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The title compound, bis(L-histidinato)cobalt(III)-chloride-nitrate-water (1/0.4/0.6/2.5), [Co(C6H8N3O2)2]Cl0.4(NO3)0.6·2.5H2O, crystallizes as a mixed chloride/nitrate hydrate salt. This crystallographic experiment validates earlier research which concluded that the red chromatographic fraction contains the trans-imidazole isomer of the complex. The asymmetric unit contains two complex cations, 0.80-chloride, 1.20-nitrate, and five solvent water molecules.
Supporting information
CCDC reference: 271829
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- H-atom completeness 84%
- Disorder in solvent or counterion
- R factor = 0.038
- wR factor = 0.103
- Data-to-parameter ratio = 9.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT430_ALERT_2_A Short Inter D...A Contact O17 .. O18 .. 2.38 Ang.
| Author Response: The short nonbonded contact appears as a result of a model
that was used in the structure refinement. The atoms in question are all
partial occupancies and are not present in every unit cell. Many of the
other alerts are also the result of the model used. I have attempted to
explain this in some detail in the text and the _publ_section_exptl_refinement
section.
|
PLAT430_ALERT_2_A Short Inter D...A Contact O31 .. O31 .. 1.78 Ang.
| Author Response: The short nonbonded contact appears as a result of a model
that was used in the structure refinement. The atoms in question are all
partial occupancies and are not present in every unit cell. Many of the
other alerts are also the result of the model used. I have attempted to
explain this in some detail in the text and the _publ_section_exptl_refinement
section.
|
Alert level B
PLAT355_ALERT_3_B Long O-H Bond (0.82A) O12 - H121 ... 1.11 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O14A .. 2.62 Ang.
| Author Response: The short nonbonded contact appears as a result of a model
that was used in the structure refinement. The atoms in question are all
partial occupancies and are not present in every unit cell. Many of the
other alerts are also the result of the model used. I have attempted to
explain this in some detail in the text and the _publ_section_exptl_refinement
section.
|
PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O14B .. 2.78 Ang.
| Author Response: The short nonbonded contact appears as a result of a model
that was used in the structure refinement. The atoms in question are all
partial occupancies and are not present in every unit cell. Many of the
other alerts are also the result of the model used. I have attempted to
explain this in some detail in the text and the _publ_section_exptl_refinement
section.
|
PLAT430_ALERT_2_B Short Inter D...A Contact O6 .. O14B .. 2.58 Ang.
| Author Response: The short nonbonded contact appears as a result of a model
that was used in the structure refinement. The atoms in question are all
partial occupancies and are not present in every unit cell. Many of the
other alerts are also the result of the model used. I have attempted to
explain this in some detail in the text and the _publ_section_exptl_refinement
section.
|
PLAT430_ALERT_2_B Short Inter D...A Contact O15A .. O15B .. 2.63 Ang.
| Author Response: The short nonbonded contact appears as a result of a model
that was used in the structure refinement. The atoms in question are all
partial occupancies and are not present in every unit cell. Many of the
other alerts are also the result of the model used. I have attempted to
explain this in some detail in the text and the _publ_section_exptl_refinement
section.
|
PLAT432_ALERT_2_B Short Inter X...Y Contact C1 .. O33 .. 2.89 Ang.
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.769 0.813
Tmin and Tmax expected: 0.616 0.813
RR = 1.248
Please check that your absorption correction is appropriate.
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 ............ 0.12 Ratio
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.25
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N30
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N13
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 26.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... <O18
PLAT323_ALERT_2_C Check Hybridisation of H131 in Solvent/Ion ?
PLAT323_ALERT_2_C Check Hybridisation of H132 in Solvent/Ion ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT430_ALERT_2_C Short Inter D...A Contact O6 .. O14A .. 2.88 Ang.
| Author Response: The short nonbonded contact appears as a result of a model
that was used in the structure refinement. The atoms in question are all
partial occupancies and are not present in every unit cell. Many of the
other alerts are also the result of the model used. I have attempted to
explain this in some detail in the text and the _publ_section_exptl_refinement
section.
|
PLAT430_ALERT_2_C Short Inter D...A Contact O14A .. O15A .. 2.87 Ang.
| Author Response: The short nonbonded contact appears as a result of a model
that was used in the structure refinement. The atoms in question are all
partial occupancies and are not present in every unit cell. Many of the
other alerts are also the result of the model used. I have attempted to
explain this in some detail in the text and the _publ_section_exptl_refinement
section.
|
PLAT430_ALERT_2_C Short Inter D...A Contact O15B .. O18 .. 2.89 Ang.
| Author Response: The short nonbonded contact appears as a result of a model
that was used in the structure refinement. The atoms in question are all
partial occupancies and are not present in every unit cell. Many of the
other alerts are also the result of the model used. I have attempted to
explain this in some detail in the text and the _publ_section_exptl_refinement
section.
|
PLAT432_ALERT_2_C Short Inter X...Y Contact O10 .. C19 .. 2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. O17 .. 2.87 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported N1 .. O17 .. 3.76 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.30 Deg.
N30 -CL -O32 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 32.40 Deg.
O16 -O17 -O32 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.10 Deg.
CL -N30 -O33 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.60 Deg.
N30 -O31 -CL 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 20.80 Deg.
O16 -O32 -O17 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 13.10 Deg.
N30 -O32 -CL 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.50 Deg.
