Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009024/cv6185sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009024/cv6185Isup2.hkl |
CCDC reference: 214582
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.052
- wR factor = 0.135
- Data-to-parameter ratio = 15.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
PLAT_368 Alert B Short C(sp2)-C(sp2) Bond C54 - C54_a = 1.13 Ang.
Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 5.00 Perc. PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C53 - C54 = 1.54 Ang.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
2 Alert Level C = Please check
A dimethylformamide solution (20 ml) containing CoCl2·6H2O (0.12 g, 0.5 mmol), 1,10-phenanthroline (0.18 g, 1 mmol) and fumaric acid (0.058 g, 0.5 mmol) was refluxed under the atmosphere for 2 h. Pale pink single crystals of the title compound were obtained from the filtrate after 2 weeks.
The H atoms on C atoms, except those on disordered C atoms, were placed in calculated positions with C—H = 0.93 Å and included in the final cycles of refinement in riding model, with Uiso(H) = 1.2Ueq of the carrier atom. Other H atoms were located with combination of difference Fourier maps and theoretical calculation (Nardelli, 1993), and were included in the final cycles of refinement with fixed coordinates and isotropic displacement parameters of 0.08 Å2. An unreasonably short distance C54 ═C54(1 − x,1 − y,-z) of 1.135 (7) Å and a longer C53—C54 distance of 1.539 (6) Å were observed in the structure. It may be due to the disorder of the structure. The larger thermal parameters implied the possible disorder of the C54 atom, but it was not successfully resolved.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Co(C12H8N2)3](C3H2O4)(C3H3O4)·C3H4O4·4H2O | Z = 2 |
Mr = 1017.81 | F(000) = 1054 |
Triclinic, P1 | Dx = 1.506 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 12.167 (2) Å | Cell parameters from 13658 reflections |
b = 12.487 (2) Å | θ = 1.5–27.0° |
c = 17.040 (2) Å | µ = 0.47 mm−1 |
α = 102.85 (2)° | T = 298 K |
β = 90.28 (1)° | Plate, pink |
γ = 116.39 (2)° | 0.42 × 0.22 × 0.08 mm |
V = 2245.0 (8) Å3 |
Bruker SMART CCD diffractometer | 9991 independent reflections |
Radiation source: fine-focus sealed tube | 5138 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω and ϕ scans | θmax = 27.6°, θmin = 1.2° |
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 1999) | h = −15→15 |
Tmin = 0.82, Tmax = 0.96 | k = −10→16 |
14499 measured reflections | l = −22→21 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 0.86 | w = 1/[σ2(Fo2) + (0.0578P)2] where P = (Fo2 + 2Fc2)/3 |
9991 reflections | (Δ/σ)max = 0.002 |
658 parameters | Δρmax = 0.76 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
[Co(C12H8N2)3](C3H2O4)(C3H3O4)·C3H4O4·4H2O | γ = 116.39 (2)° |
Mr = 1017.81 | V = 2245.0 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.167 (2) Å | Mo Kα radiation |
b = 12.487 (2) Å | µ = 0.47 mm−1 |
c = 17.040 (2) Å | T = 298 K |
α = 102.85 (2)° | 0.42 × 0.22 × 0.08 mm |
β = 90.28 (1)° |
Bruker SMART CCD diffractometer | 9991 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 1999) | 5138 reflections with I > 2σ(I) |
Tmin = 0.82, Tmax = 0.96 | Rint = 0.035 |
14499 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 0.86 | Δρmax = 0.76 e Å−3 |
9991 reflections | Δρmin = −0.46 e Å−3 |
658 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Co | 0.81131 (3) | 0.82696 (4) | 0.23014 (2) | 0.03139 (13) | |
O1 | 0.2464 (2) | 0.6364 (2) | 0.34103 (15) | 0.0691 (7) | |
O2 | 0.1733 (2) | 0.7260 (3) | 0.2717 (2) | 0.0880 (9) | |
O3 | 0.5641 (3) | 1.1219 (3) | 0.30102 (16) | 0.0793 (9) | |
O4 | 0.5679 (2) | 1.0971 (2) | 0.42327 (16) | 0.0731 (8) | |
O11 | 0.2290 (4) | 0.6913 (3) | 0.52769 (18) | 0.1089 (12) | |
O12 | 0.1134 (3) | 0.7149 (3) | 0.6200 (2) | 0.0974 (11) | |
O13 | 0.4375 (3) | 0.2793 (3) | 0.04708 (18) | 0.0944 (10) | |
O14 | 0.6300 (3) | 0.4168 (3) | 0.06735 (18) | 0.0845 (9) | |
O15 | 0.4259 (2) | 0.6419 (2) | 0.41561 (17) | 0.0729 (8) | |
O16 | 0.2972 (2) | 0.4533 (3) | 0.42391 (19) | 0.0884 (10) | |
