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The title compound, [Co(H2O)6](C16H11O7S)2·4H2O, with cobalt(II) at the centre of symmetry, exhibits alternating hydro­philic and hydro­phobic regions. Hydro­philic regions are generated by O-H...O hydrogen bonds among sulfonate groups, involving solvent water mol­ecules and coordinated water mol­ecules; [pi]-[pi] stacking inter­actions assemble the flavone skeletons into columns which form the hydro­phobic regions. A three-dimensional network is built up from an extensive array of hydrogen bonds, [pi]-[pi] stacking inter­actions and electrostatic inter­actions between the cation and anion. As a salt of the sulfonated derivative of naturally occurring tectochrysin (5-hydr­oxy-7-methoxy­flavone), this compound offers enhanced solubility and potential biological activity over the natural product.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108006975/sq3126sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108006975/sq3126Isup2.hkl
Contains datablock I

CCDC reference: 686422

Comment top

Tectochrysin (5-hydroxyl-7-methoxyflavone), a naturally occurring flavonoid and one of the effective components of propolis (Fujimoto et al., 2001), has many different biological properties such as anti-cancer (Ahmed-Belkacem et al., 2005), anti-oxidant (Lee et al., 2003) and trypanocidal activity (Takeara et al., 2003). The aqueous solubility of flavonoids in general is poor and their biological utilization rate is low. It is therefore necessary to synthesize water-soluble flavonoid derivatives in order to improve their possible biological activities, and this may be achieved by the introduction of a sulfonate group (Hiroyuki et al., 1996; Jiang et al., 2001). We have synthesized some flavonoidsulfonates (Zhang & Wang, 2005; Wang & Zhang, 2005) and studied the biological activities of sodium 4',7-dihydroxyisoflavone-3'-sulfonate (Liu et al., 2003) and sodium 4'-hydroxyl-7-methoxyisoflavone-3'-sulfonate (Zhang et al., 2002). The results show that the biological activities of flavonoidsulfonates are better in comparison with the corresponding parent flavonoids. Given the biological activity of tectochrysin, it is important to prepare and study sulfonated derivatives that may offer improved properties. In this paper, we report the crystal structure of the cobalt(II) salt of 5-hydroxyl-7-methoxyflavone-6-sulfonate, (I).

As shown in Fig. 1, (I) consists of a metal cation [Co(H2O)6]2+, two 5-hydroxyl-7-methoxyflavone-6-sulfonate anions and four water molecules. The CoII ion, lying on an inversion centre, has a nearly ideal octahedral environment of six O atoms from coordinated water molecules. The equatorial plane of the octahedron is defined by O1, O2, O1i and O2i [symmetry code: (i) -x, -y + 2, -z + 2] with the average Co—O bond length 2.072 (2) Å. The axes of the octahedron are defined by O3 and O3i with the Co—O3(O3i) bond length 2.1107 (19) Å. The dihedral angle between ring A (C1–C6) and ring C (C3–C4/O4/C8–C10) is 1.85 (11)°, and that of the benzopyrane ring A/C (C1–C6/O4/C8–C10) and ring B (C11–C16) is 1.95 (11)°. The flavone skeleton is essentially planar, with the mean deviation from the least-squares plane being 0.0248 Å; this is similar to what has been found in tectochrysin itself (Chantrapromma et al., 1989).

Sulfonate groups, coordinated water molecules and solvate water molecules in (I) are linked by numerous O—H···O hydrogen bonds (Fig. 1, Table 1). For example, a hydrogen-bond chain O1—H1B···O12—H12B···O9 exists between the sulfonate group and a coordinated water molecule, bridged by the solvate water molecule O12. O3—H3B···O9 and O12—H12B···O9 are involved in a three-centred hydrogen bond. Additionally, cyclic hydrogen-bond motifs R22(8) and R22(14) (Fig. 2) are formed by paired `soft' hydrogen bonds C9—H9···O5v and C12—H12···O5v [symmetry code: (v) -x, -y + 2, -z + 1], respectively. An independent hydrogen bond O6—H6···O5 forms an intramolecular motif S(6) (Fig. 2). The three sulfonate O atoms are involved in seven O—H···O hydrogen bonds. According to Haynes et al. (2004), this indicates that the sulfonate moiety behaves as a steric tightener, i.e. brings several hydrogen-bond acceptors into close contact. The extensive array of hydrogen bonds makes this region hydrophilic (Fig. 3).

