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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 66| Part 10| October 2010| Pages m1330-m1331
doi:10.1107/S1600536810037360

The cobalt(II) salt of the azo dye Orange G

Alan R. Kennedy,a Scott C. McKellara and Maurice O. Okothb*

aDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, and bDepartment of Chemistry and Biochemistry, Moi University, PO Box 1125-30100, Eldoret, Kenya.
*Correspondence e-mail: okothmdo@mu.ac.ke

(Received 29 July 2010; accepted 17 September 2010; online 30 September 2010)

Crystallizing the cobalt(II) salt of the azo dye Orange G from water was found to give the solvent-separated ion-pair species hexa­aqua­cobalt(II) 7-oxo-8-(2-phenyl­hydrazin-1-ylidene)-7,8-dihydro­naphthalene-1,3-disulfonate tetra­hydrate, [Co(H2O)6](C16H10N2O7S2)·4H2O. The asymmetric unit of the cobalt(II) salt contains three independent octa­hedral [Co(OH2)6]2+ cations, three azo anions, all with similar configurations, and 12 uncoordinated water mol­ecules. The structure is closely related to that of one of the known magnesium analogues. Both structures have Z′ = 3, feature nearly planar azo anions [maximum displacement of azo-N atoms from the plane of the phenyl ring = 0.058 (7) Å] in their hydrazone tautomeric form, form layer structures with hydro­philic and hydro­phobic layers alternating along the b-axis direction, and are stabilized by an extensive network of hydrogen bonds..

Related literature

For other structures of metal salts of Orange G, see: Ojala et al. (1994[Ojala, W. H., Lu, L. K., Albers, K. E., Gleason, W. B., Richardson, T. I., Lovrien, R. E. & Sudbeck, E. A. (1994). Acta Cryst. B50, 684-694.]); Kennedy et al. (2006[Kennedy, A. R., Kirkhouse, J. B. A. & Whyte, L. (2006). Inorg. Chem. 45, 2965-2971.]). For the structural classification of metal salts of other sulfonated azo dyes and pigments, see: Kennedy et al. (2001[Kennedy, A. R., Hughes, M. P., Monaghan, M. L., Staunton, E., Teat, S. J. & Smith, W. E. (2001). J. Chem. Soc. Dalton Trans. pp. 2199-2205.], 2009[Kennedy, A. R., Andrikopoulos, P. C., Arlin, J.-B., Armstrong, D. R., Duxbury, N., Graham, D. V. & Kirkhouse, J. B. A. (2009). Chem. Eur. J. 15, 9494-9504.]). For the general coordination behaviour of —RSO3 species with metals, see: Côté & Shimizu (2003[Côté, A. P. & Shimizu, G. K. H. (2003). Coord. Chem. Rev. 245, 49-64.]).

[Scheme 1]

Experimental

Crystal data

  • [Co(H2O)6](C16H10N2O7S2)·4H2O

  • Mr = 645.47

  • Triclinic, [P \overline 1]

  • a = 10.0768 (3) Å

  • b = 14.6463 (5) Å

  • c = 26.3881 (8) Å

  • α = 93.470 (2)°

  • β = 90.813 (1)°

  • γ = 101.175 (1)°

  • V = 3812.4 (2) Å3

  • Z = 6

  • Mo Kα radiation

  • μ = 0.92 mm−1

  • T = 123 K

  • 0.35 × 0.22 × 0.06 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.683, Tmax = 1.000

  • 63505 measured reflections

  • 16529 independent reflections

  • 10980 reflections with I > 2σ(I)

  • Rint = 0.086
Refinement

  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.150

  • S = 1.03

  • 16529 reflections

  • 1216 parameters

  • 90 restraints

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

  • Δρmax = 0.95 e Å−3

  • Δρmin = −1.03 e Å−3

Data collection: COLLECT (Hooft, 1988[Hooft, R. (1988). COLLECT. Nonius BV, Delft, The Netherlands.]) and DENZO (Otwin­owski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp 307-326. New York: Academic Press.]); cell refinement: COLLECT and DENZO; data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp 307-326. New York: Academic Press.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037360/wm2388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037360/wm2388Isup2.hkl

checkCIF report


Comment top

It is known that transition metal complexes of sulfonated aryl species generally form solvent-separated ion-pairs, but that s-block metals may form direct M—O3S bonds (Côté & Shimizu, 2003). A subgroup of these compounds, sulfonated azo molecules, are widely used as colourants. Despite this, there are relatively few known crystal structures of sulfonated azo colourants (Kennedy et al., 2001). This is at least partly due to the fact that their salt forms typically give poor quality crystals with extremely anisotropic habits. Recently, a systematic structural study of s-block metal salts of sulfonated azo dyes showed that it was those salts with the least electropositive s-block metals that formed solvent-separated ion-pairs when crystallized from water (Kennedy et al., 2009).

An exception to the general rule is the disulfonated naphthalene derived dye Orange G, which is found to give robust crystals. Thus a number of crystal structures of its metal salts were determined (Ojala et al., 1994; Kennedy et al., 2006). Structures with no metal-sulfonate bonds were found for the Mg (two phases), Ca and Li salts of Orange G (Ojala et al., 1994; Kennedy et al., 2006). Here we describe a transition metal salt of Orange G, viz. the Co(II) salt hexaaqua-cobalt(II) 7-oxo-8-(phenylhydrazono)-7,8-dihydronaphthalene-1,3-disulfonate tetrahydrate, [Co(OH2)6][C16H10N2O7S2].4H2O. This conforms to literature expectations and forms the expected solvent-separated ion-pair type structure. Indeed, its structure is closely related to that of the Mg phase with 3.33 lattice water molecules reported by Kennedy et al. (2006).

The asymmetric unit contains three different molecular species with Z' = 3, though both the octahedral [Co(OH2)6] cations and the azo anions are found to have similar configurations throughout. The anions are found to exist as the hydrazone tautomer. The internal hydrogen leading to a 6-membered ring (see O7-C2-C1-N1-N2-H in Fig. 1) favours approximate planarity, but the steric bulk of the 1-sulfonate competes against this. Overall, the azo N-atoms lie in plane with the phenyl ring (maximum displacement from plane 0.058 (7) Å) and somewhat out of the plane of the naphthalene group (maximum displacement from plane 0.454 (6) Å). There is a small angle between the least squares planes of the two ring systems (range 14.13 (9) to 15.27 (8) °).

Expanding the contents of the asymmetric unit (Fig. 2) gives a layered packing motif with hydrophilic ([Co(H2O)]6, water, —SO3 and ketone O moieties) and hydrophobic layers alternating along the b direction (Fig. 3). Within the hydrophilic layer, all thirty independent water molecules use both H atoms as hydrogen bond donors. All the azo anion's O atoms accept hydrogen bonds as do all the free water molecules. Unusually, two of the water molecules bound to Co (O13W and O10W) also act as hydrogen bond acceptors. In the hydrophobic layer, all the aromatic rings lie parallel, with π···π contacts connecting them along the a direction with a closest interplanar interaction of 3.371 (5) Å.

Related literature top

For other structures of metal salts of Orange G, see: Ojala et al. (1994); Kennedy et al. (2006). For the structural classification of metal salts of other sulfonated azo dyes and pigments, see: Kennedy et al. (2001, 2009). For the general coordination behaviour of —RSO3 species with metals, see: Côté & Shimizu (2003). Scheme - should be [Co(H2O)6]

Experimental top

Addition of a slight excess of Co(NO3)2 (0.167 g, 0.571 mmol), in aqueous solution, to a near saturated aqueous solution of the sodium salt of Orange G (0.188 g, 0.405 mmol) gave an orange precipitate. This was isolated by filtration and recrystallized from hot water to yield large crystals of the Co(II) salt of Orange G (0.188 g, 84% yield). λmax: 785 nm. IR[KBr]: 3461, 1623, 1497, 1423, 1283, 1215, 1142, 1027, 987, 762, 640, 508 cm-1. Raman (solid, 633 nm excitation): 1594, 1494, 1427, 1377, 1329, 1305, 1240, 1178 cm-1.

Refinement top

The position of the nitrogen-bound H atoms were refined freely, but the positions of the water H atoms were restrained such that O—H and H···H distances approximated 0.88 and 1.33 Å, respectively. The aromatic H atoms were placed in calculated positions and refined in riding modes with C—H = 0.95 Å. All Uiso(H) values were set to 1.2Ueq of their parent non-H atom. Ten low angle reflections were omitted from the final refinement, all had extremely low observed F2 values as compared to calculated F2.

