Diiso­propyl­phosphitocobalamin-acetone-water (1/3.48/7.56)

The di­iso­propyl­phosphite ligand in the title diiso­propyl­phosphitocobalamin compound, [Co(C₆₈H₁₀₂N₁₃O₁₇P₂)]·3.48C₃H₆O·7.56H₂O, coordinates to the Co^III atom via its P atom. The crystal structure is isomorphous with that of other cobalamins that adopt packing type II [Gruber, Jogl, Klintschar & Kratky (1998). Vitamin B₁₂ and B₁₂ Proteins, edited by Kräutler, Arigoni & Golding, pp. 335-347. New York: Wiley-VCH], with a Co-P bond length [2.227 (1) Å] similar to that found in other phosphitocobalamins. The structural trans influence in cobalamins is discussed.

S1. Comment

Cobalamins (Cbls; vitamin B₁₂ derivatives; Fig.1) contain a cobalt(III) ion that is coordinated to four N atoms from a delocalized corrin ring (in the equatorial plane) and one axial N atom from a 5,6-dimethylbenzimidazole ligand; the other axial ligand, R (in the upper or β-position), is variable, e.g. CN⁻ in vitamin B₁₂ itself. The trans influence in these compounds refers to the Co—N bond length trans to R, Co—N_ax (Glusker, 1982; Kratky & Kräutler, 1999). The X-ray crystal structures of dimethylphosphitoCbl, [PO(OCH₃)₂Cbl] (Kopf, 1986), hereafter DiMePC, and fluoromethylphosphitoCbl, [PO(OCH₃)(F)Cbl], hereafter FMePC, have been reported previously (Bieganowski et al., 1980; Bieganowski et al., 1981; Kopf, 1986). We have determined the X-ray crystal structure of diisopropylphosphitoCbl, [P(O)(O-ⁱPr)₂Cbl], (I) (Fig. 1), in order to compare the structural transinfluence of the P[OCH(CH₃)₂]₂O⁻ ligand with that of P(OCH₃)₂O⁻ (in DiMePc) and to ascertain the effect of the sterically large P[OCH(CH₃)₂]₂O⁻ ligand on anionic phosphitoCbls.

Compound (I) is isomorphous with the other cobalamins with packing type II (Gruber et al., 1998). The ligand coordinates to Co^III via the atom P2, in agreement with the effect of the quadrupole moment of ⁵⁹Co on the ³¹P NMR spectrum of (I) (Chemaly, 1991a). DiMePC and FMePC have been shown by electrophoresis to have a negative charge on the phosphite ligand (Bieganowski & Friedrich, 1980). It is assumed that this situation also occurs in (I), with the charge of +3 on the Co atom balanced by single negative charges on the corrin ring, the phosphito ligand and the phosphate group.

The bond lengths and bond angles of the diisopropylphosphite ligand are listed in Table 1. The geometry around atom P2 of the diisopropylphosphite ligand is close to trigonal pyramidal. The O15—P2—O16 bond angle is smaller than the O15/O16—P2—O17 bond angles, consistent with the presence of a negative charge on O17. Compared with the P2—O15/O16 bond lengths, the P2—O17 bond is short, suggesting that, notwithstanding the negative charge on atom O17, this bond has some double-bond character. These bond lengths and bond angles are similar to those of the P(OCH₃)₂O⁻ ligand trans to N(7)-bonded 3-benzyladenine in a cobaloxime complex (Toscano et al., 1981), but the P2—O and O—C bonds in (I) are slightly longer and the P2—O—C bond angles are slightly smaller.

The ¹H NMR spectrum of (I) shows that the four CH₃ groups in the ligand are all in different environments (Chemaly, 1991a) and this fact is verified by the X-ray crystal structure. A bulky axial ligand in the β-position does not have freedom of rotation about its bond to Co^III; rotation is hindered by the steric sentinel substituents above the plane of the corrin ring [the methyl groups C34 and C40, and the acetamide methylene groups C22 of the a side chain and C29 of the c side chain (Glusker,1982)]. The diisopropylphosphite ligand shows many close contacts with the corrin ring, with 26 intramolecular distances shorter than 4 Å (three shorter than 3 Å). There are nearly twice as many close contacts in (I) as in DiMePC, presumably because the steric bulk of the isopropyl group is greater than that of the methyl group.

In contrast to DiMePC, which has packing type I (Gruber et al. 1998) and in which intramolecular hydrogen bonding is observed between the amide group of the c side chain and one of the O atoms on the ligand (Kopf, 1986), the ligand in (I) does not form any hydrogen bonds, as the c side chain of the corrin ring points away from the ligand. The extensive network of intermolecular hydrogen bonds detailed in Table 2 is very similar to that observed for SCNCbl and SeCNCbl (Garau et al., 2003),which also belong to packing type II.

Table 3 shows the bond lengths and bond angles of the coordination sphere of Co^III and the pK_a of the 5,6-dimethylbenzimidazole base, for (I), DiMePC and FMePC. The Co—P bond length in P(O)(O-ⁱPr)₂Cbl is similar to the Co—P bond length in DiMePC and to the Co—P bond length for the cobaloxime containing the dimethylphosphite ligand (2.229 Å; Toscano et al., 1981). Within the limits of experimental precision, the Co—N_ax bond length in (I) is the same as the Co—N_ax bond length in DiMePC, and hence the structural trans influence is similar. It is possible that the Co—P bond is slightly elongated as a result of steric strain in (I) and that this elongation compensates for the slightly greater inductive effect of the isopropyl group. FMePC has a shorter Co—N_ax bond length than DiMePC and (I) because of the high electronegativity of the F atom. The P—Co—N_ax bond angle in (I) is similar to those in DiMePC and FMePC. Both the structural trans influence and the thermodynamic trans influence [influence on the equilibrium constants of the ligand trans to R, e.g. pK_a for the 5,6-dimethylbenzimidazole base (Pratt, 1972)] increase with increasing σ-donor ability. The Co—N_ax bond length in (I) is similar to the the Co—N_ax bond in methylcobalamin (2.162 Å; Randaccio et al., 2000). Thus the diisopropylphosphite ligand has a structural trans influence similar to that of methyl, confirming that diisopropylphosphite (as expected) is a good σ-donor ligand. It has been shown (Chemaly et al., 1987; Chemaly, 1991b) that the thermodynamic trans-influence order for anionic phosphite ligands in Cbls (pK_as for protonation of the 5,6-dimethylbenzimidazole base) is R = P(OCH₃)₂O⁻≤ P(OCH₂CH₃)₂O⁻ < P[OCH(CH₃)₂]₂O⁻ and that this order is due to both electronic and steric influences of phosphite ligands. Thus the thermodynamic trans influence is consistent with the structural trans influence.

S2. Experimental

(I) was prepared and characterized as described previously (Chemaly, 1991a). Crystals suitable for X-ray analysis were grown by dissolving (I) (20 mg) in deionized water (0.30 ml) in a small glass vial and allowing acetone vapour to diffuse into the aqueous solution in a cold room (277 K). Crystals appeared after approximately one month. The selected crystal was removed from the mother liquor and immediately mounted in a stream of liquid nitrogen at 123 K.

S3. Refinement

Non-H atoms were refined anisotropically. H atoms were positioned geometrically and allowed to refine on their respective parent atoms, with U_iso(H) = 1.2U_eq(C) [1.5U_eq(C) for methyl groups]. The structure contains six ordered water and three ordered acetone molecules. In addition, there are three disordered water molecules (site occupancy 0.52) sharing a site with an acetone molecule (site occupancy 0.48). A FLAT restraint was used to ensure that the disordered acetone molecule remained planar. No elemental analyses have been carried out, as these have been found to be unreliable with respect to the water content. The occupancies of the acetone molecule and three water molecules sharing a site sum to unity, with the atomic displacement parameters still behaving reasonably well.

Computing details

Data collection: SMART (Bruker,1998); cell refinement: SMART; data reduction: SAINT (Bruker,1999); program(s) used to solve structure: SHELXTL (Bruker,1999); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The molecular structure of diisopropylphosphitoCbl. Displacement ellipsoids are drawn at the 50%? probability level and H atoms have been omitted for clarity (for missing labels see scheme).

(I)

Crystal data

[Co(C68H102N13O17P2)]·3.48C3H6O·7.56H2O	F(000) = 3924
Mr = 1832.83	Dx = 1.338 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1013 reflections
a = 15.889 (5) Å	θ = 2.2–25.5°
b = 22.070 (7) Å	µ = 0.31 mm^−1
c = 25.941 (8) Å	T = 123 K
V = 9097 (5) Å^3	Rectangular, red
Z = 4	0.38 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer	15746 reflections with I > 2σ(I)
ϕ and ω scans	Rint = 0.047
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 27°, θmin = 1.2°
Tmin = 0.892, Tmax = 0.964	h = −20→20
54647 measured reflections	k = −19→28
19561 independent reflections	l = −31→33

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0468P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.041	(Δ/σ)max = 0.002
wR(F^2) = 0.095	Δρmax = 0.82 e Å^−3
S = 1.03	Δρmin = −0.38 e Å^−3
19561 reflections	Absolute structure: Flack H D (1983), 8794 Friedel pairs.
1144 parameters	Absolute structure parameter: −0.003 (9)
1 restraint

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. —————————————————————Alert level B PLAT413_ALERT_2_B Short Inter XH3.. XHn H68B.. H75A = 1.99 A ng.

Authors comment: H68B is in close contact with a CH3 group on a disordered acetone molecule. Short H.. H contacts involving CH3 H-atoms are often hampered by the fact that they involve H atoms at not optimal calculated positions.

PLAT417_ALERT_2_B Short Inter D—H.·H—D H1Y.. H2Y = 1.90 A ng.

Authors comment: H2Y (attached to O2W) is involved in a hydrogen bond with O9. H1Y (attached to O1W) is hydrogen bonded to O2W. O9 lies in a direction perpedicluar to O1W with respect to O2W. This results in a apparent close contact. The hydrogen bonding pattern is however correct.

———————————————–Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ ···. ?

Authors comment: It was not possible to locate or place hydrogen atoms on some of the water molecules. Their contribution to the total cell contents were however taken into account and included in the reported sum formula.

PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ···. ?

Authors comment: It was not possible to locate or place hydrogen atoms on some of the water molecules. Their contribution to the total cell contents were however taken into account and included in the reported sum formula.

PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)··· ?

Authors comment: It was not possible to locate or place hydrogen atoms on some of the water molecules. Their contribution to the total cell contents were however taken into account and included in the reported sum formula.

PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ···. 2.15

Authors comment: The structure contains disordered solvent molecules. The final residual peaks from SHELXL are as follows: Highest peak 0.82 at 0.2118 0.4764 0.5178 [0.07 A from O9W] Deepest hole −0.38 at 0.2450 0.1261 0.7686 [0.41 A from CO] This possibly indicates a slightly inadequate disorder model around O9W.

PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ······. = 3

Authors comment: The structure contains disordered solvent molecules.

PLAT220_ALERT_2_C Large Non-Solvent C U_eq(max)/U_eq(min) ··· 2.94 Ratio

Authors comment: This structure contains a large diisopropylphosphito ligand. The terminal carbon atoms on this group are slightly enlarged due to thermal libration.

PLAT220_ALERT_2_C Large Non-Solvent N U_eq(max)/U_eq(min) ··· 3.22 Ratio

Authors comment: This structure contains a number of amide side chains The terminal nitrogen atoms on this group are slightly enlarged due to thermal libration.

PLAT222_ALERT_3_C Large Non-Solvent H U_eq(max)/U_eq(min) ··· 3.94 Ratio

Authors comment: This structure contains a large diisopropylphosphito ligand, as well as a number of amide side chains. The terminal hydrogen atoms on these groups inherit the thermal ellipsoids of the parent carbon and nitrogen atoms.

PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors ···. C70

Authors comment: Three solvent water molecules share a common site with an acetone molecule. Due to the disorder the thermal ellipsoids are unreliable.

PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors ···. C73

Authors comment: Three solvent water molecules share a common site with an acetone molecule. Due to the disorder the thermal ellipsoids are unreliable.

PLAT302_ALERT_4_C Anion/Solvent Disorder ························. 14.00 Perc.

Authors comment: The structure contains six well behaved solvent water molecules and three well behaved acetone solvent molecules. In addition, there are three disordered waters and a disordered acetone molecule.

PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ···.. >O7W

Authors comment: It was not possible to locate or place hydrogen atoms on some of the water molecules.

PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ···.. >O8W

Authors comment: It was not possible to locate or place hydrogen atoms on some of the water molecules.

PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ···.. >O9W

Authors comment: It was not possible to locate or place hydrogen atoms on some of the water molecules.

PLAT432_ALERT_2_C Short Inter X···Y Contact O4.. C73 = 2.96 A ng.

Authors comment: This is an example of a short O···C contact. (see Allen et al. (1998) B54, 320–329)

PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C1.44 H2.87 O2.04

Authors comment: To be consistent with structures reported in an earlier paper (and for purposes of comparison), the main residue was moved into the same assymetric unit as the earlier structures. This resulted in some solvent molecules being outside the unit cell. This applies to all PLAT790 ALERTS.

PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 C3 H6 O

PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 7 H2 O

—————————————————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:C78.44 H138 Co1 N13 O28.04 P2 Atom count from the _atom_site data: C78.43698 H134.8739 Co1 N13 O2 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 C78.44 H138.00 Co N13 O28.04 P2 TEST: Compare cell contents of formula and atom_site data

atom Z*formula cif sites diff C 313.76 313.75 0.01 H 552.00 539.50 12.50 Co 4.00 4.00 0.00 N 52.00 52.00 0.00 O 112.16 112.17 − 0.01 P 8.00 8.00 0.00

Authors comment for both the above alerts: It was not possible to locate or place hydrogen atoms on some of the water molecules. Their contribution to the total cell contents were however taken into account and included in the reported sum formula.

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 27.00 From the CIF: _reflns_number_total 19561 Count of symmetry unique reflns 10767 Completeness (_total/calc) 181.68% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 8794 Fraction of Friedel pairs measured 0.817 Are heavy atom types Z>Si present yes ——————————————————————

