Poly[μ5-(4-meth­oxy­benzene­sulfonato)-sodium]

Chantrapromma, S.; Boonnak, N.; Fun, H.-K.

doi:10.1107/S1600536813025919

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page m558

doi:10.1107/S1600536813025919

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Poly[μ₅-(4-methoxybenzenesulfonato)-sodium]

Suchada Chantrapromma,^a ^*‡ Nawong Boonnak ^b and Hoong-Kun Fun ^c §

^aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 29 August 2013; accepted 19 September 2013; online 25 September 2013)

In the title complex, [Na(C₇H₇O₄S)]_n, the Na^I ion is coordinated in a slightly distorted pentagonal-bipyramidal environment by seven O atoms [Na—O = 2.3198 (16)–2.5585 (17) Å]. The 4-methoxybenzenesulfonate anions act as bis-chelating and bridging ligands, forming a two-dimensional polymer parallel to (001), which is further linked into a three-dimensional network by weak C—H⋯O hydrogen bonds.

CCDC reference: 962110

Related literature

For the appplications of aromatic sulfonic acids, see: Babu et al. (2003 ); Chanawanno et al. (2010 ); King (1991 ); Ruanwas et al. (2010 ); Schöngut et al. (2011 ); Siril et al. (2007 ); Taylor et al. (2006 ). For a related structure, see: Smith et al. (2004 ). For standard bond-lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

[Na(C₇H₇O₄S)]
M_r = 210.19
Orthorhombic, P b c a
a = 8.3121 (8) Å
b = 6.0287 (6) Å
c = 35.930 (3) Å
V = 1800.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 293 K
0.54 × 0.46 × 0.22 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.819, T_max = 0.920
8793 measured reflections
1769 independent reflections
1720 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.101
S = 1.20
1769 reflections
119 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1ⁱ	0.93	2.37	3.282 (3)	165
C7—H7A⋯O4ⁱⁱ	0.96	2.56	3.407 (4)	148
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ), Mercury and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 962110

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813025919/lh5648sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813025919/lh5648Isup2.hkl

checkCIF report

Comment top

Aromatic sulfonic acids are one of several useful sulfonic acids which are frequently used as chemical reagents (King, 1991) such as reagents for phenol preparation. They are also widely used as acid catalysts in organic reactions (Siril et al., 2007) such as for the deprotection of O-allylphenols (Babu et al., 2003). Salts of benzenesulfonic acid exhibit pharmaceutical and biological activities (Chanawanno et al., 2010; Taylor et al., 2006), and are also used for nonlinear optical material preparations (Ruanwas et al., 2010) and as raw materials in detergent manufacture (Schöngut et al., 2011). Based on these significant roles played by aromatic sulfonic acids, we have synthesized the sodium salt of 4-methoxybenzenesulfonate and herein we report the crystal structure of the title compound (I).

Within the title coordination polymer there are tetranuclear clusters containing four Na^I ions and four 4-methoxybenzenesulfonate ligands (Fig. 1). All three O atoms of the 4-methoxybenzenesulfonate ligands are involved in coordination to the Na^I ion. The coordination modes of the sulfonate unit are chelating bidentate and bridging monodentate linking two Na^I ions. Each Na^I is in a distorted pentagonal-bipyramidal geometry (Fig. 2) with three pairs of chelating O atoms from the three bidentate sulfonate groups and one bridging O atom from another monodentate sulfonate group which is also coordinated to a symmetry related Na^I ion. The distance of the Na^I ion from the mean plane of the O₅ equatorial atoms is 0.127 Å. Bond lengths (Allen et al., 1987) and angles in the ligand are in normal ranges. The Na—O bond distances in the equatorial plane range from 2.3198 (16) - 2.5585 (17) Å, and the two axial Na—O bond distances are 2.3734 (17) and 2.4637 (16) Å. The O—Na—O bond angles in the equatorial plane are in the range 56.76 (5)–85.88 (6) ° and the axial angle is 158.12 (7)°. These values are comparable to those reported for another Na—O donor complex (Smith et al., 2004). The overall structure is a two-dimensional polymer parallel to (001) (Fig. 3). In addition, weak C—H···O hydrogen bonds (Table 1) link the polymer into a three-dimensional network (Fig. 4).

