The asymmetric unit of the title one-dimensional coordination polymer, {[Co(C
10H
8N
2)(H
2O)
4](C
9H
6O
5)·H
2O}
n, comprises two half-cations, [Co(4,4′-bipy)(H
2O)
4]
22+ (4,4′-bipy is 4,4′-bipyridine), one 3-carboxylatophenoxyacetate (3-CPOA
2−) dianion and one non-coordinated water molecule. The Co
II ions, both of which are located on inversion centres, have approximately octahedral geometries, involving two N atoms of the centrosymmetric 4,4′-bipy ligand and four water molecules. Adjacent Co
II atoms are linked by 4,4′-bipy ligands into a chain, the shortest Co
Co separation within the polymeric chain being 11.456 (2) Å. The chains are further linked by hydrogen-bonding and π–π stacking interactions, generating a three-dimensional network.
Supporting information
CCDC reference: 262232
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.101
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.62
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.30
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10# .. O3 .. 2.66 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 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
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
catena-Poly[bis[[tetraaquacobalt(II)]-µ-4,4'-bipyridine-
κ2N:
N']] bis(3-carboxylatophenoxyacetate) dihydrate]
top
Crystal data top
[Co(C10H8N2)(H2O)4]2(C9H6O5)2·2H2O | Z = 1 |
Mr = 998.66 | F(000) = 518 |
Triclinic, P1 | Dx = 1.550 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2704 (19) Å | Cell parameters from 9892 reflections |
b = 11.161 (2) Å | θ = 3.2–27.5° |
c = 11.456 (2) Å | µ = 0.86 mm−1 |
α = 108.72 (3)° | T = 293 K |
β = 106.56 (3)° | Prism, pink |
γ = 90.39 (3)° | 0.35 × 0.26 × 0.17 mm |
V = 1069.7 (5) Å3 | |
Data collection top
Rigaku RAXIS-RAPID diffractometer | 4851 independent reflections |
Radiation source: fine-focus sealed tube | 3354 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −14→14 |
Tmin = 0.752, Tmax = 0.867 | l = −14→13 |
10238 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.1128P] where P = (Fo2 + 2Fc2)/3 |
4851 reflections | (Δ/σ)max < 0.001 |
322 parameters | Δρmax = 0.47 e Å−3 |
15 restraints | Δρmin = −0.27 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Co1 | 0.5000 | 0.0000 | 0.5000 | 0.02366 (14) | |
Co2 | 0.0000 | 0.5000 | 0.5000 | 0.02427 (14) | |
N1 | 0.5048 (2) | −0.0134 (2) | 0.30845 (18) | 0.0269 (5) | |
N2 | 0.0033 (2) | 0.4929 (2) | 0.30999 (19) | 0.0297 (5) | |
