Tetra­aqua­bis(2-oxo-1,2-dihydro­pyridine-5-sulfonato-κO2)zinc(II)

Zhu, Z.-B.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536809039774

metal-organic compounds

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Volume 65| Part 11| November 2009| Page m1310

https://doi.org/10.1107/S1600536809039774

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Tetraaquabis(2-oxo-1,2-dihydropyridine-5-sulfonato-κO²)zinc(II)

Zhi-Biao Zhu,^a Shan Gao ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 28 September 2009; accepted 30 September 2009; online 7 October 2009)

The metal atom in the title compound, [Zn(C₅H₄NO₄S)₂(H₂O)₄], lies on a center of inversion and is linked to the anionic ligand through the carbonyl O atom. In the crystal structure, the 2-oxo-1,2-dihydropyridine-5-sulfonate ligand interacts with other molecules through N—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional network structure.

Related literature

For the crystal structure of another zwitterionic tetraaquabis(amide)–metal^II complex, see: Gao et al. (2004 ).

Experimental

Crystal data

[Zn(C₅H₄NO₄S)₂(H₂O)₄]
M_r = 485.74
Monoclinic, P 2₁ /c
a = 6.7701 (2) Å
b = 13.9725 (5) Å
c = 10.0343 (3) Å
β = 115.331 (2)°
V = 857.93 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.74 mm⁻¹
T = 293 K
0.21 × 0.16 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.711, T_max = 0.768
8224 measured reflections
1951 independent reflections
1866 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.066
S = 1.06
1951 reflections
144 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.85 (1)	1.99 (1)	2.790 (2)	157 (2)
O1w—H11⋯O2ⁱⁱ	0.84 (1)	1.98 (1)	2.809 (2)	171 (2)
O1w—H12⋯O3ⁱⁱⁱ	0.84 (1)	1.93 (1)	2.767 (2)	172 (3)
O2w—H21⋯O3^iv	0.83 (1)	2.13 (1)	2.926 (2)	160 (3)
O2w—H22⋯O4^v	0.84 (1)	1.93 (1)	2.765 (2)	174 (3)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) x, y, z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039774/xu2623sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039774/xu2623Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of another zwitterionic tetraaquabis(amide)metal^II complex, see: Gao et al. (2004).

Experimental top

Zinc carbonate (0.25 g, 2 mmol) was added to a hot aqueous solution of 2-hydroxypyridine 5-sulfonic acid (0.35 g, 2 mmol); the pH value was adjusted to 6 with 0.1 M sodium hydroxide. The solution was allowed to evaporate slowly. Colorless prismatic crystals were isolated after five days. CH&N elemental analysis. Calc. for C₁₀H₁₆N₂O₁₂S₂Zn:C 24.73, H 3.32, N 5.77%; found: C 24.77, H 3.37, N 5.81%.

Structure description top

For the crystal structure of another zwitterionic tetraaquabis(amide)metal^II complex, see: Gao et al. (2004).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Zn(H₂O)₄(C₅H₄NO₄S)₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Tetraaquabis(2-oxo-1,2-dihydropyridine-5-sulfonato-κO²)zinc(II) top

Crystal data top

[Zn(C₅H₄NO₄S)₂(H₂O)₄]	F(000) = 496
M_r = 485.74	D_x = 1.880 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7685 reflections
a = 6.7701 (2) Å	θ = 3.3–27.5°
b = 13.9725 (5) Å	µ = 1.74 mm⁻¹
c = 10.0343 (3) Å	T = 293 K
β = 115.331 (2)°	Prism, colorles
V = 857.93 (5) Å³	0.21 × 0.16 × 0.16 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1951 independent reflections
Radiation source: fine-focus sealed tube	1866 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
T_min = 0.711, T_max = 0.768	k = −17→18
8224 measured reflections	l = −13→13

