Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028259/lh6301sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028259/lh6301Isup2.hkl |
CCDC reference: 258668
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.006 Å Some non-H atoms missing
- R factor = 0.059
- wR factor = 0.171
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O4 - H42O ... ? PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 111.00 A 3
Alert level C CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.99 <> 1.01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_weight 1225.08 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 68.00 816.75 H 1.01 62.00 62.50 N 14.01 8.00 112.06 O 16.00 4.00 64.00 F 19.00 3.00 56.99 S 32.07 1.00 32.07 Cu 63.55 1.00 63.55 Calculated formula weight 1207.90 DENSD01_ALERT_1_C The ratio of the submitted crystal density and that calculated from the formula is outside the range 0.99 <> 1.01 Crystal density given = 1.298 Calculated crystal density = 1.317 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT043_ALERT_1_C Check Reported Molecular Weight ................ 1225.08 PLAT046_ALERT_1_C Reported Z, MW and D(calc) are Inconsistent .... 1.32 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.80 Ratio PLAT231_ALERT_4_C Hirshfeld Test (Solvent) S - O2 .. 6.61 su PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C90 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for S PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C1 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C90 -C95 1.37 Ang. PLAT355_ALERT_3_C Long O-H Bond (0.82A) O4 - H42O ... 1.01 Ang. PLAT731_ALERT_1_C Bond Calc 1.01(9), Rep 1.00(4) ...... 2.25 su-Rat O4 -H42O 1.555 1.555
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C68 H64 Cu1 F3 N8 O5 S1 Atom count from the _atom_site data: C68 H62 Cu1 F3 N8 O4 S1 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C68 H64 Cu F3 N8 O5 S TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 272.00 272.00 0.00 H 256.00 248.00 8.00 Cu 4.00 4.00 0.00 F 12.00 12.00 0.00 N 32.00 32.00 0.00 O 20.00 16.00 4.00 S 4.00 4.00 0.00
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
[Cu(C30H26N4)2](CF3SO3)·C7H8·2H2O | F(000) = 2520 |
Mr = 1225.08 | Dx = 1.298 Mg m−3 Dm = 1.33 (1) Mg m−3 Dm measured by flotation n-heptane/2-iodo-2-methylpropane/2-bromopropane |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 956 reflections |
a = 11.1715 (7) Å | θ = 3.2–20.8° |
b = 24.1173 (10) Å | µ = 0.45 mm−1 |
c = 23.0286 (9) Å | T = 297 K |
β = 95.190 (4)° | Wedge, pale yellow |
V = 6179.1 (5) Å3 | 0.52 × 0.32 × 0.14 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 10883 independent reflections |
Radiation source: fine-focus sealed tube | 7598 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 25.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −13→8 |
Tmin = 0.731, Tmax = 0.939 | k = −26→28 |
44390 measured reflections | l = −27→27 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1023P)2 + 2.3428P] where P = (Fo2 + 2Fc2)/3 |
10883 reflections | (Δ/σ)max < 0.001 |
777 parameters | Δρmax = 0.58 e Å−3 |
15 restraints | Δρmin = −0.39 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. 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 | ||
Cu | 0.02235 (4) | 0.540501 (16) | 0.254736 (16) | 0.04109 (15) | |
N11 | 0.2942 (3) | 0.63228 (12) | 0.17586 (11) | 0.0482 (7) | |
N13 | 0.1699 (2) | 0.58112 (10) | 0.22473 (10) | 0.0380 (6) | |
N41 | −0.1755 (3) | 0.45468 (11) | 0.11602 (11) | 0.0445 (7) | |
N43 | −0.0969 (2) | 0.50097 (10) | 0.19419 (10) | 0.0373 (6) | |
N51 | −0.1196 (3) | 0.67749 (11) | 0.34829 (12) | 0.0514 (7) | |
N53 | −0.0637 (2) | 0.60941 (10) | 0.29026 (10) | 0.0408 (6) | |
N81 | 0.0806 (3) | 0.40779 (11) | 0.37909 (11) | 0.0459 (7) | |
N83 | 0.0765 (2) | 0.47304 (10) | 0.30996 (10) | 0.0395 (6) | |
C11 | 0.3531 (3) | 0.62389 (13) | 0.23062 (14) | 0.0446 (8) | |
C12 | 0.1851 (3) | 0.60638 (12) | 0.17518 (13) | 0.0395 (7) | |
C13 | 0.2754 (3) | 0.59248 (12) | 0.26094 (13) | 0.0385 (7) | |
C14 | 0.3050 (3) | 0.57854 (14) | 0.31901 (14) | 0.0486 (8) | |
H14 | 0.2539 | 0.5573 | 0.3397 | 0.058* | |
C15 | 0.4133 (3) | 0.59763 (16) | 0.34450 (16) | 0.0575 (10) | |
H15 | 0.4347 | 0.5898 | 0.3836 | 0.069* | |
C16 | 0.4909 (4) | 0.62796 (18) | 0.31386 (18) | 0.0648 (11) | |
H16 | 0.5638 | 0.6395 | 0.3327 | 0.078* | |
C17 | 0.4638 (3) | 0.64171 (16) | 0.25598 (17) | 0.0582 (10) | |
H17 | 0.5167 | 0.6618 | 0.2352 | 0.070* | |
C18 | 0.3442 (4) | 0.66336 (19) | 0.12885 (17) | 0.0702 (12) | |
