metal-organic compounds
Bis[bis(1-ethylbenzimidazol-2-ylmethyl) ether]cobalt(II) dipicrate dimethylformamide disolvate
aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: wuhuilu@163.com
In the title complex, [Co(C20H22N4O)2](C6H2N3O7)2·2C3H7NO, the CoII ion is coordinated by two sets of two N atoms and an O atom from two independent tridendate ligands in a distorted octahedral coordination environment. There are significant differences between chemically equivalent coordination bond lengths. The is stabilized by weak intermolecular C—H⋯O hydrogen bonds and weak π–π stacking interactions [centroid–centroid distance 3.495 (1) Å]. In one of the anions one nitro group is rotationally disordered about the C—N bond with refined occupancies of 0.524 (8) and 0.476 (8).
Related literature
For related structures, see: Wu, Yun, Huang et al. (2009); Wu, Yun, Li et al. (2009); Yun et al. (2008).
Experimental
Crystal data
|
Refinement
|
|
Data collection: RAPID-AUTO (Rigaku/MSC 2004); cell RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809035934/lh2889sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809035934/lh2889Isup2.hkl
To a stirred solution of 1,3-bis(1-ethylbenzimidazol-2-yl)-2-oxopropane (0.167 g, 0.5 mmol) in hot MeOH (15 ml) was added Co(C6H2N3O7)2 (0.129 g, 0.25 mmol) in MeOH (5 ml). A brown crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF resulting in a brown solution. Brown crystals suitable for X-ray diffraction studies were obtained after three days at room temperature from ether diffusion into a DMF solution of the title compound. Yield, 0.210 g (71%). (found: C, 52.41; H, 4.68; N, 16.81. Calcd. for C116H124Co2N32O36: C, 52.37; H, 4.70; N, 16.85)
All H atoms were found in difference electron maps and were subsequently refined in a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and Uiso(H) = 1.2 Ueq or Uiso(H) = 1.5Ueq of the
respectively. In one of the anions one nitro group is rotationally disordered about the C-N bond with refined occupancies of 0.524 (8) [O8,O9] and 0.476 (8) [O8',O9'].Data collection: RAPID-AUTO (Rigaku/MSC 2004); cell
RAPID-AUTO (Rigaku/MSC 2004); data reduction: RAPID-AUTO (Rigaku/MSC 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. Molecular structure and atom numbering for the cation of the title compound. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level. | |
Fig. 2. Part of the crystal structure showing weak C—H···O hydrogen bonds (dashed lines) and weak π···π stacking interactions. Only H atoms involved in hydrogen bonds are shown. The disorder is not shown. |
[Co(C20H22N4O)2](C6H2N3O7)2·2C3H7NO | Z = 2 |
Mr = 1330.17 | F(000) = 1386 |
Triclinic, P1 | Dx = 1.446 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8799 (4) Å | Cell parameters from 7749 reflections |
b = 14.6525 (4) Å | θ = 3.0–25.5° |
c = 16.5701 (3) Å | µ = 0.37 mm−1 |
α = 110.664 (1)° | T = 153 K |
β = 96.470 (1)° | Block, brown |
γ = 99.612 (1)° | 0.38 × 0.22 × 0.14 mm |
V = 3054.62 (13) Å3 |
Rigaku R-AXIS Spider diffractometer | 11225 independent reflections |
Radiation source: fine-focus sealed tube | 8833 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ϕ and ω scans | θmax = 25.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −16→16 |
Tmin = 0.873, Tmax = 0.950 | k = −17→17 |
24337 measured reflections | l = −18→20 |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0663P)2 + 2.0559P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max = 0.10 |
11225 reflections | Δρmax = 0.98 e Å−3 |
858 parameters | Δρmin = −0.90 e Å−3 |
4 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0022 (5) |
[Co(C20H22N4O)2](C6H2N3O7)2·2C3H7NO | γ = 99.612 (1)° |
Mr = 1330.17 | V = 3054.62 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.8799 (4) Å | Mo Kα radiation |
b = 14.6525 (4) Å | µ = 0.37 mm−1 |
c = 16.5701 (3) Å | T = 153 K |
α = 110.664 (1)° | 0.38 × 0.22 × 0.14 mm |
β = 96.470 (1)° |
Rigaku R-AXIS Spider diffractometer | 11225 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 8833 reflections with I > 2σ(I) |
Tmin = 0.873, Tmax = 0.950 | Rint = 0.022 |
24337 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 4 restraints |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.14 | (Δ/σ)max = 0.10 |
11225 reflections | Δρmax = 0.98 e Å−3 |
858 parameters | Δρmin = −0.90 e Å−3 |
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 | 0.28649 (2) | 0.19838 (2) | 0.46816 (2) | 0.01823 (11) | |
O1 | 0.29902 (13) | 0.30499 (13) | 0.61018 (11) | 0.0234 (4) | |
O2 | 0.29752 (13) | 0.08087 (14) | 0.34517 (11) | 0.0278 (4) | |
O3 | 0.80117 (19) | 0.5715 (2) | 0.13764 (15) | 0.0629 (7) | |
O4 | 0.5964 (3) | 0.3781 (2) | 0.17574 (16) | 0.0752 (10) | |
O5 | 0.7548 (3) | 0.4037 (3) | 0.1790 (2) | 0.0980 (12) | |
O6 | 0.41385 (18) | 0.2944 (2) | −0.11930 (18) | 0.0619 (7) | |
O7 | 0.45343 (19) | 0.3970 (2) | −0.18404 (14) | 0.0559 (7) | |
O8 | 0.7909 (5) | 0.6140 (5) | −0.0805 (3) | 0.082 (3) | 0.524 (8) |
O9 | 0.8201 (4) | 0.6944 (5) | 0.0537 (4) | 0.064 (2) | 0.524 (8) |
O8' | 0.7091 (5) | 0.6837 (5) | −0.0389 (4) | 0.089 (3) | 0.476 (8) |
O9' | 0.8490 (4) | 0.6593 (10) | 0.0175 (9) | 0.116 (4) | 0.476 (8) |
O10 | 0.67849 (16) | 0.05378 (17) | −0.11405 (13) | 0.0406 (5) | |
O11 | 0.54090 (17) | 0.13588 (18) | −0.18370 (13) | 0.0434 (5) | |
O12 | 0.40246 (16) | 0.06268 (18) | −0.16289 (14) | 0.0443 (5) | |
O13 | 0.39642 (17) | 0.17501 (17) | 0.15142 (14) | 0.0442 (5) | |
O14 | 0.52461 (17) | 0.17492 (16) | 0.23989 (12) | 0.0407 (5) | |
O15 | 0.80210 (18) | 0.0547 (2) | 0.11187 (18) | 0.0587 (7) | |
