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

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

doi:10.1107/S160053680702274X

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

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

In the crystal structure of the title compound, [Mg(H₂O)₆](C₁₃H₁₀NO₄S)₂, the packing is stabilized by O_water—H

O_anion hydrogen bonds. An intramolecular O—H

N bond occurs in the anion. The Mg atom has site symmetry $\overline{1}$ .

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702274X/hb2398sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680702274X/hb2398Isup2.hkl Contains datablock I

CCDC reference: 650673

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.006 Å
R factor = 0.064
wR factor = 0.146
Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.

Structure description top

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

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

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)₂	F(000) = 716
M_r = 684.97	D_x = 1.470 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3237 reflections
a = 6.2997 (17) Å	θ = 2.3–26.9°
b = 35.313 (9) Å	µ = 0.26 mm⁻¹
c = 6.9561 (19) Å	T = 291 K
β = 90.75 (1)°	Block, brown
V = 1547.3 (7) Å³	0.30 × 0.24 × 0.22 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	3041 independent reflections
Radiation source: sealed tube	2173 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
phi and ω scans	θ_max = 26.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
T_min = 0.93, T_max = 0.94	k = −22→43
8390 measured reflections	l = −8→8

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0657P)² + 0.77P] where P = (F_o² + 2F_c²)/3
3041 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Mg(H₂O)₆](C₁₃H₁₀NO₄S)₂	V = 1547.3 (7) Å³
M_r = 684.97	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.2997 (17) Å	µ = 0.26 mm⁻¹
b = 35.313 (9) Å	T = 291 K
c = 6.9561 (19) Å	0.30 × 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)
T_min = 0.93, T_max = 0.94	R_int = 0.044
8390 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.00	Δρ_max = 0.25 e Å⁻³
3041 reflections	Δρ_min = −0.46 e Å⁻³
205 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
C1	0.5147 (7)	0.29797 (12)	0.5190 (6)	0.0540 (10)
C2	0.6701 (8)	0.32508 (13)	0.5548 (6)	0.0647 (12)
H2	0.8064	0.3173	0.5893	0.078*
C3	0.6272 (9)	0.36279 (14)	0.5404 (7)	0.0724 (13)
H3	0.7326	0.3806	0.5663	0.087*
C4	0.4255 (9)	0.37428 (13)	0.4871 (7)	0.0712 (14)
H4	0.3957	0.4000	0.4748	0.085*
C5	0.2695 (9)	0.34828 (14)	0.4524 (6)	0.0696 (13)
H5	0.1344	0.3564	0.4158	0.083*
C6	0.3106 (8)	0.31045 (12)	0.4710 (6)	0.0575 (11)
C7	0.5634 (7)	0.25773 (12)	0.5315 (5)	0.0532 (10)
H7	0.7020	0.2506	0.5614	0.064*
C8	0.4826 (6)	0.19365 (11)	0.5055 (5)	0.0466 (9)
C9	0.3252 (6)	0.16787 (12)	0.5564 (6)	0.0556 (10)
H9	0.1914	0.1765	0.5901	0.067*
C10	0.3670 (6)	0.13009 (12)	0.5569 (6)	0.0495 (9)
H10	0.2622	0.1130	0.5925	0.059*
C11	0.5665 (5)	0.11689 (10)	0.5043 (4)	0.0349 (7)
C12	0.7255 (6)	0.14225 (11)	0.4507 (5)	0.0455 (9)
H12	0.8588	0.1336	0.4155	0.055*
C13	0.6805 (6)	0.18019 (12)	0.4514 (6)	0.0525 (10)
H13	0.7845	0.1973	0.4148	0.063*
Mg1	1.0000	0.0000	0.0000	0.0385 (4)
N1	0.4280 (5)	0.23230 (10)	0.5038 (5)	0.0536 (8)
O1	0.1544 (5)	0.28509 (10)	0.4396 (5)	0.0771 (10)
H1C	0.2119	0.2635	0.4541	0.092*
O2	0.8439 (3)	0.06285 (7)	0.4953 (3)	0.0406 (6)
O3	0.5166 (4)	0.05345 (7)	0.3242 (3)	0.0465 (6)
O4	0.5167 (4)	0.05225 (7)	0.6716 (3)	0.0452 (6)
O5	0.7139 (3)	0.02654 (7)	−0.0016 (3)	0.0421 (6)
H5A	0.7144	0.0460	−0.0981	0.063*
H5B	0.6887	0.0377	0.1221	0.063*
O6	1.1087 (4)	0.03733 (8)	0.2055 (4)	0.0536 (7)
H6B	1.2111	0.0247	0.2852	0.080*
H6C	0.9918	0.0457	0.2832	0.080*
O7	0.8927 (4)	−0.03449 (8)	0.2191 (4)	0.0519 (7)
H7B	0.7912	−0.0209	0.2956	0.078*
H7C	1.0104	−0.0419	0.2983	0.078*
S1	0.61427 (12)	0.06773 (2)	0.49840 (11)	0.0325 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.067 (3)	0.050 (2)	0.046 (2)	0.0107 (19)	0.0090 (19)	0.0048 (17)
C2	0.070 (3)	0.053 (3)	0.071 (3)	0.002 (2)	0.002 (2)	0.005 (2)
C3	0.086 (4)	0.057 (3)	0.075 (3)	−0.008 (3)	0.014 (3)	0.003 (2)
C4	0.107 (4)	0.044 (2)	0.063 (3)	0.018 (3)	0.012 (3)	0.002 (2)
C5	0.098 (4)	0.059 (3)	0.052 (3)	0.028 (3)	−0.008 (2)	0.010 (2)
C6	0.072 (3)	0.052 (2)	0.048 (2)	0.003 (2)	−0.004 (2)	0.0087 (18)
C7	0.057 (3)	0.052 (2)	0.050 (2)	0.015 (2)	−0.0015 (18)	0.0063 (18)
C8	0.049 (2)	0.041 (2)	0.049 (2)	0.0062 (17)	−0.0054 (16)	0.0030 (16)
C9	0.036 (2)	0.059 (3)	0.072 (3)	0.0088 (18)	0.0053 (18)	−0.002 (2)
C10	0.0361 (19)	0.053 (2)	0.059 (2)	0.0043 (17)	0.0096 (16)	−0.0018 (18)
C11	0.0269 (16)	0.0469 (19)	0.0309 (15)	−0.0006 (13)	−0.0022 (12)	0.0033 (14)
C12	0.0388 (19)	0.047 (2)	0.051 (2)	0.0036 (16)	0.0147 (16)	0.0013 (16)
C13	0.051 (2)	0.049 (2)	0.058 (2)	−0.0100 (18)	0.0121 (18)	−0.0013 (18)
Mg1	0.0372 (9)	0.0385 (9)	0.0398 (9)	−0.0013 (7)	−0.0019 (6)	−0.0002 (7)
N1	0.057 (2)	0.052 (2)	0.0507 (19)	0.0073 (17)	−0.0018 (15)	0.0017 (15)
O1	0.069 (2)	0.066 (2)	0.096 (3)	0.0148 (17)	−0.0236 (18)	0.0034 (17)
O2	0.0178 (10)	0.0545 (15)	0.0494 (13)	0.0060 (9)	−0.0004 (9)	−0.0018 (11)
O3	0.0340 (12)	0.0584 (16)	0.0470 (14)	0.0014 (11)	−0.0062 (10)	−0.0143 (12)
O4	0.0306 (12)	0.0580 (16)	0.0471 (14)	0.0023 (11)	0.0035 (10)	0.0138 (12)
O5	0.0310 (12)	0.0564 (15)	0.0388 (12)	0.0093 (11)	0.0012 (9)	−0.0032 (11)
O6	0.0300 (13)	0.077 (2)	0.0534 (16)	0.0003 (12)	−0.0036 (11)	−0.0246 (14)
O7	0.0286 (12)	0.0743 (19)	0.0528 (15)	−0.0006 (11)	0.0012 (10)	0.0264 (13)
S1	0.0202 (4)	0.0428 (5)	0.0345 (4)	0.0020 (3)	−0.0012 (3)	−0.0007 (3)

