In the title compound, [Co(C
10H
4O
8)(C
12H
8N
2)(H
2O)
3]·H
2O, the Co atom has an octahedral coordination geometry, involving three aqua O atoms, one carboxylate O atom and two N atoms from a 1,10-phenathroline (phen) molecule. O—H
O hydrogen bonds involving dihydrogen-1,2,4,5-benzenetetracarboxylate (H
2TCB) anions, aqua ligands and uncoordinated water molecules, along with π–π interactions between the phen and aromatic rings of symmetry-related H
2TCB anions, link the mononuclear units into a three-dimensional network structure.
Supporting information
CCDC reference: 234823
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- H-atom completeness 91%
- Disorder in solvent or counterion
- R factor = 0.052
- wR factor = 0.122
- Data-to-parameter ratio = 11.5
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 .... ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT213_ALERT_2_C Atom O8 has ADP max/min Ratio ............. 3.40 prolat
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.83 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Co1
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C13
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C22
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.39
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O12
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... <O12'
PLAT731_ALERT_1_C Bond Calc 0.82(3), Rep 0.820(10) ...... 3.00 su-Rat
O10 -H10A 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.82(3), Rep 0.820(10) ...... 3.00 su-Rat
O10 -H10B 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.82(3), Rep 0.820(10) ...... 3.00 su-Rat
O11 -H11B 1.555 1.555
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C22 H20 Co1 N2 O12
Atom count from the _atom_site data: C22 H18 Co1 N2 O12
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C22 H20 Co N2 O12
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 88.00 88.00 0.00
H 80.00 72.00 8.00
Co 4.00 4.00 0.00
N 8.00 8.00 0.00
O 48.00 48.00 0.00
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Triaqua(dihydrogen 1,2,4,5-benzenetetracarboxylate)(1,10-
phenanthroline)cobalt(II) monohydrate
top
Crystal data top
[Co(C10H4O8)(C12H8N2)(H2O)3]·H2O | F(000) = 1156 |
Mr = 563.33 | Dx = 1.597 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 812 reflections |
a = 7.0862 (7) Å | θ = 2.4–23.0° |
b = 22.547 (2) Å | µ = 0.80 mm−1 |
