The title compound, [Cu(C
16H
23N
3O
3)
2](ClO
4)
2, is a mononuclear copper(II) complex. The Cu
II atom is four-coordinated by two imine N atoms and two phenolate O atoms from two Schiff base ligands, forming a slightly distorted square-planar coordination. A perchlorate anion is disordered over two orientations. In the crystal structure, the ions are linked through intermolecular N—H
O hydrogen bonds, forming a three-dimensional network.
Supporting information
CCDC reference: 601205
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.014 Å
- Disorder in solvent or counterion
- R factor = 0.092
- wR factor = 0.115
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.105
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.75
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 29.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A .. O8 .. 2.66 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.10 Deg.
O14 -CL2 -O14' 1.555 1.555 1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.03
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 27.49
From the CIF: _reflns_number_total 8145
Count of symmetry unique reflns 4448
Completeness (_total/calc) 183.12%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 3697
Fraction of Friedel pairs measured 0.831
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
19 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Bis{2-[3-(cyclohexylamino)propyliminomethyl]-4-nitrophenolato}copper(II)
diperchlorate
top
Crystal data top
[Cu(C16H23N3O3)2](ClO4)2 | F(000) = 1820 |
Mr = 873.19 | Dx = 1.500 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 2005 reflections |
a = 26.915 (3) Å | θ = 2.4–27.7° |
b = 8.9166 (11) Å | µ = 0.78 mm−1 |
c = 18.505 (2) Å | T = 291 K |
β = 119.443 (2)° | Block, blue |
V = 3867.5 (8) Å3 | 0.25 × 0.16 × 0.03 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 8145 independent reflections |
Radiation source: fine-focus sealed tube | 3489 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.105 |
φ and ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −33→34 |
Tmin = 0.860, Tmax = 0.977 | k = −11→11 |
15254 measured reflections | l = −22→23 |
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)] = 0.092 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0221P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max = 0.004 |
8145 reflections | Δρmax = 0.72 e Å−3 |
509 parameters | Δρmin = −0.39 e Å−3 |
52 restraints | Absolute structure: Flack (1983), 4656 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (3) |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.31321 (5) | 0.05724 (10) | 0.35630 (7) | 0.0447 (3) | |
O1 | 0.3101 (3) | −0.0782 (7) | 0.2756 (4) | 0.0665 (18) | |
O2 | 0.2600 (3) | −0.7368 (7) | 0.1604 (4) | 0.082 (2) | |
O3 | 0.2228 (3) | −0.7320 (6) | 0.2393 (5) | 0.089 (2) | |
O4 | 0.3152 (3) | 0.1930 (6) | 0.4361 (4) | 0.0619 (18) | |
O5 | 0.3798 (3) | 0.8395 (6) | 0.5689 (4) | 0.0685 (18) | |
