) |
C34 | 0.0306 (18) | 0.031 (2) | 0.0265 (18) | 0.0094 (16) | 0.0114 (15) | 0.0131 (15) |
C50 | 0.042 (2) | 0.0210 (19) | 0.034 (2) | 0.0079 (17) | 0.0070 (17) | 0.0152 (16) |
O11 | 0.116 (4) | 0.054 (3) | 0.048 (2) | 0.055 (3) | −0.013 (2) | −0.0075 (19) |
C35 | 0.036 (2) | 0.033 (2) | 0.0191 (16) | 0.0074 (16) | 0.0066 (14) | 0.0080 (15) |
C30 | 0.037 (2) | 0.035 (2) | 0.0253 (18) | 0.0213 (17) | 0.0135 (15) | 0.0130 (16) |
C51 | 0.042 (2) | 0.0175 (17) | 0.0269 (18) | 0.0103 (16) | 0.0050 (16) | 0.0054 (14) |
C11 | 0.0294 (18) | 0.0245 (19) | 0.0357 (19) | 0.0082 (15) | 0.0186 (15) | 0.0143 (15) |
C43 | 0.039 (2) | 0.030 (2) | 0.031 (2) | 0.0199 (17) | 0.0094 (16) | 0.0119 (16) |
C42 | 0.038 (2) | 0.0246 (19) | 0.036 (2) | 0.0160 (16) | 0.0151 (17) | 0.0064 (16) |
O8 | 0.051 (2) | 0.051 (3) | 0.105 (4) | −0.002 (2) | 0.006 (2) | 0.051 (3) |
C31 | 0.036 (2) | 0.032 (2) | 0.034 (2) | 0.0205 (17) | 0.0134 (16) | 0.0062 (16) |
O7 | 0.054 (3) | 0.133 (5) | 0.114 (4) | 0.044 (3) | 0.055 (3) | 0.069 (4) |
O9 | 0.138 (6) | 0.089 (4) | 0.067 (3) | 0.048 (4) | −0.003 (4) | 0.000 (3) |
O12 | 0.132 (5) | 0.097 (5) | 0.050 (3) | −0.004 (4) | 0.025 (3) | 0.025 (3) |
C63 | 0.047 (2) | 0.032 (2) | 0.045 (2) | 0.0201 (19) | 0.028 (2) | 0.0056 (18) |
C32 | 0.040 (2) | 0.045 (3) | 0.042 (2) | 0.015 (2) | 0.0201 (19) | 0.004 (2) |
O13 | 0.102 (4) | 0.173 (6) | 0.046 (2) | 0.099 (4) | 0.032 (2) | 0.034 (3) |
C28 | 0.048 (2) | 0.039 (2) | 0.033 (2) | 0.018 (2) | 0.0141 (18) | 0.0095 (18) |
C59 | 0.047 (3) | 0.032 (2) | 0.063 (3) | 0.013 (2) | 0.025 (2) | 0.022 (2) |
C60 | 0.064 (3) | 0.019 (2) | 0.047 (3) | 0.008 (2) | 0.004 (2) | 0.0118 (18) |
C65 | 0.057 (3) | 0.035 (3) | 0.063 (3) | 0.012 (2) | 0.034 (3) | 0.016 (2) |
C64 | 0.071 (3) | 0.053 (3) | 0.044 (3) | 0.040 (3) | 0.020 (2) | 0.001 (2) |
C29 | 0.056 (3) | 0.054 (3) | 0.040 (3) | 0.017 (3) | 0.014 (2) | −0.005 (2) |
C61 | 0.085 (4) | 0.022 (2) | 0.058 (3) | 0.001 (3) | 0.001 (3) | 0.013 (2) |
C67 | 0.066 (4) | 0.103 (6) | 0.085 (5) | 0.049 (4) | 0.050 (4) | 0.057 (4) |
C66 | 0.117 (6) | 0.132 (7) | 0.074 (5) | 0.077 (6) | 0.034 (4) | 0.026 (5) |
Geometric parameters (Å, º) top
Br2—C33 | 1.894 (4) | C46—C45 | 1.491 (5) |
Br1—C1 | 1.892 (4) | C13—C12 | 1.403 (5) |
Co1—O1 | 2.064 (3) | C21—C26 | 1.412 (5) |
Co1—O2 | 2.047 (3) | C21—C22 | 1.376 (5) |
Co1—N2 | 2.042 (3) | C26—C25 | 1.426 (5) |
Co1—N5 | 2.044 (3) | O5—C65 | 1.392 (6) |
Co1—N4 | 2.208 (3) | C47—C52 | 1.410 (6) |
Co1—N1 | 2.188 (3) | C47—C48 | 1.407 (6) |
Cl2—O14 | 1.442 (3) | N9—C50 | 1.374 (5) |
Cl2—O11 | 1.411 (4) | N9—C60 | 1.445 (7) |
Cl2—O12 | 1.381 (6) | C15—C20 | 1.413 (5) |
Cl2—O13 | 1.435 (5) | C15—C16 | 1.418 (5) |
Cl1—O10 | 1.418 (4) | C54—C53 | 1.358 (6) |
Cl1—O8 | 1.452 (4) | C54—C55 | 1.409 (6) |
Cl1—O7 | 1.428 (6) | C37—C38 | 1.467 (6) |
Cl1—O9 | 1.386 (6) | C37—C36 | 1.389 (5) |
Cl3—C67 | 1.773 (9) | C45—C40 | 1.409 (5) |
Cl4—C67 | 1.743 (9) | C45—C44 | 1.401 (5) |
O1—C7 | 1.269 (5) | C24—C23 | 1.437 (5) |
O2—C39 | 1.271 (5) | C24—C25 | 1.366 (6) |
O3—C21 | 1.363 (4) | C24—C30 | 1.501 (5) |
O3—C20 | 1.359 (5) | C23—C22 | 1.412 (5) |
O4—C53 | 1.366 (5) | C19—C20 | 1.382 (5) |
O4—C52 | 1.361 (5) | C19—C18 | 1.389 (6) |
N2—N3 | 1.366 (4) | C40—C41 | 1.392 (5) |
N2—C6 | 1.288 (5) | C4—C3 | 1.389 (6) |
N5—N6 | 1.370 (5) | C57—C56 | 1.352 (5) |
N5—C38 | 1.288 (5) | C52—C51 | 1.387 (5) |
N4—C37 | 1.370 (5) | C33—C34 | 1.392 (5) |
N4—C33 | 1.322 (5) | C1—C2 | 1.393 (6) |
N1—C5 | 1.362 (5) | O6—C66 | 1.395 (10) |
N1—C1 | 1.318 (5) | C55—C56 | 1.447 (5) |
N6—C39 | 1.339 (5) | C17—C18 | 1.437 (6) |
N3—C7 | 1.347 (5) | C17—C16 | 1.367 (5) |
N8—C23 | 1.342 (5) | C17—C27 | 1.503 (5) |
N8—C31 | 1.456 (5) | C9—C10 | 1.387 (5) |
N10—C55 | 1.326 (6) | C56—C62 | 1.503 (5) |
N10—C63 | 1.460 (5) | C36—C35 | 1.392 (6) |
C7—C8 | 1.486 (5) | C48—C49 | 1.378 (6) |
C14—C13 | 1.494 (5) | C2—C3 | 1.384 (6) |
C14—C26 | 1.407 (5) | C44—C43 | 1.387 (6) |
C14—C15 | 1.414 (5) | C41—C42 | 1.384 (6) |
C39—C40 | 1.489 (5) | C10—C11 | 1.391 (6) |
C5—C6 | 1.453 (5) | C12—C11 | 1.387 (6) |
C5—C4 | 1.390 (5) | C49—C50 | 1.426 (7) |
C8—C13 | 1.407 (5) | C49—C59 | 1.491 (7) |
C8—C9 | 1.392 (5) | C34—C35 | 1.388 (6) |
N7—C18 | 1.361 (5) | C50—C51 | 1.384 (7) |
N7—C28 | 1.465 (6) | C43—C42 | 1.394 (6) |
C58—C46 | 1.389 (5) | C31—C32 | 1.518 (7) |
C58—C53 | 1.421 (5) | C63—C64 | 1.502 (8) |
C58—C57 | 1.434 (5) | C28—C29 | 1.505 (7) |
C46—C47 | 1.427 (5) | C60—C61 | 1.526 (7) |
| | | |
O1—Co1—N4 | 92.23 (11) | C48—C47—C52 | 117.0 (4) |
O1—Co1—N1 | 151.55 (11) | C50—N9—C60 | 123.1 (5) |
O2—Co1—O1 | 98.93 (11) | C14—C15—C16 | 124.7 (3) |
O2—Co1—N4 | 148.65 (12) | C20—C15—C14 | 119.4 (3) |
O2—Co1—N1 | 85.63 (11) | C20—C15—C16 | 115.9 (3) |
N2—Co1—O1 | 75.66 (11) | C53—C54—C55 | 120.1 (4) |
N2—Co1—O2 | 96.19 (11) | N4—C37—C38 | 116.0 (3) |
N2—Co1—N5 | 159.47 (13) | N4—C37—C36 | 122.2 (4) |
N2—Co1—N4 | 114.99 (12) | C36—C37—C38 | 121.9 (4) |
N2—Co1—N1 | 75.94 (12) | O4—C53—C58 | 120.2 (4) |
N5—Co1—O1 | 87.08 (12) | C54—C53—O4 | 116.2 (3) |
N5—Co1—O2 | 75.30 (12) | C54—C53—C58 | 123.5 (4) |
N5—Co1—N4 | 76.13 (12) | C40—C45—C46 | 124.4 (3) |
N5—Co1—N1 | 121.05 (12) | C44—C45—C46 | 116.4 (3) |
N1—Co1—N4 | 98.30 (11) | C44—C45—C40 | 119.2 (4) |
O11—Cl2—O14 | 110.2 (2) | C23—C24—C30 | 118.4 (3) |
O11—Cl2—O13 | 107.5 (4) | C25—C24—C23 | 119.5 (3) |
O12—Cl2—O14 | 112.8 (3) | C25—C24—C30 | 122.1 (4) |
O12—Cl2—O11 | 109.5 (4) | N8—C23—C24 | 119.5 (3) |
O12—Cl2—O13 | 107.6 (5) | N8—C23—C22 | 121.3 (4) |
O13—Cl2—O14 | 109.1 (3) | C22—C23—C24 | 119.2 (4) |
O10—Cl1—O8 | 108.4 (2) | C20—C19—C18 | 119.1 (4) |
O10—Cl1—O7 | 109.8 (3) | C45—C40—C39 | 118.8 (3) |
O7—Cl1—O8 | 107.0 (4) | C41—C40—C39 | 121.6 (3) |
O9—Cl1—O10 | 112.1 (4) | C41—C40—C45 | 119.6 (3) |
O9—Cl1—O8 | 111.4 (4) | C3—C4—C5 | 119.4 (4) |
O9—Cl1—O7 | 107.9 (4) | C56—C57—C58 | 122.9 (3) |
C7—O1—Co1 | 111.8 (2) | O4—C52—C47 | 121.8 (3) |
C39—O2—Co1 | 112.3 (2) | O4—C52—C51 | 115.5 (4) |
C20—O3—C21 | 120.4 (3) | C51—C52—C47 | 122.7 (4) |
