(N-{[4-(1,3-Benzothia­zol-2-yl)­anilino]carbonyl­methyl-[kappa]O}iminodiacetato-[kappa]³O,N,O')(1,10-phenanthroline-[kappa]²N,N')cobalt(II) penta­hydrate

The title compound, [Co(C₁₉H₁₅N₃O₅S)(C₁₂H₈N₂)]·5H₂O, has a moderately distorted octa­hedral coordination environment composed of two N atoms of a 1,10-phenanthroline ligand and one N and three O atoms of an N-{[4-(1,3-benzo­thia­zol-2-­yl)­anilino]­carbonyl­methyl}­imino­diacetate (ZL-5^2-) ligand. The ring systems of the phenanthroline and ZL-5^2- ligands are coplanar and the complexes pack in layers parallel to the ab plane with the rings of adjacent complexes facing one another. The layers stack along the c axis and are linked by hydrogen bonds involving the five water solvent mol­ecules in the asymmetric unit and O atoms of the acetate groups of the ZL-5^2- ligand. This is believed to be the first crystal structure of a complex of a 2-(4-amino­phenyl)­benzo­thia­zole ligand.

S1. Comment

In recent years, much effort has been directed towards the identification and characterization of novel potent and selective anticancer ligand molecules. 2-(4-Aminophenyl)benzothiazole (CJM 126) is an intriguing compound which emanated from a drug discovery programme initially aimed at developing tyrosine kinase inhibitors (Stevens et al., 1994). Novel 2-(4-aminophenyl)benzothiazoles possess remarkably selective antitumour properties (Bradshaw, Wrigley et al., 1998; Bradshaw, Shi et al., 1998) and represent a mechanistic class distinct from clinically used chemotherapeutic agents. The original (unsubstituted) member of this series, 2-(4-aminophenyl)benzothiazole, was found to exhibit potent and selective activity against certain breast carcinoma cell lines in vitro (e.g. MCF-7 and MDA 468, IC₅₀ < 1 nM) (Bradshaw et al., 2002) irrespective of oestrogen receptor status and with an unusual biphasic dose–response relationship (Shi et al., 1996). Derivatives such as 2-(4-amino-3-methylphenyl)benzothiazole (DF203, NSC 67449) and 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5 F203, NSC 703786) were selected as lead candidates for further development on the basis of superior in vivo activity (Bradshaw, Wrigley et al., 1998; Bradshaw, Shi et al., 1998; Bradshaw et al., 2001). In selective cytotoxicity experiments on various tumour cell lines, N-{[4-(1,3-benzothiazol-2-yl)anilino]carbonylmethyl}iminodiacetic acid (ZL-5) shows obvious inhibition activity on MCF-7 breast tumour cells [Quantify as above for two other compounds? Reference?].

Our interest is focused on the coordination chemistry of 2-(4-aminophenyl)benzothiazole with metals via linking to other groups such as iminodiacetic acid. We successfully synthesized ZL-5 and its complex with Co^II, the title compound, (I). As far as we know, this is the first crystal structure of a 2-(4-aminophenyl)benzothiazole complex. There are a few reports of structures involving benzothiazole derivatives, for example 2-(2-hydroxyphenyl)benzothiazole (Yu et al., 2003; Tong et al., 2005), 2-phenylbenzothiazole (Churchill et al., 1980; Laskar et al., 2005), 2-mercaptobenzothiazole (Brandenburg et al., 1987; Cheng et al., 1995) and 2-(pyridin-2-yl)benzothiazole (Hu et al., 1990; He et al., 2004). These compounds vary mainly in the group at the 2-position of the benzothiazole and they are different from ZL-5, where 2-(4-aminophenyl)benzothiazole is conjugated to iminodiacetic acid though a –CH₂CO– group. Moreover, in their complexes they are all coordinated with metals through one N atom and other atoms from the benzothiazole moiety (Churchill et al., 1980; Laskar et al., 2005; Duatti et al., 1988; Pyrz et al., 1991). By contrast, Co^II in (I) does not coordinate to ZL-5 through the 2-(4-aminophenyl)benzothiazole group, but rather through one N and two O atoms of the iminodiacetate, and one amide O atom.

Compound (I) contains a [Co(C₁₉H₁₅N₂SO₅)(C₁₂H₈N₂)] complex and five water molecules in the asymmetric unit (Fig. 1). Each Co^II ion is bonded to two pyridine N atoms of the bidentate 1,10-phenanthroline ligand, and one iminodiacetate N atom and three O atoms from the tetradentate ZL-5 ligand. This ligand set generates a slightly distorted octahedral geometry, with three N atoms and one amide O atom occupying the equatorial plane, and two carboxylate O atoms from iminodiacetate occupying the axial positions. Bond angles in the coordination sphere that differ from ideal values by more than 10° are given in Table 1. This is the first structure in which iminodiacetic acid is linked with benzothiazole by a –CH₂CO– group, allowing ZL-5 to act as a tetradentate ligand. This is a rare coordination mode for an N-(N'-subtituted-acetamide)iminodiacetic acid compound in comparison with reported examples (Kanamori et al., 2001; Radanović et al., 2003). The presence of the –CH₂CO– spacer introduces sufficient flexibility to permit a coplanar arrangement of the planes of the phenanthroline and ZL-5 ligands [dihedral angle 3.293 (2)°].

In the crystal structure of (I), adjacent complexes are packed into layers in the ab plane so as to afford face-to-face π–π interactions between the benzothiazole plane of one molecule and the phenanthroline plane of an adjacent molecule along the b direction (Fig. 2). The observed stacking in these molecules, with an interplanar distance of about 3.343 (2) Å, is similar to those encountered in the base stacking of DNA. Thus, the whole structure may easily bind to DNA in an intercalative mode. The layers stack in the c direction and are held together by a network of hydrogen bonds involving the five water molecules in the asymmetric unit and the O and N atoms of the ZL-5 ligand molecules (Table 2).

A prominent feature of the complex is the presence of an iminodiacetate group on the mother heterocyclic ring in ZL-5. When bonded to the Co^II ion, it readily makes the metal coordination environment saturated without much steric hindrance, and each carboxylate –COOH group is deprotonated to form a charge-neutral complex. Charge neutrality is an important characteristic for biological activity, allowing mobilization of intracellular metal ions through the cell membrane. Furthermore, the solubility of the complex is improved compared with that of 2-(4-aminophenyl)benzothiazole (CJM 126) by the introduction of the hydrophilic iminodiacetate group.

Related literature

For related literature, see: Bradshaw et al. (2001, 2002); Bradshaw, Shi, Schultz, Paull, Kelland, Wilson, Garner, ?, Fiebig, Wrigley & Stevens (1998); Bradshaw, Wrigley, Shi, Schultz, Paull & Stevens (1998); Brandenburg et al. (1987); Cheng et al. (1995); Churchill et al. (1980); Duatti et al. (1988); He et al. (2004); Hu et al. (1990); Kanamori et al. (2001); Laskar et al. (2005); Pyrz et al. (1991); Radanović et al. (2003); Shi (1996); Stevens et al. (1994); Tong et al. (2005); Yu et al. (2003).

S2. Experimental

In a 250 ml round-bottomed flask equipped with a magnetic stirrer and condenser were placed 2-(4-chloroacetamidophenyl)benzothiazole (5 g, 0.0165 mol), iminodiacetic acid (2.42 g, 0.0182 mol), sodium carbonate (3.0 g, 0.028 mol) and 75% ethanol solution (200 ml). The stirred mixture was heated to reflux for 12 h, after which the solid was precipitated at pH 2.5 with 5% HCl. The crude product was collected by filtration, washed with water and ethanol, and crystallized from absolute ethanol to afford ZL-5 (6.1 g, 0.015 mol, 91%) as a green powder.

Orange platelet crystals of (I) were obtained by slow evaporation of a dimethylformamide solution of ZL-5, 1,10-phenanthroline and CoCl₂·6H₂O (molar ratio 1:1:1) at room temperature.

S3. Refinement

The positional parameters of the water and imine H atoms were calculated on the basis of the positions of their parent atoms, with U_iso(H) = 1.5U_eq(O or N). All other H atoms were located in difference Fourier maps and then regenerated at ideal positions and treated as riding, with C—H(aromatic) = 0.95 Å and C—H(alkyl) = 0.99 Å, and with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC & Rigaku, 2006).