O1 | 0.5676 (2) | 0.4537 (2) | 0.29218 (19) | 0.0453 (5) | |
O2 | 0.5628 (2) | 0.3304 (2) | 0.40838 (18) | 0.0400 (5) | |
O3 | 0.2008 (2) | 0.2175 (2) | −0.13621 (18) | 0.0413 (5) | |
O4 | −0.0581 (2) | 0.1536 (2) | −0.44719 (19) | 0.0412 (5) | |
O5 | 0.1885 (2) | 0.2195 (2) | −0.36954 (18) | 0.0375 (5) | |
O1W | 0.5460 (3) | 0.19619 (19) | 0.56310 (18) | 0.0395 (5) | |
O2W | 0.2661 (2) | 0.0177 (2) | 0.44340 (18) | 0.0330 (4) | |
O3W | −0.1927 (2) | 0.5941 (2) | 0.47880 (16) | 0.0315 (4) | |
O4W | −0.1351 (2) | 0.32047 (19) | 0.41823 (18) | 0.0339 (4) | |
O5W | 0.5067 (2) | 0.6593 (2) | 0.2071 (2) | 0.0496 (6) | |
C1 | 0.6198 (3) | 0.0447 (3) | 0.2917 (2) | 0.0330 (6) | |
C2 | 0.6226 (3) | 0.0524 (3) | 0.1741 (2) | 0.0326 (6) | |
C3 | 0.5020 (3) | −0.0043 (3) | 0.0637 (2) | 0.0257 (6) | |
C4 | 0.3831 (3) | −0.0679 (3) | 0.0804 (2) | 0.0384 (7) | |
C5 | 0.3887 (3) | −0.0691 (3) | 0.2022 (2) | 0.0373 (7) | |
C6 | 0.1273 (3) | 0.5294 (3) | 0.2877 (2) | 0.0337 (7) | |
C7 | 0.1312 (3) | 0.5345 (3) | 0.1698 (2) | 0.0324 (6) | |
C8 | 0.0005 (3) | 0.4979 (3) | 0.0649 (2) | 0.0279 (6) | |
C9 | −0.1284 (3) | 0.4580 (3) | 0.0869 (2) | 0.0397 (7) | |
C10 | −0.1225 (3) | 0.4563 (3) | 0.2081 (2) | 0.0394 (7) | |
C11 | 0.5074 (3) | 0.3640 (3) | 0.3113 (2) | 0.0312 (6) | |
C12 | 0.3649 (3) | 0.2911 (3) | 0.2100 (2) | 0.0288 (6) | |
C13 | 0.2567 (3) | 0.2326 (3) | 0.2415 (3) | 0.0385 (7) | |
C14 | 0.1245 (4) | 0.1716 (3) | 0.1467 (3) | 0.0462 (8) | |
C15 | 0.1000 (3) | 0.1629 (3) | 0.0190 (3) | 0.0404 (7) | |
C16 | 0.2109 (3) | 0.2197 (3) | −0.0126 (2) | 0.0330 (6) | |
C17 | 0.3406 (3) | 0.2850 (3) | 0.0829 (3) | 0.0310 (6) | |
C18 | 0.0645 (3) | 0.1631 (3) | −0.2347 (3) | 0.0355 (7) | |
C19 | 0.0666 (3) | 0.1810 (3) | −0.3601 (3) | 0.0304 (6) | |
H1W1 | 0.524 (4) | 0.239 (3) | 0.6296 (18) | 0.059* | |
H1W2 | 0.539 (4) | 0.238 (3) | 0.512 (2) | 0.059* | |
H2W1 | 0.204 (3) | −0.0445 (17) | 0.432 (3) | 0.049* | |
H2W2 | 0.245 (3) | 0.0853 (15) | 0.492 (2) | 0.049* | |
H3W1 | −0.276 (2) | 0.549 (2) | 0.431 (2) | 0.047* | |
H3W2 | −0.183 (3) | 0.6571 (19) | 0.454 (3) | 0.047* | |
H4W1 | −0.2278 (15) | 0.324 (3) | 0.415 (3) | 0.051* | |
H4W2 | −0.099 (3) | 0.268 (2) | 0.455 (3) | 0.051* | |
H5W1 | 0.517 (4) | 0.5858 (17) | 0.212 (4) | 0.074* | |
H5W2 | 0.591 (2) | 0.697 (3) | 0.217 (4) | 0.074* | |
H1 | 0.7033 | 0.0825 | 0.3636 | 0.040* | |
H2 | 0.7056 | 0.0956 | 0.1692 | 0.039* | |
H4 | 0.3000 | −0.1096 | 0.0096 | 0.046* | |
H5 | 0.3070 | −0.1110 | 0.2105 | 0.045* | |