CL -O33 -N30 1.555 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 10
O4
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C12 H21 Cl0.4 Co1 N6.6 O8.3
Atom count from _chemical_formula_moiety:C24 H42 Cl0.8 Co2 N13.2 O16.6
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C12 H21 Cl0.4 Co1 N6.6 O8.3
Atom count from the _atom_site data: C12 H17.5 Cl0.4 Co1 N6.6 O8.3
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 8
From the CIF: _chemical_formula_sum C12 H21 Cl0.40 Co1 N6.6 O8.3
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 96.00 96.00 0.00
H 168.00 140.00 28.00
Cl 3.20 3.20 0.00
Co 8.00 8.00 0.00
N 52.80 52.80 0.00
O 66.40 66.40 0.00
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 27.54
From the CIF: _reflns_number_total 5037
Count of symmetry unique reflns 4566
Completeness (_total/calc) 110.32%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 471
Fraction of Friedel pairs measured 0.103
Are heavy atom types Z>Si present yes
2 ALERT level A = In general: serious problem
6 ALERT level B = Potentially serious problem
29 ALERT level C = Check and explain
5 ALERT level G = General alerts; check
7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
22 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
9 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XSHELL (Bruker, 1999); software used to prepare material for publication: XSCANS.
bis(
L-histidinato)cobalt(III)–chloride–nitrate–water (1/0.4/0.6/2.5)
top
Crystal data top
[Co(C6H8N3O2)2]·Cl0.4·NO30.6·2.5H2O | F(000) = 1877 |
Mr = 463.65 | Dx = 1.65 Mg m−3 Dm = 1.65 Mg m−3 Dm measured by floatation |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 62 reflections |
a = 29.398 (3) Å | θ = 12.4–17.1° |
b = 9.839 (1) Å | µ = 1.04 mm−1 |
c = 13.590 (1) Å | T = 293 K |
β = 108.189 (6)° | Plate, red |
V = 3734.4 (6) Å3 | 0.5 × 0.4 × 0.2 mm |
Z = 8 | |
Data collection top
Siemens P4 diffractometer | 4589 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 27.5°, θmin = 2.5° |
θ–2θ scans | h = −38→1 |
Absorption correction: ψ scan (XSCANS; Bruker, 1999) | k = −12→1 |
Tmin = 0.769, Tmax = 0.813 | l = −16→17 |
5319 measured reflections | 3 standard reflections every 75 reflections |
5037 independent reflections | intensity decay: none |
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0612P)2 + 2.4496P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
5037 reflections | Δρmax = 0.55 e Å−3 |
547 parameters | Δρmin = −0.45 e Å−3 |
7 restraints | Absolute structure: Flack (1983), 218 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.008 (15) |
Special details top
Experimental. There is some disorder around the Cl- whch appears to be due to a small
fraction of NO3- substitution at that site. Atom positions for the
NO3- were found on difference maps. A model was employed that included a
NO3- with positional restraints 0.20 occupancy for the atoms. The Cl-
was refined with 0.80 occupancy. This composition is in agreement with
elemental analysis of the crystals (Cl calc'd 3.06, found 2.94). Only one H on the isolated O12 atom was found from difference maps. No H atoms