O6 | 0.4119 (3) | 0.8409 (6) | 0.4820 (4) | 0.081 (2) | |
Cl1 | 0.48775 (11) | 0.4490 (3) | 0.26208 (16) | 0.0665 (7) | |
O7 | 0.4401 (3) | 0.5252 (8) | 0.2540 (6) | 0.126 (3) | |
O8 | 0.5069 (3) | 0.3498 (8) | 0.3322 (4) | 0.110 (3) | |
O9 | 0.4737 (4) | 0.3626 (9) | 0.1937 (5) | 0.136 (3) | |
O10 | 0.5315 (3) | 0.5464 (8) | 0.2771 (4) | 0.097 (2) | |
Cl2 | 0.14132 (12) | 0.5643 (3) | 0.44314 (17) | 0.0820 (8) | |
O11 | 0.1397 (7) | 0.6771 (12) | 0.3868 (8) | 0.167 (7) | 0.559 (6) |
O12 | 0.1908 (5) | 0.4798 (15) | 0.4731 (10) | 0.156 (6) | 0.559 (6) |
O13 | 0.1439 (6) | 0.6484 (15) | 0.5115 (7) | 0.145 (5) | 0.559 (6) |
O14 | 0.0909 (4) | 0.4795 (11) | 0.4039 (10) | 0.076 (4) | 0.559 (6) |
O11' | 0.1604 (8) | 0.7114 (11) | 0.4535 (13) | 0.167 (7) | 0.441 (6) |
O12' | 0.1609 (7) | 0.4868 (19) | 0.3941 (9) | 0.156 (6) | 0.441 (6) |
O13' | 0.1658 (8) | 0.4861 (18) | 0.5205 (7) | 0.145 (5) | 0.441 (6) |
O14' | 0.0816 (4) | 0.5482 (17) | 0.4031 (12) | 0.076 (4) | 0.441 (6) |
N1 | 0.2648 (3) | −0.0796 (7) | 0.3806 (4) | 0.0405 (17) | |
N2 | 0.1283 (3) | 0.0005 (7) | 0.4453 (5) | 0.063 (2) | |
H2A | 0.1471 | −0.0874 | 0.4554 | 0.075* | |
H2B | 0.0968 | −0.0072 | 0.3952 | 0.075* | |
N3 | 0.2455 (3) | −0.6721 (8) | 0.2050 (5) | 0.061 (2) | |
N4 | 0.3656 (3) | 0.1895 (7) | 0.3365 (4) | 0.0411 (17) | |
N5 | 0.4840 (3) | 0.0150 (6) | 0.2441 (5) | 0.048 (2) | |
H5A | 0.5110 | 0.0708 | 0.2852 | 0.058* | |
H5B | 0.4595 | 0.0784 | 0.2049 | 0.058* | |
N6 | 0.3874 (3) | 0.7791 (8) | 0.5161 (5) | 0.059 (2) | |
C1 | 0.2626 (3) | −0.2832 (8) | 0.2930 (5) | 0.040 (2) | |
C2 | 0.2918 (3) | −0.2119 (10) | 0.2578 (5) | 0.043 (2) | |
C3 | 0.3022 (4) | −0.2956 (9) | 0.2024 (5) | 0.065 (3) | |
H3A | 0.3200 | −0.2480 | 0.1765 | 0.078* | |
C4 | 0.2876 (4) | −0.4438 (11) | 0.1842 (6) | 0.067 (3) | |
H4 | 0.2968 | −0.4978 | 0.1494 | 0.081* | |
C5 | 0.2584 (4) | −0.5084 (9) | 0.2205 (6) | 0.046 (2) | |
C6 | 0.2448 (4) | −0.4374 (9) | 0.2733 (5) | 0.043 (2) | |
H6A | 0.2250 | −0.4860 | 0.2958 | 0.051* | |
C7 | 0.2503 (3) | −0.2094 (9) | 0.3520 (5) | 0.044 (2) | |
H7 | 0.2295 | −0.2641 | 0.3707 | 0.052* | |
C8 | 0.2421 (4) | −0.0306 (8) | 0.4368 (5) | 0.058 (2) | |
H8A | 0.2717 | 0.0226 | 0.4841 | 0.069* | |
H8B | 0.2315 | −0.1182 | 0.4573 | 0.069* | |
C9 | 0.1906 (5) | 0.0705 (10) | 0.3910 (7) | 0.080 (3) | |
H9A | 0.2020 | 0.1588 | 0.3721 | 0.096* | |
H9B | 0.1621 | 0.0180 | 0.3423 | 0.096* | |
C10 | 0.1650 (5) | 0.1181 (10) | 0.4402 (7) | 0.097 (4) | |
H10A | 0.1424 | 0.2076 | 0.4157 | 0.116* | |
H10B | 0.1949 | 0.1433 | 0.4957 | 0.116* | |
C11 | 0.1099 (4) | 0.0205 (10) | 0.5085 (6) | 0.067 (3) | |
H11 | 0.0883 | −0.0700 | 0.5054 | 0.081* | |
C12 | 0.1590 (4) | 0.0261 (12) | 0.5959 (6) | 0.085 (3) | |
H12A | 0.1804 | 0.1181 | 0.6040 | 0.102* | |
H12B | 0.1844 | −0.0577 | 0.6051 | 0.102* | |
C13 | 0.1374 (5) | 0.0193 (12) | 0.6579 (6) | 0.104 (4) | |
H13A | 0.1192 | −0.0768 | 0.6534 | 0.125* | |