H6 | 0.2168 | 0.5529 | 0.3560 | 0.040* | |
H7 | 0.2208 | 0.5622 | 0.1607 | 0.039* | |
H9 | −0.2189 | 0.4323 | 0.0198 | 0.048* | |
H10 | −0.2104 | 0.4283 | 0.2197 | 0.047* | |
H13 | 0.2730 | 0.2343 | 0.3260 | 0.046* | |
H14 | 0.0502 | 0.1354 | 0.1689 | 0.055* | |
H15 | 0.0111 | 0.1201 | −0.0443 | 0.049* | |
H17 | 0.4127 | 0.3254 | 0.0618 | 0.037* | |
H18A | −0.0195 | 0.2026 | −0.2086 | 0.043* | |
H18B | 0.0497 | 0.0730 | −0.2481 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0284 (3) | 0.0296 (3) | 0.0157 (2) | −0.0014 (2) | 0.0078 (2) | 0.0102 (2) |
Co2 | 0.0292 (3) | 0.0297 (3) | 0.0155 (2) | −0.0005 (2) | 0.0068 (2) | 0.0097 (2) |
N1 | 0.0315 (12) | 0.0335 (13) | 0.0193 (10) | 0.0010 (10) | 0.0079 (9) | 0.0137 (10) |
N2 | 0.0335 (12) | 0.0399 (15) | 0.0188 (10) | 0.0027 (11) | 0.0095 (9) | 0.0124 (10) |
O1 | 0.0419 (12) | 0.0511 (14) | 0.0420 (11) | −0.0151 (10) | −0.0012 (9) | 0.0271 (11) |
O2 | 0.0403 (11) | 0.0493 (13) | 0.0363 (10) | −0.0024 (10) | 0.0074 (9) | 0.0261 (10) |
O3 | 0.0346 (10) | 0.0596 (15) | 0.0300 (10) | −0.0048 (10) | 0.0054 (9) | 0.0194 (10) |
O4 | 0.0309 (10) | 0.0531 (14) | 0.0402 (11) | −0.0052 (9) | −0.0007 (9) | 0.0266 (10) |
O5 | 0.0333 (10) | 0.0431 (12) | 0.0381 (10) | −0.0027 (9) | 0.0099 (9) | 0.0176 (9) |
O1W | 0.0606 (13) | 0.0333 (12) | 0.0313 (10) | 0.0013 (10) | 0.0205 (10) | 0.0142 (9) |
O2W | 0.0313 (10) | 0.0403 (12) | 0.0303 (9) | −0.0001 (9) | 0.0119 (8) | 0.0137 (9) |
O3W | 0.0333 (10) | 0.0349 (12) | 0.0260 (9) | 0.0004 (9) | 0.0066 (8) | 0.0121 (8) |
O4W | 0.0323 (10) | 0.0372 (12) | 0.0325 (9) | −0.0026 (9) | 0.0044 (9) | 0.0168 (9) |
O5W | 0.0456 (12) | 0.0477 (15) | 0.0565 (13) | 0.0062 (11) | 0.0123 (12) | 0.0218 (12) |
C1 | 0.0365 (15) | 0.0434 (18) | 0.0188 (12) | −0.0053 (13) | 0.0057 (11) | 0.0127 (12) |
C2 | 0.0321 (14) | 0.0453 (18) | 0.0230 (12) | −0.0065 (13) | 0.0077 (11) | 0.0157 (12) |
C3 | 0.0348 (14) | 0.0283 (15) | 0.0179 (11) | 0.0057 (12) | 0.0115 (11) | 0.0097 (11) |
C4 | 0.0373 (16) | 0.055 (2) | 0.0189 (12) | −0.0146 (14) | 0.0025 (11) | 0.0128 (13) |
C5 | 0.0370 (15) | 0.054 (2) | 0.0229 (12) | −0.0091 (14) | 0.0090 (12) | 0.0161 (13) |
C6 | 0.0305 (15) | 0.0498 (19) | 0.0224 (12) | 0.0014 (13) | 0.0059 (11) | 0.0161 (13) |
C7 | 0.0301 (14) | 0.0479 (18) | 0.0235 (12) | 0.0041 (13) | 0.0121 (11) | 0.0144 (12) |
C8 | 0.0319 (14) | 0.0353 (16) | 0.0196 (12) | 0.0059 (13) | 0.0103 (11) | 0.0111 (11) |
C9 | 0.0313 (15) | 0.067 (2) | 0.0218 (12) | −0.0015 (15) | 0.0063 (11) | 0.0185 (14) |
