In the complex, bis[N,N'-bis(pyridin-2-ylmethyl)pyrazine-2,3-dicarboxamide]cobalt(III) tris(perchlorate) acetonitrile 3.5-solvate, [Co(C18H16N6O2)2](ClO4)3·3.5CH3CN, the result of the reaction of Co(ClO4)2 with the ligand N,N'-bis(pyridin-2-ylmethyl)pyrazine-2,3-dicarboxamide, the CoII atom has been oxidized to CoIII and has a slightly distorted octahedral coordination geometry. In each ligand, one amide NH proton has been transferred to a non-coordinated pyridine ring, thereby producing a zwitterion. This proton is hydrogen bonded to the carbonyl O atom of the adjacent deprotonated (pyridin-2-ylmethyl)amide substiutent involved in coordination.
Supporting information
CCDC reference: 234799
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.009 Å
- Disorder in solvent or counterion
- R factor = 0.048
- wR factor = 0.119
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
| Author Response: ...With the Stoe Image Plate diffraction System Mark I it is
only possible to access a maximum of ca. 93% of the Ewald sphere
in the triclinic system, if maximum atomic resolution, 0.81 \%A,
is to be obtained. Here Theta max. was 26.02\%.
|
PLAT214_ALERT_2_A Atom O37 (Anion/Solvent) ADP max/min Ratio 6.60 prolat
| Author Response: ...This concerns a highly disordered perchlorate anion where I have
tried to split the atoms to componsate for the disorder. Unfortunattely atom
O37 is prolate.
|
PLAT773_ALERT_2_A Suspect C-C Bond in CIF C52 - C52 = 1.96 Ang.
| Author Response: ...This concerns a partially occupied acteonitrile molecule
which is disorderd about a center of symmetry.
|
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc.
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 26.02
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 9551
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 10347
Completeness (_total/calc) 92.31%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92
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
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.99 Ratio
PLAT221_ALERT_4_C Large Solvent/Anion O Ueq(max)/Ueq(min) ... 3.91 Ratio
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... O31
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... O36
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... O37
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl3A
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl3B
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl2
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C42
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C45
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C48
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C51
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O32
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C22 - C32 = 1.53 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C4 = 2.98 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C24 = 2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O34 .. C52 = 2.96 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C8 .. C51 = 3.18 Ang.
PLAT731_ALERT_1_C Bond Calc 0.90(6), Rep 0.90(2) ...... 3.00 su-Rat
N6 -H6N 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.87(7), Rep 0.88(2) ...... 3.50 su-Rat
N25 -H25N 1.555 1.555
3 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
28 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 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
13 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: EXPOSE (Stoe & Cie, 2000); cell refinement: CELL (Stoe & Cie, 2000); data reduction: INTEGRATE (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
bis[
N,
N'-bis(pyridin-2-ylmethyl)pyrazine-2,3-dicarboxamide]cobalt(III) tris(perchlorate) acetonitrile 3.5-solvate
top
Crystal data top
[Co(C18H16N6O2)2](ClO4)3·3.5C2H3N | Z = 2 |
Mr = 1197.71 | F(000) = 1230 |
Triclinic, P1 | Dx = 1.519 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 13.174 (5) Å | Cell parameters from 6268 reflections |
b = 14.061 (5) Å | θ = 1.9–26.0° |
c = 15.905 (5) Å | µ = 0.56 mm−1 |
α = 100.197 (5)° | T = 153 K |
β = 111.189 (5)° | Rod, dark_red |
γ = 99.505 (5)° | 0.50 × 0.25 × 0.15 mm |
V = 2618.0 (16) Å3 | |
Data collection top
Stoe IPDS diffractometer | 3742 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.087 |
Graphite monochromator | θmax = 26.0°, θmin = 2.0° |