O16 | 0.84422 (16) | 0.1175 (2) | 0.01821 (15) | 0.0518 (6) | |
O17 | 0.10881 (18) | 0.8163 (2) | 0.20909 (15) | 0.0575 (7) | |
O18 | 0.07622 (17) | 0.40600 (18) | 0.63580 (14) | 0.0473 (6) | |
N1 | 0.20049 (14) | 0.12155 (16) | 0.52909 (12) | 0.0197 (4) | |
N2 | 0.14353 (15) | 0.10419 (16) | 0.64503 (13) | 0.0223 (5) | |
N3 | 0.33896 (15) | 0.34492 (15) | 0.47641 (13) | 0.0200 (4) | |
N4 | 0.36761 (15) | 0.51053 (15) | 0.54120 (13) | 0.0209 (4) | |
N5 | 0.16690 (15) | 0.19040 (16) | 0.36748 (13) | 0.0206 (4) | |
N6 | 0.09391 (16) | 0.13339 (17) | 0.22634 (13) | 0.0248 (5) | |
N7 | 0.42207 (15) | 0.15693 (15) | 0.49147 (12) | 0.0196 (4) | |
N8 | 0.54212 (16) | 0.07996 (16) | 0.44281 (13) | 0.0235 (5) | |
N9 | 0.6710 (3) | 0.4043 (2) | 0.14874 (18) | 0.0558 (9) | |
N10 | 0.4692 (2) | 0.3651 (2) | −0.12503 (18) | 0.0426 (7) | |
N11 | 0.7593 (3) | 0.6329 (3) | −0.01009 (19) | 0.0867 (15) | |
N12 | 0.49148 (18) | 0.10217 (18) | −0.13969 (14) | 0.0321 (5) | |
N13 | 0.48254 (19) | 0.16547 (18) | 0.16615 (15) | 0.0327 (6) | |
N14 | 0.78255 (18) | 0.0908 (2) | 0.05747 (16) | 0.0370 (6) | |
N15 | 0.1137 (2) | 0.7045 (3) | 0.07460 (19) | 0.0623 (9) | |
N16 | −0.0601 (2) | 0.4302 (2) | 0.69697 (17) | 0.0453 (7) | |
C1 | 0.14755 (17) | 0.02311 (19) | 0.50421 (16) | 0.0202 (5) | |
C2 | 0.12581 (18) | −0.0567 (2) | 0.42273 (16) | 0.0237 (5) | |
H2A | 0.1477 | −0.0491 | 0.3727 | 0.028* | |
C3 | 0.07159 (19) | −0.1465 (2) | 0.41792 (18) | 0.0278 (6) | |
H3A | 0.0565 | −0.2020 | 0.3635 | 0.033* | |
C4 | 0.0378 (2) | −0.1586 (2) | 0.49117 (18) | 0.0289 (6) | |
H4A | 0.0010 | −0.2222 | 0.4853 | 0.035* | |
C5 | 0.05712 (19) | −0.0795 (2) | 0.57183 (18) | 0.0282 (6) | |
H5A | 0.0339 | −0.0869 | 0.6214 | 0.034* | |
C6 | 0.11200 (18) | 0.01088 (19) | 0.57638 (16) | 0.0220 (5) | |
C7 | 0.19536 (17) | 0.16562 (19) | 0.61295 (15) | 0.0194 (5) | |
C8 | 0.24117 (19) | 0.27325 (19) | 0.66549 (15) | 0.0224 (5) | |
H8A | 0.1893 | 0.3122 | 0.6799 | 0.027* | |
H8B | 0.2838 | 0.2815 | 0.7208 | 0.027* | |
C9 | 0.3238 (2) | 0.40958 (18) | 0.63268 (15) | 0.0229 (5) | |
H9A | 0.3830 | 0.4412 | 0.6802 | 0.028* | |
H9B | 0.2677 | 0.4400 | 0.6523 | 0.028* | |
C10 | 0.34504 (17) | 0.42222 (19) | 0.55015 (15) | 0.0206 (5) | |
C11 | 0.37509 (18) | 0.48952 (19) | 0.45373 (16) | 0.0223 (5) | |
C12 | 0.3948 (2) | 0.5512 (2) | 0.40767 (18) | 0.0291 (6) | |
H12A | 0.4070 | 0.6220 | 0.4351 | 0.035* | |
C13 | 0.3958 (2) | 0.5032 (2) | 0.31901 (18) | 0.0346 (7) | |
H13A | 0.4087 | 0.5425 | 0.2848 | 0.041* | |
C14 | 0.3782 (2) | 0.3990 (2) | 0.27845 (18) | 0.0315 (6) | |
H14A | 0.3796 | 0.3693 | 0.2177 | 0.038* | |
C15 | 0.3590 (2) | 0.3387 (2) | 0.32506 (17) | 0.0271 (6) | |
H15A | 0.3475 | 0.2679 | 0.2977 | 0.033* | |
C16 | 0.35722 (18) | 0.38544 (19) | 0.41382 (16) | 0.0221 (5) | |
C17 | 0.1169 (2) | 0.1340 (2) | 0.73351 (17) | 0.0282 (6) | |
H17A | 0.0446 | 0.1088 | 0.7274 | 0.034* | |
H17B | 0.1312 | 0.2079 | 0.7612 | 0.034* | |
C18 | 0.1725 (3) | 0.0947 (3) | 0.7923 (2) | 0.0495 (9) | |
H18A | 0.1522 | 0.1163 | 0.8497 | 0.074* | |
H18B | 0.2441 | 0.1207 | 0.7998 | 0.074* | |
H18C | 0.1576 | 0.0215 | 0.7659 | 0.074* | |
C19 | 0.3731 (2) | 0.60909 (19) | 0.60915 (16) | 0.0263 (6) | |
H19A | 0.4201 | 0.6604 | 0.5984 | 0.032* | |
H19B | 0.3991 | 0.6091 | 0.6673 | 0.032* | |
C20 | 0.2727 (2) | 0.6357 (2) | 0.6101 (2) | 0.0423 (8) | |
H20A | 0.2791 | 0.7016 | 0.6563 | 0.063* | |
H20B | 0.2262 | 0.5855 | 0.6215 | 0.063* | |
H20C | 0.2475 | 0.6374 | 0.5531 | 0.063* | |
C21 | 0.09872 (18) | 0.24717 (19) | 0.35843 (15) | 0.0217 (5) | |
C22 | 0.0729 (2) | 0.3280 (2) | 0.42065 (17) | 0.0274 (6) | |
H22A | 0.1039 | 0.3535 | 0.4807 | 0.033* | |
C23 | 0.0009 (2) | 0.3692 (2) | 0.39152 (19) | 0.0341 (7) | |
H23A | −0.0183 | 0.4237 | 0.4326 | 0.041* | |
C24 | −0.0450 (2) | 0.3330 (2) | 0.30304 (19) | 0.0363 (7) | |
H24A | −0.0944 | 0.3636 | 0.2857 | 0.044* | |
C25 | −0.0199 (2) | 0.2536 (2) | 0.24042 (19) | 0.0332 (6) | |
H25A | −0.0503 | 0.2289 | 0.1802 | 0.040* | |
C26 | 0.05232 (19) | 0.2121 (2) | 0.27061 (16) | 0.0251 (6) | |
C27 | 0.16210 (18) | 0.12508 (19) | 0.28700 (15) | 0.0221 (5) | |
C28 | 0.22980 (19) | 0.0551 (2) | 0.26444 (16) | 0.0259 (6) | |
H28A | 0.1923 | −0.0153 | 0.2432 | 0.031* | |
H28B | 0.2658 | 0.0642 | 0.2186 | 0.031* | |
C29 | 0.38727 (18) | 0.0477 (2) | 0.33422 (16) | 0.0233 (5) | |
H29A | 0.4191 | 0.0695 | 0.2916 | 0.028* | |
H29B | 0.3748 | −0.0261 | 0.3134 | 0.028* | |
C30 | 0.45091 (18) | 0.09541 (18) | 0.42356 (15) | 0.0195 (5) | |
C31 | 0.57725 (19) | 0.13738 (19) | 0.53148 (16) | 0.0233 (5) | |
C32 | 0.6663 (2) | 0.1502 (2) | 0.58537 (18) | 0.0298 (6) | |
H32A | 0.7174 | 0.1183 | 0.5633 | 0.036* | |
C33 | 0.6775 (2) | 0.2111 (2) | 0.67244 (18) | 0.0306 (6) | |
H33A | 0.7376 | 0.2219 | 0.7115 | 0.037* | |
C34 | 0.6014 (2) | 0.2577 (2) | 0.70433 (17) | 0.0286 (6) | |
H34A | 0.6113 | 0.2992 | 0.7647 | 0.034* | |
C35 | 0.51260 (19) | 0.2449 (2) | 0.65041 (16) | 0.0251 (6) | |
H35A | 0.4612 | 0.2760 | 0.6727 | 0.030* | |
C36 | 0.50137 (18) | 0.18448 (19) | 0.56205 (15) | 0.0204 (5) | |
C37 | 0.0750 (2) | 0.0776 (2) | 0.13075 (16) | 0.0333 (7) | |
H37A | 0.0028 | 0.0625 | 0.1076 | 0.040* | |
H37B | 0.0957 | 0.0133 | 0.1182 | 0.040* | |
C38 | 0.1305 (3) | 0.1359 (3) | 0.0843 (2) | 0.0502 (9) | |
H38A | 0.1163 | 0.0963 | 0.0211 | 0.075* | |
H38B | 0.2021 | 0.1501 | 0.1065 | 0.075* | |
H38C | 0.1090 | 0.1989 | 0.0954 | 0.075* | |
C39 | 0.6008 (2) | 0.0221 (2) | 0.38379 (17) | 0.0279 (6) | |
H39A | 0.5560 | −0.0255 | 0.3289 | 0.033* | |
H39B | 0.6329 | −0.0173 | 0.4121 | 0.033* | |
