The title compound, diaquabis{2-[(5-methylpyrazol-3-yl)methyl]benzimidazole}cobalt(II) dichloride dihydrate acetone solvate, [Co(C12H12N4)2(H2O)2]Cl2·2H2O·C3H6O, is composed of the cationic complex [Co(C12H12N4)2(H2O)2]2+, with two chloride ions, two water molecules and one acetone molecule. The cobalt ion, linked to two water molecules and four N atoms of the deformed ligand, exhibits a slightly distorted octahedral coordination.
Supporting information
CCDC reference: 221619
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.037
- wR factor = 0.097
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.11 Ratio
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C44
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 27.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 15.10 Deg.
C46 -C44 -C46A 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 19.40 Deg.
C45 -C44 -C45A 1.555 1.555 1.555
1 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
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KappaCCD Software (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
diaquabis{2-[(5-methylpyrazol-3-yl)methyl]benzimidazole}cobalt(II) dichloride
dihydrate acetone solvate
top
Crystal data top
[Co(C12H12N4)2(H2O)2]Cl2·2H2O·C3H6O | F(000) = 1428 |
Mr = 684.5 | Dx = 1.39 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 45369 reflections |
a = 12.3576 (2) Å | θ = 2–26.4° |
b = 19.1210 (3) Å | µ = 0.74 mm−1 |
c = 13.9169 (2) Å | T = 293 K |
β = 96.182 (5)° | Cube, brown |
V = 3269.30 (9) Å3 | 0.3 × 0.25 × 0.25 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 5689 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 26.4°, θmin = 1.7° |
φ scan | h = 0→15 |
45369 measured reflections | k = 0→23 |
6413 independent reflections | l = −17→17 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0375P)2 + 2.0272P] where P = (Fo2 + 2Fc2)/3 |
6413 reflections | (Δ/σ)max = 0.002 |
447 parameters | Δρmax = 0.30 e Å−3 |
59 restraints | Δρmin = −0.31 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 | 0.74505 (2) | 0.097284 (13) | 0.236120 (18) | 0.03184 (9) | |
Cl1 | 0.88342 (7) | 0.31949 (4) | 0.22799 (6) | 0.0734 (2) | |
Cl2 | 0.57156 (6) | 0.29107 (3) | 0.43553 (5) | 0.06498 (19) | |