O17 | 0.4874 (4) | 0.1627 (3) | 0.1343 (2) | 0.1278 (15) | |
O18 | 0.5003 (3) | 0.0056 (3) | 0.15825 (19) | 0.0904 (10) | |
O21 | 0.1804 (3) | 0.7787 (3) | 0.11029 (18) | 0.1017 (10) | |
O22 | 0.8471 (3) | 0.3844 (3) | 0.04302 (19) | 0.0962 (10) | |
O23 | 0.0330 (3) | 0.4775 (3) | 0.1748 (2) | 0.1140 (12) | |
O24 | 0.0906 (3) | 0.3486 (4) | 0.2746 (2) | 0.1347 (15) | |
N1 | 0.9967 (2) | 0.9438 (2) | 0.27818 (14) | 0.0371 (6) | |
N2 | 0.7906 (2) | 0.9022 (2) | 0.34961 (14) | 0.0371 (6) | |
N3 | 0.8500 (2) | 0.7741 (2) | 0.11298 (14) | 0.0361 (6) | |
N4 | 0.8138 (2) | 0.9688 (2) | 0.18236 (15) | 0.0404 (6) | |
N5 | 0.6211 (2) | 0.7225 (2) | 0.20174 (14) | 0.0400 (6) | |
N6 | 0.7870 (2) | 0.6646 (2) | 0.25900 (14) | 0.0393 (6) | |
C1 | 1.0978 (3) | 0.9647 (3) | 0.24169 (19) | 0.0441 (8) | |
H1 | 1.0918 | 0.9100 | 0.1929 | 0.053* | |
C2 | 1.2133 (3) | 1.0656 (3) | 0.2732 (2) | 0.0525 (9) | |
H2 | 1.2818 | 1.0782 | 0.2453 | 0.063* | |
C3 | 1.2230 (3) | 1.1441 (3) | 0.3449 (2) | 0.0559 (10) | |
H3 | 1.2988 | 1.2118 | 0.3665 | 0.067* | |
C4 | 1.1197 (3) | 1.1241 (3) | 0.3870 (2) | 0.0465 (8) | |
C5 | 1.1235 (3) | 1.2009 (3) | 0.4649 (2) | 0.0563 (10) | |
H5 | 1.1969 | 1.2702 | 0.4887 | 0.068* | |
C6 | 1.0214 (3) | 1.1731 (3) | 0.5036 (2) | 0.0560 (10) | |
H6 | 1.0262 | 1.2223 | 0.5546 | 0.067* | |
C7 | 0.9057 (3) | 1.0690 (3) | 0.46748 (19) | 0.0442 (8) | |
C8 | 0.7961 (3) | 1.0351 (4) | 0.5047 (2) | 0.0574 (10) | |
H8 | 0.7971 | 1.0802 | 0.5563 | 0.069* | |
C9 | 0.6902 (3) | 0.9380 (3) | 0.4663 (2) | 0.0535 (9) | |
H9 | 0.6185 | 0.9139 | 0.4915 | 0.064* | |
C10 | 0.6901 (3) | 0.8741 (3) | 0.38799 (19) | 0.0466 (8) | |
H10 | 0.6160 | 0.8085 | 0.3612 | 0.056* | |
C11 | 0.8988 (3) | 0.9986 (3) | 0.39041 (17) | 0.0351 (7) | |
C12 | 1.0081 (3) | 1.0233 (3) | 0.35111 (17) | 0.0353 (7) | |
C13 | 0.8712 (3) | 0.6794 (3) | 0.07891 (19) | 0.0430 (8) | |
H13 | 0.8750 | 0.6296 | 0.1111 | 0.052* | |
C14 | 0.8881 (3) | 0.6511 (3) | −0.0019 (2) | 0.0483 (9) | |
H14 | 0.9038 | 0.5845 | −0.0227 | 0.058* | |
C15 | 0.8815 (3) | 0.7210 (3) | −0.0506 (2) | 0.0501 (9) | |
H15 | 0.8925 | 0.7024 | −0.1050 | 0.060* | |
C16 | 0.8581 (3) | 0.8206 (3) | −0.01889 (18) | 0.0414 (8) | |
C17 | 0.8512 (3) | 0.9005 (3) | −0.0649 (2) | 0.0554 (10) | |
H17 | 0.8582 | 0.8843 | −0.1201 | 0.067* | |
C18 | 0.8341 (3) | 1.0011 (4) | −0.0286 (2) | 0.0568 (10) | |
H18 | 0.8310 | 1.0528 | −0.0593 | 0.068* | |
C19 | 0.8214 (3) | 1.0262 (3) | 0.0540 (2) | 0.0435 (8) | |
C20 | 0.8089 (3) | 1.1317 (3) | 0.0956 (2) | 0.0578 (10) | |
H20 | 0.8076 | 1.1873 | 0.0677 | 0.069* | |
C21 | 0.7988 (3) | 1.1505 (3) | 0.1760 (2) | 0.0550 (9) | |
H21 | 0.7909 | 1.2195 | 0.2036 | 0.066* | |
C22 | 0.8002 (3) | 1.0668 (3) | 0.2176 (2) | 0.0481 (8) | |
H22 | 0.7911 | 1.0806 | 0.2725 | 0.058* | |
C23 | 0.8249 (3) | 0.9486 (3) | 0.10042 (18) | 0.0381 (7) | |
C24 | 0.8450 (3) | 0.8460 (3) | 0.06486 (17) | 0.0361 (7) | |
C25 | 0.5398 (3) | 0.7516 (3) | 0.1726 (2) | 0.0507 (9) | |
H25 | 0.5683 | 0.8264 | 0.1584 | 0.061* | |
C26 | 0.4119 (3) | 0.6734 (4) | 0.1622 (2) | 0.0603 (10) | |
H26 | 0.3575 | 0.6957 | 0.1401 | 0.072* | |
C27 | 0.3681 (3) | 0.5656 (4) | 0.1845 (2) | 0.0611 (11) | |
H27 | 0.2834 | 0.5148 | 0.1793 | 0.073* | |
C28 | 0.4507 (3) | 0.5307 (3) | 0.2156 (2) | 0.0499 (9) | |
C29 | 0.4146 (4) | 0.4185 (4) | 0.2399 (2) | 0.0664 (11) | |
H29 | 0.3310 | 0.3644 | 0.2366 | 0.080* | |
C30 | 0.4990 (4) | 0.3897 (3) | 0.2673 (2) | 0.0657 (11) | |
H30 | 0.4726 | 0.3153 | 0.2819 | 0.079* | |
C31 | 0.6284 (3) | 0.4701 (3) | 0.2746 (2) | 0.0517 (9) | |
C32 | 0.7199 (4) | 0.4443 (4) | 0.3023 (2) | 0.0658 (11) | |
H32 | 0.6982 | 0.3713 | 0.3180 | 0.079* | |
C33 | 0.8400 (4) | 0.5254 (4) | 0.3063 (2) | 0.0583 (10) | |
H33 | 0.9016 | 0.5080 | 0.3235 | 0.070* | |
C34 | 0.8709 (3) | 0.6355 (3) | 0.28446 (19) | 0.0484 (9) | |
H34 | 0.9540 | 0.6909 | 0.2879 | 0.058* | |
C35 | 0.6668 (3) | 0.5831 (3) | 0.25405 (18) | 0.0412 (8) | |
C36 | 0.5772 (3) | 0.6128 (3) | 0.22259 (18) | 0.0415 (8) | |
C41 | 0.2517 (3) | 0.7281 (4) | 0.3211 (2) | 0.0570 (10) | |
C42 | 0.3634 (3) | 0.8509 (4) | 0.3580 (2) | 0.0606 (10) | |
