Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000311/ng2124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000311/ng2124Isup2.hkl |
CCDC reference: 636753
Data collection: SMART-NT (Bruker, 2001 or?? 1998); cell refinement: SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL.
[Cu(C8H4F3O2S)2(C12H10N4)] | Z = 2 |
Mr = 716.12 | F(000) = 722 |
Triclinic, P1 | Dx = 1.596 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7970 (5) Å | Cell parameters from 8339 reflections |
b = 12.5007 (6) Å | θ = 2.3–26.4° |
c = 13.9823 (7) Å | µ = 0.95 mm−1 |
α = 98.453 (1)° | T = 294 K |
β = 105.171 (1)° | Prism, green |
γ = 110.736 (1)° | 0.42 × 0.28 × 0.16 mm |
V = 1490.19 (13) Å3 |
Bruker SMART APEX CCD diffractometer | 6101 independent reflections |
Radiation source: fine-focus sealed tube | 4938 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 26.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −12→12 |
Tmin = 0.816, Tmax = 1.000 | k = −15→15 |
16194 measured reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0817P)2 + 0.2214P] where P = (Fo2 + 2Fc2)/3 |
6101 reflections | (Δ/σ)max < 0.001 |
435 parameters | Δρmax = 0.45 e Å−3 |
24 restraints | Δρmin = −0.34 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. 24 restraints used to model –C4H4S (thiophene) substituent disorder. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 0.0000 | 0.5000 | 0.0000 | 0.04555 (13) | |
Cu2 | 0.5000 | 0.0000 | 0.5000 | 0.05113 (14) | |
C1 | 0.0537 (3) | 0.5299 (2) | 0.22603 (19) | 0.0527 (6) | |
H1 | 0.1374 | 0.5127 | 0.2221 | 0.063* | |
C2 | 0.0333 (3) | 0.5472 (2) | 0.3208 (2) | 0.0557 (6) | |
C3 | −0.0894 (3) | 0.5764 (3) | 0.3258 (2) | 0.0659 (7) | |
H3 | −0.1066 | 0.5908 | 0.3878 | 0.079* | |
C4 | −0.1846 (3) | 0.5835 (3) | 0.2382 (3) | 0.0701 (8) | |
H4 | −0.2671 | 0.6031 | 0.2403 | 0.084* | |
C5 | −0.1581 (3) | 0.5617 (2) | 0.1472 (2) | 0.0623 (7) | |
H5 | −0.2256 | 0.5648 | 0.0879 | 0.075* | |
C6 | 0.1309 (3) | 0.5252 (3) | 0.4079 (2) | 0.0629 (7) | |
H6 | 0.1376 | 0.5556 | 0.4746 | 0.075* | |
C7 | 0.4214 (3) | 0.2100 (3) | 0.4974 (2) | 0.0585 (6) | |
H7 | 0.3824 | 0.1744 | 0.4271 | 0.070* | |
C8 | 0.4064 (3) | 0.3134 (2) | 0.53118 (19) | 0.0566 (6) | |
C9 | 0.4686 (3) | 0.3680 (3) | 0.6364 (2) | 0.0643 (7) | |
H9 | 0.4624 | 0.4385 | 0.6621 | 0.077* | |
C10 | 0.5387 (3) | 0.3166 (3) | 0.7011 (2) | 0.0699 (8) | |
H10 | 0.5807 | 0.3517 | 0.7716 | 0.084* | |
C11 | 0.5468 (3) | 0.2126 (3) | 0.6616 (2) | 0.0652 (7) | |
