catena-Poly[[[aqua­tripyridine­cobalt(II)]-μ-5-amino-2,4,6-triiodoisophthalato-κ²O¹:O³] pyridine solvate]

The reaction of cobalt(II) nitrate with 5-amino-2,4,6-tri­iodo­isophthalic acid (ATPA) in pyridine solution leads to the formation of the title compound, {[Co(C₈H₂I₃NO₄)(C₅H₅N)₃(H₂O)]·C₅H₅N}_n. The Co²⁺ ion is six-coordinated by three N atoms, one water O atom and two O atoms from two ATPA ligands to form a distorted octa­hedral geometry. The two carboxyl­ate groups of ATPA act as bridging ligands connecting the Co^II metal centers to form one-dimensional zigzag chains along the c axis, with Co—O distances in the range 2.104 (4)–2.135 (4) Å. The average Co—N distance is 2.171 Å. A classical O—H...N hydrogen bond is formed by the coordinating water mol­ecule and the pyridine solvent mol­ecule. The structure was refined from a racemically twinned crystal with a twin ratio of approximately 8:1.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.041
• wR factor = 0.065
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   296.000
            Value of melting point given =     0.000
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10

Alert level G
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C28 H24 Co I3 N5 O5
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        112.00    112.00    0.00
           H         96.00     96.00    0.00
           Co         0.00      4.00   -4.00
           I         12.00     12.00    0.00
           N         20.00     20.00    0.00
           O         20.00     20.00    0.00
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               6038
           Count of symmetry unique reflns         3523
           Completeness (_total/calc)            171.39%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2515
           Fraction of Friedel pairs measured     0.714
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

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

---

S1. Comment

The crystal structure of ATPA (Beck & Sheldrick, 2008) is the precursor of the synthesis of a wide range of contrast agents with different amide-bound aliphatic side chains, which modulate their physical and physiological properties (Ziegler et al. 1997). However, to the best of our knowledge, there is no information about the structural characterization of its transition metal complexes.

The molecular structure of the title complex comprises of polymeric chains which extend along the c-axis. In the chain, each Co atom shows a distorted octahedron environment with a [3N+3O] coordination: three nitrogen atoms originate from pyridines, one oxygen from a water molecule and two oxygen atoms from two ATPA ligands. The two CO₂^- groups of the ATPA ligand coordinate to Co²⁺, bridging the Co metal centers. The bond lengths of the distorted octahedron are presented in Table 1. The average Co—N bond distance of the three pyridine ligands is 2.171 Å. The Co—O bond lengths in the title complex are slightly longer than those in the reported coordination polymers of cobalt and 1,3,5-benzenetricarboxylate (2.055 (2) Å) (Livage et al., 2001). The bond angles shown in Table 1 demonstrate the distorted octahedron in the Co coordination center. Compared with the data of the free ligand ATPA (Beck & Sheldrick, 2008), the C—O bond lengths are lengthened, the C—I and C—N bond distances are almost unchanged and the O—C—O bond angles are slightly expanded when the carboxylate groups are coordinated to central cations. The Co—N(py) and Co—O(H₂O) distances are in good agreement with those in diaqua-diformato-dipyridine-cobalt(II) (Zhu et al., 2004), where they are equal to 2.159 (4) Å and 2.143 (3) Å, respectively. A classic O—H···N hydrogen bond is formed by the coordinating water and the uncoordinated pyridine molecule (Table 2).

Related literature

For the structure of a monohydrate of ATPA, see: Beck & Sheldrick (2008). For the Co coordination polymer of 1,3,5-benzenetricarboxylate, see: Livage et al. (2001). For the structure of diaquadiformatodipyridine Co^II, see: Zhu et al. (2004). For a reduction of the organic iodine contrast agents in wastewater load, see: Ziegler et al. (1997).

S2. Experimental

0.29 g (1 mmol) Co(NO₃)₂.6H₂O was dissolved in 10 ml ethanol, 0.54 g (1 mmol) 5-amino-2, 4, 6-triiodoisophthalic acid was dissolved in 10 ml pyridine. To mix two solutions gave a pale purple solution which was stirred at room temperature for 2 h, then filtered. After several days well formed light purple single crystals were obtained.