O1 | 0.67167 (15) | 0.18205 (8) | 0.15112 (12) | 0.0503 (4) | |
O2 | 0.80762 (16) | 0.17976 (9) | 0.32817 (12) | 0.0552 (4) | |
O41 | 0.7937 (2) | 0.21015 (14) | 0.51331 (17) | 0.0914 (7) | |
O42 | 0.6255 (2) | 0.31375 (13) | 0.22020 (18) | 0.0807 (6) | |
N1 | 0.83323 (13) | 0.01771 (8) | 0.31915 (12) | 0.0366 (4) | |
N8 | 0.94657 (15) | −0.07192 (9) | 0.34515 (14) | 0.0451 (4) | |
H8 | 0.9920 | −0.1041 | 0.3334 | 0.054* | |
N12 | 0.88325 (14) | 0.10210 (9) | 0.16047 (13) | 0.0418 (4) | |
N13 | 0.92043 (16) | 0.15749 (10) | 0.11341 (15) | 0.0511 (5) | |
H13 | 0.8926 | 0.1987 | 0.1138 | 0.061* | |
N21 | 0.66968 (13) | 0.02383 (8) | 0.13644 (12) | 0.0360 (3) | |
N28 | 0.57628 (15) | −0.07152 (9) | 0.09027 (13) | 0.0447 (4) | |
H28 | 0.5359 | −0.1079 | 0.0937 | 0.054* | |
N32 | 0.60829 (13) | 0.08339 (8) | 0.31270 (12) | 0.0348 (3) | |
N33 | 0.56362 (14) | 0.12786 (9) | 0.37346 (12) | 0.0385 (4) | |
H33 | 0.5833 | 0.1707 | 0.3825 | 0.046* | |
C2 | 0.83665 (16) | −0.00292 (11) | 0.41596 (15) | 0.0388 (4) | |
C3 | 0.78712 (18) | 0.02555 (12) | 0.49187 (16) | 0.0458 (5) | |
H3 | 0.7396 | 0.0633 | 0.4824 | 0.055* | |
C4 | 0.8113 (2) | −0.00449 (14) | 0.58250 (17) | 0.0558 (6) | |
H4 | 0.7793 | 0.0136 | 0.6347 | 0.067* | |
C5 | 0.8818 (2) | −0.06087 (15) | 0.59729 (19) | 0.0611 (7) | |
H5 | 0.8960 | −0.0794 | 0.6591 | 0.073* | |
C6 | 0.9315 (2) | −0.09011 (13) | 0.52294 (19) | 0.0554 (6) | |
H6 | 0.9784 | −0.1281 | 0.5328 | 0.066* | |
C7 | 0.90774 (17) | −0.05974 (11) | 0.43230 (17) | 0.0435 (5) | |
C9 | 0.90133 (16) | −0.02478 (10) | 0.28117 (15) | 0.0388 (4) | |
C10 | 0.92870 (19) | −0.02290 (11) | 0.17930 (16) | 0.0454 (5) | |
H10A | 0.8697 | −0.0444 | 0.1379 | 0.054* | |
H10B | 0.9936 | −0.0508 | 0.1748 | 0.054* | |
C11 | 0.94778 (17) | 0.04913 (11) | 0.14234 (15) | 0.0405 (4) | |
C14 | 1.0056 (2) | 0.14070 (14) | 0.06616 (19) | 0.0574 (6) | |
C15 | 1.0259 (2) | 0.07159 (14) | 0.08397 (18) | 0.0537 (6) | |
H15 | 1.0808 | 0.0448 | 0.0617 | 0.064* | |
C16 | 1.0590 (3) | 0.19300 (19) | 0.0065 (3) | 0.0955 (12) | |
H16A | 1.0131 | 0.2015 | −0.0525 | 0.143* | |
H16B | 1.1278 | 0.1751 | −0.0083 | 0.143* | |
H16C | 1.0702 | 0.2359 | 0.0419 | 0.143* | |
C22 | 0.67686 (16) | 0.01285 (11) | 0.03779 (14) | 0.0390 (4) | |
C23 | 0.72845 (19) | 0.05097 (13) | −0.02892 (16) | 0.0480 (5) | |