C10 | 0.0338 (15) | 0.062 (2) | 0.0258 (13) | −0.0029 (14) | 0.0110 (12) | 0.0177 (14) |
C11 | 0.0322 (14) | 0.0339 (16) | 0.0311 (13) | 0.0030 (12) | 0.0120 (12) | 0.0138 (12) |
C12 | 0.0251 (13) | 0.0263 (15) | 0.0348 (14) | 0.0030 (11) | 0.0093 (11) | 0.0096 (12) |
C13 | 0.0419 (16) | 0.0446 (18) | 0.0310 (13) | −0.0003 (14) | 0.0134 (13) | 0.0135 (13) |
C14 | 0.0421 (17) | 0.057 (2) | 0.0437 (16) | −0.0108 (15) | 0.0204 (14) | 0.0158 (16) |
C15 | 0.0333 (15) | 0.0475 (19) | 0.0392 (15) | −0.0057 (13) | 0.0085 (13) | 0.0152 (14) |
C16 | 0.0289 (14) | 0.0394 (18) | 0.0320 (14) | 0.0044 (12) | 0.0068 (12) | 0.0159 (13) |
C17 | 0.0291 (13) | 0.0320 (15) | 0.0363 (14) | 0.0029 (11) | 0.0131 (12) | 0.0144 (12) |
C18 | 0.0283 (14) | 0.0445 (18) | 0.0347 (14) | −0.0004 (13) | 0.0037 (12) | 0.0198 (13) |
C19 | 0.0328 (14) | 0.0236 (14) | 0.0356 (14) | 0.0030 (11) | 0.0079 (12) | 0.0132 (12) |
Geometric parameters (Å, º) top
Co1—N1 | 2.1644 (19) | C1—C2 | 1.384 (3) |
Co2—N2 | 2.161 (2) | C1—H1 | 0.9300 |
Co1—O1W | 2.072 (2) | C2—C3 | 1.386 (4) |
Co1—O2W | 2.1089 (19) | C2—H2 | 0.9300 |
Co2—O3W | 2.0723 (19) | C3—C3iii | 1.483 (4) |
Co2—O4W | 2.134 (2) | C3—C4 | 1.397 (4) |
O1—C11 | 1.250 (3) | C4—C5 | 1.386 (3) |
O2—C11 | 1.259 (3) | C4—H4 | 0.9300 |
O4—C19 | 1.252 (3) | C5—H5 | 0.9300 |
O5—C19 | 1.251 (3) | C6—C7 | 1.381 (3) |
Co1—N1i | 2.1644 (19) | C6—H6 | 0.9300 |
Co2—N2ii | 2.161 (2) | C7—C8 | 1.388 (4) |
Co1—O1Wi | 2.072 (2) | C7—H7 | 0.9300 |
Co1—O2Wi | 2.1089 (19) | C8—C8iv | 1.500 (4) |
Co2—O3Wii | 2.0723 (19) | C8—C9 | 1.388 (4) |
Co2—O4Wii | 2.134 (2) | C9—C10 | 1.380 (4) |
N1—C1 | 1.335 (3) | C9—H9 | 0.9300 |
N1—C5 | 1.336 (3) | C10—H10 | 0.9300 |
N2—C6 | 1.334 (3) | C11—C12 | 1.504 (4) |
N2—C10 | 1.342 (3) | C12—C13 | 1.382 (4) |
O3—C16 | 1.385 (3) | C12—C17 | 1.388 (4) |
O3—C18 | 1.406 (3) | C13—C14 | 1.379 (4) |
O1W—H1W1 | 0.84 (3) | C13—H13 | 0.9300 |
O1W—H1W2 | 0.85 (3) | C14—C15 | 1.385 (4) |
O2W—H2W1 | 0.85 (3) | C14—H14 | 0.9300 |
O2W—H2W2 | 0.85 (3) | C15—C16 | 1.393 (4) |
O3W—H3W1 | 0.85 (3) | C15—H15 | 0.9300 |
O3W—H3W2 | 0.85 (3) | C16—C17 | 1.379 (4) |
O4W—H4W1 | 0.85 (3) | C17—H17 | 0.9300 |
O4W—H4W2 | 0.85 (3) | C18—C19 | 1.519 (4) |
O5W—H5W1 | 0.85 (2) | C18—H18A | 0.9700 |
O5W—H5W2 | 0.85 (3) | C18—H18B | 0.9700 |
| | | |
N1i—Co1—N1 | 180.0 | O4W—Co2—N2ii | 89.60 (9) |
N2ii—Co2—N2 | 180.0 | C1—N1—Co1 | 121.03 (16) |
O1W—Co1—N1 | 90.78 (8) | C1—N1—C5 | 116.0 (2) |
O1Wi—Co1—N1 | 89.22 (8) | C1—C2—C3 | 120.1 (3) |
