Bifunctional ligands containing both carboxylic and sulfonate groups can adopt versatile coordination modes to produce novel metal–organic frameworks (MOFs) with high-dimensional networks and interesting topologies. Using 2,2′-disulfonylbiphenyl-4,4′-dicarboxylic acid (H4L) as a linker and 4,4′-bipyridine (4,4′-bpy) as a co-ligand, two novel 3D CuII MOFs, {[Cu2(L)(4,4′-bpy)2.5(H2O)]·1.7H2O}n, (1), and {[Cu2(L)(4,4′-bpy)2]·DMA·3H2O}n, (2), have been synthesized and structurally characterized by X-ray crystallography (DMA is N,N-dimethylacetamide). MOF (1) shows an unprecedented trinodal 4,4,5-connected topology network with the Schläfli symbol (4.62.73)(43.65.7.8)(6.73.8.10), while MOF (2) indicates a binodal 4,6-connected fsc network with the Schläfli symbol (44.610.8)(44.62). MOFs (1) and (2) were further characterized by elemental analysis, IR spectroscopy, powder X-ray diffraction and thermogravimetric analysis. MOF (1) shows a high water and chemical stability. The proton conductivity of (1) and CO2 adsorption of (2) were also investigated.
Supporting information
CCDC references: 1921959; 1921960
For both structures, data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS2018/3 (Sheldrick, 2018); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
C39H28Cu2N5O11S2·1.7(H2O) | F(000) = 1968 |
Mr = 964.51 | Dx = 1.597 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.1292 (9) Å | Cell parameters from 6866 reflections |
b = 18.8549 (14) Å | θ = 2.8–25.4° |
c = 19.3898 (14) Å | µ = 1.24 mm−1 |
β = 99.510 (2)° | T = 296 K |
V = 4012.8 (5) Å3 | Block, blue |
Z = 4 | 0.25 × 0.23 × 0.15 mm |
Data collection top
Bruker APEXII CCD diffractometer | 6985 reflections with I > 2σ(I) |
ω scans | Rint = 0.031 |
Absorption correction: multi-scan SADABS (Bruker, 2005) | θmax = 27.3°, θmin = 1.5° |
Tmin = 0.742, Tmax = 0.831 | h = −14→13 |
31184 measured reflections | k = −24→24 |
9063 independent reflections | l = −25→25 |
Refinement top
Refinement on F2 | 96 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0496P)2 + 4.2886P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.003 |
8337 reflections | Δρmax = 0.65 e Å−3 |
605 parameters | Δρmin = −0.67 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) |
Cu1 | 0.57677 (3) | 0.51744 (2) | 0.78744 (2) | 0.02044 (9) | |
Cu2 | 0.26096 (3) | 0.75087 (2) | 1.03910 (2) | 0.02661 (10) | |
S1 | 0.43184 (6) | 0.68101 (3) | 1.18191 (3) | 0.02705 (15) | |
S2 | 0.79224 (7) | 0.79826 (4) | 1.07636 (4) | 0.03847 (18) | |
O1 | 0.59609 (17) | 0.53922 (10) | 0.88619 (10) | 0.0313 (4) | |
O2 | 0.6123 (2) | 0.64913 (12) | 0.84798 (10) | 0.0400 (5) | |
O4 | 0.6742 (6) | 0.7274 (4) | 1.4406 (4) | 0.0403 (10) | 0.452 (4) |
O3 | 0.8442 (5) | 0.7838 (3) | 1.4291 (3) | 0.0417 (9) | 0.452 (4) |
O3A | 0.7985 (5) | 0.7632 (3) | 1.4433 (3) | 0.0417 (9) | 0.548 (4) |
O4A | 0.6203 (5) | 0.7108 (3) | 1.4367 (3) | 0.0403 (10) | 0.548 (4) |
O5 | 0.41562 (17) | 0.70527 (10) | 1.10974 (10) | 0.0326 (4) | |
O6 | 0.41914 (19) | 0.60491 (11) | 1.18735 (12) | 0.0409 (5) | |
O7 | 0.3551 (2) | 0.71911 (14) | 1.22281 (12) | 0.0511 (6) | |
O8 | 0.7802 (3) | 0.83369 (14) | 1.00925 (14) | 0.0690 (8) | |
O9 | 0.7398 (2) | 0.83631 (11) | 1.12780 (13) | 0.0470 (6) | |
O10 | 0.9173 (2) | 0.77648 (14) | 1.10181 (15) | 0.0585 (7) | |
O1W | 0.1688 (2) | 0.78761 (11) | 1.12032 (11) | 0.0413 (5) | |
H1WA | 0.094075 | 0.778778 | 1.120840 | 0.050* | |
H1WB | 0.211835 | 0.763968 | 1.152670 | 0.050* | |
O2W | 0.6330 (4) | 0.7802 (3) | 0.7783 (3) | 0.1456 (19) | |
H2WA | 0.699265 | 0.780183 | 0.761845 | 0.175* | |
H2WB | 0.627204 | 0.740983 | 0.799055 | 0.175* | |
O3W | 0.5878 (11) | 0.8878 (6) | 0.8763 (6) | 0.132 (4) | 0.4 |
H3WA | 0.636033 | 0.876506 | 0.913343 | 0.158* | 0.4 |
H3WB | 0.596054 | 0.857586 | 0.844793 | 0.158* | 0.4 |
O3WA | 0.8793 (14) | 0.7693 (8) | 0.8916 (8) | 0.125 (5) | 0.3 |
H3WC | 0.955229 | 0.772783 | 0.906801 | 0.150* | 0.3 |
H3WD | 0.840921 | 0.782053 | 0.923911 | 0.150* | 0.3 |
N1 | 0.76060 (19) | 0.52073 (12) | 0.78792 (12) | 0.0280 (5) | |
N2 | 1.39120 (19) | 0.52700 (11) | 0.77794 (12) | 0.0252 (5) | |
N3 | 0.55566 (19) | 0.50631 (11) | 0.68410 (11) | 0.0233 (4) | |
N4 | 0.1699 (2) | 0.65858 (11) | 1.03174 (12) | 0.0281 (5) | |
N5 | 0.3471 (2) | 0.84396 (12) | 1.03796 (13) | 0.0393 (6) | |
C1 | 0.6141 (2) | 0.60567 (16) | 0.89630 (14) | 0.0299 (6) | |
C2 | 0.6365 (2) | 0.62907 (14) | 0.97112 (14) | 0.0267 (6) | |
C3 | 0.6888 (3) | 0.69463 (15) | 0.98951 (14) | 0.0302 (6) | |
H3 | 0.708998 | 0.724388 | 0.954930 | 0.036* | |
C4 | 0.7113 (2) | 0.71637 (14) | 1.05882 (14) | 0.0274 (6) | |
C5 | 0.6755 (2) | 0.67389 (14) | 1.11136 (13) | 0.0262 (6) | |
C6 | 0.6259 (3) | 0.60793 (15) | 1.09177 (14) | 0.0317 (6) | |
H6 | 0.603524 | 0.578302 | 1.125857 | 0.038* | |
C7 | 0.6086 (3) | 0.58499 (15) | 1.02332 (14) | 0.0308 (6) | |
H7 | 0.578223 | 0.539744 | 1.012196 | 0.037* | |
C8 | 0.6862 (2) | 0.69540 (13) | 1.18639 (14) | 0.0266 (6) | |
C9 | 0.5852 (2) | 0.69962 (13) | 1.22109 (13) | 0.0253 (5) | |
C10 | 0.6002 (3) | 0.71480 (15) | 1.29172 (14) | 0.0333 (6) | |
H10 | 0.532268 | 0.716717 | 1.313881 | 0.040* | |
C11 | 0.7142 (3) | 0.72717 (16) | 1.32989 (15) | 0.0411 (8) | |
C12 | 0.8145 (3) | 0.72483 (17) | 1.29603 (17) | 0.0429 (8) | |
H12 | 0.891685 | 0.734196 | 1.320853 | 0.051* | |
C13 | 0.8005 (3) | 0.70878 (15) | 1.22606 (16) | 0.0355 (7) | |
H13 | 0.869155 | 0.706753 | 1.204502 | 0.043* | |
C14A | 0.7515 (9) | 0.7497 (6) | 1.4049 (7) | 0.0325 (16) | 0.452 (4) |
C14B | 0.7065 (8) | 0.7330 (4) | 1.4096 (5) | 0.0325 (16) | 0.548 (4) |
C15 | 0.2889 (6) | 0.8976 (3) | 1.0013 (3) | 0.0329 (16) | 0.452 (4) |
H15 | 0.206120 | 0.892070 | 0.984817 | 0.039* | 0.452 (4) |
C15A | 0.2972 (7) | 0.9072 (3) | 1.0369 (3) | 0.060 (2) | 0.548 (4) |
H15A | 0.218351 | 0.910291 | 1.046665 | 0.071* | 0.548 (4) |
C16 | 0.3438 (4) | 0.9616 (4) | 0.9860 (3) | 0.0338 (16) | 0.452 (4) |
H16 | 0.298972 | 0.997707 | 0.961302 | 0.041* | 0.452 (4) |
