Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010749/ng2019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010749/ng2019Isup2.hkl |
CCDC reference: 605135
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.101
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C32
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Cu2(C12H8N2)2(C7H4SO5)2(H2O)2]·3H2O | F(000) = 2000 |
Mr = 977.89 | Dx = 1.648 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6431 reflections |
a = 15.7402 (8) Å | θ = 2.4–25.4° |
b = 11.0625 (6) Å | µ = 1.26 mm−1 |
c = 22.8274 (12) Å | T = 298 K |
β = 97.334 (1)° | Prism, blue |
V = 3942.3 (4) Å3 | 0.28 × 0.22 × 0.14 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 7158 independent reflections |
Radiation source: fine-focus sealed tube | 5901 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scan | θmax = 25.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −18→18 |
Tmin = 0.719, Tmax = 0.843 | k = −10→13 |
20723 measured reflections | l = −24→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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0544P)2 + 1.1268P] where P = (Fo2 + 2Fc2)/3 |
7158 reflections | (Δ/σ)max = 0.001 |
550 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.29 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 | ||
Cu1 | 0.80138 (2) | 0.61081 (3) | 0.536653 (14) | 0.03628 (10) | |
Cu2 | 0.67954 (2) | 0.38368 (3) | 0.508955 (14) | 0.03769 (11) | |
S1 | 0.54187 (4) | 0.78439 (6) | 0.62777 (3) | 0.04337 (18) | |
S2 | 0.90862 (7) | 0.10977 (8) | 0.60958 (4) | 0.0685 (3) | |
O1 | 0.72407 (12) | 0.61912 (16) | 0.59824 (8) | 0.0443 (5) | |
O2 | 0.62585 (12) | 0.48112 (18) | 0.56462 (8) | 0.0489 (5) | |
O3 | 0.54349 (12) | 0.74297 (18) | 0.56769 (8) | 0.0508 (5) | |
O4 | 0.61102 (15) | 0.86774 (19) | 0.64655 (10) | 0.0671 (6) | |
O5 | 0.45886 (14) | 0.8268 (2) | 0.63884 (10) | 0.0651 (6) | |
O6 | 0.85564 (12) | 0.46512 (17) | 0.57103 (9) | 0.0528 (5) | |
O7 | 0.75924 (12) | 0.31979 (17) | 0.57683 (8) | 0.0473 (5) | |
O8 | 0.92273 (16) | 0.1715 (3) | 0.55598 (10) | 0.0856 (8) | |
O9 | 0.82341 (19) | 0.0587 (2) | 0.60658 (13) | 0.0880 (8) | |
O10 | 0.9760 (2) | 0.0251 (3) | 0.62912 (13) | 0.1083 (11) | |
O11 | 0.89581 (13) | 0.71773 (18) | 0.59279 (10) | 0.0611 (6) | |
H11A | 0.9180 | 0.7649 | 0.5696 | 0.092* | |
H11B | 0.8673 | 0.7585 | 0.6151 | 0.092* | |
O12 | 0.59352 (15) | 0.2368 (2) | 0.51591 (10) | 0.0744 (7) | |
H12A | 0.5465 | 0.2286 | 0.4934 | 0.112* | |
H12B | 0.5912 | 0.1988 | 0.5480 | 0.112* | |
O13 | 0.80770 (16) | 0.8428 (2) | 0.67303 (11) | 0.0810 (7) | |
H13A | 0.7544 | 0.8271 | 0.6675 | 0.122* | |
H13B | 0.8162 | 0.9148 | 0.6621 | 0.122* | |
O14 | 0.63813 (18) | 0.1135 (2) | 0.61711 (14) | 0.0981 (10) | |
H14B | 0.6243 | 0.0435 | 0.6280 | 0.147* | |
H14A | 0.6892 | 0.1124 | 0.6087 | 0.147* | |
O15 | 0.9486 (3) | 0.8755 (3) | 0.5127 (2) | 0.164 (2) | |
H15A | 0.9792 | 0.8591 | 0.4856 | 0.246* | |
H15B | 0.9753 | 0.9243 | 0.5372 | 0.246* | |