C52—O4—C53 | 120.3 (3) | C24—C25—C26 | 122.7 (3) |
N3—N2—Co1 | 118.6 (2) | N5—C38—C37 | 115.6 (3) |
C6—N2—Co1 | 120.2 (3) | N4—C33—Br2 | 116.7 (3) |
C6—N2—N3 | 120.6 (3) | N4—C33—C34 | 125.7 (4) |
N6—N5—Co1 | 118.3 (2) | C34—C33—Br2 | 117.5 (3) |
C38—N5—Co1 | 119.4 (3) | O3—C20—C15 | 120.9 (3) |
C38—N5—N6 | 121.4 (3) | O3—C20—C19 | 115.7 (3) |
C37—N4—Co1 | 110.1 (2) | C19—C20—C15 | 123.3 (4) |
C33—N4—Co1 | 131.5 (3) | N1—C1—Br1 | 116.5 (3) |
C33—N4—C37 | 116.5 (3) | N1—C1—C2 | 125.6 (4) |
C5—N1—Co1 | 112.1 (2) | C2—C1—Br1 | 117.9 (3) |
C1—N1—Co1 | 130.6 (3) | N10—C55—C54 | 122.4 (4) |
C1—N1—C5 | 117.2 (3) | N10—C55—C56 | 119.2 (4) |
C39—N6—N5 | 107.0 (3) | C54—C55—C56 | 118.4 (4) |
C7—N3—N2 | 107.5 (3) | C18—C17—C27 | 119.6 (3) |
C23—N8—C31 | 125.3 (3) | C16—C17—C18 | 119.3 (4) |
C55—N10—C63 | 124.4 (4) | C16—C17—C27 | 121.1 (4) |
O1—C7—N3 | 125.9 (3) | C10—C9—C8 | 121.1 (4) |
O1—C7—C8 | 118.2 (3) | C21—C22—C23 | 119.0 (3) |
N3—C7—C8 | 115.8 (3) | C57—C56—C55 | 119.8 (4) |
C26—C14—C13 | 121.5 (3) | C57—C56—C62 | 122.5 (3) |
C26—C14—C15 | 118.8 (3) | C55—C56—C62 | 117.7 (4) |
C15—C14—C13 | 119.4 (3) | C37—C36—C35 | 119.2 (4) |
O2—C39—N6 | 125.8 (3) | N7—C18—C19 | 121.3 (4) |
O2—C39—C40 | 116.6 (3) | N7—C18—C17 | 119.0 (4) |
N6—C39—C40 | 117.7 (3) | C19—C18—C17 | 119.7 (3) |
N1—C5—C6 | 115.9 (3) | C49—C48—C47 | 122.0 (4) |
N1—C5—C4 | 121.6 (3) | C17—C16—C15 | 122.6 (4) |
C4—C5—C6 | 122.5 (3) | C3—C2—C1 | 116.6 (4) |
C13—C8—C7 | 120.5 (3) | C2—C3—C4 | 119.5 (4) |
C9—C8—C7 | 119.7 (3) | C43—C44—C45 | 120.5 (4) |
C9—C8—C13 | 119.7 (3) | C42—C41—C40 | 120.7 (4) |
C18—N7—C28 | 124.7 (4) | C9—C10—C11 | 119.5 (4) |
C46—C58—C53 | 120.0 (3) | C11—C12—C13 | 120.9 (4) |
C46—C58—C57 | 124.6 (3) | C48—C49—C50 | 118.9 (4) |
C53—C58—C57 | 115.3 (3) | C48—C49—C59 | 121.4 (4) |
C58—C46—C47 | 119.2 (4) | C50—C49—C59 | 119.7 (4) |
C58—C46—C45 | 121.4 (3) | C35—C34—C33 | 117.0 (4) |
C47—C46—C45 | 119.1 (3) | N9—C50—C49 | 119.1 (4) |
C8—C13—C14 | 124.8 (3) | N9—C50—C51 | 120.3 (4) |
C12—C13—C14 | 116.4 (3) | C51—C50—C49 | 120.6 (4) |
C12—C13—C8 | 118.7 (3) | C34—C35—C36 | 119.3 (4) |
O3—C21—C26 | 121.2 (3) | C50—C51—C52 | 118.8 (4) |
O3—C21—C22 | 115.1 (3) | C12—C11—C10 | 120.2 (4) |
C22—C21—C26 | 123.7 (3) | C44—C43—C42 | 120.0 (4) |
N2—C6—C5 | 115.6 (3) | C41—C42—C43 | 120.0 (4) |
C14—C26—C21 | 119.2 (3) | N8—C31—C32 | 113.3 (4) |
C14—C26—C25 | 124.9 (3) | N10—C63—C64 | 112.4 (4) |
C21—C26—C25 | 115.8 (3) | N7—C28—C29 | 112.5 (4) |
C52—C47—C46 | 118.3 (4) | N9—C60—C61 | 109.7 (6) |
C48—C47—C46 | 124.7 (4) | Cl4—C67—Cl3 | 112.0 (4) |
| | | |
Br2—C33—C34—C35 | 175.3 (3) | C47—C48—C49—C50 | 2.2 (6) |
Br1—C1—C2—C3 | −175.2 (3) | C47—C48—C49—C59 | −177.5 (4) |
Co1—O1—C7—N3 | 8.0 (5) | N9—C50—C51—C52 | 179.7 (4) |
Co1—O1—C7—C8 | −169.0 (2) | C15—C14—C13—C8 | −80.1 (4) |
Co1—O2—C39—N6 | 8.9 (5) | C15—C14—C13—C12 | 96.5 (4) |
Co1—O2—C39—C40 | −171.4 (2) | C15—C14—C26—C21 | −0.3 (5) |
Co1—N2—N3—C7 | −3.2 (4) | C15—C14—C26—C25 | 178.9 (3) |
Co1—N2—C6—C5 | 6.0 (4) | C54—C55—C56—C57 | −2.7 (5) |
Co1—N5—N6—C39 | −8.4 (4) | C54—C55—C56—C62 | 178.1 (3) |
Co1—N5—C38—C37 | 10.3 (4) | C37—N4—C33—Br2 | −175.0 (3) |
Co1—N4—C37—C38 | −14.3 (4) | C37—N4—C33—C34 | 3.2 (5) |
Co1—N4—C37—C36 | 165.6 (3) | C37—C36—C35—C34 | 2.0 (6) |
Co1—N4—C33—Br2 | 22.2 (4) | C53—O4—C52—C47 | −1.1 (5) |
Co1—N4—C33—C34 | −159.5 (3) | C53—O4—C52—C51 | 177.7 (3) |
Co1—N1—C5—C6 | −1.8 (4) | C53—C58—C46—C47 | 3.3 (5) |
Co1—N1—C5—C4 | 176.8 (3) | C53—C58—C46—C45 | 176.5 (3) |
Co1—N1—C1—Br1 | −0.7 (5) | C53—C58—C57—C56 | 0.5 (5) |
Co1—N1—C1—C2 | −178.3 (3) | C53—C54—C55—N10 | 179.7 (4) |
O1—C7—C8—C13 | 10.5 (5) | C53—C54—C55—C56 | 1.4 (5) |
O1—C7—C8—C9 | −172.3 (3) | C45—C46—C47—C52 | −172.9 (3) |
O2—C39—C40—C45 | −0.8 (5) | C45—C46—C47—C48 | 9.5 (5) |
O2—C39—C40—C41 | 179.5 (3) | C45—C40—C41—C42 | −0.8 (6) |
O3—C21—C26—C14 | 1.3 (5) | C45—C44—C43—C42 | −1.1 (7) |
O3—C21—C26—C25 | −178.1 (3) | C24—C23—C22—C21 | −2.2 (5) |
O3—C21—C22—C23 | −179.9 (3) | C23—N8—C31—C32 | 83.4 (5) |
O4—C52—C51—C50 | −176.5 (3) | C23—C24—C25—C26 | −1.3 (6) |
N2—N3—C7—O1 | −3.5 (5) | C40—C45—C44—C43 | 0.4 (6) |
N2—N3—C7—C8 | 173.6 (3) | C40—C41—C42—C43 | 0.1 (6) |
N5—N6—C39—O2 | −0.6 (5) | C4—C5—C6—N2 | 179.0 (3) |
N5—N6—C39—C40 | 179.7 (3) | C57—C58—C46—C47 | 179.3 (3) |
N4—C37—C38—N5 | 4.0 (5) | C57—C58—C46—C45 | −7.5 (5) |
N4—C37—C36—C35 | −1.7 (6) | C57—C58—C53—O4 | 177.5 (3) |
N4—C33—C34—C35 | −2.9 (6) | C57—C58—C53—C54 | −1.9 (5) |
N1—C5—C6—N2 | −2.4 (5) | C52—O4—C53—C58 | 5.1 (5) |
N1—C5—C4—C3 | 2.2 (6) | C52—O4—C53—C54 | −175.5 (3) |
N1—C1—C2—C3 | 2.3 (7) | C52—C47—C48—C49 | 0.4 (5) |
N6—N5—C38—C37 | 179.1 (3) | C25—C24—C23—N8 | −175.5 (4) |
N6—C39—C40—C45 | 178.9 (3) | C25—C24—C23—C22 | 3.5 (5) |
N6—C39—C40—C41 | −0.8 (5) | C38—N5—N6—C39 | −177.3 (3) |
N3—N2—C6—C5 | 176.6 (3) | C38—C37—C36—C35 | 178.1 (4) |
N3—C7—C8—C13 | −166.8 (3) | C33—N4—C37—C38 | 179.3 (3) |
N3—C7—C8—C9 | 10.4 (5) | C33—N4—C37—C36 | −0.8 (5) |
N8—C23—C22—C21 | 176.8 (4) | C33—C34—C35—C36 | 0.1 (6) |
N10—C55—C56—C57 | 178.9 (4) | C20—O3—C21—C26 | −0.8 (5) |
N10—C55—C56—C62 | −0.3 (5) | C20—O3—C21—C22 | 177.7 (3) |
C7—C8—C13—C14 | −8.1 (5) | C20—C15—C16—C17 | −1.7 (5) |
C7—C8—C13—C12 | 175.4 (3) | C20—C19—C18—N7 | 174.9 (4) |
C7—C8—C9—C10 | −176.5 (3) | C20—C19—C18—C17 | −3.1 (6) |
C14—C13—C12—C11 | −175.0 (3) | C1—N1—C5—C6 | −178.0 (3) |
C14—C26—C25—C24 | 178.6 (3) | C1—N1—C5—C4 | 0.5 (5) |
C14—C15—C20—O3 | 1.5 (5) | C1—C2—C3—C4 | 0.6 (6) |
C14—C15—C20—C19 | −177.1 (3) | C55—N10—C63—C64 | 80.8 (6) |
C14—C15—C16—C17 | 176.7 (3) | C55—C54—C53—O4 | −178.5 (3) |
C39—C40—C41—C42 | 178.9 (4) | C55—C54—C53—C58 | 1.0 (6) |
C5—N1—C1—Br1 | 174.7 (3) | C9—C8—C13—C14 | 174.7 (3) |
C5—N1—C1—C2 | −2.8 (6) | C9—C8—C13—C12 | −1.8 (5) |
C5—C4—C3—C2 | −2.7 (6) | C9—C10—C11—C12 | −0.6 (6) |
C8—C13—C12—C11 | 1.8 (5) | C22—C21—C26—C14 | −177.1 (3) |
C8—C9—C10—C11 | 0.6 (6) | C22—C21—C26—C25 | 3.5 (5) |
C58—C46—C47—C52 | 0.5 (5) | C36—C37—C38—N5 | −175.9 (4) |