C16A | 0.3509 (5) | 0.9665 (4) | 1.0230 (3) | 0.060 (2) | 0.548 (4) |
H16A | 0.307954 | 1.008877 | 1.022604 | 0.072* | 0.548 (4) |
C17 | 0.4668 (3) | 0.96822 (16) | 1.00931 (18) | 0.0523 (10) | |
C18 | 0.5260 (6) | 0.9150 (3) | 1.0489 (3) | 0.0443 (19) | 0.452 (4) |
H18 | 0.608095 | 0.919412 | 1.067609 | 0.053* | 0.452 (4) |
C18A | 0.5230 (7) | 0.9029 (3) | 1.0078 (4) | 0.074 (2) | 0.548 (4) |
H18A | 0.601053 | 0.900087 | 0.996743 | 0.089* | 0.548 (4) |
C19 | 0.4645 (4) | 0.8562 (4) | 1.0605 (3) | 0.0401 (18) | 0.452 (4) |
H19 | 0.508264 | 0.820606 | 1.086789 | 0.048* | 0.452 (4) |
C19A | 0.4603 (5) | 0.8383 (4) | 1.0234 (3) | 0.068 (2) | 0.548 (4) |
H19A | 0.498068 | 0.794280 | 1.023347 | 0.081* | 0.548 (4) |
C20 | 0.0503 (3) | 0.65856 (17) | 1.0209 (3) | 0.0641 (13) | |
H20 | 0.010121 | 0.701758 | 1.021561 | 0.077* | |
C21 | −0.0185 (3) | 0.59824 (17) | 1.0088 (3) | 0.0729 (15) | |
H21 | −0.102982 | 0.601428 | 1.002063 | 0.087* | |
C22 | 0.0356 (2) | 0.53336 (13) | 1.00658 (15) | 0.0291 (6) | |
C23 | 0.1606 (3) | 0.53392 (15) | 1.01821 (19) | 0.0430 (8) | |
H23 | 0.203009 | 0.491473 | 1.017703 | 0.052* | |
C24 | 0.2239 (3) | 0.59656 (15) | 1.03062 (17) | 0.0384 (7) | |
H24 | 0.308603 | 0.595011 | 1.038578 | 0.046* | |
C25 | 0.8149 (3) | 0.58206 (17) | 0.7775 (2) | 0.0457 (8) | |
H25 | 0.768331 | 0.623267 | 0.773089 | 0.055* | |
C26 | 0.9373 (3) | 0.58694 (17) | 0.7731 (2) | 0.0509 (9) | |
H26 | 0.972162 | 0.630782 | 0.766717 | 0.061* | |
C27 | 1.0072 (2) | 0.52638 (16) | 0.77818 (17) | 0.0346 (7) | |
C28 | 0.9502 (3) | 0.46313 (16) | 0.78738 (19) | 0.0434 (8) | |
H28 | 0.994040 | 0.420930 | 0.790393 | 0.052* | |
C29 | 0.8279 (3) | 0.46254 (16) | 0.79211 (18) | 0.0394 (7) | |
H29 | 0.791045 | 0.419306 | 0.798537 | 0.047* | |
C30 | 1.1399 (2) | 0.52836 (15) | 0.77545 (17) | 0.0342 (7) | |
C31 | 1.1939 (3) | 0.47809 (15) | 0.73838 (16) | 0.0345 (7) | |
H31 | 1.146687 | 0.443695 | 0.712304 | 0.041* | |
C32 | 1.3181 (2) | 0.47949 (15) | 0.74049 (15) | 0.0301 (6) | |
H32 | 1.352963 | 0.445908 | 0.714720 | 0.036* | |
C33 | 1.3385 (3) | 0.57669 (16) | 0.81218 (17) | 0.0376 (7) | |
H33 | 1.387420 | 0.611065 | 0.837212 | 0.045* | |
C34 | 1.2144 (3) | 0.57896 (17) | 0.81183 (19) | 0.0444 (8) | |
H34 | 1.181073 | 0.614519 | 0.836060 | 0.053* | |
C35 | 0.5117 (3) | 0.56167 (16) | 0.64619 (15) | 0.0435 (8) | |
H35 | 0.493898 | 0.602708 | 0.669123 | 0.052* | |
C36 | 0.4913 (3) | 0.56106 (17) | 0.57437 (15) | 0.0469 (9) | |
H36 | 0.462733 | 0.601709 | 0.549817 | 0.056* | |
C37 | 0.5127 (2) | 0.50099 (14) | 0.53876 (13) | 0.0266 (6) | |
C38 | 0.5611 (4) | 0.44370 (16) | 0.57869 (16) | 0.0476 (9) | |
H38 | 0.579862 | 0.402064 | 0.557061 | 0.057* | |
C39 | 0.5811 (3) | 0.44858 (16) | 0.65028 (15) | 0.0429 (8) | |
H39 | 0.613979 | 0.409651 | 0.676218 | 0.051* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.01505 (15) | 0.02898 (17) | 0.01744 (16) | 0.00000 (11) | 0.00317 (11) | −0.00236 (12) |
Cu2 | 0.02923 (18) | 0.02347 (16) | 0.02502 (18) | −0.01044 (13) | −0.00174 (13) | 0.00624 (12) |
S1 | 0.0262 (3) | 0.0290 (3) | 0.0258 (3) | −0.0046 (3) | 0.0040 (3) | 0.0033 (3) |
S2 | 0.0428 (4) | 0.0323 (4) | 0.0411 (4) | −0.0166 (3) | 0.0094 (3) | −0.0038 (3) |
O1 | 0.0310 (10) | 0.0396 (11) | 0.0226 (10) | −0.0010 (8) | 0.0023 (8) | −0.0093 (8) |
O2 | 0.0457 (13) | 0.0496 (13) | 0.0248 (11) | 0.0003 (10) | 0.0058 (9) | 0.0002 (9) |
O4 | 0.041 (3) | 0.050 (2) | 0.0300 (15) | −0.0049 (19) | 0.007 (2) | −0.0048 (16) |
O3 | 0.039 (3) | 0.049 (2) | 0.034 (2) | −0.0111 (16) | −0.0047 (17) | −0.0154 (17) |
O3A | 0.039 (3) | 0.049 (2) | 0.034 (2) | −0.0111 (16) | −0.0047 (17) | −0.0154 (17) |
O4A | 0.041 (3) | 0.050 (2) | 0.0300 (15) | −0.0049 (19) | 0.007 (2) | −0.0048 (16) |
O5 | 0.0296 (10) | 0.0359 (11) | 0.0295 (10) | −0.0073 (8) | −0.0031 (8) | 0.0108 (8) |
O6 | 0.0405 (12) | 0.0329 (11) | 0.0480 (13) | −0.0136 (9) | 0.0035 (10) | 0.0141 (9) |
O7 | 0.0364 (12) | 0.0745 (17) | 0.0449 (14) | 0.0069 (12) | 0.0136 (10) | −0.0094 (12) |
O8 | 0.102 (2) | 0.0561 (16) | 0.0483 (15) | −0.0406 (15) | 0.0118 (15) | 0.0089 (12) |
O9 | 0.0556 (15) | 0.0310 (11) | 0.0545 (14) | −0.0048 (10) | 0.0091 (11) | −0.0107 (10) |
O10 | 0.0322 (12) | 0.0555 (15) | 0.089 (2) | −0.0167 (11) | 0.0137 (13) | −0.0112 (14) |
O1W | 0.0390 (12) | 0.0415 (12) | 0.0445 (13) | −0.0064 (9) | 0.0101 (10) | −0.0027 (10) |
O2W | 0.105 (3) | 0.148 (4) | 0.196 (5) | 0.007 (3) | 0.059 (3) | 0.085 (4) |
O3W | 0.167 (8) | 0.113 (7) | 0.109 (7) | 0.007 (6) | 0.005 (6) | −0.011 (6) |
O3WA | 0.130 (8) | 0.147 (9) | 0.111 (8) | −0.018 (7) | 0.060 (7) | −0.006 (7) |
N1 | 0.0170 (11) | 0.0378 (13) | 0.0295 (12) | −0.0012 (9) | 0.0049 (9) | −0.0014 (10) |
N2 | 0.0180 (11) | 0.0298 (11) | 0.0287 (12) | −0.0006 (9) | 0.0068 (9) | −0.0009 (9) |
N3 | 0.0216 (11) | 0.0294 (11) | 0.0196 (11) | 0.0027 (9) | 0.0053 (8) | 0.0007 (9) |
N4 | 0.0264 (12) | 0.0246 (11) | 0.0319 (12) | −0.0073 (9) | 0.0012 (10) | −0.0005 (9) |
N5 | 0.0349 (14) | 0.0345 (13) | 0.0463 (15) | −0.0148 (11) | 0.0003 (12) | 0.0146 (11) |
C1 | 0.0204 (13) | 0.0455 (17) | 0.0240 (14) | 0.0013 (11) | 0.0041 (11) | −0.0049 (12) |
C2 | 0.0221 (13) | 0.0335 (14) | 0.0248 (13) | −0.0013 (11) | 0.0044 (11) | −0.0063 (11) |
C3 | 0.0336 (15) | 0.0335 (14) | 0.0252 (14) | −0.0039 (12) | 0.0096 (12) | 0.0000 (11) |
C4 | 0.0268 (14) | 0.0288 (13) | 0.0278 (14) | −0.0062 (11) | 0.0078 (11) | −0.0043 (11) |
C5 | 0.0260 (14) | 0.0309 (13) | 0.0221 (13) | −0.0051 (11) | 0.0050 (11) | −0.0049 (10) |
C6 | 0.0387 (16) | 0.0312 (14) | 0.0268 (14) | −0.0119 (12) | 0.0102 (12) | −0.0026 (11) |
C7 | 0.0339 (15) | 0.0308 (14) | 0.0282 (14) | −0.0110 (12) | 0.0065 (12) | −0.0086 (11) |
C8 | 0.0313 (14) | 0.0250 (12) | 0.0231 (13) | −0.0044 (11) | 0.0032 (11) | −0.0035 (10) |
C9 | 0.0304 (14) | 0.0243 (12) | 0.0203 (13) | −0.0035 (10) | 0.0019 (11) | −0.0006 (10) |
C10 | 0.0455 (18) | 0.0311 (14) | 0.0238 (14) | 0.0051 (12) | 0.0071 (12) | −0.0007 (11) |
C11 | 0.061 (2) | 0.0335 (15) | 0.0237 (15) | 0.0095 (14) | −0.0088 (14) | −0.0079 (12) |