c = 14.8041 (14) Å | T = 293 K |
β = 97.875 (2)° | Prism, red |
V = 2343.0 (4) Å3 | 0.52 × 0.39 × 0.29 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area detector diffractometer | 4259 independent reflections |
Radiation source: fine-focus sealed tube | 3955 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 25.3°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −8→8 |
Tmin = 0.680, Tmax = 0.801 | k = −27→27 |
17167 measured reflections | l = −17→17 |
Refinement top
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)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0466P)2 + 2.4736P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max = 0.001 |
4259 reflections | Δρmax = 0.40 e Å−3 |
371 parameters | Δρmin = −0.29 e Å−3 |
9 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0032 (5) |
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 | Occ. (<1) |
Co1 | 0.76334 (6) | 0.181444 (17) | 0.84060 (3) | 0.04000 (16) | |
O1 | 0.7459 (4) | 0.13747 (9) | 0.96402 (14) | 0.0536 (6) | |
O2 | 0.7500 (6) | 0.04271 (11) | 0.93842 (17) | 0.0956 (13) | |
O3 | 0.7864 (4) | 0.23523 (9) | 1.22322 (17) | 0.0591 (7) | |
O4 | 0.7173 (4) | 0.20307 (11) | 1.35463 (16) | 0.0609 (7) | |
O5 | 0.7249 (4) | 0.11134 (12) | 1.43856 (15) | 0.0652 (7) | |
H5A | 0.7105 | 0.1419 | 1.4083 | 0.098* | |
O6 | 0.7929 (6) | 0.01892 (14) | 1.41808 (18) | 0.0951 (12) | |
O7 | 0.7468 (4) | −0.08144 (9) | 1.15540 (16) | 0.0540 (6) | |
O8 | 0.7397 (7) | −0.04868 (11) | 1.01886 (18) | 0.1076 (15) | |
H8A | 0.7450 | −0.0167 | 0.9929 | 0.161* | |
O9 | 1.0545 (3) | 0.18392 (10) | 0.87358 (17) | 0.0490 (6) | |
H9A | 1.118 (4) | 0.2126 (9) | 0.862 (3) | 0.072 (13)* | |
H9B | 1.117 (4) | 0.1544 (9) | 0.865 (3) | 0.072 (13)* | |
O10 | 0.4769 (4) | 0.17431 (13) | 0.8067 (3) | 0.0905 (12) | |
H10A | 0.408 (4) | 0.2001 (12) | 0.781 (3) | 0.073 (13)* | |
H10B | 0.411 (4) | 0.1452 (10) | 0.812 (3) | 0.070 (13)* | |
O11 | 0.7878 (4) | 0.09840 (10) | 0.77805 (17) | 0.0589 (7) | |
H11A | 0.808 (6) | 0.0860 (16) | 0.7284 (13) | 0.068 (12)* | |
H11B | 0.790 (7) | 0.0706 (13) | 0.814 (2) | 0.104 (18)* | |
N1 | 0.7485 (4) | 0.26736 (11) | 0.90023 (18) | 0.0460 (6) | |
N2 | 0.7717 (4) | 0.23784 (11) | 0.72720 (17) | 0.0413 (6) | |
C1 | 0.7443 (6) | 0.28153 (16) | 0.9862 (2) | 0.0619 (10) | |
H1 | 0.7455 | 0.2510 | 1.0286 | 0.074* | |
C2 | 0.7383 (7) | 0.33987 (17) | 1.0171 (3) | 0.0714 (12) | |
