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metal-organic compounds
The 3-carboxyphenoxyacetate ligand in the title compound, [Cu(C9H6O5)(C5H5N)3]·3H2O, links adjacent tripyridinecopper(II) groups into a helical chain, which runs along the c axis of the hexagonal unit cell. The covalently bonded O atoms occupy trans sites in the basal plane of the square-pyramidal coordination of the Cu atom. The uncoordinated water molecules connect the chains into a three-dimensional network.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038316/xu6084sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038316/xu6084Isup2.hkl |
CCDC reference: 294037
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.009 Å
- R factor = 0.073
- wR factor = 0.146
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O3W - H3W2 ... ?
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.591 0.849 Tmin(prime) and Tmax expected: 0.714 0.844 RR(prime) = 0.823 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 5518 Count of symmetry unique reflns 3052 Completeness (_total/calc) 180.80% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2466 Fraction of Friedel pairs measured 0.808 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Cu(C9H6O5)(C5H5N)3]·3H2O | Dx = 1.407 Mg m−3 |
Mr = 549.04 | Mo Kα radiation, λ = 0.71073 Å |
Hexagonal, P65 | Cell parameters from 26385 reflections |
Hall symbol: P 65 | θ = 3.3–27.5° |
a = 14.408 (2) Å | µ = 0.89 mm−1 |
c = 21.630 (4) Å | T = 295 K |
V = 3888.6 (8) Å3 | Block, blue |
Z = 6 | 0.37 × 0.25 × 0.19 mm |
F(000) = 1710 |
Data collection top
Rigaku R-AXIS RAPID IP diffractometer | 5518 independent reflections |
Radiation source: fine-focus sealed tube | 4814 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −18→18 |
Tmin = 0.591, Tmax = 0.849 | k = −18→18 |
27636 measured reflections | l = −28→26 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.073 | H-atom parameters constrained |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0697P)2 + 0.7075P] where P = (Fo2 + 2Fc2)/3 |
S = 1.24 | (Δ/σ)max = 0.03 |
5518 reflections | Δρmax = 0.48 e Å−3 |
325 parameters | Δρmin = −0.39 e Å−3 |
19 restraints | Absolute structure: Flack (1983), 2571 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.49488 (4) | 0.00056 (4) | 0.50004 (5) | 0.0515 (2) | |
O1 | 0.3917 (3) | −0.0023 (3) | 0.5596 (2) | 0.061 (1) | |
O2 | 0.5016 (2) | 0.0021 (3) | 0.6330 (2) | 0.066 (1) | |
