The title cobalt(II) coordination polymer, [Co(C16H8O8)(C10H8N2)2]n, was obtained by the reaction of Co(OAc)2·4H2O (OAc is acetate), 4,4′-bipyridine (4,4′-bpy) and biphenyl-3,4,3′,4′-tetracarboxylic acid (H4L) under hydrothermal conditions. Each CoII atom lies at the centre of a distorted octahedron, coordinated by four O atoms from three H2L2− and two N atoms from two monodentate 4,4′-bpy ligands. Each H2L2− ligand coordinates to three CoII centres through two carboxylate groups, one acting as a bridging bidentate group and the other in a chelating bidentate fashion. Two Co atoms, two H2L2− and four 4,4′-bpy ligands form a ring dimer node, and these nodes link into an extended broad chain along the c axis.
Supporting information
CCDC reference: 293971
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.101
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.643
Value of mu given = 0.636
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.04
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.16
PLAT804_ALERT_4_C ARU-Pack Problem in PLATON Analysis ............ !
PLAT804_ALERT_4_C ARU-Pack Problem in PLATON Analysis ............ !
PLAT804_ALERT_4_C ARU-Pack Problem in PLATON Analysis ............ !
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
poly[bis(4,4'-bipyridine)(µ
3-4,4'-dicarboxy-biphenyl-3,3'-
dicarboxylato)cobalt(II)]
top
Crystal data top
[Co(C16H8O8)(C10H8N2)2] | F(000) = 1436 |
Mr = 699.52 | Dx = 1.564 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9781 (10) Å | Cell parameters from 18156 reflections |
b = 24.094 (2) Å | θ = 1.7–28.3° |
c = 10.7056 (9) Å | µ = 0.64 mm−1 |
β = 105.925 (2)° | T = 293 K |
V = 2971.1 (4) Å3 | Block, red |
Z = 4 | 0.24 × 0.23 × 0.11 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 6985 independent reflections |
Radiation source: fine-focus sealed tube | 3983 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.3°, θmin = 1.7° |
ω scans | h = −13→15 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −31→28 |
Tmin = 0.812, Tmax = 0.896 | l = −14→12 |
18276 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0415P)2] where P = (Fo2 + 2Fc2)/3 |
6985 reflections | (Δ/σ)max = 0.033 |
450 parameters | Δρmax = 0.68 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.6125 (2) | 0.19844 (11) | 0.6864 (2) | 0.0287 (6) | |
C2 | 0.8172 (2) | 0.11508 (10) | 0.7403 (2) | 0.0276 (6) | |
C3 | 1.0674 (2) | 0.06958 (10) | 1.4222 (2) | 0.0243 (6) | |
C4 | 1.2062 (2) | 0.16976 (11) | 1.5589 (3) | 0.0336 (7) | |
