Aqua­(2,2′-bipyridine-κ2N,N′){(E)-[(5-chloro-2-oxidobenzyl­idene)amino-κ2N,O]methane­sulfonato-κO}zinc

Deng, Y.-F.; Nie, X.; Zhang, C.-H.

doi:10.1107/S1600536812013050

metal-organic compounds

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Volume 68| Part 4| April 2012| Page m517

doi:10.1107/S1600536812013050

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Aqua(2,2′-bipyridine-κ²N,N′){(E)-[(5-chloro-2-oxidobenzylidene)amino-κ²N,O]methanesulfonato-κO}zinc

Yi-Fang Deng,^a ^* Xue Nie ^a and Chun-Hua Zhang ^a ^*

^aHengyang Normal University, Department of Chemistry and Materials Science, Hengyang, Hunan 421008, People's Republic of China
^*Correspondence e-mail: yifang7124@163.com, zhangchunhua668@163.com

(Received 10 March 2012; accepted 25 March 2012; online 31 March 2012)

In the title compound, [Zn(C₈H₆ClNO₄S)(C₁₀H₈N₂)(H₂O)], the Zn^II atom is six-coordinated by two O atoms and one N atom from a tridentate Schiff base ligand and two N atoms from a chelating 2,2′-bipyridine ligand and one water molecule, forming a slightly distorted octahedral geometry. In the crystal, O—H⋯O hydrogen bonds link pairs of complex molecules into dimers. An intramolecular O—H⋯O hydrogen bond is also present.

Related literature

For related complexes, see: He et al. (2007 ); Xu et al. (2007 ).

Experimental

Crystal data

[Zn(C₈H₆ClNO₄S)(C₁₀H₈N₂)(H₂O)]
M_r = 487.22
Triclinic, $[P \overline 1]$
a = 7.7332 (6) Å
b = 10.8948 (8) Å
c = 11.9112 (9) Å
α = 103.625 (1)°
β = 90.664 (2)°
γ = 98.993 (1)°
V = 962.08 (13) Å³
Z = 2
Mo Kα radiation
μ = 1.56 mm⁻¹
T = 296 K
0.18 × 0.14 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.766, T_max = 0.860
7155 measured reflections
3719 independent reflections
3345 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.077
S = 1.05
3719 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 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
O1W—H1WA⋯O4ⁱ	0.84 (3)	1.96 (3)	2.791 (2)	172 (3)
O1W—H1WB⋯O3	0.82	2.10	2.855 (2)	154
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812013050/hy2525sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013050/hy2525Isup2.hkl

checkCIF report

Comment top

Schiff base complexes containing amino acids have been studied for many years, arising interest because of their antiviral, anticancer and antibacterial activity. Herein, we choose amino-methanesulfonic acid-Schiff base to react with Zn(CH₃CO₂)₂.4H₂O as well as 2,2'-bipyridine. In the title compound, the Zn^II atom forms one five-membered and one six-membered chelating rings with the Schiff base ligand (Fig. 1). The coordinating environment of the Zn^II atom is different from that reported by He et al. (2007) and Xu et al. (2007). The bond length of Zn—O(sulfonate) is longer than that of Zn—O(aqua) and also longer than that of Zn—N(imine). It indicates that the coordinating capability of the sulfonate group is weaker than that of water and imine group. In the crystal, O—H···O hydrogen bonds link two complex molecules into a dimer (Table 1). An intramolecular O—H···O hydrogen bond is also present.

Related literature top

For related complexes, see: He et al. (2007); Xu et al. (2007).

Experimental top

The complex was prepared by mixing a methanol-water solution of 5-chlorosalicylaldelyde (1.0 mmol), aminomethanesulfonic acid (1.0 mmol) and potassium hydrate (1.0 mmol) with heating and stirring. After 2 h, an aqueous solution containing zinc acetate (1 mmol) was added dropwise under stirring. The pH value of the mixture was adjusted to 6 with 0.5 mol/L HCl solution, followed by the dropwise addition of a methanol solution containing 2,2'-bipyridine (1 mmol) with stirring. The resulting yellow filtrate was allowed to stand at room temperature and slowly evaporate for one month to afforded yellow block-shaped crystals.