H42 | 0.4004 | 0.8643 | 0.4095 | 0.073* | |
C43 | 0.4081 (3) | 0.9364 (4) | 0.3207 (2) | 0.0587 (10) | |
H43 | 0.3681 | 0.9223 | 0.2701 | 0.070* | |
C44 | 0.5217 (3) | 1.0590 (4) | 0.3529 (3) | 0.0568 (10) | |
C51 | 0.1276 (5) | 0.6567 (4) | 0.5592 (3) | 0.0837 (16) | |
C52A | −0.002 (2) | 0.5374 (14) | 0.5287 (6) | 0.058 (2) | 0.50 |
C52B | 0.0584 (9) | 0.5334 (14) | 0.4955 (10) | 0.059 (3) | 0.50 |
C53 | 0.5266 (4) | 0.3846 (4) | 0.0435 (2) | 0.0593 (10) | |
C54 | 0.4705 (5) | 0.4527 (4) | 0.0054 (3) | 0.0842 (15) | |
H54 | 0.3856 | 0.4152 | −0.0092 | 0.101* | |
C55 | 0.3967 (4) | 0.5398 (4) | 0.4379 (2) | 0.0599 (10) | |
C56 | 0.5029 (3) | 0.5442 (3) | 0.4845 (2) | 0.0651 (11) | |
H56 | 0.5784 | 0.6147 | 0.4918 | 0.078* | |
C61 | 0.4901 (4) | 0.0653 (5) | 0.1113 (3) | 0.0753 (13) | |
C62A | 0.4823 (12) | −0.0240 (17) | 0.0290 (12) | 0.078 (5) | 0.50 |
C62B | 0.4870 (11) | 0.0451 (17) | 0.0215 (9) | 0.069 (3) | 0.50 |
H03 | 0.5679 | 1.1033 | 0.2499 | 0.080* | |
H011 | 0.2885 | 0.7531 | 0.5627 | 0.080* | |
H013 | 0.4740 | 0.2606 | 0.0872 | 0.080* | |
H015 | 0.3658 | 0.6615 | 0.4237 | 0.080* | |
H211 | 0.1796 | 0.7414 | 0.1566 | 0.080* | |
H212 | 0.1993 | 0.7312 | 0.0660 | 0.080* | |
H221 | 0.7744 | 0.3958 | 0.0601 | 0.080* | |
H222 | 0.8984 | 0.4349 | 0.0952 | 0.080* | |
H231 | 0.0388 | 0.4608 | 0.2255 | 0.080* | |
H232 | 0.0578 | 0.5587 | 0.1922 | 0.080* | |
H241 | 0.0220 | 0.3206 | 0.3029 | 0.080* | |
H242 | 0.1477 | 0.3885 | 0.3136 | 0.050* | |
H52A | −0.0774 | 0.5109 | 0.5460 | 0.080* | 0.50 |
H52B | 0.0844 | 0.4974 | 0.4543 | 0.080* | 0.50 |
H62A | 0.4473 | −0.1016 | 0.0176 | 0.080* | 0.50 |
H62B | 0.4682 | 0.0825 | −0.0072 | 0.080* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co | 0.0300 (2) | 0.0293 (2) | 0.0313 (2) | 0.01135 (19) | 0.00179 (16) | 0.00572 (17) |
O1 | 0.0683 (18) | 0.0529 (18) | 0.0671 (18) | 0.0122 (15) | −0.0003 (13) | 0.0130 (15) |
O2 | 0.0585 (18) | 0.077 (2) | 0.127 (3) | 0.0256 (16) | −0.0089 (17) | 0.0330 (19) |
O3 | 0.091 (2) | 0.0663 (19) | 0.0633 (18) | 0.0158 (17) | 0.0080 (15) | 0.0263 (15) |
O4 | 0.088 (2) | 0.0647 (19) | 0.0486 (16) | 0.0209 (16) | −0.0012 (14) | 0.0117 (14) |
O11 | 0.128 (3) | 0.075 (2) | 0.064 (2) | 0.014 (2) | −0.004 (2) | −0.0244 (17) |
O12 | 0.064 (2) | 0.090 (3) | 0.106 (3) | 0.0067 (19) | 0.0007 (19) | 0.025 (2) |
O13 | 0.070 (2) | 0.108 (3) | 0.095 (2) | 0.024 (2) | −0.0140 (17) | 0.044 (2) |
O14 | 0.0628 (19) | 0.084 (2) | 0.096 (2) | 0.0246 (17) | −0.0001 (16) | 0.0224 (18) |
O15 | 0.0594 (17) | 0.0576 (18) | 0.099 (2) | 0.0195 (15) | 0.0122 (15) | 0.0294 (16) |
O16 | 0.0520 (17) | 0.0544 (19) | 0.135 (3) | 0.0007 (15) | −0.0101 (17) | 0.0303 (19) |
O17 | 0.229 (5) | 0.085 (3) | 0.059 (2) | 0.065 (3) | −0.015 (2) | 0.0155 (19) |
O18 | 0.106 (3) | 0.086 (2) | 0.073 (2) | 0.047 (2) | −0.0059 (18) | 0.0023 (18) |
O21 | 0.138 (3) | 0.098 (2) | 0.088 (2) | 0.069 (2) | −0.0017 (19) | 0.0244 (19) |
O22 | 0.111 (2) | 0.085 (2) | 0.118 (3) | 0.067 (2) | 0.018 (2) | 0.0250 (19) |
O23 | 0.095 (2) | 0.098 (3) | 0.112 (3) | 0.032 (2) | 0.021 (2) | −0.015 (2) |
O24 | 0.069 (2) | 0.161 (4) | 0.099 (3) | 0.008 (2) | −0.0045 (18) | −0.011 (2) |
N1 | 0.0343 (14) | 0.0358 (15) | 0.0390 (14) | 0.0138 (13) | 0.0035 (11) | 0.0105 (12) |
N2 | 0.0355 (14) | 0.0369 (16) | 0.0362 (14) | 0.0148 (13) | 0.0026 (11) | 0.0079 (12) |
N3 | 0.0360 (14) | 0.0299 (15) | 0.0367 (14) | 0.0123 (12) | −0.0002 (11) | 0.0036 (12) |
N4 | 0.0378 (15) | 0.0369 (16) | 0.0455 (16) | 0.0168 (13) | 0.0051 (12) | 0.0091 (13) |
N5 | 0.0369 (15) | 0.0403 (17) | 0.0380 (15) | 0.0173 (13) | −0.0018 (11) | 0.0015 (13) |
N6 | 0.0408 (15) | 0.0376 (16) | 0.0349 (14) | 0.0155 (14) | 0.0030 (11) | 0.0055 (12) |
C1 | 0.0417 (19) | 0.047 (2) | 0.0404 (18) | 0.0181 (17) | 0.0054 (15) | 0.0098 (16) |
C2 | 0.0364 (19) | 0.060 (3) | 0.055 (2) | 0.0137 (19) | 0.0090 (16) | 0.021 (2) |
C3 | 0.0354 (19) | 0.053 (2) | 0.066 (2) | 0.0049 (18) | 0.0020 (17) | 0.022 (2) |
C4 | 0.046 (2) | 0.040 (2) | 0.049 (2) | 0.0125 (17) | 0.0032 (16) | 0.0187 (17) |
C5 | 0.058 (2) | 0.036 (2) | 0.047 (2) | 0.0052 (18) | −0.0151 (18) | −0.0046 (17) |