C5 | 0.7061 (2) | 0.19548 (9) | 0.8121 (2) | 0.0240 (6) | |
C6 | 0.79263 (19) | 0.15477 (9) | 0.8382 (2) | 0.0222 (5) | |
C7 | 0.8712 (2) | 0.15271 (10) | 0.9599 (2) | 0.0266 (6) | |
H7 | 0.9268 | 0.1247 | 0.9776 | 0.032* | |
C8 | 0.8700 (2) | 0.19108 (9) | 1.0572 (2) | 0.0234 (6) | |
C9 | 0.7865 (2) | 0.23281 (10) | 1.0279 (2) | 0.0298 (6) | |
H9 | 0.7857 | 0.2600 | 1.0892 | 0.036* | |
C10 | 0.7051 (2) | 0.23412 (10) | 0.9089 (2) | 0.0278 (6) | |
H10 | 0.6481 | 0.2614 | 0.8925 | 0.033* | |
C11 | 1.1115 (2) | 0.17317 (10) | 1.4335 (2) | 0.0306 (6) | |
C12 | 1.0790 (2) | 0.22566 (10) | 1.3811 (3) | 0.0415 (7) | |
H12 | 1.1107 | 0.2570 | 1.4285 | 0.050* | |
C13 | 1.0008 (2) | 0.23216 (11) | 1.2603 (3) | 0.0388 (7) | |
H13 | 0.9797 | 0.2676 | 1.2280 | 0.047* | |
C14 | 0.9538 (2) | 0.18605 (10) | 1.1872 (2) | 0.0251 (6) | |
C15 | 0.9829 (2) | 0.13392 (10) | 1.2421 (2) | 0.0255 (6) | |
H15 | 0.9498 | 0.1028 | 1.1950 | 0.031* | |
C16 | 1.05929 (19) | 0.12651 (9) | 1.3645 (2) | 0.0228 (5) | |
C17 | 0.7604 (2) | 0.11457 (11) | 0.3844 (2) | 0.0372 (7) | |
H17 | 0.7840 | 0.1439 | 0.4421 | 0.045* | |
C18 | 0.6946 (2) | 0.12655 (11) | 0.2606 (3) | 0.0369 (7) | |
H18 | 0.6744 | 0.1631 | 0.2370 | 0.044* | |
C19 | 0.6583 (2) | 0.08453 (11) | 0.1713 (2) | 0.0302 (6) | |
C20 | 0.6922 (2) | 0.03163 (11) | 0.2143 (3) | 0.0419 (7) | |
H20 | 0.6708 | 0.0018 | 0.1578 | 0.050* | |
C21 | 0.7574 (2) | 0.02255 (11) | 0.3400 (3) | 0.0420 (7) | |
H21 | 0.7780 | −0.0138 | 0.3656 | 0.050* | |
C22 | 0.4461 (2) | 0.14970 (12) | −0.1176 (3) | 0.0414 (7) | |
H22 | 0.3993 | 0.1811 | −0.1349 | 0.050* | |
C23 | 0.5153 (2) | 0.14227 (11) | 0.0077 (3) | 0.0385 (7) | |
H23 | 0.5146 | 0.1683 | 0.0716 | 0.046* | |
C24 | 0.5855 (2) | 0.09594 (11) | 0.0374 (2) | 0.0319 (6) | |
C25 | 0.5855 (2) | 0.06126 (12) | −0.0652 (3) | 0.0494 (8) | |
H25 | 0.6339 | 0.0304 | −0.0519 | 0.059* | |
C26 | 0.5132 (3) | 0.07234 (13) | −0.1882 (3) | 0.0500 (8) | |
H26 | 0.5155 | 0.0483 | −0.2555 | 0.060* | |
C27 | 1.3868 (3) | 0.17705 (14) | 1.3172 (3) | 0.0538 (9) | |
H27 | 1.3988 | 0.2145 | 1.3371 | 0.065* | |
C28 | 1.3058 (2) | 0.16252 (12) | 1.2025 (3) | 0.0487 (8) | |
H28 | 1.2649 | 0.1900 | 1.1476 | 0.058* | |
C29 | 1.2859 (2) | 0.10762 (11) | 1.1700 (3) | 0.0340 (6) | |
C30 | 1.3455 (3) | 0.06864 (13) | 1.2593 (3) | 0.0530 (9) | |
H30 | 1.3319 | 0.0309 | 1.2444 | 0.064* | |
C31 | 1.4255 (3) | 0.08717 (15) | 1.3711 (3) | 0.0637 (10) | |
H31 | 1.4659 | 0.0608 | 1.4296 | 0.076* | |
