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

Zhang, M.; Sun, F.-Y.; Zhao, G.-Z.; Liu, Y.-Q.

doi:10.1107/S1600536812023732

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages m847-m848

doi:10.1107/S1600536812023732

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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 and Ya-Qing Liu ^a ^*

^aResearch Center for Engineering Technology of Polymeric Composites of Shanxi Province, College of Materials Science and Engineering, North University of China, Taiyuan 030051, People's Republic of China
^*Correspondence e-mail: gczx2012@gmail.com

(Received 11 May 2012; accepted 24 May 2012; online 31 May 2012)

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 ).

Experimental

Crystal data

[Na₂(C₁₃H₁₅ClN₅O₅S)₂(H₂O)₆]
M_r = 931.72
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.062
wR(F²) = 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

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

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023732/tk5096sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

For commercial and synthetic applications of related compounds, see: Candiani & Frigerio (2007); Hollink et al. (2005); Konstantion & Petrova (2002).

Experimental top

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.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted.
	Fig. 2. A view of the crystal packing for (I). Hydrogen bonds are shown as dashed lines.

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

Crystal data top

[Na₂(C₁₃H₁₅ClN₅O₅S)₂(H₂O)₆]	Z = 1
M_r = 931.72	F(000) = 484
Triclinic, P1	D_x = 1.582 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5628 (7) Å	Cell parameters from 3065 reflections
b = 8.6274 (8) Å	θ = 2.4–26.1°
c = 15.532 (2) Å	µ = 0.38 mm⁻¹
α = 97.348 (2)°	T = 113 K
β = 93.363 (4)°	Prism, colourless
γ = 102.410 (7)°	0.50 × 0.04 × 0.04 mm
V = 977.75 (18) Å³