C12 | 0.0418 (18) | 0.0405 (17) | 0.0386 (18) | 0.0017 (14) | −0.0156 (14) | −0.0118 (14) |
C13 | 0.0302 (15) | 0.0367 (15) | 0.0371 (16) | −0.0046 (12) | −0.0014 (12) | −0.0066 (13) |
C14A | 0.038 (5) | 0.027 (4) | 0.029 (2) | 0.001 (3) | −0.006 (4) | −0.005 (3) |
C14B | 0.038 (5) | 0.027 (4) | 0.029 (2) | 0.001 (3) | −0.006 (4) | −0.005 (3) |
C15 | 0.026 (3) | 0.026 (3) | 0.046 (4) | −0.007 (2) | 0.007 (3) | −0.003 (3) |
C15A | 0.065 (4) | 0.043 (3) | 0.082 (4) | −0.012 (3) | 0.044 (4) | −0.012 (3) |
C16 | 0.034 (3) | 0.023 (3) | 0.044 (4) | −0.003 (2) | 0.005 (3) | 0.013 (3) |
C16A | 0.068 (4) | 0.041 (3) | 0.081 (4) | −0.005 (3) | 0.041 (3) | −0.006 (3) |
C17 | 0.0380 (19) | 0.0360 (17) | 0.080 (3) | −0.0144 (14) | −0.0004 (18) | 0.0248 (17) |
C18 | 0.034 (3) | 0.039 (3) | 0.054 (4) | −0.015 (3) | −0.011 (3) | 0.022 (3) |
C18A | 0.053 (4) | 0.076 (4) | 0.092 (5) | −0.015 (3) | 0.008 (4) | 0.035 (4) |
C19 | 0.033 (3) | 0.028 (3) | 0.051 (4) | −0.012 (2) | −0.018 (3) | 0.013 (3) |
C19A | 0.059 (4) | 0.047 (3) | 0.091 (4) | −0.010 (3) | −0.004 (3) | 0.016 (3) |
C20 | 0.0279 (17) | 0.0261 (16) | 0.137 (4) | −0.0023 (13) | 0.010 (2) | −0.018 (2) |
C21 | 0.0217 (16) | 0.0301 (17) | 0.166 (5) | −0.0048 (13) | 0.012 (2) | −0.023 (2) |
C22 | 0.0241 (14) | 0.0234 (13) | 0.0393 (16) | −0.0054 (11) | 0.0034 (12) | −0.0040 (11) |
C23 | 0.0269 (15) | 0.0244 (14) | 0.074 (2) | 0.0015 (11) | −0.0038 (15) | −0.0037 (14) |
C24 | 0.0238 (14) | 0.0319 (15) | 0.057 (2) | −0.0044 (12) | −0.0021 (13) | −0.0010 (13) |
C25 | 0.0247 (15) | 0.0350 (16) | 0.080 (3) | 0.0032 (12) | 0.0157 (16) | 0.0000 (16) |
C26 | 0.0253 (16) | 0.0334 (16) | 0.098 (3) | −0.0040 (13) | 0.0210 (17) | −0.0025 (17) |
C27 | 0.0189 (14) | 0.0381 (16) | 0.0468 (18) | −0.0019 (11) | 0.0059 (12) | −0.0048 (13) |
C28 | 0.0232 (15) | 0.0339 (16) | 0.075 (2) | 0.0059 (12) | 0.0140 (15) | 0.0062 (15) |
C29 | 0.0244 (15) | 0.0341 (15) | 0.061 (2) | −0.0016 (12) | 0.0116 (14) | 0.0049 (14) |
C30 | 0.0187 (13) | 0.0363 (15) | 0.0493 (18) | −0.0014 (11) | 0.0102 (12) | −0.0009 (13) |
C31 | 0.0217 (14) | 0.0370 (15) | 0.0447 (17) | −0.0055 (11) | 0.0055 (12) | −0.0077 (13) |
C32 | 0.0221 (13) | 0.0348 (15) | 0.0345 (15) | −0.0003 (11) | 0.0074 (11) | −0.0058 (12) |
C33 | 0.0219 (14) | 0.0375 (16) | 0.0544 (19) | −0.0037 (12) | 0.0092 (13) | −0.0137 (14) |
C34 | 0.0234 (15) | 0.0423 (17) | 0.071 (2) | −0.0007 (12) | 0.0167 (15) | −0.0223 (16) |
C35 | 0.072 (2) | 0.0357 (16) | 0.0234 (15) | 0.0241 (16) | 0.0106 (14) | −0.0007 (12) |
C36 | 0.078 (2) | 0.0387 (17) | 0.0232 (15) | 0.0336 (17) | 0.0059 (15) | 0.0040 (12) |
C37 | 0.0314 (14) | 0.0297 (13) | 0.0191 (13) | 0.0058 (11) | 0.0050 (11) | 0.0001 (10) |
C38 | 0.088 (3) | 0.0311 (15) | 0.0242 (15) | 0.0209 (16) | 0.0104 (16) | −0.0001 (12) |
C39 | 0.073 (2) | 0.0321 (15) | 0.0231 (14) | 0.0201 (15) | 0.0061 (14) | 0.0056 (12) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.9352 (18) | C9—C10 | 1.382 (4) |
Cu1—N3 | 1.990 (2) | C10—C11 | 1.379 (4) |
Cu1—N1 | 2.045 (2) | C10—H10 | 0.9300 |
Cu1—N2i | 2.051 (2) | C11—C12 | 1.386 (5) |
Cu1—O6ii | 2.357 (2) | C11—C14A | 1.506 (13) |
Cu1—O2 | 2.747 (2) | C11—C14B | 1.565 (11) |
Cu2—O3Aiii | 1.988 (5) | C12—C13 | 1.374 (4) |
Cu2—N5 | 2.002 (2) | C12—H12 | 0.9300 |
Cu2—N4 | 2.007 (2) | C13—H13 | 0.9300 |
Cu2—O4iii | 2.035 (8) | C15—C16 | 1.406 (9) |
Cu2—O1W | 2.132 (2) | C15—H15 | 0.9300 |
Cu2—O5 | 2.1907 (19) | C15A—C16A | 1.317 (10) |
Cu2—O4Aiii | 2.427 (5) | C15A—H15A | 0.9300 |
Cu2—C14Biii | 2.503 (10) | C16—C17 | 1.374 (5) |
S1—O6 | 1.447 (2) | C16—H16 | 0.9300 |
S1—O7 | 1.448 (2) | C16A—C17 | 1.359 (5) |
S1—O5 | 1.455 (2) | C16A—H16A | 0.9300 |
S1—C9 | 1.784 (3) | C17—C18 | 1.365 (5) |
S2—O9 | 1.429 (2) | C17—C18A | 1.385 (5) |
S2—O8 | 1.449 (3) | C17—C17iv | 1.484 (6) |
S2—O10 | 1.457 (3) | C18—C19 | 1.341 (9) |
S2—C4 | 1.791 (3) | C18—H18 | 0.9300 |
O1—C1 | 1.279 (4) | C18A—C19A | 1.460 (10) |
O2—C1 | 1.242 (3) | C18A—H18A | 0.9300 |
O4—C14A | 1.261 (12) | C19—H19 | 0.9300 |
O3—C14A | 1.241 (10) | C19A—H19A | 0.9300 |
O3A—C14B | 1.256 (9) | C20—C21 | 1.369 (4) |
O4A—C14B | 1.241 (10) | C20—H20 | 0.9300 |
O1W—H1WA | 0.8499 | C21—C22 | 1.367 (4) |
O1W—H1WB | 0.8498 | C21—H21 | 0.9300 |
O2W—H2WA | 0.8501 | C22—C23 | 1.371 (4) |
O2W—H2WB | 0.8500 | C22—C22v | 1.487 (5) |
O3W—H3WA | 0.8499 | C23—C24 | 1.376 (4) |
O3W—H3WB | 0.8503 | C23—H23 | 0.9300 |
O3WA—H3WC | 0.8500 | C24—H24 | 0.9300 |
O3WA—H3WD | 0.8501 | C25—C26 | 1.382 (4) |
N1—C29 | 1.323 (4) | C25—H25 | 0.9300 |
N1—C25 | 1.335 (4) | C26—C27 | 1.376 (4) |
N2—C33 | 1.338 (4) | C26—H26 | 0.9300 |
N2—C32 | 1.340 (3) | C27—C28 | 1.376 (4) |
N3—C35 | 1.323 (4) | C27—C30 | 1.487 (4) |
N3—C39 | 1.325 (4) | C28—C29 | 1.380 (4) |
N4—C20 | 1.314 (4) | C28—H28 | 0.9300 |
N4—C24 | 1.317 (4) | C29—H29 | 0.9300 |
N5—C15A | 1.314 (4) | C30—C34 | 1.379 (4) |
N5—C19 | 1.327 (4) | C30—C31 | 1.385 (4) |
N5—C15 | 1.339 (4) | C31—C32 | 1.376 (4) |
N5—C19A | 1.340 (5) | C31—H31 | 0.9300 |
C1—C2 | 1.498 (4) | C32—H32 | 0.9300 |
C2—C7 | 1.384 (4) | C33—C34 | 1.381 (4) |
C2—C3 | 1.387 (4) | C33—H33 | 0.9300 |
C3—C4 | 1.388 (4) | C34—H34 | 0.9300 |
C3—H3 | 0.9300 | C35—C36 | 1.373 (4) |
C4—C5 | 1.405 (4) | C35—H35 | 0.9300 |
C5—C6 | 1.388 (4) | C36—C37 | 1.368 (4) |
C5—C8 | 1.496 (4) | C36—H36 | 0.9300 |
C6—C7 | 1.379 (4) | C37—C38 | 1.385 (4) |
C6—H6 | 0.9300 | C37—C37vi | 1.483 (5) |
C7—H7 | 0.9300 | C38—C39 | 1.372 (4) |
C8—C13 | 1.397 (4) | C38—H38 | 0.9300 |
C8—C9 | 1.405 (4) | C39—H39 | 0.9300 |
| | | |
O1—Cu1—N3 | 173.79 (9) | C11—C10—H10 | 119.4 |
O1—Cu1—N1 | 92.38 (9) | C9—C10—H10 | 119.4 |
N3—Cu1—N1 | 87.67 (9) | C10—C11—C12 | 118.8 (3) |
O1—Cu1—N2i | 90.91 (9) | C10—C11—C14A | 130.4 (5) |
N3—Cu1—N2i | 88.24 (9) | C12—C11—C14A | 110.6 (5) |
N1—Cu1—N2i | 171.67 (9) | C10—C11—C14B | 110.3 (4) |
O1—Cu1—O6ii | 90.42 (8) | C12—C11—C14B | 130.5 (4) |
N3—Cu1—O6ii | 95.78 (8) | C13—C12—C11 | 120.4 (3) |
N1—Cu1—O6ii | 92.51 (8) | C13—C12—H12 | 119.8 |
N2i—Cu1—O6ii | 95.12 (8) | C11—C12—H12 | 119.8 |