C32 | 1.1135 (2) | 0.10930 (11) | 0.8187 (2) | 0.0329 (6) | |
H32 | 1.1020 | 0.1336 | 0.7488 | 0.040* | |
C33 | 1.1871 (2) | 0.12533 (11) | 0.9353 (3) | 0.0352 (7) | |
H33 | 1.2240 | 0.1596 | 0.9424 | 0.042* | |
C34 | 1.2069 (2) | 0.09048 (10) | 1.0434 (2) | 0.0299 (6) | |
C35 | 1.1520 (2) | 0.03925 (11) | 1.0235 (3) | 0.0344 (7) | |
H35 | 1.1642 | 0.0137 | 1.0911 | 0.041* | |
C36 | 1.0792 (2) | 0.02643 (10) | 0.9028 (2) | 0.0308 (6) | |
H36 | 1.0430 | −0.0081 | 0.8918 | 0.037* | |
Co1 | 0.91816 (3) | 0.052633 (13) | 0.61614 (3) | 0.02609 (11) | |
N1 | 0.79286 (17) | 0.06296 (8) | 0.4272 (2) | 0.0305 (5) | |
N2 | 0.44195 (19) | 0.11485 (10) | −0.2150 (2) | 0.0402 (6) | |
N3 | 1.05768 (17) | 0.06101 (8) | 0.79996 (19) | 0.0283 (5) | |
N4 | 1.4478 (2) | 0.14026 (12) | 1.3997 (2) | 0.0511 (7) | |
O1 | 0.54251 (16) | 0.23581 (8) | 0.66041 (19) | 0.0464 (5) | |
O2 | 0.61500 (16) | 0.15656 (8) | 0.61008 (19) | 0.0399 (5) | |
O3 | 0.87348 (14) | 0.13393 (7) | 0.66506 (16) | 0.0302 (4) | |
O4 | 0.79670 (15) | 0.06433 (7) | 0.74458 (17) | 0.0352 (4) | |
O5 | 1.08982 (15) | 0.03004 (7) | 1.35570 (16) | 0.0320 (4) | |
O6 | 1.04652 (14) | 0.06467 (7) | 1.53016 (16) | 0.0312 (4) | |
O7 | 1.26811 (17) | 0.12420 (8) | 1.56766 (19) | 0.0412 (5) | |
O8 | 1.22466 (17) | 0.20579 (8) | 1.63992 (19) | 0.0566 (6) | |
H1 | 1.329 (3) | 0.1240 (15) | 1.636 (4) | 0.099 (14)* | |
H2 | 0.554 (3) | 0.1566 (12) | 0.538 (3) | 0.065 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0273 (14) | 0.0326 (16) | 0.0244 (15) | −0.0029 (12) | 0.0039 (12) | 0.0024 (12) |
C2 | 0.0296 (14) | 0.0274 (15) | 0.0191 (14) | 0.0063 (11) | −0.0046 (11) | −0.0007 (11) |
C3 | 0.0224 (13) | 0.0271 (14) | 0.0194 (14) | −0.0002 (10) | −0.0010 (11) | −0.0010 (11) |
C4 | 0.0381 (16) | 0.0329 (16) | 0.0233 (15) | −0.0029 (13) | −0.0024 (13) | 0.0037 (12) |
C5 | 0.0282 (14) | 0.0235 (13) | 0.0186 (14) | −0.0002 (11) | 0.0036 (11) | 0.0044 (11) |
C6 | 0.0290 (14) | 0.0207 (13) | 0.0168 (13) | 0.0004 (10) | 0.0061 (11) | 0.0005 (10) |
C7 | 0.0325 (14) | 0.0232 (13) | 0.0222 (14) | 0.0086 (11) | 0.0041 (12) | 0.0024 (11) |
C8 | 0.0302 (14) | 0.0209 (13) | 0.0158 (13) | 0.0005 (10) | 0.0011 (11) | −0.0005 (10) |
C9 | 0.0416 (16) | 0.0251 (14) | 0.0215 (14) | 0.0075 (12) | 0.0066 (12) | −0.0041 (11) |
C10 | 0.0343 (15) | 0.0232 (14) | 0.0245 (15) | 0.0125 (11) | 0.0054 (12) | 0.0012 (11) |
C11 | 0.0375 (15) | 0.0258 (15) | 0.0238 (14) | −0.0002 (11) | 0.0007 (12) | 0.0010 (11) |
