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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Pages m1355-m1356
doi:10.1107/S1600536808031425

Tris{N-[(anthracen-9-yl)methyl­ene­amino]thio­ureato}cobalt(III) tetra­hydrate

Jianying Zhaoa and Yu Zhanga*

aDepartment of Chemistry, Huaiyin Teachers College, Huai'an 223300, Jiangsu, People's Republic of China
*Correspondence e-mail: yuzhang@hytc.edu.cn

(Received 3 August 2008; accepted 29 September 2008; online 4 October 2008)

In the title complex, [Co(C16H12N3S)3]·4H2O, the central CoIII atom is in a distorted octa­hedral coordination environment. There are three N-[(anthracen-9-yl)­methyl­ene­amino]­thio­ureate ligands coordinated to the CoIII atom via three imine N and three thio­amide S atoms. The Co—S and Co—N bond distances are in expected ranges [2.2194 (8)—2.2545 (8) and 1.926 (2)—1.985 (2)Å, respectively]. The endocyclic S—Co—N bond angles in the five-membered chelate rings range from 82.91 (7) to 85.33 (7)°. The structure contains four water mol­ecules which are disordered over 12 sites and link the complex mol­ecules into a three-dimensional network through N—H⋯O, O—H⋯O, O—H⋯N, and O—H⋯S hydrogen bonds.

Related literature

For related structures, see: Chandra et al. (2003[Chandra, S., Kumar, U. & Verma, H. S. (2003). Orient. J. Chem. 19, 355-359.]); Funston et al. (2003[Funston, A. M., Ghiggino, K. P., Grannas, M. J., McFadyen, W. D. & Tregloan, P. A. (2003). Discuss. Faraday Soc. pp. 3704-3711.]); Casas et al. (2000[Casas, J. S., Garcia-Tasende, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197-261.]); Rodriguez-Arguelles et al. (2004[Rodriguez-Arguelles, M. C., Lopez-Silva, E. C., Sanmartin, J., Bacchi, A., Pelizzi, C. & Zani, F. (2004). Inorg. Chim. Acta. 357, 2543-2551.]); Saha et al. (2003[Saha, N. C., Butcher, R. J., Chaudhari, S. & Saha, N. (2003). Polyhedron, 22, 383-389.]). For biological activities, see: He et al. (2003[He, Y., Wu, B., Yang, J., Robinson, D., Risen, L., Ranken, R., Blyn, L., Sheng, S. & Swayze, E. E. (2003). Bioorg. Med. Chem. Lett. 13, 3253-3260.]); Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-941.]); Kabanos et al. (1992[Kabanos, T. A., Kersmidas, A. D., Mentzafos, D., Russo, U., Terzis, A. & Tsangaris, J. M. (1992). J. Chem. Soc. Dalton Trans. pp. 2729-2734.]); Navarrete-Vazquez et al. (2001[Navarrete-Vazquez, G., Cedillo, R., Hernandez-Campos, A., Yepez, J., Hernndez-Luis, F., Valldez, J., Morales, R., Cortes, R., Hernandez, M. & Castillo, R. (2001). Bioorg. Med. Chem. Lett. 11, 187-193.]); Ozden et al., 2005[Ozden, S., Atabey, D., Yildiz, S. & Goker, H. (2005). Bioorg. Med. Chem. 13, 1587-1596.]; Pawar et al. (2004[Pawar, N. S., Dalal, D. S., Shimpi, S. R. & Mahulikar, P. P. (2004). Eur. J. Pharm. Sci. 21, 115-118.]).

[Scheme 1]

Experimental

Crystal data

  • [Co(C16H12N3S)3]·4H2O

  • Mr = 966.03

  • Triclinic, [P \overline 1]

  • a = 9.8907 (19) Å

  • b = 17.073 (3) Å

  • c = 17.511 (4) Å

  • α = 91.315 (7)°

  • β = 99.920 (6)°

  • γ = 93.972 (6)°

  • V = 2903.9 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.45 mm−1

  • T = 291 (2) K

  • 0.28 × 0.22 × 0.20 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.886, Tmax = 0.916

  • 36568 measured reflections

  • 11268 independent reflections

  • 8244 reflections with I > 2σ(I)

  • Rint = 0.053
Refinement

  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.132

  • S = 1.04

  • 11268 reflections

  • 723 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.90 e Å−3

  • Δρmin = −0.92 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H3A⋯O10 0.85 (4) 2.36 (4) 3.130 (6) 151 (3)
N9—H9B⋯O7 0.85 (4) 2.38 (4) 3.162 (8) 153 (4)
N9—H9B⋯O8 0.85 (4) 2.47 (4) 3.002 (9) 122 (3)
N9—H9A⋯O11 0.85 (4) 2.24 (4) 2.957 (9) 142 (4)
O1—H1X⋯O6 0.82 1.59 2.263 (11) 137
O1—H1X⋯O11i 0.82 2.58 3.013 (11) 114
O7—H7Y⋯N3ii 0.82 2.62 3.158 (10) 124
O8—H8Y⋯S2ii 0.82 2.60 3.371 (10) 157
O9—H9Y⋯O11iii 0.82 2.59 3.300 (12) 146
O12—H12X⋯O11iii 0.82 2.25 3.003 (11) 153
O10—H10X⋯N9iv 0.82 2.26 3.033 (6) 157
O10—H10Y⋯N8iv 0.82 2.48 2.939 (6) 116
O11—H11X⋯S3 0.82 2.46 3.165 (8) 145
O11—H11X⋯N5 0.82 2.57 3.163 (9) 130
O11—H11Y⋯O1v 0.82 2.50 3.013 (11) 122
O12—H12Y⋯O9 0.82 2.06 2.494 (12) 113
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1; (iv) x-1, y, z; (v) x, y+1, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031425/pv2097sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031425/pv2097Isup2.hkl

checkCIF report


Comment top

The thiosemicarbazone derivatives and their transition metal complexes have received considerable attention because of their biological and pharmaceutical properties. These compounds have been previously investigated for their antifungal (Horton et al., 2003), antibacterial (He et al., 2003), antimicrobial (Pawar et al., 2004), antiamoebic (Ozden et al., 2005), antiparasitic (Navarrete-Vazquez et al., 2001) and antitumor activities (Kabanos et al., 1992). Although many thiosemicarbazones and their transition metal complexes have been studied (Rodriguez-Arguelles et al., 2004), there is no information available on the structural characterization of anthracene thiosemicarbazone derivatives. The pharmacological or coordinative information on the anthracene thiosemicarbazone derivatives and their complexes are also unknown (Casas et al., 2000). In this paper, we report the synthesis and crystal structure of tris(N-(9-anthracene) methylene-aniline thiourea)-cobalt(III) tetrahydrate complex, (I).