H11 | 0.5941 | 0.1781 | 0.7066 | 0.078* | |
C12 | 0.3263 (3) | 0.3600 (3) | 0.4556 (2) | 0.0587 (6) | |
H12 | 0.3047 | 0.3277 | 0.3862 | 0.070* | |
C13 | 0.3368 (3) | 0.8445 (3) | 0.0321 (2) | 0.0716 (8) | |
C14 | 0.1771 (3) | 0.7450 (2) | 0.00478 (19) | 0.0562 (6) | |
C15 | 0.0531 (3) | 0.7617 (2) | −0.0533 (2) | 0.0603 (6) | |
H15 | 0.0739 | 0.8296 | −0.0767 | 0.072* | |
C16 | −0.1041 (3) | 0.6822 (2) | −0.07980 (19) | 0.0547 (6) | |
C17A | −0.2248 (3) | 0.7190 (2) | −0.1295 (2) | 0.0617 (6) | 0.776 (4) |
C18A | −0.2195 (15) | 0.8170 (10) | −0.1636 (12) | 0.0749 (17) | 0.776 (4) |
H18A | −0.1275 | 0.8781 | −0.1585 | 0.090* | 0.776 (4) |
C19A | −0.3663 (12) | 0.8166 (11) | −0.2071 (11) | 0.0967 (14) | 0.776 (4) |
H19A | −0.3827 | 0.8752 | −0.2362 | 0.116* | 0.776 (4) |
C20A | −0.4797 (10) | 0.7212 (13) | −0.2013 (14) | 0.1038 (17) | 0.776 (4) |
H20A | −0.5844 | 0.7061 | −0.2258 | 0.125* | 0.776 (4) |
S1A | −0.41183 (16) | 0.63215 (15) | −0.1451 (2) | 0.0914 (5) | 0.776 (4) |
C17B | −0.2248 (3) | 0.7190 (2) | −0.1295 (2) | 0.0617 (6) | 0.224 (4) |
C18B | −0.3814 (18) | 0.661 (2) | −0.148 (3) | 0.0914 (5) | 0.224 (4) |
H18B | −0.4257 | 0.5892 | −0.1326 | 0.110* | 0.224 (4) |
C19B | −0.467 (2) | 0.722 (4) | −0.191 (5) | 0.1038 (17) | 0.224 (4) |
H19B | −0.5741 | 0.6952 | −0.2079 | 0.125* | 0.224 (4) |
C20B | −0.376 (3) | 0.823 (3) | −0.205 (4) | 0.0967 (14) | 0.224 (4) |
H20B | −0.4133 | 0.8747 | −0.2328 | 0.116* | 0.224 (4) |
S1B | −0.1885 (14) | 0.8470 (9) | −0.1667 (11) | 0.0749 (17) | 0.224 (4) |
C21 | 0.8095 (4) | 0.1699 (3) | 0.3366 (3) | 0.0724 (8) | |
C22 | 0.7538 (3) | 0.1179 (2) | 0.4184 (2) | 0.0583 (6) | |
C23 | 0.8656 (3) | 0.1207 (3) | 0.5044 (2) | 0.0633 (7) | |
H23 | 0.9660 | 0.1431 | 0.5028 | 0.076* | |
C24 | 0.8412 (3) | 0.0928 (2) | 0.5932 (2) | 0.0560 (6) | |
C25A | 0.9749 (3) | 0.1097 (2) | 0.6809 (2) | 0.0588 (6) | 0.818 (4) |
C26A | 1.1195 (12) | 0.1183 (17) | 0.6845 (12) | 0.0713 (16) | 0.818 (4) |
H26A | 1.1494 | 0.1116 | 0.6268 | 0.086* | 0.818 (4) |
C27A | 1.2181 (7) | 0.1385 (7) | 0.7848 (5) | 0.0836 (13) | 0.818 (4) |
H27A | 1.3212 | 0.1490 | 0.8009 | 0.100* | 0.818 (4) |
C28A | 1.1470 (5) | 0.1408 (5) | 0.8553 (4) | 0.0789 (13) | 0.818 (4) |
H28A | 1.1945 | 0.1527 | 0.9252 | 0.095* | 0.818 (4) |
S2A | 0.95748 (16) | 0.11884 (12) | 0.79931 (9) | 0.0757 (4) | 0.818 (4) |
C25B | 0.9749 (3) | 0.1097 (2) | 0.6809 (2) | 0.0588 (6) | 0.182 (4) |
C26B | 0.963 (3) | 0.102 (2) | 0.7755 (12) | 0.0757 (4) | 0.182 (4) |
