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μ-1,2-Bis(pyridin-3-yl­oxy)ethane-κ2N:N′-bis­[aqua­(pyridine-2,6-di­carboxyl­ato-κ3O2,N,O6)copper(II)] tetra­hydrate, [Cu2(C7H3NO4)2(C12H12N2O2)(H2O)2]·4H2O, (I), is a C-shaped mol­ecule based on 1,2-bis­(pyridin-3-yl­oxy)ethane (L) and CuII in the presence of pyridine-2,6-di­carb­oxy­lic acid (H2pydc). The two five-coordinated CuII centres are chelated by terminal pydc2− ligands and bridged by an L spacer. The mol­ecules are arranged in a two-dimensional sheet via 15 O—H...O hydrogen bonds, and C—H...O inter­actions further bridge neighbouring sheets into a three-dimensional supermolecular architecture. The structure includes a well-resolved cyclic water tetra­mer, which acts as a subunit to form a larger aggregate. A thermogravimetric analysis of complex (I) was also carried out.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113027996/fn3155sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113027996/fn3155Isup2.hkl
Contains datablock I

CCDC reference: 966113

Computing details top

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).

µ-1,2-Bis(pyridin-3-yloxy)ethane-κ2N:N'-bis[aqua(pyridine-2,6-dicarboxylato-κ3O2,N,O6)copper(II)] tetrahydrate top
Crystal data top
[Cu2(C7H3NO4)2(C12H12N2O2)(H2O)2]·4H2OZ = 2
Mr = 781.62F(000) = 800
Triclinic, P1Dx = 1.704 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1142 (19) ÅCell parameters from 1397 reflections
b = 11.940 (3) Åθ = 2.4–21.5°
c = 16.160 (4) ŵ = 1.48 mm1
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
Data collection top
Bruker SMART CCD area-detector
diffractometer
5571 independent reflections
Radiation source: fine-focus sealed tube3740 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 99
Tmin = 0.852, Tmax = 0.915k = 1114
8073 measured reflectionsl = 1819
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H 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 parametersΔρmax = 0.43 e Å3
12 restraintsΔρmin = 0.50 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0714 (6)0.4549 (4)1.3028 (3)0.0362 (11)
C20.1990 (5)0.4861 (3)1.2398 (3)0.0345 (11)
C30.3463 (6)0.5466 (4)1.2478 (3)0.0442 (13)
H30.37800.57311.29710.053*
C40.4441 (6)0.5663 (4)1.1810 (3)0.0483 (13)
H40.54450.60511.18580.058*
C50.3959 (5)0.5296 (4)1.1065 (3)0.0391 (12)
H50.46140.54471.06100.047*
C60.2477 (5)0.4701 (3)1.1017 (3)0.0310 (10)