Computing details top

Data collection: COLLECT (Hooft, 1988) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT (Hooft, 1988) and DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of one of the unique anions of Orange G, showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Contents of the asymmetric unit with 50% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.
[Figure 3] Fig. 3. Packing diagram with view along the a axis. Note the alternate hyrophobic and hydrophilic layers.
hexaaquacobalt(II) 7-oxo-8-(2-phenylhydrazin-1-ylidene)-7,8-dihydronaphthalene-1,3-disulfonate tetrahydrate top
Crystal data top
[Co(H2O)6](C16H10N2O7S2)·4H2OZ = 6
Mr = 645.47F(000) = 2010
Triclinic, P1Dx = 1.687 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0768 (3) ÅCell parameters from 207115 reflections
b = 14.6463 (5) Åθ = 1.0–27.1°
c = 26.3881 (8) ŵ = 0.92 mm−1
α = 93.470 (2)°T = 123 K
β = 90.813 (1)°Fragment cut from large block, orange-red
γ = 101.175 (1)°0.35 × 0.22 × 0.06 mm
V = 3812.4 (2) Å3
Data collection top
Nonius KappaCCD
diffractometer		16529 independent reflections
Radiation source: fine-focus sealed tube10980 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
ω and ϕ scansθmax = 27.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		h = −12→12
Tmin = 0.683, Tmax = 1.000k = −18→18
63505 measured reflectionsl = −33→33
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0709P)2 + 4.7352P]
where P = (Fo2 + 2Fc2)/3
16529 reflections(Δ/σ)max = 0.001
1216 parametersΔρmax = 0.95 e Å−3
90 restraintsΔρmin = −1.03 e Å−3
Crystal data top
[Co(H2O)6](C16H10N2O7S2)·4H2Oγ = 101.175 (1)°
Mr = 645.47V = 3812.4 (2) Å3
Triclinic, P1Z = 6
a = 10.0768 (3) ÅMo Kα radiation
b = 14.6463 (5) ŵ = 0.92 mm−1
c = 26.3881 (8) ÅT = 123 K
α = 93.470 (2)°0.35 × 0.22 × 0.06 mm
β = 90.813 (1)°
Data collection top
Nonius KappaCCD
diffractometer		16529 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		10980 reflections with I > 2σ(I)
Tmin = 0.683, Tmax = 1.000Rint = 0.086
63505 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05690 restraints
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.95 e Å−3
16529 reflectionsΔρmin = −1.03 e Å−3
1216 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.

