Poly[μ2-aqua-(μ3-2,5-dichloro­benzene­sulfonato)sodium]

Al-Dajani, M.T.M.; Abdallah, H.H.; Mohamed, N.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810018118

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page m699

https://doi.org/10.1107/S1600536810018118

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Poly[μ₂-aqua-(μ₃-2,5-dichlorobenzenesulfonato)sodium]

Mohammad T. M. Al-Dajani,^a Hassan H. Abdallah,^b Nornisah Mohamed,^a ‡ Chin Sing Yeap ^c § and Hoong-Kun Fun ^c ^*¶

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 11 May 2010; accepted 16 May 2010; online 22 May 2010)

In the title compound, [Na(C₆H₃Cl₂O₃S)(H₂O)]_n, the Na^I ion is pentacoordinated by three dichlorobenzenesulfonate anions and two water molecules, forming a distorted trigonal-bipyramidal geometry. The Na^I ions are bridged by the sulfonate groups and the water molecules, leading to a polymeric layer structure parallel to the bc plane in which O—H⋯O hydrogen bonds are observed.

Related literature

For general background to organic sulfonyl chloride compounds, see: Adams & Marvel (1941 ); D'Souza et al. (2008 ); Henze & Artman (1957 ); Uchiro & Kobayashi (1999 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

[Na(C₆H₃Cl₂O₃S)(H₂O)]
M_r = 267.05
Monoclinic, P 2₁ /c
a = 17.2461 (10) Å
b = 5.4568 (3) Å
c = 10.7178 (6) Å
β = 106.190 (2)°
V = 968.64 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 100 K
0.34 × 0.34 × 0.05 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.749, T_max = 0.955
15240 measured reflections
4266 independent reflections
3594 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.100
S = 1.12
4266 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3ⁱ	0.75	2.09	2.8409 (13)	172
O1W—H2W1⋯O2ⁱⁱ	0.78	2.12	2.8620 (14)	162
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810018118/is2546sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018118/is2546Isup2.hkl

checkCIF report

Comment top

Organic sulfonyl chloride compounds can be used as fundamental starting material for the synthesis of a variety of useful agricultural and medical compounds. They are widespread in many natural products and widely used as various artificial chemicals. It can be used as precursors in the synthesis of sulfonamide-based drugs (Adams & Marvel, 1941; D'Souza et al., 2008; Henze & Artman, 1957; Uchiro & Kobayashi, 1999).

The asymmetric unit of the title compound contains one dichlorobenzenesulfonate anion, one sodium cation and one water molecule (Fig. 1). Each sodium cation is pentacoordinated with three dichlorobenzenesulfonate anions and two water molecules to form a distorted trigonal bipyramidal geometry (Fig. 2). In the crystal structure (Fig. 3), the molecules are linked into polymeric planes parallel to the bc plane. The polymeric structures are stabilized by the O1W—H1W1···O3 and O1W—H2W1···O2 hydrogen bonds (Table 1).

Related literature top

For general background to organic sulfonyl chloride compounds, see: Adams & Marvel (1941); D'Souza et al. (2008); Henze & Artman (1957); Uchiro & Kobayashi (1999). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

2,5-Dichlorobenzenesulfonyl chloride (0.02 mol, 4.86 g) was dissolved in 25 ml of 1,4-dioxane (C₄H₈O₂) in round bottom flask with stirring. Sodium hydroxide (0.01 mol, 0.4 g) was added to the mixture and refluxed for 2 hours. The colour of the mixture was changed from colorless to light brown. After solvent evaporation, 50 ml of distilled water was added and mixed with 50 ml of butanol. After shaking the mixture for 15 min, butanol layer was isolated and brown precipitate was left after the butanol evaporation. The precipitate was dissolved in methanol at room temperature and left over night. The colourless plate crystals were formed, filtrated, washed with water and dried at 333 K.

Structure description top

For general background to organic sulfonyl chloride compounds, see: Adams & Marvel (1941); D'Souza et al. (2008); Henze & Artman (1957); Uchiro & Kobayashi (1999). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound with atom labels and 50% probability ellipsoids for non-H atoms.
	Fig. 2. The molecular structure of the title compound with 50% probability ellipsoids for non-H atoms, showing the coordination environment for the Na^I ion.
	Fig. 3. The crystal packing of title compound, viewed down the b axis, showing a polymeric plane parallel to the bc plane.