H18A | 0.2987 | 0.6545 | 0.0922 | 0.084* | |
H18B | 0.4266 | 0.6517 | 0.1261 | 0.084* | |
C19 | 0.3419 (6) | 0.7256 (2) | 0.1381 (2) | 0.1031 (18) | |
H19A | 0.2613 | 0.7372 | 0.1434 | 0.155* | |
H19B | 0.3687 | 0.7440 | 0.1047 | 0.155* | |
H19C | 0.3940 | 0.7351 | 0.1721 | 0.155* | |
C21 | 0.0512 (3) | 0.56331 (14) | 0.09434 (12) | 0.0411 (7) | |
C22 | 0.0933 (3) | 0.61046 (13) | 0.12535 (12) | 0.0424 (8) | |
C23 | 0.0403 (4) | 0.66168 (15) | 0.11160 (15) | 0.0559 (9) | |
H23 | 0.0683 | 0.6931 | 0.1320 | 0.067* | |
C24 | −0.0517 (4) | 0.66661 (16) | 0.06891 (15) | 0.0611 (10) | |
H24 | −0.0847 | 0.7013 | 0.0598 | 0.073* | |
C25 | −0.0958 (4) | 0.62049 (16) | 0.03930 (14) | 0.0584 (10) | |
H25 | −0.1602 | 0.6237 | 0.0109 | 0.070* | |
C26 | −0.0446 (3) | 0.56930 (16) | 0.05166 (13) | 0.0516 (9) | |
H26 | −0.0744 | 0.5383 | 0.0312 | 0.062* | |
C31 | 0.0465 (3) | 0.46444 (13) | 0.12759 (13) | 0.0399 (7) | |
C32 | 0.1081 (3) | 0.50815 (13) | 0.10426 (12) | 0.0406 (7) | |
C33 | 0.2223 (3) | 0.49785 (16) | 0.08663 (14) | 0.0509 (9) | |
H33 | 0.2653 | 0.5266 | 0.0715 | 0.061* | |
C34 | 0.2724 (3) | 0.44541 (18) | 0.09141 (16) | 0.0593 (10) | |
H34 | 0.3478 | 0.4391 | 0.0786 | 0.071* | |
C35 | 0.2119 (4) | 0.40286 (17) | 0.11488 (17) | 0.0615 (10) | |
H35 | 0.2460 | 0.3677 | 0.1183 | 0.074* | |
C36 | 0.0992 (3) | 0.41259 (15) | 0.13345 (16) | 0.0537 (9) | |
H36 | 0.0584 | 0.3839 | 0.1501 | 0.064* | |
C41 | −0.2714 (3) | 0.47119 (13) | 0.14589 (13) | 0.0421 (8) | |
C42 | −0.0744 (3) | 0.47391 (12) | 0.14670 (12) | 0.0383 (7) | |
C43 | −0.2218 (3) | 0.49923 (12) | 0.19490 (12) | 0.0368 (7) | |
C44 | −0.2954 (3) | 0.51988 (13) | 0.23553 (13) | 0.0434 (8) | |
H44 | −0.2632 | 0.5383 | 0.2688 | 0.052* | |
C45 | −0.4163 (3) | 0.51216 (16) | 0.22491 (15) | 0.0519 (9) | |
H45 | −0.4671 | 0.5251 | 0.2518 | 0.062* | |
C46 | −0.4653 (3) | 0.48543 (18) | 0.17480 (16) | 0.0625 (10) | |
H46 | −0.5483 | 0.4816 | 0.1687 | 0.075* | |
C47 | −0.3956 (3) | 0.46458 (17) | 0.13430 (16) | 0.0590 (10) | |
H47 | −0.4290 | 0.4469 | 0.1008 | 0.071* | |
C48 | −0.1853 (4) | 0.42454 (16) | 0.06023 (14) | 0.0582 (10) | |
H48A | −0.1112 | 0.4292 | 0.0419 | 0.070* | |
H48B | −0.2498 | 0.4407 | 0.0347 | 0.070* | |
C49 | −0.2092 (5) | 0.3640 (2) | 0.0665 (2) | 0.0909 (15) | |
H49A | −0.1520 | 0.3486 | 0.0958 | 0.136* | |
H49B | −0.2019 | 0.3457 | 0.0300 | 0.136* | |
H49C | −0.2890 | 0.3587 | 0.0779 | 0.136* | |
C51 | −0.1783 (3) | 0.68737 (14) | 0.29416 (17) | 0.0523 (9) | |
C52 | −0.0517 (3) | 0.63072 (12) | 0.34329 (13) | 0.0422 (8) | |
C53 | −0.1421 (3) | 0.64499 (13) | 0.25816 (14) | 0.0467 (8) | |
C54 | −0.1838 (3) | 0.64401 (16) | 0.19913 (16) | 0.0577 (10) | |
H54 | −0.1615 | 0.6159 | 0.1746 | 0.069* | |
C55 | −0.2592 (4) | 0.6862 (2) | 0.1785 (2) | 0.0748 (13) | |
H55 | −0.2872 | 0.6869 | 0.1393 | 0.090* | |
C56 | −0.2939 (4) | 0.7276 (2) | 0.2151 (3) | 0.0828 (15) | |
H56 | −0.3453 | 0.7551 | 0.1995 | 0.099* | |
C57 | −0.2564 (4) | 0.72965 (16) | 0.2727 (2) | 0.0711 (12) | |
H57 | −0.2811 | 0.7576 | 0.2967 | 0.085* | |
C58 | −0.1368 (5) | 0.70925 (15) | 0.40149 (18) | 0.0720 (12) | |
H58A | −0.1135 | 0.6865 | 0.4354 | 0.086* | |
H58B | −0.2213 | 0.7183 | 0.4021 | 0.086* | |
C59 | −0.0636 (6) | 0.76235 (18) | 0.4052 (2) | 0.0992 (17) | |
H59A | 0.0205 | 0.7534 | 0.4097 | 0.149* | |
H59B | −0.0839 | 0.7837 | 0.4381 | 0.149* | |
H59C | −0.0811 | 0.7835 | 0.3701 | 0.149* | |
C61 | 0.0125 (3) | 0.55574 (13) | 0.41363 (12) | 0.0398 (7) | |
C62 | 0.0300 (3) | 0.60892 (13) | 0.39171 (13) | 0.0434 (8) | |
C63 | 0.1291 (4) | 0.63975 (15) | 0.41305 (15) | 0.0585 (10) | |
H63 | 0.1397 | 0.6754 | 0.3989 | 0.070* | |
C64 | 0.2118 (4) | 0.61828 (18) | 0.45486 (16) | 0.0681 (11) | |
H64 | 0.2762 | 0.6399 | 0.4700 | 0.082* | |
C65 | 0.1997 (4) | 0.56514 (18) | 0.47423 (15) | 0.0618 (10) | |
H65 | 0.2580 | 0.5498 | 0.5008 | 0.074* | |
C66 | 0.0994 (3) | 0.53405 (15) | 0.45389 (13) | 0.0506 (9) | |
H66 | 0.0908 | 0.4981 | 0.4676 | 0.061* | |
C71 | −0.0959 (3) | 0.47185 (13) | 0.37049 (12) | 0.0406 (7) | |
C72 | −0.0991 (3) | 0.52413 (13) | 0.39626 (12) | 0.0390 (7) | |
C73 | −0.2111 (3) | 0.54465 (15) | 0.40896 (15) | 0.0526 (9) | |
H73 | −0.2156 | 0.5794 | 0.4261 | 0.063* | |
C74 | −0.3142 (3) | 0.51441 (18) | 0.39660 (16) | 0.0594 (10) | |
H74 | −0.3878 | 0.5291 | 0.4047 | 0.071* | |
C75 | −0.3095 (4) | 0.46236 (17) | 0.37228 (16) | 0.0587 (10) | |
H75 | −0.3793 | 0.4415 | 0.3650 | 0.070* | |
C76 | −0.2012 (3) | 0.44155 (16) | 0.35891 (14) | 0.0527 (9) | |