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*/Ueq
Co10.55837 (5)0.50041 (3)0.767621 (19)0.01612 (13)
Co21.09697 (5)0.47172 (4)0.889819 (19)0.01716 (13)
Co30.76533 (5)0.49375 (3)0.574876 (19)0.01670 (13)
S10.96481 (9)0.73184 (6)0.78316 (3)0.0152 (2)
S20.77827 (10)0.70362 (7)0.97236 (3)0.0185 (2)
S30.68205 (9)0.24597 (6)0.88288 (3)0.0153 (2)
S40.88476 (9)0.25429 (6)0.69503 (3)0.0172 (2)
S50.63595 (9)0.74418 (6)0.44610 (3)0.0162 (2)
S60.46525 (10)0.72989 (6)0.63783 (4)0.0186 (2)
O10.9712 (3)0.63918 (17)0.80008 (9)0.0186 (6)
O20.8563 (3)0.72713 (18)0.74589 (9)0.0195 (6)
O1W0.4973 (3)0.37083 (18)0.79310 (11)0.0232 (6)
H1W0.415 (2)0.342 (3)0.7953 (15)0.028*
H2W0.540 (3)0.350 (3)0.8171 (12)0.028*
O31.0961 (3)0.77837 (17)0.76568 (10)0.0198 (6)
O2W0.5992 (3)0.63442 (19)0.74398 (10)0.0225 (6)
H3W0.680 (2)0.668 (3)0.7485 (13)0.027*
H4W0.585 (4)0.639 (3)0.7117 (8)0.027*
O40.8326 (3)0.61801 (18)0.96543 (10)0.0249 (6)
O3W0.7601 (3)0.48354 (19)0.76745 (11)0.0247 (6)
H5W0.828 (3)0.527 (2)0.7756 (15)0.030*
H6W0.792 (4)0.446 (2)0.7475 (13)0.030*
O50.6328 (3)0.68611 (19)0.96374 (10)0.0257 (6)
O4W0.6049 (3)0.56462 (19)0.84107 (10)0.0212 (6)
H7W0.552 (4)0.604 (2)0.8462 (14)0.025*
H8W0.593 (4)0.532 (2)0.8668 (11)0.025*
O60.8210 (3)0.75364 (19)1.02103 (9)0.0228 (6)
O5W0.3525 (3)0.51391 (19)0.77254 (10)0.0225 (6)
H9W0.338 (4)0.5708 (16)0.7693 (14)0.027*
H10W0.314 (4)0.503 (2)0.8009 (10)0.027*
O71.0901 (3)1.11905 (18)0.79352 (10)0.0228 (6)
O6W0.5178 (3)0.4498 (2)0.69298 (10)0.0257 (6)
H11W0.440 (2)0.422 (3)0.6801 (14)0.031*
H12W0.572 (3)0.432 (3)0.6706 (13)0.031*
O80.7820 (3)0.25815 (17)0.92442 (9)0.0192 (6)
O7W1.0419 (3)0.33513 (19)0.91018 (11)0.0227 (6)
H13W1.083 (3)0.308 (3)0.9312 (13)0.027*
H14W0.9581 (19)0.310 (3)0.9125 (15)0.027*
O90.5494 (2)0.19767 (18)0.89640 (10)0.0205 (6)
O8W1.1558 (3)0.60918 (19)0.87249 (10)0.0227 (6)
H15W1.111 (3)0.623 (3)0.8474 (12)0.027*
H16W1.237 (2)0.639 (3)0.8684 (15)0.027*
O100.6780 (3)0.33652 (17)0.86250 (9)0.0190 (6)
O9W1.1383 (3)0.5181 (2)0.96528 (10)0.0250 (6)
H17W1.186 (4)0.5688 (17)0.9799 (14)0.030*
H18W1.132 (4)0.480 (2)0.9885 (12)0.030*
O110.8454 (3)0.34519 (18)0.70179 (10)0.0246 (6)
O10W1.2957 (3)0.44753 (19)0.87963 (10)0.0225 (6)
H19W1.360 (3)0.473 (2)0.9008 (13)0.027*
H20W1.304 (4)0.3896 (13)0.8779 (15)0.027*
O120.8292 (3)0.20489 (19)0.64750 (9)0.0229 (6)
O11W1.0572 (3)0.42212 (19)0.81367 (10)0.0223 (6)
H21W1.105 (4)0.380 (2)0.8056 (14)0.027*
H22W1.071 (4)0.459 (2)0.7898 (12)0.027*
O131.0300 (3)0.26048 (19)0.70050 (10)0.0238 (6)
O12W0.8971 (3)0.49024 (19)0.89176 (11)0.0223 (6)
H23W0.863 (4)0.528 (2)0.9108 (13)0.027*
H24W0.828 (3)0.447 (2)0.8840 (15)0.027*
O140.5746 (3)−0.13949 (17)0.88684 (10)0.0208 (6)
O13W0.6923 (3)0.38392 (18)0.61962 (10)0.0227 (6)
H25W0.750 (3)0.359 (2)0.6361 (14)0.027*
H26W0.634 (3)0.3351 (19)0.6094 (15)0.027*
O150.7666 (3)0.78774 (17)0.42708 (10)0.0214 (6)
O14W0.8255 (3)0.6108 (2)0.53505 (11)0.0265 (7)
H27W0.780 (3)0.627 (3)0.5104 (12)0.032*
H28W0.907 (2)0.641 (3)0.5306 (15)0.032*
O160.5229 (3)0.74048 (18)0.41075 (9)0.0205 (6)
O15W0.7972 (3)0.58080 (19)0.64190 (11)0.0253 (6)
H29W0.748 (3)0.624 (2)0.6445 (16)0.030*
H30W0.874 (2)0.610 (2)0.6552 (16)0.030*
O170.6399 (3)0.65155 (17)0.46390 (10)0.0203 (6)
O16W0.5631 (3)0.51140 (19)0.56506 (10)0.0202 (6)
H31W0.529 (3)0.547 (2)0.5869 (12)0.024*
H32W0.493 (3)0.4661 (19)0.5590 (14)0.024*
O180.5391 (3)0.65342 (19)0.63945 (10)0.0257 (6)
O17W0.7270 (3)0.4100 (2)0.50873 (10)0.0242 (6)
H33W0.784 (3)0.375 (2)0.5021 (14)0.029*
H34W0.729 (4)0.441 (2)0.4827 (11)0.029*
O190.3240 (3)0.6965 (2)0.62217 (11)0.0280 (7)
O18W0.9590 (3)0.46353 (19)0.58642 (12)0.0267 (7)
H35W0.970 (4)0.4055 (13)0.5839 (17)0.032*
H36W1.040 (2)0.493 (2)0.5890 (17)0.032*
O200.4800 (3)0.78783 (18)0.68518 (10)0.0253 (6)
O19W0.4276 (3)0.68555 (18)0.85871 (10)0.0223 (6)
H37W0.478 (4)0.7386 (18)0.8689 (13)0.027*
H38W0.403 (4)0.698 (2)0.8286 (9)0.027*
O210.7537 (3)1.13329 (17)0.44848 (9)0.0203 (6)
O20W1.0664 (3)0.6635 (2)0.66736 (11)0.0264 (7)
H39W1.072 (4)0.7158 (19)0.6845 (13)0.032*
H40W1.137 (3)0.678 (3)0.6484 (13)0.032*
O21W0.3253 (3)0.7000 (2)0.76328 (10)0.0238 (6)
H41W0.377 (3)0.732 (3)0.7419 (13)0.029*
H42W0.253 (2)0.723 (3)0.7602 (15)0.029*
O22W1.0745 (3)0.4915 (2)0.71520 (11)0.0283 (7)
H43W0.996 (3)0.460 (2)0.7045 (16)0.034*
H44W1.072 (4)0.5461 (15)0.7041 (16)0.034*
O23W0.5375 (3)0.4923 (2)0.93519 (10)0.0265 (7)
H45W0.580 (4)0.5470 (14)0.9478 (15)0.032*
H46W0.579 (4)0.456 (2)0.9506 (15)0.032*
O24W0.6319 (3)0.35913 (19)0.99677 (11)0.0273 (7)
H47W0.557 (3)0.329 (2)1.0089 (15)0.033*
H48W0.662 (4)0.311 (2)0.9830 (15)0.033*
O25W0.3178 (3)0.2676 (2)0.88730 (11)0.0263 (7)
H49W0.281 (3)0.252 (3)0.9161 (10)0.032*
H50W0.398 (2)0.253 (3)0.8923 (15)0.032*
O26W0.2200 (3)0.29879 (18)0.78462 (11)0.0249 (6)
H51W0.178 (4)0.283 (3)0.7550 (9)0.030*
H52W0.192 (4)0.2477 (19)0.7998 (12)0.030*
O27W0.2554 (3)0.3950 (2)0.66159 (12)0.0332 (7)
H53W0.231 (4)0.3340 (13)0.6620 (17)0.040*
H54W0.201 (4)0.414 (3)0.6828 (14)0.040*
O28W0.9989 (3)0.27951 (19)0.57343 (10)0.0231 (6)
H55W0.949 (3)0.238 (2)0.5906 (14)0.028*
H56W1.076 (2)0.265 (3)0.5779 (15)0.028*
O29W0.2375 (3)0.5172 (2)0.58405 (11)0.0281 (7)