C40 | 0.6796 (2) | 0.0891 (2) | 0.36196 (19) | 0.0363 (7) | |
H40A | 0.7171 | 0.0482 | 0.3226 | 0.055* | |
H40B | 0.7249 | 0.1353 | 0.4161 | 0.055* | |
H40C | 0.6479 | 0.1273 | 0.3330 | 0.055* | |
C41 | 0.7297 (2) | 0.5228 (2) | 0.07784 (18) | 0.0378 (7) | |
C42 | 0.6578 (2) | 0.4375 (2) | 0.07595 (17) | 0.0350 (7) | |
C43 | 0.5747 (2) | 0.3879 (2) | 0.01257 (18) | 0.0330 (6) | |
H43A | 0.5291 | 0.3348 | 0.0173 | 0.040* | |
C44 | 0.5576 (2) | 0.4155 (2) | −0.05849 (17) | 0.0310 (6) | |
C45 | 0.6213 (2) | 0.4953 (2) | −0.06346 (17) | 0.0367 (7) | |
H45A | 0.6087 | 0.5148 | −0.1118 | 0.044* | |
C46 | 0.7027 (2) | 0.5462 (2) | 0.00134 (19) | 0.0388 (7) | |
C47 | 0.6395 (2) | 0.0877 (2) | −0.04959 (17) | 0.0278 (6) | |
C48 | 0.5411 (2) | 0.1095 (2) | −0.05470 (16) | 0.0265 (6) | |
C49 | 0.4898 (2) | 0.1320 (2) | 0.01257 (16) | 0.0264 (6) | |
H49A | 0.4240 | 0.1413 | 0.0034 | 0.032* | |
C50 | 0.5358 (2) | 0.1411 (2) | 0.09506 (16) | 0.0261 (6) | |
C51 | 0.6320 (2) | 0.1276 (2) | 0.10885 (17) | 0.0293 (6) | |
H51A | 0.6629 | 0.1342 | 0.1654 | 0.035* | |
C52 | 0.6820 (2) | 0.1045 (2) | 0.04027 (17) | 0.0286 (6) | |
C53 | 0.0698 (3) | 0.7568 (4) | 0.1365 (3) | 0.0910 (19) | |
H53 | −0.0004 | 0.7463 | 0.1222 | 0.109* | |
C54 | 0.2175 (3) | 0.7168 (3) | 0.0886 (2) | 0.0534 (9) | |
H54A | 0.2460 | 0.7619 | 0.1493 | 0.080* | |
H54B | 0.2447 | 0.7454 | 0.0484 | 0.080* | |
H54C | 0.2344 | 0.6517 | 0.0777 | 0.080* | |
C55 | 0.0620 (4) | 0.6385 (6) | −0.0135 (4) | 0.162 (4) | |
H55A | −0.0096 | 0.6347 | −0.0175 | 0.242* | |
H55B | 0.0749 | 0.5715 | −0.0262 | 0.242* | |
H55C | 0.0860 | 0.6648 | −0.0561 | 0.242* | |
C56 | 0.0356 (2) | 0.4296 (2) | 0.6990 (2) | 0.0416 (8) | |
H56A | 0.0762 | 0.4495 | 0.7551 | 0.050* | |
C57 | −0.1274 (3) | 0.4030 (3) | 0.6141 (2) | 0.0497 (8) | |
H57A | −0.0914 | 0.3820 | 0.5656 | 0.075* | |
H57B | −0.1538 | 0.4608 | 0.6136 | 0.075* | |
H57C | −0.1825 | 0.3478 | 0.6074 | 0.075* | |
C58 | −0.1011 (4) | 0.4648 (4) | 0.7763 (3) | 0.099 (2) | |
H58A | −0.0493 | 0.4805 | 0.8275 | 0.149* | |
H58B | −0.1562 | 0.4123 | 0.7746 | 0.149* | |
H58C | −0.1255 | 0.5250 | 0.7803 | 0.149* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co | 0.01811 (18) | 0.0209 (2) | 0.01589 (17) | 0.00583 (13) | 0.00398 (12) | 0.00627 (13) |
O1 | 0.0314 (10) | 0.0197 (9) | 0.0205 (9) | 0.0050 (8) | 0.0116 (7) | 0.0075 (7) |
O2 | 0.0226 (10) | 0.0405 (12) | 0.0179 (9) | 0.0166 (8) | 0.0030 (7) | 0.0040 (8) |
O3 | 0.0526 (16) | 0.0693 (18) | 0.0400 (13) | −0.0042 (13) | −0.0136 (11) | 0.0035 (12) |
O4 | 0.139 (3) | 0.0478 (16) | 0.0359 (14) | 0.0037 (17) | 0.0277 (16) | 0.0170 (12) |
O5 | 0.126 (3) | 0.106 (3) | 0.068 (2) | 0.041 (2) | −0.024 (2) | 0.0462 (19) |
O6 | 0.0374 (14) | 0.0474 (16) | 0.0740 (18) | 0.0025 (12) | −0.0019 (12) | −0.0022 (13) |
O7 | 0.0561 (16) | 0.0713 (18) | 0.0288 (12) | 0.0351 (14) | −0.0065 (10) | 0.0000 (11) |
O8 | 0.089 (5) | 0.081 (5) | 0.070 (4) | −0.009 (4) | 0.038 (3) | 0.028 (3) |
O9 | 0.033 (3) | 0.051 (4) | 0.093 (5) | −0.008 (3) | 0.000 (3) | 0.020 (3) |
O8' | 0.115 (6) | 0.078 (5) | 0.076 (5) | −0.031 (4) | −0.014 (4) | 0.065 (4) |
O9' | 0.072 (6) | 0.120 (10) | 0.160 (11) | −0.004 (6) | 0.033 (6) | 0.066 (8) |
O10 | 0.0462 (13) | 0.0484 (14) | 0.0297 (11) | 0.0229 (11) | 0.0162 (9) | 0.0094 (9) |
O11 | 0.0488 (13) | 0.0599 (15) | 0.0291 (11) | 0.0127 (11) | 0.0105 (9) | 0.0248 (10) |
O12 | 0.0330 (13) | 0.0553 (15) | 0.0398 (12) | 0.0022 (11) | −0.0048 (9) | 0.0194 (10) |
O13 | 0.0399 (13) | 0.0526 (15) | 0.0425 (12) | 0.0184 (11) | 0.0209 (10) | 0.0132 (10) |
O14 | 0.0554 (14) | 0.0444 (13) | 0.0219 (10) | 0.0091 (11) | 0.0129 (9) | 0.0113 (9) |
O15 | 0.0397 (14) | 0.085 (2) | 0.0775 (18) | 0.0222 (13) | 0.0072 (12) | 0.0592 (16) |
O16 | 0.0307 (12) | 0.0788 (19) | 0.0536 (14) | 0.0140 (12) | 0.0156 (10) | 0.0312 (13) |
O17 | 0.0457 (14) | 0.0662 (17) | 0.0402 (13) | 0.0142 (13) | 0.0072 (11) | −0.0046 (12) |
O18 | 0.0415 (13) | 0.0523 (15) | 0.0379 (12) | 0.0189 (11) | 0.0043 (10) | 0.0022 (10) |
N1 | 0.0158 (10) | 0.0250 (12) | 0.0176 (10) | 0.0064 (9) | 0.0028 (8) | 0.0065 (8) |
N2 | 0.0191 (11) | 0.0300 (12) | 0.0197 (10) | 0.0054 (9) | 0.0062 (8) | 0.0110 (9) |
N3 | 0.0202 (11) | 0.0198 (11) | 0.0194 (10) | 0.0015 (9) | 0.0039 (8) | 0.0079 (8) |
N4 | 0.0234 (11) | 0.0159 (11) | 0.0222 (11) | 0.0032 (9) | 0.0038 (8) | 0.0063 (8) |
N5 | 0.0191 (11) | 0.0229 (11) | 0.0190 (10) | 0.0051 (9) | 0.0044 (8) | 0.0065 (8) |
N6 | 0.0232 (11) | 0.0322 (13) | 0.0166 (10) | 0.0101 (10) | 0.0012 (8) | 0.0056 (9) |
N7 | 0.0190 (11) | 0.0223 (11) | 0.0180 (10) | 0.0060 (9) | 0.0046 (8) | 0.0072 (8) |
N8 | 0.0220 (11) | 0.0263 (12) | 0.0229 (11) | 0.0103 (9) | 0.0046 (8) | 0.0078 (9) |
N9 | 0.099 (3) | 0.0392 (17) | 0.0260 (14) | 0.0201 (17) | 0.0034 (16) | 0.0089 (12) |
N10 | 0.0321 (15) | 0.0375 (16) | 0.0414 (16) | 0.0165 (13) | 0.0017 (11) | −0.0074 (12) |
N11 | 0.117 (4) | 0.079 (3) | 0.0377 (19) | −0.042 (3) | 0.007 (2) | 0.0219 (18) |
N12 | 0.0365 (14) | 0.0349 (14) | 0.0244 (12) | 0.0123 (11) | 0.0051 (10) | 0.0090 (10) |
N13 | 0.0414 (15) | 0.0270 (13) | 0.0284 (13) | 0.0057 (11) | 0.0148 (11) | 0.0073 (10) |
N14 | 0.0309 (14) | 0.0438 (16) | 0.0405 (14) | 0.0118 (12) | 0.0058 (11) | 0.0196 (12) |
N15 | 0.0422 (17) | 0.064 (2) | 0.0459 (17) | 0.0149 (15) | −0.0057 (13) | −0.0179 (15) |
N16 | 0.0410 (16) | 0.0472 (17) | 0.0354 (14) | 0.0045 (13) | 0.0070 (11) | 0.0037 (12) |
C1 | 0.0131 (12) | 0.0231 (13) | 0.0263 (13) | 0.0063 (10) | 0.0029 (9) | 0.0110 (10) |
C2 | 0.0159 (12) | 0.0313 (15) | 0.0234 (13) | 0.0079 (11) | 0.0034 (9) | 0.0087 (11) |