In the structure of (I), the central cobalt atom adopts a distorted octahedral geometry (Fig. 1). There are three ligands, N-(9-anthracene), methylene-aniline and thiourea which are coordinated to the cobalt atom via three imine nitrogen and three thioamide sulfur atoms. As expected, the sulfur and nitrogen atoms are in the mer conformation. The bond distances Co—S and Co—N, are in the expected ranges of 2.2194 (8)–2.2545 (8) and 1.926 (2)–1.985 (2) Å, respectively, which are in agreement with the literature values (Chandra et al., 2003; Saha et al., 2003). The bond lengths in the anthracene rings are typical and compareable to the values reported for the complex trans-dichloro-(6-(anthracen-9-ylmethyl) -1,4,8,11-tetraazacyclotetradecane)-cobalt(III) chloride pentahydrate (Funston et al., 2003). The endocyclic bond angles S—Co—N in the five membered rings involving chelates range from 82.91 (7) to 85.33 (7)°. In the molecule there are three anthracene rings A (C1–C14), C (C17–C30), and E(C33–C46) and three five memberd chelating rings, B (Co1/N1/N2/C16/S1), D (Co1/N4/N5/C32/S2), and F (Co1/N7/N8/C48/S3). The dihedral angles between the mean-planes of the rings A and B, C and D, and E and F are 47.60 (4), 54.95 (6), and 51.51 (4)%, respectively.

There are four disordered water molecules in the structure which are located over twelve sites with partial occupancyies and take part in a bridging role, linking the complex molecules into a three-dimensional network through N—H···O, O—H···O, O—H···N, and O—H···S type hydrogen bonds (details are given in Table 1).

Related literature top

For related structures, see: Chandra et al. (2003); Funston et al. (2003); Casas et al. (2000); Rodriguez-Arguelles et al. (2004); Saha et al. (2003). For biological activities, see: He et al. (2003); Horton et al. (2003); Kabanos et al. (1992); Navarrete-Vazquez et al. (2001); Ozden et al., 2005; Pawar et al. (2004).

Experimental top

An ethanolic (25 ml) solution of Co(ClO4).6H2O (0.267 g, 0.10 mmol) was slowly added to N-(9-anthracene) methylene-aniline thiourea (0.837 g, 0.30 mmol) in ethanol (50 ml). The mixture was allowed to stand for 16 days at room temperature. Dark brown prismatic crystals suitable for X-ray analysis were obtained.

Refinement top

H atoms bonded to N were located in the difference map and were allowed to refine with distance restraints of N—H = 0.85 (4) Å, and Uiso(H) = 1.2Ueq(N). The H-atoms bonded to C-atoms were positioned geometrically and treated in a riding model, with C—H = 0.93 Å, and Uiso(H) = 1.2 times Ueq(C). The four molecules occupy 12 positions, the occupation factors for O1 to O12 were 0.390 (10), 0.301 (12), 0.309 (11), 0.400 (13), 0.304 (9), 0.297 (14), 0.392 (9), 0.300 (12), 0.308 (11), 0.396 (9), 0.299 (11) and 0.304 (9), respectively, which were refined as the free variables. The hydrogen atoms bonded to water molecules were positioned geometrically and refined using a riding model, with O—H = 0.82 Å and H—O—H angle at 104.5° and with Uiso(H) = 1.2Ueq(O). The highest electron density in the final difference map was located close to O11.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
Tris{N-[(anthracen-9-yl)methyleneamino]thioureato}cobalt(III) tetrahydrate top
Crystal data top
[Co(C16H12N3S)3]·4H2OZ = 2
Mr = 966.03F(000) = 1004
Triclinic, P1Dx = 1.105 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8907 (19) ÅCell parameters from 5672 reflections
b = 17.073 (3) Åθ = 2.1–25.1°
c = 17.511 (4) ŵ = 0.45 mm−1
α = 91.315 (7)°T = 291 K
β = 99.920 (6)°Block, dark brown
γ = 93.972 (6)°0.28 × 0.22 × 0.20 mm
V = 2903.9 (10) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer		11268 independent reflections
Radiation source: fine-focus sealed tube8244 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ϕ and ω scansθmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −11→12
Tmin = 0.886, Tmax = 0.916k = −21→21
36568 measured reflectionsl = −21→19
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0616P)2 + 1.0884P]
where P = (Fo2 + 2Fc2)/3
11268 reflections(Δ/σ)max < 0.001
723 parametersΔρmax = 0.90 e Å−3
0 restraintsΔρmin = −0.92 e Å−3
Crystal data top
[Co(C16H12N3S)3]·4H2Oγ = 93.972 (6)°
Mr = 966.03V = 2903.9 (10) Å3
Triclinic, P1Z = 2
a = 9.8907 (19) ÅMo Kα radiation
b = 17.073 (3) ŵ = 0.45 mm−1
c = 17.511 (4) ÅT = 291 K
α = 91.315 (7)°0.28 × 0.22 × 0.20 mm
β = 99.920 (6)°
Data collection top
Bruker SMART APEX CCD
diffractometer		11268 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		8244 reflections with I > 2σ(I)
Tmin = 0.886, Tmax = 0.916Rint = 0.054
36568 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.90 e Å−3
11268 reflectionsΔρmin = −0.92 e Å−3
723 parameters
Special details top

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

2.9231 (0.0039) x + 5.2249 (0.0137) y + 14.3798 (0.0073) z = 8.0721 (0.0041)

* -0.0965 (0.0029) C1 * -0.0957 (0.0029) C2 * -0.0036 (0.0029) C3 * 0.0943 (0.0029) C4 * 0.1068 (0.0032) C5 * 0.0348 (0.0029) C6 * -0.0687 (0.0029) C7 * -0.0824 (0.0030) C8 * -0.0553 (0.0032) C9 * -0.0172 (0.0030) C10 * 0.0763 (0.0032) C11 * 0.0979 (0.0031) C12 * 0.0622 (0.0029) C13 * -0.0529 (0.0030) C14