C58—C46—C47—C48 | −177.1 (4) | C18—N7—C28—C29 | 93.5 (6) |
C58—C46—C45—C40 | 92.8 (5) | C18—C19—C20—O3 | −177.7 (3) |
C58—C46—C45—C44 | −87.3 (4) | C18—C19—C20—C15 | 1.0 (6) |
C58—C57—C56—C55 | 1.7 (6) | C18—C17—C16—C15 | −0.3 (6) |
C58—C57—C56—C62 | −179.1 (3) | C48—C47—C52—O4 | 176.1 (3) |
C46—C58—C53—O4 | −6.2 (5) | C48—C47—C52—C51 | −2.7 (5) |
C46—C58—C53—C54 | 174.4 (3) | C48—C49—C50—N9 | 178.1 (4) |
C46—C58—C57—C56 | −175.6 (4) | C48—C49—C50—C51 | −2.6 (6) |
C46—C47—C52—O4 | −1.7 (5) | C16—C15—C20—O3 | 180.0 (3) |
C46—C47—C52—C51 | 179.5 (3) | C16—C15—C20—C19 | 1.4 (5) |
C46—C47—C48—C49 | 178.0 (4) | C16—C17—C18—N7 | −175.2 (4) |
C46—C45—C40—C39 | 0.7 (5) | C16—C17—C18—C19 | 2.8 (6) |
C46—C45—C40—C41 | −179.6 (3) | C27—C17—C18—N7 | 3.6 (6) |
C46—C45—C44—C43 | −179.5 (4) | C27—C17—C18—C19 | −178.4 (4) |
C13—C14—C26—C21 | 173.4 (3) | C27—C17—C16—C15 | −179.1 (3) |
C13—C14—C26—C25 | −7.3 (5) | C44—C45—C40—C39 | −179.2 (3) |
C13—C14—C15—C20 | −174.9 (3) | C44—C45—C40—C41 | 0.5 (5) |
C13—C14—C15—C16 | 6.8 (5) | C44—C43—C42—C41 | 0.8 (7) |
C13—C8—C9—C10 | 0.7 (6) | C49—C50—C51—C52 | 0.4 (6) |
C13—C12—C11—C10 | −0.6 (6) | C50—N9—C60—C61 | 178.7 (4) |
C21—O3—C20—C15 | −0.6 (5) | C30—C24—C23—N8 | 4.2 (5) |
C21—O3—C20—C19 | 178.1 (3) | C30—C24—C23—C22 | −176.7 (3) |
C21—C26—C25—C24 | −2.1 (5) | C30—C24—C25—C26 | 179.0 (3) |
C6—N2—N3—C7 | −174.0 (3) | C31—N8—C23—C24 | 176.9 (4) |
C6—C5—C4—C3 | −179.4 (4) | C31—N8—C23—C22 | −2.2 (6) |
C26—C14—C13—C8 | 106.2 (4) | C63—N10—C55—C54 | 8.0 (7) |
C26—C14—C13—C12 | −77.2 (4) | C63—N10—C55—C56 | −173.7 (4) |
C26—C14—C15—C20 | −1.0 (5) | C28—N7—C18—C19 | −7.1 (7) |
C26—C14—C15—C16 | −179.4 (3) | C28—N7—C18—C17 | 170.9 (4) |
C26—C21—C22—C23 | −1.4 (6) | C59—C49—C50—N9 | −2.2 (6) |
C47—C46—C45—C40 | −94.0 (4) | C59—C49—C50—C51 | 177.1 (4) |
C47—C46—C45—C44 | 85.9 (4) | C60—N9—C50—C49 | 174.6 (4) |
C47—C52—C51—C50 | 2.3 (6) | C60—N9—C50—C51 | −4.6 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8···O6 | 0.86 | 2.14 | 2.913 (5) | 150 |
N10—H10···O5 | 0.86 | 2.08 | 2.877 (5) | 153 |
N7—H7···O14 | 0.86 | 2.33 | 2.951 (5) | 129 |
C6—H6···O14i | 0.93 | 2.54 | 3.373 (5) | 149 |
O5—H5···O11ii | 0.82 | 2.39 | 3.098 (8) | 145 |
O5—H5···O12ii | 0.82 | 2.50 | 3.277 (9) | 158 |
C19—H19···O10iii | 0.93 | 2.58 | 3.509 (6) | 179 |
C4—H4···O13i | 0.93 | 2.49 | 3.323 (6) | 150 |
O6—H6A···O7 | 0.82 | 2.30 | 2.919 (7) | 133 |
C2—H2···O8iv | 0.93 | 2.41 | 3.107 (6) | 132 |
C44—H44···O13v | 0.93 | 2.50 | 3.239 (6) | 137 |
C12—H12···O3vi | 0.93 | 2.54 | 3.438 (5) | 162 |
C28—H28A···O8iii | 0.97 | 2.54 | 3.382 (7) | 146 |
C67—H67A···N6 | 0.97 | 2.36 | 3.281 (7) | 159 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y, −z+1; (iv) x, y+1, z; (v) x+1, y, z+1; (vi) −x, −y, −z+1. |
Bis{
N-[(6-bromopyridin-2-yl)methylidene]-2-[6-ethylamino-3-(ethyliminiumyl)-2,7-dimethyl-3
H-xanthen-9-yl]benzene-1-carbohydrazonate}cobalt(II) bis(tetrafluoridoborate)–dichloromethane–methanol
(1/1/2) (2)
top
Crystal data top
[Co(C32H30BrN5O2)2](BF4)2·CH2Cl2·2CH4O | Z = 2 |
Mr = 1574.60 | F(000) = 1606 |
Triclinic, P1 | Dx = 1.515 Mg m−3 |
a = 13.1820 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 16.2426 (3) Å | Cell parameters from 12867 reflections |
c = 17.7898 (3) Å | θ = 4.3–76.0° |
α = 95.8495 (14)° | µ = 4.70 mm−1 |
β = 107.3297 (16)° | T = 100 K |
γ = 104.7128 (16)° | Block, clear orange |
V = 3451.18 (11) Å3 | 0.3 × 0.2 × 0.2 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an AtlasS2 detector | 13070 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 11725 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.032 |
Detector resolution: 5.2137 pixels mm-1 | θmax = 70.0°, θmin = 3.5° |
ω scans | h = −16→16 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017) | k = −19→19 |
Tmin = 0.607, Tmax = 1.000 | l = −21→15 |
24331 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0767P)2 + 4.2094P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
13070 reflections | Δρmax = 1.43 e Å−3 |
923 parameters | Δρmin = −1.16 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Co1 | 0.73545 (4) | 0.58067 (3) | 0.37985 (3) | 0.01313 (11) | |
Br1 | 0.48426 (3) | 0.45907 (3) | 0.40664 (3) | 0.03829 (12) | |
Br2 | 0.85935 (3) | 0.42392 (2) | 0.48070 (2) | 0.02339 (9) | |
N1 | 0.6343 (2) | 0.44558 (16) | 0.33073 (15) | 0.0168 (5) | |
N2 | 0.8155 (2) | 0.53433 (16) | 0.31085 (15) | 0.0153 (5) | |
N3 | 0.9064 (2) | 0.59119 (16) | 0.30256 (15) | 0.0166 (5) | |
N4 | 0.7953 (2) | 0.57032 (16) | 0.50743 (15) | 0.0161 (5) | |
N5 | 0.6786 (2) | 0.66609 (16) | 0.43614 (15) | 0.0155 (5) | |
N6 | 0.6139 (2) | 0.70897 (16) | 0.38973 (15) | 0.0173 (5) | |
N7 | 1.0850 (2) | 0.82666 (19) | 0.74955 (16) | 0.0249 (6) | |
H7 | 1.1424 | 0.8075 | 0.7690 | 0.030* | |
N8 | 0.6301 (2) | 1.01007 (18) | 0.32443 (17) | 0.0228 (5) | |
H8 | 0.6047 | 1.0112 | 0.2730 | 0.027* | |
N9 | 0.2679 (3) | 0.25194 (19) | 0.08203 (19) | 0.0338 (7) | |
H9 | 0.2053 | 0.2412 | 0.0928 | 0.041* | |
N10 | 0.9315 (3) | 0.64350 (19) | 0.0824 (2) | 0.0318 (7) | |
H10 | 0.9736 | 0.6970 | 0.0885 | 0.038* | |
O1 | 0.87392 (18) | 0.68391 (13) | 0.39508 (13) | 0.0191 (4) | |
O2 | 0.62230 (18) | 0.61089 (13) | 0.28928 (12) | 0.0190 (4) | |
O3 | 0.86477 (17) | 0.91361 (14) | 0.52946 (12) | 0.0183 (4) | |
O4 | 0.58811 (19) | 0.45861 (14) | 0.07600 (13) | 0.0214 (4) | |
O5 | 1.1013 (3) | 0.7886 (2) | 0.0707 (2) | 0.0549 (9) | |
H5 | 1.0953 | 0.7707 | 0.0231 | 0.082* | |
O6 | 0.4953 (3) | 1.0432 (3) | 0.17580 (18) | 0.0603 (10) | |
H6A | 0.4329 | 1.0381 | 0.1810 | 0.090* | |
Cl1 | 0.36095 (14) | 0.76760 (11) | 0.46623 (10) | 0.0779 (4) | |
Cl2 | 0.29729 (11) | 0.61450 (8) | 0.34169 (10) | 0.0656 (4) | |
B1 | 1.2065 (5) | 0.7122 (3) | 0.9092 (3) | 0.0460 (13) | |
B2 | 0.2630 (4) | 1.1135 (3) | 0.2669 (3) | 0.0324 (9) | |
F1 | 1.1762 (9) | 0.6530 (7) | 0.9523 (5) | 0.094 (4) | 0.561 (17) |
F2 | 1.3297 (7) | 0.7245 (9) | 0.9283 (4) | 0.068 (3) | 0.561 (17) |