H23 | 0.7659 | 0.0920 | −0.0114 | 0.058* | |
C24 | 0.7220 (2) | 0.02550 (15) | −0.12269 (17) | 0.0579 (6) | |
H24 | 0.7558 | 0.0500 | −0.1688 | 0.070* | |
C25 | 0.6664 (2) | −0.03572 (17) | −0.14925 (18) | 0.0652 (7) | |
H25 | 0.6654 | −0.0518 | −0.2124 | 0.078* | |
C26 | 0.6127 (2) | −0.07324 (15) | −0.08494 (19) | 0.0609 (7) | |
H26 | 0.5738 | −0.1136 | −0.1033 | 0.073* | |
C27 | 0.61942 (18) | −0.04781 (12) | 0.00874 (16) | 0.0442 (5) | |
C29 | 0.60849 (16) | −0.02766 (10) | 0.16355 (15) | 0.0373 (4) | |
C30 | 0.58120 (18) | −0.04033 (10) | 0.26350 (15) | 0.0417 (5) | |
H30A | 0.6422 | −0.0641 | 0.2993 | 0.050* | |
H30B | 0.5193 | −0.0718 | 0.2603 | 0.050* | |
C31 | 0.55499 (16) | 0.02336 (10) | 0.31905 (14) | 0.0351 (4) | |
C34 | 0.48496 (18) | 0.09684 (12) | 0.41782 (15) | 0.0437 (5) | |
C35 | 0.47787 (17) | 0.02952 (12) | 0.38407 (15) | 0.0436 (5) | |
H35 | 0.4308 | −0.0051 | 0.4013 | 0.052* | |
C36 | 0.4250 (2) | 0.13399 (15) | 0.4899 (2) | 0.0652 (7) | |
H36A | 0.4726 | 0.1411 | 0.5483 | 0.098* | |
H36B | 0.3636 | 0.1064 | 0.5037 | 0.098* | |
H36C | 0.4001 | 0.1785 | 0.4642 | 0.098* | |
O43 | 0.2392 (4) | 0.3371 (2) | 0.2893 (5) | 0.1297 (18) | 0.71 |
C44 | 0.2529 (3) | 0.27798 (19) | 0.2580 (3) | 0.0981 (13) | |
C45 | 0.3403 (10) | 0.2569 (6) | 0.2029 (10) | 0.169 (6) | 0.71 |
H45A | 0.3109 | 0.2450 | 0.1383 | 0.254* | 0.71 |
H45B | 0.3770 | 0.2170 | 0.2330 | 0.254* | 0.71 |
H45C | 0.3910 | 0.2948 | 0.2008 | 0.254* | 0.71 |
C46 | 0.1873 (13) | 0.2250 (8) | 0.2962 (12) | 0.210 (8) | 0.71 |
H46A | 0.1125 | 0.2396 | 0.2891 | 0.316* | 0.71 |
H46B | 0.2112 | 0.2180 | 0.3635 | 0.316* | 0.71 |
H46C | 0.1942 | 0.1821 | 0.2617 | 0.316* | 0.71 |
O43A | 0.2481 (12) | 0.3273 (8) | 0.1962 (15) | 0.179 (7) | 0.29 |
C45A | 0.3442 (19) | 0.2345 (17) | 0.222 (2) | 0.202 (19) | 0.29 |
H45D | 0.3164 | 0.2089 | 0.1657 | 0.303* | 0.29 |
H45E | 0.3718 | 0.2024 | 0.2721 | 0.303* | 0.29 |
H45F | 0.4017 | 0.2649 | 0.2071 | 0.303* | 0.29 |
C46A | 0.1661 (17) | 0.2287 (9) | 0.2747 (18) | 0.100 (6) | 0.29 |
H46D | 0.1892 | 0.2001 | 0.3298 | 0.150* | 0.29 |
H46E | 0.1504 | 0.1994 | 0.2188 | 0.150* | 0.29 |
H46F | 0.1019 | 0.2541 | 0.2863 | 0.150* | 0.29 |
H21 | 0.829 (2) | 0.2156 (9) | 0.3045 (17) | 0.070 (5)* | |