H26B | 0.8726 | 0.0897 | 0.7908 | 0.091* | 0.182 (4) |
C27B | 1.102 (3) | 0.114 (3) | 0.8466 (14) | 0.0789 (13) | 0.182 (4) |
H27B | 1.1153 | 0.1109 | 0.9143 | 0.095* | 0.182 (4) |
C28B | 1.216 (2) | 0.131 (3) | 0.8049 (18) | 0.0836 (13) | 0.182 (4) |
H28B | 1.3158 | 0.1403 | 0.8403 | 0.100* | 0.182 (4) |
S2B | 1.1521 (14) | 0.131 (2) | 0.6781 (14) | 0.0713 (16) | 0.182 (4) |
F1 | 0.4032 (3) | 0.8890 (2) | 0.13038 (17) | 0.1207 (9) | |
F2 | 0.3381 (3) | 0.9347 (2) | −0.0058 (2) | 0.1360 (11) | |
F3 | 0.4293 (3) | 0.8074 (3) | 0.0010 (3) | 0.1541 (13) | |
F4 | 0.8209 (3) | 0.28127 (19) | 0.34961 (19) | 0.1081 (7) | |
F5 | 0.7124 (2) | 0.1116 (2) | 0.24276 (15) | 0.1020 (7) | |
F6 | 0.9482 (2) | 0.1745 (2) | 0.33819 (17) | 0.1017 (7) | |
N1 | −0.0386 (2) | 0.53615 (19) | 0.14054 (17) | 0.0543 (5) | |
N2 | 0.2054 (3) | 0.4648 (2) | 0.39160 (16) | 0.0601 (5) | |
N3 | 0.2851 (3) | 0.4416 (2) | 0.48007 (17) | 0.0622 (6) | |
N4 | 0.4884 (2) | 0.1583 (2) | 0.55963 (17) | 0.0600 (5) | |
O1 | 0.1810 (2) | 0.66011 (17) | 0.04207 (14) | 0.0637 (5) | |
O2 | −0.1486 (2) | 0.58207 (16) | −0.06250 (14) | 0.0602 (4) | |
O3 | 0.6108 (2) | 0.08233 (19) | 0.39875 (16) | 0.0716 (5) | |
O4 | 0.7110 (2) | 0.05473 (18) | 0.60634 (15) | 0.0653 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0398 (2) | 0.0492 (2) | 0.0491 (2) | 0.02067 (17) | 0.01096 (16) | 0.01889 (18) |
Cu2 | 0.0389 (2) | 0.0616 (3) | 0.0526 (3) | 0.02118 (19) | 0.00989 (17) | 0.0231 (2) |
C1 | 0.0457 (12) | 0.0532 (14) | 0.0592 (15) | 0.0221 (11) | 0.0146 (11) | 0.0162 (11) |
C2 | 0.0580 (14) | 0.0496 (13) | 0.0638 (16) | 0.0234 (11) | 0.0226 (12) | 0.0208 (12) |
C3 | 0.0733 (17) | 0.0663 (17) | 0.0780 (19) | 0.0370 (14) | 0.0390 (15) | 0.0304 (15) |
C4 | 0.0621 (16) | 0.0770 (19) | 0.096 (2) | 0.0414 (15) | 0.0378 (16) | 0.0406 (17) |
C5 | 0.0508 (14) | 0.0667 (16) | 0.0826 (19) | 0.0307 (13) | 0.0251 (13) | 0.0366 (15) |
C6 | 0.0652 (16) | 0.0665 (17) | 0.0593 (16) | 0.0279 (14) | 0.0240 (13) | 0.0162 (13) |
C7 | 0.0561 (14) | 0.0722 (17) | 0.0484 (14) | 0.0277 (13) | 0.0139 (11) | 0.0235 (13) |
C8 | 0.0481 (13) | 0.0698 (16) | 0.0516 (14) | 0.0215 (12) | 0.0160 (11) | 0.0237 (12) |
C9 | 0.0600 (15) | 0.0775 (19) | 0.0566 (16) | 0.0271 (14) | 0.0219 (13) | 0.0207 (14) |
C10 | 0.0577 (15) | 0.101 (2) | 0.0474 (14) | 0.0288 (16) | 0.0162 (12) | 0.0232 (15) |
C11 | 0.0563 (14) | 0.089 (2) | 0.0536 (15) | 0.0314 (14) | 0.0149 (12) | 0.0327 (15) |
C12 | 0.0568 (14) | 0.0675 (16) | 0.0516 (14) | 0.0249 (13) | 0.0163 (11) | 0.0211 (12) |