O1—Cu1—O2 | 53.18 (7) | C12—C13—C8 | 121.8 (3) |
N3—Cu1—O2 | 120.69 (8) | C12—C13—H13 | 119.1 |
N1—Cu1—O2 | 84.12 (8) | C8—C13—H13 | 119.1 |
N2i—Cu1—O2 | 91.74 (8) | O3—C14A—O4 | 124.4 (11) |
O6ii—Cu1—O2 | 143.09 (7) | O3—C14A—C11 | 126.2 (9) |
O3Aiii—Cu2—N5 | 86.08 (17) | O4—C14A—C11 | 109.4 (7) |
O3Aiii—Cu2—N4 | 89.97 (16) | O4A—C14B—O3A | 123.6 (9) |
N5—Cu2—N4 | 175.28 (9) | O4A—C14B—C11 | 124.5 (6) |
N5—Cu2—O4iii | 88.1 (2) | O3A—C14B—C11 | 111.9 (6) |
N4—Cu2—O4iii | 87.2 (2) | C11—C14B—Cu2vii | 162.8 (5) |
O3Aiii—Cu2—O1W | 159.16 (15) | N5—C15—C16 | 124.8 (6) |
N5—Cu2—O1W | 90.75 (9) | N5—C15—H15 | 117.6 |
N4—Cu2—O1W | 92.03 (9) | C16—C15—H15 | 117.6 |
O4iii—Cu2—O1W | 114.6 (2) | N5—C15A—C16A | 124.7 (6) |
O3Aiii—Cu2—O5 | 105.50 (15) | N5—C15A—H15A | 117.7 |
N5—Cu2—O5 | 91.29 (8) | C16A—C15A—H15A | 117.7 |
N4—Cu2—O5 | 92.26 (8) | C17—C16—C15 | 117.0 (5) |
O4iii—Cu2—O5 | 150.2 (2) | C17—C16—H16 | 121.5 |
O1W—Cu2—O5 | 95.15 (8) | C15—C16—H16 | 121.5 |
N5—Cu2—O4Aiii | 88.57 (14) | C15A—C16A—C17 | 122.5 (6) |
N4—Cu2—O4Aiii | 87.17 (14) | C15A—C16A—H16A | 118.8 |
O4iii—Cu2—O4Aiii | 14.1 (2) | C17—C16A—H16A | 118.8 |
O1W—Cu2—O4Aiii | 100.58 (14) | C18—C17—C16 | 118.6 (5) |
O5—Cu2—O4Aiii | 164.27 (14) | C16A—C17—C18A | 115.5 (5) |
N5—Cu2—C14Biii | 85.4 (2) | C18—C17—C17iv | 121.1 (4) |
N4—Cu2—C14Biii | 89.9 (2) | C16—C17—C17iv | 120.2 (4) |
O4iii—Cu2—C14Biii | 15.1 (2) | C19—C18—C17 | 119.4 (6) |
O1W—Cu2—C14Biii | 129.46 (19) | C19—C18—H18 | 120.3 |
O5—Cu2—C14Biii | 135.23 (19) | C17—C18—H18 | 120.3 |
O6—S1—O7 | 112.23 (15) | C17—C18A—C19A | 120.3 (6) |
O6—S1—O5 | 112.57 (13) | C17—C18A—H18A | 119.8 |
O7—S1—O5 | 112.34 (14) | C19A—C18A—H18A | 119.8 |
O6—S1—C9 | 105.18 (12) | N5—C19—C18 | 126.1 (6) |
O7—S1—C9 | 106.15 (13) | N5—C19—H19 | 116.9 |
O5—S1—C9 | 107.80 (12) | C18—C19—H19 | 116.9 |
O9—S2—O8 | 114.05 (17) | N5—C19A—C18A | 118.4 (6) |
O9—S2—O10 | 112.51 (16) | N5—C19A—H19A | 120.8 |
O8—S2—O10 | 112.04 (18) | C18A—C19A—H19A | 120.8 |
O9—S2—C4 | 108.33 (13) | N4—C20—C21 | 123.4 (3) |
O8—S2—C4 | 104.95 (14) | N4—C20—H20 | 118.3 |
O10—S2—C4 | 104.09 (14) | C21—C20—H20 | 118.3 |
C1—O1—Cu1 | 110.39 (17) | C22—C21—C20 | 120.8 (3) |
C1—O2—Cu1 | 73.10 (16) | C22—C21—H21 | 119.6 |
C14A—O4—Cu2vii | 100.8 (6) | C20—C21—H21 | 119.6 |
S1—O5—Cu2 | 133.21 (12) | C21—C22—C23 | 115.3 (3) |
S1—O6—Cu1ii | 170.63 (14) | C21—C22—C22v | 122.5 (3) |
Cu2—O1W—H1WA | 122.4 | C23—C22—C22v | 122.2 (3) |
Cu2—O1W—H1WB | 95.4 | C22—C23—C24 | 120.8 (3) |
H1WA—O1W—H1WB | 108.8 | C22—C23—H23 | 119.6 |
H2WA—O2W—H2WB | 108.4 | C24—C23—H23 | 119.6 |
H3WA—O3W—H3WB | 108.2 | N4—C24—C23 | 122.9 (3) |
H3WC—O3WA—H3WD | 108.3 | N4—C24—H24 | 118.5 |
C29—N1—C25 | 117.5 (2) | C23—C24—H24 | 118.5 |
C29—N1—Cu1 | 122.04 (19) | N1—C25—C26 | 122.8 (3) |
C25—N1—Cu1 | 120.19 (19) | N1—C25—H25 | 118.6 |
C33—N2—C32 | 117.4 (2) | C26—C25—H25 | 118.6 |
C33—N2—Cu1viii | 122.30 (18) | C27—C26—C25 | 119.4 (3) |
C32—N2—Cu1viii | 120.12 (18) | C27—C26—H26 | 120.3 |
C35—N3—C39 | 117.6 (2) | C25—C26—H26 | 120.3 |
C35—N3—Cu1 | 116.59 (18) | C26—C27—C28 | 117.5 (3) |
C39—N3—Cu1 | 125.84 (18) | C26—C27—C30 | 122.0 (3) |
C20—N4—C24 | 116.8 (2) | C28—C27—C30 | 120.5 (3) |
C20—N4—Cu2 | 119.9 (2) | C27—C28—C29 | 119.8 (3) |
C24—N4—Cu2 | 123.03 (19) | C27—C28—H28 | 120.1 |
C19—N5—C15 | 114.0 (5) | C29—C28—H28 | 120.1 |
C15A—N5—C19A | 118.6 (5) | N1—C29—C28 | 122.9 (3) |
C15A—N5—Cu2 | 126.4 (4) | N1—C29—H29 | 118.5 |
C19—N5—Cu2 | 126.6 (3) | C28—C29—H29 | 118.5 |
C15—N5—Cu2 | 118.5 (3) | C34—C30—C31 | 117.6 (3) |
C19A—N5—Cu2 | 113.6 (4) | C34—C30—C27 | 121.0 (3) |
O2—C1—O1 | 123.2 (3) | C31—C30—C27 | 121.3 (3) |
O2—C1—C2 | 121.0 (3) | C32—C31—C30 | 119.4 (3) |
O1—C1—C2 | 115.7 (2) | C32—C31—H31 | 120.3 |
C7—C2—C3 | 118.8 (2) | C30—C31—H31 | 120.3 |
C7—C2—C1 | 120.7 (2) | N2—C32—C31 | 123.1 (3) |
C3—C2—C1 | 120.5 (2) | N2—C32—H32 | 118.5 |
C2—C3—C4 | 120.9 (3) | C31—C32—H32 | 118.5 |
C2—C3—H3 | 119.6 | N2—C33—C34 | 122.6 (3) |
C4—C3—H3 | 119.6 | N2—C33—H33 | 118.7 |
C3—C4—C5 | 120.4 (2) | C34—C33—H33 | 118.7 |
C3—C4—S2 | 116.3 (2) | C30—C34—C33 | 119.8 (3) |
C5—C4—S2 | 123.2 (2) | C30—C34—H34 | 120.1 |
C6—C5—C4 | 117.4 (2) | C33—C34—H34 | 120.1 |
C6—C5—C8 | 118.2 (2) | N3—C35—C36 | 122.7 (3) |
C4—C5—C8 | 124.3 (2) | N3—C35—H35 | 118.6 |
C7—C6—C5 | 122.0 (3) | C36—C35—H35 | 118.6 |
C7—C6—H6 | 119.0 | C37—C36—C35 | 120.3 (3) |
C5—C6—H6 | 119.0 | C37—C36—H36 | 119.8 |
C6—C7—C2 | 120.2 (2) | C35—C36—H36 | 119.8 |
C6—C7—H7 | 119.9 | C36—C37—C38 | 116.6 (3) |
C2—C7—H7 | 119.9 | C36—C37—C37vi | 120.8 (3) |
C13—C8—C9 | 117.0 (2) | C38—C37—C37vi | 122.6 (3) |
C13—C8—C5 | 120.2 (3) | C39—C38—C37 | 119.8 (3) |
C9—C8—C5 | 122.6 (2) | C39—C38—H38 | 120.1 |
C10—C9—C8 | 120.7 (3) | C37—C38—H38 | 120.1 |
C10—C9—S1 | 114.4 (2) | N3—C39—C38 | 122.9 (3) |
C8—C9—S1 | 124.7 (2) | N3—C39—H39 | 118.5 |
C11—C10—C9 | 121.1 (3) | C38—C39—H39 | 118.5 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+1, −y+2, −z+2; (v) −x, −y+1, −z+2; (vi) −x+1, −y+1, −z+1; (vii) x+1/2, −y+3/2, z+1/2; (viii) x+1, y, z. |
Crystal data top
C34H22Cu2N4O10S2·C4H9NO·3(H2O) | F(000) = 2008 |
Mr = 978.95 | Dx = 1.595 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.123 (7) Å | Cell parameters from 2565 reflections |
b = 23.956 (15) Å | θ = 2.6–20.9° |
c = 16.026 (10) Å | µ = 1.22 mm−1 |
β = 107.374 (9)° | T = 293 K |
V = 4076 (4) Å3 | Block, blue |
Z = 4 | 0.12 × 0.11 × 0.10 mm |
Data collection top
Bruker APEXII CCD diffractometer | 4973 reflections with I > 2σ(I) |
ω scans | Rint = 0.082 |
Absorption correction: multi-scan SADABS (Bruker, 2005) | θmax = 27.0°, θmin = 1.6° |
Tmin = 0.864, Tmax = 0.885 | h = −14→13 |
30310 measured reflections | k = −30→30 |
8891 independent reflections | l = −20→19 |
Refinement top
Refinement on F2 | 55 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.061 | H-atom parameters constrained |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.0779P)2 + 1.4096P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
8092 reflections | Δρmax = 1.22 e Å−3 |
