Retracted: Tetra­aqua­bis(4,4′-bipyridine)cobalt(II) pyridine-2,6-dicarboxyl­ate tetra­hydrate

In the title compound, [Co(C₁₀H₈N₂)₂(H₂O)₄](C₇H₃NO₄)·4H₂O, the Co^II ion adopts a slightly distorted trans-CoN₂O₄ octa­hedral coordination, arising from two monodentate 4,4′-bipyridine mol­ecules and four water mol­ecules. The constituent species inter­act by way of an extensive network of O—H...O and O—H...N hydrogen bonds. The crystal studied was an inversion twin.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.043
• wR factor = 0.129
• Data-to-parameter ratio = 6.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT115_ALERT_5_B ADDSYM Detects Noncrystallographic Inversion ...         86 PerFi

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.650
           From the CIF: _refine_ls_abs_structure_Flack_su    0.040
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.95
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C22    -   C27    ...       1.53 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H5W    ..  H13W    ..       2.13 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H12W   ..  H16W    ..       2.13 Ang.

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _reflns_number_total               3167
           Count of symmetry unique reflns         2736
           Completeness (_total/calc)            115.75%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       431
           Fraction of Friedel pairs measured     0.158
           Are heavy atom types Z>Si present        yes
PLAT033_ALERT_2_G Flack Parameter Value Deviates 2 * su from zero.       0.65
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         26

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

S1. Comment

As part of our studies of coordination polymer networks (Howell et al., 2001), the molecular title compound, (I), arose.

The Coⁱⁱ atom is (I) is coordinated by two monodentate 4,4'-bipyridine molecules in the axial sites and four associated water molecules in the equatorial plane with the r.m.s. deviation for the fitted atoms (Co1, O1, O2, O3, O4) being 0.012 Å (Fig. 1, Table 1). The dihedral angle between the N1 and N2 rings is 6.2 (3)°; that between the N3 and N4 rings is 6.9 (3)°.

A network of O—H···O and O—H···N hydrogen bonds (Table 2, Fig. 2) helps to establish the packing for (I).

Related literature

For general background, see: Howell et al. (2001).

S2. Experimental

A mixture of cobalt dichloride (0.5 mmol), benzene-1,3-dicarboxylic acid (0.5 mmol), sodium hydroxide (1 mmol), 4,4'-bipyridine (0.5 mmol), H₂O (8 ml) and ethanol (8 ml) in a 25-ml Teflon-lined stainless steel autoclave was heated at 453 K for one week, and then cooled to room temperature. Red blocks of (I) were obtained with a yield of 8%. Anal. Calc. for C₂₇H₃₅CoN₅O₁₂: C 47.61, H 5.14, N 10.29%; Found: C 47.56, H 5.18, N 10.22%.

S3. Refinement

The H atoms of the water molecule were located from difference density maps and were refined with distance restraints of H···H = 1.38 (2) Å and O—H = 0.82 (2) Å. All other H atoms were placed in calculated positions (C—H = 0.93 Å) and refined as riding with U_iso(H) = 1.2U_eq of the respective carrier atom.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures

	Fig. 1. The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. The packing in (I) with the O···O and O···N contacts for the hydrogen bonds indicated by dashed lines.

Tetraaquabis(4,4'-bipyridine)cobalt(II) pyridine-2,6-dicarboxylate tetrahydrate

Crystal data

[Co(C10H8N2)2(H2O)4](C7H3NO4)·4H2O	F(000) = 1420
Mr = 680.53	Dx = 1.462 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3167 reflections
a = 18.1827 (5) Å	θ = 1.6–25.0°
b = 6.8537 (10) Å	µ = 0.63 mm^−1
c = 25.1485 (5) Å	T = 293 K
β = 99.398 (10)°	Block, red
V = 3091.9 (5) Å^3	0.42 × 0.28 × 0.22 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	3167 independent reflections
Radiation source: fine-focus sealed tube	2936 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→21
Tmin = 0.779, Tmax = 0.875	k = −8→4
5091 measured reflections	l = −29→12

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.104P)^2 + 1.0603P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3167 reflections	Δρmax = 0.40 e Å^−3
456 parameters	Δρmin = −0.58 e Å^−3
26 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.65 (4)

