Tri­aqua­(di­hydrogen 1,2,4,5-benzene­tetra­carboxyl­ato)(1,10-phenanthroline)­cobalt(II) monohydrate

In the title compound, [Co(C₁₀H₄O₈)(C₁₂H₈N₂)(H₂O)₃]·H₂O, 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 (H₂TCB) anions, aqua ligands and uncoordinated water mol­ecules, along with π–π interactions between the phen and aromatic rings of symmetry-related H₂TCB anions, link the mononuclear units into a three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

[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) Å^3	0.52 × 0.39 × 0.29 mm
Z = 4

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0466P)^2 + 2.4736P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (5)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O4^i	0.82 (2)	2.04 (2)	2.827 (3)	162 (3)
O9—H9B···O7^ii	0.82 (2)	1.95 (2)	2.770 (3)	177 (3)
O10—H10A···O3^iii	0.82 (3)	1.84 (3)	2.656 (4)	171 (3)
O10—H10B···O7^iv	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.