H2 | 0.7346 | 0.3477 | 1.0785 | 0.086* | |
C3 | 0.7378 (6) | 0.38517 (16) | 0.9562 (3) | 0.0607 (10) | |
H3 | 0.7341 | 0.4243 | 0.9756 | 0.073* | |
C4 | 0.7429 (5) | 0.37222 (14) | 0.8641 (2) | 0.0451 (7) | |
C5 | 0.7454 (5) | 0.41647 (14) | 0.7940 (3) | 0.0518 (9) | |
H5 | 0.7410 | 0.4564 | 0.8096 | 0.062* | |
C6 | 0.7538 (5) | 0.40173 (14) | 0.7075 (2) | 0.0485 (8) | |
H6 | 0.7542 | 0.4315 | 0.6640 | 0.058* | |
C7 | 0.7623 (4) | 0.34082 (14) | 0.6801 (2) | 0.0427 (7) | |
C8 | 0.7757 (6) | 0.32254 (16) | 0.5910 (2) | 0.0580 (9) | |
H8 | 0.7770 | 0.3505 | 0.5448 | 0.070* | |
C9 | 0.7867 (7) | 0.26384 (16) | 0.5722 (2) | 0.0643 (11) | |
H9 | 0.7959 | 0.2513 | 0.5131 | 0.077* | |
C10 | 0.7843 (6) | 0.22270 (15) | 0.6418 (2) | 0.0540 (9) | |
H10 | 0.7919 | 0.1826 | 0.6278 | 0.065* | |
C11 | 0.7600 (4) | 0.29639 (12) | 0.7467 (2) | 0.0370 (6) | |
C12 | 0.7490 (4) | 0.31224 (13) | 0.8392 (2) | 0.0393 (7) | |
C13 | 0.7499 (5) | 0.08651 (13) | 0.9913 (2) | 0.0438 (7) | |
C14 | 0.7502 (4) | 0.07691 (12) | 1.09304 (19) | 0.0337 (6) | |
C15 | 0.7544 (4) | 0.12848 (12) | 1.14350 (19) | 0.0350 (6) | |
H15 | 0.7576 | 0.1642 | 1.1123 | 0.042* | |
C16 | 0.7542 (4) | 0.13134 (12) | 1.23716 (19) | 0.0333 (6) | |
C17 | 0.7517 (4) | 0.07737 (13) | 1.2846 (2) | 0.0379 (6) | |
C18 | 0.7482 (4) | 0.02535 (12) | 1.23457 (19) | 0.0370 (7) | |
H18 | 0.7464 | −0.0103 | 1.2661 | 0.044* | |
C19 | 0.7473 (4) | 0.02260 (12) | 1.14097 (19) | 0.0338 (6) | |
C20 | 0.7542 (4) | 0.19467 (14) | 1.2733 (2) | 0.0430 (7) | |
C21 | 0.7563 (6) | 0.06778 (16) | 1.3866 (2) | 0.0537 (9) | |
C22 | 0.7445 (5) | −0.04011 (13) | 1.1034 (2) | 0.0467 (8) | |
O12 | 0.9043 (6) | 0.06131 (17) | 0.6196 (2) | 0.0881 (15) | 0.848 (7) |
O12' | 0.619 (3) | 0.0581 (8) | 0.6139 (9) | 0.072 (7) | 0.152 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0585 (3) | 0.0259 (2) | 0.0378 (3) | 0.00405 (17) | 0.01430 (19) | 0.00843 (16) |
O1 | 0.0999 (19) | 0.0280 (11) | 0.0373 (11) | 0.0038 (11) | 0.0251 (12) | 0.0074 (9) |
O2 | 0.224 (4) | 0.0331 (14) | 0.0336 (13) | 0.0035 (18) | 0.0314 (18) | −0.0006 (11) |
O3 | 0.0940 (19) | 0.0254 (11) | 0.0580 (15) | −0.0049 (11) | 0.0108 (13) | −0.0078 (11) |
O4 | 0.0883 (19) | 0.0478 (14) | 0.0488 (14) | 0.0042 (13) | 0.0173 (13) | −0.0200 (11) |
O5 | 0.098 (2) | 0.0656 (17) | 0.0338 (12) | 0.0087 (15) | 0.0144 (13) | −0.0050 (12) |