Authors comment: Number of Friedel pairs has been added to _refine_ls_abs_structure_details as suggestd by ALERT explanation.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.34952 (15)	0.19268 (11)	0.71270 (9)	0.0145 (5)
C2	0.44592 (15)	0.20870 (11)	0.71886 (9)	0.0153 (5)
C3	0.48679 (16)	0.14430 (11)	0.72304 (9)	0.0147 (5)
H3	0.5343	0.1463	0.7482	0.018*
C4	0.41616 (15)	0.10752 (12)	0.74664 (9)	0.0135 (5)
C5	0.42836 (15)	0.04916 (11)	0.77123 (9)	0.0148 (5)
C6	0.36182 (16)	0.01241 (12)	0.78288 (9)	0.0149 (5)
C7	0.36403 (16)	−0.05238 (12)	0.80532 (10)	0.0170 (5)
C8	0.27516 (16)	−0.07576 (11)	0.78911 (9)	0.0177 (5)
H8	0.2515	−0.1031	0.8162	0.021*
C9	0.22665 (16)	−0.01764 (11)	0.78698 (9)	0.0168 (5)
C10	0.14055 (16)	−0.01414 (12)	0.79495 (9)	0.0172 (6)
H10	0.1119	−0.0511	0.8015	0.021*
C11	0.09229 (15)	0.03823 (12)	0.79423 (10)	0.0157 (5)
C12	0.00143 (16)	0.04097 (12)	0.81256 (10)	0.0189 (6)
C13	−0.02822 (15)	0.10039 (11)	0.78654 (10)	0.0163 (5)
H13	−0.0658	0.1233	0.8105	0.02*
C14	0.05456 (15)	0.13485 (12)	0.77929 (9)	0.0151 (5)
C15	0.05993 (15)	0.19535 (11)	0.76789 (9)	0.0147 (5)
C16	0.13930 (16)	0.22270 (11)	0.75312 (9)	0.0145 (5)
C17	0.15603 (15)	0.29079 (11)	0.74349 (9)	0.0146 (5)
C18	0.24426 (15)	0.28763 (10)	0.71653 (9)	0.0146 (5)
H18	0.2352	0.2794	0.679	0.018*
C19	0.28285 (14)	0.23081 (11)	0.74105 (9)	0.0142 (5)
H19	0.3061	0.2423	0.7755	0.017*
C20	0.32313 (16)	0.18485 (11)	0.65595 (9)	0.0153 (5)
H20A	0.3537	0.1506	0.6409	0.023*
H20B	0.3365	0.2219	0.6368	0.023*
H20C	0.2625	0.1771	0.6541	0.023*
C21	0.48180 (16)	0.24695 (11)	0.67472 (9)	0.0166 (5)
H21A	0.4498	0.2848	0.6718	0.025*
H21B	0.4776	0.2243	0.6423	0.025*
H21C	0.541	0.2563	0.6818	0.025*
C22	0.46041 (15)	0.24241 (12)	0.77053 (9)	0.0171 (5)
H22A	0.4292	0.2812	0.7692	0.02*
H22B	0.4353	0.2178	0.7985	0.02*
C23	0.55188 (16)	0.25620 (12)	0.78503 (10)	0.0198 (6)
C24	0.51859 (15)	0.11273 (12)	0.67315 (9)	0.0171 (5)
H24A	0.5146	0.0683	0.6778	0.02*
H24B	0.4811	0.1241	0.6442	0.02*
C25	0.60997 (16)	0.12911 (13)	0.65866 (10)	0.0213 (6)
H25A	0.6132	0.1726	0.6494	0.026*
H25B	0.6472	0.1221	0.6887	0.026*
C26	0.63937 (17)	0.09116 (13)	0.61381 (10)	0.0209 (6)
C27	0.51915 (16)	0.02989 (12)	0.78240 (10)	0.0203 (6)
H27A	0.5219	0.0103	0.8163	0.03*
H27B	0.5557	0.0657	0.7822	0.03*
H27C	0.538	0.0014	0.7559	0.03*
C28	0.43508 (16)	−0.09372 (12)	0.78652 (10)	0.0198 (6)
H28A	0.4438	−0.0875	0.7495	0.03*
H28B	0.4199	−0.1361	0.7929	0.03*
H28C	0.487	−0.084	0.8052	0.03*
C29	0.36737 (17)	−0.04556 (12)	0.86559 (9)	0.0185 (6)
H29A	0.4214	−0.0265	0.8755	0.022*
H29B	0.3213	−0.0185	0.8769	0.022*
C30	0.35904 (16)	−0.10591 (13)	0.89268 (9)	0.0192 (6)
C31	0.27674 (15)	−0.10816 (12)	0.73627 (10)	0.0207 (5)
H31A	0.3101	−0.0832	0.712	0.025*
H31B	0.3063	−0.1473	0.7404	0.025*
C32	0.19099 (17)	−0.12027 (13)	0.71226 (11)	0.0267 (7)
H32A	0.1576	−0.1464	0.7356	0.032*
H32B	0.1605	−0.0815	0.708	0.032*
C33	0.19962 (19)	−0.15077 (14)	0.66050 (12)	0.0309 (7)
C34	0.00444 (18)	0.05013 (14)	0.87165 (10)	0.0268 (7)
H34A	0.0329	0.0155	0.8877	0.04*
H34B	−0.053	0.0532	0.8851	0.04*
H34C	0.0353	0.0874	0.8796	0.04*
C35	−0.04796 (17)	−0.01630 (13)	0.80059 (12)	0.0264 (7)
H35A	−0.0454	−0.0245	0.7635	0.04*
H35B	−0.1068	−0.0108	0.811	0.04*
H35C	−0.0236	−0.0505	0.8195	0.04*
C36	−0.07065 (15)	0.09476 (12)	0.73292 (10)	0.0187 (5)
H36A	−0.0683	0.1349	0.7159	0.022*
H36B	−0.037	0.0663	0.7118	0.022*
C37	−0.16276 (15)	0.07296 (12)	0.73262 (11)	0.0213 (6)
H37A	−0.1854	0.0774	0.6973	0.026*
H37B	−0.1638	0.0293	0.7413	0.026*
C38	−0.22002 (15)	0.10630 (12)	0.76949 (10)	0.0211 (6)
C39	−0.01866 (16)	0.23414 (12)	0.77273 (10)	0.0210 (6)
H39A	−0.0649	0.2095	0.7865	0.031*
H39B	−0.0343	0.2499	0.7387	0.031*
H39C	−0.0075	0.2681	0.7961	0.031*
C40	0.16307 (17)	0.32237 (12)	0.79648 (9)	0.0196 (6)
H40A	0.1729	0.3658	0.7914	0.029*
H40B	0.2101	0.3048	0.8159	0.029*
H40C	0.1107	0.3165	0.8158	0.029*
C41	0.30079 (16)	0.34381 (11)	0.72160 (10)	0.0179 (6)
H41A	0.3043	0.3548	0.7585	0.021*
H41B	0.3582	0.3327	0.7102	0.021*
C42	0.27321 (15)	0.39936 (11)	0.69173 (9)	0.0166 (5)
C43	0.09068 (15)	0.32543 (11)	0.71122 (10)	0.0161 (5)
H43A	0.04	0.3315	0.7328	0.019*
H43B	0.1139	0.366	0.7035	0.019*
C44	0.06280 (17)	0.29674 (13)	0.66036 (10)	0.0221 (6)
H44A	0.1091	0.2993	0.6349	0.027*
H44B	0.0495	0.2534	0.6659	0.027*
C45	−0.01439 (17)	0.32935 (13)	0.63964 (10)	0.0222 (6)
C46	−0.07231 (17)	0.38968 (13)	0.56846 (10)	0.0220 (6)
H46A	−0.0516	0.4282	0.5536	0.026*
H46B	−0.118	0.3995	0.5931	0.026*
C47	−0.10746 (16)	0.35023 (13)	0.52553 (10)	0.0196 (6)
H47	−0.1352	0.3135	0.5404	0.024*
C48	−0.16921 (17)	0.38445 (14)	0.49186 (10)	0.0252 (6)
H48A	−0.1413	0.4199	0.4769	0.038*
H48B	−0.2172	0.3977	0.5128	0.038*
H48C	−0.1891	0.3579	0.4642	0.038*
C49	0.06182 (16)	0.08637 (12)	0.57713 (10)	0.0179 (6)
H49	0.0556	0.0538	0.5506	0.021*
C50	0.08569 (16)	0.14638 (12)	0.55081 (10)	0.0186 (6)
H50	0.1222	0.1396	0.52	0.022*
C51	−0.00231 (16)	0.16835 (12)	0.53547 (10)	0.0179 (6)
H51	−0.0188	0.15	0.5017	0.021*
C52	−0.06016 (16)	0.14535 (12)	0.57761 (10)	0.0191 (6)
H52	−0.0702	0.1783	0.6033	0.023*
C53	−0.14405 (18)	0.12175 (15)	0.55793 (12)	0.0330 (7)
H53A	−0.1778	0.1068	0.5874	0.04*
H53B	−0.1755	0.1554	0.5415	0.04*
C54	0.13229 (16)	0.09386 (11)	0.66272 (9)	0.0168 (5)
H54	0.0924	0.1209	0.6774	0.02*
C55	0.32318 (16)	0.01283 (11)	0.65192 (10)	0.0171 (5)
H55	0.3587	0.0177	0.6811	0.02*
C56	0.34919 (17)	−0.02185 (12)	0.61011 (10)	0.0190 (6)
C57	0.29667 (17)	−0.02919 (12)	0.56600 (10)	0.0212 (6)
C58	0.21926 (16)	−0.00110 (11)	0.56422 (10)	0.0189 (6)
H58	0.184	−0.0052	0.5349	0.023*
C59	0.19390 (16)	0.03348 (11)	0.60657 (10)	0.0169 (5)
C60	0.24439 (16)	0.04026 (10)	0.65047 (9)	0.0151 (5)
C61	0.43429 (18)	−0.05258 (14)	0.61209 (11)	0.0284 (7)
H61A	0.4613	−0.044	0.6453	0.043*
H61B	0.4697	−0.0372	0.5841	0.043*
H61C	0.427	−0.0964	0.6082	0.043*
C62	0.3271 (2)	−0.06638 (14)	0.52031 (11)	0.0324 (7)
H62A	0.3261	−0.1095	0.5293	0.049*
H62B	0.3846	−0.0543	0.5114	0.049*
H62C	0.29	−0.0593	0.4907	0.049*
C63	0.18444 (18)	0.20798 (13)	0.91115 (10)	0.0245 (6)
H63	0.2005	0.1747	0.9354	0.029*
C64	0.2385 (2)	0.26303 (14)	0.92175 (11)	0.0336 (7)
H64A	0.2962	0.2551	0.9103	0.05*
H64B	0.2384	0.2716	0.9588	0.05*
H64C	0.2158	0.298	0.903	0.05*
C65	0.0919 (2)	0.22118 (16)	0.91678 (13)	0.0396 (8)
H65A	0.075	0.2515	0.8912	0.059*
H65B	0.0808	0.2367	0.9515	0.059*
H65C	0.0597	0.1839	0.9113	0.059*
C66	0.40797 (16)	0.12197 (13)	0.89185 (10)	0.0235 (6)
H66	0.4078	0.078	0.8825	0.028*
C67	0.3841 (2)	0.12859 (17)	0.94827 (11)	0.0382 (8)
H67A	0.3845	0.1716	0.9577	0.057*
H67B	0.4248	0.1066	0.9697	0.057*
H67C	0.3277	0.1118	0.9538	0.057*
C68	0.49371 (18)	0.14777 (16)	0.88128 (12)	0.0362 (8)
H68A	0.509	0.14	0.8453	0.054*
H68B	0.535	0.1285	0.9041	0.054*
H68C	0.493	0.1915	0.8876	0.054*
C69	0.9649 (3)	−0.0678 (2)	0.55985 (14)	0.0736 (14)
H69A	1.0253	−0.0766	0.5598	0.11*
H69B	0.9541	−0.0309	0.5399	0.11*
H69C	0.9344	−0.1018	0.5443	0.11*
C70	0.9362 (2)	−0.05916 (15)	0.61278 (14)	0.0394 (8)
C71	0.8494 (2)	−0.03782 (16)	0.62062 (14)	0.0447 (9)