H22 | 0.805 (2) | 0.1863 (14) | 0.3857 (8) | 0.070 (5)* | |
H11 | 0.639 (2) | 0.1779 (14) | 0.0971 (11) | 0.070 (5)* | |
H12 | 0.653 (2) | 0.2188 (9) | 0.1742 (17) | 0.070 (5)* | |
H411 | 0.816 (3) | 0.198 (2) | 0.5689 (13) | 0.122 (8)* | |
H421 | 0.6856 (19) | 0.331 (2) | 0.213 (3) | 0.122 (8)* | |
H422 | 0.610 (4) | 0.308 (2) | 0.2764 (14) | 0.122 (8)* | |
H412 | 0.739 (2) | 0.235 (2) | 0.513 (3) | 0.122 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.03251 (14) | 0.02836 (14) | 0.03522 (15) | −0.00038 (10) | 0.00626 (10) | −0.00122 (9) |
Cl1 | 0.0819 (5) | 0.0663 (4) | 0.0726 (4) | −0.0322 (4) | 0.0110 (4) | 0.0063 (3) |
Cl2 | 0.0882 (5) | 0.0418 (3) | 0.0616 (4) | 0.0099 (3) | −0.0070 (3) | −0.0063 (3) |
O1 | 0.0679 (11) | 0.0383 (8) | 0.0433 (9) | 0.0082 (7) | 0.0004 (8) | 0.0012 (7) |
O2 | 0.0783 (12) | 0.0422 (9) | 0.0459 (9) | −0.0170 (8) | 0.0103 (9) | −0.0057 (7) |
O41 | 0.121 (2) | 0.0919 (17) | 0.0617 (13) | 0.0397 (15) | 0.0105 (13) | −0.0113 (12) |
O42 | 0.0860 (15) | 0.0762 (14) | 0.0802 (15) | 0.0138 (12) | 0.0106 (13) | −0.0089 (12) |
N1 | 0.0368 (8) | 0.0366 (8) | 0.0365 (9) | 0.0039 (7) | 0.0036 (7) | 0.0015 (7) |
N8 | 0.0458 (10) | 0.0347 (9) | 0.0540 (11) | 0.0080 (7) | 0.0022 (8) | 0.0039 (8) |
N12 | 0.0397 (9) | 0.0364 (9) | 0.0515 (10) | 0.0005 (7) | 0.0146 (8) | 0.0025 (7) |
N13 | 0.0504 (11) | 0.0393 (9) | 0.0668 (12) | −0.0002 (8) | 0.0218 (9) | 0.0076 (9) |
N21 | 0.0395 (9) | 0.0346 (8) | 0.0338 (8) | −0.0018 (7) | 0.0041 (7) | −0.0039 (6) |
N28 | 0.0478 (10) | 0.0369 (9) | 0.0486 (10) | −0.0054 (8) | 0.0021 (8) | −0.0110 (8) |
N32 | 0.0347 (8) | 0.0326 (8) | 0.0379 (9) | −0.0002 (6) | 0.0081 (7) | −0.0026 (6) |
N33 | 0.0413 (9) | 0.0346 (8) | 0.0408 (9) | 0.0017 (7) | 0.0102 (7) | −0.0049 (7) |
C2 | 0.0359 (10) | 0.0392 (10) | 0.0405 (11) | −0.0053 (8) | 0.0002 (8) | 0.0040 (8) |
C3 | 0.0420 (11) | 0.0535 (13) | 0.0421 (11) | −0.0051 (9) | 0.0052 (9) | 0.0011 (9) |
C4 | 0.0543 (14) | 0.0718 (16) | 0.0412 (12) | −0.0159 (12) | 0.0049 (11) | 0.0045 (11) |
C5 | 0.0638 (16) | 0.0692 (17) | 0.0475 (14) | −0.0183 (13) | −0.0069 (12) | 0.0189 (12) |
C6 | 0.0575 (14) | 0.0452 (12) | 0.0607 (15) | −0.0044 (11) | −0.0065 (12) | 0.0178 (11) |
C7 | 0.0402 (11) | 0.0370 (10) | 0.0516 (12) | −0.0033 (8) | −0.0022 (9) | 0.0069 (9) |