were included on O atoms with partial occupancy. |
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 | 0.711976 (17) | 0.61787 (5) | 0.42285 (3) | 0.02588 (12) | |
O1 | 0.70636 (11) | 0.4692 (3) | 0.3322 (2) | 0.0345 (6) | |
O2 | 0.69968 (12) | 0.4213 (4) | 0.1696 (3) | 0.0451 (8) | |
O3 | 0.74803 (11) | 0.5107 (3) | 0.5348 (2) | 0.0348 (6) | |
O4 | 0.77401 (13) | 0.5020 (4) | 0.7051 (2) | 0.0499 (9) | |
N1 | 0.67869 (11) | 0.7193 (4) | 0.3001 (2) | 0.0304 (7) | |
H1A | 0.6469 | 0.7164 | 0.2888 | 0.036* | |
H1B | 0.6882 | 0.8067 | 0.3067 | 0.036* | |
N2 | 0.77079 (11) | 0.6736 (4) | 0.3981 (3) | 0.0307 (7) | |
N3 | 0.84586 (13) | 0.7117 (6) | 0.4247 (3) | 0.0516 (11) | |
H3NA | 0.8760 | 0.7208 | 0.4563 | 0.062* | |
N4 | 0.71800 (13) | 0.7584 (4) | 0.5238 (2) | 0.0315 (7) | |
H4A | 0.7435 | 0.8111 | 0.5279 | 0.038* | |
H4B | 0.6916 | 0.8109 | 0.5066 | 0.038* | |
N5 | 0.65384 (12) | 0.5626 (4) | 0.4509 (2) | 0.0302 (7) | |
N6 | 0.58368 (15) | 0.4746 (5) | 0.4320 (3) | 0.0487 (11) | |
H6NA | 0.5567 | 0.4344 | 0.4043 | 0.058* | |
C1 | 0.69890 (15) | 0.5037 (5) | 0.2374 (3) | 0.0348 (9) | |
C2 | 0.69114 (15) | 0.6532 (5) | 0.2128 (3) | 0.0328 (9) | |
H2A | 0.6651 | 0.6658 | 0.1477 | 0.039* | |
C3 | 0.73693 (15) | 0.7129 (5) | 0.2041 (3) | 0.0380 (10) | |
H3A | 0.7461 | 0.6645 | 0.1510 | 0.046* | |
H3B | 0.7315 | 0.8072 | 0.1829 | 0.046* | |
C4 | 0.77703 (15) | 0.7054 (5) | 0.3040 (3) | 0.0358 (9) | |
C5 | 0.82407 (16) | 0.7290 (7) | 0.3216 (4) | 0.0500 (13) | |
H5A | 0.8388 | 0.7526 | 0.2725 | 0.060* | |
C6 | 0.81315 (15) | 0.6787 (6) | 0.4685 (4) | 0.0416 (10) | |
H6A | 0.8192 | 0.6616 | 0.5387 | 0.050* | |
C7 | 0.75119 (15) | 0.5580 (5) | 0.6246 (3) | 0.0344 (9) | |
C8 | 0.72410 (16) | 0.6890 (5) | 0.6241 (3) | 0.0352 (9) | |
H8A | 0.7421 | 0.7473 | 0.6815 | 0.042* | |
C9 | 0.67484 (17) | 0.6579 (6) | 0.6330 (3) | 0.0452 (12) | |
H9A | 0.6787 | 0.6031 | 0.6944 | 0.054* | |
H9B | 0.6597 | 0.7425 | 0.6420 | 0.054* | |
C10 | 0.64248 (15) | 0.5843 (5) | 0.5409 (3) | 0.0355 (10) | |
C11 | 0.59905 (18) | 0.5299 (6) | 0.5292 (4) | 0.0483 (12) | |
H11A | 0.5827 | 0.5298 | 0.5778 | 0.058* | |
C12 | 0.61751 (16) | 0.4940 (5) | 0.3880 (4) | 0.0392 (10) | |
H12A | 0.6160 | 0.4636 | 0.3223 | 0.047* | |
Co2 | 0.901024 (17) | 0.74604 (6) | 0.09180 (4) | 0.02714 (13) | |
O5 | 0.84316 (11) | 0.6628 (4) | 0.0966 (2) | 0.0419 (8) | |
O6 | 0.78278 (13) | 0.5398 (5) | 0.0000 (3) | 0.0622 (12) | |
O7 | 0.92940 (10) | 0.7485 (4) | 0.2396 (2) | 0.0370 (7) | |
O8 | 0.98300 (12) | 0.8615 (5) | 0.3632 (2) | 0.0504 (9) | |
N7 | 0.87244 (11) | 0.7382 (4) | −0.0555 (2) | 0.0297 (7) | |
H7B | 0.8559 | 0.8148 | −0.0790 | 0.036* | |
H7A | 0.8951 | 0.7286 | −0.0867 | 0.036* | |
N8 | 0.92751 (13) | 0.5694 (4) | 0.0848 (3) | 0.0343 (8) | |
N9 | 0.97512 (17) | 0.3957 (5) | 0.1226 (4) | 0.0563 (12) | |
H9NA | 0.9985 | 0.3440 | 0.1557 | 0.068* | |
N10 | 0.95953 (11) | 0.8342 (4) | 0.0917 (2) | 0.0285 (7) | |
H10A | 0.9818 | 0.7720 | 0.0903 | 0.034* | |
H10B | 0.9543 | 0.8884 | 0.0359 | 0.034* | |
N11 | 0.87395 (12) | 0.9225 (4) | 0.1000 (3) | 0.0333 (8) | |
N12 | 0.82189 (15) | 1.0819 (6) | 0.0954 (3) | 0.0510 (12) | |