C13 | 0.0595 (16) | 0.082 (2) | 0.0660 (18) | 0.0207 (15) | 0.0161 (14) | 0.0304 (16) |
C14 | 0.0604 (15) | 0.0596 (15) | 0.0480 (13) | 0.0218 (12) | 0.0196 (11) | 0.0174 (12) |
C15 | 0.0622 (15) | 0.0542 (14) | 0.0591 (15) | 0.0193 (12) | 0.0135 (12) | 0.0240 (12) |
C16 | 0.0637 (15) | 0.0557 (15) | 0.0456 (13) | 0.0253 (12) | 0.0184 (11) | 0.0142 (11) |
C17A | 0.0661 (16) | 0.0636 (16) | 0.0510 (14) | 0.0289 (13) | 0.0142 (12) | 0.0070 (12) |
C18A | 0.080 (4) | 0.071 (5) | 0.0790 (16) | 0.033 (4) | 0.022 (2) | 0.038 (3) |
C19A | 0.123 (4) | 0.108 (3) | 0.077 (2) | 0.080 (3) | 0.017 (2) | 0.022 (2) |
C20A | 0.081 (3) | 0.124 (4) | 0.098 (5) | 0.062 (3) | 0.002 (3) | 0.009 (3) |
S1A | 0.0627 (8) | 0.0878 (11) | 0.1060 (9) | 0.0287 (7) | 0.0137 (7) | 0.0081 (9) |
C17B | 0.0661 (16) | 0.0636 (16) | 0.0510 (14) | 0.0289 (13) | 0.0142 (12) | 0.0070 (12) |
C18B | 0.0627 (8) | 0.0878 (11) | 0.1060 (9) | 0.0287 (7) | 0.0137 (7) | 0.0081 (9) |
C19B | 0.081 (3) | 0.124 (4) | 0.098 (5) | 0.062 (3) | 0.002 (3) | 0.009 (3) |
C20B | 0.123 (4) | 0.108 (3) | 0.077 (2) | 0.080 (3) | 0.017 (2) | 0.022 (2) |
S1B | 0.080 (4) | 0.071 (5) | 0.0790 (16) | 0.033 (4) | 0.022 (2) | 0.038 (3) |
C21 | 0.0632 (17) | 0.073 (2) | 0.074 (2) | 0.0226 (15) | 0.0181 (15) | 0.0221 (15) |
C22 | 0.0476 (13) | 0.0531 (14) | 0.0655 (16) | 0.0169 (11) | 0.0131 (12) | 0.0120 (12) |
C23 | 0.0454 (13) | 0.0748 (18) | 0.0634 (16) | 0.0206 (12) | 0.0148 (12) | 0.0172 (14) |
C24 | 0.0463 (13) | 0.0534 (14) | 0.0625 (16) | 0.0204 (11) | 0.0126 (11) | 0.0104 (12) |
C25A | 0.0552 (14) | 0.0554 (15) | 0.0582 (15) | 0.0217 (12) | 0.0121 (12) | 0.0097 (12) |
C26A | 0.047 (4) | 0.085 (4) | 0.074 (2) | 0.027 (4) | 0.013 (3) | 0.0168 (17) |
C27A | 0.0636 (19) | 0.091 (3) | 0.084 (3) | 0.0356 (18) | 0.002 (2) | 0.021 (2) |
C28A | 0.071 (3) | 0.074 (4) | 0.063 (2) | 0.017 (3) | −0.002 (2) | 0.015 (2) |
S2A | 0.0762 (6) | 0.0819 (7) | 0.0625 (7) | 0.0261 (5) | 0.0211 (5) | 0.0208 (6) |
C25B | 0.0552 (14) | 0.0554 (15) | 0.0582 (15) | 0.0217 (12) | 0.0121 (12) | 0.0097 (12) |
C26B | 0.0762 (6) | 0.0819 (7) | 0.0625 (7) | 0.0261 (5) | 0.0211 (5) | 0.0208 (6) |
C27B | 0.071 (3) | 0.074 (4) | 0.063 (2) | 0.017 (3) | −0.002 (2) | 0.015 (2) |
C28B | 0.0636 (19) | 0.091 (3) | 0.084 (3) | 0.0356 (18) | 0.002 (2) | 0.021 (2) |
S2B | 0.047 (4) | 0.085 (4) | 0.074 (2) | 0.027 (4) | 0.013 (3) | 0.0168 (17) |
F1 | 0.0948 (15) | 0.1192 (19) | 0.0767 (14) | −0.0080 (13) | −0.0057 (11) | 0.0181 (13) |