S3. Refinement

H atoms were positioned geometrically and refined using a riding model with C—H distances = 0.93 Å, N—H distances = 0.86 Å, and O—H distances = 0.85 Å with U_iso(H) = 1.2 times U_eq(C, N, O).

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures

Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. Atoms labelled with an A belong to the symmetry-related ligand ATPA with symmetry code [A = -x + 3/2, -y, z + 1/2)].

catena-Poly[[[aquatripyridinecobalt(II)]-µ-5-amino-2,4,6- triiodoisophthalato-κ²O¹:O³] pyridine solvate]

Crystal data

[Co(C8H2I3NO4)(C5H5N)3(H2O)]·C5H5N	F(000) = 1812
Mr = 950.15	Dx = 1.974 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7120 reflections
a = 9.7759 (2) Å	θ = 4.7–43.0°
b = 16.9083 (4) Å	µ = 3.48 mm^−1
c = 19.3380 (4) Å	T = 296 K
V = 3196.45 (12) Å^3	Sheet, light purple
Z = 4	0.30 × 0.25 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer	6038 independent reflections
Radiation source: fine-focus sealed tube	4577 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ϕ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→9
Tmin = 0.38, Tmax = 0.75	k = −13→20
16692 measured reflections	l = −15→23

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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.0243P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
6038 reflections	Δρmax = 0.68 e Å^−3
379 parameters	Δρmin = −0.67 e Å^−3
3 restraints	Absolute structure: Flack (1983), with 2515 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.13 (2)