C70.1685 (5)0.4201 (4)1.0292 (3)0.0344 (11)
C80.3710 (5)0.2834 (4)1.2033 (3)0.0350 (11)
H80.34220.30741.25390.042*
C90.5257 (5)0.2375 (4)1.1901 (3)0.0374 (11)
H90.60040.23171.23120.045*
C100.5704 (5)0.2004 (3)1.1170 (3)0.0318 (10)
H100.67510.16921.10730.038*
C110.4562 (5)0.2104 (4)1.0582 (3)0.0332 (11)
C120.3052 (5)0.2589 (4)1.0748 (3)0.0377 (11)
H120.22950.26721.03400.045*
C130.634 (4)0.163 (2)0.9443 (19)0.032 (4)0.57 (3)
H13A0.71700.12540.98060.038*0.57 (3)
H13B0.66330.24340.92610.038*0.57 (3)
C140.6351 (5)0.1117 (4)0.8700 (3)0.0375 (11)0.57 (3)
H14A0.73420.13430.83260.045*0.57 (3)
H14B0.63660.02890.88790.045*0.57 (3)
C150.4748 (5)0.0954 (4)0.7585 (3)0.0394 (12)
C160.5926 (5)0.0360 (3)0.7182 (3)0.0352 (11)
H160.69200.01350.74160.042*
C170.5598 (5)0.0107 (4)0.6423 (3)0.0401 (12)
H170.63630.03070.61390.048*
C180.4135 (6)0.0469 (3)0.6088 (3)0.0388 (12)
H180.39300.02990.55720.047*
C190.3311 (5)0.1295 (4)0.7208 (3)0.0448 (13)
H190.25290.17120.74800.054*
C200.0460 (6)0.1224 (4)0.4310 (3)0.0404 (12)
C210.1051 (5)0.1869 (3)0.4596 (3)0.0304 (10)
C220.2468 (6)0.2182 (4)0.4185 (3)0.0401 (12)
H220.25890.19990.36620.048*
C230.3705 (5)0.2773 (4)0.4569 (3)0.0436 (12)
H230.46600.30060.42990.052*
C240.3514 (6)0.3016 (4)0.5355 (3)0.0430 (12)
H240.43420.34070.56200.052*
C250.2086 (5)0.2672 (3)0.5737 (3)0.0331 (11)
C260.1641 (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)
H13E0.61620.05351.00020.038*0.43 (3)
H13F0.73310.16020.97040.038*0.43 (3)
C14'0.6351 (5)0.1117 (4)0.8700 (3)0.0375 (11)0.43 (3)
H14E0.68010.18030.83240.045*0.43 (3)
H14F0.70880.04820.86300.045*0.43 (3)
Cu10.03803 (6)0.35908 (4)1.16228 (3)0.03274 (16)
Cu20.10622 (7)0.17035 (5)0.58813 (3)0.03902 (18)
N10.1578 (4)0.4496 (3)1.1680 (2)0.0288 (8)
N20.2611 (4)0.2947 (3)1.1458 (2)0.0286 (8)
N30.2992 (4)0.1055 (3)0.6475 (2)0.0344 (9)
N40.0919 (4)0.2133 (3)0.5340 (2)0.0299 (8)
O10.0507 (4)0.3939 (2)1.27781 (17)0.0415 (8)
O20.0877 (4)0.4853 (3)1.37055 (19)0.0508 (9)
O30.2348 (4)0.4338 (3)0.96221 (19)0.0463 (8)
O40.0346 (3)0.3639 (2)1.04561 (17)0.0357 (7)
O50.4727 (15)0.1540 (14)0.9926 (9)0.032 (3)0.57 (3)
O60.4977 (17)0.1462 (14)0.8270 (9)0.038 (3)0.57 (3)
O70.0294 (4)0.2284 (3)0.68209 (17)0.0429 (8)
O80.2549 (4)0.3339 (2)0.70240 (18)0.0451 (8)
O90.0499 (4)0.0860 (3)0.36494 (19)0.0523 (9)
O100.1600 (4)0.1082 (3)0.48231 (18)0.0439 (8)
O110.2334 (4)0.3453 (3)0.5511 (2)0.0479 (9)