N1 | 0.85177 (13) | 0.58255 (19) | 0.46123 (9) | 0.0363 (5) | |
N2 | 0.74702 (13) | 0.75003 (19) | 0.49063 (9) | 0.0370 (5) | |
N3 | 0.63113 (13) | 0.48710 (19) | 0.44021 (9) | 0.0382 (5) | |
N4 | 0.73526 (14) | 0.3001 (2) | 0.44646 (11) | 0.0497 (6) | |
C1 | 0.90546 (17) | 0.4956 (3) | 0.44841 (13) | 0.0467 (7) | |
H1 | 0.9249 | 0.4394 | 0.4773 | 0.056* | |
C2 | 0.93322 (19) | 0.4868 (3) | 0.39294 (15) | 0.0562 (8) | |
H2 | 0.9714 | 0.4264 | 0.3854 | 0.067* | |
C3 | 0.90401 (19) | 0.5673 (3) | 0.34984 (15) | 0.0572 (8) | |
H3 | 0.9213 | 0.5608 | 0.3125 | 0.069* | |
C4 | 0.84776 (17) | 0.6599 (3) | 0.36178 (12) | 0.0456 (7) | |
C5 | 0.8131 (2) | 0.7496 (3) | 0.32023 (14) | 0.0603 (9) | |
H5 | 0.8278 | 0.7483 | 0.2821 | 0.072* | |
C6 | 0.7598 (2) | 0.8351 (3) | 0.33530 (13) | 0.0587 (8) | |
H6 | 0.7382 | 0.8917 | 0.3071 | 0.070* | |
C7 | 0.73488 (17) | 0.8423 (3) | 0.39333 (12) | 0.0452 (7) | |
C8 | 0.6799 (2) | 0.9290 (3) | 0.41292 (15) | 0.0553 (8) | |
H8 | 0.6559 | 0.9886 | 0.3872 | 0.066* | |
C9 | 0.6619 (2) | 0.9258 (3) | 0.46928 (15) | 0.0591 (8) | |
H9 | 0.6263 | 0.9843 | 0.4825 | 0.071* | |
C10 | 0.69623 (19) | 0.8353 (3) | 0.50777 (13) | 0.0490 (7) | |
H10 | 0.6832 | 0.8347 | 0.5464 | 0.059* | |
C11 | 0.76714 (16) | 0.7542 (2) | 0.43463 (11) | 0.0372 (6) | |
C12 | 0.82425 (15) | 0.6630 (2) | 0.41879 (11) | 0.0372 (6) | |
C13 | 0.65862 (16) | 0.5568 (2) | 0.60155 (11) | 0.0377 (6) | |
C14 | 0.61851 (16) | 0.5631 (2) | 0.65811 (11) | 0.0374 (6) | |
C15 | 0.56510 (16) | 0.6550 (2) | 0.67338 (11) | 0.0382 (6) | |
C16 | 0.52874 (18) | 0.6469 (3) | 0.72559 (12) | 0.0465 (7) | |
H16 | 0.4918 | 0.7072 | 0.7353 | 0.056* | |
C17 | 0.54720 (19) | 0.5500 (3) | 0.76316 (12) | 0.0513 (8) | |
H17 | 0.5233 | 0.5459 | 0.7983 | 0.062* | |
C18 | 0.60058 (19) | 0.4598 (3) | 0.74882 (12) | 0.0511 (7) | |
H18 | 0.6134 | 0.3950 | 0.7744 | 0.061* | |
C19 | 0.63524 (18) | 0.4655 (3) | 0.69623 (12) | 0.0457 (7) | |
H19 | 0.6703 | 0.4031 | 0.6862 | 0.055* | |
C20 | 0.82659 (17) | 0.3742 (2) | 0.59469 (12) | 0.0388 (6) | |
C21 | 0.87666 (16) | 0.3371 (2) | 0.65247 (11) | 0.0393 (6) | |
C22 | 0.91359 (17) | 0.2243 (3) | 0.66465 (12) | 0.0455 (7) | |
C23 | 0.9587 (2) | 0.2023 (3) | 0.72017 (15) | 0.0653 (9) | |
H23 | 0.9839 | 0.1271 | 0.7284 | 0.078* | |
C24 | 0.9666 (2) | 0.2903 (4) | 0.76289 (14) | 0.0693 (10) | |
H24 | 0.9971 | 0.2747 | 0.7997 | 0.083* | |
C25 | 0.9297 (2) | 0.4002 (3) | 0.75126 (14) | 0.0629 (10) | |
H25 | 0.9344 | 0.4593 | 0.7805 | 0.075* | |
C26 | 0.88576 (19) | 0.4247 (3) | 0.69684 (13) | 0.0524 (7) | |
H26 | 0.8616 | 0.5007 | 0.6893 | 0.063* | |
C27 | 0.57798 (18) | 0.5804 (3) | 0.43896 (15) | 0.0521 (7) | |
H27 | 0.5562 | 0.6024 | 0.4734 | 0.062* | |
C28 | 0.5541 (2) | 0.6459 (3) | 0.38793 (18) | 0.0684 (10) | |
H28 | 0.5160 | 0.7100 | 0.3883 | 0.082* | |
C29 | 0.5859 (3) | 0.6170 (4) | 0.33761 (19) | 0.0778 (12) | |
H29 | 0.5715 | 0.6632 | 0.3038 | 0.093* | |