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
C1	0.8251 (6)	0.2139 (3)	0.8550 (3)	0.0319 (15)
C2	0.8423 (6)	0.2494 (3)	0.7900 (3)	0.0344 (16)
C3	0.7752 (6)	0.2152 (3)	0.7335 (3)	0.0299 (15)
C4	0.6949 (6)	0.1483 (3)	0.7390 (3)	0.0229 (14)
C5	0.6819 (6)	0.1159 (3)	0.8047 (3)	0.0286 (15)
C6	0.7445 (6)	0.1478 (3)	0.8629 (3)	0.0243 (14)
C7	0.6216 (7)	0.1144 (3)	0.6765 (3)	0.0276 (15)
C8	0.7222 (7)	0.1122 (3)	0.9341 (3)	0.0305 (15)
C9	0.9902 (7)	0.0943 (4)	1.1534 (4)	0.052 (2)
H9	1.0468	0.0501	1.1540	0.063*
C10	1.0171 (8)	0.1565 (5)	1.1968 (4)	0.067 (2)
H10	1.0909	0.1528	1.2270	0.080*
C11	0.9406 (10)	0.2230 (5)	1.1973 (4)	0.078 (3)
H11	0.9607	0.2651	1.2266	0.093*
C12	0.8332 (9)	0.2254 (5)	1.1531 (4)	0.078 (3)
H12	0.7768	0.2697	1.1520	0.093*
C13	0.8073 (7)	0.1626 (4)	1.1100 (4)	0.060 (2)
H13	0.7342	0.1661	1.0793	0.072*
C14	1.1101 (6)	−0.0851 (4)	1.0269 (3)	0.0397 (18)
H14	1.0619	−0.1279	1.0447	0.048*
C15	1.2437 (7)	−0.0963 (4)	1.0090 (3)	0.0488 (19)
H15	1.2859	−0.1451	1.0151	0.059*
C16	1.3142 (7)	−0.0329 (5)	0.9817 (3)	0.053 (2)
H16	1.4044	−0.0391	0.9674	0.064*
C17	1.2528 (6)	0.0377 (4)	0.9759 (3)	0.0471 (19)
H17	1.3000	0.0815	0.9592	0.057*
C18	1.1168 (7)	0.0434 (4)	0.9955 (3)	0.0448 (18)
H18	1.0733	0.0921	0.9911	0.054*
C19	0.6591 (7)	−0.1424 (4)	0.9923 (4)	0.0470 (19)
H19	0.6114	−0.1305	1.0326	0.056*
C20	0.6061 (7)	−0.1985 (4)	0.9494 (4)	0.057 (2)
H20	0.5249	−0.2240	0.9608	0.068*
C21	0.6717 (9)	−0.2166 (4)	0.8905 (4)	0.069 (2)
H21	0.6357	−0.2536	0.8599	0.082*
C22	0.7916 (9)	−0.1797 (4)	0.8766 (4)	0.063 (2)
H22	0.8416	−0.1925	0.8372	0.076*
C23	0.8384 (7)	−0.1222 (4)	0.9223 (4)	0.052 (2)
H23	0.9188	−0.0956	0.9113	0.062*
C24	−0.0436 (7)	0.0013 (4)	0.7430 (5)	0.062 (2)
H24	−0.1309	−0.0202	0.7465	0.074*
C25	0.0132 (9)	0.0325 (5)	0.8004 (4)	0.064 (2)
H25	−0.0337	0.0321	0.8422	0.076*
C26	0.1384 (11)	0.0640 (5)	0.7959 (5)	0.096 (3)
H26	0.1804	0.0855	0.8348	0.115*
C27	0.2020 (9)	0.0641 (6)	0.7351 (5)	0.101 (3)
H27	0.2884	0.0867	0.7309	0.121*
C28	0.1404 (9)	0.0313 (5)	0.6790 (4)	0.082 (3)
H28	0.1862	0.0311	0.6369	0.098*
Co1	0.83021 (7)	−0.00406 (5)	1.04654 (4)	0.0312 (2)
I1	0.92570 (5)	0.26385 (3)	0.94026 (2)	0.05269 (14)
I2	0.78262 (5)	0.27575 (3)	0.63848 (2)	0.05874 (16)
I3	0.56454 (5)	0.01146 (3)	0.81795 (2)	0.05039 (14)
N1	0.9245 (6)	0.3143 (3)	0.7821 (3)	0.0630 (17)
H1A	0.9357	0.3349	0.7418	0.076*
H1B	0.9649	0.3345	0.8174	0.076*
N2	0.8833 (5)	0.0964 (3)	1.1102 (2)	0.0393 (14)
N3	1.0452 (5)	−0.0175 (3)	1.0205 (2)	0.0348 (13)
N4	0.7763 (6)	−0.1033 (3)	0.9799 (3)	0.0379 (14)
N5	0.0172 (7)	−0.0004 (4)	0.6829 (3)	0.0660 (19)
O1	0.6899 (4)	0.0730 (2)	0.6366 (2)	0.0386 (11)
O2	0.5004 (5)	0.1311 (3)	0.6709 (2)	0.0555 (14)
O3	0.8147 (4)	0.0677 (2)	0.95601 (19)	0.0329 (10)
O4	0.6139 (4)	0.1298 (2)	0.9646 (2)	0.0460 (12)
O5	0.6191 (3)	0.0161 (2)	1.05937 (18)	0.0423 (11)
H5B	0.5951	0.0603	1.0423	0.051*