H57W0.276 (4)0.5714 (15)0.5985 (15)0.034*
H58W0.263 (4)0.479 (2)0.6045 (14)0.034*
O30W0.9102 (3)0.30277 (19)0.47948 (11)0.0237 (6)
H59W0.941 (4)0.286 (2)0.5067 (10)0.028*
H60W0.853 (3)0.252 (2)0.4683 (13)0.028*
N10.9773 (3)0.9315 (2)0.76101 (11)0.0156 (7)
N21.0132 (3)0.9896 (2)0.72600 (12)0.0179 (7)
H1N1.049 (4)1.047 (3)0.7371 (15)0.021*
N30.6850 (3)0.0514 (2)0.91295 (11)0.0162 (7)
N40.6534 (3)−0.0023 (2)0.95014 (12)0.0171 (7)
H2N0.615 (4)−0.052 (3)0.9427 (16)0.021*
N50.6475 (3)0.9429 (2)0.42117 (11)0.0159 (7)
N60.6777 (3)0.9984 (2)0.38471 (12)0.0175 (7)
H3N0.713 (4)1.051 (3)0.3951 (16)0.021*
C10.9985 (4)0.9627 (3)0.81018 (14)0.0169 (8)
C21.0459 (4)1.0606 (3)0.82555 (15)0.0209 (8)
C31.0344 (4)1.0913 (3)0.87812 (14)0.0203 (8)
H31.06371.15520.88880.024*
C40.9824 (4)1.0297 (3)0.91211 (14)0.0194 (8)
H40.97241.05220.94610.023*
C50.9413 (4)0.9311 (3)0.89878 (14)0.0179 (8)
C60.9548 (3)0.8952 (3)0.84803 (13)0.0150 (8)
C70.9268 (3)0.7966 (2)0.83949 (13)0.0147 (8)
C80.8724 (4)0.7397 (3)0.87726 (14)0.0164 (8)
H80.84920.67410.87020.020*
C90.8516 (4)0.7778 (3)0.92547 (13)0.0168 (8)
C100.8892 (4)0.8724 (3)0.93646 (14)0.0186 (8)
H100.87960.89790.96990.022*
C110.9855 (4)0.9627 (3)0.67409 (14)0.0185 (8)
C121.0236 (4)1.0308 (3)0.63942 (15)0.0207 (8)
H121.06441.09270.65100.025*
C131.0014 (4)1.0071 (3)0.58792 (15)0.0247 (9)
H131.02641.05330.56420.030*
C140.9431 (4)0.9169 (3)0.57058 (15)0.0258 (9)
H140.92940.90110.53520.031*
C150.9049 (4)0.8498 (3)0.60534 (15)0.0257 (9)
H150.86470.78790.59350.031*
C160.9246 (4)0.8720 (3)0.65739 (15)0.0235 (9)
H160.89710.82610.68100.028*
C170.6620 (4)0.0152 (3)0.86506 (14)0.0158 (8)
C180.6150 (4)−0.0844 (3)0.85263 (14)0.0184 (8)
C190.6216 (4)−0.1191 (3)0.80070 (14)0.0187 (8)
H190.5901−0.18360.79170.022*
C200.6717 (4)−0.0616 (3)0.76451 (14)0.0185 (8)
H200.6789−0.08730.73100.022*
C210.7145 (4)0.0373 (2)0.77505 (14)0.0156 (8)
C220.7032 (4)0.0783 (3)0.82477 (13)0.0152 (8)
C230.7332 (3)0.1779 (3)0.83067 (13)0.0145 (8)
C240.7888 (4)0.2306 (3)0.79142 (14)0.0174 (8)
H240.81400.29640.79680.021*
C250.8081 (4)0.1874 (3)0.74396 (13)0.0160 (8)
C260.7663 (4)0.0926 (3)0.73539 (14)0.0176 (8)
H260.77250.06420.70240.021*
C270.6836 (4)0.0304 (3)1.00097 (14)0.0181 (8)
C280.6471 (4)−0.0325 (3)1.03830 (14)0.0217 (9)
H280.6060−0.09551.02930.026*
C290.6721 (4)−0.0012 (3)1.08900 (15)0.0260 (9)
H290.6483−0.04351.11480.031*
C300.7311 (4)0.0907 (3)1.10243 (15)0.0242 (9)
H300.74580.11171.13720.029*
C310.7686 (4)0.1519 (3)1.06474 (14)0.0231 (9)
H310.81020.21481.07380.028*
C320.7460 (4)0.1223 (3)1.01391 (15)0.0235 (9)
H320.77290.16420.98820.028*
C330.6712 (4)0.9774 (2)0.46917 (14)0.0159 (8)
C340.7143 (4)1.0771 (3)0.48250 (14)0.0177 (8)
C350.7050 (4)1.1104 (3)0.53434 (14)0.0174 (8)
H350.73071.17520.54360.021*
C360.6603 (4)1.0508 (3)0.57003 (15)0.0194 (8)
H360.65341.07520.60390.023*
C370.6226 (4)0.9514 (2)0.55889 (14)0.0160 (8)
C380.6340 (4)0.9126 (2)0.50909 (13)0.0149 (8)
C390.6059 (3)0.8128 (2)0.50205 (13)0.0145 (7)
C400.5558 (4)0.7592 (3)0.54198 (14)0.0166 (8)
H400.53360.69320.53670.020*
C410.5377 (4)0.8009 (3)0.58955 (14)0.0168 (8)
C420.5753 (4)0.8957 (3)0.59870 (14)0.0165 (8)
H420.56920.92340.63190.020*
C430.6465 (4)0.9681 (3)0.33345 (14)0.0186 (8)
C440.6822 (4)1.0328 (3)0.29734 (14)0.0203 (8)
H440.72291.09550.30740.024*
C450.6579 (4)1.0052 (3)0.24633 (15)0.0266 (9)
H450.68231.04910.22140.032*
C460.5985 (4)0.9142 (3)0.23155 (15)0.0286 (10)
H460.58240.89560.19650.034*
C470.5624 (4)0.8500 (3)0.26805 (15)0.0251 (9)
H470.52130.78750.25780.030*
C480.5859 (4)0.8763 (3)0.31951 (15)0.0222 (9)
H480.56110.83250.34450.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0150 (3)0.0196 (3)0.0138 (3)0.0030 (2)0.0032 (2)0.0019 (2)
Co20.0152 (3)0.0232 (3)0.0135 (3)0.0035 (2)0.0034 (2)0.0043 (2)
Co30.0153 (3)0.0196 (3)0.0153 (3)0.0029 (2)0.0037 (2)0.0028 (2)
S10.0163 (5)0.0174 (5)0.0120 (5)0.0032 (4)0.0039 (4)0.0005 (4)
S20.0193 (5)0.0241 (5)0.0123 (5)0.0043 (4)0.0045 (4)0.0013 (4)
S30.0158 (5)0.0178 (5)0.0127 (5)0.0036 (4)0.0040 (4)0.0016 (4)
S40.0177 (5)0.0209 (5)0.0129 (5)0.0024 (4)0.0048 (4)0.0037 (4)
S50.0175 (5)0.0163 (5)0.0143 (5)0.0019 (4)0.0027 (4)0.0014 (4)
S60.0223 (5)0.0190 (5)0.0143 (5)0.0021 (4)0.0040 (4)0.0040 (4)
O10.0192 (14)0.0207 (14)0.0161 (14)0.0041 (11)0.0057 (11)0.0006 (11)
O20.0209 (14)0.0225 (14)0.0132 (13)−0.0002 (11)−0.0001 (11)0.0006 (11)
O1W0.0194 (15)0.0216 (15)0.0287 (17)0.0028 (12)0.0003 (12)0.0073 (12)
O30.0170 (14)0.0229 (14)0.0202 (14)0.0053 (11)0.0076 (11)0.0018 (11)
O2W0.0181 (15)0.0300 (16)0.0196 (15)0.0036 (12)0.0027 (12)0.0063 (12)
O40.0376 (17)0.0276 (15)0.0126 (14)0.0118 (13)0.0103 (12)0.0059 (11)
O3W0.0162 (15)0.0243 (16)0.0325 (17)0.0035 (12)0.0029 (13)−0.0072 (13)
O50.0185 (15)0.0357 (17)0.0226 (15)0.0030 (12)0.0063 (12)0.0061 (13)
O4W0.0228 (15)0.0264 (16)0.0149 (14)0.0058 (12)0.0034 (12)0.0029 (12)
O60.0253 (15)0.0307 (16)0.0118 (14)0.0043 (12)0.0041 (11)0.0004 (11)
O5W0.0183 (15)0.0272 (16)0.0228 (16)0.0063 (12)0.0065 (12)0.0023 (12)
O70.0242 (15)0.0229 (15)0.0203 (15)0.0016 (12)0.0037 (12)0.0025 (12)
O6W0.0165 (15)0.0420 (18)0.0171 (15)0.0035 (13)0.0040 (12)−0.0041 (13)
O80.0224 (15)0.0216 (14)0.0121 (13)0.0009 (11)0.0002 (11)0.0014 (11)