C30 | 0.6407 (2) | 0.5170 (4) | 0.33633 (13) | 0.0639 (10) | |
C31 | 0.6750 (3) | 0.4729 (5) | 0.28517 (16) | 0.0907 (15) | |
H31 | 0.6624 | 0.5137 | 0.2495 | 0.109* | |
C32 | 0.7241 (3) | 0.3760 (5) | 0.28739 (18) | 0.0997 (18) | |
H32 | 0.7446 | 0.3498 | 0.2531 | 0.120* | |
C33 | 0.7470 (2) | 0.3088 (4) | 0.34189 (17) | 0.0749 (12) | |
C34 | 0.7975 (3) | 0.2050 (5) | 0.3488 (3) | 0.1028 (18) | |
H34 | 0.8180 | 0.1709 | 0.3161 | 0.123* | |
C35 | 0.8169 (3) | 0.1536 (4) | 0.4024 (3) | 0.1000 (17) | |
H35 | 0.8519 | 0.0856 | 0.4066 | 0.120* | |
C36 | 0.7846 (2) | 0.2022 (3) | 0.45175 (18) | 0.0714 (10) | |
H36 | 0.7978 | 0.1657 | 0.4885 | 0.086* | |
C37 | 0.71598 (18) | 0.3526 (3) | 0.39304 (13) | 0.0489 (7) | |
C38 | 0.66172 (17) | 0.4549 (3) | 0.38950 (12) | 0.0454 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03799 (19) | 0.03693 (19) | 0.03446 (19) | −0.00029 (13) | 0.00665 (13) | 0.00613 (13) |
Cu2 | 0.0424 (2) | 0.03841 (19) | 0.03115 (19) | 0.00165 (14) | 0.00036 (14) | −0.00111 (12) |
S1 | 0.0456 (4) | 0.0475 (4) | 0.0372 (4) | 0.0010 (3) | 0.0062 (3) | −0.0029 (3) |
S2 | 0.0783 (6) | 0.0657 (6) | 0.0577 (6) | 0.0301 (5) | −0.0056 (4) | −0.0028 (4) |
O1 | 0.0437 (11) | 0.0523 (12) | 0.0392 (11) | −0.0064 (9) | 0.0146 (8) | 0.0036 (8) |
O2 | 0.0469 (11) | 0.0621 (13) | 0.0386 (11) | −0.0023 (10) | 0.0092 (9) | −0.0114 (9) |
O3 | 0.0497 (11) | 0.0679 (13) | 0.0348 (11) | 0.0135 (10) | 0.0059 (8) | 0.0001 (9) |
O4 | 0.0777 (16) | 0.0518 (13) | 0.0678 (15) | −0.0192 (11) | −0.0066 (12) | 0.0093 (10) |
O5 | 0.0632 (14) | 0.0741 (15) | 0.0610 (14) | 0.0235 (12) | 0.0195 (11) | −0.0029 (11) |
O6 | 0.0490 (12) | 0.0464 (12) | 0.0639 (14) | 0.0059 (9) | 0.0103 (10) | 0.0236 (10) |
O7 | 0.0444 (11) | 0.0482 (12) | 0.0452 (11) | −0.0021 (9) | −0.0101 (9) | 0.0060 (9) |
O8 | 0.0872 (18) | 0.127 (2) | 0.0425 (14) | 0.0387 (17) | 0.0058 (12) | −0.0026 (14) |
O9 | 0.099 (2) | 0.0549 (15) | 0.105 (2) | 0.0016 (14) | −0.0060 (16) | −0.0063 (14) |
O10 | 0.129 (2) | 0.096 (2) | 0.090 (2) | 0.0716 (19) | −0.0223 (18) | −0.0129 (16) |
O11 | 0.0523 (12) | 0.0560 (13) | 0.0721 (15) | −0.0035 (10) | −0.0032 (11) | −0.0093 (11) |
O12 | 0.0698 (14) | 0.0744 (16) | 0.0707 (16) | −0.0301 (13) | −0.0232 (12) | 0.0251 (12) |
O13 | 0.0800 (17) | 0.0922 (18) | 0.0691 (17) | −0.0154 (15) | 0.0026 (13) | −0.0044 (14) |
O14 | 0.094 (2) | 0.086 (2) | 0.112 (2) | −0.0075 (15) | 0.0046 (17) | 0.0486 (16) |
O15 | 0.206 (4) | 0.110 (3) | 0.209 (4) | −0.083 (3) | 0.150 (4) | −0.066 (3) |
N1 | 0.0310 (11) | 0.0378 (12) | 0.0405 (13) | −0.0029 (9) | 0.0060 (9) | 0.0018 (9) |
N2 | 0.0367 (12) | 0.0380 (12) | 0.0375 (12) | −0.0005 (9) | 0.0094 (9) | 0.0040 (9) |
N3 | 0.0355 (11) | 0.0446 (13) | 0.0335 (12) | −0.0035 (10) | 0.0005 (9) | 0.0012 (9) |
N4 | 0.0419 (13) | 0.0533 (15) | 0.0524 (16) | 0.0011 (11) | 0.0008 (11) | −0.0196 (12) |
C1 | 0.0361 (15) | 0.0459 (16) | 0.0580 (19) | 0.0023 (13) | 0.0063 (13) | −0.0021 (13) |