Figures

	Fig. 1. A drawing of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A packing diagram for (I), showing the π–π interactions along the b direction.

(N-{[4-(1,3-Benzothiazol-2-yl)anilino]carbonylmethyl-κO}iminodiacetato- κ³O,N,O')(1,10-phenanthroline-κ²N,N')cobalt(II) pentahydrate

Crystal data

[Co(C19H15N3O5S)(C12H8N2)]·5H2O	Z = 2
Mr = 726.62	F(000) = 754.00
Triclinic, P1	Dx = 1.547 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 8.9990 (7) Å	Cell parameters from 13624 reflections
b = 12.7766 (7) Å	θ = 3.0–27.5°
c = 14.0652 (8) Å	µ = 0.69 mm^−1
α = 92.661 (2)°	T = 123 K
β = 102.770 (2)°	Platelet, orange
γ = 97.389 (2)°	0.50 × 0.50 × 0.20 mm
V = 1559.39 (17) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	6151 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.030
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.703, Tmax = 0.872	k = −16→15
15300 measured reflections	l = −18→18
7094 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0704P)^2 + 0.1918P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.118	(Δ/σ)max = 0.001
S = 1.12	Δρmax = 0.56 e Å^−3
7094 reflections	Δρmin = −0.83 e Å^−3
434 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Co1	0.75225 (3)	0.491016 (18)	0.223227 (17)	0.01972 (8)
S1	0.14617 (6)	1.03698 (4)	−0.11015 (3)	0.02550 (12)
O1	1.09449 (15)	0.66212 (11)	0.43687 (10)	0.0274 (3)
O2	0.95974 (15)	0.57971 (10)	0.29437 (10)	0.0241 (2)
O3	0.40562 (17)	0.30933 (11)	0.30747 (11)	0.0303 (3)
O4	0.55117 (15)	0.39093 (11)	0.21629 (10)	0.0254 (2)
O5	0.64477 (15)	0.62339 (11)	0.18280 (10)	0.0241 (2)
O6	0.4149 (2)	0.20729 (12)	0.47528 (11)	0.0376 (3)
O7	0.33363 (17)	0.78664 (11)	0.37750 (11)	0.0296 (3)
O8	0.3104 (2)	1.01132 (12)	0.37460 (12)	0.0405 (3)
O9	0.61863 (16)	0.88950 (11)	−0.21649 (11)	0.0296 (3)
O10	0.2537 (2)	0.49183 (15)	0.33575 (16)	0.0526 (4)
N1	0.49215 (18)	0.73715 (12)	0.22776 (11)	0.0224 (3)
N2	0.32545 (18)	0.93921 (13)	−0.19224 (12)	0.0243 (3)
N3	0.69718 (17)	0.53770 (12)	0.36237 (11)	0.0195 (3)
N4	0.77969 (18)	0.45710 (12)	0.08105 (11)	0.0213 (3)
N5	0.87612 (18)	0.35589 (12)	0.24202 (11)	0.0217 (3)
C1	0.4470 (2)	0.78843 (14)	0.14151 (13)	0.0210 (3)
C2	0.3494 (2)	0.86382 (15)	0.14557 (14)	0.0249 (3)
C3	0.2964 (2)	0.91685 (15)	0.06405 (14)	0.0253 (3)
C4	0.3390 (2)	0.89541 (14)	−0.02336 (14)	0.0222 (3)
C5	0.4360 (2)	0.81875 (16)	−0.02700 (15)	0.0271 (4)
C6	0.4916 (2)	0.76662 (15)	0.05463 (14)	0.0262 (3)
C7	0.2828 (2)	0.95029 (15)	−0.11056 (14)	0.0226 (3)
C8	0.1469 (2)	1.05893 (15)	−0.23085 (14)	0.0248 (3)
C9	0.0601 (2)	1.12155 (16)	−0.29365 (15)	0.0300 (4)
C10	0.0758 (2)	1.12087 (17)	−0.38912 (15)	0.0313 (4)
C11	0.1765 (2)	1.06051 (17)	−0.42183 (16)	0.0311 (4)
C12	0.2650 (2)	1.00064 (17)	−0.35943 (15)	0.0294 (4)
C13	0.2492 (2)	0.99887 (15)	−0.26247 (14)	0.0242 (3)
C14	0.5814 (2)	0.66065 (14)	0.24393 (13)	0.0205 (3)
C15	0.5950 (2)	0.62040 (15)	0.34447 (14)	0.0248 (3)
C16	0.8440 (2)	0.57667 (16)	0.43285 (14)	0.0260 (3)
C17	0.6129 (2)	0.44056 (14)	0.38882 (14)	0.0224 (3)
C18	0.9763 (2)	0.61095 (14)	0.38395 (14)	0.0225 (3)
C19	0.5148 (2)	0.37546 (14)	0.29677 (14)	0.0236 (3)
C20	0.7221 (2)	0.50246 (15)	0.00039 (14)	0.0238 (3)
C21	0.7551 (2)	0.47879 (15)	−0.09022 (14)	0.0250 (3)
C22	0.8532 (2)	0.40592 (15)	−0.09668 (14)	0.0258 (3)
C23	0.9150 (2)	0.35521 (14)	−0.01298 (14)	0.0237 (3)
C24	0.8722 (2)	0.38217 (14)	0.07398 (13)	0.0206 (3)
C25	1.0193 (2)	0.27868 (15)	−0.01230 (15)	0.0271 (4)
C26	1.0721 (2)	0.23030 (15)	0.06969 (15)	0.0271 (4)
C27	1.0232 (2)	0.25196 (15)	0.15783 (14)	0.0237 (3)
C28	0.9260 (2)	0.32933 (14)	0.16105 (14)	0.0212 (3)
C29	1.0664 (2)	0.19872 (15)	0.24302 (15)	0.0255 (3)
C30	1.0133 (2)	0.22397 (15)	0.32406 (15)	0.0261 (3)
C31	0.9192 (2)	0.30402 (15)	0.32097 (14)	0.0256 (3)
H1	0.4568	0.7583	0.2778	0.027*
H2	0.3191	0.8790	0.2047	0.030*
H3	0.2301	0.9684	0.0678	0.030*
H5	0.4641	0.8022	−0.0866	0.032*
H6	0.5598	0.7163	0.0515	0.031*
H9	−0.0074	1.1632	−0.2714	0.036*
H10	0.0171	1.1622	−0.4335	0.038*
H11	0.1840	1.0608	−0.4881	0.037*
H12	0.3352	0.9614	−0.3816	0.035*
H20	0.6553	0.5535	0.0045	0.029*
H21	0.7107	0.5124	−0.1462	0.030*
H22	0.8791	0.3899	−0.1571	0.031*