Additionally, π···π stacking interactions between the flavone skeletons are observed (Fig. 3). The ring B of the flavone at (x, y, z) has stacking interactions with the ring C of the flavone at (-x + 1, -y + 2, -z + 1), with a centroid–centroid (CgBCgC*) [* indicates the symmetry operation (-x, -y + 2, -z + 1)] distance of 3.5553 (16) Å and a perpendicular distance (CgB on ring C*) of 3.429 (2) Å. The ring B of the flavone at (x, y, z) has stacking interactions with the ring A of the flavone at (-x + 1, -y + 1, -z + 1), with a centroid–centroid (CgBCgA#) [# indicates the symmetry operation (-x + 1, -y + 1, -z + 1)] distance of 3.6396 (16) Å and a perpendicular distance (CgB on ring A#) of 3.458 (2) Å. These values are close to those reported for typical aromatic π···π stacking interactions (Hunter, 1994). The arrangement of the flavone skeletons of (I) in antiparallel fashion and stacked into columns along the (101) direction is driven by these interactions. The columns are linked by hydrogen-bond motifs R22(8) and R22(14) forming the hydrophobic regions of (I) (Fig. 3). The structure of (I) is quite different from the zinc complex of the related 5,7-dihydroxyflavone-6-sulfonate, [Zn(C15H8O7S)(DMSO)]2·H2O [DMSO = dimethyl sulfoxide?] (Zhang et al., 2006). The Zn compound is a coordination polymer in which the cation and anion are linked together by Zn—O coordination bonds. By contrast, (I) is a metal salt of 5-hydroxyl-7-methoxyflavone-6-sulfonate in which the cation and anion are linked together by hydrogen bonds and electrostatic interactions.

Related literature top

For related literature, see: Ahmed-Belkacem, Pozza, Munoz-Martinez, Bates, Castanys, Gamarro, Di Pietro & Perez-Victoria (2005); Chantrapromma et al. (1989); Fujimoto et al. (2001); Haynes et al. (2004); Hiroyuki et al. (1996); Hunter (1994); Jiang et al. (2001); Lee et al. (2003); Liu et al. (2003); Takeara et al. (2003); Wang & Zhang (2005); Zhang & Wang (2005); Zhang et al. (2002).

Experimental top

Tectochrysin (2.0 g) was slowly added to concentrated sulfuric acid (10 ml) while stirring. The reaction was maintained at room temperature for 15 h, then poured into a saturated aqueous NaCl solution (50 ml) and a yellow precipitate appeared. After 5 h, the precipitate was filtered and washed with saturated aqueous NaCl solution until the pH value of the filtrate was 7. The precipitate was recrystallized from an ethanol–water (v/v = 1:1) solution to afford sodium tectochrysin-6-sulfonate. The product was dried at 378 K for 10 h under vacuum. Yield = 75%. IR (cm-1, KBr) ν: 3465, 1646, 1607, 1487, 1447, 1205, 1144, 1099, 1045, 899, 807, 771, 687. 1H NMR (DMSO-d6, 300 MHz) δ: 13.15 (s, 1H, H–C5–OH), 7.58–7.88 (m, 5H, H–C2', C3', C4', C5', C6'), 6.77 (s, 1H, H–C8), 6.53 (s, 1H, H–C3), 3.88 (s, 3H, C7–OCH3). 13C NMR (DMSO-d6, 75 MHz) δ: 177.5 (C4), 162.1 (C7), 160.4 (C2), 158.8 (C8A), 156.2 (C5), 131.6 (C1'), 130.5 (C4'), 129.0 (C3', C5'), 126.0 (C2', C6'), 115.6 (C6), 107.6 (C4A), 106.6 (C3), 91.4 (C8), 56.4 (C7–OCH3). Analysis calculated for C16H11NaO7S (%): C 51.89, H 2.99; found C 51.15, H 3.21. An aqueous solution of CoCl2·6H2O (10%, 5 ml) was mixed with a hot aqueous solution of sodium tectochrysin-6-sulfonate (5%, 10 ml) and (I) was obtained after 24 h. It was recrystallized from an ethanol–water (v/v = 3:1) solution. Pink block-shaped crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent for about 5 d at room temperature. Yield = 81%. IR (cm-1, KBr) ν: 3460, 1646, 1611, 1488, 1445, 1208, 1179, 1099, 1042, 887, 804, 769, 687.

Refinement top

H atoms bonded to C atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C). H atoms of the water molecules were found in difference maps and positionally refined with constraints of O—H = 0.82 (4) Å and Uiso(H) = 1.5Ueq(O). The phenol hydroxyl H atom was positioned geometrically with O—H = 0.82 Å and included as a riding atom with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT or SAINT-Plus (Bruker, 1999); 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. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Hydrogen-bond motifs R22(8), R22(14) and S(6) in (I). Displacement ellipsoids are drawn at the 30% probability level. The dashed lines indicate hydrogen bonds. Symmetry codes: (v) -x, -y + 2, -z + 1.
[Figure 3] Fig. 3. A view of the packing of (I), illustrating the alternating hydrophilic and hydrophobic regions and non-bonded contacts. CgA, CgB and CgC are the centroids of rings A, B and C, respectively. Atoms labelled # and * are generated by the symmetry operations (-x + 1, -y + 1, -z + 1) and (-x + 1, -y + 2, -z + 1), respectively.
Hexaquacobalt(II) bis(5-hydroxy-7-methoxy-4-oxo-2-phenyl-4H-chromene-6-sulfonate) tetrahydrate top
Crystal data top
[Co(H2O)6](C16H11O7S)2·4H2OZ = 1
Mr = 933.71F(000) = 485
Triclinic, P1Dx = 1.549 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.978 (2) ÅCell parameters from 2496 reflections
b = 7.2034 (2) Åθ = 2.9–27.0°
c = 20.145 (1) ŵ = 0.62 mm1
α = 83.970 (2)°T = 296 K
β = 89.286 (3)°Block, pink
γ = 83.597 (2)°0.34 × 0.25 × 0.14 mm
V = 1000.7 (3) Å3
Data collection top
CCD area detector
diffractometer
3500 independent reflections
Radiation source: fine-focus sealed tube2949 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
ϕ and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 86
Tmin = 0.814, Tmax = 0.915k = 88
5062 measured reflectionsl = 2423
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0967P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3500 reflectionsΔρmax = 0.30 e Å3
311 parametersΔρmin = 0.41 e Å3
10 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: none
Crystal data top
[Co(H2O)6](C16H11O7S)2·4H2Oγ = 83.597 (2)°
Mr = 933.71V = 1000.7 (3) Å3
Triclinic, P1Z = 1
a = 6.978 (2) ÅMo Kα radiation
b = 7.2034 (2) ŵ = 0.62 mm1
c = 20.145 (1) ÅT = 296 K
α = 83.970 (2)°0.34 × 0.25 × 0.14 mm
β = 89.286 (3)°
Data collection top
CCD area detector
diffractometer
3500 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
2949 reflections with I > 2σ(I)
Tmin = 0.814, Tmax = 0.915Rint = 0.013
5062 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03710 restraints
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.30 e Å3
3500 reflectionsΔρmin = 0.41 e Å3
311 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
Co10.00001.00001.00000.03652 (19)
S10.29042 (8)0.58372 (8)0.84070 (3)0.0332 (2)
O20.2360 (3)0.7967 (3)0.99917 (10)0.0523 (5)
O30.0478 (3)0.9960 (3)0.89693 (9)0.0459 (5)
O40.5501 (2)0.6859 (3)0.55930 (8)0.0389 (4)
O50.0121 (3)0.8628 (3)0.59487 (10)0.0607 (6)
O60.0480 (2)0.7771 (3)0.71944 (9)0.0495 (5)
H60.00880.81650.68450.074*
O70.6606 (2)0.4719 (3)0.78698 (8)0.0432 (5)
O90.0915 (2)0.6584 (3)0.84767 (8)0.0421 (4)
O80.3191 (3)0.3820 (3)0.85733 (9)0.0494 (5)
O100.4180 (3)0.6845 (3)0.87757 (8)0.0447 (5)
C160.7270 (5)0.7106 (4)0.43960 (14)0.0513 (7)
H160.79390.65770.47790.062*
C150.8212 (5)0.7232 (5)0.37834 (16)0.0616 (8)
H150.95110.67850.37570.074*
C140.7231 (5)0.8017 (5)0.32147 (15)0.0605 (9)
H140.78620.80890.28050.073*
C130.5319 (5)0.8693 (4)0.32543 (14)0.0544 (8)
H130.46620.92280.28700.065*
C120.4365 (4)0.8587 (4)0.38562 (13)0.0489 (7)
H120.30730.90610.38780.059*
C110.5340 (4)0.7765 (4)0.44366 (12)0.0393 (6)
C100.4303 (4)0.7657 (4)0.50846 (12)0.0371 (6)
C90.2458 (4)0.8245 (4)0.51869 (13)0.0449 (6)
H90.16920.87600.48240.054*
C80.1611 (4)0.8103 (4)0.58466 (13)0.0426 (6)
C30.2921 (3)0.7306 (3)0.63808 (11)0.0329 (5)
C20.2289 (3)0.7121 (3)0.70590 (12)0.0339 (5)
C10.3564 (3)0.6245 (3)0.75516 (11)0.0305 (5)
C60.5477 (3)0.5604 (3)0.73677 (11)0.0329 (5)
C50.6115 (3)0.5848 (4)0.67143 (11)0.0360 (6)
H50.73820.54600.66010.043*
C40.4802 (3)0.6690 (3)0.62351 (11)0.0332 (5)
C70.8427 (3)0.3752 (4)0.77083 (13)0.0414 (6)
H7A0.82360.28610.73990.062*
H7B0.90180.31030.81080.062*
H7C0.92490.46400.75100.062*
H2B0.240 (5)0.695 (3)1.0209 (16)0.075 (12)*
H3B0.001 (6)0.906 (4)0.878 (2)0.100 (15)*
H2C0.302 (4)0.780 (5)0.9660 (11)0.065 (10)*
H3C0.153 (3)1.025 (5)0.8785 (15)0.068 (11)*
O120.2187 (3)0.5481 (3)0.92937 (9)0.0455 (5)
H12B0.122 (4)0.568 (7)0.9073 (19)0.112 (17)*
H12C0.309 (3)0.587 (5)0.9046 (14)0.069 (11)*
O10.1787 (4)0.7928 (3)1.02398 (10)0.0583 (6)
H1B0.212 (5)0.721 (4)0.9987 (15)0.078 (12)*
H1C0.209 (5)0.743 (5)1.0600 (9)0.068 (10)*
O110.4146 (4)1.0457 (4)0.84568 (13)0.0628 (6)
H11C0.476 (6)1.147 (4)0.852 (2)0.108 (17)*
H11B0.485 (5)0.964 (5)0.857 (2)0.095 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0457 (3)0.0317 (3)0.0311 (3)0.0020 (2)0.0080 (2)0.0020 (2)
S10.0343 (3)0.0357 (4)0.0289 (3)0.0013 (3)0.0078 (2)0.0038 (2)
O20.0641 (13)0.0431 (12)0.0450 (12)0.0117 (10)0.0163 (10)0.0035 (10)
O30.0546 (13)0.0457 (12)0.0360 (10)0.0011 (10)0.0021 (9)0.0055 (9)
O40.0414 (9)0.0466 (11)0.0270 (8)0.0001 (8)0.0062 (7)0.0019 (7)
O50.0367 (11)0.0880 (17)0.0492 (11)0.0063 (10)0.0033 (9)0.0173 (11)
O60.0323 (10)0.0659 (14)0.0434 (10)0.0092 (9)0.0090 (8)0.0101 (10)
O70.0351 (9)0.0575 (12)0.0324 (9)0.0093 (8)0.0031 (7)0.0012 (8)
O90.0346 (9)0.0533 (12)0.0379 (9)0.0010 (8)0.0098 (7)0.0073 (8)
O80.0624 (12)0.0384 (11)0.0436 (10)0.0010 (9)0.0220 (9)0.0044 (8)
O100.0415 (10)0.0576 (12)0.0363 (9)0.0044 (9)0.0031 (7)0.0133 (8)
C160.0625 (18)0.0495 (18)0.0397 (15)0.0002 (14)0.0089 (13)0.0015 (13)
C150.069 (2)0.060 (2)0.0527 (18)0.0004 (16)0.0263 (15)0.0064 (15)
C140.090 (3)0.0549 (19)0.0384 (16)0.0136 (18)0.0230 (16)0.0083 (14)
C130.081 (2)0.0518 (18)0.0321 (14)0.0173 (16)0.0055 (14)0.0034 (13)
C120.0583 (18)0.0512 (17)0.0381 (14)0.0112 (14)0.0010 (12)0.0036 (12)
C110.0537 (16)0.0319 (13)0.0337 (13)0.0085 (12)0.0075 (11)0.0073 (10)
C100.0431 (14)0.0348 (13)0.0340 (13)0.0079 (11)0.0016 (11)0.0026 (10)
C90.0470 (15)0.0523 (17)0.0329 (13)0.0047 (13)0.0033 (11)0.0063 (12)
C80.0370 (14)0.0465 (16)0.0415 (14)0.0025 (11)0.0020 (11)0.0061 (12)
C30.0325 (12)0.0347 (13)0.0311 (12)0.0047 (10)0.0016 (9)0.0001 (10)
C20.0313 (12)0.0311 (13)0.0384 (13)0.0029 (10)0.0050 (10)0.0007 (10)
C10.0320 (12)0.0298 (12)0.0295 (12)0.0023 (10)0.0059 (9)0.0032 (9)
C60.0314 (12)0.0351 (13)0.0317 (12)0.0018 (10)0.0024 (9)0.0028 (10)
C50.0304 (12)0.0427 (14)0.0335 (13)0.0022 (10)0.0043 (10)0.0050 (11)
C40.0381 (13)0.0315 (12)0.0303 (12)0.0052 (10)0.0050 (10)0.0039 (10)
C70.0303 (12)0.0471 (16)0.0436 (14)0.0043 (11)0.0014 (10)0.0008 (12)
O120.0433 (11)0.0509 (12)0.0408 (10)0.0026 (9)0.0024 (9)0.0012 (9)
O10.0880 (16)0.0528 (13)0.0392 (11)0.0316 (12)0.0168 (11)0.0061 (10)
O110.0556 (14)0.0555 (15)0.0752 (15)0.0004 (12)0.0009 (11)0.0028 (13)
Geometric parameters (Å, º) top
Co1—O1i2.065 (2)C14—H140.9300
Co1—O12.065 (2)C13—C121.375 (4)
Co1—O22.079 (2)C13—H130.9300
Co1—O2i2.079 (2)C12—C111.402 (4)
Co1—O32.1107 (19)C12—H120.9300
Co1—O3i2.1107 (19)C11—C101.484 (3)
S1—O91.4424 (18)C10—C91.331 (4)
S1—O81.449 (2)C9—C81.446 (4)
S1—O101.4650 (19)C9—H90.9300
S1—C11.781 (2)C8—C31.449 (3)
O2—H2B0.81 (3)C3—C41.376 (3)
O2—H2C0.816 (10)C3—C21.428 (3)
O3—H3B0.82 (3)C2—C11.393 (3)
O3—H3C0.821 (10)C1—C61.421 (3)
O4—C101.367 (3)C6—C51.384 (3)
O4—C41.375 (3)C5—C41.384 (3)
O5—C81.247 (3)C5—H50.9300
O6—C21.332 (3)C7—H7A0.9600
O6—H60.8200C7—H7B0.9600
O7—C61.350 (3)C7—H7C0.9600
O7—C71.431 (3)O12—H12B0.82 (3)
C16—C111.381 (4)O12—H12C0.82 (3)
C16—C151.391 (4)O1—H1B0.82 (3)
C16—H160.9300O1—H1C0.811 (10)
C15—C141.378 (5)O11—H11C0.82 (3)
C15—H150.9300O11—H11B0.82 (4)
C14—C131.372 (5)
O1i—Co1—O1180.0C13—C12—H12120.0
O1i—Co1—O289.89 (10)C11—C12—H12120.0
O1—Co1—O290.11 (10)C16—C11—C12119.1 (2)
O1i—Co1—O2i90.11 (10)C16—C11—C10121.1 (2)
O1—Co1—O2i89.89 (10)C12—C11—C10119.7 (2)
O2—Co1—O2i180.000 (1)C9—C10—O4122.1 (2)
O1i—Co1—O388.29 (8)C9—C10—C11126.7 (2)
O1—Co1—O391.71 (8)O4—C10—C11111.2 (2)
O2—Co1—O391.90 (8)C10—C9—C8121.7 (2)
O2i—Co1—O388.10 (8)C10—C9—H9119.1
O1i—Co1—O3i91.71 (8)C8—C9—H9119.1
O1—Co1—O3i88.29 (8)O5—C8—C9122.4 (2)
O2—Co1—O3i88.10 (8)O5—C8—C3122.4 (2)
O2i—Co1—O3i91.90 (8)C9—C8—C3115.2 (2)
O3—Co1—O3i180.000 (1)C4—C3—C2119.0 (2)
O9—S1—O8112.03 (11)C4—C3—C8119.8 (2)
O9—S1—O10111.03 (11)C2—C3—C8121.2 (2)
O8—S1—O10113.28 (12)O6—C2—C1122.4 (2)
O9—S1—C1108.22 (11)O6—C2—C3118.3 (2)
O8—S1—C1105.95 (10)C1—C2—C3119.2 (2)
O10—S1—C1105.88 (11)C2—C1—C6119.0 (2)
Co1—O2—H2B123 (3)C2—C1—S1123.19 (18)
Co1—O2—H2C123 (3)C6—C1—S1117.76 (17)
H2B—O2—H2C106 (4)O7—C6—C5122.7 (2)
Co1—O3—H3B119 (3)O7—C6—C1115.47 (19)
Co1—O3—H3C124 (2)C5—C6—C1121.8 (2)
H3B—O3—H3C104 (4)C4—C5—C6117.7 (2)
C10—O4—C4119.4 (2)C4—C5—H5121.2
C2—O6—H6109.5C6—C5—H5121.2
C6—O7—C7118.63 (18)O4—C4—C3121.7 (2)
C11—C16—C15120.0 (3)O4—C4—C5115.2 (2)
C11—C16—H16120.0C3—C4—C5123.1 (2)
C15—C16—H16120.0O7—C7—H7A109.5
C14—C15—C16120.3 (3)O7—C7—H7B109.5
C14—C15—H15119.9H7A—C7—H7B109.5
C16—C15—H15119.9O7—C7—H7C109.5
C13—C14—C15119.9 (3)H7A—C7—H7C109.5
C13—C14—H14120.1H7B—C7—H7C109.5
C15—C14—H14120.1H12B—O12—H12C105 (4)
C14—C13—C12120.7 (3)Co1—O1—H1B126 (3)
C14—C13—H13119.7Co1—O1—H1C130 (3)
C12—C13—H13119.7H1B—O1—H1C102 (4)
C13—C12—C11120.0 (3)H11C—O11—H11B107 (5)
C11—C16—C15—C140.1 (5)O6—C2—C1—C6179.4 (2)
C16—C15—C14—C130.6 (5)C3—C2—C1—C61.7 (3)
C15—C14—C13—C120.3 (5)O6—C2—C1—S11.9 (3)
C14—C13—C12—C110.6 (4)C3—C2—C1—S1176.98 (18)
C15—C16—C11—C121.1 (4)O9—S1—C1—C20.8 (2)
C15—C16—C11—C10179.6 (3)O8—S1—C1—C2119.5 (2)
C13—C12—C11—C161.3 (4)O10—S1—C1—C2120.0 (2)
C13—C12—C11—C10179.9 (2)O9—S1—C1—C6179.56 (18)
C4—O4—C10—C91.5 (4)O8—S1—C1—C659.2 (2)
C4—O4—C10—C11178.2 (2)O10—S1—C1—C661.3 (2)
C16—C11—C10—C9179.9 (3)C7—O7—C6—C59.6 (4)
C12—C11—C10—C91.3 (4)C7—O7—C6—C1169.3 (2)
C16—C11—C10—O40.2 (3)C2—C1—C6—O7178.1 (2)
C12—C11—C10—O4178.4 (2)S1—C1—C6—O70.7 (3)
O4—C10—C9—C81.1 (4)C2—C1—C6—C50.8 (4)
C11—C10—C9—C8178.6 (3)S1—C1—C6—C5179.6 (2)
C10—C9—C8—O5179.2 (3)O7—C6—C5—C4176.7 (2)
C10—C9—C8—C30.8 (4)C1—C6—C5—C42.1 (4)
O5—C8—C3—C4177.7 (3)C10—O4—C4—C30.0 (3)
C9—C8—C3—C42.2 (4)C10—O4—C4—C5179.4 (2)
O5—C8—C3—C21.4 (4)C2—C3—C4—O4178.9 (2)
C9—C8—C3—C2178.6 (2)C8—C3—C4—O41.9 (4)
C4—C3—C2—O6178.1 (2)C2—C3—C4—C51.7 (4)
C8—C3—C2—O62.7 (4)C8—C3—C4—C5177.4 (2)
C4—C3—C2—C13.0 (4)C6—C5—C4—O4178.6 (2)
C8—C3—C2—C1176.2 (2)C6—C5—C4—C30.8 (4)
Symmetry code: (i) x, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O120.82 (3)1.97 (3)2.765 (3)164 (3)
O1—H1C···O8ii0.81 (2)2.00 (3)2.801 (3)172 (3)
O2—H2B···O12ii0.81 (3)1.94 (3)2.751 (3)173 (4)
O2—H2C···O100.82 (2)2.10 (3)2.894 (3)164 (3)
O3—H3B···O90.83 (3)1.98 (3)2.793 (3)165 (4)
O3—H3C···O110.82 (2)1.93 (2)2.744 (3)168 (3)
O6—H6···O50.821.802.549 (3)151
O11—H11B···O10iii0.82 (4)2.19 (4)2.976 (3)160 (4)
O11—H11C···O8iv0.83 (3)2.10 (3)2.912 (3)166 (4)
O12—H12B···O90.82 (3)2.02 (3)2.837 (3)169 (4)
O12—H12C···O10iii0.82 (3)2.02 (2)2.789 (3)158 (3)
C7—H7C···O6v0.962.523.430 (3)159
C9—H9···O5vi0.932.483.340 (3)154
C12—H12···O5vi0.932.543.429 (4)159
Symmetry codes: (ii) x, y+1, z+2; (iii) x1, y, z; (iv) x1, y+1, z; (v) x+1, y, z; (vi) x, y+2, z+1.

Experimental details

Crystal data
Chemical formula[Co(H2O)6](C16H11O7S)2·4H2O
Mr933.71
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)6.978 (2), 7.2034 (2), 20.145 (1)
α, β, γ (°)83.970 (2), 89.286 (3), 83.597 (2)
V3)1000.7 (3)
Z1
Radiation typeMo Kα
µ (mm1)0.62
Crystal size (mm)0.34 × 0.25 × 0.14
Data collection
DiffractometerCCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.814, 0.915
No. of measured, independent and
observed [I > 2σ(I)] reflections
5062, 3500, 2949
Rint0.013
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.131, 1.04
No. of reflections3500
No. of parameters311
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.41

Computer programs: SMART (Bruker, 1999), SAINT or SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O120.82 (3)1.97 (3)2.765 (3)164 (3)
O1—H1C···O8i0.81 (2)2.00 (3)2.801 (3)172 (3)
O2—H2B···O12i0.81 (3)1.94 (3)2.751 (3)173 (4)
O2—H2C···O100.82 (2)2.10 (3)2.894 (3)164 (3)
O3—H3B···O90.83 (3)1.98 (3)2.793 (3)165 (4)
O3—H3C···O110.82 (2)1.93 (2)2.744 (3)168 (3)
O6—H6···O50.821.802.549 (3)151
O11—H11B···O10ii0.82 (4)2.19 (4)2.976 (3)160 (4)
O11—H11C···O8iii0.83 (3)2.10 (3)2.912 (3)166 (4)
O12—H12B···O90.82 (3)2.02 (3)2.837 (3)169 (4)
O12—H12C···O10ii0.82 (3)2.02 (2)2.789 (3)158 (3)
C7—H7C···O6iv0.962.523.430 (3)159
C9—H9···O5v0.932.483.340 (3)154
C12—H12···O5v0.932.543.429 (4)159
Symmetry codes: (i) x, y+1, z+2; (ii) x1, y, z; (iii) x1, y+1, z; (iv) x+1, y, z; (v) x, y+2, z+1.
 

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