Download citation
Download citation
link to html
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-52-) ligand. The ring systems of the phenanthroline and ZL-52- 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-52- ligand. This is believed to be the first crystal structure of a complex of a 2-(4-amino­phenyl)­benzo­thia­zole ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108006306/sq3122sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108006306/sq3122Isup2.hkl
Contains datablock I

CCDC reference: 670230

Comment top

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 CoII, 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, CoII 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 CoII 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 ππ 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 CoII 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 top

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).

Experimental top

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.

Refinement top

The positional parameters of the water and imine H atoms were calculated on the basis of the positions of their parent atoms, with Uiso(H) = 1.5Ueq(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 CH(alkyl) = 0.99 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

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 top
[Figure 1] 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.
[Figure 2] Fig. 2. A packing diagram for (I), showing the ππ 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 top
Crystal data top
[Co(C19H15N3O5S)(C12H8N2)]·5H2OZ = 2
Mr = 726.62F(000) = 754.00
Triclinic, P1Dx = 1.547 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 8.9990 (7) ÅCell parameters from 13624 reflections
b = 12.7766 (7) Åθ = 3.0–27.5°
c = 14.0652 (8) ŵ = 0.69 mm1
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) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6151 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.030
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1111
Tmin = 0.703, Tmax = 0.872k = 1615
15300 measured reflectionsl = 1818
7094 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0704P)2 + 0.1918P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.118(Δ/σ)max = 0.001
S = 1.12Δρmax = 0.56 e Å3
7094 reflectionsΔρmin = 0.83 e Å3
434 parameters
Crystal data top
[Co(C19H15N3O5S)(C12H8N2)]·5H2Oγ = 97.389 (2)°
Mr = 726.62V = 1559.39 (17) Å3
Triclinic, P1Z = 2
a = 8.9990 (7) ÅMo Kα radiation
b = 12.7766 (7) ŵ = 0.69 mm1
c = 14.0652 (8) ÅT = 123 K
α = 92.661 (2)°0.50 × 0.50 × 0.20 mm
β = 102.770 (2)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
7094 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
6151 reflections with F2 > 2σ(F2)
Tmin = 0.703, Tmax = 0.872Rint = 0.030
15300 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041434 parameters
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.56 e Å3
7094 reflectionsΔρmin = 0.83 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Co10.75225 (3)0.491016 (18)0.223227 (17)0.01972 (8)
S10.14617 (6)1.03698 (4)0.11015 (3)0.02550 (12)
O11.09449 (15)0.66212 (11)0.43687 (10)0.0274 (3)
O20.95974 (15)0.57971 (10)0.29437 (10)0.0241 (2)
O30.40562 (17)0.30933 (11)0.30747 (11)0.0303 (3)
O40.55117 (15)0.39093 (11)0.21629 (10)0.0254 (2)
O50.64477 (15)0.62339 (11)0.18280 (10)0.0241 (2)
O60.4149 (2)0.20729 (12)0.47528 (11)0.0376 (3)
O70.33363 (17)0.78664 (11)0.37750 (11)0.0296 (3)
O80.3104 (2)1.01132 (12)0.37460 (12)0.0405 (3)
O90.61863 (16)0.88950 (11)0.21649 (11)0.0296 (3)
O100.2537 (2)0.49183 (15)0.33575 (16)0.0526 (4)
N10.49215 (18)0.73715 (12)0.22776 (11)0.0224 (3)
N20.32545 (18)0.93921 (13)0.19224 (12)0.0243 (3)
N30.69718 (17)0.53770 (12)0.36237 (11)0.0195 (3)
N40.77969 (18)0.45710 (12)0.08105 (11)0.0213 (3)
N50.87612 (18)0.35589 (12)0.24202 (11)0.0217 (3)
C10.4470 (2)0.78843 (14)0.14151 (13)0.0210 (3)
C20.3494 (2)0.86382 (15)0.14557 (14)0.0249 (3)
C30.2964 (2)0.91685 (15)0.06405 (14)0.0253 (3)