C12 | 0.0556 (18) | 0.0262 (15) | 0.0290 (16) | −0.0071 (14) | −0.0116 (14) | −0.0038 (13) |
C13 | 0.0538 (18) | 0.0206 (14) | 0.0318 (16) | 0.0009 (12) | −0.0057 (14) | 0.0021 (12) |
C14 | 0.0301 (14) | 0.0257 (14) | 0.0160 (14) | 0.0032 (11) | 0.0004 (11) | 0.0001 (10) |
C15 | 0.0328 (14) | 0.0208 (13) | 0.0199 (14) | −0.0002 (11) | 0.0022 (11) | −0.0033 (10) |
C16 | 0.0280 (14) | 0.0222 (13) | 0.0165 (13) | 0.0042 (10) | 0.0030 (11) | 0.0011 (10) |
C17 | 0.0466 (17) | 0.0360 (16) | 0.0226 (15) | 0.0016 (13) | −0.0012 (13) | −0.0034 (12) |
C18 | 0.0489 (17) | 0.0327 (15) | 0.0242 (15) | 0.0055 (13) | 0.0018 (13) | 0.0043 (12) |
C19 | 0.0265 (14) | 0.0415 (17) | 0.0197 (14) | 0.0017 (12) | 0.0014 (11) | −0.0028 (12) |
C20 | 0.0489 (18) | 0.0351 (16) | 0.0302 (17) | 0.0079 (14) | −0.0088 (14) | −0.0109 (13) |
C21 | 0.0523 (18) | 0.0329 (16) | 0.0297 (17) | 0.0127 (13) | −0.0076 (14) | −0.0012 (13) |
C22 | 0.0355 (16) | 0.0440 (18) | 0.0396 (19) | 0.0078 (13) | 0.0019 (14) | 0.0113 (15) |
C23 | 0.0409 (16) | 0.0393 (17) | 0.0293 (16) | 0.0026 (13) | −0.0006 (13) | −0.0006 (12) |
C24 | 0.0276 (14) | 0.0393 (16) | 0.0250 (15) | 0.0010 (12) | 0.0010 (12) | 0.0008 (12) |
C25 | 0.0506 (19) | 0.057 (2) | 0.0298 (17) | 0.0252 (16) | −0.0069 (14) | −0.0039 (15) |
C26 | 0.0553 (19) | 0.060 (2) | 0.0253 (17) | 0.0119 (16) | −0.0044 (14) | −0.0063 (14) |
C27 | 0.058 (2) | 0.051 (2) | 0.045 (2) | −0.0122 (16) | 0.0008 (17) | −0.0138 (16) |
C28 | 0.0498 (19) | 0.0429 (19) | 0.0413 (19) | −0.0030 (15) | −0.0078 (15) | −0.0025 (14) |
C29 | 0.0300 (15) | 0.0405 (17) | 0.0271 (15) | −0.0002 (13) | 0.0005 (12) | −0.0065 (13) |
C30 | 0.062 (2) | 0.0466 (19) | 0.0342 (18) | 0.0103 (15) | −0.0144 (16) | −0.0101 (14) |
C31 | 0.069 (2) | 0.067 (3) | 0.037 (2) | 0.0188 (19) | −0.0146 (17) | −0.0081 (17) |
C32 | 0.0352 (15) | 0.0362 (16) | 0.0248 (15) | −0.0041 (12) | 0.0036 (12) | 0.0061 (12) |
C33 | 0.0369 (16) | 0.0292 (15) | 0.0353 (17) | −0.0054 (12) | 0.0031 (13) | −0.0009 (12) |
C34 | 0.0266 (14) | 0.0350 (15) | 0.0251 (15) | 0.0049 (12) | 0.0018 (12) | −0.0025 (12) |
C35 | 0.0410 (16) | 0.0365 (16) | 0.0227 (15) | −0.0029 (13) | 0.0034 (13) | 0.0038 (12) |
C36 | 0.0389 (15) | 0.0251 (14) | 0.0263 (16) | −0.0032 (12) | 0.0053 (13) | −0.0013 (11) |
Co1 | 0.0344 (2) | 0.02349 (19) | 0.01775 (19) | 0.00300 (16) | 0.00274 (14) | −0.00093 (15) |
N1 | 0.0339 (12) | 0.0301 (13) | 0.0225 (12) | 0.0037 (10) | −0.0003 (10) | −0.0015 (10) |