H25	1.0517	0.2617	−0.0703	0.032*
H26	1.1427	0.1812	0.0686	0.033*
H29	1.1318	0.1458	0.2442	0.031*
H30	1.0397	0.1878	0.3816	0.031*
H31	0.8848	0.3219	0.3780	0.031*
H6A	0.3872	0.1401	0.4487	0.044*
H6B	0.4192	0.2461	0.4267	0.044*
H7A	0.2501	0.7434	0.3875	0.037*
H7B	0.4071	0.7824	0.4335	0.036*
H8A	0.3240	0.9425	0.3846	0.051*
H8B	0.3390	1.0265	0.3126	0.051*
H9A	0.6021	0.8246	−0.2446	0.036*
H9B	0.5251	0.8986	−0.2126	0.036*
H10A	0.2598	0.4155	0.3144	0.064*
H10B	0.1448	0.5135	0.3224	0.064*
H15A	0.6355	0.6805	0.3944	0.030*
H15B	0.4913	0.5911	0.3520	0.030*
H16A	0.8725	0.5200	0.4761	0.031*
H16B	0.8292	0.6375	0.4742	0.031*
H17A	0.5456	0.4598	0.4319	0.027*
H17B	0.6871	0.3975	0.4252	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.01609 (14)	0.02246 (14)	0.02111 (14)	0.00427 (10)	0.00476 (9)	0.00006 (10)
S1	0.0267 (2)	0.0271 (2)	0.0241 (2)	0.01063 (19)	0.00511 (18)	0.0013 (2)
O1	0.0182 (6)	0.0321 (7)	0.0290 (7)	−0.0022 (5)	0.0030 (5)	−0.0001 (6)
O2	0.0185 (6)	0.0280 (6)	0.0263 (6)	0.0024 (5)	0.0076 (5)	−0.0019 (5)
O3	0.0247 (7)	0.0268 (6)	0.0395 (8)	−0.0028 (5)	0.0127 (6)	−0.0027 (6)
O4	0.0206 (6)	0.0279 (6)	0.0267 (6)	0.0013 (5)	0.0054 (5)	−0.0029 (5)
O5	0.0231 (6)	0.0272 (6)	0.0243 (6)	0.0089 (5)	0.0071 (5)	0.0017 (5)
O6	0.0437 (9)	0.0340 (7)	0.0311 (7)	−0.0062 (6)	0.0080 (6)	−0.0029 (6)
O7	0.0268 (7)	0.0317 (7)	0.0325 (7)	0.0024 (5)	0.0119 (5)	0.0042 (6)
O8	0.0549 (10)	0.0302 (7)	0.0417 (8)	0.0027 (7)	0.0250 (7)	−0.0009 (7)
O9	0.0263 (7)	0.0279 (6)	0.0374 (7)	0.0054 (5)	0.0129 (5)	−0.0014 (6)
O10	0.0306 (9)	0.0498 (10)	0.0780 (13)	0.0106 (7)	0.0132 (8)	−0.0057 (9)
N1	0.0217 (7)	0.0249 (7)	0.0218 (7)	0.0071 (6)	0.0059 (5)	−0.0004 (6)
N2	0.0197 (7)	0.0272 (7)	0.0263 (7)	0.0047 (6)	0.0050 (6)	0.0037 (6)
N3	0.0157 (7)	0.0205 (6)	0.0217 (7)	0.0037 (5)	0.0020 (5)	0.0028 (6)
N4	0.0180 (7)	0.0221 (7)	0.0238 (7)	0.0030 (5)	0.0049 (5)	−0.0006 (6)
N5	0.0177 (7)	0.0237 (7)	0.0228 (7)	0.0029 (5)	0.0036 (5)	−0.0025 (6)
C1	0.0175 (8)	0.0214 (8)	0.0223 (8)	0.0020 (6)	0.0015 (6)	0.0008 (7)
C2	0.0271 (9)	0.0253 (8)	0.0231 (8)	0.0080 (7)	0.0053 (7)	−0.0012 (7)
C3	0.0233 (9)	0.0249 (8)	0.0270 (9)	0.0075 (7)	0.0024 (7)	−0.0007 (7)
C4	0.0186 (8)	0.0217 (8)	0.0247 (8)	0.0020 (6)	0.0023 (6)	0.0014 (7)
C5	0.0264 (9)	0.0317 (9)	0.0266 (9)	0.0096 (8)	0.0099 (7)	0.0042 (8)
C6	0.0249 (9)	0.0291 (9)	0.0285 (9)	0.0114 (7)	0.0093 (7)	0.0045 (8)
C7	0.0182 (8)	0.0229 (8)	0.0255 (8)	0.0027 (6)	0.0033 (6)	−0.0012 (7)
C8	0.0226 (9)	0.0235 (8)	0.0271 (9)	0.0028 (7)	0.0032 (7)	0.0019 (7)
C9	0.0277 (10)	0.0298 (9)	0.0325 (10)	0.0086 (8)	0.0044 (8)	0.0024 (8)
C10	0.0297 (10)	0.0317 (10)	0.0302 (10)	0.0043 (8)	0.0015 (8)	0.0061 (8)
C11	0.0304 (10)	0.0357 (10)	0.0269 (9)	0.0019 (8)	0.0063 (7)	0.0070 (8)
C12	0.0242 (10)	0.0353 (10)	0.0312 (9)	0.0049 (8)	0.0102 (7)	0.0057 (9)
C13	0.0187 (9)	0.0249 (8)	0.0277 (9)	0.0014 (7)	0.0033 (7)	0.0031 (7)
C14	0.0163 (8)	0.0211 (8)	0.0229 (8)	0.0020 (6)	0.0027 (6)	−0.0001 (7)
C15	0.0278 (9)	0.0269 (8)	0.0232 (8)	0.0110 (7)	0.0096 (7)	0.0020 (7)
C16	0.0189 (9)	0.0352 (9)	0.0222 (8)	−0.0005 (7)	0.0036 (7)	0.0006 (8)
C17	0.0202 (8)	0.0228 (8)	0.0260 (8)	0.0027 (6)	0.0086 (6)	0.0037 (7)
C18	0.0197 (8)	0.0214 (8)	0.0273 (9)	0.0060 (6)	0.0051 (6)	0.0036 (7)
C19	0.0184 (8)	0.0230 (8)	0.0303 (9)	0.0048 (6)	0.0067 (7)	0.0011 (7)
C20	0.0198 (9)	0.0243 (8)	0.0265 (9)	0.0015 (7)	0.0048 (7)	0.0001 (7)
C21	0.0230 (9)	0.0279 (9)	0.0217 (8)	−0.0009 (7)	0.0029 (6)	0.0018 (7)
C22	0.0247 (9)	0.0287 (9)	0.0225 (8)	−0.0022 (7)	0.0071 (7)	−0.0036 (8)
C23	0.0188 (8)	0.0239 (8)	0.0272 (9)	−0.0013 (7)	0.0062 (7)	−0.0038 (7)
C24	0.0154 (8)	0.0214 (8)	0.0239 (8)	0.0010 (6)	0.0039 (6)	−0.0023 (7)
C25	0.0233 (9)	0.0277 (9)	0.0304 (9)	0.0017 (7)	0.0097 (7)	−0.0076 (8)
C26	0.0214 (9)	0.0263 (9)	0.0340 (10)	0.0052 (7)	0.0072 (7)	−0.0047 (8)
C27	0.0157 (8)	0.0241 (8)	0.0293 (9)	0.0019 (6)	0.0026 (6)	−0.0049 (7)
C28	0.0150 (8)	0.0216 (8)	0.0256 (8)	0.0010 (6)	0.0034 (6)	−0.0032 (7)
C29	0.0173 (8)	0.0236 (8)	0.0338 (10)	0.0034 (6)	0.0021 (7)	−0.0011 (8)
C30	0.0215 (9)	0.0263 (8)	0.0285 (9)	0.0047 (7)	0.0002 (7)	0.0038 (8)
C31	0.0220 (9)	0.0285 (9)	0.0254 (9)	0.0048 (7)	0.0035 (7)	0.0001 (8)