Poly[µ₂-aqua-(µ₃-2,5-dichlorobenzenesulfonato)sodium] top

Crystal data top

[Na(C₆H₃Cl₂O₃S)(H₂O)]	F(000) = 536
M_r = 267.05	D_x = 1.831 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5321 reflections
a = 17.2461 (10) Å	θ = 3.7–34.9°
b = 5.4568 (3) Å	µ = 0.91 mm⁻¹
c = 10.7178 (6) Å	T = 100 K
β = 106.190 (2)°	Plate, colourless
V = 968.64 (9) Å³	0.34 × 0.34 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4266 independent reflections
Radiation source: fine-focus sealed tube	3594 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 35.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→26
T_min = 0.749, T_max = 0.955	k = −8→7
15240 measured reflections	l = −17→17

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0518P)² + 0.1259P] where P = (F_o² + 2F_c²)/3
4266 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

[Na(C₆H₃Cl₂O₃S)(H₂O)]	V = 968.64 (9) Å³
M_r = 267.05	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.2461 (10) Å	µ = 0.91 mm⁻¹
b = 5.4568 (3) Å	T = 100 K
c = 10.7178 (6) Å	0.34 × 0.34 × 0.05 mm
β = 106.190 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4266 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3594 reflections with I > 2σ(I)
T_min = 0.749, T_max = 0.955	R_int = 0.034
15240 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.12	Δρ_max = 0.77 e Å⁻³
4266 reflections	Δρ_min = −0.68 e Å⁻³
127 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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) top

	x	y	z	U_iso*/U_eq
Na1	0.08149 (3)	0.90539 (10)	0.72118 (5)	0.01189 (11)
S1	0.148184 (17)	0.41852 (5)	0.54858 (3)	0.00956 (7)
Cl1	0.42170 (2)	0.19246 (8)	0.92304 (3)	0.02371 (9)
Cl2	0.25118 (2)	0.84404 (7)	0.45028 (3)	0.02048 (8)
O1	0.12791 (6)	0.21059 (18)	0.61606 (9)	0.01572 (18)
O2	0.13814 (6)	0.37277 (18)	0.41079 (8)	0.01294 (16)
O3	0.10928 (6)	0.64583 (17)	0.57044 (8)	0.01330 (17)
C1	0.29337 (8)	0.3214 (2)	0.72508 (11)	0.0135 (2)
H1A	0.2667	0.1916	0.7514	0.016*
C2	0.37368 (8)	0.3708 (3)	0.78932 (12)	0.0157 (2)
C3	0.41525 (8)	0.5610 (3)	0.75190 (13)	0.0191 (3)
H3A	0.4688	0.5921	0.7967	0.023*
C4	0.37588 (8)	0.7047 (3)	0.64672 (14)	0.0191 (2)
H4A	0.4032	0.8323	0.6199	0.023*
C5	0.29559 (8)	0.6583 (2)	0.58129 (12)	0.0139 (2)
C6	0.25339 (7)	0.4687 (2)	0.62083 (11)	0.01083 (19)
O1W	0.04880 (6)	0.57236 (17)	0.84097 (9)	0.01383 (17)
H1W1	0.0610	0.6420	0.9041	0.021*
H2W1	0.0771	0.4600	0.8467	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0144 (2)	0.0106 (2)	0.0110 (2)	−0.00028 (18)	0.00418 (17)	−0.00018 (16)
S1	0.01175 (13)	0.00815 (12)	0.00837 (11)	−0.00060 (9)	0.00211 (9)	0.00033 (8)
Cl1	0.01946 (16)	0.02930 (19)	0.01790 (14)	0.00684 (13)	−0.00218 (11)	0.00674 (12)
Cl2	0.01613 (15)	0.02089 (16)	0.02309 (15)	−0.00208 (11)	0.00327 (11)	0.01191 (12)
O1	0.0187 (4)	0.0124 (4)	0.0152 (4)	−0.0036 (3)	0.0034 (3)	0.0044 (3)
O2	0.0173 (4)	0.0120 (4)	0.0083 (3)	0.0001 (3)	0.0017 (3)	−0.0012 (3)
O3	0.0148 (4)	0.0117 (4)	0.0137 (4)	0.0018 (3)	0.0045 (3)	−0.0010 (3)
C1	0.0146 (5)	0.0136 (5)	0.0118 (4)	0.0021 (4)	0.0025 (4)	0.0005 (4)
C2	0.0143 (5)	0.0184 (6)	0.0127 (5)	0.0052 (4)	0.0009 (4)	0.0007 (4)
C3	0.0112 (5)	0.0232 (7)	0.0209 (6)	0.0010 (5)	0.0010 (4)	−0.0002 (5)
C4	0.0128 (5)	0.0203 (6)	0.0233 (6)	−0.0025 (5)	0.0038 (5)	0.0029 (5)
C5	0.0131 (5)	0.0136 (5)	0.0148 (5)	0.0000 (4)	0.0037 (4)	0.0025 (4)
C6	0.0113 (5)	0.0104 (5)	0.0105 (4)	0.0004 (4)	0.0027 (4)	−0.0003 (3)
O1W	0.0159 (4)	0.0109 (4)	0.0133 (4)	0.0000 (3)	0.0019 (3)	−0.0002 (3)