C9 | 0.0374 (10) | 0.0323 (9) | 0.0461 (11) | 0.0041 (8) | 0.0024 (9) | 0.0003 (8) |
C10 | 0.0484 (12) | 0.0413 (11) | 0.0473 (12) | 0.0112 (9) | 0.0089 (10) | −0.0040 (9) |
C11 | 0.0380 (10) | 0.0444 (11) | 0.0395 (11) | 0.0067 (8) | 0.0064 (9) | −0.0034 (8) |
C14 | 0.0501 (13) | 0.0631 (15) | 0.0624 (15) | −0.0054 (11) | 0.0222 (12) | 0.0063 (12) |
C15 | 0.0457 (12) | 0.0656 (15) | 0.0526 (14) | 0.0088 (11) | 0.0174 (11) | 0.0004 (11) |
C16 | 0.095 (2) | 0.089 (2) | 0.113 (3) | −0.009 (2) | 0.055 (2) | 0.029 (2) |
C22 | 0.0386 (10) | 0.0431 (11) | 0.0344 (10) | 0.0074 (8) | 0.0003 (8) | −0.0036 (8) |
C23 | 0.0474 (12) | 0.0557 (13) | 0.0411 (11) | 0.0092 (10) | 0.0060 (10) | 0.0034 (10) |
C24 | 0.0572 (14) | 0.0788 (18) | 0.0383 (12) | 0.0199 (13) | 0.0072 (11) | 0.0053 (11) |
C25 | 0.0663 (16) | 0.092 (2) | 0.0360 (12) | 0.0208 (15) | −0.0012 (12) | −0.0128 (13) |
C26 | 0.0616 (15) | 0.0690 (16) | 0.0496 (14) | 0.0086 (13) | −0.0054 (12) | −0.0238 (12) |
C27 | 0.0426 (11) | 0.0456 (11) | 0.0432 (11) | 0.0073 (9) | −0.0016 (9) | −0.0083 (9) |
C29 | 0.0390 (10) | 0.0306 (9) | 0.0416 (11) | −0.0004 (8) | 0.0015 (8) | −0.0054 (8) |
C30 | 0.0469 (11) | 0.0334 (10) | 0.0458 (11) | −0.0077 (8) | 0.0097 (9) | −0.0018 (8) |
C31 | 0.0361 (10) | 0.0348 (9) | 0.0343 (10) | −0.0031 (8) | 0.0036 (8) | 0.0008 (7) |
C34 | 0.0428 (11) | 0.0524 (12) | 0.0372 (11) | 0.0014 (9) | 0.0108 (9) | 0.0005 (9) |
C35 | 0.0429 (11) | 0.0486 (12) | 0.0406 (11) | −0.0092 (9) | 0.0106 (9) | 0.0023 (9) |
C36 | 0.0719 (17) | 0.0688 (17) | 0.0607 (16) | 0.0007 (14) | 0.0338 (14) | −0.0087 (13) |
O43 | 0.125 (4) | 0.069 (2) | 0.194 (5) | −0.007 (2) | 0.009 (4) | −0.023 (3) |
C44 | 0.099 (3) | 0.058 (2) | 0.131 (3) | −0.0077 (18) | −0.019 (3) | 0.015 (2) |
C45 | 0.201 (12) | 0.141 (8) | 0.184 (10) | −0.075 (8) | 0.103 (10) | −0.053 (7) |
C46 | 0.247 (17) | 0.199 (13) | 0.203 (13) | −0.002 (11) | 0.104 (12) | 0.072 (10) |
O43A | 0.132 (10) | 0.101 (9) | 0.296 (19) | 0.012 (8) | −0.009 (13) | 0.071 (12) |
C45A | 0.12 (2) | 0.28 (4) | 0.20 (3) | 0.13 (3) | −0.001 (18) | 0.06 (3) |
C46A | 0.099 (10) | 0.069 (9) | 0.135 (15) | −0.041 (8) | 0.027 (10) | −0.039 (10) |
Geometric parameters (Å, º) top
Co1—N12 | 2.1026 (17) | C11—C15 | 1.395 (3) |