582 parameters | Δρmin = −0.60 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) |
Cu1 | 0.95063 (6) | 0.02448 (2) | 0.37089 (4) | 0.02914 (19) | |
Cu2 | 1.13542 (5) | 0.39212 (2) | 0.37413 (4) | 0.02786 (18) | |
S1 | 1.06947 (17) | 0.23664 (6) | 0.78325 (9) | 0.0354 (4) | 0.92 |
S1A | 1.1423 (19) | 0.2343 (6) | 0.7811 (9) | 0.0354 (4) | 0.08 |
S2 | 1.22202 (14) | 0.36838 (6) | 0.60278 (10) | 0.0415 (4) | |
O1 | 0.9775 (3) | 0.09507 (13) | 0.4332 (2) | 0.0330 (8) | |
O2 | 1.0249 (3) | 0.06110 (14) | 0.5685 (2) | 0.0373 (9) | |
O3 | 1.1260 (3) | 0.18404 (14) | 0.8236 (2) | 0.0384 (9) | |
O4 | 1.1548 (6) | 0.28273 (18) | 0.8101 (3) | 0.0577 (15) | 0.92 |
O5 | 0.9464 (5) | 0.2455 (2) | 0.7956 (3) | 0.0617 (14) | 0.92 |
O4A | 1.092 (5) | 0.283 (2) | 0.812 (5) | 0.05 (2)* | 0.08 |
O5A | 1.267 (4) | 0.246 (3) | 0.777 (5) | 0.11 (2)* | 0.08 |
O6 | 1.2854 (4) | 0.3189 (2) | 0.6458 (3) | 0.0766 (16) | |
O7 | 1.2913 (5) | 0.4198 (2) | 0.6297 (4) | 0.0904 (19) | |
O8 | 1.1829 (4) | 0.36183 (18) | 0.5081 (2) | 0.0535 (11) | |
O9 | 0.9001 (3) | 0.51810 (13) | 0.7545 (2) | 0.0312 (8) | |
O1O | 0.8656 (3) | 0.52647 (13) | 0.6108 (2) | 0.0298 (8) | |
O11 | 0.5321 (6) | 0.1425 (2) | 0.5979 (4) | 0.101 (2) | |
O1W | 0.4383 (8) | 0.2823 (4) | 0.8009 (5) | 0.186 (4) | |
H1WA | 0.413663 | 0.294090 | 0.748453 | 0.279* | |
H1WB | 0.373593 | 0.278560 | 0.818253 | 0.279* | |
O2W | 0.5488 (16) | 0.4439 (11) | 0.6480 (11) | 0.190 (10) | 0.523 (17) |
H2WA | 0.565797 | 0.477962 | 0.641975 | 0.228* | 0.523 (17) |
H2WB | 0.470137 | 0.440852 | 0.640444 | 0.228* | 0.523 (17) |
O2WA | 0.5618 (13) | 0.3835 (9) | 0.6584 (10) | 0.135 (8) | 0.477 (17) |
H2WC | 0.484998 | 0.389798 | 0.654210 | 0.162* | 0.477 (17) |
H2WD | 0.586557 | 0.355488 | 0.691600 | 0.162* | 0.477 (17) |
O3W | 0.6795 (10) | 0.2904 (4) | 0.7709 (9) | 0.255 (6) | |
H3WA | 0.649243 | 0.274208 | 0.807366 | 0.383* | |
H3WB | 0.753123 | 0.278118 | 0.776426 | 0.383* | |
N1 | 0.7687 (4) | 0.02679 (18) | 0.3688 (3) | 0.0377 (11) | |
N2 | 0.1298 (4) | 0.02681 (17) | 0.3706 (3) | 0.0337 (10) | |
N3 | 0.9505 (4) | 0.39542 (18) | 0.3649 (3) | 0.0364 (11) | |
N4 | 0.3138 (4) | 0.39625 (17) | 0.3711 (3) | 0.0348 (11) | |
N5 | 0.5390 (13) | 0.2216 (6) | 0.5299 (11) | 0.099 (5) | 0.541 (8) |
N5A | 0.4442 (16) | 0.2185 (7) | 0.5333 (13) | 0.099 (5) | 0.459 (8) |
C1 | 1.0049 (4) | 0.10055 (19) | 0.5150 (3) | 0.0242 (11) | |
C2 | 1.0125 (4) | 0.1603 (2) | 0.5486 (3) | 0.0275 (11) | |
C3 | 1.0385 (4) | 0.17056 (19) | 0.6373 (3) | 0.0267 (11) | |
H3 | 1.054589 | 0.140905 | 0.676528 | 0.032* | |
C4 | 1.0408 (5) | 0.2254 (2) | 0.6683 (3) | 0.0307 (12) | |
C5 | 1.0155 (5) | 0.2702 (2) | 0.6102 (4) | 0.0354 (13) | |
C6 | 0.9933 (6) | 0.2588 (2) | 0.5210 (4) | 0.0432 (15) | |
H6 | 0.979319 | 0.288306 | 0.481530 | 0.052* | |
C7 | 0.9918 (6) | 0.2050 (2) | 0.4907 (4) | 0.0406 (14) | |
H7 | 0.976824 | 0.198553 | 0.431215 | 0.049* | |
C8 | 0.9990 (5) | 0.3298 (2) | 0.6360 (3) | 0.0345 (13) | |
C9 | 1.0776 (5) | 0.3752 (2) | 0.6328 (3) | 0.0312 (12) | |
C10 | 1.0443 (5) | 0.4288 (2) | 0.6504 (3) | 0.0337 (13) | |
H10 | 1.096952 | 0.458539 | 0.648019 | 0.040* | |
C11 | 0.9337 (5) | 0.43892 (19) | 0.6715 (3) | 0.0278 (11) | |
C12 | 0.8566 (5) | 0.3952 (2) | 0.6769 (4) | 0.0382 (13) | |
H12 | 0.783279 | 0.401436 | 0.691961 | 0.046* | |
C13 | 0.8901 (6) | 0.3404 (2) | 0.6592 (4) | 0.0444 (15) | |
H13 | 0.838063 | 0.310809 | 0.663103 | 0.053* | |
C14 | 0.8966 (4) | 0.49831 (19) | 0.6812 (3) | 0.0252 (11) | |
C15 | 0.7062 (5) | 0.0746 (2) | 0.3664 (4) | 0.0515 (17) | |
H15 | 0.748379 | 0.107886 | 0.364855 | 0.062* | |
C16 | 0.5838 (6) | 0.0771 (2) | 0.3661 (5) | 0.0560 (18) | |
H16 | 0.544722 | 0.111647 | 0.363676 | 0.067* | |
C17 | 0.5163 (5) | 0.0286 (2) | 0.3693 (4) | 0.0394 (14) | |
C18 | 0.5826 (6) | −0.0202 (2) | 0.3733 (5) | 0.065 (2) | |
H18 | 0.543428 | −0.054119 | 0.376463 | 0.078* | |
C19 | 0.7044 (6) | −0.0198 (2) | 0.3727 (5) | 0.066 (2) | |
H19 | 0.745491 | −0.053801 | 0.375073 | 0.079* | |
C20 | 0.3831 (5) | 0.0283 (2) | 0.3699 (4) | 0.0373 (13) | |
C21 | 0.3117 (5) | 0.0775 (2) | 0.3616 (4) | 0.0438 (15) | |
H21 | 0.347461 | 0.111694 | 0.355205 | 0.053* | |
C22 | 0.1887 (5) | 0.0750 (2) | 0.3629 (4) | 0.0389 (14) | |
H22 | 0.143868 | 0.108188 | 0.358275 | 0.047* | |
C23 | 0.1991 (6) | −0.0197 (3) | 0.3772 (5) | 0.0568 (18) | |
H23 | 0.160349 | −0.053571 | 0.380920 | 0.068* | |
C24 | 0.3218 (6) | −0.0209 (2) | 0.3787 (5) | 0.0584 (19) | |
H24 | 0.364890 | −0.054640 | 0.385674 | 0.070* | |
C25 | 0.8589 (5) | 0.3725 (3) | 0.3012 (5) | 0.0581 (19) | |
H25 | 0.879385 | 0.354832 | 0.255638 | 0.070* | |
C26 | 0.7339 (6) | 0.3740 (3) | 0.3001 (5) | 0.064 (2) | |
H26 | 0.672997 | 0.356834 | 0.254587 | 0.077* | |
C27 | 0.6976 (5) | 0.4013 (2) | 0.3668 (4) | 0.0387 (14) | |
C28 | 0.7936 (5) | 0.4277 (3) | 0.4308 (4) | 0.0438 (15) | |
H28 | 0.775336 | 0.447800 | 0.475149 | 0.053* | |
C29 | 0.9162 (5) | 0.4240 (2) | 0.4279 (4) | 0.0402 (14) | |
H29 | 0.978957 | 0.441886 | 0.471244 | 0.048* | |
C30 | 0.5653 (5) | 0.4014 (2) | 0.3675 (4) | 0.0427 (14) | |
C31 | 0.4717 (6) | 0.3766 (4) | 0.3008 (4) | 0.074 (2) | |
H31 | 0.490821 | 0.361553 | 0.252824 | 0.089* | |
C32 | 0.3495 (6) | 0.3743 (3) | 0.3056 (4) | 0.065 (2) | |
H32 | 0.288897 | 0.356434 | 0.260709 | 0.078* | |
C33 | 0.4047 (6) | 0.4198 (3) | 0.4359 (5) | 0.070 (2) | |
H33 | 0.383490 | 0.434835 | 0.483068 | 0.084* | |
C34 | 0.5289 (6) | 0.4227 (3) | 0.4358 (5) | 0.080 (3) | |
H34 | 0.588605 | 0.439366 | 0.482576 | 0.096* | |
C35 | 0.499 (2) | 0.2796 (7) | 0.5118 (17) | 0.126 (6) | 0.541 (8) |
H35A | 0.557981 | 0.299222 | 0.489782 | 0.188* | 0.541 (8) |
H35B | 0.417013 | 0.280582 | 0.469130 | 0.188* | 0.541 (8) |
H35C | 0.494283 | 0.297078 | 0.564775 | 0.188* | 0.541 (8) |
C35A | 0.423 (3) | 0.2707 (8) | 0.4853 (18) | 0.126 (6) | 0.459 (8) |
H35D | 0.429209 | 0.301174 | 0.525362 | 0.188* | 0.459 (8) |
H35E | 0.340218 | 0.270437 | 0.443807 | 0.188* | 0.459 (8) |
H35F | 0.484789 | 0.275095 | 0.455066 | 0.188* | 0.459 (8) |