Geometric parameters (Å, º)

Co1—O2	2.0728 (11)	C23—C24	1.402 (2)
Co1—O4	2.0577 (13)	C23—C25	1.439 (2)
Co1—O5	2.0943 (14)	C24—C28	1.445 (2)
Co1—N3	2.1973 (16)	C25—C26	1.356 (2)
Co1—N4	2.1007 (16)	C26—C27	1.431 (3)
Co1—N5	2.1680 (16)	C27—C28	1.408 (2)
S1—C7	1.758 (2)	C27—C29	1.410 (2)
S1—C8	1.735 (2)	C29—C30	1.370 (3)
O1—C18	1.2403 (19)	C30—C31	1.405 (2)
O2—C18	1.274 (2)	O6—H6A	0.901
O3—C19	1.251 (2)	O6—H6B	0.867
O4—C19	1.263 (2)	O7—H7A	0.915
O5—C14	1.241 (2)	O7—H7B	0.919
N1—C1	1.411 (2)	O8—H8A	0.916
N1—C14	1.339 (2)	O8—H8B	0.982
N2—C7	1.297 (2)	O9—H9A	0.882
N2—C13	1.390 (2)	O9—H9B	0.878
N3—C15	1.482 (2)	O10—H10A	1.019
N3—C16	1.477 (2)	O10—H10B	1.033
N3—C17	1.477 (2)	N1—H1	0.880
N4—C20	1.330 (2)	C2—H2	0.950
N4—C24	1.361 (2)	C3—H3	0.950
N5—C28	1.357 (2)	C5—H5	0.950
N5—C31	1.329 (2)	C6—H6	0.950
C1—C2	1.392 (2)	C9—H9	0.950
C1—C6	1.395 (2)	C10—H10	0.950
C2—C3	1.384 (2)	C11—H11	0.950
C3—C4	1.392 (2)	C12—H12	0.950
C4—C5	1.399 (2)	C15—H15A	0.990
C4—C7	1.466 (2)	C15—H15B	0.990
C5—C6	1.384 (2)	C16—H16A	0.990
C8—C9	1.397 (2)	C16—H16B	0.990
C8—C13	1.402 (3)	C17—H17A	0.990
C9—C10	1.381 (3)	C17—H17B	0.990
C10—C11	1.400 (3)	C20—H20	0.950
C11—C12	1.378 (3)	C21—H21	0.950
C12—C13	1.403 (3)	C22—H22	0.950
C14—C15	1.512 (2)	C25—H25	0.950
C16—C18	1.529 (2)	C26—H26	0.950
C17—C19	1.534 (2)	C29—H29	0.950
C20—C21	1.400 (2)	C30—H30	0.950
C21—C22	1.376 (2)	C31—H31	0.950
C22—C23	1.410 (2)
S1···C29^i	3.5547 (18)	H9···H8B^xi	3.515
O1···O7^ii	2.810 (2)	H10···O1^iii	2.573
O1···O10^ii	3.198 (2)	H10···O7^xi	3.548
O1···C10^iii	3.361 (2)	H10···C11^xv	3.449
O1···C31^iv	3.445 (2)	H10···C16^iii	3.408
O2···O10^ii	2.957 (2)	H10···C18^iii	2.940
O2···C22^v	3.555 (2)	H10···C30^xvii	3.530
O3···O6	2.739 (2)	H10···H11^xv	3.179
O3···O9^i	2.752 (2)	H10···H30^xvii	2.686
O3···O10	2.905 (2)	H10···H31^xvii	3.514
O3···C27^vi	3.580 (2)	H10···H7A^xi	3.003
O3···C29^vi	3.112 (2)	H10···H8A^xi	3.412
O4···C21^i	3.579 (2)	H10···H15A^iii	3.411
O5···C21^i	3.594 (2)	H10···H16B^iii	2.893
O6···O3	2.739 (2)	H11···O6^xiii	2.765
O6···O7^vii	2.699 (2)	H11···O8^xiv	2.542
O6···O8^viii	2.763 (2)	H11···C10^xv	3.207
O6···C11^ix	3.287 (2)	H11···C11^xv	3.352
O6···C15^vii	3.304 (2)	H11···H10^xv	3.179
O6···C19	3.568 (2)	H11···H11^xv	3.411
O7···O1^vi	2.810 (2)	H11···H30^xvii	2.728
O7···O6^vii	2.699 (2)	H11···H6A^xiii	2.342
O7···O8	2.906 (2)	H11···H6B^xiii	3.408
O7···N1	2.882 (2)	H11···H8A^xiv	2.882
O7···C2	3.479 (2)	H11···H8B^xiv	3.429
O7···C15	3.455 (2)	H11···H15A^iii	3.545
O8···O6^x	2.763 (2)	H12···O8^xiv	3.481
O8···O7	2.906 (2)	H12···O8^iii	3.142
O8···O9^iii	2.764 (2)	H12···O9	3.305
O8···C9^xi	3.462 (2)	H12···H6A^xiii	3.443
O8···C11^xii	3.406 (3)	H12···H6A^i	3.252
O9···O3^i	2.752 (2)	H12···H8A^xiv	3.263
O9···O8^iii	2.764 (2)	H12···H8A^iii	3.164
O9···N2	2.879 (2)	H12···H8B^iii	2.859
O9···C2^iii	3.219 (2)	H12···H9A	3.447
O9···C3^iii	3.098 (2)	H12···H9B	2.819
O9···C5	3.522 (2)	H20···O4^i	3.405
O9···C19^i	3.490 (2)	H20···C20^i	3.364
O9···C29^v	3.270 (2)	H20···C25^v	3.378
O10···O1^vi	3.198 (2)	H20···H20^i	2.921
O10···O2^vi	2.957 (2)	H20···H25^v	3.241
O10···O3	2.905 (2)	H21···O3^i	3.386
O10···N5^vi	3.548 (2)	H21···O4^i	2.807
O10···C15	3.265 (2)	H21···O5^i	3.357
O10···C17	3.310 (2)	H21···O10^i	2.753
O10···C18^vi	3.262 (2)	H21···N1^i	3.472
O10···C19	3.070 (2)	H21···C14^i	3.211
O10···C21^i	3.476 (3)	H21···C19^i	3.127
O10···C31^vi	3.561 (2)	H21···C26^v	3.588
N1···O7	2.882 (2)	H21···H10A^i	2.632
N1···C21^i	3.511 (2)	H21···H10B^i	3.066
N1···C22^i	3.478 (2)	H21···H15B^i	3.182
N2···O9	2.879 (2)	H22···O2^v	2.673
N2···C2^iii	3.525 (2)	H22···O10^i	3.085
N2···C30^i	3.548 (2)	H22···N1^i	3.431
N4···C22^v	3.490 (2)	H22···N4^v	3.347
N5···O10^ii	3.548 (2)	H22···C1^i	3.531
C1···C22^i	3.353 (2)	H22···C24^v	3.422
C1···C23^i	3.578 (2)	H22···H1^i	3.401
C2···O7	3.479 (2)	H22···H7A^i	3.474
C2···O9^iii	3.219 (2)	H22···H10A^i	3.568
C2···N2^iii	3.525 (2)	H22···H10B^i	2.662
C2···C23^i	3.580 (2)	H25···S1^xviii	3.158
C3···O9^iii	3.098 (2)	H25···C9^xviii	3.564
C3···C25^i	3.454 (2)	H25···C20^v	3.384
C5···O9	3.522 (2)	H25···H6^v	3.421
C5···C24^i	3.452 (2)	H25···H9^xviii	2.950
C7···C27^i	3.450 (2)	H25···H20^v	3.241
C7···C29^i	3.537 (2)	H26···S1^xviii	3.056
C8···C29^i	3.567 (2)	H26···O9^v	2.907
C9···O8^xi	3.462 (2)	H26···H3^xviii	2.927
C10···O1^iii	3.361 (2)	H26···H5^v	3.469
C10···C18^iii	3.517 (2)	H26···H9A^v	2.992
C11···O6^xiii	3.287 (2)	H26···H9B^v	3.518
C11···O8^xiv	3.406 (3)	H29···S1^i	3.357
C11···C11^xv	3.557 (2)	H29···O3^ii	2.960
C13···C30^i	3.402 (2)	H29···O8^xviii	2.932
C14···C21^i	3.519 (2)	H29···O9^v	2.456
C15···O6^vii	3.304 (2)	H29···C8^i	3.350
C15···O7	3.455 (2)	H29···H6A^ii	3.272
C15···O10	3.265 (2)	H29···H6B^ii	3.291
C17···O10	3.310 (2)	H29···H8B^xviii	2.607