H12N | 0.7948 | 1.1219 | 0.0857 | 0.061* | |
C13 | 0.81904 (14) | 0.6066 (6) | 0.0109 (3) | 0.0406 (10) | |
C14 | 0.84015 (14) | 0.6197 (6) | −0.0770 (3) | 0.0353 (9) | |
H14A | 0.8144 | 0.6336 | −0.1423 | 0.042* | |
C15 | 0.86779 (19) | 0.4922 (6) | −0.0840 (4) | 0.0446 (11) | |
H15A | 0.8469 | 0.4142 | −0.0904 | 0.053* | |
H15B | 0.8773 | 0.4967 | −0.1461 | 0.053* | |
C16 | 0.91115 (16) | 0.4719 (5) | 0.0069 (3) | 0.0382 (10) | |
C17 | 0.94119 (19) | 0.3658 (6) | 0.0306 (5) | 0.0537 (13) | |
H17A | 0.9393 | 0.2869 | −0.0082 | 0.064* | |
C18 | 0.96590 (17) | 0.5173 (5) | 0.1521 (4) | 0.0436 (11) | |
H18A | 0.9841 | 0.5606 | 0.2124 | 0.052* | |
C19 | 0.96276 (14) | 0.8373 (5) | 0.2712 (3) | 0.0366 (10) | |
C20 | 0.97570 (14) | 0.9147 (5) | 0.1874 (3) | 0.0344 (9) | |
H20A | 1.0105 | 0.9266 | 0.2076 | 0.041* | |
C21 | 0.95180 (17) | 1.0510 (6) | 0.1696 (4) | 0.0423 (10) | |
H21A | 0.9615 | 1.0992 | 0.1171 | 0.051* | |
H21B | 0.9626 | 1.1034 | 0.2332 | 0.051* | |
C22 | 0.89784 (16) | 1.0419 (5) | 0.1357 (3) | 0.0373 (9) | |
C23 | 0.86527 (19) | 1.1409 (6) | 0.1323 (4) | 0.0503 (13) | |
H23A | 0.8716 | 1.2314 | 0.1517 | 0.060* | |
C24 | 0.82774 (15) | 0.9528 (6) | 0.0764 (3) | 0.0406 (11) | |
H24A | 0.8029 | 0.8913 | 0.0500 | 0.049* | |
Cl | 0.57549 (8) | 0.5311 (2) | 0.11574 (14) | 0.0567 (4) | 0.80 |
N13 | 0.92413 (16) | 0.6745 (6) | 0.7476 (3) | 0.0520 (11) | |
O9 | 0.94434 (13) | 0.6911 (5) | 0.8406 (3) | 0.0627 (11) | |
O10 | 0.9476 (2) | 0.6770 (10) | 0.6887 (4) | 0.116 (3) | |
O11 | 0.88122 (17) | 0.6532 (10) | 0.7147 (4) | 0.108 (3) | |
O12 | 0.94412 (13) | 0.6848 (6) | 0.4772 (3) | 0.0627 (11) | |
H121 | 0.9640 | 0.7469 | 0.4362 | 0.080* | |
O13 | 0.8766 (2) | 0.3922 (7) | 0.5743 (5) | 0.108 (2) | |
H131 | 0.8909 | 0.4716 | 0.5827 | 0.080* | |
H132 | 0.8687 | 0.4398 | 0.6183 | 0.080* | |
O14A | 0.7760 (11) | 0.322 (3) | 0.1360 (14) | 0.070 (4) | 0.50 |
O14B | 0.7748 (11) | 0.327 (3) | 0.1044 (14) | 0.079 (5) | 0.50 |
O15A | 0.8667 (4) | 0.4404 (8) | 0.2481 (7) | 0.068 (2) | 0.50 |
O15B | 0.9324 (5) | 0.4112 (14) | 0.4295 (11) | 0.110 (4) | 0.50 |
O16 | 0.5592 (3) | 0.7594 (12) | 0.2348 (6) | 0.063 (2) | 0.50 |
O17 | 0.5472 (5) | 0.748 (2) | 0.2682 (12) | 0.042 (4)* | 0.25 |
O18 | 1.0081 (9) | 1.247 (3) | 0.3970 (18) | 0.100 (7)* | 0.25 |
N30 | 0.5645 (6) | 0.5953 (19) | 0.1272 (12) | 0.030 (4)* | 0.20 |
O31 | 0.5277 (6) | 0.586 (2) | 0.0509 (12) | 0.057 (5)* | 0.20 |
O32 | 0.5690 (7) | 0.690 (2) | 0.1909 (13) | 0.054 (5)* | 0.20 |
O33 | 0.5963 (10) | 0.505 (3) | 0.143 (3) | 0.117 (15)* | 0.20 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0292 (2) | 0.0250 (2) | 0.0221 (2) | 0.0013 (2) | 0.00596 (18) | −0.0011 (2) |
O1 | 0.0438 (16) | 0.0291 (15) | 0.0290 (13) | 0.0022 (13) | 0.0089 (12) | −0.0045 (13) |
O2 | 0.0471 (17) | 0.051 (2) | 0.0377 (16) | −0.0100 (17) | 0.0142 (14) | −0.0205 (16) |
O3 | 0.0430 (16) | 0.0308 (15) | 0.0274 (13) | 0.0057 (14) | 0.0062 (12) | 0.0020 (12) |
O4 | 0.060 (2) | 0.049 (2) | 0.0280 (15) | −0.0030 (18) | −0.0047 (14) | 0.0082 (15) |
N1 | 0.0288 (15) | 0.0331 (19) | 0.0291 (15) | 0.0047 (15) | 0.0086 (12) | 0.0015 (14) |