N2 | 0.0363 (13) | 0.0526 (16) | 0.0253 (14) | 0.0002 (12) | −0.0025 (11) | 0.0051 (12) |
N3 | 0.0300 (12) | 0.0329 (13) | 0.0205 (12) | −0.0001 (10) | 0.0046 (9) | −0.0005 (10) |
N4 | 0.0432 (15) | 0.0666 (19) | 0.0356 (16) | −0.0016 (13) | −0.0024 (13) | −0.0145 (14) |
O1 | 0.0436 (12) | 0.0460 (12) | 0.0378 (12) | 0.0164 (10) | −0.0085 (9) | 0.0020 (10) |
O2 | 0.0365 (11) | 0.0467 (12) | 0.0276 (12) | 0.0030 (9) | −0.0064 (9) | −0.0098 (10) |
O3 | 0.0391 (10) | 0.0313 (10) | 0.0201 (10) | 0.0032 (8) | 0.0078 (8) | −0.0003 (8) |
O4 | 0.0487 (11) | 0.0245 (10) | 0.0310 (11) | 0.0019 (8) | 0.0087 (9) | −0.0043 (8) |
O5 | 0.0494 (11) | 0.0200 (9) | 0.0258 (11) | 0.0034 (8) | 0.0092 (9) | −0.0017 (8) |
O6 | 0.0364 (10) | 0.0375 (11) | 0.0186 (10) | −0.0006 (8) | 0.0057 (8) | 0.0036 (8) |
O7 | 0.0362 (12) | 0.0481 (13) | 0.0299 (12) | 0.0053 (10) | −0.0067 (10) | −0.0016 (9) |
O8 | 0.0711 (15) | 0.0450 (13) | 0.0335 (12) | 0.0032 (11) | −0.0195 (11) | −0.0148 (10) |
Geometric parameters (Å, º) top
C1—O1 | 1.210 (3) | C22—N2 | 1.330 (3) |
C1—O2 | 1.304 (3) | C22—C23 | 1.381 (3) |
C1—C5 | 1.498 (3) | C22—H22 | 0.9300 |
C2—O4 | 1.250 (3) | C23—C24 | 1.382 (3) |
C2—O3 | 1.267 (3) | C23—H23 | 0.9300 |
C2—C6 | 1.507 (3) | C24—C25 | 1.380 (4) |
C3—O6 | 1.254 (3) | C25—C26 | 1.389 (4) |
C3—O5 | 1.261 (3) | C25—H25 | 0.9300 |
C3—C16 | 1.496 (3) | C26—N2 | 1.314 (3) |
C4—O8 | 1.204 (3) | C26—H26 | 0.9300 |
C4—O7 | 1.313 (3) | C27—N4 | 1.321 (4) |
C4—C11 | 1.504 (3) | C27—C28 | 1.385 (4) |
C5—C10 | 1.395 (3) | C27—H27 | 0.9300 |
C5—C6 | 1.399 (3) | C28—C29 | 1.372 (4) |
C6—C7 | 1.383 (3) | C28—H28 | 0.9300 |
C7—C8 | 1.395 (3) | C29—C30 | 1.390 (4) |
C7—H7 | 0.9300 | C29—C34 | 1.483 (3) |
C8—C9 | 1.392 (3) | C30—C31 | 1.385 (4) |
C8—C14 | 1.481 (3) | C30—H30 | 0.9300 |
C9—C10 | 1.376 (3) | C31—N4 | 1.325 (4) |
C9—H9 | 0.9300 | C31—H31 | 0.9300 |
C10—H10 | 0.9300 | C32—N3 | 1.329 (3) |
C11—C16 | 1.395 (3) | C32—C33 | 1.371 (3) |
C11—C12 | 1.395 (3) | C32—H32 | 0.9300 |
C12—C13 | 1.381 (3) | C33—C34 | 1.396 (3) |
C12—H12 | 0.9300 | C33—H33 | 0.9300 |
C13—C14 | 1.387 (3) | C34—C35 | 1.387 (3) |
C13—H13 | 0.9300 | C35—C36 | 1.381 (3) |
C14—C15 | 1.390 (3) | C35—H35 | 0.9300 |
C15—C16 | 1.389 (3) | C36—N3 | 1.348 (3) |
C15—H15 | 0.9300 | C36—H36 | 0.9300 |
C17—N1 | 1.345 (3) | Co1—O6i | 2.0180 (17) |
C17—C18 | 1.374 (3) | Co1—O5ii | 2.0209 (16) |
C17—H17 | 0.9300 | Co1—O3 | 2.1333 (16) |
C18—C19 | 1.378 (3) | Co1—N1 | 2.177 (2) |
C18—H18 | 0.9300 | Co1—N3 | 2.214 (2) |