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
Co1	0.67783 (8)	0.76266 (9)	0.87717 (6)	0.0355 (2)
C1	0.6043 (3)	0.8586 (8)	0.9833 (2)	0.0364 (12)
H1	0.5597	0.8604	0.9591	0.044*
C2	0.7306 (3)	0.8503 (9)	0.9992 (2)	0.0437 (14)
H2	0.7757	0.8458	0.9864	0.052*
C3	0.7327 (3)	0.8594 (8)	1.0542 (2)	0.0395 (13)
H3	0.7782	0.8620	1.0773	0.047*
C4	0.6013 (3)	0.8673 (9)	1.0380 (2)	0.0389 (13)
H4	0.5556	0.8749	1.0499	0.047*
C5	0.6670 (3)	0.8644 (6)	1.0746 (2)	0.0265 (10)
C6	0.6670 (3)	0.8625 (7)	1.1340 (2)	0.0277 (11)
C7	0.6017 (3)	0.8496 (9)	1.1560 (2)	0.0444 (14)
H7	0.5557	0.8446	1.1335	0.053*
C8	0.7334 (3)	0.8700 (10)	1.1714 (2)	0.0467 (14)
H8	0.7790	0.8794	1.1594	0.056*
C9	0.7313 (4)	0.8637 (9)	1.2261 (2)	0.0461 (14)
H9	0.7763	0.8682	1.2498	0.055*
C10	0.6052 (4)	0.8443 (10)	1.2112 (3)	0.0553 (17)
H10	0.5605	0.8351	1.2245	0.066*
C11	0.6226 (3)	0.6744 (10)	0.7540 (2)	0.0452 (14)
H11	0.5770	0.6870	0.7658	0.054*
C12	0.7481 (4)	0.6476 (10)	0.7726 (2)	0.0481 (15)
H12	0.7920	0.6429	0.7974	0.058*
C13	0.7532 (3)	0.6281 (10)	0.7186 (2)	0.0459 (14)
H13	0.7994	0.6063	0.7083	0.055*
C14	0.6228 (3)	0.6587 (9)	0.6993 (2)	0.0430 (14)
H14	0.5777	0.6599	0.6757	0.052*
C15	0.6886 (3)	0.6411 (6)	0.6791 (2)	0.0261 (10)
C16	0.6920 (3)	0.6373 (6)	0.62062 (19)	0.0272 (11)
C17	0.6269 (3)	0.6348 (8)	0.5828 (2)	0.0359 (12)
H17	0.5804	0.6339	0.5937	0.043*
C18	0.7592 (3)	0.6372 (8)	0.6013 (2)	0.0388 (12)
H18	0.8043	0.6375	0.6249	0.047*
C19	0.7576 (4)	0.6368 (8)	0.5461 (2)	0.0429 (13)
H19	0.8031	0.6383	0.5337	0.051*
C20	0.6327 (3)	0.6335 (8)	0.5279 (2)	0.0379 (12)
H20	0.5889	0.6318	0.5029	0.045*
C21	0.4269 (3)	0.8255 (8)	0.6808 (2)	0.0369 (12)
C22	0.4210 (3)	0.9008 (7)	0.4797 (2)	0.0329 (10)
C23	0.4286 (6)	0.7341 (6)	0.6267 (4)	0.0317 (8)
C24	0.4309 (3)	0.5329 (7)	0.6202 (2)	0.0372 (11)
H24	0.4319	0.4520	0.6500	0.045*
C25	0.4317 (3)	0.4511 (7)	0.5695 (2)	0.0381 (11)
H25	0.4338	0.3163	0.5658	0.046*
C26	0.4295 (3)	0.5684 (7)	0.5248 (2)	0.0371 (11)
H26	0.4301	0.5125	0.4911	0.044*
C27	0.4265 (4)	0.7722 (7)	0.5299 (3)	0.0321 (14)
N1	0.6684 (2)	0.8477 (6)	0.96340 (16)	0.0301 (10)
N2	0.6678 (3)	0.8514 (6)	1.24685 (19)	0.0403 (11)
N3	0.6852 (2)	0.6725 (6)	0.79132 (17)	0.0325 (10)