O6 | 0.185 (4) | 0.0650 (19) | 0.0373 (14) | 0.021 (2) | 0.0203 (18) | 0.0160 (13) |
O7 | 0.0790 (17) | 0.0221 (11) | 0.0613 (15) | −0.0010 (10) | 0.0112 (12) | 0.0081 (10) |
O8 | 0.256 (5) | 0.0263 (13) | 0.0423 (15) | 0.000 (2) | 0.026 (2) | −0.0078 (11) |
O9 | 0.0552 (14) | 0.0303 (12) | 0.0621 (15) | 0.0015 (11) | 0.0105 (12) | 0.0052 (11) |
O10 | 0.0503 (16) | 0.0492 (17) | 0.171 (3) | 0.0011 (13) | 0.0126 (19) | 0.057 (2) |
O11 | 0.104 (2) | 0.0354 (12) | 0.0400 (13) | −0.0002 (13) | 0.0199 (14) | −0.0019 (11) |
N1 | 0.0667 (18) | 0.0313 (13) | 0.0437 (15) | 0.0088 (12) | 0.0207 (13) | 0.0075 (11) |
N2 | 0.0551 (16) | 0.0293 (13) | 0.0392 (14) | −0.0004 (11) | 0.0058 (11) | 0.0074 (10) |
C1 | 0.100 (3) | 0.0416 (19) | 0.050 (2) | 0.0134 (19) | 0.032 (2) | 0.0111 (16) |
C2 | 0.117 (4) | 0.053 (2) | 0.051 (2) | 0.012 (2) | 0.034 (2) | −0.0028 (18) |
C3 | 0.086 (3) | 0.0368 (18) | 0.063 (2) | 0.0079 (17) | 0.022 (2) | −0.0037 (16) |
C4 | 0.0489 (18) | 0.0340 (16) | 0.0532 (19) | 0.0049 (13) | 0.0096 (15) | 0.0039 (14) |
C5 | 0.058 (2) | 0.0266 (15) | 0.071 (2) | 0.0012 (14) | 0.0090 (17) | 0.0083 (15) |
C6 | 0.059 (2) | 0.0310 (16) | 0.054 (2) | −0.0016 (14) | 0.0034 (16) | 0.0163 (14) |
C7 | 0.0429 (17) | 0.0358 (16) | 0.0475 (18) | −0.0027 (13) | 0.0000 (13) | 0.0130 (13) |
C8 | 0.083 (3) | 0.048 (2) | 0.0403 (18) | −0.0041 (18) | −0.0007 (17) | 0.0164 (15) |
C9 | 0.107 (3) | 0.050 (2) | 0.0341 (17) | −0.003 (2) | 0.0008 (18) | 0.0035 (15) |
C10 | 0.087 (3) | 0.0350 (17) | 0.0388 (18) | −0.0008 (17) | 0.0046 (17) | 0.0024 (14) |
C11 | 0.0393 (15) | 0.0301 (14) | 0.0415 (16) | 0.0007 (12) | 0.0050 (12) | 0.0087 (12) |
C12 | 0.0435 (17) | 0.0291 (15) | 0.0468 (17) | 0.0047 (12) | 0.0114 (13) | 0.0096 (13) |
C13 | 0.067 (2) | 0.0308 (16) | 0.0349 (16) | 0.0003 (14) | 0.0113 (14) | 0.0010 (13) |
C14 | 0.0461 (16) | 0.0243 (13) | 0.0313 (14) | −0.0011 (12) | 0.0073 (12) | 0.0003 (11) |
C15 | 0.0476 (17) | 0.0230 (13) | 0.0348 (15) | 0.0001 (12) | 0.0065 (12) | 0.0035 (11) |
C16 | 0.0358 (15) | 0.0278 (14) | 0.0357 (15) | 0.0015 (11) | 0.0032 (12) | −0.0020 (11) |
C17 | 0.0426 (16) | 0.0385 (16) | 0.0322 (15) | 0.0007 (13) | 0.0039 (12) | −0.0005 (12) |
C18 | 0.0515 (18) | 0.0269 (14) | 0.0326 (15) | −0.0011 (12) | 0.0058 (13) | 0.0077 (11) |
C19 | 0.0442 (16) | 0.0223 (13) | 0.0349 (15) | −0.0006 (11) | 0.0052 (12) | 0.0004 (11) |