C18···O10^ii	3.262 (2)	H29···H9A^v	2.375
C18···C10^iii	3.517 (2)	H29···H9B^v	3.330
C19···O6	3.568 (2)	H29···H10A^ii	3.512
C19···O9^i	3.490 (2)	H30···O6^ii	3.314
C19···O10	3.070 (2)	H30···O8^xviii	3.539
C20···C23^v	3.491 (2)	H30···C10^xix	3.332
C20···C25^v	3.372 (2)	H30···C11^xix	3.352
C21···O4^i	3.579 (2)	H30···C12^i	3.357
C21···O5^i	3.594 (2)	H30···C13^i	3.371
C21···O10^i	3.476 (3)	H30···H10^xix	2.686
C21···N1^i	3.511 (2)	H30···H11^xix	2.728
C21···C14^i	3.519 (2)	H30···H6A^ii	3.207
C21···C23^v	3.407 (2)	H30···H6B^ii	3.311
C21···C24^v	3.542 (2)	H30···H10A^ii	3.589
C21···C25^v	3.532 (2)	H30···H16B^iv	2.886
C22···O2^v	3.555 (2)	H31···O1^iv	2.566
C22···N1^i	3.478 (2)	H31···C16^iv	3.272
C22···N4^v	3.490 (2)	H31···C18^iv	3.334
C22···C1^i	3.353 (2)	H31···H10^xix	3.514
C22···C23^v	3.542 (2)	H31···H10B^ii	3.404
C22···C24^v	3.374 (2)	H31···H16A^iv	3.091
C23···C1^i	3.578 (2)	H31···H16B^iv	2.899
C23···C2^i	3.580 (2)	H6A···O3	3.017
C23···C20^v	3.491 (2)	H6A···O7^vii	3.103
C23···C21^v	3.407 (2)	H6A···O8^viii	1.871
C23···C22^v	3.542 (2)	H6A···O9^i	3.259
C24···C5^i	3.452 (2)	H6A···C11^ix	3.024
C24···C21^v	3.542 (2)	H6A···C12^ix	3.594
C24···C22^v	3.374 (2)	H6A···H11^ix	2.342
C25···C3^i	3.454 (2)	H6A···H12^ix	3.443
C25···C20^v	3.372 (2)	H6A···H12^i	3.252
C25···C21^v	3.532 (2)	H6A···H29^vi	3.272
C27···O3^ii	3.580 (2)	H6A···H30^vi	3.207
C27···C7^i	3.450 (2)	H6A···H7B^vii	2.273
C29···S1^i	3.5547 (18)	H6A···H8A^viii	2.589
C29···O3^ii	3.112 (2)	H6A···H8A^vii	3.406
C29···O9^v	3.270 (2)	H6A···H8B^viii	2.274
C29···C7^i	3.537 (2)	H6A···H9A^i	2.947
C29···C8^i	3.567 (2)	H6A···H15A^vii	3.165
C30···N2^i	3.548 (2)	H6B···O3	1.882
C30···C13^i	3.402 (2)	H6B···O7^vii	3.216
C31···O1^iv	3.445 (2)	H6B···O8^viii	3.036
C31···O10^ii	3.561 (2)	H6B···O9^i	3.285
Co1···H10B^ii	3.469	H6B···C17	2.985
S1···H3^xi	3.559	H6B···C19	2.724
S1···H25^xvi	3.158	H6B···C29^vi	3.586
S1···H26^xvi	3.056	H6B···C30^vi	3.588
S1···H29^i	3.357	H6B···H11^ix	3.408
O1···H9^iii	3.337	H6B···H29^vi	3.291
O1···H10^iii	2.573	H6B···H30^vi	3.311
O1···H31^iv	2.566	H6B···H7A^vii	3.482
O1···H7A^ii	1.909	H6B···H7B^vii	2.300
O1···H7B^ii	3.038	H6B···H8B^viii	3.085
O1···H10B^ii	2.581	H6B···H9A^i	2.634
O1···H16A^iv	2.698	H6B···H10A	3.058
O1···H17B^iv	2.654	H6B···H15A^vii	2.811
O2···H9^iii	3.298	H6B···H15B^vii	3.539
O2···H22^v	2.673	H6B···H16B^vii	3.345
O2···H7A^ii	3.122	H6B···H17A	2.810
O2···H10A^ii	3.598	H6B···H17B	2.895
O2···H10B^ii	1.936	H7A···O1^vi	1.909
O3···H21^i	3.386	H7A···O2^vi	3.122
O3···H29^vi	2.960	H7A···O6^vii	3.168
O3···H6A	3.017	H7A···O8	3.416
O3···H6B	1.882	H7A···O10	3.268
O3···H8B^viii	3.593	H7A···N1	3.463
O3···H9A^i	1.876	H7A···C9^xi	3.512
O3···H9B^i	3.114	H7A···C10^xi	3.598
O3···H10A	2.018	H7A···C18^vi	2.793
O4···H5^i	2.970	H7A···H1	2.661
O4···H20^i	3.405	H7A···H2	3.293
O4···H21^i	2.807	H7A···H9^xi	2.852
O4···H9A^i	3.002	H7A···H10^xi	3.003
O4···H10A	3.263	H7A···H22^i	3.474
O5···H21^i	3.357	H7A···H6B^vii	3.482
O6···H1^vii	3.397	H7A···H8A	2.550
O6···H11^ix	2.765	H7A···H10B	3.003
O6···H30^vi	3.314	H7A···H15B	3.198
O6···H7A^vii	3.168	H7A···H17B^vii	3.247
O6···H7B^vii	1.803	H7B···O1^vi	3.038
O6···H8A^viii	3.488	H7B···O6^vii	1.803
O6···H8A^vii	3.540	H7B···O8	3.250
O6···H8B^viii	3.074	H7B···N1	3.199
O6···H9A^i	3.218	H7B···C15	3.211
O6···H15A^vii	2.432	H7B···H1	2.344
O6···H15B^vii	3.347	H7B···H2	3.465
O6···H16B^vii	3.307	H7B···H6A^vii	2.273
O6···H17A	3.419	H7B···H6B^vii	2.300
O6···H17B	3.434	H7B···H8A	2.348
O7···H1	2.017	H7B···H15A	2.711
O7···H2	2.736	H7B···H15B	2.910
O7···H9^xi	3.145	H7B···H17B^vii	3.258
O7···H10^xi	3.548	H8A···O6^x	3.488
O7···H6A^vii	3.103	H8A···O6^vii	3.540
O7···H6B^vii	3.216	H8A···O7	2.004
O7···H8A	2.004	H8A···O9^iii	3.346
O7···H8B	3.236	H8A···C2	3.529
O7···H15A	3.158	H8A···C9^xi	3.387
O7···H15B	3.072	H8A···C10^xi	3.600
O8···H2	2.884	H8A···H1	3.227
O8···H9^xi	3.301	H8A···H2	2.611
O8···H11^xii	2.542	H8A···H9^xi	3.046
O8···H12^xii	3.481	H8A···H10^xi	3.412
O8···H12^iii	3.142	H8A···H11^xii	2.882
O8···H29^xvi	2.932	H8A···H12^xii	3.263
O8···H30^xvi	3.539	H8A···H12^iii	3.164
O8···H6A^x	1.871	H8A···H6A^x	2.589
O8···H6B^x	3.036	H8A···H6A^vii	3.406
O8···H7A	3.416	H8A···H7A	2.550
O8···H7B	3.250	H8A···H7B	2.348
O8···H9A^iii	2.987	H8B···O3^x	3.593
O8···H9B^iii	3.163	H8B···O6^x	3.074
O9···H2^iii	2.929	H8B···O7	3.236
O9···H3^iii	2.698	H8B···O9^iii	1.839
O9···H5	2.726	H8B···C2	3.090
O9···H12	3.305	H8B···C12^iii	3.544
O9···H26^v	2.907	H8B···C29^xvi	3.513
O9···H29^v	2.456	H8B···H2	2.328
O9···H6A^i	3.259	H8B···H3	3.385
O9···H6B^i	3.285	H8B···H9^xi	3.515
O9···H8A^iii	3.346	H8B···H11^xii	3.429
O9···H8B^iii	1.839	H8B···H12^iii	2.859
O10···H21^i	2.753	H8B···H29^xvi	2.607
O10···H22^i	3.085	H8B···H6A^x	2.274
O10···H7A	3.268	H8B···H6B^x	3.085