O1W—Co1—O1Wi | 180.00 | C1—C2—H2 | 119.9 |
O1W—Co1—O2W | 89.93 (9) | C2—C1—H1 | 117.9 |
O1Wi—Co1—O2W | 90.07 (9) | C2—C3—C4 | 115.8 (2) |
O2Wi—Co1—N1 | 90.69 (8) | C2—C3—C3iii | 122.1 (3) |
O2W—Co1—N1 | 89.31 (8) | C3—C2—H2 | 119.9 |
O2Wi—Co1—O2W | 180.0 | C3—C4—H4 | 119.9 |
O3W—Co2—N2 | 89.86 (8) | C4—C3—C3iii | 122.1 (3) |
O3Wii—Co2—N2 | 90.14 (8) | C4—C5—H5 | 118.2 |
O3W—Co2—O3Wii | 180.0 | C5—N1—Co1 | 122.68 (17) |
O3W—Co2—O4W | 90.75 (8) | C5—C4—C3 | 120.2 (2) |
O3Wii—Co2—O4W | 89.25 (8) | C5—C4—H4 | 119.9 |
O4Wii—Co2—N2 | 89.60 (9) | C6—N2—Co2 | 122.54 (16) |
O4W—Co2—N2 | 90.40 (9) | C6—N2—C10 | 116.0 (2) |
O4Wii—Co2—O4W | 180.0 | C6—C7—C8 | 119.7 (3) |
Co1—O1W—H1W1 | 118 (2) | C6—C7—H7 | 120.2 |
Co1—O1W—H1W2 | 123 (2) | C7—C6—H6 | 117.9 |
Co1—O2W—H2W1 | 119 (2) | C7—C8—C9 | 116.4 (2) |
Co1—O2W—H2W2 | 112 (2) | C7—C8—C8iv | 121.5 (3) |
Co2—O3W—H3W1 | 117 (2) | C8—C7—H7 | 120.2 |
Co2—O3W—H3W2 | 112 (2) | C8—C9—H9 | 119.9 |
Co2—O4W—H4W1 | 115 (2) | C9—C8—C8iv | 122.1 (3) |
Co2—O4W—H4W2 | 113 (2) | C9—C10—H10 | 118.2 |
N1—C1—C2 | 124.2 (2) | C10—N2—Co2 | 121.35 (18) |
N1—C1—H1 | 117.9 | C10—C9—C8 | 120.2 (2) |
N1—C5—C4 | 123.7 (3) | C10—C9—H9 | 119.9 |
N1—C5—H5 | 118.2 | C12—C13—H13 | 120.2 |
N2—C6—C7 | 124.2 (2) | C12—C17—H17 | 119.6 |
N2—C6—H6 | 117.9 | C13—C12—C17 | 119.6 (3) |
N2—C10—C9 | 123.5 (3) | C13—C12—C11 | 121.4 (2) |
N2—C10—H10 | 118.2 | C13—C14—C15 | 121.5 (3) |
O1—C11—O2 | 123.2 (3) | C13—C14—H14 | 119.3 |
O1—C11—C12 | 117.5 (2) | C14—C13—C12 | 119.5 (3) |
O2—C11—C12 | 119.3 (3) | C14—C13—H13 | 120.2 |
O3—C16—C15 | 124.5 (2) | C14—C15—C16 | 118.7 (3) |
O3—C18—C19 | 110.8 (2) | C14—C15—H15 | 120.6 |
O3—C18—H18A | 109.5 | C15—C14—H14 | 119.3 |
O3—C18—H18B | 109.5 | C16—O3—C18 | 117.7 (2) |
O4—C19—C18 | 115.1 (2) | C16—C15—H15 | 120.6 |
O5—C19—O4 | 125.6 (2) | C16—C17—C12 | 120.7 (3) |
O5—C19—C18 | 119.3 (2) | C16—C17—H17 | 119.6 |
O1W—Co1—N1i | 89.22 (8) | C17—C12—C11 | 119.0 (2) |
O1Wi—Co1—N1i | 90.78 (8) | C17—C16—O3 | 115.5 (2) |
O1W—Co1—O2Wi | 90.07 (9) | C17—C16—C15 | 119.9 (2) |
O1Wi—Co1—O2Wi | 89.93 (9) | C19—C18—H18A | 109.5 |
O2Wi—Co1—N1i | 89.31 (8) | C19—C18—H18B | 109.5 |
O2W—Co1—N1i | 90.69 (8) | H1W1—O1W—H1W2 | 110.8 (16) |
O3W—Co2—N2ii | 90.14 (8) | H2W1—O2W—H2W2 | 109.3 (16) |
O3Wii—Co2—N2ii | 89.86 (8) | H3W1—O3W—H3W2 | 108.4 (15) |
O3W—Co2—O4Wii | 89.25 (8) | H4W1—O4W—H4W2 | 109.4 (16) |
O3Wii—Co2—O4Wii | 90.75 (8) | H5W1—O5W—H5W2 | 111 (4) |
O4Wii—Co2—N2ii | 90.40 (9) | H18A—C18—H18B | 108.1 |