C2 | 0.0422 (16) | 0.060 (2) | 0.069 (2) | 0.0039 (14) | 0.0168 (15) | −0.0119 (16) |
C3 | 0.0487 (18) | 0.073 (2) | 0.054 (2) | −0.0050 (16) | 0.0228 (15) | −0.0087 (17) |
C4 | 0.0398 (15) | 0.0589 (18) | 0.0398 (16) | −0.0070 (13) | 0.0119 (12) | 0.0010 (13) |
C5 | 0.061 (2) | 0.083 (2) | 0.0380 (17) | −0.0046 (18) | 0.0131 (15) | 0.0109 (15) |
C6 | 0.0586 (19) | 0.073 (2) | 0.0436 (18) | 0.0011 (17) | 0.0028 (15) | 0.0205 (16) |
C7 | 0.0419 (15) | 0.0489 (16) | 0.0440 (16) | −0.0025 (13) | 0.0021 (12) | 0.0117 (13) |
C8 | 0.0559 (19) | 0.0465 (17) | 0.061 (2) | 0.0082 (15) | 0.0000 (15) | 0.0137 (15) |
C9 | 0.059 (2) | 0.0509 (18) | 0.069 (2) | 0.0168 (15) | 0.0137 (17) | 0.0052 (16) |
C10 | 0.0577 (18) | 0.0426 (16) | 0.0489 (18) | 0.0057 (14) | 0.0153 (14) | 0.0013 (13) |
C11 | 0.0348 (14) | 0.0405 (15) | 0.0362 (15) | −0.0045 (11) | 0.0040 (11) | 0.0041 (11) |
C12 | 0.0302 (13) | 0.0434 (15) | 0.0381 (15) | −0.0050 (11) | 0.0046 (11) | 0.0019 (12) |
C13 | 0.0389 (15) | 0.0436 (15) | 0.0307 (14) | 0.0055 (12) | 0.0048 (11) | 0.0036 (11) |
C14 | 0.0359 (14) | 0.0458 (15) | 0.0301 (14) | −0.0088 (12) | 0.0023 (11) | −0.0001 (11) |
C15 | 0.0372 (14) | 0.0467 (15) | 0.0302 (14) | −0.0093 (12) | 0.0029 (11) | −0.0064 (11) |
C16 | 0.0440 (16) | 0.0595 (18) | 0.0375 (16) | −0.0112 (14) | 0.0106 (12) | −0.0084 (13) |
C17 | 0.0507 (17) | 0.074 (2) | 0.0311 (15) | −0.0196 (16) | 0.0111 (13) | −0.0013 (14) |
C18 | 0.0545 (18) | 0.062 (2) | 0.0356 (16) | −0.0158 (15) | 0.0022 (13) | 0.0118 (13) |
C19 | 0.0456 (16) | 0.0495 (17) | 0.0415 (16) | −0.0056 (13) | 0.0042 (12) | 0.0037 (12) |
C20 | 0.0412 (15) | 0.0378 (15) | 0.0382 (15) | 0.0075 (12) | 0.0084 (12) | 0.0060 (11) |
C21 | 0.0356 (14) | 0.0464 (15) | 0.0360 (15) | −0.0089 (12) | 0.0044 (11) | 0.0055 (12) |
C22 | 0.0425 (15) | 0.0538 (17) | 0.0393 (16) | 0.0056 (13) | 0.0015 (12) | 0.0092 (13) |
C23 | 0.059 (2) | 0.085 (3) | 0.050 (2) | 0.0196 (18) | 0.0005 (16) | 0.0196 (18) |
C24 | 0.0514 (19) | 0.120 (3) | 0.0343 (18) | −0.010 (2) | −0.0038 (14) | 0.0137 (19) |
C25 | 0.058 (2) | 0.089 (3) | 0.0419 (19) | −0.0329 (19) | 0.0060 (15) | −0.0072 (17) |
C26 | 0.0548 (18) | 0.0539 (18) | 0.0486 (18) | −0.0165 (15) | 0.0065 (14) | −0.0020 (14) |
C27 | 0.0439 (17) | 0.0489 (17) | 0.060 (2) | −0.0027 (14) | −0.0045 (14) | 0.0050 (14) |
C28 | 0.061 (2) | 0.059 (2) | 0.077 (3) | −0.0048 (17) | −0.0217 (19) | 0.0192 (18) |
C29 | 0.069 (2) | 0.086 (3) | 0.069 (3) | −0.028 (2) | −0.029 (2) | 0.039 (2) |
C30 | 0.057 (2) | 0.096 (3) | 0.0356 (17) | −0.038 (2) | −0.0072 (14) | 0.0137 (16) |
C31 | 0.086 (3) | 0.152 (5) | 0.035 (2) | −0.055 (3) | 0.0126 (19) | −0.002 (2) |
C32 | 0.084 (3) | 0.174 (5) | 0.047 (2) | −0.054 (3) | 0.033 (2) | −0.039 (3) |
C33 | 0.053 (2) | 0.108 (3) | 0.068 (3) | −0.029 (2) | 0.0234 (18) | −0.043 (2) |
C34 | 0.066 (3) | 0.129 (4) | 0.120 (4) | −0.018 (3) | 0.039 (3) | −0.076 (4) |
C35 | 0.059 (2) | 0.090 (3) | 0.151 (5) | 0.016 (2) | 0.009 (3) | −0.065 (3) |
