Retracted: (Dihydroxyglyoxime-κ2N,N′)bis(1,10-phenanthroline-κ2N,N′)cobalt(II) dinitrate dihydrate
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031224/sg2186sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031224/sg2186Isup2.hkl |
CCDC reference: 1293555
Cobalt dinitrate hexahydrate (146 mg, 0.5 mmol), phen (198 mg, 1 mmol) and dihydroxyglyoxime (120 mg, 1 mmol) were dissolved in ethanol (15 ml). The mixture was heated for 5 h under reflux with stirring. It was then filtered to give a clear solution, into which diethyl ether vapour was allowed to condense in a closed vessel. After being allowed to stand for a few days at room temperature, some pink single crystals suitable for X-ray diffraction analysis precipitated.
H atoms of the water molecules were located in a difference synthesis and refined isotropically [O—H = 0.833 (10)–0.86 (8) Å, Uiso(H) = 0.532 (13)–0.603 (11) Å2]. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.2 for aromatic H atoms and x = 1.5 for all other H atoms.
The crystal structure of bis(1,10-phenanthroline-N,N')(dihydroxy glyoxime) copper(II) dinitrate dihydrate, (II), has previously been reported (Liu et al., 2007). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six nitrogen atoms are coordinated to the cobalt atom, in a distorted octahedral arrangement (Table 1). The dihydroxyglyoxime and two phen ligands are each planar and the phen ligands are nearly perpendicular to each other, with a dihedral angle of 86.94 (7)°, as in (II).
In the crystal structure, the molecules are linked into a three-dimensional framework (Fig. 2) by O—H···O, C—H···O, C—H···N and O—H···N hydrogen bonds (Table 2). There are stacking interactions between adjacent phen ligands with centroid-centroid distance of 3.585 (3)Å (symmetry code: 1 - x, 2 - y, -z) leading to a supramolecular network structure (Fig. 2), as in (II).
For a related structure, see: Liu et al. (2007). For related literature, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.
[Co(C12H8N2)2(C2H4N2O4)](NO3)2·2H2O | F(000) = 1436 |
Mr = 699.46 | Dx = 1.520 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5619 reflections |
a = 13.8695 (11) Å | θ = 2.2–25.0° |
b = 12.044 (5) Å | µ = 0.64 mm−1 |
c = 18.401 (3) Å | T = 273 K |
β = 95.997 (5)° | Prism, pink |
V = 3057.1 (13) Å3 | 0.30 × 0.23 × 0.18 mm |
Z = 4 |
Bruker APEXII area-detector diffractometer | 6137 independent reflections |