Structure description top

For related complexes, see: He et al. (2007); Xu et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

Aqua(2,2'-bipyridine-κ²N,N'){(E)-[(5-chloro-2- oxidobenzylidene)amino-κ²N,O]methanesulfonato-κO}zinc top

Crystal data top

[Zn(C₈H₆ClNO₄S)(C₁₀H₈N₂)(H₂O)]	Z = 2
M_r = 487.22	F(000) = 496
Triclinic, P1	D_x = 1.682 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7332 (6) Å	Cell parameters from 4928 reflections
b = 10.8948 (8) Å	θ = 2.3–27.5°
c = 11.9112 (9) Å	µ = 1.56 mm⁻¹
α = 103.625 (1)°	T = 296 K
β = 90.664 (2)°	Block, yellow
γ = 98.993 (1)°	0.18 × 0.14 × 0.10 mm
V = 962.08 (13) Å³

Data collection top

Bruker APEX CCD diffractometer	3719 independent reflections
Radiation source: fine-focus sealed tube	3345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→9
T_min = 0.766, T_max = 0.860	k = −13→13
7155 measured reflections	l = −14→14

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.039P)² + 0.2378P] where P = (F_o² + 2F_c²)/3
3719 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Zn(C₈H₆ClNO₄S)(C₁₀H₈N₂)(H₂O)]	γ = 98.993 (1)°
M_r = 487.22	V = 962.08 (13) Å³
Triclinic, P1	Z = 2
a = 7.7332 (6) Å	Mo Kα radiation
b = 10.8948 (8) Å	µ = 1.56 mm⁻¹
c = 11.9112 (9) Å	T = 296 K
α = 103.625 (1)°	0.18 × 0.14 × 0.10 mm
β = 90.664 (2)°

