supplementary materials
Hexaaquamagnesium bis(4-amino-3-methylbenzenesulfonate)
In the title molecular salt, [Mg(H2O)6](C7H8NO3S)2, the Mg2+ cation lies on an inversion centre. In the crystal, the components are linked by N-H
O and O-HO hydrogen bonds, thereby generating sheets parallel to (001).
A solution of 1.0 mmol 4-amino-3-methyl-benzenesulfonic acid and 1.0 mmol NaOH
in 10 ml ethanol was added to a solution of 0.5 mmol MgCl26H2O in 5 ml
ethanol at room temperature. The mixture was refluxed for 3 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 ethanol at room temperature.
The H atoms were positioned geometrically (C—H = 0.93–0.96, N—H = 0.86,
O—H = 0.85Å) and refined as riding with
Uiso(H)= 1.2 Ueq(C,N) or 1.5 Ueq(O).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).
Hexaaquamagnesium bis(4-amino-3-methylbenzenesulfonate)
top
Crystal data top
| [Mg(H2O)6](C7H8NO3S)2 | F(000) = 532 |
| Mr = 504.81 | Dx = 1.555 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 3577 reflections |
| a = 6.3048 (13) Å | θ = 3.0–28.6° |
| b = 7.0395 (15) Å | µ = 0.34 mm−1 |
| c = 24.356 (5) Å | T = 273 K |
| β = 93.921 (3)° | Block, colourless |
| V = 1078.5 (4) Å3 | 0.23 × 0.16 × 0.12 mm |
| Z = 2 | |
Data collection top
Bruker SMART CCD
diffractometer | 1918 independent reflections |
| Radiation source: fine-focus sealed tube | 1779 reflections with I > 2σ(I) |
| graphite | Rint = 0.020 |
| ω scans | θmax = 25.1°, θmin = 1.7° |
Absorption correction: multi-scan
(SADABS; Bruker, 2000) | h = −6→7 |
| Tmin = 0.926, Tmax = 0.960 | k = −8→8 |
| 5398 measured reflections | l = −28→25 |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.138 | H-atom parameters constrained |
| S = 1.27 | w = 1/[σ2(Fo2) + (0.0175P)2 + 3.9593P]
where P = (Fo2 + 2Fc2)/3 |
| 1918 reflections | (Δ/σ)max < 0.001 |
| 144 parameters | Δρmax = 0.37 e Å−3 |
| 9 restraints | Δρmin = −0.42 e Å−3 |
Crystal data top
| [Mg(H2O)6](C7H8NO3S)2 | V = 1078.5 (4) Å3 |
| Mr = 504.81 | Z = 2 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 6.3048 (13) Å | µ = 0.34 mm−1 |
| b = 7.0395 (15) Å | T = 273 K |
| c = 24.356 (5) Å | 0.23 × 0.16 × 0.12 mm |
| β = 93.921 (3)° | |
Data collection top
Bruker SMART CCD
diffractometer | 1918 independent reflections |
Absorption correction: multi-scan
(SADABS; Bruker, 2000) | 1779 reflections with I > 2σ(I) |
| Tmin = 0.926, Tmax = 0.960 | Rint = 0.020 |
| 5398 measured reflections | θmax = 25.1° |
Refinement top
| R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
| wR(F2) = 0.138 | Δρmax = 0.37 e Å−3 |
| S = 1.27 | Δρmin = −0.42 e Å−3 |
| 1918 reflections | Absolute structure: ? |
| 144 parameters | Flack parameter: ? |
| 9 restraints | Rogers 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| | x | y | z | Uiso*/Ueq | |
| Mg1 | 0.0000 | 0.0000 | 0.0000 | 0.0216 (4) | |
| S1 | 0.40358 (14) | 0.50773 (14) | 0.09733 (4) | 0.0218 (3) | |
| O1 | 0.4934 (5) | 0.6661 (4) | 0.06800 (11) | 0.0317 (7) | |
| O2 | 0.1712 (4) | 0.5034 (4) | 0.09088 (12) | 0.0297 (7) | |
| O3 | 0.4968 (4) | 0.3258 (4) | 0.08251 (12) | 0.0304 (7) | |
| O4 | 0.2913 (5) | 0.0074 (4) | 0.04083 (13) | 0.0375 (8) | |
| H7 | 0.3575 | 0.1051 | 0.0533 | 0.056* | |
| H8 | 0.3647 | −0.0883 | 0.0519 | 0.056* | |
| O5 | −0.0976 (5) | −0.1937 (4) | 0.05737 (13) | 0.0366 (8) | |
| H9 | −0.0146 | −0.2881 | 0.0624 | 0.055* | |
| H10 | −0.2222 | −0.2401 | 0.0564 | 0.055* | |
| O6 | −0.1022 (5) | 0.2297 (4) | 0.04427 (13) | 0.0340 (7) | |
| H12 | −0.2251 | 0.2721 | 0.0498 | 0.052 (16)* | |
| H11 | −0.0147 | 0.3033 | 0.0618 | 0.11 (3)* | |
| N1 | 0.6584 (7) | 0.6327 (6) | 0.33201 (15) | 0.0465 (11) | |
| H1A | 0.7828 | 0.6779 | 0.3408 | 0.056* | |
| H1B | 0.5739 | 0.6070 | 0.3573 | 0.056* | |
| C1 | 0.4753 (6) | 0.5435 (5) | 0.16775 (16) | 0.0217 (8) | |
| C2 | 0.3351 (6) | 0.5006 (6) | 0.20762 (16) | 0.0248 (8) | |
| H2 | 0.2013 | 0.4519 | 0.1971 | 0.030* | |
| C3 | 0.3929 (6) | 0.5297 (5) | 0.26277 (16) | 0.0254 (9) | |
| C4 | 0.5949 (7) | 0.6021 (6) | 0.27807 (16) | 0.0280 (9) | |
| C5 | 0.7335 (7) | 0.6445 (6) | 0.23738 (17) | 0.0305 (9) | |
| H5 | 0.8675 | 0.6936 | 0.2474 | 0.037* | |
| C6 | 0.6748 (6) | 0.6147 (6) | 0.18287 (17) | 0.0276 (9) | |
| H6 | 0.7689 | 0.6424 | 0.1562 | 0.033* | |
| C7 | 0.2434 (7) | 0.4831 (7) | 0.30672 (18) | 0.0363 (10) | |
| H7A | 0.1193 | 0.4209 | 0.2903 | 0.054* | |
| H7B | 0.2022 | 0.5982 | 0.3243 | 0.054* | |
| H7C | 0.3136 | 0.4006 | 0.3336 | 0.054* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Mg1 | 0.0199 (9) | 0.0211 (9) | 0.0240 (9) | −0.0004 (8) | 0.0032 (7) | 0.0008 (8) |
| S1 | 0.0198 (5) | 0.0208 (5) | 0.0249 (5) | −0.0004 (4) | 0.0011 (3) | −0.0008 (4) |
| O1 | 0.0331 (16) | 0.0318 (16) | 0.0304 (15) | −0.0064 (13) | 0.0045 (12) | 0.0080 (13) |
| O2 | 0.0208 (14) | 0.0326 (16) | 0.0351 (16) | 0.0015 (13) | −0.0024 (11) | −0.0017 (13) |
| O3 | 0.0299 (16) | 0.0279 (16) | 0.0335 (16) | 0.0043 (13) | 0.0021 (12) | −0.0089 (13) |
| O4 | 0.0303 (16) | 0.0275 (16) | 0.0527 (19) | −0.0020 (13) | −0.0117 (14) | −0.0009 (15) |
| O5 | 0.0264 (16) | 0.0361 (17) | 0.0486 (19) | 0.0009 (13) | 0.0121 (14) | 0.0161 (15) |
| O6 | 0.0273 (16) | 0.0312 (16) | 0.0442 (18) | 0.0002 (14) | 0.0083 (13) | −0.0131 (14) |
| N1 | 0.051 (2) | 0.060 (3) | 0.028 (2) | −0.018 (2) | −0.0021 (17) | −0.004 (2) |
| C1 | 0.0220 (19) | 0.0166 (18) | 0.0266 (19) | 0.0008 (15) | 0.0018 (15) | −0.0004 (15) |
| C2 | 0.0227 (19) | 0.0198 (19) | 0.032 (2) | −0.0004 (16) | 0.0019 (16) | 0.0006 (17) |
| C3 | 0.032 (2) | 0.0158 (19) | 0.029 (2) | 0.0006 (16) | 0.0067 (16) | 0.0000 (16) |
| C4 | 0.034 (2) | 0.022 (2) | 0.028 (2) | −0.0019 (17) | 0.0015 (17) | −0.0017 (17) |
| C5 | 0.027 (2) | 0.029 (2) | 0.035 (2) | −0.0064 (18) | −0.0047 (18) | −0.0018 (18) |
| C6 | 0.023 (2) | 0.030 (2) | 0.031 (2) | −0.0028 (17) | 0.0046 (16) | 0.0009 (18) |
| C7 | 0.047 (3) | 0.030 (2) | 0.033 (2) | −0.006 (2) | 0.012 (2) | 0.002 (2) |
Geometric parameters (Å, °) top
| Mg1—O4i | 2.029 (3) | N1—C4 | 1.364 (5) |
| Mg1—O4 | 2.029 (3) | N1—H1A | 0.8600 |
| Mg1—O6i | 2.071 (3) | N1—H1B | 0.8600 |
| Mg1—O6 | 2.071 (3) | C1—C6 | 1.380 (5) |
| Mg1—O5 | 2.075 (3) | C1—C2 | 1.390 (5) |
| Mg1—O5i | 2.075 (3) | C2—C3 | 1.383 (6) |
| S1—O1 | 1.459 (3) | C2—H2 | 0.9300 |
| S1—O2 | 1.463 (3) | C3—C4 | 1.399 (6) |
| S1—O3 | 1.465 (3) | C3—C7 | 1.510 (6) |
| S1—C1 | 1.762 (4) | C4—C5 | 1.398 (6) |
| O4—H7 | 0.8499 | C5—C6 | 1.370 (6) |
| O4—H8 | 0.8500 | C5—H5 | 0.9300 |
| O5—H9 | 0.8500 | C6—H6 | 0.9300 |
| O5—H10 | 0.8500 | C7—H7A | 0.9600 |
| O6—H12 | 0.8500 | C7—H7B | 0.9600 |
| O6—H11 | 0.8500 | C7—H7C | 0.9600 |
| | | |
| O4i—Mg1—O4 | 180.0 | H12—O6—H11 | 105.9 |
| O4i—Mg1—O6i | 91.62 (13) | C4—N1—H1A | 120.0 |
| O4—Mg1—O6i | 88.38 (13) | C4—N1—H1B | 120.0 |
| O4i—Mg1—O6 | 88.38 (13) | H1A—N1—H1B | 120.0 |
| O4—Mg1—O6 | 91.62 (13) | C6—C1—C2 | 120.3 (4) |
| O6i—Mg1—O6 | 180.0 | C6—C1—S1 | 118.7 (3) |
| O4i—Mg1—O5 | 90.75 (12) | C2—C1—S1 | 121.0 (3) |
| O4—Mg1—O5 | 89.25 (12) | C3—C2—C1 | 120.6 (4) |
| O6i—Mg1—O5 | 87.41 (12) | C3—C2—H2 | 119.7 |
| O6—Mg1—O5 | 92.59 (12) | C1—C2—H2 | 119.7 |
| O4i—Mg1—O5i | 89.25 (12) | C2—C3—C4 | 119.2 (4) |
| O4—Mg1—O5i | 90.75 (12) | C2—C3—C7 | 121.4 (4) |
| O6i—Mg1—O5i | 92.59 (12) | C4—C3—C7 | 119.4 (4) |
| O6—Mg1—O5i | 87.41 (12) | N1—C4—C5 | 119.5 (4) |
| O5—Mg1—O5i | 180.0 | N1—C4—C3 | 121.1 (4) |
| O1—S1—O2 | 112.49 (18) | C5—C4—C3 | 119.4 (4) |
| O1—S1—O3 | 111.84 (17) | C6—C5—C4 | 120.9 (4) |
| O2—S1—O3 | 111.78 (17) | C6—C5—H5 | 119.5 |
| O1—S1—C1 | 106.55 (17) | C4—C5—H5 | 119.5 |
| O2—S1—C1 | 107.23 (17) | C5—C6—C1 | 119.7 (4) |
| O3—S1—C1 | 106.52 (17) | C5—C6—H6 | 120.2 |
| Mg1—O4—H7 | 127.0 | C1—C6—H6 | 120.2 |
| Mg1—O4—H8 | 126.1 | C3—C7—H7A | 109.5 |
| H7—O4—H8 | 106.5 | C3—C7—H7B | 109.5 |
| Mg1—O5—H9 | 113.8 | H7A—C7—H7B | 109.5 |
| Mg1—O5—H10 | 123.4 | C3—C7—H7C | 109.5 |
| H9—O5—H10 | 105.2 | H7A—C7—H7C | 109.5 |
| Mg1—O6—H12 | 132.6 | H7B—C7—H7C | 109.5 |
| Mg1—O6—H11 | 121.5 | | |
| | | |
| O1—S1—C1—C6 | −38.2 (4) | C2—C3—C4—N1 | −179.9 (4) |
| O2—S1—C1—C6 | −158.9 (3) | C7—C3—C4—N1 | −0.5 (6) |
| O3—S1—C1—C6 | 81.3 (3) | C2—C3—C4—C5 | 0.4 (6) |
| O1—S1—C1—C2 | 142.0 (3) | C7—C3—C4—C5 | 179.8 (4) |
| O2—S1—C1—C2 | 21.4 (4) | N1—C4—C5—C6 | 179.8 (4) |
| O3—S1—C1—C2 | −98.4 (3) | C3—C4—C5—C6 | −0.5 (6) |
| C6—C1—C2—C3 | 0.4 (6) | C4—C5—C6—C1 | 0.6 (6) |
| S1—C1—C2—C3 | −179.8 (3) | C2—C1—C6—C5 | −0.5 (6) |
| C1—C2—C3—C4 | −0.3 (6) | S1—C1—C6—C5 | 179.7 (3) |
| C1—C2—C3—C7 | −179.7 (4) | | |
| Symmetry codes: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O3ii | 0.86 | 2.48 | 3.208 (5) | 143 |
| N1—H1B···O6iii | 0.86 | 2.54 | 3.133 (5) | 127 |
| O4—H7···O3 | 0.85 | 1.90 | 2.748 (4) | 178 |
| O4—H8···O1iv | 0.85 | 1.94 | 2.778 (4) | 169 |
| O5—H9···O2iv | 0.85 | 1.97 | 2.810 (4) | 168 |
| O5—H10···O1v | 0.85 | 1.95 | 2.790 (4) | 170 |
| O6—H11···O2 | 0.85 | 1.94 | 2.776 (4) | 169 |
| O6—H12···O3vi | 0.85 | 2.01 | 2.835 (4) | 163 |
| Symmetry codes: (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) x, y−1, z; (v) x−1, y−1, z; (vi) x−1, y, z. |
Table 1
Selected geometric parameters (Å) top| Mg1—O4 | 2.029 (3) | Mg1—O5 | 2.075 (3) |
| Mg1—O6 | 2.071 (3) | | |
Table 2
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O3i | 0.86 | 2.48 | 3.208 (5) | 143 |
| N1—H1B···O6ii | 0.86 | 2.54 | 3.133 (5) | 127 |
| O4—H7···O3 | 0.85 | 1.90 | 2.748 (4) | 178 |
| O4—H8···O1iii | 0.85 | 1.94 | 2.778 (4) | 169 |
| O5—H9···O2iii | 0.85 | 1.97 | 2.810 (4) | 168 |
| O5—H10···O1iv | 0.85 | 1.95 | 2.790 (4) | 170 |
| O6—H11···O2 | 0.85 | 1.94 | 2.776 (4) | 169 |
| O6—H12···O3v | 0.85 | 2.01 | 2.835 (4) | 163 |
| Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) x−1, y−1, z; (v) x−1, y, z. |
The authors would like to thank the Program for New Century Excellent Talents in
Universities for a research grant.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Zhang, W. & Chen, Y.-T. (2009). Acta Cryst. E65, m0000. [HB5188]
![[Figure 1]](./hb5189fig1thm.gif)
