In the title compound, [Cu(C
14H
9O
3)
2(C
5H
5NO)
2]·2CH
3OH, the Cu atom (site symmetry
) is chelated by two 9-hydroxyfluorene-9-carboxylate ligands. Two N-bound 3-hydroxypyridine molecules, which are disordered over two adjacent positions, complete the coordination of the distorted CuO
4N
2 octahedron. Various O—H
O hydrogen bonds link the metal-bearing unit and the methanol solvent molecules into a linear chain structure.
Supporting information
CCDC reference: 274774
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.033
- wR factor = 0.101
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.684 0.889
Tmin(prime) and Tmax expected: 0.771 0.886
RR(prime) = 0.884
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 ............. 0.88
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.71 Ratio
PLAT301_ALERT_3_C Main Residue Disorder ......................... 20.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: difference Fourier, with Cu at 1/2, 1/2, 1/2; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis(9-hydroxyfluorene-9-carboxylato-
κ2O,
O')bis(3-hydroxypyridine-
κN)copper(II) methanol disolvate
top
Crystal data top
[Cu(C14H9O3)2(C5H5NO)2]·2CH4O | F(000) = 798 |
Mr = 768.25 | Dx = 1.422 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 14783 reflections |
a = 14.877 (3) Å | θ = 3.0–27.5° |
b = 7.872 (2) Å | µ = 0.67 mm−1 |
c = 16.527 (3) Å | T = 295 K |
β = 112.04 (3)° | Block, blue |
V = 1794.2 (6) Å3 | 0.38 × 0.26 × 0.18 mm |
Z = 2 | |
Data collection top
Rigaku RAXIS-RAPID IP diffractometer | 4101 independent reflections |
Radiation source: fine-focus sealed tube | 3706 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −19→19 |
Tmin = 0.684, Tmax = 0.889 | k = −10→10 |
16937 measured reflections | l = −21→21 |
Refinement top
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0675P)2 + 0.3683P] where P = (Fo2 + 2Fc2)/3 |
4101 reflections | (Δ/σ)max = 0.001 |
298 parameters | Δρmax = 0.39 e Å−3 |
93 restraints | Δρmin = −0.42 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.0306 (1) | |
O1 | 0.5232 (1) | 0.7003 (1) | 0.4387 (1) | 0.0356 (2) | |