F4 | 1.2026 (10) | 0.7880 (7) | 0.9469 (4) | 0.061 (3) | 0.561 (17) |
F1A | 1.1179 (19) | 0.6930 (9) | 0.9397 (10) | 0.134 (8) | 0.439 (17) |
F2A | 1.2650 (15) | 0.6640 (8) | 0.9285 (6) | 0.096 (8) | 0.439 (17) |
F4A | 1.2445 (9) | 0.7998 (8) | 0.9261 (9) | 0.072 (3) | 0.439 (17) |
F3 | 1.1547 (3) | 0.6923 (2) | 0.82789 (14) | 0.0566 (8) | |
F5 | 0.3106 (3) | 1.1425 (2) | 0.34795 (17) | 0.0718 (9) | |
F6 | 0.3382 (2) | 1.0840 (2) | 0.23837 (18) | 0.0538 (7) | |
F7 | 0.24318 (19) | 1.18239 (15) | 0.23005 (17) | 0.0469 (6) | |
F8 | 0.16478 (19) | 1.04844 (14) | 0.24758 (16) | 0.0408 (5) | |
C1 | 0.5421 (3) | 0.3996 (2) | 0.34021 (19) | 0.0222 (6) | |
C2 | 0.4842 (3) | 0.3137 (2) | 0.3045 (2) | 0.0273 (7) | |
H2 | 0.4200 | 0.2837 | 0.3156 | 0.033* | |
C3 | 0.5238 (3) | 0.2738 (2) | 0.25222 (19) | 0.0245 (7) | |
H3 | 0.4874 | 0.2148 | 0.2267 | 0.029* | |
C4 | 0.6172 (3) | 0.3204 (2) | 0.23702 (18) | 0.0204 (6) | |
H4 | 0.6434 | 0.2946 | 0.1992 | 0.024* | |
C5 | 0.6718 (2) | 0.40552 (19) | 0.27804 (17) | 0.0165 (6) | |
C6 | 0.7730 (2) | 0.45778 (19) | 0.26759 (18) | 0.0177 (6) | |
H6 | 0.8049 | 0.4366 | 0.2313 | 0.021* | |
C7 | 0.9262 (2) | 0.66784 (19) | 0.34841 (17) | 0.0155 (5) | |
C8 | 1.0149 (2) | 0.74102 (19) | 0.34113 (17) | 0.0161 (6) | |
C9 | 1.0830 (3) | 0.7251 (2) | 0.29835 (19) | 0.0205 (6) | |
H9A | 1.0754 | 0.6669 | 0.2771 | 0.025* | |
C10 | 1.1619 (3) | 0.7923 (2) | 0.2861 (2) | 0.0242 (7) | |
H10A | 1.2084 | 0.7801 | 0.2574 | 0.029* | |
C11 | 1.1721 (3) | 0.8775 (2) | 0.3161 (2) | 0.0229 (6) | |
H11 | 1.2249 | 0.9239 | 0.3072 | 0.027* | |
C12 | 1.1048 (3) | 0.8947 (2) | 0.35911 (19) | 0.0195 (6) | |
H12 | 1.1119 | 0.9532 | 0.3790 | 0.023* | |
C13 | 1.0272 (2) | 0.82761 (19) | 0.37357 (17) | 0.0152 (5) | |
C14 | 0.9654 (2) | 0.85261 (18) | 0.42578 (18) | 0.0155 (6) | |
C15 | 0.8784 (2) | 0.88856 (18) | 0.39709 (18) | 0.0160 (6) | |
C16 | 0.8314 (2) | 0.89565 (19) | 0.31525 (18) | 0.0181 (6) | |
H16 | 0.8592 | 0.8735 | 0.2766 | 0.022* | |
C17 | 0.7485 (2) | 0.93274 (19) | 0.29041 (18) | 0.0185 (6) | |
C18 | 0.7067 (2) | 0.96827 (19) | 0.34835 (19) | 0.0190 (6) | |
C19 | 0.7476 (3) | 0.9589 (2) | 0.42864 (19) | 0.0195 (6) | |
H19 | 0.7183 | 0.9793 | 0.4671 | 0.023* | |
C20 | 0.8302 (2) | 0.92008 (18) | 0.45077 (17) | 0.0161 (6) | |
C21 | 0.9497 (2) | 0.87930 (18) | 0.55859 (18) | 0.0165 (6) | |
C22 | 0.9763 (3) | 0.8749 (2) | 0.63867 (19) | 0.0197 (6) | |
H22 | 0.9384 | 0.8965 | 0.6702 | 0.024* | |
C23 | 1.0602 (3) | 0.8380 (2) | 0.67307 (18) | 0.0199 (6) | |
C24 | 1.1198 (2) | 0.80925 (19) | 0.62430 (19) | 0.0184 (6) | |
C25 | 1.0904 (2) | 0.81530 (19) | 0.54580 (18) | 0.0176 (6) | |
H25 | 1.1298 | 0.7958 | 0.5144 | 0.021* | |
C26 | 1.0028 (2) | 0.84963 (18) | 0.50824 (18) | 0.0162 (6) | |
C27 | 0.6992 (3) | 0.9388 (2) | 0.20430 (19) | 0.0247 (7) | |
H27A | 0.6194 | 0.9074 | 0.1845 | 0.037* | |
H27B | 0.7362 | 0.9131 | 0.1721 | 0.037* | |
H27C | 0.7097 | 0.9998 | 0.2000 | 0.037* | |
C28 | 0.5860 (3) | 1.0536 (2) | 0.3772 (2) | 0.0274 (7) | |
H28A | 0.5623 | 1.1010 | 0.3534 | 0.033* | |
H28B | 0.6460 | 1.0799 | 0.4294 | 0.033* | |
C29 | 0.4883 (3) | 0.9934 (3) | 0.3916 (2) | 0.0370 (8) | |
H29A | 0.4279 | 0.9679 | 0.3403 | 0.055* | |
H29B | 0.4622 | 1.0261 | 0.4273 | 0.055* | |
H29C | 0.5116 | 0.9471 | 0.4165 | 0.055* | |
C30 | 1.2107 (3) | 0.7709 (2) | 0.66154 (19) | 0.0237 (6) | |
H30A | 1.1791 | 0.7175 | 0.6785 | 0.036* | |
H30B | 1.2667 | 0.8126 | 0.7083 | 0.036* | |
H30C | 1.2456 | 0.7576 | 0.6222 | 0.036* | |
C31 | 1.0241 (3) | 0.8437 (2) | 0.8027 (2) | 0.0274 (7) | |
H31A | 1.0276 | 0.8029 | 0.8405 | 0.033* | |
H31B | 0.9449 | 0.8327 | 0.7703 | 0.033* | |
C32 | 1.0702 (3) | 0.9362 (3) | 0.8502 (2) | 0.0417 (10) | |
H32A | 1.0659 | 0.9768 | 0.8130 | 0.063* | |
H32B | 1.1481 | 0.9469 | 0.8835 | 0.063* | |
H32C | 1.0264 | 0.9444 | 0.8846 | 0.063* | |
C33 | 0.8567 (2) | 0.5230 (2) | 0.54457 (18) | 0.0187 (6) | |
C34 | 0.9168 (3) | 0.5409 (2) | 0.62615 (19) | 0.0227 (6) | |
H34 | 0.9621 | 0.5066 | 0.6490 | 0.027* | |
C35 | 0.9084 (3) | 0.6107 (2) | 0.67284 (19) | 0.0248 (7) | |
H35 | 0.9486 | 0.6255 | 0.7288 | 0.030* | |
C36 | 0.8404 (3) | 0.6590 (2) | 0.63714 (19) | 0.0219 (6) | |
H36 | 0.8310 | 0.7054 | 0.6688 | 0.026* | |
C37 | 0.7867 (2) | 0.63832 (19) | 0.55459 (18) | 0.0176 (6) | |
C38 | 0.7173 (2) | 0.68845 (19) | 0.51310 (18) | 0.0180 (6) | |
H38 | 0.7020 | 0.7343 | 0.5410 | 0.022* | |
C39 | 0.5910 (2) | 0.67350 (18) | 0.31311 (18) | 0.0167 (6) | |
C40 | 0.5215 (2) | 0.70879 (19) | 0.24975 (18) | 0.0168 (6) | |
C41 | 0.4829 (3) | 0.7775 (2) | 0.26929 (19) | 0.0207 (6) | |
H41 | 0.5020 | 0.8033 | 0.3239 | 0.025* | |
C42 | 0.4165 (3) | 0.8085 (2) | 0.2092 (2) | 0.0250 (7) | |
H42 | 0.3900 | 0.8552 | 0.2228 | 0.030* | |
C43 | 0.3891 (3) | 0.7710 (2) | 0.1291 (2) | 0.0269 (7) | |
H43 | 0.3439 | 0.7923 | 0.0881 | 0.032* | |
C44 | 0.4273 (3) | 0.7030 (2) | 0.1089 (2) | 0.0238 (6) | |
H44 | 0.4081 | 0.6775 | 0.0541 | 0.029* | |
C45 | 0.4940 (2) | 0.67149 (19) | 0.16883 (18) | 0.0175 (6) | |
C46 | 0.5309 (2) | 0.59787 (19) | 0.14141 (17) | 0.0176 (6) | |
C47 | 0.6287 (2) | 0.61252 (19) | 0.12226 (17) | 0.0175 (6) | |
C48 | 0.7065 (3) | 0.69576 (19) | 0.13478 (17) | 0.0174 (6) | |
H48 | 0.6891 | 0.7454 | 0.1537 | 0.021* | |
C49 | 0.8046 (3) | 0.7073 (2) | 0.12085 (18) | 0.0194 (6) | |
C50 | 0.8330 (3) | 0.6318 (2) | 0.09377 (19) | 0.0223 (6) | |
C51 | 0.7569 (3) | 0.5487 (2) | 0.07965 (18) | 0.0220 (6) | |
H51 | 0.7740 | 0.4986 | 0.0612 | 0.026* | |
C52 | 0.6584 (3) | 0.54092 (19) | 0.09271 (17) | 0.0192 (6) | |
C53 | 0.4918 (3) | 0.4434 (2) | 0.09308 (17) | 0.0199 (6) | |
C54 | 0.4281 (3) | 0.3575 (2) | 0.07636 (18) | 0.0224 (6) | |
H54 | 0.4499 | 0.3138 | 0.0511 | 0.027* | |
C55 | 0.3322 (3) | 0.3356 (2) | 0.09668 (19) | 0.0261 (7) | |
C56 | 0.3003 (3) | 0.4027 (2) | 0.1351 (2) | 0.0262 (7) | |
C57 | 0.3634 (3) | 0.4871 (2) | 0.14754 (19) | 0.0224 (6) | |
H57 | 0.3404 | 0.5312 | 0.1708 | 0.027* | |
C58 | 0.4612 (3) | 0.5114 (2) | 0.12723 (18) | 0.0193 (6) | |
