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Acta Cryst. (2007). E63, m2260-m2261    [ doi:10.1107/S160053680703694X ]

Hexaaquacobalt(II) 3-ammonionaphthalene-1,5-disulfonate tetrahydrate

D. J. Genther, P. J. Squattrito, K. Kirschbaum and A. A. Pinkerton

Abstract top

The title compound, [Co(H2O)6][H3NC10H5(SO3)2]2·4H2O, is part of an isostructural family that includes the nickel(II) and zinc(II) analogues. The salts contain centrosymmetric hexaaquametal cations and protonated ammonionaphthalenedisulfonate anions arranged in alternating layers. The anions stack so that the charged groups face the cationic layers, maximizing electrostatic interactions. The non-coordinated water molecules are located in the cation layers. An extensive network of strong near-linear N-H...O and O-H...O hydrogen bonds involving the ammonio group, water molecules and sulfonate O atoms further anchors the packing. One of the uncoordinated water molecules is disordered over at least two sites (modelled over two positions with almost equal site occupancies).

Comment top

Metal sulfonate salts have been actively studied in recent years as part of the growing field of mixed inorganic-organic structures of interest in crystal engineering. Key results have been summarized in two recent reviews (Cote & Shimizu, 2003; Cai, 2004).

We have characterized a variety of naphthalenesulfonate salts of main group and transition metals (Gunderman & Squattrito, 1995; Gunderman, Kabell et al., 1997; Morris et al., 2003; Downer et al., 2006) with the goal of discerning structural trends as functions of metal cation and substitution of the sulfonate group. As part of our continuing interest in this chemistry, we have synthesized a series of salts of 3-aminonaphthalene-1,5-sulfonate with divalent transition metals.

The result is a family of isostructural salts of formula [M(H2O)6](H3NC10H5(SO3)2)2·4H2O where M = Co, Ni & Zn. The title cobalt compound consists of hexaaquacobalt(II) cations, 3-ammonionaphthalene-1,5-disulfonate anions, and water molecules of crystallization (Fig. 1). Owing to the protonation of the amine group, each anion carries a single negative charge and the salt has the same 1:2 stoichiometry as would be observed with a monosulfonate anion. The cations reside on centers of inversion and display very regular octahedral geometry with maximum deviation from ideal 90° bond angles of just under 5°. This feature is very similar to what is found in other cobalt sulfonates (Gunderman, Dubey & Squattrito, 1997; Leonard et al., 1999).

The crystal packing (Fig. 2) is typical for transition metal arene- and naphthalenesulfonates (Chen et al., 2002; Gunderman, Dubey & Squattrito, 1997), consisting of alternating layers of hexaaquametal cations and sulfonate anions parallel to the ac plane, with the anions positioned so that the charged groups (i.e., NH3+ and SO3_) line the surface of the layer. The anions are positioned so that all the rings are parallel with contacts between adjacent rings of ca 3.7 Å. Neighboring rows of anions running along the a axis have the ammonio groups inverted. The water molecules of crystallization are located in between the cations in close association with the charged groups and coordinated water molecules so as to participate in hydrogen bonding interactions. One of the two crystallographically independent water molecules is disordered over at least two positions.

The layers are held together by a series of strong O—H···O and N—H···O hydrogen bonds involving water and ammonio donors and sulfonate and water acceptors (Table 2).

Related literature top

The title compound is isostructural with its nickel(II) (Gunderman, Kabell et al., 1997) and zinc(II) (Genther et al., 2007) analogues. For background, see: Cote & Shimizu (2003); Cai (2004); Gunderman & Squattrito (1995); Morris et al. (2003); Downer et al. (2006); Gunderman, Dubey & Squattrito (1997); Leonard et al. (1999). For related literature, see: Chen et al. (2002).

Experimental top

The title compound was prepared by direct reaction of Co(NO3)2·6H2O and disodium 3-aminonaphthalene-1,5-disulfonate (1:2 stoichiometry) in aqueous solution. Following approximately one hour of heating, during which most of the reactants dissolved, the resulting solution was gravity filtered and set out in open air. Upon evaporation of the water, many small reddish, needles of (I) were recovered.