C36 | 0.6732 (9) | 0.2092 (5) | 0.5460 (8) | 0.142 (5) | |
H36D | 0.656703 | 0.243314 | 0.513172 | 0.213* | 0.459 (8) |
H36E | 0.732720 | 0.216054 | 0.602227 | 0.213* | 0.459 (8) |
H36F | 0.707211 | 0.182090 | 0.515052 | 0.213* | 0.459 (8) |
H36A | 0.711138 | 0.237797 | 0.520292 | 0.213* | 0.541 (8) |
H36B | 0.714193 | 0.207790 | 0.607833 | 0.213* | 0.541 (8) |
H36C | 0.682063 | 0.173768 | 0.520369 | 0.213* | 0.541 (8) |
C37 | 0.4699 (12) | 0.1853 (6) | 0.5617 (11) | 0.065 (4) | 0.541 (8) |
C37A | 0.5487 (14) | 0.1866 (7) | 0.5581 (13) | 0.065 (4) | 0.459 (8) |
C38 | 0.3305 (8) | 0.1972 (4) | 0.5469 (7) | 0.114 (3) | |
H38A | 0.309323 | 0.232651 | 0.518221 | 0.171* | 0.541 (8) |
H38B | 0.281079 | 0.168427 | 0.510872 | 0.171* | 0.541 (8) |
H38C | 0.313325 | 0.198101 | 0.602084 | 0.171* | 0.541 (8) |
H38D | 0.264041 | 0.224026 | 0.526397 | 0.171* | 0.459 (8) |
H38E | 0.307294 | 0.162938 | 0.515128 | 0.171* | 0.459 (8) |
H38F | 0.344376 | 0.190508 | 0.608061 | 0.171* | 0.459 (8) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0291 (3) | 0.0238 (3) | 0.0376 (4) | −0.0031 (3) | 0.0147 (3) | −0.0098 (3) |
Cu2 | 0.0265 (3) | 0.0214 (3) | 0.0389 (4) | 0.0025 (3) | 0.0147 (3) | 0.0021 (3) |
S1 | 0.0591 (11) | 0.0221 (8) | 0.0262 (8) | 0.0005 (8) | 0.0145 (8) | −0.0017 (6) |
S1A | 0.0591 (11) | 0.0221 (8) | 0.0262 (8) | 0.0005 (8) | 0.0145 (8) | −0.0017 (6) |
S2 | 0.0431 (8) | 0.0426 (9) | 0.0428 (9) | 0.0068 (7) | 0.0187 (7) | −0.0003 (7) |
O1 | 0.048 (2) | 0.0234 (19) | 0.030 (2) | −0.0004 (16) | 0.0163 (17) | −0.0072 (16) |
O2 | 0.056 (2) | 0.0201 (19) | 0.040 (2) | 0.0010 (17) | 0.0202 (19) | 0.0018 (17) |
O3 | 0.056 (2) | 0.026 (2) | 0.036 (2) | 0.0036 (17) | 0.0178 (18) | 0.0066 (16) |
O4 | 0.093 (5) | 0.033 (3) | 0.041 (3) | −0.025 (3) | 0.010 (3) | −0.001 (2) |
O5 | 0.074 (3) | 0.074 (3) | 0.049 (3) | 0.027 (3) | 0.037 (3) | −0.003 (3) |
O6 | 0.076 (3) | 0.086 (4) | 0.077 (4) | 0.049 (3) | 0.037 (3) | 0.039 (3) |
O7 | 0.067 (3) | 0.083 (4) | 0.138 (5) | −0.032 (3) | 0.057 (3) | −0.057 (4) |
O8 | 0.058 (3) | 0.079 (3) | 0.028 (2) | 0.019 (2) | 0.019 (2) | 0.012 (2) |
O9 | 0.049 (2) | 0.0211 (18) | 0.026 (2) | 0.0081 (16) | 0.0162 (17) | 0.0016 (15) |
O1O | 0.043 (2) | 0.0221 (18) | 0.028 (2) | 0.0037 (16) | 0.0149 (16) | 0.0007 (15) |
O11 | 0.114 (5) | 0.059 (4) | 0.124 (5) | 0.013 (3) | 0.028 (4) | 0.028 (3) |
O1W | 0.158 (8) | 0.209 (9) | 0.148 (8) | −0.008 (6) | −0.020 (6) | 0.075 (7) |
O2W | 0.180 (12) | 0.208 (14) | 0.179 (12) | −0.004 (8) | 0.049 (8) | 0.002 (9) |
O2WA | 0.096 (9) | 0.183 (13) | 0.132 (10) | −0.007 (7) | 0.042 (7) | 0.002 (8) |
O3W | 0.192 (10) | 0.248 (12) | 0.367 (18) | 0.008 (9) | 0.146 (12) | −0.024 (11) |
N1 | 0.037 (3) | 0.034 (3) | 0.046 (3) | 0.000 (2) | 0.018 (2) | −0.009 (2) |
N2 | 0.036 (2) | 0.024 (2) | 0.045 (3) | 0.000 (2) | 0.017 (2) | −0.006 (2) |
N3 | 0.027 (2) | 0.037 (3) | 0.045 (3) | 0.002 (2) | 0.011 (2) | 0.002 (2) |
N4 | 0.031 (2) | 0.027 (2) | 0.050 (3) | 0.000 (2) | 0.019 (2) | −0.001 (2) |
N5 | 0.140 (15) | 0.058 (6) | 0.099 (8) | 0.000 (10) | 0.038 (11) | 0.029 (5) |
N5A | 0.140 (15) | 0.058 (6) | 0.099 (8) | 0.000 (10) | 0.038 (11) | 0.029 (5) |
C1 | 0.024 (2) | 0.018 (3) | 0.033 (3) | −0.002 (2) | 0.013 (2) | −0.007 (2) |
C2 | 0.032 (3) | 0.019 (3) | 0.035 (3) | 0.003 (2) | 0.014 (2) | −0.003 (2) |
C3 | 0.038 (3) | 0.019 (3) | 0.026 (3) | −0.001 (2) | 0.013 (2) | 0.000 (2) |
C4 | 0.039 (3) | 0.024 (3) | 0.032 (3) | 0.001 (2) | 0.016 (2) | −0.001 (2) |
C5 | 0.052 (3) | 0.019 (3) | 0.040 (3) | 0.004 (2) | 0.021 (3) | −0.002 (2) |
C6 | 0.078 (4) | 0.019 (3) | 0.034 (3) | 0.008 (3) | 0.019 (3) | 0.004 (2) |
C7 | 0.070 (4) | 0.025 (3) | 0.028 (3) | −0.003 (3) | 0.016 (3) | −0.003 (2) |
C8 | 0.047 (3) | 0.025 (3) | 0.033 (3) | 0.007 (3) | 0.014 (3) | 0.002 (2) |
C9 | 0.040 (3) | 0.025 (3) | 0.028 (3) | 0.012 (2) | 0.011 (2) | −0.001 (2) |
C10 | 0.036 (3) | 0.030 (3) | 0.034 (3) | 0.002 (2) | 0.010 (2) | −0.003 (2) |
C11 | 0.041 (3) | 0.018 (3) | 0.024 (3) | 0.006 (2) | 0.009 (2) | −0.001 (2) |
C12 | 0.051 (3) | 0.025 (3) | 0.046 (4) | 0.001 (3) | 0.025 (3) | −0.001 (3) |
C13 | 0.063 (4) | 0.020 (3) | 0.055 (4) | −0.009 (3) | 0.024 (3) | −0.001 (3) |
C14 | 0.024 (3) | 0.016 (2) | 0.039 (3) | 0.000 (2) | 0.015 (2) | 0.000 (2) |
C15 | 0.035 (3) | 0.034 (3) | 0.088 (5) | −0.001 (3) | 0.023 (3) | 0.006 (3) |
C16 | 0.040 (3) | 0.033 (3) | 0.104 (6) | 0.000 (3) | 0.035 (4) | 0.010 (3) |
C17 | 0.034 (3) | 0.038 (3) | 0.049 (4) | 0.003 (3) | 0.016 (3) | −0.006 (3) |
C18 | 0.046 (4) | 0.028 (3) | 0.130 (7) | −0.004 (3) | 0.042 (4) | −0.006 (4) |
C19 | 0.041 (4) | 0.020 (3) | 0.141 (7) | −0.003 (3) | 0.033 (4) | −0.011 (4) |
C20 | 0.032 (3) | 0.033 (3) | 0.049 (4) | 0.007 (2) | 0.016 (3) | −0.002 (3) |
C21 | 0.035 (3) | 0.032 (3) | 0.066 (4) | −0.002 (3) | 0.018 (3) | 0.002 (3) |
C22 | 0.036 (3) | 0.030 (3) | 0.054 (4) | 0.004 (2) | 0.019 (3) | 0.003 (3) |
C23 | 0.047 (4) | 0.034 (3) | 0.101 (6) | −0.001 (3) | 0.040 (4) | −0.003 (3) |
C24 | 0.043 (4) | 0.029 (3) | 0.111 (6) | 0.005 (3) | 0.036 (4) | 0.000 (3) |
C25 | 0.032 (3) | 0.075 (5) | 0.072 (5) | −0.005 (3) | 0.023 (3) | −0.029 (4) |
C26 | 0.041 (4) | 0.086 (5) | 0.068 (5) | −0.014 (3) | 0.018 (3) | −0.044 (4) |
C27 | 0.031 (3) | 0.041 (3) | 0.050 (4) | 0.000 (3) | 0.021 (3) | 0.000 (3) |
C28 | 0.039 (3) | 0.058 (4) | 0.039 (3) | −0.002 (3) | 0.021 (3) | −0.008 (3) |
C29 | 0.033 (3) | 0.055 (4) | 0.036 (3) | −0.002 (3) | 0.016 (3) | −0.003 (3) |
C30 | 0.032 (3) | 0.048 (4) | 0.049 (4) | 0.002 (3) | 0.013 (3) | −0.002 (3) |
C31 | 0.034 (3) | 0.148 (7) | 0.046 (4) | −0.013 (4) | 0.021 (3) | −0.029 (4) |
C32 | 0.034 (3) | 0.118 (6) | 0.047 (4) | −0.008 (4) | 0.019 (3) | −0.019 (4) |
C33 | 0.042 (4) | 0.095 (6) | 0.078 (5) | −0.014 (4) | 0.024 (4) | −0.045 (4) |
C34 | 0.034 (4) | 0.110 (6) | 0.104 (6) | −0.025 (4) | 0.034 (4) | −0.065 (5) |
C35 | 0.136 (9) | 0.101 (7) | 0.132 (8) | 0.004 (6) | 0.028 (7) | 0.026 (6) |
C35A | 0.136 (9) | 0.101 (7) | 0.132 (8) | 0.004 (6) | 0.028 (7) | 0.026 (6) |