C19—C20 | 1.378 (3) | Co1—O4 | 2.2769 (18) |
C19—C24 | 1.485 (3) | O2—H2 | 0.91 (3) |
C20—C21 | 1.375 (4) | O5—Co1ii | 2.0209 (16) |
C20—H20 | 0.9300 | O6—Co1iii | 2.0180 (17) |
C21—N1 | 1.336 (3) | O7—H1 | 0.88 (4) |
C21—H21 | 0.9300 | | |
| | | |
O1—C1—O2 | 124.4 (2) | C23—C24—C25 | 116.0 (2) |
O1—C1—C5 | 122.9 (2) | C23—C24—C19 | 122.1 (2) |
O2—C1—C5 | 112.7 (2) | C25—C24—C19 | 121.9 (2) |
O4—C2—O3 | 121.2 (2) | C24—C25—C26 | 120.2 (3) |
O4—C2—C6 | 121.1 (2) | C24—C25—H25 | 119.9 |
O3—C2—C6 | 117.0 (2) | C26—C25—H25 | 119.9 |
O6—C3—O5 | 125.2 (2) | N2—C26—C25 | 123.7 (3) |
O6—C3—C16 | 117.4 (2) | N2—C26—H26 | 118.1 |
O5—C3—C16 | 117.3 (2) | C25—C26—H26 | 118.1 |
O8—C4—O7 | 124.3 (2) | N4—C27—C28 | 123.2 (3) |
O8—C4—C11 | 123.2 (2) | N4—C27—H27 | 118.4 |
O7—C4—C11 | 112.5 (2) | C28—C27—H27 | 118.4 |
C10—C5—C6 | 118.4 (2) | C29—C28—C27 | 120.0 (3) |
C10—C5—C1 | 118.6 (2) | C29—C28—H28 | 120.0 |
C6—C5—C1 | 122.9 (2) | C27—C28—H28 | 120.0 |
C7—C6—C5 | 119.3 (2) | C28—C29—C30 | 117.1 (3) |
C7—C6—C2 | 114.9 (2) | C28—C29—C34 | 121.6 (2) |
C5—C6—C2 | 125.6 (2) | C30—C29—C34 | 121.3 (2) |
C6—C7—C8 | 122.4 (2) | C31—C30—C29 | 118.7 (3) |
C6—C7—H7 | 118.8 | C31—C30—H30 | 120.7 |
C8—C7—H7 | 118.8 | C29—C30—H30 | 120.7 |
C9—C8—C7 | 117.6 (2) | N4—C31—C30 | 124.0 (3) |
C9—C8—C14 | 122.0 (2) | N4—C31—H31 | 118.0 |
C7—C8—C14 | 120.3 (2) | C30—C31—H31 | 118.0 |
C10—C9—C8 | 120.5 (2) | N3—C32—C33 | 123.7 (2) |
C10—C9—H9 | 119.7 | N3—C32—H32 | 118.1 |
C8—C9—H9 | 119.7 | C33—C32—H32 | 118.1 |
C9—C10—C5 | 121.6 (2) | C32—C33—C34 | 120.4 (2) |
C9—C10—H10 | 119.2 | C32—C33—H33 | 119.8 |
C5—C10—H10 | 119.2 | C34—C33—H33 | 119.8 |
C16—C11—C12 | 118.9 (2) | C35—C34—C33 | 116.3 (2) |
C16—C11—C4 | 123.2 (2) | C35—C34—C29 | 123.0 (2) |
C12—C11—C4 | 117.9 (2) | C33—C34—C29 | 120.7 (2) |
C13—C12—C11 | 121.5 (2) | C36—C35—C34 | 119.6 (2) |
C13—C12—H12 | 119.3 | C36—C35—H35 | 120.2 |
C11—C12—H12 | 119.3 | C34—C35—H35 | 120.2 |
C12—C13—C14 | 120.3 (2) | N3—C36—C35 | 123.8 (2) |
C12—C13—H13 | 119.9 | N3—C36—H36 | 118.1 |
C14—C13—H13 | 119.9 | C35—C36—H36 | 118.1 |
C13—C14—C15 | 118.0 (2) | O6i—Co1—O5ii | 106.42 (7) |
C13—C14—C8 | 122.1 (2) | O6i—Co1—O3 | 104.71 (7) |
C15—C14—C8 | 119.9 (2) | O5ii—Co1—O3 | 147.47 (7) |
C14—C15—C16 | 122.6 (2) | O6i—Co1—N1 | 88.69 (7) |
C14—C15—H15 | 118.7 | O5ii—Co1—N1 | 101.68 (7) |
C16—C15—H15 | 118.7 | O3—Co1—N1 | 88.15 (7) |
C15—C16—C11 | 118.6 (2) | O6i—Co1—N3 | 84.75 (7) |
C15—C16—C3 | 117.3 (2) | O5ii—Co1—N3 | 90.71 (7) |