Rms deviation of fitted atoms = 0.0741

- 4.9814 (0.0075) x + 4.3447 (0.0118) y + 15.7855 (0.0071) z = 7.5113 (0.0076)

Angle to previous plane (with approximate e.s.d.) = 47.70 (0.05)

* -0.0696 (0.0009) Co1 * 0.0932 (0.0014) N1 * -0.0516 (0.0018) N2 * -0.0286 (0.0017) C16 * 0.0566 (0.0011) S1

Rms deviation of fitted atoms = 0.0636

2.8734 (0.0035) x + 5.6841 (0.0129) y + 14.2322 (0.0068) z = 7.3855 (0.0124)

Angle to previous plane (with approximate e.s.d.) = 47.60 (0.05)

* 0.0309 (0.0024) C17 * 0.0141 (0.0027) C18 * -0.0339 (0.0027) C19 * -0.0535 (0.0030) C20 * -0.0297 (0.0030) C21 * 0.0358 (0.0030) C22 * 0.0565 (0.0029) C23 * 0.0204 (0.0029) C24 * 0.0095 (0.0030) C25 * -0.0415 (0.0030) C26 * -0.0419 (0.0028) C27 * -0.0195 (0.0027) C28 * 0.0296 (0.0027) C29 * 0.0231 (0.0027) C30

Rms deviation of fitted atoms = 0.0341

- 9.1789 (0.0035) x + 2.1487 (0.0123) y - 3.5707 (0.0144) z = 0.8355 (0.0111)

Angle to previous plane (with approximate e.s.d.) = 54.95 (0.06)

* -0.0837 (0.0009) Co1 * 0.1056 (0.0013) N4 * -0.0460 (0.0017) N5 * -0.0487 (0.0018) C32 * 0.0728 (0.0012) S2

Rms deviation of fitted atoms = 0.0748

6.3204 (0.0049) x + 12.0610 (0.0065) y + 0.3576 (0.0128) z = 7.7520 (0.0036)

Angle to previous plane (with approximate e.s.d.) = 52.76 (0.06)

* 0.0549 (0.0024) C33 * 0.0124 (0.0026) C34 * 0.0290 (0.0026) C35 * -0.0236 (0.0026) C36 * -0.0270 (0.0027) C37 * -0.0047 (0.0027) C38 * -0.0022 (0.0027) C39 * -0.0012 (0.0030) C40 * 0.0058 (0.0030) C41 * 0.0210 (0.0032) C42 * 0.0245 (0.0031) C43 * -0.0395 (0.0030) C44 * -0.0445 (0.0030) C45 * -0.0047 (0.0028) C46

Rms deviation of fitted atoms = 0.0267

- 0.9842 (0.0075) x + 16.5335 (0.0046) y - 4.5518 (0.0118) z = 10.6006 (0.0060)

Angle to previous plane (with approximate e.s.d.) = 51.51 (0.05)