C3 | 0.0222 (14) | 0.0249 (14) | 0.0318 (14) | 0.0080 (11) | −0.0003 (10) | 0.0058 (11) |
C4 | 0.0234 (14) | 0.0220 (14) | 0.0408 (16) | 0.0025 (11) | 0.0024 (11) | 0.0138 (12) |
C5 | 0.0218 (14) | 0.0323 (16) | 0.0366 (15) | 0.0064 (12) | 0.0060 (11) | 0.0201 (12) |
C6 | 0.0149 (12) | 0.0261 (14) | 0.0252 (13) | 0.0055 (10) | 0.0025 (9) | 0.0101 (10) |
C7 | 0.0170 (12) | 0.0238 (13) | 0.0188 (12) | 0.0070 (10) | 0.0038 (9) | 0.0087 (10) |
C8 | 0.0245 (13) | 0.0247 (14) | 0.0165 (12) | 0.0032 (11) | 0.0068 (9) | 0.0062 (10) |
C9 | 0.0290 (14) | 0.0168 (13) | 0.0199 (12) | 0.0037 (11) | 0.0040 (10) | 0.0039 (10) |
C10 | 0.0159 (12) | 0.0248 (14) | 0.0191 (12) | 0.0043 (10) | 0.0015 (9) | 0.0064 (10) |
C11 | 0.0185 (13) | 0.0221 (13) | 0.0259 (13) | 0.0027 (10) | 0.0049 (10) | 0.0091 (10) |
C12 | 0.0330 (15) | 0.0230 (14) | 0.0337 (15) | 0.0056 (12) | 0.0082 (11) | 0.0133 (11) |
C13 | 0.0389 (17) | 0.0405 (18) | 0.0329 (15) | 0.0069 (14) | 0.0124 (12) | 0.0232 (13) |
C14 | 0.0387 (16) | 0.0347 (16) | 0.0241 (13) | 0.0079 (13) | 0.0123 (11) | 0.0129 (12) |
C15 | 0.0302 (15) | 0.0257 (14) | 0.0254 (13) | 0.0073 (12) | 0.0091 (11) | 0.0078 (11) |
C16 | 0.0176 (12) | 0.0256 (14) | 0.0242 (13) | 0.0049 (10) | 0.0051 (9) | 0.0105 (10) |
C17 | 0.0264 (14) | 0.0394 (17) | 0.0244 (13) | 0.0104 (12) | 0.0111 (11) | 0.0155 (12) |
C18 | 0.059 (2) | 0.073 (3) | 0.0339 (17) | 0.0341 (19) | 0.0170 (15) | 0.0302 (17) |
C19 | 0.0324 (15) | 0.0192 (14) | 0.0239 (13) | 0.0041 (11) | 0.0059 (11) | 0.0048 (10) |
C20 | 0.0413 (18) | 0.0342 (18) | 0.0475 (18) | 0.0171 (15) | 0.0096 (14) | 0.0067 (14) |
C21 | 0.0180 (12) | 0.0268 (14) | 0.0215 (12) | 0.0044 (11) | 0.0053 (9) | 0.0104 (10) |
C22 | 0.0272 (14) | 0.0306 (15) | 0.0255 (13) | 0.0092 (12) | 0.0083 (10) | 0.0096 (11) |
C23 | 0.0337 (16) | 0.0365 (17) | 0.0357 (16) | 0.0163 (13) | 0.0127 (12) | 0.0124 (13) |
C24 | 0.0321 (16) | 0.0439 (19) | 0.0404 (16) | 0.0198 (14) | 0.0075 (12) | 0.0196 (14) |
C25 | 0.0275 (15) | 0.0430 (18) | 0.0307 (15) | 0.0145 (13) | 0.0017 (11) | 0.0140 (13) |
C26 | 0.0232 (14) | 0.0293 (15) | 0.0224 (13) | 0.0070 (11) | 0.0046 (10) | 0.0085 (11) |
C27 | 0.0183 (12) | 0.0264 (14) | 0.0183 (12) | 0.0038 (10) | 0.0024 (9) | 0.0055 (10) |
C28 | 0.0236 (14) | 0.0328 (15) | 0.0163 (12) | 0.0096 (11) | −0.0005 (10) | 0.0033 (10) |
C29 | 0.0220 (13) | 0.0281 (14) | 0.0211 (12) | 0.0108 (11) | 0.0077 (10) | 0.0076 (10) |
C30 | 0.0198 (13) | 0.0173 (13) | 0.0239 (12) | 0.0048 (10) | 0.0066 (10) | 0.0099 (10) |
C31 | 0.0223 (13) | 0.0234 (14) | 0.0242 (13) | 0.0047 (11) | 0.0032 (10) | 0.0095 (10) |
C32 | 0.0245 (14) | 0.0348 (16) | 0.0336 (15) | 0.0129 (12) | 0.0049 (11) | 0.0145 (12) |
C33 | 0.0266 (15) | 0.0321 (16) | 0.0307 (14) | 0.0058 (12) | −0.0032 (11) | 0.0117 (12) |
C34 | 0.0317 (15) | 0.0285 (15) | 0.0234 (13) | 0.0062 (12) | 0.0012 (11) | 0.0085 (11) |
C35 | 0.0249 (14) | 0.0286 (15) | 0.0239 (13) | 0.0071 (11) | 0.0067 (10) | 0.0113 (11) |
C36 | 0.0202 (13) | 0.0205 (13) | 0.0215 (12) | 0.0032 (10) | 0.0031 (9) | 0.0100 (10) |
C37 | 0.0302 (15) | 0.0452 (18) | 0.0164 (13) | 0.0120 (13) | −0.0031 (10) | 0.0028 (12) |
C38 | 0.053 (2) | 0.070 (3) | 0.0279 (16) | 0.0150 (18) | 0.0104 (14) | 0.0173 (16) |
C39 | 0.0272 (14) | 0.0299 (15) | 0.0280 (14) | 0.0170 (12) | 0.0071 (11) | 0.0072 (11) |
C40 | 0.0296 (16) | 0.0451 (19) | 0.0368 (16) | 0.0135 (14) | 0.0137 (12) | 0.0138 (13) |
C41 | 0.0352 (17) | 0.0419 (18) | 0.0256 (14) | 0.0057 (14) | 0.0027 (12) | 0.0023 (12) |
C42 | 0.0490 (19) | 0.0379 (17) | 0.0203 (13) | 0.0196 (14) | 0.0074 (12) | 0.0088 (12) |
C43 | 0.0399 (17) | 0.0237 (15) | 0.0342 (15) | 0.0115 (13) | 0.0138 (12) | 0.0055 (12) |
C44 | 0.0299 (15) | 0.0321 (16) | 0.0232 (13) | 0.0129 (13) | 0.0006 (11) | −0.0004 (11) |
C45 | 0.0517 (19) | 0.0356 (17) | 0.0189 (13) | 0.0081 (14) | 0.0042 (12) | 0.0072 (12) |
C46 | 0.0436 (18) | 0.0348 (17) | 0.0306 (15) | −0.0025 (14) | 0.0094 (13) | 0.0080 (13) |
C47 | 0.0317 (15) | 0.0265 (15) | 0.0263 (14) | 0.0110 (12) | 0.0095 (11) | 0.0081 (11) |
C48 | 0.0317 (15) | 0.0258 (14) | 0.0204 (13) | 0.0075 (12) | 0.0028 (10) | 0.0071 (10) |
C49 | 0.0273 (14) | 0.0262 (14) | 0.0262 (13) | 0.0082 (11) | 0.0066 (11) | 0.0092 (11) |
C50 | 0.0329 (15) | 0.0262 (14) | 0.0214 (13) | 0.0085 (12) | 0.0095 (11) | 0.0094 (10) |
C51 | 0.0329 (15) | 0.0313 (16) | 0.0229 (13) | 0.0052 (12) | 0.0039 (11) | 0.0105 (11) |
C52 | 0.0257 (14) | 0.0303 (15) | 0.0301 (14) | 0.0084 (12) | 0.0052 (11) | 0.0108 (11) |
C53 | 0.040 (2) | 0.113 (4) | 0.067 (3) | 0.030 (2) | −0.0079 (19) | −0.030 (3) |
C54 | 0.053 (2) | 0.057 (2) | 0.0446 (19) | 0.0150 (18) | 0.0175 (16) | 0.0084 (16) |
C55 | 0.083 (4) | 0.187 (7) | 0.093 (4) | 0.039 (4) | −0.027 (3) | −0.082 (4) |
C56 | 0.046 (2) | 0.0370 (18) | 0.0321 (16) | 0.0078 (15) | −0.0047 (14) | 0.0058 (13) |
C57 | 0.0376 (19) | 0.052 (2) | 0.059 (2) | 0.0071 (16) | −0.0016 (15) | 0.0237 (17) |
C58 | 0.071 (3) | 0.108 (4) | 0.066 (3) | −0.019 (3) | 0.036 (2) | −0.018 (3) |
Co—N1 | 2.083 (2) | C13—H13A | 0.9500 |
Co—N3 | 2.099 (2) | C14—C15 | 1.378 (4) |
Co—N7 | 2.108 (2) | C14—H14A | 0.9500 |
Co—N5 | 2.174 (2) | C15—C16 | 1.391 (4) |
Co—O2 | 2.1961 (17) | C15—H15A | 0.9500 |
Co—O1 | 2.2872 (16) | C17—C18 | 1.501 (4) |
O1—C9 | 1.413 (3) | C17—H17A | 0.9900 |
O1—C8 | 1.429 (3) | C17—H17B | 0.9900 |
O2—C29 | 1.419 (3) | C18—H18A | 0.9800 |
O2—C28 | 1.434 (3) | C18—H18B | 0.9800 |
O3—C41 | 1.232 (4) | C18—H18C | 0.9800 |
O4—N9 | 1.230 (4) | C19—C20 | 1.510 (4) |
O5—N9 | 1.217 (5) | C19—H19A | 0.9900 |
O6—N10 | 1.222 (4) | C19—H19B | 0.9900 |