Related literature top

For the appplications of aromatic sulfonic acids, see: Babu et al. (2003); Chanawanno et al. (2010); King (1991); Ruanwas et al. (2010); Schöngut et al. (2011); Siril et al. (2007); Taylor et al. (2006). For a related structure, see: Smith et al. (2004). For standard bond-lengths, see Allen et al. (1987).

Experimental top

To a solution of 4-methoxybenzenesulfonyl chloride (3.00 g, 14.50 mmol) in hot methanol, sodium hydroxide (0.58 g, 14.50 mmol) was added. The suspension was stirred for 1 h. The reaction mixture was then cooled to the room temperature and the resulting white solid formed was filtered off and washed with CH₃OH. Colorless needle-shaped single crystals suitable for X-ray structure determination were recrystallized from a solution of (I) in CH₃OH by slow evaporation at room temperature over a few days.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Part of the polymeric structure of (I) showing a tetranuclear cluster with 50% probability displacement ellipsoids. Atoms labelled with the suffix A, B, and C are generated by the symmetry operations (x + 1/2, -y + 1/2, -z + 2), (-x + 1, -y, -z + 2) and (-x + 1/2, y + 1/2, z), respectively.
	Fig. 2. Part of the polymeric structure of (I) showing the coordination environment of Na^I ions in (I).
	Fig. 3. The two-dimensional polymer of (I) viewed along the b axis. Hydrogen bonds are drawn as dashed lines.
	Fig. 4. The crystal packing of (I), viewed along the c axis.

Poly[µ₅-(4-methoxybenzenesulfonato)-sodium] top

Crystal data top

[Na(C₇H₇O₄S)]	F(000) = 864
M_r = 210.19	D_x = 1.551 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1769 reflections
a = 8.3121 (8) Å	θ = 2.3–26.0°
b = 6.0287 (6) Å	µ = 0.38 mm⁻¹
c = 35.930 (3) Å	T = 293 K
V = 1800.5 (3) Å³	Needle, colorless
Z = 8	0.54 × 0.46 × 0.22 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	1769 independent reflections
Radiation source: sealed tube	1720 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→10
T_min = 0.819, T_max = 0.920	k = −7→7
8793 measured reflections	l = −37→44

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0372P)² + 1.6253P] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max = 0.001
1769 reflections	Δρ_max = 0.28 e Å⁻³
119 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (3)