O2 | 0.6256 (1) | 0.8724 (1) | 0.4115 (1) | 0.0454 (3) | |
O3 | 0.6524 (1) | 0.4568 (1) | 0.4995 (1) | 0.0331 (2) | |
O5 | 0.7311 (1) | 0.1504 (2) | 0.5008 (1) | 0.0563 (3) | |
N1 | 0.4370 (1) | 0.3747 (2) | 0.3853 (1) | 0.0358 (3) | |
C1 | 0.6049 (1) | 0.7332 (2) | 0.4354 (1) | 0.0305 (3) | |
C2 | 0.6820 (1) | 0.5906 (2) | 0.4573 (1) | 0.0289 (3) | |
C3 | 0.6948 (1) | 0.5356 (2) | 0.3738 (1) | 0.0320 (3) | |
C4 | 0.6266 (1) | 0.4689 (2) | 0.2986 (1) | 0.0423 (4) | |
C5 | 0.6560 (2) | 0.4254 (2) | 0.2307 (1) | 0.0520 (4) | |
C6 | 0.7512 (2) | 0.4480 (3) | 0.2382 (1) | 0.0546 (5) | |
C7 | 0.8188 (2) | 0.5162 (2) | 0.3124 (1) | 0.0469 (4) | |
C8 | 0.7904 (1) | 0.5623 (2) | 0.3807 (1) | 0.0356 (3) | |
C9 | 0.8447 (1) | 0.6384 (2) | 0.4659 (1) | 0.0359 (3) | |
C10 | 0.9411 (1) | 0.6894 (2) | 0.5039 (1) | 0.0485 (4) | |
C11 | 0.9744 (1) | 0.7551 (3) | 0.5874 (1) | 0.0547 (5) | |
C12 | 0.9138 (1) | 0.7688 (2) | 0.6334 (1) | 0.0518 (4) | |
C13 | 0.8168 (1) | 0.7196 (2) | 0.5955 (1) | 0.0420 (4) | |
C14 | 0.7832 (1) | 0.6558 (2) | 0.5120 (1) | 0.0320 (3) | |
O4 | 0.4598 (5) | −0.0181 (5) | 0.2856 (2) | 0.090 (2) | 0.66 (1) |
C15 | 0.4668 (3) | 0.2205 (5) | 0.3747 (4) | 0.037 (1) | 0.66 (1) |
C16 | 0.4288 (4) | 0.1357 (5) | 0.2957 (3) | 0.048 (1) | 0.66 (1) |
C17 | 0.3585 (5) | 0.217 (1) | 0.2257 (4) | 0.053 (2) | 0.66 (1) |
C18 | 0.3283 (7) | 0.376 (1) | 0.2379 (7) | 0.050 (2) | 0.66 (1) |
C19 | 0.3689 (4) | 0.454 (1) | 0.3180 (5) | 0.040 (1) | 0.66 (1) |
C20 | 0.8202 (2) | 0.1491 (3) | 0.4902 (2) | 0.0653 (6) | |
O4' | 0.4092 (6) | −0.0694 (9) | 0.3085 (5) | 0.065 (2) | 0.34 (1) |
C15' | 0.4467 (5) | 0.202 (1) | 0.3852 (6) | 0.032 (1) | 0.34 (1) |
C16' | 0.4024 (5) | 0.100 (1) | 0.3116 (5) | 0.041 (2) | 0.34 (1) |
C17' | 0.3445 (8) | 0.182 (2) | 0.2351 (8) | 0.043 (2) | 0.34 (1) |
C18' | 0.334 (1) | 0.356 (2) | 0.235 (1) | 0.049 (4) | 0.34 (1) |
C19' | 0.3813 (7) | 0.449 (2) | 0.3101 (8) | 0.038 (3) | 0.34 (1) |
H3o | 0.6530 | 0.3670 | 0.4746 | 0.040* | |
H5o | 0.6957 | 0.0767 | 0.4699 | 0.068* | |
H4 | 0.5627 | 0.4535 | 0.2935 | 0.051* | |
H5 | 0.6111 | 0.3803 | 0.1795 | 0.062* | |