C6 | 0.066 (2) | 0.043 (2) | 0.0378 (19) | 0.015 (2) | −0.0065 (18) | −0.0081 (17) |
C7 | 0.052 (2) | 0.040 (2) | 0.0419 (19) | 0.0217 (18) | 0.0056 (16) | 0.0110 (16) |
C8 | 0.071 (3) | 0.071 (3) | 0.043 (2) | 0.043 (2) | 0.0165 (19) | 0.0130 (19) |
C9 | 0.046 (2) | 0.059 (3) | 0.049 (2) | 0.021 (2) | 0.0118 (17) | 0.0056 (19) |
C10 | 0.0380 (19) | 0.051 (2) | 0.047 (2) | 0.0180 (17) | 0.0082 (15) | 0.0111 (17) |
C11 | 0.0391 (18) | 0.0293 (17) | 0.0325 (16) | 0.0136 (15) | −0.0005 (13) | 0.0042 (14) |
C12 | 0.0361 (17) | 0.0294 (17) | 0.0331 (16) | 0.0091 (15) | −0.0009 (13) | 0.0070 (14) |
C13 | 0.0426 (19) | 0.039 (2) | 0.0461 (19) | 0.0185 (17) | 0.0047 (15) | 0.0084 (16) |
C14 | 0.048 (2) | 0.043 (2) | 0.047 (2) | 0.0205 (18) | 0.0076 (16) | −0.0013 (17) |
C15 | 0.046 (2) | 0.051 (2) | 0.0385 (19) | 0.0136 (18) | 0.0067 (15) | 0.0020 (17) |
C16 | 0.0366 (18) | 0.037 (2) | 0.0369 (17) | 0.0068 (16) | −0.0004 (14) | 0.0057 (15) |
C17 | 0.058 (2) | 0.058 (3) | 0.039 (2) | 0.014 (2) | 0.0004 (16) | 0.0169 (19) |
C18 | 0.058 (2) | 0.056 (2) | 0.056 (2) | 0.018 (2) | 0.0050 (18) | 0.032 (2) |
C19 | 0.0405 (19) | 0.036 (2) | 0.047 (2) | 0.0100 (16) | −0.0005 (15) | 0.0135 (16) |
C20 | 0.052 (2) | 0.045 (2) | 0.075 (3) | 0.0150 (19) | −0.0001 (19) | 0.028 (2) |
C21 | 0.059 (2) | 0.036 (2) | 0.069 (3) | 0.0231 (19) | 0.0034 (19) | 0.0079 (19) |
C22 | 0.053 (2) | 0.038 (2) | 0.052 (2) | 0.0228 (18) | 0.0046 (16) | 0.0034 (17) |
C23 | 0.0354 (17) | 0.0324 (18) | 0.0379 (17) | 0.0094 (15) | −0.0018 (13) | 0.0060 (15) |
C24 | 0.0325 (17) | 0.0349 (18) | 0.0349 (17) | 0.0104 (15) | 0.0002 (13) | 0.0079 (15) |
C25 | 0.047 (2) | 0.055 (2) | 0.053 (2) | 0.0294 (19) | 0.0022 (16) | 0.0056 (18) |
C26 | 0.044 (2) | 0.073 (3) | 0.055 (2) | 0.030 (2) | −0.0060 (17) | −0.009 (2) |
C27 | 0.035 (2) | 0.063 (3) | 0.058 (2) | 0.015 (2) | 0.0020 (17) | −0.018 (2) |
C28 | 0.0375 (19) | 0.045 (2) | 0.045 (2) | 0.0072 (17) | 0.0067 (15) | −0.0047 (17) |
C29 | 0.051 (2) | 0.046 (3) | 0.068 (3) | −0.001 (2) | 0.014 (2) | 0.001 (2) |
C30 | 0.072 (3) | 0.035 (2) | 0.064 (3) | 0.003 (2) | 0.020 (2) | 0.0091 (19) |
C31 | 0.061 (2) | 0.042 (2) | 0.047 (2) | 0.017 (2) | 0.0168 (17) | 0.0157 (17) |
C32 | 0.090 (3) | 0.051 (3) | 0.065 (3) | 0.032 (2) | 0.018 (2) | 0.030 (2) |
C33 | 0.075 (3) | 0.059 (3) | 0.055 (2) | 0.040 (2) | 0.0068 (19) | 0.020 (2) |
C34 | 0.049 (2) | 0.055 (2) | 0.046 (2) | 0.0261 (19) | 0.0064 (16) | 0.0164 (18) |
C35 | 0.0418 (19) | 0.036 (2) | 0.0370 (17) | 0.0121 (16) | 0.0081 (14) | 0.0056 (15) |
C36 | 0.0384 (19) | 0.040 (2) | 0.0383 (18) | 0.0135 (16) | 0.0078 (14) | 0.0051 (15) |
C41 | 0.045 (2) | 0.048 (3) | 0.063 (2) | 0.017 (2) | −0.0011 (18) | −0.005 (2) |
C42 | 0.063 (3) | 0.059 (3) | 0.065 (2) | 0.033 (2) | 0.017 (2) | 0.015 (2) |
C43 | 0.057 (2) | 0.055 (3) | 0.068 (3) | 0.029 (2) | 0.0096 (19) | 0.016 (2) |
C44 | 0.053 (2) | 0.053 (3) | 0.073 (3) | 0.028 (2) | 0.021 (2) | 0.024 (2) |
C51 | 0.097 (4) | 0.046 (3) | 0.072 (3) | 0.003 (3) | −0.036 (3) | 0.012 (3) |
C52A | 0.061 (7) | 0.050 (8) | 0.048 (5) | 0.015 (8) | 0.010 (7) | 0.009 (6) |
C52B | 0.052 (6) | 0.041 (7) | 0.050 (6) | 0.001 (6) | −0.001 (7) | −0.013 (5) |
C53 | 0.078 (3) | 0.058 (3) | 0.048 (2) | 0.040 (3) | 0.002 (2) | 0.007 (2) |
C54 | 0.097 (4) | 0.065 (4) | 0.056 (3) | 0.015 (3) | 0.016 (2) | 0.000 (3) |
C55 | 0.049 (2) | 0.050 (3) | 0.068 (3) | 0.014 (2) | 0.008 (2) | 0.011 (2) |
C56 | 0.045 (2) | 0.051 (3) | 0.085 (3) | 0.009 (2) | 0.006 (2) | 0.019 (2) |
C61 | 0.065 (3) | 0.086 (4) | 0.047 (3) | 0.020 (3) | 0.003 (2) | −0.005 (3) |
C62A | 0.068 (7) | 0.088 (10) | 0.097 (16) | 0.044 (7) | −0.001 (7) | 0.041 (9) |
C62B | 0.066 (6) | 0.120 (12) | 0.032 (5) | 0.053 (7) | 0.011 (4) | 0.020 (7) |
Co—N5 | 2.078 (2) | C13—H13 | 0.930 |
Co—N3 | 2.084 (2) | C14—C15 | 1.358 (4) |
Co—N6 | 2.086 (3) | C14—H14 | 0.930 |
Co—N4 | 2.097 (3) | C15—C16 | 1.391 (4) |
Co—N1 | 2.101 (2) | C15—H15 | 0.930 |
Co—N2 | 2.111 (2) | C16—C24 | 1.417 (4) |
O1—C41 | 1.242 (4) | C16—C17 | 1.429 (5) |
O2—C41 | 1.255 (4) | C17—C18 | 1.375 (5) |
O3—C44 | 1.272 (4) | C17—H17 | 0.930 |