Crystal data top

[Na(C₇H₇O₄S)]	V = 1800.5 (3) Å³
M_r = 210.19	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.3121 (8) Å	µ = 0.38 mm⁻¹
b = 6.0287 (6) Å	T = 293 K
c = 35.930 (3) Å	0.54 × 0.46 × 0.22 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	1769 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1720 reflections with I > 2σ(I)
T_min = 0.819, T_max = 0.920	R_int = 0.022
8793 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.20	Δρ_max = 0.28 e Å⁻³
1769 reflections	Δρ_min = −0.28 e Å⁻³
119 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
S1	0.50598 (6)	0.11687 (8)	0.950009 (13)	0.0257 (2)
O1	0.67113 (17)	0.0690 (2)	0.96029 (4)	0.0328 (4)
O2	0.39805 (19)	−0.0717 (3)	0.95165 (4)	0.0386 (4)
O3	0.44483 (18)	0.3026 (2)	0.97215 (4)	0.0324 (4)
O4	0.4881 (4)	0.4270 (4)	0.79459 (6)	0.0843 (8)
C1	0.5047 (2)	0.2071 (4)	0.90315 (6)	0.0300 (5)
C2	0.4151 (4)	0.0971 (4)	0.87675 (7)	0.0483 (6)
H2A	0.3570	−0.0291	0.8831	0.058*
C3	0.4122 (4)	0.1762 (5)	0.84065 (7)	0.0603 (8)
H3A	0.3511	0.1036	0.8227	0.072*
C4	0.4991 (4)	0.3615 (5)	0.83113 (7)	0.0526 (7)
C5	0.5888 (4)	0.4721 (5)	0.85733 (7)	0.0573 (8)
H5A	0.6477	0.5974	0.8508	0.069*
C6	0.5902 (3)	0.3942 (4)	0.89371 (7)	0.0482 (7)
H6A	0.6493	0.4688	0.9118	0.058*
C7	0.5762 (7)	0.6163 (7)	0.78319 (10)	0.1151 (19)
H7A	0.5575	0.6431	0.7572	0.173*
H7B	0.6888	0.5913	0.7873	0.173*
H7C	0.5418	0.7428	0.7973	0.173*
Na	0.18295 (10)	0.12772 (12)	0.98998 (2)	0.0314 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0260 (3)	0.0239 (3)	0.0273 (3)	−0.00035 (18)	0.00168 (17)	0.00130 (18)
O1	0.0280 (7)	0.0355 (8)	0.0349 (8)	0.0061 (6)	0.0021 (6)	0.0032 (6)
O2	0.0435 (9)	0.0347 (8)	0.0376 (8)	−0.0131 (7)	0.0013 (7)	0.0018 (6)
O3	0.0333 (8)	0.0311 (8)	0.0330 (8)	0.0078 (6)	0.0023 (6)	−0.0011 (6)
O4	0.143 (2)	0.0803 (16)	0.0299 (10)	−0.0139 (15)	−0.0124 (11)	0.0134 (10)
C1	0.0332 (11)	0.0318 (11)	0.0250 (10)	−0.0001 (8)	−0.0003 (8)	0.0022 (8)
C2	0.0630 (17)	0.0453 (13)	0.0367 (12)	−0.0158 (12)	−0.0037 (11)	−0.0029 (10)
C3	0.086 (2)	0.0616 (17)	0.0337 (13)	−0.0154 (16)	−0.0139 (13)	−0.0076 (12)
C4	0.077 (2)	0.0512 (16)	0.0294 (13)	0.0020 (14)	−0.0036 (11)	0.0044 (11)
C5	0.078 (2)	0.0531 (15)	0.0404 (13)	−0.0231 (15)	−0.0043 (13)	0.0139 (12)
C6	0.0598 (16)	0.0497 (14)	0.0351 (12)	−0.0218 (12)	−0.0102 (11)	0.0076 (10)
C7	0.210 (6)	0.091 (3)	0.0443 (19)	−0.023 (3)	−0.002 (3)	0.0328 (19)
Na	0.0295 (4)	0.0227 (4)	0.0420 (5)	−0.0004 (3)	0.0039 (3)	0.0000 (3)

Geometric parameters (Å, º) top

S1—O2	1.4495 (16)	C3—C4	1.374 (4)
S1—O1	1.4506 (15)	C3—H3A	0.9300
S1—O3	1.4644 (15)	C4—C5	1.374 (4)
S1—C1	1.769 (2)	C5—C6	1.389 (3)
S1—Naⁱ	3.0304 (10)	C5—H5A	0.9300
S1—Na	3.0457 (10)	C6—H6A	0.9300
O1—Naⁱⁱ	2.4637 (16)	C7—H7A	0.9600
O1—Naⁱ	2.5585 (17)	C7—H7B	0.9600
O2—Naⁱⁱⁱ	2.3734 (17)	C7—H7C	0.9600
O2—Na	2.5572 (18)	Na—O3ⁱⁱⁱ	2.3198 (16)
O3—Na^iv	2.3198 (16)	Na—O2^iv	2.3734 (17)
O3—Naⁱ	2.4384 (17)	Na—O3^v	2.4384 (17)
O3—Na	2.5021 (17)	Na—O1ⁱⁱ	2.4637 (16)
O4—C4	1.374 (3)	Na—O1^v	2.5585 (17)
O4—C7	1.416 (5)	Na—S1^v	3.0304 (9)
C1—C6	1.376 (3)	Na—Na^iv	3.2138 (6)
C1—C2	1.377 (3)	Na—Naⁱⁱⁱ	3.2138 (6)
C2—C3	1.382 (4)	Na—Na^vi	3.4843 (16)
C2—H2A	0.9300