Radiation source: fine-focus sealed tube | 3126 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 26.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.833, Tmax = 0.895 | k = −15→15 |
19977 measured reflections | l = −22→23 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3 |
6137 reflections | (Δ/σ)max = 0.008 |
444 parameters | Δρmax = 0.73 e Å−3 |
12 restraints | Δρmin = −0.45 e Å−3 |
[Co(C12H8N2)2(C2H4N2O4)](NO3)2·2H2O | V = 3057.1 (13) Å3 |
Mr = 699.46 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.8695 (11) Å | µ = 0.64 mm−1 |
b = 12.044 (5) Å | T = 273 K |
c = 18.401 (3) Å | 0.30 × 0.23 × 0.18 mm |
β = 95.997 (5)° |
Bruker APEXII area-detector diffractometer | 6137 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3126 reflections with I > 2σ(I) |
Tmin = 0.833, Tmax = 0.895 | Rint = 0.041 |
19977 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 12 restraints |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.73 e Å−3 |
6137 reflections | Δρmin = −0.45 e Å−3 |
444 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 | ||
Co1 | 0.77581 (3) | 0.75563 (4) | 0.03828 (3) | 0.03933 (19) | |
O1 | 0.7960 (2) | 0.9966 (2) | 0.04754 (15) | 0.0549 (8) | |
H1A | 0.8015 | 0.9965 | 0.0036 | 0.082* | |
O2 | 0.8342 (2) | 0.6030 (2) | 0.14801 (17) | 0.0630 (9) | |
H2A | 0.8674 | 0.5937 | 0.1871 | 0.094* | |
O3 | 0.9313 (3) | 0.7553 (5) | 0.2464 (3) | 0.1361 (17) | |
H3A | 0.9888 | 0.7720 | 0.2476 | 0.204* | |
O4 | 0.9034 (4) | 0.9954 (4) | 0.1832 (3) | 0.1475 (18) | |
H4A | 0.9512 | 0.9799 | 0.2114 | 0.221* | |
O5 | 0.7740 (3) | 0.1306 (3) | 0.9098 (2) | 0.0897 (12) | |
O6 | 0.8931 (2) | 0.0156 (3) | 0.92845 (19) | 0.0716 (9) | |
O7 | 0.8893 (3) | 0.1352 (4) | 0.8431 (3) | 0.1246 (17) | |
O8 | 0.7401 (6) | 0.8817 (7) | 0.2869 (4) | 0.193 (3) | |
O9 | 0.6166 (6) | 0.8846 (6) | 0.3348 (4) | 0.200 (3) | |
O10 | 0.6399 (8) | 1.0082 (6) | 0.2621 (5) | 0.372 (10) | |
O11 | 0.5564 (12) | 0.4278 (12) | 0.1447 (9) | 0.537 (12) | |
O12 | 0.7018 (18) | 0.3345 (17) | 0.2011 (10) | 0.612 (18) | |
N1 | 0.6532 (2) | 0.7801 (2) | 0.07677 (19) | 0.0430 (8) | |
N2 | 0.7067 (2) | 0.8185 (2) | −0.05307 (18) | 0.0404 (8) | |
N3 | 0.7384 (2) | 0.6056 (2) | 0.00412 (18) | 0.0444 (8) | |
N4 | 0.8938 (2) | 0.7245 (2) | −0.00711 (17) | 0.0400 (8) | |
N5 | 0.8376 (2) | 0.7049 (3) | 0.12949 (19) | 0.0438 (8) | |
N6 | 0.8222 (2) | 0.8935 (3) | 0.07666 (19) | 0.0412 (8) | |
N7 | 0.8513 (3) | 0.0928 (3) | 0.8921 (3) | 0.0647 (11) | |