Detector resolution: 0.81Å pixels mm-1 | h = −16→16 |
φ oscillation scans | k = −17→17 |
20558 measured reflections | l = −17→19 |
9551 independent 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = [exp{3(sinθ/λ)2}]/[σ2(Fo2) + (0.032P)2] where P = (Fo2 + 2Fc2)/3 |
9551 reflections | (Δ/σ)max = 0.006 |
787 parameters | Δρmax = 0.66 e Å−3 |
5 restraints | Δρmin = −0.44 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) |
Co1 | 0.13188 (6) | 1.01687 (5) | 0.29214 (5) | 0.02931 (18) | |
O1 | 0.0430 (3) | 1.2569 (2) | 0.3898 (3) | 0.0407 (9) | |
O2 | −0.0790 (3) | 1.2090 (3) | 0.5307 (3) | 0.0499 (10) | |
O3 | 0.0537 (3) | 0.7455 (2) | 0.1227 (2) | 0.0358 (8) | |
O4 | −0.0591 (3) | 0.7569 (2) | −0.0951 (2) | 0.0416 (9) | |
N1 | 0.0166 (3) | 0.9934 (3) | 0.3416 (3) | 0.0292 (9) | |
N2 | −0.1453 (4) | 0.9899 (3) | 0.4144 (3) | 0.0414 (11) | |
N3 | 0.1319 (3) | 1.1508 (3) | 0.3311 (3) | 0.0301 (10) | |
N4 | 0.2455 (3) | 1.0742 (3) | 0.2526 (3) | 0.0340 (10) | |
N5 | −0.2021 (4) | 1.1958 (3) | 0.3836 (3) | 0.0405 (11) | |
H5N | −0.233 (4) | 1.162 (4) | 0.3234 (18) | 0.053 (18)* | |
N6 | −0.0909 (4) | 1.3784 (3) | 0.3815 (4) | 0.0456 (12) | |
H6N | −0.061 (5) | 1.325 (3) | 0.384 (5) | 0.09 (2)* | |
N21 | 0.0162 (3) | 0.9925 (3) | 0.1674 (3) | 0.0291 (9) | |
N22 | −0.1399 (3) | 0.9333 (3) | −0.0179 (3) | 0.0355 (10) | |
N23 | 0.1271 (3) | 0.8822 (3) | 0.2504 (3) | 0.0314 (10) | |
N24 | 0.2477 (3) | 1.0063 (3) | 0.4050 (3) | 0.0349 (10) | |
N25 | −0.1844 (4) | 0.6973 (3) | −0.0376 (3) | 0.0358 (10) | |
H25N | −0.219 (5) | 0.703 (5) | 0.000 (4) | 0.09 (2)* | |
N26 | −0.0853 (4) | 0.5638 (3) | 0.0492 (3) | 0.0358 (10) | |
H26N | −0.049 (4) | 0.6289 (18) | 0.069 (4) | 0.07 (2)* | |
C1 | −0.0086 (4) | 1.0803 (3) | 0.3727 (3) | 0.0297 (11) | |
C2 | −0.0897 (4) | 1.0756 (3) | 0.4091 (3) | 0.0330 (12) | |
C3 | −0.1196 (4) | 0.9071 (4) | 0.3835 (4) | 0.0403 (13) | |
H3A | −0.1564 | 0.8452 | 0.3877 | 0.048* | |
C4 | −0.0392 (4) | 0.9086 (3) | 0.3447 (3) | 0.0333 (12) | |
H4A | −0.0251 | 0.8478 | 0.3204 | 0.040* | |
C5 | 0.0580 (4) | 1.1714 (3) | 0.3658 (3) | 0.0287 (11) | |
C6 | 0.2032 (4) | 1.2268 (4) | 0.3126 (4) | 0.0381 (13) | |
H6A | 0.2559 | 1.2761 | 0.3714 | 0.046* | |
H6B | 0.1572 | 1.2623 | 0.2709 | 0.046* | |
C7 | 0.2665 (4) | 1.1740 (4) | 0.2666 (4) | 0.0362 (12) | |
C8 | 0.3451 (4) | 1.2250 (4) | 0.2400 (4) | 0.0502 (16) | |
H8A | 0.3586 | 1.2953 | 0.2492 | 0.068 (19)* | |
C9 | 0.4035 (5) | 1.1720 (4) | 0.1998 (5) | 0.0587 (18) | |
H9A | 0.4577 | 1.2054 | 0.1814 | 0.070* | |
C10 | 0.3813 (5) | 1.0704 (4) | 0.1872 (4) | 0.0495 (15) | |
H10A | 0.4211 | 1.0329 | 0.1607 | 0.059* | |
C11 | 0.3025 (4) | 1.0235 (4) | 0.2125 (4) | 0.0405 (13) | |
H11A | 0.2869 | 0.9529 | 0.2018 | 0.049* | |
C12 | −0.1213 (4) | 1.1683 (4) | 0.4471 (4) | 0.0358 (12) | |
C13 | −0.2432 (5) | 1.2817 (4) | 0.4073 (4) | 0.0492 (15) | |
H13A | −0.2334 | 1.2928 | 0.4733 | 0.059* | |
H13B | −0.3248 | 1.2665 | 0.3684 | 0.059* | |
C14 | −0.1873 (5) | 1.3747 (4) | 0.3947 (4) | 0.0468 (15) | |
C15 | −0.2231 (6) | 1.4623 (5) | 0.3986 (5) | 0.070 (2) | |
H15A | −0.2909 | 1.4637 | 0.4066 | 0.084* | |
C16 | −0.1620 (6) | 1.5465 (5) | 0.3912 (6) | 0.079 (2) | |
H16A | −0.1864 | 1.6064 | 0.3966 | 0.094* | |
C17 | −0.0660 (5) | 1.5457 (4) | 0.3760 (5) | 0.0668 (19) | |
H17A | −0.0248 | 1.6033 | 0.3683 | 0.080* | |
C18 | −0.0317 (5) | 1.4589 (4) | 0.3722 (4) | 0.0532 (16) | |
H18A | 0.0351 | 1.4562 | 0.3629 | 0.064* | |
C21 | −0.0062 (4) | 0.8982 (3) | 0.1135 (3) | 0.0266 (11) | |
C22 | −0.0829 (4) | 0.8708 (3) | 0.0226 (3) | 0.0292 (11) | |
C23 | −0.1190 (4) | 1.0236 (3) | 0.0372 (4) | 0.0359 (13) | |
H23A | −0.1595 | 1.0693 | 0.0123 | 0.043* | |
C24 | −0.0413 (4) | 1.0542 (3) | 0.1287 (4) | 0.0320 (12) | |
H24A | −0.0288 | 1.1200 | 0.1646 | 0.038* | |
C25 | 0.0622 (4) | 0.8342 (3) | 0.1634 (4) | 0.0304 (11) | |
C26 | 0.2004 (4) | 0.8354 (4) | 0.3134 (3) | 0.0378 (12) | |
H26A | 0.2500 | 0.8090 | 0.2861 | 0.045* | |
H26B | 0.1555 | 0.7795 | 0.3251 | 0.045* | |
C27 | 0.2683 (4) | 0.9140 (3) | 0.4016 (4) | 0.0355 (12) | |
C28 | 0.3492 (4) | 0.8975 (4) | 0.4786 (4) | 0.0449 (14) | |
H28A | 0.3623 | 0.8329 | 0.4770 | 0.054* | |
C29 | 0.4106 (4) | 0.9746 (5) | 0.5570 (4) | 0.0494 (15) | |
H29A | 0.4666 | 0.9636 | 0.6094 | 0.059* | |
C30 | 0.3906 (4) | 1.0678 (4) | 0.5594 (4) | 0.0477 (14) | |
H30A | 0.4326 | 1.1219 | 0.6130 | 0.057* | |