C40.3390 (2)0.89541 (14)0.02336 (14)0.0222 (3)
C50.4360 (2)0.81875 (16)0.02700 (15)0.0271 (4)
C60.4916 (2)0.76662 (15)0.05463 (14)0.0262 (3)
C70.2828 (2)0.95029 (15)0.11056 (14)0.0226 (3)
C80.1469 (2)1.05893 (15)0.23085 (14)0.0248 (3)
C90.0601 (2)1.12155 (16)0.29365 (15)0.0300 (4)
C100.0758 (2)1.12087 (17)0.38912 (15)0.0313 (4)
C110.1765 (2)1.06051 (17)0.42183 (16)0.0311 (4)
C120.2650 (2)1.00064 (17)0.35943 (15)0.0294 (4)
C130.2492 (2)0.99887 (15)0.26247 (14)0.0242 (3)
C140.5814 (2)0.66065 (14)0.24393 (13)0.0205 (3)
C150.5950 (2)0.62040 (15)0.34447 (14)0.0248 (3)
C160.8440 (2)0.57667 (16)0.43285 (14)0.0260 (3)
C170.6129 (2)0.44056 (14)0.38882 (14)0.0224 (3)
C180.9763 (2)0.61095 (14)0.38395 (14)0.0225 (3)
C190.5148 (2)0.37546 (14)0.29677 (14)0.0236 (3)
C200.7221 (2)0.50246 (15)0.00039 (14)0.0238 (3)
C210.7551 (2)0.47879 (15)0.09022 (14)0.0250 (3)
C220.8532 (2)0.40592 (15)0.09668 (14)0.0258 (3)
C230.9150 (2)0.35521 (14)0.01298 (14)0.0237 (3)
C240.8722 (2)0.38217 (14)0.07398 (13)0.0206 (3)
C251.0193 (2)0.27868 (15)0.01230 (15)0.0271 (4)
C261.0721 (2)0.23030 (15)0.06969 (15)0.0271 (4)
C271.0232 (2)0.25196 (15)0.15783 (14)0.0237 (3)
C280.9260 (2)0.32933 (14)0.16105 (14)0.0212 (3)
C291.0664 (2)0.19872 (15)0.24302 (15)0.0255 (3)
C301.0133 (2)0.22397 (15)0.32406 (15)0.0261 (3)
C310.9192 (2)0.30402 (15)0.32097 (14)0.0256 (3)
H10.45680.75830.27780.027*
H20.31910.87900.20470.030*
H30.23010.96840.06780.030*
H50.46410.80220.08660.032*
H60.55980.71630.05150.031*
H90.00741.16320.27140.036*
H100.01711.16220.43350.038*
H110.18401.06080.48810.037*
H120.33520.96140.38160.035*
H200.65530.55350.00450.029*
H210.71070.51240.14620.030*
H220.87910.38990.15710.031*
H251.05170.26170.07030.032*
H261.14270.18120.06860.033*
H291.13180.14580.24420.031*
H301.03970.18780.38160.031*
H310.88480.32190.37800.031*
H6A0.38720.14010.44870.044*
H6B0.41920.24610.42670.044*
H7A0.25010.74340.38750.037*
H7B0.40710.78240.43350.036*
H8A0.32400.94250.38460.051*
H8B0.33901.02650.31260.051*
H9A0.60210.82460.24460.036*
H9B0.52510.89860.21260.036*
H10A0.25980.41550.31440.064*
H10B0.14480.51350.32240.064*
H15A0.63550.68050.39440.030*
H15B0.49130.59110.35200.030*
H16A0.87250.52000.47610.031*
H16B0.82920.63750.47420.031*
H17A0.54560.45980.43190.027*
H17B0.68710.39750.42520.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.01609 (14)0.02246 (14)0.02111 (14)0.00427 (10)0.00476 (9)0.00006 (10)
S10.0267 (2)0.0271 (2)0.0241 (2)0.01063 (19)0.00511 (18)0.0013 (2)
O10.0182 (6)0.0321 (7)0.0290 (7)0.0022 (5)0.0030 (5)0.0001 (6)
O20.0185 (6)0.0280 (6)0.0263 (6)0.0024 (5)0.0076 (5)0.0019 (5)
O30.0247 (7)0.0268 (6)0.0395 (8)0.0028 (5)0.0127 (6)0.0027 (6)
O40.0206 (6)0.0279 (6)0.0267 (6)0.0013 (5)0.0054 (5)0.0029 (5)
O50.0231 (6)0.0272 (6)0.0243 (6)0.0089 (5)0.0071 (5)0.0017 (5)
O60.0437 (9)0.0340 (7)0.0311 (7)0.0062 (6)0.0080 (6)0.0029 (6)
O70.0268 (7)0.0317 (7)0.0325 (7)0.0024 (5)0.0119 (5)0.0042 (6)
O80.0549 (10)0.0302 (7)0.0417 (8)0.0027 (7)0.0250 (7)0.0009 (7)
O90.0263 (7)0.0279 (6)0.0374 (7)0.0054 (5)0.0129 (5)0.0014 (6)
O100.0306 (9)0.0498 (10)0.0780 (13)0.0106 (7)0.0132 (8)0.0057 (9)
N10.0217 (7)0.0249 (7)0.0218 (7)0.0071 (6)0.0059 (5)0.0004 (6)
N20.0197 (7)0.0272 (7)0.0263 (7)0.0047 (6)0.0050 (6)0.0037 (6)
N30.0157 (7)0.0205 (6)0.0217 (7)0.0037 (5)0.0020 (5)0.0028 (6)
N40.0180 (7)0.0221 (7)0.0238 (7)0.0030 (5)0.0049 (5)0.0006 (6)
N50.0177 (7)0.0237 (7)0.0228 (7)0.0029 (5)0.0036 (5)0.0025 (6)
C10.0175 (8)0.0214 (8)0.0223 (8)0.0020 (6)0.0015 (6)0.0008 (7)
C20.0271 (9)0.0253 (8)0.0231 (8)0.0080 (7)0.0053 (7)0.0012 (7)
C30.0233 (9)0.0249 (8)0.0270 (9)0.0075 (7)0.0024 (7)0.0007 (7)
C40.0186 (8)0.0217 (8)0.0247 (8)0.0020 (6)0.0023 (6)0.0014 (7)
C50.0264 (9)0.0317 (9)0.0266 (9)0.0096 (8)0.0099 (7)0.0042 (8)
C60.0249 (9)0.0291 (9)0.0285 (9)0.0114 (7)0.0093 (7)0.0045 (8)
C70.0182 (8)0.0229 (8)0.0255 (8)0.0027 (6)0.0033 (6)0.0012 (7)
C80.0226 (9)0.0235 (8)0.0271 (9)0.0028 (7)0.0032 (7)0.0019 (7)
C90.0277 (10)0.0298 (9)0.0325 (10)0.0086 (8)0.0044 (8)0.0024 (8)
