Diaqua­bis(3,7-dichloro­quinoline-8-carboxyl­ato)zinc(II) monohydrate

An, L.-T.; Zhou, J.; Zhou, J.-F.; Xia, M.

doi:10.1107/S1600536808025671

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1170

doi:10.1107/S1600536808025671

Open

access

Diaquabis(3,7-dichloroquinoline-8-carboxylato)zinc(II) monohydrate

Li-Tao An,^a ^* Jian Zhou,^b Jian-Feng Zhou ^a and Min Xia ^a

^aJiangsu Key Laboratory for Chemistry of Low-dimensional Materials, Department of Chemistry, Huaiyin Teachers College, Huaian 223300, Jiangsu Province, People's Republic of China, and ^bDepartment of Chemistry and Biology, Yulin Normal University, Yulin 537000, People's Republic of China
^*Correspondence e-mail: annleet@126.com

(Received 7 August 2008; accepted 8 August 2008; online 16 August 2008)

In the title compound, [Zn(C₁₀H₄Cl₂NO₂)₂(H₂O)₂]·H₂O, the Zn atom has a distorted square-pyramidal geometry comprising two O atoms and one N atom from two distinct 3,7-dichloroquinoline-8-carboxylate ligands, and two water molecules. The free water molecules are involved in intermolecular O—H⋯O hydrogen bonding with the coordinated water molecules and carboxylate O atoms, to give a one-dimensional helical chain along the [100] direction.

Related literature

For related literature, see: Adnan et al. (2003 ); Che et al. (2005 ); Chen et al. (2001 ); Li et al. (2008 ); Lumme et al. (1984 ); Yang et al. (2005 ); Zhang et al. (2007 ).

Experimental

Crystal data

[Zn(C₁₀H₄Cl₂NO₂)₂(H₂O)₂]·H₂O
M_r = 601.50
Triclinic, $[P \overline 1]$
a = 6.8678 (3) Å
b = 12.6996 (5) Å
c = 12.9317 (5) Å
α = 87.572 (1)°
β = 82.893 (1)°
γ = 82.255 (1)°
V = 1108.63 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.64 mm⁻¹
T = 296 (2) K
0.21 × 0.17 × 0.15 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001 ) T_min = 0.725, T_max = 0.791
14022 measured reflections
4308 independent reflections
3099 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.094
S = 0.97
4308 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 1.20 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1ⁱ	0.85	2.05	2.889 (4)	166
O5—H5B⋯N2	0.86	2.16	3.002 (4)	169
O6—H6A⋯O4ⁱⁱ	0.85	1.78	2.628 (4)	174
O6—H6B⋯O7ⁱⁱⁱ	0.85	1.87	2.677 (4)	156
O7—H7B⋯O2^iv	0.85	2.04	2.827 (4)	153
O7—H7C⋯O1^v	0.85	2.25	3.029 (4)	153
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x+1, y, z; (iii) x, y+1, z; (iv) -x+1, -y+1, -z+1; (v) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025671/sg2255sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025671/sg2255Isup2.hkl

checkCIF report

Comment top

Quinolinecarboxylate derivatives and their complexes have attracted considerable interest, because of their interesting high germicidal, antitumoral and pharmacological properties (Adnan et al., 2003; Lumme et al., 1984). Although some transition metal complexes of quinolinecarboxylate ligands have been reported (Che et al., 2005; Chen et al., 2001; Yang et al., 2005), the crystal structures of the 3,7-Dichloro-8-quinolinecarboxylate and its complexes are limited in number, the only two examples are [M(C₁₀H₄Cl₂NO₂)₂]_n(M = Ni, Co) (Li et al., 2008; Zhang et al., 2007). we report herein on the structure of [Zn(C₁₀H₄Cl₂NO₂)₂(H₂O)₂].H₂O, (I).

The title complex, (I) crystallizes in the triclinic space group P1, with free water molecules in the crystal structure.The Zn(II) center exhibits a distorted square-pyramidal geometry defined by two O atoms and one N atom from two distinct 3,7-Dichloro-8-quinolinecarboxylate ligands, and two water molecules (Fig.1). The N1, O1, O3 and O5 atoms form the base plane, while the O6 atom occupies the axial position.The carboxylate group is bound in a monodentate fashion, with a weak intramolecular O—H···O H-bond between the carboxylate O atom and water molecules. The [Zn(C₁₀H₄Cl₂NO₂)₂(H₂O)₂] molecules are linked via these H-bond interactions into a 1-D helical chain along the [100] direction (Fig. 2).