C59 | 0.8856 (3) | 0.7957 (2) | 0.13296 (19) | 0.0213 (6) | |
H59A | 0.8517 | 0.8404 | 0.1448 | 0.032* | |
H59B | 0.9042 | 0.8021 | 0.0841 | 0.032* | |
H59C | 0.9535 | 0.8021 | 0.1779 | 0.032* | |
C60 | 0.9727 (4) | 0.5729 (3) | 0.0605 (3) | 0.0443 (10) | |
H60A | 1.0280 | 0.5938 | 0.0340 | 0.053* | |
H60B | 0.9102 | 0.5255 | 0.0217 | 0.053* | |
C61 | 1.0244 (5) | 0.5392 (4) | 0.1303 (3) | 0.0655 (15) | |
H61A | 1.0292 | 0.4816 | 0.1126 | 0.098* | |
H61B | 0.9792 | 0.5349 | 0.1655 | 0.098* | |
H61C | 1.0993 | 0.5785 | 0.1596 | 0.098* | |
C62 | 0.1995 (3) | 0.3777 (3) | 0.1602 (3) | 0.0380 (9) | |
H62A | 0.1909 | 0.4297 | 0.1876 | 0.057* | |
H62B | 0.2083 | 0.3368 | 0.1966 | 0.057* | |
H62C | 0.1333 | 0.3505 | 0.1126 | 0.057* | |
C63 | 0.2975 (4) | 0.1796 (2) | 0.0496 (2) | 0.0368 (9) | |
H63A | 0.3696 | 0.1777 | 0.0863 | 0.044* | |
H63B | 0.3060 | 0.1873 | −0.0029 | 0.044* | |
C64 | 0.2081 (4) | 0.0951 (3) | 0.0392 (3) | 0.0481 (12) | |
H64A | 0.1362 | 0.0980 | 0.0046 | 0.072* | |
H64B | 0.2032 | 0.0858 | 0.0917 | 0.072* | |
H64C | 0.2271 | 0.0470 | 0.0146 | 0.072* | |
C65 | 1.1436 (4) | 0.8792 (3) | 0.0891 (3) | 0.0434 (10) | |
H65A | 1.1092 | 0.9032 | 0.0431 | 0.065* | |
H65B | 1.2244 | 0.8965 | 0.1013 | 0.065* | |
H65C | 1.1266 | 0.9014 | 0.1358 | 0.065* | |
C66 | 0.4824 (7) | 1.0272 (5) | 0.0938 (3) | 0.086 (2) | |
H66A | 0.4045 | 0.9954 | 0.0628 | 0.128* | |
H66B | 0.5304 | 0.9927 | 0.0852 | 0.128* | |
H66C | 0.5032 | 1.0825 | 0.0764 | 0.128* | |
C67 | 0.3882 (5) | 0.6714 (4) | 0.4391 (4) | 0.0669 (16) | |
H67A | 0.3794 | 0.6339 | 0.4787 | 0.080* | |
H67B | 0.4662 | 0.6848 | 0.4401 | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0130 (2) | 0.0141 (2) | 0.0127 (2) | 0.00330 (17) | 0.00610 (18) | 0.00073 (17) |
Br1 | 0.0334 (2) | 0.0309 (2) | 0.0544 (3) | −0.00025 (15) | 0.03232 (19) | −0.00306 (17) |
Br2 | 0.02712 (17) | 0.02236 (17) | 0.02187 (17) | 0.01075 (13) | 0.00747 (13) | 0.00319 (12) |
N1 | 0.0161 (11) | 0.0181 (12) | 0.0155 (11) | 0.0042 (9) | 0.0053 (9) | 0.0027 (9) |
N2 | 0.0155 (11) | 0.0147 (11) | 0.0171 (12) | 0.0050 (9) | 0.0074 (9) | 0.0023 (9) |
N3 | 0.0168 (12) | 0.0156 (12) | 0.0195 (12) | 0.0040 (9) | 0.0100 (10) | 0.0025 (9) |
N4 | 0.0159 (11) | 0.0167 (12) | 0.0156 (12) | 0.0022 (9) | 0.0077 (9) | 0.0018 (9) |
N5 | 0.0145 (11) | 0.0155 (11) | 0.0158 (12) | 0.0019 (9) | 0.0069 (9) | 0.0012 (9) |
N6 | 0.0173 (12) | 0.0176 (12) | 0.0178 (12) | 0.0063 (10) | 0.0069 (10) | 0.0012 (9) |
N7 | 0.0278 (14) | 0.0327 (15) | 0.0182 (13) | 0.0161 (12) | 0.0072 (11) | 0.0054 (11) |
N8 | 0.0218 (13) | 0.0271 (14) | 0.0214 (13) | 0.0122 (11) | 0.0061 (11) | 0.0038 (11) |
N9 | 0.0386 (17) | 0.0199 (14) | 0.0343 (16) | −0.0003 (12) | 0.0070 (14) | 0.0066 (12) |
N10 | 0.0347 (16) | 0.0235 (14) | 0.0468 (18) | 0.0105 (12) | 0.0280 (15) | 0.0011 (13) |
O1 | 0.0197 (10) | 0.0170 (10) | 0.0214 (10) | 0.0009 (8) | 0.0134 (9) | −0.0010 (8) |
O2 | 0.0222 (10) | 0.0182 (10) | 0.0164 (10) | 0.0081 (8) | 0.0056 (8) | −0.0001 (8) |
O3 | 0.0194 (10) | 0.0208 (10) | 0.0166 (10) | 0.0093 (8) | 0.0069 (8) | 0.0008 (8) |
O4 | 0.0282 (11) | 0.0158 (10) | 0.0185 (10) | 0.0068 (9) | 0.0070 (9) | −0.0018 (8) |
O5 | 0.064 (2) | 0.0357 (16) | 0.076 (2) | 0.0028 (15) | 0.052 (2) | 0.0028 (15) |
O6 | 0.079 (2) | 0.101 (3) | 0.0319 (15) | 0.071 (2) | 0.0235 (16) | 0.0196 (17) |
Cl1 | 0.0729 (9) | 0.0761 (10) | 0.0783 (10) | 0.0187 (8) | 0.0261 (8) | −0.0058 (8) |
Cl2 | 0.0511 (7) | 0.0456 (6) | 0.1033 (11) | 0.0112 (5) | 0.0362 (7) | 0.0061 (6) |
B1 | 0.086 (4) | 0.047 (3) | 0.026 (2) | 0.045 (3) | 0.026 (2) | 0.0115 (19) |
B2 | 0.0269 (19) | 0.030 (2) | 0.041 (2) | 0.0049 (16) | 0.0136 (17) | 0.0124 (17) |
F1 | 0.116 (8) | 0.093 (7) | 0.046 (4) | 0.001 (6) | 0.006 (4) | 0.037 (4) |
F2 | 0.070 (4) | 0.139 (9) | 0.031 (3) | 0.072 (5) | 0.028 (3) | 0.028 (4) |
F4 | 0.086 (6) | 0.068 (5) | 0.030 (3) | 0.057 (5) | 0.000 (3) | −0.013 (3) |
F1A | 0.228 (18) | 0.097 (9) | 0.122 (11) | 0.021 (10) | 0.147 (13) | 0.015 (8) |
F2A | 0.147 (14) | 0.076 (9) | 0.043 (4) | 0.090 (10) | −0.040 (6) | −0.019 (5) |
F4A | 0.057 (6) | 0.055 (5) | 0.081 (8) | 0.004 (4) | 0.006 (5) | 0.002 (5) |
F3 | 0.088 (2) | 0.0722 (18) | 0.0287 (12) | 0.0606 (17) | 0.0164 (13) | 0.0105 (12) |
F5 | 0.088 (2) | 0.078 (2) | 0.0362 (15) | 0.0192 (18) | 0.0089 (15) | 0.0032 (14) |
F6 | 0.0363 (13) | 0.0726 (18) | 0.0706 (18) | 0.0267 (13) | 0.0294 (13) | 0.0306 (15) |
F7 | 0.0320 (12) | 0.0351 (12) | 0.0702 (17) | 0.0040 (9) | 0.0116 (11) | 0.0276 (12) |
F8 | 0.0319 (11) | 0.0240 (10) | 0.0717 (16) | 0.0064 (9) | 0.0245 (11) | 0.0154 (10) |
C1 | 0.0210 (15) | 0.0239 (16) | 0.0219 (15) | 0.0058 (12) | 0.0085 (12) | 0.0040 (12) |
C2 | 0.0209 (15) | 0.0247 (17) | 0.0316 (18) | −0.0011 (13) | 0.0090 (13) | 0.0046 (13) |
C3 | 0.0241 (16) | 0.0166 (14) | 0.0227 (15) | −0.0007 (12) | 0.0004 (13) | 0.0007 (12) |
C4 | 0.0257 (15) | 0.0188 (14) | 0.0171 (14) | 0.0088 (12) | 0.0058 (12) | 0.0038 (11) |
C5 | 0.0184 (14) | 0.0170 (14) | 0.0157 (13) | 0.0071 (11) | 0.0061 (11) | 0.0039 (11) |
C6 | 0.0199 (14) | 0.0167 (14) | 0.0195 (14) | 0.0070 (11) | 0.0100 (12) | 0.0025 (11) |
C7 | 0.0152 (13) | 0.0182 (14) | 0.0143 (13) | 0.0052 (11) | 0.0063 (11) | 0.0036 (11) |
C8 | 0.0144 (13) | 0.0171 (14) | 0.0177 (14) | 0.0046 (11) | 0.0069 (11) | 0.0034 (11) |
C9 | 0.0195 (14) | 0.0205 (15) | 0.0254 (16) | 0.0076 (12) | 0.0119 (12) | 0.0048 (12) |
C10 | 0.0223 (15) | 0.0272 (16) | 0.0317 (17) | 0.0091 (13) | 0.0190 (14) | 0.0083 (13) |
C11 | 0.0194 (14) | 0.0232 (16) | 0.0300 (16) | 0.0036 (12) | 0.0145 (13) | 0.0098 (13) |
C12 | 0.0187 (14) | 0.0161 (14) | 0.0241 (15) | 0.0049 (11) | 0.0078 (12) | 0.0039 (11) |
C13 | 0.0137 (13) | 0.0175 (14) | 0.0150 (13) | 0.0055 (11) | 0.0049 (11) | 0.0027 (11) |
C14 | 0.0140 (13) | 0.0108 (13) | 0.0198 (14) | 0.0001 (10) | 0.0067 (11) | 0.0003 (10) |
C15 | 0.0149 (13) | 0.0137 (13) | 0.0188 (14) | 0.0029 (10) | 0.0064 (11) | 0.0012 (11) |
