Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113027996/fn3155sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113027996/fn3155Isup2.hkl |
CCDC reference: 966113
Data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Cu2(C7H3NO4)2(C12H12N2O2)(H2O)2]·4H2O | Z = 2 |
Mr = 781.62 | F(000) = 800 |
Triclinic, P1 | Dx = 1.704 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1142 (19) Å | Cell parameters from 1397 reflections |
b = 11.940 (3) Å | θ = 2.4–21.5° |
c = 16.160 (4) Å | µ = 1.48 mm−1 |
α = 77.797 (4)° | T = 298 K |
β = 84.782 (4)° | Needle, green |
γ = 88.231 (4)° | 0.23 × 0.09 × 0.06 mm |
V = 1523.8 (6) Å3 |
Bruker SMART CCD area-detector diffractometer | 5571 independent reflections |
Radiation source: fine-focus sealed tube | 3740 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
φ and ω scans | θmax = 25.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −9→9 |
Tmin = 0.852, Tmax = 0.915 | k = −11→14 |
8073 measured reflections | l = −18→19 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0284P)2] where P = (Fo2 + 2Fc2)/3 |
5571 reflections | (Δ/σ)max < 0.001 |
503 parameters | Δρmax = 0.43 e Å−3 |
12 restraints | Δρmin = −0.50 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 | Occ. (<1) | |
C1 | −0.0714 (6) | 0.4549 (4) | 1.3028 (3) | 0.0362 (11) | |
C2 | −0.1990 (5) | 0.4861 (3) | 1.2398 (3) | 0.0345 (11) | |
C3 | −0.3463 (6) | 0.5466 (4) | 1.2478 (3) | 0.0442 (13) | |
H3 | −0.3780 | 0.5731 | 1.2971 | 0.053* | |
C4 | −0.4441 (6) | 0.5663 (4) | 1.1810 (3) | 0.0483 (13) | |
H4 | −0.5445 | 0.6051 | 1.1858 | 0.058* | |
C5 | −0.3959 (5) | 0.5296 (4) | 1.1065 (3) | 0.0391 (12) | |
H5 | −0.4614 | 0.5447 | 1.0610 | 0.047* | |
C6 | −0.2477 (5) | 0.4701 (3) | 1.1017 (3) | 0.0310 (10) | |
C7 | −0.1685 (5) | 0.4201 (4) | 1.0292 (3) | 0.0344 (11) | |
C8 | 0.3710 (5) | 0.2834 (4) | 1.2033 (3) | 0.0350 (11) | |
H8 | 0.3422 | 0.3074 | 1.2539 | 0.042* | |
C9 | 0.5257 (5) | 0.2375 (4) | 1.1901 (3) | 0.0374 (11) | |
H9 | 0.6004 | 0.2317 | 1.2312 | 0.045* | |
C10 | 0.5704 (5) | 0.2004 (3) | 1.1170 (3) | 0.0318 (10) | |
H10 | 0.6751 | 0.1692 | 1.1073 | 0.038* | |
C11 | 0.4562 (5) | 0.2104 (4) | 1.0582 (3) | 0.0332 (11) | |
C12 | 0.3052 (5) | 0.2589 (4) | 1.0748 (3) | 0.0377 (11) | |
H12 | 0.2295 | 0.2672 | 1.0340 | 0.045* | |
C13 | 0.634 (4) | 0.163 (2) | 0.9443 (19) | 0.032 (4) | 0.57 (3) |
H13A | 0.7170 | 0.1254 | 0.9806 | 0.038* | 0.57 (3) |
H13B | 0.6633 | 0.2434 | 0.9261 | 0.038* | 0.57 (3) |
C14 | 0.6351 (5) | 0.1117 (4) | 0.8700 (3) | 0.0375 (11) | 0.57 (3) |
H14A | 0.7342 | 0.1343 | 0.8326 | 0.045* | 0.57 (3) |
H14B | 0.6366 | 0.0289 | 0.8879 | 0.045* | 0.57 (3) |