O3—H03 | 0.858 | C18—C19 | 1.399 (4) |
O4—C44 | 1.217 (4) | C18—H18 | 0.930 |
O11—C51 | 1.277 (6) | C19—C23 | 1.394 (4) |
O11—H011 | 0.877 | C19—C20 | 1.422 (5) |
O12—C51 | 1.188 (6) | C20—C21 | 1.355 (5) |
O13—C53 | 1.295 (5) | C20—H20 | 0.930 |
O13—H013 | 0.937 | C21—C22 | 1.392 (4) |
O14—C53 | 1.176 (4) | C21—H21 | 0.930 |
O15—C55 | 1.307 (4) | C22—H22 | 0.930 |
O15—H015 | 0.872 | C23—C24 | 1.414 (4) |
O16—C55 | 1.188 (4) | C25—C26 | 1.405 (4) |
O17—C61 | 1.207 (6) | C25—H25 | 0.930 |
O18—C61 | 1.248 (5) | C26—C27 | 1.353 (5) |
O21—H211 | 1.000 | C26—H26 | 0.930 |
O21—H212 | 0.948 | C27—C28 | 1.403 (5) |
O22—H221 | 0.991 | C27—H27 | 0.930 |
O22—H222 | 0.987 | C28—C36 | 1.406 (4) |
O23—H231 | 0.942 | C28—C29 | 1.428 (5) |
O23—H232 | 0.895 | C29—C30 | 1.343 (5) |
O24—H241 | 0.933 | C29—H29 | 0.930 |
O24—H242 | 0.844 | C30—C31 | 1.428 (5) |
N1—C1 | 1.328 (4) | C30—H30 | 0.930 |
N1—C12 | 1.370 (4) | C31—C32 | 1.396 (5) |
N2—C10 | 1.332 (4) | C31—C35 | 1.403 (4) |
N2—C11 | 1.370 (4) | C32—C33 | 1.348 (5) |
N3—C13 | 1.330 (4) | C32—H32 | 0.930 |
N3—C24 | 1.364 (4) | C33—C34 | 1.392 (5) |
N4—C22 | 1.319 (4) | C33—H33 | 0.930 |
N4—C23 | 1.381 (4) | C34—H34 | 0.930 |
N5—C25 | 1.324 (4) | C35—C36 | 1.434 (4) |
N5—C36 | 1.362 (4) | C41—C42 | 1.518 (5) |
N6—C34 | 1.326 (4) | C42—C43 | 1.276 (5) |
N6—C35 | 1.349 (4) | C42—H42 | 0.930 |
C1—C2 | 1.402 (4) | C43—C44 | 1.514 (5) |
C1—H1 | 0.930 | C43—H43 | 0.930 |
C2—C3 | 1.354 (5) | C51—C52B | 1.534 (18) |
C2—H2 | 0.930 | C51—C52A | 1.59 (2) |
C3—C4 | 1.402 (4) | C52A—C52Ai | 1.21 (2) |
C3—H3 | 0.930 | C52A—H52A | 0.90 |
C4—C12 | 1.389 (4) | C52B—C52Bi | 1.32 (2) |
C4—C5 | 1.442 (5) | C52B—H52B | 0.88 |
C5—C6 | 1.351 (5) | C53—C54 | 1.539 (6) |
C5—H5 | 0.930 | C54—C54ii | 1.135 (7) |
C6—C7 | 1.436 (4) | C54—H54 | 0.930 |
C6—H6 | 0.930 | C55—C56 | 1.486 (5) |
C7—C11 | 1.387 (4) | C56—C56iii | 1.302 (7) |
C7—C8 | 1.409 (4) | C56—H56 | 0.930 |
C8—C9 | 1.345 (5) | C61—C62B | 1.492 (16) |
C8—H8 | 0.930 | C61—C62A | 1.56 (3) |
C9—C10 | 1.394 (4) | C62A—C62Aiv | 1.25 (3) |
C9—H9 | 0.930 | C62A—H62A | 0.841 |
C10—H10 | 0.930 | C62B—C62Biv | 1.36 (3) |
C11—C12 | 1.432 (4) | C62B—H62B | 0.839 |
C13—C14 | 1.383 (4) | ||
N5—Co—N3 | 94.50 (9) | C21—C20—C19 | 119.5 (3) |
N5—Co—N6 | 79.85 (10) | C21—C20—H20 | 120.2 |
N3—Co—N6 | 93.64 (10) | C19—C20—H20 | 120.2 |
N5—Co—N4 | 92.65 (10) | C20—C21—C22 | 120.1 (3) |
N3—Co—N4 | 79.77 (10) | C20—C21—H21 | 120.0 |
N6—Co—N4 | 169.66 (10) | C22—C21—H21 | 120.0 |
N5—Co—N1 | 170.34 (9) | N4—C22—C21 | 122.9 (3) |
N3—Co—N1 | 95.12 (9) | N4—C22—H22 | 118.6 |
N6—Co—N1 | 100.40 (10) | C21—C22—H22 | 118.6 |
N4—Co—N1 | 88.20 (9) | N4—C23—C19 | 122.9 (3) |
N5—Co—N2 | 91.21 (9) | N4—C23—C24 | 116.7 (3) |
N3—Co—N2 | 172.92 (9) | C19—C23—C24 | 120.4 (3) |
N6—Co—N2 | 91.49 (10) | N3—C24—C23 | 118.2 (3) |
N4—Co—N2 | 95.80 (10) | N3—C24—C16 | 122.2 (3) |
N1—Co—N2 | 79.13 (9) | C23—C24—C16 | 119.6 (3) |
C44—O3—H03 | 134.1 | N5—C25—C26 | 122.3 (3) |
C51—O11—H011 | 109.7 | N5—C25—H25 | 118.8 |
C53—O13—H013 | 100.5 | C26—C25—H25 | 118.8 |
C55—O15—H015 | 108.2 | C27—C26—C25 | 119.9 (4) |
H211—O21—H212 | 105.4 | C27—C26—H26 | 120.1 |
H221—O22—H222 | 93.6 | C25—C26—H26 | 120.1 |
H231—O23—H232 | 98.2 | C26—C27—C28 | 119.8 (3) |
H241—O24—H242 | 100.3 | C26—C27—H27 | 120.1 |
C1—N1—C12 | 117.6 (3) | C28—C27—H27 | 120.1 |
C1—N1—Co | 128.7 (2) | C27—C28—C36 | 116.8 (3) |
C12—N1—Co | 112.36 (19) | C27—C28—C29 | 124.4 (3) |
C10—N2—C11 | 117.4 (3) | C36—C28—C29 | 118.7 (3) |
C10—N2—Co | 130.3 (2) | C30—C29—C28 | 121.2 (4) |
C11—N2—Co | 112.30 (18) | C30—C29—H29 | 119.4 |
C13—N3—C24 | 117.5 (3) | C28—C29—H29 | 119.4 |
C13—N3—Co | 129.9 (2) | C29—C30—C31 | 121.8 (4) |
C24—N3—Co | 112.5 (2) | C29—C30—H30 | 119.1 |
C22—N4—C23 | 117.8 (3) | C31—C30—H30 | 119.1 |
C22—N4—Co | 129.9 (2) | C32—C31—C35 | 117.5 (3) |
C23—N4—Co | 112.2 (2) | C32—C31—C30 | 124.1 (4) |
C25—N5—C36 | 117.9 (3) | C35—C31—C30 | 118.5 (4) |
C25—N5—Co | 129.3 (2) | C33—C32—C31 | 119.8 (3) |
C36—N5—Co | 112.6 (2) | C33—C32—H32 | 120.1 |
C34—N6—C35 | 117.9 (3) | C31—C32—H32 | 120.1 |
C34—N6—Co | 129.4 (2) | C32—C33—C34 | 119.4 (4) |