O7—N10 | 1.237 (4) | C20—H20A | 0.9800 |
O8—N11 | 1.249 (3) | C20—H20B | 0.9800 |
O9—N11 | 1.230 (3) | C20—H20C | 0.9800 |
O8'—N11 | 1.271 (3) | C21—C26 | 1.395 (3) |
O9'—N11 | 1.223 (3) | C21—C22 | 1.399 (4) |
O10—C47 | 1.236 (3) | C22—C23 | 1.376 (4) |
O11—N12 | 1.225 (3) | C22—H22A | 0.9500 |
O12—N12 | 1.227 (3) | C23—C24 | 1.402 (4) |
O13—O13 | 0.000 (5) | C23—H23A | 0.9500 |
O13—N13 | 1.234 (3) | C24—C25 | 1.384 (4) |
O14—O14 | 0.000 (5) | C24—H24A | 0.9500 |
O14—N13 | 1.243 (3) | C25—C26 | 1.389 (4) |
O15—N14 | 1.223 (3) | C25—H25A | 0.9500 |
O16—N14 | 1.226 (3) | C27—C28 | 1.485 (4) |
O17—C53 | 1.206 (4) | C28—H28A | 0.9900 |
O18—C56 | 1.216 (4) | C28—H28B | 0.9900 |
N1—C7 | 1.326 (3) | C29—C30 | 1.493 (3) |
N1—C1 | 1.396 (3) | C29—H29A | 0.9900 |
N2—C7 | 1.348 (3) | C29—H29B | 0.9900 |
N2—C6 | 1.395 (3) | C31—C32 | 1.384 (4) |
N2—C17 | 1.484 (3) | C31—C36 | 1.399 (4) |
N3—C10 | 1.323 (3) | C32—C33 | 1.378 (4) |
N3—C16 | 1.391 (3) | C32—H32A | 0.9500 |
N4—C10 | 1.343 (3) | C33—C34 | 1.404 (4) |
N4—C11 | 1.391 (3) | C33—H33A | 0.9500 |
N4—C19 | 1.468 (3) | C34—C35 | 1.382 (4) |
N5—C27 | 1.325 (3) | C34—H34A | 0.9500 |
N5—C21 | 1.389 (3) | C35—C36 | 1.392 (3) |
N6—C27 | 1.353 (3) | C35—H35A | 0.9500 |
N6—C26 | 1.387 (3) | C37—C38 | 1.513 (4) |
N6—C37 | 1.472 (3) | C37—H37A | 0.9900 |
N7—C30 | 1.321 (3) | C37—H37B | 0.9900 |
N7—C36 | 1.404 (3) | C38—H38A | 0.9800 |
N8—C30 | 1.346 (3) | C38—H38B | 0.9800 |
N8—C31 | 1.391 (3) | C38—H38C | 0.9800 |
N8—C39 | 1.472 (3) | C39—C40 | 1.507 (4) |
N9—C42 | 1.455 (4) | C39—H39A | 0.9900 |
N10—C44 | 1.444 (4) | C39—H39B | 0.9900 |
N11—C46 | 1.463 (4) | C40—H40A | 0.9800 |
N12—C48 | 1.456 (3) | C40—H40B | 0.9800 |
N13—O13 | 1.234 (3) | C40—H40C | 0.9800 |
N13—O14 | 1.243 (3) | C41—C46 | 1.452 (4) |
N13—C50 | 1.432 (3) | C41—C42 | 1.452 (4) |
N14—C52 | 1.454 (4) | C42—C43 | 1.367 (4) |
N15—C53 | 1.324 (5) | C43—C44 | 1.383 (4) |
N15—C54 | 1.405 (5) | C43—H43A | 0.9500 |
N15—C55 | 1.455 (5) | C44—C45 | 1.375 (4) |
N16—C56 | 1.327 (4) | C45—C46 | 1.366 (4) |
N16—C58 | 1.450 (5) | C45—H45A | 0.9500 |
N16—C57 | 1.455 (4) | C47—C48 | 1.453 (4) |
C1—C2 | 1.400 (4) | C47—C52 | 1.456 (4) |
C1—C6 | 1.400 (3) | C48—C49 | 1.362 (4) |
C2—C3 | 1.372 (4) | C49—C50 | 1.393 (4) |
C2—H2A | 0.9500 | C49—H49A | 0.9500 |
C3—C4 | 1.407 (4) | C50—C51 | 1.388 (4) |
C3—H3A | 0.9500 | C51—C52 | 1.368 (4) |
C4—C5 | 1.387 (4) | C51—H51A | 0.9500 |
C4—H4A | 0.9500 | C53—H53 | 0.9500 |
C5—C6 | 1.386 (4) | C54—H54A | 0.9800 |
C5—H5A | 0.9500 | C54—H54B | 0.9800 |
C7—C8 | 1.490 (3) | C54—H54C | 0.9800 |
C8—H8A | 0.9900 | C55—H55A | 0.9800 |
C8—H8B | 0.9900 | C55—H55B | 0.9800 |
C9—C10 | 1.498 (3) | C55—H55C | 0.9800 |
C9—H9A | 0.9900 | C56—H56A | 0.9500 |
C9—H9B | 0.9900 | C57—H57A | 0.9800 |
C11—C12 | 1.388 (4) | C57—H57B | 0.9800 |
C11—C16 | 1.396 (4) | C57—H57C | 0.9800 |
C12—C13 | 1.390 (4) | C58—H58A | 0.9800 |
C12—H12A | 0.9500 | C58—H58B | 0.9800 |
C13—C14 | 1.399 (4) | C58—H58C | 0.9800 |
N1—Co—N3 | 140.20 (8) | N4—C19—H19B | 109.3 |
N1—Co—N7 | 99.60 (8) | C20—C19—H19B | 109.3 |
N3—Co—N7 | 100.49 (8) | H19A—C19—H19B | 107.9 |
N1—Co—N5 | 97.14 (8) | C19—C20—H20A | 109.5 |
N3—Co—N5 | 85.56 (8) | C19—C20—H20B | 109.5 |
N7—Co—N5 | 144.80 (7) | H20A—C20—H20B | 109.5 |
N1—Co—O2 | 103.97 (8) | C19—C20—H20C | 109.5 |
N3—Co—O2 | 114.58 (7) | H20A—C20—H20C | 109.5 |
N7—Co—O2 | 73.35 (7) | H20B—C20—H20C | 109.5 |
N5—Co—O2 | 72.66 (7) | N5—C21—C26 | 109.4 (2) |
N1—Co—O1 | 72.54 (7) | N5—C21—C22 | 130.8 (2) |
N3—Co—O1 | 71.85 (7) | C26—C21—C22 | 119.8 (2) |
N7—Co—O1 | 94.77 (7) | C23—C22—C21 | 117.5 (3) |
N5—Co—O1 | 119.81 (7) | C23—C22—H22A | 121.3 |
O2—Co—O1 | 167.10 (7) | C21—C22—H22A | 121.3 |
C9—O1—C8 | 114.91 (18) | C22—C23—C24 | 122.0 (3) |
C9—O1—Co | 120.08 (13) | C22—C23—H23A | 119.0 |
C8—O1—Co | 119.10 (14) | C24—C23—H23A | 119.0 |
C29—O2—C28 | 113.99 (18) | C25—C24—C23 | 121.4 (3) |
C29—O2—Co | 120.85 (14) | C25—C24—H24A | 119.3 |
C28—O2—Co | 122.57 (15) | C23—C24—H24A | 119.3 |
O13—O13—N13 | 0 (10) | C24—C25—C26 | 116.1 (3) |
O14—O14—N13 | 0 (10) | C24—C25—H25A | 121.9 |
C7—N1—C1 | 104.94 (19) | C26—C25—H25A | 121.9 |
C7—N1—Co | 120.31 (17) | N6—C26—C25 | 130.9 (2) |
C1—N1—Co | 134.50 (15) | N6—C26—C21 | 105.9 (2) |
C7—N2—C6 | 106.7 (2) | C25—C26—C21 | 123.2 (2) |
C7—N2—C17 | 125.9 (2) | N5—C27—N6 | 113.1 (2) |
C6—N2—C17 | 127.1 (2) | N5—C27—C28 | 123.5 (2) |
C10—N3—C16 | 105.6 (2) | N6—C27—C28 | 123.2 (2) |
C10—N3—Co | 120.51 (16) | O2—C28—C27 | 104.38 (19) |
C16—N3—Co | 133.02 (16) | O2—C28—H28A | 110.9 |
C10—N4—C11 | 106.8 (2) | C27—C28—H28A | 110.9 |
C10—N4—C19 | 125.9 (2) | O2—C28—H28B | 110.9 |
C11—N4—C19 | 127.0 (2) | C27—C28—H28B | 110.9 |
C27—N5—C21 | 105.0 (2) | H28A—C28—H28B | 108.9 |
C27—N5—Co | 116.83 (17) | O2—C29—C30 | 104.42 (19) |
C21—N5—Co | 137.15 (16) | O2—C29—H29A | 110.9 |
C27—N6—C26 | 106.5 (2) | C30—C29—H29A | 110.9 |
C27—N6—C37 | 126.9 (2) | O2—C29—H29B | 110.9 |
C26—N6—C37 | 126.2 (2) | C30—C29—H29B | 110.9 |
C30—N7—C36 | 105.0 (2) | H29A—C29—H29B | 108.9 |
C30—N7—Co | 117.67 (16) | N7—C30—N8 | 113.7 (2) |
C36—N7—Co | 136.96 (16) | N7—C30—C29 | 122.6 (2) |
C30—N8—C31 | 106.5 (2) | N8—C30—C29 | 123.7 (2) |
C30—N8—C39 | 129.1 (2) | C32—C31—N8 | 131.2 (2) |
C31—N8—C39 | 124.2 (2) | C32—C31—C36 | 122.7 (2) |
O5—N9—O4 | 123.9 (3) | N8—C31—C36 | 106.2 (2) |
O5—N9—C42 | 118.2 (4) | C33—C32—C31 | 116.9 (3) |
O4—N9—C42 | 117.9 (3) | C33—C32—H32A | 121.5 |
O6—N10—O7 | 123.9 (3) | C31—C32—H32A | 121.5 |
O6—N10—C44 | 118.3 (3) | C32—C33—C34 | 121.0 (3) |
O7—N10—C44 | 117.9 (3) | C32—C33—H33A | 119.5 |