C15 | 0.4748 (5) | 0.0954 (4) | 0.7585 (3) | 0.0394 (12) | |
C16 | 0.5926 (5) | 0.0360 (3) | 0.7182 (3) | 0.0352 (11) | |
H16 | 0.6920 | 0.0135 | 0.7416 | 0.042* | |
C17 | 0.5598 (5) | 0.0107 (4) | 0.6423 (3) | 0.0401 (12) | |
H17 | 0.6363 | −0.0307 | 0.6139 | 0.048* | |
C18 | 0.4135 (6) | 0.0469 (3) | 0.6088 (3) | 0.0388 (12) | |
H18 | 0.3930 | 0.0299 | 0.5572 | 0.047* | |
C19 | 0.3311 (5) | 0.1295 (4) | 0.7208 (3) | 0.0448 (13) | |
H19 | 0.2529 | 0.1712 | 0.7480 | 0.054* | |
C20 | 0.0460 (6) | 0.1224 (4) | 0.4310 (3) | 0.0404 (12) | |
C21 | −0.1051 (5) | 0.1869 (3) | 0.4596 (3) | 0.0304 (10) | |
C22 | −0.2468 (6) | 0.2182 (4) | 0.4185 (3) | 0.0401 (12) | |
H22 | −0.2589 | 0.1999 | 0.3662 | 0.048* | |
C23 | −0.3705 (5) | 0.2773 (4) | 0.4569 (3) | 0.0436 (12) | |
H23 | −0.4660 | 0.3006 | 0.4299 | 0.052* | |
C24 | −0.3514 (6) | 0.3016 (4) | 0.5355 (3) | 0.0430 (12) | |
H24 | −0.4342 | 0.3407 | 0.5620 | 0.052* | |
C25 | −0.2086 (5) | 0.2672 (3) | 0.5737 (3) | 0.0331 (11) | |
C26 | −0.1641 (6) | 0.2798 (4) | 0.6594 (3) | 0.0352 (11) | |
C13' | 0.631 (6) | 0.127 (3) | 0.961 (3) | 0.032 (4) | 0.43 (3) |
H13E | 0.6162 | 0.0535 | 1.0002 | 0.038* | 0.43 (3) |
H13F | 0.7331 | 0.1602 | 0.9704 | 0.038* | 0.43 (3) |
C14' | 0.6351 (5) | 0.1117 (4) | 0.8700 (3) | 0.0375 (11) | 0.43 (3) |
H14E | 0.6801 | 0.1803 | 0.8324 | 0.045* | 0.43 (3) |
H14F | 0.7088 | 0.0482 | 0.8630 | 0.045* | 0.43 (3) |
Cu1 | 0.03803 (6) | 0.35908 (4) | 1.16228 (3) | 0.03274 (16) | |
Cu2 | 0.10622 (7) | 0.17035 (5) | 0.58813 (3) | 0.03902 (18) | |
N1 | −0.1578 (4) | 0.4496 (3) | 1.1680 (2) | 0.0288 (8) | |
N2 | 0.2611 (4) | 0.2947 (3) | 1.1458 (2) | 0.0286 (8) | |
N3 | 0.2992 (4) | 0.1055 (3) | 0.6475 (2) | 0.0344 (9) | |
N4 | −0.0919 (4) | 0.2133 (3) | 0.5340 (2) | 0.0299 (8) | |
O1 | 0.0507 (4) | 0.3939 (2) | 1.27781 (17) | 0.0415 (8) | |
O2 | −0.0877 (4) | 0.4853 (3) | 1.37055 (19) | 0.0508 (9) | |
O3 | −0.2348 (4) | 0.4338 (3) | 0.96221 (19) | 0.0463 (8) | |
O4 | −0.0346 (3) | 0.3639 (2) | 1.04561 (17) | 0.0357 (7) | |
O5 | 0.4727 (15) | 0.1540 (14) | 0.9926 (9) | 0.032 (3) | 0.57 (3) |
O6 | 0.4977 (17) | 0.1462 (14) | 0.8270 (9) | 0.038 (3) | 0.57 (3) |
O7 | −0.0294 (4) | 0.2284 (3) | 0.68209 (17) | 0.0429 (8) | |
O8 | −0.2549 (4) | 0.3339 (2) | 0.70240 (18) | 0.0451 (8) | |
O9 | 0.0499 (4) | 0.0860 (3) | 0.36494 (19) | 0.0523 (9) | |
O10 | 0.1600 (4) | 0.1082 (3) | 0.48231 (18) | 0.0439 (8) | |
O11 | 0.2334 (4) | 0.3453 (3) | 0.5511 (2) | 0.0479 (9) | |
H11A | 0.237 (6) | 0.369 (4) | 0.4977 (8) | 0.060 (18)* | |
H11B | 0.178 (5) | 0.397 (3) | 0.570 (3) | 0.067 (18)* | |
O12 | −0.0784 (4) | 0.1850 (3) | 1.2165 (2) | 0.0379 (8) | |