F2 | 0.0815 (14) | 0.1165 (18) | 0.164 (2) | −0.0036 (12) | 0.0021 (14) | 0.0896 (18) |
F3 | 0.0933 (16) | 0.141 (2) | 0.214 (3) | 0.0205 (16) | 0.089 (2) | 0.007 (2) |
F4 | 0.1337 (19) | 0.0739 (13) | 0.1165 (17) | 0.0363 (13) | 0.0419 (14) | 0.0421 (12) |
F5 | 0.0928 (14) | 0.1205 (17) | 0.0644 (11) | 0.0245 (12) | 0.0130 (10) | 0.0175 (11) |
F6 | 0.0742 (12) | 0.143 (2) | 0.1052 (15) | 0.0441 (12) | 0.0424 (11) | 0.0614 (14) |
N1 | 0.0465 (10) | 0.0548 (12) | 0.0627 (13) | 0.0216 (9) | 0.0155 (9) | 0.0224 (10) |
N2 | 0.0612 (13) | 0.0714 (14) | 0.0520 (12) | 0.0325 (11) | 0.0152 (10) | 0.0219 (11) |
N3 | 0.0608 (13) | 0.0754 (15) | 0.0528 (12) | 0.0311 (12) | 0.0158 (10) | 0.0224 (11) |
N4 | 0.0528 (11) | 0.0763 (15) | 0.0555 (13) | 0.0298 (11) | 0.0150 (10) | 0.0279 (11) |
O1 | 0.0629 (11) | 0.0640 (11) | 0.0648 (11) | 0.0270 (9) | 0.0162 (9) | 0.0264 (9) |
O2 | 0.0602 (10) | 0.0568 (11) | 0.0633 (11) | 0.0205 (8) | 0.0226 (9) | 0.0213 (9) |
O3 | 0.0484 (10) | 0.0851 (14) | 0.0762 (13) | 0.0259 (10) | 0.0119 (9) | 0.0278 (11) |
O4 | 0.0493 (10) | 0.0781 (13) | 0.0689 (12) | 0.0261 (9) | 0.0186 (8) | 0.0238 (10) |
Cu1—O1i | 2.0225 (19) | C15—C16 | 1.417 (4) |
Cu1—O1 | 2.0225 (19) | C15—H15 | 0.9300 |
Cu1—N1 | 2.111 (2) | C16—O2 | 1.254 (3) |
Cu1—N1i | 2.111 (2) | C16—C17A | 1.463 (4) |
Cu1—O2i | 2.1426 (18) | C17A—C18A | 1.368 (10) |
Cu1—O2 | 2.1426 (18) | C17A—S1A | 1.701 (3) |
Cu2—O4 | 2.0108 (18) | C18A—C19A | 1.405 (12) |
Cu2—O4ii | 2.0108 (18) | C18A—H18A | 0.9300 |
Cu2—N4 | 2.086 (2) | C19A—C20A | 1.342 (7) |
Cu2—N4ii | 2.086 (2) | C19A—H19A | 0.9300 |
Cu2—O3 | 2.164 (2) | C20A—S1A | 1.675 (9) |
Cu2—O3ii | 2.164 (2) | C20A—H20A | 0.9300 |
C1—N1 | 1.328 (3) | C18B—C19B | 1.405 (16) |
C1—C2 | 1.389 (4) | C18B—H18B | 0.9300 |
C1—H1 | 0.9300 | C19B—C20B | 1.342 (10) |
C2—C3 | 1.389 (4) | C19B—H19B | 0.9300 |
C2—C6 | 1.465 (4) | C20B—S1B | 1.675 (15) |
C3—C4 | 1.368 (4) | C20B—H20B | 0.9300 |
C3—H3 | 0.9300 | C21—F5 | 1.316 (4) |
C4—C5 | 1.372 (4) | C21—F6 | 1.334 (4) |
C4—H4 | 0.9300 | C21—F4 | 1.337 (4) |
C5—N1 | 1.340 (3) | C21—C22 | 1.524 (4) |
C5—H5 | 0.9300 | C22—O3 | 1.248 (3) |
C6—N2 | 1.257 (3) | C22—C23 | 1.385 (4) |
C6—H6 | 0.9300 | C23—C24 | 1.394 (4) |
C7—N4 | 1.331 (3) | C23—H23 | 0.9300 |
C7—C8 | 1.381 (4) | C24—O4 | 1.267 (3) |
C7—H7 | 0.9300 | C24—C25A | 1.467 (4) |
C8—C9 | 1.394 (4) | C25A—C26A | 1.369 (9) |
C8—C12 | 1.464 (4) | C25A—S2A | 1.700 (3) |
C9—C10 | 1.365 (4) | C26A—C27A | 1.407 (14) |