H6 | 0.7694 | 0.4165 | 0.1923 | 0.066* | |
H7 | 0.8825 | 0.5315 | 0.3171 | 0.056* | |
H10 | 0.9823 | 0.6794 | 0.4736 | 0.058* | |
H11 | 1.0385 | 0.7907 | 0.6132 | 0.066* | |
H12 | 0.9379 | 0.8112 | 0.6901 | 0.062* | |
H13 | 0.7759 | 0.7297 | 0.6261 | 0.050* | |
H4o | 0.5023 | −0.0646 | 0.3267 | 0.109* | 0.66 (1) |
H15 | 0.5146 | 0.1679 | 0.4216 | 0.045* | 0.66 (1) |
H17 | 0.3323 | 0.1637 | 0.1716 | 0.064* | 0.66 (1) |
H18 | 0.2804 | 0.4312 | 0.1920 | 0.060* | 0.66 (1) |
H19 | 0.3491 | 0.5633 | 0.3256 | 0.048* | 0.66 (1) |
H20a | 0.8613 | 0.2365 | 0.5257 | 0.098* | |
H20b | 0.8097 | 0.1693 | 0.4301 | 0.098* | |
H20c | 0.8508 | 0.0406 | 0.5077 | 0.098* | |
H4'o | 0.4426 | −0.1222 | 0.3522 | 0.078* | 0.34 (1) |
H15' | 0.4848 | 0.1491 | 0.4371 | 0.038* | 0.34 (1) |
H17' | 0.3129 | 0.1195 | 0.1846 | 0.051* | 0.34 (1) |
H18' | 0.2960 | 0.4118 | 0.1837 | 0.059* | 0.34 (1) |
H19' | 0.3740 | 0.5663 | 0.3086 | 0.046* | 0.34 (1) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0291 (2) | 0.0303 (2) | 0.0365 (2) | −0.0027 (1) | 0.0169 (1) | −0.0035 (1) |
O1 | 0.031 (1) | 0.033 (1) | 0.046 (1) | 0.004 (1) | 0.019 (1) | 0.003 (1) |
O2 | 0.047 (1) | 0.029 (1) | 0.065 (1) | 0.003 (1) | 0.027 (1) | 0.010 (1) |
O3 | 0.036 (1) | 0.025 (1) | 0.046 (1) | 0.001 (1) | 0.023 (1) | 0.003 (1) |
O5 | 0.054 (1) | 0.033 (1) | 0.090 (1) | −0.001 (1) | 0.036 (1) | −0.007 (1) |
N1 | 0.031 (1) | 0.039 (1) | 0.039 (1) | −0.002 (1) | 0.015 (1) | −0.004 (1) |
C1 | 0.033 (1) | 0.027 (1) | 0.034 (1) | 0.002 (1) | 0.014 (1) | −0.001 (1) |
C2 | 0.029 (1) | 0.026 (1) | 0.036 (1) | 0.000 (1) | 0.017 (1) | 0.001 (1) |
C3 | 0.036 (1) | 0.026 (1) | 0.039 (1) | 0.004 (1) | 0.020 (1) | 0.002 (1) |
C4 | 0.045 (1) | 0.039 (1) | 0.043 (1) | 0.001 (1) | 0.017 (1) | −0.004 (1) |
C5 | 0.071 (1) | 0.045 (1) | 0.043 (1) | 0.004 (1) | 0.024 (1) | −0.006 (1) |
C6 | 0.083 (1) | 0.043 (1) | 0.054 (1) | 0.009 (1) | 0.045 (1) | −0.002 (1) |
C7 | 0.058 (1) | 0.037 (1) | 0.064 (1) | 0.006 (1) | 0.043 (1) | 0.004 (1) |
C8 | 0.040 (1) | 0.027 (1) | 0.048 (1) | 0.005 (1) | 0.026 (1) | 0.005 (1) |