* 0.1181 (0.0009) Co1 * -0.1461 (0.0013) N7 * 0.0569 (0.0016) N8 * 0.0834 (0.0015) C48 * -0.1122 (0.0010) S3

Rms deviation of fitted atoms = 0.1078

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1−0.0004 (4)0.49552 (19)0.37467 (18)0.0451 (8)
C20.1076 (3)0.44401 (18)0.37149 (18)0.0414 (7)
C30.2263 (4)0.4681 (2)0.3450 (2)0.0495 (8)
H30.23510.51780.32490.059*
C40.3333 (4)0.4189 (2)0.3479 (2)0.0504 (8)
H40.41310.43550.32960.060*
C50.3203 (4)0.3449 (2)0.3783 (2)0.0605 (10)
H50.39140.31180.37990.073*
C60.2032 (4)0.3201 (2)0.4062 (2)0.0525 (9)
H60.19580.27070.42700.063*
C70.0951 (4)0.3695 (2)0.40299 (18)0.0464 (8)
C8−0.0213 (4)0.34682 (19)0.4339 (2)0.0501 (9)
H8−0.02990.29630.45210.060*
C9−0.1257 (4)0.39649 (19)0.4390 (2)0.0507 (9)
C10−0.2356 (4)0.3693 (2)0.4739 (2)0.0557 (10)
H10−0.24340.31850.49140.067*
C11−0.3298 (4)0.4211 (2)0.4807 (2)0.0638 (11)
H11−0.40330.40550.50500.077*
C12−0.3229 (4)0.4970 (2)0.4532 (2)0.0530 (9)
H12−0.39240.52980.45810.064*
C13−0.2153 (4)0.5235 (2)0.4192 (2)0.0504 (8)
H13−0.20870.57480.40280.060*
C14−0.1148 (4)0.47218 (18)0.40945 (18)0.0424 (7)
C150.0225 (3)0.57617 (17)0.34798 (17)0.0354 (6)
H150.10310.60450.37160.043*
C16−0.2661 (3)0.61425 (16)0.22101 (18)0.0339 (6)
C17−0.0070 (3)0.93633 (15)0.14856 (15)0.0295 (6)
C18−0.1222 (3)0.98154 (16)0.15258 (17)0.0344 (6)
C19−0.2345 (3)0.95054 (17)0.18427 (19)0.0401 (7)
H19−0.23480.90010.20320.048*
C20−0.3452 (4)0.9954 (2)0.1873 (2)0.0496 (8)
H20−0.41960.97500.20840.060*
C21−0.3457 (4)1.07082 (19)0.1590 (2)0.0496 (8)
H21−0.42081.10040.16030.060*
C22−0.2347 (4)1.1015 (2)0.1289 (2)0.0521 (9)
H22−0.23431.15220.11070.062*
C23−0.1224 (3)1.05713 (18)0.12542 (19)0.0419 (7)
C24−0.0095 (4)1.08603 (19)0.08854 (19)0.0464 (8)
H24−0.01091.13570.06780.056*
C250.0994 (4)1.0419 (2)0.08340 (19)0.0481 (8)
C260.2076 (4)1.0709 (2)0.0464 (2)0.0522 (9)
H260.20441.12020.02500.063*
C270.3174 (4)1.0272 (2)0.0417 (2)0.0516 (9)
H270.38831.04800.01790.062*
C280.3252 (3)0.95342 (19)0.07113 (19)0.0458 (8)
H280.39940.92410.06670.055*
C290.2176 (4)0.92301 (19)0.1084 (2)0.0462 (8)
H290.22240.87370.12980.055*
C300.1043 (3)0.96635 (17)0.11354 (17)0.0377 (7)
C31−0.0046 (3)0.85530 (15)0.17471 (16)0.0285 (6)
H31−0.00420.81680.13630.034*
C32−0.0260 (3)0.86221 (17)0.36530 (18)0.0384 (7)
C330.0539 (3)0.61759 (16)0.04899 (16)0.0329 (6)
C34−0.0004 (3)0.64474 (17)−0.02610 (18)0.0388 (7)
C35−0.1012 (3)0.69926 (18)−0.0367 (2)0.0460 (8)
H35−0.13460.71940.00560.055*
C36−0.1496 (4)0.7224 (2)−0.1095 (2)0.0504 (9)
H36−0.21970.7565−0.11630.060*
C37−0.0970 (4)0.6965 (2)−0.1755 (2)0.0519 (9)
H37−0.13120.7145−0.22430.062*
C380.0059 (4)0.6442 (2)−0.1668 (2)0.0516 (9)
H380.04200.6276−0.20960.062*
C390.0548 (3)0.61660 (19)−0.09285 (19)0.0450 (8)
C400.1544 (4)0.56412 (17)−0.0809 (2)0.0524 (9)
H400.18960.5466−0.12360.063*
C410.2052 (3)0.53602 (18)−0.0105 (2)0.0451 (8)
C420.3102 (4)0.4819 (2)0.0004 (2)0.0568 (9)
H420.34590.4651−0.04240.068*
C430.3600 (4)0.4540 (2)0.0715 (2)0.0538 (9)
H430.43080.42040.07740.065*
C440.3018 (4)0.4773 (2)0.1356 (2)0.0519 (9)
H440.33180.45680.18380.062*
C450.2022 (4)0.5293 (2)0.1283 (2)0.0524 (9)
H450.16700.54390.17200.063*
C460.1509 (3)0.56158 (18)0.05700 (19)0.0427 (7)
C47−0.0038 (3)0.64530 (16)0.11451 (16)0.0336 (6)
H47−0.09780.63420.11220.040*
C480.2714 (3)0.72902 (16)0.24213 (17)0.0329 (6)
Co1−0.01722 (4)0.72094 (2)0.26757 (2)0.02906 (11)
N1−0.0574 (2)0.61179 (13)0.29523 (14)0.0318 (5)
N2−0.1777 (2)0.56985 (13)0.25965 (13)0.0324 (5)
N3−0.3917 (3)0.58207 (18)0.18756 (17)0.0433 (6)
H3B−0.382 (4)0.534 (2)0.179 (2)0.052*
H3A−0.440 (4)0.598 (2)0.147 (2)0.052*
N4−0.0029 (2)0.83041 (12)0.24356 (13)0.0254 (5)
N50.0057 (2)0.88954 (13)0.29963 (14)0.0320 (5)
N6−0.0234 (3)0.91326 (19)0.42362 (19)0.0514 (8)
H6B−0.088 (4)0.901 (2)0.448 (2)0.062*
H6A−0.033 (4)0.959 (2)0.406 (2)0.062*
N70.0635 (2)0.68505 (13)0.17780 (14)0.0327 (5)
N80.1979 (2)0.70442 (13)0.17449 (14)0.0330 (5)
N90.4071 (3)0.7494 (2)0.2452 (2)0.0519 (8)
H9B0.454 (4)0.721 (2)0.278 (2)0.062*
H9A0.425 (4)0.798 (2)0.259 (2)0.062*
O10.1493 (6)0.0369 (3)0.3188 (4)0.048 (3)0.390 (10)
H1X0.23000.03920.31320.058*0.39 (8)
H1Y0.15210.05170.36400.058*0.39 (8)
O20.2155 (9)0.8786 (6)0.6169 (6)0.061 (4)0.301 (12)
H2X0.20500.89590.57320.073*0.301 (9)
H2Y0.23850.83390.61130.073*0.301 (9)
O30.1224 (8)0.7650 (6)0.7284 (5)0.055 (4)0.309 (11)
H3X0.16720.72690.72470.065*0.309 (9)
H3Y0.15480.78510.77120.065*0.309 (8)
O40.4442 (8)0.7059 (5)0.7923 (5)0.076 (4)0.400 (13)