H12A | −0.030 (5) | 0.156 (4) | 1.2607 (18) | 0.064 (18)* | |
H12B | −0.055 (5) | 0.143 (3) | 1.181 (2) | 0.047 (15)* | |
O13 | 0.0089 (6) | 0.9395 (4) | 0.9051 (3) | 0.0757 (13) | |
H13C | 0.043 (5) | 1.0064 (17) | 0.903 (3) | 0.041 (15)* | |
H13D | −0.046 (6) | 0.906 (4) | 0.950 (2) | 0.09 (2)* | |
O14 | 0.3027 (5) | 0.4278 (4) | 0.3781 (2) | 0.0525 (9) | |
H14C | 0.301 (7) | 0.5002 (10) | 0.363 (3) | 0.09 (2)* | |
H14D | 0.215 (4) | 0.413 (5) | 0.358 (3) | 0.08 (2)* | |
O15 | 0.9560 (5) | 0.3192 (3) | 0.8497 (3) | 0.0593 (10) | |
H15A | 0.917 (7) | 0.321 (5) | 0.803 (2) | 0.10 (3)* | |
H15B | 0.890 (6) | 0.357 (4) | 0.878 (3) | 0.10 (3)* | |
O16 | 0.8639 (5) | 0.8567 (3) | 0.0740 (2) | 0.0546 (9) | |
H16A | 0.922 (6) | 0.801 (3) | 0.098 (3) | 0.07 (2)* | |
H16B | 0.7626 (19) | 0.853 (4) | 0.091 (3) | 0.050 (16)* | |
O5' | 0.491 (2) | 0.2027 (17) | 0.9712 (10) | 0.029 (3) | 0.43 (3) |
O6' | 0.4785 (19) | 0.0910 (19) | 0.8458 (10) | 0.036 (4) | 0.43 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.036 (3) | 0.035 (3) | 0.038 (3) | −0.004 (2) | −0.001 (2) | −0.009 (2) |
C2 | 0.033 (3) | 0.033 (3) | 0.037 (3) | −0.001 (2) | 0.002 (2) | −0.009 (2) |
C3 | 0.038 (3) | 0.045 (3) | 0.049 (3) | 0.006 (2) | 0.009 (3) | −0.016 (2) |
C4 | 0.031 (3) | 0.051 (3) | 0.058 (4) | 0.013 (2) | 0.006 (3) | −0.007 (3) |
C5 | 0.022 (3) | 0.046 (3) | 0.046 (3) | 0.010 (2) | −0.005 (2) | −0.002 (2) |
C6 | 0.028 (3) | 0.029 (3) | 0.035 (3) | −0.002 (2) | −0.002 (2) | −0.005 (2) |
C7 | 0.031 (3) | 0.036 (3) | 0.037 (3) | 0.000 (2) | −0.006 (2) | −0.008 (2) |
C8 | 0.034 (3) | 0.051 (3) | 0.024 (3) | 0.003 (2) | −0.001 (2) | −0.017 (2) |
C9 | 0.024 (3) | 0.059 (3) | 0.035 (3) | 0.004 (2) | −0.014 (2) | −0.016 (2) |
C10 | 0.020 (2) | 0.040 (3) | 0.035 (3) | 0.005 (2) | −0.0004 (19) | −0.008 (2) |
C11 | 0.029 (3) | 0.043 (3) | 0.032 (3) | 0.002 (2) | −0.005 (2) | −0.018 (2) |
C12 | 0.028 (3) | 0.055 (3) | 0.035 (3) | 0.005 (2) | −0.011 (2) | −0.016 (2) |
C13 | 0.027 (3) | 0.045 (13) | 0.022 (11) | 0.010 (11) | −0.008 (7) | −0.001 (9) |
C14 | 0.025 (3) | 0.053 (3) | 0.039 (3) | 0.008 (2) | −0.007 (2) | −0.018 (2) |
C15 | 0.031 (3) | 0.065 (3) | 0.026 (3) | 0.005 (2) | −0.005 (2) | −0.019 (2) |
C16 | 0.032 (3) | 0.041 (3) | 0.032 (3) | 0.009 (2) | −0.004 (2) | −0.008 (2) |
C17 | 0.036 (3) | 0.049 (3) | 0.040 (3) | 0.019 (2) | −0.006 (2) | −0.020 (2) |
C18 | 0.048 (3) | 0.044 (3) | 0.029 (3) | 0.008 (2) | −0.006 (2) | −0.017 (2) |
C19 | 0.030 (3) | 0.071 (4) | 0.041 (3) | 0.018 (2) | −0.006 (2) | −0.030 (3) |
C20 | 0.050 (3) | 0.041 (3) | 0.030 (3) | 0.018 (2) | −0.007 (2) | −0.007 (2) |