Related literature top

For related literature, see: Adnan et al. (2003); Che et al. (2005); Chen et al. (2001); Li et al. (2008); Lumme et al. (1984); Yang et al. (2005); Zhang et al. (2007).

Experimental top

The source materials of Zinc hydroxide (0.005 g) and Quinclorac (3,7-Dichloro-8-quinolinecarboxylic acid) (0.024 g) dissolved in 10 ml distilled water and were carefully mixed, and then loaded into a Teflon-lined stainless steel autoclave. The sealed autoclave was heated to 433 K and maintained at this temperature for 48 h. After cooling to room temperature, then some colorless column crystal was obtained.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear (Rigaku/MSC, 2001); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), with the atomic numbering scheme and displacement ellipsoids at the 50% probability level. All H atoms have been omitted for clarity.
	Fig. 2. Part of the crystal structure of (I), showing the 1-D helical chain.H atoms bonded to C atoms have been omitted for clarity.

Diaquabis(3,7-dichloroquinoline-8-carboxylato)zinc(II) monohydrate top

Crystal data top

[Zn(C₁₀H₄Cl₂NO₂)₂(H₂O)₂]·H₂O	Z = 2
M_r = 601.50	F(000) = 604
Triclinic, P1	D_x = 1.802 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8678 (3) Å	Cell parameters from 1973 reflections
b = 12.6996 (5) Å	θ = 1.6–26.0°
c = 12.9317 (5) Å	µ = 1.64 mm⁻¹
α = 87.572 (1)°	T = 296 K
β = 82.893 (1)°	Column, colourless
γ = 82.255 (1)°	0.21 × 0.17 × 0.15 mm
V = 1108.63 (8) Å³

Data collection top

Rigaku Mercury diffractometer	4308 independent reflections
Radiation source: fine-focus sealed tube	3099 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
Detector resolution: 7.31 pixels mm^-1	θ_max = 26.0°, θ_min = 1.6°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	k = −15→15
T_min = 0.725, T_max = 0.791	l = −15→14
14022 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0408P)²] where P = (F_o² + 2F_c²)/3
4308 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 1.20 e Å⁻³
0 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

[Zn(C₁₀H₄Cl₂NO₂)₂(H₂O)₂]·H₂O	γ = 82.255 (1)°
M_r = 601.50	V = 1108.63 (8) Å³
Triclinic, P1	Z = 2
a = 6.8678 (3) Å	Mo Kα radiation
b = 12.6996 (5) Å	µ = 1.64 mm⁻¹
c = 12.9317 (5) Å	T = 296 K
α = 87.572 (1)°	0.21 × 0.17 × 0.15 mm
β = 82.893 (1)°