Co1—N32 | 2.1096 (16) | C14—C15 | 1.363 (4) |
Co1—N21 | 2.1181 (16) | C14—C16 | 1.498 (4) |
Co1—O2 | 2.1243 (16) | C15—H15 | 0.9300 |
Co1—N1 | 2.1369 (16) | C16—H16A | 0.9600 |
Co1—O1 | 2.1489 (15) | C16—H16B | 0.9600 |
O1—H11 | 0.82 (2) | C16—H16C | 0.9600 |
O1—H12 | 0.82 (2) | C22—C23 | 1.388 (3) |
O2—H21 | 0.82 (2) | C22—C27 | 1.397 (3) |
O2—H22 | 0.81 (1) | C23—C24 | 1.387 (3) |
O41—H411 | 0.83 (2) | C23—H23 | 0.9300 |
O41—H412 | 0.82 (3) | C24—C25 | 1.388 (4) |
O42—H421 | 0.83 (3) | C24—H24 | 0.9300 |
O42—H422 | 0.83 (3) | C25—C26 | 1.373 (4) |
N1—C9 | 1.321 (3) | C25—H25 | 0.9300 |
N1—C2 | 1.400 (3) | C26—C27 | 1.386 (3) |
N8—C9 | 1.346 (3) | C26—H26 | 0.9300 |
N8—C7 | 1.372 (3) | C29—C30 | 1.486 (3) |
N8—H8 | 0.8600 | C30—C31 | 1.496 (3) |
N12—C11 | 1.330 (3) | C30—H30A | 0.9700 |
N12—N13 | 1.352 (2) | C30—H30B | 0.9700 |
N13—C14 | 1.339 (3) | C31—C35 | 1.388 (3) |
N13—H13 | 0.8600 | C34—C35 | 1.370 (3) |
N21—C29 | 1.321 (3) | C34—C36 | 1.490 (3) |
N21—C22 | 1.401 (3) | C35—H35 | 0.9300 |
N28—C29 | 1.347 (3) | C36—H36A | 0.9600 |
N28—C27 | 1.381 (3) | C36—H36B | 0.9600 |
N28—H28 | 0.8600 | C36—H36C | 0.9600 |
N32—C31 | 1.331 (2) | O43—C44 | 1.229 (6) |
N32—N33 | 1.358 (2) | C44—O43A | 1.273 (12) |
N33—C34 | 1.344 (3) | C44—C46 | 1.436 (10) |
N33—H33 | 0.8600 | C44—C45 | 1.448 (9) |
C2—C3 | 1.388 (3) | C44—C46A | 1.465 (12) |
C2—C7 | 1.400 (3) | C44—C45A | 1.525 (15) |
C3—C4 | 1.389 (3) | C45—H45A | 0.9600 |
C3—H3 | 0.9300 | C45—H45B | 0.9600 |
C4—C5 | 1.388 (4) | C45—H45C | 0.9600 |
C4—H4 | 0.9300 | C46—H46A | 0.9600 |
C5—C6 | 1.377 (4) | C46—H46B | 0.9600 |
C5—H5 | 0.9300 | C46—H46C | 0.9600 |
C6—C7 | 1.391 (3) | C45A—H45D | 0.9600 |
C6—H6 | 0.9300 | C45A—H45E | 0.9600 |
C9—C10 | 1.493 (3) | C45A—H45F | 0.9600 |
C10—C11 | 1.498 (3) | C46A—H46D | 0.9600 |
C10—H10A | 0.9700 | C46A—H46E | 0.9600 |
C10—H10B | 0.9700 | C46A—H46F | 0.9600 |
| | | |
N12—Co1—N32 | 175.25 (6) | C11—C15—H15 | 126.9 |
N12—Co1—N21 | 91.41 (7) | C14—C16—H16A | 109.5 |
N32—Co1—N21 | 85.85 (6) | C14—C16—H16B | 109.5 |
N12—Co1—O2 | 90.40 (7) | H16A—C16—H16B | 109.5 |
N32—Co1—O2 | 92.76 (7) | C14—C16—H16C | 109.5 |
N21—Co1—O2 | 173.25 (7) | H16A—C16—H16C | 109.5 |
N12—Co1—N1 | 84.69 (7) | H16B—C16—H16C | 109.5 |
