In the title complex, [Cu(C9H7O3)(C27H27N7)]ClO4·0.5C3H7NO, the CuII ion five-coordinate with an N4O ligand set and has a distorted trigonal–bipyramidal geometry.
Supporting information
CCDC reference: 627349
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- Disorder in solvent or counterion
- R factor = 0.062
- wR factor = 0.206
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N8
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
(4-Hydroxycinnamato)[tris(
N-methylbenzimidazol-2-ylmethyl)amine]copper(II)] perchlorate dimethylformamide hemisolvate
top
Crystal data top
[Cu(C9H7O3)(C27H27N7)]ClO4·0.5C3H7NO | F(000) = 1684 |
Mr = 812.24 | Dx = 1.390 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9619 reflections |
a = 15.1645 (8) Å | θ = 1.9–28.3° |
b = 13.1277 (7) Å | µ = 0.69 mm−1 |
c = 19.6013 (10) Å | T = 293 K |
β = 96.034 (2)° | Block, green |
V = 3880.5 (4) Å3 | 0.39 × 0.35 × 0.28 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD diffractometer | 9619 independent reflections |
Radiation source: fine-focus sealed tube | 4890 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
Detector resolution: 9.00 cm pixels mm-1 | θmax = 28.3°, θmin = 1.9° |
φ and ω scans | h = −15→20 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −17→15 |
Tmin = 0.767, Tmax = 0.828 | l = −23→26 |
28111 measured reflections | |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.206 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.1183P)2] where P = (Fo2 + 2Fc2)/3 |
9619 reflections | (Δ/σ)max < 0.001 |
519 parameters | Δρmax = 0.93 e Å−3 |
30 restraints | Δρmin = −0.50 e Å−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 | 0.27535 (3) | 0.34152 (3) | 0.01749 (2) | 0.04117 (17) | |
Cl1 | 0.48498 (12) | 0.44305 (13) | 0.37230 (7) | 0.0871 (5) | |
O1 | −0.1510 (2) | 0.9095 (2) | −0.23440 (14) | 0.0555 (8) | |
H1 | −0.1584 | 0.9128 | −0.2764 | 0.100* | |
O2 | 0.2064 (2) | 0.4567 (2) | −0.01637 (12) | 0.0527 (8) | |
O3 | 0.18326 (19) | 0.4085 (2) | −0.12528 (13) | 0.0487 (7) | |
O4 | 0.3960 (4) | 0.4645 (5) | 0.3779 (3) | 0.153 (2) | |
O5 | 0.4868 (4) | 0.3721 (5) | 0.3170 (3) | 0.148 (2) | |
O6 | 0.5233 (4) | 0.3980 (5) | 0.4325 (3) | 0.145 (2) | |
O7 | 0.5366 (4) | 0.5225 (4) | 0.3541 (2) | 0.135 (2) | |
O8 | 0.2579 (7) | 0.8316 (9) | 0.1228 (5) | 0.125 (3) | 0.50 |