Data collection top

Rigaku Mercury diffractometer	4308 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	3099 reflections with I > 2σ(I)
T_min = 0.725, T_max = 0.791	R_int = 0.080
14022 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 0.97	Δρ_max = 1.20 e Å⁻³
4308 reflections	Δρ_min = −0.80 e Å⁻³
307 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
C1	0.2965 (5)	0.6256 (3)	0.2794 (3)	0.0197 (8)
H1	0.3070	0.6713	0.2215	0.024*
C2	0.3295 (5)	0.5161 (3)	0.2636 (3)	0.0194 (8)
C3	0.3176 (5)	0.4475 (3)	0.3464 (3)	0.0209 (8)
H3	0.3380	0.3746	0.3366	0.025*
C4	0.2565 (5)	0.4215 (3)	0.5377 (3)	0.0210 (8)
H4	0.2778	0.3480	0.5315	0.025*
C5	0.2088 (5)	0.4641 (3)	0.6336 (3)	0.0241 (9)
H5	0.1921	0.4201	0.6925	0.029*
C6	0.1848 (5)	0.5751 (3)	0.6434 (3)	0.0186 (8)
C7	0.2042 (5)	0.6439 (3)	0.5590 (3)	0.0176 (8)
C8	0.2434 (5)	0.5998 (3)	0.4583 (3)	0.0173 (8)
C9	0.2741 (5)	0.4879 (3)	0.4474 (3)	0.0188 (8)
C10	0.2017 (6)	0.7613 (3)	0.5715 (3)	0.0220 (8)
C11	−0.2472 (5)	1.1168 (3)	0.1346 (3)	0.0194 (8)
H11	−0.2486	1.1675	0.1846	0.023*
C12	−0.2620 (5)	1.1520 (3)	0.0307 (3)	0.0182 (8)
C13	−0.2648 (5)	1.0809 (3)	−0.0443 (3)	0.0179 (8)
H13	−0.2756	1.1034	−0.1129	0.022*
C14	−0.2534 (5)	0.8915 (3)	−0.0880 (3)	0.0221 (8)
H14	−0.2643	0.9098	−0.1577	0.027*
C15	−0.2399 (5)	0.7872 (3)	−0.0559 (3)	0.0213 (8)
H15	−0.2427	0.7346	−0.1034	0.026*
C16	−0.2218 (5)	0.7597 (3)	0.0488 (3)	0.0196 (8)
C17	−0.2162 (5)	0.8341 (3)	0.1213 (3)	0.0167 (8)
C18	−0.2329 (5)	0.9426 (3)	0.0898 (3)	0.0170 (8)
C19	−0.2509 (5)	0.9721 (3)	−0.0157 (3)	0.0172 (8)
C20	−0.1707 (5)	0.8066 (3)	0.2315 (3)	0.0179 (8)
Cl1	0.37704 (15)	0.47230 (7)	0.13739 (7)	0.0300 (2)
Cl2	0.12831 (15)	0.62268 (8)	0.76860 (7)	0.0300 (2)
Cl3	−0.28261 (14)	1.28675 (7)	0.00156 (7)	0.0247 (2)
Cl4	−0.19519 (15)	0.62565 (7)	0.08517 (8)	0.0295 (2)
N1	0.2514 (4)	0.6674 (2)	0.3722 (2)	0.0185 (7)
N2	−0.2316 (4)	1.0165 (2)	0.1644 (2)	0.0190 (7)
O1	0.0705 (4)	0.82485 (19)	0.52664 (19)	0.0294 (7)
O2	0.3222 (4)	0.7909 (2)	0.6231 (2)	0.0325 (7)
O3	0.0098 (3)	0.80624 (19)	0.24133 (19)	0.0222 (6)
O4	−0.3021 (4)	0.78885 (19)	0.3020 (2)	0.0289 (6)
O5	−0.0852 (4)	0.9774 (2)	0.3738 (2)	0.0336 (7)
H5A	−0.0800	1.0295	0.4126	0.040*
H5B	−0.1398	0.9842	0.3175	0.040*
O6	0.3458 (4)	0.9015 (2)	0.3214 (2)	0.0350 (7)
H6A	0.4589	0.8647	0.3195	0.042*
H6B	0.3090	0.9657	0.3391	0.042*
O7	0.3413 (5)	0.1059 (3)	0.3655 (3)	0.0858 (14)
H7B	0.4519	0.1189	0.3815	0.103*
H7C	0.2491	0.1273	0.4129	0.103*
Zn1	0.10699 (6)	0.83389 (3)	0.37255 (3)	0.01835 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.020 (2)	0.0198 (19)	0.019 (2)	0.0004 (15)	−0.0046 (16)	−0.0023 (16)