C16 | 0.0176 (14) | 0.0185 (14) | 0.0193 (14) | 0.0043 (11) | 0.0088 (11) | 0.0044 (11) |
C17 | 0.0175 (14) | 0.0179 (14) | 0.0198 (15) | 0.0038 (11) | 0.0072 (12) | 0.0036 (11) |
C18 | 0.0163 (13) | 0.0160 (14) | 0.0229 (15) | 0.0042 (11) | 0.0058 (12) | 0.0007 (11) |
C19 | 0.0180 (14) | 0.0187 (14) | 0.0219 (15) | 0.0066 (11) | 0.0074 (12) | −0.0011 (11) |
C20 | 0.0155 (13) | 0.0124 (13) | 0.0166 (13) | 0.0015 (10) | 0.0039 (11) | −0.0015 (10) |
C21 | 0.0153 (13) | 0.0137 (13) | 0.0193 (14) | 0.0042 (11) | 0.0055 (11) | −0.0001 (11) |
C22 | 0.0205 (14) | 0.0194 (14) | 0.0199 (15) | 0.0075 (12) | 0.0079 (12) | −0.0002 (11) |
C23 | 0.0215 (14) | 0.0180 (14) | 0.0187 (14) | 0.0056 (12) | 0.0052 (12) | 0.0018 (11) |
C24 | 0.0174 (14) | 0.0143 (13) | 0.0220 (15) | 0.0040 (11) | 0.0060 (12) | 0.0007 (11) |
C25 | 0.0141 (13) | 0.0162 (14) | 0.0223 (15) | 0.0037 (11) | 0.0073 (11) | 0.0011 (11) |
C26 | 0.0150 (13) | 0.0144 (13) | 0.0180 (14) | 0.0031 (11) | 0.0059 (11) | 0.0005 (11) |
C27 | 0.0243 (15) | 0.0320 (17) | 0.0217 (16) | 0.0133 (13) | 0.0088 (13) | 0.0072 (13) |
C28 | 0.0262 (16) | 0.0301 (17) | 0.0290 (17) | 0.0167 (14) | 0.0082 (14) | 0.0013 (14) |
C29 | 0.0328 (19) | 0.045 (2) | 0.037 (2) | 0.0147 (17) | 0.0166 (16) | 0.0016 (17) |
C30 | 0.0236 (15) | 0.0255 (16) | 0.0215 (15) | 0.0093 (13) | 0.0056 (12) | 0.0038 (12) |
C31 | 0.0282 (17) | 0.0348 (19) | 0.0212 (16) | 0.0125 (14) | 0.0089 (13) | 0.0048 (13) |
C32 | 0.032 (2) | 0.052 (3) | 0.032 (2) | 0.0077 (18) | 0.0090 (16) | −0.0129 (18) |
C33 | 0.0149 (13) | 0.0217 (15) | 0.0186 (14) | 0.0021 (11) | 0.0070 (11) | 0.0048 (11) |
C34 | 0.0196 (14) | 0.0284 (16) | 0.0188 (15) | 0.0062 (12) | 0.0053 (12) | 0.0048 (12) |
C35 | 0.0227 (15) | 0.0307 (17) | 0.0165 (14) | 0.0030 (13) | 0.0050 (12) | 0.0015 (12) |
C36 | 0.0218 (15) | 0.0229 (15) | 0.0184 (15) | 0.0028 (12) | 0.0076 (12) | −0.0005 (12) |
C37 | 0.0155 (13) | 0.0189 (14) | 0.0168 (14) | 0.0012 (11) | 0.0073 (11) | 0.0009 (11) |
C38 | 0.0181 (14) | 0.0194 (14) | 0.0164 (14) | 0.0031 (11) | 0.0092 (11) | −0.0005 (11) |
C39 | 0.0174 (13) | 0.0141 (13) | 0.0189 (14) | 0.0030 (11) | 0.0082 (11) | 0.0024 (11) |
C40 | 0.0146 (13) | 0.0159 (13) | 0.0193 (14) | 0.0024 (11) | 0.0071 (11) | 0.0029 (11) |
C41 | 0.0197 (14) | 0.0188 (14) | 0.0234 (15) | 0.0058 (12) | 0.0081 (12) | 0.0012 (12) |
C42 | 0.0226 (15) | 0.0213 (15) | 0.0332 (18) | 0.0114 (12) | 0.0090 (13) | 0.0034 (13) |
C43 | 0.0229 (15) | 0.0285 (17) | 0.0299 (17) | 0.0136 (13) | 0.0046 (13) | 0.0070 (14) |
C44 | 0.0228 (15) | 0.0242 (16) | 0.0211 (15) | 0.0085 (13) | 0.0023 (12) | 0.0018 (12) |
C45 | 0.0147 (13) | 0.0155 (13) | 0.0198 (14) | 0.0022 (11) | 0.0045 (11) | 0.0018 (11) |
C46 | 0.0195 (14) | 0.0189 (14) | 0.0119 (13) | 0.0062 (11) | 0.0012 (11) | 0.0025 (11) |
C47 | 0.0200 (14) | 0.0187 (14) | 0.0135 (13) | 0.0075 (12) | 0.0037 (11) | 0.0024 (11) |
C48 | 0.0224 (14) | 0.0180 (14) | 0.0130 (13) | 0.0090 (12) | 0.0054 (11) | 0.0023 (11) |
C49 | 0.0235 (15) | 0.0210 (15) | 0.0148 (13) | 0.0084 (12) | 0.0067 (12) | 0.0030 (11) |
C50 | 0.0277 (16) | 0.0234 (16) | 0.0204 (15) | 0.0101 (13) | 0.0126 (13) | 0.0034 (12) |
C51 | 0.0302 (16) | 0.0202 (15) | 0.0178 (14) | 0.0110 (13) | 0.0100 (13) | −0.0013 (11) |
C52 | 0.0265 (15) | 0.0174 (14) | 0.0116 (13) | 0.0069 (12) | 0.0035 (12) | 0.0009 (11) |
C53 | 0.0229 (15) | 0.0207 (15) | 0.0135 (13) | 0.0072 (12) | 0.0020 (11) | 0.0030 (11) |
C54 | 0.0304 (16) | 0.0157 (14) | 0.0157 (14) | 0.0071 (12) | 0.0007 (12) | 0.0004 (11) |
C55 | 0.0311 (17) | 0.0214 (16) | 0.0200 (15) | 0.0041 (13) | 0.0025 (13) | 0.0061 (12) |
C56 | 0.0259 (16) | 0.0243 (16) | 0.0251 (16) | 0.0043 (13) | 0.0057 (13) | 0.0072 (13) |
C57 | 0.0235 (15) | 0.0209 (15) | 0.0200 (15) | 0.0062 (12) | 0.0037 (12) | 0.0046 (12) |
C58 | 0.0236 (15) | 0.0170 (14) | 0.0149 (13) | 0.0057 (12) | 0.0038 (12) | 0.0020 (11) |
C59 | 0.0243 (15) | 0.0222 (15) | 0.0220 (15) | 0.0093 (12) | 0.0123 (12) | 0.0050 (12) |
C60 | 0.042 (2) | 0.036 (2) | 0.066 (3) | 0.0192 (18) | 0.033 (2) | −0.002 (2) |
C61 | 0.084 (4) | 0.067 (3) | 0.053 (3) | 0.045 (3) | 0.020 (3) | −0.003 (3) |
C62 | 0.038 (2) | 0.0278 (19) | 0.049 (2) | 0.0036 (15) | 0.0206 (18) | 0.0110 (17) |
C63 | 0.049 (2) | 0.0186 (17) | 0.0302 (18) | 0.0056 (16) | 0.0004 (17) | 0.0029 (14) |
C64 | 0.064 (3) | 0.0215 (18) | 0.036 (2) | −0.0025 (18) | −0.002 (2) | 0.0064 (16) |
C65 | 0.045 (2) | 0.035 (2) | 0.058 (3) | 0.0108 (18) | 0.028 (2) | 0.0163 (19) |
C66 | 0.110 (5) | 0.133 (6) | 0.049 (3) | 0.088 (5) | 0.031 (3) | 0.030 (4) |
C67 | 0.054 (3) | 0.097 (5) | 0.074 (4) | 0.037 (3) | 0.036 (3) | 0.040 (3) |
Geometric parameters (Å, º) top
Co1—N1 | 2.187 (3) | C24—C25 | 1.355 (4) |
Co1—N2 | 2.043 (2) | C24—C30 | 1.501 (4) |
Co1—N4 | 2.209 (2) | C25—H25 | 0.9500 |
Co1—N5 | 2.045 (2) | C25—C26 | 1.426 (4) |
Co1—O1 | 2.068 (2) | C27—H27A | 0.9800 |
Co1—O2 | 2.040 (2) | C27—H27B | 0.9800 |
Br1—C1 | 1.894 (3) | C27—H27C | 0.9800 |
Br2—C33 | 1.887 (3) | C28—H28A | 0.9900 |
N1—C1 | 1.323 (4) | C28—H28B | 0.9900 |
N1—C5 | 1.364 (4) | C28—C29 | 1.512 (5) |
N2—N3 | 1.371 (3) | C29—H29A | 0.9800 |
N2—C6 | 1.283 (4) | C29—H29B | 0.9800 |
N3—C7 | 1.336 (4) | C29—H29C | 0.9800 |
N4—C33 | 1.335 (4) | C30—H30A | 0.9800 |
N4—C37 | 1.367 (4) | C30—H30B | 0.9800 |
N5—N6 | 1.376 (4) | C30—H30C | 0.9800 |
N5—C38 | 1.286 (4) | C31—H31A | 0.9900 |
N6—C39 | 1.337 (4) | C31—H31B | 0.9900 |
N7—H7 | 0.8800 | C31—C32 | 1.521 (5) |
N7—C23 | 1.345 (4) | C32—H32A | 0.9800 |
N7—C31 | 1.458 (4) | C32—H32B | 0.9800 |
N8—H8 | 0.8800 | C32—H32C | 0.9800 |
N8—C18 | 1.347 (4) | C33—C34 | 1.390 (4) |
N8—C28 | 1.455 (4) | C34—H34 | 0.9500 |
N9—H9 | 0.8800 | C34—C35 | 1.383 (5) |
N9—C55 | 1.358 (4) | C35—H35 | 0.9500 |
N9—C63 | 1.447 (5) | C35—C36 | 1.393 (5) |
N10—H10 | 0.8800 | C36—H36 | 0.9500 |
N10—C50 | 1.343 (4) | C36—C37 | 1.389 (4) |
N10—C60 | 1.454 (4) | C37—C38 | 1.463 (4) |
O1—C7 | 1.273 (4) | C38—H38 | 0.9500 |
O2—C39 | 1.270 (4) | C39—C40 | 1.491 (4) |