N1 | 0.3543 (2) | 0.2216 (2) | 0.06619 (16) | 0.0435 (7) | |
N2 | 0.3921 (2) | 0.3623 (2) | −0.02518 (16) | 0.0437 (8) | |
N3 | 0.5388 (2) | 0.3436 (3) | −0.00956 (18) | 0.0504 (8) | |
N4 | 0.1995 (2) | 0.2131 (2) | −0.01462 (16) | 0.0443 (8) | |
N5 | 0.1993 (2) | 0.0450 (2) | −0.02885 (16) | 0.0482 (8) | |
N6 | 0.2546 (2) | 0.3673 (2) | 0.11749 (15) | 0.0394 (7) | |
N7 | 0.2752 (2) | 0.3169 (2) | 0.22623 (15) | 0.0429 (8) | |
N8 | 0.3057 (4) | 0.7807 (6) | 0.2269 (4) | 0.0531 (18) | 0.50 |
C1 | 0.4477 (3) | 0.2560 (3) | 0.0725 (2) | 0.0496 (10) | |
H1A | 0.4610 | 0.2951 | 0.1143 | 0.100* | |
H1B | 0.4872 | 0.1978 | 0.0741 | 0.100* | |
C2 | 0.4601 (3) | 0.3198 (3) | 0.0122 (2) | 0.0470 (10) | |
C3 | 0.4291 (3) | 0.4171 (3) | −0.0766 (2) | 0.0444 (9) | |
C4 | 0.3888 (3) | 0.4714 (3) | −0.1318 (2) | 0.0497 (10) | |
H4A | 0.3276 | 0.4793 | −0.1386 | 0.100* | |
C5 | 0.4441 (3) | 0.5137 (4) | −0.1768 (2) | 0.0603 (12) | |
H5A | 0.4195 | 0.5499 | −0.2149 | 0.100* | |
C6 | 0.5376 (4) | 0.5021 (4) | −0.1648 (3) | 0.0644 (13) | |
H6A | 0.5733 | 0.5310 | −0.1954 | 0.100* | |
C7 | 0.5760 (3) | 0.4499 (4) | −0.1099 (3) | 0.0640 (12) | |
H7A | 0.6373 | 0.4436 | −0.1017 | 0.100* | |
C8 | 0.5208 (3) | 0.4065 (3) | −0.0667 (2) | 0.0496 (10) | |
C9 | 0.6262 (3) | 0.3070 (4) | 0.0177 (3) | 0.0705 (14) | |
H9A | 0.6206 | 0.2633 | 0.0563 | 0.100* | |
H9B | 0.6634 | 0.3639 | 0.0319 | 0.100* | |
H9C | 0.6522 | 0.2695 | −0.0172 | 0.100* | |
C10 | 0.3413 (3) | 0.1309 (3) | 0.0213 (2) | 0.0534 (11) | |
H10A | 0.3556 | 0.0694 | 0.0477 | 0.100* | |
H10B | 0.3798 | 0.1346 | −0.0152 | 0.100* | |
C11 | 0.2471 (3) | 0.1293 (3) | −0.0079 (2) | 0.0453 (9) | |
C12 | 0.1145 (3) | 0.0781 (3) | −0.05093 (18) | 0.0453 (9) | |
C13 | 0.0392 (3) | 0.0248 (4) | −0.0771 (2) | 0.0606 (12) | |
H13A | 0.0400 | −0.0452 | −0.0846 | 0.100* | |
C14 | −0.0371 (3) | 0.0825 (4) | −0.0913 (2) | 0.0610 (12) | |
H14A | −0.0893 | 0.0502 | −0.1086 | 0.100* | |
C15 | −0.0381 (3) | 0.1863 (4) | −0.0806 (2) | 0.0579 (12) | |
H15A | −0.0911 | 0.2216 | −0.0899 | 0.100* | |
C16 | 0.0375 (3) | 0.2393 (3) | −0.05645 (19) | 0.0485 (10) | |
H16A | 0.0366 | 0.3095 | −0.0503 | 0.100* | |
C17 | 0.1148 (3) | 0.1834 (3) | −0.04182 (18) | 0.0429 (9) | |
C18 | 0.2329 (4) | −0.0596 (3) | −0.0297 (3) | 0.0662 (13) | |
H18A | 0.2270 | −0.0846 | −0.0760 | 0.100* | |