H76 | −0.1981 | 0.4067 | 0.3419 | 0.063* | |
C81 | 0.1851 (3) | 0.40107 (13) | 0.35196 (14) | 0.0479 (8) | |
C82 | 0.0199 (3) | 0.45123 (12) | 0.35229 (12) | 0.0383 (7) | |
C83 | 0.1807 (3) | 0.44156 (13) | 0.30848 (13) | 0.0431 (8) | |
C84 | 0.2738 (3) | 0.44540 (14) | 0.27276 (16) | 0.0539 (9) | |
H84 | 0.2716 | 0.4713 | 0.2427 | 0.065* | |
C85 | 0.3693 (4) | 0.40979 (16) | 0.28315 (19) | 0.0670 (11) | |
H85 | 0.4331 | 0.4119 | 0.2600 | 0.080* | |
C86 | 0.3725 (4) | 0.37093 (16) | 0.3274 (2) | 0.0713 (12) | |
H86 | 0.4390 | 0.3477 | 0.3333 | 0.086* | |
C87 | 0.2807 (4) | 0.36551 (15) | 0.36271 (18) | 0.0627 (10) | |
H87 | 0.2831 | 0.3392 | 0.3923 | 0.075* | |
C88 | 0.0477 (4) | 0.37581 (15) | 0.42960 (15) | 0.0606 (10) | |
H88A | −0.0109 | 0.3967 | 0.4493 | 0.073* | |
H88B | 0.1185 | 0.3710 | 0.4568 | 0.073* | |
C89 | −0.0034 (5) | 0.32004 (18) | 0.4133 (2) | 0.0891 (15) | |
H89A | −0.0815 | 0.3244 | 0.3928 | 0.134* | |
H89B | −0.0100 | 0.2986 | 0.4480 | 0.134* | |
H89C | 0.0486 | 0.3013 | 0.3887 | 0.134* | |
S | 0.37821 (14) | 0.27195 (7) | 0.00025 (6) | 0.0946 (4) | |
O1 | 0.3599 (5) | 0.2950 (2) | 0.0553 (2) | 0.1439 (17) | |
F1 | 0.4489 (6) | 0.1834 (2) | 0.0525 (3) | 0.230 (3) | |
F3 | 0.5134 (4) | 0.1919 (2) | −0.0279 (2) | 0.1683 (17) | |
O2 | 0.2762 (4) | 0.2402 (2) | −0.0235 (2) | 0.1378 (16) | |
O3 | 0.4346 (5) | 0.3070 (2) | −0.0376 (3) | 0.177 (2) | |
C1 | 0.4846 (6) | 0.2205 (3) | 0.0181 (3) | 0.116 (2) | |
F2 | 0.5899 (5) | 0.2392 (3) | 0.0406 (3) | 0.221 (3) | |
C90 | 0.7079 (5) | 0.29936 (19) | 0.21109 (18) | 0.0738 (12) | |
C91 | 0.7629 (5) | 0.2484 (2) | 0.2115 (2) | 0.0833 (14) | |
H91 | 0.7182 | 0.2176 | 0.1985 | 0.100* | |
C92 | 0.8798 (6) | 0.2420 (3) | 0.2301 (3) | 0.0984 (17) | |
H92 | 0.9142 | 0.2069 | 0.2307 | 0.118* | |
C93 | 0.9481 (6) | 0.2867 (4) | 0.2480 (2) | 0.114 (2) | |
H93 | 1.0285 | 0.2820 | 0.2614 | 0.136* | |
C94 | 0.8980 (7) | 0.3389 (3) | 0.2464 (2) | 0.105 (2) | |
H94 | 0.9446 | 0.3699 | 0.2568 | 0.126* | |
C95 | 0.7777 (6) | 0.3442 (2) | 0.22893 (19) | 0.0853 (15) | |
H95 | 0.7424 | 0.3791 | 0.2292 | 0.102* | |
C96 | 0.5752 (6) | 0.3043 (3) | 0.1923 (3) | 0.127 (2) | |
H96A | 0.5528 | 0.2770 | 0.1631 | 0.190* | |
H96B | 0.5585 | 0.3407 | 0.1766 | 0.190* | |
H96C | 0.5301 | 0.2986 | 0.2253 | 0.190* | |
O4 | 0.5114 (7) | 0.4255 (3) | −0.0202 (3) | 0.191 (2) | |
H41O | 0.510 (11) | 0.388 (3) | −0.006 (5) | 0.287* | |
H42O | 0.445 (8) | 0.422 (5) | −0.053 (4) | 0.287* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0383 (3) | 0.0405 (2) | 0.0438 (2) | −0.00231 (17) | 0.00058 (17) | −0.00063 (16) |
N11 | 0.0448 (18) | 0.0547 (17) | 0.0462 (14) | −0.0131 (14) | 0.0088 (13) | −0.0014 (12) |
N13 | 0.0356 (15) | 0.0383 (14) | 0.0397 (13) | −0.0039 (11) | 0.0002 (11) | −0.0019 (11) |
N41 | 0.0386 (17) | 0.0547 (17) | 0.0402 (13) | −0.0070 (13) | 0.0036 (12) | −0.0100 (12) |
N43 | 0.0350 (16) | 0.0376 (14) | 0.0394 (13) | −0.0024 (11) | 0.0038 (11) | −0.0032 (11) |
N51 | 0.062 (2) | 0.0335 (15) | 0.0617 (17) | 0.0060 (14) | 0.0197 (15) | −0.0008 (12) |
N53 | 0.0449 (17) | 0.0354 (14) | 0.0424 (13) | 0.0008 (12) | 0.0058 (12) | 0.0022 (11) |
N81 | 0.0520 (19) | 0.0381 (15) | 0.0480 (14) | 0.0020 (13) | 0.0069 (13) | 0.0070 (12) |
N83 | 0.0404 (17) | 0.0356 (14) | 0.0424 (13) | −0.0011 (12) | 0.0032 (12) | 0.0001 (11) |
C11 | 0.0367 (19) | 0.0447 (18) | 0.0524 (18) | −0.0044 (15) | 0.0041 (15) | −0.0088 (14) |
C12 | 0.0391 (19) | 0.0373 (17) | 0.0422 (16) | −0.0070 (14) | 0.0035 (14) | −0.0024 (13) |
C13 | 0.0329 (18) | 0.0366 (17) | 0.0456 (16) | −0.0007 (14) | 0.0012 (14) | −0.0077 (13) |
C14 | 0.044 (2) | 0.050 (2) | 0.0505 (18) | 0.0028 (16) | −0.0051 (16) | −0.0064 (15) |
C15 | 0.046 (2) | 0.070 (2) | 0.0531 (19) | 0.0079 (19) | −0.0123 (18) | −0.0079 (18) |
C16 | 0.042 (2) | 0.078 (3) | 0.072 (2) | −0.005 (2) | −0.0091 (19) | −0.019 (2) |
C17 | 0.033 (2) | 0.066 (2) | 0.077 (2) | −0.0105 (17) | 0.0090 (18) | −0.0134 (19) |
C18 | 0.065 (3) | 0.091 (3) | 0.056 (2) | −0.024 (2) | 0.020 (2) | 0.002 (2) |
C19 | 0.117 (5) | 0.089 (4) | 0.106 (4) | −0.039 (3) | 0.026 (3) | 0.031 (3) |
C21 | 0.040 (2) | 0.0497 (19) | 0.0337 (14) | −0.0048 (15) | 0.0058 (14) | 0.0036 (13) |
C22 | 0.045 (2) | 0.0462 (19) | 0.0363 (15) | −0.0112 (15) | 0.0069 (14) | 0.0027 (13) |
C23 | 0.070 (3) | 0.045 (2) | 0.0523 (19) | −0.0100 (18) | −0.0006 (19) | 0.0037 (15) |
C24 | 0.074 (3) | 0.053 (2) | 0.054 (2) | 0.001 (2) | −0.001 (2) | 0.0138 (17) |
C25 | 0.064 (3) | 0.067 (2) | 0.0412 (17) | 0.001 (2) | −0.0089 (17) | 0.0085 (17) |