Data collection top

Rigaku Saturn724 CCD diffractometer	3418 independent reflections
Radiation source: rotating anode	1459 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.106
Detector resolution: 14.22 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
ω and ϕ scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 2005)	k = −10→10
T_min = 0.834, T_max = 0.985	l = −18→18
8262 measured reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ²(F_o²) + (0.0293P)²] where P = (F_o² + 2F_c²)/3
3418 reflections	(Δ/σ)_max = 0.001
283 parameters	Δρ_max = 0.52 e Å⁻³
20 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Na₂(C₁₃H₁₅ClN₅O₅S)₂(H₂O)₆]	γ = 102.410 (7)°
M_r = 931.72	V = 977.75 (18) Å³
Triclinic, P1	Z = 1
a = 7.5628 (7) Å	Mo Kα radiation
b = 8.6274 (8) Å	µ = 0.38 mm⁻¹
c = 15.532 (2) Å	T = 113 K
α = 97.348 (2)°	0.50 × 0.04 × 0.04 mm
β = 93.363 (4)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3418 independent reflections
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 2005)	1459 reflections with I > 2σ(I)
T_min = 0.834, T_max = 0.985	R_int = 0.106
8262 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	20 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	Δρ_max = 0.52 e Å⁻³
3418 reflections	Δρ_min = −0.52 e Å⁻³
283 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
Na1	0.9529 (2)	0.8060 (2)	0.46061 (12)	0.0216 (5)
S1	0.55329 (16)	0.91677 (15)	0.34804 (8)	0.0191 (3)
Cl1	1.02875 (15)	1.27203 (14)	−0.25219 (8)	0.0221 (4)
O1	0.9492 (4)	0.5459 (4)	−0.0875 (2)	0.0213 (9)
H1	0.934 (6)	0.443 (3)	−0.099 (3)	0.032*
O2	0.4874 (4)	0.5163 (4)	−0.3219 (2)	0.0234 (9)
H2	0.504 (6)	0.421 (3)	−0.330 (3)	0.035*
O3	0.4056 (4)	0.7718 (3)	0.32366 (19)	0.0210 (8)
O4	0.7162 (4)	0.8814 (4)	0.3889 (2)	0.0216 (9)
O5	0.4936 (4)	1.0469 (4)	0.40039 (19)	0.0194 (8)
N1	0.7584 (5)	0.7287 (4)	−0.1875 (2)	0.0161 (10)
N2	0.7670 (5)	0.9391 (4)	−0.0807 (2)	0.0162 (10)
N3	0.8817 (5)	0.9841 (4)	−0.2196 (2)	0.0150 (9)
N4	0.8923 (5)	1.2084 (4)	−0.1092 (2)	0.0175 (10)
N5	0.7900 (5)	1.1689 (5)	0.0233 (3)	0.0170 (10)
H5	0.851 (5)	1.272 (5)	0.029 (3)	0.020*
C1	0.7906 (5)	0.5903 (5)	−0.0571 (3)	0.0195 (12)
H1A	0.8270	0.6892	−0.0142	0.023*
H1B	0.7234	0.5042	−0.0271	0.023*
C2	0.6672 (6)	0.6188 (5)	−0.1302 (3)	0.0207 (12)
H2A	0.6108	0.5145	−0.1660	0.025*
H2B	0.5682	0.6632	−0.1048	0.025*
C3	0.8018 (6)	0.6556 (5)	−0.2719 (3)	0.0192 (12)
H3A	0.8331	0.5519	−0.2650	0.023*
H3B	0.9100	0.7264	−0.2901	0.023*
C4	0.6466 (6)	0.6270 (5)	−0.3431 (3)	0.0227 (13)
H4A	0.6151	0.7303	−0.3507	0.027*
H4B	0.6862	0.5828	−0.3989	0.027*
C5	0.8033 (6)	0.8880 (6)	−0.1625 (3)	0.0189 (12)
C6	0.9213 (6)	1.1378 (5)	−0.1863 (3)	0.0169 (12)
C7	0.8149 (6)	1.0990 (6)	−0.0576 (3)	0.0158 (12)
C8	0.7265 (6)	1.0979 (5)	0.0957 (3)	0.0130 (11)