H18B | 0.1995 | −0.1021 | −0.0020 | 0.100* | |
H18C | 0.2943 | −0.0606 | −0.0117 | 0.100* | |
C19 | 0.3252 (3) | 0.2007 (3) | 0.13570 (19) | 0.0473 (9) | |
H19A | 0.2809 | 0.1470 | 0.1326 | 0.100* | |
H19B | 0.3753 | 0.1790 | 0.1672 | 0.100* | |
C20 | 0.2873 (2) | 0.2960 (3) | 0.16047 (18) | 0.0382 (8) | |
C21 | 0.2152 (3) | 0.4384 (3) | 0.15708 (18) | 0.0399 (8) | |
C22 | 0.1678 (3) | 0.5263 (3) | 0.1386 (2) | 0.0521 (10) | |
H22A | 0.1595 | 0.5483 | 0.0933 | 0.100* | |
C23 | 0.1334 (4) | 0.5799 (3) | 0.1905 (2) | 0.0647 (13) | |
H23A | 0.1005 | 0.6386 | 0.1796 | 0.100* | |
C24 | 0.1468 (4) | 0.5484 (4) | 0.2586 (2) | 0.0669 (13) | |
H24A | 0.1226 | 0.5867 | 0.2919 | 0.100* | |
C25 | 0.1944 (3) | 0.4629 (4) | 0.2779 (2) | 0.0602 (12) | |
H25A | 0.2035 | 0.4422 | 0.3235 | 0.100* | |
C26 | 0.2288 (3) | 0.4084 (3) | 0.22554 (19) | 0.0438 (9) | |
C27 | 0.3032 (3) | 0.2544 (3) | 0.2871 (2) | 0.0589 (12) | |
H27A | 0.3079 | 0.1845 | 0.2737 | 0.100* | |
H27B | 0.2602 | 0.2603 | 0.3195 | 0.100* | |
H27C | 0.3598 | 0.2778 | 0.3078 | 0.100* | |
C28 | −0.0964 (3) | 0.8296 (3) | −0.21518 (19) | 0.0396 (8) | |
C29 | −0.0782 (3) | 0.8085 (3) | −0.1452 (2) | 0.0461 (9) | |
H29A | −0.1028 | 0.8491 | −0.1133 | 0.100* | |
C30 | −0.0247 (3) | 0.7291 (3) | −0.12356 (18) | 0.0458 (9) | |
H30A | −0.0128 | 0.7166 | −0.0768 | 0.100* | |
C31 | 0.0128 (3) | 0.6660 (3) | −0.17032 (18) | 0.0425 (9) | |
C32 | −0.0083 (3) | 0.6870 (3) | −0.23920 (19) | 0.0492 (10) | |
H32A | 0.0141 | 0.6450 | −0.2715 | 0.100* | |
C33 | −0.0611 (3) | 0.7677 (3) | −0.26143 (19) | 0.0493 (10) | |
H33A | −0.0729 | 0.7804 | −0.3082 | 0.100* | |
C34 | 0.0700 (3) | 0.5799 (3) | −0.14984 (19) | 0.0479 (10) | |
H34A | 0.0789 | 0.5344 | −0.1848 | 0.100* | |
C35 | 0.1111 (3) | 0.5567 (3) | −0.0893 (2) | 0.0489 (10) | |
H35A | 0.1025 | 0.5982 | −0.0521 | 0.100* | |
C36 | 0.1704 (3) | 0.4674 (3) | −0.07796 (19) | 0.0424 (9) | |
C37 | 0.3097 (7) | 0.7868 (11) | 0.1639 (7) | 0.088 (4) | 0.50 |
H37A | 0.3569 | 0.7539 | 0.1466 | 0.100* | 0.50 |
C38 | 0.2373 (7) | 0.8256 (8) | 0.2609 (6) | 0.071 (3) | 0.50 |
H38A | 0.1806 | 0.8045 | 0.2390 | 0.100* | 0.50 |
H38B | 0.2418 | 0.8985 | 0.2588 | 0.100* | 0.50 |
H38C | 0.2430 | 0.8043 | 0.3081 | 0.100* | 0.50 |
C39 | 0.3711 (7) | 0.7121 (8) | 0.2649 (5) | 0.072 (3) | 0.50 |
H39A | 0.4216 | 0.7043 | 0.2396 | 0.100* | 0.50 |