H71A	0.8098	−0.0687	0.6083	0.067*
H71B	0.8407	−0.0001	0.6014	0.067*
H71C	0.8398	−0.0304	0.6574	0.067*
C72	0.1702 (3)	−0.30877 (19)	0.60671 (15)	0.0621 (11)
H72A	0.1796	−0.2937	0.6418	0.093*
H72B	0.1895	−0.3508	0.6043	0.093*
H72C	0.11	−0.3069	0.5987	0.093*
C73	0.2178 (2)	−0.27070 (16)	0.56939 (12)	0.0371 (8)
C74	0.3109 (2)	−0.2775 (3)	0.56867 (16)	0.0754 (15)
H74A	0.3257	−0.3171	0.554	0.113*
H74B	0.3327	−0.2747	0.6039	0.113*
H74C	0.3357	−0.2453	0.5476	0.113*
C75	0.3775 (6)	−0.4740 (4)	0.5849 (4)	0.064 (3)	0.479 (5)
H75A	0.4298	−0.454	0.5743	0.096*	0.479 (5)
H75B	0.3827	−0.5178	0.5795	0.096*	0.479 (5)
H75C	0.3669	−0.4658	0.6214	0.096*	0.479 (5)
C76	0.3070 (6)	−0.4505 (3)	0.5538 (3)	0.065 (3)	0.479 (5)
C77	0.2264 (6)	−0.4804 (4)	0.5601 (3)	0.062 (3)	0.479 (5)
H77A	0.1812	−0.4502	0.5585	0.093*	0.479 (5)
H77B	0.2248	−0.5011	0.5935	0.093*	0.479 (5)
H77C	0.2187	−0.5102	0.5324	0.093*	0.479 (5)
C78	0.4628 (2)	0.31597 (16)	0.96113 (14)	0.0442 (9)
H78A	0.4927	0.287	0.9392	0.066*
H78B	0.4263	0.294	0.9851	0.066*
H78C	0.5037	0.3401	0.9807	0.066*
C79	0.41066 (19)	0.35694 (14)	0.92832 (13)	0.0323 (7)
C80	0.3599 (2)	0.40414 (17)	0.95548 (14)	0.0475 (9)
H80A	0.3407	0.4345	0.9305	0.071*
H80B	0.3946	0.4238	0.9818	0.071*
H80C	0.311	0.3851	0.9719	0.071*
N1	0.34346 (12)	0.13315 (9)	0.74072 (7)	0.0127 (4)
N2	0.27771 (12)	0.02972 (9)	0.77700 (7)	0.0145 (4)
N3	0.12087 (12)	0.09341 (9)	0.78058 (8)	0.0141 (4)
N4	0.20870 (12)	0.19123 (9)	0.74941 (7)	0.0136 (4)
N5	0.56136 (14)	0.29646 (11)	0.82289 (8)	0.0238 (5)
H5A	0.6121	0.3064	0.8335	0.029*
H5B	0.5168	0.3131	0.8373	0.029*
N6	0.62488 (15)	0.11288 (12)	0.56680 (9)	0.0298 (6)
H6A	0.6407	0.0921	0.5395	0.036*
H6B	0.5995	0.148	0.563	0.036*
N7	0.43025 (14)	−0.13429 (11)	0.90592 (9)	0.0244 (5)
H7A	0.4281	−0.1698	0.9214	0.029*
H7B	0.4793	−0.1175	0.8992	0.029*
N8	0.13259 (17)	−0.14682 (13)	0.62895 (10)	0.0409 (7)
H8A	0.134	−0.1641	0.5984	0.049*
H8B	0.0874	−0.127	0.6389	0.049*
N9	−0.23307 (14)	0.16460 (10)	0.75988 (9)	0.0254 (5)
H9A	−0.2658	0.186	0.7803	0.03*
H9B	−0.209	0.1819	0.7331	0.03*
N10	0.28196 (14)	0.45164 (9)	0.71580 (9)	0.0215 (5)
H10A	0.2696	0.4857	0.6998	0.026*
H10B	0.3002	0.4525	0.7478	0.026*
N11	−0.00418 (14)	0.36020 (10)	0.59595 (8)	0.0213 (5)
H11	0.0469	0.3628	0.583	0.026*
N12	0.12198 (13)	0.06759 (10)	0.61584 (8)	0.0172 (5)
N13	0.20311 (13)	0.07829 (9)	0.68593 (8)	0.0139 (4)
P1	−0.02271 (4)	0.26410 (3)	0.47698 (3)	0.01655 (14)
P2	0.25455 (4)	0.12881 (3)	0.84696 (2)	0.01566 (14)
O1	0.61305 (11)	0.23217 (9)	0.76412 (8)	0.0311 (5)
O2	0.67490 (14)	0.04189 (10)	0.62021 (8)	0.0385 (6)
O1W	0.73140 (12)	0.24032 (9)	0.46884 (7)	0.0281 (4)
H1Y	0.7268	0.2465	0.505	0.034*
H1Z	0.7886	0.2434	0.4598	0.034*
O3	0.28873 (12)	−0.12763 (9)	0.90133 (7)	0.0283 (5)
O2W	0.27781 (12)	−0.24678 (9)	0.92405 (7)	0.0283 (5)
H2Y	0.3329	−0.2595	0.9319	0.034*
H2Z	0.2817	−0.2049	0.9182	0.034*
O4	0.26371 (15)	−0.17836 (11)	0.64747 (8)	0.0472 (6)
O3W	0.88606 (12)	0.12331 (10)	0.41852 (8)	0.0360 (5)
H3Y	0.8929	0.1664	0.427	0.043*
H3Z	0.8435	0.1255	0.3911	0.043*
O5	−0.25274 (13)	0.07987 (9)	0.80689 (7)	0.0307 (5)
O4W	0.16340 (12)	0.37320 (10)	0.55218 (8)	0.0377 (5)
H4Y	0.1926	0.3362	0.5507	0.045*
H4Z	0.1912	0.3852	0.5824	0.045*
O6	0.24772 (11)	0.39488 (8)	0.64639 (6)	0.0221 (4)
O5W	0.81924 (14)	0.22270 (10)	0.66569 (8)	0.0369 (5)
H5Y	0.7863	0.2347	0.6371	0.044*
H5Z	0.8553	0.2562	0.6605	0.044*
O7	−0.08214 (12)	0.32791 (10)	0.66359 (8)	0.0303 (5)
O6W	0.64046 (14)	−0.05007 (10)	0.68568 (7)	0.0365 (5)
H6Y	0.636	−0.0829	0.6628	0.044*
H6Z	0.6458	−0.0184	0.6616	0.044*
O8	−0.10021 (11)	0.23738 (9)	0.45334 (7)	0.0219 (4)
O7W	0.2950 (8)	−0.4400 (5)	0.5854 (4)	0.148 (3)*	0.521 (5)
O9	0.05539 (11)	0.26211 (8)	0.44516 (7)	0.0221 (4)
O8W	0.4525 (7)	−0.5010 (5)	0.5680 (4)	0.148 (3)*	0.521 (5)
O10	−0.00724 (12)	0.23330 (8)	0.53212 (6)	0.0205 (4)
O9W	0.2133 (7)	−0.5211 (5)	0.5164 (4)	0.148 (3)*	0.521 (5)
O11	−0.03558 (11)	0.33220 (8)	0.49344 (6)	0.0191 (4)
O12	−0.01609 (11)	0.09590 (8)	0.60220 (7)	0.0225 (4)
O13	0.12468 (12)	0.18466 (8)	0.58699 (6)	0.0205 (4)
H13A	0.15	0.2126	0.5715	0.031*
O14	−0.13344 (16)	0.07404 (11)	0.52156 (8)	0.0443 (6)
H14	−0.1308	0.0886	0.4917	0.067*
O15	0.19881 (11)	0.18811 (8)	0.85805 (6)	0.0196 (4)
O16	0.34838 (11)	0.15421 (8)	0.85864 (6)	0.0189 (4)
O17	0.23369 (12)	0.07739 (8)	0.88144 (6)	0.0208 (4)
O18	0.98242 (16)	−0.06959 (14)	0.64992 (10)	0.0612 (8)
O19	0.18216 (17)	−0.23642 (13)	0.54090 (9)	0.0541 (7)
O20	0.3155 (4)	−0.4076 (3)	0.5240 (2)	0.0597 (19)	0.479 (5)
O21	0.40926 (13)	0.35214 (10)	0.88104 (8)	0.0338 (5)
Co	0.23566 (2)	0.109708 (15)	0.763470 (12)	0.01285 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0151 (13)	0.0089 (12)	0.0194 (12)	−0.0005 (10)	−0.0032 (10)	0.0019 (10)
C2	0.0148 (13)	0.0133 (13)	0.0178 (13)	0.0008 (10)	−0.0006 (10)	0.0003 (11)
C3	0.0150 (12)	0.0147 (13)	0.0143 (12)	−0.0011 (10)	−0.0011 (10)	0.0016 (10)
C4	0.0140 (12)	0.0146 (12)	0.0118 (12)	0.0008 (11)	−0.0008 (9)	−0.0009 (10)
C5	0.0142 (12)	0.0168 (13)	0.0136 (13)	0.0033 (10)	−0.0027 (10)	0.0014 (11)
C6	0.0193 (13)	0.0142 (13)	0.0111 (11)	0.0039 (11)	−0.0016 (10)	−0.0004 (10)
C7	0.0149 (13)	0.0170 (14)	0.0192 (13)	0.0016 (11)	−0.0009 (10)	0.0048 (11)
C8	0.0182 (14)	0.0153 (13)	0.0196 (13)	0.0034 (11)	−0.0018 (11)	0.0048 (11)
C9	0.0201 (14)	0.0146 (12)	0.0157 (12)	−0.0007 (11)	−0.0041 (11)	0.0020 (10)
C10	0.0177 (13)	0.0117 (13)	0.0222 (14)	−0.0016 (11)	0.0000 (11)	0.0034 (11)
C11	0.0142 (13)	0.0174 (14)	0.0156 (13)	−0.0030 (11)	−0.0016 (10)	0.0019 (11)
C12	0.0135 (13)	0.0164 (14)	0.0267 (14)	0.0012 (11)	0.0003 (11)	0.0057 (11)
C13	0.0140 (12)	0.0127 (13)	0.0222 (13)	−0.0006 (10)	0.0008 (10)	0.0003 (11)
C14	0.0133 (12)	0.0173 (13)	0.0146 (12)	0.0026 (10)	−0.0009 (9)	−0.0011 (11)
C15	0.0130 (12)	0.0156 (13)	0.0154 (12)	0.0019 (10)	−0.0004 (10)	−0.0011 (11)
C16	0.0171 (13)	0.0142 (13)	0.0122 (12)	0.0023 (10)	−0.0020 (9)	−0.0011 (10)
C17	0.0155 (13)	0.0124 (12)	0.0158 (12)	−0.0009 (10)	−0.0003 (10)	−0.0013 (10)
C18	0.0138 (13)	0.0144 (12)	0.0157 (11)	0.0003 (10)	−0.0009 (10)	−0.0011 (10)
C19	0.0144 (13)	0.0141 (12)	0.0142 (12)	−0.0017 (10)	−0.0012 (10)	−0.0013 (11)
C20	0.0176 (13)	0.0128 (13)	0.0154 (12)	0.0013 (10)	0.0013 (10)	0.0014 (10)
C21	0.0159 (13)	0.0123 (13)	0.0215 (13)	0.0004 (11)	0.0024 (10)	−0.0002 (11)
C22	0.0130 (12)	0.0203 (14)	0.0179 (13)	0.0010 (10)	−0.0011 (10)	−0.0008 (11)
C23	0.0167 (13)	0.0185 (14)	0.0243 (14)	0.0000 (11)	−0.0047 (11)	0.0016 (12)
C24	0.0152 (12)	0.0159 (13)	0.0201 (12)	−0.0001 (11)	0.0023 (10)	−0.0016 (11)
C25	0.0156 (13)	0.0267 (15)	0.0217 (14)	−0.0025 (12)	0.0024 (10)	0.0011 (12)
C26	0.0161 (13)	0.0214 (15)	0.0252 (14)	−0.0012 (11)	0.0046 (11)	0.0026 (12)
C27	0.0165 (13)	0.0215 (14)	0.0230 (14)	0.0030 (11)	−0.0020 (11)	0.0054 (12)
C28	0.0187 (14)	0.0188 (14)	0.0219 (13)	0.0039 (11)	−0.0023 (11)	0.0033 (11)
C29	0.0197 (14)	0.0155 (13)	0.0204 (13)	0.0021 (11)	0.0000 (11)	0.0018 (11)
C30	0.0206 (14)	0.0206 (14)	0.0164 (12)	0.0021 (12)	0.0002 (10)	0.0023 (12)