C9	0.7404 (6)	1.2041 (5)	0.1720 (3)	0.0180 (12)
H9	0.7876	1.3154	0.1720	0.022*
C10	0.6857 (6)	1.1488 (5)	0.2486 (3)	0.0180 (12)
H10	0.6997	1.2221	0.3010	0.022*
C11	0.6109 (6)	0.9878 (5)	0.2493 (3)	0.0149 (11)
C12	0.5925 (6)	0.8800 (6)	0.1722 (3)	0.0203 (12)
H12	0.5421	0.7691	0.1720	0.024*
C13	0.6486 (5)	0.9361 (5)	0.0955 (3)	0.0166 (11)
H13	0.6335	0.8634	0.0428	0.020*
O6	1.1240 (4)	1.0471 (3)	0.41494 (19)	0.0191 (8)
H6A	1.2558	1.0514	0.4142	0.023*
H6B	1.0732	1.0718	0.3594	0.023*
O7	0.8355 (4)	0.5359 (4)	0.4260 (2)	0.0349 (11)
H7A	0.825 (6)	0.466 (5)	0.462 (2)	0.042*
H7B	0.747 (5)	0.518 (5)	0.390 (2)	0.042*
O8	1.2365 (4)	0.7394 (4)	0.4857 (2)	0.0226 (9)
H8A	1.297 (5)	0.813 (4)	0.518 (2)	0.027*
H8B	1.267 (5)	0.717 (5)	0.4365 (17)	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0141 (10)	0.0229 (12)	0.0293 (12)	0.0041 (9)	0.0094 (9)	0.0061 (9)
S1	0.0148 (7)	0.0226 (8)	0.0217 (8)	0.0051 (6)	0.0093 (6)	0.0052 (6)
Cl1	0.0211 (7)	0.0231 (8)	0.0241 (8)	0.0047 (6)	0.0125 (6)	0.0067 (6)
O1	0.0155 (18)	0.0163 (19)	0.035 (2)	0.0071 (17)	0.0074 (16)	0.0067 (18)
O2	0.0204 (19)	0.019 (2)	0.028 (2)	−0.0016 (18)	0.0032 (16)	0.0022 (18)
O3	0.0175 (18)	0.020 (2)	0.024 (2)	−0.0023 (16)	0.0067 (16)	0.0032 (16)
O4	0.0116 (17)	0.033 (2)	0.026 (2)	0.0147 (16)	0.0025 (15)	0.0102 (16)
O5	0.0145 (18)	0.024 (2)	0.022 (2)	0.0094 (15)	0.0118 (15)	0.0004 (15)
N1	0.018 (2)	0.016 (2)	0.014 (2)	0.0025 (19)	0.0096 (18)	0.0017 (18)
N2	0.013 (2)	0.021 (2)	0.015 (2)	0.0022 (19)	0.0068 (18)	0.0026 (19)
N3	0.012 (2)	0.015 (2)	0.018 (2)	0.0017 (18)	0.0083 (18)	0.0018 (18)
N4	0.015 (2)	0.022 (3)	0.016 (2)	0.002 (2)	0.0080 (19)	0.0045 (19)
N5	0.016 (2)	0.018 (2)	0.016 (2)	−0.0009 (19)	0.0084 (19)	0.004 (2)
C1	0.015 (3)	0.016 (3)	0.030 (3)	0.004 (2)	0.008 (2)	0.010 (2)
C2	0.023 (3)	0.016 (3)	0.026 (3)	0.008 (2)	0.009 (2)	0.004 (2)
C3	0.019 (3)	0.019 (3)	0.019 (3)	0.004 (2)	0.009 (2)	0.000 (2)
C4	0.028 (3)	0.018 (3)	0.023 (3)	0.005 (3)	0.005 (2)	0.006 (2)
C5	0.009 (3)	0.023 (3)	0.025 (3)	0.002 (2)	0.002 (2)	0.005 (2)
C6	0.015 (3)	0.020 (3)	0.020 (3)	0.009 (2)	0.004 (2)	0.007 (2)
C7	0.008 (3)	0.023 (3)	0.018 (3)	0.007 (2)	0.002 (2)	0.004 (2)
C8	0.009 (3)	0.018 (3)	0.014 (3)	0.007 (2)	0.007 (2)	0.003 (2)
C9	0.016 (3)	0.015 (3)	0.024 (3)	0.003 (2)	0.010 (2)	0.001 (2)
C10	0.017 (3)	0.018 (3)	0.020 (3)	0.004 (2)	0.013 (2)	0.002 (2)
C11	0.011 (2)	0.017 (3)	0.020 (3)	0.009 (2)	0.010 (2)	0.002 (2)
C12	0.016 (3)	0.018 (3)	0.028 (3)	0.004 (2)	0.005 (2)	0.005 (2)
C13	0.013 (3)	0.021 (3)	0.017 (3)	0.004 (2)	0.007 (2)	0.003 (2)
O6	0.0091 (17)	0.030 (2)	0.021 (2)	0.0056 (15)	0.0023 (15)	0.0114 (16)
O7	0.021 (2)	0.034 (3)	0.048 (3)	−0.0018 (19)	−0.0035 (19)	0.017 (2)
O8	0.018 (2)	0.026 (2)	0.022 (2)	0.0009 (17)	0.0065 (17)	0.0023 (18)