C26 | 0.055 (2) | 0.061 (2) | 0.0384 (16) | −0.0068 (19) | −0.0022 (16) | −0.0047 (15) |
C31 | 0.0363 (19) | 0.0433 (18) | 0.0396 (15) | −0.0011 (15) | 0.0012 (14) | −0.0102 (13) |
C32 | 0.0374 (19) | 0.053 (2) | 0.0308 (14) | −0.0059 (15) | 0.0018 (13) | −0.0089 (13) |
C33 | 0.039 (2) | 0.070 (2) | 0.0446 (17) | −0.0096 (18) | 0.0055 (15) | −0.0111 (16) |
C34 | 0.029 (2) | 0.086 (3) | 0.062 (2) | 0.004 (2) | 0.0032 (17) | −0.029 (2) |
C35 | 0.053 (3) | 0.057 (2) | 0.074 (2) | 0.012 (2) | −0.001 (2) | −0.0179 (19) |
C36 | 0.051 (2) | 0.046 (2) | 0.065 (2) | −0.0018 (17) | 0.0088 (18) | −0.0129 (16) |
C41 | 0.038 (2) | 0.0459 (18) | 0.0425 (16) | −0.0026 (15) | 0.0040 (14) | −0.0015 (13) |
C42 | 0.0384 (19) | 0.0370 (16) | 0.0392 (15) | −0.0026 (14) | 0.0026 (14) | 0.0002 (13) |
C43 | 0.0356 (18) | 0.0368 (16) | 0.0378 (15) | −0.0026 (14) | 0.0023 (13) | −0.0001 (12) |
C44 | 0.045 (2) | 0.0441 (18) | 0.0416 (16) | −0.0003 (15) | 0.0050 (15) | −0.0058 (14) |
C45 | 0.036 (2) | 0.068 (2) | 0.0539 (19) | 0.0009 (17) | 0.0111 (16) | −0.0044 (17) |
C46 | 0.031 (2) | 0.093 (3) | 0.064 (2) | −0.005 (2) | 0.0032 (18) | −0.007 (2) |
C47 | 0.041 (2) | 0.083 (3) | 0.0516 (19) | −0.0076 (19) | −0.0026 (17) | −0.0130 (18) |
C48 | 0.054 (2) | 0.077 (3) | 0.0438 (17) | −0.007 (2) | 0.0053 (17) | −0.0210 (17) |
C49 | 0.101 (4) | 0.083 (3) | 0.088 (3) | −0.008 (3) | 0.005 (3) | −0.039 (3) |
C51 | 0.043 (2) | 0.0364 (18) | 0.080 (2) | −0.0001 (16) | 0.0191 (19) | 0.0136 (17) |
C52 | 0.046 (2) | 0.0328 (16) | 0.0488 (17) | −0.0022 (15) | 0.0107 (15) | 0.0033 (13) |
C53 | 0.044 (2) | 0.0392 (18) | 0.0581 (19) | 0.0011 (15) | 0.0092 (16) | 0.0144 (15) |
C54 | 0.053 (2) | 0.059 (2) | 0.060 (2) | −0.0017 (19) | 0.0028 (18) | 0.0190 (17) |
C55 | 0.057 (3) | 0.079 (3) | 0.087 (3) | −0.001 (2) | −0.002 (2) | 0.043 (3) |
C56 | 0.052 (3) | 0.064 (3) | 0.132 (4) | 0.013 (2) | 0.007 (3) | 0.048 (3) |
C57 | 0.053 (3) | 0.047 (2) | 0.116 (4) | 0.0083 (19) | 0.018 (3) | 0.019 (2) |
C58 | 0.099 (4) | 0.044 (2) | 0.078 (3) | 0.005 (2) | 0.040 (2) | −0.0088 (18) |
C59 | 0.138 (5) | 0.052 (3) | 0.112 (4) | −0.004 (3) | 0.034 (4) | −0.029 (3) |
C61 | 0.044 (2) | 0.0422 (18) | 0.0342 (14) | 0.0003 (15) | 0.0083 (14) | −0.0018 (13) |
C62 | 0.054 (2) | 0.0368 (17) | 0.0405 (15) | −0.0021 (16) | 0.0095 (15) | −0.0043 (13) |
C63 | 0.073 (3) | 0.046 (2) | 0.058 (2) | −0.0170 (19) | 0.009 (2) | −0.0083 (16) |
C64 | 0.071 (3) | 0.076 (3) | 0.055 (2) | −0.026 (2) | −0.005 (2) | −0.012 (2) |
C65 | 0.061 (3) | 0.080 (3) | 0.0435 (18) | −0.004 (2) | −0.0034 (18) | 0.0011 (18) |
C66 | 0.055 (2) | 0.056 (2) | 0.0406 (16) | −0.0016 (18) | 0.0058 (16) | 0.0042 (15) |
C71 | 0.044 (2) | 0.0402 (18) | 0.0370 (15) | −0.0034 (15) | 0.0032 (14) | 0.0065 (13) |
C72 | 0.041 (2) | 0.0408 (17) | 0.0349 (14) | 0.0026 (14) | 0.0034 (13) | 0.0064 (12) |
C73 | 0.050 (2) | 0.055 (2) | 0.0544 (19) | 0.0123 (18) | 0.0120 (17) | 0.0100 (16) |
C74 | 0.037 (2) | 0.079 (3) | 0.063 (2) | 0.009 (2) | 0.0060 (17) | 0.019 (2) |
C75 | 0.039 (2) | 0.079 (3) | 0.056 (2) | −0.014 (2) | −0.0027 (17) | 0.0109 (19) |
C76 | 0.051 (2) | 0.055 (2) | 0.0524 (19) | −0.0112 (18) | 0.0051 (17) | −0.0001 (16) |
C81 | 0.052 (2) | 0.0347 (17) | 0.0568 (19) | 0.0031 (16) | 0.0039 (17) | 0.0001 (14) |
C82 | 0.044 (2) | 0.0305 (16) | 0.0405 (15) | −0.0003 (14) | 0.0010 (14) | 0.0013 (12) |
C83 | 0.047 (2) | 0.0333 (16) | 0.0495 (17) | 0.0016 (15) | 0.0045 (15) | −0.0013 (13) |
C84 | 0.051 (2) | 0.0432 (19) | 0.069 (2) | 0.0008 (17) | 0.0179 (19) | −0.0019 (16) |
C85 | 0.058 (3) | 0.052 (2) | 0.095 (3) | 0.005 (2) | 0.028 (2) | −0.002 (2) |
C86 | 0.060 (3) | 0.047 (2) | 0.107 (3) | 0.015 (2) | 0.007 (2) | −0.002 (2) |
C87 | 0.066 (3) | 0.044 (2) | 0.079 (2) | 0.0119 (19) | 0.007 (2) | 0.0071 (18) |
C88 | 0.080 (3) | 0.053 (2) | 0.0494 (19) | 0.005 (2) | 0.0109 (19) | 0.0136 (16) |
C89 | 0.117 (4) | 0.056 (3) | 0.096 (3) | −0.016 (3) | 0.019 (3) | 0.020 (2) |
S | 0.0835 (10) | 0.1121 (11) | 0.0886 (8) | 0.0300 (8) | 0.0105 (7) | 0.0287 (8) |
O1 | 0.154 (4) | 0.139 (4) | 0.143 (4) | 0.022 (3) | 0.040 (3) | −0.041 (3) |
F1 | 0.251 (7) | 0.227 (6) | 0.222 (5) | 0.120 (5) | 0.071 (5) | 0.146 (5) |
F3 | 0.161 (4) | 0.171 (4) | 0.177 (4) | 0.060 (3) | 0.038 (3) | −0.032 (3) |
O2 | 0.090 (3) | 0.172 (4) | 0.143 (4) | 0.009 (3) | −0.034 (3) | −0.011 (3) |
O3 | 0.169 (5) | 0.176 (5) | 0.198 (5) | 0.033 (4) | 0.071 (4) | 0.106 (4) |
C1 | 0.123 (6) | 0.135 (5) | 0.092 (4) | 0.042 (5) | 0.023 (4) | 0.014 (4) |
F2 | 0.117 (4) | 0.260 (6) | 0.268 (6) | 0.075 (4) | −0.086 (4) | −0.067 (5) |