H39B | 0.3444 | 0.6468 | 0.2706 | 0.100* | 0.50 |
H39C | 0.3897 | 0.7409 | 0.3091 | 0.100* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0432 (3) | 0.0436 (3) | 0.0356 (3) | 0.0105 (2) | −0.00073 (19) | 0.00060 (19) |
Cl1 | 0.0962 (12) | 0.0988 (11) | 0.0674 (8) | −0.0386 (9) | 0.0140 (8) | 0.0019 (8) |
O1 | 0.063 (2) | 0.0444 (16) | 0.0568 (17) | 0.0095 (14) | −0.0047 (14) | 0.0077 (13) |
O2 | 0.065 (2) | 0.0561 (17) | 0.0346 (14) | 0.0260 (14) | −0.0044 (13) | −0.0006 (12) |
O3 | 0.0529 (17) | 0.0486 (16) | 0.0424 (14) | 0.0084 (13) | −0.0050 (12) | −0.0060 (12) |
O4 | 0.121 (4) | 0.184 (5) | 0.157 (5) | 0.020 (4) | 0.030 (4) | 0.022 (4) |
O5 | 0.163 (5) | 0.148 (4) | 0.137 (4) | −0.062 (4) | 0.032 (4) | −0.049 (4) |
O6 | 0.133 (4) | 0.175 (5) | 0.132 (4) | 0.035 (4) | 0.040 (3) | 0.059 (4) |
O7 | 0.167 (5) | 0.131 (4) | 0.106 (3) | −0.091 (4) | 0.008 (3) | 0.000 (3) |
O8 | 0.082 (6) | 0.201 (8) | 0.091 (5) | 0.007 (6) | 0.006 (5) | 0.027 (5) |
N1 | 0.0396 (18) | 0.0469 (18) | 0.0430 (17) | 0.0090 (14) | −0.0011 (14) | −0.0014 (14) |
N2 | 0.0375 (18) | 0.0514 (19) | 0.0419 (17) | 0.0035 (14) | 0.0020 (14) | −0.0023 (14) |
N3 | 0.0376 (19) | 0.057 (2) | 0.056 (2) | 0.0027 (15) | 0.0027 (16) | −0.0047 (17) |
N4 | 0.0459 (19) | 0.0403 (18) | 0.0457 (18) | 0.0035 (14) | 0.0006 (15) | −0.0025 (14) |
N5 | 0.061 (2) | 0.0417 (19) | 0.0419 (18) | 0.0015 (16) | 0.0055 (16) | −0.0003 (14) |
N6 | 0.0379 (17) | 0.0440 (17) | 0.0357 (16) | 0.0045 (13) | 0.0013 (13) | 0.0027 (13) |
N7 | 0.0445 (19) | 0.0499 (19) | 0.0335 (16) | −0.0077 (14) | 0.0001 (14) | 0.0055 (13) |
N8 | 0.038 (4) | 0.068 (5) | 0.053 (4) | −0.013 (3) | 0.001 (3) | −0.031 (4) |
C1 | 0.044 (2) | 0.053 (2) | 0.051 (2) | 0.0095 (19) | −0.0001 (19) | 0.0021 (18) |
C2 | 0.042 (2) | 0.050 (2) | 0.049 (2) | 0.0052 (17) | −0.0009 (18) | −0.0084 (17) |
C3 | 0.044 (2) | 0.042 (2) | 0.048 (2) | −0.0014 (17) | 0.0073 (18) | −0.0095 (17) |
C4 | 0.053 (3) | 0.049 (2) | 0.047 (2) | −0.0044 (19) | 0.0069 (19) | −0.0031 (18) |
C5 | 0.071 (3) | 0.058 (3) | 0.054 (3) | −0.009 (2) | 0.011 (2) | −0.001 (2) |
C6 | 0.072 (3) | 0.063 (3) | 0.064 (3) | −0.014 (2) | 0.030 (3) | −0.004 (2) |
C7 | 0.056 (3) | 0.062 (3) | 0.076 (3) | −0.005 (2) | 0.016 (2) | −0.010 (3) |
C8 | 0.045 (2) | 0.047 (2) | 0.058 (2) | −0.0027 (18) | 0.010 (2) | −0.0136 (19) |