C20 | 0.0425 (17) | 0.0373 (17) | 0.0481 (19) | 0.0014 (13) | 0.0019 (14) | −0.0128 (14) |
C21 | 0.077 (2) | 0.054 (2) | 0.0299 (16) | 0.0016 (18) | 0.0063 (16) | 0.0054 (15) |
C22 | 0.067 (2) | 0.0247 (15) | 0.0476 (19) | −0.0005 (14) | 0.0054 (16) | −0.0006 (14) |
O12 | 0.137 (4) | 0.090 (3) | 0.0402 (18) | 0.027 (2) | 0.0204 (19) | 0.0030 (17) |
O12' | 0.135 (18) | 0.059 (11) | 0.019 (7) | −0.032 (10) | 0.000 (8) | −0.001 (7) |
Geometric parameters (Å, º) top
Co1—O10 | 2.030 (3) | C2—H2 | 0.93 |
Co1—O9 | 2.055 (2) | C3—C4 | 1.400 (5) |
Co1—O1 | 2.097 (2) | C3—H3 | 0.93 |
Co1—O11 | 2.106 (2) | C4—C12 | 1.404 (4) |
Co1—N2 | 2.113 (2) | C4—C5 | 1.441 (5) |
Co1—N1 | 2.137 (3) | C5—C6 | 1.333 (5) |
O1—C13 | 1.217 (4) | C5—H5 | 0.93 |
O2—C13 | 1.260 (4) | C6—C7 | 1.436 (5) |
O3—C20 | 1.219 (4) | C6—H6 | 0.93 |
O4—C20 | 1.280 (4) | C7—C8 | 1.397 (5) |
O5—C21 | 1.286 (4) | C7—C11 | 1.407 (4) |
O5—H5A | 0.82 | C8—C9 | 1.357 (5) |
O6—C21 | 1.211 (4) | C8—H8 | 0.93 |
O7—C22 | 1.207 (4) | C9—C10 | 1.389 (5) |
O8—C22 | 1.263 (4) | C9—H9 | 0.93 |
O8—H8A | 0.82 | C10—H10 | 0.93 |
O9—H9A | 0.82 (1) | C11—C12 | 1.428 (4) |
O9—H9B | 0.82 (1) | C13—C14 | 1.521 (4) |
O10—H10A | 0.82 (1) | C14—C15 | 1.380 (4) |
O10—H10B | 0.82 (1) | C14—C19 | 1.417 (4) |
O11—H11A | 0.82 (1) | C15—C16 | 1.388 (4) |
O11—H11B | 0.82 (1) | C15—H15 | 0.93 |
N1—C1 | 1.317 (4) | C16—C17 | 1.406 (4) |
N1—C12 | 1.357 (4) | C16—C20 | 1.525 (4) |
N2—C10 | 1.324 (4) | C17—C18 | 1.385 (4) |
N2—C11 | 1.356 (4) | C17—C21 | 1.521 (4) |
C1—C2 | 1.395 (5) | C18—C19 | 1.386 (4) |
C1—H1 | 0.93 | C18—H18 | 0.93 |
C2—C3 | 1.362 (5) | C19—C22 | 1.518 (4) |
| | | |
O10—Co1—O9 | 176.95 (11) | C7—C6—H6 | 119.4 |
O10—Co1—O1 | 90.10 (12) | C8—C7—C11 | 117.4 (3) |
O9—Co1—O1 | 89.03 (10) | C8—C7—C6 | 124.1 (3) |
O10—Co1—O11 | 87.73 (14) | C11—C7—C6 | 118.5 (3) |
O9—Co1—O11 | 89.32 (11) | C9—C8—C7 | 119.6 (3) |
O1—Co1—O11 | 88.91 (9) | C9—C8—H8 | 120.2 |
O10—Co1—N2 | 89.26 (12) | C7—C8—H8 | 120.2 |
O9—Co1—N2 | 92.05 (10) | C8—C9—C10 | 119.5 (3) |
O1—Co1—N2 | 171.09 (9) | C8—C9—H9 | 120.3 |
O11—Co1—N2 | 99.94 (10) | C10—C9—H9 | 120.3 |
O10—Co1—N1 | 94.01 (13) | N2—C10—C9 | 123.1 (3) |
O9—Co1—N1 | 88.96 (10) | N2—C10—H10 | 118.5 |
O1—Co1—N1 | 93.24 (9) | C9—C10—H10 | 118.5 |
O11—Co1—N1 | 177.23 (10) | N2—C11—C7 | 122.5 (3) |
N2—Co1—N1 | 77.94 (9) | N2—C11—C12 | 117.4 (2) |
C13—O1—Co1 | 137.2 (2) | C7—C11—C12 | 120.1 (3) |