C21 | 0.033 (3) | 0.033 (3) | 0.026 (3) | 0.003 (2) | −0.005 (2) | −0.008 (2) |
C22 | 0.040 (3) | 0.051 (3) | 0.030 (3) | 0.008 (2) | −0.010 (2) | −0.010 (2) |
C23 | 0.027 (3) | 0.057 (3) | 0.045 (3) | 0.009 (2) | −0.011 (2) | −0.003 (3) |
C24 | 0.032 (3) | 0.046 (3) | 0.051 (3) | 0.010 (2) | −0.001 (2) | −0.013 (2) |
C25 | 0.029 (3) | 0.037 (3) | 0.031 (3) | 0.006 (2) | 0.003 (2) | −0.006 (2) |
C26 | 0.030 (3) | 0.044 (3) | 0.032 (3) | 0.000 (2) | 0.005 (2) | −0.010 (2) |
C13' | 0.027 (3) | 0.045 (13) | 0.022 (11) | 0.010 (11) | −0.008 (7) | −0.001 (9) |
C14' | 0.025 (3) | 0.053 (3) | 0.039 (3) | 0.008 (2) | −0.007 (2) | −0.018 (2) |
Cu1 | 0.0260 (3) | 0.0431 (4) | 0.0333 (3) | 0.0102 (2) | −0.0070 (2) | −0.0170 (3) |
Cu2 | 0.0317 (4) | 0.0602 (4) | 0.0300 (3) | 0.0158 (3) | −0.0086 (2) | −0.0202 (3) |
N1 | 0.020 (2) | 0.032 (2) | 0.035 (2) | 0.0042 (15) | −0.0005 (16) | −0.0112 (17) |
N2 | 0.027 (2) | 0.033 (2) | 0.027 (2) | 0.0032 (16) | −0.0038 (16) | −0.0105 (16) |
N3 | 0.029 (2) | 0.048 (2) | 0.028 (2) | 0.0120 (18) | −0.0073 (16) | −0.0134 (18) |
N4 | 0.022 (2) | 0.038 (2) | 0.030 (2) | 0.0067 (16) | −0.0038 (16) | −0.0091 (17) |
O1 | 0.039 (2) | 0.052 (2) | 0.040 (2) | 0.0150 (16) | −0.0100 (15) | −0.0249 (16) |
O2 | 0.053 (2) | 0.064 (2) | 0.042 (2) | 0.0062 (17) | 0.0011 (16) | −0.0293 (18) |
O3 | 0.042 (2) | 0.061 (2) | 0.040 (2) | 0.0098 (16) | −0.0155 (16) | −0.0158 (16) |
O4 | 0.0282 (18) | 0.049 (2) | 0.0330 (18) | 0.0133 (14) | −0.0081 (14) | −0.0151 (14) |
O5 | 0.021 (4) | 0.044 (7) | 0.033 (6) | −0.010 (5) | 0.008 (4) | −0.015 (5) |
O6 | 0.030 (5) | 0.055 (8) | 0.034 (6) | 0.016 (6) | −0.011 (4) | −0.019 (6) |
O7 | 0.036 (2) | 0.067 (2) | 0.0308 (18) | 0.0129 (16) | −0.0035 (14) | −0.0221 (15) |
O8 | 0.044 (2) | 0.052 (2) | 0.042 (2) | 0.0081 (16) | 0.0078 (16) | −0.0217 (16) |
O9 | 0.062 (2) | 0.068 (2) | 0.035 (2) | 0.0321 (18) | −0.0200 (17) | −0.0273 (17) |
O10 | 0.039 (2) | 0.067 (2) | 0.0314 (18) | 0.0249 (16) | −0.0129 (15) | −0.0238 (16) |
O11 | 0.047 (2) | 0.053 (2) | 0.045 (3) | 0.0103 (18) | 0.0008 (18) | −0.017 (2) |
O12 | 0.040 (2) | 0.046 (2) | 0.031 (2) | 0.0076 (16) | −0.0106 (16) | −0.0125 (17) |
O13 | 0.124 (4) | 0.054 (3) | 0.052 (3) | −0.023 (3) | 0.011 (3) | −0.022 (2) |
O14 | 0.048 (3) | 0.059 (3) | 0.053 (2) | 0.010 (2) | −0.0170 (19) | −0.014 (2) |
O15 | 0.065 (3) | 0.073 (3) | 0.043 (3) | −0.010 (2) | −0.002 (2) | −0.019 (2) |
O16 | 0.039 (3) | 0.066 (3) | 0.062 (3) | −0.008 (2) | 0.003 (2) | −0.022 (2) |
O5' | 0.028 (7) | 0.036 (9) | 0.023 (7) | 0.006 (6) | −0.003 (5) | −0.007 (6) |
O6' | 0.027 (5) | 0.058 (11) | 0.026 (7) | −0.007 (7) | 0.001 (4) | −0.018 (7) |