C9 | 0.032 (1) | 0.029 (1) | 0.052 (1) | 0.003 (1) | 0.021 (1) | 0.005 (1) |
C10 | 0.032 (1) | 0.041 (1) | 0.077 (1) | 0.000 (1) | 0.025 (1) | 0.002 (1) |
C11 | 0.031 (1) | 0.048 (1) | 0.076 (1) | −0.003 (1) | 0.008 (1) | 0.003 (1) |
C12 | 0.047 (1) | 0.046 (1) | 0.050 (1) | −0.006 (1) | 0.004 (1) | 0.000 (1) |
C13 | 0.042 (1) | 0.041 (1) | 0.043 (1) | −0.004 (1) | 0.016 (1) | 0.001 (1) |
C14 | 0.030 (1) | 0.028 (1) | 0.040 (1) | 0.000 (1) | 0.015 (1) | 0.004 (1) |
O4 | 0.128 (4) | 0.053 (2) | 0.055 (2) | 0.032 (2) | −0.007 (2) | −0.020 (1) |
C15 | 0.033 (2) | 0.042 (2) | 0.037 (2) | 0.005 (1) | 0.013 (1) | −0.003 (1) |
C16 | 0.064 (2) | 0.034 (2) | 0.039 (2) | 0.003 (2) | 0.009 (1) | −0.004 (1) |
C17 | 0.062 (3) | 0.048 (3) | 0.035 (2) | −0.005 (2) | 0.001 (2) | −0.001 (2) |
C18 | 0.048 (3) | 0.047 (3) | 0.049 (4) | 0.008 (2) | 0.010 (2) | 0.007 (2) |
C19 | 0.039 (2) | 0.042 (2) | 0.041 (2) | 0.005 (2) | 0.018 (2) | 0.004 (2) |
C20 | 0.060 (1) | 0.048 (1) | 0.101 (2) | 0.0057 (9) | 0.044 (1) | 0.005 (1) |
O4' | 0.075 (4) | 0.044 (3) | 0.052 (3) | 0.020 (3) | −0.005 (2) | −0.014 (2) |
C15' | 0.020 (3) | 0.048 (3) | 0.030 (3) | 0.005 (2) | 0.012 (2) | −0.008 (2) |
C16' | 0.042 (3) | 0.041 (3) | 0.037 (3) | 0.006 (2) | 0.011 (2) | −0.002 (2) |
C17' | 0.044 (3) | 0.035 (5) | 0.043 (4) | −0.004 (3) | 0.010 (3) | −0.009 (3) |
C18' | 0.051 (7) | 0.053 (7) | 0.030 (5) | 0.001 (4) | 0.000 (4) | −0.002 (4) |
C19' | 0.037 (4) | 0.036 (4) | 0.048 (5) | −0.002 (3) | 0.025 (3) | −0.002 (3) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.973 (1) | C16—C17 | 1.389 (6) |
Cu1—O1i | 1.973 (1) | C17—C18 | 1.373 (6) |
Cu1—N1 | 2.028 (1) | C18—C19 | 1.377 (6) |
Cu1—N1i | 2.028 (1) | O4'—C16' | 1.340 (6) |
Cu1—O3 | 2.295 (1) | C15'—C16' | 1.399 (8) |
Cu1—O3i | 2.295 (1) | C16'—C17' | 1.392 (9) |
O1—C1 | 1.265 (2) | C17'—C18' | 1.382 (9) |
O2—C1 | 1.242 (2) | C18'—C19' | 1.386 (9) |
O3—C2 | 1.422 (2) | O3—H3o | 0.82 |
O5—C20 | 1.402 (2) | O5—H5o | 0.82 |
N1—C15 | 1.326 (4) | C4—H4 | 0.93 |
N1—C19' | 1.341 (9) | C5—H5 | 0.93 |
N1—C19 | 1.346 (5) | C6—H6 | 0.93 |
N1—C15' | 1.368 (8) | C7—H7 | 0.93 |