N4	0.6963 (3)	0.6345 (6)	0.50961 (18)	0.0367 (11)
N5	0.4265 (3)	0.8515 (7)	0.5801 (2)	0.0432 (11)
O1	0.7932 (2)	0.8702 (5)	0.88665 (16)	0.0386 (9)
O2	0.6401 (3)	1.0475 (5)	0.84774 (15)	0.0448 (10)
O3	0.5623 (2)	0.6581 (6)	0.86976 (17)	0.0434 (9)
O4	0.7151 (2)	0.4793 (6)	0.90703 (17)	0.0445 (9)
O5	0.8406 (4)	0.2547 (5)	0.8925 (2)	0.0455 (14)
O6	0.4356 (3)	0.3084 (8)	0.7615 (2)	0.0700 (13)
O7	0.4362 (3)	0.8505 (6)	0.81861 (18)	0.0525 (11)
O8	0.5140 (4)	0.7287 (7)	0.3640 (3)	0.0559 (16)
O9	0.4161 (2)	1.0788 (5)	0.48651 (15)	0.0432 (9)
O10	0.4189 (2)	0.8175 (6)	0.43492 (16)	0.0446 (9)
O11	0.4273 (3)	0.7097 (7)	0.72046 (19)	0.0511 (13)
O12	0.4261 (2)	1.0060 (6)	0.68432 (16)	0.0459 (9)
H1W	0.825 (3)	0.793 (7)	0.901 (3)	0.069*
H2W	0.804 (4)	0.986 (3)	0.892 (3)	0.069*
H3W	0.607 (3)	1.117 (9)	0.854 (2)	0.069*
H4W	0.645 (4)	1.026 (10)	0.8169 (10)	0.069*
H5W	0.526 (3)	0.715 (8)	0.853 (3)	0.069*
H6W	0.559 (4)	0.5395 (18)	0.870 (3)	0.069*
H7W	0.745 (3)	0.416 (8)	0.893 (3)	0.069*
H8W	0.702 (4)	0.419 (8)	0.932 (2)	0.069*
H9W	0.859 (4)	0.280 (10)	0.9234 (10)	0.069*
H10W	0.867 (4)	0.278 (11)	0.870 (2)	0.069*
H11W	0.415 (4)	0.262 (8)	0.7327 (16)	0.069*
H13W	0.458 (4)	0.956 (5)	0.823 (2)	0.069*
H14W	0.431 (5)	0.813 (9)	0.7873 (10)	0.069*
H15W	0.492 (4)	0.739 (10)	0.3897 (19)	0.069*
H16W	0.487 (3)	0.724 (11)	0.3347 (14)	0.069*
H12W	0.425 (4)	0.422 (4)	0.767 (3)	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0370 (3)	0.0440 (3)	0.0255 (3)	0.0009 (3)	0.0054 (2)	0.0012 (3)
C1	0.028 (3)	0.057 (3)	0.023 (3)	0.008 (2)	0.001 (2)	−0.005 (2)
C2	0.032 (3)	0.070 (4)	0.030 (3)	−0.007 (3)	0.007 (2)	−0.007 (3)
C3	0.027 (3)	0.068 (3)	0.022 (3)	−0.007 (3)	0.001 (2)	−0.006 (2)
C4	0.030 (3)	0.066 (3)	0.020 (3)	0.003 (3)	0.003 (2)	−0.003 (2)
C5	0.034 (3)	0.027 (2)	0.019 (2)	0.0008 (19)	0.004 (2)	−0.0007 (18)
C6	0.031 (3)	0.029 (2)	0.025 (3)	0.002 (2)	0.009 (2)	−0.0010 (18)
C7	0.031 (3)	0.071 (4)	0.031 (3)	−0.005 (3)	0.006 (2)	−0.005 (3)
C8	0.034 (3)	0.073 (4)	0.034 (3)	0.002 (3)	0.008 (3)	0.000 (3)
C9	0.044 (3)	0.070 (3)	0.025 (3)	0.003 (3)	0.006 (3)	0.002 (3)
C10	0.054 (4)	0.083 (4)	0.034 (3)	−0.008 (3)	0.021 (3)	−0.007 (3)
C11	0.028 (3)	0.084 (4)	0.025 (3)	−0.005 (3)	0.010 (2)	−0.007 (3)