H4X0.44620.69270.83720.091*0.400 (11)
H4Y0.52150.69930.78360.091*0.400 (10)
O50.5254 (7)0.7669 (6)1.0002 (6)0.055 (4)0.304 (11)
H5X0.54280.80961.02360.066*0.304 (9)
H5Y0.52340.77700.95450.066*0.304 (9)
O60.3423 (14)0.1055 (6)0.2972 (7)0.076 (6)0.297 (14)
H6X0.29570.12550.26040.091*0.297 (12)
H6Y0.41690.10140.28370.091*0.297 (10)
O70.4935 (8)0.6024 (4)0.3438 (5)0.065 (3)0.392 (12)
H7X0.42040.60010.36010.078*0.392 (9)
H7Y0.48040.57090.30680.078*0.392 (10)
O80.6008 (10)0.7804 (7)0.3965 (6)0.066 (5)0.300 (12)
H8X0.56130.74850.42100.079*0.300 (10)
H8Y0.67490.76240.39460.079*0.300 (9)
O90.5014 (9)0.1250 (5)0.5405 (6)0.057 (4)0.308 (11)
H9X0.55420.16290.53530.068*0.308 (8)
H9Y0.54610.09870.57300.068*0.308 (9)
O10−0.5834 (6)0.6894 (3)0.0820 (3)0.040 (2)0.396 (9)
H10X−0.57520.71740.12150.048*0.396 (7)
H10Y−0.65620.66300.08080.048*0.396 (7)
O110.3213 (9)0.9052 (5)0.2864 (5)0.051 (3)0.299 (11)
H11X0.26170.87380.29750.061*0.299 (8)
H11Y0.32860.94080.31940.061*0.299 (8)
O120.3964 (8)0.0380 (4)0.6305 (4)0.041 (3)0.304 (9)
H12X0.46810.06590.64280.049*0.304 (7)
H12Y0.37820.04010.58310.049*0.304 (7)
S1−0.23532 (7)0.71424 (4)0.20858 (4)0.03045 (16)
S2−0.06780 (7)0.76419 (4)0.37977 (4)0.03041 (16)
S30.20521 (7)0.73627 (4)0.32576 (4)0.03020 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.055 (2)0.0498 (18)0.0292 (17)0.0107 (15)−0.0014 (14)0.0085 (14)
C20.0452 (18)0.0451 (16)0.0315 (16)−0.0018 (13)0.0016 (14)−0.0007 (13)
C30.054 (2)0.056 (2)0.040 (2)0.0048 (16)0.0127 (16)−0.0105 (15)
C40.050 (2)0.061 (2)0.040 (2)0.0086 (16)0.0090 (16)−0.0141 (16)
C50.061 (2)0.068 (2)0.052 (2)−0.0215 (19)0.0207 (19)0.0004 (18)
C60.055 (2)0.0536 (19)0.043 (2)−0.0176 (16)0.0001 (16)0.0068 (16)
C70.054 (2)0.0527 (18)0.0256 (16)−0.0164 (16)−0.0026 (14)−0.0070 (14)
C80.054 (2)0.0430 (17)0.045 (2)−0.0120 (15)−0.0091 (16)0.0158 (15)
C90.058 (2)0.0423 (17)0.044 (2)−0.0014 (15)−0.0107 (17)0.0074 (14)
C100.045 (2)0.0503 (19)0.060 (2)−0.0008 (15)−0.0211 (18)0.0073 (17)
C110.054 (2)0.075 (3)0.055 (2)0.0200 (19)−0.0152 (19)0.004 (2)
C120.054 (2)0.068 (2)0.0380 (19)0.0226 (17)0.0055 (16)0.0048 (16)
C130.047 (2)0.070 (2)0.0362 (19)0.0193 (16)0.0070 (15)0.0017 (16)
C140.054 (2)0.0458 (17)0.0261 (16)0.0120 (14)0.0000 (14)0.0045 (13)
C150.0332 (15)0.0418 (15)0.0308 (16)0.0037 (12)0.0032 (12)0.0059 (12)
C160.0304 (15)0.0316 (13)0.0392 (17)0.0005 (11)0.0066 (12)−0.0048 (12)
C170.0335 (14)0.0313 (13)0.0199 (13)−0.0092 (11)−0.0005 (11)−0.0029 (10)
C180.0319 (15)0.0376 (14)0.0323 (16)−0.0071 (11)0.0070 (12)−0.0089 (12)
C190.0446 (17)0.0360 (15)0.0425 (19)0.0025 (12)0.0156 (14)0.0011 (13)
C200.0437 (19)0.0543 (19)0.051 (2)0.0133 (15)0.0053 (16)−0.0027 (16)
C210.0474 (19)0.0459 (18)0.058 (2)0.0074 (14)0.0158 (17)−0.0156 (16)
C220.0446 (19)0.0510 (19)0.060 (2)−0.0004 (15)0.0111 (17)−0.0119 (17)
C230.0414 (17)0.0415 (16)0.0420 (18)−0.0150 (13)0.0141 (14)−0.0114 (14)
C240.058 (2)0.0477 (17)0.0354 (18)−0.0217 (15)0.0259 (15)−0.0075 (14)
C250.056 (2)0.0495 (18)0.0337 (18)−0.0192 (16)0.0042 (15)−0.0006 (14)
C260.061 (2)0.056 (2)0.038 (2)−0.0121 (17)0.0085 (17)0.0184 (16)
C270.058 (2)0.0489 (18)0.0406 (19)−0.0233 (16)−0.0036 (16)0.0122 (15)
C280.0393 (17)0.0466 (17)0.0426 (19)−0.0135 (13)−0.0124 (14)0.0100 (14)
C290.053 (2)0.0393 (16)0.0402 (19)−0.0077 (14)−0.0051 (15)0.0033 (13)
C300.0427 (17)0.0417 (15)0.0246 (15)−0.0119 (13)0.0011 (13)−0.0011 (12)
C310.0326 (14)0.0260 (12)0.0261 (15)0.0078 (10)0.0011 (11)−0.0001 (10)
C320.0441 (17)0.0351 (14)0.0339 (17)−0.0042 (12)0.0049 (13)−0.0089 (12)
C330.0406 (16)0.0355 (14)0.0200 (14)−0.0050 (12)0.0016 (12)−0.0038 (11)
C340.0409 (17)0.0396 (15)0.0317 (16)−0.0076 (12)−0.0014 (13)0.0037 (12)
C350.0468 (19)0.0441 (17)0.048 (2)−0.0062 (14)0.0135 (16)0.0017 (15)
C360.0457 (19)0.0495 (18)0.053 (2)−0.0158 (15)0.0091 (16)−0.0041 (16)
C370.054 (2)0.0531 (19)0.044 (2)−0.0133 (16)0.0030 (16)0.0041 (16)
C380.064 (2)0.0493 (18)0.042 (2)−0.0105 (16)0.0150 (17)0.0034 (15)
C390.0414 (18)0.0444 (17)0.0424 (19)−0.0155 (14)−0.0034 (15)−0.0053 (14)
C400.079 (3)0.0286 (14)0.045 (2)−0.0024 (15)0.0009 (18)−0.0004 (13)
C410.0434 (18)0.0377 (15)0.050 (2)0.0052 (13)−0.0036 (15)−0.0020 (14)
C420.064 (2)0.052 (2)0.054 (2)0.0149 (17)0.0047 (19)0.0014 (17)
C430.057 (2)0.0507 (19)0.049 (2)0.0201 (16)−0.0081 (17)−0.0192 (16)
C440.049 (2)0.0514 (19)0.053 (2)0.0117 (15)0.0029 (17)−0.0125 (16)
C450.055 (2)0.055 (2)0.047 (2)0.0086 (16)0.0036 (17)0.0029 (16)
C460.0429 (17)0.0398 (16)0.0400 (18)−0.0031 (13)−0.0047 (14)−0.0065 (13)