C31 | 0.3079 (4) | 1.0808 (4) | 0.4820 (4) | 0.0384 (13) | |
H31A | 0.2933 | 1.1449 | 0.4834 | 0.046* | |
C32 | −0.1061 (4) | 0.7680 (3) | −0.0415 (3) | 0.0305 (11) | |
C33 | −0.2151 (4) | 0.5949 (3) | −0.0919 (4) | 0.0410 (13) | |
H33A | −0.1843 | 0.5918 | −0.1404 | 0.049* | |
H33B | −0.2980 | 0.5720 | −0.1239 | 0.049* | |
C34 | −0.1722 (4) | 0.5257 (3) | −0.0330 (4) | 0.0363 (12) | |
C35 | −0.2168 (5) | 0.4230 (4) | −0.0601 (4) | 0.0440 (14) | |
H35A | −0.2785 | 0.3929 | −0.1184 | 0.053* | |
C36 | −0.1716 (5) | 0.3649 (4) | −0.0022 (5) | 0.0471 (15) | |
H36A | −0.2011 | 0.2945 | −0.0215 | 0.057* | |
C37 | −0.0838 (5) | 0.4082 (4) | 0.0834 (4) | 0.0436 (14) | |
H37A | −0.0537 | 0.3689 | 0.1245 | 0.052* | |
C38 | −0.0413 (4) | 0.5090 (4) | 0.1075 (4) | 0.0429 (14) | |
H38A | 0.0198 | 0.5406 | 0.1659 | 0.051* | |
Cl1 | 0.75860 (14) | 0.69518 (11) | 0.16511 (11) | 0.0552 (4) | |
O11 | 0.8585 (5) | 0.6721 (4) | 0.2182 (4) | 0.1033 (19) | |
O12 | 0.7923 (4) | 0.7862 (3) | 0.1416 (3) | 0.0685 (13) | |
O13 | 0.6943 (5) | 0.7125 (4) | 0.2177 (4) | 0.109 (2) | |
O14 | 0.6985 (4) | 0.6192 (4) | 0.0814 (4) | 0.0963 (18) | |
Cl2 | 0.71679 (15) | 0.15619 (14) | 0.13896 (12) | 0.0679 (5) | |
O21A | 0.6552 (10) | 0.1983 (9) | 0.1806 (7) | 0.092 (4) | 0.724 (18) |
O22A | 0.6531 (11) | 0.0915 (13) | 0.0471 (8) | 0.136 (6) | 0.724 (18) |
O23A | 0.8068 (9) | 0.2220 (7) | 0.1413 (10) | 0.127 (6) | 0.724 (18) |
O21B | 0.761 (5) | 0.2684 (15) | 0.182 (2) | 0.21 (3) | 0.276 (18) |
O22B | 0.592 (3) | 0.137 (4) | 0.116 (4) | 0.153 (19) | 0.276 (18) |
O23B | 0.7058 (18) | 0.1579 (18) | 0.0517 (14) | 0.053 (7) | 0.276 (18) |
O24 | 0.7685 (4) | 0.0922 (3) | 0.1940 (3) | 0.0724 (13) | |
N41 | 0.4991 (7) | 0.3988 (5) | 0.1795 (7) | 0.126 (3) | |
C42 | 0.5442 (9) | 0.3937 (6) | 0.1313 (10) | 0.132 (5) | |
C43 | 0.5991 (11) | 0.3876 (7) | 0.0670 (10) | 0.189 (7) | |
H43A | 0.6652 | 0.4441 | 0.0904 | 0.284* | |
H43B | 0.5466 | 0.3896 | 0.0056 | 0.284* | |
H43C | 0.6226 | 0.3250 | 0.0616 | 0.284* | |
N44 | 0.6737 (7) | 0.6851 (6) | 0.4358 (5) | 0.112 (3) | |
C45 | 0.5978 (7) | 0.6615 (5) | 0.3673 (6) | 0.067 (2) | |
C46 | 0.5016 (6) | 0.6310 (6) | 0.2788 (5) | 0.079 (2) | |
H46A | 0.4722 | 0.6888 | 0.2658 | 0.119* | |
H46B | 0.4432 | 0.5800 | 0.2815 | 0.119* | |
H46C | 0.5243 | 0.6035 | 0.2293 | 0.119* | |
N47 | 0.4117 (6) | 0.8212 (5) | 0.1841 (6) | 0.101 (2) | |
C48 | 0.4784 (7) | 0.8482 (5) | 0.1582 (7) | 0.084 (3) | |
C49 | 0.5630 (7) | 0.8828 (7) | 0.1223 (9) | 0.145 (5) | |
H49A | 0.6382 | 0.8864 | 0.1678 | 0.218* | |
H49B | 0.5590 | 0.9490 | 0.1120 | 0.218* | |
H49C | 0.5478 | 0.8359 | 0.0631 | 0.218* | |
N50 | 0.5055 (9) | 0.2621 (8) | 0.4511 (8) | 0.071 (3)* | 0.50 |
C51 | 0.4990 (10) | 0.3402 (9) | 0.4514 (9) | 0.053 (3)* | 0.50 |
C52 | 0.5067 (16) | 0.4361 (14) | 0.4690 (13) | 0.136 (7)* | 0.50 |
H52A | 0.5703 | 0.4702 | 0.4583 | 0.204* | 0.50 |
H52B | 0.5185 | 0.4614 | 0.5342 | 0.204* | 0.50 |
H52C | 0.4371 | 0.4487 | 0.4279 | 0.204* | 0.50 |
Cl3A | 0.2496 (6) | 0.5732 (4) | 0.3486 (5) | 0.0586 (17) | 0.50 |
Cl3B | 0.2368 (5) | 0.5275 (4) | 0.3280 (4) | 0.0458 (14) | 0.50 |
O31 | 0.2450 (5) | 0.5986 (4) | 0.2717 (6) | 0.121 (2) | |
O32 | 0.1379 (8) | 0.4557 (6) | 0.2726 (6) | 0.109 (3) | 0.75 |
O33 | 0.2437 (8) | 0.5597 (8) | 0.4220 (6) | 0.079 (3) | 0.50 |
O34 | 0.3196 (7) | 0.4858 (6) | 0.3275 (6) | 0.070 (3) | 0.50 |
O35 | 0.1570 (7) | 0.6080 (6) | 0.3541 (7) | 0.074 (3) | 0.50 |
O36 | 0.3473 (9) | 0.6323 (9) | 0.4165 (9) | 0.125 (5) | 0.50 |
O37 | 0.2320 (16) | 0.4676 (14) | 0.351 (2) | 0.104 (11) | 0.25 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0369 (4) | 0.0284 (3) | 0.0321 (4) | 0.0138 (3) | 0.0196 (3) | 0.0135 (3) |
O1 | 0.045 (2) | 0.0258 (17) | 0.060 (3) | 0.0154 (16) | 0.0278 (19) | 0.0124 (17) |
O2 | 0.071 (3) | 0.050 (2) | 0.041 (2) | 0.033 (2) | 0.029 (2) | 0.013 (2) |
O3 | 0.045 (2) | 0.0209 (16) | 0.047 (2) | 0.0151 (15) | 0.0216 (18) | 0.0101 (16) |
O4 | 0.066 (3) | 0.0305 (18) | 0.043 (2) | 0.0156 (17) | 0.037 (2) | 0.0106 (17) |
N1 | 0.037 (2) | 0.025 (2) | 0.026 (2) | 0.0094 (18) | 0.0115 (19) | 0.0072 (18) |
N2 | 0.046 (3) | 0.039 (2) | 0.049 (3) | 0.011 (2) | 0.029 (2) | 0.014 (2) |
N3 | 0.035 (2) | 0.033 (2) | 0.032 (2) | 0.0127 (19) | 0.022 (2) | 0.0105 (19) |
N4 | 0.037 (2) | 0.038 (2) | 0.041 (3) | 0.020 (2) | 0.024 (2) | 0.020 (2) |
N5 | 0.045 (3) | 0.044 (3) | 0.045 (3) | 0.023 (2) | 0.024 (3) | 0.017 (3) |