C31	0.0202 (13)	0.0164 (12)	0.0254 (13)	0.0000 (11)	−0.0019 (11)	0.0020 (12)
C32	0.0236 (15)	0.0256 (16)	0.0309 (15)	0.0048 (12)	−0.0078 (12)	−0.0047 (13)
C33	0.0245 (16)	0.0323 (17)	0.0358 (17)	0.0060 (14)	−0.0097 (13)	−0.0067 (15)
C34	0.0245 (16)	0.0335 (17)	0.0223 (14)	0.0027 (13)	0.0060 (12)	0.0084 (13)
C35	0.0136 (14)	0.0186 (15)	0.0468 (18)	−0.0006 (12)	−0.0031 (12)	0.0054 (14)
C36	0.0160 (13)	0.0170 (14)	0.0231 (13)	0.0015 (10)	−0.0011 (11)	−0.0005 (12)
C37	0.0165 (13)	0.0204 (14)	0.0269 (14)	0.0001 (11)	−0.0027 (11)	−0.0012 (12)
C38	0.0130 (13)	0.0216 (14)	0.0286 (14)	−0.0030 (11)	−0.0043 (11)	−0.0015 (13)
C39	0.0193 (13)	0.0162 (13)	0.0275 (15)	0.0016 (11)	0.0027 (11)	0.0037 (12)
C40	0.0217 (14)	0.0185 (14)	0.0185 (13)	0.0027 (11)	−0.0006 (11)	−0.0032 (11)
C41	0.0156 (13)	0.0150 (13)	0.0231 (14)	0.0020 (10)	−0.0021 (10)	0.0000 (11)
C42	0.0106 (12)	0.0174 (13)	0.0218 (13)	−0.0016 (11)	0.0036 (10)	0.0020 (11)
C43	0.0146 (13)	0.0125 (13)	0.0213 (13)	0.0016 (10)	−0.0014 (10)	0.0024 (11)
C44	0.0207 (14)	0.0213 (14)	0.0245 (14)	0.0056 (12)	−0.0019 (11)	−0.0007 (12)
C45	0.0210 (15)	0.0226 (15)	0.0229 (14)	0.0016 (12)	−0.0051 (11)	−0.0026 (12)
C46	0.0230 (14)	0.0217 (14)	0.0212 (13)	0.0065 (13)	−0.0039 (11)	−0.0005 (12)
C47	0.0175 (13)	0.0211 (14)	0.0202 (13)	0.0040 (11)	0.0020 (11)	−0.0003 (12)
C48	0.0251 (14)	0.0298 (16)	0.0206 (14)	0.0092 (13)	−0.0050 (11)	0.0012 (13)
C49	0.0153 (13)	0.0205 (14)	0.0178 (13)	0.0021 (11)	−0.0046 (10)	−0.0005 (11)
C50	0.0181 (14)	0.0231 (15)	0.0146 (13)	0.0007 (11)	0.0009 (10)	0.0019 (11)
C51	0.0194 (14)	0.0169 (13)	0.0172 (13)	0.0020 (11)	−0.0030 (10)	−0.0026 (11)
C52	0.0171 (14)	0.0188 (14)	0.0213 (13)	0.0030 (11)	−0.0019 (11)	0.0026 (11)
C53	0.0184 (14)	0.039 (2)	0.0420 (18)	−0.0007 (14)	−0.0066 (13)	0.0116 (16)
C54	0.0183 (13)	0.0137 (13)	0.0183 (13)	0.0007 (10)	−0.0015 (10)	0.0019 (11)
C55	0.0201 (14)	0.0144 (13)	0.0167 (13)	0.0000 (11)	−0.0008 (11)	0.0022 (11)
C56	0.0207 (14)	0.0145 (14)	0.0218 (13)	0.0036 (11)	0.0004 (11)	0.0013 (11)
C57	0.0248 (15)	0.0162 (14)	0.0226 (14)	0.0017 (12)	0.0012 (11)	−0.0012 (12)
C58	0.0207 (15)	0.0183 (14)	0.0177 (13)	−0.0026 (11)	−0.0050 (10)	−0.0029 (11)
C59	0.0154 (13)	0.0141 (13)	0.0213 (13)	−0.0020 (11)	−0.0028 (10)	0.0023 (11)
C60	0.0177 (13)	0.0113 (11)	0.0161 (12)	−0.0007 (10)	−0.0011 (10)	0.0015 (10)
C61	0.0267 (16)	0.0331 (17)	0.0254 (15)	0.0093 (14)	−0.0014 (12)	−0.0050 (14)
C62	0.0358 (18)	0.0324 (18)	0.0290 (16)	0.0083 (14)	−0.0031 (13)	−0.0119 (14)
C63	0.0334 (16)	0.0259 (16)	0.0141 (13)	0.0043 (13)	0.0055 (12)	−0.0003 (12)
C64	0.0435 (19)	0.0332 (17)	0.0241 (14)	−0.0012 (16)	−0.0045 (14)	−0.0060 (13)
C65	0.043 (2)	0.040 (2)	0.0360 (18)	0.0002 (16)	0.0167 (15)	−0.0081 (16)
C66	0.0212 (14)	0.0265 (16)	0.0227 (14)	0.0028 (12)	−0.0072 (11)	0.0047 (12)
C67	0.0303 (17)	0.061 (2)	0.0235 (15)	−0.0019 (16)	−0.0076 (13)	0.0087 (16)
C68	0.0234 (16)	0.055 (2)	0.0299 (16)	−0.0015 (15)	−0.0048 (13)	0.0030 (16)
C69	0.091 (4)	0.085 (3)	0.045 (2)	0.040 (3)	0.016 (2)	0.008 (2)
C70	0.0353 (19)	0.0336 (19)	0.049 (2)	0.0032 (15)	0.0044 (16)	0.0074 (17)
C71	0.042 (2)	0.039 (2)	0.053 (2)	0.0113 (17)	0.0076 (17)	0.0076 (18)
C72	0.072 (3)	0.058 (3)	0.056 (2)	−0.003 (2)	−0.001 (2)	0.005 (2)
C73	0.037 (2)	0.050 (2)	0.0246 (16)	0.0042 (16)	−0.0004 (14)	−0.0104 (16)
C74	0.047 (3)	0.130 (4)	0.049 (2)	0.015 (3)	−0.0046 (19)	−0.033 (3)
C75	0.053 (6)	0.048 (5)	0.090 (7)	0.010 (4)	−0.018 (5)	−0.010 (5)
C76	0.067 (6)	0.034 (5)	0.095 (8)	−0.004 (4)	−0.018 (6)	0.021 (5)
C77	0.068 (6)	0.054 (5)	0.063 (6)	−0.012 (5)	0.001 (5)	0.001 (5)
C78	0.038 (2)	0.044 (2)	0.050 (2)	−0.0046 (17)	0.0007 (16)	0.0139 (18)
C79	0.0217 (16)	0.0312 (18)	0.044 (2)	−0.0084 (13)	0.0020 (13)	0.0032 (15)
C80	0.057 (2)	0.042 (2)	0.044 (2)	0.0059 (18)	0.0045 (18)	−0.0017 (17)
N1	0.0154 (10)	0.0128 (10)	0.0100 (9)	−0.0001 (8)	−0.0010 (8)	0.0010 (9)
N2	0.0138 (11)	0.0130 (10)	0.0165 (10)	0.0007 (9)	−0.0010 (8)	0.0019 (8)
N3	0.0121 (10)	0.0131 (11)	0.0172 (10)	−0.0006 (8)	−0.0011 (8)	0.0005 (9)
N4	0.0152 (10)	0.0116 (10)	0.0139 (10)	−0.0007 (8)	−0.0023 (8)	0.0004 (8)
N5	0.0148 (11)	0.0296 (14)	0.0270 (12)	−0.0028 (10)	−0.0035 (9)	−0.0065 (11)
N6	0.0300 (13)	0.0344 (15)	0.0251 (13)	0.0103 (12)	0.0008 (10)	−0.0042 (12)
N7	0.0203 (12)	0.0220 (13)	0.0309 (13)	−0.0006 (10)	−0.0013 (10)	0.0099 (11)
N8	0.0324 (15)	0.0496 (18)	0.0408 (15)	0.0140 (13)	−0.0172 (12)	−0.0141 (14)
N9	0.0195 (11)	0.0229 (12)	0.0338 (12)	0.0051 (10)	0.0008 (11)	0.0005 (11)
N10	0.0263 (13)	0.0133 (11)	0.0251 (12)	0.0001 (10)	−0.0053 (10)	0.0008 (10)
N11	0.0210 (12)	0.0232 (12)	0.0199 (11)	0.0050 (10)	−0.0044 (9)	−0.0017 (10)
N12	0.0150 (11)	0.0193 (12)	0.0173 (11)	0.0012 (9)	−0.0038 (9)	0.0007 (9)
N13	0.0132 (10)	0.0125 (11)	0.0161 (10)	0.0012 (9)	0.0000 (8)	0.0002 (9)
P1	0.0175 (3)	0.0173 (3)	0.0148 (3)	0.0020 (3)	−0.0008 (3)	0.0011 (3)
P2	0.0145 (3)	0.0171 (3)	0.0154 (3)	0.0002 (3)	−0.0008 (2)	0.0013 (3)
O1	0.0151 (10)	0.0304 (11)	0.0477 (12)	0.0040 (8)	−0.0022 (9)	−0.0125 (11)
O2	0.0442 (14)	0.0274 (12)	0.0438 (13)	0.0153 (11)	0.0170 (11)	0.0106 (10)
O1W	0.0231 (10)	0.0351 (11)	0.0261 (10)	0.0045 (10)	−0.0003 (8)	0.0007 (9)
O3	0.0206 (10)	0.0321 (11)	0.0322 (11)	0.0006 (9)	0.0008 (8)	0.0136 (9)
O2W	0.0234 (11)	0.0227 (10)	0.0387 (11)	−0.0010 (9)	−0.0004 (9)	0.0046 (9)
O4	0.0350 (13)	0.0617 (15)	0.0449 (13)	0.0257 (12)	−0.0184 (11)	−0.0252 (12)
O3W	0.0285 (11)	0.0353 (13)	0.0441 (13)	−0.0038 (10)	−0.0089 (10)	−0.0131 (11)
O5	0.0340 (12)	0.0249 (10)	0.0332 (10)	−0.0028 (9)	0.0091 (10)	0.0004 (9)
O4W	0.0233 (11)	0.0462 (14)	0.0437 (12)	0.0029 (10)	−0.0026 (9)	−0.0149 (11)
O6	0.0250 (10)	0.0214 (9)	0.0197 (9)	0.0000 (9)	−0.0014 (8)	0.0029 (8)
O5W	0.0376 (13)	0.0369 (13)	0.0363 (12)	0.0001 (11)	−0.0024 (10)	0.0068 (11)
O7	0.0190 (11)	0.0387 (13)	0.0331 (11)	0.0044 (9)	−0.0009 (9)	0.0085 (10)
O6W	0.0530 (14)	0.0321 (12)	0.0244 (11)	−0.0021 (11)	−0.0065 (10)	0.0056 (10)
O8	0.0185 (10)	0.0245 (10)	0.0228 (10)	0.0007 (8)	−0.0046 (8)	0.0005 (9)
O9	0.0213 (10)	0.0223 (10)	0.0226 (10)	−0.0005 (8)	0.0038 (8)	−0.0033 (8)
O10	0.0296 (11)	0.0150 (9)	0.0170 (9)	0.0041 (8)	−0.0044 (8)	0.0013 (8)
O11	0.0196 (10)	0.0195 (10)	0.0183 (9)	0.0032 (8)	0.0033 (7)	0.0000 (8)
O12	0.0154 (9)	0.0267 (11)	0.0255 (10)	0.0007 (8)	−0.0008 (8)	0.0098 (9)
O13	0.0222 (10)	0.0188 (10)	0.0204 (9)	−0.0059 (8)	−0.0048 (8)	0.0023 (8)
O14	0.0543 (15)	0.0405 (14)	0.0383 (12)	−0.0198 (12)	−0.0178 (12)	0.0024 (11)
O15	0.0226 (10)	0.0214 (10)	0.0149 (9)	0.0028 (8)	0.0005 (7)	−0.0033 (8)
O16	0.0179 (10)	0.0210 (10)	0.0177 (9)	−0.0024 (8)	−0.0030 (7)	0.0025 (8)
O17	0.0226 (10)	0.0213 (10)	0.0186 (9)	−0.0019 (9)	0.0013 (8)	0.0049 (8)
O18	0.0444 (16)	0.083 (2)	0.0563 (16)	0.0163 (15)	−0.0088 (13)	0.0078 (16)
O19	0.0651 (17)	0.0673 (18)	0.0299 (13)	0.0079 (15)	−0.0116 (12)	−0.0040 (13)
O20	0.070 (4)	0.048 (4)	0.061 (4)	0.000 (3)	0.002 (3)	0.016 (3)
O21	0.0309 (12)	0.0333 (13)	0.0374 (13)	−0.0062 (10)	0.0017 (10)	−0.0004 (10)
Co	0.01131 (15)	0.01201 (15)	0.01524 (15)	0.00065 (14)	−0.00052 (13)	0.00114 (14)