C470.0365 (15)0.0388 (14)0.0247 (15)0.0169 (12)−0.0030 (12)0.0035 (11)
C480.0381 (16)0.0325 (13)0.0293 (15)0.0083 (11)0.0076 (12)−0.0040 (11)
Co10.0298 (2)0.02984 (19)0.0273 (2)0.00171 (14)0.00459 (15)−0.00025 (14)
N10.0262 (12)0.0308 (11)0.0387 (14)0.0020 (9)0.0062 (10)0.0010 (10)
N20.0363 (13)0.0337 (12)0.0248 (12)−0.0071 (10)0.0023 (10)0.0033 (9)
N30.0337 (14)0.0530 (16)0.0384 (16)−0.0031 (12)−0.0049 (12)0.0016 (13)
N40.0235 (11)0.0252 (10)0.0251 (12)−0.0057 (8)0.0016 (9)−0.0074 (9)
N50.0302 (12)0.0365 (12)0.0295 (13)0.0019 (9)0.0077 (10)−0.0101 (10)
N60.0503 (17)0.0517 (16)0.0505 (19)−0.0176 (14)0.0152 (14)−0.0189 (14)
N70.0421 (14)0.0288 (11)0.0273 (13)−0.0043 (10)0.0102 (10)−0.0050 (9)
N80.0378 (13)0.0291 (11)0.0289 (13)−0.0081 (9)0.0017 (10)−0.0025 (9)
N90.0481 (18)0.0562 (18)0.055 (2)0.0013 (14)0.0224 (15)−0.0152 (15)
O10.038 (4)0.066 (4)0.037 (4)−0.020 (3)0.005 (3)−0.002 (3)
O20.057 (6)0.063 (6)0.067 (7)0.006 (4)0.022 (5)0.006 (4)
O30.035 (5)0.089 (7)0.038 (5)0.002 (4)0.003 (3)−0.012 (4)
O40.058 (5)0.090 (6)0.074 (7)−0.024 (4)0.011 (4)−0.013 (4)
O50.031 (4)0.081 (7)0.050 (6)−0.013 (4)0.006 (3)0.010 (4)
O60.084 (9)0.083 (8)0.064 (8)−0.025 (6)0.038 (6)−0.030 (6)
O70.054 (5)0.057 (4)0.077 (6)−0.011 (3)−0.001 (4)0.005 (4)
O80.040 (6)0.099 (8)0.054 (6)−0.003 (5)0.005 (4)−0.033 (5)
O90.052 (6)0.049 (5)0.068 (7)0.003 (4)0.009 (4)−0.008 (4)
O100.034 (3)0.049 (3)0.035 (4)0.005 (2)0.004 (2)−0.016 (2)
O110.064 (6)0.046 (5)0.036 (5)−0.006 (4)−0.003 (4)0.008 (4)
O120.051 (5)0.038 (4)0.027 (4)−0.015 (3)−0.003 (3)−0.001 (3)
S10.0306 (4)0.0308 (3)0.0294 (4)0.0021 (3)0.0041 (3)0.0000 (3)
S20.0318 (4)0.0314 (3)0.0277 (4)0.0015 (3)0.0048 (3)−0.0006 (3)
S30.0316 (4)0.0317 (3)0.0270 (4)0.0016 (3)0.0047 (3)−0.0002 (3)
Geometric parameters (Å, º) top
C1—C141.413 (5)C35—H350.9300
C1—C21.437 (5)C36—C371.419 (5)
C1—C151.479 (4)C36—H360.9300
C2—C31.376 (5)C37—C381.392 (5)
C2—C71.404 (4)C37—H370.9300
C3—C41.390 (5)C38—C391.406 (5)
C3—H30.9300C38—H380.9300
C4—C51.389 (5)C39—C401.370 (5)
C4—H40.9300C40—C411.360 (5)
C5—C61.376 (5)C40—H400.9300
C5—H50.9300C41—C421.429 (5)
C6—C71.401 (5)C41—C461.450 (5)
C6—H60.9300C42—C431.366 (5)
C7—C81.390 (5)C42—H420.9300
C8—C91.394 (5)C43—C441.408 (5)
C8—H80.9300C43—H430.9300
C9—C101.393 (5)C44—C451.363 (5)
C9—C141.407 (4)C44—H440.9300
C10—C111.346 (5)C45—C461.404 (5)
C10—H100.9300C45—H450.9300
C11—C121.392 (5)C47—N71.334 (4)
C11—H110.9300C47—H470.9300
C12—C131.362 (5)C48—N81.322 (4)
C12—H120.9300C48—N91.354 (4)
C13—C141.398 (5)C48—S31.710 (3)
C13—H130.9300Co1—N41.926 (2)
C15—N11.300 (4)Co1—N11.967 (2)
C15—H150.9300Co1—N71.985 (2)
C16—N21.307 (4)Co1—S12.2195 (9)
C16—N31.353 (4)Co1—S22.2314 (9)
C16—S11.738 (3)Co1—S32.2544 (9)
C17—C301.421 (4)N1—N21.386 (3)
C17—C181.430 (4)N3—O103.130 (6)
C17—C311.468 (3)N3—H3B0.85 (4)
C18—C231.386 (4)N3—H3A0.85 (4)
C18—C191.403 (4)N4—N51.380 (3)
C19—C201.386 (4)N6—H6B0.85 (4)
C19—H190.9300N6—H6A0.85 (4)
C20—C211.390 (5)N7—N81.359 (3)
C20—H200.9300N9—O83.002 (9)
C21—C221.375 (5)N9—O73.162 (8)
C21—H210.9300N9—H9B0.85 (4)
C22—C231.395 (5)N9—H9A0.85 (4)
C22—H220.9300O1—H1X0.8200
C23—C241.447 (4)O1—H1Y0.8200
C24—C251.370 (5)O2—H2X0.8200
C24—H240.9300O2—H2Y0.8200
C25—C301.406 (4)O3—H3X0.8200
C25—C261.410 (5)O3—H3Y0.8200
C26—C271.372 (5)O4—H4X0.8200
C26—H260.9300O4—H4Y0.8200
C27—C281.374 (4)O5—H5X0.8200
C27—H270.9300O5—H5Y0.8200
C28—C291.416 (5)O6—H6X0.8200
C28—H280.9300O6—H6Y0.8200
C29—C301.399 (5)O7—H7X0.8200
C29—H290.9300O7—H7Y0.8200
C31—N41.285 (3)O8—H8X0.8200
C31—H310.9300O8—H8Y0.8200
C32—N61.323 (4)O9—H9X0.8200
C32—N51.329 (4)O9—H9Y0.8200
C32—S21.731 (3)O10—H10X0.8200
C33—C461.393 (4)O10—H10Y0.8200
C33—C341.432 (4)O11—H11X0.8200
C33—C471.450 (4)O11—H11Y0.8200
C34—C351.403 (5)O12—H12X0.8200
C34—C391.458 (5)O12—H12Y0.8200
C35—C361.360 (5)
C14—C1—C2120.9 (3)C35—C36—C37122.5 (4)
C14—C1—C15122.2 (3)C35—C36—H36118.7
C2—C1—C15116.5 (3)C37—C36—H36118.7
C3—C2—C7119.7 (3)C38—C37—C36119.7 (3)
C3—C2—C1122.0 (3)C38—C37—H37120.2
C7—C2—C1118.1 (3)C36—C37—H37120.2
C2—C3—C4120.7 (3)C37—C38—C39119.4 (3)
C2—C3—H3119.6C37—C38—H38120.3
C4—C3—H3119.6C39—C38—H38120.3
C5—C4—C3119.6 (4)C40—C39—C38122.1 (3)
C5—C4—H4120.2C40—C39—C34118.3 (3)
C3—C4—H4120.2C38—C39—C34119.6 (3)
C6—C5—C4120.6 (4)C41—C40—C39124.2 (4)
C6—C5—H5119.7C41—C40—H40117.9
C4—C5—H5119.7C39—C40—H40117.9
C5—C6—C7119.9 (3)C40—C41—C42123.0 (4)
C5—C6—H6120.1C40—C41—C46119.0 (3)
C7—C6—H6120.1C42—C41—C46118.0 (3)
C8—C7—C6120.6 (3)C43—C42—C41122.3 (4)