| | | |
Co1—N1—C1—C2 | −172.4 (2) | O4W—Co2—N2—C10 | 43.9 (2) |
Co1—N1—C5—C4 | 173.4 (2) | C1—N1—C5—C4 | −0.5 (4) |
Co2—N2—C6—C7 | −175.3 (2) | C1—C2—C3—C3iii | 178.3 (3) |
Co2—N2—C10—C9 | 175.7 (3) | C1—C2—C3—C4 | −0.5 (4) |
N1—C1—C2—C3 | −1.1 (5) | C2—C3—C4—C5 | 1.6 (4) |
N2—C6—C7—C8 | −1.2 (5) | C3—C4—C5—N1 | −1.1 (5) |
O1—C11—C12—C13 | −151.4 (3) | C3iii—C3—C4—C5 | −177.3 (3) |
O1—C11—C12—C17 | 27.3 (4) | C5—N1—C1—C2 | 1.6 (4) |
O2—C11—C12—C13 | 30.7 (4) | C6—N2—C10—C9 | −1.5 (5) |
O2—C11—C12—C17 | −150.7 (3) | C6—C7—C8—C8iv | 179.9 (3) |
O3—C16—C17—C12 | −178.5 (2) | C6—C7—C8—C9 | 0.1 (4) |
O3—C18—C19—O4 | −169.3 (2) | C7—C8—C9—C10 | 0.1 (5) |
O3—C18—C19—O5 | 11.4 (4) | C8—C9—C10—N2 | 0.6 (5) |
O1W—Co1—N1—C1 | 49.9 (2) | C8iv—C8—C9—C10 | −179.7 (3) |
O1Wi—Co1—N1—C1 | −130.1 (2) | C10—N2—C6—C7 | 1.8 (4) |
O1W—Co1—N1—C5 | −123.7 (2) | C11—C12—C13—C14 | 177.1 (3) |
O1Wi—Co1—N1—C5 | 56.3 (2) | C11—C12—C17—C16 | −179.6 (3) |
O2Wi—Co1—N1—C1 | −40.2 (2) | C12—C13—C14—C15 | 2.7 (5) |
O2W—Co1—N1—C1 | 139.8 (2) | C13—C12—C17—C16 | −0.9 (4) |
O2Wi—Co1—N1—C5 | 146.2 (2) | C13—C14—C15—C16 | −1.3 (5) |
O2W—Co1—N1—C5 | −33.8 (2) | C14—C15—C16—O3 | 179.6 (3) |
O3W—Co2—N2—C6 | 130.2 (2) | C14—C15—C16—C17 | −1.2 (4) |
O3Wii—Co2—N2—C6 | −49.8 (2) | C15—C16—C17—C12 | 2.3 (4) |
O3W—Co2—N2—C10 | −46.8 (2) | C16—O3—C18—C19 | 174.0 (2) |
O3Wii—Co2—N2—C10 | 133.2 (2) | C17—C12—C13—C14 | −1.6 (4) |
O4Wii—Co2—N2—C6 | 40.9 (2) | C18—O3—C16—C15 | 5.3 (4) |
O4W—Co2—N2—C6 | −139.1 (2) | C18—O3—C16—C17 | −173.9 (3) |
O4Wii—Co2—N2—C10 | −136.1 (2) | | |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z; (iv) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O5Wv | 0.84 (3) | 1.95 (3) | 2.791 (3) | 174 (3) |
O1W—H1W2···O2 | 0.85 (3) | 1.86 (3) | 2.696 (3) | 170 (3) |
O2W—H2W1···O4vi | 0.85 (3) | 1.89 (3) | 2.726 (3) | 164 (3) |
O2W—H2W2···O5vii | 0.85 (3) | 1.99 (3) | 2.826 (3) | 168 (3) |
O3W—H3W1···O1viii | 0.85 (3) | 1.83 (3) | 2.657 (3) | 164 (3) |
O3W—H3W2···O5iv | 0.85 (3) | 1.91 (3) | 2.756 (3) | 170 (3) |
O4W—H4W1···O2viii | 0.85 (3) | 1.92 (3) | 2.774 (3) | 179 (3) |
O4W—H4W2···O4vii | 0.85 (3) | 1.93 (3) | 2.754 (3) | 167 (2) |
O5W—H5W1···O1 | 0.85 (2) | 1.97 (3) | 2.771 (3) | 159 (3) |
O5W—H5W2···O3ix | 0.85 (3) | 2.66 (3) | 3.440 (3) | 154 (3) |
O5W—H5W2···O5ix | 0.85 (3) | 2.23 (2) | 2.938 (3) | 141 (3) |
Symmetry codes: (iv) −x, −y+1, −z; (v) −x+1, −y+1, −z+1; (vi) −x, −y, −z; (vii) x, y, z+1; (viii) x−1, y, z; (ix) −x+1, −y+1, −z. |