N8 | 0.6661 (6) | 0.9309 (8) | 0.2892 (5) | 0.147 (4) | |
C1 | 0.6298 (3) | 0.7616 (3) | 0.1433 (2) | 0.0545 (11) | |
H1 | 0.6772 | 0.7353 | 0.1786 | 0.065* | |
C2 | 0.5370 (3) | 0.7801 (4) | 0.1627 (3) | 0.0658 (13) | |
H2 | 0.5234 | 0.7671 | 0.2104 | 0.079* | |
C3 | 0.4661 (3) | 0.8170 (4) | 0.1120 (3) | 0.0623 (13) | |
H3 | 0.4036 | 0.8283 | 0.1246 | 0.075* | |
C4 | 0.4871 (3) | 0.8380 (3) | 0.0408 (3) | 0.0519 (12) | |
C5 | 0.4202 (3) | 0.8799 (4) | −0.0165 (3) | 0.0637 (13) | |
H5 | 0.3563 | 0.8926 | −0.0078 | 0.076* | |
C6 | 0.4482 (3) | 0.9018 (4) | −0.0842 (3) | 0.0674 (14) | |
H6 | 0.4030 | 0.9294 | −0.1206 | 0.081* | |
C7 | 0.5457 (3) | 0.8831 (3) | −0.1000 (3) | 0.0534 (12) | |
C8 | 0.5799 (4) | 0.9060 (4) | −0.1658 (3) | 0.0657 (14) | |
H8 | 0.5383 | 0.9346 | −0.2041 | 0.079* | |
C9 | 0.6762 (4) | 0.8863 (4) | −0.1750 (3) | 0.0678 (14) | |
H9 | 0.7001 | 0.9037 | −0.2190 | 0.081* | |
C10 | 0.7373 (3) | 0.8399 (3) | −0.1173 (2) | 0.0512 (11) | |
H10 | 0.8012 | 0.8237 | −0.1244 | 0.061* | |
C11 | 0.6127 (3) | 0.8402 (3) | −0.0444 (2) | 0.0430 (10) | |
C12 | 0.5836 (3) | 0.8182 (3) | 0.0253 (2) | 0.0417 (10) | |
C13 | 0.6608 (3) | 0.5463 (4) | 0.0149 (3) | 0.0611 (13) | |
H13 | 0.6147 | 0.5759 | 0.0427 | 0.073* | |
C14 | 0.6471 (3) | 0.4405 (4) | −0.0146 (3) | 0.0757 (16) | |
H14 | 0.5918 | 0.4005 | −0.0067 | 0.091* | |
C15 | 0.7133 (4) | 0.3950 (4) | −0.0548 (3) | 0.0731 (15) | |
H15 | 0.7034 | 0.3245 | −0.0748 | 0.088* | |
C16 | 0.7967 (3) | 0.4548 (3) | −0.0659 (2) | 0.0495 (11) | |
C17 | 0.8725 (4) | 0.4155 (4) | −0.1058 (2) | 0.0583 (12) | |
H17 | 0.8662 | 0.3466 | −0.1286 | 0.070* | |
C18 | 0.9520 (4) | 0.4752 (4) | −0.1112 (2) | 0.0568 (12) | |
H18 | 1.0005 | 0.4463 | −0.1370 | 0.068* | |
C19 | 0.9653 (3) | 0.5831 (3) | −0.0784 (2) | 0.0445 (10) | |
C20 | 1.0469 (3) | 0.6507 (4) | −0.0801 (2) | 0.0541 (12) | |
H20 | 1.0990 | 0.6270 | −0.1041 | 0.065* | |
C21 | 1.0496 (3) | 0.7503 (4) | −0.0467 (2) | 0.0540 (11) | |
H21 | 1.1038 | 0.7954 | −0.0481 | 0.065* | |
C22 | 0.9725 (3) | 0.7868 (3) | −0.0102 (2) | 0.0472 (11) | |
H22 | 0.9761 | 0.8560 | 0.0124 | 0.057* | |
C23 | 0.8908 (3) | 0.6240 (3) | −0.0407 (2) | 0.0413 (10) | |
C24 | 0.8063 (3) | 0.5592 (3) | −0.0347 (2) | 0.0408 (10) | |
C25 | 0.8805 (3) | 0.7816 (3) | 0.1717 (2) | 0.0451 (10) | |
C26 | 0.8677 (3) | 0.8917 (3) | 0.1413 (2) | 0.0477 (11) | |
H11A | 0.514 (3) | 0.401 (3) | 0.113 (3) | 0.532 (13)* | |