Data collection top

Bruker APEX CCD diffractometer	3719 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3345 reflections with I > 2σ(I)
T_min = 0.766, T_max = 0.860	R_int = 0.026
7155 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.27 e Å⁻³
3719 reflections	Δρ_min = −0.52 e Å⁻³
267 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
Zn1	0.62092 (3)	0.62060 (2)	0.841029 (19)	0.03292 (9)
C1	0.8756 (3)	0.68019 (19)	1.04504 (17)	0.0312 (4)
C2	0.9837 (3)	0.6387 (2)	1.11991 (18)	0.0382 (5)
H2	0.9938	0.5524	1.1046	0.046*
C3	1.0741 (3)	0.7212 (2)	1.21429 (18)	0.0382 (5)
H3	1.1456	0.6911	1.2614	0.046*
C4	1.0588 (3)	0.8500 (2)	1.23969 (18)	0.0367 (5)
C5	0.9626 (3)	0.8967 (2)	1.16761 (18)	0.0343 (4)
H5	0.9573	0.9838	1.1839	0.041*
C6	0.8707 (2)	0.81353 (18)	1.06824 (17)	0.0298 (4)
C7	0.7749 (3)	0.87525 (18)	0.99868 (17)	0.0305 (4)
H7	0.7835	0.9637	1.0229	0.037*
C8	0.5976 (3)	0.90082 (19)	0.84771 (18)	0.0358 (5)
H8A	0.6656	0.9161	0.7830	0.043*
H8B	0.5928	0.9827	0.9007	0.043*
C9	0.8962 (3)	0.7207 (2)	0.6752 (2)	0.0458 (6)
H9	0.9395	0.7860	0.7392	0.055*
C10	0.9547 (3)	0.7293 (2)	0.5682 (2)	0.0515 (6)
H10	1.0374	0.7980	0.5600	0.062*
C11	0.8876 (3)	0.6336 (3)	0.4738 (2)	0.0500 (6)
H11	0.9206	0.6389	0.4001	0.060*
C12	0.7714 (3)	0.5298 (2)	0.48847 (19)	0.0407 (5)
H12	0.7273	0.4634	0.4254	0.049*
C13	0.7217 (2)	0.52624 (19)	0.59897 (17)	0.0298 (4)
C14	0.6071 (2)	0.41548 (18)	0.62564 (17)	0.0299 (4)
C15	0.5698 (3)	0.2974 (2)	0.54736 (19)	0.0393 (5)
H15	0.6097	0.2864	0.4729	0.047*
C16	0.4727 (3)	0.1964 (2)	0.5817 (2)	0.0467 (6)
H16	0.4458	0.1166	0.5302	0.056*
C17	0.4161 (3)	0.2143 (2)	0.6919 (2)	0.0495 (6)
H17	0.3520	0.1469	0.7167	0.059*
C18	0.4562 (3)	0.3343 (2)	0.7653 (2)	0.0419 (5)
H18	0.4170	0.3465	0.8400	0.050*
Cl1	1.15819 (9)	0.95211 (6)	1.36830 (5)	0.05451 (17)
H1WA	0.340 (4)	0.550 (3)	0.984 (2)	0.050 (8)*
N1	0.7798 (2)	0.62241 (16)	0.69110 (15)	0.0341 (4)
N2	0.5490 (2)	0.43414 (15)	0.73402 (14)	0.0315 (4)
N3	0.6788 (2)	0.81919 (15)	0.90636 (14)	0.0315 (4)
O1	0.4109 (2)	0.69189 (14)	0.73855 (13)	0.0399 (4)
O2	0.3186 (2)	0.89098 (16)	0.72147 (16)	0.0539 (4)
O3	0.2802 (2)	0.81929 (16)	0.89951 (15)	0.0504 (4)
O4	0.7824 (2)	0.59406 (13)	0.96069 (12)	0.0381 (3)
O1W	0.3995 (2)	0.60387 (17)	0.95374 (16)	0.0495 (4)
H1WB	0.3365	0.6563	0.9481	0.074*
S1	0.38106 (7)	0.82061 (5)	0.79767 (5)	0.03552 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.04229 (15)	0.02405 (14)	0.02831 (14)	0.00326 (10)	−0.00157 (10)	−0.00023 (10)
C1	0.0363 (10)	0.0297 (10)	0.0269 (10)	0.0079 (8)	0.0033 (8)	0.0039 (8)
C2	0.0467 (12)	0.0351 (11)	0.0361 (11)	0.0177 (9)	0.0029 (9)	0.0078 (9)
C3	0.0365 (11)	0.0483 (13)	0.0330 (11)	0.0121 (9)	−0.0015 (9)	0.0127 (10)
C4	0.0355 (11)	0.0407 (12)	0.0302 (11)	−0.0001 (9)	−0.0058 (8)	0.0060 (9)
C5	0.0378 (11)	0.0279 (10)	0.0346 (11)	0.0012 (8)	−0.0033 (8)	0.0052 (8)
C6	0.0316 (10)	0.0268 (10)	0.0293 (10)	0.0033 (8)	−0.0009 (8)	0.0044 (8)
C7	0.0344 (10)	0.0221 (9)	0.0320 (10)	0.0023 (8)	−0.0019 (8)	0.0022 (8)
C8	0.0432 (11)	0.0285 (10)	0.0351 (11)	0.0029 (9)	−0.0066 (9)	0.0089 (9)
C9	0.0433 (12)	0.0347 (12)	0.0544 (15)	−0.0009 (10)	0.0061 (11)	0.0053 (10)
C10	0.0452 (13)	0.0442 (14)	0.0691 (17)	0.0052 (11)	0.0157 (12)	0.0223 (13)
C11	0.0506 (14)	0.0620 (16)	0.0459 (14)	0.0147 (12)	0.0137 (11)	0.0255 (12)
C12	0.0427 (12)	0.0491 (13)	0.0316 (11)	0.0126 (10)	−0.0002 (9)	0.0091 (10)
C13	0.0291 (9)	0.0311 (10)	0.0297 (10)	0.0089 (8)	−0.0020 (8)	0.0057 (8)
C14	0.0279 (9)	0.0298 (10)	0.0298 (10)	0.0058 (8)	−0.0046 (8)	0.0022 (8)
C15	0.0435 (12)	0.0357 (12)	0.0330 (11)	0.0064 (9)	−0.0040 (9)	−0.0025 (9)
C16	0.0468 (13)	0.0305 (12)	0.0524 (14)	0.0001 (10)	−0.0051 (11)	−0.0061 (10)
C17	0.0467 (13)	0.0311 (12)	0.0643 (16)	−0.0058 (10)	0.0063 (12)	0.0069 (11)
C18	0.0437 (12)	0.0353 (12)	0.0439 (13)	0.0006 (9)	0.0102 (10)	0.0076 (10)
Cl1	0.0662 (4)	0.0497 (4)	0.0402 (3)	−0.0031 (3)	−0.0221 (3)	0.0057 (3)
N1	0.0362 (9)	0.0283 (9)	0.0346 (9)	0.0031 (7)	0.0010 (7)	0.0028 (7)
N2	0.0331 (8)	0.0270 (9)	0.0313 (9)	0.0035 (7)	0.0022 (7)	0.0019 (7)
N3	0.0369 (9)	0.0246 (8)	0.0321 (9)	0.0045 (7)	−0.0043 (7)	0.0058 (7)
O1	0.0480 (9)	0.0319 (8)	0.0350 (8)	0.0072 (6)	−0.0069 (7)	−0.0015 (6)
O2	0.0584 (10)	0.0472 (10)	0.0587 (11)	0.0110 (8)	−0.0202 (8)	0.0173 (8)
O3	0.0540 (10)	0.0400 (9)	0.0562 (11)	0.0119 (8)	0.0149 (8)	0.0062 (8)
O4	0.0517 (9)	0.0242 (7)	0.0351 (8)	0.0062 (6)	−0.0060 (7)	0.0010 (6)
O1W	0.0585 (11)	0.0410 (10)	0.0561 (11)	0.0136 (8)	0.0200 (9)	0.0211 (8)
S1	0.0397 (3)	0.0292 (3)	0.0357 (3)	0.0067 (2)	−0.0064 (2)	0.0036 (2)