C1—O2 | 1.219 (5) | C19—N3 | 1.325 (5) |
C1—O1 | 1.296 (5) | C19—H19 | 0.9300 |
C1—C2 | 1.502 (6) | C20—O9 | 1.232 (5) |
C2—N1 | 1.334 (5) | C20—O10 | 1.282 (5) |
C2—C3 | 1.388 (6) | C20—C21 | 1.517 (6) |
C3—C4 | 1.374 (6) | C21—N4 | 1.321 (5) |
C3—H3 | 0.9300 | C21—C22 | 1.383 (6) |
C4—C5 | 1.385 (6) | C22—C23 | 1.385 (6) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—C6 | 1.382 (5) | C23—C24 | 1.384 (6) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C6—N1 | 1.327 (5) | C24—C25 | 1.374 (6) |
C6—C7 | 1.510 (6) | C24—H24 | 0.9300 |
C7—O3 | 1.230 (5) | C25—N4 | 1.322 (5) |
C7—O4 | 1.278 (5) | C25—C26 | 1.502 (6) |
C8—N2 | 1.329 (5) | C26—O8 | 1.228 (5) |
C8—C9 | 1.371 (5) | C26—O7 | 1.282 (5) |
C8—H8 | 0.9300 | C13'—O5' | 1.45 (5) |
C9—C10 | 1.362 (5) | C13'—H13E | 0.9700 |
C9—H9 | 0.9300 | C13'—H13F | 0.9700 |
C10—C11 | 1.372 (5) | Cu1—N1 | 1.900 (3) |
C10—H10 | 0.9300 | Cu1—N2 | 1.962 (3) |
C11—O5 | 1.366 (13) | Cu1—O1 | 2.009 (3) |
C11—C12 | 1.367 (5) | Cu1—O4 | 2.015 (3) |
C11—O5' | 1.431 (17) | Cu1—O12 | 2.277 (3) |
C12—N2 | 1.323 (5) | Cu2—N4 | 1.905 (3) |
C12—H12 | 0.9300 | Cu2—N3 | 1.964 (3) |
C13—O5 | 1.46 (4) | Cu2—O10 | 2.012 (3) |
C13—C14 | 1.46 (3) | Cu2—O7 | 2.023 (3) |
C13—H13A | 0.9700 | Cu2—O11 | 2.298 (4) |
C13—H13B | 0.9700 | O11—H11A | 0.846 (10) |
C14—O6 | 1.373 (12) | O11—H11B | 0.844 (10) |
C14—H14A | 0.9700 | O12—H12A | 0.847 (10) |
C14—H14B | 0.9700 | O12—H12B | 0.845 (10) |
C15—C16 | 1.372 (5) | O13—H13C | 0.847 (10) |
C15—C19 | 1.375 (6) | O13—H13D | 0.847 (10) |
C15—O6 | 1.399 (13) | O14—O14 | 0.000 (8) |
C15—O6' | 1.404 (17) | O14—H14C | 0.849 (10) |
C16—C17 | 1.374 (5) | O14—H14D | 0.848 (10) |
C16—H16 | 0.9300 | O15—H15A | 0.848 (10) |
C17—C18 | 1.369 (6) | O15—H15B | 0.846 (10) |
C17—H17 | 0.9300 | O16—H16A | 0.846 (10) |
C18—N3 | 1.334 (5) | O16—H16B | 0.842 (10) |
C18—H18 | 0.9300 | ||
O2—C1—O1 | 125.6 (4) | N4—C21—C22 | 119.4 (4) |
O2—C1—C2 | 120.9 (4) | N4—C21—C20 | 112.2 (4) |
O1—C1—C2 | 113.6 (4) | C22—C21—C20 | 128.4 (4) |
N1—C2—C3 | 119.1 (4) | C21—C22—C23 | 118.5 (4) |
N1—C2—C1 | 112.6 (4) | C21—C22—H22 | 120.7 |
C3—C2—C1 | 128.3 (4) | C23—C22—H22 | 120.7 |
C4—C3—C2 | 118.2 (4) | C24—C23—C22 | 119.8 (4) |
C4—C3—H3 | 120.9 | C24—C23—H23 | 120.1 |
C2—C3—H3 | 120.9 | C22—C23—H23 | 120.1 |
C3—C4—C5 | 121.3 (4) | C25—C24—C23 | 119.0 (4) |
C3—C4—H4 | 119.4 | C25—C24—H24 | 120.5 |
C5—C4—H4 | 119.4 | C23—C24—H24 | 120.5 |
C6—C5—C4 | 118.1 (4) | N4—C25—C24 | 119.3 (4) |
C6—C5—H5 | 120.9 | N4—C25—C26 | 112.4 (4) |
C4—C5—H5 | 120.9 | C24—C25—C26 | 128.3 (4) |
N1—C6—C5 | 119.4 (4) | O8—C26—O7 | 125.2 (4) |
N1—C6—C7 | 111.9 (4) | O8—C26—C25 | 120.6 (4) |