C35—N6—Co | 112.6 (2) | C32—C33—H33 | 120.3 |
N1—C1—C2 | 123.1 (3) | C34—C33—H33 | 120.3 |
N1—C1—H1 | 118.4 | N6—C34—C33 | 122.9 (3) |
C2—C1—H1 | 118.4 | N6—C34—H34 | 118.6 |
C3—C2—C1 | 118.6 (3) | C33—C34—H34 | 118.6 |
C3—C2—H2 | 120.7 | N6—C35—C31 | 122.5 (3) |
C1—C2—H2 | 120.7 | N6—C35—C36 | 117.4 (3) |
C2—C3—C4 | 120.4 (3) | C31—C35—C36 | 120.0 (3) |
C2—C3—H3 | 119.8 | N5—C36—C28 | 123.2 (3) |
C4—C3—H3 | 119.8 | N5—C36—C35 | 116.9 (3) |
C12—C4—C3 | 117.4 (3) | C28—C36—C35 | 119.8 (3) |
C12—C4—C5 | 118.8 (3) | O1—C41—O2 | 124.9 (4) |
C3—C4—C5 | 123.7 (3) | O1—C41—C42 | 116.9 (4) |
C6—C5—C4 | 120.6 (3) | O2—C41—C42 | 118.2 (4) |
C6—C5—H5 | 119.7 | C43—C42—C41 | 122.1 (4) |
C4—C5—H5 | 119.7 | C43—C42—H42 | 118.9 |
C5—C6—C7 | 121.2 (3) | C41—C42—H42 | 118.9 |
C5—C6—H6 | 119.4 | C42—C43—C44 | 124.7 (4) |
C7—C6—H6 | 119.4 | C42—C43—H43 | 117.7 |
C11—C7—C8 | 117.2 (3) | C44—C43—H43 | 117.7 |
C11—C7—C6 | 118.9 (3) | O4—C44—O3 | 121.9 (4) |
C8—C7—C6 | 123.9 (3) | O4—C44—C43 | 123.4 (3) |
C9—C8—C7 | 120.6 (3) | O3—C44—C43 | 114.7 (4) |
C9—C8—H8 | 119.7 | O12—C51—O11 | 123.7 (4) |
C7—C8—H8 | 119.7 | O12—C51—C52B | 140.7 (8) |
C8—C9—C10 | 118.7 (3) | O11—C51—C52B | 95.6 (7) |
C8—C9—H9 | 120.6 | O12—C51—C52A | 105.9 (7) |
C10—C9—H9 | 120.6 | O11—C51—C52A | 130.4 (7) |
N2—C10—C9 | 123.4 (3) | C52Ai—C52A—C51 | 113 (3) |
N2—C10—H10 | 118.3 | C52Ai—C52A—H52A | 112 |
C9—C10—H10 | 118.3 | C51—C52A—H52A | 134.4 |
N2—C11—C7 | 122.7 (3) | C52Bi—C52B—C51 | 116 (2) |
N2—C11—C12 | 117.2 (3) | C52Bi—C52B—H52B | 114 |
C7—C11—C12 | 120.1 (3) | C51—C52B—H52B | 130.7 |
N1—C12—C4 | 122.7 (3) | O14—C53—O13 | 122.8 (4) |
N1—C12—C11 | 117.1 (3) | O14—C53—C54 | 129.3 (4) |
C4—C12—C11 | 120.2 (3) | O13—C53—C54 | 107.9 (4) |
N3—C13—C14 | 123.4 (3) | C54ii—C54—C53 | 122.2 (7) |
N3—C13—H13 | 118.3 | C54ii—C54—H54 | 118.9 |
C14—C13—H13 | 118.3 | C53—C54—H54 | 118.9 |
C15—C14—C13 | 119.6 (3) | O16—C55—O15 | 124.7 (4) |
C15—C14—H14 | 120.2 | O16—C55—C56 | 123.1 (4) |
C13—C14—H14 | 120.2 | O15—C55—C56 | 112.1 (3) |
C14—C15—C16 | 119.8 (3) | C56iii—C56—C55 | 124.2 (5) |
C14—C15—H15 | 120.1 | C56iii—C56—H56 | 117.9 |
C16—C15—H15 | 120.1 | C55—C56—H56 | 117.9 |
C15—C16—C24 | 117.5 (3) | O17—C61—O18 | 123.3 (4) |
C15—C16—C17 | 124.0 (3) | O17—C61—C62B | 104.5 (9) |
C24—C16—C17 | 118.5 (3) | O18—C61—C62B | 132.1 (9) |
C18—C17—C16 | 120.9 (3) | O17—C61—C62A | 137.6 (7) |
C18—C17—H17 | 119.6 | O18—C61—C62A | 99.0 (7) |
C16—C17—H17 | 119.6 | C62Aiv—C62A—C61 | 116 (2) |
C17—C18—C19 | 120.6 (3) | C62Aiv—C62A—H62A | 116 |
C17—C18—H18 | 119.7 | C61—C62A—H62A | 127.0 |
C19—C18—H18 | 119.7 | C62Biv—C62B—C61 | 119 (2) |
C23—C19—C18 | 120.1 (3) | C62Biv—C62B—H62B | 114 |
C23—C19—C20 | 116.8 (3) | C61—C62B—H62B | 126.8 |
C18—C19—C20 | 123.1 (3) | ||
N3—Co—N1—C1 | −3.1 (3) | Co—N3—C13—C14 | 175.7 (2) |
N6—Co—N1—C1 | 91.6 (3) | N3—C13—C14—C15 | −0.9 (5) |
N4—Co—N1—C1 | −82.7 (3) | C13—C14—C15—C16 | 0.1 (5) |
N2—Co—N1—C1 | −178.9 (3) | C14—C15—C16—C24 | 1.4 (5) |
N3—Co—N1—C12 | 163.4 (2) | C14—C15—C16—C17 | 179.1 (3) |
N6—Co—N1—C12 | −102.0 (2) | C15—C16—C17—C18 | −176.6 (3) |
N4—Co—N1—C12 | 83.8 (2) | C24—C16—C17—C18 | 1.1 (5) |
N2—Co—N1—C12 | −12.44 (19) | C16—C17—C18—C19 | −0.9 (5) |
N5—Co—N2—C10 | 7.2 (3) | C17—C18—C19—C23 | −0.5 (5) |
N6—Co—N2—C10 | −72.7 (3) | C17—C18—C19—C20 | 177.2 (3) |
N4—Co—N2—C10 | 100.0 (3) | C23—C19—C20—C21 | −1.2 (5) |
N1—Co—N2—C10 | −173.0 (3) | C18—C19—C20—C21 | −179.0 (3) |
N5—Co—N2—C11 | −169.4 (2) | C19—C20—C21—C22 | −0.3 (5) |
N6—Co—N2—C11 | 110.7 (2) | C23—N4—C22—C21 | −1.1 (5) |
N4—Co—N2—C11 | −76.6 (2) | Co—N4—C22—C21 | −177.1 (2) |
N1—Co—N2—C11 | 10.41 (19) | C20—C21—C22—N4 | 1.5 (5) |
N5—Co—N3—C13 | −90.1 (3) | C22—N4—C23—C19 | −0.5 (4) |
N6—Co—N3—C13 | −10.0 (3) | Co—N4—C23—C19 | 176.1 (2) |
N4—Co—N3—C13 | 178.0 (3) | C22—N4—C23—C24 | 177.2 (3) |
N1—Co—N3—C13 | 90.8 (3) | Co—N4—C23—C24 | −6.1 (3) |
N5—Co—N3—C24 | 85.8 (2) | C18—C19—C23—N4 | 179.6 (3) |
N6—Co—N3—C24 | 165.9 (2) | C20—C19—C23—N4 | 1.7 (4) |
N4—Co—N3—C24 | −6.04 (19) | C18—C19—C23—C24 | 1.9 (5) |
N1—Co—N3—C24 | −93.3 (2) | C20—C19—C23—C24 | −176.0 (3) |
N5—Co—N4—C22 | 88.6 (3) | C13—N3—C24—C23 | −178.8 (2) |