C11—C16—C3 | 123.5 (2) | O3—Co1—N3 | 82.94 (7) |
N1—C17—C18 | 123.9 (2) | N1—Co1—N3 | 167.22 (8) |
N1—C17—H17 | 118.0 | O6i—Co1—O4 | 161.94 (7) |
C18—C17—H17 | 118.0 | O5ii—Co1—O4 | 88.16 (6) |
C17—C18—C19 | 120.2 (2) | O3—Co1—O4 | 59.55 (6) |
C17—C18—H18 | 119.9 | N1—Co1—O4 | 98.92 (7) |
C19—C18—H18 | 119.9 | N3—Co1—O4 | 84.46 (7) |
C20—C19—C18 | 116.1 (2) | C21—N1—C17 | 115.4 (2) |
C20—C19—C24 | 122.3 (2) | C21—N1—Co1 | 124.92 (17) |
C18—C19—C24 | 121.6 (2) | C17—N1—Co1 | 118.89 (17) |
C21—C20—C19 | 120.7 (2) | C26—N2—C22 | 116.0 (2) |
C21—C20—H20 | 119.7 | C32—N3—C36 | 116.2 (2) |
C19—C20—H20 | 119.7 | C32—N3—Co1 | 116.08 (16) |
N1—C21—C20 | 123.7 (3) | C36—N3—Co1 | 126.75 (17) |
N1—C21—H21 | 118.2 | C27—N4—C31 | 116.9 (3) |
C20—C21—H21 | 118.2 | C1—O2—H2 | 112.5 (19) |
N2—C22—C23 | 124.3 (3) | C2—O3—Co1 | 92.28 (14) |
N2—C22—H22 | 117.9 | C2—O4—Co1 | 86.22 (15) |
C23—C22—H22 | 117.9 | C3—O5—Co1ii | 129.37 (16) |
C24—C23—C22 | 119.6 (3) | C3—O6—Co1iii | 143.49 (16) |
C24—C23—H23 | 120.2 | C4—O7—H1 | 113 (2) |
C22—C23—H23 | 120.2 | | |
| | | |
O1—C1—C5—C10 | 7.0 (4) | C27—C28—C29—C34 | −175.0 (3) |
O2—C1—C5—C10 | −172.6 (2) | C28—C29—C30—C31 | −3.7 (5) |
O1—C1—C5—C6 | −174.8 (2) | C34—C29—C30—C31 | 174.6 (3) |
O2—C1—C5—C6 | 5.6 (3) | C29—C30—C31—N4 | 1.1 (5) |
C10—C5—C6—C7 | 2.6 (3) | N3—C32—C33—C34 | −0.3 (4) |
C1—C5—C6—C7 | −175.7 (2) | C32—C33—C34—C35 | 2.4 (4) |
C10—C5—C6—C2 | −170.9 (2) | C32—C33—C34—C29 | −179.7 (2) |
C1—C5—C6—C2 | 10.9 (4) | C28—C29—C34—C35 | −156.2 (3) |
O4—C2—C6—C7 | 75.3 (3) | C30—C29—C34—C35 | 25.7 (4) |
O3—C2—C6—C7 | −95.5 (3) | C28—C29—C34—C33 | 26.0 (4) |
O4—C2—C6—C5 | −111.0 (3) | C30—C29—C34—C33 | −152.2 (3) |
O3—C2—C6—C5 | 78.2 (3) | C33—C34—C35—C36 | −2.4 (4) |
C5—C6—C7—C8 | −2.2 (4) | C29—C34—C35—C36 | 179.7 (2) |
C2—C6—C7—C8 | 171.9 (2) | C34—C35—C36—N3 | 0.4 (4) |
C6—C7—C8—C9 | −0.5 (4) | C20—C21—N1—C17 | 0.0 (4) |
C6—C7—C8—C14 | 178.1 (2) | C20—C21—N1—Co1 | −169.7 (2) |
C7—C8—C9—C10 | 2.9 (4) | C18—C17—N1—C21 | 0.5 (4) |
C14—C8—C9—C10 | −175.7 (2) | C18—C17—N1—Co1 | 170.9 (2) |
C8—C9—C10—C5 | −2.6 (4) | O6i—Co1—N1—C21 | 85.4 (2) |
C6—C5—C10—C9 | −0.2 (4) | O5ii—Co1—N1—C21 | −21.1 (2) |
C1—C5—C10—C9 | 178.1 (2) | O3—Co1—N1—C21 | −169.8 (2) |
O8—C4—C11—C16 | −154.0 (3) | N3—Co1—N1—C21 | 144.5 (3) |
O7—C4—C11—C16 | 28.0 (4) | O4—Co1—N1—C21 | −111.0 (2) |
O8—C4—C11—C12 | 29.3 (4) | O6i—Co1—N1—C17 | −83.96 (19) |
O7—C4—C11—C12 | −148.6 (3) | O5ii—Co1—N1—C17 | 169.53 (19) |
C16—C11—C12—C13 | −3.1 (4) | O3—Co1—N1—C17 | 20.80 (19) |