C9—H9 | 0.9300 | C26A—H26A | 0.9300 |
C10—C11 | 1.373 (4) | C27A—C28A | 1.350 (6) |
C10—H10 | 0.9300 | C27A—H27A | 0.9300 |
C11—N4 | 1.354 (4) | C28A—S2A | 1.717 (5) |
C11—H11 | 0.9300 | C28A—H28A | 0.9300 |
C12—N3 | 1.258 (3) | C26B—C27B | 1.407 (16) |
C12—H12 | 0.9300 | C26B—H26B | 0.9300 |
C13—F3 | 1.292 (4) | C27B—C28B | 1.352 (10) |
C13—F1 | 1.293 (4) | C27B—H27B | 0.9300 |
C13—F2 | 1.312 (4) | C28B—S2B | 1.721 (11) |
C13—C14 | 1.520 (4) | C28B—H28B | 0.9300 |
C14—O1 | 1.257 (3) | N2—N3 | 1.409 (3) |
C14—C15 | 1.375 (4) | ||
O1i—Cu1—O1 | 179.999 (1) | C15—C14—C13 | 116.7 (2) |
O1i—Cu1—N1 | 88.71 (8) | C14—C15—C16 | 124.4 (2) |
O1—Cu1—N1 | 91.29 (8) | C14—C15—H15 | 117.8 |
O1i—Cu1—N1i | 91.29 (8) | C16—C15—H15 | 117.8 |
O1—Cu1—N1i | 88.71 (8) | O2—C16—C15 | 124.7 (2) |
N1—Cu1—N1i | 180.0 | O2—C16—C17A | 116.9 (2) |
O1i—Cu1—O2i | 88.10 (7) | C15—C16—C17A | 118.4 (2) |
O1—Cu1—O2i | 91.90 (7) | C18A—C17A—C16 | 132.7 (6) |
N1—Cu1—O2i | 91.14 (7) | C18A—C17A—S1A | 109.3 (5) |
N1i—Cu1—O2i | 88.86 (7) | C16—C17A—S1A | 118.0 (2) |
O1i—Cu1—O2 | 91.90 (7) | C17A—C18A—C19A | 113.7 (7) |
O1—Cu1—O2 | 88.10 (7) | C17A—C18A—H18A | 123.2 |
N1—Cu1—O2 | 88.86 (7) | C19A—C18A—H18A | 123.2 |
N1i—Cu1—O2 | 91.14 (7) | C20A—C19A—C18A | 111.5 (7) |
O2i—Cu1—O2 | 180.00 (7) | C20A—C19A—H19A | 124.2 |
O4—Cu2—O4ii | 180.0 | C18A—C19A—H19A | 124.2 |
O4—Cu2—N4 | 89.81 (8) | C19A—C20A—S1A | 112.5 (6) |
O4ii—Cu2—N4 | 90.19 (8) | C19A—C20A—H20A | 123.8 |
O4—Cu2—N4ii | 90.19 (8) | S1A—C20A—H20A | 123.8 |
O4ii—Cu2—N4ii | 89.81 (8) | C20A—S1A—C17A | 92.9 (4) |
N4—Cu2—N4ii | 180.00 (6) | C19B—C18B—H18B | 123.6 |
O4—Cu2—O3 | 88.84 (7) | C20B—C19B—C18B | 111.9 (15) |
O4ii—Cu2—O3 | 91.16 (7) | C20B—C19B—H19B | 124.0 |
N4—Cu2—O3 | 89.74 (8) | C18B—C19B—H19B | 124.0 |
N4ii—Cu2—O3 | 90.26 (8) | C19B—C20B—S1B | 112.8 (13) |
O4—Cu2—O3ii | 91.16 (7) | C19B—C20B—H20B | 123.6 |
O4ii—Cu2—O3ii | 88.84 (7) | S1B—C20B—H20B | 123.6 |
N4—Cu2—O3ii | 90.26 (8) | F5—C21—F6 | 106.8 (3) |
N4ii—Cu2—O3ii | 89.74 (8) | F5—C21—F4 | 106.2 (3) |
O3—Cu2—O3ii | 180.0 | F6—C21—F4 | 106.5 (3) |
N1—C1—C2 | 124.2 (2) | F5—C21—C22 | 112.7 (3) |
N1—C1—H1 | 117.9 | F6—C21—C22 | 114.4 (2) |
C2—C1—H1 | 117.9 | F4—C21—C22 | 109.7 (3) |
C3—C2—C1 | 117.0 (2) | O3—C22—C23 | 129.1 (3) |
C3—C2—C6 | 122.8 (3) | O3—C22—C21 | 113.5 (2) |
C1—C2—C6 | 120.0 (2) | C23—C22—C21 | 117.2 (2) |
C4—C3—C2 | 119.1 (3) | C22—C23—C24 | 125.9 (2) |
C4—C3—H3 | 120.4 | C22—C23—H23 | 117.1 |
C2—C3—H3 | 120.4 | C24—C23—H23 | 117.1 |