O2—S1—O1	114.78 (10)	O2^iv—Na—O3	77.09 (6)
O2—S1—O3	111.27 (9)	O3^v—Na—O3	140.94 (4)
O1—S1—O3	110.02 (9)	O1ⁱⁱ—Na—O3	87.72 (6)
O2—S1—C1	106.03 (10)	O3ⁱⁱⁱ—Na—O2	76.94 (6)
O1—S1—C1	108.00 (9)	O2^iv—Na—O2	104.17 (7)
O3—S1—C1	106.25 (9)	O3^v—Na—O2	161.64 (6)
O2—S1—Naⁱ	132.07 (7)	O1ⁱⁱ—Na—O2	79.63 (5)
O1—S1—Naⁱ	57.36 (6)	O3—Na—O2	56.76 (5)
O3—S1—Naⁱ	52.67 (6)	O3ⁱⁱⁱ—Na—O1^v	141.19 (6)
C1—S1—Naⁱ	121.58 (8)	O2^iv—Na—O1^v	81.30 (6)
O2—S1—Na	56.77 (7)	O3^v—Na—O1^v	57.04 (5)
O1—S1—Na	135.93 (6)	O1ⁱⁱ—Na—O1^v	81.74 (5)
O3—S1—Na	54.65 (6)	O3—Na—O1^v	84.91 (5)
C1—S1—Na	115.90 (7)	O2—Na—O1^v	137.65 (6)
Naⁱ—S1—Na	94.675 (17)	O3ⁱⁱⁱ—Na—S1^v	113.81 (5)
S1—O1—Naⁱⁱ	138.27 (9)	O2^iv—Na—S1^v	83.53 (4)
S1—O1—Naⁱ	94.12 (7)	O3^v—Na—S1^v	28.52 (4)
Naⁱⁱ—O1—Naⁱ	79.55 (5)	O1ⁱⁱ—Na—S1^v	88.14 (4)
S1—O2—Naⁱⁱⁱ	142.94 (10)	O3—Na—S1^v	112.98 (4)
S1—O2—Na	94.92 (8)	O2—Na—S1^v	164.05 (5)
Naⁱⁱⁱ—O2—Na	81.26 (5)	O1^v—Na—S1^v	28.52 (3)
S1—O3—Na^iv	162.75 (9)	O3ⁱⁱⁱ—Na—S1	104.79 (5)
S1—O3—Naⁱ	98.81 (8)	O2^iv—Na—S1	89.59 (5)
Na^iv—O3—Naⁱ	94.12 (6)	O3^v—Na—S1	169.25 (5)
S1—O3—Na	96.83 (8)	O1ⁱⁱ—Na—S1	84.13 (4)
Na^iv—O3—Na	83.51 (5)	O3—Na—S1	28.52 (3)
Naⁱ—O3—Na	129.48 (6)	O2—Na—S1	28.31 (4)
C4—O4—C7	118.3 (3)	O1^v—Na—S1	112.25 (4)
C6—C1—C2	120.3 (2)	S1^v—Na—S1	140.75 (3)
C6—C1—S1	118.91 (17)	O3ⁱⁱⁱ—Na—Na^iv	162.05 (5)