H5A	0.5963	0.0143	1.1018	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.041 (4)	0.029 (4)	0.026 (4)	0.003 (3)	−0.003 (3)	−0.007 (3)
C2	0.043 (4)	0.029 (4)	0.032 (4)	−0.014 (3)	0.003 (3)	−0.004 (3)
C3	0.038 (3)	0.029 (4)	0.023 (3)	−0.005 (3)	−0.004 (3)	0.001 (3)
C4	0.026 (4)	0.022 (3)	0.020 (3)	0.004 (3)	−0.001 (3)	−0.007 (3)
C5	0.032 (3)	0.032 (4)	0.022 (4)	−0.002 (3)	0.003 (3)	−0.003 (3)
C6	0.033 (4)	0.022 (3)	0.017 (3)	0.006 (3)	−0.004 (3)	−0.002 (3)
C7	0.041 (4)	0.020 (4)	0.021 (4)	0.010 (3)	0.005 (3)	0.004 (3)
C8	0.045 (4)	0.027 (4)	0.019 (4)	−0.006 (3)	−0.005 (4)	−0.007 (3)
C9	0.050 (4)	0.053 (5)	0.053 (5)	−0.004 (4)	−0.023 (4)	0.006 (4)
C10	0.078 (6)	0.071 (6)	0.052 (5)	−0.045 (5)	−0.022 (5)	−0.004 (5)
C11	0.122 (8)	0.054 (6)	0.058 (5)	−0.033 (6)	0.009 (6)	−0.022 (5)
C12	0.103 (7)	0.056 (6)	0.075 (6)	0.004 (5)	−0.025 (5)	−0.024 (5)
C13	0.067 (5)	0.054 (5)	0.059 (5)	0.011 (5)	−0.006 (5)	−0.020 (4)
C14	0.042 (4)	0.043 (4)	0.035 (4)	0.004 (4)	0.001 (3)	0.000 (4)
C15	0.046 (5)	0.057 (5)	0.043 (5)	0.020 (4)	0.002 (4)	−0.008 (4)
C16	0.028 (4)	0.088 (6)	0.044 (5)	0.013 (4)	0.003 (3)	−0.009 (4)
C17	0.032 (4)	0.064 (6)	0.045 (4)	−0.008 (4)	−0.001 (3)	0.010 (4)
C18	0.046 (5)	0.041 (4)	0.048 (5)	0.001 (4)	0.003 (4)	0.004 (4)
C19	0.048 (5)	0.037 (4)	0.056 (5)	0.005 (4)	0.003 (4)	0.004 (4)
C20	0.047 (5)	0.043 (5)	0.080 (6)	−0.017 (4)	−0.010 (4)	0.001 (5)
C21	0.088 (7)	0.050 (5)	0.068 (5)	−0.009 (5)	−0.026 (5)	−0.008 (5)
C22	0.085 (6)	0.060 (6)	0.046 (5)	0.000 (5)	−0.004 (5)	−0.028 (4)
C23	0.055 (5)	0.051 (5)	0.049 (5)	−0.011 (4)	0.006 (4)	−0.005 (4)
C24	0.041 (5)	0.061 (5)	0.083 (6)	0.005 (4)	0.005 (5)	−0.002 (6)
C25	0.078 (6)	0.067 (6)	0.046 (5)	0.019 (5)	0.010 (5)	0.001 (5)
C26	0.115 (9)	0.122 (8)	0.050 (6)	−0.044 (7)	−0.034 (6)	0.010 (6)
C27	0.059 (6)	0.167 (10)	0.078 (7)	−0.047 (6)	−0.011 (6)	0.020 (8)
C28	0.063 (6)	0.131 (9)	0.051 (6)	−0.003 (6)	0.014 (5)	0.023 (6)
Co1	0.0333 (4)	0.0350 (5)	0.0254 (5)	−0.0001 (4)	−0.0013 (4)	0.0022 (5)
I1	0.0737 (3)	0.0481 (3)	0.0363 (3)	−0.0171 (3)	−0.0127 (3)	−0.0058 (2)
I2	0.0883 (4)	0.0569 (3)	0.0311 (3)	−0.0191 (3)	0.0001 (3)	0.0134 (3)
I3	0.0633 (3)	0.0495 (3)	0.0384 (3)	−0.0231 (3)	−0.0053 (2)	0.0067 (2)
N1	0.092 (4)	0.062 (4)	0.035 (3)	−0.045 (4)	−0.014 (4)	0.007 (3)
N2	0.048 (4)	0.042 (4)	0.027 (3)	−0.004 (3)	0.000 (3)	−0.001 (3)
N3	0.031 (3)	0.038 (3)	0.035 (3)	0.002 (3)	0.003 (2)	0.006 (3)
N4	0.043 (3)	0.039 (4)	0.031 (3)	0.003 (3)	0.002 (3)	−0.002 (3)
N5	0.063 (4)	0.089 (5)	0.047 (4)	0.014 (4)	−0.012 (4)	−0.011 (4)
O1	0.047 (3)	0.041 (3)	0.028 (2)	−0.001 (2)	0.002 (2)	−0.013 (2)
O2	0.048 (3)	0.075 (4)	0.044 (3)	0.015 (3)	−0.012 (3)	−0.020 (3)
O3	0.037 (3)	0.036 (3)	0.026 (2)	0.001 (2)	−0.005 (2)	0.007 (2)
O4	0.049 (3)	0.064 (3)	0.025 (3)	0.021 (2)	0.010 (2)	0.001 (2)
O5	0.045 (3)	0.048 (3)	0.034 (2)	0.007 (2)	0.006 (2)	0.010 (2)