N6 | 0.057 (3) | 0.037 (3) | 0.066 (3) | 0.024 (2) | 0.042 (3) | 0.024 (2) |
N21 | 0.040 (2) | 0.027 (2) | 0.036 (3) | 0.0154 (18) | 0.026 (2) | 0.0164 (19) |
N22 | 0.044 (3) | 0.035 (2) | 0.036 (3) | 0.019 (2) | 0.019 (2) | 0.015 (2) |
N23 | 0.041 (3) | 0.035 (2) | 0.030 (3) | 0.020 (2) | 0.019 (2) | 0.017 (2) |
N24 | 0.035 (2) | 0.036 (2) | 0.043 (3) | 0.011 (2) | 0.023 (2) | 0.014 (2) |
N25 | 0.047 (3) | 0.028 (2) | 0.040 (3) | 0.015 (2) | 0.022 (2) | 0.012 (2) |
N26 | 0.039 (3) | 0.028 (2) | 0.042 (3) | 0.008 (2) | 0.018 (2) | 0.009 (2) |
C1 | 0.035 (3) | 0.024 (2) | 0.032 (3) | 0.010 (2) | 0.015 (2) | 0.007 (2) |
C2 | 0.038 (3) | 0.036 (3) | 0.035 (3) | 0.013 (2) | 0.022 (2) | 0.011 (2) |
C3 | 0.044 (3) | 0.036 (3) | 0.052 (4) | 0.012 (2) | 0.029 (3) | 0.017 (3) |
C4 | 0.045 (3) | 0.027 (2) | 0.034 (3) | 0.010 (2) | 0.020 (3) | 0.012 (2) |
C5 | 0.032 (3) | 0.027 (2) | 0.025 (3) | 0.005 (2) | 0.011 (2) | 0.007 (2) |
C6 | 0.042 (3) | 0.037 (3) | 0.048 (3) | 0.011 (2) | 0.028 (3) | 0.019 (3) |
C7 | 0.037 (3) | 0.041 (3) | 0.044 (3) | 0.019 (2) | 0.022 (3) | 0.023 (3) |
C8 | 0.051 (4) | 0.045 (3) | 0.083 (5) | 0.019 (3) | 0.045 (3) | 0.038 (3) |
C9 | 0.059 (4) | 0.066 (4) | 0.089 (5) | 0.027 (3) | 0.055 (4) | 0.048 (4) |
C10 | 0.056 (4) | 0.063 (4) | 0.065 (4) | 0.038 (3) | 0.044 (3) | 0.039 (3) |
C11 | 0.049 (3) | 0.050 (3) | 0.042 (3) | 0.026 (3) | 0.027 (3) | 0.025 (3) |
C12 | 0.042 (3) | 0.038 (3) | 0.039 (3) | 0.014 (2) | 0.026 (3) | 0.013 (3) |
C13 | 0.050 (4) | 0.045 (3) | 0.068 (4) | 0.022 (3) | 0.033 (3) | 0.020 (3) |
C14 | 0.056 (4) | 0.050 (3) | 0.056 (4) | 0.032 (3) | 0.034 (3) | 0.023 (3) |
C15 | 0.075 (5) | 0.063 (4) | 0.116 (6) | 0.045 (4) | 0.065 (5) | 0.043 (4) |
C16 | 0.085 (5) | 0.049 (4) | 0.139 (7) | 0.045 (4) | 0.067 (5) | 0.040 (4) |
C17 | 0.074 (5) | 0.049 (4) | 0.104 (6) | 0.032 (3) | 0.049 (4) | 0.037 (4) |
C18 | 0.066 (4) | 0.049 (3) | 0.074 (5) | 0.030 (3) | 0.047 (4) | 0.031 (3) |
C21 | 0.038 (3) | 0.020 (2) | 0.034 (3) | 0.012 (2) | 0.025 (2) | 0.011 (2) |
C22 | 0.044 (3) | 0.025 (2) | 0.030 (3) | 0.015 (2) | 0.023 (2) | 0.010 (2) |
C23 | 0.049 (3) | 0.028 (3) | 0.035 (3) | 0.017 (2) | 0.019 (3) | 0.009 (3) |
C24 | 0.044 (3) | 0.024 (2) | 0.038 (3) | 0.016 (2) | 0.023 (3) | 0.011 (2) |
C25 | 0.040 (3) | 0.032 (3) | 0.036 (3) | 0.017 (2) | 0.026 (3) | 0.022 (3) |
C26 | 0.045 (3) | 0.046 (3) | 0.035 (3) | 0.019 (3) | 0.021 (3) | 0.024 (3) |
C27 | 0.035 (3) | 0.039 (3) | 0.048 (4) | 0.017 (2) | 0.024 (3) | 0.027 (3) |
C28 | 0.037 (3) | 0.055 (3) | 0.054 (4) | 0.018 (3) | 0.018 (3) | 0.035 (3) |
C29 | 0.031 (3) | 0.076 (4) | 0.041 (4) | 0.012 (3) | 0.007 (3) | 0.030 (3) |
C30 | 0.038 (3) | 0.055 (4) | 0.044 (4) | 0.005 (3) | 0.009 (3) | 0.019 (3) |
C31 | 0.040 (3) | 0.039 (3) | 0.044 (4) | 0.012 (3) | 0.022 (3) | 0.017 (3) |
C32 | 0.043 (3) | 0.023 (2) | 0.027 (3) | 0.012 (2) | 0.013 (2) | 0.010 (2) |
C33 | 0.046 (3) | 0.030 (3) | 0.040 (3) | 0.005 (2) | 0.016 (3) | 0.002 (2) |
C34 | 0.042 (3) | 0.031 (3) | 0.040 (3) | 0.011 (2) | 0.024 (3) | 0.002 (3) |
C35 | 0.047 (3) | 0.034 (3) | 0.050 (4) | 0.005 (3) | 0.023 (3) | 0.008 (3) |
C36 | 0.054 (4) | 0.026 (3) | 0.073 (5) | 0.010 (3) | 0.039 (4) | 0.009 (3) |
C37 | 0.049 (3) | 0.031 (3) | 0.063 (4) | 0.017 (3) | 0.032 (3) | 0.017 (3) |
C38 | 0.044 (3) | 0.044 (3) | 0.052 (4) | 0.024 (3) | 0.023 (3) | 0.022 (3) |
Cl1 | 0.0697 (10) | 0.0526 (9) | 0.0581 (10) | 0.0154 (8) | 0.0408 (9) | 0.0172 (8) |
O11 | 0.130 (5) | 0.096 (4) | 0.082 (4) | 0.064 (4) | 0.022 (4) | 0.029 (3) |
O12 | 0.096 (3) | 0.056 (2) | 0.086 (4) | 0.025 (2) | 0.062 (3) | 0.038 (2) |
O13 | 0.148 (5) | 0.098 (4) | 0.141 (5) | 0.026 (3) | 0.131 (5) | 0.030 (4) |
O14 | 0.091 (4) | 0.082 (3) | 0.086 (4) | −0.028 (3) | 0.042 (3) | −0.019 (3) |
Cl2 | 0.0702 (12) | 0.0880 (12) | 0.0574 (12) | 0.0220 (10) | 0.0357 (10) | 0.0244 (11) |
O21A | 0.084 (7) | 0.169 (11) | 0.084 (7) | 0.094 (8) | 0.065 (6) | 0.058 (7) |
O22A | 0.109 (9) | 0.181 (13) | 0.065 (7) | 0.041 (9) | −0.006 (6) | −0.008 (8) |
O23A | 0.132 (9) | 0.068 (7) | 0.273 (16) | 0.042 (6) | 0.156 (11) | 0.091 (8) |
O21B | 0.31 (5) | 0.042 (13) | 0.11 (2) | 0.03 (2) | −0.07 (3) | −0.018 (14) |
O22B | 0.08 (2) | 0.27 (4) | 0.23 (4) | 0.11 (3) | 0.11 (3) | 0.22 (4) |
O23B | 0.056 (15) | 0.088 (15) | 0.035 (11) | 0.035 (12) | 0.028 (11) | 0.030 (12) |