N3—Co—N4—C22 | −177.3 (3) | Co—N3—C24—C23 | 4.8 (3) |
N6—Co—N4—C22 | 131.7 (5) | C13—N3—C24—C16 | 1.7 (4) |
N1—Co—N4—C22 | −81.8 (3) | Co—N3—C24—C16 | −174.7 (2) |
N2—Co—N4—C22 | −2.9 (3) | N4—C23—C24—N3 | 0.9 (4) |
N5—Co—N4—C23 | −87.6 (2) | C19—C23—C24—N3 | 178.8 (3) |
N3—Co—N4—C23 | 6.52 (18) | N4—C23—C24—C16 | −179.5 (2) |
N6—Co—N4—C23 | −44.4 (6) | C19—C23—C24—C16 | −1.7 (4) |
N1—Co—N4—C23 | 102.1 (2) | C15—C16—C24—N3 | −2.4 (4) |
N2—Co—N4—C23 | −179.07 (19) | C17—C16—C24—N3 | 179.7 (3) |
N3—Co—N5—C25 | −86.3 (3) | C15—C16—C24—C23 | 178.1 (3) |
N6—Co—N5—C25 | −179.2 (3) | C17—C16—C24—C23 | 0.3 (4) |
N4—Co—N5—C25 | −6.4 (3) | C36—N5—C25—C26 | −0.4 (5) |
N2—Co—N5—C25 | 89.5 (3) | Co—N5—C25—C26 | −175.0 (2) |
N3—Co—N5—C36 | 98.9 (2) | N5—C25—C26—C27 | 1.8 (5) |
N6—Co—N5—C36 | 6.0 (2) | C25—C26—C27—C28 | −1.9 (5) |
N4—Co—N5—C36 | 178.8 (2) | C26—C27—C28—C36 | 0.6 (5) |
N2—Co—N5—C36 | −85.3 (2) | C26—C27—C28—C29 | −179.1 (3) |
N5—Co—N6—C34 | 177.1 (3) | C27—C28—C29—C30 | 178.3 (4) |
N3—Co—N6—C34 | 83.2 (3) | C36—C28—C29—C30 | −1.4 (5) |
N4—Co—N6—C34 | 133.2 (5) | C28—C29—C30—C31 | 0.9 (6) |
N1—Co—N6—C34 | −12.7 (3) | C29—C30—C31—C32 | −179.6 (4) |
N2—Co—N6—C34 | −91.9 (3) | C29—C30—C31—C35 | 1.3 (5) |
N5—Co—N6—C35 | −6.62 (19) | C35—C31—C32—C33 | −1.7 (5) |
N3—Co—N6—C35 | −100.5 (2) | C30—C31—C32—C33 | 179.3 (3) |
N4—Co—N6—C35 | −50.6 (6) | C31—C32—C33—C34 | 1.5 (5) |
N1—Co—N6—C35 | 163.57 (19) | C35—N6—C34—C33 | −0.2 (5) |
N2—Co—N6—C35 | 84.3 (2) | Co—N6—C34—C33 | 175.9 (2) |
C12—N1—C1—C2 | −1.9 (5) | C32—C33—C34—N6 | −0.5 (5) |
Co—N1—C1—C2 | 164.0 (2) | C34—N6—C35—C31 | −0.1 (4) |
N1—C1—C2—C3 | 1.3 (5) | Co—N6—C35—C31 | −176.8 (2) |
C1—C2—C3—C4 | 0.5 (5) | C34—N6—C35—C36 | −176.9 (3) |
C2—C3—C4—C12 | −1.6 (5) | Co—N6—C35—C36 | 6.3 (3) |
C2—C3—C4—C5 | 177.7 (3) | C32—C31—C35—N6 | 1.0 (5) |
C12—C4—C5—C6 | 2.1 (5) | C30—C31—C35—N6 | −179.9 (3) |
C3—C4—C5—C6 | −177.1 (3) | C32—C31—C35—C36 | 177.8 (3) |
C4—C5—C6—C7 | −1.9 (6) | C30—C31—C35—C36 | −3.1 (5) |
C5—C6—C7—C11 | −2.0 (5) | C25—N5—C36—C28 | −0.9 (4) |
C5—C6—C7—C8 | 179.9 (3) | Co—N5—C36—C28 | 174.6 (2) |
C11—C7—C8—C9 | 0.2 (5) | C25—N5—C36—C35 | −180.0 (3) |
C6—C7—C8—C9 | 178.4 (3) | Co—N5—C36—C35 | −4.5 (3) |
C7—C8—C9—C10 | −2.1 (5) | C27—C28—C36—N5 | 0.8 (5) |
C11—N2—C10—C9 | 0.4 (5) | C29—C28—C36—N5 | −179.5 (3) |
Co—N2—C10—C9 | −176.0 (2) | C27—C28—C36—C35 | 179.9 (3) |
C8—C9—C10—N2 | 1.8 (5) | C29—C28—C36—C35 | −0.4 (5) |
C10—N2—C11—C7 | −2.4 (4) | N6—C35—C36—N5 | −1.3 (4) |
Co—N2—C11—C7 | 174.7 (2) | C31—C35—C36—N5 | −178.2 (3) |
C10—N2—C11—C12 | 176.0 (3) | N6—C35—C36—C28 | 179.6 (3) |
Co—N2—C11—C12 | −7.0 (3) | C31—C35—C36—C28 | 2.6 (5) |
C8—C7—C11—N2 | 2.1 (5) | O1—C41—C42—C43 | 149.4 (4) |
C6—C7—C11—N2 | −176.1 (3) | O2—C41—C42—C43 | −29.2 (5) |
C8—C7—C11—C12 | −176.2 (3) | C41—C42—C43—C44 | −177.8 (3) |
C6—C7—C11—C12 | 5.6 (5) | C42—C43—C44—O4 | −14.0 (6) |
C1—N1—C12—C4 | 0.7 (4) | C42—C43—C44—O3 | 167.8 (4) |
Co—N1—C12—C4 | −167.4 (2) | O12—C51—C52A—C52Ai | −172.8 (10) |
C1—N1—C12—C11 | −179.1 (3) | O11—C51—C52A—C52Ai | 8.9 (14) |
Co—N1—C12—C11 | 12.8 (3) | O12—C51—C52B—C52Bi | 4.6 (18) |
C3—C4—C12—N1 | 1.0 (5) | O11—C51—C52B—C52Bi | −177.6 (11) |
C5—C4—C12—N1 | −178.4 (3) | O14—C53—C54—C54ii | 1.7 (9) |
C3—C4—C12—C11 | −179.2 (3) | O13—C53—C54—C54ii | −179.2 (6) |
C5—C4—C12—C11 | 1.5 (5) | O16—C55—C56—C56iii | −1.4 (8) |
N2—C11—C12—N1 | −3.9 (4) | O15—C55—C56—C56iii | 177.9 (5) |
C7—C11—C12—N1 | 174.5 (3) | O17—C61—C62A—C62Aiv | 27 (2) |
N2—C11—C12—C4 | 176.2 (3) | O18—C61—C62A—C62Aiv | −153.7 (16) |
C7—C11—C12—C4 | −5.4 (5) | O17—C61—C62B—C62Biv | 167.4 (16) |
C24—N3—C13—C14 | −0.1 (4) | O18—C61—C62B—C62Biv | −9 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H03···O18v | 0.86 | 1.69 | 2.457 (4) | 147 |
O13—H013···O17 | 0.94 | 1.67 | 2.537 (5) | 152 |
O15—H015···O1 | 0.87 | 1.89 | 2.488 (4) | 124 |
O11—H011···O4vi | 0.88 | 1.87 | 2.642 (5) | 146 |
O21—H211···O2 | 1.00 | 2.01 | 2.962 (5) | 158 |
O21—H212···O22ii | 0.95 | 1.98 | 2.847 (5) | 151 |
O22—H221···O14 | 0.99 | 1.89 | 2.863 (6) | 167 |
O22—H222···O23vii | 0.99 | 1.92 | 2.822 (5) | 151 |