C2	0.0166 (19)	0.022 (2)	0.020 (2)	−0.0014 (15)	−0.0030 (15)	−0.0076 (15)
C3	0.020 (2)	0.0158 (19)	0.027 (2)	−0.0019 (15)	−0.0032 (16)	−0.0063 (16)
C4	0.019 (2)	0.0162 (18)	0.029 (2)	−0.0035 (15)	−0.0068 (17)	−0.0012 (16)
C5	0.024 (2)	0.023 (2)	0.026 (2)	−0.0050 (16)	−0.0072 (17)	0.0055 (17)
C6	0.0165 (19)	0.026 (2)	0.0133 (19)	−0.0017 (15)	−0.0024 (15)	−0.0039 (15)
C7	0.0130 (18)	0.0215 (19)	0.019 (2)	0.0014 (15)	−0.0071 (15)	−0.0027 (15)
C8	0.0145 (18)	0.0200 (19)	0.017 (2)	−0.0006 (15)	−0.0037 (15)	−0.0004 (15)
C9	0.0177 (19)	0.0184 (19)	0.019 (2)	0.0008 (15)	−0.0025 (15)	−0.0004 (15)
C10	0.032 (2)	0.0191 (19)	0.0123 (19)	0.0004 (17)	0.0038 (17)	−0.0019 (15)
C11	0.020 (2)	0.0167 (19)	0.021 (2)	0.0004 (15)	−0.0006 (16)	−0.0068 (15)
C12	0.0152 (18)	0.0160 (18)	0.022 (2)	0.0006 (15)	0.0008 (15)	0.0017 (15)
C13	0.0128 (18)	0.0232 (19)	0.018 (2)	−0.0009 (15)	−0.0041 (15)	0.0017 (16)
C14	0.023 (2)	0.029 (2)	0.014 (2)	−0.0046 (17)	0.0010 (16)	0.0006 (16)
C15	0.0192 (19)	0.022 (2)	0.023 (2)	−0.0018 (16)	−0.0013 (16)	−0.0082 (16)
C16	0.0161 (19)	0.0153 (18)	0.028 (2)	−0.0011 (15)	−0.0049 (16)	0.0000 (16)
C17	0.0068 (17)	0.0229 (19)	0.021 (2)	−0.0022 (14)	−0.0032 (14)	0.0007 (15)
C18	0.0106 (17)	0.0219 (19)	0.0188 (19)	−0.0006 (14)	−0.0037 (15)	−0.0023 (15)
C19	0.0087 (17)	0.0237 (19)	0.019 (2)	−0.0008 (15)	−0.0023 (14)	−0.0016 (15)
C20	0.022 (2)	0.0102 (17)	0.021 (2)	0.0001 (15)	−0.0038 (16)	−0.0012 (15)
Cl1	0.0431 (6)	0.0251 (5)	0.0207 (5)	−0.0030 (4)	0.0021 (4)	−0.0090 (4)
Cl2	0.0445 (6)	0.0278 (5)	0.0170 (5)	−0.0053 (4)	−0.0006 (4)	−0.0009 (4)
Cl3	0.0300 (5)	0.0170 (5)	0.0251 (5)	0.0009 (4)	−0.0006 (4)	0.0019 (4)
Cl4	0.0426 (6)	0.0176 (5)	0.0297 (6)	−0.0056 (4)	−0.0077 (5)	−0.0008 (4)
N1	0.0214 (16)	0.0166 (15)	0.0173 (17)	0.0003 (13)	−0.0044 (13)	−0.0005 (13)
N2	0.0186 (16)	0.0175 (16)	0.0202 (17)	−0.0007 (13)	−0.0011 (13)	−0.0023 (13)
O1	0.0448 (18)	0.0228 (14)	0.0167 (14)	0.0110 (13)	−0.0039 (13)	−0.0015 (11)
O2	0.0441 (18)	0.0280 (15)	0.0284 (16)	−0.0120 (13)	−0.0078 (14)	−0.0041 (12)
O3	0.0171 (14)	0.0299 (14)	0.0196 (14)	0.0019 (11)	−0.0063 (11)	−0.0047 (11)
O4	0.0284 (15)	0.0272 (15)	0.0289 (16)	−0.0032 (12)	0.0019 (13)	0.0085 (12)
O5	0.0471 (18)	0.0223 (14)	0.0319 (17)	0.0073 (13)	−0.0161 (14)	−0.0108 (12)
O6	0.0202 (15)	0.0234 (15)	0.060 (2)	−0.0003 (12)	−0.0006 (14)	−0.0041 (13)
O7	0.050 (2)	0.075 (3)	0.132 (4)	−0.030 (2)	0.031 (2)	−0.055 (3)
Zn1	0.0206 (2)	0.0172 (2)	0.0168 (2)	−0.00023 (17)	−0.00297 (17)	−0.00061 (17)