O24 | 0.093 (3) | 0.072 (3) | 0.065 (3) | 0.033 (3) | 0.037 (3) | 0.026 (3) |
N41 | 0.112 (6) | 0.084 (5) | 0.241 (11) | 0.036 (4) | 0.126 (7) | 0.054 (6) |
C42 | 0.142 (9) | 0.060 (5) | 0.280 (16) | 0.049 (5) | 0.155 (10) | 0.075 (7) |
C43 | 0.273 (15) | 0.099 (7) | 0.37 (2) | 0.093 (9) | 0.282 (16) | 0.112 (10) |
N44 | 0.115 (6) | 0.126 (6) | 0.072 (5) | 0.079 (5) | 0.009 (4) | −0.012 (5) |
C45 | 0.082 (5) | 0.056 (4) | 0.075 (6) | 0.035 (4) | 0.041 (5) | 0.008 (4) |
C46 | 0.063 (5) | 0.092 (5) | 0.073 (5) | 0.003 (4) | 0.021 (4) | 0.024 (4) |
N47 | 0.084 (5) | 0.078 (5) | 0.134 (7) | 0.027 (4) | 0.033 (5) | 0.028 (4) |
C48 | 0.058 (5) | 0.045 (4) | 0.131 (8) | 0.017 (4) | 0.012 (5) | 0.035 (4) |
C49 | 0.072 (6) | 0.118 (7) | 0.273 (16) | 0.043 (6) | 0.064 (8) | 0.112 (9) |
Cl3A | 0.074 (4) | 0.071 (4) | 0.063 (4) | 0.040 (4) | 0.046 (4) | 0.034 (4) |
Cl3B | 0.035 (2) | 0.059 (4) | 0.041 (3) | 0.010 (3) | 0.0116 (18) | 0.015 (3) |
O31 | 0.117 (5) | 0.116 (5) | 0.154 (7) | 0.031 (4) | 0.065 (5) | 0.070 (5) |
O32 | 0.125 (7) | 0.109 (6) | 0.103 (7) | 0.024 (6) | 0.062 (6) | 0.021 (5) |
O33 | 0.071 (7) | 0.112 (8) | 0.039 (5) | −0.007 (6) | 0.037 (5) | −0.020 (5) |
O34 | 0.061 (6) | 0.066 (6) | 0.086 (7) | 0.004 (5) | 0.047 (5) | 0.000 (5) |
O35 | 0.058 (6) | 0.071 (6) | 0.112 (8) | 0.033 (5) | 0.049 (6) | 0.022 (6) |
O36 | 0.050 (6) | 0.127 (10) | 0.132 (11) | 0.018 (6) | 0.010 (7) | −0.066 (9) |
O37 | 0.048 (13) | 0.030 (10) | 0.20 (3) | 0.001 (9) | 0.003 (15) | 0.070 (16) |
Geometric parameters (Å, º) top
Co1—N3 | 1.875 (4) | C26—H26A | 0.9900 |
Co1—N23 | 1.875 (4) | C26—H26B | 0.9900 |
Co1—N4 | 1.936 (4) | C27—C28 | 1.388 (7) |
Co1—N24 | 1.939 (4) | C28—C29 | 1.374 (8) |
Co1—N21 | 1.944 (4) | C28—H28A | 0.9500 |
Co1—N1 | 1.956 (4) | C29—C30 | 1.374 (8) |
O1—C5 | 1.264 (5) | C29—H29A | 0.9500 |
O2—C12 | 1.223 (6) | C30—C31 | 1.383 (7) |
O3—C25 | 1.266 (5) | C30—H30A | 0.9500 |
O4—C32 | 1.224 (5) | C31—H31A | 0.9500 |
N1—C4 | 1.312 (6) | C33—C34 | 1.505 (7) |
N1—C1 | 1.373 (5) | C33—H33A | 0.9900 |
N2—C3 | 1.327 (6) | C33—H33B | 0.9900 |
N2—C2 | 1.335 (6) | C34—C35 | 1.390 (7) |
N3—C5 | 1.327 (5) | C35—C36 | 1.379 (8) |
N3—C6 | 1.447 (6) | C35—H35A | 0.9500 |
N4—C7 | 1.346 (6) | C36—C37 | 1.378 (8) |
N4—C11 | 1.358 (6) | C36—H36A | 0.9500 |
N5—C12 | 1.342 (7) | C37—C38 | 1.364 (7) |
N5—C13 | 1.448 (6) | C37—H37A | 0.9500 |
N5—H5N | 0.90 (2) | C38—H38A | 0.9500 |
N6—C18 | 1.326 (7) | Cl1—O13 | 1.409 (4) |
N6—C14 | 1.355 (6) | Cl1—O11 | 1.410 (5) |
N6—H6N | 0.90 (2) | Cl1—O14 | 1.412 (5) |
N21—C24 | 1.333 (6) | Cl1—O12 | 1.440 (4) |
N21—C21 | 1.366 (5) | Cl2—O23B | 1.347 (16) |
N22—C23 | 1.332 (6) | Cl2—O21A | 1.362 (7) |
N22—C22 | 1.349 (6) | Cl2—O23A | 1.363 (8) |
N23—C25 | 1.313 (6) | Cl2—O22A | 1.435 (10) |
N23—C26 | 1.454 (6) | Cl2—O24 | 1.446 (5) |
N24—C31 | 1.340 (6) | Cl2—O22B | 1.52 (3) |
N24—C27 | 1.365 (6) | Cl2—O21B | 1.52 (2) |
N25—C32 | 1.337 (6) | N41—C42 | 1.127 (11) |
N25—C33 | 1.449 (6) | C42—C43 | 1.449 (13) |
N25—H25N | 0.88 (2) | C43—H43A | 0.9800 |
N26—C34 | 1.332 (7) | C43—H43B | 0.9800 |
N26—C38 | 1.341 (7) | C43—H43C | 0.9800 |
N26—H26N | 0.90 (2) | N44—C45 | 1.128 (9) |
C1—C2 | 1.386 (6) | C45—C46 | 1.444 (11) |
C1—C5 | 1.473 (6) | C46—H46A | 0.9800 |
C2—C12 | 1.523 (6) | C46—H46B | 0.9800 |
C3—C4 | 1.404 (6) | C46—H46C | 0.9800 |
C3—H3A | 0.9500 | N47—C48 | 1.138 (10) |
C4—H4A | 0.9500 | C48—C49 | 1.478 (13) |
C6—C7 | 1.495 (6) | C49—H49A | 0.9800 |
C6—H6A | 0.9900 | C49—H49B | 0.9800 |
C6—H6B | 0.9900 | C49—H49C | 0.9800 |
C7—C8 | 1.394 (7) | N50—C51 | 1.115 (14) |
C8—C9 | 1.390 (7) | C51—C52 | 1.307 (19) |
C8—H8A | 0.9500 | C52—C52i | 1.96 (4) |
C9—C10 | 1.373 (7) | C52—H52A | 0.9800 |
C9—H9A | 0.9500 | C52—H52B | 0.9800 |
C10—C11 | 1.358 (7) | C52—H52C | 0.9800 |
C10—H10A | 0.9500 | Cl3A—Cl3B | 0.631 (5) |
C11—H11A | 0.9500 | Cl3A—O33 | 1.242 (12) |
C13—C14 | 1.476 (7) | Cl3A—O31 | 1.317 (10) |
C13—H13A | 0.9900 | Cl3A—O36 | 1.356 (13) |
C13—H13B | 0.9900 | Cl3A—O35 | 1.412 (10) |
C14—C15 | 1.388 (7) | Cl3A—O37 | 1.473 (16) |
C15—C16 | 1.366 (9) | Cl3A—O34 | 1.710 (9) |
C15—H15A | 0.9500 | Cl3A—O32 | 1.886 (10) |
C16—C17 | 1.372 (8) | Cl3B—O37 | 0.98 (2) |
C16—H16A | 0.9500 | Cl3B—O34 | 1.323 (10) |
C17—C18 | 1.370 (7) | Cl3B—O32 | 1.383 (10) |
C17—H17A | 0.9500 | Cl3B—O33 | 1.449 (9) |
C18—H18A | 0.9500 | Cl3B—O31 | 1.470 (9) |
C21—C22 | 1.370 (7) | Cl3B—O35 | 1.761 (9) |