H13B | 0.1693 | 0.0284 | 0.7138 | 0.125* | |
C14 | 0.0968 (5) | 0.1391 (12) | 0.6424 (7) | 0.104 (4) | |
H14A | 0.1171 | 0.2340 | 0.6561 | 0.125* | |
H14B | 0.0812 | 0.1263 | 0.6794 | 0.125* | |
C15 | 0.0487 (4) | 0.1470 (11) | 0.5554 (6) | 0.082 (3) | |
H15A | 0.0265 | 0.2367 | 0.5489 | 0.099* | |
H15B | 0.0239 | 0.0610 | 0.5447 | 0.099* | |
C16 | 0.0697 (4) | 0.1495 (10) | 0.4919 (6) | 0.081 (3) | |
H16A | 0.0375 | 0.1416 | 0.4362 | 0.097* | |
H16B | 0.0891 | 0.2435 | 0.4961 | 0.097* | |
C17 | 0.3651 (3) | 0.3997 (8) | 0.4201 (4) | 0.036 (2) | |
C18 | 0.3322 (4) | 0.3294 (9) | 0.4526 (5) | 0.044 (2) | |
C19 | 0.3192 (4) | 0.4155 (9) | 0.5045 (5) | 0.068 (3) | |
H19 | 0.2965 | 0.3736 | 0.5242 | 0.081* | |
C20 | 0.3385 (4) | 0.5577 (10) | 0.5269 (6) | 0.062 (3) | |
H20 | 0.3306 | 0.6092 | 0.5638 | 0.074* | |
C21 | 0.3704 (4) | 0.6279 (9) | 0.4952 (5) | 0.045 (2) | |
C22 | 0.3823 (4) | 0.5500 (9) | 0.4416 (5) | 0.046 (3) | |
H22 | 0.4021 | 0.5976 | 0.4189 | 0.055* | |
C23 | 0.3807 (3) | 0.3234 (9) | 0.3658 (5) | 0.041 (2) | |
H23 | 0.4039 | 0.3754 | 0.3502 | 0.050* | |
C24 | 0.3885 (3) | 0.1347 (8) | 0.2824 (5) | 0.043 (2) | |
H24A | 0.4028 | 0.2185 | 0.2647 | 0.051* | |
H24B | 0.3583 | 0.0866 | 0.2335 | 0.051* | |
C25 | 0.4358 (4) | 0.0247 (9) | 0.3304 (6) | 0.055 (3) | |
H25A | 0.4240 | −0.0420 | 0.3607 | 0.066* | |
H25B | 0.4690 | 0.0795 | 0.3709 | 0.066* | |
C26 | 0.4528 (4) | −0.0696 (9) | 0.2775 (5) | 0.063 (3) | |
H26A | 0.4765 | −0.1521 | 0.3108 | 0.076* | |
H26B | 0.4187 | −0.1121 | 0.2317 | 0.076* | |
C27 | 0.5124 (3) | −0.0800 (8) | 0.2067 (5) | 0.044 (2) | |
H27 | 0.5370 | −0.1541 | 0.2479 | 0.053* | |
C28 | 0.4689 (3) | −0.1605 (10) | 0.1313 (5) | 0.060 (3) | |
H28A | 0.4425 | −0.0891 | 0.0914 | 0.073* | |
H28B | 0.4475 | −0.2292 | 0.1462 | 0.073* | |
C29 | 0.4995 (4) | −0.2467 (12) | 0.0936 (6) | 0.091 (3) | |
H29A | 0.5239 | −0.3221 | 0.1328 | 0.109* | |
H29B | 0.4714 | −0.2980 | 0.0440 | 0.109* | |
C30 | 0.5347 (5) | −0.1467 (13) | 0.0718 (6) | 0.103 (4) | |
H30A | 0.5538 | −0.2062 | 0.0487 | 0.123* | |
H30B | 0.5102 | −0.0748 | 0.0301 | 0.123* | |
C31 | 0.5777 (5) | −0.0664 (11) | 0.1462 (7) | 0.091 (3) | |
H31A | 0.5992 | 0.0011 | 0.1307 | 0.109* | |
H31B | 0.6042 | −0.1381 | 0.1859 | 0.109* | |
C32 | 0.5496 (4) | 0.0230 (9) | 0.1865 (6) | 0.066 (3) | |
H32A | 0.5262 | 0.1018 | 0.1491 | 0.080* | |
H32B | 0.5787 | 0.0696 | 0.2370 | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0549 (6) | 0.0368 (5) | 0.0571 (6) | −0.0101 (6) | 0.0390 (5) | −0.0095 (7) |
O1 | 0.097 (5) | 0.046 (4) | 0.079 (5) | −0.034 (4) | 0.060 (4) | −0.030 (4) |
O2 | 0.102 (6) | 0.049 (4) | 0.087 (5) | 0.001 (4) | 0.040 (5) | −0.026 (4) |
O3 | 0.114 (6) | 0.037 (4) | 0.134 (7) | −0.029 (4) | 0.075 (5) | −0.017 (4) |
O4 | 0.106 (5) | 0.037 (4) | 0.085 (5) | −0.027 (4) | 0.080 (4) | −0.027 (3) |
O5 | 0.088 (5) | 0.042 (4) | 0.072 (5) | −0.005 (3) | 0.037 (4) | −0.021 (3) |