H12A | 0.673 (8) | 0.284 (4) | 0.224 (5) | 0.60 (3)* | |
H11B | 0.5583 (19) | 0.4957 (13) | 0.1533 (16) | 0.540 (7)* | |
H12B | 0.732 (2) | 0.307 (3) | 0.1681 (16) | 0.603 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0360 (3) | 0.0383 (3) | 0.0430 (4) | 0.0023 (2) | 0.0010 (2) | −0.0024 (3) |
O1 | 0.0668 (19) | 0.0416 (16) | 0.055 (2) | 0.0082 (14) | 0.0002 (17) | −0.0014 (15) |
O2 | 0.065 (2) | 0.058 (2) | 0.063 (2) | 0.0029 (15) | −0.0081 (16) | 0.0171 (16) |
O3 | 0.128 (4) | 0.167 (5) | 0.105 (4) | −0.001 (4) | −0.027 (3) | 0.020 (3) |
O4 | 0.162 (5) | 0.123 (4) | 0.150 (5) | −0.015 (3) | −0.016 (4) | −0.045 (3) |
O5 | 0.063 (2) | 0.092 (3) | 0.116 (3) | 0.017 (2) | 0.019 (2) | 0.006 (2) |
O6 | 0.071 (2) | 0.056 (2) | 0.087 (3) | 0.0072 (17) | 0.0028 (19) | 0.0148 (19) |
O7 | 0.123 (4) | 0.129 (4) | 0.131 (4) | 0.029 (3) | 0.055 (3) | 0.058 (3) |
O8 | 0.156 (6) | 0.238 (8) | 0.188 (7) | −0.047 (6) | 0.034 (6) | −0.063 (5) |
O9 | 0.234 (8) | 0.198 (7) | 0.163 (7) | 0.006 (6) | 0.002 (6) | −0.017 (5) |
O10 | 0.523 (18) | 0.131 (6) | 0.379 (14) | −0.077 (7) | −0.348 (13) | 0.124 (7) |
O11 | 0.51 (3) | 0.72 (3) | 0.46 (2) | 0.08 (2) | 0.36 (2) | 0.14 (2) |
O12 | 0.45 (3) | 0.96 (5) | 0.41 (3) | −0.05 (3) | −0.050 (18) | −0.42 (3) |
N1 | 0.0409 (19) | 0.0402 (19) | 0.047 (2) | 0.0019 (14) | 0.0008 (16) | −0.0009 (16) |
N2 | 0.045 (2) | 0.0349 (19) | 0.040 (2) | 0.0033 (15) | −0.0008 (16) | −0.0055 (16) |
N3 | 0.0398 (19) | 0.0398 (19) | 0.053 (2) | −0.0021 (16) | 0.0019 (17) | −0.0016 (17) |
N4 | 0.0372 (19) | 0.0357 (19) | 0.046 (2) | 0.0032 (14) | −0.0022 (15) | −0.0015 (15) |
N5 | 0.0390 (19) | 0.043 (2) | 0.049 (2) | 0.0039 (16) | 0.0040 (16) | 0.0065 (18) |
N6 | 0.0392 (19) | 0.0381 (19) | 0.046 (2) | 0.0026 (15) | 0.0027 (16) | −0.0012 (16) |
N7 | 0.056 (3) | 0.061 (3) | 0.078 (3) | −0.005 (2) | 0.009 (2) | 0.011 (2) |
N8 | 0.100 (5) | 0.227 (11) | 0.117 (7) | −0.055 (6) | 0.021 (5) | −0.085 (7) |
C1 | 0.047 (2) | 0.067 (3) | 0.050 (3) | 0.008 (2) | 0.005 (2) | 0.007 (2) |
C2 | 0.058 (3) | 0.077 (3) | 0.064 (4) | 0.003 (3) | 0.015 (3) | −0.004 (3) |
C3 | 0.043 (3) | 0.062 (3) | 0.084 (4) | −0.004 (2) | 0.019 (3) | −0.015 (3) |
C4 | 0.040 (3) | 0.039 (2) | 0.075 (4) | −0.0002 (19) | −0.001 (2) | −0.009 (2) |
C5 | 0.041 (3) | 0.058 (3) | 0.090 (4) | 0.005 (2) | −0.005 (3) | −0.006 (3) |
C6 | 0.055 (3) | 0.052 (3) | 0.088 (4) | 0.011 (2) | −0.021 (3) | −0.006 (3) |
C7 | 0.056 (3) | 0.044 (3) | 0.056 (3) | 0.004 (2) | −0.011 (2) | −0.005 (2) |
C8 | 0.074 (4) | 0.057 (3) | 0.061 (4) | 0.011 (3) | −0.018 (3) | 0.000 (3) |
C9 | 0.103 (4) | 0.051 (3) | 0.047 (3) | −0.002 (3) | −0.004 (3) | −0.003 (2) |
C10 | 0.064 (3) | 0.047 (3) | 0.042 (3) | 0.002 (2) | 0.002 (2) | −0.004 (2) |
C11 | 0.046 (3) | 0.032 (2) | 0.049 (3) | 0.0018 (18) | −0.006 (2) | −0.001 (2) |
C12 | 0.037 (2) | 0.033 (2) | 0.053 (3) | 0.0013 (17) | 0.000 (2) | −0.005 (2) |
C13 | 0.049 (3) | 0.048 (3) | 0.087 (4) | −0.005 (2) | 0.008 (2) | −0.005 (3) |
C14 | 0.058 (3) | 0.050 (3) | 0.119 (5) | −0.014 (2) | 0.009 (3) | −0.009 (3) |
C15 | 0.075 (4) | 0.041 (3) | 0.101 (5) | −0.008 (3) | −0.005 (3) | −0.015 (3) |
C16 | 0.056 (3) | 0.038 (2) | 0.052 (3) | 0.005 (2) | −0.008 (2) | −0.002 (2) |
C17 | 0.080 (3) | 0.045 (3) | 0.047 (3) | 0.013 (3) | −0.004 (3) | −0.008 (2) |
C18 | 0.074 (3) | 0.056 (3) | 0.039 (3) | 0.026 (3) | 0.002 (2) | −0.006 (2) |
C19 | 0.046 (3) | 0.050 (3) | 0.037 (3) | 0.013 (2) | −0.0006 (19) | 0.003 (2) |
C20 | 0.050 (3) | 0.067 (3) | 0.046 (3) | 0.014 (2) | 0.011 (2) | 0.003 (2) |
C21 | 0.042 (2) | 0.064 (3) | 0.056 (3) | −0.002 (2) | 0.005 (2) | 0.004 (3) |
C22 | 0.042 (2) | 0.045 (2) | 0.053 (3) | 0.0017 (19) | 0.001 (2) | −0.003 (2) |
C23 | 0.043 (2) | 0.041 (2) | 0.038 (3) | 0.0071 (19) | −0.0049 (18) | 0.0025 (19) |
C24 | 0.046 (2) | 0.036 (2) | 0.039 (3) | 0.0069 (19) | −0.0025 (19) | 0.0001 (19) |
C25 | 0.041 (2) | 0.054 (3) | 0.039 (3) | 0.0025 (19) | −0.0007 (19) | 0.002 (2) |
C26 | 0.045 (2) | 0.050 (3) | 0.047 (3) | −0.003 (2) | 0.002 (2) | −0.012 (2) |
Co1—N1 | 1.932 (3) | C3—C4 | 1.394 (6) |
Co1—N2 | 1.995 (3) | C3—H3 | 0.9300 |
Co1—N3 | 1.965 (3) | C4—C12 | 1.417 (5) |
Co1—N4 | 1.949 (3) | C4—C5 | 1.422 (6) |
Co1—N5 | 1.904 (3) | C5—C6 | 1.369 (6) |
Co1—N6 | 1.891 (3) | C5—H5 | 0.9300 |
O1—N6 | 1.385 (4) | C6—C7 | 1.431 (6) |
O1—H1A | 0.8200 | C6—H6 | 0.9300 |
O2—N5 | 1.276 (4) | C7—C8 | 1.373 (6) |
O2—H2A | 0.8200 | C7—C11 | 1.406 (6) |
O3—C25 | 1.511 (5) | C8—C9 | 1.384 (6) |
O3—H3A | 0.8200 | C8—H8 | 0.9300 |
O4—C26 | 1.522 (5) | C9—C10 | 1.405 (6) |
O4—H4A | 0.8200 | C9—H9 | 0.9300 |
O5—N7 | 1.238 (4) | C10—H10 | 0.9300 |
O6—N7 | 1.252 (5) | C11—C12 | 1.409 (5) |
O7—N7 | 1.204 (5) | C13—C14 | 1.391 (6) |
O8—N8 | 1.189 (8) | C13—H13 | 0.9300 |
O9—N8 | 1.268 (8) | C14—C15 | 1.354 (6) |
O10—N8 | 1.100 (10) | C14—H14 | 0.9300 |
O11—H11A | 0.85 (5) | C15—C16 | 1.395 (6) |
O11—H11B | 0.833 (10) | C15—H15 | 0.9300 |