N2 | 0.0271 (15) | 0.0331 (18) | 0.0310 (16) | 0.0005 (15) | 0.0075 (13) | −0.0032 (15) |
N3 | 0.0293 (17) | 0.068 (3) | 0.055 (2) | −0.002 (2) | 0.0089 (16) | −0.001 (2) |
N4 | 0.0393 (17) | 0.0261 (17) | 0.0295 (15) | −0.0016 (16) | 0.0114 (13) | −0.0004 (15) |
N5 | 0.0310 (16) | 0.0324 (17) | 0.0267 (15) | −0.0040 (15) | 0.0083 (13) | −0.0021 (15) |
N6 | 0.039 (2) | 0.059 (3) | 0.045 (2) | −0.017 (2) | 0.0094 (17) | 0.000 (2) |
C1 | 0.033 (2) | 0.042 (3) | 0.0273 (19) | −0.0043 (19) | 0.0060 (16) | −0.0083 (19) |
C2 | 0.0354 (19) | 0.041 (2) | 0.0207 (16) | −0.0011 (18) | 0.0069 (15) | −0.0033 (16) |
C3 | 0.041 (2) | 0.046 (3) | 0.0296 (18) | −0.003 (2) | 0.0146 (16) | −0.0030 (19) |
C4 | 0.038 (2) | 0.039 (2) | 0.0342 (19) | −0.0021 (19) | 0.0162 (16) | −0.0037 (18) |
C5 | 0.039 (2) | 0.071 (4) | 0.044 (2) | −0.003 (3) | 0.0179 (18) | −0.002 (3) |
C6 | 0.033 (2) | 0.048 (3) | 0.039 (2) | −0.001 (2) | 0.0045 (17) | −0.002 (2) |
C7 | 0.035 (2) | 0.037 (2) | 0.0280 (19) | −0.0117 (19) | 0.0048 (16) | −0.0017 (18) |
C8 | 0.043 (2) | 0.038 (2) | 0.0231 (17) | −0.008 (2) | 0.0073 (16) | −0.0025 (18) |
C9 | 0.048 (2) | 0.057 (3) | 0.034 (2) | −0.012 (2) | 0.0183 (18) | −0.013 (2) |
C10 | 0.037 (2) | 0.040 (3) | 0.0307 (19) | −0.0038 (18) | 0.0112 (16) | −0.0002 (17) |
C11 | 0.045 (3) | 0.061 (3) | 0.041 (2) | −0.012 (3) | 0.016 (2) | 0.001 (2) |
C12 | 0.038 (2) | 0.042 (2) | 0.034 (2) | −0.010 (2) | 0.0072 (17) | −0.001 (2) |
Co2 | 0.0230 (2) | 0.0359 (3) | 0.0214 (2) | −0.0044 (2) | 0.00535 (17) | 0.0013 (2) |
O5 | 0.0336 (14) | 0.060 (2) | 0.0327 (15) | −0.0138 (15) | 0.0109 (12) | 0.0019 (15) |
O6 | 0.0419 (18) | 0.086 (3) | 0.056 (2) | −0.033 (2) | 0.0105 (16) | 0.001 (2) |
O7 | 0.0338 (13) | 0.0490 (18) | 0.0249 (12) | −0.0115 (16) | 0.0046 (10) | 0.0005 (15) |
O8 | 0.0499 (18) | 0.067 (3) | 0.0274 (14) | −0.0155 (19) | 0.0015 (13) | −0.0059 (17) |
N7 | 0.0275 (14) | 0.0354 (18) | 0.0259 (14) | 0.0013 (16) | 0.0080 (12) | 0.0024 (16) |
N8 | 0.0321 (17) | 0.0331 (18) | 0.0337 (17) | −0.0043 (15) | 0.0045 (14) | 0.0048 (16) |
N9 | 0.052 (2) | 0.041 (2) | 0.063 (3) | 0.009 (2) | −0.002 (2) | 0.009 (2) |
N10 | 0.0246 (15) | 0.0316 (18) | 0.0291 (16) | 0.0005 (14) | 0.0081 (13) | 0.0027 (14) |
N11 | 0.0265 (15) | 0.047 (2) | 0.0249 (15) | 0.0038 (16) | 0.0057 (13) | −0.0039 (16) |
N12 | 0.041 (2) | 0.068 (3) | 0.045 (2) | 0.021 (2) | 0.0145 (17) | 0.001 (2) |
C13 | 0.0295 (19) | 0.052 (3) | 0.037 (2) | −0.008 (2) | 0.0048 (15) | 0.001 (2) |
C14 | 0.0292 (18) | 0.043 (2) | 0.0289 (17) | −0.008 (2) | 0.0018 (14) | 0.002 (2) |
C15 | 0.050 (3) | 0.045 (3) | 0.034 (2) | −0.010 (2) | 0.008 (2) | −0.003 (2) |
C16 | 0.042 (2) | 0.034 (2) | 0.036 (2) | −0.0081 (19) | 0.0084 (18) | 0.0037 (19) |
C17 | 0.057 (3) | 0.037 (3) | 0.061 (3) | 0.002 (2) | 0.008 (2) | 0.002 (3) |
C18 | 0.042 (2) | 0.040 (3) | 0.040 (2) | −0.003 (2) | 0.0001 (19) | 0.007 (2) |
C19 | 0.0306 (19) | 0.045 (3) | 0.0284 (19) | 0.000 (2) | 0.0015 (15) | −0.0006 (19) |
C20 | 0.0241 (17) | 0.041 (2) | 0.034 (2) | −0.0040 (18) | 0.0035 (15) | −0.0020 (19) |
C21 | 0.042 (2) | 0.039 (2) | 0.045 (2) | −0.005 (2) | 0.011 (2) | −0.006 (2) |