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.037P)² + 0.5079P] where P = (F_o² + 2F_c²)/3
1951 reflections	(Δ/σ)_max = 0.001
144 parameters	Δρ_max = 0.37 e Å⁻³
5 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Zn(C₅H₄NO₄S)₂(H₂O)₄]	V = 857.93 (5) Å³
M_r = 485.74	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.7701 (2) Å	µ = 1.74 mm⁻¹
b = 13.9725 (5) Å	T = 293 K
c = 10.0343 (3) Å	0.21 × 0.16 × 0.16 mm
β = 115.331 (2)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1951 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1866 reflections with I > 2σ(I)
T_min = 0.711, T_max = 0.768	R_int = 0.021
8224 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	5 restraints
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.37 e Å⁻³
1951 reflections	Δρ_min = −0.39 e Å⁻³
144 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.5000	0.5000	0.5000	0.02207 (10)
S1	0.81951 (6)	0.69216 (3)	−0.07941 (4)	0.01923 (11)
O1	0.4186 (2)	0.54472 (10)	0.28771 (14)	0.0295 (3)
O3	0.9550 (2)	0.77155 (9)	0.00655 (14)	0.0290 (3)
O2	0.95353 (19)	0.61832 (9)	−0.10431 (13)	0.0264 (3)
O4	0.63570 (19)	0.72213 (9)	−0.21315 (13)	0.0271 (3)
O1W	0.20020 (19)	0.43039 (9)	0.40362 (13)	0.0252 (2)
O2W	0.3496 (2)	0.62596 (11)	0.53828 (17)	0.0406 (3)
C2	0.7484 (3)	0.55821 (12)	0.25390 (18)	0.0234 (3)
H2	0.8360	0.5271	0.3413	0.028*
C1	0.5190 (3)	0.56850 (11)	0.21274 (17)	0.0214 (3)
N1	0.4007 (2)	0.60683 (10)	0.07675 (15)	0.0229 (3)
C5	0.4880 (2)	0.64352 (13)	−0.01119 (17)	0.0221 (3)
H5	0.3979	0.6715	−0.1009	0.027*
C4	0.7072 (2)	0.63937 (11)	0.03179 (17)	0.0201 (3)
C3	0.8395 (3)	0.59340 (11)	0.16668 (18)	0.0227 (3)
H3	0.9891	0.5873	0.1956	0.027*
H1	0.2625 (16)	0.6084 (16)	0.045 (2)	0.035 (6)*
H11	0.158 (4)	0.4218 (18)	0.3125 (12)	0.048 (7)*
H12	0.166 (4)	0.3815 (12)	0.438 (3)	0.045 (7)*
H21	0.223 (2)	0.6479 (18)	0.509 (3)	0.051 (7)*
H22	0.431 (4)	0.6538 (17)	0.6168 (18)	0.049 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02021 (15)	0.02605 (16)	0.02093 (15)	−0.00103 (9)	0.00973 (11)	0.00145 (9)
S1	0.01744 (18)	0.02194 (19)	0.01890 (19)	−0.00059 (13)	0.00834 (14)	0.00027 (13)
O1	0.0244 (6)	0.0417 (7)	0.0246 (6)	−0.0023 (5)	0.0125 (5)	0.0061 (5)
O3	0.0276 (6)	0.0281 (6)	0.0320 (7)	−0.0085 (5)	0.0133 (5)	−0.0060 (5)
O2	0.0222 (5)	0.0329 (6)	0.0252 (6)	0.0046 (5)	0.0111 (5)	−0.0021 (5)
O4	0.0241 (6)	0.0313 (6)	0.0233 (6)	0.0017 (5)	0.0076 (5)	0.0071 (5)
O1W	0.0249 (6)	0.0286 (6)	0.0223 (6)	−0.0043 (5)	0.0104 (5)	0.0014 (5)
O2W	0.0268 (7)	0.0401 (8)	0.0447 (8)	0.0077 (6)	0.0056 (6)	−0.0145 (6)
C2	0.0214 (7)	0.0268 (8)	0.0198 (7)	0.0036 (6)	0.0069 (6)	0.0030 (6)
C1	0.0223 (7)	0.0218 (7)	0.0204 (7)	−0.0023 (6)	0.0094 (6)	−0.0005 (6)
N1	0.0151 (6)	0.0316 (7)	0.0216 (7)	−0.0009 (5)	0.0074 (5)	0.0019 (5)
C5	0.0203 (7)	0.0264 (8)	0.0190 (7)	0.0007 (6)	0.0079 (6)	0.0024 (5)
C4	0.0198 (7)	0.0215 (7)	0.0204 (7)	−0.0012 (6)	0.0101 (6)	−0.0006 (5)
C3	0.0178 (7)	0.0266 (8)	0.0229 (8)	0.0021 (6)	0.0078 (6)	0.0001 (6)

Geometric parameters (Å, º) top

Zn1—O1ⁱ	2.0560 (12)	O2W—H21	0.833 (10)
Zn1—O1	2.0560 (12)	O2W—H22	0.838 (10)
Zn1—O1Wⁱ	2.0788 (12)	C2—C3	1.360 (2)
Zn1—O1W	2.0788 (12)	C2—C1	1.434 (2)
Zn1—O2W	2.1487 (14)	C2—H2	0.9300
Zn1—O2Wⁱ	2.1487 (14)	C1—N1	1.362 (2)
S1—O4	1.4477 (12)	N1—C5	1.356 (2)
S1—O3	1.4626 (12)	N1—H1	0.850 (10)
S1—O2	1.4643 (12)	C5—C4	1.358 (2)
S1—C4	1.7588 (15)	C5—H5	0.9300
O1—C1	1.2553 (19)	C4—C3	1.418 (2)
O1W—H11	0.841 (10)	C3—H3	0.9300
O1W—H12	0.841 (10)