C12	0.038 (3)	0.076 (4)	0.028 (3)	0.014 (3)	0.000 (3)	−0.004 (3)
C13	0.029 (3)	0.079 (4)	0.032 (3)	0.008 (3)	0.010 (2)	−0.010 (3)
C14	0.023 (3)	0.077 (4)	0.027 (3)	−0.001 (3)	−0.002 (2)	−0.006 (3)
C15	0.028 (3)	0.028 (2)	0.022 (3)	0.0014 (19)	0.005 (2)	0.0001 (18)
C16	0.032 (3)	0.025 (2)	0.023 (3)	0.0024 (19)	0.002 (2)	−0.0028 (18)
C17	0.033 (3)	0.057 (3)	0.018 (3)	0.000 (2)	0.005 (2)	−0.003 (2)
C18	0.035 (3)	0.055 (3)	0.028 (3)	0.003 (2)	0.009 (2)	−0.003 (2)
C19	0.043 (3)	0.055 (3)	0.033 (3)	0.001 (3)	0.015 (3)	0.000 (2)
C20	0.037 (3)	0.047 (3)	0.026 (3)	−0.004 (2)	−0.006 (2)	−0.003 (2)
C21	0.028 (3)	0.045 (3)	0.036 (3)	0.006 (2)	0.003 (2)	−0.002 (2)
C22	0.027 (2)	0.041 (2)	0.031 (2)	−0.003 (2)	0.0067 (19)	−0.005 (2)
C23	0.0186 (16)	0.042 (2)	0.033 (2)	0.002 (2)	−0.0011 (14)	0.002 (2)
C24	0.032 (2)	0.041 (2)	0.036 (3)	0.002 (2)	0.000 (2)	0.002 (2)
C25	0.037 (3)	0.029 (2)	0.046 (3)	0.004 (2)	0.001 (2)	−0.002 (2)
C26	0.035 (3)	0.041 (3)	0.034 (3)	−0.001 (2)	0.001 (2)	−0.011 (2)
C27	0.024 (3)	0.036 (3)	0.037 (3)	0.000 (2)	0.005 (2)	−0.007 (2)
N1	0.031 (2)	0.037 (2)	0.021 (2)	−0.0023 (18)	0.0028 (19)	−0.0010 (17)
N2	0.053 (3)	0.042 (2)	0.026 (2)	−0.005 (2)	0.010 (2)	−0.004 (2)
N3	0.034 (2)	0.040 (2)	0.024 (2)	0.0030 (19)	0.0038 (19)	−0.0017 (18)
N4	0.049 (3)	0.041 (2)	0.021 (2)	0.003 (2)	0.009 (2)	−0.0004 (18)
N5	0.033 (2)	0.050 (3)	0.046 (3)	0.003 (2)	0.005 (2)	−0.002 (2)
O1	0.035 (2)	0.0408 (17)	0.039 (2)	−0.0036 (16)	0.0040 (17)	0.0008 (16)
O2	0.066 (3)	0.044 (2)	0.0266 (19)	0.0210 (19)	0.0154 (18)	0.0088 (17)
O3	0.034 (2)	0.050 (2)	0.045 (2)	−0.0060 (18)	0.0060 (18)	−0.0033 (19)
O4	0.057 (3)	0.045 (2)	0.036 (2)	0.0186 (18)	0.0198 (18)	0.0104 (17)
O5	0.047 (3)	0.051 (3)	0.040 (3)	−0.0054 (17)	0.008 (3)	−0.0061 (17)
O6	0.087 (4)	0.077 (3)	0.045 (3)	−0.010 (3)	0.009 (2)	−0.014 (2)
O7	0.066 (3)	0.049 (2)	0.043 (3)	−0.008 (2)	0.012 (2)	−0.0047 (19)
O8	0.056 (4)	0.063 (3)	0.055 (4)	−0.009 (2)	0.028 (3)	−0.015 (2)
O9	0.055 (2)	0.0404 (19)	0.0336 (19)	0.0007 (17)	0.0046 (17)	−0.0005 (16)
O10	0.049 (2)	0.055 (2)	0.031 (2)	−0.005 (2)	0.0108 (18)	−0.0114 (18)
O11	0.067 (4)	0.061 (2)	0.025 (2)	0.005 (3)	0.006 (2)	0.003 (2)
O12	0.054 (2)	0.048 (2)	0.035 (2)	0.0018 (18)	0.0044 (17)	−0.0097 (17)