O6 | 0.119 (6) | 0.051 (4) | 0.096 (5) | −0.030 (4) | 0.070 (5) | −0.013 (4) |
Cl1 | 0.070 (2) | 0.0489 (16) | 0.076 (2) | −0.0143 (17) | 0.0326 (16) | 0.0007 (17) |
O7 | 0.076 (6) | 0.095 (6) | 0.218 (9) | 0.032 (5) | 0.081 (6) | 0.018 (6) |
O8 | 0.095 (6) | 0.110 (6) | 0.089 (6) | −0.029 (5) | 0.017 (5) | 0.028 (5) |
O9 | 0.169 (9) | 0.115 (7) | 0.079 (6) | −0.012 (6) | 0.026 (6) | −0.040 (5) |
O10 | 0.094 (6) | 0.097 (5) | 0.087 (6) | −0.037 (5) | 0.034 (5) | 0.008 (4) |
Cl2 | 0.064 (2) | 0.0637 (19) | 0.099 (2) | −0.0112 (17) | 0.0252 (18) | −0.0089 (18) |
O11 | 0.272 (18) | 0.052 (7) | 0.27 (2) | −0.081 (8) | 0.20 (2) | −0.083 (9) |
O12 | 0.093 (12) | 0.132 (10) | 0.171 (16) | 0.069 (9) | 0.010 (11) | −0.045 (13) |
O13 | 0.145 (12) | 0.142 (11) | 0.105 (9) | −0.007 (11) | 0.028 (9) | −0.056 (10) |
O14 | 0.060 (6) | 0.031 (10) | 0.107 (6) | −0.008 (6) | 0.017 (5) | 0.012 (8) |
O11' | 0.272 (18) | 0.052 (7) | 0.27 (2) | −0.081 (8) | 0.20 (2) | −0.083 (9) |
O12' | 0.093 (12) | 0.132 (10) | 0.171 (16) | 0.069 (9) | 0.010 (11) | −0.045 (13) |
O13' | 0.145 (12) | 0.142 (11) | 0.105 (9) | −0.007 (11) | 0.028 (9) | −0.056 (10) |
O14' | 0.060 (6) | 0.031 (10) | 0.107 (6) | −0.008 (6) | 0.017 (5) | 0.012 (8) |
N1 | 0.052 (5) | 0.020 (4) | 0.060 (5) | −0.012 (3) | 0.035 (4) | −0.006 (4) |
N2 | 0.058 (6) | 0.070 (5) | 0.083 (6) | 0.004 (4) | 0.052 (5) | 0.005 (5) |
N3 | 0.059 (6) | 0.040 (6) | 0.067 (6) | −0.008 (5) | 0.017 (5) | −0.008 (5) |
N4 | 0.043 (5) | 0.036 (4) | 0.052 (5) | −0.016 (4) | 0.029 (4) | −0.011 (4) |
N5 | 0.060 (6) | 0.026 (4) | 0.062 (5) | 0.000 (4) | 0.033 (5) | −0.006 (3) |
N6 | 0.084 (7) | 0.041 (5) | 0.056 (6) | −0.009 (4) | 0.038 (5) | −0.017 (4) |
C1 | 0.035 (5) | 0.025 (5) | 0.060 (6) | −0.011 (4) | 0.024 (5) | −0.006 (4) |
C2 | 0.042 (6) | 0.053 (6) | 0.028 (5) | 0.003 (5) | 0.011 (5) | −0.014 (5) |
C3 | 0.106 (8) | 0.052 (6) | 0.068 (7) | −0.032 (6) | 0.066 (6) | −0.019 (5) |
C4 | 0.062 (9) | 0.059 (8) | 0.076 (9) | −0.005 (6) | 0.030 (7) | −0.028 (6) |
C5 | 0.031 (6) | 0.031 (6) | 0.052 (6) | −0.017 (4) | 0.002 (5) | −0.011 (4) |
C6 | 0.034 (6) | 0.043 (7) | 0.045 (7) | 0.010 (5) | 0.015 (5) | 0.007 (5) |
C7 | 0.054 (6) | 0.042 (5) | 0.053 (6) | 0.003 (5) | 0.040 (5) | 0.012 (5) |
C8 | 0.090 (7) | 0.039 (6) | 0.076 (7) | −0.009 (5) | 0.065 (6) | −0.005 (5) |
C9 | 0.117 (10) | 0.060 (7) | 0.101 (9) | 0.025 (7) | 0.083 (8) | 0.013 (7) |
C10 | 0.125 (10) | 0.065 (7) | 0.153 (11) | −0.014 (7) | 0.109 (9) | −0.008 (7) |
C11 | 0.067 (8) | 0.085 (8) | 0.064 (8) | 0.009 (6) | 0.043 (7) | −0.003 (6) |
C12 | 0.071 (8) | 0.102 (9) | 0.084 (8) | 0.012 (7) | 0.039 (7) | 0.034 (7) |
C13 | 0.118 (10) | 0.122 (11) | 0.071 (8) | 0.014 (8) | 0.046 (8) | 0.001 (7) |
C14 | 0.134 (12) | 0.108 (9) | 0.088 (10) | 0.032 (9) | 0.068 (9) | 0.002 (8) |
C15 | 0.090 (9) | 0.097 (8) | 0.085 (8) | 0.025 (7) | 0.063 (8) | −0.009 (7) |
C16 | 0.083 (8) | 0.088 (8) | 0.084 (8) | 0.030 (6) | 0.050 (7) | 0.019 (6) |