C36 | 0.055 (2) | 0.060 (2) | 0.094 (3) | 0.0110 (17) | −0.0074 (19) | −0.0301 (19) |
C37 | 0.0379 (15) | 0.069 (2) | 0.0401 (17) | −0.0166 (14) | 0.0056 (12) | −0.0156 (14) |
C38 | 0.0382 (15) | 0.0619 (19) | 0.0352 (15) | −0.0205 (14) | 0.0016 (12) | −0.0041 (13) |
Cu1—O1 | 1.9755 (18) | C6—H6 | 0.9300 |
Cu1—O6 | 1.9420 (18) | C7—C8 | 1.403 (4) |
Cu1—O11 | 2.183 (2) | C7—C11 | 1.405 (4) |
Cu1—N1 | 2.010 (2) | C8—C9 | 1.353 (4) |
Cu1—N2 | 1.995 (2) | C8—H8 | 0.9300 |
Cu2—O2 | 1.9404 (18) | C9—C10 | 1.395 (4) |
Cu2—O7 | 1.9943 (18) | C9—H9 | 0.9300 |
Cu2—O12 | 2.134 (2) | C10—H10 | 0.9300 |
Cu2—N3 | 2.012 (2) | C11—C12 | 1.428 (4) |
Cu2—N4 | 1.995 (2) | C13—C14 | 1.510 (3) |
S1—O5 | 1.441 (2) | C14—C15 | 1.391 (4) |
S1—O4 | 1.449 (2) | C14—C19 | 1.391 (4) |
S1—O3 | 1.4494 (19) | C15—C16 | 1.389 (4) |
S1—C15 | 1.781 (3) | C16—C17 | 1.381 (4) |
S2—O10 | 1.442 (2) | C16—H16 | 0.9300 |
S2—O8 | 1.443 (3) | C17—C18 | 1.371 (4) |
S2—O9 | 1.449 (3) | C17—H17 | 0.9300 |
S2—C22 | 1.779 (3) | C18—C19 | 1.382 (4) |
O1—C13 | 1.250 (3) | C18—H18 | 0.9300 |
O2—C13 | 1.251 (3) | C19—H19 | 0.9300 |
O6—C20 | 1.255 (3) | C20—C21 | 1.505 (4) |
O7—C20 | 1.242 (3) | C21—C22 | 1.390 (4) |
O11—H11A | 0.8500 | C21—C26 | 1.396 (4) |
O11—H11B | 0.8498 | C22—C23 | 1.393 (4) |
O12—H12A | 0.8499 | C23—C24 | 1.372 (5) |
O12—H12B | 0.8499 | C23—H23 | 0.9300 |
O13—H13A | 0.8498 | C24—C25 | 1.359 (5) |
O13—H13B | 0.8500 | C24—H24 | 0.9300 |
O14—H14B | 0.8499 | C25—C26 | 1.369 (4) |
O14—H14A | 0.8501 | C25—H25 | 0.9300 |
O15—H15A | 0.8500 | C26—H26 | 0.9300 |
O15—H15B | 0.8501 | C27—C28 | 1.382 (4) |
N1—C1 | 1.337 (3) | C27—H27 | 0.9300 |
N1—C12 | 1.346 (3) | C28—C29 | 1.349 (6) |
N2—C10 | 1.327 (3) | C28—H28 | 0.9300 |
N2—C11 | 1.357 (3) | C29—C30 | 1.406 (5) |
N3—C27 | 1.327 (3) | C29—H29 | 0.9300 |
N3—C38 | 1.357 (3) | C30—C38 | 1.397 (4) |
N4—C36 | 1.329 (4) | C30—C31 | 1.433 (5) |
N4—C37 | 1.350 (4) | C31—C32 | 1.319 (6) |
C1—C2 | 1.395 (4) | C31—H31 | 0.9300 |
C1—H1 | 0.9300 | C32—C33 | 1.454 (6) |
C2—C3 | 1.362 (5) | C32—H32 | 0.9300 |
C2—H2 | 0.9300 | C33—C34 | 1.394 (6) |
C3—C4 | 1.404 (4) | C33—C37 | 1.408 (4) |
C3—H3 | 0.9300 | C34—C35 | 1.348 (7) |
C4—C12 | 1.398 (4) | C34—H34 | 0.9300 |
C4—C5 | 1.432 (4) | C35—C36 | 1.402 (6) |
C5—C6 | 1.338 (4) | C35—H35 | 0.9300 |
C5—H5 | 0.9300 | C36—H36 | 0.9300 |
C6—C7 | 1.431 (4) | C37—C38 | 1.414 (4) |
O1—Cu1—O11 | 89.55 (8) | C9—C10—H10 | 119.2 |
O6—Cu1—O1 | 91.73 (8) | N2—C11—C7 | 123.2 (2) |
O6—Cu1—O11 | 88.92 (8) | N2—C11—C12 | 116.4 (2) |
O6—Cu1—N2 | 172.14 (9) | C7—C11—C12 | 120.4 (2) |
O1—Cu1—N2 | 94.42 (8) | N1—C12—C4 | 123.7 (2) |
O6—Cu1—N1 | 90.91 (9) | N1—C12—C11 | 116.1 (2) |
O1—Cu1—N1 | 164.40 (8) | C4—C12—C11 | 120.2 (2) |
N1—Cu1—O11 | 105.88 (8) | O1—C13—O2 | 126.9 (2) |
N2—Cu1—N1 | 81.87 (8) | O1—C13—C14 | 117.6 (2) |
N2—Cu1—O11 | 96.02 (8) | O2—C13—C14 | 115.2 (2) |
O2—Cu2—O7 | 88.36 (8) | C15—C14—C19 | 118.9 (2) |
O2—Cu2—O12 | 92.33 (9) | C15—C14—C13 | 125.5 (2) |