O10···H15B	2.300	H8B···H9A^iii	2.224
O10···H16A^vii	3.104	H8B···H9B^iii	2.231
O10···H16B^vii	3.377	H9A···O3^i	1.876
O10···H17A	2.766	H9A···O4^i	3.002
O10···H17A^vii	3.353	H9A···O6^i	3.218
O10···H17B^vii	3.487	H9A···O8^iii	2.987
N1···H21^i	3.472	H9A···N2	3.245
N1···H22^i	3.431	H9A···C19^i	2.641
N1···H7A	3.463	H9A···C26^v	3.556
N1···H7B	3.199	H9A···C27^v	3.600
N2···H9A	3.245	H9A···C29^v	3.031
N2···H9B	2.008	H9A···H3^iii	3.488
N4···H22^v	3.347	H9A···H5	2.784
N5···H10A^ii	3.352	H9A···H12	3.447
N5···H10B^ii	2.917	H9A···H26^v	2.992
C1···H22^i	3.531	H9A···H29^v	2.375
C2···H8A	3.529	H9A···H6A^i	2.947
C2···H8B	3.090	H9A···H6B^i	2.634
C2···H9B^iii	3.124	H9A···H8B^iii	2.224
C3···H9B^iii	3.097	H9B···O3^i	3.114
C4···H9B	3.443	H9B···O8^iii	3.163
C5···H9B	3.076	H9B···N2	2.008
C7···H9B	2.986	H9B···C2^iii	3.124
C8···H29^i	3.350	H9B···C3^iii	3.097
C9···H25^xvi	3.564	H9B···C4	3.443
C9···H7A^xi	3.512	H9B···C5	3.076
C9···H8A^xi	3.387	H9B···C7	2.986
C10···H11^xv	3.207	H9B···C12	3.215
C10···H30^xvii	3.332	H9B···C13	2.903
C10···H7A^xi	3.598	H9B···C19^i	3.591
C10···H8A^xi	3.600	H9B···H2^iii	2.988
C10···H15A^iii	3.406	H9B···H3^iii	2.936
C10···H16B^iii	3.436	H9B···H5	2.328
C11···H10^xv	3.449	H9B···H12	2.819
C11···H11^xv	3.352	H9B···H26^v	3.518
C11···H30^xvii	3.352	H9B···H29^v	3.330
C11···H6A^xiii	3.024	H9B···H8B^iii	2.231
C11···H15A^iii	3.480	H10A···O2^vi	3.598
C12···H30^i	3.357	H10A···O3	2.018
C12···H6A^xiii	3.594	H10A···O4	3.263
C12···H8B^iii	3.544	H10A···N5^vi	3.352
C12···H9B	3.215	H10A···C17	3.087
C13···H30^i	3.371	H10A···C19	2.476
C13···H9B	2.903	H10A···C21^i	3.470
C14···H21^i	3.211	H10A···C27^vi	3.179
C15···H7B	3.211	H10A···C28^vi	3.310
C16···H10^iii	3.408	H10A···C29^vi	3.072
C16···H31^iv	3.272	H10A···C30^vi	3.114
C16···H10B^ii	3.563	H10A···C31^vi	3.232
C16···H16A^iv	3.031	H10A···H21^i	2.632
C17···H6B	2.985	H10A···H22^i	3.568
C17···H10A	3.087	H10A···H29^vi	3.512
C17···H17A^vii	3.431	H10A···H30^vi	3.589
C18···H9^iii	3.365	H10A···H6B	3.058
C18···H10^iii	2.940	H10A···H15B	2.802
C18···H31^iv	3.334	H10A···H16A^vii	3.515
C18···H7A^ii	2.793	H10A···H16B^vii	3.323
C18···H10B^ii	2.359	H10A···H17A	2.706
C18···H16A^iv	2.869	H10B···Co1^vi	3.469
C18···H17B^iv	3.593	H10B···O1^vi	2.581
C19···H21^i	3.127	H10B···O2^vi	1.936
C19···H6B	2.724	H10B···N5^vi	2.917
C19···H9A^i	2.641	H10B···C16^vi	3.563
C19···H9B^i	3.591	H10B···C18^vi	2.359
C19···H10A	2.476	H10B···C21^i	3.577
C20···H6^i	3.457	H10B···C22^i	3.386
C20···H20^i	3.364	H10B···C28^vi	3.302
C20···H25^v	3.384	H10B···C31^vi	3.141
C21···H10A^i	3.470	H10B···H21^i	3.066
C21···H10B^i	3.577	H10B···H22^i	2.662
C22···H10B^i	3.386	H10B···H31^vi	3.404
C24···H22^v	3.422	H10B···H7A	3.003
C25···H3^i	3.576	H10B···H15B	3.078
C25···H20^v	3.378	H10B···H16A^vii	2.920
C26···H21^v	3.588	H10B···H16B^vii	3.506
C26···H9A^v	3.556	H15A···O6^vii	2.432
C27···H9A^v	3.600	H15A···O7	3.158
C27···H10A^ii	3.179	H15A···C10^iii	3.406
C28···H5^i	3.597	H15A···C11^iii	3.480
C28···H10A^ii	3.310	H15A···H10^iii	3.411
C28···H10B^ii	3.302	H15A···H11^iii	3.545
C29···H6B^ii	3.586	H15A···H6A^vii	3.165
C29···H8B^xviii	3.513	H15A···H6B^vii	2.811
C29···H9A^v	3.031	H15A···H7B	2.711
C29···H10A^ii	3.072	H15B···O6^vii	3.347
C30···H10^xix	3.530	H15B···O7	3.072
C30···H6B^ii	3.588	H15B···O10	2.300
C30···H10A^ii	3.114	H15B···H21^i	3.182
C30···H16B^iv	3.210	H15B···H6B^vii	3.539
C31···H10A^ii	3.232	H15B···H7A	3.198
C31···H10B^ii	3.141	H15B···H7B	2.910
C31···H16A^iv	3.559	H15B···H10A	2.802
C31···H16B^iv	3.235	H15B···H10B	3.078
H1···O6^vii	3.397	H15B···H17A^vii	3.217
H1···O7	2.017	H16A···O1^iv	2.698
H1···H22^i	3.401	H16A···O10^vii	3.104
H1···H7A	2.661	H16A···C16^iv	3.031
H1···H7B	2.344	H16A···C18^iv	2.869
H1···H8A	3.227	H16A···C31^iv	3.559
H2···O7	2.736	H16A···H31^iv	3.091
H2···O8	2.884	H16A···H10A^vii	3.515
H2···O9^iii	2.929	H16A···H10B^vii	2.920
H2···H9^xi	3.140	H16A···H16A^iv	2.372
H2···H7A	3.293	H16A···H16B^iv	3.526
H2···H7B	3.465	H16B···O6^vii	3.307
H2···H8A	2.611	H16B···O10^vii	3.377
H2···H8B	2.328	H16B···C10^iii	3.436
H2···H9B^iii	2.988	H16B···C30^iv	3.210
H3···S1^xi	3.559	H16B···C31^iv	3.235
H3···O9^iii	2.698	H16B···H10^iii	2.893
H3···C25^i	3.576	H16B···H30^iv	2.886
H3···H26^xvi	2.927	H16B···H31^iv	2.899
H3···H8B	3.385	H16B···H6B^vii	3.345
H3···H9A^iii	3.488	H16B···H10A^vii	3.323
H3···H9B^iii	2.936	H16B···H10B^vii	3.506
H5···O4^i	2.970	H16B···H16A^iv	3.526
H5···O9	2.726	H17A···O6	3.419
H5···C28^i	3.597	H17A···O10	2.766
H5···H26^v	3.469	H17A···O10^vii	3.353
H5···H9A	2.784	H17A···C17^vii	3.431
H5···H9B	2.328	H17A···H6B	2.810
H6···C20^i	3.457	H17A···H10A	2.706
H6···H25^v	3.421	H17A···H15B^vii	3.217
H9···O1^iii	3.337	H17A···H17A^vii	2.476
H9···O2^iii	3.298	H17B···O1^iv	2.654