C22 | 0.038 (2) | 0.038 (2) | 0.037 (2) | 0.004 (2) | 0.0133 (18) | −0.001 (2) |
C23 | 0.052 (3) | 0.046 (3) | 0.055 (3) | 0.014 (2) | 0.019 (2) | −0.002 (2) |
C24 | 0.030 (2) | 0.064 (3) | 0.0287 (19) | 0.010 (2) | 0.0107 (16) | 0.000 (2) |
Cl | 0.0572 (11) | 0.0659 (13) | 0.0496 (9) | −0.0038 (10) | 0.0205 (8) | −0.0019 (9) |
N13 | 0.052 (2) | 0.057 (3) | 0.051 (2) | 0.000 (2) | 0.021 (2) | 0.012 (2) |
O9 | 0.0408 (17) | 0.080 (3) | 0.070 (2) | −0.013 (2) | 0.0210 (17) | −0.023 (2) |
O10 | 0.097 (3) | 0.201 (9) | 0.068 (3) | 0.044 (5) | 0.049 (3) | 0.049 (4) |
O11 | 0.062 (3) | 0.187 (8) | 0.063 (3) | −0.028 (4) | 0.002 (2) | 0.008 (4) |
O12 | 0.0428 (18) | 0.091 (3) | 0.051 (2) | −0.002 (2) | 0.0101 (15) | 0.004 (2) |
O13 | 0.091 (4) | 0.069 (4) | 0.155 (6) | −0.030 (3) | 0.028 (4) | −0.015 (4) |
O14A | 0.102 (8) | 0.075 (7) | 0.056 (10) | 0.052 (6) | 0.057 (9) | 0.043 (9) |
O14B | 0.092 (9) | 0.108 (11) | 0.066 (12) | 0.055 (8) | 0.065 (11) | 0.044 (11) |
O15A | 0.117 (7) | 0.033 (4) | 0.067 (5) | 0.004 (5) | 0.046 (5) | 0.015 (4) |
O15B | 0.114 (9) | 0.071 (7) | 0.109 (9) | −0.004 (7) | −0.017 (7) | 0.004 (7) |
O16 | 0.051 (4) | 0.083 (7) | 0.042 (4) | 0.011 (5) | −0.005 (4) | −0.007 (5) |
Geometric parameters (Å, º) top
Co1—O3 | 1.882 (3) | O8—C19 | 1.229 (5) |
Co1—O1 | 1.886 (3) | N7—C14 | 1.474 (6) |
Co1—N4 | 1.916 (3) | N7—H7B | 0.9000 |
Co1—N1 | 1.928 (3) | N7—H7A | 0.9000 |
Co1—N2 | 1.941 (3) | N8—C18 | 1.315 (6) |
Co1—N5 | 1.942 (3) | N8—C16 | 1.398 (6) |
O1—C1 | 1.282 (5) | N9—C18 | 1.316 (8) |
O2—C1 | 1.233 (6) | N9—C17 | 1.367 (7) |
O3—C7 | 1.282 (5) | N9—H9NA | 0.8600 |
O4—C7 | 1.222 (6) | N10—C20 | 1.469 (5) |
N1—C2 | 1.495 (5) | N10—H10A | 0.9000 |
N1—H1A | 0.9000 | N10—H10B | 0.9000 |
N1—H1B | 0.9000 | N11—C24 | 1.329 (5) |
N2—C6 | 1.313 (5) | N11—C22 | 1.377 (6) |
N2—C4 | 1.383 (5) | N12—C24 | 1.317 (8) |
N3—C6 | 1.319 (6) | N12—C23 | 1.348 (7) |
N3—C5 | 1.358 (6) | N12—H12N | 0.8600 |
N3—H3NA | 0.8600 | C13—C14 | 1.513 (6) |
N4—C8 | 1.484 (5) | C14—C15 | 1.513 (8) |
N4—H4A | 0.9000 | C14—H14A | 0.9800 |
N4—H4B | 0.9000 | C15—C16 | 1.485 (6) |
N5—C12 | 1.325 (6) | C15—H15A | 0.9700 |
N5—C10 | 1.381 (5) | C15—H15B | 0.9700 |
N6—C12 | 1.324 (6) | C16—C17 | 1.340 (7) |
N6—C11 | 1.368 (7) | C17—H17A | 0.9300 |
N6—H6NA | 0.8600 | C18—H18A | 0.9300 |
C1—C2 | 1.510 (7) | C19—C20 | 1.514 (6) |
C2—C3 | 1.507 (6) | C20—C21 | 1.499 (7) |
C2—H2A | 0.9800 | C20—H20A | 0.9800 |
C3—C4 | 1.496 (6) | C21—C22 | 1.510 (6) |
C3—H3A | 0.9700 | C21—H21A | 0.9700 |
C3—H3B | 0.9700 | C21—H21B | 0.9700 |
C4—C5 | 1.348 (6) | C22—C23 | 1.357 (7) |
C5—H5A | 0.9300 | C23—H23A | 0.9300 |
C6—H6A | 0.9300 | C24—H24A | 0.9300 |
C7—C8 | 1.514 (7) | Cl—O33 | 0.66 (2) |
C8—C9 | 1.522 (6) | Cl—N30 | 0.747 (17) |
C8—H8A | 0.9800 | Cl—O31 | 1.507 (16) |
C9—C10 | 1.501 (6) | Cl—O32 | 1.910 (18) |
C9—H9A | 0.9700 | N13—O10 | 1.210 (6) |
C9—H9B | 0.9700 | N13—O11 | 1.218 (6) |
C10—C11 | 1.348 (7) | N13—O9 | 1.228 (6) |
C11—H11A | 0.9300 | O12—H121 | 1.1094 |
C12—H12A | 0.9300 | O13—H131 | 0.8785 |
Co2—O5 | 1.907 (3) | O13—H132 | 0.8463 |
Co2—N7 | 1.915 (3) | O16—O17 | 0.665 (14) |
Co2—N8 | 1.919 (4) | O16—O32 | 1.006 (19) |
Co2—O7 | 1.920 (3) | O17—O32 | 1.50 (2) |
Co2—N10 | 1.926 (3) | N30—O31 | 1.247 (16) |
Co2—N11 | 1.928 (4) | N30—O32 | 1.251 (17) |
O5—C13 | 1.284 (5) | N30—O33 | 1.259 (18) |
O6—C13 | 1.222 (6) | O31—O31i | 1.78 (3) |
O7—C19 | 1.283 (6) | | |
| | | |
O3—Co1—O1 | 90.36 (13) | N10—Co2—N11 | 88.83 (16) |
O3—Co1—N4 | 85.55 (14) | C13—O5—Co2 | 113.6 (3) |
O1—Co1—N4 | 175.32 (15) | C19—O7—Co2 | 113.3 (3) |
O3—Co1—N1 | 174.23 (14) | C14—N7—Co2 | 106.5 (2) |
O1—Co1—N1 | 85.33 (14) | C14—N7—H7B | 110.4 |
N4—Co1—N1 | 98.90 (15) | Co2—N7—H7B | 110.4 |
O3—Co1—N2 | 89.48 (15) | C14—N7—H7A | 110.4 |
O1—Co1—N2 | 90.41 (14) | Co2—N7—H7A | 110.4 |
N4—Co1—N2 | 91.82 (15) | H7B—N7—H7A | 108.6 |
N1—Co1—N2 | 86.73 (14) | C18—N8—C16 | 106.1 (4) |
O3—Co1—N5 | 89.56 (15) | C18—N8—Co2 | 126.3 (3) |
O1—Co1—N5 | 90.46 (15) | C16—N8—Co2 | 127.6 (3) |
N4—Co1—N5 | 87.24 (15) | C18—N9—C17 | 108.3 (5) |
N1—Co1—N5 | 94.30 (14) | C18—N9—H9NA | 125.9 |
N2—Co1—N5 | 178.71 (14) | C17—N9—H9NA | 125.9 |
C1—O1—Co1 | 113.8 (3) | C20—N10—Co2 | 106.5 (2) |
C7—O3—Co1 | 114.9 (3) | C20—N10—H10A | 110.4 |
C2—N1—Co1 | 106.1 (3) | Co2—N10—H10A | 110.4 |
C2—N1—H1A | 110.5 | C20—N10—H10B | 110.4 |
Co1—N1—H1A | 110.5 | Co2—N10—H10B | 110.4 |
C2—N1—H1B | 110.5 | H10A—N10—H10B | 108.6 |
Co1—N1—H1B | 110.5 | C24—N11—C22 | 105.3 (4) |
H1A—N1—H1B | 108.7 | C24—N11—Co2 | 126.7 (4) |
C6—N2—C4 | 107.2 (4) | C22—N11—Co2 | 127.9 (3) |
C6—N2—Co1 | 125.4 (3) | C24—N12—C23 | 108.8 (4) |
C4—N2—Co1 | 127.3 (3) | C24—N12—H12N | 125.6 |
C6—N3—C5 | 108.7 (4) | C23—N12—H12N | 125.6 |
C6—N3—H3NA | 125.6 | O6—C13—O5 | 123.7 (4) |
C5—N3—H3NA | 125.6 | O6—C13—C14 | 120.5 (4) |
C8—N4—Co1 | 106.5 (3) | O5—C13—C14 | 115.6 (4) |
C8—N4—H4A | 110.4 | N7—C14—C13 | 108.0 (4) |
Co1—N4—H4A | 110.4 | N7—C14—C15 | 110.1 (3) |
C8—N4—H4B | 110.4 | C13—C14—C15 | 109.8 (4) |
Co1—N4—H4B | 110.4 | N7—C14—H14A | 109.7 |
H4A—N4—H4B | 108.6 | C13—C14—H14A | 109.7 |
C12—N5—C10 | 106.3 (4) | C15—C14—H14A | 109.7 |
C12—N5—Co1 | 126.7 (3) | C16—C15—C14 | 113.4 (4) |
C10—N5—Co1 | 127.0 (3) | C16—C15—H15A | 108.9 |
C12—N6—C11 | 108.1 (4) | C14—C15—H15A | 108.9 |
C12—N6—H6NA | 126.0 | C16—C15—H15B | 108.9 |
C11—N6—H6NA | 126.0 | C14—C15—H15B | 108.9 |
O2—C1—O1 | 122.7 (5) | H15A—C15—H15B | 107.7 |
O2—C1—C2 | 120.7 (4) | C17—C16—N8 | 107.9 (4) |
O1—C1—C2 | 116.6 (4) | C17—C16—C15 | 129.4 (5) |
N1—C2—C3 | 109.8 (3) | N8—C16—C15 | 122.7 (4) |
N1—C2—C1 | 107.7 (3) | C16—C17—N9 | 106.9 (5) |
C3—C2—C1 | 108.7 (4) | C16—C17—H17A | 126.6 |
N1—C2—H2A | 110.2 | N9—C17—H17A | 126.6 |
C3—C2—H2A | 110.2 | N8—C18—N9 | 110.9 (5) |
C1—C2—H2A | 110.2 | N8—C18—H18A | 124.5 |
C4—C3—C2 | 112.3 (3) | N9—C18—H18A | 124.5 |
C4—C3—H3A | 109.1 | O8—C19—O7 | 123.3 (4) |
C2—C3—H3A | 109.1 | O8—C19—C20 | 120.8 (4) |
C4—C3—H3B | 109.1 | O7—C19—C20 | 115.9 (3) |
C2—C3—H3B | 109.1 | N10—C20—C21 | 109.5 (4) |
H3A—C3—H3B | 107.9 | N10—C20—C19 | 107.9 (4) |
C5—C4—N2 | 107.5 (4) | C21—C20—C19 | 110.9 (4) |
C5—C4—C3 | 128.8 (4) | N10—C20—H20A | 109.5 |
N2—C4—C3 | 123.8 (4) | C21—C20—H20A | 109.5 |
C4—C5—N3 | 106.7 (4) | C19—C20—H20A | 109.5 |
C4—C5—H5A | 126.6 | C20—C21—C22 | 113.0 (4) |