Geometric parameters (Å, º) top

Na1—O1ⁱ	2.2775 (10)	C1—C2	1.3905 (18)
Na1—O3	2.2974 (10)	C1—C6	1.3930 (17)
Na1—O2ⁱⁱ	2.3329 (10)	C1—H1A	0.9300
Na1—O1Wⁱⁱⁱ	2.3427 (11)	C2—C3	1.383 (2)
Na1—O1W	2.3816 (11)	C3—C4	1.386 (2)
S1—O1	1.4400 (10)	C3—H3A	0.9300
S1—O2	1.4597 (9)	C4—C5	1.3900 (19)
S1—O3	1.4599 (10)	C4—H4A	0.9300
S1—C6	1.7841 (12)	C5—C6	1.3971 (17)
Cl1—C2	1.7393 (13)	O1W—H1W1	0.7531
Cl2—C5	1.7279 (13)	O1W—H2W1	0.7754

O1ⁱ—Na1—O3	86.09 (4)	C2—C1—C6	119.15 (12)
O1ⁱ—Na1—O2ⁱⁱ	86.09 (4)	C2—C1—H1A	120.4
O3—Na1—O2ⁱⁱ	144.45 (4)	C6—C1—H1A	120.4
O1ⁱ—Na1—O1Wⁱⁱⁱ	90.95 (4)	C3—C2—C1	121.83 (12)
O3—Na1—O1Wⁱⁱⁱ	114.30 (4)	C3—C2—Cl1	119.52 (10)
O2ⁱⁱ—Na1—O1Wⁱⁱⁱ	100.45 (4)	C1—C2—Cl1	118.63 (11)
O1ⁱ—Na1—O1W	173.38 (4)	C2—C3—C4	118.99 (12)
O3—Na1—O1W	92.05 (4)	C2—C3—H3A	120.5
O2ⁱⁱ—Na1—O1W	91.77 (4)	C4—C3—H3A	120.5
O1Wⁱⁱⁱ—Na1—O1W	95.60 (3)	C3—C4—C5	120.04 (13)
O1ⁱ—Na1—H1W1	160.3	C3—C4—H4A	120.0
O3—Na1—H1W1	107.2	C5—C4—H4A	120.0
O2ⁱⁱ—Na1—H1W1	74.6	C4—C5—C6	120.79 (12)
O1Wⁱⁱⁱ—Na1—H1W1	96.4	C4—C5—Cl2	117.17 (10)
O1W—Na1—H1W1	17.3	C6—C5—Cl2	122.04 (10)
O1—S1—O2	113.36 (6)	C1—C6—C5	119.18 (11)
O1—S1—O3	113.71 (6)	C1—C6—S1	118.40 (9)
O2—S1—O3	112.18 (5)	C5—C6—S1	122.32 (9)
O1—S1—C6	105.24 (6)	Na1^vi—O1W—Na1	119.73 (4)
O2—S1—C6	106.54 (5)	Na1^vi—O1W—H1W1	117.2
O3—S1—C6	104.91 (6)	Na1—O1W—H1W1	92.9
S1—O1—Na1^iv	173.06 (7)	Na1^vi—O1W—H2W1	104.3
S1—O2—Na1^v	134.05 (6)	Na1—O1W—H2W1	114.1
S1—O3—Na1	146.31 (6)	H1W1—O1W—H2W1	108.4

O1—S1—O2—Na1^v	135.33 (8)	C3—C4—C5—Cl2	−179.44 (11)
O3—S1—O2—Na1^v	4.87 (10)	C2—C1—C6—C5	1.66 (18)
C6—S1—O2—Na1^v	−109.39 (8)	C2—C1—C6—S1	−174.79 (9)
O1—S1—O3—Na1	49.56 (13)	C4—C5—C6—C1	−1.65 (19)
O2—S1—O3—Na1	179.85 (10)	Cl2—C5—C6—C1	178.27 (10)
C6—S1—O3—Na1	−64.89 (12)	C4—C5—C6—S1	174.65 (10)
O1ⁱ—Na1—O3—S1	130.29 (11)	Cl2—C5—C6—S1	−5.43 (16)
O2ⁱⁱ—Na1—O3—S1	52.59 (14)	O1—S1—C6—C1	−3.24 (11)
O1Wⁱⁱⁱ—Na1—O3—S1	−140.43 (10)	O2—S1—C6—C1	−123.88 (10)
O1W—Na1—O3—S1	−43.34 (11)	O3—S1—C6—C1	117.01 (10)
C6—C1—C2—C3	−0.5 (2)	O1—S1—C6—C5	−179.57 (10)
C6—C1—C2—Cl1	177.65 (9)	O2—S1—C6—C5	59.79 (12)
C1—C2—C3—C4	−0.6 (2)	O3—S1—C6—C5	−59.32 (11)
Cl1—C2—C3—C4	−178.80 (11)	O3—Na1—O1W—Na1^vi	−84.32 (5)
C2—C3—C4—C5	0.6 (2)	O2ⁱⁱ—Na1—O1W—Na1^vi	131.02 (5)
C3—C4—C5—C6	0.5 (2)	O1Wⁱⁱⁱ—Na1—O1W—Na1^vi	30.34 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3ⁱⁱ	0.75	2.09	2.8409 (13)	172
O1W—H2W1···O2^vii	0.78	2.12	2.8620 (14)	162

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

Experimental details

Crystal data
Chemical formula	[Na(C₆H₃Cl₂O₃S)(H₂O)]
M_r	267.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	17.2461 (10), 5.4568 (3), 10.7178 (6)
β (°)	106.190 (2)
V (Å³)	968.64 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.34 × 0.34 × 0.05

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.749, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	15240, 4266, 3594
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.809

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.100, 1.12
No. of reflections	4266
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.68

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3ⁱ	0.7500	2.0900	2.8409 (13)	172.00
O1W—H2W1···O2ⁱⁱ	0.7800	2.1200	2.8620 (14)	162.00

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

Footnotes

‡Additional correspondence author, email: nornisah@usm.my.

§Thomson Reuters ResearcherID: A-5523-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NM gratefully acknowledges funding from Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815025). HKF thanks USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY thanks USM for the award of a USM Fellowship.

References

Adams, R. & Marvel, C. S. (1941). Org. Synth. Coll. 1, 504–512. Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
D'Souza, M. J., Yaakoubd, S. L. & Kevill, D. N. (2008). Int. J. Mol. Sci. 9, 914–925. Web of Science PubMed CAS Google Scholar
Henze, H. R. & Artman, N. E. (1957). J. Org. Chem. 22, 1410–1413. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Uchiro, H. & Kobayashi, S. (1999). Tetrahedron Lett. 40, 3179–3182. Web of Science CrossRef CAS Google Scholar