C5—C6—C7 | 128.7 (4) | O7—C26—C25 | 114.2 (4) |
O3—C7—O4 | 125.9 (4) | O5'—C13'—H13E | 110.7 |
O3—C7—C6 | 120.0 (4) | O5'—C13'—H13F | 110.7 |
O4—C7—C6 | 114.1 (4) | H13E—C13'—H13F | 108.8 |
N2—C8—C9 | 121.9 (4) | N1—Cu1—N2 | 168.63 (14) |
N2—C8—H8 | 119.1 | N1—Cu1—O1 | 80.82 (13) |
C9—C8—H8 | 119.1 | N2—Cu1—O1 | 99.23 (13) |
C10—C9—C8 | 120.3 (4) | N1—Cu1—O4 | 80.40 (13) |
C10—C9—H9 | 119.9 | N2—Cu1—O4 | 98.50 (12) |
C8—C9—H9 | 119.9 | O1—Cu1—O4 | 160.91 (11) |
C9—C10—C11 | 117.9 (4) | N1—Cu1—O12 | 97.55 (13) |
C9—C10—H10 | 121.1 | N2—Cu1—O12 | 93.80 (13) |
C11—C10—H10 | 121.1 | O1—Cu1—O12 | 93.00 (12) |
O5—C11—C12 | 117.3 (7) | O4—Cu1—O12 | 92.81 (12) |
O5—C11—C10 | 122.6 (7) | N4—Cu2—N3 | 172.46 (15) |
C12—C11—C10 | 118.8 (4) | N4—Cu2—O10 | 80.64 (13) |
O5—C11—O5' | 25.7 (5) | N3—Cu2—O10 | 97.35 (13) |
C12—C11—O5' | 113.6 (7) | N4—Cu2—O7 | 80.33 (13) |
C10—C11—O5' | 125.5 (8) | N3—Cu2—O7 | 100.59 (13) |
N2—C12—C11 | 123.5 (4) | O10—Cu2—O7 | 159.65 (13) |
N2—C12—H12 | 118.3 | N4—Cu2—O11 | 97.86 (13) |
C11—C12—H12 | 118.3 | N3—Cu2—O11 | 89.65 (14) |
O5—C13—C14 | 112 (2) | O10—Cu2—O11 | 101.44 (13) |
O5—C13—H13A | 109.3 | O7—Cu2—O11 | 88.26 (13) |
C14—C13—H13A | 109.3 | C6—N1—C2 | 123.9 (4) |
O5—C13—H13B | 109.3 | C6—N1—Cu1 | 118.4 (3) |
C14—C13—H13B | 109.3 | C2—N1—Cu1 | 117.8 (3) |
H13A—C13—H13B | 108.0 | C12—N2—C8 | 117.6 (4) |
O6—C14—C13 | 110.5 (14) | C12—N2—Cu1 | 119.1 (3) |
O6—C14—H14A | 109.6 | C8—N2—Cu1 | 123.3 (3) |
C13—C14—H14A | 109.6 | C19—N3—C18 | 117.9 (4) |
O6—C14—H14B | 109.6 | C19—N3—Cu2 | 122.1 (3) |
C13—C14—H14B | 109.6 | C18—N3—Cu2 | 119.5 (3) |
H14A—C14—H14B | 108.1 | C21—N4—C25 | 123.9 (4) |
C16—C15—C19 | 119.2 (4) | C21—N4—Cu2 | 118.2 (3) |
C16—C15—O6 | 125.8 (6) | C25—N4—Cu2 | 117.9 (3) |
C19—C15—O6 | 113.7 (6) | C1—O1—Cu1 | 115.1 (3) |
C16—C15—O6' | 119.2 (9) | C7—O4—Cu1 | 115.2 (3) |
C19—C15—O6' | 119.0 (8) | C11—O5—C13 | 115.3 (16) |
O6—C15—O6' | 28.1 (5) | C14—O6—C15 | 116.7 (9) |
C15—C16—C17 | 118.2 (4) | C26—O7—Cu2 | 114.1 (3) |
C15—C16—H16 | 120.9 | C20—O10—Cu2 | 115.1 (3) |
C17—C16—H16 | 120.9 | Cu2—O11—H11A | 109 (3) |
C18—C17—C16 | 119.4 (4) | Cu2—O11—H11B | 112 (3) |
C18—C17—H17 | 120.3 | H11A—O11—H11B | 104 (4) |
C16—C17—H17 | 120.3 | Cu1—O12—H12A | 106 (3) |
N3—C18—C17 | 122.5 (4) | Cu1—O12—H12B | 107 (3) |
N3—C18—H18 | 118.7 | H12A—O12—H12B | 108 (4) |
C17—C18—H18 | 118.7 | H13C—O13—H13D | 117 (5) |
N3—C19—C15 | 122.8 (4) | O14—O14—H14C | 0 (10) |
N3—C19—H19 | 118.6 | O14—O14—H14D | 0 (10) |
C15—C19—H19 | 118.6 | H14C—O14—H14D | 99 (5) |
O9—C20—O10 | 125.7 (4) | H15A—O15—H15B | 108 (6) |
O9—C20—C21 | 120.4 (4) | H16A—O16—H16B | 114 (5) |
O10—C20—C21 | 113.9 (4) | C11—O5'—C13' | 111 (2) |