Geometric parameters (Å, º) top

Zn1—O4	1.9851 (15)	C9—C10	1.376 (3)
Zn1—N3	2.0936 (16)	C9—H9	0.9300
Zn1—N2	2.1144 (16)	C10—C11	1.372 (4)
Zn1—N1	2.1817 (18)	C10—H10	0.9300
Zn1—O1W	2.1999 (17)	C11—C12	1.377 (3)
Zn1—O1	2.3507 (15)	C11—H11	0.9300
C1—O4	1.318 (2)	C12—C13	1.383 (3)
C1—C2	1.411 (3)	C12—H12	0.9300
C1—C6	1.420 (3)	C13—N1	1.343 (3)
C2—C3	1.367 (3)	C13—C14	1.482 (3)
C2—H2	0.9300	C14—N2	1.352 (3)
C3—C4	1.388 (3)	C14—C15	1.386 (3)
C3—H3	0.9300	C15—C16	1.379 (3)
C4—C5	1.364 (3)	C15—H15	0.9300
C4—Cl1	1.754 (2)	C16—C17	1.368 (3)
C5—C6	1.414 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.378 (3)
C6—C7	1.446 (3)	C17—H17	0.9300
C7—N3	1.287 (2)	C18—N2	1.338 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—N3	1.459 (3)	O1—S1	1.4682 (15)
C8—S1	1.788 (2)	O2—S1	1.4416 (17)
C8—H8A	0.9700	O3—S1	1.4513 (17)
C8—H8B	0.9700	O1W—H1WA	0.84 (3)
C9—N1	1.338 (3)	O1W—H1WB	0.8200