C90 | 0.085 (4) | 0.069 (3) | 0.068 (2) | 0.005 (3) | 0.015 (2) | 0.005 (2) |
C91 | 0.097 (4) | 0.064 (3) | 0.095 (3) | −0.002 (3) | 0.043 (3) | 0.003 (2) |
C92 | 0.104 (5) | 0.099 (4) | 0.097 (4) | 0.035 (4) | 0.033 (4) | 0.002 (3) |
C93 | 0.076 (4) | 0.194 (8) | 0.073 (3) | 0.022 (5) | 0.016 (3) | −0.030 (4) |
C94 | 0.119 (6) | 0.124 (5) | 0.075 (3) | −0.040 (4) | 0.025 (3) | −0.033 (3) |
C95 | 0.133 (5) | 0.060 (3) | 0.064 (3) | 0.006 (3) | 0.013 (3) | −0.002 (2) |
C96 | 0.103 (5) | 0.139 (6) | 0.138 (5) | 0.014 (4) | 0.010 (4) | −0.003 (4) |
O4 | 0.178 (5) | 0.201 (6) | 0.196 (5) | −0.021 (5) | 0.022 (4) | −0.034 (5) |
Cu—N13 | 2.088 (3) | C51—C53 | 1.399 (5) |
Cu—N43 | 2.072 (2) | C51—C57 | 1.402 (5) |
Cu—N53 | 2.121 (3) | C52—C62 | 1.472 (5) |
Cu—N83 | 2.119 (2) | C53—C54 | 1.397 (5) |
N11—C12 | 1.368 (4) | C54—C55 | 1.377 (6) |
N11—C11 | 1.383 (4) | C54—H54 | 0.9300 |
N11—C18 | 1.468 (4) | C55—C56 | 1.383 (7) |
N13—C12 | 1.318 (4) | C55—H55 | 0.9300 |
N13—C13 | 1.407 (4) | C56—C57 | 1.356 (7) |
N41—C42 | 1.359 (4) | C56—H56 | 0.9300 |
N41—C41 | 1.383 (4) | C57—H57 | 0.9300 |
N41—C48 | 1.472 (4) | C58—C59 | 1.518 (6) |
N43—C42 | 1.317 (4) | C58—H58A | 0.9700 |
N43—C43 | 1.398 (4) | C58—H58B | 0.9700 |
N51—C52 | 1.370 (4) | C59—H59A | 0.9600 |
N51—C51 | 1.376 (5) | C59—H59B | 0.9600 |
N51—C58 | 1.472 (5) | C59—H59C | 0.9600 |
N53—C52 | 1.321 (4) | C61—C66 | 1.383 (5) |
N53—C53 | 1.390 (4) | C61—C62 | 1.398 (4) |
N81—C82 | 1.365 (4) | C61—C72 | 1.485 (5) |
N81—C81 | 1.382 (4) | C62—C63 | 1.387 (5) |
N81—C88 | 1.470 (4) | C63—C64 | 1.374 (6) |
N83—C82 | 1.319 (4) | C63—H63 | 0.9300 |
N83—C83 | 1.393 (4) | C64—C65 | 1.368 (6) |
C11—C17 | 1.387 (5) | C64—H64 | 0.9300 |
C11—C13 | 1.387 (4) | C65—C66 | 1.393 (5) |
C12—C22 | 1.472 (4) | C65—H65 | 0.9300 |
C13—C14 | 1.389 (4) | C66—H66 | 0.9300 |
C14—C15 | 1.375 (5) | C71—C76 | 1.390 (5) |
C14—H14 | 0.9300 | C71—C72 | 1.395 (4) |
C15—C16 | 1.377 (6) | C71—C82 | 1.481 (5) |
C15—H15 | 0.9300 | C72—C73 | 1.401 (5) |
C16—C17 | 1.381 (6) | C73—C74 | 1.371 (5) |
C16—H16 | 0.9300 | C73—H73 | 0.9300 |
C17—H17 | 0.9300 | C74—C75 | 1.378 (6) |
C18—C19 | 1.517 (7) | C74—H74 | 0.9300 |
C18—H18A | 0.9700 | C75—C76 | 1.371 (5) |
C18—H18B | 0.9700 | C75—H75 | 0.9300 |
C19—H19A | 0.9600 | C76—H76 | 0.9300 |
C19—H19B | 0.9600 | C81—C87 | 1.375 (5) |
C19—H19C | 0.9600 | C81—C83 | 1.396 (4) |
C21—C26 | 1.393 (5) | C83—C84 | 1.386 (5) |
C21—C22 | 1.401 (4) | C84—C85 | 1.374 (5) |
C21—C32 | 1.483 (5) | C84—H84 | 0.9300 |
C22—C23 | 1.394 (5) | C85—C86 | 1.382 (6) |
C23—C24 | 1.362 (5) | C85—H85 | 0.9300 |
C23—H23 | 0.9300 | C86—C87 | 1.372 (6) |
C24—C25 | 1.373 (5) | C86—H86 | 0.9300 |
C24—H24 | 0.9300 | C87—H87 | 0.9300 |
C25—C26 | 1.380 (5) | C88—C89 | 1.495 (6) |
C25—H25 | 0.9300 | C88—H88A | 0.9700 |
C26—H26 | 0.9300 | C88—H88B | 0.9700 |
C31—C36 | 1.383 (5) | C89—H89A | 0.9600 |
C31—C32 | 1.393 (4) | C89—H89B | 0.9600 |
C31—C42 | 1.475 (5) | C89—H89C | 0.9600 |
C32—C33 | 1.396 (5) | S—O3 | 1.404 (4) |
C33—C34 | 1.384 (5) | S—O1 | 1.416 (4) |
C33—H33 | 0.9300 | S—O2 | 1.439 (4) |
C34—C35 | 1.367 (6) | S—C1 | 1.741 (6) |
C34—H34 | 0.9300 | F1—C1 | 1.283 (6) |
C35—C36 | 1.386 (5) | F3—C1 | 1.327 (6) |
C35—H35 | 0.9300 | C1—F2 | 1.321 (6) |
C36—H36 | 0.9300 | C90—C91 | 1.373 (7) |
C41—C43 | 1.387 (4) | C90—C95 | 1.374 (7) |
C41—C47 | 1.398 (5) | C90—C96 | 1.511 (8) |
C43—C44 | 1.393 (4) | C91—C92 | 1.347 (7) |
C44—C45 | 1.363 (5) | C91—H91 | 0.9300 |
C44—H44 | 0.9300 | C92—C93 | 1.363 (9) |
C45—C46 | 1.390 (5) | C92—H92 | 0.9300 |
C45—H45 | 0.9300 | C93—C94 | 1.376 (9) |
C46—C47 | 1.364 (5) | C93—H93 | 0.9300 |
C46—H46 | 0.9300 | C94—C95 | 1.373 (8) |
C47—H47 | 0.9300 | C94—H94 | 0.9300 |
C48—C49 | 1.494 (6) | C95—H95 | 0.9300 |
C48—H48A | 0.9700 | C96—H96A | 0.9600 |
C48—H48B | 0.9700 | C96—H96B | 0.9600 |
C49—H49A | 0.9600 | C96—H96C | 0.9600 |
C49—H49B | 0.9600 | O4—H41O | 0.96 (4) |
C49—H49C | 0.9600 | O4—H42O | 1.00 (4) |
N83—Cu—N53 | 119.01 (9) | N53—C52—C62 | 124.4 (3) |
N43—Cu—N13 | 118.16 (9) | N51—C52—C62 | 122.7 (3) |
N13—Cu—N83 | 111.57 (10) | N53—C53—C54 | 130.2 (3) |
N43—Cu—N53 | 109.51 (10) | N53—C53—C51 | 109.8 (3) |
N43—Cu—N83 | 100.48 (10) | C54—C53—C51 | 120.0 (3) |
N13—Cu—N53 | 99.15 (10) | C55—C54—C53 | 117.5 (4) |
C12—N11—C11 | 107.0 (3) | C55—C54—H54 | 121.2 |
C12—N11—C18 | 128.5 (3) | C53—C54—H54 | 121.2 |
C11—N11—C18 | 124.5 (3) | C54—C55—C56 | 121.3 (4) |
C12—N13—C13 | 104.9 (3) | C54—C55—H55 | 119.4 |
C12—N13—Cu | 132.1 (2) | C56—C55—H55 | 119.4 |