Geometric parameters (Å, º) top

C1—N1	1.316 (4)	C13—H13	0.9300
C1—C2	1.399 (5)	C14—C15	1.365 (5)
C1—H1	0.9300	C14—C19	1.419 (5)
C2—C3	1.352 (5)	C14—H14	0.9300
C2—Cl1	1.725 (4)	C15—C16	1.400 (5)
C3—C9	1.407 (5)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.366 (5)
C4—C5	1.359 (5)	C16—Cl4	1.739 (3)
C4—C9	1.414 (5)	C17—C18	1.414 (5)
C4—H4	0.9300	C17—C20	1.514 (5)
C5—C6	1.406 (5)	C18—N2	1.376 (4)
C5—H5	0.9300	C18—C19	1.415 (5)
C6—C7	1.374 (5)	C20—O4	1.237 (4)
C6—Cl2	1.732 (4)	C20—O3	1.261 (4)
C7—C8	1.421 (5)	N1—Zn1	2.211 (3)
C7—C10	1.504 (5)	O1—Zn1	1.978 (2)
C8—N1	1.377 (4)	O3—Zn1	1.960 (2)
C8—C9	1.419 (5)	O5—Zn1	2.101 (2)
C10—O2	1.231 (4)	O5—H5A	0.85
C10—O1	1.301 (4)	O5—H5B	0.86
C11—N2	1.310 (4)	O6—Zn1	1.982 (2)
C11—C12	1.410 (5)	O6—H6A	0.85
C11—H11	0.9300	O6—H6B	0.85
C12—C13	1.356 (5)	O7—H7B	0.85
C12—Cl3	1.727 (3)	O7—H7C	0.85
C13—C19	1.409 (5)

N1—C1—C2	123.4 (3)	C14—C15—C16	119.8 (3)
N1—C1—H1	118.3	C14—C15—H15	120.1
C2—C1—H1	118.3	C16—C15—H15	120.1
C3—C2—C1	119.8 (3)	C17—C16—C15	122.2 (3)
C3—C2—Cl1	121.7 (3)	C17—C16—Cl4	119.5 (3)
C1—C2—Cl1	118.5 (3)	C15—C16—Cl4	118.2 (3)
C2—C3—C9	119.2 (3)	C16—C17—C18	118.8 (3)
C2—C3—H3	120.4	C16—C17—C20	123.6 (3)
C9—C3—H3	120.4	C18—C17—C20	117.3 (3)
C5—C4—C9	120.5 (3)	N2—C18—C17	118.0 (3)
C5—C4—H4	119.7	N2—C18—C19	122.2 (3)
C9—C4—H4	119.7	C17—C18—C19	119.9 (3)
C4—C5—C6	119.7 (3)	C13—C19—C18	118.2 (3)
C4—C5—H5	120.1	C13—C19—C14	122.8 (3)
C6—C5—H5	120.1	C18—C19—C14	119.0 (3)
C7—C6—C5	122.6 (3)	O4—C20—O3	125.9 (3)
C7—C6—Cl2	120.7 (3)	O4—C20—C17	121.5 (3)
C5—C6—Cl2	116.7 (3)	O3—C20—C17	112.6 (3)
C6—C7—C8	117.8 (3)	C1—N1—C8	118.3 (3)
C6—C7—C10	121.9 (3)	C1—N1—Zn1	115.1 (2)
C8—C7—C10	120.1 (3)	C8—N1—Zn1	123.8 (2)
N1—C8—C9	121.0 (3)	C11—N2—C18	117.6 (3)
N1—C8—C7	118.9 (3)	C10—O1—Zn1	117.0 (2)
C9—C8—C7	120.1 (3)	C20—O3—Zn1	123.7 (2)
C3—C9—C4	122.6 (3)	Zn1—O5—H5A	124.5
C3—C9—C8	118.3 (3)	Zn1—O5—H5B	109.3
C4—C9—C8	119.1 (3)	H5A—O5—H5B	123.2
O2—C10—O1	124.4 (3)	Zn1—O6—H6A	119.1
O2—C10—C7	118.4 (3)	Zn1—O6—H6B	101.5
O1—C10—C7	117.2 (3)	H6A—O6—H6B	129.9
N2—C11—C12	123.4 (3)	H7B—O7—H7C	110.1
N2—C11—H11	118.3	O3—Zn1—O1	147.92 (11)
C12—C11—H11	118.3	O3—Zn1—O6	101.43 (11)
C13—C12—C11	120.2 (3)	O1—Zn1—O6	110.65 (12)
C13—C12—Cl3	120.9 (3)	O3—Zn1—O5	86.43 (10)
C11—C12—Cl3	118.9 (3)	O1—Zn1—O5	90.82 (10)
C12—C13—C19	118.4 (3)	O6—Zn1—O5	94.10 (11)
C12—C13—H13	120.8	O3—Zn1—N1	87.67 (10)
C19—C13—H13	120.8	O1—Zn1—N1	88.61 (10)
C15—C14—C19	120.3 (3)	O6—Zn1—N1	97.37 (11)
C15—C14—H14	119.8	O5—Zn1—N1	167.94 (11)
C19—C14—H14	119.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1ⁱ	0.85	2.05	2.889 (4)	166
O5—H5B···N2	0.86	2.16	3.002 (4)	169
O6—H6A···O4ⁱⁱ	0.85	1.78	2.628 (4)	174
O6—H6B···O7ⁱⁱⁱ	0.85	1.87	2.677 (4)	156
O7—H7B···O2^iv	0.85	2.04	2.827 (4)	153
O7—H7C···O1^v	0.85	2.25	3.029 (4)	153