Geometric parameters (Å, º)

C1—N1	1.504 (3)	C49—C50	1.538 (4)
C1—C19	1.540 (3)	C49—H49	1
C1—C20	1.540 (3)	C50—O13	1.407 (3)
C1—C2	1.580 (3)	C50—C51	1.532 (4)
C2—C21	1.532 (3)	C50—H50	1
C2—C22	1.550 (3)	C51—O10	1.438 (3)
C2—C3	1.566 (3)	C51—C52	1.516 (4)
C3—C4	1.514 (3)	C51—H51	1
C3—C24	1.554 (3)	C52—O12	1.445 (3)
C3—H3	1	C52—C53	1.519 (4)
C4—N1	1.295 (3)	C52—H52	1
C4—C5	1.450 (3)	C53—O14	1.424 (4)
C5—C6	1.366 (4)	C53—H53A	0.99
C5—C27	1.532 (3)	C53—H53B	0.99
C6—N2	1.398 (3)	C54—N13	1.322 (3)
C6—C7	1.544 (4)	C54—N12	1.357 (3)
C7—C28	1.531 (3)	C54—H54	0.95
C7—C8	1.561 (4)	C55—C56	1.390 (4)
C7—C29	1.571 (4)	C55—C60	1.391 (4)
C8—C9	1.497 (3)	C55—H55	0.95
C8—C31	1.546 (4)	C56—C57	1.425 (4)
C8—H8	1	C56—C61	1.514 (4)
C9—N2	1.348 (3)	C57—C58	1.378 (4)
C9—C10	1.386 (4)	C57—C62	1.520 (4)
C10—C11	1.387 (4)	C58—C59	1.397 (4)
C10—H10	0.95	C58—H58	0.95
C11—N3	1.347 (3)	C59—N12	1.390 (3)
C11—C12	1.521 (4)	C59—C60	1.401 (3)
C12—C35	1.520 (4)	C60—N13	1.408 (3)
C12—C34	1.547 (4)	C61—H61A	0.98
C12—C13	1.548 (4)	C61—H61B	0.98
C13—C14	1.531 (3)	C61—H61C	0.98
C13—C36	1.551 (3)	C62—H62A	0.98
C13—H13	1	C62—H62B	0.98
C14—C15	1.370 (4)	C62—H62C	0.98
C14—N3	1.396 (3)	C63—O15	1.464 (3)
C15—C16	1.450 (3)	C63—C65	1.506 (4)
C15—C39	1.519 (3)	C63—C64	1.513 (4)
C16—N4	1.307 (3)	C63—H63	1
C16—C17	1.546 (3)	C64—H64A	0.98
C17—C43	1.537 (3)	C64—H64B	0.98
C17—C40	1.545 (3)	C64—H64C	0.98
C17—C18	1.568 (3)	C65—H65A	0.98
C18—C19	1.534 (3)	C65—H65B	0.98
C18—C41	1.537 (3)	C65—H65C	0.98
C18—H18	1	C66—O16	1.464 (3)
C19—N4	1.483 (3)	C66—C68	1.502 (4)
C19—H19	1	C66—C67	1.519 (4)
C20—H20A	0.98	C66—H66	1
C20—H20B	0.98	C67—H67A	0.98
C20—H20C	0.98	C67—H67B	0.98
C21—H21A	0.98	C67—H67C	0.98
C21—H21B	0.98	C68—H68A	0.98
C21—H21C	0.98	C68—H68B	0.98
C22—C23	1.532 (3)	C68—H68C	0.98
C22—H22A	0.99	C69—C70	1.459 (5)
C22—H22B	0.99	C69—H69A	0.98
C23—O1	1.233 (3)	C69—H69B	0.98
C23—N5	1.333 (3)	C69—H69C	0.98
C24—C25	1.543 (3)	C70—O18	1.233 (4)
C24—H24A	0.99	C70—C71	1.472 (5)
C24—H24B	0.99	C71—H71A	0.98
C25—C26	1.508 (4)	C71—H71B	0.98
C25—H25A	0.99	C71—H71C	0.98
C25—H25B	0.99	C72—C73	1.488 (5)
C26—O2	1.236 (3)	C72—H72A	0.98
C26—N6	1.331 (3)	C72—H72B	0.98
C27—H27A	0.98	C72—H72C	0.98
C27—H27B	0.98	C73—O19	1.199 (4)
C27—H27C	0.98	C73—C74	1.488 (5)
C28—H28A	0.98	C74—H74A	0.98
C28—H28B	0.98	C74—H74B	0.98
C28—H28C	0.98	C74—H74C	0.98
C29—C30	1.512 (4)	C75—C76	1.473 (12)
C29—H29A	0.99	C75—H75A	0.98
C29—H29B	0.99	C75—H75B	0.98
C30—O3	1.236 (3)	C75—H75C	0.98
C30—N7	1.338 (3)	C76—O20	1.232 (10)
C31—C32	1.522 (4)	C76—C77	1.449 (13)
C31—H31A	0.99	C77—H77A	0.98
C31—H31B	0.99	C77—H77B	0.98
C32—C33	1.508 (4)	C77—H77C	0.98
C32—H32A	0.99	C78—C79	1.493 (5)
C32—H32B	0.99	C78—H78A	0.98
C33—O4	1.234 (4)	C78—H78B	0.98
C33—N8	1.346 (4)	C78—H78C	0.98
C34—H34A	0.98	C79—O21	1.231 (4)
C34—H34B	0.98	C79—C80	1.494 (5)
C34—H34C	0.98	C80—H80A	0.98
C35—H35A	0.98	C80—H80B	0.98
C35—H35B	0.98	C80—H80C	0.98
C35—H35C	0.98	N1—Co	1.884 (2)
C36—C37	1.541 (3)	N2—Co	1.920 (2)
C36—H36A	0.99	N3—Co	1.911 (2)
C36—H36B	0.99	N4—Co	1.885 (2)
C37—C38	1.511 (4)	N5—H5A	0.88
C37—H37A	0.99	N5—H5B	0.88
C37—H37B	0.99	N6—H6A	0.88
C38—O5	1.246 (3)	N6—H6B	0.88
C38—N9	1.327 (3)	N7—H7A	0.88
C39—H39A	0.98	N7—H7B	0.88
C39—H39B	0.98	N8—H8A	0.88
C39—H39C	0.98	N8—H8B	0.88
C40—H40A	0.98	N9—H9A	0.88
C40—H40B	0.98	N9—H9B	0.88
C40—H40C	0.98	N10—H10A	0.88
C41—C42	1.515 (3)	N10—H10B	0.88
C41—H41A	0.99	N11—H11	0.88
C41—H41B	0.99	N13—Co	2.189 (2)
C42—O6	1.248 (3)	P1—O9	1.4911 (19)
C42—N10	1.319 (3)	P1—O8	1.4968 (19)
C43—C44	1.529 (4)	P1—O11	1.5758 (19)
C43—H43A	0.99	P1—O10	1.6028 (18)
C43—H43B	0.99	P2—O17	1.4823 (18)
C44—C45	1.520 (4)	P2—O15	1.6064 (19)
C44—H44A	0.99	P2—O16	1.6213 (19)
C44—H44B	0.99	P2—Co	2.2269 (10)
C45—O7	1.243 (3)	O1W—H1Y	0.9512
C45—N11	1.332 (3)	O1W—H1Z	0.9416
C46—N11	1.450 (3)	O2W—H2Y	0.9424
C46—C47	1.520 (4)	O2W—H2Z	0.9397
C46—H46A	0.99	O3W—H3Y	0.9816
C46—H46B	0.99	O3W—H3Z	0.9829
C47—O11	1.468 (3)	O4W—H4Y	0.939
C47—C48	1.515 (4)	O4W—H4Z	0.9386
C47—H47	1	O5W—H5Y	0.9455
C48—H48A	0.98	O5W—H5Z	0.9445
C48—H48B	0.98	O6W—H6Y	0.9388
C48—H48C	0.98	O6W—H6Z	0.9402
C49—O12	1.414 (3)	O13—H13A	0.84
C49—N12	1.447 (3)	O14—H14	0.84
N1—C1—C19	101.68 (18)	C46—C47—H47	110
N1—C1—C20	110.27 (19)	C47—C48—H48A	109.5
C19—C1—C20	109.3 (2)	C47—C48—H48B	109.5
N1—C1—C2	102.04 (18)	H48A—C48—H48B	109.5
C19—C1—C2	119.8 (2)	C47—C48—H48C	109.5
C20—C1—C2	112.7 (2)	H48A—C48—H48C	109.5
C21—C2—C22	109.1 (2)	H48B—C48—H48C	109.5
C21—C2—C3	113.4 (2)	O12—C49—N12	107.57 (19)
C22—C2—C3	108.3 (2)	O12—C49—C50	107.0 (2)
C21—C2—C1	114.1 (2)	N12—C49—C50	113.1 (2)
C22—C2—C1	109.80 (19)	O12—C49—H49	109.7
C3—C2—C1	101.88 (19)	N12—C49—H49	109.7
C4—C3—C24	109.7 (2)	C50—C49—H49	109.7
C4—C3—C2	101.96 (19)	O13—C50—C51	112.7 (2)
C24—C3—C2	118.9 (2)	O13—C50—C49	109.2 (2)
C4—C3—H3	108.6	C51—C50—C49	99.4 (2)
C24—C3—H3	108.6	O13—C50—H50	111.7
C2—C3—H3	108.6	C51—C50—H50	111.7
N1—C4—C5	124.0 (2)	C49—C50—H50	111.7
N1—C4—C3	112.3 (2)	O10—C51—C52	110.1 (2)
C5—C4—C3	123.7 (2)	O10—C51—C50	112.4 (2)
C6—C5—C4	121.4 (2)	C52—C51—C50	105.1 (2)
C6—C5—C27	121.5 (2)	O10—C51—H51	109.7
C4—C5—C27	117.1 (2)	C52—C51—H51	109.7
C5—C6—N2	123.6 (2)	C50—C51—H51	109.7
C5—C6—C7	128.0 (2)	O12—C52—C51	106.1 (2)
N2—C6—C7	108.4 (2)	O12—C52—C53	108.3 (2)
C28—C7—C6	116.6 (2)	C51—C52—C53	113.9 (2)
C28—C7—C8	112.6 (2)	O12—C52—H52	109.5
C6—C7—C8	100.60 (19)	C51—C52—H52	109.5
C28—C7—C29	110.4 (2)	C53—C52—H52	109.5
C6—C7—C29	106.7 (2)	O14—C53—C52	111.9 (2)
C8—C7—C29	109.3 (2)	O14—C53—H53A	109.2
C9—C8—C31	111.8 (2)	C52—C53—H53A	109.2
C9—C8—C7	101.1 (2)	O14—C53—H53B	109.2
C31—C8—C7	112.1 (2)	C52—C53—H53B	109.2
C9—C8—H8	110.5	H53A—C53—H53B	107.9
C31—C8—H8	110.5	N13—C54—N12	113.6 (2)
C7—C8—H8	110.5	N13—C54—H54	123.2
N2—C9—C10	125.4 (2)	N12—C54—H54	123.2
N2—C9—C8	111.2 (2)	C56—C55—C60	119.1 (2)
C10—C9—C8	123.4 (2)	C56—C55—H55	120.5
C9—C10—C11	126.2 (2)	C60—C55—H55	120.5
C9—C10—H10	116.9	C55—C56—C57	121.0 (2)
C11—C10—H10	116.9	C55—C56—C61	119.1 (2)
N3—C11—C10	124.8 (2)	C57—C56—C61	119.9 (2)
N3—C11—C12	111.5 (2)	C58—C57—C56	119.9 (2)
C10—C11—C12	123.6 (2)	C58—C57—C62	120.0 (2)
C35—C12—C11	113.1 (2)	C56—C57—C62	120.1 (2)
C35—C12—C34	109.1 (2)	C57—C58—C59	118.5 (2)
C11—C12—C34	106.6 (2)	C57—C58—H58	120.8
C35—C12—C13	117.3 (2)	C59—C58—H58	120.8
C11—C12—C13	100.7 (2)	N12—C59—C58	132.0 (2)
C34—C12—C13	109.3 (2)	N12—C59—C60	105.8 (2)
C14—C13—C12	102.29 (19)	C58—C59—C60	122.2 (2)
C14—C13—C36	107.6 (2)	C55—C60—C59	119.4 (2)
C12—C13—C36	117.1 (2)	C55—C60—N13	131.4 (2)
C14—C13—H13	109.8	C59—C60—N13	109.2 (2)
C12—C13—H13	109.8	C56—C61—H61A	109.5
C36—C13—H13	109.8	C56—C61—H61B	109.5
C15—C14—N3	126.6 (2)	H61A—C61—H61B	109.5
C15—C14—C13	124.3 (2)	C56—C61—H61C	109.5
N3—C14—C13	108.7 (2)	H61A—C61—H61C	109.5
C14—C15—C16	121.1 (2)	H61B—C61—H61C	109.5
C14—C15—C39	118.7 (2)	C57—C62—H62A	109.5
C16—C15—C39	120.1 (2)	C57—C62—H62B	109.5
N4—C16—C15	122.2 (2)	H62A—C62—H62B	109.5
N4—C16—C17	111.1 (2)	C57—C62—H62C	109.5
C15—C16—C17	126.7 (2)	H62A—C62—H62C	109.5
C43—C17—C40	108.0 (2)	H62B—C62—H62C	109.5
C43—C17—C16	117.1 (2)	O15—C63—C65	107.5 (2)
C40—C17—C16	107.88 (19)	O15—C63—C64	108.9 (2)
C43—C17—C18	112.53 (19)	C65—C63—C64	112.4 (3)
C40—C17—C18	110.6 (2)	O15—C63—H63	109.3
C16—C17—C18	100.52 (19)	C65—C63—H63	109.3
C19—C18—C41	113.0 (2)	C64—C63—H63	109.3
C19—C18—C17	102.04 (19)	C63—C64—H64A	109.5