C8—C7—C2119.8 (3)C43—C42—H42118.8
C6—C7—C2119.5 (3)C41—C42—H42118.8
C7—C8—C9122.9 (3)C42—C43—C44118.6 (3)
C7—C8—H8118.5C42—C43—H43120.7
C9—C8—H8118.5C44—C43—H43120.7
C10—C9—C8118.6 (3)C45—C44—C43121.3 (4)
C10—C9—C14122.8 (3)C45—C44—H44119.4
C8—C9—C14118.6 (3)C43—C44—H44119.4
C11—C10—C9116.0 (4)C44—C45—C46122.2 (4)
C11—C10—H10122.0C44—C45—H45118.9
C9—C10—H10122.0C46—C45—H45118.9
C10—C11—C12123.4 (4)C33—C46—C45123.1 (3)
C10—C11—H11118.3C33—C46—C41119.3 (3)
C12—C11—H11118.3C45—C46—C41117.5 (3)
C13—C12—C11120.6 (4)N7—C47—C33127.0 (3)
C13—C12—H12119.7N7—C47—H47116.5
C11—C12—H12119.7C33—C47—H47116.5
C12—C13—C14118.9 (3)N8—C48—N9118.0 (3)
C12—C13—H13120.6N8—C48—S3123.8 (2)
C14—C13—H13120.6N9—C48—S3118.3 (2)
C13—C14—C9118.3 (3)N4—Co1—N1172.00 (9)
C13—C14—C1122.0 (3)N4—Co1—N794.66 (9)
C9—C14—C1119.6 (3)N1—Co1—N791.26 (10)
N1—C15—C1127.2 (3)N4—Co1—S188.56 (7)
N1—C15—H15116.4N1—Co1—S185.33 (7)
C1—C15—H15116.4N7—Co1—S197.49 (8)
N2—C16—N3119.4 (3)N4—Co1—S284.94 (7)
N2—C16—S1124.8 (2)N1—Co1—S290.23 (8)
N3—C16—S1115.9 (2)N7—Co1—S2169.43 (7)
C30—C17—C18120.9 (3)S1—Co1—S293.06 (3)
C30—C17—C31117.6 (3)N4—Co1—S387.64 (6)
C18—C17—C31121.3 (2)N1—Co1—S398.44 (7)
C23—C18—C19119.5 (3)N7—Co1—S382.91 (7)
C23—C18—C17119.7 (3)S1—Co1—S3176.20 (3)
C19—C18—C17120.8 (3)S2—Co1—S386.52 (3)
C20—C19—C18119.7 (3)C15—N1—N2116.8 (2)
C20—C19—H19120.1C15—N1—Co1123.06 (19)
C18—C19—H19120.1N2—N1—Co1120.16 (17)
C19—C20—C21120.5 (3)C16—N2—N1112.9 (2)
C19—C20—H20119.8C16—N3—O10117.1 (2)
C21—C20—H20119.8C16—N3—H3B106 (3)
C22—C21—C20119.7 (3)O10—N3—H3B127 (3)
C22—C21—H21120.2C16—N3—H3A126 (3)
C20—C21—H21120.2H3B—N3—H3A106 (4)
C21—C22—C23120.6 (3)C31—N4—N5113.9 (2)
C21—C22—H22119.7C31—N4—Co1123.90 (18)
C23—C22—H22119.7N5—N4—Co1122.16 (17)
C18—C23—C22120.0 (3)C32—N5—N4111.6 (2)
C18—C23—C24118.5 (3)C32—N6—H6B110 (3)
C22—C23—C24121.4 (3)C32—N6—H6A110 (3)
C25—C24—C23121.6 (3)H6B—N6—H6A109 (4)
C25—C24—H24119.2C47—N7—N8113.1 (2)
C23—C24—H24119.2C47—N7—Co1126.3 (2)
C24—C25—C30120.7 (3)N8—N7—Co1120.45 (17)
C24—C25—C26120.6 (3)C48—N8—N7113.3 (2)
C30—C25—C26118.6 (3)C48—N9—O8121.9 (3)
C27—C26—C25120.9 (3)C48—N9—O792.1 (2)
C27—C26—H26119.6O8—N9—O762.7 (3)
C25—C26—H26119.6C48—N9—H9B109 (3)
C26—C27—C28121.7 (3)O8—N9—H9B45 (3)
C26—C27—H27119.2C48—N9—H9A110 (3)
C28—C27—H27119.2O8—N9—H9A65 (3)
C27—C28—C29118.5 (3)O7—N9—H9A127 (3)
C27—C28—H28120.7H9B—N9—H9A109 (4)
C29—C28—H28120.7H1X—O1—H1Y104.5
C30—C29—C28120.7 (3)H2X—O2—H2Y104.5
C30—C29—H29119.6H3X—O3—H3Y104.5
C28—C29—H29119.6H4X—O4—H4Y104.5
C29—C30—C25119.6 (3)H5X—O5—H5Y104.5
C29—C30—C17121.9 (3)H6X—O6—H6Y104.5
C25—C30—C17118.5 (3)N9—O7—H7X90.9
N4—C31—C17128.7 (2)N9—O7—H7Y95.5
N4—C31—H31115.7H7X—O7—H7Y104.5
C17—C31—H31115.7N9—O8—H8X95.9
N6—C32—N5117.7 (3)N9—O8—H8Y110.5
N6—C32—S2118.1 (3)H8X—O8—H8Y104.5
N5—C32—S2124.2 (2)H9X—O9—H9Y104.5
C46—C33—C34120.4 (3)N3—O10—H10X84.2
C46—C33—C47121.6 (3)N3—O10—H10Y98.0
C34—C33—C47117.8 (3)H10X—O10—H10Y104.5
C35—C34—C33122.0 (3)H11X—O11—H11Y104.5
C35—C34—C39119.4 (3)H12X—O12—H12Y104.5
C33—C34—C39118.6 (3)C16—S1—Co195.29 (10)
C36—C35—C34119.3 (3)C32—S2—Co194.97 (11)
C36—C35—H35120.3C48—S3—Co195.59 (10)
C34—C35—H35120.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O100.85 (4)2.36 (4)3.130 (6)151 (3)
N9—H9B···O70.85 (4)2.38 (4)3.162 (8)153 (4)
N9—H9B···O80.85 (4)2.47 (4)3.002 (9)122 (3)
N9—H9A···O110.85 (4)2.24 (4)2.957 (9)142 (4)
O1—H1X···O60.821.592.263 (11)137
O1—H1X···O11i0.822.583.013 (11)114
O7—H7Y···N3ii0.822.623.158 (10)124
O8—H8Y···S2ii0.822.603.371 (10)157
O9—H9Y···O11iii0.822.593.300 (12)146
O12—H12X···O11iii0.822.253.003 (11)153
O10—H10X···N9iv0.822.263.033 (6)157
O10—H10Y···N8iv0.822.482.939 (6)116
O11—H11X···S30.822.463.165 (8)145
O11—H11X···N50.822.573.163 (9)130
O11—H11Y···O1v0.822.503.013 (11)122
O12—H12Y···O90.822.062.494 (12)113
Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z; (v) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Co(C16H12N3S)3]·4H2O
Mr966.03
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)9.8907 (19), 17.073 (3), 17.511 (4)
α, β, γ (°)91.315 (7), 99.920 (6), 93.972 (6)
V (Å3)2903.9 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.45
Crystal size (mm)0.28 × 0.22 × 0.20
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.886, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections		36568, 11268, 8244
Rint0.054
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.132, 1.04
No. of reflections11268
No. of parameters723
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.90, −0.92