C9 | 0.040 (3) | 0.084 (3) | 0.085 (3) | 0.009 (2) | −0.001 (2) | −0.006 (3) |
C10 | 0.051 (3) | 0.048 (2) | 0.060 (3) | 0.0149 (19) | −0.001 (2) | −0.0095 (19) |
C11 | 0.050 (2) | 0.045 (2) | 0.040 (2) | 0.0030 (18) | 0.0023 (18) | −0.0027 (16) |
C12 | 0.052 (3) | 0.052 (2) | 0.0319 (19) | −0.0046 (19) | 0.0073 (17) | 0.0032 (16) |
C13 | 0.068 (3) | 0.064 (3) | 0.050 (2) | −0.021 (2) | 0.006 (2) | 0.000 (2) |
C14 | 0.059 (3) | 0.077 (3) | 0.046 (2) | −0.021 (2) | −0.002 (2) | 0.008 (2) |
C15 | 0.049 (3) | 0.082 (3) | 0.042 (2) | −0.005 (2) | 0.0020 (19) | 0.013 (2) |
C16 | 0.047 (2) | 0.062 (3) | 0.036 (2) | 0.0021 (19) | −0.0003 (17) | 0.0024 (18) |
C17 | 0.046 (2) | 0.051 (2) | 0.0310 (18) | −0.0018 (17) | 0.0021 (16) | 0.0010 (16) |
C18 | 0.090 (4) | 0.039 (2) | 0.070 (3) | 0.005 (2) | 0.009 (3) | −0.005 (2) |
C19 | 0.052 (2) | 0.046 (2) | 0.043 (2) | 0.0087 (18) | −0.0003 (18) | 0.0055 (17) |
C20 | 0.0348 (19) | 0.0413 (19) | 0.0374 (19) | −0.0011 (15) | −0.0012 (15) | 0.0032 (15) |
C21 | 0.040 (2) | 0.043 (2) | 0.0379 (19) | −0.0012 (16) | 0.0070 (16) | −0.0012 (15) |
C22 | 0.061 (3) | 0.048 (2) | 0.048 (2) | 0.010 (2) | 0.011 (2) | 0.0001 (18) |
C23 | 0.084 (4) | 0.052 (3) | 0.061 (3) | 0.013 (2) | 0.022 (3) | −0.004 (2) |
C24 | 0.090 (4) | 0.059 (3) | 0.055 (3) | 0.010 (3) | 0.025 (3) | −0.009 (2) |
C25 | 0.078 (3) | 0.061 (3) | 0.043 (2) | −0.007 (2) | 0.015 (2) | −0.005 (2) |
C26 | 0.047 (2) | 0.045 (2) | 0.039 (2) | −0.0073 (17) | 0.0045 (17) | 0.0020 (16) |
C27 | 0.067 (3) | 0.063 (3) | 0.044 (2) | −0.010 (2) | −0.008 (2) | 0.018 (2) |
C28 | 0.037 (2) | 0.038 (2) | 0.042 (2) | −0.0024 (15) | −0.0028 (16) | 0.0073 (15) |
C29 | 0.053 (2) | 0.044 (2) | 0.042 (2) | 0.0028 (18) | 0.0037 (18) | −0.0020 (17) |
C30 | 0.053 (2) | 0.053 (2) | 0.0307 (18) | 0.0056 (19) | 0.0017 (17) | 0.0044 (16) |
C31 | 0.046 (2) | 0.047 (2) | 0.0331 (18) | 0.0065 (17) | −0.0007 (16) | 0.0018 (16) |
C32 | 0.048 (2) | 0.067 (3) | 0.0331 (19) | 0.013 (2) | 0.0056 (17) | −0.0017 (18) |
C33 | 0.052 (2) | 0.060 (3) | 0.0348 (19) | 0.007 (2) | 0.0001 (18) | 0.0075 (18) |
C34 | 0.051 (2) | 0.051 (2) | 0.041 (2) | 0.0114 (19) | 0.0010 (18) | −0.0007 (17) |
C35 | 0.055 (3) | 0.051 (2) | 0.040 (2) | 0.0114 (19) | 0.0026 (18) | 0.0002 (17) |
C36 | 0.042 (2) | 0.044 (2) | 0.041 (2) | 0.0053 (17) | 0.0017 (17) | 0.0011 (16) |