Geometric parameters (Å, º)

Co1—O4	2.151 (4)	C17—C20	1.402 (8)
Co1—O2	2.160 (4)	C17—H17	0.9300
Co1—O3	2.199 (4)	C18—C19	1.384 (8)
Co1—O1	2.200 (4)	C18—H18	0.9300
Co1—N1	2.279 (5)	C19—N4	1.323 (8)
Co1—N3	2.271 (5)	C19—H19	0.9300
C1—N1	1.344 (7)	C20—N4	1.311 (8)
C1—C4	1.388 (8)	C20—H20	0.9300
C1—H1	0.9300	C21—O12	1.241 (7)
C2—N1	1.326 (7)	C21—O11	1.274 (8)
C2—C3	1.377 (8)	C21—C23	1.503 (11)
C2—H2	0.9300	C22—O9	1.237 (6)
C3—C5	1.377 (7)	C22—O10	1.258 (6)
C3—H3	0.9300	C22—C27	1.529 (8)
C4—C5	1.384 (7)	C23—C24	1.390 (7)
C4—H4	0.9300	C23—N5	1.416 (10)
C5—C6	1.493 (6)	C24—C25	1.397 (8)
C6—C7	1.392 (8)	C24—H24	0.9300
C6—C8	1.407 (8)	C25—C26	1.377 (8)
C7—C10	1.380 (9)	C25—H25	0.9300
C7—H7	0.9300	C26—C27	1.405 (7)
C8—C9	1.381 (8)	C26—H26	0.9300
C8—H8	0.9300	C27—N5	1.375 (8)
C9—N2	1.346 (8)	O1—H1W	0.82 (6)
C9—H9	0.9300	O1—H2W	0.82 (3)
C10—N2	1.329 (9)	O2—H3W	0.80 (6)
C10—H10	0.9300	O2—H4W	0.81 (3)
C11—N3	1.351 (7)	O3—H5W	0.82 (6)
C11—C14	1.379 (8)	O3—H6W	0.816 (11)
C11—H11	0.9300	O4—H7W	0.82 (6)
C12—N3	1.317 (8)	O4—H8W	0.82 (5)
C12—C13	1.383 (8)	O5—H9W	0.81 (4)
C12—H12	0.9300	O5—H10W	0.82 (7)
C13—C15	1.413 (8)	O6—H11W	0.82 (4)
C13—H13	0.9300	O6—H12W	0.82 (3)
C14—C15	1.380 (8)	O7—H13W	0.82 (5)
C14—H14	0.9300	O7—H14W	0.82 (3)
C15—C16	1.482 (7)	O8—H15W	0.82 (6)
C16—C18	1.387 (8)	O8—H16W	0.82 (4)
C16—C17	1.393 (7)
O4—Co1—O2	179.6 (2)	C18—C16—C15	122.0 (5)
O4—Co1—O3	88.71 (17)	C17—C16—C15	120.7 (4)
O2—Co1—O3	91.11 (18)	C16—C17—C20	118.7 (5)
O4—Co1—O1	91.40 (17)	C16—C17—H17	120.6
O2—Co1—O1	88.77 (17)	C20—C17—H17	120.6
O3—Co1—O1	178.5 (2)	C19—C18—C16	118.4 (5)
O4—Co1—N1	88.11 (16)	C19—C18—H18	120.8
O2—Co1—N1	91.48 (15)	C16—C18—H18	120.8
O3—Co1—N1	86.82 (17)	N4—C19—C18	125.0 (6)
O1—Co1—N1	91.71 (16)	N4—C19—H19	117.6
O4—Co1—N3	91.27 (16)	C18—C19—H19	117.5
O2—Co1—N3	89.13 (16)	N4—C20—C17	123.9 (5)
O3—Co1—N3	91.97 (17)	N4—C20—H20	118.0
O1—Co1—N3	89.49 (17)	C17—C20—H20	118.0
N1—Co1—N3	178.66 (19)	O12—C21—O11	124.3 (6)
N1—C1—C4	123.2 (5)	O12—C21—C23	118.8 (5)
N1—C1—H1	118.4	O11—C21—C23	116.8 (5)
C4—C1—H1	118.4	O9—C22—O10	125.3 (5)
N1—C2—C3	124.4 (6)	O9—C22—C27	116.9 (4)
N1—C2—H2	117.8	O10—C22—C27	117.7 (4)
C3—C2—H2	117.8	C24—C23—N5	117.7 (8)
C2—C3—C5	119.4 (5)	C24—C23—C21	121.6 (7)
C2—C3—H3	120.3	N5—C23—C21	120.7 (4)
C5—C3—H3	120.3	C23—C24—C25	120.6 (7)
C5—C4—C1	119.4 (5)	C23—C24—H24	119.7
C5—C4—H4	120.3	C25—C24—H24	119.7