N32—Co1—N1 | 91.54 (6) | C23—C22—C27 | 119.9 (2) |
N21—Co1—N1 | 92.56 (6) | C23—C22—N21 | 131.2 (2) |
O2—Co1—N1 | 94.08 (7) | C27—C22—N21 | 108.92 (18) |
N12—Co1—O1 | 90.50 (7) | C24—C23—C22 | 117.4 (2) |
N32—Co1—O1 | 93.41 (7) | C24—C23—H23 | 121.3 |
N21—Co1—O1 | 90.57 (6) | C22—C23—H23 | 121.3 |
O2—Co1—O1 | 82.91 (7) | C23—C24—C25 | 121.6 (2) |
N1—Co1—O1 | 174.32 (7) | C23—C24—H24 | 119.2 |
Co1—O1—H11 | 124.8 (18) | C25—C24—H24 | 119.2 |
Co1—O1—H12 | 123.6 (18) | C26—C25—C24 | 121.9 (2) |
H11—O1—H12 | 108.2 (16) | C26—C25—H25 | 119.1 |
Co1—O2—H21 | 119.5 (19) | C24—C25—H25 | 119.1 |
Co1—O2—H22 | 130.9 (19) | C25—C26—C27 | 116.5 (3) |
H21—O2—H22 | 109 (2) | C25—C26—H26 | 121.8 |
H411—O41—H412 | 111 (2) | C27—C26—H26 | 121.8 |
H421—O42—H422 | 118 (5) | N28—C27—C26 | 131.9 (2) |
C9—N1—C2 | 104.91 (16) | N28—C27—C22 | 105.30 (18) |
C9—N1—Co1 | 122.11 (14) | C26—C27—C22 | 122.8 (2) |
C2—N1—Co1 | 132.98 (13) | N21—C29—N28 | 112.30 (18) |
C9—N8—C7 | 108.14 (17) | N21—C29—C30 | 125.69 (17) |
C9—N8—H8 | 125.9 | N28—C29—C30 | 121.93 (18) |
C7—N8—H8 | 125.9 | C29—C30—C31 | 115.75 (17) |
C11—N12—N13 | 105.24 (17) | C29—C30—H30A | 108.3 |
C11—N12—Co1 | 126.70 (14) | C31—C30—H30A | 108.3 |
N13—N12—Co1 | 127.86 (13) | C29—C30—H30B | 108.3 |
C14—N13—N12 | 112.11 (19) | C31—C30—H30B | 108.3 |
C14—N13—H13 | 123.9 | H30A—C30—H30B | 107.4 |
N12—N13—H13 | 123.9 | N32—C31—C35 | 110.46 (18) |
C29—N21—C22 | 105.47 (16) | N32—C31—C30 | 122.09 (17) |
C29—N21—Co1 | 122.15 (13) | C35—C31—C30 | 127.43 (18) |
C22—N21—Co1 | 132.17 (13) | N33—C34—C35 | 106.25 (18) |
C29—N28—C27 | 107.99 (18) | N33—C34—C36 | 122.4 (2) |
C29—N28—H28 | 126.0 | C35—C34—C36 | 131.4 (2) |
C27—N28—H28 | 126.0 | C34—C35—C31 | 106.28 (18) |
C31—N32—N33 | 105.15 (15) | C34—C35—H35 | 126.9 |
C31—N32—Co1 | 124.83 (13) | C31—C35—H35 | 126.9 |
N33—N32—Co1 | 129.60 (12) | C34—C36—H36A | 109.5 |
C34—N33—N32 | 111.86 (17) | C34—C36—H36B | 109.5 |
C34—N33—H33 | 124.1 | H36A—C36—H36B | 109.5 |
N32—N33—H33 | 124.1 | C34—C36—H36C | 109.5 |
C3—C2—N1 | 130.68 (19) | H36A—C36—H36C | 109.5 |
C3—C2—C7 | 120.1 (2) | H36B—C36—H36C | 109.5 |
N1—C2—C7 | 109.17 (19) | O43—C44—O43A | 64.0 (10) |
C2—C3—C4 | 117.4 (2) | O43—C44—C46 | 114.3 (8) |
C2—C3—H3 | 121.3 | O43A—C44—C46 | 141.8 (11) |
C4—C3—H3 | 121.3 | O43—C44—C45 | 125.6 (6) |