Geometric parameters (Å, º) top

Na1—O7	2.290 (4)	N5—H5	0.90 (4)
Na1—O4	2.306 (3)	C1—C2	1.505 (5)
Na1—O6ⁱ	2.346 (4)	C1—H1A	0.9900
Na1—O8	2.361 (4)	C1—H1B	0.9900
Na1—O6	2.415 (3)	C2—H2A	0.9900
Na1—Cl1ⁱⁱ	3.239 (2)	C2—H2B	0.9900
Na1—Na1ⁱ	3.322 (4)	C3—C4	1.522 (5)
Na1—H8B	2.68 (4)	C3—H3A	0.9900
S1—O4	1.461 (3)	C3—H3B	0.9900
S1—O5	1.467 (3)	C4—H4A	0.9900
S1—O3	1.478 (3)	C4—H4B	0.9900
S1—C11	1.766 (5)	C8—C9	1.386 (6)
Cl1—C6	1.746 (5)	C8—C13	1.393 (6)
Cl1—Na1ⁱⁱ	3.238 (2)	C9—C10	1.391 (6)
O1—C1	1.423 (5)	C9—H9	0.9500
O1—H1	0.87 (2)	C10—C11	1.384 (6)
O2—C4	1.451 (5)	C10—H10	0.9500
O2—H2	0.86 (3)	C11—C12	1.400 (6)
N1—C5	1.343 (5)	C12—C13	1.397 (6)
N1—C3	1.467 (5)	C12—H12	0.9500
N1—C2	1.474 (5)	C13—H13	0.9500
N2—C7	1.344 (5)	O6—Na1ⁱ	2.346 (4)
N2—C5	1.354 (6)	O6—H6A	0.9900
N3—C6	1.323 (5)	O6—H6B	0.9900
N3—C5	1.365 (6)	O7—H7A	0.87 (2)
N4—C6	1.324 (5)	O7—H7B	0.82 (2)
N4—C7	1.374 (5)	O8—H8A	0.80 (2)
N5—C7	1.364 (6)	O8—H8B	0.82 (2)
N5—C8	1.408 (5)

O7—Na1—O4	95.45 (13)	C1—C2—H2A	108.7
O7—Na1—O6ⁱ	121.20 (14)	N1—C2—H2B	108.7
O4—Na1—O6ⁱ	85.08 (12)	C1—C2—H2B	108.7
O7—Na1—O8	86.24 (13)	H2A—C2—H2B	107.6
O4—Na1—O8	159.53 (15)	N1—C3—C4	113.2 (4)
O6ⁱ—Na1—O8	111.51 (12)	N1—C3—H3A	108.9
O7—Na1—O6	146.92 (15)	C4—C3—H3A	108.9
O4—Na1—O6	81.63 (11)	N1—C3—H3B	108.9
O6ⁱ—Na1—O6	91.52 (12)	C4—C3—H3B	108.9
O8—Na1—O6	85.87 (12)	H3A—C3—H3B	107.7
O7—Na1—Cl1ⁱⁱ	74.72 (11)	O2—C4—C3	111.2 (4)
O4—Na1—Cl1ⁱⁱ	70.57 (9)	O2—C4—H4A	109.4
O6ⁱ—Na1—Cl1ⁱⁱ	152.67 (10)	C3—C4—H4A	109.4
O8—Na1—Cl1ⁱⁱ	90.36 (10)	O2—C4—H4B	109.4
O6—Na1—Cl1ⁱⁱ	73.26 (9)	C3—C4—H4B	109.4
O7—Na1—Na1ⁱ	167.15 (14)	H4A—C4—H4B	108.0
O4—Na1—Na1ⁱ	80.42 (10)	N1—C5—N2	115.8 (5)
O6ⁱ—Na1—Na1ⁱ	46.62 (8)	N1—C5—N3	118.7 (5)
O8—Na1—Na1ⁱ	101.92 (11)	N2—C5—N3	125.5 (4)
O6—Na1—Na1ⁱ	44.91 (8)	N3—C6—N4	130.0 (5)
Cl1ⁱⁱ—Na1—Na1ⁱ	114.70 (8)	N3—C6—Cl1	116.6 (4)
O7—Na1—H8B	82.4 (8)	N4—C6—Cl1	113.4 (3)
O4—Na1—H8B	142.8 (7)	N2—C7—N5	121.3 (5)
O6ⁱ—Na1—H8B	127.8 (6)	N2—C7—N4	125.9 (5)
O8—Na1—H8B	17.3 (6)	N5—C7—N4	112.8 (4)
O6—Na1—H8B	80.6 (9)	C9—C8—C13	119.3 (4)
Cl1ⁱⁱ—Na1—H8B	73.1 (6)	C9—C8—N5	114.7 (4)
Na1ⁱ—Na1—H8B	108.3 (8)	C13—C8—N5	126.0 (4)
O4—S1—O5	112.25 (18)	C8—C9—C10	120.4 (4)
O4—S1—O3	112.36 (19)	C8—C9—H9	119.8
O5—S1—O3	112.56 (18)	C10—C9—H9	119.8
O4—S1—C11	107.4 (2)	C11—C10—C9	120.6 (4)
O5—S1—C11	105.8 (2)	C11—C10—H10	119.7
O3—S1—C11	105.9 (2)	C9—C10—H10	119.7
C6—Cl1—Na1ⁱⁱ	125.53 (17)	C10—C11—C12	119.4 (4)
C1—O1—H1	112 (3)	C10—C11—S1	120.3 (4)
C4—O2—H2	110 (3)	C12—C11—S1	120.2 (4)
S1—O4—Na1	173.9 (2)	C13—C12—C11	119.7 (4)
C5—N1—C3	121.7 (4)	C13—C12—H12	120.1
C5—N1—C2	121.4 (4)	C11—C12—H12	120.1
C3—N1—C2	116.9 (4)	C8—C13—C12	120.5 (4)
C7—N2—C5	114.2 (4)	C8—C13—H13	119.8
C6—N3—C5	112.4 (4)	C12—C13—H13	119.8
C6—N4—C7	111.9 (4)	Na1ⁱ—O6—Na1	88.48 (12)
C7—N5—C8	129.8 (4)	Na1ⁱ—O6—H6A	113.9
C7—N5—H5	106 (3)	Na1—O6—H6A	113.9
C8—N5—H5	122 (3)	Na1ⁱ—O6—H6B	113.9
O1—C1—C2	112.1 (4)	Na1—O6—H6B	113.9
O1—C1—H1A	109.2	H6A—O6—H6B	111.1
C2—C1—H1A	109.2	Na1—O7—H7A	126 (3)
O1—C1—H1B	109.2	Na1—O7—H7B	111 (3)
C2—C1—H1B	109.2	H7A—O7—H7B	112 (3)
H1A—C1—H1B	107.9	Na1—O8—H8A	106 (3)
N1—C2—C1	114.4 (4)	Na1—O8—H8B	104 (3)
N1—C2—H2A	108.7	H8A—O8—H8B	120 (3)

O5—S1—O4—Na1	90 (2)	C5—N2—C7—N5	−178.9 (4)
O3—S1—O4—Na1	−38 (2)	C5—N2—C7—N4	0.8 (6)
C11—S1—O4—Na1	−154 (2)	C8—N5—C7—N2	4.3 (7)
O7—Na1—O4—S1	48 (2)	C8—N5—C7—N4	−175.4 (4)
O6ⁱ—Na1—O4—S1	−73 (2)	C6—N4—C7—N2	−1.9 (6)
O8—Na1—O4—S1	141.4 (19)	C6—N4—C7—N5	177.8 (4)
O6—Na1—O4—S1	−166 (2)	C7—N5—C8—C9	171.8 (4)
Cl1ⁱⁱ—Na1—O4—S1	119 (2)	C7—N5—C8—C13	−10.3 (7)
Na1ⁱ—Na1—O4—S1	−120 (2)	C13—C8—C9—C10	3.2 (7)
C5—N1—C2—C1	−76.6 (5)	N5—C8—C9—C10	−178.8 (4)
C3—N1—C2—C1	101.9 (4)	C8—C9—C10—C11	−2.2 (7)
O1—C1—C2—N1	−50.9 (5)	C9—C10—C11—C12	0.7 (6)
C5—N1—C3—C4	−94.4 (5)	C9—C10—C11—S1	176.5 (3)
C2—N1—C3—C4	87.0 (5)	O4—S1—C11—C10	−86.3 (4)
N1—C3—C4—O2	−61.9 (5)	O5—S1—C11—C10	33.7 (4)
C3—N1—C5—N2	−175.5 (4)	O3—S1—C11—C10	153.4 (3)
C2—N1—C5—N2	2.9 (6)	O4—S1—C11—C12	89.4 (4)
C3—N1—C5—N3	3.9 (6)	O5—S1—C11—C12	−150.5 (4)
C2—N1—C5—N3	−177.7 (3)	O3—S1—C11—C12	−30.8 (4)
C7—N2—C5—N1	179.5 (4)	C10—C11—C12—C13	−0.4 (7)
C7—N2—C5—N3	0.1 (7)	S1—C11—C12—C13	−176.2 (3)
C6—N3—C5—N1	−179.1 (4)	C9—C8—C13—C12	−2.9 (6)
C6—N3—C5—N2	0.3 (7)	N5—C8—C13—C12	179.3 (4)
C5—N3—C6—N4	−1.8 (7)	C11—C12—C13—C8	1.5 (7)
C5—N3—C6—Cl1	178.1 (3)	O7—Na1—O6—Na1ⁱ	171.9 (2)
C7—N4—C6—N3	2.6 (7)	O4—Na1—O6—Na1ⁱ	84.80 (11)
C7—N4—C6—Cl1	−177.4 (3)	O6ⁱ—Na1—O6—Na1ⁱ	0.0
Na1ⁱⁱ—Cl1—C6—N3	16.5 (4)	O8—Na1—O6—Na1ⁱ	−111.45 (12)
Na1ⁱⁱ—Cl1—C6—N4	−163.6 (2)	Cl1ⁱⁱ—Na1—O6—Na1ⁱ	156.93 (10)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4ⁱⁱⁱ	0.87 (2)	1.96 (3)	2.823 (5)	172 (5)
O2—H2···O3^iv	0.86 (3)	1.94 (3)	2.772 (4)	165 (4)
O6—H6A···O5^v	0.99	1.83	2.817 (4)	174
O6—H6B···N3ⁱⁱ	0.99	2.23	3.009 (5)	135
O7—H7A···O8^vi	0.87 (2)	2.02 (3)	2.861 (5)	164 (4)
O7—H7B···O2^iv	0.82 (2)	1.95 (2)	2.767 (4)	169 (5)
O8—H8A···O5ⁱ	0.80 (2)	2.03 (3)	2.797 (4)	162 (4)
O8—H8B···O3^v	0.82 (2)	2.15 (3)	2.907 (5)	154 (4)
N5—H5···O1ⁱⁱ	0.90 (4)	2.01 (4)	2.828 (5)	151 (4)

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

Experimental details

Crystal data
Chemical formula	[Na₂(C₁₃H₁₅ClN₅O₅S)₂(H₂O)₆]
M_r	931.72
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	7.5628 (7), 8.6274 (8), 15.532 (2)
α, β, γ (°)	97.348 (2), 93.363 (4), 102.410 (7)
V (Å³)	977.75 (18)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.50 × 0.04 × 0.04

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 2005)
T_min, T_max	0.834, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	8262, 3418, 1459
R_int	0.106
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.131, 0.87
No. of reflections	3418
No. of parameters	283
No. of restraints	20
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.52

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	173.5
O6—H6B···N3^iv	0.99	2.23	3.009 (5)	135.0
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)

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

Acknowledgements

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,

References

Candiani, G. & Frigerio, M. (2007). Chem. Med. Chem. 2, 292–296. CrossRef PubMed CAS Google Scholar
Hollink, E., Simanek, E. E. & Bergbreiter, D. E. (2005). Tetrahedron Lett. 46, 2005–2008. Web of Science CrossRef CAS Google Scholar
Konstantion, T. N. & Petrova, P. (2002). Dyes Pigm. 52, 115–120. Google Scholar
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Pages m847-m848

doi:10.1107/S1600536812023732

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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metal-organic compounds

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