O23—H231···O24 | 0.94 | 2.09 | 2.860 (5) | 138 |
O23—H232···O2 | 0.90 | 2.07 | 2.874 (5) | 149 |
O24—H241···O12i | 0.93 | 2.07 | 2.990 (5) | 171 |
O24—H242···O16 | 0.84 | 2.34 | 3.168 (5) | 167 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z; (v) x, y+1, z; (vi) −x+1, −y+2, −z+1; (vii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Co(C12H8N2)3](C3H2O4)(C3H3O4)·C3H4O4·4H2O |
Mr | 1017.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 12.167 (2), 12.487 (2), 17.040 (2) |
α, β, γ (°) | 102.85 (2), 90.28 (1), 116.39 (2) |
V (Å3) | 2245.0 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.47 |
Crystal size (mm) | 0.42 × 0.22 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.82, 0.96 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14499, 9991, 5138 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.652 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.135, 0.86 |
No. of reflections | 9991 |
No. of parameters | 658 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.76, −0.46 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Co—N5 | 2.078 (2) | O4—C44 | 1.217 (4) |
Co—N3 | 2.084 (2) | O11—C51 | 1.277 (6) |
Co—N6 | 2.086 (3) | O12—C51 | 1.188 (6) |
Co—N4 | 2.097 (3) | O13—C53 | 1.295 (5) |
Co—N1 | 2.101 (2) | O14—C53 | 1.176 (4) |
Co—N2 | 2.111 (2) | O15—C55 | 1.307 (4) |
O1—C41 | 1.242 (4) | O16—C55 | 1.188 (4) |
O2—C41 | 1.255 (4) | O17—C61 | 1.207 (6) |
O3—C44 | 1.272 (4) | O18—C61 | 1.248 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H03···O18i | 0.86 | 1.69 | 2.457 (4) | 147 |
O13—H013···O17 | 0.94 | 1.67 | 2.537 (5) | 152 |
O15—H015···O1 | 0.87 | 1.89 | 2.488 (4) | 124 |
O11—H011···O4ii | 0.88 | 1.87 | 2.642 (5) | 146 |
O21—H211···O2 | 1.00 | 2.01 | 2.962 (5) | 158 |
O21—H212···O22iii | 0.95 | 1.98 | 2.847 (5) | 151 |
O22—H221···O14 | 0.99 | 1.89 | 2.863 (6) | 167 |
O22—H222···O23iv | 0.99 | 1.92 | 2.822 (5) | 151 |
O23—H231···O24 | 0.94 | 2.09 | 2.860 (5) | 138 |
O23—H232···O2 | 0.90 | 2.07 | 2.874 (5) | 149 |
O24—H241···O12v | 0.93 | 2.07 | 2.990 (5) | 171 |
O24—H242···O16 | 0.84 | 2.34 | 3.168 (5) | 167 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z; (iv) x+1, y, z; (v) −x, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The crystals were occasionally obtained during the preparing the CoII complex bridged by fumarate. The CoII complex displays an octahedron geometry (Fig. 1), formed by three chelating phenanthroline (phen) molecules. Together with the CoII complex, the fumarate dianion, fumarate monoanion and fumaric acid occur in the crystal. They were recognized by comparing the differences in C—O bonds in the same carboxyl group. The smaller differences of 0.013 (6) Å in the C41-carboxyl group and 0.041 (8) Å in the C61-carboxyl group (Table 1) indicate that both C41- and C61-carboxyl are deprotonated groups, while the larger differences of 0.055 (6) Å in the C44-carboxyl, 0.089 (8) Å in the C51-carboxyl and 0.119 (6) Å in the C53- and C55-carboxyl groups showed that these carboxyl groups are neutral. The fumarate monoanion is located in the crystallographic general position, while fumarate dianion and neutral fumaric acid molecule are located in individual inversion centers. The CoII complex displays an octahedron coordination geometry, formed by three chelating phen molecules with normal bond distances and angles.
An extensive hydrogen-bonding network occurs between carboxyl/carboxylate groups and lattice water, as shown in Fig. 1 and Table 2. The separations of 3.342 (8) and 3.493 (15) Å indicate the existence of the π–π-stacking interaction between neighboring phen molecules related by the inversion center, as shown in Fig. 2. An approximately parallel arrangement of the C53-fumaric acid with the N5-phen ring is observed (Fig. 3). The shorter distances to the N5-phen plane of 3.341 (4) Å (C53) and 3.419 (5) Å (C54) may suggest the existence of the π–π interaction between the fumaric acid and phen ring.
The carbon skeleton of the C51-fumaric acid and C61-fumarate dianion show the disordered arrangement, like those found in manganese complex (Liu et al., 2003).