O4—Zn1—N3	90.71 (6)	C11—C10—H10	120.9
O4—Zn1—N2	102.79 (6)	C9—C10—H10	120.9
N3—Zn1—N2	164.81 (7)	C10—C11—C12	120.0 (2)
O4—Zn1—N1	104.54 (7)	C10—C11—H11	120.0
N3—Zn1—N1	93.88 (6)	C12—C11—H11	120.0
N2—Zn1—N1	76.17 (6)	C11—C12—C13	118.6 (2)
O4—Zn1—O1W	90.69 (7)	C11—C12—H12	120.7
N3—Zn1—O1W	92.08 (7)	C13—C12—H12	120.7
N2—Zn1—O1W	94.66 (7)	N1—C13—C12	121.86 (19)
N1—Zn1—O1W	163.55 (7)	N1—C13—C14	115.00 (17)
O4—Zn1—O1	165.47 (5)	C12—C13—C14	123.10 (18)
N3—Zn1—O1	78.29 (6)	N2—C14—C15	121.59 (19)
N2—Zn1—O1	89.43 (6)	N2—C14—C13	115.84 (16)
N1—Zn1—O1	85.85 (6)	C15—C14—C13	122.45 (19)
O1W—Zn1—O1	80.36 (6)	C16—C15—C14	119.0 (2)
O4—C1—C2	118.78 (18)	C16—C15—H15	120.5
O4—C1—C6	124.10 (18)	C14—C15—H15	120.5
C2—C1—C6	117.09 (18)	C17—C16—C15	119.6 (2)
C3—C2—C1	122.1 (2)	C17—C16—H16	120.2
C3—C2—H2	118.9	C15—C16—H16	120.2
C1—C2—H2	118.9	C16—C17—C18	118.6 (2)
C2—C3—C4	119.88 (19)	C16—C17—H17	120.7
C2—C3—H3	120.1	C18—C17—H17	120.7
C4—C3—H3	120.1	N2—C18—C17	123.0 (2)
C5—C4—C3	120.61 (19)	N2—C18—H18	118.5
C5—C4—Cl1	119.85 (17)	C17—C18—H18	118.5
C3—C4—Cl1	119.50 (16)	C9—N1—C13	118.41 (19)
C4—C5—C6	120.4 (2)	C9—N1—Zn1	126.34 (15)
C4—C5—H5	119.8	C13—N1—Zn1	113.33 (13)
C6—C5—H5	119.8	C18—N2—C14	118.20 (17)
C5—C6—C1	119.71 (18)	C18—N2—Zn1	125.78 (14)
C5—C6—C7	114.88 (17)	C14—N2—Zn1	116.00 (13)
C1—C6—C7	125.40 (17)	C7—N3—C8	116.93 (17)
N3—C7—C6	126.09 (18)	C7—N3—Zn1	124.61 (14)
N3—C7—H7	117.0	C8—N3—Zn1	118.37 (13)
C6—C7—H7	117.0	S1—O1—Zn1	111.64 (8)
N3—C8—S1	107.87 (14)	C1—O4—Zn1	128.73 (13)
N3—C8—H8A	110.1	Zn1—O1W—H1WA	140.4 (18)
S1—C8—H8A	110.1	Zn1—O1W—H1WB	109.5
N3—C8—H8B	110.1	H1WA—O1W—H1WB	106.3
S1—C8—H8B	110.1	O2—S1—O3	114.48 (11)
H8A—C8—H8B	108.4	O2—S1—O1	113.83 (10)
N1—C9—C10	122.9 (2)	O3—S1—O1	111.93 (10)
N1—C9—H9	118.6	O2—S1—C8	106.08 (10)
C10—C9—H9	118.6	O3—S1—C8	106.82 (10)
C11—C10—C9	118.2 (2)	O1—S1—C8	102.52 (9)