O7W0.0181 (14)0.0251 (15)0.0257 (16)0.0040 (12)−0.0005 (12)0.0090 (12)
O90.0144 (14)0.0244 (15)0.0227 (15)0.0028 (11)0.0078 (11)0.0028 (11)
O8W0.0183 (15)0.0273 (16)0.0225 (16)0.0030 (12)−0.0003 (12)0.0069 (12)
O100.0225 (15)0.0184 (14)0.0171 (14)0.0063 (11)0.0033 (11)0.0017 (11)
O9W0.0329 (17)0.0269 (16)0.0133 (14)0.0004 (13)0.0009 (12)0.0032 (12)
O110.0300 (16)0.0240 (15)0.0211 (15)0.0067 (12)0.0093 (12)0.0053 (12)
O10W0.0179 (15)0.0255 (15)0.0240 (16)0.0038 (12)0.0009 (12)0.0011 (12)
O120.0224 (15)0.0334 (16)0.0108 (14)0.0002 (12)0.0021 (11)0.0006 (11)
O11W0.0244 (16)0.0281 (16)0.0166 (15)0.0090 (12)0.0036 (12)0.0045 (12)
O130.0164 (14)0.0359 (17)0.0181 (15)0.0012 (12)0.0052 (11)0.0065 (12)
O12W0.0160 (14)0.0254 (16)0.0255 (16)0.0054 (11)0.0037 (12)−0.0026 (12)
O140.0243 (15)0.0205 (14)0.0170 (14)0.0017 (11)0.0024 (11)0.0052 (11)
O13W0.0208 (15)0.0256 (15)0.0207 (15)0.0009 (12)−0.0010 (12)0.0058 (12)
O150.0203 (14)0.0211 (14)0.0243 (15)0.0064 (11)0.0083 (12)0.0046 (12)
O14W0.0197 (15)0.0325 (17)0.0268 (17)0.0001 (13)0.0014 (13)0.0146 (13)
O160.0230 (15)0.0219 (14)0.0146 (14)−0.0001 (11)−0.0019 (11)0.0006 (11)
O15W0.0241 (16)0.0283 (16)0.0222 (16)0.0038 (13)0.0019 (13)−0.0054 (13)
O170.0244 (15)0.0169 (14)0.0197 (14)0.0044 (11)0.0045 (12)0.0003 (11)
O16W0.0155 (14)0.0225 (15)0.0234 (15)0.0054 (11)0.0037 (12)0.0009 (12)
O180.0366 (17)0.0268 (15)0.0159 (14)0.0102 (13)0.0074 (12)0.0030 (12)
O17W0.0265 (16)0.0307 (17)0.0164 (15)0.0079 (13)0.0040 (12)0.0015 (12)
O190.0237 (16)0.0337 (17)0.0247 (16)0.0000 (13)0.0079 (12)0.0041 (13)
O18W0.0138 (14)0.0236 (15)0.0425 (19)0.0035 (12)0.0009 (13)0.0005 (14)
O200.0398 (18)0.0207 (14)0.0157 (14)0.0057 (13)0.0097 (13)0.0008 (11)
O19W0.0248 (16)0.0216 (15)0.0190 (15)0.0005 (12)0.0036 (12)0.0010 (12)
O210.0252 (15)0.0195 (14)0.0151 (14)0.0005 (11)0.0027 (11)0.0049 (11)
O20W0.0236 (16)0.0305 (17)0.0235 (16)0.0020 (13)0.0092 (12)−0.0023 (13)
O21W0.0200 (15)0.0330 (17)0.0221 (15)0.0115 (13)0.0082 (12)0.0091 (12)
O22W0.0252 (16)0.0326 (17)0.0262 (17)0.0024 (13)−0.0001 (13)0.0060 (13)
O23W0.0321 (17)0.0263 (16)0.0204 (16)0.0046 (13)−0.0044 (13)0.0010 (12)
O24W0.0295 (17)0.0306 (17)0.0218 (16)0.0068 (13)0.0076 (13)−0.0029 (13)
O25W0.0221 (16)0.0370 (17)0.0234 (16)0.0113 (13)0.0080 (13)0.0097 (13)
O26W0.0268 (16)0.0221 (15)0.0246 (16)0.0008 (12)0.0029 (13)0.0039 (12)
O27W0.0253 (17)0.0468 (19)0.0255 (17)0.0017 (15)0.0047 (13)0.0035 (15)
O28W0.0204 (15)0.0300 (16)0.0203 (15)0.0060 (12)0.0057 (12)0.0075 (12)
O29W0.0259 (17)0.0304 (17)0.0262 (17)0.0008 (13)0.0032 (13)0.0009 (13)
O30W0.0247 (16)0.0246 (15)0.0210 (16)0.0027 (12)0.0042 (12)0.0006 (12)
N10.0140 (16)0.0193 (16)0.0146 (16)0.0052 (13)0.0041 (13)0.0029 (13)
N20.0183 (17)0.0189 (17)0.0162 (17)0.0022 (14)0.0059 (13)0.0029 (14)
N30.0139 (16)0.0202 (16)0.0163 (17)0.0064 (13)0.0044 (13)0.0033 (13)
N40.0190 (18)0.0183 (17)0.0134 (17)0.0013 (14)0.0029 (13)0.0036 (14)
N50.0136 (16)0.0207 (17)0.0150 (17)0.0063 (13)0.0023 (13)0.0034 (13)
N60.0183 (17)0.0203 (17)0.0135 (17)0.0012 (14)0.0032 (13)0.0047 (14)
C10.0147 (19)0.0196 (19)0.017 (2)0.0034 (15)0.0024 (15)0.0032 (15)
C20.015 (2)0.024 (2)0.023 (2)0.0029 (16)0.0000 (16)0.0051 (17)
C30.017 (2)0.022 (2)0.021 (2)0.0041 (16)−0.0003 (16)−0.0024 (16)
C40.017 (2)0.025 (2)0.017 (2)0.0050 (16)0.0024 (16)−0.0014 (16)
C50.0112 (18)0.024 (2)0.018 (2)0.0034 (15)0.0020 (15)−0.0004 (16)
C60.0089 (18)0.023 (2)0.0134 (19)0.0035 (15)0.0026 (14)0.0017 (15)
C70.0118 (18)0.0209 (19)0.0113 (18)0.0025 (15)0.0014 (14)0.0012 (15)
C80.0151 (19)0.0169 (19)0.017 (2)0.0026 (15)0.0009 (15)0.0002 (15)
C90.0157 (19)0.027 (2)0.0097 (18)0.0068 (16)0.0034 (15)0.0025 (15)
C100.019 (2)0.023 (2)0.0145 (19)0.0048 (16)0.0039 (15)−0.0002 (16)
C110.0147 (19)0.026 (2)0.016 (2)0.0073 (16)0.0050 (15)0.0046 (16)
C120.018 (2)0.023 (2)0.022 (2)0.0050 (16)0.0054 (16)0.0047 (16)
C130.022 (2)0.035 (2)0.020 (2)0.0091 (18)0.0056 (17)0.0130 (18)
C140.023 (2)0.040 (3)0.018 (2)0.0135 (19)0.0045 (17)0.0043 (18)
C150.025 (2)0.030 (2)0.022 (2)0.0063 (18)0.0020 (18)0.0004 (18)
C160.026 (2)0.026 (2)0.020 (2)0.0054 (17)0.0068 (17)0.0067 (17)
C170.0149 (19)0.020 (2)0.0131 (19)0.0050 (15)0.0040 (15)0.0018 (15)
C180.0142 (19)0.022 (2)0.020 (2)0.0050 (15)0.0016 (15)0.0026 (16)
C190.019 (2)0.019 (2)0.016 (2)0.0010 (16)0.0005 (16)−0.0032 (16)
C200.0160 (19)0.023 (2)0.016 (2)0.0036 (16)0.0032 (15)−0.0013 (16)
C210.0143 (19)0.0183 (19)0.0148 (19)0.0041 (15)0.0042 (15)0.0024 (15)
C220.0116 (18)0.022 (2)0.0124 (18)0.0032 (15)0.0023 (14)0.0035 (15)
C230.0113 (18)0.023 (2)0.0091 (18)0.0041 (15)0.0007 (14)−0.0003 (15)
C240.0147 (19)0.020 (2)0.018 (2)0.0030 (15)0.0012 (15)0.0032 (15)
C250.0143 (19)0.024 (2)0.0101 (18)0.0044 (15)0.0048 (14)0.0047 (15)
C260.017 (2)0.025 (2)0.0108 (19)0.0048 (16)0.0011 (15)0.0024 (15)
C270.0153 (19)0.027 (2)0.0134 (19)0.0061 (16)0.0029 (15)0.0039 (16)
C280.020 (2)0.026 (2)0.018 (2)0.0027 (17)0.0021 (16)0.0087 (17)
C290.021 (2)0.041 (3)0.018 (2)0.0066 (19)0.0059 (17)0.0114 (18)
C300.019 (2)0.043 (3)0.013 (2)0.0102 (19)0.0028 (16)0.0004 (18)
C310.026 (2)0.027 (2)0.016 (2)0.0050 (18)0.0009 (17)−0.0023 (17)
C320.027 (2)0.024 (2)0.020 (2)0.0037 (17)0.0064 (17)0.0068 (17)