O3—C20 | 1.361 (4) | C40—C41 | 1.393 (4) |
O3—C21 | 1.365 (4) | C40—C45 | 1.404 (4) |
O4—C52 | 1.364 (4) | C41—H41 | 0.9500 |
O4—C53 | 1.360 (4) | C41—C42 | 1.393 (5) |
O5—H5 | 0.8400 | C42—H42 | 0.9500 |
O5—C65 | 1.401 (5) | C42—C43 | 1.391 (5) |
O6—H6A | 0.8400 | C43—H43 | 0.9500 |
O6—C66 | 1.405 (6) | C43—C44 | 1.384 (5) |
Cl1—C67 | 1.743 (6) | C44—H44 | 0.9500 |
Cl2—C67 | 1.779 (7) | C44—C45 | 1.397 (4) |
B1—F1 | 1.344 (9) | C45—C46 | 1.491 (4) |
B1—F2 | 1.512 (9) | C46—C47 | 1.399 (4) |
B1—F4 | 1.360 (8) | C46—C58 | 1.420 (4) |
B1—F1A | 1.407 (14) | C47—C48 | 1.424 (4) |
B1—F2A | 1.236 (9) | C47—C52 | 1.418 (4) |
B1—F4A | 1.353 (13) | C48—H48 | 0.9500 |
B1—F3 | 1.367 (5) | C48—C49 | 1.359 (4) |
B2—F5 | 1.366 (6) | C49—C50 | 1.447 (4) |
B2—F6 | 1.401 (5) | C49—C59 | 1.506 (4) |
B2—F7 | 1.395 (5) | C50—C51 | 1.409 (5) |
B2—F8 | 1.370 (5) | C51—H51 | 0.9500 |
C1—C2 | 1.387 (5) | C51—C52 | 1.363 (5) |
C2—H2 | 0.9500 | C53—C54 | 1.383 (4) |
C2—C3 | 1.377 (5) | C53—C58 | 1.409 (4) |
C3—H3 | 0.9500 | C54—H54 | 0.9500 |
C3—C4 | 1.389 (5) | C54—C55 | 1.387 (5) |
C4—H4 | 0.9500 | C55—C56 | 1.444 (5) |
C4—C5 | 1.392 (4) | C56—C57 | 1.367 (5) |
C5—C6 | 1.462 (4) | C56—C62 | 1.499 (5) |
C6—H6 | 0.9500 | C57—H57 | 0.9500 |
C7—C8 | 1.487 (4) | C57—C58 | 1.414 (5) |
C8—C9 | 1.393 (4) | C59—H59A | 0.9800 |
C8—C13 | 1.414 (4) | C59—H59B | 0.9800 |
C9—H9A | 0.9500 | C59—H59C | 0.9800 |
C9—C10 | 1.388 (4) | C60—H60A | 0.9900 |
C10—H10A | 0.9500 | C60—H60B | 0.9900 |
C10—C11 | 1.389 (5) | C60—C61 | 1.458 (7) |
C11—H11 | 0.9500 | C61—H61A | 0.9800 |
C11—C12 | 1.392 (4) | C61—H61B | 0.9800 |
C12—H12 | 0.9500 | C61—H61C | 0.9800 |
C12—C13 | 1.396 (4) | C62—H62A | 0.9800 |
C13—C14 | 1.494 (4) | C62—H62B | 0.9800 |
C14—C15 | 1.404 (4) | C62—H62C | 0.9800 |
C14—C26 | 1.412 (4) | C63—H63A | 0.9900 |
C15—C16 | 1.432 (4) | C63—H63B | 0.9900 |
C15—C20 | 1.416 (4) | C63—C64 | 1.518 (5) |
C16—H16 | 0.9500 | C64—H64A | 0.9800 |
C16—C17 | 1.361 (4) | C64—H64B | 0.9800 |
C17—C18 | 1.441 (4) | C64—H64C | 0.9800 |
C17—C27 | 1.500 (4) | C65—H65A | 0.9800 |
C18—C19 | 1.407 (4) | C65—H65B | 0.9800 |
C19—H19 | 0.9500 | C65—H65C | 0.9800 |
C19—C20 | 1.372 (4) | C66—H66A | 0.9800 |
C21—C22 | 1.376 (4) | C66—H66B | 0.9800 |
C21—C26 | 1.407 (4) | C66—H66C | 0.9800 |
C22—H22 | 0.9500 | C67—H67A | 0.9900 |
C22—C23 | 1.401 (4) | C67—H67B | 0.9900 |
C23—C24 | 1.448 (4) | | |
| | | |
N1—Co1—N4 | 98.15 (9) | C28—C29—H29B | 109.5 |
N2—Co1—N1 | 75.81 (10) | C28—C29—H29C | 109.5 |
N2—Co1—N4 | 114.92 (10) | H29A—C29—H29B | 109.5 |
N2—Co1—N5 | 159.69 (10) | H29A—C29—H29C | 109.5 |
N2—Co1—O1 | 75.69 (9) | H29B—C29—H29C | 109.5 |
N5—Co1—N1 | 121.20 (10) | C24—C30—H30A | 109.5 |
N5—Co1—N4 | 75.84 (10) | C24—C30—H30B | 109.5 |
N5—Co1—O1 | 87.12 (9) | C24—C30—H30C | 109.5 |
O1—Co1—N1 | 151.44 (9) | H30A—C30—H30B | 109.5 |
O1—Co1—N4 | 92.07 (9) | H30A—C30—H30C | 109.5 |
O2—Co1—N1 | 86.02 (9) | H30B—C30—H30C | 109.5 |
O2—Co1—N2 | 96.67 (9) | N7—C31—H31A | 109.1 |
O2—Co1—N4 | 148.25 (9) | N7—C31—H31B | 109.1 |
O2—Co1—N5 | 75.17 (9) | N7—C31—C32 | 112.6 (3) |
O2—Co1—O1 | 99.14 (9) | H31A—C31—H31B | 107.8 |
C1—N1—Co1 | 131.1 (2) | C32—C31—H31A | 109.1 |
C1—N1—C5 | 116.5 (3) | C32—C31—H31B | 109.1 |
C5—N1—Co1 | 112.28 (19) | C31—C32—H32A | 109.5 |
N3—N2—Co1 | 118.11 (18) | C31—C32—H32B | 109.5 |
C6—N2—Co1 | 120.6 (2) | C31—C32—H32C | 109.5 |
C6—N2—N3 | 120.5 (2) | H32A—C32—H32B | 109.5 |
C7—N3—N2 | 107.9 (2) | H32A—C32—H32C | 109.5 |
C33—N4—Co1 | 131.2 (2) | H32B—C32—H32C | 109.5 |
C33—N4—C37 | 116.9 (3) | N4—C33—Br2 | 116.9 (2) |
C37—N4—Co1 | 110.16 (19) | N4—C33—C34 | 124.8 (3) |
N6—N5—Co1 | 118.14 (18) | C34—C33—Br2 | 118.3 (2) |
C38—N5—Co1 | 119.7 (2) | C33—C34—H34 | 121.3 |
C38—N5—N6 | 121.2 (3) | C35—C34—C33 | 117.5 (3) |
C39—N6—N5 | 107.0 (2) | C35—C34—H34 | 121.3 |
C23—N7—H7 | 117.5 | C34—C35—H35 | 120.2 |
C23—N7—C31 | 125.0 (3) | C34—C35—C36 | 119.5 (3) |
C31—N7—H7 | 117.5 | C36—C35—H35 | 120.2 |
C18—N8—H8 | 117.5 | C35—C36—H36 | 120.5 |
C18—N8—C28 | 124.9 (3) | C37—C36—C35 | 119.0 (3) |
C28—N8—H8 | 117.5 | C37—C36—H36 | 120.5 |
C55—N9—H9 | 118.5 | N4—C37—C36 | 122.2 (3) |
C55—N9—C63 | 123.0 (3) | N4—C37—C38 | 116.1 (3) |
C63—N9—H9 | 118.5 | C36—C37—C38 | 121.7 (3) |
C50—N10—H10 | 118.1 | N5—C38—C37 | 115.3 (3) |
C50—N10—C60 | 123.8 (3) | N5—C38—H38 | 122.4 |
C60—N10—H10 | 118.1 | C37—C38—H38 | 122.4 |
C7—O1—Co1 | 111.58 (18) | N6—C39—C40 | 117.9 (3) |
C39—O2—Co1 | 112.79 (18) | O2—C39—N6 | 125.5 (3) |
C20—O3—C21 | 120.3 (2) | O2—C39—C40 | 116.6 (3) |
C53—O4—C52 | 120.2 (2) | C41—C40—C39 | 121.3 (3) |
C65—O5—H5 | 109.5 | C41—C40—C45 | 119.5 (3) |
C66—O6—H6A | 109.5 | C45—C40—C39 | 119.1 (3) |
F1—B1—F2 | 103.6 (6) | C40—C41—H41 | 119.8 |
F1—B1—F4 | 105.1 (7) | C40—C41—C42 | 120.4 (3) |
F1—B1—F3 | 117.8 (6) | C42—C41—H41 | 119.8 |
F4—B1—F2 | 103.8 (6) | C41—C42—H42 | 120.1 |
F4—B1—F3 | 115.6 (5) | C43—C42—C41 | 119.8 (3) |
F2A—B1—F1A | 110.0 (10) | C43—C42—H42 | 120.1 |
F2A—B1—F4A | 124.6 (10) | C42—C43—H43 | 119.8 |
F2A—B1—F3 | 108.8 (5) | C44—C43—C42 | 120.3 (3) |
F4A—B1—F1A | 103.7 (8) | C44—C43—H43 | 119.8 |
F4A—B1—F3 | 104.1 (7) | C43—C44—H44 | 119.9 |
F3—B1—F2 | 109.4 (4) | C43—C44—C45 | 120.2 (3) |
F3—B1—F1A | 103.7 (10) | C45—C44—H44 | 119.9 |
F5—B2—F6 | 108.7 (4) | C40—C45—C46 | 123.9 (3) |
F5—B2—F7 | 109.3 (4) | C44—C45—C40 | 119.7 (3) |
F5—B2—F8 | 111.6 (4) | C44—C45—C46 | 116.4 (3) |
F7—B2—F6 | 107.7 (3) | C47—C46—C45 | 121.1 (3) |
F8—B2—F6 | 110.1 (3) | C47—C46—C58 | 118.8 (3) |
F8—B2—F7 | 109.3 (3) | C58—C46—C45 | 119.9 (3) |
N1—C1—Br1 | 116.0 (2) | C46—C47—C48 | 124.3 (3) |
N1—C1—C2 | 125.7 (3) | C46—C47—C52 | 119.5 (3) |
C2—C1—Br1 | 118.3 (2) | C52—C47—C48 | 116.0 (3) |
C1—C2—H2 | 121.5 | C47—C48—H48 | 118.5 |
C3—C2—C1 | 117.1 (3) | C49—C48—C47 | 122.9 (3) |
C3—C2—H2 | 121.5 | C49—C48—H48 | 118.5 |
C2—C3—H3 | 120.2 | C48—C49—C50 | 118.9 (3) |
C2—C3—C4 | 119.5 (3) | C48—C49—C59 | 122.6 (3) |
C4—C3—H3 | 120.2 | C50—C49—C59 | 118.6 (3) |
C3—C4—H4 | 120.5 | N10—C50—C49 | 118.6 (3) |