C21—C25 | 1.502 (6) | Cl3B—O36 | 1.830 (11) |
C22—C32 | 1.526 (6) | O32—O37 | 1.36 (2) |
C23—C24 | 1.382 (7) | O33—O37 | 1.51 (3) |
C23—H23A | 0.9500 | O33—O35 | 1.600 (14) |
C24—H24A | 0.9500 | O33—O36 | 1.603 (16) |
C26—C27 | 1.486 (7) | O34—O37 | 1.33 (3) |
| | | |
N3—Co1—N23 | 178.17 (19) | N24—C27—C28 | 119.9 (5) |
N3—Co1—N4 | 82.89 (16) | N24—C27—C26 | 116.7 (4) |
N23—Co1—N4 | 97.92 (16) | C28—C27—C26 | 123.4 (4) |
N3—Co1—N24 | 98.94 (17) | C29—C28—C27 | 120.0 (5) |
N23—Co1—N24 | 82.71 (17) | C29—C28—H28A | 120.0 |
N4—Co1—N24 | 90.42 (17) | C27—C28—H28A | 120.0 |
N3—Co1—N21 | 95.70 (16) | C30—C29—C28 | 119.8 (5) |
N23—Co1—N21 | 82.65 (17) | C30—C29—H29A | 120.1 |
N4—Co1—N21 | 90.78 (17) | C28—C29—H29A | 120.1 |
N24—Co1—N21 | 165.34 (15) | C29—C30—C31 | 118.4 (5) |
N3—Co1—N1 | 82.90 (15) | C29—C30—H30A | 120.8 |
N23—Co1—N1 | 96.28 (16) | C31—C30—H30A | 120.8 |
N4—Co1—N1 | 165.79 (15) | N24—C31—C30 | 122.4 (5) |
N24—Co1—N1 | 92.05 (16) | N24—C31—H31A | 118.8 |
N21—Co1—N1 | 90.36 (16) | C30—C31—H31A | 118.8 |
C4—N1—C1 | 119.1 (4) | O4—C32—N25 | 125.1 (4) |
C4—N1—Co1 | 128.9 (3) | O4—C32—C22 | 120.0 (4) |
C1—N1—Co1 | 111.9 (3) | N25—C32—C22 | 114.7 (4) |
C3—N2—C2 | 117.3 (4) | N25—C33—C34 | 112.6 (4) |
C5—N3—C6 | 122.1 (4) | N25—C33—H33A | 109.1 |
C5—N3—Co1 | 118.7 (3) | C34—C33—H33A | 109.1 |
C6—N3—Co1 | 118.9 (3) | N25—C33—H33B | 109.1 |
C7—N4—C11 | 119.0 (4) | C34—C33—H33B | 109.1 |
C7—N4—Co1 | 114.7 (3) | H33A—C33—H33B | 107.8 |
C11—N4—Co1 | 126.3 (3) | N26—C34—C35 | 117.4 (5) |
C12—N5—C13 | 122.6 (5) | N26—C34—C33 | 118.9 (4) |
C12—N5—H5N | 121 (3) | C35—C34—C33 | 123.7 (5) |
C13—N5—H5N | 116 (3) | C36—C35—C34 | 120.0 (5) |
C18—N6—C14 | 124.0 (4) | C36—C35—H35A | 120.0 |
C18—N6—H6N | 117 (4) | C34—C35—H35A | 120.0 |
C14—N6—H6N | 119 (4) | C37—C36—C35 | 120.4 (5) |
C24—N21—C21 | 117.4 (4) | C37—C36—H36A | 119.8 |
C24—N21—Co1 | 129.2 (3) | C35—C36—H36A | 119.8 |
C21—N21—Co1 | 113.4 (3) | C38—C37—C36 | 118.2 (6) |
C23—N22—C22 | 115.5 (4) | C38—C37—H37A | 120.9 |
C25—N23—C26 | 121.6 (4) | C36—C37—H37A | 120.9 |
C25—N23—Co1 | 119.1 (3) | N26—C38—C37 | 120.3 (5) |
C26—N23—Co1 | 119.2 (3) | N26—C38—H38A | 119.8 |
C31—N24—C27 | 119.5 (5) | C37—C38—H38A | 119.8 |
C31—N24—Co1 | 125.7 (3) | O13—Cl1—O11 | 111.1 (4) |
C27—N24—Co1 | 114.8 (3) | O13—Cl1—O14 | 112.8 (3) |
C32—N25—C33 | 122.3 (4) | O11—Cl1—O14 | 109.7 (3) |
C32—N25—H25N | 127 (4) | O13—Cl1—O12 | 108.3 (3) |
C33—N25—H25N | 111 (4) | O11—Cl1—O12 | 106.4 (3) |
C34—N26—C38 | 123.7 (5) | O14—Cl1—O12 | 108.3 (3) |
C34—N26—H26N | 122 (4) | O21A—Cl2—O23A | 114.4 (6) |
C38—N26—H26N | 114 (4) | O21A—Cl2—O22A | 115.3 (6) |
N1—C1—C2 | 118.6 (4) | O23A—Cl2—O22A | 111.0 (9) |
N1—C1—C5 | 115.0 (4) | O23B—Cl2—O24 | 127.9 (8) |
C2—C1—C5 | 126.4 (4) | O21A—Cl2—O24 | 107.3 (4) |
N2—C2—C1 | 122.7 (4) | O23A—Cl2—O24 | 103.0 (5) |
N2—C2—C12 | 115.0 (4) | O22A—Cl2—O24 | 104.5 (7) |
C1—C2—C12 | 122.3 (4) | O23B—Cl2—O22B | 94.9 (16) |
N2—C3—C4 | 121.6 (5) | O24—Cl2—O22B | 111.9 (10) |
N2—C3—H3A | 119.2 | O23B—Cl2—O21B | 97.0 (17) |
C4—C3—H3A | 119.2 | O24—Cl2—O21B | 116.9 (10) |
N1—C4—C3 | 120.5 (4) | O22B—Cl2—O21B | 104 (2) |
N1—C4—H4A | 119.7 | N41—C42—C43 | 178.2 (14) |
C3—C4—H4A | 119.7 | C42—C43—H43A | 109.5 |
O1—C5—N3 | 126.2 (4) | C42—C43—H43B | 109.5 |
O1—C5—C1 | 122.4 (4) | H43A—C43—H43B | 109.5 |
N3—C5—C1 | 111.3 (4) | C42—C43—H43C | 109.5 |
N3—C6—C7 | 106.4 (4) | H43A—C43—H43C | 109.5 |
N3—C6—H6A | 110.5 | H43B—C43—H43C | 109.5 |
C7—C6—H6A | 110.5 | N44—C45—C46 | 179.1 (8) |
N3—C6—H6B | 110.5 | C45—C46—H46A | 109.5 |
C7—C6—H6B | 110.5 | C45—C46—H46B | 109.5 |
H6A—C6—H6B | 108.6 | H46A—C46—H46B | 109.5 |
N4—C7—C8 | 120.8 (4) | C45—C46—H46C | 109.5 |
N4—C7—C6 | 117.1 (4) | H46A—C46—H46C | 109.5 |
C8—C7—C6 | 122.1 (4) | H46B—C46—H46C | 109.5 |
C9—C8—C7 | 119.4 (5) | N47—C48—C49 | 178.7 (11) |
C9—C8—H8A | 120.3 | C48—C49—H49A | 109.5 |
C7—C8—H8A | 120.3 | C48—C49—H49B | 109.5 |
C10—C9—C8 | 118.6 (5) | H49A—C49—H49B | 109.5 |
C10—C9—H9A | 120.7 | C48—C49—H49C | 109.5 |
C8—C9—H9A | 120.7 | H49A—C49—H49B | 109.5 |
C11—C10—C9 | 120.1 (5) | H49A—C49—H49B | 109.5 |
C11—C10—H10A | 119.9 | N50—C51—C52 | 168.3 (16) |
C9—C10—H10A | 119.9 | C51—C52—H52A | 109.5 |
C10—C11—N4 | 122.0 (5) | C51—C52—H52B | 109.5 |
C10—C11—H11A | 119.0 | H52A—C52—H52B | 109.5 |
N4—C11—H11A | 119.0 | C51—C52—H52C | 109.5 |
O2—C12—N5 | 124.2 (4) | H52A—C52—H52C | 109.5 |