C330.0134 (19)0.0178 (19)0.017 (2)0.0039 (15)0.0027 (15)0.0024 (15)
C340.0132 (19)0.020 (2)0.021 (2)0.0033 (15)0.0028 (15)0.0064 (16)
C350.0165 (19)0.0167 (19)0.018 (2)0.0016 (15)0.0035 (15)0.0010 (15)
C360.017 (2)0.024 (2)0.017 (2)0.0025 (16)0.0016 (16)−0.0020 (16)
C370.0141 (18)0.0196 (19)0.0146 (19)0.0033 (15)0.0034 (15)0.0027 (15)
C380.0137 (18)0.0180 (19)0.0128 (19)0.0023 (15)0.0021 (14)0.0021 (15)
C390.0111 (18)0.0184 (19)0.0144 (19)0.0038 (14)0.0007 (14)0.0014 (15)
C400.0155 (19)0.0175 (19)0.017 (2)0.0025 (15)0.0027 (15)0.0041 (15)
C410.0156 (19)0.022 (2)0.0127 (19)0.0033 (15)0.0029 (15)0.0017 (15)
C420.0145 (19)0.022 (2)0.0124 (19)0.0037 (15)−0.0007 (15)−0.0015 (15)
C430.0155 (19)0.027 (2)0.015 (2)0.0076 (16)0.0041 (15)0.0041 (16)
C440.018 (2)0.026 (2)0.018 (2)0.0059 (16)0.0045 (16)0.0047 (16)
C450.020 (2)0.041 (3)0.021 (2)0.0102 (19)0.0073 (17)0.0104 (19)
C460.022 (2)0.052 (3)0.014 (2)0.011 (2)0.0021 (17)0.0021 (19)
C470.023 (2)0.031 (2)0.021 (2)0.0051 (18)0.0008 (17)−0.0041 (18)
C480.023 (2)0.026 (2)0.017 (2)0.0034 (17)0.0011 (16)0.0029 (17)
Geometric parameters (Å, º) top
Co1—O1W2.036 (3)O27W—H54W0.865 (18)
Co1—O2W2.062 (3)O28W—H55W0.866 (18)
Co1—O6W2.068 (3)O28W—H56W0.858 (18)
Co1—O3W2.094 (3)O29W—H57W0.874 (18)
Co1—O4W2.108 (3)O29W—H58W0.867 (18)
Co1—O5W2.127 (3)O30W—H59W0.844 (18)
Co2—O8W2.066 (3)O30W—H60W0.880 (18)
Co2—O9W2.074 (3)N1—N21.302 (4)
Co2—O7W2.075 (3)N1—C11.349 (5)
Co2—O12W2.085 (3)N2—C111.411 (5)
Co2—O11W2.101 (3)N2—H1N0.88 (4)
Co2—O10W2.118 (3)N3—N41.298 (4)
Co3—O17W2.059 (3)N3—C171.339 (5)
Co3—O14W2.060 (3)N4—C271.406 (5)
Co3—O13W2.078 (3)N4—H2N0.77 (4)
Co3—O15W2.100 (3)N5—N61.298 (4)
Co3—O18W2.105 (3)N5—C331.336 (5)
Co3—O16W2.117 (3)N6—C431.409 (5)
S1—O21.449 (3)N6—H3N0.82 (4)
S1—O31.461 (3)C1—C21.452 (5)
S1—O11.467 (3)C1—C61.460 (5)
S1—C71.800 (4)C2—C31.445 (5)
S2—O51.450 (3)C3—C41.349 (5)
S2—O61.456 (3)C3—H30.9500
S2—O41.465 (3)C4—C51.444 (5)
S2—C91.771 (4)C4—H40.9500
S3—O91.447 (3)C5—C101.395 (5)
S3—O81.457 (3)C5—C61.427 (5)
S3—O101.469 (3)C6—C71.420 (5)
S3—C231.792 (4)C7—C81.388 (5)
S4—O131.454 (3)C8—C91.393 (5)
S4—O121.457 (3)C8—H80.9500
S4—O111.463 (3)C9—C101.375 (5)
S4—C251.764 (4)C10—H100.9500
S5—O161.453 (3)C11—C161.392 (5)
S5—O151.457 (3)C11—C121.398 (5)
S5—O171.470 (3)C12—C131.387 (6)
S5—C391.798 (4)C12—H120.9500
S6—O201.456 (3)C13—C141.384 (6)
S6—O191.457 (3)C13—H130.9500
S6—O181.462 (3)C14—C151.389 (6)
S6—C411.770 (4)C14—H140.9500
O1W—H1W0.862 (18)C15—C161.395 (6)
O1W—H2W0.863 (18)C15—H150.9500
O2W—H3W0.863 (18)C16—H160.9500
O2W—H4W0.872 (18)C17—C181.460 (5)
O3W—H5W0.853 (18)C17—C221.463 (5)
O3W—H6W0.849 (18)C18—C191.440 (5)
O4W—H7W0.858 (18)C19—C201.350 (5)
O4W—H8W0.853 (18)C19—H190.9500
O5W—H9W0.882 (18)C20—C211.437 (5)
O5W—H10W0.855 (18)C20—H200.9500
O7—C21.263 (4)C21—C261.407 (5)
O6W—H11W0.864 (18)C21—C221.425 (5)
O6W—H12W0.868 (18)C22—C231.429 (5)
O7W—H13W0.853 (18)C23—C241.389 (5)
O7W—H14W0.859 (18)C24—C251.402 (5)
O8W—H15W0.857 (18)C24—H240.9500
O8W—H16W0.858 (18)C25—C261.374 (5)
O9W—H17W0.869 (18)C26—H260.9500
O9W—H18W0.847 (18)C27—C321.390 (5)
O10W—H19W0.860 (18)C27—C281.394 (5)
O10W—H20W0.866 (18)C28—C291.391 (6)
O11W—H21W0.866 (18)C28—H280.9500
O11W—H22W0.855 (18)C29—C301.385 (6)
O12W—H23W0.852 (18)C29—H290.9500
O12W—H24W0.856 (18)C30—C311.386 (5)
O14—C181.266 (4)C30—H300.9500
O13W—H25W0.872 (18)C31—C321.387 (5)
O13W—H26W0.862 (18)C31—H310.9500
O14W—H27W0.856 (18)C32—H320.9500
O14W—H28W0.864 (18)C33—C341.459 (5)
O15W—H29W0.870 (18)C33—C381.465 (5)
O15W—H30W0.866 (18)C34—C351.435 (5)
O16W—H31W0.870 (18)C35—C361.345 (5)
O16W—H32W0.875 (18)C35—H350.9500
O17W—H33W0.859 (18)C36—C371.443 (5)
O17W—H34W0.849 (18)C36—H360.9500
O18W—H35W0.877 (18)C37—C421.402 (5)
O18W—H36W0.846 (18)C37—C381.415 (5)
O19W—H37W0.867 (18)C38—C391.434 (5)
O19W—H38W0.870 (18)C39—C401.394 (5)
O21—C341.271 (4)C40—C411.392 (5)
O20W—H39W0.858 (18)C40—H400.9500
O20W—H40W0.880 (18)C41—C421.371 (5)
O21W—H41W0.872 (18)C42—H420.9500
O21W—H42W0.865 (18)C43—C441.387 (5)
O22W—H43W0.872 (18)C43—C481.390 (5)
O22W—H44W0.873 (18)C44—C451.387 (6)
O23W—H45W0.877 (18)C44—H440.9500
O23W—H46W0.856 (18)C45—C461.381 (6)
O24W—H47W0.875 (18)C45—H450.9500
O24W—H48W0.877 (18)C46—C471.390 (6)
O25W—H49W0.877 (18)C46—H460.9500
O25W—H50W0.880 (18)C47—C481.393 (5)
O26W—H51W0.879 (18)C47—H470.9500
O26W—H52W0.871 (18)C48—H480.9500
O27W—H53W0.881 (18)
O1W—Co1—O2W173.61 (11)N3—N4—C27121.6 (3)
O1W—Co1—O6W91.55 (12)N3—N4—H2N116 (3)
O2W—Co1—O6W89.54 (12)C27—N4—H2N122 (3)
O1W—Co1—O3W91.02 (11)N6—N5—C33118.9 (3)
O2W—Co1—O3W95.18 (11)N5—N6—C43121.7 (3)
O6W—Co1—O3W94.49 (11)N5—N6—H3N113 (3)
O1W—Co1—O4W93.86 (11)C43—N6—H3N126 (3)
O2W—Co1—O4W85.06 (11)N1—C1—C2122.3 (3)
O6W—Co1—O4W174.58 (11)N1—C1—C6116.7 (3)
O3W—Co1—O4W85.61 (11)C2—C1—C6120.5 (3)
O1W—Co1—O5W86.34 (11)O7—C2—C3120.2 (4)
O2W—Co1—O5W87.40 (11)O7—C2—C1121.2 (4)
O6W—Co1—O5W88.23 (11)C3—C2—C1118.5 (3)
O3W—Co1—O5W176.26 (11)C4—C3—C2120.5 (4)
O4W—Co1—O5W91.92 (11)C4—C3—H3119.8
O8W—Co2—O9W86.98 (11)C2—C3—H3119.8
O8W—Co2—O7W177.60 (12)C3—C4—C5122.5 (4)
O9W—Co2—O7W90.72 (11)C3—C4—H4118.7
O8W—Co2—O12W89.06 (11)C5—C4—H4118.7
O9W—Co2—O12W93.82 (11)C10—C5—C6121.2 (3)
O7W—Co2—O12W91.79 (11)C10—C5—C4118.6 (3)
O8W—Co2—O11W93.99 (11)C6—C5—C4120.2 (3)
O9W—Co2—O11W178.69 (11)C7—C6—C5116.5 (3)
O7W—Co2—O11W88.29 (11)C7—C6—C1126.2 (3)
O12W—Co2—O11W87.07 (11)C5—C6—C1117.3 (3)
O8W—Co2—O10W91.38 (11)C8—C7—C6120.9 (3)
O9W—Co2—O10W92.32 (11)C8—C7—S1113.0 (3)
O7W—Co2—O10W88.01 (11)C6—C7—S1126.0 (3)
O12W—Co2—O10W173.86 (11)C7—C8—C9120.7 (3)
O11W—Co2—O10W86.78 (11)C7—C8—H8119.7
O17W—Co3—O14W91.59 (12)C9—C8—H8119.7
O17W—Co3—O13W92.58 (11)C10—C9—C8119.9 (3)
O14W—Co3—O13W173.89 (12)C10—C9—S2120.5 (3)
O17W—Co3—O15W177.78 (11)C8—C9—S2119.6 (3)
O14W—Co3—O15W87.98 (12)C9—C10—C5120.3 (3)
O13W—Co3—O15W87.68 (11)C9—C10—H10119.8
O17W—Co3—O18W93.78 (11)C5—C10—H10119.8
O14W—Co3—O18W96.96 (11)C16—C11—C12120.7 (4)
O13W—Co3—O18W87.21 (11)C16—C11—N2122.2 (3)
O15W—Co3—O18W88.44 (11)C12—C11—N2117.1 (3)
O17W—Co3—O16W84.57 (11)C13—C12—C11119.2 (4)
O14W—Co3—O16W88.13 (11)C13—C12—H12120.4
O13W—Co3—O16W87.83 (11)C11—C12—H12120.4
O15W—Co3—O16W93.24 (11)C14—C13—C12120.9 (4)
O18W—Co3—O16W174.70 (11)C14—C13—H13119.6
O2—S1—O3113.05 (15)C12—C13—H13119.6
O2—S1—O1111.34 (15)C13—C14—C15119.4 (4)
O3—S1—O1111.08 (15)C13—C14—H14120.3
O2—S1—C7108.61 (16)C15—C14—H14120.3
O3—S1—C7107.80 (16)C14—C15—C16120.9 (4)
O1—S1—C7104.52 (16)C14—C15—H15119.6
O5—S2—O6112.94 (16)C16—C15—H15119.6
O5—S2—O4111.83 (17)C11—C16—C15118.9 (4)
O6—S2—O4111.87 (16)C11—C16—H16120.6
O5—S2—C9107.29 (17)C15—C16—H16120.6
O6—S2—C9105.89 (17)N3—C17—C18122.5 (3)
O4—S2—C9106.52 (16)N3—C17—C22116.8 (3)
O9—S3—O8113.44 (15)C18—C17—C22120.2 (3)
O9—S3—O10112.07 (15)O14—C18—C19120.7 (3)
O8—S3—O10109.83 (15)O14—C18—C17121.0 (3)
O9—S3—C23106.34 (16)C19—C18—C17118.2 (3)
O8—S3—C23110.14 (16)C20—C19—C18121.1 (4)
O10—S3—C23104.58 (16)C20—C19—H19119.5
O13—S4—O12112.53 (16)C18—C19—H19119.5
O13—S4—O11112.68 (17)C19—C20—C21122.2 (4)
O12—S4—O11111.26 (16)C19—C20—H20118.9
O13—S4—C25107.35 (16)C21—C20—H20118.9
O12—S4—C25106.12 (17)C26—C21—C22120.8 (3)
O11—S4—C25106.41 (16)C26—C21—C20118.8 (3)
O16—S5—O15114.18 (16)C22—C21—C20120.4 (3)
O16—S5—O17111.30 (15)C21—C22—C23116.8 (3)
O15—S5—O17111.24 (15)C21—C22—C17117.4 (3)
O16—S5—C39107.52 (16)C23—C22—C17125.9 (3)
O15—S5—C39107.18 (16)C24—C23—C22120.9 (3)
O17—S5—C39104.82 (16)C24—C23—S3113.6 (3)
O20—S6—O19112.47 (17)C22—C23—S3124.9 (3)
O20—S6—O18112.27 (16)C23—C24—C25120.5 (3)
O19—S6—O18111.72 (17)C23—C24—H24119.7
O20—S6—C41107.48 (17)C25—C24—H24119.7
O19—S6—C41105.72 (17)C26—C25—C24119.9 (3)
O18—S6—C41106.70 (17)C26—C25—S4119.8 (3)
Co1—O1W—H1W126 (2)C24—C25—S4120.3 (3)
Co1—O1W—H2W123 (3)C25—C26—C21120.5 (3)
H1W—O1W—H2W104 (2)C25—C26—H26119.7
Co1—O2W—H3W120 (3)C21—C26—H26119.7
Co1—O2W—H4W115 (3)C32—C27—C28120.9 (4)
H3W—O2W—H4W101 (2)C32—C27—N4121.6 (3)
Co1—O3W—H5W125 (3)C28—C27—N4117.5 (3)
Co1—O3W—H6W125 (3)C29—C28—C27118.7 (4)
H5W—O3W—H6W104 (3)C29—C28—H28120.6
Co1—O4W—H7W107 (3)C27—C28—H28120.6
Co1—O4W—H8W120 (3)C30—C29—C28120.9 (4)
H7W—O4W—H8W104 (2)C30—C29—H29119.5
Co1—O5W—H9W115 (3)C28—C29—H29119.5
Co1—O5W—H10W117 (3)C29—C30—C31119.5 (4)
H9W—O5W—H10W99 (2)C29—C30—H30120.3
Co1—O6W—H11W126 (3)C31—C30—H30120.3
Co1—O6W—H12W129 (3)C30—C31—C32120.7 (4)
H11W—O6W—H12W101 (2)C30—C31—H31119.7
Co2—O7W—H13W127 (3)C32—C31—H31119.7
Co2—O7W—H14W121 (2)C31—C32—C27119.2 (4)
H13W—O7W—H14W105 (3)C31—C32—H32120.4
Co2—O8W—H15W113 (3)C27—C32—H32120.4
Co2—O8W—H16W127 (3)N5—C33—C34122.4 (3)
H15W—O8W—H16W104 (3)N5—C33—C38117.1 (3)
Co2—O9W—H17W133 (3)C34—C33—C38120.0 (3)
Co2—O9W—H18W121 (3)O21—C34—C35120.9 (3)
H17W—O9W—H18W103 (2)O21—C34—C33120.5 (3)
Co2—O10W—H19W120 (3)C35—C34—C33118.5 (3)
Co2—O10W—H20W116 (3)C36—C35—C34120.7 (3)
H19W—O10W—H20W102 (2)C36—C35—H35119.6
Co2—O11W—H21W110 (3)C34—C35—H35119.6
Co2—O11W—H22W121 (3)C35—C36—C37122.5 (4)
H21W—O11W—H22W104 (2)C35—C36—H36118.7
Co2—O12W—H23W129 (3)C37—C36—H36118.7
Co2—O12W—H24W125 (2)C42—C37—C38121.8 (3)
H23W—O12W—H24W102 (2)C42—C37—C36118.0 (3)
Co3—O13W—H25W119 (3)C38—C37—C36120.2 (3)
Co3—O13W—H26W124 (3)C37—C38—C39116.8 (3)
H25W—O13W—H26W101 (2)C37—C38—C33117.5 (3)
Co3—O14W—H27W125 (3)C39—C38—C33125.7 (3)
Co3—O14W—H28W128 (3)C40—C39—C38119.9 (3)
H27W—O14W—H28W103 (3)C40—C39—S5113.3 (3)
Co3—O15W—H29W115 (3)C38—C39—S5126.7 (3)
Co3—O15W—H30W127 (3)C41—C40—C39121.0 (3)
H29W—O15W—H30W102 (2)C41—C40—H40119.5
Co3—O16W—H31W120 (2)C39—C40—H40119.5
Co3—O16W—H32W125 (3)C42—C41—C40120.4 (3)
H31W—O16W—H32W100 (2)C42—C41—S6120.6 (3)
Co3—O17W—H33W116 (3)C40—C41—S6119.0 (3)
Co3—O17W—H34W112 (3)C41—C42—C37119.7 (3)
H33W—O17W—H34W103 (3)C41—C42—H42120.2
Co3—O18W—H35W120 (2)C37—C42—H42120.2
Co3—O18W—H36W138 (3)C44—C43—C48121.3 (4)
H35W—O18W—H36W102 (2)C44—C43—N6117.3 (3)
H37W—O19W—H38W101 (2)C48—C43—N6121.4 (3)
H39W—O20W—H40W99 (2)C45—C44—C43119.3 (4)
H41W—O21W—H42W101 (2)C45—C44—H44120.4
H43W—O22W—H44W101 (2)C43—C44—H44120.4
H45W—O23W—H46W101 (2)C46—C45—C44120.5 (4)
H47W—O24W—H48W99 (2)C46—C45—H45119.8
H49W—O25W—H50W99 (2)C44—C45—H45119.8
H51W—O26W—H52W100 (2)C45—C46—C47119.8 (4)
H53W—O27W—H54W102 (3)C45—C46—H46120.1
H55W—O28W—H56W100 (2)C47—C46—H46120.1
H57W—O29W—H58W101 (2)C46—C47—C48120.7 (4)
H59W—O30W—H60W103 (2)C46—C47—H47119.7
N2—N1—C1118.8 (3)C48—C47—H47119.7
N1—N2—C11121.3 (3)C43—C48—C47118.5 (4)
N1—N2—H1N115 (3)C43—C48—H48120.8
C11—N2—H1N123 (3)C47—C48—H48120.8
