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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m422.
Published online 2010 March 20. doi:  10.1107/S1600536810009748
PMCID: PMC2983805

Hexaaqua­magnesium(II) bis­[4-(3-eth­oxy-2-hydroxy­benzyl­ideneamino)-3-methyl­benzene­sulfonate]

Abstract

In the title compound, [Mg(H2O)6](C16H16NO5S)2, the Mg2+ ion (site symmetry 2) adopts an almost regular octa­hedral coordination geometry. The anion is stabilized by an intra­molecular O—H(...)N hydrogen bond, generating an S(6) ring, and the dihedral angle between the aromatic rings is 41.02 (7)°. In the crystal, the cations and anions are linked by O—H(...)O hydrogen bonds, generating sheets lying parallel to (100).

Related literature

For background to the properties of Schiff bases, see: Qiu et al. (2008 [triangle]); Tai et al. (2003 [triangle]).

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Object name is e-66-0m422-scheme1.jpg

Experimental

Crystal data

  • [Mg(H2O)6](C16H16NO5S)
  • M r = 801.12
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m422-efi1.jpg
  • a = 38.710 (11) Å
  • b = 7.531 (2) Å
  • c = 13.087 (3) Å
  • β = 104.986 (4)°
  • V = 3685.6 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 293 K
  • 0.19 × 0.16 × 0.12 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.956, T max = 0.972
  • 9339 measured reflections
  • 3253 independent reflections
  • 2924 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.088
  • S = 1.07
  • 3253 reflections
  • 241 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.48 e Å−3

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009748/hb5354sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009748/hb5354Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors would like to thank the Natural Science Foundation of Shandong (Y2007B60) for a research grant.

supplementary crystallographic information

Comment

Schiff bases play an important role in the field of bioinorganic chemistry because they have remarkable wide biological and pharmacological activities, such as antitumor, antidiabetic, antitubercular activities [Tai, et al., 2003; Qiu, et al., 2008]. Therefore, investigating the synthesis and proper ties of hydrazone of these compounds seems to be a very interesting problem. as one part of our systematic work, In this paper, we report on the synthesis and crystal structure of the title compound, (I), (Scheme I).

The bond distances of Mg—O are in the range of 2.0510 (11)-2.0638 (12). The bond distances of C8—N1(1.282 (2)), S1—O2 (1.4588 (11)) and S1—O3 (1.4590 (11)) are consistent with the carbon-nitrogen and sulphur-oxygen double-bond lengths, respectively. In the crystal packing, the molecules form a one-dimensional chain structure by hydrogen bonds.

Experimental

A solution of 1.0 mmol 3-ethoxysalicylaldehyde was added to a solution of 1.0 mmol 4-amino-3-methyl-benzenesulfonic acid in 5 ml 95% ethanol at room temperature. The mixture was refluxed for 4 h with stirring, then the resulting precipitate was filtered, washed, and dried in vacuo over P4O10 for 48 h. Colourless blocks of (I) were obtained by slowly evaporating from methanol at room temperature.

Figures

Fig. 1.
The molecular structure of (I) showing 30% displacement ellipsoids.