H9···O7^xi	3.145	H17B···O6	3.434
H9···O8^xi	3.301	H17B···O10^vii	3.487
H9···C18^iii	3.365	H17B···C18^iv	3.593
H9···H2^xi	3.140	H17B···H6B	2.895
H9···H25^xvi	2.950	H17B···H7A^vii	3.247
H9···H7A^xi	2.852	H17B···H7B^vii	3.258
H9···H8A^xi	3.046
O2—Co1—O4	154.50 (5)	C22—C23—C24	117.51 (17)
O2—Co1—O5	94.27 (5)	C22—C23—C25	123.61 (19)
O2—Co1—N3	79.77 (5)	C24—C23—C25	118.87 (17)
O2—Co1—N4	104.18 (5)	N4—C24—C23	122.81 (16)
O2—Co1—N5	85.50 (5)	N4—C24—C28	117.09 (17)
O4—Co1—O5	95.29 (5)	C23—C24—C28	120.10 (17)
O4—Co1—N3	78.63 (5)	C23—C25—C26	121.1 (2)
O4—Co1—N4	98.96 (5)	C25—C26—C27	121.03 (19)
O4—Co1—N5	88.92 (5)	C26—C27—C28	119.40 (17)
O5—Co1—N3	80.30 (5)	C26—C27—C29	123.31 (18)
O5—Co1—N4	92.52 (5)	C28—C27—C29	117.29 (19)
O5—Co1—N5	170.28 (6)	N5—C28—C24	117.46 (16)
N3—Co1—N4	172.11 (6)	N5—C28—C27	123.22 (17)
N3—Co1—N5	109.17 (5)	C24—C28—C27	119.30 (18)
N4—Co1—N5	78.15 (6)	C27—C29—C30	119.44 (18)
C7—S1—C8	89.29 (9)	C29—C30—C31	119.15 (18)
Co1—O2—C18	117.91 (12)	N5—C31—C30	123.11 (19)
Co1—O4—C19	116.17 (10)	H6A—O6—H6B	105.8
Co1—O5—C14	115.24 (12)	H7A—O7—H7B	102.6
C1—N1—C14	128.94 (17)	H8A—O8—H8B	106.7
C7—N2—C13	111.38 (17)	H9A—O9—H9B	101.0
Co1—N3—C15	108.10 (11)	H10A—O10—H10B	115.9
Co1—N3—C16	107.51 (12)	C1—N1—H1	115.5
Co1—N3—C17	104.54 (10)	C14—N1—H1	115.5
C15—N3—C16	112.18 (14)	C1—C2—H2	119.8
C15—N3—C17	110.05 (14)	C3—C2—H2	119.8
C16—N3—C17	113.97 (14)	C2—C3—H3	119.7
Co1—N4—C20	127.63 (14)	C4—C3—H3	119.7
Co1—N4—C24	114.35 (11)	C4—C5—H5	119.4
C20—N4—C24	117.98 (17)	C6—C5—H5	119.4
Co1—N5—C28	111.96 (11)	C1—C6—H6	120.2
Co1—N5—C31	130.00 (14)	C5—C6—H6	120.2
C28—N5—C31	117.76 (17)	C8—C9—H9	121.1
N1—C1—C2	116.14 (17)	C10—C9—H9	121.1
N1—C1—C6	124.26 (17)	C9—C10—H10	119.4
C2—C1—C6	119.59 (17)	C11—C10—H10	119.4
C1—C2—C3	120.43 (19)	C10—C11—H11	119.5
C2—C3—C4	120.63 (19)	C12—C11—H11	119.5
C3—C4—C5	118.52 (17)	C11—C12—H12	120.7
C3—C4—C7	121.28 (18)	C13—C12—H12	120.7
C5—C4—C7	120.19 (18)	N3—C15—H15A	109.0
C4—C5—C6	121.2 (2)	N3—C15—H15B	109.0
C1—C6—C5	119.60 (19)	C14—C15—H15A	109.0
S1—C7—N2	115.08 (14)	C14—C15—H15B	109.0
S1—C7—C4	120.43 (15)	H15A—C15—H15B	107.8
N2—C7—C4	124.49 (18)	N3—C16—H16A	108.9
S1—C8—C9	129.13 (17)	N3—C16—H16B	108.9
S1—C8—C13	109.32 (14)	C18—C16—H16A	108.9
C9—C8—C13	121.52 (19)	C18—C16—H16B	108.9
C8—C9—C10	117.8 (2)	H16A—C16—H16B	107.7
C9—C10—C11	121.3 (2)	N3—C17—H17A	109.5
C10—C11—C12	121.1 (2)	N3—C17—H17B	109.6
C11—C12—C13	118.6 (2)	C19—C17—H17A	109.6
N2—C13—C8	114.93 (18)	C19—C17—H17B	109.5
N2—C13—C12	125.35 (19)	H17A—C17—H17B	108.1
C8—C13—C12	119.71 (18)	N4—C20—H20	118.4
O5—C14—N1	124.39 (17)	C21—C20—H20	118.4
O5—C14—C15	122.21 (17)	C20—C21—H21	120.6
N1—C14—C15	113.38 (17)	C22—C21—H21	120.6
N3—C15—C14	112.86 (17)	C21—C22—H22	120.2
N3—C16—C18	113.33 (15)	C23—C22—H22	120.2
N3—C17—C19	110.50 (15)	C23—C25—H25	119.4
O1—C18—O2	125.49 (19)	C26—C25—H25	119.4
O1—C18—C16	116.69 (17)	C25—C26—H26	119.5
O2—C18—C16	117.69 (14)	C27—C26—H26	119.5
O3—C19—O4	124.75 (16)	C27—C29—H29	120.3
O3—C19—C17	117.19 (17)	C30—C29—H29	120.3
O4—C19—C17	118.05 (15)	C29—C30—H30	120.4
N4—C20—C21	123.26 (18)	C31—C30—H30	120.4
C20—C21—C22	118.81 (17)	N5—C31—H31	118.4
C21—C22—C23	119.55 (19)	C30—C31—H31	118.5
O2—Co1—O4—C19	11.8 (2)	C20—C21—C22—C23	1.5 (2)
O4—Co1—O2—C18	−24.8 (2)	C21—C22—C23—C24	0.1 (2)
O2—Co1—O5—C14	−87.79 (12)	C21—C22—C23—C25	−179.49 (17)
O5—Co1—O2—C18	86.97 (14)	C22—C23—C24—N4	−2.6 (2)
O2—Co1—N3—C15	105.94 (11)	C22—C23—C24—C28	177.10 (15)
O2—Co1—N3—C16	−15.37 (11)	C22—C23—C25—C26	−178.27 (18)
O2—Co1—N3—C17	−136.84 (11)	C24—C23—C25—C26	2.1 (2)
N3—Co1—O2—C18	7.64 (13)	C25—C23—C24—N4	177.03 (16)
O2—Co1—N4—C20	−103.14 (15)	C25—C23—C24—C28	−3.3 (2)
O2—Co1—N4—C24	74.39 (12)	N4—C24—C28—N5	2.1 (2)
N4—Co1—O2—C18	−179.34 (13)	N4—C24—C28—C27	−179.36 (15)
O2—Co1—N5—C28	−96.76 (11)	C23—C24—C28—N5	−177.58 (15)
O2—Co1—N5—C31	76.90 (15)	C23—C24—C28—C27	0.9 (2)
N5—Co1—O2—C18	−102.78 (14)	C23—C25—C26—C27	1.4 (2)
O4—Co1—O5—C14	68.54 (12)	C25—C26—C27—C28	−3.8 (2)
O5—Co1—O4—C19	−99.76 (14)	C25—C26—C27—C29	175.58 (17)
O4—Co1—N3—C15	−87.70 (10)	C26—C27—C28—N5	−178.99 (15)
O4—Co1—N3—C16	150.99 (12)	C26—C27—C28—C24	2.6 (2)
O4—Co1—N3—C17	29.52 (10)	C26—C27—C29—C30	−179.52 (17)
N3—Co1—O4—C19	−20.78 (14)	C28—C27—C29—C30	−0.1 (2)
O4—Co1—N4—C20	87.67 (15)	C29—C27—C28—N5	1.6 (2)
O4—Co1—N4—C24	−94.80 (12)	C29—C27—C28—C24	−176.84 (15)
N4—Co1—O4—C19	166.84 (14)	C27—C29—C30—C31	−1.2 (2)
O4—Co1—N5—C28	108.15 (11)	C29—C30—C31—N5	1.3 (2)
O4—Co1—N5—C31	−78.19 (16)	H1—N1—C1—C2	−1.6
N5—Co1—O4—C19	89.02 (14)	H1—N1—C1—C6	179.6
O5—Co1—N3—C15	9.75 (10)	H1—N1—C14—O5	−177.8
O5—Co1—N3—C16	−111.56 (12)	H1—N1—C14—C15	3.9
O5—Co1—N3—C17	126.97 (11)	Co1—N3—C15—H15A	−131.0
N3—Co1—O5—C14	−8.95 (11)	Co1—N3—C15—H15B	111.6