O4—C1—C2—C3	−175.1 (2)	C15—C14—N2—C18	1.2 (3)
C6—C1—C2—C3	3.1 (3)	C13—C14—N2—C18	−174.98 (18)
C1—C2—C3—C4	0.9 (3)	C15—C14—N2—Zn1	179.59 (15)
C2—C3—C4—C5	−3.9 (3)	C13—C14—N2—Zn1	3.4 (2)
C2—C3—C4—Cl1	173.90 (17)	O4—Zn1—N2—C18	65.54 (19)
C3—C4—C5—C6	2.6 (3)	N3—Zn1—N2—C18	−142.3 (2)
Cl1—C4—C5—C6	−175.13 (16)	N1—Zn1—N2—C18	167.61 (19)
C4—C5—C6—C1	1.5 (3)	O1W—Zn1—N2—C18	−26.24 (19)
C4—C5—C6—C7	−179.6 (2)	O1—Zn1—N2—C18	−106.52 (18)
O4—C1—C6—C5	173.83 (19)	O4—Zn1—N2—C14	−112.71 (14)
C2—C1—C6—C5	−4.3 (3)	N3—Zn1—N2—C14	39.5 (3)
O4—C1—C6—C7	−5.0 (3)	N1—Zn1—N2—C14	−10.64 (13)
C2—C1—C6—C7	176.93 (19)	O1W—Zn1—N2—C14	155.51 (14)
C5—C6—C7—N3	−178.2 (2)	O1—Zn1—N2—C14	75.23 (14)
C1—C6—C7—N3	0.6 (3)	C6—C7—N3—C8	−178.30 (19)
N1—C9—C10—C11	1.2 (4)	C6—C7—N3—Zn1	5.2 (3)
C9—C10—C11—C12	−3.0 (4)	S1—C8—N3—C7	−140.80 (16)
C10—C11—C12—C13	1.6 (4)	S1—C8—N3—Zn1	35.87 (18)
C11—C12—C13—N1	1.8 (3)	O4—Zn1—N3—C7	−5.63 (17)
C11—C12—C13—C14	−175.8 (2)	N2—Zn1—N3—C7	−158.6 (2)
N1—C13—C14—N2	11.9 (2)	N1—Zn1—N3—C7	−110.26 (17)
C12—C13—C14—N2	−170.33 (19)	O1W—Zn1—N3—C7	85.09 (17)
N1—C13—C14—C15	−164.25 (19)	O1—Zn1—N3—C7	164.80 (18)
C12—C13—C14—C15	13.5 (3)	O4—Zn1—N3—C8	177.97 (15)
N2—C14—C15—C16	−0.7 (3)	N2—Zn1—N3—C8	25.0 (3)
C13—C14—C15—C16	175.22 (19)	N1—Zn1—N3—C8	73.34 (15)
C14—C15—C16—C17	−0.4 (4)	O1W—Zn1—N3—C8	−91.31 (15)
C15—C16—C17—C18	0.9 (4)	O1—Zn1—N3—C8	−11.60 (14)
C16—C17—C18—N2	−0.4 (4)	O4—Zn1—O1—S1	20.4 (3)
C10—C9—N1—C13	2.1 (3)	N3—Zn1—O1—S1	−21.04 (9)
C10—C9—N1—Zn1	−161.05 (18)	N2—Zn1—O1—S1	167.95 (10)
C12—C13—N1—C9	−3.6 (3)	N1—Zn1—O1—S1	−115.88 (10)
C14—C13—N1—C9	174.19 (19)	O1W—Zn1—O1—S1	73.13 (10)
C12—C13—N1—Zn1	161.63 (16)	C2—C1—O4—Zn1	−179.41 (14)
C14—C13—N1—Zn1	−20.6 (2)	C6—C1—O4—Zn1	2.5 (3)
O4—Zn1—N1—C9	−79.2 (2)	N3—Zn1—O4—C1	1.91 (17)
N3—Zn1—N1—C9	12.5 (2)	N2—Zn1—O4—C1	174.89 (17)
N2—Zn1—N1—C9	−179.1 (2)	N1—Zn1—O4—C1	96.10 (17)
O1W—Zn1—N1—C9	123.5 (2)	O1W—Zn1—O4—C1	−90.18 (17)
O1—Zn1—N1—C9	90.44 (19)	O1—Zn1—O4—C1	−38.5 (3)
O4—Zn1—N1—C13	116.92 (14)	Zn1—O1—S1—O2	154.40 (10)
N3—Zn1—N1—C13	−151.34 (14)	Zn1—O1—S1—O3	−73.84 (11)
N2—Zn1—N1—C13	17.03 (13)	Zn1—O1—S1—C8	40.30 (11)
O1W—Zn1—N1—C13	−40.4 (3)	N3—C8—S1—O2	−168.93 (14)
O1—Zn1—N1—C13	−73.40 (14)	N3—C8—S1—O3	68.55 (16)
C17—C18—N2—C14	−0.6 (3)	N3—C8—S1—O1	−49.28 (16)
C17—C18—N2—Zn1	−178.84 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4ⁱ	0.84 (3)	1.96 (3)	2.791 (2)	172 (3)
O1W—H1WB···O3	0.82	2.10	2.855 (2)	154

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₆ClNO₄S)(C₁₀H₈N₂)(H₂O)]
M_r	487.22
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.7332 (6), 10.8948 (8), 11.9112 (9)
α, β, γ (°)	103.625 (1), 90.664 (2), 98.993 (1)
V (Å³)	962.08 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.18 × 0.14 × 0.10

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.766, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	7155, 3719, 3345
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.077, 1.05
No. of reflections	3719
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.52

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4ⁱ	0.84 (3)	1.96 (3)	2.791 (2)	172 (3)
O1W—H1WB···O3	0.82	2.10	2.855 (2)	154

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

This work was supported by the Open Fund Project of Key Laboratories in Hunan Universities (11 K009).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
He, K.-H., Li, J.-M. & Jiang, Y.-M. (2007). Acta Cryst. E63, m2992–m2993. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, J.-S., Zhang, C.-H., Kuang, D.-Z., Feng, Y.-L. & Peng, Y.-L. (2007). Acta Cryst. E63, m2250. Web of Science CSD CrossRef IUCr Journals Google Scholar

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