C41—C18—C17	116.6 (2)	C63—C64—H64B	109.5
C19—C18—H18	108.3	H64A—C64—H64B	109.5
C41—C18—H18	108.3	C63—C64—H64C	109.5
C17—C18—H18	108.3	H64A—C64—H64C	109.5
N4—C19—C18	102.98 (18)	H64B—C64—H64C	109.5
N4—C19—C1	107.13 (19)	C63—C65—H65A	109.5
C18—C19—C1	121.6 (2)	C63—C65—H65B	109.5
N4—C19—H19	108.2	H65A—C65—H65B	109.5
C18—C19—H19	108.2	C63—C65—H65C	109.5
C1—C19—H19	108.2	H65A—C65—H65C	109.5
C1—C20—H20A	109.5	H65B—C65—H65C	109.5
C1—C20—H20B	109.5	O16—C66—C68	107.2 (2)
H20A—C20—H20B	109.5	O16—C66—C67	111.0 (2)
C1—C20—H20C	109.5	C68—C66—C67	111.5 (2)
H20A—C20—H20C	109.5	O16—C66—H66	109
H20B—C20—H20C	109.5	C68—C66—H66	109
C2—C21—H21A	109.5	C67—C66—H66	109
C2—C21—H21B	109.5	C66—C67—H67A	109.5
H21A—C21—H21B	109.5	C66—C67—H67B	109.5
C2—C21—H21C	109.5	H67A—C67—H67B	109.5
H21A—C21—H21C	109.5	C66—C67—H67C	109.5
H21B—C21—H21C	109.5	H67A—C67—H67C	109.5
C23—C22—C2	116.7 (2)	H67B—C67—H67C	109.5
C23—C22—H22A	108.1	C66—C68—H68A	109.5
C2—C22—H22A	108.1	C66—C68—H68B	109.5
C23—C22—H22B	108.1	H68A—C68—H68B	109.5
C2—C22—H22B	108.1	C66—C68—H68C	109.5
H22A—C22—H22B	107.3	H68A—C68—H68C	109.5
O1—C23—N5	121.5 (2)	H68B—C68—H68C	109.5
O1—C23—C22	123.7 (2)	C70—C69—H69A	109.5
N5—C23—C22	114.9 (2)	C70—C69—H69B	109.5
C25—C24—C3	113.8 (2)	H69A—C69—H69B	109.5
C25—C24—H24A	108.8	C70—C69—H69C	109.5
C3—C24—H24A	108.8	H69A—C69—H69C	109.5
C25—C24—H24B	108.8	H69B—C69—H69C	109.5
C3—C24—H24B	108.8	O18—C70—C69	121.6 (3)
H24A—C24—H24B	107.7	O18—C70—C71	120.7 (3)
C26—C25—C24	110.4 (2)	C69—C70—C71	117.7 (3)
C26—C25—H25A	109.6	C70—C71—H71A	109.5
C24—C25—H25A	109.6	C70—C71—H71B	109.5
C26—C25—H25B	109.6	H71A—C71—H71B	109.5
C24—C25—H25B	109.6	C70—C71—H71C	109.5
H25A—C25—H25B	108.1	H71A—C71—H71C	109.5
O2—C26—N6	121.3 (3)	H71B—C71—H71C	109.5
O2—C26—C25	121.8 (2)	C73—C72—H72A	109.5
N6—C26—C25	117.0 (2)	C73—C72—H72B	109.5
C5—C27—H27A	109.5	H72A—C72—H72B	109.5
C5—C27—H27B	109.5	C73—C72—H72C	109.5
H27A—C27—H27B	109.5	H72A—C72—H72C	109.5
C5—C27—H27C	109.5	H72B—C72—H72C	109.5
H27A—C27—H27C	109.5	O19—C73—C74	121.7 (4)
H27B—C27—H27C	109.5	O19—C73—C72	121.1 (3)
C7—C28—H28A	109.5	C74—C73—C72	117.2 (4)
C7—C28—H28B	109.5	C73—C74—H74A	109.5
H28A—C28—H28B	109.5	C73—C74—H74B	109.5
C7—C28—H28C	109.5	H74A—C74—H74B	109.5
H28A—C28—H28C	109.5	C73—C74—H74C	109.5
H28B—C28—H28C	109.5	H74A—C74—H74C	109.5
C30—C29—C7	112.0 (2)	H74B—C74—H74C	109.5
C30—C29—H29A	109.2	O20—C76—C77	121.1 (8)
C7—C29—H29A	109.2	O20—C76—C75	122.1 (9)
C30—C29—H29B	109.2	C77—C76—C75	116.8 (8)
C7—C29—H29B	109.2	C79—C78—H78A	109.5
H29A—C29—H29B	107.9	C79—C78—H78B	109.5
O3—C30—N7	122.4 (3)	H78A—C78—H78B	109.5
O3—C30—C29	120.3 (2)	C79—C78—H78C	109.5
N7—C30—C29	117.2 (2)	H78A—C78—H78C	109.5
C32—C31—C8	115.4 (2)	H78B—C78—H78C	109.5
C32—C31—H31A	108.4	O21—C79—C78	121.7 (3)
C8—C31—H31A	108.4	O21—C79—C80	121.3 (3)
C32—C31—H31B	108.4	C78—C79—C80	117.0 (3)
C8—C31—H31B	108.4	C79—C80—H80A	109.5
H31A—C31—H31B	107.5	C79—C80—H80B	109.5
C33—C32—C31	111.2 (2)	H80A—C80—H80B	109.5
C33—C32—H32A	109.4	C79—C80—H80C	109.5
C31—C32—H32A	109.4	H80A—C80—H80C	109.5
C33—C32—H32B	109.4	H80B—C80—H80C	109.5
C31—C32—H32B	109.4	C4—N1—C1	112.4 (2)
H32A—C32—H32B	108	C4—N1—Co	130.81 (17)
O4—C33—N8	121.2 (3)	C1—N1—Co	116.69 (15)
O4—C33—C32	122.6 (3)	C9—N2—C6	110.0 (2)
N8—C33—C32	116.1 (3)	C9—N2—Co	122.59 (17)
C12—C34—H34A	109.5	C6—N2—Co	127.14 (17)
C12—C34—H34B	109.5	C11—N3—C14	110.1 (2)
H34A—C34—H34B	109.5	C11—N3—Co	123.56 (17)
C12—C34—H34C	109.5	C14—N3—Co	126.27 (16)
H34A—C34—H34C	109.5	C16—N4—C19	111.6 (2)
H34B—C34—H34C	109.5	C16—N4—Co	133.22 (17)
C12—C35—H35A	109.5	C19—N4—Co	114.21 (15)
C12—C35—H35B	109.5	C23—N5—H5A	120
H35A—C35—H35B	109.5	C23—N5—H5B	120
C12—C35—H35C	109.5	H5A—N5—H5B	120
H35A—C35—H35C	109.5	C26—N6—H6A	120
H35B—C35—H35C	109.5	C26—N6—H6B	120
C37—C36—C13	116.3 (2)	H6A—N6—H6B	120
C37—C36—H36A	108.2	C30—N7—H7A	120
C13—C36—H36A	108.2	C30—N7—H7B	120
C37—C36—H36B	108.2	H7A—N7—H7B	120
C13—C36—H36B	108.2	C33—N8—H8A	120
H36A—C36—H36B	107.4	C33—N8—H8B	120
C38—C37—C36	114.6 (2)	H8A—N8—H8B	120
C38—C37—H37A	108.6	C38—N9—H9A	120
C36—C37—H37A	108.6	C38—N9—H9B	120
C38—C37—H37B	108.6	H9A—N9—H9B	120
C36—C37—H37B	108.6	C42—N10—H10A	120
H37A—C37—H37B	107.6	C42—N10—H10B	120
O5—C38—N9	122.3 (3)	H10A—N10—H10B	120
O5—C38—C37	121.1 (2)	C45—N11—C46	123.8 (2)
N9—C38—C37	116.6 (2)	C45—N11—H11	118.1
C15—C39—H39A	109.5	C46—N11—H11	118.1
C15—C39—H39B	109.5	C54—N12—C59	106.7 (2)
H39A—C39—H39B	109.5	C54—N12—C49	125.4 (2)
C15—C39—H39C	109.5	C59—N12—C49	125.3 (2)
H39A—C39—H39C	109.5	C54—N13—C60	104.7 (2)
H39B—C39—H39C	109.5	C54—N13—Co	122.50 (17)
C17—C40—H40A	109.5	C60—N13—Co	132.78 (16)
C17—C40—H40B	109.5	O9—P1—O8	116.50 (11)
H40A—C40—H40B	109.5	O9—P1—O11	106.63 (10)
C17—C40—H40C	109.5	O8—P1—O11	112.34 (11)
H40A—C40—H40C	109.5	O9—P1—O10	110.73 (11)
H40B—C40—H40C	109.5	O8—P1—O10	108.94 (10)
C42—C41—C18	116.1 (2)	O11—P1—O10	100.52 (10)
C42—C41—H41A	108.3	O17—P2—O15	113.11 (10)
C18—C41—H41A	108.3	O17—P2—O16	110.95 (10)
C42—C41—H41B	108.3	O15—P2—O16	101.06 (10)
C18—C41—H41B	108.3	O17—P2—Co	114.32 (8)
H41A—C41—H41B	107.4	O15—P2—Co	104.71 (7)
O6—C42—N10	123.3 (2)	O16—P2—Co	111.78 (7)
O6—C42—C41	120.8 (2)	H1Y—O1W—H1Z	108.1
N10—C42—C41	115.8 (2)	H2Y—O2W—H2Z	105.5
C44—C43—C17	117.4 (2)	H3Y—O3W—H3Z	101
C44—C43—H43A	108	H4Y—O4W—H4Z	92.7
C17—C43—H43A	108	H5Y—O5W—H5Z	90.2
C44—C43—H43B	108	H6Y—O6W—H6Z	99.2
C17—C43—H43B	108	C51—O10—P1	119.02 (15)
H43A—C43—H43B	107.2	C47—O11—P1	120.86 (16)
C45—C44—C43	110.0 (2)	C49—O12—C52	109.49 (18)
C45—C44—H44A	109.7	C50—O13—H13A	109.5
C43—C44—H44A	109.7	C53—O14—H14	109.5
C45—C44—H44B	109.7	C63—O15—P2	119.91 (16)
C43—C44—H44B	109.7	C66—O16—P2	122.44 (16)
H44A—C44—H44B	108.2	N1—Co—N4	83.33 (9)
O7—C45—N11	122.9 (3)	N1—Co—N3	172.73 (9)
O7—C45—C44	120.6 (2)	N4—Co—N3	90.44 (9)
N11—C45—C44	116.4 (2)	N1—Co—N2	89.62 (9)
N11—C46—C47	112.2 (2)	N4—Co—N2	172.77 (9)
N11—C46—H46A	109.2	N3—Co—N2	96.70 (9)
C47—C46—H46A	109.2	N1—Co—N13	90.80 (8)
N11—C46—H46B	109.2	N4—Co—N13	94.06 (8)
C47—C46—H46B	109.2	N3—Co—N13	85.89 (8)
H46A—C46—H46B	107.9	N2—Co—N13	87.65 (8)
O11—C47—C48	108.2 (2)	N1—Co—P2	97.47 (6)
O11—C47—C46	106.5 (2)	N4—Co—P2	92.18 (6)
C48—C47—C46	112.0 (2)	N3—Co—P2	86.47 (6)
O11—C47—H47	110	N2—Co—P2	87.10 (6)
C48—C47—H47	110	N13—Co—P2	170.16 (6)
N1—C1—C2—C21	151.0 (2)	C60—C55—C56—C61	−179.0 (2)
C19—C1—C2—C21	−97.9 (3)	C55—C56—C57—C58	0.7 (4)
C20—C1—C2—C21	32.7 (3)	C61—C56—C57—C58	−179.9 (3)
N1—C1—C2—C22	−86.3 (2)	C55—C56—C57—C62	178.9 (3)
C19—C1—C2—C22	24.9 (3)	C61—C56—C57—C62	−1.7 (4)
C20—C1—C2—C22	155.5 (2)	C56—C57—C58—C59	−0.9 (4)
N1—C1—C2—C3	28.4 (2)	C62—C57—C58—C59	−179.0 (3)
C19—C1—C2—C3	139.5 (2)	C57—C58—C59—N12	178.4 (3)
C20—C1—C2—C3	−89.9 (2)	C57—C58—C59—C60	−0.1 (4)
C21—C2—C3—C4	−151.7 (2)	C56—C55—C60—C59	−1.4 (4)
C22—C2—C3—C4	87.1 (2)	C56—C55—C60—N13	−178.3 (2)
C1—C2—C3—C4	−28.7 (2)	N12—C59—C60—C55	−177.6 (2)
C21—C2—C3—C24	−31.0 (3)	C58—C59—C60—C55	1.3 (4)
C22—C2—C3—C24	−152.2 (2)	N12—C59—C60—N13	0.0 (3)
C1—C2—C3—C24	92.1 (2)	C58—C59—C60—N13	178.9 (2)
C24—C3—C4—N1	−107.3 (2)	C5—C4—N1—C1	−178.5 (2)
C2—C3—C4—N1	19.7 (3)	C3—C4—N1—C1	−0.8 (3)
C24—C3—C4—C5	70.4 (3)	C5—C4—N1—Co	4.3 (4)
C2—C3—C4—C5	−162.6 (2)	C3—C4—N1—Co	−177.95 (16)
N1—C4—C5—C6	10.4 (4)	C19—C1—N1—C4	−142.5 (2)
C3—C4—C5—C6	−167.0 (2)	C20—C1—N1—C4	101.6 (2)
N1—C4—C5—C27	−170.9 (2)	C2—C1—N1—C4	−18.3 (2)
C3—C4—C5—C27	11.6 (3)	C19—C1—N1—Co	35.1 (2)