O3 | 0.3345 (2) | 0.0087 (3) | 0.8301 (2) | 0.074 (1) | |
O4 | 0.2685 (3) | −0.0082 (3) | 0.9884 (2) | 0.068 (1) | |
O5 | 0.4064 (2) | −0.0022 (3) | 0.9377 (1) | 0.057 (1) | |
O1W | 0.6947 (5) | 0.0025 (6) | 0.6174 (3) | 0.140 (2) | |
O2W | 0.8857 (6) | 0.0568 (5) | 0.6762 (3) | 0.153 (2) | |
O3w | 0.9723 (9) | −0.0003 (8) | 0.7682 (7) | 0.224 (5) | |
N1 | 0.4281 (3) | −0.1623 (3) | 0.5108 (2) | 0.056 (1) | |
N2 | 0.3847 (3) | −0.0051 (3) | 0.4194 (2) | 0.061 (1) | |
N3 | 0.5853 (3) | 0.1641 (3) | 0.5095 (2) | 0.053 (1) | |
C1 | 0.4879 (4) | −0.2089 (4) | 0.5137 (2) | 0.068 (1) | |
C2 | 0.4450 (5) | −0.3187 (5) | 0.5173 (3) | 0.080 (2) | |
C3 | 0.3375 (6) | −0.3827 (5) | 0.5187 (3) | 0.088 (2) | |
C4 | 0.2742 (5) | −0.3359 (5) | 0.5161 (3) | 0.086 (2) | |
C5 | 0.3231 (4) | −0.2256 (5) | 0.5123 (2) | 0.072 (1) | |
C6 | 0.2907 (5) | −0.0092 (6) | 0.4291 (3) | 0.088 (2) | |
C7 | 0.2264 (6) | −0.0115 (7) | 0.3827 (5) | 0.114 (3) | |
C8 | 0.2566 (8) | −0.0110 (7) | 0.3230 (4) | 0.119 (3) | |
C9 | 0.3535 (6) | −0.0069 (5) | 0.3111 (3) | 0.092 (2) | |
C10 | 0.4121 (5) | −0.0044 (4) | 0.3609 (2) | 0.070 (1) | |
C11 | 0.5377 (4) | 0.2232 (4) | 0.5104 (2) | 0.064 (1) | |
C12 | 0.5962 (4) | 0.3341 (4) | 0.5150 (3) | 0.071 (1) | |
C13 | 0.7045 (5) | 0.3843 (4) | 0.5193 (2) | 0.069 (1) | |
C14 | 0.7541 (4) | 0.3228 (5) | 0.5190 (2) | 0.070 (1) | |
C15 | 0.6908 (4) | 0.2136 (4) | 0.5139 (2) | 0.059 (1) | |
C16 | 0.4187 (4) | −0.0019 (3) | 0.6157 (2) | 0.049 (1) | |
C17 | 0.3398 (3) | −0.0076 (3) | 0.6637 (2) | 0.045 (1) | |
C18 | 0.2378 (3) | −0.0280 (3) | 0.6474 (2) | 0.052 (1) | |
C19 | 0.1669 (4) | −0.0353 (4) | 0.6931 (2) | 0.054 (1) | |
C20 | 0.1953 (3) | −0.0227 (3) | 0.7550 (2) | 0.052 (1) | |
C21 | 0.2973 (3) | −0.0039 (3) | 0.7704 (2) | 0.050 (1) | |
C22 | 0.3678 (3) | 0.0041 (4) | 0.7254 (2) | 0.050 (1) | |
C23 | 0.2649 (4) | −0.0051 (4) | 0.8796 (2) | 0.059 (1) | |
C24 | 0.3179 (4) | −0.0046 (4) | 0.9400 (2) | 0.053 (1) | |
H1W1 | 0.6281 | −0.0374 | 0.6248 | 0.168* | |
H1W2 | 0.7083 | −0.0099 | 0.5809 | 0.168* | |
H2W1 | 0.9357 | 0.0979 | 0.6514 | 0.183* | |
H2w2 | 0.8383 | 0.0030 | 0.6555 | 0.183* | |
H3w1 | 0.9504 | 0.0179 | 0.7357 | 0.269* | |
H3w2 | 0.9992 | −0.0406 | 0.7548 | 0.269* | |
H1 | 0.5621 | −0.1654 | 0.5134 | 0.081* | |
H2 | 0.4897 | −0.3481 | 0.5187 | 0.096* | |
H3 | 0.3067 | −0.4567 | 0.5213 | 0.106* | |
H4 | 0.1999 | −0.3779 | 0.5170 | 0.104* | |