C1—C2 | 1.548 (2) | C10—H10 | 0.93 |
C2—C14 | 1.525 (2) | C11—H11 | 0.93 |
C2—C3 | 1.525 (2) | C12—H12 | 0.93 |
C3—C4 | 1.379 (2) | C13—H13 | 0.93 |
C3—C8 | 1.398 (2) | O4—H4o | 0.82 |
C4—C5 | 1.392 (2) | C15—H15 | 0.93 |
C5—C6 | 1.386 (3) | C17—H17 | 0.93 |
C6—C7 | 1.371 (3) | C18—H18 | 0.93 |
C7—C8 | 1.395 (2) | C19—H19 | 0.93 |
C8—C9 | 1.462 (2) | C20—H20a | 0.96 |
C9—C10 | 1.391 (2) | C20—H20b | 0.96 |
C9—C14 | 1.400 (2) | C20—H20c | 0.96 |
C10—C11 | 1.380 (3) | O4'—H4'o | 0.82 |
C11—C12 | 1.385 (3) | C15'—H15' | 0.93 |
C12—C13 | 1.394 (2) | C17'—H17' | 0.93 |
C13—C14 | 1.375 (2) | C18'—H18' | 0.93 |
O4—C16 | 1.328 (4) | C19'—H19' | 0.93 |
C15—C16 | 1.384 (5) | | |
| | | |
O1—Cu1—O1i | 180 | C15—C16—C17 | 118.5 (5) |
O3—Cu1—O3i | 180 | C18—C17—C16 | 118.9 (8) |
N1i—Cu1—N1 | 180 | C19—C18—C17 | 120 (1) |
O1i—Cu1—O3i | 75.74 (4) | N1—C19—C18 | 121 (1) |
O1i—Cu1—O3 | 104.26 (4) | N1—C15'—C16' | 123.8 (8) |
O1i—Cu1—N1i | 90.99 (5) | O4'—C16'—C17' | 117.1 (8) |
O1i—Cu1—N1 | 89.01 (5) | O4'—C16'—C15' | 125.9 (6) |
O3i—Cu1—N1i | 92.00 (5) | C17'—C16'—C15' | 117.0 (9) |
O3i—Cu1—N1 | 88.00 (5) | C18'—C17'—C16' | 120 (1) |
O1—Cu1—O3 | 75.74 (4) | C17'—C18'—C19' | 120 (2) |
O1—Cu1—O3i | 104.26 (4) | C2—O3—H3o | 109.1 |
O1—Cu1—N1 | 90.99 (5) | Cu1—O3—H3o | 109.1 |
O1—Cu1—N1i | 89.01 (5) | C20—O5—H5o | 109.5 |
O3—Cu1—N1 | 92.00 (5) | C3—C4—H4 | 120.9 |
O3—Cu1—N1i | 88.00 (5) | C5—C4—H4 | 120.9 |
C1—O1—Cu1 | 122.82 (9) | C6—C5—H5 | 119.5 |
C2—O3—Cu1 | 112.37 (8) | C4—C5—H5 | 119.5 |
C15—N1—C19 | 120.1 (6) | C7—C6—H6 | 119.6 |
C19'—N1—C15' | 117 (1) | C5—C6—H6 | 119.6 |
C15—N1—Cu1 | 120.6 (3) | C6—C7—H7 | 120.6 |
C19'—N1—Cu1 | 124.2 (9) | C8—C7—H7 | 120.6 |
C19—N1—Cu1 | 119.1 (5) | C11—C10—H10 | 120.6 |
C15'—N1—Cu1 | 118.2 (4) | C9—C10—H10 | 120.6 |
O2—C1—O1 | 123.5 (1) | C10—C11—H11 | 119.5 |
O2—C1—C2 | 117.7 (1) | C12—C11—H11 | 119.5 |
O1—C1—C2 | 118.8 (1) | C11—C12—H12 | 119.7 |
O3—C2—C14 | 112.2 (1) | C13—C12—H12 | 119.7 |
O3—C2—C3 | 113.6 (1) | C14—C13—H13 | 120.7 |
C14—C2—C3 | 101.6 (1) | C12—C13—H13 | 120.7 |
O3—C2—C1 | 108.2 (1) | C16—O4—H4o | 120.0 |
C14—C2—C1 | 112.0 (1) | N1—C15—H15 | 119.1 |