C5—C4—C3 | 121.7 (2) | O43A—C44—C45 | 80.3 (11) |
C5—C4—H4 | 119.1 | C46—C44—C45 | 118.9 (9) |
C3—C4—H4 | 119.1 | O43—C44—C46A | 113.8 (9) |
C6—C5—C4 | 121.8 (2) | O43A—C44—C46A | 127.0 (13) |
C6—C5—H5 | 119.1 | C46—C44—C46A | 15.1 (17) |
C4—C5—H5 | 119.1 | C45—C44—C46A | 120.4 (9) |
C5—C6—C7 | 116.4 (2) | O43—C44—C45A | 138.6 (15) |
C5—C6—H6 | 121.8 | O43A—C44—C45A | 99.6 (13) |
C7—C6—H6 | 121.8 | C46—C44—C45A | 101.7 (16) |
N8—C7—C6 | 132.2 (2) | C45—C44—C45A | 19.4 (13) |
N8—C7—C2 | 105.15 (18) | C46A—C44—C45A | 106.3 (14) |
C6—C7—C2 | 122.6 (2) | C44—C45—H45A | 109.5 |
N1—C9—N8 | 112.62 (19) | C44—C45—H45B | 109.5 |
N1—C9—C10 | 125.77 (18) | C44—C45—H45C | 109.5 |
N8—C9—C10 | 121.61 (18) | C44—C46—H46A | 109.5 |
C9—C10—C11 | 114.11 (17) | C44—C46—H46B | 109.5 |
C9—C10—H10A | 108.7 | C44—C46—H46C | 109.5 |
C11—C10—H10A | 108.7 | C44—C45A—H45D | 109.5 |
C9—C10—H10B | 108.7 | C44—C45A—H45E | 109.5 |
C11—C10—H10B | 108.7 | H45D—C45A—H45E | 109.5 |
H10A—C10—H10B | 107.6 | C44—C45A—H45F | 109.5 |
N12—C11—C15 | 110.0 (2) | H45D—C45A—H45F | 109.5 |
N12—C11—C10 | 121.02 (18) | H45E—C45A—H45F | 109.5 |
C15—C11—C10 | 128.88 (19) | C44—C46A—H46D | 109.5 |
N13—C14—C15 | 106.4 (2) | C44—C46A—H46E | 109.5 |
N13—C14—C16 | 121.9 (3) | H46D—C46A—H46E | 109.5 |
C15—C14—C16 | 131.7 (3) | C44—C46A—H46F | 109.5 |
C14—C15—C11 | 106.2 (2) | H46D—C46A—H46F | 109.5 |
C14—C15—H15 | 126.9 | H46E—C46A—H46F | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H22···O41 | 0.81 (1) | 1.85 (1) | 2.665 (3) | 174 (3) |
O1—H12···O42 | 0.82 (2) | 1.97 (1) | 2.777 (3) | 171 (3) |
O41—H412···O1i | 0.82 (3) | 2.69 (3) | 3.290 (3) | 131 (3) |
N13—H13···O41ii | 0.86 | 2.47 | 3.214 (4) | 145 |
N8—H8···Cl1iii | 0.86 | 2.35 | 3.1971 (19) | 169 |
N28—H28···Cl2iv | 0.86 | 2.35 | 3.1983 (19) | 167 |
N13—H13···Cl1 | 0.86 | 2.81 | 3.536 (2) | 143 |
N33—H33···Cl2 | 0.86 | 2.43 | 3.2367 (18) | 157 |
O2—H21···Cl1 | 0.82 (2) | 2.39 (1) | 3.2001 (18) | 177 (3) |
O1—H11···Cl2ii | 0.82 (2) | 2.39 (2) | 3.1618 (17) | 158 (3) |
O41—H411···Cl1i | 0.83 (2) | 2.31 (1) | 3.125 (2) | 171 (4) |
O42—H421···Cl1 | 0.83 (3) | 2.44 (3) | 3.180 (3) | 149 (4) |
O42—H422···Cl2 | 0.83 (3) | 2.34 (1) | 3.169 (3) | 179 (4) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2. |