O12—H12A | 0.86 (8) | C16—C24 | 1.382 (5) |
O12—H12B | 0.84 (4) | C16—C17 | 1.425 (6) |
N1—C1 | 1.318 (5) | C17—C18 | 1.329 (6) |
N1—C12 | 1.360 (5) | C17—H17 | 0.9300 |
N2—C10 | 1.322 (5) | C18—C19 | 1.436 (6) |
N2—C11 | 1.356 (5) | C18—H18 | 0.9300 |
N3—C13 | 1.323 (5) | C19—C23 | 1.393 (5) |
N3—C24 | 1.360 (5) | C19—C20 | 1.398 (5) |
N4—C22 | 1.331 (5) | C20—C21 | 1.347 (5) |
N4—C23 | 1.358 (4) | C20—H20 | 0.9300 |
N5—C25 | 1.309 (5) | C21—C22 | 1.392 (5) |
N6—C26 | 1.288 (5) | C21—H21 | 0.9300 |
C1—C2 | 1.390 (6) | C22—H22 | 0.9300 |
C1—H1 | 0.9300 | C23—C24 | 1.422 (5) |
C2—C3 | 1.359 (6) | C25—C26 | 1.442 (5) |
C2—H2 | 0.9300 | ||
N1—Co1—N2 | 83.53 (14) | C7—C6—H6 | 119.4 |
N1—Co1—N3 | 92.55 (13) | C8—C7—C11 | 116.9 (4) |
N1—Co1—N4 | 175.38 (13) | C8—C7—C6 | 124.6 (4) |
N1—Co1—N5 | 93.33 (14) | C11—C7—C6 | 118.4 (5) |
N1—Co1—N6 | 90.43 (13) | C7—C8—C9 | 120.0 (4) |
N2—Co1—N3 | 89.53 (12) | C7—C8—H8 | 120.0 |
N2—Co1—N4 | 93.60 (13) | C9—C8—H8 | 120.0 |
N2—Co1—N5 | 175.51 (13) | C8—C9—C10 | 119.3 (5) |
N2—Co1—N6 | 95.53 (13) | C8—C9—H9 | 120.4 |
N3—Co1—N4 | 83.79 (13) | C10—C9—H9 | 120.4 |
N3—Co1—N5 | 93.82 (14) | N2—C10—C9 | 121.9 (4) |
N3—Co1—N6 | 174.40 (13) | N2—C10—H10 | 119.0 |
N4—Co1—N5 | 89.74 (13) | C9—C10—H10 | 119.0 |
N4—Co1—N6 | 93.46 (13) | N2—C11—C7 | 123.7 (4) |
N5—Co1—N6 | 81.26 (15) | N2—C11—C12 | 116.2 (3) |
N6—O1—H1A | 109.5 | C7—C11—C12 | 120.1 (4) |
N5—O2—H2A | 109.5 | N1—C12—C11 | 116.6 (4) |
C25—O3—H3A | 109.5 | N1—C12—C4 | 122.2 (4) |
C26—O4—H4A | 109.5 | C11—C12—C4 | 121.2 (4) |
H11A—O11—H11B | 121 (3) | N3—C13—C14 | 121.1 (4) |
H12A—O12—H12B | 111 (3) | N3—C13—H13 | 119.5 |
C1—N1—C12 | 118.6 (4) | C14—C13—H13 | 119.5 |
C1—N1—Co1 | 128.8 (3) | C15—C14—C13 | 120.7 (4) |
C12—N1—Co1 | 112.6 (3) | C15—C14—H14 | 119.6 |
C10—N2—C11 | 118.1 (4) | C13—C14—H14 | 119.6 |
C10—N2—Co1 | 131.0 (3) | C14—C15—C16 | 119.4 (4) |
C11—N2—Co1 | 110.9 (3) | C14—C15—H15 | 120.3 |
C13—N3—C24 | 118.4 (4) | C16—C15—H15 | 120.3 |
C13—N3—Co1 | 129.8 (3) | C24—C16—C15 | 117.0 (4) |
C24—N3—Co1 | 111.8 (2) | C24—C16—C17 | 118.2 (4) |
C22—N4—C23 | 118.0 (3) | C15—C16—C17 | 124.8 (4) |
C22—N4—Co1 | 129.7 (3) | C18—C17—C16 | 121.5 (4) |
C23—N4—Co1 | 112.3 (2) | C18—C17—H17 | 119.3 |
O2—N5—C25 | 123.2 (4) | C16—C17—H17 | 119.3 |
O2—N5—Co1 | 121.2 (3) | C17—C18—C19 | 121.9 (4) |
C25—N5—Co1 | 115.6 (3) | C17—C18—H18 | 119.1 |
C26—N6—O1 | 117.1 (3) | C19—C18—H18 | 119.1 |
C26—N6—Co1 | 116.4 (3) | C23—C19—C20 | 116.7 (4) |