O2—C1—C2—N1 | 177.5 (4) | O12—Cu1—N2—C12 | 86.0 (3) |
O1—C1—C2—N1 | −3.1 (5) | N1—Cu1—N2—C8 | 89.9 (8) |
O2—C1—C2—C3 | −1.8 (7) | O1—Cu1—N2—C8 | 0.6 (3) |
O1—C1—C2—C3 | 177.6 (4) | O4—Cu1—N2—C8 | 173.5 (3) |
N1—C2—C3—C4 | 0.1 (7) | O12—Cu1—N2—C8 | −93.1 (3) |
C1—C2—C3—C4 | 179.3 (4) | C15—C19—N3—C18 | −0.8 (7) |
C2—C3—C4—C5 | −1.6 (7) | C15—C19—N3—Cu2 | −172.5 (4) |
C3—C4—C5—C6 | 1.4 (7) | C17—C18—N3—C19 | 0.4 (7) |
C4—C5—C6—N1 | 0.4 (6) | C17—C18—N3—Cu2 | 172.3 (3) |
C4—C5—C6—C7 | 179.3 (4) | N4—Cu2—N3—C19 | −111.6 (11) |
N1—C6—C7—O3 | −178.4 (4) | O10—Cu2—N3—C19 | 174.4 (4) |
C5—C6—C7—O3 | 2.6 (7) | O7—Cu2—N3—C19 | −15.2 (4) |
N1—C6—C7—O4 | 2.7 (5) | O11—Cu2—N3—C19 | 72.9 (4) |
C5—C6—C7—O4 | −176.3 (4) | N4—Cu2—N3—C18 | 76.9 (11) |
N2—C8—C9—C10 | −0.8 (7) | O10—Cu2—N3—C18 | 2.9 (3) |
C8—C9—C10—C11 | −0.1 (6) | O7—Cu2—N3—C18 | 173.2 (3) |
C9—C10—C11—O5 | −165.1 (9) | O11—Cu2—N3—C18 | −98.6 (3) |
C9—C10—C11—C12 | 1.3 (6) | C22—C21—N4—C25 | 1.2 (6) |
C9—C10—C11—O5' | 164.0 (11) | C20—C21—N4—C25 | −178.4 (4) |
O5—C11—C12—N2 | 165.4 (9) | C22—C21—N4—Cu2 | −179.3 (3) |
C10—C11—C12—N2 | −1.6 (7) | C20—C21—N4—Cu2 | 1.1 (5) |
O5'—C11—C12—N2 | −166.3 (10) | C24—C25—N4—C21 | −1.9 (7) |
O5—C13—C14—O6 | 46 (3) | C26—C25—N4—C21 | 176.7 (4) |
C19—C15—C16—C17 | −1.5 (7) | C24—C25—N4—Cu2 | 178.5 (3) |
O6—C15—C16—C17 | −167.7 (10) | C26—C25—N4—Cu2 | −2.9 (5) |
O6'—C15—C16—C17 | 159.7 (10) | N3—Cu2—N4—C21 | −75.3 (11) |
C15—C16—C17—C18 | 1.2 (7) | O10—Cu2—N4—C21 | −0.2 (3) |
C16—C17—C18—N3 | −0.6 (7) | O7—Cu2—N4—C21 | −173.0 (3) |
C16—C15—C19—N3 | 1.4 (7) | O11—Cu2—N4—C21 | 100.2 (3) |
O6—C15—C19—N3 | 169.2 (9) | N3—Cu2—N4—C25 | 104.3 (11) |
O6'—C15—C19—N3 | −159.9 (11) | O10—Cu2—N4—C25 | 179.4 (3) |
O9—C20—C21—N4 | 176.1 (4) | O7—Cu2—N4—C25 | 6.7 (3) |
O10—C20—C21—N4 | −1.9 (6) | O11—Cu2—N4—C25 | −80.2 (3) |
O9—C20—C21—C22 | −3.4 (7) | O2—C1—O1—Cu1 | 179.9 (4) |
O10—C20—C21—C22 | 178.5 (4) | C2—C1—O1—Cu1 | 0.5 (5) |
N4—C21—C22—C23 | 0.4 (6) | N1—Cu1—O1—C1 | 1.3 (3) |
C20—C21—C22—C23 | 180.0 (4) | N2—Cu1—O1—C1 | 169.8 (3) |
C21—C22—C23—C24 | −1.3 (7) | O4—Cu1—O1—C1 | 11.7 (6) |
C22—C23—C24—C25 | 0.6 (7) | O12—Cu1—O1—C1 | −95.8 (3) |
C23—C24—C25—N4 | 1.0 (7) | O3—C7—O4—Cu1 | −180.0 (4) |
C23—C24—C25—C26 | −177.3 (4) | C6—C7—O4—Cu1 | −1.1 (5) |
N4—C25—C26—O8 | 175.7 (4) | N1—Cu1—O4—C7 | −0.3 (3) |
C24—C25—C26—O8 | −5.9 (7) | N2—Cu1—O4—C7 | −168.9 (3) |
N4—C25—C26—O7 | −5.5 (6) | O1—Cu1—O4—C7 | −10.7 (5) |
C24—C25—C26—O7 | 172.8 (4) | O12—Cu1—O4—C7 | 96.8 (3) |
C5—C6—N1—C2 | −2.0 (6) | C12—C11—O5—C13 | 144.9 (16) |
C7—C6—N1—C2 | 178.9 (4) | C10—C11—O5—C13 | −49 (2) |