C13—N13—Cu | 122.61 (19) | C57—C56—C55 | 122.9 (4) |
C42—N41—C41 | 106.7 (2) | C57—C56—H56 | 118.5 |
C42—N41—C48 | 128.0 (3) | C55—C56—H56 | 118.5 |
C41—N41—C48 | 125.2 (3) | C56—C57—C51 | 116.4 (4) |
C42—N43—C43 | 105.1 (2) | C56—C57—H57 | 121.8 |
C42—N43—Cu | 128.8 (2) | C51—C57—H57 | 121.8 |
C43—N43—Cu | 126.01 (19) | N51—C58—C59 | 112.1 (3) |
C52—N51—C51 | 106.8 (3) | N51—C58—H58A | 109.2 |
C52—N51—C58 | 127.8 (3) | C59—C58—H58A | 109.2 |
C51—N51—C58 | 125.2 (3) | N51—C58—H58B | 109.2 |
C52—N53—C53 | 104.9 (3) | C59—C58—H58B | 109.2 |
C52—N53—Cu | 130.6 (2) | H58A—C58—H58B | 107.9 |
C53—N53—Cu | 124.4 (2) | C58—C59—H59A | 109.5 |
C82—N81—C81 | 106.9 (3) | C58—C59—H59B | 109.5 |
C82—N81—C88 | 127.6 (3) | H59A—C59—H59B | 109.5 |
C81—N81—C88 | 125.3 (3) | C58—C59—H59C | 109.5 |
C82—N83—C83 | 105.0 (2) | H59A—C59—H59C | 109.5 |
C82—N83—Cu | 128.3 (2) | H59B—C59—H59C | 109.5 |
C83—N83—Cu | 126.7 (2) | C66—C61—C62 | 118.4 (3) |
N11—C11—C17 | 132.1 (3) | C66—C61—C72 | 120.5 (3) |
N11—C11—C13 | 105.7 (3) | C62—C61—C72 | 121.0 (3) |
C17—C11—C13 | 122.1 (3) | C63—C62—C61 | 119.8 (3) |
N13—C12—N11 | 112.7 (3) | C63—C62—C52 | 119.8 (3) |
N13—C12—C22 | 124.8 (3) | C61—C62—C52 | 120.2 (3) |
N11—C12—C22 | 122.4 (3) | C64—C63—C62 | 120.7 (3) |
C11—C13—C14 | 120.7 (3) | C64—C63—H63 | 119.6 |
C11—C13—N13 | 109.7 (3) | C62—C63—H63 | 119.6 |
C14—C13—N13 | 129.6 (3) | C65—C64—C63 | 120.1 (4) |
C15—C14—C13 | 117.0 (3) | C65—C64—H64 | 120.0 |
C15—C14—H14 | 121.5 | C63—C64—H64 | 120.0 |
C13—C14—H14 | 121.5 | C64—C65—C66 | 119.7 (4) |
C14—C15—C16 | 122.0 (3) | C64—C65—H65 | 120.2 |
C14—C15—H15 | 119.0 | C66—C65—H65 | 120.2 |
C16—C15—H15 | 119.0 | C61—C66—C65 | 121.1 (3) |
C15—C16—C17 | 121.9 (4) | C61—C66—H66 | 119.5 |
C15—C16—H16 | 119.0 | C65—C66—H66 | 119.5 |
C17—C16—H16 | 119.0 | C76—C71—C72 | 120.2 (3) |
C16—C17—C11 | 116.2 (4) | C76—C71—C82 | 121.0 (3) |
C16—C17—H17 | 121.9 | C72—C71—C82 | 118.7 (3) |
C11—C17—H17 | 121.9 | C71—C72—C73 | 117.8 (3) |
N11—C18—C19 | 112.9 (3) | C71—C72—C61 | 121.7 (3) |
N11—C18—H18A | 109.0 | C73—C72—C61 | 120.4 (3) |
C19—C18—H18A | 109.0 | C74—C73—C72 | 121.2 (3) |
N11—C18—H18B | 109.0 | C74—C73—H73 | 119.4 |
C19—C18—H18B | 109.0 | C72—C73—H73 | 119.4 |
H18A—C18—H18B | 107.8 | C73—C74—C75 | 120.5 (4) |
C18—C19—H19A | 109.5 | C73—C74—H74 | 119.8 |
C18—C19—H19B | 109.5 | C75—C74—H74 | 119.8 |
H19A—C19—H19B | 109.5 | C76—C75—C74 | 119.5 (4) |
C18—C19—H19C | 109.5 | C76—C75—H75 | 120.3 |
H19A—C19—H19C | 109.5 | C74—C75—H75 | 120.3 |
H19B—C19—H19C | 109.5 | C75—C76—C71 | 120.9 (3) |
C26—C21—C22 | 118.4 (3) | C75—C76—H76 | 119.6 |
C26—C21—C32 | 119.5 (3) | C71—C76—H76 | 119.6 |
C22—C21—C32 | 122.0 (3) | C87—C81—N81 | 131.7 (3) |
C23—C22—C21 | 119.2 (3) | C87—C81—C83 | 122.8 (3) |
C23—C22—C12 | 119.2 (3) | N81—C81—C83 | 105.5 (3) |
C21—C22—C12 | 121.4 (3) | N83—C82—N81 | 112.8 (3) |
C24—C23—C22 | 121.2 (3) | N83—C82—C71 | 124.4 (3) |
C24—C23—H23 | 119.4 | N81—C82—C71 | 122.8 (3) |
C22—C23—H23 | 119.4 | C84—C83—N83 | 130.6 (3) |
C23—C24—C25 | 120.1 (4) | C84—C83—C81 | 119.6 (3) |
C23—C24—H24 | 119.9 | N83—C83—C81 | 109.8 (3) |
C25—C24—H24 | 119.9 | C85—C84—C83 | 117.9 (3) |
C24—C25—C26 | 119.9 (3) | C85—C84—H84 | 121.1 |
C24—C25—H25 | 120.0 | C83—C84—H84 | 121.1 |
C26—C25—H25 | 120.0 | C84—C85—C86 | 121.3 (4) |
C25—C26—C21 | 121.1 (3) | C84—C85—H85 | 119.3 |
C25—C26—H26 | 119.5 | C86—C85—H85 | 119.3 |
C21—C26—H26 | 119.5 | C87—C86—C85 | 122.1 (4) |
C36—C31—C32 | 120.1 (3) | C87—C86—H86 | 119.0 |
C36—C31—C42 | 120.2 (3) | C85—C86—H86 | 119.0 |
C32—C31—C42 | 119.7 (3) | C86—C87—C81 | 116.4 (4) |
C31—C32—C33 | 118.3 (3) | C86—C87—H87 | 121.8 |
C31—C32—C21 | 121.3 (3) | C81—C87—H87 | 121.8 |
C33—C32—C21 | 120.3 (3) | N81—C88—C89 | 113.0 (3) |
C34—C33—C32 | 120.9 (3) | N81—C88—H88A | 109.0 |
C34—C33—H33 | 119.5 | C89—C88—H88A | 109.0 |
C32—C33—H33 | 119.5 | N81—C88—H88B | 109.0 |
C35—C34—C33 | 120.4 (3) | C89—C88—H88B | 109.0 |
C35—C34—H34 | 119.8 | H88A—C88—H88B | 107.8 |
C33—C34—H34 | 119.8 | C88—C89—H89A | 109.5 |
C34—C35—C36 | 119.4 (4) | C88—C89—H89B | 109.5 |
C34—C35—H35 | 120.3 | H89A—C89—H89B | 109.5 |
C36—C35—H35 | 120.3 | C88—C89—H89C | 109.5 |
C31—C36—C35 | 120.9 (4) | H89A—C89—H89C | 109.5 |
C31—C36—H36 | 119.6 | H89B—C89—H89C | 109.5 |
C35—C36—H36 | 119.6 | O3—S—O1 | 115.4 (4) |
N41—C41—C43 | 105.9 (3) | O3—S—O2 | 118.0 (4) |
N41—C41—C47 | 132.3 (3) | O1—S—O2 | 112.1 (3) |
C43—C41—C47 | 121.8 (3) | O3—S—C1 | 103.9 (3) |
N43—C42—N41 | 112.9 (3) | O1—S—C1 | 102.6 (3) |
N43—C42—C31 | 125.0 (3) | O2—S—C1 | 102.1 (3) |