H11A0.237 (6)0.369 (4)0.4977 (8)0.060 (18)*
H11B0.178 (5)0.397 (3)0.570 (3)0.067 (18)*
O120.0784 (4)0.1850 (3)1.2165 (2)0.0379 (8)
H12A0.030 (5)0.156 (4)1.2607 (18)0.064 (18)*
H12B0.055 (5)0.143 (3)1.181 (2)0.047 (15)*
O130.0089 (6)0.9395 (4)0.9051 (3)0.0757 (13)
H13C0.043 (5)1.0064 (17)0.903 (3)0.041 (15)*
H13D0.046 (6)0.906 (4)0.950 (2)0.09 (2)*
O140.3027 (5)0.4278 (4)0.3781 (2)0.0525 (9)
H14C0.301 (7)0.5002 (10)0.363 (3)0.09 (2)*
H14D0.215 (4)0.413 (5)0.358 (3)0.08 (2)*
O150.9560 (5)0.3192 (3)0.8497 (3)0.0593 (10)
H15A0.917 (7)0.321 (5)0.803 (2)0.10 (3)*
H15B0.890 (6)0.357 (4)0.878 (3)0.10 (3)*
O160.8639 (5)0.8567 (3)0.0740 (2)0.0546 (9)
H16A0.922 (6)0.801 (3)0.098 (3)0.07 (2)*
H16B0.7626 (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)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.036 (3)0.035 (3)0.038 (3)0.004 (2)0.001 (2)0.009 (2)
C20.033 (3)0.033 (3)0.037 (3)0.001 (2)0.002 (2)0.009 (2)
C30.038 (3)0.045 (3)0.049 (3)0.006 (2)0.009 (3)0.016 (2)
C40.031 (3)0.051 (3)0.058 (4)0.013 (2)0.006 (3)0.007 (3)
C50.022 (3)0.046 (3)0.046 (3)0.010 (2)0.005 (2)0.002 (2)
C60.028 (3)0.029 (3)0.035 (3)0.002 (2)0.002 (2)0.005 (2)
C70.031 (3)0.036 (3)0.037 (3)0.000 (2)0.006 (2)0.008 (2)
C80.034 (3)0.051 (3)0.024 (3)0.003 (2)0.001 (2)0.017 (2)
C90.024 (3)0.059 (3)0.035 (3)0.004 (2)0.014 (2)0.016 (2)
C100.020 (2)0.040 (3)0.035 (3)0.005 (2)0.0004 (19)0.008 (2)
C110.029 (3)0.043 (3)0.032 (3)0.002 (2)0.005 (2)0.018 (2)
C120.028 (3)0.055 (3)0.035 (3)0.005 (2)0.011 (2)0.016 (2)
C130.027 (3)0.045 (13)0.022 (11)0.010 (11)0.008 (7)0.001 (9)
C140.025 (3)0.053 (3)0.039 (3)0.008 (2)0.007 (2)0.018 (2)
C150.031 (3)0.065 (3)0.026 (3)0.005 (2)0.005 (2)0.019 (2)
C160.032 (3)0.041 (3)0.032 (3)0.009 (2)0.004 (2)0.008 (2)
C170.036 (3)0.049 (3)0.040 (3)0.019 (2)0.006 (2)0.020 (2)
C180.048 (3)0.044 (3)0.029 (3)0.008 (2)0.006 (2)0.017 (2)
C190.030 (3)0.071 (4)0.041 (3)0.018 (2)0.006 (2)0.030 (3)
C200.050 (3)0.041 (3)0.030 (3)0.018 (2)0.007 (2)0.007 (2)
C210.033 (3)0.033 (3)0.026 (3)0.003 (2)0.005 (2)0.008 (2)
C220.040 (3)0.051 (3)0.030 (3)0.008 (2)0.010 (2)0.010 (2)
C230.027 (3)0.057 (3)0.045 (3)0.009 (2)0.011 (2)0.003 (3)
C240.032 (3)0.046 (3)0.051 (3)0.010 (2)0.001 (2)0.013 (2)
C250.029 (3)0.037 (3)0.031 (3)0.006 (2)0.003 (2)0.006 (2)
C260.030 (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)
Cu10.0260 (3)0.0431 (4)0.0333 (3)0.0102 (2)0.0070 (2)0.0170 (3)