C100.0297 (10)0.0317 (10)0.0302 (10)0.0043 (8)0.0015 (8)0.0061 (8)
C110.0304 (10)0.0357 (10)0.0269 (9)0.0019 (8)0.0063 (7)0.0070 (8)
C120.0242 (10)0.0353 (10)0.0312 (9)0.0049 (8)0.0102 (7)0.0057 (9)
C130.0187 (9)0.0249 (8)0.0277 (9)0.0014 (7)0.0033 (7)0.0031 (7)
C140.0163 (8)0.0211 (8)0.0229 (8)0.0020 (6)0.0027 (6)0.0001 (7)
C150.0278 (9)0.0269 (8)0.0232 (8)0.0110 (7)0.0096 (7)0.0020 (7)
C160.0189 (9)0.0352 (9)0.0222 (8)0.0005 (7)0.0036 (7)0.0006 (8)
C170.0202 (8)0.0228 (8)0.0260 (8)0.0027 (6)0.0086 (6)0.0037 (7)
C180.0197 (8)0.0214 (8)0.0273 (9)0.0060 (6)0.0051 (6)0.0036 (7)
C190.0184 (8)0.0230 (8)0.0303 (9)0.0048 (6)0.0067 (7)0.0011 (7)
C200.0198 (9)0.0243 (8)0.0265 (9)0.0015 (7)0.0048 (7)0.0001 (7)
C210.0230 (9)0.0279 (9)0.0217 (8)0.0009 (7)0.0029 (6)0.0018 (7)
C220.0247 (9)0.0287 (9)0.0225 (8)0.0022 (7)0.0071 (7)0.0036 (8)
C230.0188 (8)0.0239 (8)0.0272 (9)0.0013 (7)0.0062 (7)0.0038 (7)
C240.0154 (8)0.0214 (8)0.0239 (8)0.0010 (6)0.0039 (6)0.0023 (7)
C250.0233 (9)0.0277 (9)0.0304 (9)0.0017 (7)0.0097 (7)0.0076 (8)
C260.0214 (9)0.0263 (9)0.0340 (10)0.0052 (7)0.0072 (7)0.0047 (8)
C270.0157 (8)0.0241 (8)0.0293 (9)0.0019 (6)0.0026 (6)0.0049 (7)
C280.0150 (8)0.0216 (8)0.0256 (8)0.0010 (6)0.0034 (6)0.0032 (7)
C290.0173 (8)0.0236 (8)0.0338 (10)0.0034 (6)0.0021 (7)0.0011 (8)
C300.0215 (9)0.0263 (8)0.0285 (9)0.0047 (7)0.0002 (7)0.0038 (8)
C310.0220 (9)0.0285 (9)0.0254 (9)0.0048 (7)0.0035 (7)0.0001 (8)
Geometric parameters (Å, º) top
Co1—O22.0728 (11)C23—C241.402 (2)
Co1—O42.0577 (13)C23—C251.439 (2)
Co1—O52.0943 (14)C24—C281.445 (2)
Co1—N32.1973 (16)C25—C261.356 (2)
Co1—N42.1007 (16)C26—C271.431 (3)
Co1—N52.1680 (16)C27—C281.408 (2)
S1—C71.758 (2)C27—C291.410 (2)
S1—C81.735 (2)C29—C301.370 (3)
O1—C181.2403 (19)C30—C311.405 (2)
O2—C181.274 (2)O6—H6A0.901
O3—C191.251 (2)O6—H6B0.867
O4—C191.263 (2)O7—H7A0.915
O5—C141.241 (2)O7—H7B0.919
N1—C11.411 (2)O8—H8A0.916
N1—C141.339 (2)O8—H8B0.982
N2—C71.297 (2)O9—H9A0.882
N2—C131.390 (2)O9—H9B0.878
N3—C151.482 (2)O10—H10A1.019
N3—C161.477 (2)O10—H10B1.033
N3—C171.477 (2)N1—H10.880
N4—C201.330 (2)C2—H20.950
N4—C241.361 (2)C3—H30.950
N5—C281.357 (2)C5—H50.950
N5—C311.329 (2)C6—H60.950
C1—C21.392 (2)C9—H90.950
C1—C61.395 (2)C10—H100.950
C2—C31.384 (2)C11—H110.950
C3—C41.392 (2)C12—H120.950
C4—C51.399 (2)C15—H15A0.990
C4—C71.466 (2)C15—H15B0.990
C5—C61.384 (2)C16—H16A0.990
C8—C91.397 (2)C16—H16B0.990
C8—C131.402 (3)C17—H17A0.990
C9—C101.381 (3)C17—H17B0.990
C10—C111.400 (3)C20—H200.950
C11—C121.378 (3)C21—H210.950
C12—C131.403 (3)C22—H220.950
C14—C151.512 (2)C25—H250.950
C16—C181.529 (2)C26—H260.950
C17—C191.534 (2)C29—H290.950
C20—C211.400 (2)C30—H300.950
C21—C221.376 (2)C31—H310.950
C22—C231.410 (2)
S1···C29i3.5547 (18)H9···H8Bxi3.515
O1···O7ii2.810 (2)H10···O1iii2.573
O1···O10ii3.198 (2)H10···O7xi3.548
O1···C10iii3.361 (2)H10···C11xv3.449
O1···C31iv3.445 (2)H10···C16iii3.408
O2···O10ii2.957 (2)H10···C18iii2.940
O2···C22v3.555 (2)H10···C30xvii3.530
O3···O62.739 (2)H10···H11xv3.179
O3···O9i2.752 (2)H10···H30xvii2.686
O3···O102.905 (2)H10···H31xvii3.514
O3···C27vi3.580 (2)H10···H7Axi3.003
O3···C29vi3.112 (2)H10···H8Axi3.412
O4···C21i3.579 (2)H10···H15Aiii3.411
O5···C21i3.594 (2)H10···H16Biii2.893
O6···O32.739 (2)H11···O6xiii2.765
O6···O7vii2.699 (2)H11···O8xiv2.542
O6···O8viii2.763 (2)H11···C10xv3.207
O6···C11ix3.287 (2)H11···C11xv3.352
O6···C15vii3.304 (2)H11···H10xv3.179
O6···C193.568 (2)H11···H11xv3.411
O7···O1vi2.810 (2)H11···H30xvii2.728
O7···O6vii2.699 (2)H11···H6Axiii2.342
O7···O82.906 (2)H11···H6Bxiii3.408
O7···N12.882 (2)H11···H8Axiv2.882
O7···C23.479 (2)H11···H8Bxiv3.429
O7···C153.455 (2)H11···H15Aiii3.545
O8···O6x2.763 (2)H12···O8xiv3.481
O8···O72.906 (2)H12···O8iii3.142
O8···O9iii2.764 (2)H12···O93.305
O8···C9xi3.462 (2)H12···H6Axiii3.443
O8···C11xii3.406 (3)H12···H6Ai3.252
O9···O3i2.752 (2)H12···H8Axiv3.263
O9···O8iii2.764 (2)H12···H8Aiii3.164
O9···N22.879 (2)H12···H8Biii2.859
O9···C2iii3.219 (2)H12···H9A3.447
O9···C3iii3.098 (2)H12···H9B2.819
O9···C53.522 (2)H20···O4i3.405