Geometric parameters (Å, º)

C1—C6	1.376 (7)	C18—N3	1.336 (7)
C1—C2	1.404 (7)	C18—H18	0.9300
C1—I1	2.097 (6)	C19—N4	1.344 (7)
C2—N1	1.368 (7)	C19—C20	1.363 (9)
C2—C3	1.400 (7)	C19—H19	0.9300
C3—C4	1.381 (7)	C20—C21	1.342 (9)
C3—I2	2.105 (5)	C20—H20	0.9300
C4—C5	1.389 (7)	C21—C22	1.355 (9)
C4—C7	1.517 (8)	C21—H21	0.9300
C5—C6	1.390 (7)	C22—C23	1.391 (8)
C5—I3	2.122 (6)	C22—H22	0.9300
C6—C8	1.519 (4)	C23—N4	1.309 (7)
C7—O2	1.223 (6)	C23—H23	0.9300
C7—O1	1.238 (6)	C24—N5	1.306 (8)
C8—O4	1.248 (6)	C24—C25	1.348 (9)
C8—O3	1.250 (6)	C24—H24	0.9300
C9—N2	1.337 (7)	C25—C26	1.338 (10)
C9—C10	1.372 (9)	C25—H25	0.9300
C9—H9	0.9300	C26—C27	1.331 (11)
C10—C11	1.350 (10)	C26—H26	0.9300
C10—H10	0.9300	C27—C28	1.359 (11)
C11—C12	1.355 (10)	C27—H27	0.9300
C11—H11	0.9300	C28—N5	1.321 (9)
C12—C13	1.373 (9)	C28—H28	0.9300
C12—H12	0.9300	Co1—O1^i	2.104 (4)
C13—N2	1.345 (7)	Co1—O5	2.106 (3)
C13—H13	0.9300	Co1—O3	2.135 (4)
C14—N3	1.312 (7)	Co1—N2	2.161 (5)
C14—C15	1.365 (8)	Co1—N3	2.173 (5)
C14—H14	0.9300	Co1—N4	2.180 (5)
C15—C16	1.379 (9)	N1—H1A	0.8600
C15—H15	0.9300	N1—H1B	0.8600
C16—C17	1.342 (8)	O1—Co1^ii	2.104 (4)
C16—H16	0.9300	O5—H5B	0.8500
C17—C18	1.386 (8)	O5—H5A	0.8499
C17—H17	0.9300
C6—C1—C2	121.0 (5)	C19—C20—H20	120.2
C6—C1—I1	120.6 (4)	C20—C21—C22	118.4 (8)
C2—C1—I1	118.4 (4)	C20—C21—H21	120.8
N1—C2—C3	121.3 (5)	C22—C21—H21	120.8
N1—C2—C1	120.9 (5)	C21—C22—C23	118.7 (8)
C3—C2—C1	117.8 (5)	C21—C22—H22	120.6
C4—C3—C2	123.0 (5)	C23—C22—H22	120.6
C4—C3—I2	119.1 (4)	N4—C23—C22	124.0 (7)
C2—C3—I2	117.7 (4)	N4—C23—H23	118.0
C3—C4—C5	116.5 (5)	C22—C23—H23	118.0
C3—C4—C7	121.1 (5)	N5—C24—C25	123.6 (7)
C5—C4—C7	122.5 (5)	N5—C24—H24	118.2
C4—C5—C6	123.2 (5)	C25—C24—H24	118.2
C4—C5—I3	119.2 (4)	C26—C25—C24	118.6 (8)
C6—C5—I3	117.6 (4)	C26—C25—H25	120.7
C1—C6—C5	118.5 (5)	C24—C25—H25	120.7
C1—C6—C8	120.3 (5)	C27—C26—C25	119.0 (9)
C5—C6—C8	121.1 (5)	C27—C26—H26	120.5
O2—C7—O1	126.7 (7)	C25—C26—H26	120.5
O2—C7—C4	116.2 (6)	C26—C27—C28	119.9 (8)
O1—C7—C4	117.2 (5)	C26—C27—H27	120.1
O4—C8—O3	126.7 (5)	C28—C27—H27	120.1
O4—C8—C6	117.0 (6)	N5—C28—C27	121.6 (8)
O3—C8—C6	116.2 (5)	N5—C28—H28	119.2
N2—C9—C10	120.7 (7)	C27—C28—H28	119.2
N2—C9—H9	119.6	O1^i—Co1—O5	84.29 (15)
C10—C9—H9	119.6	O1^i—Co1—O3	170.52 (16)
C11—C10—C9	122.5 (8)	O5—Co1—O3	86.29 (15)
C11—C10—H10	118.7	O1^i—Co1—N2	89.21 (16)
C9—C10—H10	118.7	O5—Co1—N2	92.37 (17)
C10—C11—C12	116.7 (8)	O3—Co1—N2	92.18 (17)
C10—C11—H11	121.7	O1^i—Co1—N3	102.93 (17)
C12—C11—H11	121.7	O5—Co1—N3	172.68 (17)
C11—C12—C13	120.2 (8)	O3—Co1—N3	86.47 (17)
C11—C12—H12	119.9	N2—Co1—N3	88.95 (19)
C13—C12—H12	119.9	O1^i—Co1—N4	92.29 (17)
N2—C13—C12	122.7 (7)	O5—Co1—N4	87.53 (18)
N2—C13—H13	118.7	O3—Co1—N4	86.31 (16)
C12—C13—H13	118.7	N2—Co1—N4	178.48 (19)
N3—C14—C15	124.1 (6)	N3—Co1—N4	91.0 (2)
N3—C14—H14	118.0	C2—N1—H1A	120.0
C15—C14—H14	118.0	C2—N1—H1B	120.0
C14—C15—C16	117.8 (7)	H1A—N1—H1B	120.0
C14—C15—H15	121.1	C9—N2—C13	117.2 (6)
C16—C15—H15	121.1	C9—N2—Co1	121.5 (5)
C17—C16—C15	120.0 (6)	C13—N2—Co1	121.3 (5)
C17—C16—H16	120.0	C14—N3—C18	116.9 (5)
C15—C16—H16	120.0	C14—N3—Co1	122.5 (4)
C16—C17—C18	117.9 (7)	C18—N3—Co1	120.7 (4)
C16—C17—H17	121.0	C23—N4—C19	115.3 (6)
C18—C17—H17	121.0	C23—N4—Co1	125.4 (5)
N3—C18—C17	123.2 (6)	C19—N4—Co1	118.7 (5)
N3—C18—H18	118.4	C24—N5—C28	117.2 (7)
C17—C18—H18	118.4	C7—O1—Co1^ii	141.2 (4)
N4—C19—C20	123.9 (7)	C8—O3—Co1	132.1 (4)
N4—C19—H19	118.0	Co1—O5—H5B	111.5
C20—C19—H19	118.0	Co1—O5—H5A	111.4
C21—C20—C19	119.6 (7)	H5B—O5—H5A	109.4
C21—C20—H20	120.2

Symmetry codes: (i) −x+3/2, −y, z+1/2; (ii) −x+3/2, −y, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N5^iii	0.85	1.94	2.748 (7)	159

Symmetry code: (iii) −x+1/2, −y, z+1/2.