O9'—N11—O9 | 39.6 (6) | C34—C33—H33A | 119.5 |
O9'—N11—O8 | 79.5 (8) | C35—C34—C33 | 121.9 (2) |
O9—N11—O8 | 113.3 (6) | C35—C34—H34A | 119.0 |
O9'—N11—O8' | 123.6 (8) | C33—C34—H34A | 119.0 |
O9—N11—O8' | 105.6 (6) | C34—C35—C36 | 117.4 (2) |
O8—N11—O8' | 84.5 (5) | C34—C35—H35A | 121.3 |
O9'—N11—C46 | 119.3 (7) | C36—C35—H35A | 121.3 |
O9—N11—C46 | 117.2 (5) | C35—C36—C31 | 120.1 (2) |
O8—N11—C46 | 115.1 (4) | C35—C36—N7 | 131.4 (2) |
O8'—N11—C46 | 116.5 (4) | C31—C36—N7 | 108.6 (2) |
O11—N12—O12 | 123.9 (2) | N6—C37—C38 | 111.9 (2) |
O11—N12—C48 | 118.1 (2) | N6—C37—H37A | 109.2 |
O12—N12—C48 | 118.0 (2) | C38—C37—H37A | 109.2 |
O13—N13—O13 | 0.0 (2) | N6—C37—H37B | 109.2 |
O13—N13—O14 | 122.8 (2) | C38—C37—H37B | 109.2 |
O13—N13—O14 | 122.8 (2) | H37A—C37—H37B | 107.9 |
O13—N13—O14 | 122.8 (2) | C37—C38—H38A | 109.5 |
O13—N13—O14 | 122.8 (2) | C37—C38—H38B | 109.5 |
O14—N13—O14 | 0.00 (19) | H38A—C38—H38B | 109.5 |
O13—N13—C50 | 118.6 (2) | C37—C38—H38C | 109.5 |
O13—N13—C50 | 118.6 (2) | H38A—C38—H38C | 109.5 |
O14—N13—C50 | 118.6 (2) | H38B—C38—H38C | 109.5 |
O14—N13—C50 | 118.6 (2) | N8—C39—C40 | 111.6 (2) |
O15—N14—O16 | 123.0 (3) | N8—C39—H39A | 109.3 |
O15—N14—C52 | 118.2 (2) | C40—C39—H39A | 109.3 |
O16—N14—C52 | 118.7 (2) | N8—C39—H39B | 109.3 |
C53—N15—C54 | 120.6 (3) | C40—C39—H39B | 109.3 |
C53—N15—C55 | 124.2 (4) | H39A—C39—H39B | 108.0 |
C54—N15—C55 | 115.0 (3) | C39—C40—H40A | 109.5 |
C56—N16—C58 | 122.2 (3) | C39—C40—H40B | 109.5 |
C56—N16—C57 | 120.8 (3) | H40A—C40—H40B | 109.5 |
C58—N16—C57 | 116.8 (3) | C39—C40—H40C | 109.5 |
N1—C1—C2 | 130.4 (2) | H40A—C40—H40C | 109.5 |
N1—C1—C6 | 109.3 (2) | H40B—C40—H40C | 109.5 |
C2—C1—C6 | 120.3 (2) | O3—C41—C46 | 124.5 (3) |
C3—C2—C1 | 117.4 (2) | O3—C41—C42 | 125.1 (3) |
C3—C2—H2A | 121.3 | C46—C41—C42 | 110.4 (2) |
C1—C2—H2A | 121.3 | C43—C42—C41 | 124.9 (3) |
C2—C3—C4 | 122.0 (2) | C43—C42—N9 | 116.5 (3) |
C2—C3—H3A | 119.0 | C41—C42—N9 | 118.5 (3) |
C4—C3—H3A | 119.0 | C42—C43—C44 | 119.5 (3) |
C5—C4—C3 | 121.2 (3) | C42—C43—H43A | 120.2 |
C5—C4—H4A | 119.4 | C44—C43—H43A | 120.2 |
C3—C4—H4A | 119.4 | C45—C44—C43 | 120.3 (3) |
C6—C5—C4 | 116.6 (2) | C45—C44—N10 | 119.5 (3) |
C6—C5—H5A | 121.7 | C43—C44—N10 | 120.1 (3) |
C4—C5—H5A | 121.7 | C46—C45—C44 | 119.8 (3) |
C5—C6—N2 | 131.9 (2) | C46—C45—H45A | 120.1 |
C5—C6—C1 | 122.6 (2) | C44—C45—H45A | 120.1 |
N2—C6—C1 | 105.6 (2) | C45—C46—C41 | 125.0 (3) |
N1—C7—N2 | 113.5 (2) | C45—C46—N11 | 113.4 (3) |
N1—C7—C8 | 122.8 (2) | C41—C46—N11 | 121.6 (3) |
N2—C7—C8 | 123.7 (2) | O10—C47—C48 | 124.0 (2) |
O1—C8—C7 | 104.67 (18) | O10—C47—C52 | 125.0 (3) |
O1—C8—H8A | 110.8 | C48—C47—C52 | 110.9 (2) |
C7—C8—H8A | 110.8 | C49—C48—C47 | 125.3 (2) |
O1—C8—H8B | 110.8 | C49—C48—N12 | 117.3 (2) |
C7—C8—H8B | 110.8 | C47—C48—N12 | 117.3 (2) |
H8A—C8—H8B | 108.9 | C48—C49—C50 | 118.7 (3) |
O1—C9—C10 | 104.92 (19) | C48—C49—H49A | 120.6 |
O1—C9—H9A | 110.8 | C50—C49—H49A | 120.6 |
C10—C9—H9A | 110.8 | C51—C50—C49 | 120.9 (2) |
O1—C9—H9B | 110.8 | C51—C50—N13 | 120.1 (2) |
C10—C9—H9B | 110.8 | C49—C50—N13 | 119.0 (2) |
H9A—C9—H9B | 108.8 | C52—C51—C50 | 119.4 (2) |
N3—C10—N4 | 112.9 (2) | C52—C51—H51A | 120.3 |
N3—C10—C9 | 122.2 (2) | C50—C51—H51A | 120.3 |
N4—C10—C9 | 124.8 (2) | C51—C52—N14 | 117.7 (2) |
C12—C11—N4 | 131.8 (2) | C51—C52—C47 | 124.4 (3) |
C12—C11—C16 | 122.3 (2) | N14—C52—C47 | 117.8 (2) |
N4—C11—C16 | 105.9 (2) | O17—C53—N15 | 127.5 (4) |
C11—C12—C13 | 116.0 (3) | O17—C53—H53 | 116.3 |
C11—C12—H12A | 122.0 | N15—C53—H53 | 116.3 |
C13—C12—H12A | 122.0 | N15—C54—H54A | 109.5 |
C12—C13—C14 | 122.2 (2) | N15—C54—H54B | 109.5 |
C12—C13—H13A | 118.9 | H54A—C54—H54B | 109.5 |
C14—C13—H13A | 118.9 | N15—C54—H54C | 109.5 |
C15—C14—C13 | 121.2 (2) | H54A—C54—H54C | 109.5 |
C15—C14—H14A | 119.4 | H54B—C54—H54C | 109.5 |
C13—C14—H14A | 119.4 | N15—C55—H55A | 109.5 |
C14—C15—C16 | 117.4 (3) | N15—C55—H55B | 109.5 |
C14—C15—H15A | 121.3 | H55A—C55—H55B | 109.5 |
C16—C15—H15A | 121.3 | N15—C55—H55C | 109.5 |
C15—C16—N3 | 130.4 (2) | H55A—C55—H55C | 109.5 |
C15—C16—C11 | 120.9 (2) | H55B—C55—H55C | 109.5 |
N3—C16—C11 | 108.7 (2) | O18—C56—N16 | 126.1 (3) |
N2—C17—C18 | 112.7 (2) | O18—C56—H56A | 117.0 |
N2—C17—H17A | 109.0 | N16—C56—H56A | 117.0 |
C18—C17—H17A | 109.0 | N16—C57—H57A | 109.5 |
N2—C17—H17B | 109.0 | N16—C57—H57B | 109.5 |
C18—C17—H17B | 109.0 | H57A—C57—H57B | 109.5 |
H17A—C17—H17B | 107.8 | N16—C57—H57C | 109.5 |
C17—C18—H18A | 109.5 | H57A—C57—H57C | 109.5 |
C17—C18—H18B | 109.5 | H57B—C57—H57C | 109.5 |
H18A—C18—H18B | 109.5 | N16—C58—H58A | 109.5 |
C17—C18—H18C | 109.5 | N16—C58—H58B | 109.5 |
H18A—C18—H18C | 109.5 | H58A—C58—H58B | 109.5 |
H18B—C18—H18C | 109.5 | N16—C58—H58C | 109.5 |
N4—C19—C20 | 111.7 (2) | H58A—C58—H58C | 109.5 |
N4—C19—H19A | 109.3 | H58B—C58—H58C | 109.5 |
C20—C19—H19A | 109.3 | ||
N1—Co—O1—C9 | −155.93 (19) | Co—N5—C21—C26 | 168.72 (18) |
N3—Co—O1—C9 | 6.00 (17) | C27—N5—C21—C22 | −178.8 (3) |
N7—Co—O1—C9 | 105.49 (18) | Co—N5—C21—C22 | −11.2 (4) |
N5—Co—O1—C9 | −67.64 (19) | N5—C21—C22—C23 | −179.5 (3) |
O2—Co—O1—C9 | 128.0 (3) | C26—C21—C22—C23 | 0.6 (4) |
N1—Co—O1—C8 | −4.36 (17) | C21—C22—C23—C24 | −0.6 (4) |
N3—Co—O1—C8 | 157.56 (18) | C22—C23—C24—C25 | 0.0 (5) |
N7—Co—O1—C8 | −102.94 (17) | C23—C24—C25—C26 | 0.4 (4) |
N5—Co—O1—C8 | 83.92 (18) | C27—N6—C26—C25 | 179.1 (3) |
O2—Co—O1—C8 | −80.5 (4) | C37—N6—C26—C25 | 5.1 (5) |
N1—Co—O2—C29 | −106.16 (18) | C27—N6—C26—C21 | −0.6 (3) |
N3—Co—O2—C29 | 84.01 (19) | C37—N6—C26—C21 | −174.5 (2) |
N7—Co—O2—C29 | −10.14 (17) | C24—C25—C26—N6 | 179.9 (3) |
N5—Co—O2—C29 | 160.60 (19) | C24—C25—C26—C21 | −0.4 (4) |
O1—Co—O2—C29 | −33.6 (4) | N5—C21—C26—N6 | −0.3 (3) |
N1—Co—O2—C28 | 93.21 (19) | C22—C21—C26—N6 | 179.6 (2) |
N3—Co—O2—C28 | −76.6 (2) | N5—C21—C26—C25 | 180.0 (2) |
N7—Co—O2—C28 | −170.8 (2) | C22—C21—C26—C25 | −0.1 (4) |
N5—Co—O2—C28 | −0.04 (18) | C21—N5—C27—N6 | −1.6 (3) |
O1—Co—O2—C28 | 165.8 (3) | Co—N5—C27—N6 | −172.15 (16) |
N3—Co—N1—C7 | −28.3 (2) | C21—N5—C27—C28 | 174.0 (2) |
N7—Co—N1—C7 | 91.11 (19) | Co—N5—C27—C28 | 3.5 (3) |
N5—Co—N1—C7 | −119.97 (18) | C26—N6—C27—N5 | 1.4 (3) |
O2—Co—N1—C7 | 166.19 (18) | C37—N6—C27—N5 | 175.3 (2) |
O1—Co—N1—C7 | −0.91 (17) | C26—N6—C27—C28 | −174.2 (2) |
N3—Co—N1—C1 | 158.5 (2) | C37—N6—C27—C28 | −0.3 (4) |
N7—Co—N1—C1 | −82.1 (2) | C29—O2—C28—C27 | −160.4 (2) |
N5—Co—N1—C1 | 66.8 (2) | Co—O2—C28—C27 | 1.5 (3) |
O2—Co—N1—C1 | −7.0 (2) | N5—C27—C28—O2 | −3.2 (3) |
O1—Co—N1—C1 | −174.1 (2) | N6—C27—C28—O2 | 172.0 (2) |
N1—Co—N3—C10 | 21.8 (3) | C28—O2—C29—C30 | 171.8 (2) |
N7—Co—N3—C10 | −97.34 (19) | Co—O2—C29—C30 | 9.6 (3) |
N5—Co—N3—C10 | 117.65 (19) | C36—N7—C30—N8 | −0.1 (3) |
O2—Co—N3—C10 | −173.70 (17) | Co—N7—C30—N8 | 174.38 (16) |
O1—Co—N3—C10 | −5.72 (18) | C36—N7—C30—C29 | 179.7 (2) |
N1—Co—N3—C16 | −146.1 (2) | Co—N7—C30—C29 | −5.9 (3) |
N7—Co—N3—C16 | 94.8 (2) | C31—N8—C30—N7 | −0.6 (3) |
N5—Co—N3—C16 | −50.2 (2) | C39—N8—C30—N7 | −175.7 (2) |
O2—Co—N3—C16 | 18.4 (2) | C31—N8—C30—C29 | 179.6 (2) |
O1—Co—N3—C16 | −173.6 (2) | C39—N8—C30—C29 | 4.5 (4) |
N1—Co—N5—C27 | −104.17 (18) | O2—C29—C30—N7 | −2.4 (3) |
N3—Co—N5—C27 | 115.76 (18) | O2—C29—C30—N8 | 177.3 (2) |
N7—Co—N5—C27 | 13.8 (3) | C30—N8—C31—C32 | −179.7 (3) |
O2—Co—N5—C27 | −1.72 (17) | C39—N8—C31—C32 | −4.2 (4) |
O1—Co—N5—C27 | −178.11 (16) | C30—N8—C31—C36 | 1.1 (3) |
N1—Co—N5—C21 | 89.3 (2) | C39—N8—C31—C36 | 176.5 (2) |
N3—Co—N5—C21 | −50.8 (2) | N8—C31—C32—C33 | −178.2 (3) |
N7—Co—N5—C21 | −152.7 (2) | C36—C31—C32—C33 | 0.9 (4) |
O2—Co—N5—C21 | −168.3 (2) | C31—C32—C33—C34 | 0.1 (4) |
O1—Co—N5—C21 | 15.3 (3) | C32—C33—C34—C35 | −0.1 (4) |
N1—Co—N7—C30 | 109.79 (18) | C33—C34—C35—C36 | −0.8 (4) |
N3—Co—N7—C30 | −104.75 (18) | C34—C35—C36—C31 | 1.7 (4) |
N5—Co—N7—C30 | −7.5 (3) | C34—C35—C36—N7 | −179.9 (3) |
O2—Co—N7—C30 | 7.96 (17) | C32—C31—C36—C35 | −1.9 (4) |
O1—Co—N7—C30 | −177.14 (17) | N8—C31—C36—C35 | 177.5 (2) |
N1—Co—N7—C36 | −78.0 (2) | C32—C31—C36—N7 | 179.5 (2) |
N3—Co—N7—C36 | 67.5 (2) | N8—C31—C36—N7 | −1.2 (3) |
N5—Co—N7—C36 | 164.7 (2) | C30—N7—C36—C35 | −177.6 (3) |
O2—Co—N7—C36 | −179.8 (2) | Co—N7—C36—C35 | 9.5 (4) |
O1—Co—N7—C36 | −4.9 (2) | C30—N7—C36—C31 | 0.8 (3) |
O13—O13—N13—O14 | 0.00 (19) | Co—N7—C36—C31 | −172.02 (18) |
O13—O13—N13—O14 | 0.00 (19) | C27—N6—C37—C38 | −95.6 (3) |
O13—O13—N13—C50 | 0.00 (14) | C26—N6—C37—C38 | 77.1 (3) |
O14—O14—N13—O13 | 0.00 (10) | C30—N8—C39—C40 | 101.1 (3) |
O14—O14—N13—O13 | 0.00 (10) | C31—N8—C39—C40 | −73.2 (3) |
O14—O14—N13—C50 | 0.00 (15) | O3—C41—C42—C43 | 175.2 (3) |
C7—N1—C1—C2 | 178.0 (3) | C46—C41—C42—C43 | −1.8 (4) |
Co—N1—C1—C2 | −8.1 (4) | O3—C41—C42—N9 | −1.4 (5) |
C7—N1—C1—C6 | −0.5 (3) | C46—C41—C42—N9 | −178.4 (3) |
Co—N1—C1—C6 | 173.48 (17) | O5—N9—C42—C43 | 142.6 (3) |
N1—C1—C2—C3 | 179.9 (2) | O4—N9—C42—C43 | −37.0 (4) |
C6—C1—C2—C3 | −1.9 (4) | O5—N9—C42—C41 | −40.5 (4) |
C1—C2—C3—C4 | 0.7 (4) | O4—N9—C42—C41 | 139.9 (3) |
C2—C3—C4—C5 | 0.6 (4) | C41—C42—C43—C44 | 3.3 (4) |
C3—C4—C5—C6 | −0.7 (4) | N9—C42—C43—C44 | 180.0 (3) |
C4—C5—C6—N2 | 179.2 (3) | C42—C43—C44—C45 | −2.9 (4) |
C4—C5—C6—C1 | −0.5 (4) | C42—C43—C44—N10 | −178.8 (2) |
C7—N2—C6—C5 | 179.6 (3) | O6—N10—C44—C45 | 179.9 (3) |
C17—N2—C6—C5 | −6.3 (4) | O7—N10—C44—C45 | −0.9 (4) |
C7—N2—C6—C1 | −0.6 (3) | O6—N10—C44—C43 | −4.2 (4) |
C17—N2—C6—C1 | 173.5 (2) | O7—N10—C44—C43 | 175.0 (2) |
N1—C1—C6—C5 | −179.5 (2) | C43—C44—C45—C46 | 1.1 (4) |
C2—C1—C6—C5 | 1.9 (4) | N10—C44—C45—C46 | 177.0 (3) |
N1—C1—C6—N2 | 0.7 (3) | C44—C45—C46—C41 | 0.4 (5) |
C2—C1—C6—N2 | −177.9 (2) | C44—C45—C46—N11 | −176.1 (3) |
C1—N1—C7—N2 | 0.0 (3) | O3—C41—C46—C45 | −177.1 (3) |
Co—N1—C7—N2 | −174.95 (16) | C42—C41—C46—C45 | −0.1 (4) |
C1—N1—C7—C8 | −178.9 (2) | O3—C41—C46—N11 | −0.9 (5) |
Co—N1—C7—C8 | 6.1 (3) | C42—C41—C46—N11 | 176.1 (3) |
C6—N2—C7—N1 | 0.4 (3) | O9'—N11—C46—C45 | −150.0 (9) |
C17—N2—C7—N1 | −173.8 (2) | O9—N11—C46—C45 | 164.8 (6) |
C6—N2—C7—C8 | 179.3 (2) | O8—N11—C46—C45 | −58.3 (6) |
C17—N2—C7—C8 | 5.1 (4) | O8'—N11—C46—C45 | 38.4 (5) |
C9—O1—C8—C7 | 160.6 (2) | O9'—N11—C46—C41 | 33.4 (10) |
Co—O1—C8—C7 | 7.6 (2) | O9—N11—C46—C41 | −11.7 (7) |
N1—C7—C8—O1 | −8.8 (3) | O8—N11—C46—C41 | 125.2 (5) |
N2—C7—C8—O1 | 172.4 (2) | O8'—N11—C46—C41 | −138.2 (5) |
C8—O1—C9—C10 | −157.7 (2) | O10—C47—C48—C49 | 169.2 (3) |
Co—O1—C9—C10 | −5.0 (2) | C52—C47—C48—C49 | −6.8 (4) |
C16—N3—C10—N4 | −1.1 (3) | O10—C47—C48—N12 | −7.7 (4) |
Co—N3—C10—N4 | −171.93 (16) | C52—C47—C48—N12 | 176.3 (2) |
C16—N3—C10—C9 | 176.2 (2) | O11—N12—C48—C49 | 140.6 (3) |
Co—N3—C10—C9 | 5.4 (3) | O12—N12—C48—C49 | −39.2 (4) |
C11—N4—C10—N3 | 1.3 (3) | O11—N12—C48—C47 | −42.2 (4) |
C19—N4—C10—N3 | 175.7 (2) | O12—N12—C48—C47 | 138.0 (3) |
C11—N4—C10—C9 | −176.0 (2) | C47—C48—C49—C50 | 4.0 (4) |
C19—N4—C10—C9 | −1.5 (4) | N12—C48—C49—C50 | −179.1 (2) |
O1—C9—C10—N3 | 0.0 (3) | C48—C49—C50—C51 | 0.0 (4) |
O1—C9—C10—N4 | 177.0 (2) | C48—C49—C50—N13 | 179.5 (2) |
C10—N4—C11—C12 | 178.7 (3) | O13—N13—C50—C51 | −178.5 (3) |
C19—N4—C11—C12 | 4.3 (4) | O13—N13—C50—C51 | −178.5 (3) |
C10—N4—C11—C16 | −0.9 (3) | O14—N13—C50—C51 | 0.6 (4) |
C19—N4—C11—C16 | −175.3 (2) | O14—N13—C50—C51 | 0.6 (4) |