C17 | 0.046 (6) | 0.033 (5) | 0.031 (5) | 0.004 (4) | 0.021 (5) | 0.000 (4) |
C18 | 0.066 (7) | 0.032 (5) | 0.052 (6) | −0.004 (5) | 0.043 (6) | −0.003 (5) |
C19 | 0.114 (9) | 0.046 (6) | 0.077 (7) | −0.023 (6) | 0.072 (7) | −0.018 (5) |
C20 | 0.109 (9) | 0.046 (7) | 0.059 (7) | −0.014 (6) | 0.063 (7) | −0.017 (5) |
C21 | 0.061 (7) | 0.029 (6) | 0.040 (6) | −0.004 (5) | 0.021 (5) | −0.010 (4) |
C22 | 0.049 (7) | 0.039 (6) | 0.049 (7) | −0.015 (5) | 0.024 (6) | 0.003 (5) |
C23 | 0.026 (5) | 0.049 (6) | 0.052 (6) | −0.003 (4) | 0.021 (5) | 0.000 (5) |
C24 | 0.046 (6) | 0.042 (5) | 0.054 (6) | −0.003 (4) | 0.035 (5) | −0.006 (4) |
C25 | 0.063 (7) | 0.065 (6) | 0.067 (6) | 0.003 (5) | 0.055 (6) | 0.006 (5) |
C26 | 0.080 (7) | 0.045 (5) | 0.096 (7) | 0.004 (5) | 0.067 (6) | 0.015 (6) |
C27 | 0.041 (6) | 0.033 (5) | 0.060 (6) | 0.008 (4) | 0.027 (5) | 0.002 (5) |
C28 | 0.050 (7) | 0.053 (6) | 0.059 (6) | −0.006 (5) | 0.012 (6) | −0.018 (5) |
C29 | 0.090 (9) | 0.101 (9) | 0.068 (8) | 0.012 (7) | 0.029 (7) | −0.032 (7) |
C30 | 0.155 (13) | 0.099 (9) | 0.070 (8) | 0.050 (8) | 0.067 (9) | −0.005 (7) |
C31 | 0.127 (10) | 0.085 (8) | 0.114 (9) | 0.005 (8) | 0.099 (8) | 0.000 (8) |
C32 | 0.091 (8) | 0.055 (6) | 0.078 (7) | −0.004 (5) | 0.061 (6) | −0.010 (5) |
Geometric parameters (Å, º) top
Cu1—O4 | 1.889 (5) | C10—H10B | 0.9700 |
Cu1—O1 | 1.891 (6) | C11—C16 | 1.504 (11) |
Cu1—N1 | 1.991 (6) | C11—C12 | 1.504 (11) |
Cu1—N4 | 2.005 (6) | C11—H11 | 0.9800 |
O1—C2 | 1.269 (9) | C12—C13 | 1.521 (11) |
O2—N3 | 1.217 (8) | C12—H12A | 0.9700 |
O3—N3 | 1.203 (8) | C12—H12B | 0.9700 |
O4—C18 | 1.283 (8) | C13—C14 | 1.452 (12) |
O5—N6 | 1.217 (7) | C13—H13A | 0.9700 |
O6—N6 | 1.244 (7) | C13—H13B | 0.9700 |
Cl1—O9 | 1.367 (7) | C14—C15 | 1.491 (12) |
Cl1—O10 | 1.378 (7) | C14—H14A | 0.9700 |
Cl1—O7 | 1.393 (7) | C14—H14B | 0.9700 |
Cl1—O8 | 1.439 (7) | C15—C16 | 1.534 (10) |
Cl2—O11' | 1.387 (8) | C15—H15A | 0.9700 |
Cl2—O12 | 1.387 (7) | C15—H15B | 0.9700 |
Cl2—O14 | 1.404 (7) | C16—H16A | 0.9700 |
Cl2—O14' | 1.409 (8) | C16—H16B | 0.9700 |
Cl2—O13' | 1.430 (8) | C17—C22 | 1.410 (10) |
Cl2—O12' | 1.432 (8) | C17—C23 | 1.436 (9) |
Cl2—O11 | 1.434 (8) | C17—C18 | 1.437 (9) |
Cl2—O13 | 1.443 (7) | C18—C19 | 1.402 (9) |
N1—C7 | 1.252 (8) | C19—C20 | 1.356 (10) |
N1—C8 | 1.507 (9) | C19—H19 | 0.9300 |
N2—C10 | 1.475 (10) | C20—C21 | 1.402 (11) |
N2—C11 | 1.490 (10) | C20—H20 | 0.9300 |
N2—H2A | 0.9000 | C21—C22 | 1.371 (10) |
N2—H2B | 0.9000 | C22—H22 | 0.9300 |
N3—C5 | 1.495 (11) | C23—H23 | 0.9300 |
N4—C23 | 1.292 (8) | C24—C25 | 1.503 (10) |
N4—C24 | 1.492 (8) | C24—H24A | 0.9700 |
N5—C26 | 1.473 (9) | C24—H24B | 0.9700 |
N5—C27 | 1.516 (9) | C25—C26 | 1.523 (10) |
N5—H5A | 0.9000 | C25—H25A | 0.9700 |
N5—H5B | 0.9000 | C25—H25B | 0.9700 |
N6—C21 | 1.416 (10) | C26—H26A | 0.9700 |
C1—C2 | 1.396 (10) | C26—H26B | 0.9700 |
C1—C6 | 1.442 (10) | C27—C28 | 1.492 (10) |