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O100.85 (4)2.36 (4)3.130 (6)151 (3)
N9—H9B···O70.85 (4)2.38 (4)3.162 (8)153 (4)
N9—H9B···O80.85 (4)2.47 (4)3.002 (9)122 (3)
N9—H9A···O110.85 (4)2.24 (4)2.957 (9)142 (4)
O1—H1X···O60.821.592.263 (11)137
O1—H1X···O11i0.822.583.013 (11)114
O7—H7Y···N3ii0.822.623.158 (10)124
O8—H8Y···S2ii0.822.603.371 (10)157
O9—H9Y···O11iii0.822.593.300 (12)146
O12—H12X···O11iii0.822.253.003 (11)153
O10—H10X···N9iv0.822.263.033 (6)157
O10—H10Y···N8iv0.822.482.939 (6)116
O11—H11X···S30.822.463.165 (8)145
O11—H11X···N50.822.573.163 (9)130
O11—H11Y···O1v0.822.503.013 (11)122
O12—H12Y···O90.822.062.494 (12)113
Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z; (v) x, y+1, z.
 

Acknowledgements

This work was supported financially by the Natural Science Foundation of Jiangsu Province Education office (grant No. 04KJB150015). The authors also thank Dr Zaichao Zhang for his support.

References

First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCasas, J. S., Garcia-Tasende, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197–261.  Web of Science CrossRef CAS Google Scholar
 First citationChandra, S., Kumar, U. & Verma, H. S. (2003). Orient. J. Chem. 19, 355–359.  CAS Google Scholar
 First citationFunston, A. M., Ghiggino, K. P., Grannas, M. J., McFadyen, W. D. & Tregloan, P. A. (2003). Discuss. Faraday Soc. pp. 3704–3711.  Google Scholar
 First citationHe, Y., Wu, B., Yang, J., Robinson, D., Risen, L., Ranken, R., Blyn, L., Sheng, S. & Swayze, E. E. (2003). Bioorg. Med. Chem. Lett. 13, 3253–3260.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationHorton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893–941.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationKabanos, T. A., Kersmidas, A. D., Mentzafos, D., Russo, U., Terzis, A. & Tsangaris, J. M. (1992). J. Chem. Soc. Dalton Trans. pp. 2729–2734.  CSD CrossRef Web of Science Google Scholar
 First citationNavarrete-Vazquez, G., Cedillo, R., Hernandez-Campos, A., Yepez, J., Hernndez-Luis, F., Valldez, J., Morales, R., Cortes, R., Hernandez, M. & Castillo, R. (2001). Bioorg. Med. Chem. Lett. 11, 187–193.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationOzden, S., Atabey, D., Yildiz, S. & Goker, H. (2005). Bioorg. Med. Chem. 13, 1587–1596.  Web of Science CrossRef PubMed Google Scholar
 First citationPawar, N. S., Dalal, D. S., Shimpi, S. R. & Mahulikar, P. P. (2004). Eur. J. Pharm. Sci. 21, 115–118.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationRodriguez-Arguelles, M. C., Lopez-Silva, E. C., Sanmartin, J., Bacchi, A., Pelizzi, C. & Zani, F. (2004). Inorg. Chim. Acta. 357, 2543–2551.  Web of Science CSD CrossRef Google Scholar
 First citationSaha, N. C., Butcher, R. J., Chaudhari, S. & Saha, N. (2003). Polyhedron, 22, 383–389.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 64| Part 11| November 2008| Pages m1355-m1356
doi:10.1107/S1600536808031425
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