O9···C19i3.490 (2)H20···C20i3.364
O9···C29v3.270 (2)H20···C25v3.378
O10···O1vi3.198 (2)H20···H20i2.921
O10···O2vi2.957 (2)H20···H25v3.241
O10···O32.905 (2)H21···O3i3.386
O10···N5vi3.548 (2)H21···O4i2.807
O10···C153.265 (2)H21···O5i3.357
O10···C173.310 (2)H21···O10i2.753
O10···C18vi3.262 (2)H21···N1i3.472
O10···C193.070 (2)H21···C14i3.211
O10···C21i3.476 (3)H21···C19i3.127
O10···C31vi3.561 (2)H21···C26v3.588
N1···O72.882 (2)H21···H10Ai2.632
N1···C21i3.511 (2)H21···H10Bi3.066
N1···C22i3.478 (2)H21···H15Bi3.182
N2···O92.879 (2)H22···O2v2.673
N2···C2iii3.525 (2)H22···O10i3.085
N2···C30i3.548 (2)H22···N1i3.431
N4···C22v3.490 (2)H22···N4v3.347
N5···O10ii3.548 (2)H22···C1i3.531
C1···C22i3.353 (2)H22···C24v3.422
C1···C23i3.578 (2)H22···H1i3.401
C2···O73.479 (2)H22···H7Ai3.474
C2···O9iii3.219 (2)H22···H10Ai3.568
C2···N2iii3.525 (2)H22···H10Bi2.662
C2···C23i3.580 (2)H25···S1xviii3.158
C3···O9iii3.098 (2)H25···C9xviii3.564
C3···C25i3.454 (2)H25···C20v3.384
C5···O93.522 (2)H25···H6v3.421
C5···C24i3.452 (2)H25···H9xviii2.950
C7···C27i3.450 (2)H25···H20v3.241
C7···C29i3.537 (2)H26···S1xviii3.056
C8···C29i3.567 (2)H26···O9v2.907
C9···O8xi3.462 (2)H26···H3xviii2.927
C10···O1iii3.361 (2)H26···H5v3.469
C10···C18iii3.517 (2)H26···H9Av2.992
C11···O6xiii3.287 (2)H26···H9Bv3.518
C11···O8xiv3.406 (3)H29···S1i3.357
C11···C11xv3.557 (2)H29···O3ii2.960
C13···C30i3.402 (2)H29···O8xviii2.932
C14···C21i3.519 (2)H29···O9v2.456
C15···O6vii3.304 (2)H29···C8i3.350
C15···O73.455 (2)H29···H6Aii3.272
C15···O103.265 (2)H29···H6Bii3.291
C17···O103.310 (2)H29···H8Bxviii2.607
C18···O10ii3.262 (2)H29···H9Av2.375
C18···C10iii3.517 (2)H29···H9Bv3.330
C19···O63.568 (2)H29···H10Aii3.512
C19···O9i3.490 (2)H30···O6ii3.314
C19···O103.070 (2)H30···O8xviii3.539
C20···C23v3.491 (2)H30···C10xix3.332
C20···C25v3.372 (2)H30···C11xix3.352
C21···O4i3.579 (2)H30···C12i3.357
C21···O5i3.594 (2)H30···C13i3.371
C21···O10i3.476 (3)H30···H10xix2.686
C21···N1i3.511 (2)H30···H11xix2.728
C21···C14i3.519 (2)H30···H6Aii3.207
C21···C23v3.407 (2)H30···H6Bii3.311
C21···C24v3.542 (2)H30···H10Aii3.589
C21···C25v3.532 (2)H30···H16Biv2.886
C22···O2v3.555 (2)H31···O1iv2.566
C22···N1i3.478 (2)H31···C16iv3.272
C22···N4v3.490 (2)H31···C18iv3.334
C22···C1i3.353 (2)H31···H10xix3.514
C22···C23v3.542 (2)H31···H10Bii3.404
C22···C24v3.374 (2)H31···H16Aiv3.091
C23···C1i3.578 (2)H31···H16Biv2.899
C23···C2i3.580 (2)H6A···O33.017
C23···C20v3.491 (2)H6A···O7vii3.103
C23···C21v3.407 (2)H6A···O8viii1.871
C23···C22v3.542 (2)H6A···O9i3.259
C24···C5i3.452 (2)H6A···C11ix3.024
C24···C21v3.542 (2)H6A···C12ix3.594
C24···C22v3.374 (2)H6A···H11ix2.342
C25···C3i3.454 (2)H6A···H12ix3.443
C25···C20v3.372 (2)H6A···H12i3.252
C25···C21v3.532 (2)H6A···H29vi3.272
C27···O3ii3.580 (2)H6A···H30vi3.207
C27···C7i3.450 (2)H6A···H7Bvii2.273
C29···S1i3.5547 (18)H6A···H8Aviii2.589
C29···O3ii3.112 (2)H6A···H8Avii3.406
C29···O9v3.270 (2)H6A···H8Bviii2.274
C29···C7i3.537 (2)H6A···H9Ai2.947
C29···C8i3.567 (2)H6A···H15Avii3.165
C30···N2i3.548 (2)H6B···O31.882
C30···C13i3.402 (2)H6B···O7vii3.216
C31···O1iv3.445 (2)H6B···O8viii3.036
C31···O10ii3.561 (2)H6B···O9i3.285
Co1···H10Bii3.469H6B···C172.985
S1···H3xi3.559H6B···C192.724
S1···H25xvi3.158H6B···C29vi3.586
S1···H26xvi3.056H6B···C30vi3.588
S1···H29i3.357H6B···H11ix3.408
O1···H9iii3.337H6B···H29vi3.291
O1···H10iii2.573H6B···H30vi3.311
O1···H31iv2.566H6B···H7Avii3.482
O1···H7Aii1.909H6B···H7Bvii2.300
O1···H7Bii3.038H6B···H8Bviii3.085
O1···H10Bii2.581H6B···H9Ai2.634
O1···H16Aiv2.698H6B···H10A3.058
O1···H17Biv2.654H6B···H15Avii2.811
O2···H9iii3.298H6B···H15Bvii3.539
O2···H22v2.673H6B···H16Bvii3.345
O2···H7Aii3.122H6B···H17A2.810
O2···H10Aii3.598H6B···H17B2.895
O2···H10Bii1.936H7A···O1vi1.909
O3···H21i3.386H7A···O2vi3.122
O3···H29vi2.960H7A···O6vii3.168
O3···H6A3.017H7A···O83.416
O3···H6B1.882H7A···O103.268
O3···H8Bviii3.593H7A···N13.463
O3···H9Ai1.876H7A···C9xi3.512
O3···H9Bi3.114H7A···C10xi3.598
O3···H10A2.018H7A···C18vi2.793
O4···H5i2.970H7A···H12.661
O4···H20i3.405H7A···H23.293