C1—C7 | 1.445 (9) | C27—C32 | 1.533 (10) |
C2—C3 | 1.404 (10) | C27—H27 | 0.9800 |
C3—C4 | 1.372 (10) | C28—C29 | 1.524 (11) |
C3—H3A | 0.9300 | C28—H28A | 0.9700 |
C4—C5 | 1.385 (12) | C28—H28B | 0.9700 |
C4—H4 | 0.9300 | C29—C30 | 1.495 (12) |
C5—C6 | 1.357 (11) | C29—H29A | 0.9700 |
C6—H6A | 0.9300 | C29—H29B | 0.9700 |
C7—H7 | 0.9300 | C30—C31 | 1.477 (12) |
C8—C9 | 1.516 (10) | C30—H30A | 0.9700 |
C8—H8A | 0.9700 | C30—H30B | 0.9700 |
C8—H8B | 0.9700 | C31—C32 | 1.522 (10) |
C9—C10 | 1.448 (10) | C31—H31A | 0.9700 |
C9—H9A | 0.9700 | C31—H31B | 0.9700 |
C9—H9B | 0.9700 | C32—H32A | 0.9700 |
C10—H10A | 0.9700 | C32—H32B | 0.9700 |
| | | |
O4—Cu1—O1 | 179.2 (3) | N2—C11—H11 | 105.8 |
O4—Cu1—N1 | 89.2 (2) | C16—C11—H11 | 105.8 |
O1—Cu1—N1 | 90.4 (2) | C12—C11—H11 | 105.8 |
O4—Cu1—N4 | 90.8 (2) | C11—C12—C13 | 110.5 (8) |
O1—Cu1—N4 | 89.6 (3) | C11—C12—H12A | 109.6 |
N1—Cu1—N4 | 177.0 (3) | C13—C12—H12A | 109.6 |
C2—O1—Cu1 | 131.7 (5) | C11—C12—H12B | 109.6 |
C18—O4—Cu1 | 131.5 (5) | C13—C12—H12B | 109.6 |
O9—Cl1—O10 | 111.2 (5) | H12A—C12—H12B | 108.1 |
O9—Cl1—O7 | 110.8 (6) | C14—C13—C12 | 110.5 (9) |
O10—Cl1—O7 | 111.4 (5) | C14—C13—H13A | 109.5 |
O9—Cl1—O8 | 107.6 (5) | C12—C13—H13A | 109.5 |
O10—Cl1—O8 | 108.3 (4) | C14—C13—H13B | 109.5 |
O7—Cl1—O8 | 107.4 (5) | C12—C13—H13B | 109.5 |
O11'—Cl2—O12 | 104.0 (11) | H13A—C13—H13B | 108.1 |
O11'—Cl2—O14 | 141.1 (10) | C13—C14—C15 | 114.7 (9) |
O12—Cl2—O14 | 114.1 (7) | C13—C14—H14A | 108.6 |
O11'—Cl2—O14' | 114.7 (8) | C15—C14—H14A | 108.6 |
O12—Cl2—O14' | 141.1 (9) | C13—C14—H14B | 108.6 |
O14—Cl2—O14' | 27.1 (8) | C15—C14—H14B | 108.6 |
O11'—Cl2—O13' | 111.5 (8) | H14A—C14—H14B | 107.6 |
O12—Cl2—O13' | 57.1 (9) | C14—C15—C16 | 112.0 (8) |
O14—Cl2—O13' | 96.1 (10) | C14—C15—H15A | 109.2 |
O14'—Cl2—O13' | 108.8 (8) | C16—C15—H15A | 109.2 |
O11'—Cl2—O12' | 108.5 (8) | C14—C15—H15B | 109.2 |
O12—Cl2—O12' | 53.9 (8) | C16—C15—H15B | 109.2 |
O14—Cl2—O12' | 88.6 (10) | H15A—C15—H15B | 107.9 |
O14'—Cl2—O12' | 107.3 (8) | C11—C16—C15 | 109.4 (7) |
O13'—Cl2—O12' | 105.5 (8) | C11—C16—H16A | 109.8 |
O11'—Cl2—O11 | 46.7 (8) | C15—C16—H16A | 109.8 |
O12—Cl2—O11 | 110.6 (8) | C11—C16—H16B | 109.8 |
O14—Cl2—O11 | 109.0 (8) | C15—C16—H16B | 109.8 |
O14'—Cl2—O11 | 94.0 (11) | H16A—C16—H16B | 108.2 |
O13'—Cl2—O11 | 154.9 (10) | C22—C17—C23 | 118.8 (7) |
O12'—Cl2—O11 | 76.5 (9) | C22—C17—C18 | 118.6 (7) |
O11'—Cl2—O13 | 62.1 (8) | C23—C17—C18 | 122.6 (7) |
O12—Cl2—O13 | 108.0 (7) | O4—C18—C19 | 120.1 (7) |
O14—Cl2—O13 | 110.6 (8) | O4—C18—C17 | 122.4 (7) |
O14'—Cl2—O13 | 93.8 (11) | C19—C18—C17 | 117.5 (7) |
O13'—Cl2—O13 | 64.9 (7) | C20—C19—C18 | 122.3 (8) |
O12'—Cl2—O13 | 158.9 (9) | C20—C19—H19 | 118.9 |
O11—Cl2—O13 | 104.2 (6) | C18—C19—H19 | 118.9 |
C7—N1—C8 | 114.4 (6) | C19—C20—C21 | 120.7 (8) |
C7—N1—Cu1 | 125.0 (5) | C19—C20—H20 | 119.6 |
C8—N1—Cu1 | 120.7 (5) | C21—C20—H20 | 119.6 |
C10—N2—C11 | 117.2 (7) | C22—C21—C20 | 119.0 (8) |
C10—N2—H2A | 108.0 | C22—C21—N6 | 121.4 (8) |
C11—N2—H2A | 108.0 | C20—C21—N6 | 119.5 (8) |
C10—N2—H2B | 108.0 | C21—C22—C17 | 121.8 (8) |
C11—N2—H2B | 108.0 | C21—C22—H22 | 119.1 |
H2A—N2—H2B | 107.2 | C17—C22—H22 | 119.1 |
O3—N3—O2 | 124.3 (9) | N4—C23—C17 | 126.2 (7) |
O3—N3—C5 | 117.5 (8) | N4—C23—H23 | 116.9 |
O2—N3—C5 | 118.1 (9) | C17—C23—H23 | 116.9 |
C23—N4—C24 | 115.8 (6) | N4—C24—C25 | 109.0 (6) |
C23—N4—Cu1 | 124.9 (5) | N4—C24—H24A | 109.9 |
C24—N4—Cu1 | 119.3 (5) | C25—C24—H24A | 109.9 |
C26—N5—C27 | 115.1 (6) | N4—C24—H24B | 109.9 |
C26—N5—H5A | 108.5 | C25—C24—H24B | 109.9 |
C27—N5—H5A | 108.5 | H24A—C24—H24B | 108.3 |
C26—N5—H5B | 108.5 | C24—C25—C26 | 114.6 (7) |
C27—N5—H5B | 108.5 | C24—C25—H25A | 108.6 |
H5A—N5—H5B | 107.5 | C26—C25—H25A | 108.6 |
O5—N6—O6 | 123.5 (8) | C24—C25—H25B | 108.6 |
O5—N6—C21 | 118.8 (8) | C26—C25—H25B | 108.6 |
O6—N6—C21 | 117.6 (7) | H25A—C25—H25B | 107.6 |
C2—C1—C6 | 120.6 (8) | N5—C26—C25 | 113.7 (7) |
C2—C1—C7 | 122.3 (7) | N5—C26—H26A | 108.8 |
C6—C1—C7 | 117.0 (8) | C25—C26—H26A | 108.8 |
O1—C2—C1 | 122.8 (7) | N5—C26—H26B | 108.8 |
O1—C2—C3 | 119.8 (8) | C25—C26—H26B | 108.8 |
C1—C2—C3 | 117.3 (8) | H26A—C26—H26B | 107.7 |
C4—C3—C2 | 123.7 (9) | C28—C27—N5 | 110.8 (7) |
C4—C3—H3A | 118.2 | C28—C27—C32 | 111.5 (7) |
C2—C3—H3A | 118.2 | N5—C27—C32 | 108.2 (6) |
C3—C4—C5 | 116.4 (9) | C28—C27—H27 | 108.8 |
C3—C4—H4 | 121.8 | N5—C27—H27 | 108.8 |
C5—C4—H4 | 121.8 | C32—C27—H27 | 108.8 |
C6—C5—C4 | 125.0 (8) | C27—C28—C29 | 108.6 (7) |
C6—C5—N3 | 118.3 (8) | C27—C28—H28A | 110.0 |
C4—C5—N3 | 116.5 (9) | C29—C28—H28A | 110.0 |
C5—C6—C1 | 116.9 (8) | C27—C28—H28B | 110.0 |
C5—C6—H6A | 121.5 | C29—C28—H28B | 110.0 |
C1—C6—H6A | 121.5 | H28A—C28—H28B | 108.4 |
N1—C7—C1 | 127.0 (7) | C30—C29—C28 | 112.3 (8) |
N1—C7—H7 | 116.5 | C30—C29—H29A | 109.1 |
C1—C7—H7 | 116.5 | C28—C29—H29A | 109.1 |
N1—C8—C9 | 110.8 (7) | C30—C29—H29B | 109.1 |
N1—C8—H8A | 109.5 | C28—C29—H29B | 109.1 |
C9—C8—H8A | 109.5 | H29A—C29—H29B | 107.9 |
N1—C8—H8B | 109.5 | C31—C30—C29 | 110.4 (8) |
C9—C8—H8B | 109.5 | C31—C30—H30A | 109.6 |
H8A—C8—H8B | 108.1 | C29—C30—H30A | 109.6 |
C10—C9—C8 | 114.2 (9) | C31—C30—H30B | 109.6 |
C10—C9—H9A | 108.7 | C29—C30—H30B | 109.6 |
C8—C9—H9A | 108.7 | H30A—C30—H30B | 108.1 |
C10—C9—H9B | 108.7 | C30—C31—C32 | 111.1 (9) |
C8—C9—H9B | 108.7 | C30—C31—H31A | 109.4 |
H9A—C9—H9B | 107.6 | C32—C31—H31A | 109.4 |
C9—C10—N2 | 111.8 (8) | C30—C31—H31B | 109.4 |
C9—C10—H10A | 109.3 | C32—C31—H31B | 109.4 |
N2—C10—H10A | 109.3 | H31A—C31—H31B | 108.0 |
C9—C10—H10B | 109.3 | C31—C32—C27 | 110.3 (7) |
N2—C10—H10B | 109.3 | C31—C32—H32A | 109.6 |
H10A—C10—H10B | 107.9 | C27—C32—H32A | 109.6 |
N2—C11—C16 | 114.6 (7) | C31—C32—H32B | 109.6 |
N2—C11—C12 | 113.1 (8) | C27—C32—H32B | 109.6 |
C16—C11—C12 | 111.0 (8) | H32A—C32—H32B | 108.1 |
| | | |
N1—Cu1—O1—C2 | −10.1 (7) | C11—C12—C13—C14 | −56.1 (13) |
N4—Cu1—O1—C2 | 166.8 (8) | C12—C13—C14—C15 | 53.1 (14) |
N1—Cu1—O4—C18 | −168.3 (8) | C13—C14—C15—C16 | −51.9 (13) |
N4—Cu1—O4—C18 | 14.7 (8) | N2—C11—C16—C15 | 173.5 (8) |
O4—Cu1—N1—C7 | −173.0 (7) | C12—C11—C16—C15 | −56.8 (11) |
O1—Cu1—N1—C7 | 7.7 (7) | C14—C15—C16—C11 | 52.1 (12) |
O4—Cu1—N1—C8 | 7.3 (6) | Cu1—O4—C18—C19 | 167.7 (6) |
O1—Cu1—N1—C8 | −172.0 (6) | Cu1—O4—C18—C17 | −12.8 (13) |
O4—Cu1—N4—C23 | −9.1 (6) | C22—C17—C18—O4 | −179.7 (8) |
O1—Cu1—N4—C23 | 170.2 (7) | C23—C17—C18—O4 | 1.0 (12) |
O4—Cu1—N4—C24 | 172.6 (6) | C22—C17—C18—C19 | −0.2 (12) |
O1—Cu1—N4—C24 | −8.1 (5) | C23—C17—C18—C19 | −179.5 (8) |
Cu1—O1—C2—C1 | 7.6 (13) | O4—C18—C19—C20 | 176.7 (9) |
Cu1—O1—C2—C3 | −170.6 (6) | C17—C18—C19—C20 | −2.8 (14) |
C6—C1—C2—O1 | −177.4 (7) | C18—C19—C20—C21 | 3.4 (15) |
C7—C1—C2—O1 | 0.7 (13) | C19—C20—C21—C22 | −0.7 (14) |
C6—C1—C2—C3 | 0.8 (12) | C19—C20—C21—N6 | 176.5 (8) |
C7—C1—C2—C3 | 178.9 (7) | O5—N6—C21—C22 | −174.3 (8) |
O1—C2—C3—C4 | 175.3 (9) | O6—N6—C21—C22 | 2.4 (13) |
C1—C2—C3—C4 | −3.0 (14) | O5—N6—C21—C20 | 8.5 (13) |
C2—C3—C4—C5 | 3.4 (15) | O6—N6—C21—C20 | −174.8 (8) |
C3—C4—C5—C6 | −1.6 (15) | C20—C21—C22—C17 | −2.4 (14) |
C3—C4—C5—N3 | −176.4 (8) | N6—C21—C22—C17 | −179.6 (8) |
O3—N3—C5—C6 | 1.2 (13) | C23—C17—C22—C21 | −177.9 (8) |
O2—N3—C5—C6 | −176.9 (8) | C18—C17—C22—C21 | 2.8 (13) |
O3—N3—C5—C4 | 176.4 (9) | C24—N4—C23—C17 | −178.9 (7) |
O2—N3—C5—C4 | −1.8 (12) | Cu1—N4—C23—C17 | 2.8 (11) |
C4—C5—C6—C1 | −0.3 (14) | C22—C17—C23—N4 | −175.7 (8) |
N3—C5—C6—C1 | 174.4 (7) | C18—C17—C23—N4 | 3.5 (12) |
C2—C1—C6—C5 | 0.8 (12) | C23—N4—C24—C25 | 104.5 (8) |
C7—C1—C6—C5 | −177.4 (7) | Cu1—N4—C24—C25 | −77.1 (7) |
C8—N1—C7—C1 | 176.1 (7) | N4—C24—C25—C26 | 165.2 (6) |
Cu1—N1—C7—C1 | −3.6 (12) | C27—N5—C26—C25 | 167.7 (7) |
C2—C1—C7—N1 | −2.3 (13) | C24—C25—C26—N5 | 72.0 (10) |
C6—C1—C7—N1 | 175.8 (8) | C26—N5—C27—C28 | 65.4 (9) |
C7—N1—C8—C9 | −100.7 (8) | C26—N5—C27—C32 | −172.1 (7) |
Cu1—N1—C8—C9 | 79.1 (8) | N5—C27—C28—C29 | 176.8 (7) |
N1—C8—C9—C10 | 177.9 (7) | C32—C27—C28—C29 | 56.2 (9) |
C8—C9—C10—N2 | −79.5 (12) | C27—C28—C29—C30 | −57.8 (11) |
C11—N2—C10—C9 | 166.7 (9) | C28—C29—C30—C31 | 58.5 (11) |
C10—N2—C11—C16 | 67.5 (12) | C29—C30—C31—C32 | −56.7 (11) |
C10—N2—C11—C12 | −61.1 (11) | C30—C31—C32—C27 | 55.7 (11) |
N2—C11—C12—C13 | −170.1 (7) | C28—C27—C32—C31 | −56.2 (10) |
C16—C11—C12—C13 | 59.5 (12) | N5—C27—C32—C31 | −178.3 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O11i | 0.90 | 2.41 | 3.147 (14) | 139 |
N2—H2A···O13i | 0.90 | 2.59 | 3.321 (16) | 139 |
N2—H2B···O10ii | 0.90 | 2.08 | 2.944 (11) | 161 |
N2—H2B···O8ii | 0.90 | 2.46 | 3.185 (10) | 137 |
N5—H5A···O14iii | 0.90 | 2.34 | 2.959 (14) | 126 |
N5—H5A···O8 | 0.90 | 2.66 | 3.311 (10) | 131 |
N5—H5B···O5iv | 0.90 | 2.48 | 3.336 (10) | 158 |
N5—H5B···O9 | 0.90 | 2.59 | 3.209 (10) | 127 |
Symmetry codes: (i) x, y−1, z; (ii) x−1/2, y−1/2, z; (iii) x+1/2, y−1/2, z; (iv) x, −y+1, z−1/2. |