Geometric parameters (Å, º) top

C1—C2	1.389 (6)	C11—C12	1.398 (5)
C1—C6	1.396 (6)	C11—S1	1.762 (4)
C1—C7	1.456 (6)	C12—C13	1.369 (5)
C2—C3	1.362 (7)	C12—H12	0.9300
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.380 (7)	Mg1—O5	2.031 (2)
C3—H3	0.9300	Mg1—O5ⁱ	2.031 (2)
C4—C5	1.364 (7)	Mg1—O6	2.055 (2)
C4—H4	0.9300	Mg1—O6ⁱ	2.055 (2)
C5—C6	1.366 (6)	Mg1—O7ⁱ	2.071 (2)
C5—H5	0.9300	Mg1—O7	2.071 (2)
C6—O1	1.346 (5)	O1—H1C	0.8500
C7—N1	1.251 (5)	O2—S1	1.457 (2)
C7—H7	0.9300	O3—S1	1.443 (2)
C8—C13	1.391 (5)	O4—S1	1.465 (2)
C8—C9	1.395 (6)	O5—H5A	0.9599
C8—N1	1.408 (5)	O5—H5B	0.9618
C9—C10	1.360 (6)	O6—H6B	0.9551
C9—H9	0.9300	O6—H6C	0.9653
C10—C11	1.394 (5)	O7—H7B	0.9645
C10—H10	0.9300	O7—H7C	0.9544