C4—C5—C6—N2	−6.4 (4)	C20—C1—N1—Co	−80.8 (2)
C27—C5—C6—N2	175.1 (2)	C2—C1—N1—Co	159.31 (14)
C4—C5—C6—C7	175.3 (2)	C10—C9—N2—C6	166.3 (2)
C27—C5—C6—C7	−3.2 (4)	C8—C9—N2—C6	−13.0 (3)
C5—C6—C7—C28	−36.9 (4)	C10—C9—N2—Co	−8.2 (3)
N2—C6—C7—C28	144.6 (2)	C8—C9—N2—Co	172.46 (15)
C5—C6—C7—C8	−159.0 (2)	C5—C6—N2—C9	174.3 (2)
N2—C6—C7—C8	22.5 (2)	C7—C6—N2—C9	−7.1 (3)
C5—C6—C7—C29	87.0 (3)	C5—C6—N2—Co	−11.4 (3)
N2—C6—C7—C29	−91.5 (2)	C7—C6—N2—Co	167.19 (16)
C28—C7—C8—C9	−152.6 (2)	C10—C11—N3—C14	174.3 (2)
C6—C7—C8—C9	−27.7 (2)	C12—C11—N3—C14	−9.7 (3)
C29—C7—C8—C9	84.3 (2)	C10—C11—N3—Co	−3.7 (4)
C28—C7—C8—C31	−33.3 (3)	C12—C11—N3—Co	172.26 (16)
C6—C7—C8—C31	91.6 (2)	C15—C14—N3—C11	178.8 (2)
C29—C7—C8—C31	−156.4 (2)	C13—C14—N3—C11	−7.8 (3)
C31—C8—C9—N2	−92.9 (2)	C15—C14—N3—Co	−3.2 (4)
C7—C8—C9—N2	26.6 (3)	C13—C14—N3—Co	170.12 (16)
C31—C8—C9—C10	87.7 (3)	C15—C16—N4—C19	−171.9 (2)
C7—C8—C9—C10	−152.8 (2)	C17—C16—N4—C19	4.3 (3)
N2—C9—C10—C11	−0.2 (4)	C15—C16—N4—Co	−4.1 (4)
C8—C9—C10—C11	179.0 (2)	C17—C16—N4—Co	172.06 (16)
C9—C10—C11—N3	6.9 (4)	C18—C19—N4—C16	−24.6 (2)
C9—C10—C11—C12	−168.6 (2)	C1—C19—N4—C16	−153.86 (19)
N3—C11—C12—C35	148.3 (2)	C18—C19—N4—Co	165.16 (14)
C10—C11—C12—C35	−35.6 (3)	C1—C19—N4—Co	35.9 (2)
N3—C11—C12—C34	−91.8 (3)	O7—C45—N11—C46	−7.2 (4)
C10—C11—C12—C34	84.3 (3)	C44—C45—N11—C46	174.6 (2)
N3—C11—C12—C13	22.3 (3)	C47—C46—N11—C45	−95.7 (3)
C10—C11—C12—C13	−161.7 (2)	N13—C54—N12—C59	−2.4 (3)
C35—C12—C13—C14	−147.7 (2)	N13—C54—N12—C49	−164.9 (2)
C11—C12—C13—C14	−24.5 (2)	C58—C59—N12—C54	−177.4 (3)
C34—C12—C13—C14	87.5 (2)	C60—C59—N12—C54	1.4 (3)
C35—C12—C13—C36	−30.3 (3)	C58—C59—N12—C49	−14.8 (4)
C11—C12—C13—C36	92.9 (2)	C60—C59—N12—C49	163.9 (2)
C34—C12—C13—C36	−155.1 (2)	O12—C49—N12—C54	−45.5 (3)
C12—C13—C14—C15	−165.3 (2)	C50—C49—N12—C54	72.4 (3)
C36—C13—C14—C15	70.7 (3)	O12—C49—N12—C59	155.1 (2)
C12—C13—C14—N3	21.1 (3)	C50—C49—N12—C59	−87.0 (3)
C36—C13—C14—N3	−102.8 (2)	N12—C54—N13—C60	2.3 (3)
N3—C14—C15—C16	2.8 (4)	N12—C54—N13—Co	−177.20 (16)
C13—C14—C15—C16	−169.5 (2)	C55—C60—N13—C54	175.9 (3)
N3—C14—C15—C39	−175.1 (2)	C59—C60—N13—C54	−1.3 (3)
C13—C14—C15—C39	12.5 (4)	C55—C60—N13—Co	−4.7 (4)
C14—C15—C16—N4	0.8 (4)	C59—C60—N13—Co	178.10 (17)
C39—C15—C16—N4	178.7 (2)	C52—C51—O10—P1	−129.82 (18)
C14—C15—C16—C17	−174.8 (2)	C50—C51—O10—P1	113.4 (2)
C39—C15—C16—C17	3.2 (4)	O9—P1—O10—C51	−74.9 (2)
N4—C16—C17—C43	139.4 (2)	O8—P1—O10—C51	54.5 (2)
C15—C16—C17—C43	−44.6 (3)	O11—P1—O10—C51	172.67 (18)
N4—C16—C17—C40	−98.7 (2)	C48—C47—O11—P1	−107.4 (2)
C15—C16—C17—C40	77.3 (3)	C46—C47—O11—P1	132.05 (19)
N4—C16—C17—C18	17.2 (2)	O9—P1—O11—C47	−179.88 (17)
C15—C16—C17—C18	−166.8 (2)	O8—P1—O11—C47	51.3 (2)
C43—C17—C18—C19	−155.6 (2)	O10—P1—O11—C47	−64.34 (18)
C40—C17—C18—C19	83.6 (2)	N12—C49—O12—C52	145.7 (2)
C16—C17—C18—C19	−30.2 (2)	C50—C49—O12—C52	23.9 (3)
C43—C17—C18—C41	80.8 (3)	C51—C52—O12—C49	−1.9 (3)
C40—C17—C18—C41	−40.1 (3)	C53—C52—O12—C49	120.8 (2)
C16—C17—C18—C41	−153.9 (2)	C65—C63—O15—P2	−132.9 (2)
C41—C18—C19—N4	159.38 (19)	C64—C63—O15—P2	105.0 (2)
C17—C18—C19—N4	33.3 (2)	O17—P2—O15—C63	44.5 (2)
C41—C18—C19—C1	−80.9 (3)	O16—P2—O15—C63	−74.2 (2)
C17—C18—C19—C1	153.1 (2)	Co—P2—O15—C63	169.55 (17)
N1—C1—C19—N4	−42.0 (2)	C68—C66—O16—P2	163.44 (19)
C20—C1—C19—N4	74.6 (2)	C67—C66—O16—P2	−74.6 (3)
C2—C1—C19—N4	−153.3 (2)	O17—P2—O16—C66	10.9 (2)
N1—C1—C19—C18	−159.7 (2)	O15—P2—O16—C66	131.07 (18)
C20—C1—C19—C18	−43.2 (3)	Co—P2—O16—C66	−118.03 (17)
C2—C1—C19—C18	89.0 (3)	C4—N1—Co—N4	162.9 (2)
C21—C2—C22—C23	−59.8 (3)	C1—N1—Co—N4	−14.22 (16)
C3—C2—C22—C23	64.1 (3)	C4—N1—Co—N2	−15.5 (2)
C1—C2—C22—C23	174.5 (2)	C1—N1—Co—N2	167.42 (16)
C2—C22—C23—O1	−15.0 (4)	C4—N1—Co—N13	−103.1 (2)
C2—C22—C23—N5	165.5 (2)	C1—N1—Co—N13	79.78 (16)
C4—C3—C24—C25	−155.8 (2)	C4—N1—Co—P2	71.5 (2)
C2—C3—C24—C25	87.5 (3)	C1—N1—Co—P2	−105.56 (15)
C3—C24—C25—C26	173.2 (2)	C16—N4—Co—N1	179.4 (2)
C24—C25—C26—O2	−90.5 (3)	C19—N4—Co—N1	−13.06 (16)
C24—C25—C26—N6	89.1 (3)	C16—N4—Co—N3	3.1 (2)
C28—C7—C29—C30	−59.3 (3)	C19—N4—Co—N3	170.69 (16)
C6—C7—C29—C30	173.0 (2)	C16—N4—Co—N13	89.1 (2)
C8—C7—C29—C30	65.1 (3)	C19—N4—Co—N13	−103.40 (16)
C7—C29—C30—O3	−84.5 (3)	C16—N4—Co—P2	−83.3 (2)
C7—C29—C30—N7	94.7 (3)	C19—N4—Co—P2	84.20 (15)
C9—C8—C31—C32	−54.6 (3)	C11—N3—Co—N4	178.2 (2)
C7—C8—C31—C32	−167.4 (2)	C14—N3—Co—N4	0.5 (2)
C8—C31—C32—C33	178.8 (2)	C11—N3—Co—N2	−3.0 (2)
C31—C32—C33—O4	20.6 (4)	C14—N3—Co—N2	179.32 (19)
C31—C32—C33—N8	−160.0 (3)	C11—N3—Co—N13	84.1 (2)
C14—C13—C36—C37	−168.2 (2)	C14—N3—Co—N13	−93.5 (2)
C12—C13—C36—C37	77.4 (3)	C11—N3—Co—P2	−89.65 (19)
C13—C36—C37—C38	49.5 (3)	C14—N3—Co—P2	92.67 (19)
C36—C37—C38—O5	−114.6 (3)	C9—N2—Co—N1	−167.84 (19)
C36—C37—C38—N9	65.3 (3)	C6—N2—Co—N1	18.6 (2)
C19—C18—C41—C42	171.4 (2)	C9—N2—Co—N3	8.6 (2)
C17—C18—C41—C42	−70.8 (3)	C6—N2—Co—N3	−165.0 (2)
C18—C41—C42—O6	−43.5 (3)	C9—N2—Co—N13	−77.02 (19)
C18—C41—C42—N10	139.7 (2)	C6—N2—Co—N13	109.4 (2)
C40—C17—C43—C44	−170.6 (2)	C9—N2—Co—P2	94.66 (19)
C16—C17—C43—C44	−48.7 (3)	C6—N2—Co—P2	−78.94 (19)
C18—C17—C43—C44	67.0 (3)	C54—N13—Co—N1	−130.9 (2)
C17—C43—C44—C45	167.8 (2)	C60—N13—Co—N1	49.8 (2)
C43—C44—C45—O7	−64.8 (3)	C54—N13—Co—N4	−47.6 (2)
C43—C44—C45—N11	113.4 (3)	C60—N13—Co—N4	133.1 (2)
N11—C46—C47—O11	−53.3 (3)	C54—N13—Co—N3	42.6 (2)
N11—C46—C47—C48	−171.4 (2)	C60—N13—Co—N3	−136.7 (2)
O12—C49—C50—O13	83.2 (2)	C54—N13—Co—N2	139.5 (2)
N12—C49—C50—O13	−35.0 (3)	C60—N13—Co—N2	−39.8 (2)
O12—C49—C50—C51	−34.9 (2)	O17—P2—Co—N1	−127.41 (11)
N12—C49—C50—C51	−153.1 (2)	O15—P2—Co—N1	108.26 (10)
O13—C50—C51—O10	37.1 (3)	O16—P2—Co—N1	−0.31 (10)
C49—C50—C51—O10	152.6 (2)	O17—P2—Co—N4	149.03 (11)
O13—C50—C51—C52	−82.7 (2)	O15—P2—Co—N4	24.70 (10)
C49—C50—C51—C52	32.8 (2)	O16—P2—Co—N4	−83.87 (10)
O10—C51—C52—O12	−141.9 (2)	O17—P2—Co—N3	58.73 (10)
C50—C51—C52—O12	−20.7 (3)	O15—P2—Co—N3	−65.60 (10)
O10—C51—C52—C53	99.0 (3)	O16—P2—Co—N3	−174.18 (10)
C50—C51—C52—C53	−139.8 (2)	O17—P2—Co—N2	−38.17 (10)
O12—C52—C53—O14	−60.0 (3)	O15—P2—Co—N2	−162.50 (9)
C51—C52—C53—O14	57.8 (3)	O16—P2—Co—N2	88.92 (10)
C60—C55—C56—C57	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1Y···O2W^i	0.95	1.85	2.797 (3)	176
O1W—H1Z···O8^ii	0.94	1.78	2.706 (3)	168
O2W—H2Y···O9^iii	0.94	1.81	2.727 (3)	164
O2W—H2Z···O3	0.94	1.76	2.700 (3)	175
O3W—H3Y···O8^ii	0.98	1.71	2.684 (3)	169
O3W—H3Z···O6^iv	0.98	1.86	2.798 (3)	158
O4W—H4Y···O1W^v	0.94	1.87	2.782 (3)	164
O4W—H4Z···O6	0.94	1.90	2.828 (3)	170
N5—H5A···O4^i	0.88	2.06	2.937 (3)	173
N5—H5B···O21	0.88	2.22	3.103 (3)	174
O5W—H5Y···O2W^i	0.95	1.93	2.872 (3)	175
O5W—H5Z···O7^ii	0.95	1.87	2.802 (3)	168
N6—H6A···O4W^iv	0.88	2.52	3.162 (3)	130
N6—H6A···O9W^vi	0.88	2.43	3.276 (11)	162
N6—H6B···O9^iv	0.88	2.11	2.988 (3)	172
N6—H6B···O11^iv	0.88	2.63	3.227 (3)	126
O6W—H6Y···O21^vii	0.94	1.97	2.877 (3)	163
O6W—H6Z···O2	0.94	1.77	2.702 (3)	170
N7—H7A···O9^iii	0.88	2.14	3.008 (3)	166
N7—H7B···O3W^viii	0.88	2.20	2.947 (3)	142
N8—H8A···O19	0.88	2.31	3.122 (4)	153
N8—H8B···O18^ix	0.88	2.11	2.982 (4)	169
N9—H9A···O1^ix	0.88	2.22	2.866 (3)	130
N9—H9B···O5W^ix	0.88	2.02	2.882 (3)	167
N10—H10A···O5^x	0.88	2.10	2.928 (3)	156
N10—H10B···O6W^i	0.88	1.97	2.838 (3)	170
N11—H11···O4W	0.88	2.03	2.909 (3)	177
O13—H13A···O1W^v	0.84	1.96	2.777 (3)	164
O14—H14···O3W^ix	0.84	2.06	2.902 (3)	175

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