Cu20.0317 (4)0.0602 (4)0.0300 (3)0.0158 (3)0.0086 (2)0.0202 (3)
N10.020 (2)0.032 (2)0.035 (2)0.0042 (15)0.0005 (16)0.0112 (17)
N20.027 (2)0.033 (2)0.027 (2)0.0032 (16)0.0038 (16)0.0105 (16)
N30.029 (2)0.048 (2)0.028 (2)0.0120 (18)0.0073 (16)0.0134 (18)
N40.022 (2)0.038 (2)0.030 (2)0.0067 (16)0.0038 (16)0.0091 (17)
O10.039 (2)0.052 (2)0.040 (2)0.0150 (16)0.0100 (15)0.0249 (16)
O20.053 (2)0.064 (2)0.042 (2)0.0062 (17)0.0011 (16)0.0293 (18)
O30.042 (2)0.061 (2)0.040 (2)0.0098 (16)0.0155 (16)0.0158 (16)
O40.0282 (18)0.049 (2)0.0330 (18)0.0133 (14)0.0081 (14)0.0151 (14)
O50.021 (4)0.044 (7)0.033 (6)0.010 (5)0.008 (4)0.015 (5)
O60.030 (5)0.055 (8)0.034 (6)0.016 (6)0.011 (4)0.019 (6)
O70.036 (2)0.067 (2)0.0308 (18)0.0129 (16)0.0035 (14)0.0221 (15)
O80.044 (2)0.052 (2)0.042 (2)0.0081 (16)0.0078 (16)0.0217 (16)
O90.062 (2)0.068 (2)0.035 (2)0.0321 (18)0.0200 (17)0.0273 (17)
O100.039 (2)0.067 (2)0.0314 (18)0.0249 (16)0.0129 (15)0.0238 (16)
O110.047 (2)0.053 (2)0.045 (3)0.0103 (18)0.0008 (18)0.017 (2)
O120.040 (2)0.046 (2)0.031 (2)0.0076 (16)0.0106 (16)0.0125 (17)
O130.124 (4)0.054 (3)0.052 (3)0.023 (3)0.011 (3)0.022 (2)
O140.048 (3)0.059 (3)0.053 (2)0.010 (2)0.0170 (19)0.014 (2)
O150.065 (3)0.073 (3)0.043 (3)0.010 (2)0.002 (2)0.019 (2)
O160.039 (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)
Geometric parameters (Å, º) top
C1—O21.219 (5)C19—N31.325 (5)
C1—O11.296 (5)C19—H190.9300
C1—C21.502 (6)C20—O91.232 (5)
C2—N11.334 (5)C20—O101.282 (5)
C2—C31.388 (6)C20—C211.517 (6)
C3—C41.374 (6)C21—N41.321 (5)
C3—H30.9300C21—C221.383 (6)
C4—C51.385 (6)C22—C231.385 (6)
C4—H40.9300C22—H220.9300
C5—C61.382 (5)C23—C241.384 (6)
C5—H50.9300C23—H230.9300
C6—N11.327 (5)C24—C251.374 (6)
C6—C71.510 (6)C24—H240.9300
C7—O31.230 (5)C25—N41.322 (5)
C7—O41.278 (5)C25—C261.502 (6)
C8—N21.329 (5)C26—O81.228 (5)
C8—C91.371 (5)C26—O71.282 (5)
C8—H80.9300C13'—O5'1.45 (5)
C9—C101.362 (5)C13'—H13E0.9700
C9—H90.9300C13'—H13F0.9700
C10—C111.372 (5)Cu1—N11.900 (3)
C10—H100.9300Cu1—N21.962 (3)
C11—O51.366 (13)Cu1—O12.009 (3)
C11—C121.367 (5)Cu1—O42.015 (3)
C11—O5'1.431 (17)Cu1—O122.277 (3)
C12—N21.323 (5)Cu2—N41.905 (3)
C12—H120.9300Cu2—N31.964 (3)
C13—O51.46 (4)Cu2—O102.012 (3)
C13—C141.46 (3)Cu2—O72.023 (3)
C13—H13A0.9700Cu2—O112.298 (4)
C13—H13B0.9700O11—H11A0.846 (10)
C14—O61.373 (12)O11—H11B0.844 (10)
C14—H14A0.9700O12—H12A0.847 (10)
C14—H14B0.9700O12—H12B0.845 (10)
C15—C161.372 (5)O13—H13C0.847 (10)
C15—C191.375 (6)O13—H13D0.847 (10)
C15—O61.399 (13)O14—O140.000 (8)
C15—O6'1.404 (17)O14—H14C0.849 (10)
C16—C171.374 (5)O14—H14D0.848 (10)
C16—H160.9300O15—H15A0.848 (10)
C17—C181.369 (6)O15—H15B0.846 (10)
C17—H170.9300O16—H16A0.846 (10)
C18—N31.334 (5)O16—H16B0.842 (10)
C18—H180.9300
O2—C1—O1125.6 (4)N4—C21—C22119.4 (4)
O2—C1—C2120.9 (4)N4—C21—C20112.2 (4)
O1—C1—C2113.6 (4)C22—C21—C20128.4 (4)
N1—C2—C3119.1 (4)C21—C22—C23118.5 (4)
N1—C2—C1112.6 (4)C21—C22—H22120.7
C3—C2—C1128.3 (4)C23—C22—H22120.7
C4—C3—C2118.2 (4)C24—C23—C22119.8 (4)
C4—C3—H3120.9C24—C23—H23120.1
C2—C3—H3120.9C22—C23—H23120.1
C3—C4—C5121.3 (4)C25—C24—C23119.0 (4)
C3—C4—H4119.4C25—C24—H24120.5
C5—C4—H4119.4C23—C24—H24120.5
C6—C5—C4118.1 (4)N4—C25—C24119.3 (4)
C6—C5—H5120.9N4—C25—C26112.4 (4)
C4—C5—H5120.9C24—C25—C26128.3 (4)
N1—C6—C5119.4 (4)O8—C26—O7125.2 (4)
N1—C6—C7111.9 (4)O8—C26—C25120.6 (4)
C5—C6—C7128.7 (4)O7—C26—C25114.2 (4)
O3—C7—O4125.9 (4)O5'—C13'—H13E110.7
O3—C7—C6120.0 (4)O5'—C13'—H13F110.7
O4—C7—C6114.1 (4)H13E—C13'—H13F108.8
N2—C8—C9121.9 (4)N1—Cu1—N2168.63 (14)
N2—C8—H8119.1N1—Cu1—O180.82 (13)
C9—C8—H8119.1N2—Cu1—O199.23 (13)
C10—C9—C8120.3 (4)N1—Cu1—O480.40 (13)
C10—C9—H9119.9N2—Cu1—O498.50 (12)
C8—C9—H9119.9O1—Cu1—O4160.91 (11)
C9—C10—C11117.9 (4)N1—Cu1—O1297.55 (13)
C9—C10—H10121.1N2—Cu1—O1293.80 (13)
C11—C10—H10121.1O1—Cu1—O1293.00 (12)
O5—C11—C12117.3 (7)O4—Cu1—O1292.81 (12)
O5—C11—C10122.6 (7)N4—Cu2—N3172.46 (15)
C12—C11—C10118.8 (4)N4—Cu2—O1080.64 (13)
O5—C11—O5'25.7 (5)N3—Cu2—O1097.35 (13)
C12—C11—O5'113.6 (7)N4—Cu2—O780.33 (13)
C10—C11—O5'125.5 (8)N3—Cu2—O7100.59 (13)
N2—C12—C11123.5 (4)O10—Cu2—O7159.65 (13)
N2—C12—H12118.3N4—Cu2—O1197.86 (13)
C11—C12—H12118.3N3—Cu2—O1189.65 (14)
O5—C13—C14112 (2)O10—Cu2—O11101.44 (13)
O5—C13—H13A109.3O7—Cu2—O1188.26 (13)
C14—C13—H13A109.3C6—N1—C2123.9 (4)
O5—C13—H13B109.3C6—N1—Cu1118.4 (3)
C14—C13—H13B109.3C2—N1—Cu1117.8 (3)
H13A—C13—H13B108.0C12—N2—C8117.6 (4)
O6—C14—C13110.5 (14)C12—N2—Cu1119.1 (3)
O6—C14—H14A109.6C8—N2—Cu1123.3 (3)
C13—C14—H14A109.6C19—N3—C18117.9 (4)
O6—C14—H14B109.6C19—N3—Cu2122.1 (3)
C13—C14—H14B109.6C18—N3—Cu2119.5 (3)
H14A—C14—H14B108.1C21—N4—C25123.9 (4)
C16—C15—C19119.2 (4)C21—N4—Cu2118.2 (3)
C16—C15—O6125.8 (6)C25—N4—Cu2117.9 (3)
C19—C15—O6113.7 (6)C1—O1—Cu1115.1 (3)
C16—C15—O6'119.2 (9)C7—O4—Cu1115.2 (3)
C19—C15—O6'119.0 (8)C11—O5—C13115.3 (16)
O6—C15—O6'28.1 (5)C14—O6—C15116.7 (9)
C15—C16—C17118.2 (4)C26—O7—Cu2114.1 (3)
C15—C16—H16120.9C20—O10—Cu2115.1 (3)
C17—C16—H16120.9Cu2—O11—H11A109 (3)
C18—C17—C16119.4 (4)Cu2—O11—H11B112 (3)
C18—C17—H17120.3H11A—O11—H11B104 (4)
C16—C17—H17120.3Cu1—O12—H12A106 (3)
N3—C18—C17122.5 (4)Cu1—O12—H12B107 (3)
N3—C18—H18118.7H12A—O12—H12B108 (4)
C17—C18—H18118.7H13C—O13—H13D117 (5)
N3—C19—C15122.8 (4)O14—O14—H14C0 (10)
N3—C19—H19118.6O14—O14—H14D0 (10)
C15—C19—H19118.6H14C—O14—H14D99 (5)
O9—C20—O10125.7 (4)H15A—O15—H15B108 (6)
O9—C20—C21120.4 (4)H16A—O16—H16B114 (5)
O10—C20—C21113.9 (4)C11—O5'—C13'111 (2)
O2—C1—C2—N1177.5 (4)O12—Cu1—N2—C1286.0 (3)
O1—C1—C2—N13.1 (5)N1—Cu1—N2—C889.9 (8)
O2—C1—C2—C31.8 (7)O1—Cu1—N2—C80.6 (3)
O1—C1—C2—C3177.6 (4)O4—Cu1—N2—C8173.5 (3)
N1—C2—C3—C40.1 (7)O12—Cu1—N2—C893.1 (3)
C1—C2—C3—C4179.3 (4)C15—C19—N3—C180.8 (7)
C2—C3—C4—C51.6 (7)C15—C19—N3—Cu2172.5 (4)
C3—C4—C5—C61.4 (7)C17—C18—N3—C190.4 (7)
C4—C5—C6—N10.4 (6)C17—C18—N3—Cu2172.3 (3)
C4—C5—C6—C7179.3 (4)N4—Cu2—N3—C19111.6 (11)
N1—C6—C7—O3178.4 (4)O10—Cu2—N3—C19174.4 (4)
C5—C6—C7—O32.6 (7)O7—Cu2—N3—C1915.2 (4)
N1—C6—C7—O42.7 (5)O11—Cu2—N3—C1972.9 (4)
C5—C6—C7—O4176.3 (4)N4—Cu2—N3—C1876.9 (11)
N2—C8—C9—C100.8 (7)O10—Cu2—N3—C182.9 (3)
C8—C9—C10—C110.1 (6)O7—Cu2—N3—C18173.2 (3)
C9—C10—C11—O5165.1 (9)O11—Cu2—N3—C1898.6 (3)
C9—C10—C11—C121.3 (6)C22—C21—N4—C251.2 (6)
C9—C10—C11—O5'164.0 (11)C20—C21—N4—C25178.4 (4)
O5—C11—C12—N2165.4 (9)C22—C21—N4—Cu2179.3 (3)
C10—C11—C12—N21.6 (7)C20—C21—N4—Cu21.1 (5)
O5'—C11—C12—N2166.3 (10)C24—C25—N4—C211.9 (7)
O5—C13—C14—O646 (3)C26—C25—N4—C21176.7 (4)
C19—C15—C16—C171.5 (7)C24—C25—N4—Cu2178.5 (3)
O6—C15—C16—C17167.7 (10)C26—C25—N4—Cu22.9 (5)
O6'—C15—C16—C17159.7 (10)N3—Cu2—N4—C2175.3 (11)
C15—C16—C17—C181.2 (7)O10—Cu2—N4—C210.2 (3)
C16—C17—C18—N30.6 (7)O7—Cu2—N4—C21173.0 (3)
C16—C15—C19—N31.4 (7)O11—Cu2—N4—C21100.2 (3)
O6—C15—C19—N3169.2 (9)N3—Cu2—N4—C25104.3 (11)
O6'—C15—C19—N3159.9 (11)O10—Cu2—N4—C25179.4 (3)
O9—C20—C21—N4176.1 (4)O7—Cu2—N4—C256.7 (3)
O10—C20—C21—N41.9 (6)O11—Cu2—N4—C2580.2 (3)
O9—C20—C21—C223.4 (7)O2—C1—O1—Cu1179.9 (4)
O10—C20—C21—C22178.5 (4)C2—C1—O1—Cu10.5 (5)
N4—C21—C22—C230.4 (6)N1—Cu1—O1—C11.3 (3)
C20—C21—C22—C23180.0 (4)N2—Cu1—O1—C1169.8 (3)
C21—C22—C23—C241.3 (7)O4—Cu1—O1—C111.7 (6)
C22—C23—C24—C250.6 (7)O12—Cu1—O1—C195.8 (3)
C23—C24—C25—N41.0 (7)O3—C7—O4—Cu1180.0 (4)