O1—N6—Co1 | 125.2 (2) | C23—C19—C18 | 117.4 (4) |
O7—N7—O5 | 120.0 (5) | C20—C19—C18 | 125.9 (4) |
O7—N7—O6 | 120.0 (4) | C21—C20—C19 | 119.5 (4) |
O5—N7—O6 | 119.8 (4) | C21—C20—H20 | 120.2 |
O10—N8—O8 | 130.7 (11) | C19—C20—H20 | 120.2 |
O10—N8—O9 | 119.7 (10) | C20—C21—C22 | 121.0 (4) |
O8—N8—O9 | 109.5 (11) | C20—C21—H21 | 119.5 |
N1—C1—C2 | 122.4 (4) | C22—C21—H21 | 119.5 |
N1—C1—H1 | 118.8 | N4—C22—C21 | 121.2 (4) |
C2—C1—H1 | 118.8 | N4—C22—H22 | 119.4 |
C3—C2—C1 | 119.9 (5) | C21—C22—H22 | 119.4 |
C3—C2—H2 | 120.0 | N4—C23—C19 | 123.6 (4) |
C1—C2—H2 | 120.0 | N4—C23—C24 | 116.1 (3) |
C2—C3—C4 | 119.8 (4) | C19—C23—C24 | 120.3 (4) |
C2—C3—H3 | 120.1 | N3—C24—C16 | 123.4 (4) |
C4—C3—H3 | 120.1 | N3—C24—C23 | 115.9 (3) |
C3—C4—C12 | 117.0 (4) | C16—C24—C23 | 120.8 (4) |
C3—C4—C5 | 125.2 (4) | N5—C25—C26 | 112.9 (4) |
C12—C4—C5 | 117.9 (4) | N5—C25—O3 | 122.1 (4) |
C6—C5—C4 | 121.2 (4) | C26—C25—O3 | 124.8 (4) |
C6—C5—H5 | 119.4 | N6—C26—C25 | 113.7 (4) |
C4—C5—H5 | 119.4 | N6—C26—O4 | 123.7 (4) |
C5—C6—C7 | 121.3 (5) | C25—C26—O4 | 122.6 (4) |
C5—C6—H6 | 119.4 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N2 | 0.82 | 2.67 | 3.014 (4) | 107 |
O2—H2A···O3 | 0.82 | 2.36 | 2.819 (6) | 116 |
C1—H1···N5 | 0.93 | 2.51 | 2.998 (5) | 113 |
C13—H13···N1 | 0.93 | 2.58 | 3.043 (6) | 112 |
C22—H22···N6 | 0.93 | 2.58 | 3.041 (5) | 110 |
O1—H1A···O5i | 0.82 | 2.37 | 2.994 (5) | 134 |
O1—H1A···O6i | 0.82 | 1.99 | 2.699 (4) | 146 |
C3—H3···O5ii | 0.93 | 2.53 | 3.372 (6) | 151 |
C5—H5···O1iii | 0.93 | 2.54 | 3.343 (5) | 145 |
C18—H18···O2iv | 0.93 | 2.40 | 3.249 (6) | 152 |
C22—H22···O6v | 0.93 | 2.54 | 3.289 (5) | 138 |
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Co(C12H8N2)2(C2H4N2O4)](NO3)2·2H2O |
Mr | 699.46 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 13.8695 (11), 12.044 (5), 18.401 (3) |
β (°) | 95.997 (5) |
V (Å3) | 3057.1 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.64 |
Crystal size (mm) | 0.30 × 0.23 × 0.18 |
Data collection | |
Diffractometer | Bruker APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.833, 0.895 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19977, 6137, 3126 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.152, 0.99 |
No. of reflections | 6137 |
No. of parameters | 444 |
No. of restraints | 12 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.73, −0.45 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.