C36 | 0.087 (7) | 0.155 (11) | 0.199 (13) | −0.042 (7) | 0.066 (8) | −0.024 (9) |
C37 | 0.084 (11) | 0.050 (6) | 0.064 (7) | −0.009 (8) | 0.025 (9) | 0.008 (5) |
C37A | 0.084 (11) | 0.050 (6) | 0.064 (7) | −0.009 (8) | 0.025 (9) | 0.008 (5) |
C38 | 0.070 (6) | 0.143 (9) | 0.138 (9) | 0.009 (6) | 0.045 (6) | −0.013 (7) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.941 (3) | C9—C10 | 1.390 (7) |
Cu1—N2i | 1.995 (4) | C10—C11 | 1.390 (7) |
Cu1—N1 | 2.015 (5) | C10—H10 | 0.9300 |
Cu1—O9ii | 2.052 (3) | C11—C12 | 1.373 (7) |
Cu1—O2iii | 2.250 (4) | C11—C14 | 1.503 (6) |
Cu2—O1Oiv | 1.966 (3) | C12—C13 | 1.414 (7) |
Cu2—O3ii | 1.986 (4) | C12—H12 | 0.9300 |
Cu2—N4i | 2.002 (4) | C13—H13 | 0.9300 |
Cu2—N3 | 2.020 (4) | C15—C16 | 1.361 (8) |
Cu2—O8 | 2.177 (4) | C15—H15 | 0.9300 |
S1—O4 | 1.436 (5) | C16—C17 | 1.392 (8) |
S1—O5 | 1.456 (5) | C16—H16 | 0.9300 |
S1—O3 | 1.469 (4) | C17—C18 | 1.374 (8) |
S1—C4 | 1.794 (5) | C17—C20 | 1.485 (7) |
S1A—O3 | 1.421 (14) | C18—C19 | 1.358 (8) |
S1A—O5A | 1.44 (2) | C18—H18 | 0.9300 |
S1A—O4A | 1.44 (2) | C19—H19 | 0.9300 |
S1A—C4 | 1.837 (15) | C20—C24 | 1.389 (7) |
S2—O6 | 1.445 (4) | C20—C21 | 1.405 (7) |
S2—O7 | 1.448 (5) | C21—C22 | 1.375 (7) |
S2—O8 | 1.457 (4) | C21—H21 | 0.9300 |
S2—C9 | 1.817 (5) | C22—H22 | 0.9300 |
O1—C1 | 1.261 (6) | C23—C24 | 1.358 (8) |
O2—C1 | 1.251 (6) | C23—H23 | 0.9300 |
O9—C14 | 1.256 (6) | C24—H24 | 0.9300 |
O1O—C14 | 1.271 (6) | C25—C26 | 1.385 (8) |
O11—C37 | 1.277 (12) | C25—H25 | 0.9300 |
O11—C37A | 1.277 (13) | C26—C27 | 1.411 (8) |
O1W—H1WA | 0.8499 | C26—H26 | 0.9300 |
O1W—H1WB | 0.8502 | C27—C28 | 1.392 (8) |
O2W—H2WA | 0.8499 | C27—C30 | 1.475 (7) |
O2W—H2WB | 0.8501 | C28—C29 | 1.382 (7) |
O2WA—H2WC | 0.8500 | C28—H28 | 0.9300 |
O2WA—H2WD | 0.8494 | C29—H29 | 0.9300 |
O3W—H3WA | 0.8497 | C30—C34 | 1.373 (8) |
O3W—H3WB | 0.8498 | C30—C31 | 1.384 (8) |
N1—C15 | 1.334 (7) | C31—C32 | 1.385 (8) |
N1—C19 | 1.336 (7) | C31—H31 | 0.9300 |
N2—C23 | 1.341 (7) | C32—H32 | 0.9300 |
N2—C22 | 1.351 (6) | C33—C34 | 1.384 (8) |
N3—C25 | 1.326 (7) | C33—H33 | 0.9300 |
N3—C29 | 1.363 (7) | C34—H34 | 0.9300 |
N4—C32 | 1.336 (7) | C35—H35A | 0.9600 |
N4—C33 | 1.339 (7) | C35—H35B | 0.9600 |
N5—C37 | 1.357 (14) | C35—H35C | 0.9600 |
N5—C35 | 1.461 (14) | C35A—H35D | 0.9600 |
N5—C36 | 1.468 (12) | C35A—H35E | 0.9600 |
N5A—C37A | 1.348 (15) | C35A—H35F | 0.9600 |
N5A—C38 | 1.439 (13) | C36—C37A | 1.551 (14) |
N5A—C35A | 1.450 (15) | C36—H36D | 0.9600 |
C1—C2 | 1.522 (6) | C36—H36E | 0.9600 |
C2—C3 | 1.385 (7) | C36—H36F | 0.9600 |
C2—C7 | 1.392 (7) | C36—H36A | 0.9600 |
C3—C4 | 1.402 (7) | C36—H36B | 0.9600 |
C3—H3 | 0.9300 | C36—H36C | 0.9600 |
C4—C5 | 1.394 (7) | C37—C38 | 1.524 (13) |
C5—C6 | 1.402 (7) | C38—H38A | 0.9600 |
C5—C8 | 1.512 (7) | C38—H38B | 0.9600 |
C6—C7 | 1.376 (7) | C38—H38C | 0.9600 |
C6—H6 | 0.9300 | C38—H38D | 0.9600 |
C7—H7 | 0.9300 | C38—H38E | 0.9600 |
C8—C13 | 1.392 (7) | C38—H38F | 0.9600 |
C8—C9 | 1.405 (7) | | |
| | | |
O1—Cu1—N2i | 88.65 (16) | C12—C13—H13 | 119.2 |
O1—Cu1—N1 | 89.09 (16) | O9—C14—O1O | 123.7 (4) |
N2i—Cu1—N1 | 176.66 (18) | O9—C14—C11 | 121.4 (4) |
O1—Cu1—O9ii | 149.23 (14) | O1O—C14—C11 | 114.9 (4) |
N2i—Cu1—O9ii | 90.82 (16) | N1—C15—C16 | 123.4 (5) |
N1—Cu1—O9ii | 89.87 (16) | N1—C15—H15 | 118.3 |
O1—Cu1—O2iii | 126.25 (14) | C16—C15—H15 | 118.3 |
N2i—Cu1—O2iii | 91.98 (15) | C15—C16—C17 | 120.8 (6) |
N1—Cu1—O2iii | 91.34 (16) | C15—C16—H16 | 119.6 |
O9ii—Cu1—O2iii | 84.52 (13) | C17—C16—H16 | 119.6 |
O1Oiv—Cu2—O3ii | 163.75 (14) | C18—C17—C16 | 115.1 (5) |
O1Oiv—Cu2—N4i | 89.79 (15) | C18—C17—C20 | 121.2 (5) |
O3ii—Cu2—N4i | 88.13 (16) | C16—C17—C20 | 123.6 (5) |
O1Oiv—Cu2—N3 | 85.80 (16) | C19—C18—C17 | 121.0 (6) |
O3ii—Cu2—N3 | 94.46 (17) | C19—C18—H18 | 119.5 |
N4i—Cu2—N3 | 172.64 (18) | C17—C18—H18 | 119.5 |
O1Oiv—Cu2—O8 | 102.60 (15) | N1—C19—C18 | 123.8 (6) |
O3ii—Cu2—O8 | 93.64 (16) | N1—C19—H19 | 118.1 |
N4i—Cu2—O8 | 95.17 (17) | C18—C19—H19 | 118.1 |
N3—Cu2—O8 | 91.54 (17) | C24—C20—C21 | 116.1 (5) |
O4—S1—O5 | 114.3 (3) | C24—C20—C17 | 121.7 (5) |
O4—S1—O3 | 111.7 (3) | C21—C20—C17 | 122.2 (5) |
O5—S1—O3 | 111.2 (3) | C22—C21—C20 | 119.9 (5) |
O4—S1—C4 | 108.8 (3) | C22—C21—H21 | 120.0 |
O5—S1—C4 | 106.0 (3) | C20—C21—H21 | 120.0 |
O3—S1—C4 | 104.2 (2) | N2—C22—C21 | 123.4 (5) |
O3—S1A—O5A | 117 (3) | N2—C22—H22 | 118.3 |
O3—S1A—O4A | 114 (3) | C21—C22—H22 | 118.3 |
O5A—S1A—O4A | 109 (4) | N2—C23—C24 | 124.8 (6) |
O3—S1A—C4 | 104.2 (9) | N2—C23—H23 | 117.6 |
O5A—S1A—C4 | 107 (3) | C24—C23—H23 | 117.6 |
O4A—S1A—C4 | 104 (3) | C23—C24—C20 | 120.1 (5) |
O6—S2—O7 | 114.5 (4) | C23—C24—H24 | 120.0 |
O6—S2—O8 | 111.1 (3) | C20—C24—H24 | 120.0 |
O7—S2—O8 | 111.6 (3) | N3—C25—C26 | 122.4 (6) |
O6—S2—C9 | 106.9 (3) | N3—C25—H25 | 118.8 |
O7—S2—C9 | 106.2 (3) | C26—C25—H25 | 118.8 |
O8—S2—C9 | 105.8 (2) | C25—C26—C27 | 121.0 (6) |
C1—O1—Cu1 | 125.3 (3) | C25—C26—H26 | 119.5 |
C1—O2—Cu1iii | 163.4 (3) | C27—C26—H26 | 119.5 |
S1—O3—Cu2v | 158.5 (3) | C28—C27—C26 | 116.0 (5) |
S2—O8—Cu2 | 154.2 (3) | C28—C27—C30 | 122.8 (5) |
C14—O9—Cu1v | 125.9 (3) | C26—C27—C30 | 121.2 (5) |
C14—O1O—Cu2iv | 115.3 (3) | C29—C28—C27 | 119.6 (5) |
H1WA—O1W—H1WB | 107.8 | C29—C28—H28 | 120.2 |
H2WA—O2W—H2WB | 108.7 | C27—C28—H28 | 120.2 |
H2WC—O2WA—H2WD | 108.7 | N3—C29—C28 | 123.7 (5) |
H3WA—O3W—H3WB | 109.7 | N3—C29—H29 | 118.2 |
C15—N1—C19 | 115.9 (5) | C28—C29—H29 | 118.2 |
C15—N1—Cu1 | 122.4 (4) | C34—C30—C31 | 116.2 (5) |
C19—N1—Cu1 | 121.7 (4) | C34—C30—C27 | 122.6 (5) |
C23—N2—C22 | 115.6 (5) | C31—C30—C27 | 121.0 (5) |
C23—N2—Cu1vi | 121.9 (4) | C30—C31—C32 | 119.9 (6) |
C22—N2—Cu1vi | 122.5 (3) | C30—C31—H31 | 120.0 |
C25—N3—C29 | 117.2 (5) | C32—C31—H31 | 120.0 |
C25—N3—Cu2 | 124.8 (4) | N4—C32—C31 | 123.6 (6) |
C29—N3—Cu2 | 118.0 (4) | N4—C32—H32 | 118.2 |
C32—N4—C33 | 116.3 (5) | C31—C32—H32 | 118.2 |
C32—N4—Cu2vi | 121.9 (4) | N4—C33—C34 | 122.9 (6) |
C33—N4—Cu2vi | 121.8 (4) | N4—C33—H33 | 118.5 |
C37—N5—C35 | 120.5 (15) | C34—C33—H33 | 118.5 |