C5—C6—N1—Cu1 | 176.0 (3) | O5'—C11—O5—C13 | 57 (2) |
C7—C6—N1—Cu1 | −3.1 (5) | C14—C13—O5—C11 | −173.6 (9) |
C3—C2—N1—C6 | 1.8 (6) | C13—C14—O6—C15 | −174.5 (11) |
C1—C2—N1—C6 | −177.6 (4) | C16—C15—O6—C14 | −16.1 (19) |
C3—C2—N1—Cu1 | −176.2 (3) | C19—C15—O6—C14 | 177.1 (10) |
C1—C2—N1—Cu1 | 4.4 (5) | O6'—C15—O6—C14 | 70 (2) |
N2—Cu1—N1—C6 | 87.4 (8) | O8—C26—O7—Cu2 | −170.5 (4) |
O1—Cu1—N1—C6 | 178.6 (3) | C25—C26—O7—Cu2 | 10.8 (5) |
O4—Cu1—N1—C6 | 2.0 (3) | N4—Cu2—O7—C26 | −9.8 (3) |
O12—Cu1—N1—C6 | −89.6 (3) | N3—Cu2—O7—C26 | 177.8 (3) |
N2—Cu1—N1—C2 | −94.4 (8) | O10—Cu2—O7—C26 | −30.7 (5) |
O1—Cu1—N1—C2 | −3.3 (3) | O11—Cu2—O7—C26 | 88.5 (3) |
O4—Cu1—N1—C2 | −179.8 (3) | O9—C20—O10—Cu2 | −176.1 (4) |
O12—Cu1—N1—C2 | 88.6 (3) | C21—C20—O10—Cu2 | 1.8 (5) |
C11—C12—N2—C8 | 0.7 (6) | N4—Cu2—O10—C20 | −1.0 (3) |
C11—C12—N2—Cu1 | −178.4 (3) | N3—Cu2—O10—C20 | 171.7 (3) |
C9—C8—N2—C12 | 0.6 (6) | O7—Cu2—O10—C20 | 20.0 (6) |
C9—C8—N2—Cu1 | 179.7 (3) | O11—Cu2—O10—C20 | −97.2 (3) |
N1—Cu1—N2—C12 | −91.0 (8) | O5—C11—O5'—C13' | −62 (3) |
O1—Cu1—N2—C12 | 179.7 (3) | C12—C11—O5'—C13' | −166 (2) |
O4—Cu1—N2—C12 | −7.4 (3) | C10—C11—O5'—C13' | 31 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11A···O14 | 0.85 (1) | 1.94 (2) | 2.773 (5) | 166 (5) |
O11—H11B···O2i | 0.84 (1) | 1.95 (2) | 2.785 (4) | 168 (5) |
O12—H12A···O9ii | 0.85 (1) | 1.88 (1) | 2.723 (4) | 173 (5) |
O12—H12B···O13i | 0.85 (1) | 1.87 (1) | 2.715 (5) | 175 (4) |
O13—H13C···O16iii | 0.85 (1) | 1.94 (2) | 2.769 (6) | 166 (4) |
O13—H13D···O16iv | 0.85 (1) | 2.04 (2) | 2.857 (6) | 163 (6) |
O14—H14C···O8v | 0.85 (1) | 2.08 (2) | 2.898 (5) | 163 (6) |
O14—H14D···O1vi | 0.85 (1) | 1.99 (2) | 2.811 (5) | 163 (5) |
O14—H14D···O2vi | 0.85 (1) | 2.59 (4) | 3.228 (5) | 133 (5) |
O15—H15A···O8vii | 0.85 (1) | 2.21 (2) | 3.028 (5) | 162 (6) |
O15—H15A···O7vii | 0.85 (1) | 2.43 (4) | 3.114 (5) | 138 (5) |
O15—H15B···O3vii | 0.85 (1) | 1.99 (2) | 2.826 (5) | 169 (6) |
O16—H16A···O15viii | 0.85 (1) | 1.82 (1) | 2.666 (6) | 179 (6) |
O16—H16B···O6′ix | 0.84 (1) | 2.28 (3) | 3.061 (17) | 156 (4) |
O16—H16B···O5ix | 0.84 (1) | 2.45 (4) | 3.041 (13) | 128 (4) |
O16—H16B···O6ix | 0.84 (1) | 2.39 (2) | 3.209 (15) | 164 (4) |
O16—H16B···O5′ix | 0.84 (1) | 2.53 (4) | 3.175 (19) | 134 (4) |
C17—H17···O10x | 0.93 | 2.46 | 3.379 (5) | 169 |
C23—H23···O14xi | 0.93 | 2.47 | 3.352 (6) | 158 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, y, z+1; (iii) −x+1, −y+2, −z+1; (iv) x−1, y, z+1; (v) −x, −y+1, −z+1; (vi) x, y, z−1; (vii) x+1, y, z; (viii) −x+2, −y+1, −z+1; (ix) −x+1, −y+1, −z+1; (x) −x+1, −y, −z+1; (xi) x−1, y, z. |
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