N41—C42—C31 | 122.2 (3) | F1—C1—F2 | 108.1 (6) |
C41—C43—C44 | 120.3 (3) | F1—C1—F3 | 104.0 (6) |
C41—C43—N43 | 109.3 (3) | F2—C1—F3 | 102.6 (6) |
C44—C43—N43 | 130.4 (3) | F1—C1—S | 113.5 (5) |
C45—C44—C43 | 117.8 (3) | F2—C1—S | 114.5 (5) |
C45—C44—H44 | 121.1 | F3—C1—S | 113.0 (4) |
C43—C44—H44 | 121.1 | C91—C90—C95 | 117.4 (5) |
C44—C45—C46 | 121.4 (3) | C91—C90—C96 | 120.0 (5) |
C44—C45—H45 | 119.3 | C95—C90—C96 | 122.6 (5) |
C46—C45—H45 | 119.3 | C92—C91—C90 | 121.7 (5) |
C47—C46—C45 | 122.2 (3) | C92—C91—H91 | 119.2 |
C47—C46—H46 | 118.9 | C90—C91—H91 | 119.2 |
C45—C46—H46 | 118.9 | C91—C92—C93 | 120.4 (6) |
C46—C47—C41 | 116.4 (3) | C91—C92—H92 | 119.8 |
C46—C47—H47 | 121.8 | C93—C92—H92 | 119.8 |
C41—C47—H47 | 121.8 | C92—C93—C94 | 120.0 (6) |
N41—C48—C49 | 113.4 (3) | C92—C93—H93 | 120.0 |
N41—C48—H48A | 108.9 | C94—C93—H93 | 120.0 |
C49—C48—H48A | 108.9 | C95—C94—C93 | 118.5 (6) |
N41—C48—H48B | 108.9 | C95—C94—H94 | 120.7 |
C49—C48—H48B | 108.9 | C93—C94—H94 | 120.7 |
H48A—C48—H48B | 107.7 | C94—C95—C90 | 121.9 (5) |
C48—C49—H49A | 109.5 | C94—C95—H95 | 119.1 |
C48—C49—H49B | 109.5 | C90—C95—H95 | 119.1 |
H49A—C49—H49B | 109.5 | C90—C96—H96A | 109.5 |
C48—C49—H49C | 109.5 | C90—C96—H96B | 109.5 |
H49A—C49—H49C | 109.5 | H96A—C96—H96B | 109.5 |
H49B—C49—H49C | 109.5 | C90—C96—H96C | 109.5 |
N51—C51—C53 | 105.7 (3) | H96A—C96—H96C | 109.5 |
N51—C51—C57 | 132.5 (4) | H96B—C96—H96C | 109.5 |
C53—C51—C57 | 121.8 (4) | H41O—O4—H42O | 99 (6) |
N53—C52—N51 | 112.8 (3) | ||
N43—Cu—N13—C12 | 30.9 (3) | C43—C41—C47—C46 | −2.3 (5) |
N83—Cu—N13—C12 | 146.6 (3) | C42—N41—C48—C49 | 104.9 (4) |
N53—Cu—N13—C12 | −87.1 (3) | C41—N41—C48—C49 | −78.5 (5) |
N43—Cu—N13—C13 | −157.7 (2) | C52—N51—C51—C53 | 0.0 (4) |
N83—Cu—N13—C13 | −42.0 (2) | C58—N51—C51—C53 | −175.3 (3) |
N53—Cu—N13—C13 | 84.3 (2) | C52—N51—C51—C57 | −177.9 (4) |
N13—Cu—N43—C42 | 36.2 (3) | C58—N51—C51—C57 | 6.8 (6) |
N83—Cu—N43—C42 | −85.4 (3) | C53—N53—C52—N51 | 1.3 (4) |
N53—Cu—N43—C42 | 148.6 (2) | Cu—N53—C52—N51 | 176.9 (2) |
N13—Cu—N43—C43 | −141.7 (2) | C53—N53—C52—C62 | −175.7 (3) |
N83—Cu—N43—C43 | 96.8 (2) | Cu—N53—C52—C62 | −0.1 (5) |
N53—Cu—N43—C43 | −29.3 (3) | C51—N51—C52—N53 | −0.8 (4) |
N43—Cu—N53—C52 | 145.4 (3) | C58—N51—C52—N53 | 174.3 (3) |
N13—Cu—N53—C52 | −90.2 (3) | C51—N51—C52—C62 | 176.3 (3) |
N83—Cu—N53—C52 | 30.8 (3) | C58—N51—C52—C62 | −8.6 (5) |
N43—Cu—N53—C53 | −39.7 (3) | C52—N53—C53—C54 | 177.6 (4) |
N13—Cu—N53—C53 | 84.6 (3) | Cu—N53—C53—C54 | 1.6 (5) |
N83—Cu—N53—C53 | −154.4 (2) | C52—N53—C53—C51 | −1.3 (4) |
N43—Cu—N83—C82 | −81.0 (3) | Cu—N53—C53—C51 | −177.3 (2) |
N13—Cu—N83—C82 | 152.9 (2) | N51—C51—C53—N53 | 0.8 (4) |
N53—Cu—N83—C82 | 38.4 (3) | C57—C51—C53—N53 | 179.0 (3) |
N43—Cu—N83—C83 | 98.2 (3) | N51—C51—C53—C54 | −178.2 (3) |
N13—Cu—N83—C83 | −27.9 (3) | C57—C51—C53—C54 | 0.0 (5) |
N53—Cu—N83—C83 | −142.4 (2) | N53—C53—C54—C55 | −178.0 (4) |
C12—N11—C11—C17 | −178.1 (4) | C51—C53—C54—C55 | 0.8 (5) |
C18—N11—C11—C17 | 2.1 (6) | C53—C54—C55—C56 | −1.0 (6) |
C12—N11—C11—C13 | 0.3 (3) | C54—C55—C56—C57 | 0.4 (7) |
C18—N11—C11—C13 | −179.5 (3) | C55—C56—C57—C51 | 0.4 (7) |
C13—N13—C12—N11 | 1.6 (3) | N51—C51—C57—C56 | 177.0 (4) |
Cu—N13—C12—N11 | 174.1 (2) | C53—C51—C57—C56 | −0.6 (6) |
C13—N13—C12—C22 | −174.2 (3) | C52—N51—C58—C59 | 103.4 (5) |
Cu—N13—C12—C22 | −1.7 (5) | C51—N51—C58—C59 | −82.3 (5) |
C11—N11—C12—N13 | −1.2 (4) | C66—C61—C62—C63 | −3.8 (5) |
C18—N11—C12—N13 | 178.6 (3) | C72—C61—C62—C63 | 173.5 (3) |
C11—N11—C12—C22 | 174.7 (3) | C66—C61—C62—C52 | 171.9 (3) |
C18—N11—C12—C22 | −5.5 (5) | C72—C61—C62—C52 | −10.8 (4) |
N11—C11—C13—C14 | −177.2 (3) | N53—C52—C62—C63 | 111.8 (4) |
C17—C11—C13—C14 | 1.4 (5) | N51—C52—C62—C63 | −64.9 (4) |
N11—C11—C13—N13 | 0.6 (3) | N53—C52—C62—C61 | −63.9 (4) |
C17—C11—C13—N13 | 179.2 (3) | N51—C52—C62—C61 | 119.4 (3) |
C12—N13—C13—C11 | −1.3 (3) | C61—C62—C63—C64 | 1.2 (5) |
Cu—N13—C13—C11 | −174.8 (2) | C52—C62—C63—C64 | −174.6 (3) |
C12—N13—C13—C14 | 176.2 (3) | C62—C63—C64—C65 | 2.7 (6) |
Cu—N13—C13—C14 | 2.8 (4) | C63—C64—C65—C66 | −3.7 (6) |
C11—C13—C14—C15 | 0.5 (5) | C62—C61—C66—C65 | 2.8 (5) |
N13—C13—C14—C15 | −176.8 (3) | C72—C61—C66—C65 | −174.5 (3) |
C13—C14—C15—C16 | −1.7 (5) | C64—C65—C66—C61 | 1.0 (6) |
C14—C15—C16—C17 | 1.0 (6) | C76—C71—C72—C73 | −0.9 (4) |
C15—C16—C17—C11 | 0.8 (6) | C82—C71—C72—C73 | 175.1 (3) |
N11—C11—C17—C16 | 176.1 (4) | C76—C71—C72—C61 | 175.0 (3) |
C13—C11—C17—C16 | −2.0 (5) | C82—C71—C72—C61 | −9.1 (4) |
C12—N11—C18—C19 | 104.8 (5) | C66—C61—C72—C71 | −60.0 (4) |