O4···H21i2.807H7A···H9xi2.852
O4···H9Ai3.002H7A···H10xi3.003
O4···H10A3.263H7A···H22i3.474
O5···H21i3.357H7A···H6Bvii3.482
O6···H1vii3.397H7A···H8A2.550
O6···H11ix2.765H7A···H10B3.003
O6···H30vi3.314H7A···H15B3.198
O6···H7Avii3.168H7A···H17Bvii3.247
O6···H7Bvii1.803H7B···O1vi3.038
O6···H8Aviii3.488H7B···O6vii1.803
O6···H8Avii3.540H7B···O83.250
O6···H8Bviii3.074H7B···N13.199
O6···H9Ai3.218H7B···C153.211
O6···H15Avii2.432H7B···H12.344
O6···H15Bvii3.347H7B···H23.465
O6···H16Bvii3.307H7B···H6Avii2.273
O6···H17A3.419H7B···H6Bvii2.300
O6···H17B3.434H7B···H8A2.348
O7···H12.017H7B···H15A2.711
O7···H22.736H7B···H15B2.910
O7···H9xi3.145H7B···H17Bvii3.258
O7···H10xi3.548H8A···O6x3.488
O7···H6Avii3.103H8A···O6vii3.540
O7···H6Bvii3.216H8A···O72.004
O7···H8A2.004H8A···O9iii3.346
O7···H8B3.236H8A···C23.529
O7···H15A3.158H8A···C9xi3.387
O7···H15B3.072H8A···C10xi3.600
O8···H22.884H8A···H13.227
O8···H9xi3.301H8A···H22.611
O8···H11xii2.542H8A···H9xi3.046
O8···H12xii3.481H8A···H10xi3.412
O8···H12iii3.142H8A···H11xii2.882
O8···H29xvi2.932H8A···H12xii3.263
O8···H30xvi3.539H8A···H12iii3.164
O8···H6Ax1.871H8A···H6Ax2.589
O8···H6Bx3.036H8A···H6Avii3.406
O8···H7A3.416H8A···H7A2.550
O8···H7B3.250H8A···H7B2.348
O8···H9Aiii2.987H8B···O3x3.593
O8···H9Biii3.163H8B···O6x3.074
O9···H2iii2.929H8B···O73.236
O9···H3iii2.698H8B···O9iii1.839
O9···H52.726H8B···C23.090
O9···H123.305H8B···C12iii3.544
O9···H26v2.907H8B···C29xvi3.513
O9···H29v2.456H8B···H22.328
O9···H6Ai3.259H8B···H33.385
O9···H6Bi3.285H8B···H9xi3.515
O9···H8Aiii3.346H8B···H11xii3.429
O9···H8Biii1.839H8B···H12iii2.859
O10···H21i2.753H8B···H29xvi2.607
O10···H22i3.085H8B···H6Ax2.274
O10···H7A3.268H8B···H6Bx3.085
O10···H15B2.300H8B···H9Aiii2.224
O10···H16Avii3.104H8B···H9Biii2.231
O10···H16Bvii3.377H9A···O3i1.876
O10···H17A2.766H9A···O4i3.002
O10···H17Avii3.353H9A···O6i3.218
O10···H17Bvii3.487H9A···O8iii2.987
N1···H21i3.472H9A···N23.245
N1···H22i3.431H9A···C19i2.641
N1···H7A3.463H9A···C26v3.556
N1···H7B3.199H9A···C27v3.600
N2···H9A3.245H9A···C29v3.031
N2···H9B2.008H9A···H3iii3.488
N4···H22v3.347H9A···H52.784
N5···H10Aii3.352H9A···H123.447
N5···H10Bii2.917H9A···H26v2.992
C1···H22i3.531H9A···H29v2.375
C2···H8A3.529H9A···H6Ai2.947
C2···H8B3.090H9A···H6Bi2.634
C2···H9Biii3.124H9A···H8Biii2.224
C3···H9Biii3.097H9B···O3i3.114
C4···H9B3.443H9B···O8iii3.163
C5···H9B3.076H9B···N22.008
C7···H9B2.986H9B···C2iii3.124
C8···H29i3.350H9B···C3iii3.097
C9···H25xvi3.564H9B···C43.443
C9···H7Axi3.512H9B···C53.076
C9···H8Axi3.387H9B···C72.986
C10···H11xv3.207H9B···C123.215
C10···H30xvii3.332H9B···C132.903
C10···H7Axi3.598H9B···C19i3.591
C10···H8Axi3.600H9B···H2iii2.988
C10···H15Aiii3.406H9B···H3iii2.936
C10···H16Biii3.436H9B···H52.328
C11···H10xv3.449H9B···H122.819
C11···H11xv3.352H9B···H26v3.518
C11···H30xvii3.352H9B···H29v3.330
C11···H6Axiii3.024H9B···H8Biii2.231
C11···H15Aiii3.480H10A···O2vi3.598
C12···H30i3.357H10A···O32.018
C12···H6Axiii3.594H10A···O43.263
C12···H8Biii3.544H10A···N5vi3.352
C12···H9B3.215H10A···C173.087
C13···H30i3.371H10A···C192.476
C13···H9B2.903H10A···C21i3.470
C14···H21i3.211H10A···C27vi3.179
C15···H7B3.211H10A···C28vi3.310
C16···H10iii3.408H10A···C29vi3.072
C16···H31iv3.272H10A···C30vi3.114
C16···H10Bii3.563H10A···C31vi3.232
C16···H16Aiv3.031H10A···H21i2.632
C17···H6B2.985H10A···H22i3.568
C17···H10A3.087H10A···H29vi3.512
C17···H17Avii3.431H10A···H30vi3.589
C18···H9iii3.365H10A···H6B3.058
C18···H10iii2.940H10A···H15B2.802
C18···H31iv3.334H10A···H16Avii3.515
C18···H7Aii2.793H10A···H16Bvii3.323
C18···H10Bii2.359H10A···H17A2.706
C18···H16Aiv2.869H10B···Co1vi3.469
C18···H17Biv3.593H10B···O1vi2.581
C19···H21i3.127H10B···O2vi1.936
C19···H6B2.724H10B···N5vi2.917
C19···H9Ai2.641H10B···C16vi3.563
C19···H9Bi3.591H10B···C18vi2.359
C19···H10A2.476H10B···C21i3.577
C20···H6i3.457H10B···C22i3.386
C20···H20i3.364H10B···C28vi3.302
C20···H25v3.384H10B···C31vi3.141
C21···H10Ai3.470H10B···H21i3.066
C21···H10Bi3.577H10B···H22i2.662
C22···H10Bi3.386H10B···H31vi3.404
C24···H22v3.422H10B···H7A3.003