O5—Co1—N4—C20	−8.09 (15)	Co1—N3—C16—H16A	−100.5
O5—Co1—N4—C24	169.44 (12)	Co1—N3—C16—H16B	142.2
N4—Co1—O5—C14	167.77 (12)	Co1—N3—C17—H17A	−155.1
N3—Co1—N5—C28	−174.28 (10)	Co1—N3—C17—H17B	86.5
N3—Co1—N5—C31	−0.63 (16)	C15—N3—C16—H16A	140.7
N5—Co1—N3—C15	−172.52 (10)	C15—N3—C16—H16B	23.5
N5—Co1—N3—C16	66.17 (12)	C16—N3—C15—H15A	−12.5
N5—Co1—N3—C17	−55.30 (11)	C16—N3—C15—H15B	−130.0
N4—Co1—N5—C28	8.77 (11)	C15—N3—C17—H17A	−39.3
N4—Co1—N5—C31	−177.58 (16)	C15—N3—C17—H17B	−157.7
N5—Co1—N4—C20	174.65 (15)	C17—N3—C15—H15A	115.5
N5—Co1—N4—C24	−7.82 (11)	C17—N3—C15—H15B	−2.0
C7—S1—C8—C9	178.16 (18)	C16—N3—C17—H17A	87.8
C7—S1—C8—C13	0.34 (13)	C16—N3—C17—H17B	−30.6
C8—S1—C7—N2	0.35 (14)	C17—N3—C16—H16A	14.9
C8—S1—C7—C4	−178.86 (14)	C17—N3—C16—H16B	−102.4
Co1—O2—C18—O1	178.08 (15)	Co1—N4—C20—H20	−4.2
Co1—O2—C18—C16	2.4 (2)	C24—N4—C20—H20	178.4
Co1—O4—C19—O3	−172.48 (16)	Co1—N5—C31—H31	6.7
Co1—O4—C19—C17	6.3 (2)	C28—N5—C31—H31	−179.9
Co1—O5—C14—N1	−172.12 (13)	N1—C1—C2—H2	1.3
Co1—O5—C14—C15	6.1 (2)	N1—C1—C6—H6	−2.5
C1—N1—C14—O5	2.2 (2)	C2—C1—C6—H6	178.8
C1—N1—C14—C15	−176.11 (15)	C6—C1—C2—H2	−179.8
C14—N1—C1—C2	178.38 (16)	C1—C2—C3—H3	−179.7
C14—N1—C1—C6	−0.4 (2)	H2—C2—C3—C4	−179.7
C7—N2—C13—C8	1.2 (2)	H2—C2—C3—H3	0.3
C7—N2—C13—C12	−177.24 (17)	H3—C3—C4—C5	−179.6
C13—N2—C7—S1	−0.95 (19)	H3—C3—C4—C7	−0.4
C13—N2—C7—C4	178.23 (15)	C3—C4—C5—H5	178.6
Co1—N3—C15—C14	−9.67 (16)	C7—C4—C5—H5	−0.5
Co1—N3—C16—C18	20.84 (19)	C4—C5—C6—H6	−178.1
Co1—N3—C17—C19	−34.33 (17)	H5—C5—C6—C1	−178.1
C15—N3—C16—C18	−97.9 (2)	H5—C5—C6—H6	1.9
C16—N3—C15—C14	108.70 (17)	S1—C8—C9—H9	3.7
C15—N3—C17—C19	81.54 (19)	C13—C8—C9—H9	−178.6
C17—N3—C15—C14	−123.28 (15)	C8—C9—C10—H10	179.3
C16—N3—C17—C19	−151.43 (17)	H9—C9—C10—C11	179.3
C17—N3—C16—C18	136.21 (17)	H9—C9—C10—H10	−0.7
Co1—N4—C20—C21	175.81 (13)	C9—C10—C11—H11	179.2
Co1—N4—C24—C23	−174.44 (13)	H10—C10—C11—C12	179.2
Co1—N4—C24—C28	5.86 (19)	H10—C10—C11—H11	−0.8
C20—N4—C24—C23	3.3 (2)	C10—C11—C12—H12	−178.2
C20—N4—C24—C28	−176.36 (15)	H11—C11—C12—C13	−178.2
C24—N4—C20—C21	−1.6 (2)	H11—C11—C12—H12	1.8
Co1—N5—C28—C24	−8.61 (18)	H12—C12—C13—N2	−2.7
Co1—N5—C28—C27	172.94 (13)	H12—C12—C13—C8	178.9
Co1—N5—C31—C30	−173.26 (13)	O5—C14—C15—H15A	124.4
C28—N5—C31—C30	0.09 (19)	O5—C14—C15—H15B	−118.2
C31—N5—C28—C24	176.88 (15)	N1—C14—C15—H15A	−57.3
C31—N5—C28—C27	−1.6 (2)	N1—C14—C15—H15B	60.2
N1—C1—C2—C3	−178.69 (15)	H16A—C16—C18—O1	−71.5
N1—C1—C6—C5	177.53 (16)	H16A—C16—C18—O2	104.7
C2—C1—C6—C5	−1.2 (2)	H16B—C16—C18—O1	45.8
C6—C1—C2—C3	0.2 (2)	H16B—C16—C18—O2	−138.1
C1—C2—C3—C4	0.3 (2)	H17A—C17—C19—O3	−39.0
C2—C3—C4—C5	0.4 (2)	H17A—C17—C19—O4	142.2
C2—C3—C4—C7	179.51 (16)	H17B—C17—C19—O3	79.4
C3—C4—C5—C6	−1.4 (2)	H17B—C17—C19—O4	−99.4
C3—C4—C7—S1	−5.5 (2)	N4—C20—C21—H21	179.3
C3—C4—C7—N2	175.41 (17)	H20—C20—C21—C22	179.3
C5—C4—C7—S1	173.68 (13)	H20—C20—C21—H21	−0.7
C5—C4—C7—N2	−5.5 (2)	C20—C21—C22—H22	−178.5
C7—C4—C5—C6	179.40 (16)	H21—C21—C22—C23	−178.5
C4—C5—C6—C1	1.9 (2)	H21—C21—C22—H22	1.5
S1—C8—C9—C10	−176.25 (15)	H22—C22—C23—C24	−179.9
S1—C8—C13—N2	−0.96 (19)	H22—C22—C23—C25	0.6
S1—C8—C13—C12	177.62 (14)	C22—C23—C25—H25	1.7
C9—C8—C13—N2	−178.97 (16)	C24—C23—C25—H25	−177.9
C9—C8—C13—C12	−0.4 (2)	C23—C25—C26—H26	−178.6
C13—C8—C9—C10	1.3 (2)	H25—C25—C26—C27	−178.5
C8—C9—C10—C11	−0.7 (2)	H25—C25—C26—H26	1.5
C9—C10—C11—C12	−0.8 (3)	H26—C26—C27—C28	176.2
C10—C11—C12—C13	1.8 (2)	H26—C26—C27—C29	−4.4
C11—C12—C13—N2	177.26 (17)	C26—C27—C29—H29	0.5
C11—C12—C13—C8	−1.2 (2)	C28—C27—C29—H29	179.9
O5—C14—C15—N3	3.1 (2)	C27—C29—C30—H30	178.8
N1—C14—C15—N3	−178.55 (13)	H29—C29—C30—C31	178.8
N3—C16—C18—O1	167.17 (16)	H29—C29—C30—H30	−1.2
N3—C16—C18—O2	−16.8 (2)	C29—C30—C31—H31	−178.7
N3—C17—C19—O3	−159.80 (17)	H30—C30—C31—N5	−178.7
N3—C17—C19—O4	21.3 (2)	H30—C30—C31—H31	1.3
N4—C20—C21—C22	−0.7 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z+1; (v) −x+2, −y+1, −z; (vi) x−1, y, z; (vii) −x+1, −y+1, −z+1; (viii) x, y−1, z; (ix) x, y−1, z+1; (x) x, y+1, z; (xi) −x, −y+2, −z; (xii) x, y, z+1; (xiii) x, y+1, z−1; (xiv) x, y, z−1; (xv) −x, −y+2, −z−1; (xvi) x−1, y+1, z; (xvii) x−1, y+1, z−1; (xviii) x+1, y−1, z; (xix) x+1, y−1, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O8^viii	0.90	1.87	2.763 (2)	170
O6—H6B···O3	0.87	1.88	2.739 (2)	170
O7—H7A···O1^vi	0.92	1.91	2.810 (2)	168
O7—H7B···O6^vii	0.92	1.80	2.699 (2)	164
O8—H8A···O7	0.92	2.00	2.906 (2)	168
O8—H8B···O9^iii	0.98	1.84	2.764 (2)	156
O9—H9A···O3^i	0.88	1.88	2.752 (2)	172
O9—H9B···N2	0.88	2.01	2.879 (2)	172
O10—H10A···O3	1.02	2.02	2.905 (2)	144
O10—H10B···O1^vi	1.03	2.58	3.198 (2)	118
O10—H10B···O2^vi	1.03	1.94	2.957 (2)	169
N1—H1···O7	0.88	2.02	2.882 (2)	168

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