Refinement top

The O11 atom, corresponding to one water of crystallization, was found to be disordered and was refined on split positions ca 0.5 Å apart with occupancy factors constrained to sum to 1. Final occupancies were roughly 53% (O11A) and 47% (O11B). The B site has a significantly prolate displacement ellipsoid, but further splitting of the position could not be successfully modeled. The H atoms attached to the disordered water molecule could not be located. All other H atoms were located in difference maps and positionally refined either freely or with distance restraints of O—H = 0.82 (2) Å, and with Uiso(H) = 1.2Ueq(N,C) or Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. Symmetry-equivalent water molecules (marked 'i') are included to show the full coordination sphere of the cobalt cation. [symmetry operation (i): −x, −y, −z]
[Figure 2] Fig. 2. The packing of (I), viewed down the a axis, showing layers connected by O—H···O and N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted.
hexaaquacobalt(II) 3-ammonionahthalene-1,5-disulfonate tetrahydrate top
Crystal data top
[Co(H2O1)6](C10H8NO6S2)2·4H2OZ = 1
Mr = 843.68F000 = 437
Triclinic, P1Dx = 1.758 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 5.45490 (10) ÅCell parameters from 6586 reflections
b = 12.7528 (3) Åθ = 3.0–34.4º
c = 12.9382 (3) ŵ = 0.90 mm−1
α = 114.646 (1)ºT = 140 (2) K
β = 101.477 (1)ºTriangular prism, red
γ = 90.919 (1)º0.25 × 0.22 × 0.10 mm
V = 796.73 (3) Å3
Data collection top
Bruker SMART 6000 CCD area-detector
diffractometer		6574 independent reflections
Radiation source: fine-focus sealed tube6288 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.016
T = 140(2) Kθmax = 35.6º
ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −8→8
Tmin = 0.765, Tmax = 0.910k = −20→20
11827 measured reflectionsl = −20→21
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.098  w = 1/[σ2(Fo2) + (0.0405P)2 + 0.5867P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
6574 reflectionsΔρmax = 1.10 e Å−3
281 parametersΔρmin = −0.82 e Å−3
8 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Co(H2O1)6](C10H8NO6S2)2·4H2Oγ = 90.919 (1)º
Mr = 843.68V = 796.73 (3) Å3
Triclinic, P1Z = 1
a = 5.45490 (10) ÅMo Kα
b = 12.7528 (3) ŵ = 0.90 mm−1
c = 12.9382 (3) ÅT = 140 (2) K
α = 114.646 (1)º0.25 × 0.22 × 0.10 mm
β = 101.477 (1)º
Data collection top
Bruker SMART 6000 CCD area-detector
diffractometer		6574 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		6288 reflections with I > 2σ(I)
Tmin = 0.765, Tmax = 0.910Rint = 0.016
11827 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0358 restraints
wR(F2) = 0.098H atoms treated by a mixture of
independent and constrained refinement
S = 1.07Δρmax = 1.10 e Å−3
6574 reflectionsΔρmin = −0.82 e Å−3
281 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 > 2sigma(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)
Co10.00000.00000.00000.01194 (5)
O7−0.26578 (18)−0.12241 (8)−0.00331 (8)0.01604 (16)
H9−0.347 (4)−0.1672 (18)−0.0681 (15)0.024*
H10−0.224 (4)−0.1529 (19)0.0394 (18)0.024*
O8−0.05274 (19)0.10605 (9)0.16887 (9)0.01862 (17)
H11−0.168 (4)0.1482 (18)0.178 (2)0.028*
H120.070 (4)0.1440 (19)0.2203 (18)0.028*
O90.30321 (19)−0.05179 (10)0.08400 (10)0.02177 (19)
H130.435 (4)−0.064 (2)0.061 (2)0.033*
H140.283 (5)−0.088 (2)0.121 (2)0.033*
S10.53450 (5)0.32370 (2)0.32171 (2)0.01216 (6)
O10.57766 (18)0.25223 (8)0.20469 (8)0.01694 (16)
O20.30255 (18)0.28088 (8)0.33761 (9)0.01758 (16)
O30.75299 (19)0.33977 (8)0.41332 (9)0.01965 (18)
S20.02330 (6)0.76432 (3)0.20505 (3)0.01597 (6)
O40.2482 (2)0.80285 (11)0.18029 (11)0.0254 (2)
O5−0.2059 (2)0.75551 (10)0.12117 (10)0.0231 (2)
O60.0067 (2)0.83554 (9)0.32609 (9)0.02269 (19)
N10.8711 (2)0.75479 (10)0.47987 (10)0.01682 (18)
H60.947 (4)0.7786 (19)0.4385 (19)0.020*
H70.971 (4)0.7319 (19)0.5194 (19)0.020*
H80.816 (4)0.808 (2)0.523 (2)0.020*
C10.4958 (2)0.46391 (9)0.32593 (10)0.01224 (17)
C20.6852 (2)0.55077 (10)0.39846 (10)0.01341 (18)
H10.825 (4)0.5357 (18)0.4432 (18)0.016*
C30.6687 (2)0.66256 (10)0.40344 (10)0.01317 (18)
C40.4698 (2)0.68835 (10)0.33892 (10)0.01455 (19)
H20.455 (4)0.7608 (18)0.3429 (18)0.017*
C50.0561 (2)0.62243 (10)0.19476 (10)0.01454 (19)
C6−0.1328 (2)0.53561 (11)0.12103 (11)0.0175 (2)
H3−0.262 (4)0.5579 (19)0.0848 (19)0.021*
C7−0.1188 (2)0.42229 (11)0.11258 (12)0.0181 (2)
H4−0.263 (4)0.3552 (19)0.0557 (19)0.022*
C80.0825 (2)0.39777 (10)0.17861 (11)0.01547 (19)
H50.086 (4)0.3219 (19)0.1696 (19)0.019*
C90.2820 (2)0.48519 (10)0.25561 (10)0.01230 (17)
C100.2705 (2)0.60020 (10)0.26370 (10)0.01281 (17)
O10−0.2264 (4)0.04228 (14)0.34619 (16)0.0478 (4)
H15−0.173 (7)−0.028 (2)0.342 (3)0.072*
H16−0.244 (7)0.043 (3)0.274 (2)0.072*
O11A0.5969 (16)0.9484 (5)0.5775 (6)0.087 (3)0.526 (16)
O11B0.6756 (17)0.9458 (5)0.5908 (11)0.109 (4)0.474 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.01256 (9)0.01138 (9)0.01237 (10)0.00226 (7)0.00272 (7)0.00557 (8)
O70.0172 (4)0.0157 (4)0.0156 (4)−0.0004 (3)0.0007 (3)0.0084 (3)
O80.0165 (4)0.0186 (4)0.0162 (4)0.0040 (3)0.0024 (3)0.0036 (3)
O90.0180 (4)0.0309 (5)0.0297 (5)0.0095 (4)0.0095 (4)0.0236 (4)
S10.01264 (11)0.00967 (11)0.01284 (12)0.00055 (8)0.00019 (8)0.00475 (9)
O10.0182 (4)0.0134 (4)0.0163 (4)0.0037 (3)0.0043 (3)0.0034 (3)
O20.0171 (4)0.0168 (4)0.0192 (4)−0.0025 (3)0.0030 (3)0.0087 (3)
O30.0184 (4)0.0162 (4)0.0214 (4)−0.0005 (3)−0.0059 (3)0.0100 (4)
S20.01772 (13)0.01645 (13)0.01914 (13)0.00369 (9)0.00455 (10)0.01259 (11)
O40.0209 (4)0.0322 (5)0.0375 (6)0.0037 (4)0.0091 (4)0.0275 (5)
O50.0209 (4)0.0261 (5)0.0286 (5)0.0057 (4)0.0015 (4)0.0194 (4)
O60.0349 (5)0.0148 (4)0.0217 (5)0.0050 (4)0.0090 (4)0.0098 (4)
N10.0210 (5)0.0127 (4)0.0141 (4)−0.0036 (3)−0.0023 (3)0.0061 (4)
C10.0135 (4)0.0102 (4)0.0121 (4)0.0010 (3)0.0017 (3)0.0045 (4)
C20.0147 (4)0.0112 (4)0.0128 (4)−0.0004 (3)−0.0001 (3)0.0053 (4)
C30.0157 (4)0.0106 (4)0.0113 (4)−0.0016 (3)0.0002 (3)0.0041 (4)
C40.0178 (5)0.0117 (4)0.0141 (5)0.0005 (3)0.0014 (4)0.0064 (4)
C50.0154 (4)0.0146 (5)0.0150 (5)0.0030 (4)0.0023 (4)0.0082 (4)
C60.0161 (5)0.0184 (5)0.0180 (5)0.0017 (4)−0.0003 (4)0.0097 (4)
C70.0158 (5)0.0168 (5)0.0190 (5)−0.0006 (4)−0.0015 (4)0.0075 (4)
C80.0153 (5)0.0124 (4)0.0164 (5)0.0005 (3)−0.0001 (4)0.0057 (4)
C90.0128 (4)0.0110 (4)0.0122 (4)0.0013 (3)0.0015 (3)0.0047 (4)
C100.0146 (4)0.0118 (4)0.0120 (4)0.0015 (3)0.0016 (3)0.0057 (4)
O100.0634 (11)0.0327 (7)0.0484 (9)0.0123 (7)0.0125 (8)0.0185 (7)
O11A0.098 (4)0.043 (2)0.062 (3)0.033 (3)−0.037 (3)−0.010 (2)
O11B0.079 (4)0.0177 (17)0.199 (9)−0.010 (2)0.106 (5)−0.015 (3)
Geometric parameters (Å, °) top
Co1—O9i2.0667 (10)N1—H60.88 (2)
Co1—O92.0667 (10)N1—H70.82 (2)
Co1—O7i2.0946 (9)N1—H80.79 (2)
Co1—O72.0946 (9)C1—C21.3735 (16)
Co1—O8i2.1175 (10)C1—C91.4334 (16)
Co1—O82.1175 (10)C2—C31.4052 (16)
O7—H90.818 (16)C2—H10.94 (2)
O7—H100.800 (15)C3—C41.3644 (16)
O8—H110.830 (16)C4—C101.4214 (16)
O8—H120.819 (16)C4—H20.91 (2)
O9—H130.826 (16)C5—C61.3747 (18)
O9—H140.818 (16)C5—C101.4317 (16)
S1—O31.4474 (10)C6—C71.4076 (18)
S1—O21.4548 (10)C6—H30.88 (2)
S1—O11.4752 (10)C7—C81.3762 (17)
S1—C11.7833 (11)C7—H41.06 (2)
S2—O51.4515 (11)C8—C91.4224 (16)
S2—O41.4553 (11)C8—H50.93 (2)
S2—O61.4691 (11)C9—C101.4296 (16)
S2—C51.7730 (12)O10—H150.925 (18)
N1—C31.4610 (16)O10—H160.924 (18)
O9i—Co1—O9180.0C3—N1—H7110.2 (15)
O9i—Co1—O7i94.83 (4)H6—N1—H7111 (2)
O9—Co1—O7i85.17 (4)C3—N1—H8110.2 (16)
O9i—Co1—O785.17 (4)H6—N1—H8108 (2)
O9—Co1—O794.83 (4)H7—N1—H8108 (2)
O7i—Co1—O7180.0C2—C1—C9121.31 (10)
O9i—Co1—O8i86.09 (4)C2—C1—S1116.45 (8)
O9—Co1—O8i93.91 (4)C9—C1—S1122.22 (8)
O7i—Co1—O8i85.98 (4)C1—C2—C3119.16 (10)
O7—Co1—O8i94.02 (4)C1—C2—H1120.6 (13)
O9i—Co1—O893.91 (4)C3—C2—H1120.2 (13)
O9—Co1—O886.09 (4)C4—C3—C2122.30 (10)
O7i—Co1—O894.02 (4)C4—C3—N1118.50 (10)
O7—Co1—O885.98 (4)C2—C3—N1119.20 (10)
O8i—Co1—O8180.0C3—C4—C10119.66 (10)
Co1—O7—H9115.7 (16)C3—C4—H2123.1 (13)
Co1—O7—H10117.1 (16)C10—C4—H2117.2 (13)
H9—O7—H10113 (2)C6—C5—C10121.30 (11)
Co1—O8—H11121.2 (17)C6—C5—S2118.00 (9)
Co1—O8—H12118.7 (17)C10—C5—S2120.67 (9)
H11—O8—H12106 (2)C5—C6—C7120.07 (11)
Co1—O9—H13122.3 (17)C5—C6—H3115.2 (14)
Co1—O9—H14120.9 (18)C7—C6—H3124.6 (14)
H13—O9—H14112 (2)C8—C7—C6120.39 (11)
O3—S1—O2114.09 (6)C8—C7—H4119.2 (12)
O3—S1—O1112.03 (6)C6—C7—H4120.4 (12)
O2—S1—O1111.47 (6)C7—C8—C9121.18 (11)
O3—S1—C1105.87 (5)C7—C8—H5117.7 (13)
O2—S1—C1107.54 (6)C9—C8—H5121.1 (13)
O1—S1—C1105.17 (5)C8—C9—C10118.76 (10)
O5—S2—O4113.34 (6)C8—C9—C1123.26 (10)
O5—S2—O6112.50 (7)C10—C9—C1117.97 (10)
O4—S2—O6111.14 (7)C4—C10—C9119.59 (10)
O5—S2—C5106.52 (6)C4—C10—C5122.13 (10)
O4—S2—C5107.20 (6)C9—C10—C5118.29 (10)
O6—S2—C5105.57 (6)H15—O10—H16109 (3)
C3—N1—H6110.3 (14)
O3—S1—C1—C28.14 (11)S2—C5—C6—C7−178.09 (10)
O2—S1—C1—C2130.48 (9)C5—C6—C7—C80.6 (2)
O1—S1—C1—C2−110.61 (10)C6—C7—C8—C9−0.8 (2)
O3—S1—C1—C9−173.34 (10)C7—C8—C9—C100.05 (18)
O2—S1—C1—C9−51.01 (11)C7—C8—C9—C1−179.85 (12)
O1—S1—C1—C967.90 (10)C2—C1—C9—C8179.47 (12)
C9—C1—C2—C3−0.10 (17)S1—C1—C9—C81.02 (16)
S1—C1—C2—C3178.43 (9)C2—C1—C9—C10−0.43 (17)
C1—C2—C3—C40.27 (18)S1—C1—C9—C10−178.88 (9)
C1—C2—C3—N1−179.52 (11)C3—C4—C10—C9−0.65 (18)
C2—C3—C4—C100.11 (18)C3—C4—C10—C5179.42 (11)
N1—C3—C4—C10179.90 (11)C8—C9—C10—C4−179.11 (11)
O5—S2—C5—C6−3.92 (12)C1—C9—C10—C40.80 (17)
O4—S2—C5—C6−125.54 (11)C8—C9—C10—C50.82 (17)
O6—S2—C5—C6115.89 (11)C1—C9—C10—C5−179.27 (10)
O5—S2—C5—C10177.64 (10)C6—C5—C10—C4178.90 (12)
O4—S2—C5—C1056.02 (11)S2—C5—C10—C4−2.71 (16)
O6—S2—C5—C10−62.55 (11)C6—C5—C10—C9−1.03 (18)
C10—C5—C6—C70.34 (19)S2—C5—C10—C9177.36 (9)
Symmetry codes: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H9···O1i0.818 (16)1.832 (16)2.6404 (13)169 (2)
O7—H10···O5ii0.800 (15)1.867 (16)2.6501 (13)166 (2)
O8—H11···O1iii0.830 (16)1.915 (16)2.7435 (13)177 (2)
O8—H12···O20.819 (16)1.977 (17)2.7589 (14)159 (2)
O9—H13···O7iv0.826 (16)1.993 (17)2.8092 (14)170 (2)
O9—H14···O4ii0.818 (16)1.865 (17)2.6713 (14)168 (3)
N1—H6···O6iv0.88 (2)1.95 (2)2.7993 (15)162 (2)
N1—H7···O3v0.82 (2)2.01 (2)2.8124 (15)168 (2)
N1—H8···O11A0.79 (2)2.12 (2)2.863 (7)159 (2)
O10—H15···O6ii0.925 (18)1.97 (2)2.8816 (19)167 (3)
O10—H16···O80.924 (18)2.25 (3)3.036 (2)143 (3)
Symmetry codes: (i) −x, −y, −z; (ii) x, y−1, z; (iii) x−1, y, z; (iv) x+1, y, z; (v) −x+2, −y+1, −z+1.
Selected geometric parameters (Å) top
Co1—O92.0667 (10)Co1—O82.1175 (10)
Co1—O72.0946 (9)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H9···O1i0.818 (16)1.832 (16)2.6404 (13)169 (2)
O7—H10···O5ii0.800 (15)1.867 (16)2.6501 (13)166 (2)
O8—H11···O1iii0.830 (16)1.915 (16)2.7435 (13)177 (2)
O8—H12···O20.819 (16)1.977 (17)2.7589 (14)159 (2)
O9—H13···O7iv0.826 (16)1.993 (17)2.8092 (14)170 (2)
O9—H14···O4ii0.818 (16)1.865 (17)2.6713 (14)168 (3)
N1—H6···O6iv0.88 (2)1.95 (2)2.7993 (15)162 (2)
N1—H7···O3v0.82 (2)2.01 (2)2.8124 (15)168 (2)
N1—H8···O11A0.79 (2)2.12 (2)2.863 (7)159 (2)
O10—H15···O6ii0.925 (18)1.97 (2)2.8816 (19)167 (3)
O10—H16···O80.924 (18)2.25 (3)3.036 (2)143 (3)
Symmetry codes: (i) −x, −y, −z; (ii) x, y−1, z; (iii) x−1, y, z; (iv) x+1, y, z; (v) −x+2, −y+1, −z+1.
Acknowledgements top

Funding from the Office of Naval Research (grant No. N00014–97-1–0409) to purchase the CCD detector at the University of Toledo is gratefully acknowledged.

references
References top

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