Crystal data

[Mg(H2O)6](C16H16NO5S)F(000) = 1688
Mr = 801.12Dx = 1.444 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5727 reflections
a = 38.710 (11) Åθ = 3.1–28.3°
b = 7.531 (2) ŵ = 0.24 mm1
c = 13.087 (3) ÅT = 293 K
β = 104.986 (4)°Block, colourless
V = 3685.6 (17) Å30.19 × 0.16 × 0.12 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer3253 independent reflections
Radiation source: fine-focus sealed tube2924 reflections with I > 2σ(I)
graphiteRint = 0.024
ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −46→41
Tmin = 0.956, Tmax = 0.972k = −8→8
9339 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0466P)2 + 2.1281P] where P = (Fo2 + 2Fc2)/3
3253 reflections(Δ/σ)max < 0.001
241 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.48 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/Ueq
Mg10.00000.76200 (8)0.75000.02561 (17)
S10.053241 (9)0.73171 (5)0.12108 (3)0.02690 (12)
N10.21154 (3)0.64726 (18)0.21861 (10)0.0358 (3)
O10.03738 (3)0.57836 (14)0.05783 (8)0.0372 (3)
O20.04508 (3)0.89760 (14)0.06222 (8)0.0357 (3)
O30.04451 (3)0.73756 (14)0.22300 (8)0.0352 (3)
O40.27591 (3)0.69109 (17)0.34589 (8)0.0414 (3)
H40.25400.68760.32930.062*
O50.34554 (3)0.68788 (17)0.37345 (9)0.0426 (3)
O6−0.03010 (3)0.76330 (14)0.85798 (9)0.0404 (3)
H15−0.03330.85680.89080.061*
H16−0.03200.67140.89380.061*
O7−0.03189 (3)0.56722 (15)0.66233 (8)0.0409 (3)
H17−0.03290.55090.59740.061*
H18−0.03530.46620.68700.061*
O8−0.03191 (3)0.95651 (15)0.66277 (8)0.0458 (3)
H19−0.03681.05460.68800.069*
H20−0.03590.96800.59610.069*
C10.10021 (4)0.70263 (19)0.14849 (11)0.0280 (3)
C20.11930 (4)0.63608 (19)0.24591 (11)0.0309 (3)
H20.10710.60550.29600.037*
C30.15615 (4)0.6144 (2)0.26994 (11)0.0320 (3)
C40.17378 (4)0.6597 (2)0.19257 (12)0.0318 (3)
C50.15439 (4)0.7242 (2)0.09457 (12)0.0356 (4)
H50.16630.75360.04370.043*
C60.11778 (4)0.7452 (2)0.07202 (12)0.0340 (4)
H60.10510.78750.00630.041*
C70.17670 (4)0.5461 (2)0.37649 (12)0.0431 (4)
H7A0.19020.44320.36720.065*
H7B0.16030.51480.41740.065*
H7C0.19270.63670.41270.065*
C80.22688 (4)0.5956 (2)0.14795 (13)0.0380 (4)
H80.21270.56090.08230.046*
C90.26537 (4)0.5886 (2)0.16581 (12)0.0353 (3)
C100.28823 (4)0.6380 (2)0.26306 (12)0.0327 (3)
C110.32543 (4)0.6332 (2)0.27646 (12)0.0343 (3)
C120.33903 (4)0.5734 (2)0.19455 (13)0.0387 (4)
H120.36360.56980.20350.046*
C130.31630 (5)0.5186 (2)0.09917 (13)0.0417 (4)
H130.32580.47560.04550.050*
C140.27993 (5)0.5279 (2)0.08417 (13)0.0414 (4)
H140.26480.49390.01970.050*
C150.38322 (4)0.7012 (2)0.38726 (13)0.0384 (4)
H15A0.38850.78890.33920.046*
H15B0.39290.58780.37290.046*
C160.39945 (5)0.7556 (2)0.49975 (15)0.0470 (4)
H16A0.39080.87120.51180.070*
H16B0.42500.75900.51290.070*
H16C0.39290.67140.54660.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mg10.0316 (4)0.0244 (3)0.0216 (3)0.0000.0083 (3)0.000
S10.0321 (2)0.0256 (2)0.0227 (2)−0.00147 (13)0.00662 (15)−0.00049 (13)
N10.0347 (7)0.0373 (7)0.0357 (7)−0.0021 (6)0.0095 (6)−0.0026 (6)
O10.0446 (6)0.0337 (6)0.0315 (6)−0.0093 (5)0.0067 (5)−0.0049 (5)
O20.0427 (6)0.0314 (6)0.0324 (6)0.0033 (5)0.0087 (5)0.0052 (4)
O30.0422 (6)0.0378 (6)0.0285 (6)0.0008 (5)0.0143 (5)−0.0002 (4)
O40.0356 (6)0.0564 (7)0.0342 (6)0.0017 (6)0.0126 (5)−0.0072 (5)
O50.0323 (6)0.0569 (7)0.0391 (6)0.0010 (5)0.0098 (5)−0.0048 (6)
O60.0551 (7)0.0334 (6)0.0411 (7)0.0028 (5)0.0277 (6)0.0015 (5)
O70.0572 (7)0.0356 (6)0.0294 (5)−0.0140 (5)0.0103 (5)−0.0040 (5)
O80.0668 (8)0.0374 (6)0.0299 (6)0.0180 (6)0.0067 (5)0.0026 (5)
C10.0334 (8)0.0251 (7)0.0251 (7)−0.0015 (6)0.0066 (6)−0.0025 (6)
C20.0373 (8)0.0315 (8)0.0251 (7)−0.0013 (6)0.0099 (6)0.0006 (6)
C30.0380 (8)0.0291 (8)0.0274 (7)0.0004 (6)0.0059 (6)−0.0010 (6)
C40.0343 (8)0.0284 (8)0.0329 (8)−0.0009 (6)0.0088 (6)−0.0038 (6)
C50.0412 (9)0.0383 (9)0.0309 (8)0.0005 (7)0.0158 (7)0.0031 (6)
C60.0415 (9)0.0346 (8)0.0258 (8)0.0037 (6)0.0084 (6)0.0035 (6)
C70.0425 (9)0.0536 (11)0.0316 (8)0.0066 (8)0.0067 (7)0.0057 (8)
C80.0399 (9)0.0393 (9)0.0337 (8)−0.0004 (7)0.0077 (7)−0.0044 (7)
C90.0383 (8)0.0344 (8)0.0346 (8)0.0009 (7)0.0119 (6)−0.0007 (7)
C100.0380 (8)0.0298 (8)0.0328 (8)0.0012 (6)0.0138 (6)0.0011 (6)
C110.0363 (8)0.0323 (8)0.0355 (8)0.0033 (6)0.0116 (6)0.0042 (6)
C120.0398 (9)0.0378 (9)0.0425 (9)0.0054 (7)0.0178 (7)0.0057 (7)
C130.0528 (10)0.0403 (9)0.0388 (9)0.0064 (8)0.0241 (8)0.0011 (7)
C140.0491 (10)0.0440 (10)0.0326 (8)0.0011 (8)0.0132 (7)−0.0031 (7)
C150.0335 (8)0.0371 (9)0.0458 (9)0.0024 (7)0.0124 (7)0.0042 (7)
C160.0405 (10)0.0506 (11)0.0481 (11)−0.0012 (7)0.0083 (8)−0.0010 (8)

Geometric parameters (Å, °)

Mg1—O6i2.0510 (11)C3—C41.402 (2)
Mg1—O62.0510 (11)C3—C71.506 (2)
Mg1—O8i2.0605 (12)C4—C51.395 (2)
Mg1—O82.0605 (12)C5—C61.380 (2)
Mg1—O72.0638 (12)C5—H50.9300
Mg1—O7i2.0638 (12)C6—H60.9300
S1—O21.4588 (11)C7—H7A0.9600
S1—O31.4590 (11)C7—H7B0.9600
S1—O11.4605 (11)C7—H7C0.9600
S1—C11.7735 (16)C8—C91.448 (2)
N1—C81.282 (2)C8—H80.9300
N1—C41.416 (2)C9—C101.399 (2)
O4—C101.3526 (18)C9—C141.407 (2)
O4—H40.8200C10—C111.405 (2)
O5—C111.3695 (19)C11—C121.386 (2)
O5—C151.4262 (19)C12—C131.391 (2)
O6—H150.8499C12—H120.9300
O6—H160.8499C13—C141.372 (2)
O7—H170.8500C13—H130.9300
O7—H180.8500C14—H140.9300
O8—H190.8497C15—C161.500 (2)
O8—H200.8498C15—H15A0.9700
C1—C61.385 (2)C15—H15B0.9700
C1—C21.391 (2)C16—H16A0.9600
C2—C31.389 (2)C16—H16B0.9600
C2—H20.9300C16—H16C0.9600
O6i—Mg1—O6179.45 (7)C6—C5—C4121.00 (14)
O6i—Mg1—O8i90.71 (5)C6—C5—H5119.5
O6—Mg1—O8i88.90 (5)C4—C5—H5119.5
O6i—Mg1—O888.90 (5)C5—C6—C1119.21 (14)
O6—Mg1—O890.71 (5)C5—C6—H6120.4
O8i—Mg1—O889.38 (7)C1—C6—H6120.4
O6i—Mg1—O789.14 (5)C3—C7—H7A109.5
O6—Mg1—O791.25 (5)C3—C7—H7B109.5
O8i—Mg1—O7179.85 (5)H7A—C7—H7B109.5
O8—Mg1—O790.61 (5)C3—C7—H7C109.5
O6i—Mg1—O7i91.25 (5)H7A—C7—H7C109.5
O6—Mg1—O7i89.14 (5)H7B—C7—H7C109.5
O8i—Mg1—O7i90.61 (5)N1—C8—C9122.93 (15)
O8—Mg1—O7i179.85 (5)N1—C8—H8118.5
O7—Mg1—O7i89.40 (7)C9—C8—H8118.5
O2—S1—O3112.78 (6)C10—C9—C14119.59 (15)
O2—S1—O1112.09 (7)C10—C9—C8121.29 (14)
O3—S1—O1112.28 (6)C14—C9—C8119.11 (14)
O2—S1—C1106.45 (7)O4—C10—C9122.43 (14)
O3—S1—C1106.66 (7)O4—C10—C11118.02 (13)
O1—S1—C1106.00 (7)C9—C10—C11119.55 (14)
C8—N1—C4119.24 (13)O5—C11—C12125.18 (14)
C10—O4—H4109.5O5—C11—C10115.24 (13)
C11—O5—C15117.14 (12)C12—C11—C10119.57 (14)
Mg1—O6—H15122.3C11—C12—C13120.80 (15)
Mg1—O6—H16121.5C11—C12—H12119.6
H15—O6—H16110.6C13—C12—H12119.6
Mg1—O7—H17121.6C14—C13—C12120.05 (15)
Mg1—O7—H18123.7C14—C13—H13120.0
H17—O7—H18106.2C12—C13—H13120.0
Mg1—O8—H19124.4C13—C14—C9120.37 (15)
Mg1—O8—H20124.3C13—C14—H14119.8
H19—O8—H20108.1C9—C14—H14119.8
C6—C1—C2120.12 (14)O5—C15—C16107.37 (14)
C6—C1—S1119.63 (11)O5—C15—H15A110.2
C2—C1—S1120.24 (11)C16—C15—H15A110.2
C3—C2—C1121.40 (14)O5—C15—H15B110.2
C3—C2—H2119.3C16—C15—H15B110.2
C1—C2—H2119.3H15A—C15—H15B108.5
C2—C3—C4118.12 (13)C15—C16—H16A109.5
C2—C3—C7121.04 (14)C15—C16—H16B109.5
C4—C3—C7120.84 (14)H16A—C16—H16B109.5
C5—C4—C3120.14 (14)C15—C16—H16C109.5
C5—C4—N1121.40 (14)H16A—C16—H16C109.5
C3—C4—N1118.38 (13)H16B—C16—H16C109.5
O2—S1—C1—C6−39.83 (13)C4—N1—C8—C9176.38 (14)
O3—S1—C1—C6−160.48 (12)N1—C8—C9—C100.3 (3)
O1—S1—C1—C679.69 (13)N1—C8—C9—C14179.19 (16)
O2—S1—C1—C2140.68 (12)C14—C9—C10—O4−177.47 (15)
O3—S1—C1—C220.03 (14)C8—C9—C10—O41.4 (2)
O1—S1—C1—C2−99.81 (13)C14—C9—C10—C112.6 (2)
C6—C1—C2—C31.4 (2)C8—C9—C10—C11−178.57 (14)
S1—C1—C2—C3−179.08 (11)C15—O5—C11—C126.7 (2)
C1—C2—C3—C4−0.7 (2)C15—O5—C11—C10−174.24 (13)
C1—C2—C3—C7178.62 (15)O4—C10—C11—O5−1.4 (2)
C2—C3—C4—C5−0.1 (2)C9—C10—C11—O5178.52 (14)
C7—C3—C4—C5−179.45 (15)O4—C10—C11—C12177.67 (14)
C2—C3—C4—N1176.55 (13)C9—C10—C11—C12−2.4 (2)
C7—C3—C4—N1−2.8 (2)O5—C11—C12—C13179.20 (15)
C8—N1—C4—C5−39.8 (2)C10—C11—C12—C130.2 (2)
C8—N1—C4—C3143.58 (16)C11—C12—C13—C141.8 (3)
C3—C4—C5—C60.2 (2)C12—C13—C14—C9−1.6 (3)
N1—C4—C5—C6−176.35 (14)C10—C9—C14—C13−0.6 (2)
C4—C5—C6—C10.5 (2)C8—C9—C14—C13−179.48 (15)
C2—C1—C6—C5−1.3 (2)C11—O5—C15—C16−177.74 (14)
S1—C1—C6—C5179.20 (11)

Symmetry codes: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4···N10.821.912.6355 (18)146
O6—H15···O2ii0.852.042.8744 (16)168
O6—H16···O1iii0.852.012.8416 (16)165
O7—H17···O1iv0.852.002.8349 (17)166
O7—H18···O3iii0.852.022.8528 (16)166
O8—H19···O3ii0.852.022.8563 (16)168
O8—H20···O2iv0.852.082.8895 (17)159

Symmetry codes: (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z+1; (iv) −x, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5354).

References

  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Qiu, X. Y., Luo, Z. G., Liu, W. S. & Zhu, H. L. (2008). Chin. J. Struct. Chem.27, 707–711.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tai, X. S., Yin, X. H. & Tan, M. Y. (2003). Pol. J. Chem.77, 411–414.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography