Di-μ-aqua-bis­{diaqua­[μ-4-({4-[bis­(2-hy­droxy­eth­yl)amino]-6-chloro-1,3,5-triazin-2-yl}amino)­benzene­sulfonato]­sodium(I)}

Mei Zhang; Fu-Yu Sun; Gui-Zhe Zhao; Ya-Qing Liu

doi:10.1107/S1600536812023732

. 2012 May 31;68(Pt 6):m847–m848. doi: 10.1107/S1600536812023732

Di-μ-aqua-bis{diaqua[μ-4-({4-[bis(2-hydroxyethyl)amino]-6-chloro-1,3,5-triazin-2-yl}amino)benzenesulfonato]sodium(I)}

Mei Zhang ^a, Fu-Yu Sun ^a, Gui-Zhe Zhao ^a, Ya-Qing Liu ^a,^*

PMCID: PMC3379186 PMID: 22719384

Abstract

In the dinuclear title compound, [Na₂(C₁₃H₁₅ClN₅O₅S)₂(H₂O)₆]_n, two Na⁺ cations, disposed about a centre of inversion, are linked by two bridging water molecules. The coordination geometry is based on an O₅ donor set defined by four water molecules and a 4-aminobenzenesulfonate O atom in a distorted trigonal–bipyramidal geometry. In the crystal, significant O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds lead to the formation of a three-dimensional architecture.

Related literature

For commercial and synthetic applications of related compounds, see: Candiani & Frigerio (2007 ▶); Hollink et al. (2005 ▶); Konstantion & Petrova (2002 ▶). graphic file with name e-68-0m847-scheme1.jpg

Experimental

Crystal data

[Na₂(C₁₃H₁₅ClN₅O₅S)₂(H₂O)₆]
M _r = 931.72
Triclinic,
a = 7.5628 (7) Å
b = 8.6274 (8) Å
c = 15.532 (2) Å
α = 97.348 (2)°
β = 93.363 (4)°
γ = 102.410 (7)°
V = 977.75 (18) Å³
Z = 1
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 113 K
0.50 × 0.04 × 0.04 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 2005 ▶) T _min = 0.834, T _max = 0.985
8262 measured reflections
3418 independent reflections
1459 reflections with I > 2σ(I)
R _int = 0.106

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.131
S = 0.87
3418 reflections
283 parameters
20 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalClear.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023732/tk5096sup1.cif

e-68-0m847-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023732/tk5096Isup2.hkl

e-68-0m847-Isup2.hkl^{(167.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N4ⁱ	0.87 (2)	1.96 (3)	2.823 (5)	172 (5)
O2—H2⋯O3ⁱⁱ	0.86 (3)	1.94 (3)	2.772 (4)	165 (4)
O6—H6A⋯O5ⁱⁱⁱ	0.99	1.83	2.817 (4)	174
O6—H6B⋯N3^iv	0.99	2.23	3.009 (5)	135
O7—H7A⋯O8^v	0.87 (2)	2.02 (3)	2.861 (5)	164 (4)
O7—H7B⋯O2ⁱⁱ	0.82 (2)	1.95 (2)	2.767 (4)	169 (5)
O8—H8A⋯O5^vi	0.80 (2)	2.03 (3)	2.797 (4)	162 (4)
O8—H8B⋯O3ⁱⁱⁱ	0.82 (2)	2.15 (3)	2.907 (5)	154 (4)
N5—H5⋯O1^iv	0.90 (4)	2.01 (4)	2.828 (5)	151 (4)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

This work was supported financially by the Research Center for Engineering Technology of Polymeric Composites of Shanxi Province, College of Materials Science and Engineering, North University of China,

supplementary crystallographic information

Comment

Cyanuric chloride derivatives are widely used in commercial chemicals, especially in pesticides, reactive dyes, fluorescent brighteners, liposome and polymer photostabilizers (Hollink et al., 2005; Candiani & Frigerio, 2007). The widespread use of these compounds is due to their higher reactive activity (Konstantion & Petrova, 2002). The title compound belongs to the cyanuric chloride derivatives and its structure is reported herein.

The asymmetric unit is shown in Fig. 1. The dihedral angle between the benzene ring and the triazine ring is 8.6 (2)°. As shown in Fig. 2, the crystal packing displays O—H···O, O—H···N and N—H···O hydrogen bonds, Table 1.

Experimental

Cyanuric chloride (0.1 mol) was dissolved in acetone (120 ml). This solution was poured into distilled water (150 ml) with crushed ice (150 g). The reaction system was stirred maintaining the temperature at 0–5 °C in the ice-bath. An aqueous solution of sodium sulfate (0.1 mol) was slowly dropped into the above reaction vessel within 0.5 h, and then a 20% aqueous solution of sodium carbonate was added drop-wise to the reaction mixture to keep the pH at 7–8. Then the mixture was kept stirring for 5 h at 0–5 °C. After the reaction was completed, the white precipitate was filtered, washed with acetone and water twice, respectively, and dried at room temperatuer under vacuum to constant weight. This white powder is intermediate I. The intermediate I (0.05 mol) and a mixed solution of water and acetone (160 ml) were added into 250 ml four-neck flask. After stirring for 0.5 h at 25 °C, an aqueous solution of diethanol amine (0.06 mol) was slowly dropped into the reaction vessel within 0.5 h, and then a 20% aqueous solution of sodium carbonate was added drop-wise to the reaction mixture to keep the pH at 8–9. Then the mixture was kept stirring for 6 h at 45 °C. After the reaction was completed, the solution was rotary evaporated, washed with anhydrous alcohol twice, and dried at room temperature under vacuum to constant weight. The target product was obtained. Crystals of the title compound were obtained by slow evaporation of its methanol/n-hexane solution held at room temperature.