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₀H₄Cl₂NO₂)₂(H₂O)₂]·H₂O
M_r	601.50
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.8678 (3), 12.6996 (5), 12.9317 (5)
α, β, γ (°)	87.572 (1), 82.893 (1), 82.255 (1)
V (Å³)	1108.63 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.64
Crystal size (mm)	0.21 × 0.17 × 0.15

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2001)
T_min, T_max	0.725, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	14022, 4308, 3099
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.094, 0.97
No. of reflections	4308
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.20, −0.80

Computer programs: CrystalClear (Rigaku/MSC, 2001), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1ⁱ	0.85	2.05	2.889 (4)	166.4
O5—H5B···N2	0.86	2.16	3.002 (4)	169.3
O6—H6A···O4ⁱⁱ	0.85	1.78	2.628 (4)	174.4
O6—H6B···O7ⁱⁱⁱ	0.85	1.87	2.677 (4)	156.2
O7—H7B···O2^iv	0.85	2.04	2.827 (4)	153.2
O7—H7C···O1^v	0.85	2.25	3.029 (4)	152.8

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

Acknowledgements

This work was supported by the Program for Excellent Talents in Huaiyin Teachers College (grant Nos. ETHYTC and 07QNZC010) and by the Natural Science Foundation of the Education Committee of Guangxi Province.

References

Adnan, B., Hesham, F., Sherif, R. & Azza, B. (2003). Eur. J. Med. Chem. 38, 27–36. Web of Science CrossRef PubMed Google Scholar
Che, G.-B., Liu, C.-B., Cui, Y.-C. & Li, C.-B. (2005). Acta Cryst. E61, m2207–m2208. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chen, Z. F., Zhang, P., Xiong, R. G., Liu, D. J. & You, X. Z. (2001). Inorg. Chem. Commun. 5, 35–37. Web of Science CSD CrossRef CAS Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Li, Z., Wu, F., Gong, Y., Zhang, Y. & Bai, C. (2008). Acta Cryst. E64, m227. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lumme, P., Elo, H. & Janne, J. (1984). Inorg. Chim. Acta, 92, 241–251. CrossRef CAS Web of Science Google Scholar
Rigaku/MSC (2001). CrystalClear. Version 1.30. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Version 3.6.0. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, G. W., Yuan, R. X. & Xie, Y. R. (2005). Chin. J. Inorg. Chem. 21, 120–121. Google Scholar
Zhang, Y.-H., Wu, F.-J., Li, X.-M., Zhu, M.-C. & Gong, Y. (2007). Acta Cryst. E63, m1557. Web of Science CSD CrossRef IUCr Journals Google Scholar