C3—C2—C1 | 109.1 (1) | C16—C15—H15 | 119.1 |
C4—C3—C8 | 120.9 (2) | C18—C17—H17 | 120.5 |
C4—C3—C2 | 128.6 (1) | C16—C17—H17 | 120.5 |
C8—C3—C2 | 110.6 (1) | C19—C18—H18 | 120.0 |
C3—C4—C5 | 118.2 (2) | C17—C18—H18 | 120.0 |
C6—C5—C4 | 121.1 (2) | N1—C19—H19 | 119.7 |
C7—C6—C5 | 120.8 (2) | C18—C19—H19 | 119.7 |
C6—C7—C8 | 118.9 (2) | O5—C20—H20a | 109.5 |
C7—C8—C3 | 120.1 (2) | O5—C20—H20b | 109.5 |
C7—C8—C9 | 131.3 (2) | H20a—C20—H20b | 109.5 |
C3—C8—C9 | 108.6 (1) | O5—C20—H20C | 109.5 |
C10—C9—C14 | 120.0 (2) | H20a—C20—H20c | 109.5 |
C10—C9—C8 | 131.1 (2) | H20b—C20—H20c | 109.5 |
C14—C9—C8 | 109.0 (1) | C16'—O4'—H4'o | 120.0 |
C11—C10—C9 | 118.9 (2) | N1—C15'—H15' | 118.1 |
C10—C11—C12 | 121.0 (2) | C16'—C15'—H15' | 118.1 |
C11—C12—C13 | 120.6 (2) | C18'—C17'—H17' | 120.2 |
C14—C13—C12 | 118.6 (2) | C16'—C17'—H17' | 120.2 |
C13—C14—C9 | 121.0 (1) | C17'—C18'—H18' | 120.0 |
C13—C14—C2 | 128.7 (1) | C19'—C18'—H18' | 120.0 |
C9—C14—C2 | 110.3 (1) | N1—C19'—C18' | 122.2 (17) |
N1—C15—C16 | 121.9 (4) | N1—C19'—H19' | 118.9 |
O4—C16—C15 | 121.3 (4) | C18'—C19'—H19' | 118.9 |
O4—C16—C17 | 120.2 (5) | | |
| | | |
N1i—Cu1—O1—C1 | 78.7 (1) | C2—C3—C8—C9 | −1.3 (2) |
N1—Cu1—O1—C1 | −101.3 (1) | C7—C8—C9—C10 | 0.9 (3) |
O3i—Cu1—O1—C1 | 170.5 (1) | C3—C8—C9—C10 | −179.7 (2) |
O3—Cu1—O1—C1 | −9.5 (1) | C7—C8—C9—C14 | −178.5 (2) |
O1—Cu1—O3—C2 | −0.0 (1) | C3—C8—C9—C14 | 1.0 (2) |
O1i—Cu1—O3—C2 | 180.0 (1) | C14—C9—C10—C11 | 0.7 (2) |
N1i—Cu1—O3—C2 | −89.5 (1) | C8—C9—C10—C11 | −178.6 (2) |
N1—Cu1—O3—C2 | 90.5 (1) | C9—C10—C11—C12 | 0.7 (3) |
O1—Cu1—N1—C15 | 127.4 (2) | C10—C11—C12—C13 | −1.4 (3) |
O1i—Cu1—N1—C15 | −52.6 (2) | C11—C12—C13—C14 | 0.6 (3) |
O3i—Cu1—N1—C15 | −128.4 (2) | C12—C13—C14—C9 | 0.7 (2) |
O3—Cu1—N1—C15 | 51.6 (2) | C12—C13—C14—C2 | 178.7 (2) |
O1—Cu1—N1—C19' | −36.2 (5) | C10—C9—C14—C13 | −1.4 (2) |
O1i—Cu1—N1—C19' | 143.8 (5) | C8—C9—C14—C13 | 178.0 (1) |
O3i—Cu1—N1—C19' | 68.0 (5) | C10—C9—C14—C2 | −179.7 (1) |
O3—Cu1—N1—C19' | −112.0 (5) | C8—C9—C14—C2 | −0.3 (2) |
O1—Cu1—N1—C19 | −48.1 (3) | O3—C2—C14—C13 | −56.9 (2) |
O1i—Cu1—N1—C19 | 131.9 (3) | C3—C2—C14—C13 | −178.6 (2) |