C1—C4—H4	120.3	C26—C25—C24	120.6 (5)
C3—C5—C4	117.3 (5)	C26—C25—H25	119.7
C3—C5—C6	121.0 (5)	C24—C25—H25	119.7
C4—C5—C6	121.7 (5)	C25—C26—C27	120.1 (5)
C7—C6—C8	115.5 (5)	C25—C26—H26	119.9
C7—C6—C5	122.5 (5)	C27—C26—H26	119.9
C8—C6—C5	121.9 (5)	N5—C27—C26	118.9 (6)
C10—C7—C6	120.0 (6)	N5—C27—C22	121.4 (4)
C10—C7—H7	120.0	C26—C27—C22	119.7 (5)
C6—C7—H7	120.0	C2—N1—C1	116.2 (5)
C9—C8—C6	120.3 (6)	C2—N1—Co1	117.5 (4)
C9—C8—H8	119.9	C1—N1—Co1	124.9 (3)
C6—C8—H8	119.8	C10—N2—C9	115.8 (5)
N2—C9—C8	123.6 (6)	C12—N3—C11	115.8 (5)
N2—C9—H9	118.2	C12—N3—Co1	124.3 (4)
C8—C9—H9	118.2	C11—N3—Co1	119.0 (4)
N2—C10—C7	124.8 (6)	C20—N4—C19	116.6 (5)
N2—C10—H10	117.6	C27—N5—C23	122.1 (5)
C7—C10—H10	117.6	Co1—O1—H1W	115 (5)
N3—C11—C14	123.6 (5)	Co1—O1—H2W	123 (5)
N3—C11—H11	118.2	H1W—O1—H2W	115 (3)
C14—C11—H11	118.2	Co1—O2—H3W	132 (5)
N3—C12—C13	124.4 (5)	Co1—O2—H4W	95 (5)
N3—C12—H12	117.8	H3W—O2—H4W	120 (3)
C13—C12—H12	117.8	Co1—O3—H5W	125 (5)
C12—C13—C15	120.2 (5)	Co1—O3—H6W	114 (5)
C12—C13—H13	119.9	H5W—O3—H6W	114 (3)
C15—C13—H13	119.9	Co1—O4—H7W	122 (4)
C11—C14—C15	121.2 (5)	Co1—O4—H8W	127 (4)
C11—C14—H14	119.4	H7W—O4—H8W	111 (7)
C15—C14—H14	119.4	H9W—O5—H10W	115 (7)
C14—C15—C13	114.7 (5)	H11W—O6—H12W	116 (7)
C14—C15—C16	123.1 (4)	H13W—O7—H14W	112 (3)
C13—C15—C16	122.2 (5)	H15W—O8—H16W	115 (3)
C18—C16—C17	117.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···O10^i	0.82 (6)	1.93 (6)	2.728 (6)	162 (7)
O1—H2W···O5^ii	0.82 (3)	1.96 (2)	2.769 (6)	169 (8)
O2—H3W···O8^iii	0.80 (6)	2.05 (6)	2.843 (8)	173 (8)
O2—H4W···N2^iv	0.81 (3)	2.06 (4)	2.755 (6)	145 (7)
O3—H5W···O7	0.82 (6)	1.95 (6)	2.772 (6)	176 (10)
O3—H6W···O8^v	0.82 (1)	2.01 (3)	2.789 (7)	161 (6)
O4—H7W···O5	0.82 (6)	2.06 (3)	2.826 (7)	155 (7)
O4—H8W···N4^v	0.82 (5)	2.00 (3)	2.769 (6)	155 (7)
O5—H9W···O9^i	0.81 (4)	2.00 (3)	2.777 (7)	161 (7)
O5—H10W···O7^vi	0.82 (7)	2.01 (6)	2.822 (8)	176 (7)
O6—H11W···O12^vii	0.82 (4)	2.16 (4)	2.825 (6)	137 (6)
O7—H14W···O11	0.82 (3)	1.82 (4)	2.631 (7)	174 (8)
O8—H15W···O10	0.82 (6)	1.96 (7)	2.746 (8)	162 (7)
O8—H16W···O6^viii	0.82 (4)	1.94 (4)	2.747 (9)	172 (8)
O6—H12W···O11	0.82 (3)	2.30 (5)	2.933 (7)	135 (7)

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x, y+1, z; (iii) x, −y+2, z+1/2; (iv) x, −y+2, z−1/2; (v) x, −y+1, z+1/2; (vi) x+1/2, y−1/2, z; (vii) x, y−1, z; (viii) x, −y+1, z−1/2.