C37—N5—C36 | 117.6 (10) | C30—C34—C33 | 120.9 (6) |
C35—N5—C36 | 117.7 (14) | C30—C34—H34 | 119.5 |
C37A—N5A—C38 | 118.3 (11) | C33—C34—H34 | 119.5 |
C37A—N5A—C35A | 129.5 (16) | N5—C35—H35A | 109.5 |
C38—N5A—C35A | 111.9 (16) | N5—C35—H35B | 109.5 |
O2—C1—O1 | 124.9 (4) | H35A—C35—H35B | 109.5 |
O2—C1—C2 | 119.2 (4) | N5—C35—H35C | 109.5 |
O1—C1—C2 | 115.9 (4) | H35A—C35—H35C | 109.5 |
C3—C2—C7 | 119.3 (5) | H35B—C35—H35C | 109.5 |
C3—C2—C1 | 120.2 (4) | N5A—C35A—H35D | 109.5 |
C7—C2—C1 | 120.5 (5) | N5A—C35A—H35E | 109.5 |
C2—C3—C4 | 120.4 (4) | H35D—C35A—H35E | 109.5 |
C2—C3—H3 | 119.8 | N5A—C35A—H35F | 109.5 |
C4—C3—H3 | 119.8 | H35D—C35A—H35F | 109.5 |
C5—C4—C3 | 120.5 (5) | H35E—C35A—H35F | 109.5 |
C5—C4—S1 | 120.6 (4) | C37A—C36—H36D | 109.5 |
C3—C4—S1 | 118.9 (4) | C37A—C36—H36E | 109.5 |
C5—C4—S1A | 120.7 (6) | H36D—C36—H36E | 109.5 |
C3—C4—S1A | 113.5 (6) | C37A—C36—H36F | 109.5 |
C4—C5—C6 | 118.0 (5) | H36D—C36—H36F | 109.5 |
C4—C5—C8 | 124.1 (5) | H36E—C36—H36F | 109.5 |
C6—C5—C8 | 117.7 (4) | N5—C36—H36A | 109.5 |
C7—C6—C5 | 121.5 (5) | N5—C36—H36B | 109.5 |
C7—C6—H6 | 119.2 | H36A—C36—H36B | 109.5 |
C5—C6—H6 | 119.2 | N5—C36—H36C | 109.5 |
C6—C7—C2 | 120.2 (5) | H36A—C36—H36C | 109.5 |
C6—C7—H7 | 119.9 | H36B—C36—H36C | 109.5 |
C2—C7—H7 | 119.9 | O11—C37—N5 | 113.3 (11) |
C13—C8—C9 | 118.0 (5) | O11—C37—C38 | 127.6 (11) |
C13—C8—C5 | 115.6 (5) | N5—C37—C38 | 119.0 (11) |
C9—C8—C5 | 126.3 (5) | O11—C37A—N5A | 112.1 (12) |
C10—C9—C8 | 120.1 (5) | O11—C37A—C36 | 128.2 (13) |
C10—C9—S2 | 116.5 (4) | N5A—C37A—C36 | 119.3 (12) |
C8—C9—S2 | 123.3 (4) | C37—C38—H38A | 109.5 |
C9—C10—C11 | 121.3 (5) | C37—C38—H38B | 109.5 |
C9—C10—H10 | 119.4 | H38A—C38—H38B | 109.5 |
C11—C10—H10 | 119.4 | C37—C38—H38C | 109.5 |
C12—C11—C10 | 119.8 (5) | H38A—C38—H38C | 109.5 |
C12—C11—C14 | 121.3 (5) | H38B—C38—H38C | 109.5 |
C10—C11—C14 | 118.7 (4) | N5A—C38—H38D | 109.5 |
C11—C12—C13 | 119.2 (5) | N5A—C38—H38E | 109.5 |
C11—C12—H12 | 120.4 | H38D—C38—H38E | 109.5 |
C13—C12—H12 | 120.4 | N5A—C38—H38F | 109.5 |
C8—C13—C12 | 121.7 (5) | H38D—C38—H38F | 109.5 |
C8—C13—H13 | 119.2 | H38E—C38—H38F | 109.5 |
| | | |
O5A—S1A—O3—Cu2v | −28 (5) | C5—C8—C13—C12 | −174.0 (5) |
O4A—S1A—O3—Cu2v | −158 (4) | C11—C12—C13—C8 | −0.3 (9) |
C4—S1A—O3—Cu2v | 89 (3) | Cu1v—O9—C14—O1O | −179.4 (3) |
O4—S1—O3—Cu2v | 148.8 (6) | Cu1v—O9—C14—C11 | −1.5 (6) |
O5—S1—O3—Cu2v | 19.8 (7) | Cu2iv—O1O—C14—O9 | 15.0 (6) |
C4—S1—O3—Cu2v | −93.9 (7) | Cu2iv—O1O—C14—C11 | −163.0 (3) |
O6—S2—O8—Cu2 | −152.6 (5) | C12—C11—C14—O9 | 74.4 (6) |
O7—S2—O8—Cu2 | −23.5 (7) | C10—C11—C14—O9 | −110.3 (5) |
C9—S2—O8—Cu2 | 91.7 (6) | C12—C11—C14—O1O | −107.6 (5) |
Cu1iii—O2—C1—O1 | −0.3 (15) | C10—C11—C14—O1O | 67.8 (6) |
Cu1iii—O2—C1—C2 | 179.3 (9) | C19—N1—C15—C16 | −1.2 (10) |
Cu1—O1—C1—O2 | 3.7 (7) | Cu1—N1—C15—C16 | −179.1 (5) |
Cu1—O1—C1—C2 | −175.9 (3) | N1—C15—C16—C17 | 0.7 (11) |
O2—C1—C2—C3 | −1.4 (7) | C15—C16—C17—C18 | 0.4 (10) |
O1—C1—C2—C3 | 178.2 (4) | C15—C16—C17—C20 | 179.5 (6) |
O2—C1—C2—C7 | 179.4 (5) | C16—C17—C18—C19 | −0.9 (11) |
O1—C1—C2—C7 | −1.0 (7) | C20—C17—C18—C19 | 180.0 (7) |
C7—C2—C3—C4 | 1.7 (7) | C15—N1—C19—C18 | 0.7 (11) |
C1—C2—C3—C4 | −177.5 (4) | Cu1—N1—C19—C18 | 178.6 (6) |
C2—C3—C4—C5 | 0.7 (8) | C17—C18—C19—N1 | 0.4 (13) |
C2—C3—C4—S1 | 177.8 (4) | C18—C17—C20—C24 | 3.1 (10) |
C2—C3—C4—S1A | −153.6 (8) | C16—C17—C20—C24 | −175.9 (6) |
O4—S1—C4—C5 | −45.3 (6) | C18—C17—C20—C21 | −176.8 (6) |
O5—S1—C4—C5 | 78.0 (5) | C16—C17—C20—C21 | 4.2 (9) |
O3—S1—C4—C5 | −164.6 (4) | C24—C20—C21—C22 | 0.3 (9) |
O4—S1—C4—C3 | 137.5 (5) | C17—C20—C21—C22 | −179.7 (5) |
O5—S1—C4—C3 | −99.1 (4) | C23—N2—C22—C21 | 0.1 (9) |
O3—S1—C4—C3 | 18.3 (5) | Cu1vi—N2—C22—C21 | −179.3 (4) |
O3—S1A—C4—C5 | 169.1 (8) | C20—C21—C22—N2 | −1.1 (9) |
O5A—S1A—C4—C5 | −66 (4) | C22—N2—C23—C24 | 1.7 (10) |
O4A—S1A—C4—C5 | 49 (3) | Cu1vi—N2—C23—C24 | −178.9 (6) |
O3—S1A—C4—C3 | −36.7 (14) | N2—C23—C24—C20 | −2.5 (12) |
O5A—S1A—C4—C3 | 88 (3) | C21—C20—C24—C23 | 1.3 (10) |
O4A—S1A—C4—C3 | −156 (3) | C17—C20—C24—C23 | −178.6 (6) |
C3—C4—C5—C6 | −2.7 (8) | C29—N3—C25—C26 | −3.9 (10) |
S1—C4—C5—C6 | −179.7 (4) | Cu2—N3—C25—C26 | 177.2 (5) |
S1A—C4—C5—C6 | 149.8 (9) | N3—C25—C26—C27 | 1.2 (11) |
C3—C4—C5—C8 | 171.6 (5) | C25—C26—C27—C28 | 2.3 (10) |
S1—C4—C5—C8 | −5.4 (8) | C25—C26—C27—C30 | −178.0 (6) |
S1A—C4—C5—C8 | −36.0 (11) | C26—C27—C28—C29 | −2.8 (9) |
C4—C5—C6—C7 | 2.3 (9) | C30—C27—C28—C29 | 177.4 (5) |
C8—C5—C6—C7 | −172.3 (5) | C25—N3—C29—C28 | 3.3 (9) |
C5—C6—C7—C2 | 0.0 (9) | Cu2—N3—C29—C28 | −177.7 (4) |
C3—C2—C7—C6 | −2.0 (8) | C27—C28—C29—N3 | 0.1 (9) |
C1—C2—C7—C6 | 177.2 (5) | C28—C27—C30—C34 | −6.8 (10) |
C4—C5—C8—C13 | −69.5 (7) | C26—C27—C30—C34 | 173.4 (7) |
C6—C5—C8—C13 | 104.8 (6) | C28—C27—C30—C31 | 177.3 (7) |
C4—C5—C8—C9 | 115.3 (6) | C26—C27—C30—C31 | −2.5 (10) |
C6—C5—C8—C9 | −70.4 (8) | C34—C30—C31—C32 | −0.1 (11) |
C13—C8—C9—C10 | −1.5 (8) | C27—C30—C31—C32 | 176.0 (6) |
C5—C8—C9—C10 | 173.6 (5) | C33—N4—C32—C31 | −2.3 (11) |
C13—C8—C9—S2 | −179.4 (4) | Cu2vi—N4—C32—C31 | 179.5 (6) |
C5—C8—C9—S2 | −4.3 (8) | C30—C31—C32—N4 | 1.8 (12) |
O6—S2—C9—C10 | 139.8 (4) | C32—N4—C33—C34 | 1.2 (11) |
O7—S2—C9—C10 | 17.1 (5) | Cu2vi—N4—C33—C34 | 179.4 (6) |
O8—S2—C9—C10 | −101.7 (4) | C31—C30—C34—C33 | −0.9 (12) |
O6—S2—C9—C8 | −42.2 (5) | C27—C30—C34—C33 | −177.0 (7) |
O7—S2—C9—C8 | −165.0 (5) | N4—C33—C34—C30 | 0.3 (13) |
O8—S2—C9—C8 | 76.3 (5) | C35—N5—C37—O11 | −160.6 (17) |
C8—C9—C10—C11 | 0.1 (8) | C36—N5—C37—O11 | −4 (2) |
S2—C9—C10—C11 | 178.1 (4) | C35—N5—C37—C38 | 23 (3) |
C9—C10—C11—C12 | 1.3 (8) | C36—N5—C37—C38 | 179.5 (12) |
C9—C10—C11—C14 | −174.1 (5) | C38—N5A—C37A—O11 | −5 (3) |
C10—C11—C12—C13 | −1.2 (8) | C35A—N5A—C37A—O11 | −178 (2) |
C14—C11—C12—C13 | 174.1 (5) | C38—N5A—C37A—C36 | −178.7 (15) |
C9—C8—C13—C12 | 1.6 (8) | C35A—N5A—C37A—C36 | 8 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) −x+2, −y, −z+1; (iv) −x+2, −y+1, −z+1; (v) x, −y+1/2, z+1/2; (vi) x−1, y, z. |