N4—N3—C17119.3 (3)
C1—N1—N2—C11−175.7 (3)O10—S3—C23—C2416.1 (3)
C17—N3—N4—C27175.7 (3)O9—S3—C23—C22−36.0 (3)
C33—N5—N6—C43−175.4 (3)O8—S3—C23—C2287.3 (3)
N2—N1—C1—C26.9 (5)O10—S3—C23—C22−154.7 (3)
N2—N1—C1—C6179.2 (3)C22—C23—C24—C254.4 (5)
N1—C1—C2—O7−11.4 (6)S3—C23—C24—C25−166.8 (3)
C6—C1—C2—O7176.6 (3)C23—C24—C25—C262.9 (5)
N1—C1—C2—C3165.0 (3)C23—C24—C25—S4−177.6 (3)
C6—C1—C2—C3−7.0 (5)O13—S4—C25—C26−92.0 (3)
O7—C2—C3—C4177.4 (4)O12—S4—C25—C2628.5 (3)
C1—C2—C3—C40.9 (5)O11—S4—C25—C26147.1 (3)
C2—C3—C4—C52.6 (6)O13—S4—C25—C2488.4 (3)
C3—C4—C5—C10179.7 (4)O12—S4—C25—C24−151.0 (3)
C3—C4—C5—C6−0.1 (6)O11—S4—C25—C24−32.4 (3)
C10—C5—C6—C7−6.8 (5)C24—C25—C26—C21−5.3 (5)
C4—C5—C6—C7173.0 (3)S4—C25—C26—C21175.2 (3)
C10—C5—C6—C1174.4 (3)C22—C21—C26—C250.5 (5)
C4—C5—C6—C1−5.8 (5)C20—C21—C26—C25179.9 (3)
N1—C1—C6—C718.2 (5)N3—N4—C27—C321.4 (5)
C2—C1—C6—C7−169.3 (3)N3—N4—C27—C28−179.3 (3)
N1—C1—C6—C5−163.2 (3)C32—C27—C28—C291.2 (6)
C2—C1—C6—C59.3 (5)N4—C27—C28—C29−178.1 (3)
C5—C6—C7—C88.1 (5)C27—C28—C29—C300.4 (6)
C1—C6—C7—C8−173.2 (3)C28—C29—C30—C31−1.4 (6)
C5—C6—C7—S1−167.8 (3)C29—C30—C31—C320.8 (6)
C1—C6—C7—S110.8 (5)C30—C31—C32—C270.8 (6)
O2—S1—C7—C899.6 (3)C28—C27—C32—C31−1.8 (6)
O3—S1—C7—C8−137.5 (3)N4—C27—C32—C31177.4 (3)
O1—S1—C7—C8−19.3 (3)N6—N5—C33—C347.6 (5)
O2—S1—C7—C6−84.1 (3)N6—N5—C33—C38179.2 (3)
O3—S1—C7—C638.7 (4)N5—C33—C34—O21−12.4 (5)
O1—S1—C7—C6156.9 (3)C38—C33—C34—O21176.2 (3)
C6—C7—C8—C9−3.9 (5)N5—C33—C34—C35164.7 (3)
S1—C7—C8—C9172.5 (3)C38—C33—C34—C35−6.7 (5)
C7—C8—C9—C10−2.1 (5)O21—C34—C35—C36178.5 (4)
C7—C8—C9—S2178.5 (3)C33—C34—C35—C361.4 (5)
O5—S2—C9—C1098.1 (3)C34—C35—C36—C371.4 (6)
O6—S2—C9—C10−22.7 (4)C35—C36—C37—C42−179.0 (4)
O4—S2—C9—C10−142.0 (3)C35—C36—C37—C381.1 (6)
O5—S2—C9—C8−82.5 (3)C42—C37—C38—C39−5.2 (5)
O6—S2—C9—C8156.7 (3)C36—C37—C38—C39174.7 (3)
O4—S2—C9—C837.4 (3)C42—C37—C38—C33173.9 (3)
C8—C9—C10—C53.5 (6)C36—C37—C38—C33−6.3 (5)
S2—C9—C10—C5−177.1 (3)N5—C33—C38—C37−162.8 (3)
C6—C5—C10—C91.1 (6)C34—C33—C38—C379.0 (5)
C4—C5—C10—C9−178.7 (3)N5—C33—C38—C3916.1 (5)
N1—N2—C11—C16−3.1 (5)C34—C33—C38—C39−172.0 (3)
N1—N2—C11—C12177.8 (3)C37—C38—C39—C406.7 (5)
C16—C11—C12—C13−0.6 (6)C33—C38—C39—C40−172.3 (3)
N2—C11—C12—C13178.5 (3)C37—C38—C39—S5−170.1 (3)
C11—C12—C13—C14−0.5 (6)C33—C38—C39—S511.0 (5)
C12—C13—C14—C150.9 (6)O16—S5—C39—C40100.8 (3)
C13—C14—C15—C16−0.1 (6)O15—S5—C39—C40−136.0 (3)
C12—C11—C16—C151.3 (6)O17—S5—C39—C40−17.7 (3)
N2—C11—C16—C15−177.7 (3)O16—S5—C39—C38−82.2 (3)
C14—C15—C16—C11−1.0 (6)O15—S5—C39—C3840.9 (4)
N4—N3—C17—C18−6.2 (5)O17—S5—C39—C38159.2 (3)
N4—N3—C17—C22−178.3 (3)C38—C39—C40—C41−2.7 (5)
N3—C17—C18—O1410.6 (5)S5—C39—C40—C41174.4 (3)
C22—C17—C18—O14−177.5 (3)C39—C40—C41—C42−3.2 (6)
N3—C17—C18—C19−166.6 (3)C39—C40—C41—S6176.6 (3)
C22—C17—C18—C195.3 (5)O20—S6—C41—C42−10.1 (4)
O14—C18—C19—C20−176.2 (3)O19—S6—C41—C42110.3 (3)
C17—C18—C19—C201.0 (5)O18—S6—C41—C42−130.7 (3)
C18—C19—C20—C21−3.2 (6)O20—S6—C41—C40170.1 (3)
C19—C20—C21—C26179.7 (4)O19—S6—C41—C40−69.5 (3)
C19—C20—C21—C22−0.9 (6)O18—S6—C41—C4049.5 (3)
C26—C21—C22—C236.4 (5)C40—C41—C42—C374.8 (5)
C20—C21—C22—C23−173.0 (3)S6—C41—C42—C37−175.0 (3)
C26—C21—C22—C17−173.6 (3)C38—C37—C42—C41−0.5 (6)
C20—C21—C22—C177.0 (5)C36—C37—C42—C41179.7 (3)
N3—C17—C22—C21163.2 (3)N5—N6—C43—C44179.6 (3)
C18—C17—C22—C21−9.1 (5)N5—N6—C43—C48−2.2 (5)
N3—C17—C22—C23−16.8 (5)C48—C43—C44—C45−0.5 (6)
C18—C17—C22—C23170.9 (3)N6—C43—C44—C45177.7 (3)
C21—C22—C23—C24−8.8 (5)C43—C44—C45—C460.1 (6)
C17—C22—C23—C24171.2 (3)C44—C45—C46—C470.2 (6)
C21—C22—C23—S3161.4 (3)C45—C46—C47—C48−0.2 (6)
C17—C22—C23—S3−18.6 (5)C44—C43—C48—C470.5 (6)
O9—S3—C23—C24134.8 (3)N6—C43—C48—C47−177.6 (3)
O8—S3—C23—C24−101.9 (3)C46—C47—C48—C43−0.1 (6)

Experimental details

Crystal data
Chemical formula[Co(H2O)6](C16H10N2O7S2)·4H2O
Mr645.47
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)10.0768 (3), 14.6463 (5), 26.3881 (8)
α, β, γ (°)93.470 (2), 90.813 (1), 101.175 (1)
V (Å3)3812.4 (2)
Z6
Radiation typeMo Kα
µ (mm−1)0.92
Crystal size (mm)0.35 × 0.22 × 0.06
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.683, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		63505, 16529, 10980
Rint0.086
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.150, 1.03
No. of reflections16529
No. of parameters1216
No. of restraints90
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.95, −1.03

Computer programs: COLLECT (Hooft, 1988) and DENZO (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

 

Acknowledgements

MOO thanks the Commonwealth Scholarship Commission and the British Council for funding and Moi University for sabatical leave.

References

First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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 First citationOjala, W. H., Lu, L. K., Albers, K. E., Gleason, W. B., Richardson, T. I., Lovrien, R. E. & Sudbeck, E. A. (1994). Acta Cryst. B50, 684–694.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.  Google Scholar
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ISSN: 2056-9890
Volume 66| Part 10| October 2010| Pages m1330-m1331
doi:10.1107/S1600536810037360
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