C21—O5—H5A | 109.5 | N1—C12—C4 | 122.8 (3) |
C22—O8—H8A | 109.5 | N1—C12—C11 | 117.2 (3) |
Co1—O9—H9A | 122 (3) | C4—C12—C11 | 120.0 (3) |
Co1—O9—H9B | 119 (3) | O1—C13—O2 | 122.4 (3) |
H9A—O9—H9B | 107 (2) | O1—C13—C14 | 117.4 (3) |
Co1—O10—H10A | 125 (2) | O2—C13—C14 | 120.2 (3) |
Co1—O10—H10B | 127 (2) | C15—C14—C19 | 117.2 (2) |
H10A—O10—H10B | 108 (2) | C15—C14—C13 | 114.4 (2) |
Co1—O11—H11A | 137 (3) | C19—C14—C13 | 128.4 (2) |
Co1—O11—H11B | 113 (3) | C14—C15—C16 | 125.2 (3) |
H11A—O11—H11B | 109 (2) | C14—C15—H15 | 117.4 |
C1—N1—C12 | 117.7 (3) | C16—C15—H15 | 117.4 |
C1—N1—Co1 | 128.9 (2) | C15—C16—C17 | 117.4 (2) |
C12—N1—Co1 | 113.3 (2) | C15—C16—C20 | 113.2 (2) |
C10—N2—C11 | 117.9 (3) | C17—C16—C20 | 129.4 (3) |
C10—N2—Co1 | 128.0 (2) | C18—C17—C16 | 117.8 (3) |
C11—N2—Co1 | 114.05 (19) | C18—C17—C21 | 114.0 (3) |
N1—C1—C2 | 123.5 (3) | C16—C17—C21 | 128.2 (3) |
N1—C1—H1 | 118.3 | C17—C18—C19 | 124.7 (3) |
C2—C1—H1 | 118.3 | C17—C18—H18 | 117.7 |
C3—C2—C1 | 119.2 (3) | C19—C18—H18 | 117.7 |
C3—C2—H2 | 120.4 | C18—C19—C14 | 117.6 (2) |
C1—C2—H2 | 120.4 | C18—C19—C22 | 113.9 (2) |
C2—C3—C4 | 119.4 (3) | C14—C19—C22 | 128.5 (3) |
C2—C3—H3 | 120.3 | O3—C20—O4 | 122.7 (3) |
C4—C3—H3 | 120.3 | O3—C20—C16 | 118.7 (3) |
C3—C4—C12 | 117.5 (3) | O4—C20—C16 | 118.6 (3) |
C3—C4—C5 | 124.1 (3) | O6—C21—O5 | 120.7 (3) |
C12—C4—C5 | 118.3 (3) | O6—C21—C17 | 119.1 (3) |
C6—C5—C4 | 121.7 (3) | O5—C21—C17 | 120.2 (3) |
C6—C5—H5 | 119.1 | O7—C22—O8 | 120.7 (3) |
C4—C5—H5 | 119.1 | O7—C22—C19 | 119.2 (3) |
C5—C6—C7 | 121.3 (3) | O8—C22—C19 | 120.2 (3) |
C5—C6—H6 | 119.4 | | |
| | | |
O10—Co1—O1—C13 | 88.6 (4) | Co1—N1—C12—C4 | −179.0 (2) |
O9—Co1—O1—C13 | −88.5 (4) | C1—N1—C12—C11 | 177.9 (3) |
O11—Co1—O1—C13 | 0.8 (4) | Co1—N1—C12—C11 | −0.3 (4) |
N1—Co1—O1—C13 | −177.4 (4) | C3—C4—C12—N1 | 0.5 (5) |
O10—Co1—N1—C1 | 94.5 (3) | C5—C4—C12—N1 | 179.6 (3) |
O9—Co1—N1—C1 | −84.8 (3) | C3—C4—C12—C11 | −178.2 (3) |
O1—Co1—N1—C1 | 4.2 (3) | C5—C4—C12—C11 | 0.9 (5) |
N2—Co1—N1—C1 | −177.1 (4) | N2—C11—C12—N1 | −0.9 (4) |
O10—Co1—N1—C12 | −87.5 (2) | C7—C11—C12—N1 | −179.6 (3) |
O9—Co1—N1—C12 | 93.2 (2) | N2—C11—C12—C4 | 177.9 (3) |
O1—Co1—N1—C12 | −177.8 (2) | C7—C11—C12—C4 | −0.9 (5) |
N2—Co1—N1—C12 | 0.9 (2) | Co1—O1—C13—O2 | −7.2 (6) |
O10—Co1—N2—C10 | −86.2 (3) | Co1—O1—C13—C14 | 174.2 (2) |
O9—Co1—N2—C10 | 91.1 (3) | O1—C13—C14—C15 | −2.7 (5) |