O7—Cu2—O12 | 90.83 (8) | C19—C14—C13 | 115.6 (2) |
O2—Cu2—N4 | 173.68 (10) | C16—C15—C14 | 119.8 (3) |
O2—Cu2—N3 | 92.39 (9) | C16—C15—S1 | 118.5 (2) |
O7—Cu2—N3 | 161.02 (8) | C14—C15—S1 | 121.75 (19) |
O7—Cu2—N4 | 95.80 (9) | C17—C16—C15 | 120.4 (3) |
N4—Cu2—N3 | 82.13 (10) | C17—C16—H16 | 119.8 |
N3—Cu2—O12 | 108.08 (8) | C15—C16—H16 | 119.8 |
N4—Cu2—O12 | 92.37 (10) | C18—C17—C16 | 120.3 (3) |
O5—S1—O4 | 113.87 (15) | C18—C17—H17 | 119.9 |
O5—S1—O3 | 113.26 (13) | C16—C17—H17 | 119.9 |
O4—S1—O3 | 112.20 (13) | C17—C18—C19 | 119.8 (3) |
O5—S1—C15 | 106.41 (13) | C17—C18—H18 | 120.1 |
O4—S1—C15 | 104.38 (12) | C19—C18—H18 | 120.1 |
O3—S1—C15 | 105.78 (12) | C18—C19—C14 | 121.0 (3) |
O10—S2—O8 | 112.52 (18) | C18—C19—H19 | 119.5 |
O10—S2—O9 | 113.62 (19) | C14—C19—H19 | 119.5 |
O8—S2—O9 | 112.72 (17) | O7—C20—O6 | 126.1 (3) |
O10—S2—C22 | 106.23 (15) | O7—C20—C21 | 119.0 (2) |
O8—S2—C22 | 105.36 (15) | O6—C20—C21 | 114.7 (2) |
O9—S2—C22 | 105.54 (15) | C22—C21—C26 | 118.5 (3) |
C13—O1—Cu1 | 127.19 (17) | C22—C21—C20 | 125.4 (2) |
C13—O2—Cu2 | 129.51 (17) | C26—C21—C20 | 116.1 (3) |
C20—O6—Cu1 | 132.32 (18) | C21—C22—C23 | 119.4 (3) |
C20—O7—Cu2 | 120.61 (17) | C21—C22—S2 | 121.2 (2) |
Cu1—O11—H11A | 105.6 | C23—C22—S2 | 119.3 (2) |
Cu1—O11—H11B | 105.5 | C24—C23—C22 | 120.8 (3) |
H11A—O11—H11B | 109.7 | C24—C23—H23 | 119.6 |
Cu2—O12—H12A | 123.3 | C22—C23—H23 | 119.6 |
Cu2—O12—H12B | 122.6 | C25—C24—C23 | 119.9 (3) |
H12A—O12—H12B | 109.7 | C25—C24—H24 | 120.1 |
H13A—O13—H13B | 109.7 | C23—C24—H24 | 120.1 |
H14B—O14—H14A | 109.7 | C24—C25—C26 | 120.5 (3) |
H15A—O15—H15B | 109.7 | C24—C25—H25 | 119.8 |
C1—N1—C12 | 118.2 (2) | C26—C25—H25 | 119.8 |
C1—N1—Cu1 | 128.98 (19) | C25—C26—C21 | 121.0 (3) |
C12—N1—Cu1 | 112.81 (17) | C25—C26—H26 | 119.5 |
C10—N2—C11 | 118.4 (2) | C21—C26—H26 | 119.5 |
C10—N2—Cu1 | 128.87 (19) | N3—C27—C28 | 121.9 (3) |
C11—N2—Cu1 | 112.74 (16) | N3—C27—H27 | 119.0 |
C27—N3—C38 | 118.5 (2) | C28—C27—H27 | 119.0 |
C27—N3—Cu2 | 129.4 (2) | C29—C28—C27 | 120.2 (4) |
C38—N3—Cu2 | 112.09 (18) | C29—C28—H28 | 119.9 |
C36—N4—C37 | 119.6 (3) | C27—C28—H28 | 119.9 |
C36—N4—Cu2 | 128.2 (2) | C28—C29—C30 | 120.0 (3) |
C37—N4—Cu2 | 112.21 (19) | C28—C29—H29 | 120.0 |
N1—C1—C2 | 122.0 (3) | C30—C29—H29 | 120.0 |
N1—C1—H1 | 119.0 | C38—C30—C29 | 116.5 (3) |
C2—C1—H1 | 119.0 | C38—C30—C31 | 118.0 (4) |
C3—C2—C1 | 119.6 (3) | C29—C30—C31 | 125.5 (4) |
C3—C2—H2 | 120.2 | C32—C31—C30 | 121.7 (4) |
C1—C2—H2 | 120.2 | C32—C31—H31 | 119.2 |
C2—C3—C4 | 120.0 (3) | C30—C31—H31 | 119.2 |
C2—C3—H3 | 120.0 | C31—C32—C33 | 121.9 (4) |
C4—C3—H3 | 120.0 | C31—C32—H32 | 119.1 |
C12—C4—C3 | 116.6 (3) | C33—C32—H32 | 119.1 |
C12—C4—C5 | 118.4 (3) | C34—C33—C37 | 116.2 (4) |
C3—C4—C5 | 125.0 (3) | C34—C33—C32 | 126.4 (4) |
C6—C5—C4 | 121.2 (3) | C37—C33—C32 | 117.4 (4) |
C6—C5—H5 | 119.4 | C35—C34—C33 | 120.7 (4) |
C4—C5—H5 | 119.4 | C35—C34—H34 | 119.7 |
C5—C6—C7 | 122.1 (3) | C33—C34—H34 | 119.7 |
C5—C6—H6 | 118.9 | C34—C35—C36 | 120.2 (4) |