C3—C4—C5 | 119.0 (3) | N10—C50—C51 | 121.9 (3) |
C5—C4—H4 | 120.5 | C51—C50—C49 | 119.5 (3) |
N1—C5—C4 | 122.1 (3) | C50—C51—H51 | 120.4 |
N1—C5—C6 | 115.6 (3) | C52—C51—C50 | 119.2 (3) |
C4—C5—C6 | 122.3 (3) | C52—C51—H51 | 120.4 |
N2—C6—C5 | 115.3 (3) | O4—C52—C47 | 120.8 (3) |
N2—C6—H6 | 122.4 | C51—C52—O4 | 115.8 (3) |
C5—C6—H6 | 122.4 | C51—C52—C47 | 123.4 (3) |
N3—C7—C8 | 116.1 (3) | O4—C53—C54 | 115.8 (3) |
O1—C7—N3 | 126.0 (3) | O4—C53—C58 | 121.5 (3) |
O1—C7—C8 | 117.9 (3) | C54—C53—C58 | 122.8 (3) |
C9—C8—C7 | 120.0 (3) | C53—C54—H54 | 120.2 |
C9—C8—C13 | 119.2 (3) | C53—C54—C55 | 119.5 (3) |
C13—C8—C7 | 120.7 (3) | C55—C54—H54 | 120.2 |
C8—C9—H9A | 119.3 | N9—C55—C54 | 121.4 (3) |
C10—C9—C8 | 121.5 (3) | N9—C55—C56 | 118.9 (3) |
C10—C9—H9A | 119.3 | C54—C55—C56 | 119.6 (3) |
C9—C10—H10A | 120.3 | C55—C56—C62 | 119.1 (3) |
C9—C10—C11 | 119.4 (3) | C57—C56—C55 | 118.8 (3) |
C11—C10—H10A | 120.3 | C57—C56—C62 | 122.1 (3) |
C10—C11—H11 | 120.0 | C56—C57—H57 | 118.6 |
C10—C11—C12 | 120.0 (3) | C56—C57—C58 | 122.8 (3) |
C12—C11—H11 | 120.0 | C58—C57—H57 | 118.6 |
C11—C12—H12 | 119.4 | C53—C58—C46 | 119.0 (3) |
C11—C12—C13 | 121.1 (3) | C53—C58—C57 | 116.4 (3) |
C13—C12—H12 | 119.4 | C57—C58—C46 | 124.6 (3) |
C8—C13—C14 | 124.2 (3) | C49—C59—H59A | 109.5 |
C12—C13—C8 | 118.8 (3) | C49—C59—H59B | 109.5 |
C12—C13—C14 | 117.0 (3) | C49—C59—H59C | 109.5 |
C15—C14—C13 | 121.5 (3) | H59A—C59—H59B | 109.5 |
C15—C14—C26 | 118.4 (3) | H59A—C59—H59C | 109.5 |
C26—C14—C13 | 119.7 (3) | H59B—C59—H59C | 109.5 |
C14—C15—C16 | 124.8 (3) | N10—C60—H60A | 109.2 |
C14—C15—C20 | 119.7 (3) | N10—C60—H60B | 109.2 |
C20—C15—C16 | 115.5 (3) | N10—C60—C61 | 111.9 (4) |
C15—C16—H16 | 118.6 | H60A—C60—H60B | 107.9 |
C17—C16—C15 | 122.8 (3) | C61—C60—H60A | 109.2 |
C17—C16—H16 | 118.6 | C61—C60—H60B | 109.2 |
C16—C17—C18 | 119.4 (3) | C60—C61—H61A | 109.5 |
C16—C17—C27 | 122.2 (3) | C60—C61—H61B | 109.5 |
C18—C17—C27 | 118.4 (3) | C60—C61—H61C | 109.5 |
N8—C18—C17 | 119.2 (3) | H61A—C61—H61B | 109.5 |
N8—C18—C19 | 121.7 (3) | H61A—C61—H61C | 109.5 |
C19—C18—C17 | 119.1 (3) | H61B—C61—H61C | 109.5 |
C18—C19—H19 | 120.3 | C56—C62—H62A | 109.5 |
C20—C19—C18 | 119.3 (3) | C56—C62—H62B | 109.5 |
C20—C19—H19 | 120.3 | C56—C62—H62C | 109.5 |
O3—C20—C15 | 120.9 (3) | H62A—C62—H62B | 109.5 |
O3—C20—C19 | 115.5 (3) | H62A—C62—H62C | 109.5 |
C19—C20—C15 | 123.7 (3) | H62B—C62—H62C | 109.5 |
O3—C21—C22 | 115.1 (3) | N9—C63—H63A | 109.6 |
O3—C21—C26 | 121.0 (3) | N9—C63—H63B | 109.6 |
C22—C21—C26 | 123.9 (3) | N9—C63—C64 | 110.2 (4) |
C21—C22—H22 | 120.5 | H63A—C63—H63B | 108.1 |
C21—C22—C23 | 119.0 (3) | C64—C63—H63A | 109.6 |
C23—C22—H22 | 120.5 | C64—C63—H63B | 109.6 |
N7—C23—C22 | 121.8 (3) | C63—C64—H64A | 109.5 |
N7—C23—C24 | 119.1 (3) | C63—C64—H64B | 109.5 |
C22—C23—C24 | 119.1 (3) | C63—C64—H64C | 109.5 |
C23—C24—C30 | 119.0 (3) | H64A—C64—H64B | 109.5 |
C25—C24—C23 | 119.5 (3) | H64A—C64—H64C | 109.5 |
C25—C24—C30 | 121.5 (3) | H64B—C64—H64C | 109.5 |
C24—C25—H25 | 118.6 | O5—C65—H65A | 109.5 |
C24—C25—C26 | 122.8 (3) | O5—C65—H65B | 109.5 |
C26—C25—H25 | 118.6 | O5—C65—H65C | 109.5 |
C14—C26—C25 | 124.6 (3) | H65A—C65—H65B | 109.5 |
C21—C26—C14 | 119.7 (3) | H65A—C65—H65C | 109.5 |
C21—C26—C25 | 115.7 (3) | H65B—C65—H65C | 109.5 |
C17—C27—H27A | 109.5 | O6—C66—H66A | 109.5 |
C17—C27—H27B | 109.5 | O6—C66—H66B | 109.5 |
C17—C27—H27C | 109.5 | O6—C66—H66C | 109.5 |
H27A—C27—H27B | 109.5 | H66A—C66—H66B | 109.5 |
H27A—C27—H27C | 109.5 | H66A—C66—H66C | 109.5 |
H27B—C27—H27C | 109.5 | H66B—C66—H66C | 109.5 |
N8—C28—H28A | 109.0 | Cl1—C67—Cl2 | 111.8 (3) |
N8—C28—H28B | 109.0 | Cl1—C67—H67A | 109.3 |
N8—C28—C29 | 113.1 (3) | Cl1—C67—H67B | 109.3 |
H28A—C28—H28B | 107.8 | Cl2—C67—H67A | 109.3 |
C29—C28—H28A | 109.0 | Cl2—C67—H67B | 109.3 |
C29—C28—H28B | 109.0 | H67A—C67—H67B | 107.9 |
C28—C29—H29A | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···F3 | 0.88 | 2.25 | 2.903 (4) | 130 |
N8—H8···O6 | 0.88 | 2.10 | 2.900 (4) | 151 |
N10—H10···O5 | 0.88 | 2.07 | 2.882 (4) | 153 |
O5—H5···F4i | 0.84 | 2.22 | 2.897 (11) | 137 |
O5—H5···F1Ai | 0.84 | 1.99 | 2.762 (10) | 153 |
O6—H6A···F6 | 0.84 | 2.06 | 2.809 (4) | 149 |
C2—H2···F7ii | 0.95 | 2.43 | 3.142 (4) | 132 |
C4—H4···F2iii | 0.95 | 2.40 | 3.275 (6) | 153 |
C6—H6···F3iii | 0.95 | 2.50 | 3.323 (4) | 146 |
C12—H12···O3iv | 0.95 | 2.46 | 3.379 (4) | 162 |
C22—H22···F8v | 0.95 | 2.52 | 3.466 (4) | 179 |
C31—H31B···F7v | 0.99 | 2.43 | 3.302 (4) | 147 |
C44—H44···F2vi | 0.95 | 2.46 | 3.177 (6) | 133 |
C67—H67B···N6 | 0.99 | 2.34 | 3.277 (6) | 158 |
Symmetry codes: (i) x, y, z−1; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+2, −z+1; (v) −x+1, −y+2, −z+1; (vi) x−1, y, z−1. |
Selected bond lengths (Å) and angles (°) for complexes (1) and (2) top | (1) | (2) |
Co1—O1 | 2.064 (3) | 2.068 (2) |
Co1—O2 | 2.047 (3) | 2.040 (2) |
Co1—N1 | 2.188 (3) | 2.187 (3) |
Co1—N2 | 2.042 (3) | 2.043 (2) |
Co1—N4 | 2.208 (3) | 2.209 (2) |
Co1—N5 | 2.044 (3) | 2.045 (2) |
C7—O1 | 1.269 (5) | 1.273 (4) |
C39—O2 | 1.271 (5) | 1.270 (4) |
C1—Br1 | 1.892 (4) | 1.894 (3) |
C33—Br2 | 1.894 (4) | 1.887 (3) |
O1—Co1—N4 | 92.23 (11) | 92.07 (9) |
O1—Co1—N1 | 151.55 (11) | 151.44 (9) |
O2—Co1—O1 | 98.93 (11) | 99.14 (9) |
O2—Co1—N4 | 148.65 (12) | 148.25 (9) |
O2—Co1—N1 | 85.63 (11) | 86.02 (9) |
N2—Co1—O1 | 75.66 (11) | 75.69 (9) |
N2—Co1—O2 | 96.19 (11) | 96.67 (9) |
N2—Co1—N5 | 159.47 (13) | 159.69 (10) |
N2—Co1—N4 | 114.99 (12) | 114.92 (10) |
N2—Co1—N1 | 75.94 (12) | 75.81 (10) |
N5—Co1—O1 | 87.08 (12) | 87.12 (9) |
N5—Co1—O2 | 75.30 (12) | 75.17 (9) |
N5—Co1—N4 | 76.13 (12) | 75.84 (10) |
N5—Co1—N1 | 121.05 (12) | 121.20 (10) |
N1—Co1—N4 | 98.30 (11) | 98.15 (9) |
Obtained fit parameters for the magnetism of complexes (1) and (2) topParameter | (1) | (2) |
α | 1.27 (1) | 1.11 (1) |
λ (cm-1) | -61.3 (5) | -73.1 (6) |
Δ (cm-1) | -999 (7) | -855 (7) |
χTIP (ml mol-1) | 0.00266 (2) | 0.00281 (2) |
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