C11—N11—C18—C19 | −75.4 (5) | C62—C61—C72—C71 | 122.8 (3) |
C26—C21—C22—C23 | −1.6 (5) | C66—C61—C72—C73 | 115.8 (3) |
C32—C21—C22—C23 | 176.3 (3) | C62—C61—C72—C73 | −61.5 (4) |
C26—C21—C22—C12 | 173.4 (3) | C71—C72—C73—C74 | 0.1 (5) |
C32—C21—C22—C12 | −8.7 (5) | C61—C72—C73—C74 | −175.8 (3) |
N13—C12—C22—C23 | 109.8 (4) | C72—C73—C74—C75 | 1.3 (5) |
N11—C12—C22—C23 | −65.6 (4) | C73—C74—C75—C76 | −1.9 (5) |
N13—C12—C22—C21 | −65.1 (4) | C74—C75—C76—C71 | 1.1 (5) |
N11—C12—C22—C21 | 119.4 (3) | C72—C71—C76—C75 | 0.2 (5) |
C21—C22—C23—C24 | 0.4 (5) | C82—C71—C76—C75 | −175.6 (3) |
C12—C22—C23—C24 | −174.7 (3) | C82—N81—C81—C87 | 176.9 (4) |
C22—C23—C24—C25 | 1.4 (6) | C88—N81—C81—C87 | 0.4 (6) |
C23—C24—C25—C26 | −1.9 (6) | C82—N81—C81—C83 | −0.8 (3) |
C24—C25—C26—C21 | 0.6 (6) | C88—N81—C81—C83 | −177.2 (3) |
C22—C21—C26—C25 | 1.1 (5) | C83—N83—C82—N81 | 0.6 (3) |
C32—C21—C26—C25 | −176.8 (3) | Cu—N83—C82—N81 | 179.9 (2) |
C36—C31—C32—C33 | 0.8 (4) | C83—N83—C82—C71 | 179.2 (3) |
C42—C31—C32—C33 | 179.9 (3) | Cu—N83—C82—C71 | −1.5 (4) |
C36—C31—C32—C21 | 176.5 (3) | C81—N81—C82—N83 | 0.1 (4) |
C42—C31—C32—C21 | −4.3 (4) | C88—N81—C82—N83 | 176.5 (3) |
C26—C21—C32—C31 | −67.9 (4) | C81—N81—C82—C71 | −178.5 (3) |
C22—C21—C32—C31 | 114.2 (3) | C88—N81—C82—C71 | −2.1 (5) |
C26—C21—C32—C33 | 107.7 (4) | C76—C71—C82—N83 | 109.1 (4) |
C22—C21—C32—C33 | −70.2 (4) | C72—C71—C82—N83 | −66.8 (4) |
C31—C32—C33—C34 | 0.9 (4) | C76—C71—C82—N81 | −72.4 (4) |
C21—C32—C33—C34 | −174.9 (3) | C72—C71—C82—N81 | 111.6 (3) |
C32—C33—C34—C35 | −1.6 (5) | C82—N83—C83—C84 | 179.8 (3) |
C33—C34—C35—C36 | 0.5 (5) | Cu—N83—C83—C84 | 0.4 (5) |
C32—C31—C36—C35 | −1.8 (5) | C82—N83—C83—C81 | −1.1 (3) |
C42—C31—C36—C35 | 179.0 (3) | Cu—N83—C83—C81 | 179.6 (2) |
C34—C35—C36—C31 | 1.2 (5) | C87—C81—C83—C84 | 2.5 (5) |
C42—N41—C41—C43 | −1.2 (3) | N81—C81—C83—C84 | −179.6 (3) |
C48—N41—C41—C43 | −178.5 (3) | C87—C81—C83—N83 | −176.8 (3) |
C42—N41—C41—C47 | 178.2 (4) | N81—C81—C83—N83 | 1.1 (4) |
C48—N41—C41—C47 | 0.9 (6) | N83—C83—C84—C85 | 177.0 (3) |
C43—N43—C42—N41 | 0.2 (3) | C81—C83—C84—C85 | −2.1 (5) |
Cu—N43—C42—N41 | −178.0 (2) | C83—C84—C85—C86 | 0.6 (6) |
C43—N43—C42—C31 | −179.5 (3) | C84—C85—C86—C87 | 0.5 (7) |
Cu—N43—C42—C31 | 2.3 (4) | C85—C86—C87—C81 | −0.2 (6) |
C41—N41—C42—N43 | 0.6 (4) | N81—C81—C87—C86 | −178.6 (4) |
C48—N41—C42—N43 | 177.8 (3) | C83—C81—C87—C86 | −1.3 (6) |
C41—N41—C42—C31 | −179.6 (3) | C82—N81—C88—C89 | 103.9 (4) |
C48—N41—C42—C31 | −2.5 (5) | C81—N81—C88—C89 | −80.4 (5) |
C36—C31—C42—N43 | 105.5 (4) | O3—S—C1—F1 | −179.3 (6) |
C32—C31—C42—N43 | −73.6 (4) | O1—S—C1—F1 | 60.1 (6) |
C36—C31—C42—N41 | −74.2 (4) | O2—S—C1—F1 | −56.1 (6) |
C32—C31—C42—N41 | 106.6 (3) | O3—S—C1—F2 | 55.9 (6) |
N41—C41—C43—C44 | −178.0 (3) | O1—S—C1—F2 | −64.6 (6) |
C47—C41—C43—C44 | 2.6 (5) | O2—S—C1—F2 | 179.2 (5) |
N41—C41—C43—N43 | 1.4 (3) | O3—S—C1—F3 | −61.2 (6) |
C47—C41—C43—N43 | −178.0 (3) | O1—S—C1—F3 | 178.3 (5) |
C42—N43—C43—C41 | −1.0 (3) | O2—S—C1—F3 | 62.1 (6) |
Cu—N43—C43—C41 | 177.2 (2) | C95—C90—C91—C92 | 1.8 (7) |
C42—N43—C43—C44 | 178.3 (3) | C96—C90—C91—C92 | −177.4 (5) |
Cu—N43—C43—C44 | −3.5 (5) | C90—C91—C92—C93 | −1.5 (8) |
C41—C43—C44—C45 | −0.8 (5) | C91—C92—C93—C94 | −1.0 (8) |
N43—C43—C44—C45 | 179.9 (3) | C92—C93—C94—C95 | 2.9 (8) |
C43—C44—C45—C46 | −1.1 (5) | C93—C94—C95—C90 | −2.6 (8) |
C44—C45—C46—C47 | 1.3 (6) | C91—C90—C95—C94 | 0.3 (7) |
C45—C46—C47—C41 | 0.4 (6) | C96—C90—C95—C94 | 179.4 (5) |
N41—C41—C47—C46 | 178.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H41O···O3 | 0.96 (8) | 2.22 (9) | 3.000 (9) | 137 (10) |
C—H | N or Cg(J) | H···N, Cg(J) | C—H···N, Cg(J) |
C14—H14 | N83 | 2.877 | 135.2 |
C44—H44 | N53 | 2.820 | 132.5 |
C54—H54 | N43 | 2.889 | 133.0 |
C84—H84 | N13 | 2.898 | 134.6 |
C66—H66 | N81 | 2.979 | 116.6 |
C14—H14 | Cg(10) | 2.872 | 130.5 |
C44—H44 | Cg(11) | 2.885 | 127.9 |
C54—H54 | Cg(6) | 2.909 | 131.7 |
C17—H17 | Cg(9)ii | 3.012 | 140.1 |
C45—H45 | Cg(5)iii | 2.818 | 148.4 |
C65—H65 | Cg(11)iv | 2.958 | 123.1 |
C88—H88A | Cg(10)iv | 3.052 | 143.5 |
C91—H91 | Cg(5) | 2.854 | 153.7 |
C92—H92 | Cg(3) | 2.794 | 141.1 |
C94—H94 | Cg(4)v | 2.981 | 152.5 |
C95—H95 | Cg(8)v | 3.036 | 158.9 |
Notes: Cg(J) corresponds to the center of gravity of the Jth ring, as defined in Fig. 5. Interactions with H···Cg distances shorter than 3.10Å are reported. Symmetry codes: (ii) x-1, y, z; (iii) x+1, y, z; (iv) 2-x, -y, -z; (v), 2-x, 1/2+y, 1/2-z. |
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