C2—C1—S1	120.73 (18)	O2^iv—Na—Na^iv	51.86 (4)
C1—C2—C3	119.3 (2)	O3^v—Na—Na^iv	96.89 (4)
C1—C2—H2A	120.3	O1ⁱⁱ—Na—Na^iv	106.30 (5)
C3—C2—H2A	120.3	O3—Na—Na^iv	45.82 (4)
C4—C3—C2	120.3 (2)	O2—Na—Na^iv	101.45 (5)
C4—C3—H3A	119.8	O1^v—Na—Na^iv	48.93 (4)
C2—C3—H3A	119.8	S1^v—Na—Na^iv	72.048 (19)
C3—C4—C5	120.6 (2)	S1—Na—Na^iv	73.41 (3)
C3—C4—O4	115.9 (3)	O3ⁱⁱⁱ—Na—Naⁱⁱⁱ	50.67 (4)
C5—C4—O4	123.4 (3)	O2^iv—Na—Naⁱⁱⁱ	144.53 (4)
C4—C5—C6	119.0 (2)	O3^v—Na—Naⁱⁱⁱ	116.30 (4)
C4—C5—H5A	120.5	O1ⁱⁱ—Na—Naⁱⁱⁱ	51.52 (4)
C6—C5—H5A	120.5	O3—Na—Naⁱⁱⁱ	95.36 (5)
C1—C6—C5	120.3 (2)	O2—Na—Naⁱⁱⁱ	46.88 (4)
C1—C6—H6A	119.8	O1^v—Na—Naⁱⁱⁱ	133.13 (4)
C5—C6—H6A	119.8	S1^v—Na—Naⁱⁱⁱ	130.16 (2)
O4—C7—H7A	109.5	S1—Na—Naⁱⁱⁱ	70.98 (3)
O4—C7—H7B	109.5	Na^iv—Na—Naⁱⁱⁱ	139.42 (5)
H7A—C7—H7B	109.5	O3ⁱⁱⁱ—Na—Na^vi	44.27 (4)
O4—C7—H7C	109.5	O2^iv—Na—Na^vi	102.10 (6)
H7A—C7—H7C	109.5	O3^v—Na—Na^vi	41.61 (4)
H7B—C7—H7C	109.5	O1ⁱⁱ—Na—Na^vi	93.85 (5)
O3ⁱⁱⁱ—Na—O2^iv	110.78 (7)	O3—Na—Na^vi	176.92 (6)
O3ⁱⁱⁱ—Na—O3^v	85.88 (6)	O2—Na—Na^vi	120.91 (5)
O2^iv—Na—O3^v	87.82 (6)	O1^v—Na—Na^vi	97.94 (5)
O3ⁱⁱⁱ—Na—O1ⁱⁱ	91.09 (6)	S1^v—Na—Na^vi	69.75 (3)
O2^iv—Na—O1ⁱⁱ	158.12 (7)	S1—Na—Na^vi	149.03 (4)
O3^v—Na—O1ⁱⁱ	94.46 (6)	Na^iv—Na—Na^vi	135.83 (4)
O3ⁱⁱⁱ—Na—O3	133.13 (7)	Naⁱⁱⁱ—Na—Na^vi	83.58 (3)