C4—C11—C12—C13 | 173.7 (3) | N3—Co1—N1—C17 | −24.9 (5) |
C11—C12—C13—C14 | −0.9 (4) | O4—Co1—N1—C17 | 79.6 (2) |
C12—C13—C14—C15 | 3.4 (4) | C25—C26—N2—C22 | 3.4 (4) |
C12—C13—C14—C8 | −179.8 (2) | C23—C22—N2—C26 | −3.1 (4) |
C9—C8—C14—C13 | −36.5 (4) | C33—C32—N3—C36 | −1.8 (4) |
C7—C8—C14—C13 | 144.9 (3) | C33—C32—N3—Co1 | 168.0 (2) |
C9—C8—C14—C15 | 140.2 (3) | C35—C36—N3—C32 | 1.7 (4) |
C7—C8—C14—C15 | −38.4 (3) | C35—C36—N3—Co1 | −166.73 (19) |
C13—C14—C15—C16 | −2.0 (4) | O6i—Co1—N3—C32 | 61.16 (18) |
C8—C14—C15—C16 | −178.9 (2) | O5ii—Co1—N3—C32 | 167.58 (18) |
C14—C15—C16—C11 | −1.9 (4) | O3—Co1—N3—C32 | −44.41 (18) |
C14—C15—C16—C3 | 169.5 (2) | N1—Co1—N3—C32 | 1.7 (5) |
C12—C11—C16—C15 | 4.4 (4) | O4—Co1—N3—C32 | −104.34 (18) |
C4—C11—C16—C15 | −172.2 (2) | O6i—Co1—N3—C36 | −130.4 (2) |
C12—C11—C16—C3 | −166.4 (2) | O5ii—Co1—N3—C36 | −24.0 (2) |
C4—C11—C16—C3 | 17.0 (4) | O3—Co1—N3—C36 | 124.1 (2) |
O6—C3—C16—C15 | −122.6 (2) | N1—Co1—N3—C36 | 170.2 (3) |
O5—C3—C16—C15 | 54.5 (3) | O4—Co1—N3—C36 | 64.1 (2) |
O6—C3—C16—C11 | 48.4 (3) | C28—C27—N4—C31 | −2.6 (5) |
O5—C3—C16—C11 | −134.5 (2) | C30—C31—N4—C27 | 2.0 (5) |
N1—C17—C18—C19 | −0.5 (4) | O4—C2—O3—Co1 | −9.0 (2) |
C17—C18—C19—C20 | −0.1 (4) | C6—C2—O3—Co1 | 161.79 (18) |
C17—C18—C19—C24 | 179.0 (2) | O6i—Co1—O3—C2 | −165.48 (13) |
C18—C19—C20—C21 | 0.6 (4) | O5ii—Co1—O3—C2 | −2.7 (2) |
C24—C19—C20—C21 | −178.5 (3) | N1—Co1—O3—C2 | 106.35 (14) |
C19—C20—C21—N1 | −0.6 (5) | N3—Co1—O3—C2 | −82.83 (14) |
N2—C22—C23—C24 | −0.3 (4) | O4—Co1—O3—C2 | 4.88 (13) |
C22—C23—C24—C25 | 3.4 (4) | O3—C2—O4—Co1 | 8.4 (2) |
C22—C23—C24—C19 | −177.5 (2) | C6—C2—O4—Co1 | −162.0 (2) |
C20—C19—C24—C23 | 154.3 (3) | O6i—Co1—O4—C2 | 26.5 (3) |
C18—C19—C24—C23 | −24.8 (4) | O5ii—Co1—O4—C2 | 170.99 (14) |
C20—C19—C24—C25 | −26.6 (4) | O3—Co1—O4—C2 | −4.96 (13) |
C18—C19—C24—C25 | 154.3 (3) | N1—Co1—O4—C2 | −87.48 (14) |
C23—C24—C25—C26 | −3.1 (4) | N3—Co1—O4—C2 | 80.10 (14) |
C19—C24—C25—C26 | 177.8 (3) | O6—C3—O5—Co1ii | 8.1 (4) |
C24—C25—C26—N2 | −0.3 (5) | C16—C3—O5—Co1ii | −168.70 (15) |
N4—C27—C28—C29 | −0.1 (5) | O5—C3—O6—Co1iii | −89.1 (3) |
C27—C28—C29—C30 | 3.2 (4) | C16—C3—O6—Co1iii | 87.7 (3) |
Symmetry codes: (i) x, y, z−1; (ii) −x+2, −y, −z+2; (iii) x, y, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H1···N2iv | 0.88 (4) | 1.80 (4) | 2.672 (4) | 171 (5) |
O2—H2···N4v | 0.90 (3) | 1.71 (4) | 2.600 (3) | 166 (4) |
Symmetry codes: (iv) x+1, y, z+2; (v) x−1, y, z−1. |