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Acta Cryst. (2007). E63, m1664    [ doi:10.1107/S160053680702274X ]

Hexaaquamagnesium(II) bis[4-(2-hydroxybenzylideneamino)benzenesulfonate]

L.-H. Wang, J. Yin and X.-S. Tai

Abstract top

In the crystal structure of the title compound, [Mg(H2O)6](C13H10NO4S)2, the packing is stabilized by Owater-H...Oanion hydrogen bonds. An intramolecular O-H...N bond occurs in the anion. The Mg atom has site symmetry \overline{1}.

Comment top

As part of our ongoing studies of the coordination chemistry of Schiff base ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1). Here, however, the ligand is not coordinated to the metal, but instead, a molecular salt arises.

In the crystal of (I), the Mg(II) center (site symmetry 1) is six-coordinate to water molecules. The C7—N1 distance [1.251 (5) Å] in the anion is close to a double-bond value. Otherwise, the geometrical parameters for (I) are normal. The dihedral angle between the two benzene ring is 32.6 (2)°, indicating that the molecule is non-planar, which perhaps correlates with the intramolecular hydrogen bond (Table 1).

Related literature top

For related literature: see Tai et al. (2003).

Experimental top

1 mmol of magnesium perchlorate was added to a solution of salicylaldehyde-4-aminobenzene sulfonic acid (1 mmol) in 10 ml of 95% ethanol. The mixture was stirred for 3 h at refluxing temperature. Evaporating some ethanol, clear blocks of (I) were obtained after two weeks.

Refinement top

The O-bound H atoms were located in difference maps and refined as riding in their as-found relative positions with Uiso(H) = 1.2Ueq(O).

The other H atoms were placed geometrically (C—H = 0.93–0.96 Å, and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids (arbitrary spheres for the H atoms). Atoms with the suffix A are generated by the symmetry operator (2 - x, -y, -z).
Hexaaquamagnesium(II) bis[4-(2-hydroxybenzylideneamino)benzenesulfonate] top
Crystal data top
[Mg(H2O)6](C13H10NO4S)2F(000) = 716
Mr = 684.97Dx = 1.470 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3237 reflections
a = 6.2997 (17) Åθ = 2.3–26.9°
b = 35.313 (9) ŵ = 0.26 mm−1
c = 6.9561 (19) ÅT = 291 K
β = 90.75 (1)°Block, brown
V = 1547.3 (7) Å30.30 × 0.24 × 0.22 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer		3041 independent reflections
Radiation source: sealed tube2173 reflections with I > 2σ(I)
graphiteRint = 0.044
phi and ω scansθmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −7→7
Tmin = 0.93, Tmax = 0.94k = −22→43
8390 measured reflectionsl = −8→8
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0657P)2 + 0.77P]
where P = (Fo2 + 2Fc2)/3
3041 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
[Mg(H2O)6](C13H10NO4S)2V = 1547.3 (7) Å3
Mr = 684.97Z = 2
Monoclinic, P21/nMo Kα radiation
a = 6.2997 (17) ŵ = 0.26 mm−1
b = 35.313 (9) ÅT = 291 K
c = 6.9561 (19) Å0.30 × 0.24 × 0.22 mm
β = 90.75 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		3041 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2173 reflections with I > 2σ(I)
Tmin = 0.93, Tmax = 0.94Rint = 0.044
8390 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.146Δρmax = 0.25 e Å−3
S = 1.00Δρmin = −0.46 e Å−3
3041 reflectionsAbsolute structure: ?
205 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
C10.5147 (7)0.29797 (12)0.5190 (6)0.0540 (10)
C20.6701 (8)0.32508 (13)0.5548 (6)0.0647 (12)
H20.80640.31730.58930.078*
C30.6272 (9)0.36279 (14)0.5404 (7)0.0724 (13)
H30.73260.38060.56630.087*
C40.4255 (9)0.37428 (13)0.4871 (7)0.0712 (14)
H40.39570.40000.47480.085*
C50.2695 (9)0.34828 (14)0.4524 (6)0.0696 (13)
H50.13440.35640.41580.083*
C60.3106 (8)0.31045 (12)0.4710 (6)0.0575 (11)
C70.5634 (7)0.25773 (12)0.5315 (5)0.0532 (10)
H70.70200.25060.56140.064*
C80.4826 (6)0.19365 (11)0.5055 (5)0.0466 (9)
C90.3252 (6)0.16787 (12)0.5564 (6)0.0556 (10)
H90.19140.17650.59010.067*
C100.3670 (6)0.13009 (12)0.5569 (6)0.0495 (9)
H100.26220.11300.59250.059*
C110.5665 (5)0.11689 (10)0.5043 (4)0.0349 (7)
C120.7255 (6)0.14225 (11)0.4507 (5)0.0455 (9)
H120.85880.13360.41550.055*
C130.6805 (6)0.18019 (12)0.4514 (6)0.0525 (10)
H130.78450.19730.41480.063*
Mg11.00000.00000.00000.0385 (4)
N10.4280 (5)0.23230 (10)0.5038 (5)0.0536 (8)
O10.1544 (5)0.28509 (10)0.4396 (5)0.0771 (10)
H1C0.21190.26350.45410.092*
O20.8439 (3)0.06285 (7)0.4953 (3)0.0406 (6)
O30.5166 (4)0.05345 (7)0.3242 (3)0.0465 (6)
O40.5167 (4)0.05225 (7)0.6716 (3)0.0452 (6)
O50.7139 (3)0.02654 (7)−0.0016 (3)0.0421 (6)
H5A0.71440.0460−0.09810.063*
H5B0.68870.03770.12210.063*
O61.1087 (4)0.03733 (8)0.2055 (4)0.0536 (7)
H6B1.21110.02470.28520.080*
H6C0.99180.04570.28320.080*
O70.8927 (4)−0.03449 (8)0.2191 (4)0.0519 (7)
H7B0.7912−0.02090.29560.078*
H7C1.0104−0.04190.29830.078*
S10.61427 (12)0.06773 (2)0.49840 (11)0.0325 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.067 (3)0.050 (2)0.046 (2)0.0107 (19)0.0090 (19)0.0048 (17)
C20.070 (3)0.053 (3)0.071 (3)0.002 (2)0.002 (2)0.005 (2)
C30.086 (4)0.057 (3)0.075 (3)−0.008 (3)0.014 (3)0.003 (2)
C40.107 (4)0.044 (2)0.063 (3)0.018 (3)0.012 (3)0.002 (2)
C50.098 (4)0.059 (3)0.052 (3)0.028 (3)−0.008 (2)0.010 (2)
C60.072 (3)0.052 (2)0.048 (2)0.003 (2)−0.004 (2)0.0087 (18)
C70.057 (3)0.052 (2)0.050 (2)0.015 (2)−0.0015 (18)0.0063 (18)
C80.049 (2)0.041 (2)0.049 (2)0.0062 (17)−0.0054 (16)0.0030 (16)
C90.036 (2)0.059 (3)0.072 (3)0.0088 (18)0.0053 (18)−0.002 (2)
C100.0361 (19)0.053 (2)0.059 (2)0.0043 (17)0.0096 (16)−0.0018 (18)
C110.0269 (16)0.0469 (19)0.0309 (15)−0.0006 (13)−0.0022 (12)0.0033 (14)
C120.0388 (19)0.047 (2)0.051 (2)0.0036 (16)0.0147 (16)0.0013 (16)
C130.051 (2)0.049 (2)0.058 (2)−0.0100 (18)0.0121 (18)−0.0013 (18)
Mg10.0372 (9)0.0385 (9)0.0398 (9)−0.0013 (7)−0.0019 (6)−0.0002 (7)
N10.057 (2)0.052 (2)0.0507 (19)0.0073 (17)−0.0018 (15)0.0017 (15)
O10.069 (2)0.066 (2)0.096 (3)0.0148 (17)−0.0236 (18)0.0034 (17)
O20.0178 (10)0.0545 (15)0.0494 (13)0.0060 (9)−0.0004 (9)−0.0018 (11)
O30.0340 (12)0.0584 (16)0.0470 (14)0.0014 (11)−0.0062 (10)−0.0143 (12)
O40.0306 (12)0.0580 (16)0.0471 (14)0.0023 (11)0.0035 (10)0.0138 (12)
O50.0310 (12)0.0564 (15)0.0388 (12)0.0093 (11)0.0012 (9)−0.0032 (11)
O60.0300 (13)0.077 (2)0.0534 (16)0.0003 (12)−0.0036 (11)−0.0246 (14)
O70.0286 (12)0.0743 (19)0.0528 (15)−0.0006 (11)0.0012 (10)0.0264 (13)
S10.0202 (4)0.0428 (5)0.0345 (4)0.0020 (3)−0.0012 (3)−0.0007 (3)
Geometric parameters (Å, °) top
C1—C21.389 (6)C11—C121.398 (5)
C1—C61.396 (6)C11—S11.762 (4)
C1—C71.456 (6)C12—C131.369 (5)
C2—C31.362 (7)C12—H120.9300
C2—H20.9300C13—H130.9300
C3—C41.380 (7)Mg1—O52.031 (2)
C3—H30.9300Mg1—O5i2.031 (2)
C4—C51.364 (7)Mg1—O62.055 (2)
C4—H40.9300Mg1—O6i2.055 (2)
C5—C61.366 (6)Mg1—O7i2.071 (2)
C5—H50.9300Mg1—O72.071 (2)
C6—O11.346 (5)O1—H1C0.8500
C7—N11.251 (5)O2—S11.457 (2)
C7—H70.9300O3—S11.443 (2)
C8—C131.391 (5)O4—S11.465 (2)
C8—C91.395 (6)O5—H5A0.9599
C8—N11.408 (5)O5—H5B0.9618
C9—C101.360 (6)O6—H6B0.9551
C9—H90.9300O6—H6C0.9653
C10—C111.394 (5)O7—H7B0.9645
C10—H100.9300O7—H7C0.9544
C2—C1—C6118.0 (4)C12—C13—C8121.4 (4)
C2—C1—C7121.0 (4)C12—C13—H13119.3
C6—C1—C7121.0 (4)C8—C13—H13119.3
C3—C2—C1121.5 (5)O5—Mg1—O5i180.0
C3—C2—H2119.3O5—Mg1—O689.73 (10)
C1—C2—H2119.3O5i—Mg1—O690.27 (10)
C2—C3—C4119.2 (5)O5—Mg1—O6i90.27 (10)
C2—C3—H3120.4O5i—Mg1—O6i89.73 (10)
C4—C3—H3120.4O6—Mg1—O6i180.0
C5—C4—C3120.6 (4)O5—Mg1—O7i91.30 (10)
C5—C4—H4119.7O5i—Mg1—O7i88.70 (10)
C3—C4—H4119.7O6—Mg1—O7i91.47 (11)
C4—C5—C6120.4 (5)O6i—Mg1—O7i88.53 (11)
C4—C5—H5119.8O5—Mg1—O788.70 (10)
C6—C5—H5119.8O5i—Mg1—O791.30 (10)
O1—C6—C5119.9 (4)O6—Mg1—O788.53 (11)
O1—C6—C1119.9 (4)O6i—Mg1—O791.47 (11)
C5—C6—C1120.2 (5)O7i—Mg1—O7180.0
N1—C7—C1123.3 (4)C7—N1—C8121.9 (4)
N1—C7—H7118.4C6—O1—H1C105.6
C1—C7—H7118.4Mg1—O5—H5A108.8
C13—C8—C9119.2 (4)Mg1—O5—H5B110.0
C13—C8—N1123.3 (4)H5A—O5—H5B109.5
C9—C8—N1117.4 (4)Mg1—O6—H6B108.7
C10—C9—C8120.2 (4)Mg1—O6—H6C109.7
C10—C9—H9119.9H6B—O6—H6C109.4
C8—C9—H9119.9Mg1—O7—H7B109.8
C9—C10—C11120.2 (4)Mg1—O7—H7C109.1
C9—C10—H10119.9H7B—O7—H7C109.5
C11—C10—H10119.9O3—S1—O2111.04 (14)
C10—C11—C12120.5 (3)O3—S1—O4112.40 (15)
C10—C11—S1119.4 (3)O2—S1—O4113.27 (14)
C12—C11—S1120.1 (3)O3—S1—C11107.02 (15)
C13—C12—C11118.5 (3)O2—S1—C11106.65 (14)
C13—C12—H12120.8O4—S1—C11105.96 (15)
C11—C12—H12120.8
Symmetry codes: (i) −x+2, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N10.851.782.574 (5)154
O5—H5A···O4ii0.962.032.732 (3)129
O5—H5B···O30.961.872.768 (3)154
O6—H6B···O3iii0.962.192.749 (3)116
O6—H6C···O20.971.862.783 (3)160
O7—H7B···O4iv0.962.252.770 (3)113
O7—H7C···O2v0.951.852.760 (3)159
Symmetry codes: (ii) x, y, z−1; (iii) x+1, y, z; (iv) −x+1, −y, −z+1; (v) −x+2, −y, −z+1.
Table 1
Selected geometric parameters (Å) top
Mg1—O52.031 (2)Mg1—O72.071 (2)
Mg1—O62.055 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N10.851.782.574 (5)154
O5—H5A···O4i0.962.032.732 (3)129
O5—H5B···O30.961.872.768 (3)154
O6—H6B···O3ii0.962.192.749 (3)116
O6—H6C···O20.971.862.783 (3)160
O7—H7B···O4iii0.962.252.770 (3)113
O7—H7C···O2iv0.951.852.760 (3)159
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) −x+2, −y, −z+1.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (20671073), NingXia Natural Gas Transfering Key Laboratory (2004007), the Science and Technology Foundation of Weifang, and Weifang University for research grants.

references
References top

Bruker (2000). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Tai, X.-S., Yin, X.-H., Tan, M.-Y. & Li, Y.-Z. (2003). Acta Cryst. E59, o681–o682.