C3—C4—C5 | 119.8 (2) | O4—C24—C23 | 125.4 (2) |
C3—C4—H4 | 120.1 | O4—C24—C25A | 115.6 (2) |
C5—C4—H4 | 120.1 | C23—C24—C25A | 118.9 (2) |
N1—C5—C4 | 122.4 (3) | C26A—C25A—C24 | 130.0 (7) |
N1—C5—H5 | 118.8 | C26A—C25A—S2A | 111.1 (6) |
C4—C5—H5 | 118.8 | C24—C25A—S2A | 118.9 (2) |
N2—C6—C2 | 119.4 (3) | C25A—C26A—C27A | 112.8 (9) |
N2—C6—H6 | 120.3 | C25A—C26A—H26A | 123.6 |
C2—C6—H6 | 120.3 | C27A—C26A—H26A | 123.6 |
N4—C7—C8 | 123.8 (2) | C28A—C27A—C26A | 112.7 (5) |
N4—C7—H7 | 118.1 | C28A—C27A—H27A | 123.7 |
C8—C7—H7 | 118.1 | C26A—C27A—H27A | 123.7 |
C7—C8—C9 | 117.8 (2) | C27A—C28A—S2A | 111.4 (4) |
C7—C8—C12 | 118.8 (2) | C27A—C28A—H28A | 124.3 |
C9—C8—C12 | 123.3 (3) | S2A—C28A—H28A | 124.3 |
C10—C9—C8 | 119.0 (3) | C25A—S2A—C28A | 92.0 (2) |
C10—C9—H9 | 120.5 | C27B—C26B—H26B | 123.8 |
C8—C9—H9 | 120.5 | C28B—C27B—C26B | 111.9 (13) |
C9—C10—C11 | 119.6 (3) | C28B—C27B—H27B | 124.0 |
C9—C10—H10 | 120.2 | C26B—C27B—H27B | 124.0 |
C11—C10—H10 | 120.2 | C27B—C28B—S2B | 111.7 (11) |
N4—C11—C10 | 122.5 (3) | C27B—C28B—H28B | 124.1 |
N4—C11—H11 | 118.7 | S2B—C28B—H28B | 124.1 |
C10—C11—H11 | 118.7 | C1—N1—C5 | 117.4 (2) |
N3—C12—C8 | 123.0 (2) | C1—N1—Cu1 | 120.26 (16) |
N3—C12—H12 | 118.5 | C5—N1—Cu1 | 122.30 (18) |
C8—C12—H12 | 118.5 | C6—N2—N3 | 114.3 (2) |
F3—C13—F1 | 106.0 (3) | C12—N3—N2 | 110.5 (2) |
F3—C13—F2 | 106.4 (3) | C7—N4—C11 | 117.2 (3) |
F1—C13—F2 | 105.5 (3) | C7—N4—Cu2 | 120.39 (19) |
F3—C13—C14 | 111.7 (3) | C11—N4—Cu2 | 122.36 (18) |
F1—C13—C14 | 111.8 (3) | C14—O1—Cu1 | 123.97 (17) |
F2—C13—C14 | 114.9 (2) | C16—O2—Cu1 | 125.31 (17) |
O1—C14—C15 | 130.3 (3) | C22—O3—Cu2 | 121.23 (18) |
O1—C14—C13 | 112.9 (2) | C24—O4—Cu2 | 127.45 (18) |
N1—C1—C2—C3 | −2.0 (4) | C26A—C25A—S2A—C28A | 2.5 (9) |
N1—C1—C2—C6 | 173.1 (2) | C24—C25A—S2A—C28A | −178.5 (3) |
C1—C2—C3—C4 | 1.6 (4) | C27A—C28A—S2A—C25A | −1.3 (4) |
C6—C2—C3—C4 | −173.3 (3) | C26B—C27B—C28B—S2B | 0.0 (5) |
C2—C3—C4—C5 | 0.1 (4) | C2—C1—N1—C5 | 0.5 (4) |
C3—C4—C5—N1 | −1.8 (4) | C2—C1—N1—Cu1 | −177.16 (19) |
C3—C2—C6—N2 | 157.8 (3) | C4—C5—N1—C1 | 1.4 (4) |
C1—C2—C6—N2 | −16.9 (4) | C4—C5—N1—Cu1 | 179.0 (2) |
N4—C7—C8—C9 | 1.6 (4) | O1i—Cu1—N1—C1 | 103.69 (19) |
N4—C7—C8—C12 | −178.2 (2) | O1—Cu1—N1—C1 | −76.31 (19) |
C7—C8—C9—C10 | −1.1 (4) | O2i—Cu1—N1—C1 | 15.62 (19) |
C12—C8—C9—C10 | 178.8 (3) | O2—Cu1—N1—C1 | −164.38 (19) |
C8—C9—C10—C11 | 0.1 (4) | O1i—Cu1—N1—C5 | −73.8 (2) |
C9—C10—C11—N4 | 0.5 (4) | O1—Cu1—N1—C5 | 106.2 (2) |