N3—C5—H5A | 126.6 | C20—C21—H21A | 109.0 |
N2—C6—N3 | 109.9 (4) | C22—C21—H21A | 109.0 |
N2—C6—H6A | 125.0 | C20—C21—H21B | 109.0 |
N3—C6—H6A | 125.0 | C22—C21—H21B | 109.0 |
O4—C7—O3 | 123.0 (5) | H21A—C21—H21B | 107.8 |
O4—C7—C8 | 122.0 (4) | C23—C22—N11 | 108.9 (4) |
O3—C7—C8 | 115.0 (4) | C23—C22—C21 | 129.1 (5) |
N4—C8—C7 | 108.0 (3) | N11—C22—C21 | 122.0 (4) |
N4—C8—C9 | 108.7 (4) | N12—C23—C22 | 106.2 (5) |
C7—C8—C9 | 109.9 (4) | N12—C23—H23A | 126.9 |
N4—C8—H8A | 110.1 | C22—C23—H23A | 126.9 |
C7—C8—H8A | 110.1 | N12—C24—N11 | 110.8 (5) |
C9—C8—H8A | 110.1 | N12—C24—H24A | 124.6 |
C10—C9—C8 | 113.7 (4) | N11—C24—H24A | 124.6 |
C10—C9—H9A | 108.8 | O33—Cl—N30 | 126 (3) |
C8—C9—H9A | 108.8 | O33—Cl—O31 | 178 (3) |
C10—C9—H9B | 108.8 | N30—Cl—O31 | 55.5 (12) |
C8—C9—H9B | 108.8 | O33—Cl—O32 | 104 (2) |
H9A—C9—H9B | 107.7 | N30—Cl—O32 | 22.3 (12) |
C11—C10—N5 | 108.4 (4) | O31—Cl—O32 | 77.7 (7) |
C11—C10—C9 | 128.3 (4) | O10—N13—O11 | 120.0 (6) |
N5—C10—C9 | 123.2 (4) | O10—N13—O9 | 119.0 (5) |
C10—C11—N6 | 106.7 (4) | O11—N13—O9 | 120.9 (4) |
C10—C11—H11A | 126.7 | H131—O13—H132 | 69.0 |
N6—C11—H11A | 126.7 | O17—O16—O32 | 127 (3) |
N6—C12—N5 | 110.5 (4) | O16—O17—O32 | 32.4 (19) |
N6—C12—H12A | 124.8 | Cl—N30—O31 | 94.9 (16) |
N5—C12—H12A | 124.8 | Cl—N30—O32 | 144.7 (18) |
O5—Co2—N7 | 85.02 (13) | O31—N30—O32 | 120.3 (14) |
O5—Co2—N8 | 89.58 (16) | Cl—N30—O33 | 25.1 (15) |
N7—Co2—N8 | 87.94 (16) | O31—N30—O33 | 119.9 (15) |
O5—Co2—O7 | 94.04 (12) | O32—N30—O33 | 119.7 (14) |
N7—Co2—O7 | 178.38 (19) | N30—O31—Cl | 29.6 (8) |
N8—Co2—O7 | 90.73 (16) | N30—O31—O31i | 173.7 (17) |
O5—Co2—N10 | 177.77 (15) | Cl—O31—O31i | 156.3 (10) |
N7—Co2—N10 | 96.78 (14) | O16—O32—N30 | 158 (2) |
N8—Co2—N10 | 91.80 (16) | O16—O32—O17 | 20.8 (11) |
O7—Co2—N10 | 84.19 (13) | N30—O32—O17 | 142.2 (19) |
O5—Co2—N11 | 89.78 (16) | O16—O32—Cl | 165.4 (18) |
N7—Co2—N11 | 92.44 (16) | N30—O32—Cl | 13.1 (7) |
N8—Co2—N11 | 179.22 (16) | O17—O32—Cl | 145.0 (15) |
O7—Co2—N11 | 88.88 (16) | Cl—O33—N30 | 28.5 (16) |
Symmetry code: (i) −x+1, y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O17 | 0.90 | 2.87 | 3.764 (15) | 171 |
N1—H1B···O4ii | 0.90 | 2.25 | 3.121 (6) | 162 |
N3—H3NA···O12 | 0.86 | 1.97 | 2.764 (5) | 154 |
N4—H4A···O3ii | 0.90 | 2.19 | 2.880 (5) | 134 |
N4—H4A···O1ii | 0.90 | 2.54 | 3.219 (5) | 133 |
N4—H4B···O13ii | 0.90 | 2.12 | 2.988 (6) | 162 |
N6—H6NA···O8iii | 0.86 | 2.18 | 3.024 (5) | 166 |
N7—H7B···O2iv | 0.90 | 2.01 | 2.845 (5) | 154 |
N7—H7A···O9v | 0.90 | 2.02 | 2.922 (5) | 175 |
N9—H9NA···O16vi | 0.86 | 1.96 | 2.807 (9) | 169 |
N9—H9NA···O17vi | 0.86 | 1.98 | 2.811 (17) | 162 |
N10—H10A···O9vii | 0.90 | 2.23 | 3.032 (5) | 149 |
N10—H10B···Cliv | 0.90 | 2.42 | 3.309 (4) | 169 |
N12—H12N···O14Bviii | 0.86 | 2.14 | 2.80 (3) | 134 |
N12—H12N···O14Aviii | 0.86 | 2.21 | 2.86 (3) | 132 |
N12—H12N···O6iv | 0.86 | 2.36 | 2.971 (6) | 129 |
Symmetry codes: (ii) −x+3/2, y+1/2, −z+1; (iii) x−1/2, y−1/2, z; (iv) −x+3/2, y+1/2, −z; (v) x, y, z−1; (vi) x+1/2, y−1/2, z; (vii) −x+2, y, −z+1; (viii) x, y+1, z. |
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