O2—S1—O1—Naⁱⁱ	−46.59 (17)	Naⁱ—O3—Na—Na^iv	90.00 (8)
O3—S1—O1—Naⁱⁱ	79.82 (15)	S1—O3—Na—Naⁱⁱⁱ	30.86 (7)
C1—S1—O1—Naⁱⁱ	−164.62 (13)	Na^iv—O3—Na—Naⁱⁱⁱ	−166.50 (4)
Naⁱ—S1—O1—Naⁱⁱ	78.90 (12)	Naⁱ—O3—Na—Naⁱⁱⁱ	−76.51 (7)
Na—S1—O1—Naⁱⁱ	20.4 (2)	S1—O2—Na—O3ⁱⁱⁱ	169.52 (8)
O2—S1—O1—Naⁱ	−125.50 (8)	Naⁱⁱⁱ—O2—Na—O3ⁱⁱⁱ	−47.62 (6)
O3—S1—O1—Naⁱ	0.91 (9)	S1—O2—Na—O2^iv	61.03 (8)
C1—S1—O1—Naⁱ	116.48 (9)	Naⁱⁱⁱ—O2—Na—O2^iv	−156.11 (6)
Na—S1—O1—Naⁱ	−58.50 (10)	S1—O2—Na—O3^v	−169.45 (17)
O1—S1—O2—Naⁱⁱⁱ	48.05 (19)	Naⁱⁱⁱ—O2—Na—O3^v	−26.6 (2)
O3—S1—O2—Naⁱⁱⁱ	−77.71 (18)	S1—O2—Na—O1ⁱⁱ	−96.90 (8)
C1—S1—O2—Naⁱⁱⁱ	167.19 (15)	Naⁱⁱⁱ—O2—Na—O1ⁱⁱ	45.95 (5)
Naⁱ—S1—O2—Naⁱⁱⁱ	−19.4 (2)	S1—O2—Na—O3	−2.80 (6)
Na—S1—O2—Naⁱⁱⁱ	−82.01 (16)	Naⁱⁱⁱ—O2—Na—O3	140.06 (7)
O1—S1—O2—Na	130.06 (8)	S1—O2—Na—O1^v	−31.57 (12)
O3—S1—O2—Na	4.30 (10)	Naⁱⁱⁱ—O2—Na—O1^v	111.29 (8)
C1—S1—O2—Na	−110.81 (8)	S1—O2—Na—S1^v	−56.4 (2)
Naⁱ—S1—O2—Na	62.61 (10)	Naⁱⁱⁱ—O2—Na—S1^v	86.49 (17)
O2—S1—O3—Na^iv	−94.5 (3)	Naⁱⁱⁱ—O2—Na—S1	142.86 (10)
O1—S1—O3—Na^iv	137.1 (3)	S1—O2—Na—Na^iv	7.82 (8)
C1—S1—O3—Na^iv	20.5 (4)	Naⁱⁱⁱ—O2—Na—Na^iv	150.67 (4)
Naⁱ—S1—O3—Na^iv	138.1 (4)	S1—O2—Na—Naⁱⁱⁱ	−142.86 (10)
Na—S1—O3—Na^iv	−90.1 (3)	S1—O2—Na—Na^vi	174.81 (6)
O2—S1—O3—Naⁱ	127.40 (8)	Naⁱⁱⁱ—O2—Na—Na^vi	−42.33 (7)
O1—S1—O3—Naⁱ	−0.97 (10)	O2—S1—Na—O3ⁱⁱⁱ	−10.56 (9)
C1—S1—O3—Naⁱ	−117.63 (8)	O1—S1—Na—O3ⁱⁱⁱ	−103.07 (11)
Na—S1—O3—Naⁱ	131.81 (8)	O3—S1—Na—O3ⁱⁱⁱ	174.35 (10)
O2—S1—O3—Na	−4.41 (10)	C1—S1—Na—O3ⁱⁱⁱ	82.24 (9)
O1—S1—O3—Na	−132.77 (7)	Naⁱ—S1—Na—O3ⁱⁱⁱ	−149.16 (5)
C1—S1—O3—Na	110.56 (8)	O2—S1—Na—O2^iv	−121.97 (9)
Naⁱ—S1—O3—Na	−131.81 (8)	O1—S1—Na—O2^iv	145.51 (10)
O2—S1—C1—C6	176.20 (19)	O3—S1—Na—O2^iv	62.94 (8)
O1—S1—C1—C6	−60.3 (2)	C1—S1—Na—O2^iv	−29.17 (9)
O3—S1—C1—C6	57.7 (2)	Naⁱ—S1—Na—O2^iv	99.43 (5)
Naⁱ—S1—C1—C6	1.9 (2)	O2—S1—Na—O3^v	162.0 (3)
Na—S1—C1—C6	115.82 (19)	O1—S1—Na—O3^v	69.5 (3)
O2—S1—C1—C2	−1.4 (2)	O3—S1—Na—O3^v	−13.1 (3)
O1—S1—C1—C2	122.1 (2)	C1—S1—Na—O3^v	−105.2 (3)
O3—S1—C1—C2	−119.9 (2)	Naⁱ—S1—Na—O3^v	23.4 (3)
Naⁱ—S1—C1—C2	−175.71 (18)	O2—S1—Na—O1ⁱⁱ	79.02 (9)
Na—S1—C1—C2	−61.8 (2)	O1—S1—Na—O1ⁱⁱ	−13.49 (13)
C6—C1—C2—C3	0.2 (4)	O3—S1—Na—O1ⁱⁱ	−96.07 (8)
S1—C1—C2—C3	177.8 (2)	C1—S1—Na—O1ⁱⁱ	171.82 (9)
C1—C2—C3—C4	0.6 (5)	Naⁱ—S1—Na—O1ⁱⁱ	−59.58 (4)
C2—C3—C4—C5	−0.6 (5)	O2—S1—Na—O3	175.09 (11)
C2—C3—C4—O4	−179.9 (3)	O1—S1—Na—O3	82.58 (12)
C7—O4—C4—C3	−179.6 (4)	C1—S1—Na—O3	−92.11 (11)
C7—O4—C4—C5	1.2 (5)	Naⁱ—S1—Na—O3	36.49 (7)
C3—C4—C5—C6	−0.1 (5)	O1—S1—Na—O2	−92.51 (12)
O4—C4—C5—C6	179.1 (3)	O3—S1—Na—O2	−175.09 (11)
C2—C1—C6—C5	−0.9 (4)	C1—S1—Na—O2	92.80 (11)
S1—C1—C6—C5	−178.6 (2)	Naⁱ—S1—Na—O2	−138.60 (8)
C4—C5—C6—C1	0.9 (5)	O2—S1—Na—O1^v	157.60 (9)
S1—O3—Na—O3ⁱⁱⁱ	−7.49 (14)	O1—S1—Na—O1^v	65.09 (12)
Na^iv—O3—Na—O3ⁱⁱⁱ	155.15 (6)	O3—S1—Na—O1^v	−17.49 (8)
Naⁱ—O3—Na—O3ⁱⁱⁱ	−114.86 (10)	C1—S1—Na—O1^v	−109.60 (9)
S1—O3—Na—O2^iv	−113.99 (8)	Naⁱ—S1—Na—O1^v	19.00 (4)
Na^iv—O3—Na—O2^iv	48.64 (6)	O2—S1—Na—S1^v	158.80 (9)
Naⁱ—O3—Na—O2^iv	138.64 (9)	O1—S1—Na—S1^v	66.29 (11)
S1—O3—Na—O3^v	176.15 (9)	O3—S1—Na—S1^v	−16.29 (8)
Na^iv—O3—Na—O3^v	−21.21 (9)	C1—S1—Na—S1^v	−108.40 (9)
Naⁱ—O3—Na—O3^v	68.79 (11)	Naⁱ—S1—Na—S1^v	20.20 (4)
S1—O3—Na—O1ⁱⁱ	81.88 (7)	O2—S1—Na—Na^iv	−172.01 (8)
Na^iv—O3—Na—O1ⁱⁱ	−115.49 (5)	O1—S1—Na—Na^iv	95.48 (10)
Naⁱ—O3—Na—O1ⁱⁱ	−25.49 (8)	O3—S1—Na—Na^iv	12.91 (7)
S1—O3—Na—O2	2.78 (6)	C1—S1—Na—Na^iv	−79.21 (8)
Na^iv—O3—Na—O2	165.42 (7)	Naⁱ—S1—Na—Na^iv	49.40 (2)
Naⁱ—O3—Na—O2	−104.59 (9)	O2—S1—Na—Naⁱⁱⁱ	27.79 (8)
S1—O3—Na—O1^v	163.79 (7)	O1—S1—Na—Naⁱⁱⁱ	−64.73 (10)
Na^iv—O3—Na—O1^v	−33.58 (5)	O3—S1—Na—Naⁱⁱⁱ	−147.30 (7)
Naⁱ—O3—Na—O1^v	56.42 (8)	C1—S1—Na—Naⁱⁱⁱ	120.59 (8)
S1—O3—Na—S1^v	168.89 (5)	Naⁱ—S1—Na—Naⁱⁱⁱ	−110.811 (19)
Na^iv—O3—Na—S1^v	−28.48 (6)	O2—S1—Na—Na^vi	−8.67 (11)
Naⁱ—O3—Na—S1^v	61.52 (8)	O1—S1—Na—Na^vi	−101.19 (12)
Na^iv—O3—Na—S1	162.63 (10)	O3—S1—Na—Na^vi	176.24 (12)
Naⁱ—O3—Na—S1	−107.37 (11)	C1—S1—Na—Na^vi	84.13 (12)
S1—O3—Na—Na^iv	−162.63 (10)	Naⁱ—S1—Na—Na^vi	−147.27 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1^vii	0.93	2.37	3.282 (3)	165
C7—H7A···O4^viii	0.96	2.56	3.407 (4)	148

Symmetry codes: (vii) −x+3/2, y+1/2, z; (viii) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1ⁱ	0.93	2.37	3.282 (3)	165
C7—H7A···O4ⁱⁱ	0.96	2.56	3.407 (4)	148

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1, y+1/2, −z+3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, email: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Prince of Songkla University for generous support. The authors also thank the Universiti Sains Malaysia for the APEX DE2012 grant No.1002/PFIZIK/910323.

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