H5 | 0.2800 | −0.1945 | 0.5106 | 0.087* | |
H6 | 0.2686 | −0.0106 | 0.4697 | 0.106* | |
H7 | 0.1623 | −0.0133 | 0.3915 | 0.136* | |
H8 | 0.2131 | −0.0133 | 0.2906 | 0.142* | |
H9 | 0.3770 | −0.0059 | 0.2709 | 0.110* | |
H10 | 0.4768 | −0.0020 | 0.3533 | 0.083* | |
H11 | 0.4634 | 0.1892 | 0.5079 | 0.077* | |
H12 | 0.5613 | 0.3737 | 0.5152 | 0.085* | |
H13 | 0.7449 | 0.4585 | 0.5224 | 0.083* | |
H14 | 0.8282 | 0.3547 | 0.5221 | 0.084* | |
H15 | 0.7239 | 0.1723 | 0.5136 | 0.071* | |
H18 | 0.2173 | −0.0366 | 0.6061 | 0.062* | |
H19 | 0.0989 | −0.0490 | 0.6819 | 0.065* | |
H20 | 0.1478 | −0.0266 | 0.7853 | 0.063* | |
H22 | 0.4358 | 0.0177 | 0.7367 | 0.059* | |
H23a | 0.1984 | −0.0725 | 0.8749 | 0.071* | |
H23b | 0.2483 | 0.0523 | 0.8794 | 0.071* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0544 (3) | 0.0654 (3) | 0.0384 (2) | 0.0328 (3) | 0.0004 (2) | −0.0032 (2) |
O1 | 0.066 (2) | 0.077 (2) | 0.044 (2) | 0.039 (2) | 0.006 (1) | −0.002 (1) |
O2 | 0.055 (2) | 0.083 (2) | 0.062 (2) | 0.036 (2) | 0.002 (1) | −0.001 (2) |
O3 | 0.047 (2) | 0.129 (3) | 0.037 (2) | 0.037 (2) | −0.002 (1) | −0.002 (2) |
O4 | 0.074 (2) | 0.100 (3) | 0.041 (2) | 0.050 (2) | 0.011 (2) | 0.010 (2) |
O5 | 0.055 (2) | 0.080 (2) | 0.040 (2) | 0.036 (2) | 0.001 (1) | 0.003 (1) |
O1w | 0.130 (4) | 0.255 (7) | 0.086 (3) | 0.135 (5) | −0.023 (3) | −0.036 (4) |
O2w | 0.164 (5) | 0.116 (4) | 0.162 (5) | 0.058 (4) | −0.028 (4) | 0.020 (4) |
O3w | 0.232 (7) | 0.226 (7) | 0.25 (1) | 0.144 (6) | −0.026 (6) | 0.009 (5) |
N1 | 0.058 (2) | 0.067 (2) | 0.047 (2) | 0.033 (2) | 0.001 (2) | −0.005 (2) |
N2 | 0.060 (2) | 0.070 (2) | 0.053 (2) | 0.033 (2) | −0.014 (2) | −0.008 (2) |
N3 | 0.057 (2) | 0.067 (2) | 0.041 (2) | 0.035 (2) | −0.003 (2) | 0.002 (2) |
C1 | 0.066 (3) | 0.071 (3) | 0.065 (3) | 0.034 (3) | 0.007 (2) | 0.005 (2) |
C2 | 0.097 (4) | 0.087 (4) | 0.072 (4) | 0.058 (4) | 0.012 (3) | 0.008 (3) |
C3 | 0.115 (5) | 0.067 (4) | 0.078 (4) | 0.042 (4) | 0.004 (3) | 0.001 (3) |
C4 | 0.076 (4) | 0.070 (4) | 0.094 (5) | 0.022 (3) | 0.003 (3) | −0.002 (3) |
C5 | 0.067 (3) | 0.081 (4) | 0.068 (3) | 0.037 (3) | −0.001 (2) | −0.008 (3) |
C6 | 0.074 (4) | 0.121 (5) | 0.084 (4) | 0.059 (4) | −0.013 (3) | −0.011 (4) |
C7 | 0.082 (4) | 0.141 (7) | 0.137 (7) | 0.071 (5) | −0.039 (5) | −0.018 (5) |
C8 | 0.147 (7) | 0.137 (6) | 0.091 (5) | 0.085 (6) | −0.064 (5) | −0.032 (5) |
C9 | 0.124 (5) | 0.110 (5) | 0.066 (4) | 0.078 (4) | −0.030 (4) | −0.015 (3) |
C10 | 0.088 (4) | 0.064 (3) | 0.062 (3) | 0.042 (3) | −0.017 (3) | −0.006 (2) |
C11 | 0.059 (3) | 0.080 (3) | 0.060 (3) | 0.039 (3) | −0.005 (2) | 0.001 (2) |
C12 | 0.078 (3) | 0.075 (3) | 0.078 (4) | 0.052 (3) | −0.007 (3) | −0.002 (3) |
C13 | 0.073 (3) | 0.061 (3) | 0.069 (3) | 0.032 (3) | −0.002 (2) | −0.003 (2) |
C14 | 0.058 (3) | 0.079 (4) | 0.072 (3) | 0.034 (3) | −0.007 (2) | −0.002 (3) |
C15 | 0.062 (3) | 0.062 (3) | 0.064 (3) | 0.039 (2) | −0.011 (2) | −0.003 (2) |
C16 | 0.052 (3) | 0.048 (2) | 0.045 (2) | 0.024 (2) | 0.006 (2) | 0.002 (2) |
C17 | 0.046 (2) | 0.041 (2) | 0.046 (2) | 0.019 (2) | 0.001 (2) | −0.001 (2) |
C18 | 0.052 (2) | 0.056 (2) | 0.040 (2) | 0.022 (2) | −0.009 (2) | 0.000 (2) |
C19 | 0.043 (2) | 0.071 (3) | 0.049 (2) | 0.029 (2) | −0.006 (2) | 0.001 (2) |
C20 | 0.044 (2) | 0.058 (2) | 0.048 (2) | 0.021 (2) | 0.006 (2) | 0.009 (2) |
C21 | 0.048 (2) | 0.058 (2) | 0.039 (2) | 0.023 (2) | −0.002 (2) | 0.005 (2) |
C22 | 0.037 (2) | 0.063 (3) | 0.048 (2) | 0.025 (2) | −0.003 (2) | 0.003 (2) |
C23 | 0.046 (2) | 0.084 (3) | 0.045 (2) | 0.031 (2) | 0.003 (2) | 0.003 (2) |
C24 | 0.057 (3) | 0.059 (3) | 0.041 (2) | 0.028 (2) | 0.004 (2) | 0.003 (2) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.952 (3) | C18—C19 | 1.386 (6) |
Cu1—O5i | 1.951 (3) | C19—C20 | 1.384 (6) |
Cu1—N1 | 2.057 (4) | C20—C21 | 1.395 (6) |
Cu1—N2 | 2.332 (4) | C21—C22 | 1.369 (6) |
Cu1—N3 | 2.055 (4) | C23—C24 | 1.512 (7) |
O1—C16 | 1.274 (5) | O1w—H1w1 | 0.85 |
O2—C16 | 1.224 (5) | O1w—H1w2 | 0.85 |
O3—C21 | 1.375 (5) | O2w—H2w1 | 0.86 |
O3—C23 | 1.411 (6) | O2w—H2w2 | 0.86 |
O4—C24 | 1.252 (5) | O3w—H3w1 | 0.86 |
O5—C24 | 1.259 (5) | O3w—H3w2 | 0.89 |
N1—C5 | 1.320 (7) | C1—H1 | 0.93 |
N1—C1 | 1.331 (6) | C2—H2 | 0.93 |
N2—C10 | 1.324 (7) | C3—H3 | 0.93 |
N2—C6 | 1.343 (7) | C4—H4 | 0.93 |
N3—C15 | 1.321 (6) | C5—H5 | 0.93 |
N3—C11 | 1.334 (6) | C6—H6 | 0.93 |
C1—C2 | 1.384 (8) | C7—H7 | 0.93 |
C2—C3 | 1.350 (10) | C8—H8 | 0.93 |
C3—C4 | 1.379 (9) | C9—H9 | 0.93 |
C4—C5 | 1.382 (8) | C10—H10 | 0.93 |
C6—C7 | 1.356 (10) | C11—H11 | 0.93 |
C7—C8 | 1.362 (13) | C12—H12 | 0.93 |
C8—C9 | 1.392 (12) | C13—H13 | 0.93 |
C9—C10 | 1.359 (8) | C14—H14 | 0.93 |
C11—C12 | 1.388 (8) | C15—H15 | 0.93 |
C12—C13 | 1.356 (8) | C18—H18 | 0.93 |
C13—C14 | 1.389 (8) | C19—H19 | 0.93 |
C14—C15 | 1.372 (7) | C20—H20 | 0.93 |
C16—C17 | 1.511 (6) | C22—H22 | 0.93 |
C17—C22 | 1.380 (6) | C23—H23a | 0.97 |
C17—C18 | 1.393 (6) | C23—H23b | 0.97 |
O1—Cu1—O5i | 177.5 (2) | C22—C21—C20 | 120.8 (4) |
O1—Cu1—N1 | 89.1 (2) | O3—C21—C20 | 123.6 (4) |
O1—Cu1—N2 | 89.7 (1) | C21—C22—C17 | 121.1 (4) |
O1—Cu1—N3 | 89.9 (1) | C21—C22—H22 | 119.4 |
O5i—Cu1—N1 | 90.8 (1) | C17—C22—H22 | 119.4 |
O5i—Cu1—N2 | 87.9 (2) | O3—C23—C24 | 109.5 (4) |
O5i—Cu1—N3 | 90.8 (1) | O4—C24—O5 | 125.5 (4) |
N1—Cu1—N2 | 97.1 (2) | O4—C24—C23 | 116.5 (4) |
N1—Cu1—N3 | 164.6 (2) | O5—C24—C23 | 117.9 (4) |
N2—Cu1—N3 | 98.3 (1) | N1—C1—H1 | 118.4 |
C16—O1—Cu1 | 113.7 (3) | C2—C1—H1 | 118.4 |
C21—O3—C23 | 119.4 (3) | C3—C2—H2 | 120.5 |
C24—O5—Cu1ii | 134.0 (3) | C1—C2—H2 | 120.5 |
H1w1—O1w—H1w2 | 109.3 | C2—C3—H3 | 120.7 |
H2w1—O2w—H2w2 | 108.2 | C4—C3—H3 | 120.7 |
H3w1—O3w—H3w2 | 106.2 | C5—C4—H4 | 120.6 |
C5—N1—C1 | 117.2 (5) | C3—C4—H4 | 120.6 |
C5—N1—Cu1 | 120.7 (4) | N1—C5—H5 | 118.5 |
C1—N1—Cu1 | 121.9 (3) | C4—C5—H5 | 118.5 |
C10—N2—C6 | 116.2 (5) | N2—C6—H6 | 118.4 |
C10—N2—Cu1 | 121.2 (3) | C7—C6—H6 | 118.4 |
C6—N2—Cu1 | 122.6 (4) | C6—C7—H7 | 120.3 |
C15—N3—C11 | 118.3 (4) | C8—C7—H7 | 120.3 |
C15—N3—Cu1 | 121.7 (3) | C7—C8—H8 | 120.4 |
C11—N3—Cu1 | 120.0 (3) | C9—C8—H8 | 120.4 |
N1—C1—C2 | 123.2 (5) | C10—C9—H9 | 121.6 |
C3—C2—C1 | 119.0 (6) | C8—C9—H9 | 121.6 |
C2—C3—C4 | 118.6 (6) | N2—C10—H10 | 117.3 |
C5—C4—C3 | 118.9 (6) | C9—C10—H10 | 117.3 |
N1—C5—C4 | 123.0 (6) | N3—C11—H11 | 119.2 |
N2—C6—C7 | 123.1 (7) | C12—C11—H11 | 119.2 |
C6—C7—C8 | 119.4 (7) | C13—C12—H12 | 120.2 |
C7—C8—C9 | 119.1 (6) | C11—C12—H12 | 120.2 |
C10—C9—C8 | 116.8 (7) | C12—C13—H13 | 120.6 |
N2—C10—C9 | 125.3 (6) | C14—C13—H13 | 120.6 |
N3—C11—C12 | 121.7 (5) | C15—C14—H14 | 120.9 |
C13—C12—C11 | 119.6 (5) | C13—C14—H14 | 120.9 |
C12—C13—C14 | 118.8 (5) | N3—C15—H15 | 118.3 |
C15—C14—C13 | 118.2 (5) | C14—C15—H15 | 118.3 |
N3—C15—C14 | 123.4 (4) | C19—C18—H18 | 120.2 |
O2—C16—O1 | 125.4 (4) | C17—C18—H18 | 120.2 |
O2—C16—C17 | 118.9 (4) | C20—C19—H19 | 119.3 |
O1—C16—C17 | 115.8 (4) | C18—C19—H19 | 119.3 |
C22—C17—C18 | 118.9 (4) | C19—C20—H20 | 121.0 |
C22—C17—C16 | 119.4 (4) | C21—C20—H20 | 121.0 |
C18—C17—C16 | 121.6 (4) | O3—C23—H23a | 109.8 |
C19—C18—C17 | 119.7 (4) | C24—C23—H23a | 109.8 |
C20—C19—C18 | 121.4 (4) | O3—C23—H23b | 109.8 |
C19—C20—C21 | 118.0 (4) | C24—C23—H23b | 109.8 |
C22—C21—O3 | 115.6 (4) | H23a—C23—H23b | 108.2 |
N3—Cu1—O1—C16 | −82.7 (3) | N2—C6—C7—C8 | 0.9 (12) |
N1—Cu1—O1—C16 | 82.0 (3) | C6—C7—C8—C9 | −0.7 (13) |
N2—Cu1—O1—C16 | 179.0 (3) | C7—C8—C9—C10 | 0.4 (11) |
O5i—Cu1—N1—C5 | −133.8 (4) | C6—N2—C10—C9 | 0.3 (8) |
O1—Cu1—N1—C5 | 43.8 (4) | Cu1—N2—C10—C9 | −179.6 (5) |
N3—Cu1—N1—C5 | 130.1 (5) | C8—C9—C10—N2 | −0.3 (10) |
N2—Cu1—N1—C5 | −45.8 (4) | C15—N3—C11—C12 | 0.9 (7) |
O5i—Cu1—N1—C1 | 43.2 (4) | Cu1—N3—C11—C12 | −178.2 (4) |
O1—Cu1—N1—C1 | −139.3 (4) | N3—C11—C12—C13 | −0.6 (8) |
N3—Cu1—N1—C1 | −52.9 (7) | C11—C12—C13—C14 | 0.0 (8) |
N2—Cu1—N1—C1 | 131.1 (4) | C12—C13—C14—C15 | 0.4 (8) |
O5i—Cu1—N2—C10 | −0.8 (4) | C11—N3—C15—C14 | −0.5 (7) |
O1—Cu1—N2—C10 | 179.5 (4) | Cu1—N3—C15—C14 | 178.6 (4) |
N3—Cu1—N2—C10 | 89.7 (4) | C13—C14—C15—N3 | −0.2 (8) |
N1—Cu1—N2—C10 | −91.4 (4) | Cu1—O1—C16—O2 | 1.4 (5) |
O5i—Cu1—N2—C6 | 179.2 (5) | Cu1—O1—C16—C17 | −178.1 (2) |
O1—Cu1—N2—C6 | −0.4 (4) | O2—C16—C17—C22 | 7.4 (6) |
N3—Cu1—N2—C6 | −90.3 (4) | O1—C16—C17—C22 | −173.0 (4) |
N1—Cu1—N2—C6 | 88.6 (4) | O2—C16—C17—C18 | −170.5 (4) |
O5i—Cu1—N3—C15 | −45.3 (3) | O1—C16—C17—C18 | 9.1 (6) |
O1—Cu1—N3—C15 | 137.1 (3) | C22—C17—C18—C19 | 0.4 (6) |
N1—Cu1—N3—C15 | 50.8 (7) | C16—C17—C18—C19 | 178.4 (4) |
N2—Cu1—N3—C15 | −133.2 (3) | C17—C18—C19—C20 | 0.1 (7) |
O5i—Cu1—N3—C11 | 133.8 (3) | C18—C19—C20—C21 | −1.0 (7) |
O1—Cu1—N3—C11 | −43.8 (4) | C23—O3—C21—C22 | −176.0 (5) |
N1—Cu1—N3—C11 | −130.1 (5) | C23—O3—C21—C20 | 4.6 (7) |
N2—Cu1—N3—C11 | 45.8 (4) | C19—C20—C21—C22 | 1.4 (6) |
C5—N1—C1—C2 | 1.0 (8) | C19—C20—C21—O3 | −179.2 (4) |
Cu1—N1—C1—C2 | −176.0 (4) | O3—C21—C22—C17 | 179.6 (4) |
N1—C1—C2—C3 | −0.9 (9) | C20—C21—C22—C17 | −0.9 (7) |
C1—C2—C3—C4 | 0.4 (9) | C18—C17—C22—C21 | 0.0 (6) |
C2—C3—C4—C5 | 0.0 (10) | C16—C17—C22—C21 | −178.0 (4) |
C1—N1—C5—C4 | −0.6 (8) | C21—O3—C23—C24 | 171.1 (4) |
Cu1—N1—C5—C4 | 176.5 (5) | Cu1ii—O5—C24—O4 | −1.1 (7) |
C3—C4—C5—N1 | 0.1 (9) | Cu1ii—O5—C24—C23 | 180.0 (3) |
C10—N2—C6—C7 | −0.6 (9) | O3—C23—C24—O4 | 174.9 (4) |
Cu1—N2—C6—C7 | 179.3 (6) | O3—C23—C24—O5 | −6.1 (6) |
Symmetry codes: (i) −x+1, −y, z−1/2; (ii) −x+1, −y, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2 | 0.85 | 2.17 | 2.800 (6) | 131 |
O1w—H1w2···O4i | 0.85 | 2.03 | 2.835 (6) | 158 |
O2w—H2w1···O4iii | 0.86 | 2.25 | 2.789 (7) | 121 |
O2w—H2w2···O1w | 0.86 | 2.22 | 2.766 (8) | 121 |
O3w—H3w1···O2w | 0.86 | 1.83 | 2.69 (1) | 170 |
Symmetry codes: (i) −x+1, −y, z−1/2; (iii) −y+1, x−y, z−1/3. |
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