O1ⁱ—Zn1—O1	180.0	Zn1—O1W—H12	125.1 (18)
O1ⁱ—Zn1—O1Wⁱ	83.37 (5)	H11—O1W—H12	108 (2)
O1—Zn1—O1Wⁱ	96.63 (5)	Zn1—O2W—H21	137.0 (19)
O1ⁱ—Zn1—O1W	96.63 (5)	Zn1—O2W—H22	112.2 (18)
O1—Zn1—O1W	83.37 (5)	H21—O2W—H22	109 (3)
O1Wⁱ—Zn1—O1W	180.00 (6)	C3—C2—C1	120.81 (15)
O1ⁱ—Zn1—O2W	90.07 (6)	C3—C2—H2	119.6
O1—Zn1—O2W	89.93 (6)	C1—C2—H2	119.6
O1Wⁱ—Zn1—O2W	88.66 (5)	O1—C1—N1	117.88 (14)
O1W—Zn1—O2W	91.34 (5)	O1—C1—C2	126.76 (15)
O1ⁱ—Zn1—O2Wⁱ	89.93 (6)	N1—C1—C2	115.35 (14)
O1—Zn1—O2Wⁱ	90.07 (6)	C5—N1—C1	124.58 (13)
O1Wⁱ—Zn1—O2Wⁱ	91.34 (5)	C5—N1—H1	117.5 (16)
O1W—Zn1—O2Wⁱ	88.66 (5)	C1—N1—H1	118.0 (16)
O2W—Zn1—O2Wⁱ	180.0	N1—C5—C4	119.93 (14)
O4—S1—O3	113.63 (8)	N1—C5—H5	120.0
O4—S1—O2	113.28 (7)	C4—C5—H5	120.0
O3—S1—O2	110.91 (7)	C5—C4—C3	118.76 (14)
O4—S1—C4	106.01 (7)	C5—C4—S1	119.40 (12)
O3—S1—C4	106.05 (7)	C3—C4—S1	121.84 (12)
O2—S1—C4	106.28 (7)	C2—C3—C4	120.17 (14)
C1—O1—Zn1	136.67 (11)	C2—C3—H3	119.9
Zn1—O1W—H11	112.6 (17)	C4—C3—H3	119.9

O1Wⁱ—Zn1—O1—C1	28.28 (18)	N1—C5—C4—C3	2.1 (2)
O1W—Zn1—O1—C1	−151.72 (18)	N1—C5—C4—S1	−177.08 (12)
O2W—Zn1—O1—C1	116.92 (17)	O4—S1—C4—C5	−6.85 (15)
O2Wⁱ—Zn1—O1—C1	−63.08 (17)	O3—S1—C4—C5	114.25 (14)
Zn1—O1—C1—N1	−171.26 (12)	O2—S1—C4—C5	−127.66 (13)
Zn1—O1—C1—C2	9.9 (3)	O4—S1—C4—C3	173.98 (13)
C3—C2—C1—O1	−175.15 (17)	O3—S1—C4—C3	−64.92 (15)
C3—C2—C1—N1	6.0 (2)	O2—S1—C4—C3	53.17 (15)
O1—C1—N1—C5	173.90 (16)	C1—C2—C3—C4	−1.2 (2)
C2—C1—N1—C5	−7.1 (2)	C5—C4—C3—C2	−3.0 (2)
C1—N1—C5—C4	3.2 (3)	S1—C4—C3—C2	176.21 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱⁱ	0.85 (1)	1.99 (1)	2.790 (2)	157 (2)
O1w—H11···O2ⁱⁱⁱ	0.84 (1)	1.98 (1)	2.809 (2)	171 (2)
O1w—H12···O3^iv	0.84 (1)	1.93 (1)	2.767 (2)	172 (3)
O2w—H21···O3^v	0.83 (1)	2.13 (1)	2.926 (2)	160 (3)
O2w—H22···O4^vi	0.84 (1)	1.93 (1)	2.765 (2)	174 (3)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₅H₄NO₄S)₂(H₂O)₄]
M_r	485.74
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.7701 (2), 13.9725 (5), 10.0343 (3)
β (°)	115.331 (2)
V (Å³)	857.93 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.74
Crystal size (mm)	0.21 × 0.16 × 0.16

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.711, 0.768
No. of measured, independent and observed [I > 2σ(I)] reflections	8224, 1951, 1866
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.066, 1.06
No. of reflections	1951
No. of parameters	144
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.39

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.85 (1)	1.99 (1)	2.790 (2)	157 (2)
O1w—H11···O2ⁱⁱ	0.84 (1)	1.98 (1)	2.809 (2)	171 (2)
O1w—H12···O3ⁱⁱⁱ	0.84 (1)	1.93 (1)	2.767 (2)	172 (3)
O2w—H21···O3^iv	0.83 (1)	2.13 (1)	2.926 (2)	160 (3)
O2w—H22···O4^v	0.84 (1)	1.93 (1)	2.765 (2)	174 (3)

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

Acknowledgements

We thank the Natural Science Foundation of Heilongjiang Province (No. B200501), Heilongjiang University, China, and the University of Malaya for supporting this study.

References

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