C25···H3i3.576H10B···H15B3.078
C25···H20v3.378H10B···H16Avii2.920
C26···H21v3.588H10B···H16Bvii3.506
C26···H9Av3.556H15A···O6vii2.432
C27···H9Av3.600H15A···O73.158
C27···H10Aii3.179H15A···C10iii3.406
C28···H5i3.597H15A···C11iii3.480
C28···H10Aii3.310H15A···H10iii3.411
C28···H10Bii3.302H15A···H11iii3.545
C29···H6Bii3.586H15A···H6Avii3.165
C29···H8Bxviii3.513H15A···H6Bvii2.811
C29···H9Av3.031H15A···H7B2.711
C29···H10Aii3.072H15B···O6vii3.347
C30···H10xix3.530H15B···O73.072
C30···H6Bii3.588H15B···O102.300
C30···H10Aii3.114H15B···H21i3.182
C30···H16Biv3.210H15B···H6Bvii3.539
C31···H10Aii3.232H15B···H7A3.198
C31···H10Bii3.141H15B···H7B2.910
C31···H16Aiv3.559H15B···H10A2.802
C31···H16Biv3.235H15B···H10B3.078
H1···O6vii3.397H15B···H17Avii3.217
H1···O72.017H16A···O1iv2.698
H1···H22i3.401H16A···O10vii3.104
H1···H7A2.661H16A···C16iv3.031
H1···H7B2.344H16A···C18iv2.869
H1···H8A3.227H16A···C31iv3.559
H2···O72.736H16A···H31iv3.091
H2···O82.884H16A···H10Avii3.515
H2···O9iii2.929H16A···H10Bvii2.920
H2···H9xi3.140H16A···H16Aiv2.372
H2···H7A3.293H16A···H16Biv3.526
H2···H7B3.465H16B···O6vii3.307
H2···H8A2.611H16B···O10vii3.377
H2···H8B2.328H16B···C10iii3.436
H2···H9Biii2.988H16B···C30iv3.210
H3···S1xi3.559H16B···C31iv3.235
H3···O9iii2.698H16B···H10iii2.893
H3···C25i3.576H16B···H30iv2.886
H3···H26xvi2.927H16B···H31iv2.899
H3···H8B3.385H16B···H6Bvii3.345
H3···H9Aiii3.488H16B···H10Avii3.323
H3···H9Biii2.936H16B···H10Bvii3.506
H5···O4i2.970H16B···H16Aiv3.526
H5···O92.726H17A···O63.419
H5···C28i3.597H17A···O102.766
H5···H26v3.469H17A···O10vii3.353
H5···H9A2.784H17A···C17vii3.431
H5···H9B2.328H17A···H6B2.810
H6···C20i3.457H17A···H10A2.706
H6···H25v3.421H17A···H15Bvii3.217
H9···O1iii3.337H17A···H17Avii2.476
H9···O2iii3.298H17B···O1iv2.654
H9···O7xi3.145H17B···O63.434
H9···O8xi3.301H17B···O10vii3.487
H9···C18iii3.365H17B···C18iv3.593
H9···H2xi3.140H17B···H6B2.895
H9···H25xvi2.950H17B···H7Avii3.247
H9···H7Axi2.852H17B···H7Bvii3.258
H9···H8Axi3.046
O2—Co1—O4154.50 (5)C22—C23—C24117.51 (17)
O2—Co1—O594.27 (5)C22—C23—C25123.61 (19)
O2—Co1—N379.77 (5)C24—C23—C25118.87 (17)
O2—Co1—N4104.18 (5)N4—C24—C23122.81 (16)
O2—Co1—N585.50 (5)N4—C24—C28117.09 (17)
O4—Co1—O595.29 (5)C23—C24—C28120.10 (17)
O4—Co1—N378.63 (5)C23—C25—C26121.1 (2)
O4—Co1—N498.96 (5)C25—C26—C27121.03 (19)
O4—Co1—N588.92 (5)C26—C27—C28119.40 (17)
O5—Co1—N380.30 (5)C26—C27—C29123.31 (18)
O5—Co1—N492.52 (5)C28—C27—C29117.29 (19)
O5—Co1—N5170.28 (6)N5—C28—C24117.46 (16)
N3—Co1—N4172.11 (6)N5—C28—C27123.22 (17)
N3—Co1—N5109.17 (5)C24—C28—C27119.30 (18)
N4—Co1—N578.15 (6)C27—C29—C30119.44 (18)
C7—S1—C889.29 (9)C29—C30—C31119.15 (18)
Co1—O2—C18117.91 (12)N5—C31—C30123.11 (19)
Co1—O4—C19116.17 (10)H6A—O6—H6B105.8
Co1—O5—C14115.24 (12)H7A—O7—H7B102.6
C1—N1—C14128.94 (17)H8A—O8—H8B106.7
C7—N2—C13111.38 (17)H9A—O9—H9B101.0
Co1—N3—C15108.10 (11)H10A—O10—H10B115.9
Co1—N3—C16107.51 (12)C1—N1—H1115.5
Co1—N3—C17104.54 (10)C14—N1—H1115.5
C15—N3—C16112.18 (14)C1—C2—H2119.8
C15—N3—C17110.05 (14)C3—C2—H2119.8
C16—N3—C17113.97 (14)C2—C3—H3119.7
Co1—N4—C20127.63 (14)C4—C3—H3119.7
Co1—N4—C24114.35 (11)C4—C5—H5119.4
C20—N4—C24117.98 (17)C6—C5—H5119.4
Co1—N5—C28111.96 (11)C1—C6—H6120.2
Co1—N5—C31130.00 (14)C5—C6—H6120.2
C28—N5—C31117.76 (17)C8—C9—H9121.1
N1—C1—C2116.14 (17)C10—C9—H9121.1
N1—C1—C6124.26 (17)C9—C10—H10119.4
C2—C1—C6119.59 (17)C11—C10—H10119.4
C1—C2—C3120.43 (19)C10—C11—H11119.5
C2—C3—C4120.63 (19)C12—C11—H11119.5
C3—C4—C5118.52 (17)C11—C12—H12120.7
C3—C4—C7121.28 (18)C13—C12—H12120.7
C5—C4—C7120.19 (18)N3—C15—H15A109.0
C4—C5—C6121.2 (2)N3—C15—H15B109.0
C1—C6—C5119.60 (19)C14—C15—H15A109.0
S1—C7—N2115.08 (14)C14—C15—H15B109.0
S1—C7—C4120.43 (15)H15A—C15—H15B107.8
N2—C7—C4124.49 (18)N3—C16—H16A108.9
S1—C8—C9129.13 (17)N3—C16—H16B108.9
S1—C8—C13109.32 (14)C18—C16—H16A108.9
C9—C8—C13121.52 (19)C18—C16—H16B108.9
C8—C9—C10117.8 (2)H16A—C16—H16B107.7
C9—C10—C11121.3 (2)N3—C17—H17A109.5
C10—C11—C12121.1 (2)N3—C17—H17B109.6
C11—C12—C13118.6 (2)C19—C17—H17A109.6
N2—C13—C8114.93 (18)C19—C17—H17B109.5