O3i—Cu1—N1—C19 | 56.1 (3) | C1—C2—C14—C13 | 65.0 (2) |
O3—Cu1—N1—C19 | −123.9 (3) | O3—C2—C14—C9 | 121.2 (1) |
O1—Cu1—N1—C15' | 148.0 (3) | C3—C2—C14—C9 | −0.5 (2) |
O1i—Cu1—N1—C15' | −32.0 (3) | C1—C2—C14—C9 | −116.9 (1) |
O3i—Cu1—N1—C15' | −107.7 (3) | C19'—N1—C15—C16 | −11.2 (6) |
O3—Cu1—N1—C15' | 72.3 (3) | C19—N1—C15—C16 | −1.0 (3) |
Cu1—O1—C1—O2 | −166.3 (1) | C15'—N1—C15—C16 | 96 (2) |
Cu1—O1—C1—C2 | 17.1 (2) | Cu1—N1—C15—C16 | −176.5 (2) |
Cu1—O3—C2—C14 | 130.9 (1) | N1—C15—C16—O4 | 179.5 (2) |
Cu1—O3—C2—C3 | −114.6 (1) | N1—C15—C16—C17 | 0.9 (4) |
Cu1—O3—C2—C1 | 6.8 (1) | O4—C16—C17—C18 | −179.6 (4) |
O2—C1—C2—O3 | 168.3 (1) | C15—C16—C17—C18 | −1.0 (6) |
O1—C1—C2—O3 | −14.9 (2) | C16—C17—C18—C19 | 1.2 (7) |
O2—C1—C2—C14 | 44.1 (2) | C15—N1—C19—C18 | 1.1 (5) |
O1—C1—C2—C14 | −139.1 (1) | C19'—N1—C19—C18 | 57 (6) |
O2—C1—C2—C3 | −67.6 (2) | C15'—N1—C19—C18 | −19.9 (5) |
O1—C1—C2—C3 | 109.2 (1) | Cu1—N1—C19—C18 | 176.7 (3) |
O3—C2—C3—C4 | 60.9 (2) | C17—C18—C19—N1 | −1.2 (7) |
C14—C2—C3—C4 | −178.5 (2) | C15—N1—C15'—C16' | −81 (2) |
C1—C2—C3—C4 | −60.0 (2) | C19'—N1—C15'—C16' | 0.4 (4) |
O3—C2—C3—C8 | −119.6 (1) | C19—N1—C15'—C16' | 12.8 (6) |
C14—C2—C3—C8 | 1.1 (2) | Cu1—N1—C15'—C16' | 176.4 (3) |
C1—C2—C3—C8 | 119.5 (1) | N1—C15'—C16'—O4' | −179.5 (3) |
C8—C3—C4—C5 | 1.5 (2) | N1—C15'—C16'—C17' | −0.9 (5) |
C2—C3—C4—C5 | −179.0 (2) | O4'—C16'—C17'—C18' | 179.5 (5) |
C3—C4—C5—C6 | 0.1 (3) | C15'—C16'—C17'—C18' | 0.8 (7) |
C4—C5—C6—C7 | −0.9 (3) | C16'—C17'—C18'—C19' | −0.2 (8) |
C5—C6—C7—C8 | 0.2 (3) | C15—N1—C19'—C18' | 19.9 (6) |
C6—C7—C8—C3 | 1.3 (2) | C19—N1—C19'—C18' | −109 (6) |
C6—C7—C8—C9 | −179.2 (2) | C15'—N1—C19'—C18' | 0.3 (6) |
C4—C3—C8—C7 | −2.2 (2) | Cu1—N1—C19'—C18' | −175.5 (5) |
C2—C3—C8—C7 | 178.2 (1) | C17'—C18'—C19'—N1 | −0.4 (9) |
C4—C3—C8—C9 | 178.3 (1) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3o···O5 | 0.82 | 2.02 | 2.677 (2) | 137 |
O5—H5o···O2ii | 0.82 | 1.96 | 2.773 (2) | 170 |
O4—H4o···O2ii | 0.82 | 1.91 | 2.702 (4) | 162 |
O4′—H4′o···O1ii | 0.82 | 2.04 | 2.838 (6) | 166 |
Symmetry code: (ii) x, y−1, z. |