C7—C6—H6 | 118.9 | C34—C35—H35 | 119.9 |
C8—C7—C11 | 116.4 (3) | C36—C35—H35 | 119.9 |
C8—C7—C6 | 125.9 (3) | N4—C36—C35 | 120.5 (4) |
C11—C7—C6 | 117.7 (3) | N4—C36—H36 | 119.8 |
C9—C8—C7 | 119.9 (3) | C35—C36—H36 | 119.8 |
C9—C8—H8 | 120.1 | N4—C37—C33 | 122.7 (3) |
C7—C8—H8 | 120.1 | N4—C37—C38 | 117.4 (2) |
C8—C9—C10 | 120.4 (3) | C33—C37—C38 | 119.9 (3) |
C8—C9—H9 | 119.8 | N3—C38—C30 | 122.8 (3) |
C10—C9—H9 | 119.8 | N3—C38—C37 | 116.0 (2) |
N2—C10—C9 | 121.6 (3) | C30—C38—C37 | 121.2 (3) |
N2—C10—H10 | 119.2 | ||
O6—Cu1—O1—C13 | −77.1 (2) | O1—C13—C14—C15 | 79.8 (3) |
N2—Cu1—O1—C13 | 97.9 (2) | O2—C13—C14—C15 | −105.7 (3) |
N1—Cu1—O1—C13 | 22.5 (4) | O1—C13—C14—C19 | −102.6 (3) |
O11—Cu1—O1—C13 | −166.0 (2) | O2—C13—C14—C19 | 71.9 (3) |
O7—Cu2—O2—C13 | 55.9 (2) | C19—C14—C15—C16 | −0.9 (4) |
N3—Cu2—O2—C13 | −105.1 (2) | C13—C14—C15—C16 | 176.7 (2) |
O12—Cu2—O2—C13 | 146.7 (2) | C19—C14—C15—S1 | 178.9 (2) |
O1—Cu1—O6—C20 | 38.2 (3) | C13—C14—C15—S1 | −3.6 (4) |
N1—Cu1—O6—C20 | −126.4 (3) | O5—S1—C15—C16 | −27.7 (2) |
O11—Cu1—O6—C20 | 127.7 (3) | O4—S1—C15—C16 | 93.0 (2) |
O2—Cu2—O7—C20 | −87.0 (2) | O3—S1—C15—C16 | −148.5 (2) |
N4—Cu2—O7—C20 | 88.2 (2) | O5—S1—C15—C14 | 152.5 (2) |
N3—Cu2—O7—C20 | 5.6 (4) | O4—S1—C15—C14 | −86.7 (2) |
O12—Cu2—O7—C20 | −179.3 (2) | O3—S1—C15—C14 | 31.8 (2) |
O6—Cu1—N1—C1 | −3.4 (2) | C14—C15—C16—C17 | 1.8 (4) |
O1—Cu1—N1—C1 | −103.1 (4) | S1—C15—C16—C17 | −178.0 (2) |
N2—Cu1—N1—C1 | 179.7 (2) | C15—C16—C17—C18 | −1.0 (4) |
O11—Cu1—N1—C1 | 85.7 (2) | C16—C17—C18—C19 | −0.7 (4) |
O6—Cu1—N1—C12 | 175.01 (18) | C17—C18—C19—C14 | 1.6 (4) |
O1—Cu1—N1—C12 | 75.3 (4) | C15—C14—C19—C18 | −0.8 (4) |
N2—Cu1—N1—C12 | −1.87 (17) | C13—C14—C19—C18 | −178.6 (2) |
O11—Cu1—N1—C12 | −95.86 (18) | Cu2—O7—C20—O6 | −6.1 (4) |
O1—Cu1—N2—C10 | 17.6 (2) | Cu2—O7—C20—C21 | 168.64 (17) |
N1—Cu1—N2—C10 | −177.7 (2) | Cu1—O6—C20—O7 | 42.5 (4) |
O11—Cu1—N2—C10 | −72.5 (2) | Cu1—O6—C20—C21 | −132.5 (2) |
O1—Cu1—N2—C11 | −162.82 (17) | O7—C20—C21—C22 | 62.1 (4) |
N1—Cu1—N2—C11 | 1.94 (17) | O6—C20—C21—C22 | −122.5 (3) |
O11—Cu1—N2—C11 | 107.17 (17) | O7—C20—C21—C26 | −117.8 (3) |
O2—Cu2—N3—C27 | −3.8 (2) | O6—C20—C21—C26 | 57.6 (3) |
O7—Cu2—N3—C27 | −95.7 (3) | C26—C21—C22—C23 | −0.4 (4) |
N4—Cu2—N3—C27 | 179.4 (2) | C20—C21—C22—C23 | 179.7 (3) |
O12—Cu2—N3—C27 | 89.4 (2) | C26—C21—C22—S2 | −177.4 (2) |
O2—Cu2—N3—C38 | 173.85 (17) | C20—C21—C22—S2 | 2.7 (4) |
O7—Cu2—N3—C38 | 81.9 (3) | O10—S2—C22—C21 | 160.2 (3) |
N4—Cu2—N3—C38 | −2.98 (17) | O8—S2—C22—C21 | 40.6 (3) |
O12—Cu2—N3—C38 | −92.91 (18) | O9—S2—C22—C21 | −78.9 (3) |
O7—Cu2—N4—C36 | 22.2 (3) | O10—S2—C22—C23 | −16.8 (3) |
N3—Cu2—N4—C36 | −176.8 (3) | O8—S2—C22—C23 | −136.4 (3) |
O12—Cu2—N4—C36 | −68.8 (3) | O9—S2—C22—C23 | 104.2 (3) |
O7—Cu2—N4—C37 | −159.51 (19) | C21—C22—C23—C24 | 0.4 (5) |
N3—Cu2—N4—C37 | 1.49 (19) | S2—C22—C23—C24 | 177.5 (3) |
O12—Cu2—N4—C37 | 109.41 (19) | C22—C23—C24—C25 | 0.3 (5) |