N2—C13—C12125.35 (19)H17A—C17—H17B108.1
C8—C13—C12119.71 (18)N4—C20—H20118.4
O5—C14—N1124.39 (17)C21—C20—H20118.4
O5—C14—C15122.21 (17)C20—C21—H21120.6
N1—C14—C15113.38 (17)C22—C21—H21120.6
N3—C15—C14112.86 (17)C21—C22—H22120.2
N3—C16—C18113.33 (15)C23—C22—H22120.2
N3—C17—C19110.50 (15)C23—C25—H25119.4
O1—C18—O2125.49 (19)C26—C25—H25119.4
O1—C18—C16116.69 (17)C25—C26—H26119.5
O2—C18—C16117.69 (14)C27—C26—H26119.5
O3—C19—O4124.75 (16)C27—C29—H29120.3
O3—C19—C17117.19 (17)C30—C29—H29120.3
O4—C19—C17118.05 (15)C29—C30—H30120.4
N4—C20—C21123.26 (18)C31—C30—H30120.4
C20—C21—C22118.81 (17)N5—C31—H31118.4
C21—C22—C23119.55 (19)C30—C31—H31118.5
O2—Co1—O4—C1911.8 (2)C20—C21—C22—C231.5 (2)
O4—Co1—O2—C1824.8 (2)C21—C22—C23—C240.1 (2)
O2—Co1—O5—C1487.79 (12)C21—C22—C23—C25179.49 (17)
O5—Co1—O2—C1886.97 (14)C22—C23—C24—N42.6 (2)
O2—Co1—N3—C15105.94 (11)C22—C23—C24—C28177.10 (15)
O2—Co1—N3—C1615.37 (11)C22—C23—C25—C26178.27 (18)
O2—Co1—N3—C17136.84 (11)C24—C23—C25—C262.1 (2)
N3—Co1—O2—C187.64 (13)C25—C23—C24—N4177.03 (16)
O2—Co1—N4—C20103.14 (15)C25—C23—C24—C283.3 (2)
O2—Co1—N4—C2474.39 (12)N4—C24—C28—N52.1 (2)
N4—Co1—O2—C18179.34 (13)N4—C24—C28—C27179.36 (15)
O2—Co1—N5—C2896.76 (11)C23—C24—C28—N5177.58 (15)
O2—Co1—N5—C3176.90 (15)C23—C24—C28—C270.9 (2)
N5—Co1—O2—C18102.78 (14)C23—C25—C26—C271.4 (2)
O4—Co1—O5—C1468.54 (12)C25—C26—C27—C283.8 (2)
O5—Co1—O4—C1999.76 (14)C25—C26—C27—C29175.58 (17)
O4—Co1—N3—C1587.70 (10)C26—C27—C28—N5178.99 (15)
O4—Co1—N3—C16150.99 (12)C26—C27—C28—C242.6 (2)
O4—Co1—N3—C1729.52 (10)C26—C27—C29—C30179.52 (17)
N3—Co1—O4—C1920.78 (14)C28—C27—C29—C300.1 (2)
O4—Co1—N4—C2087.67 (15)C29—C27—C28—N51.6 (2)
O4—Co1—N4—C2494.80 (12)C29—C27—C28—C24176.84 (15)
N4—Co1—O4—C19166.84 (14)C27—C29—C30—C311.2 (2)
O4—Co1—N5—C28108.15 (11)C29—C30—C31—N51.3 (2)
O4—Co1—N5—C3178.19 (16)H1—N1—C1—C21.6
N5—Co1—O4—C1989.02 (14)H1—N1—C1—C6179.6
O5—Co1—N3—C159.75 (10)H1—N1—C14—O5177.8
O5—Co1—N3—C16111.56 (12)H1—N1—C14—C153.9
O5—Co1—N3—C17126.97 (11)Co1—N3—C15—H15A131.0
N3—Co1—O5—C148.95 (11)Co1—N3—C15—H15B111.6
O5—Co1—N4—C208.09 (15)Co1—N3—C16—H16A100.5
O5—Co1—N4—C24169.44 (12)Co1—N3—C16—H16B142.2
N4—Co1—O5—C14167.77 (12)Co1—N3—C17—H17A155.1
N3—Co1—N5—C28174.28 (10)Co1—N3—C17—H17B86.5
N3—Co1—N5—C310.63 (16)C15—N3—C16—H16A140.7
N5—Co1—N3—C15172.52 (10)C15—N3—C16—H16B23.5
N5—Co1—N3—C1666.17 (12)C16—N3—C15—H15A12.5
N5—Co1—N3—C1755.30 (11)C16—N3—C15—H15B130.0
N4—Co1—N5—C288.77 (11)C15—N3—C17—H17A39.3
N4—Co1—N5—C31177.58 (16)C15—N3—C17—H17B157.7
N5—Co1—N4—C20174.65 (15)C17—N3—C15—H15A115.5
N5—Co1—N4—C247.82 (11)C17—N3—C15—H15B2.0
C7—S1—C8—C9178.16 (18)C16—N3—C17—H17A87.8
C7—S1—C8—C130.34 (13)C16—N3—C17—H17B30.6
C8—S1—C7—N20.35 (14)C17—N3—C16—H16A14.9
C8—S1—C7—C4178.86 (14)C17—N3—C16—H16B102.4
Co1—O2—C18—O1178.08 (15)Co1—N4—C20—H204.2
Co1—O2—C18—C162.4 (2)C24—N4—C20—H20178.4
Co1—O4—C19—O3172.48 (16)Co1—N5—C31—H316.7
Co1—O4—C19—C176.3 (2)C28—N5—C31—H31179.9
Co1—O5—C14—N1172.12 (13)N1—C1—C2—H21.3
Co1—O5—C14—C156.1 (2)N1—C1—C6—H62.5
C1—N1—C14—O52.2 (2)C2—C1—C6—H6178.8
C1—N1—C14—C15176.11 (15)C6—C1—C2—H2179.8
C14—N1—C1—C2178.38 (16)C1—C2—C3—H3179.7
C14—N1—C1—C60.4 (2)H2—C2—C3—C4179.7
C7—N2—C13—C81.2 (2)H2—C2—C3—H30.3
C7—N2—C13—C12177.24 (17)H3—C3—C4—C5179.6
C13—N2—C7—S10.95 (19)H3—C3—C4—C70.4
C13—N2—C7—C4178.23 (15)C3—C4—C5—H5178.6
Co1—N3—C15—C149.67 (16)C7—C4—C5—H50.5
Co1—N3—C16—C1820.84 (19)C4—C5—C6—H6178.1
Co1—N3—C17—C1934.33 (17)H5—C5—C6—C1178.1
C15—N3—C16—C1897.9 (2)H5—C5—C6—H61.9
C16—N3—C15—C14108.70 (17)S1—C8—C9—H93.7
C15—N3—C17—C1981.54 (19)C13—C8—C9—H9178.6
C17—N3—C15—C14123.28 (15)C8—C9—C10—H10179.3
C16—N3—C17—C19151.43 (17)H9—C9—C10—C11179.3
C17—N3—C16—C18136.21 (17)H9—C9—C10—H100.7
Co1—N4—C20—C21175.81 (13)C9—C10—C11—H11179.2
Co1—N4—C24—C23174.44 (13)H10—C10—C11—C12179.2
Co1—N4—C24—C285.86 (19)H10—C10—C11—H110.8
C20—N4—C24—C233.3 (2)C10—C11—C12—H12178.2
C20—N4—C24—C28176.36 (15)H11—C11—C12—C13178.2
C24—N4—C20—C211.6 (2)H11—C11—C12—H121.8
Co1—N5—C28—C248.61 (18)H12—C12—C13—N22.7
Co1—N5—C28—C27172.94 (13)H12—C12—C13—C8178.9