O11—Co1—N2—C10 | 1.4 (3) | O2—C13—C14—C15 | 178.6 (4) |
N1—Co1—N2—C10 | 179.6 (3) | O1—C13—C14—C19 | 177.4 (3) |
O10—Co1—N2—C11 | 92.9 (2) | O2—C13—C14—C19 | −1.2 (6) |
O9—Co1—N2—C11 | −89.8 (2) | C19—C14—C15—C16 | −0.6 (5) |
O11—Co1—N2—C11 | −179.5 (2) | C13—C14—C15—C16 | 179.5 (3) |
N1—Co1—N2—C11 | −1.3 (2) | C14—C15—C16—C17 | 0.7 (5) |
C12—N1—C1—C2 | 0.8 (6) | C14—C15—C16—C20 | −178.5 (3) |
Co1—N1—C1—C2 | 178.7 (3) | C15—C16—C17—C18 | −0.4 (4) |
N1—C1—C2—C3 | −0.4 (7) | C20—C16—C17—C18 | 178.7 (3) |
C1—C2—C3—C4 | 0.2 (7) | C15—C16—C17—C21 | 178.2 (3) |
C2—C3—C4—C12 | −0.2 (6) | C20—C16—C17—C21 | −2.7 (5) |
C2—C3—C4—C5 | −179.2 (4) | C16—C17—C18—C19 | 0.1 (5) |
C3—C4—C5—C6 | 178.7 (3) | C21—C17—C18—C19 | −178.7 (3) |
C12—C4—C5—C6 | −0.2 (5) | C17—C18—C19—C14 | 0.0 (5) |
C4—C5—C6—C7 | −0.5 (5) | C17—C18—C19—C22 | 179.7 (3) |
C5—C6—C7—C8 | −178.5 (3) | C15—C14—C19—C18 | 0.2 (4) |
C5—C6—C7—C11 | 0.5 (5) | C13—C14—C19—C18 | −180.0 (3) |
C11—C7—C8—C9 | −0.3 (5) | C15—C14—C19—C22 | −179.4 (3) |
C6—C7—C8—C9 | 178.7 (4) | C13—C14—C19—C22 | 0.5 (5) |
C7—C8—C9—C10 | 0.1 (6) | C15—C16—C20—O3 | −12.2 (4) |
C11—N2—C10—C9 | 0.2 (5) | C17—C16—C20—O3 | 168.7 (3) |
Co1—N2—C10—C9 | 179.3 (3) | C15—C16—C20—O4 | 166.7 (3) |
C8—C9—C10—N2 | −0.1 (6) | C17—C16—C20—O4 | −12.4 (5) |
C10—N2—C11—C7 | −0.5 (5) | C18—C17—C21—O6 | 13.9 (5) |
Co1—N2—C11—C7 | −179.7 (2) | C16—C17—C21—O6 | −164.8 (4) |
C10—N2—C11—C12 | −179.2 (3) | C18—C17—C21—O5 | −167.3 (3) |
Co1—N2—C11—C12 | 1.6 (3) | C16—C17—C21—O5 | 14.0 (6) |
C8—C7—C11—N2 | 0.5 (5) | C18—C19—C22—O7 | −1.3 (5) |
C6—C7—C11—N2 | −178.5 (3) | C14—C19—C22—O7 | 178.2 (3) |
C8—C7—C11—C12 | 179.2 (3) | C18—C19—C22—O8 | 178.6 (4) |
C6—C7—C11—C12 | 0.2 (4) | C14—C19—C22—O8 | −1.8 (6) |
C1—N1—C12—C4 | −0.8 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O4 | 0.82 | 1.60 | 2.410 (4) | 171 |
O8—H8A···O2 | 0.82 | 1.57 | 2.386 (4) | 177 |
O9—H9A···O4i | 0.82 (2) | 2.04 (2) | 2.827 (3) | 162 (3) |
O9—H9B···O7ii | 0.82 (2) | 1.95 (2) | 2.770 (3) | 177 (3) |
O10—H10A···O3iii | 0.82 (3) | 1.84 (3) | 2.656 (4) | 171 (3) |
O10—H10B···O7iv | 0.82 (3) | 1.92 (3) | 2.731 (4) | 170 (4) |
O11—H11A···O12 | 0.82 (2) | 1.92 (3) | 2.723 (4) | 169 (4) |
O11—H11B···O2 | 0.82 (3) | 2.00 (3) | 2.731 (4) | 147 (3) |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+2, −y, −z+2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1, −y, −z+2. |