N4—C11—C12—C13 | −179.5 (3) | O13—N13—C50—C49 | 1.9 (4) |
C16—C11—C12—C13 | 0.1 (4) | O13—N13—C50—C49 | 1.9 (4) |
C11—C12—C13—C14 | −0.2 (4) | O14—N13—C50—C49 | −178.9 (2) |
C12—C13—C14—C15 | 0.1 (5) | O14—N13—C50—C49 | −178.9 (2) |
C13—C14—C15—C16 | 0.3 (4) | C49—C50—C51—C52 | −0.3 (4) |
C14—C15—C16—N3 | 179.1 (3) | N13—C50—C51—C52 | −179.8 (3) |
C14—C15—C16—C11 | −0.5 (4) | C50—C51—C52—N14 | −179.9 (3) |
C10—N3—C16—C15 | −179.2 (3) | C50—C51—C52—C47 | −3.3 (4) |
Co—N3—C16—C15 | −10.0 (4) | O15—N14—C52—C51 | 33.4 (4) |
C10—N3—C16—C11 | 0.5 (3) | O16—N14—C52—C51 | −145.2 (3) |
Co—N3—C16—C11 | 169.68 (17) | O15—N14—C52—C47 | −143.4 (3) |
C12—C11—C16—C15 | 0.3 (4) | O16—N14—C52—C47 | 38.0 (4) |
N4—C11—C16—C15 | 180.0 (2) | O10—C47—C52—C51 | −169.6 (3) |
C12—C11—C16—N3 | −179.4 (2) | C48—C47—C52—C51 | 6.4 (4) |
N4—C11—C16—N3 | 0.2 (3) | O10—C47—C52—N14 | 7.0 (4) |
C7—N2—C17—C18 | −110.1 (3) | C48—C47—C52—N14 | −177.0 (2) |
C6—N2—C17—C18 | 76.9 (3) | C54—N15—C53—O17 | −1.8 (9) |
C10—N4—C19—C20 | −86.1 (3) | C55—N15—C53—O17 | −176.0 (7) |
C11—N4—C19—C20 | 87.2 (3) | C58—N16—C56—O18 | −176.6 (4) |
C27—N5—C21—C26 | 1.1 (3) | C57—N16—C56—O18 | −1.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18B···O12i | 0.98 | 2.57 | 3.342 (4) | 135 |
C15—H15A···O13 | 0.95 | 2.56 | 3.191 (3) | 124 |
C18—H18B···O12i | 0.98 | 2.57 | 3.342 (4) | 135 |
C28—H28A···O17ii | 0.99 | 2.38 | 3.365 (4) | 173 |
C28—H28B···O10iii | 0.99 | 2.29 | 2.994 (3) | 128 |
C29—H29A···O14 | 0.99 | 2.39 | 3.331 (3) | 158 |
C35—H35A···O7i | 0.95 | 2.44 | 3.158 (3) | 133 |
C53—H53···O9′iv | 0.95 | 2.39 | 3.242 (7) | 148 |
C56—H56A···O3v | 0.95 | 2.46 | 3.335 (4) | 154 |
Symmetry codes: (i) x, y, z+1; (ii) x, y−1, z; (iii) −x+1, −y, −z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Co(C20H22N4O)2](C6H2N3O7)2·2C3H7NO |
Mr | 1330.17 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 153 |
a, b, c (Å) | 13.8799 (4), 14.6525 (4), 16.5701 (3) |
α, β, γ (°) | 110.664 (1), 96.470 (1), 99.612 (1) |
V (Å3) | 3054.62 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.38 × 0.22 × 0.14 |
Data collection | |
Diffractometer | Rigaku R-AXIS Spider diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.873, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24337, 11225, 8833 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.136, 1.14 |
No. of reflections | 11225 |
No. of parameters | 858 |
No. of restraints | 4 |
H-atom treatment | H-atom parameters constrained |
(Δ/σ)max | 0.10 |
Δρmax, Δρmin (e Å−3) | 0.98, −0.90 |
Computer programs: RAPID-AUTO (Rigaku/MSC 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).
Co—N1 | 2.083 (2) | Co—N5 | 2.174 (2) |
Co—N3 | 2.099 (2) | Co—O2 | 2.1961 (17) |
Co—N7 | 2.108 (2) | Co—O1 | 2.2872 (16) |
N1—Co—N3 | 140.20 (8) | N7—Co—O2 | 73.35 (7) |
N1—Co—N7 | 99.60 (8) | N5—Co—O2 | 72.66 (7) |
N3—Co—N7 | 100.49 (8) | N1—Co—O1 | 72.54 (7) |
N1—Co—N5 | 97.14 (8) | N3—Co—O1 | 71.85 (7) |
N3—Co—N5 | 85.56 (8) | N7—Co—O1 | 94.77 (7) |
N7—Co—N5 | 144.80 (7) | N5—Co—O1 | 119.81 (7) |
N1—Co—O2 | 103.97 (8) | O2—Co—O1 | 167.10 (7) |
N3—Co—O2 | 114.58 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18B···O12i | 0.98 | 2.57 | 3.342 (4) | 135.3 |
C15—H15A···O13 | 0.95 | 2.56 | 3.191 (3) | 124.3 |
C18—H18B···O12i | 0.98 | 2.57 | 3.342 (4) | 135.3 |
C28—H28A···O17ii | 0.99 | 2.38 | 3.365 (4) | 173.2 |
C28—H28B···O10iii | 0.99 | 2.29 | 2.994 (3) | 127.6 |
C29—H29A···O14 | 0.99 | 2.39 | 3.331 (3) | 158.0 |
C35—H35A···O7i | 0.95 | 2.44 | 3.158 (3) | 132.5 |
C53—H53···O9'iv | 0.95 | 2.39 | 3.242 (7) | 148.4 |
C56—H56A···O3v | 0.95 | 2.46 | 3.335 (4) | 153.8 |
Symmetry codes: (i) x, y, z+1; (ii) x, y−1, z; (iii) −x+1, −y, −z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1. |
Acknowledgements
The authors acknowledge financial support and a grant from the `Qing Lan' Talent Engineering Funds and the Students' Science and Technology Innovation Funds (grant No. DXS2008–041) of Lanzhou Jiaotong University. A grant from the `Long Yuan Qing Nian' of Gansu Province also is acknowledged.
References
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, H., Yun, R., Huang, X., Sun, Q. & Qi, B. (2009). Acta Cryst. E65, m851. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wu, H., Yun, R., Li, K., Tao, S. & Wang, K. (2009). Acta Cryst. E65, m786. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yun, R., Ying, W., Qi, B., Fan, X. & Wu, H. (2008). Acta Cryst. E64, m1529. Web of Science CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Interest in bis(2-benzimidazolyl)alkanes and their derivatives are widespread and we have previously reported the crystal structure of some related complexes (Wu, Yun, Huang et al., 2009; Wu, Yun, Li et al., 2009; Yun et al., 2008). The asymmetric unit of the title compound consists of a di[1,3-bis(1-ethylbenzimidazol-2-yl)-2-oxopropane] cobalt(II) cation (Fig. 1), two picrate anions and two molecules of DMF. The CoII ion is six-coordinated with a N4O2 ligand set. The Etobb (1,3-bis(1-ethylbenzimidazol-2-yl)-2-oxopropane) ligand acts as a tridentate donor. The four N atoms are not in an ideal equatorial plane and the coordination geometry of the CoII may be best described as distorted octahedral. There are significant differnces between chemically equivalent coordination bond lengths. The crystal structure is stabilized by weak intermolecular C—H···O hydrogen bond interactions and weak π···π stacking interactions (Fig. 2) with centroid to centroid distances of 3.495 (1)Å between inversion related benzimidazole rings systems.