C23—C24—C25—C26177.3 (4)C6—C7—O4—Cu11.1 (5)
N4—C25—C26—O8175.7 (4)N1—Cu1—O4—C70.3 (3)
C24—C25—C26—O85.9 (7)N2—Cu1—O4—C7168.9 (3)
N4—C25—C26—O75.5 (6)O1—Cu1—O4—C710.7 (5)
C24—C25—C26—O7172.8 (4)O12—Cu1—O4—C796.8 (3)
C5—C6—N1—C22.0 (6)C12—C11—O5—C13144.9 (16)
C7—C6—N1—C2178.9 (4)C10—C11—O5—C1349 (2)
C5—C6—N1—Cu1176.0 (3)O5'—C11—O5—C1357 (2)
C7—C6—N1—Cu13.1 (5)C14—C13—O5—C11173.6 (9)
C3—C2—N1—C61.8 (6)C13—C14—O6—C15174.5 (11)
C1—C2—N1—C6177.6 (4)C16—C15—O6—C1416.1 (19)
C3—C2—N1—Cu1176.2 (3)C19—C15—O6—C14177.1 (10)
C1—C2—N1—Cu14.4 (5)O6'—C15—O6—C1470 (2)
N2—Cu1—N1—C687.4 (8)O8—C26—O7—Cu2170.5 (4)
O1—Cu1—N1—C6178.6 (3)C25—C26—O7—Cu210.8 (5)
O4—Cu1—N1—C62.0 (3)N4—Cu2—O7—C269.8 (3)
O12—Cu1—N1—C689.6 (3)N3—Cu2—O7—C26177.8 (3)
N2—Cu1—N1—C294.4 (8)O10—Cu2—O7—C2630.7 (5)
O1—Cu1—N1—C23.3 (3)O11—Cu2—O7—C2688.5 (3)
O4—Cu1—N1—C2179.8 (3)O9—C20—O10—Cu2176.1 (4)
O12—Cu1—N1—C288.6 (3)C21—C20—O10—Cu21.8 (5)
C11—C12—N2—C80.7 (6)N4—Cu2—O10—C201.0 (3)
C11—C12—N2—Cu1178.4 (3)N3—Cu2—O10—C20171.7 (3)
C9—C8—N2—C120.6 (6)O7—Cu2—O10—C2020.0 (6)
C9—C8—N2—Cu1179.7 (3)O11—Cu2—O10—C2097.2 (3)
N1—Cu1—N2—C1291.0 (8)O5—C11—O5'—C13'62 (3)
O1—Cu1—N2—C12179.7 (3)C12—C11—O5'—C13'166 (2)
O4—Cu1—N2—C127.4 (3)C10—C11—O5'—C13'31 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H11A···O140.85 (1)1.94 (2)2.773 (5)166 (5)
O11—H11B···O2i0.84 (1)1.95 (2)2.785 (4)168 (5)
O12—H12A···O9ii0.85 (1)1.88 (1)2.723 (4)173 (5)
O12—H12B···O13i0.85 (1)1.87 (1)2.715 (5)175 (4)
O13—H13C···O16iii0.85 (1)1.94 (2)2.769 (6)166 (4)
O13—H13D···O16iv0.85 (1)2.04 (2)2.857 (6)163 (6)
O14—H14C···O8v0.85 (1)2.08 (2)2.898 (5)163 (6)
O14—H14D···O1vi0.85 (1)1.99 (2)2.811 (5)163 (5)
O14—H14D···O2vi0.85 (1)2.59 (4)3.228 (5)133 (5)
O15—H15A···O8vii0.85 (1)2.21 (2)3.028 (5)162 (6)
O15—H15A···O7vii0.85 (1)2.43 (4)3.114 (5)138 (5)
O15—H15B···O3vii0.85 (1)1.99 (2)2.826 (5)169 (6)
O16—H16A···O15viii0.85 (1)1.82 (1)2.666 (6)179 (6)
O16—H16B···O6ix0.84 (1)2.28 (3)3.061 (17)156 (4)
O16—H16B···O5ix0.84 (1)2.45 (4)3.041 (13)128 (4)
O16—H16B···O6ix0.84 (1)2.39 (2)3.209 (15)164 (4)
O16—H16B···O5ix0.84 (1)2.53 (4)3.175 (19)134 (4)
C17—H17···O10x0.932.463.379 (5)169
C23—H23···O14xi0.932.473.352 (6)158
Symmetry codes: (i) x, y+1, z+2; (ii) x, y, z+1; (iii) x+1, y+2, z+1; (iv) x1, y, z+1; (v) x, y+1, z+1; (vi) x, y, z1; (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) x1, y, z.
 

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