C12—N1—C1—C2 | 0.1 (4) | C23—C24—C25—C26 | −1.0 (5) |
Cu1—N1—C1—C2 | 178.5 (2) | C24—C25—C26—C21 | 1.0 (5) |
N1—C1—C2—C3 | −1.2 (4) | C22—C21—C26—C25 | −0.3 (4) |
C1—C2—C3—C4 | 1.4 (5) | C20—C21—C26—C25 | 179.6 (3) |
C2—C3—C4—C12 | −0.5 (4) | C38—N3—C27—C28 | −0.8 (4) |
C2—C3—C4—C5 | 179.9 (3) | Cu2—N3—C27—C28 | 176.7 (2) |
C12—C4—C5—C6 | 0.4 (5) | N3—C27—C28—C29 | −1.0 (5) |
C3—C4—C5—C6 | −179.9 (3) | C27—C28—C29—C30 | 2.6 (5) |
C4—C5—C6—C7 | 0.3 (5) | C28—C29—C30—C38 | −2.3 (5) |
C5—C6—C7—C8 | 179.6 (3) | C28—C29—C30—C31 | 176.4 (3) |
C5—C6—C7—C11 | −1.2 (5) | C38—C30—C31—C32 | 0.8 (5) |
C11—C7—C8—C9 | 1.1 (4) | C29—C30—C31—C32 | −177.9 (4) |
C6—C7—C8—C9 | −179.7 (3) | C30—C31—C32—C33 | −0.6 (6) |
C7—C8—C9—C10 | −1.3 (5) | C31—C32—C33—C34 | 179.4 (4) |
C11—N2—C10—C9 | 1.8 (4) | C31—C32—C33—C37 | −1.2 (6) |
Cu1—N2—C10—C9 | −178.6 (2) | C37—C33—C34—C35 | −2.1 (6) |
C8—C9—C10—N2 | −0.2 (5) | C32—C33—C34—C35 | 177.4 (4) |
C10—N2—C11—C7 | −1.9 (4) | C33—C34—C35—C36 | 1.6 (7) |
Cu1—N2—C11—C7 | 178.4 (2) | C37—N4—C36—C35 | 0.2 (5) |
C10—N2—C11—C12 | 177.9 (2) | Cu2—N4—C36—C35 | 178.4 (3) |
Cu1—N2—C11—C12 | −1.7 (3) | C34—C35—C36—N4 | −0.7 (6) |
C8—C7—C11—N2 | 0.5 (4) | C36—N4—C37—C33 | −0.8 (4) |
C6—C7—C11—N2 | −178.7 (3) | Cu2—N4—C37—C33 | −179.2 (2) |
C8—C7—C11—C12 | −179.4 (2) | C36—N4—C37—C38 | 178.7 (3) |
C6—C7—C11—C12 | 1.4 (4) | Cu2—N4—C37—C38 | 0.2 (3) |
C1—N1—C12—C4 | 0.9 (4) | C34—C33—C37—N4 | 1.7 (5) |
Cu1—N1—C12—C4 | −177.7 (2) | C32—C33—C37—N4 | −177.8 (3) |
C1—N1—C12—C11 | −179.9 (2) | C34—C33—C37—C38 | −177.8 (3) |
Cu1—N1—C12—C11 | 1.5 (3) | C32—C33—C37—C38 | 2.7 (4) |
C3—C4—C12—N1 | −0.7 (4) | C27—N3—C38—C30 | 1.1 (4) |
C5—C4—C12—N1 | 179.0 (3) | Cu2—N3—C38—C30 | −176.9 (2) |
C3—C4—C12—C11 | −179.9 (3) | C27—N3—C38—C37 | −178.1 (2) |
C5—C4—C12—C11 | −0.2 (4) | Cu2—N3—C38—C37 | 4.0 (3) |
N2—C11—C12—N1 | 0.2 (3) | C29—C30—C38—N3 | 0.5 (4) |
C7—C11—C12—N1 | −180.0 (2) | C31—C30—C38—N3 | −178.4 (3) |
N2—C11—C12—C4 | 179.4 (2) | C29—C30—C38—C37 | 179.6 (3) |
C7—C11—C12—C4 | −0.7 (4) | C31—C30—C38—C37 | 0.8 (4) |
Cu1—O1—C13—O2 | −4.5 (4) | N4—C37—C38—N3 | −2.9 (4) |
Cu1—O1—C13—C14 | 169.27 (17) | C33—C37—C38—N3 | 176.6 (2) |
Cu2—O2—C13—O1 | 27.7 (4) | N4—C37—C38—C30 | 177.9 (2) |
Cu2—O2—C13—C14 | −146.15 (19) | C33—C37—C38—C30 | −2.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H15B···O10i | 0.85 | 2.37 | 3.115 (5) | 146 |
O15—H15A···O8ii | 0.85 | 1.94 | 2.763 (4) | 162 |
O14—H14A···O9 | 0.85 | 2.20 | 3.018 (4) | 161 |
O14—H14B···O4iii | 0.85 | 2.01 | 2.846 (3) | 169 |
O13—H13B···O9i | 0.85 | 2.05 | 2.857 (4) | 159 |
O13—H13A···O4 | 0.85 | 2.29 | 3.090 (3) | 157 |
O12—H12B···O14 | 0.85 | 1.90 | 2.697 (3) | 155 |
O12—H12A···O3iv | 0.85 | 1.88 | 2.700 (3) | 161 |
O11—H11B···O13 | 0.85 | 1.95 | 2.800 (3) | 174 |
O11—H11A···O15 | 0.85 | 1.89 | 2.733 (4) | 171 |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z+1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1. |
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