Co1—N5—C31—C30173.26 (13)O5—C14—C15—H15A124.4
C28—N5—C31—C300.09 (19)O5—C14—C15—H15B118.2
C31—N5—C28—C24176.88 (15)N1—C14—C15—H15A57.3
C31—N5—C28—C271.6 (2)N1—C14—C15—H15B60.2
N1—C1—C2—C3178.69 (15)H16A—C16—C18—O171.5
N1—C1—C6—C5177.53 (16)H16A—C16—C18—O2104.7
C2—C1—C6—C51.2 (2)H16B—C16—C18—O145.8
C6—C1—C2—C30.2 (2)H16B—C16—C18—O2138.1
C1—C2—C3—C40.3 (2)H17A—C17—C19—O339.0
C2—C3—C4—C50.4 (2)H17A—C17—C19—O4142.2
C2—C3—C4—C7179.51 (16)H17B—C17—C19—O379.4
C3—C4—C5—C61.4 (2)H17B—C17—C19—O499.4
C3—C4—C7—S15.5 (2)N4—C20—C21—H21179.3
C3—C4—C7—N2175.41 (17)H20—C20—C21—C22179.3
C5—C4—C7—S1173.68 (13)H20—C20—C21—H210.7
C5—C4—C7—N25.5 (2)C20—C21—C22—H22178.5
C7—C4—C5—C6179.40 (16)H21—C21—C22—C23178.5
C4—C5—C6—C11.9 (2)H21—C21—C22—H221.5
S1—C8—C9—C10176.25 (15)H22—C22—C23—C24179.9
S1—C8—C13—N20.96 (19)H22—C22—C23—C250.6
S1—C8—C13—C12177.62 (14)C22—C23—C25—H251.7
C9—C8—C13—N2178.97 (16)C24—C23—C25—H25177.9
C9—C8—C13—C120.4 (2)C23—C25—C26—H26178.6
C13—C8—C9—C101.3 (2)H25—C25—C26—C27178.5
C8—C9—C10—C110.7 (2)H25—C25—C26—H261.5
C9—C10—C11—C120.8 (3)H26—C26—C27—C28176.2
C10—C11—C12—C131.8 (2)H26—C26—C27—C294.4
C11—C12—C13—N2177.26 (17)C26—C27—C29—H290.5
C11—C12—C13—C81.2 (2)C28—C27—C29—H29179.9
O5—C14—C15—N33.1 (2)C27—C29—C30—H30178.8
N1—C14—C15—N3178.55 (13)H29—C29—C30—C31178.8
N3—C16—C18—O1167.17 (16)H29—C29—C30—H301.2
N3—C16—C18—O216.8 (2)C29—C30—C31—H31178.7
N3—C17—C19—O3159.80 (17)H30—C30—C31—N5178.7
N3—C17—C19—O421.3 (2)H30—C30—C31—H311.3
N4—C20—C21—C220.7 (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) x1, y, z; (vii) x+1, y+1, z+1; (viii) x, y1, z; (ix) x, y1, z+1; (x) x, y+1, z; (xi) x, y+2, z; (xii) x, y, z+1; (xiii) x, y+1, z1; (xiv) x, y, z1; (xv) x, y+2, z1; (xvi) x1, y+1, z; (xvii) x1, y+1, z1; (xviii) x+1, y1, z; (xix) x+1, y1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O8viii0.901.872.763 (2)170
O6—H6B···O30.871.882.739 (2)170
O7—H7A···O1vi0.921.912.810 (2)168
O7—H7B···O6vii0.921.802.699 (2)164
O8—H8A···O70.922.002.906 (2)168
O8—H8B···O9iii0.981.842.764 (2)156
O9—H9A···O3i0.881.882.752 (2)172
O9—H9B···N20.882.012.879 (2)172
O10—H10A···O31.022.022.905 (2)144
O10—H10B···O1vi1.032.583.198 (2)118
O10—H10B···O2vi1.031.942.957 (2)169
N1—H1···O70.882.022.882 (2)168
Symmetry codes: (i) x+1, y+1, z; (iii) x+1, y+2, z; (vi) x1, y, z; (vii) x+1, y+1, z+1; (viii) x, y1, z.

Experimental details

Crystal data
Chemical formula[Co(C19H15N3O5S)(C12H8N2)]·5H2O
Mr726.62
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)8.9990 (7), 12.7766 (7), 14.0652 (8)
α, β, γ (°)92.661 (2), 102.770 (2), 97.389 (2)
V3)1559.39 (17)
Z2
Radiation typeMo Kα
µ (mm1)0.69
Crystal size (mm)0.50 × 0.50 × 0.20
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.703, 0.872
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
15300, 7094, 6151
Rint0.030
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.118, 1.12
No. of reflections7094
No. of parameters434
No. of restraints?
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.56, 0.83

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC & Rigaku, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top
Co1—O22.0728 (11)Co1—N32.1973 (16)
Co1—O42.0577 (13)Co1—N42.1007 (16)
Co1—O52.0943 (14)Co1—N52.1680 (16)
O2—Co1—O4154.50 (5)O4—Co1—N378.63 (5)
O2—Co1—N379.77 (5)N3—Co1—N5109.17 (5)
O2—Co1—N4104.18 (5)N4—Co1—N578.15 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O8i0.9011.8712.763 (2)169.8
O6—H6B···O30.8671.8822.739 (2)169.6
O7—H7A···O1ii0.9151.9092.810 (2)167.9
O7—H7B···O6iii0.9191.8032.699 (2)164.3
O8—H8A···O70.9162.0042.906 (2)168.3
O8—H8B···O9iv0.9821.8392.764 (2)155.6
O9—H9A···O3v0.8821.8762.752 (2)172.1
O9—H9B···N20.8782.0082.879 (2)171.7
O10—H10A···O31.0192.0182.905 (2)144.0
O10—H10B···O1ii1.0332.5813.198 (2)117.9
O10—H10B···O2ii1.0331.9362.957 (2)169.4
N1—H1···O70.8802.0172.882 (2)167.6
Symmetry codes: (i) x, y1, z; (ii) x1, y, z; (iii) x+1, y+1, z+1; (iv) x+1, y+2, z; (v) x+1, y+1, z.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds