Hexaaqua­magnesium bis­(4-amino-3-methyl­benzene­sulfonate)

Zhang, W.; Chen, Y.-T.

doi:10.1107/S1600536809046595

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1549

doi:10.1107/S1600536809046595

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Hexaaquamagnesium bis(4-amino-3-methylbenzenesulfonate)

Wei Zhang ^a and Yuan-Tao Chen ^a ^*

^aDepartment of Chemistry, Qinghai Normal University, Xining 810008, People's Republic of China
^*Correspondence e-mail: chenyt@qhnu.edu.cn

(Received 26 October 2009; accepted 4 November 2009; online 11 November 2009)

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—H⋯O hydrogen bonds, thereby generating sheets parallel to (001).

Related literature

For the isostructural cobalt-containing compound, see: Zhang & Chen (2009 ).

Experimental

Crystal data

[Mg(H₂O)₆](C₇H₈NO₃S)₂
M_r = 504.81
Monoclinic, P 2₁ /n
a = 6.3048 (13) Å
b = 7.0395 (15) Å
c = 24.356 (5) Å
β = 93.921 (3)°
V = 1078.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 273 K
0.23 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.926, T_max = 0.960
5398 measured reflections
1918 independent reflections
1779 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.138
S = 1.27
1918 reflections
144 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected bond lengths (Å)

Mg1—O4	2.029 (3)
Mg1—O6	2.071 (3)
Mg1—O5	2.075 (3)

Table 2
Hydrogen-bond geometry (Å, °)

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⋯O1^iv	0.85	1.95	2.790 (4)	170
O6—H11⋯O2	0.85	1.94	2.776 (4)	169
O6—H12⋯O3^v	0.85	2.01	2.835 (4)	163
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) x-1, y-1, z; (v) x-1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046595/hb5189sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046595/hb5189Isup2.hkl

checkCIF report

Related literature top

For the isostructural cobalt-containing compound, see: Zhang & Chen (2009).

Experimental top

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.

Computing details top

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).

Figures top

Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids. Atoms with the suffix A are generated by (–x, –y, –z).

Hexaaquamagnesium bis(4-amino-3-methylbenzenesulfonate) top

Crystal data top

[Mg(H₂O)₆](C₇H₈NO₃S)₂	F(000) = 532
M_r = 504.81	D_x = 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 monochromator	R_int = 0.020
ω scans	θ_max = 25.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→7
T_min = 0.926, T_max = 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(F_o²) + (0.0175P)² + 3.9593P] where P = (F_o² + 2F_c²)/3
1918 reflections	(Δ/σ)_max < 0.001
144 parameters	Δρ_max = 0.37 e Å⁻³
9 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Mg(H₂O)₆](C₇H₈NO₃S)₂	V = 1078.5 (4) Å³
M_r = 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)
T_min = 0.926, T_max = 0.960	R_int = 0.020
5398 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	9 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.27	Δρ_max = 0.37 e Å⁻³
1918 reflections	Δρ_min = −0.42 e Å⁻³
144 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

	x	y	z	U_iso*/U_eq
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, º) 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 code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) 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···O1^iv	0.85	1.94	2.778 (4)	169
O5—H9···O2^iv	0.85	1.97	2.810 (4)	168
O5—H10···O1^v	0.85	1.95	2.790 (4)	170
O6—H11···O2	0.85	1.94	2.776 (4)	169
O6—H12···O3^vi	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.

Experimental details

Crystal data
Chemical formula	[Mg(H₂O)₆](C₇H₈NO₃S)₂
M_r	504.81
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	6.3048 (13), 7.0395 (15), 24.356 (5)
β (°)	93.921 (3)
V (Å³)	1078.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.23 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.926, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	5398, 1918, 1779
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.138, 1.27
No. of reflections	1918
No. of parameters	144
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.42

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Mg1—O4	2.029 (3)	Mg1—O5	2.075 (3)
Mg1—O6	2.071 (3)

Hydrogen-bond geometry (Å, º) 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···O1^iv	0.85	1.95	2.790 (4)	170
O6—H11···O2	0.85	1.94	2.776 (4)	169
O6—H12···O3^v	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.

Acknowledgements

The authors would like to thank the Program for New Century Excellent Talents in Universities for a research grant.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, W. & Chen, Y.-T. (2009). Acta Cryst. E65, m1548. Web of Science CSD CrossRef IUCr Journals Google Scholar