O2—C12—C2 | 120.6 (5) | H52B—C52—H52C | 109.5 |
N5—C12—C2 | 115.0 (5) | O33—Cl3A—O31 | 170.0 (8) |
N5—C13—C14 | 114.6 (4) | O33—Cl3A—O36 | 76.0 (8) |
N5—C13—H13A | 108.6 | O31—Cl3A—O36 | 105.1 (8) |
C14—C13—H13A | 108.6 | O33—Cl3A—O35 | 73.8 (7) |
N5—C13—H13B | 108.6 | O31—Cl3A—O35 | 96.7 (7) |
C14—C13—H13B | 108.6 | O36—Cl3A—O35 | 110.7 (6) |
H13A—C13—H13B | 107.6 | O33—Cl3A—O37 | 66.8 (13) |
N6—C14—C15 | 115.9 (5) | O31—Cl3A—O37 | 120.5 (14) |
N6—C14—C13 | 118.8 (4) | O36—Cl3A—O37 | 113.4 (12) |
C15—C14—C13 | 125.2 (5) | O35—Cl3A—O37 | 109.1 (11) |
C16—C15—C14 | 120.9 (5) | O33—Cl3A—O34 | 100.2 (7) |
C16—C15—H15A | 119.5 | O31—Cl3A—O34 | 89.8 (5) |
C14—C15—H15A | 119.5 | O36—Cl3A—O34 | 89.6 (6) |
C15—C16—C17 | 120.8 (5) | O35—Cl3A—O34 | 156.1 (7) |
C15—C16—H16A | 119.6 | O37—Cl3A—O34 | 48.9 (10) |
C17—C16—H16A | 119.6 | O33—Cl3A—O32 | 94.0 (7) |
C18—C17—C16 | 117.6 (6) | O31—Cl3A—O32 | 87.9 (5) |
C18—C17—H17A | 121.2 | O36—Cl3A—O32 | 159.1 (8) |
C16—C17—H17A | 121.2 | O35—Cl3A—O32 | 83.3 (6) |
N6—C18—C17 | 120.7 (5) | O37—Cl3A—O32 | 45.9 (10) |
N6—C18—H18A | 119.7 | O34—Cl3A—O32 | 73.9 (4) |
C17—C18—H18A | 119.7 | O37—Cl3B—O34 | 69.1 (14) |
N21—C21—C22 | 120.2 (4) | O37—Cl3B—O32 | 68.1 (13) |
N21—C21—C25 | 113.4 (4) | O34—Cl3B—O32 | 106.4 (6) |
C22—C21—C25 | 126.4 (4) | O37—Cl3B—O33 | 74.0 (19) |
N22—C22—C21 | 122.9 (4) | O34—Cl3B—O33 | 110.9 (7) |
N22—C22—C32 | 115.1 (4) | O32—Cl3B—O33 | 110.7 (6) |
C21—C22—C32 | 121.9 (4) | O37—Cl3B—O31 | 164 (2) |
N22—C23—C24 | 123.1 (4) | O34—Cl3B—O31 | 100.9 (6) |
N22—C23—H23A | 118.4 | O32—Cl3B—O31 | 104.8 (6) |
C24—C23—H23A | 118.4 | O33—Cl3B—O31 | 121.7 (7) |
N21—C24—C23 | 120.8 (4) | O37—Cl3B—O35 | 115.3 (17) |
N21—C24—H24A | 119.6 | O34—Cl3B—O35 | 164.2 (6) |
C23—C24—H24A | 119.6 | O32—Cl3B—O35 | 89.0 (5) |
O3—C25—N23 | 127.3 (4) | O33—Cl3B—O35 | 58.8 (6) |
O3—C25—C21 | 121.4 (4) | O31—Cl3B—O35 | 77.7 (5) |
N23—C25—C21 | 111.4 (4) | O37—Cl3B—O36 | 111.2 (17) |
N23—C26—C27 | 106.6 (4) | O34—Cl3B—O36 | 85.6 (5) |
N23—C26—H26A | 110.4 | O32—Cl3B—O36 | 166.0 (6) |
C27—C26—H26A | 110.4 | O33—Cl3B—O36 | 57.1 (6) |
N23—C26—H26B | 110.4 | O31—Cl3B—O36 | 79.2 (6) |
C27—C26—H26B | 110.4 | O35—Cl3B—O36 | 78.7 (5) |
H26A—C26—H26B | 108.6 | | |
| | | |
N3—Co1—N1—C4 | −179.7 (5) | C11—N4—C7—C6 | −178.9 (5) |
N23—Co1—N1—C4 | 2.0 (5) | Co1—N4—C7—C6 | 1.8 (6) |
N4—Co1—N1—C4 | 179.3 (6) | N3—C6—C7—N4 | 0.2 (6) |
N24—Co1—N1—C4 | −80.9 (5) | N3—C6—C7—C8 | −179.0 (5) |
N21—Co1—N1—C4 | 84.6 (4) | N4—C7—C8—C9 | −0.9 (9) |
N3—Co1—N1—C1 | 3.3 (3) | C6—C7—C8—C9 | 178.3 (6) |
N23—Co1—N1—C1 | −175.1 (3) | C7—C8—C9—C10 | 0.3 (9) |
N4—Co1—N1—C1 | 2.2 (9) | C8—C9—C10—C11 | 1.0 (10) |
N24—Co1—N1—C1 | 102.0 (3) | C9—C10—C11—N4 | −1.6 (9) |
N21—Co1—N1—C1 | −92.4 (3) | C7—N4—C11—C10 | 0.9 (8) |
N4—Co1—N3—C5 | 175.7 (4) | Co1—N4—C11—C10 | −179.8 (4) |
N24—Co1—N3—C5 | −95.0 (4) | C13—N5—C12—O2 | 3.9 (8) |
N21—Co1—N3—C5 | 85.6 (4) | C13—N5—C12—C2 | 179.6 (4) |
N1—Co1—N3—C5 | −4.1 (4) | N2—C2—C12—O2 | 83.0 (6) |
N4—Co1—N3—C6 | 2.7 (4) | C1—C2—C12—O2 | −96.4 (6) |
N24—Co1—N3—C6 | 92.0 (4) | N2—C2—C12—N5 | −92.8 (6) |
N21—Co1—N3—C6 | −87.4 (4) | C1—C2—C12—N5 | 87.7 (6) |
N1—Co1—N3—C6 | −177.0 (4) | C12—N5—C13—C14 | 93.9 (7) |
N3—Co1—N4—C7 | −2.4 (4) | C18—N6—C14—C15 | −0.2 (9) |
N23—Co1—N4—C7 | 175.9 (4) | C18—N6—C14—C13 | −177.9 (6) |
N24—Co1—N4—C7 | −101.4 (4) | N5—C13—C14—N6 | −13.2 (8) |
N21—Co1—N4—C7 | 93.2 (4) | N5—C13—C14—C15 | 169.4 (6) |
N1—Co1—N4—C7 | −1.4 (10) | N6—C14—C15—C16 | −1.2 (11) |
N3—Co1—N4—C11 | 178.3 (4) | C13—C14—C15—C16 | 176.3 (7) |
N23—Co1—N4—C11 | −3.3 (4) | C14—C15—C16—C17 | 2.6 (13) |
N24—Co1—N4—C11 | 79.4 (4) | C15—C16—C17—C18 | −2.5 (12) |
N21—Co1—N4—C11 | −86.0 (4) | C14—N6—C18—C17 | 0.3 (10) |
N1—Co1—N4—C11 | 179.4 (6) | C16—C17—C18—N6 | 1.1 (11) |
N3—Co1—N21—C24 | −1.1 (4) | C24—N21—C21—C22 | 1.7 (6) |
N23—Co1—N21—C24 | 178.1 (4) | Co1—N21—C21—C22 | −177.6 (3) |
N4—Co1—N21—C24 | −84.1 (4) | C24—N21—C21—C25 | −179.6 (4) |
N24—Co1—N21—C24 | −178.7 (5) | Co1—N21—C21—C25 | 1.1 (4) |
N1—Co1—N21—C24 | 81.8 (4) | C23—N22—C22—C21 | −1.7 (7) |
N3—Co1—N21—C21 | 178.1 (3) | C23—N22—C22—C32 | −179.1 (4) |
N23—Co1—N21—C21 | −2.7 (3) | N21—C21—C22—N22 | −0.3 (7) |
N4—Co1—N21—C21 | 95.1 (3) | C25—C21—C22—N22 | −178.8 (4) |
N24—Co1—N21—C21 | 0.5 (8) | N21—C21—C22—C32 | 176.8 (4) |
N1—Co1—N21—C21 | −99.0 (3) | C25—C21—C22—C32 | −1.7 (7) |
N4—Co1—N23—C25 | −85.5 (4) | C22—N22—C23—C24 | 2.5 (7) |
N24—Co1—N23—C25 | −174.9 (4) | C21—N21—C24—C23 | −1.0 (6) |
N21—Co1—N23—C25 | 4.3 (3) | Co1—N21—C24—C23 | 178.2 (4) |
N1—Co1—N23—C25 | 93.9 (4) | N22—C23—C24—N21 | −1.2 (8) |
N4—Co1—N23—C26 | 90.7 (4) | C26—N23—C25—O3 | −0.3 (7) |
N24—Co1—N23—C26 | 1.3 (3) | Co1—N23—C25—O3 | 175.7 (3) |
N21—Co1—N23—C26 | −179.6 (4) | C26—N23—C25—C21 | 179.3 (4) |
N1—Co1—N23—C26 | −90.0 (4) | Co1—N23—C25—C21 | −4.6 (5) |
N3—Co1—N24—C31 | −2.9 (4) | N21—C21—C25—O3 | −178.2 (4) |
N23—Co1—N24—C31 | 177.9 (4) | C22—C21—C25—O3 | 0.4 (7) |
N4—Co1—N24—C31 | 79.9 (4) | N21—C21—C25—N23 | 2.1 (5) |
N21—Co1—N24—C31 | 174.6 (5) | C22—C21—C25—N23 | −179.3 (4) |
N1—Co1—N24—C31 | −86.1 (4) | C25—N23—C26—C27 | 174.6 (4) |
N3—Co1—N24—C27 | 178.5 (3) | Co1—N23—C26—C27 | −1.5 (5) |
N23—Co1—N24—C27 | −0.7 (3) | C31—N24—C27—C28 | 1.6 (7) |
N4—Co1—N24—C27 | −98.6 (3) | Co1—N24—C27—C28 | −179.7 (4) |
N21—Co1—N24—C27 | −4.0 (8) | C31—N24—C27—C26 | −178.6 (4) |
N1—Co1—N24—C27 | 95.4 (3) | Co1—N24—C27—C26 | 0.1 (5) |
C4—N1—C1—C2 | 2.1 (7) | N23—C26—C27—N24 | 0.8 (6) |
Co1—N1—C1—C2 | 179.5 (4) | N23—C26—C27—C28 | −179.4 (4) |
C4—N1—C1—C5 | −179.6 (4) | N24—C27—C28—C29 | −1.7 (7) |
Co1—N1—C1—C5 | −2.2 (5) | C26—C27—C28—C29 | 178.5 (5) |
C3—N2—C2—C1 | 0.5 (8) | C27—C28—C29—C30 | 0.8 (8) |
C3—N2—C2—C12 | −179.0 (5) | C28—C29—C30—C31 | 0.3 (8) |
N1—C1—C2—N2 | −0.8 (8) | C27—N24—C31—C30 | −0.5 (7) |
C5—C1—C2—N2 | −178.8 (5) | Co1—N24—C31—C30 | −179.0 (4) |
N1—C1—C2—C12 | 178.7 (5) | C29—C30—C31—N24 | −0.5 (8) |
C5—C1—C2—C12 | 0.6 (8) | C33—N25—C32—O4 | 6.1 (8) |
C2—N2—C3—C4 | −1.5 (8) | C33—N25—C32—C22 | −178.4 (4) |
C1—N1—C4—C3 | −3.2 (7) | N22—C22—C32—O4 | 80.4 (6) |
Co1—N1—C4—C3 | 179.9 (4) | C21—C22—C32—O4 | −96.9 (6) |
N2—C3—C4—N1 | 3.0 (8) | N22—C22—C32—N25 | −95.4 (5) |
C6—N3—C5—O1 | −2.9 (8) | C21—C22—C32—N25 | 87.3 (6) |
Co1—N3—C5—O1 | −175.6 (4) | C32—N25—C33—C34 | 107.3 (5) |
C6—N3—C5—C1 | 176.5 (4) | C38—N26—C34—C35 | −1.8 (7) |
Co1—N3—C5—C1 | 3.8 (5) | C38—N26—C34—C33 | 179.3 (4) |
N1—C1—C5—O1 | 178.5 (4) | N25—C33—C34—N26 | −21.9 (6) |
C2—C1—C5—O1 | −3.4 (8) | N25—C33—C34—C35 | 159.2 (4) |
N1—C1—C5—N3 | −0.8 (6) | N26—C34—C35—C36 | 0.4 (7) |
C2—C1—C5—N3 | 177.3 (5) | C33—C34—C35—C36 | 179.3 (5) |
C5—N3—C6—C7 | −175.0 (4) | C34—C35—C36—C37 | 1.5 (8) |
Co1—N3—C6—C7 | −2.3 (5) | C35—C36—C37—C38 | −2.0 (8) |
C11—N4—C7—C8 | 0.3 (8) | C34—N26—C38—C37 | 1.3 (7) |
Co1—N4—C7—C8 | −179.0 (4) | C36—C37—C38—N26 | 0.7 (7) |
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 |
N5—H5N···O21Aii | 0.90 (3) | 2.41 (4) | 3.104 (11) | 134 (5) |
N5—H5N···O24ii | 0.90 (3) | 2.13 (4) | 2.963 (6) | 155 (5) |
N6—H6N···O1 | 0.90 (6) | 1.78 (7) | 2.637 (7) | 157 (6) |
N6—H6N···N5 | 0.90 (6) | 2.37 (6) | 2.750 (7) | 105 (5) |
N25—H25N···O12iii | 0.87 (7) | 2.29 (6) | 3.046 (7) | 145 (6) |
N25—H25N···O14iii | 0.87 (7) | 2.32 (7) | 3.075 (8) | 145 (6) |
N26—H26N···O3 | 0.90 (4) | 1.78 (4) | 2.664 (6) | 165 (4) |
N26—H26N···N25 | 0.90 (4) | 2.44 (5) | 2.749 (7) | 101 (4) |
C4—H4A···O11iii | 0.95 | 2.57 | 3.334 (7) | 137 |
C6—H6B···O4iv | 0.99 | 2.56 | 3.362 (7) | 138 |
C11—H11A···N23 | 0.95 | 2.60 | 3.093 (7) | 112 |
C13—H13A···O33v | 0.99 | 2.48 | 3.197 (12) | 129 |
C13—H13A···O35v | 0.99 | 2.58 | 3.509 (12) | 156 |
C16—H16A···N44ii | 0.95 | 2.50 | 3.317 (13) | 143 |
C17—H17A···O35vi | 0.95 | 2.48 | 3.085 (12) | 122 |
C18—H18A···O32vi | 0.95 | 2.30 | 3.173 (13) | 152 |
C18—H18A···O35vi | 0.95 | 2.51 | 3.109 (12) | 121 |
C24—H24A···O4iv | 0.95 | 2.55 | 2.991 (6) | 109 |
C26—H26B···O35 | 0.99 | 2.54 | 3.371 (11) | 142 |
C28—H28A···N50i | 0.95 | 2.45 | 3.273 (13) | 145 |
C31—H31A···N3 | 0.95 | 2.61 | 3.110 (7) | 113 |
C31—H31A···N44vii | 0.95 | 2.39 | 3.254 (10) | 151 |
C33—H33A···O4 | 0.99 | 2.43 | 2.826 (6) | 103 |
C33—H33A···O32viii | 0.99 | 2.41 | 3.381 (11) | 166 |
C33—H33B···N41viii | 0.99 | 2.60 | 3.512 (12) | 153 |
C37—H37A···O4viii | 0.95 | 2.58 | 3.211 (7) | 125 |
C38—H38A···O32 | 0.95 | 2.48 | 3.135 (11) | 126 |
C43—H43A···O14 | 0.98 | 2.47 | 3.238 (12) | 135 |
C46—H46A···N47 | 0.98 | 2.53 | 3.465 (11) | 160 |
C46—H46B···O34 | 0.98 | 2.33 | 3.287 (13) | 165 |
C46—H46C···O13 | 0.98 | 2.58 | 3.149 (11) | 117 |
C52—H52C···O34 | 0.98 | 2.00 | 2.96 (2) | 165 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y+1, z; (iii) x−1, y, z; (iv) −x, −y+2, −z; (v) −x, −y+2, −z+1; (vi) x, y+1, z; (vii) −x+1, −y+2, −z+1; (viii) −x, −y+1, −z. |