C7—C8—C12—N3 | 168.1 (3) | O2i—Cu1—N1—C5 | −161.9 (2) |
C9—C8—C12—N3 | −11.7 (4) | O2—Cu1—N1—C5 | 18.1 (2) |
F3—C13—C14—O1 | 58.4 (4) | C2—C6—N2—N3 | −175.2 (2) |
F1—C13—C14—O1 | −60.1 (4) | C8—C12—N3—N2 | −177.6 (2) |
F2—C13—C14—O1 | 179.6 (3) | C6—N2—N3—C12 | 164.8 (3) |
F3—C13—C14—C15 | −123.0 (3) | C8—C7—N4—C11 | −1.1 (4) |
F1—C13—C14—C15 | 118.4 (3) | C8—C7—N4—Cu2 | 178.63 (19) |
F2—C13—C14—C15 | −1.8 (4) | C10—C11—N4—C7 | 0.0 (4) |
O1—C14—C15—C16 | 2.8 (5) | C10—C11—N4—Cu2 | −179.7 (2) |
C13—C14—C15—C16 | −175.5 (3) | O4—Cu2—N4—C7 | 143.5 (2) |
C14—C15—C16—O2 | −7.5 (4) | O4ii—Cu2—N4—C7 | −36.5 (2) |
C14—C15—C16—C17A | 171.5 (2) | O3—Cu2—N4—C7 | 54.6 (2) |
O2—C16—C17A—C18A | −176.4 (10) | O3ii—Cu2—N4—C7 | −125.4 (2) |
C15—C16—C17A—C18A | 4.6 (11) | O4—Cu2—N4—C11 | −36.8 (2) |
O2—C16—C17A—S1A | 7.8 (3) | O4ii—Cu2—N4—C11 | 143.2 (2) |
C15—C16—C17A—S1A | −171.3 (2) | O3—Cu2—N4—C11 | −125.7 (2) |
C16—C17A—C18A—C19A | −179.7 (7) | O3ii—Cu2—N4—C11 | 54.3 (2) |
S1A—C17A—C18A—C19A | −3.6 (12) | C15—C14—O1—Cu1 | 14.3 (4) |
C17A—C18A—C19A—C20A | 2.6 (12) | C13—C14—O1—Cu1 | −167.42 (18) |
C18A—C19A—C20A—S1A | −0.3 (8) | N1—Cu1—O1—C14 | −107.3 (2) |
C19A—C20A—S1A—C17A | −1.5 (6) | N1i—Cu1—O1—C14 | 72.7 (2) |
C18A—C17A—S1A—C20A | 2.9 (9) | O2i—Cu1—O1—C14 | 161.5 (2) |
C16—C17A—S1A—C20A | 179.6 (6) | O2—Cu1—O1—C14 | −18.5 (2) |
C18B—C19B—C20B—S1B | 0.0 (5) | C15—C16—O2—Cu1 | −5.2 (4) |
F5—C21—C22—O3 | −38.1 (4) | C17A—C16—O2—Cu1 | 175.81 (16) |
F6—C21—C22—O3 | −160.3 (3) | O1i—Cu1—O2—C16 | −165.2 (2) |
F4—C21—C22—O3 | 80.0 (3) | O1—Cu1—O2—C16 | 14.8 (2) |
F5—C21—C22—C23 | 144.5 (3) | N1—Cu1—O2—C16 | 106.1 (2) |
F6—C21—C22—C23 | 22.3 (4) | N1i—Cu1—O2—C16 | −73.9 (2) |
F4—C21—C22—C23 | −97.4 (3) | C23—C22—O3—Cu2 | −4.7 (4) |
O3—C22—C23—C24 | −6.2 (5) | C21—C22—O3—Cu2 | 178.29 (19) |
C21—C22—C23—C24 | 170.7 (3) | O4—Cu2—O3—C22 | 11.9 (2) |
C22—C23—C24—O4 | 3.9 (5) | O4ii—Cu2—O3—C22 | −168.1 (2) |
C22—C23—C24—C25A | −175.0 (3) | N4—Cu2—O3—C22 | 101.7 (2) |
O4—C24—C25A—C26A | 160.6 (11) | N4ii—Cu2—O3—C22 | −78.3 (2) |
C23—C24—C25A—C26A | −20.3 (11) | C23—C24—O4—Cu2 | 9.9 (4) |
O4—C24—C25A—S2A | −18.3 (3) | C25A—C24—O4—Cu2 | −171.13 (17) |
C23—C24—C25A—S2A | 160.8 (2) | N4—Cu2—O4—C24 | −104.5 (2) |
C24—C25A—C26A—C27A | 178.0 (5) | N4ii—Cu2—O4—C24 | 75.5 (2) |
S2A—C25A—C26A—C27A | −3.1 (14) | O3—Cu2—O4—C24 | −14.7 (2) |
C25A—C26A—C27A—C28A | 2.2 (13) | O3ii—Cu2—O4—C24 | 165.3 (2) |
C26A—C27A—C28A—S2A | −0.3 (8) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y, −z+1. |