C37 | 0.039 (6) | 0.129 (10) | 0.090 (8) | 0.004 (6) | −0.024 (6) | −0.007 (8) |
C38 | 0.051 (6) | 0.080 (7) | 0.085 (7) | −0.011 (5) | 0.026 (5) | −0.034 (6) |
C39 | 0.069 (7) | 0.067 (6) | 0.080 (7) | 0.021 (5) | 0.000 (5) | −0.014 (5) |
Geometric parameters (Å, º) top
Cu1—O2 | 1.917 (3) | C10—H10B | 0.9700 |
Cu1—N6 | 2.046 (3) | C12—C13 | 1.390 (6) |
Cu1—N2 | 2.055 (3) | C12—C17 | 1.394 (5) |
Cu1—N4 | 2.100 (3) | C13—C14 | 1.387 (7) |
Cu1—N1 | 2.140 (3) | C13—H13A | 0.9300 |
Cl1—O7 | 1.374 (4) | C14—C15 | 1.379 (7) |
Cl1—O6 | 1.391 (6) | C14—H14A | 0.9300 |
Cl1—O4 | 1.394 (6) | C15—C16 | 1.380 (6) |
Cl1—O5 | 1.432 (5) | C15—H15A | 0.9300 |
O1—C28 | 1.364 (4) | C16—C17 | 1.387 (6) |
O1—H1 | 0.8200 | C16—H16A | 0.9300 |
O2—C36 | 1.279 (4) | C18—H18A | 0.9600 |
O3—C36 | 1.239 (4) | C18—H18B | 0.9600 |
O8—C37 | 1.217 (14) | C18—H18C | 0.9600 |
N1—C1 | 1.480 (5) | C19—C20 | 1.480 (5) |
N1—C10 | 1.481 (5) | C19—H19A | 0.9700 |
N1—C19 | 1.501 (5) | C19—H19B | 0.9700 |
N2—C2 | 1.323 (5) | C21—C22 | 1.388 (5) |
N2—C3 | 1.402 (5) | C21—C26 | 1.393 (5) |
N3—C2 | 1.345 (5) | C22—C23 | 1.383 (6) |
N3—C8 | 1.395 (5) | C22—H22A | 0.9300 |
N3—C9 | 1.458 (6) | C23—C24 | 1.391 (7) |
N4—C11 | 1.315 (5) | C23—H23A | 0.9300 |
N4—C17 | 1.393 (5) | C24—C25 | 1.367 (7) |
N5—C11 | 1.361 (5) | C24—H24A | 0.9300 |
N5—C12 | 1.384 (5) | C25—C26 | 1.397 (6) |
N5—C18 | 1.465 (5) | C25—H25A | 0.9300 |
N6—C20 | 1.321 (4) | C27—H27A | 0.9600 |
N6—C21 | 1.388 (5) | C27—H27B | 0.9600 |
N7—C20 | 1.349 (5) | C27—H27C | 0.9600 |
N7—C26 | 1.391 (5) | C28—C33 | 1.368 (5) |
N7—C27 | 1.473 (5) | C28—C29 | 1.397 (5) |
N8—C37 | 1.245 (14) | C29—C30 | 1.362 (5) |
N8—C38 | 1.421 (11) | C29—H29A | 0.9300 |
N8—C39 | 1.480 (12) | C30—C31 | 1.400 (5) |
C1—C2 | 1.476 (6) | C30—H30A | 0.9300 |
C1—H1A | 0.9700 | C31—C32 | 1.382 (5) |
C1—H1B | 0.9700 | C31—C34 | 1.455 (5) |
C3—C4 | 1.384 (6) | C32—C33 | 1.371 (6) |
C3—C8 | 1.391 (6) | C32—H32A | 0.9300 |
C4—C5 | 1.394 (6) | C33—H33A | 0.9300 |
C4—H4A | 0.9300 | C34—C35 | 1.316 (5) |
C5—C6 | 1.421 (7) | C34—H34A | 0.9300 |
C5—H5A | 0.9300 | C35—C36 | 1.479 (5) |
C6—C7 | 1.356 (7) | C35—H35A | 0.9300 |
C6—H6A | 0.9300 | C37—H37A | 0.9300 |
C7—C8 | 1.375 (6) | C38—H38A | 0.9600 |
C7—H7A | 0.9300 | C38—H38B | 0.9600 |
C9—H9A | 0.9600 | C38—H38C | 0.9600 |
C9—H9B | 0.9600 | C39—H39A | 0.9600 |
C9—H9C | 0.9600 | C39—H39B | 0.9600 |
C10—C11 | 1.484 (6) | C39—H39C | 0.9600 |
C10—H10A | 0.9700 | | |
| | | |
O2—Cu1—N6 | 93.88 (11) | C15—C14—C13 | 122.1 (4) |
O2—Cu1—N2 | 102.51 (13) | C15—C14—H14A | 119.0 |
N6—Cu1—N2 | 126.45 (12) | C13—C14—H14A | 119.0 |
O2—Cu1—N4 | 105.53 (13) | C14—C15—C16 | 121.9 (4) |
N6—Cu1—N4 | 106.58 (13) | C14—C15—H15A | 119.0 |
N2—Cu1—N4 | 116.94 (13) | C16—C15—H15A | 119.0 |
O2—Cu1—N1 | 173.53 (11) | C15—C16—C17 | 117.2 (4) |
N6—Cu1—N1 | 80.19 (12) | C15—C16—H16A | 121.4 |
N2—Cu1—N1 | 79.24 (13) | C17—C16—H16A | 121.4 |
N4—Cu1—N1 | 78.86 (12) | C16—C17—N4 | 131.0 (4) |
O7—Cl1—O6 | 110.1 (4) | C16—C17—C12 | 120.4 (4) |
O7—Cl1—O4 | 116.7 (4) | N4—C17—C12 | 108.5 (4) |
O6—Cl1—O4 | 109.9 (4) | N5—C18—H18A | 109.5 |
O7—Cl1—O5 | 103.9 (3) | N5—C18—H18B | 109.5 |
O6—Cl1—O5 | 109.0 (4) | H18A—C18—H18B | 109.5 |
O4—Cl1—O5 | 106.7 (4) | N5—C18—H18C | 109.5 |
C28—O1—H1 | 109.5 | H18A—C18—H18C | 109.5 |
C36—O2—Cu1 | 125.2 (2) | H18B—C18—H18C | 109.5 |
C1—N1—C10 | 111.2 (3) | C20—C19—N1 | 107.7 (3) |
C1—N1—C19 | 110.5 (3) | C20—C19—H19A | 110.2 |
C10—N1—C19 | 111.0 (3) | N1—C19—H19A | 110.2 |
C1—N1—Cu1 | 107.4 (2) | C20—C19—H19B | 110.2 |
C10—N1—Cu1 | 107.1 (2) | N1—C19—H19B | 110.2 |
C19—N1—Cu1 | 109.6 (2) | H19A—C19—H19B | 108.5 |
C2—N2—C3 | 105.5 (3) | N6—C20—N7 | 112.7 (3) |
C2—N2—Cu1 | 111.9 (3) | N6—C20—C19 | 121.5 (3) |
C3—N2—Cu1 | 141.9 (3) | N7—C20—C19 | 125.6 (3) |
C2—N3—C8 | 106.7 (3) | C22—C21—N6 | 130.9 (3) |
C2—N3—C9 | 127.6 (4) | C22—C21—C26 | 120.4 (4) |
C8—N3—C9 | 125.6 (4) | N6—C21—C26 | 108.6 (3) |
C11—N4—C17 | 106.1 (3) | C23—C22—C21 | 117.2 (4) |
C11—N4—Cu1 | 111.3 (3) | C23—C22—H22A | 121.4 |
C17—N4—Cu1 | 142.5 (3) | C21—C22—H22A | 121.4 |
C11—N5—C12 | 106.6 (3) | C22—C23—C24 | 121.7 (4) |
C11—N5—C18 | 126.2 (4) | C22—C23—H23A | 119.1 |
C12—N5—C18 | 127.1 (4) | C24—C23—H23A | 119.1 |
C20—N6—C21 | 105.9 (3) | C25—C24—C23 | 122.0 (4) |
C20—N6—Cu1 | 114.1 (2) | C25—C24—H24A | 119.0 |
C21—N6—Cu1 | 140.0 (2) | C23—C24—H24A | 119.0 |
C20—N7—C26 | 106.6 (3) | C24—C25—C26 | 116.4 (4) |
C20—N7—C27 | 127.2 (4) | C24—C25—H25A | 121.8 |
C26—N7—C27 | 126.2 (3) | C26—C25—H25A | 121.8 |
C37—N8—C38 | 123.5 (10) | N7—C26—C21 | 106.1 (3) |
C37—N8—C39 | 116.0 (9) | N7—C26—C25 | 131.5 (4) |
C38—N8—C39 | 120.0 (8) | C21—C26—C25 | 122.3 (4) |
C2—C1—N1 | 107.9 (3) | N7—C27—H27A | 109.5 |
C2—C1—H1A | 110.1 | N7—C27—H27B | 109.5 |
N1—C1—H1A | 110.1 | H27A—C27—H27B | 109.5 |
C2—C1—H1B | 110.1 | N7—C27—H27C | 109.5 |
N1—C1—H1B | 110.1 | H27A—C27—H27C | 109.5 |
H1A—C1—H1B | 108.4 | H27B—C27—H27C | 109.5 |
N2—C2—N3 | 113.1 (4) | O1—C28—C33 | 122.8 (3) |
N2—C2—C1 | 121.7 (4) | O1—C28—C29 | 118.3 (3) |
N3—C2—C1 | 125.2 (4) | C33—C28—C29 | 118.8 (3) |
C4—C3—C8 | 120.9 (4) | C30—C29—C28 | 120.5 (4) |
C4—C3—N2 | 130.5 (4) | C30—C29—H29A | 119.7 |
C8—C3—N2 | 108.5 (4) | C28—C29—H29A | 119.7 |
C3—C4—C5 | 117.0 (4) | C29—C30—C31 | 121.2 (3) |
C3—C4—H4A | 121.5 | C29—C30—H30A | 119.4 |
C5—C4—H4A | 121.5 | C31—C30—H30A | 119.4 |
C4—C5—C6 | 120.6 (4) | C32—C31—C30 | 117.0 (3) |
C4—C5—H5A | 119.7 | C32—C31—C34 | 119.6 (3) |
C6—C5—H5A | 119.7 | C30—C31—C34 | 123.4 (3) |
C7—C6—C5 | 121.5 (4) | C33—C32—C31 | 122.1 (4) |
C7—C6—H6A | 119.2 | C33—C32—H32A | 118.9 |
C5—C6—H6A | 119.2 | C31—C32—H32A | 118.9 |
C6—C7—C8 | 117.4 (5) | C28—C33—C32 | 120.3 (3) |
C6—C7—H7A | 121.3 | C28—C33—H33A | 119.8 |
C8—C7—H7A | 121.3 | C32—C33—H33A | 119.8 |
C7—C8—C3 | 122.5 (4) | C35—C34—C31 | 129.8 (4) |
C7—C8—N3 | 131.3 (4) | C35—C34—H34A | 115.1 |
C3—C8—N3 | 106.2 (4) | C31—C34—H34A | 115.1 |
N3—C9—H9A | 109.5 | C34—C35—C36 | 122.8 (4) |
N3—C9—H9B | 109.5 | C34—C35—H35A | 118.6 |
H9A—C9—H9B | 109.5 | C36—C35—H35A | 118.6 |
N3—C9—H9C | 109.5 | O3—C36—O2 | 123.5 (3) |
H9A—C9—H9C | 109.5 | O3—C36—C35 | 121.5 (3) |
H9B—C9—H9C | 109.5 | O2—C36—C35 | 114.9 (3) |
N1—C10—C11 | 107.6 (3) | O8—C37—N8 | 126.4 (12) |
N1—C10—H10A | 110.2 | O8—C37—H37A | 116.8 |
C11—C10—H10A | 110.2 | N8—C37—H37A | 116.8 |
N1—C10—H10B | 110.2 | N8—C38—H38A | 109.5 |
C11—C10—H10B | 110.2 | N8—C38—H38B | 109.5 |
H10A—C10—H10B | 108.5 | H38A—C38—H38B | 109.5 |
N4—C11—N5 | 112.4 (4) | N8—C38—H38C | 109.5 |
N4—C11—C10 | 121.5 (4) | H38A—C38—H38C | 109.5 |
N5—C11—C10 | 126.0 (4) | H38B—C38—H38C | 109.5 |
N5—C12—C13 | 131.1 (4) | N8—C39—H39A | 109.5 |
N5—C12—C17 | 106.3 (3) | N8—C39—H39B | 109.5 |
C13—C12—C17 | 122.6 (4) | H39A—C39—H39B | 109.5 |
C14—C13—C12 | 115.7 (4) | N8—C39—H39C | 109.5 |
C14—C13—H13A | 122.1 | H39A—C39—H39C | 109.5 |
C12—C13—H13A | 122.1 | H39B—C39—H39C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 1.93 | 2.742 (4) | 174.1 |
Symmetry code: (i) −x, y+1/2, −z−1/2. |