C2—C1—C6	118.0 (4)	C12—C13—C8	121.4 (4)
C2—C1—C7	121.0 (4)	C12—C13—H13	119.3
C6—C1—C7	121.0 (4)	C8—C13—H13	119.3
C3—C2—C1	121.5 (5)	O5—Mg1—O5ⁱ	180.0
C3—C2—H2	119.3	O5—Mg1—O6	89.73 (10)
C1—C2—H2	119.3	O5ⁱ—Mg1—O6	90.27 (10)
C2—C3—C4	119.2 (5)	O5—Mg1—O6ⁱ	90.27 (10)
C2—C3—H3	120.4	O5ⁱ—Mg1—O6ⁱ	89.73 (10)
C4—C3—H3	120.4	O6—Mg1—O6ⁱ	180.0
C5—C4—C3	120.6 (4)	O5—Mg1—O7ⁱ	91.30 (10)
C5—C4—H4	119.7	O5ⁱ—Mg1—O7ⁱ	88.70 (10)
C3—C4—H4	119.7	O6—Mg1—O7ⁱ	91.47 (11)
C4—C5—C6	120.4 (5)	O6ⁱ—Mg1—O7ⁱ	88.53 (11)
C4—C5—H5	119.8	O5—Mg1—O7	88.70 (10)
C6—C5—H5	119.8	O5ⁱ—Mg1—O7	91.30 (10)
O1—C6—C5	119.9 (4)	O6—Mg1—O7	88.53 (11)
O1—C6—C1	119.9 (4)	O6ⁱ—Mg1—O7	91.47 (11)
C5—C6—C1	120.2 (5)	O7ⁱ—Mg1—O7	180.0
N1—C7—C1	123.3 (4)	C7—N1—C8	121.9 (4)
N1—C7—H7	118.4	C6—O1—H1C	105.6
C1—C7—H7	118.4	Mg1—O5—H5A	108.8
C13—C8—C9	119.2 (4)	Mg1—O5—H5B	110.0
C13—C8—N1	123.3 (4)	H5A—O5—H5B	109.5
C9—C8—N1	117.4 (4)	Mg1—O6—H6B	108.7
C10—C9—C8	120.2 (4)	Mg1—O6—H6C	109.7
C10—C9—H9	119.9	H6B—O6—H6C	109.4
C8—C9—H9	119.9	Mg1—O7—H7B	109.8
C9—C10—C11	120.2 (4)	Mg1—O7—H7C	109.1
C9—C10—H10	119.9	H7B—O7—H7C	109.5
C11—C10—H10	119.9	O3—S1—O2	111.04 (14)
C10—C11—C12	120.5 (3)	O3—S1—O4	112.40 (15)
C10—C11—S1	119.4 (3)	O2—S1—O4	113.27 (14)
C12—C11—S1	120.1 (3)	O3—S1—C11	107.02 (15)
C13—C12—C11	118.5 (3)	O2—S1—C11	106.65 (14)
C13—C12—H12	120.8	O4—S1—C11	105.96 (15)
C11—C12—H12	120.8

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N1	0.85	1.78	2.574 (5)	154
O5—H5A···O4ⁱⁱ	0.96	2.03	2.732 (3)	129
O5—H5B···O3	0.96	1.87	2.768 (3)	154
O6—H6B···O3ⁱⁱⁱ	0.96	2.19	2.749 (3)	116
O6—H6C···O2	0.97	1.86	2.783 (3)	160
O7—H7B···O4^iv	0.96	2.25	2.770 (3)	113
O7—H7C···O2^v	0.95	1.85	2.760 (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.

Experimental details

Crystal data
Chemical formula	[Mg(H₂O)₆](C₁₃H₁₀NO₄S)₂
M_r	684.97
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	6.2997 (17), 35.313 (9), 6.9561 (19)
β (°)	90.75 (1)
V (Å³)	1547.3 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.30 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.93, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections	8390, 3041, 2173
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.146, 1.00
No. of reflections	3041
No. of parameters	205
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.46

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL.

Selected bond lengths (Å) top

Mg1—O5	2.031 (2)	Mg1—O7	2.071 (2)
Mg1—O6	2.055 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N1	0.85	1.78	2.574 (5)	154
O5—H5A···O4ⁱ	0.96	2.03	2.732 (3)	129
O5—H5B···O3	0.96	1.87	2.768 (3)	154
O6—H6B···O3ⁱⁱ	0.96	2.19	2.749 (3)	116
O6—H6C···O2	0.97	1.86	2.783 (3)	160
O7—H7B···O4ⁱⁱⁱ	0.96	2.25	2.770 (3)	113
O7—H7C···O2^iv	0.95	1.85	2.760 (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.

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