Co1—N1 | 1.932 (3) | Co1—N4 | 1.949 (3) |
Co1—N2 | 1.995 (3) | Co1—N5 | 1.904 (3) |
Co1—N3 | 1.965 (3) | Co1—N6 | 1.891 (3) |
N1—Co1—N2 | 83.53 (14) | N2—Co1—N6 | 95.53 (13) |
N1—Co1—N3 | 92.55 (13) | N3—Co1—N4 | 83.79 (13) |
N1—Co1—N4 | 175.38 (13) | N3—Co1—N5 | 93.82 (14) |
N1—Co1—N5 | 93.33 (14) | N3—Co1—N6 | 174.40 (13) |
N1—Co1—N6 | 90.43 (13) | N4—Co1—N5 | 89.74 (13) |
N2—Co1—N3 | 89.53 (12) | N4—Co1—N6 | 93.46 (13) |
N2—Co1—N4 | 93.60 (13) | N5—Co1—N6 | 81.26 (15) |
N2—Co1—N5 | 175.51 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N2 | 0.82 | 2.67 | 3.014 (4) | 107 |
O2—H2A···O3 | 0.82 | 2.36 | 2.819 (6) | 116 |
C1—H1···N5 | 0.93 | 2.51 | 2.998 (5) | 113 |
C13—H13···N1 | 0.93 | 2.58 | 3.043 (6) | 112 |
C22—H22···N6 | 0.93 | 2.58 | 3.041 (5) | 110 |
O1—H1A···O5i | 0.82 | 2.37 | 2.994 (5) | 134 |
O1—H1A···O6i | 0.82 | 1.99 | 2.699 (4) | 146 |
C3—H3···O5ii | 0.93 | 2.53 | 3.372 (6) | 151 |
C5—H5···O1iii | 0.93 | 2.54 | 3.343 (5) | 145 |
C18—H18···O2iv | 0.93 | 2.40 | 3.249 (6) | 152 |
C22—H22···O6v | 0.93 | 2.54 | 3.289 (5) | 138 |
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1. |
The crystal structure of bis(1,10-phenanthroline-N,N')(dihydroxy glyoxime) copper(II) dinitrate dihydrate, (II), has previously been reported (Liu et al., 2007). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six nitrogen atoms are coordinated to the cobalt atom, in a distorted octahedral arrangement (Table 1). The dihydroxyglyoxime and two phen ligands are each planar and the phen ligands are nearly perpendicular to each other, with a dihedral angle of 86.94 (7)°, as in (II).
In the crystal structure, the molecules are linked into a three-dimensional framework (Fig. 2) by O—H···O, C—H···O, C—H···N and O—H···N hydrogen bonds (Table 2). There are stacking interactions between adjacent phen ligands with centroid-centroid distance of 3.585 (3)Å (symmetry code: 1 - x, 2 - y, -z) leading to a supramolecular network structure (Fig. 2), as in (II).