Triaqua­(2,2′-bipyridine-κ2N,N′)(5-nitro­isophthalato-κO1)zinc(II) monohydrate

Hao, L.; Liu, X.

doi:10.1107/S1600536808035174

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1498

doi:10.1107/S1600536808035174

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Triaqua(2,2′-bipyridine-κ²N,N′)(5-nitroisophthalato-κO¹)zinc(II) monohydrate

Lujiang Hao ^a ^* and Xia Liu ^b

^aCollege of Food and Biological Engineering, Shandong Institute of Light Industry, Jinan 250353, People's Republic of China, and ^bMaize Research Institute, Shandong Academy of Agricultural Science, Jinan 250100, People's Republic of China
^*Correspondence e-mail: lujianghao001@yahoo.com.cn

(Received 26 September 2008; accepted 28 October 2008; online 8 November 2008)

In the title compound, [Zn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O, the Zn^II cation is hexacoordinated by a chelating 2,2′-bipyridine ligand, one carboxylate O atom from a 5-nitroisophthalate dianion and three water molecules in a slightly distorted octahedral geometry. The structure contains isolated neutral complexes, in contrast to coordination polymers formed by Mn^II, Co^II and Cu^II with the same ligand set. An extensive network of hydrogen bonds is formed between the water molecules and the carboxylate groups.

Related literature

For related coordination polymers formed with the same ligand set and Mn^II, Co^II or Cu^II, see: Xiao et al. (2005 ); Xie et al. (2005 , 2006 ). For other examples of transition-metal complexes containing benzene carboxylates and pyridine-based ligands, see: Kim et al. (2001 ).

Experimental

Crystal data

[Zn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O
M_r = 502.73
Triclinic, $[P \overline 1]$
a = 7.5200 (10) Å
b = 10.6700 (15) Å
c = 12.8300 (15) Å
α = 90.024 (10)°
β = 87.670 (10)°
γ = 74.720 (10)°
V = 992.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.30 mm⁻¹
T = 293 (2) K
0.32 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.592, T_max = 0.747
5594 measured reflections
3801 independent reflections
3240 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.147
S = 1.06
3801 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 1.13 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H2W⋯O3ⁱ	0.84	1.96	2.776 (4)	165
O7—H1W⋯O10ⁱⁱ	0.84	1.78	2.607 (4)	168
O8—H3W⋯O5	0.84	1.94	2.715 (4)	153
O8—H4W⋯O3ⁱⁱⁱ	0.84	1.89	2.721 (4)	172
O9—H5W⋯O3^iv	0.84	1.94	2.727 (4)	156
O10—H8W⋯O4^vi	0.84	1.79	2.631 (4)	180
O10—H7W⋯O5	0.84	1.87	2.713 (5)	180
Symmetry codes: (i) x+1, y-1, z; (ii) x+1, y, z; (iii) x, y-1, z; (iv) -x+1, -y+2, -z+2; (v) -x+1, -y+1, -z+2; (vi) -x, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035174/bi2306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035174/bi2306Isup2.hkl

checkCIF report

Comment top

In recent years, carboxylic acids have been widely used in materials science as polydentate ligands which can coordinate to transition-metal or rare-earth cations to yield complexes with interesting or useful properties. For example, Kim et al. (2001) have focused on the syntheses of transition-metal complexes containing benzene carboxylate and rigid aromatic pyridine ligands in order to study their electronic conductivity and magnetic properties. The importance of transition-metal dicarboxylate complexes motivated us to pursue synthetic strategies for these compounds, using 5-nitroisophthalic acid as a polydentate ligand.

Related literature top

For related coordination polymers formed with the same ligand set and Mn^II, Co^II or Cu^II, see: Xiao et al. (2005); Xie et al. (2005, 2006). For other examples of transition-metal complexes containing benzene carboxylates and pyridine-based ligands, see: Kim et al. (2001).

Experimental top

A mixture of zinc dichloride (0.5 mmol), 2,2'-bipyridine (0.5 mmol), and 5-nitroisophthalic acid (0.5 mmol) in H₂O (8 ml) and ethanol (8 ml) was sealed in a 25 ml Teflon-lined stainless steel autoclave and kept at 413 K for three days. Colourless crystals were obtained after cooling to room temperature with a yield of 27%. Elemental analysis calculated: C 42.97, H 3.78, N 9.55%; found: C 42.86, H 3.76, N 9.51%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound showing displacement ellipsoids at 50% probability for non-H atoms.

Triaqua(2,2'-bipyridine-κ²N,N')(5-nitroisophthalato-κO¹)zinc(II) monohydrate top

Crystal data top

[Zn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O	Z = 2
M_r = 502.73	F(000) = 516
Triclinic, P1	D_x = 1.683 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.520 (1) Å	Cell parameters from 3801 reflections
b = 10.6700 (15) Å	θ = 1.6–26.0°
c = 12.8300 (15) Å	µ = 1.30 mm⁻¹
α = 90.024 (10)°	T = 293 K
β = 87.67 (1)°	Block, colorless
γ = 74.72 (1)°	0.32 × 0.28 × 0.22 mm
V = 992.2 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	3801 independent reflections
Radiation source: fine-focus sealed tube	3240 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.592, T_max = 0.747	k = −13→13
5594 measured reflections	l = 0→15

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0817P)² + 1.7563P] where P = (F_o² + 2F_c²)/3
3801 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 1.13 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Zn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O	γ = 74.72 (1)°
M_r = 502.73	V = 992.2 (2) Å³
Triclinic, P1	Z = 2
a = 7.520 (1) Å	Mo Kα radiation
b = 10.6700 (15) Å	µ = 1.30 mm⁻¹
c = 12.8300 (15) Å	T = 293 K
α = 90.024 (10)°	0.32 × 0.28 × 0.22 mm
β = 87.67 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3801 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3240 reflections with I > 2σ(I)
T_min = 0.592, T_max = 0.747	R_int = 0.016
5594 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.06	Δρ_max = 1.13 e Å⁻³
3801 reflections	Δρ_min = −0.72 e Å⁻³
289 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.72904 (6)	0.47118 (4)	0.78573 (3)	0.02670 (18)
C1	0.5256 (5)	1.0550 (3)	0.6738 (3)	0.0200 (7)
C2	0.4383 (5)	1.1472 (3)	0.7462 (3)	0.0204 (7)
H2A	0.4166	1.2351	0.7314	0.024*
C3	0.3825 (5)	1.1075 (3)	0.8421 (3)	0.0185 (7)
C4	0.2892 (5)	1.2039 (3)	0.9251 (3)	0.0192 (7)
C5	0.4090 (5)	0.9779 (3)	0.8610 (3)	0.0206 (7)
H5A	0.3675	0.9513	0.9243	0.025*
C6	0.4968 (5)	0.8863 (3)	0.7869 (3)	0.0212 (7)
C7	0.5604 (5)	0.9247 (3)	0.6925 (3)	0.0230 (7)
H7A	0.6248	0.8637	0.6433	0.028*
C8	0.5179 (5)	0.7461 (3)	0.8070 (3)	0.0258 (8)
C9	0.7336 (6)	0.5092 (4)	0.5475 (3)	0.0323 (9)
H9A	0.6630	0.5932	0.5630	0.039*
C10	0.7887 (7)	0.4771 (5)	0.4446 (3)	0.0434 (11)
H10A	0.7530	0.5368	0.3917	0.052*
C11	0.8961 (8)	0.3562 (5)	0.4235 (3)	0.0491 (13)
H11A	0.9383	0.3321	0.3554	0.059*
C12	0.9428 (7)	0.2692 (4)	0.5027 (3)	0.0396 (11)
H12A	1.0183	0.1861	0.4890	0.048*
C13	0.8759 (5)	0.3064 (3)	0.6038 (3)	0.0216 (7)
C14	0.9011 (5)	0.2164 (3)	0.6926 (3)	0.0190 (7)
C15	0.9850 (5)	0.0861 (4)	0.6817 (3)	0.0279 (8)
H15A	1.0429	0.0516	0.6187	0.033*
C16	0.9811 (6)	0.0076 (4)	0.7667 (4)	0.0355 (10)
H16A	1.0358	−0.0812	0.7611	0.043*
C17	0.8971 (6)	0.0598 (4)	0.8594 (3)	0.0326 (9)
H17A	0.8908	0.0071	0.9165	0.039*
C18	0.8232 (5)	0.1903 (4)	0.8660 (3)	0.0267 (8)
H18A	0.7700	0.2267	0.9295	0.032*
N1	0.5836 (5)	1.0974 (3)	0.5725 (2)	0.0275 (7)
N2	0.7767 (4)	0.4257 (3)	0.6256 (2)	0.0215 (6)
N3	0.8239 (4)	0.2684 (3)	0.7848 (2)	0.0192 (6)
O1	0.6969 (4)	1.0197 (3)	0.5172 (2)	0.0373 (7)
O2	0.5184 (5)	1.2084 (3)	0.5476 (2)	0.0445 (8)
O3	0.2776 (4)	1.3214 (2)	0.9070 (2)	0.0255 (6)
O4	0.2275 (4)	1.1635 (3)	1.0056 (2)	0.0337 (7)
O5	0.3987 (5)	0.7173 (3)	0.8669 (3)	0.0524 (10)
O6	0.6527 (4)	0.6677 (2)	0.7630 (2)	0.0254 (6)
O7	1.0013 (4)	0.4817 (3)	0.7943 (2)	0.0272 (6)
H1W	1.0042	0.5549	0.8172	0.041*
H2W	1.0698	0.4272	0.8325	0.041*
O8	0.4497 (4)	0.4721 (2)	0.7915 (2)	0.0273 (6)
H3W	0.3989	0.5451	0.8186	0.041*
H4W	0.4061	0.4197	0.8264	0.041*
O9	0.7038 (4)	0.4909 (3)	0.9526 (2)	0.0347 (7)
H5W	0.7188	0.5586	0.9802	0.052*
H6W	0.6784	0.4397	0.9970	0.052*
O10	0.0498 (5)	0.6904 (4)	0.8813 (5)	0.113 (3)
H7W	0.1579	0.6986	0.8768	0.169*
H8W	−0.0387	0.7370	0.9175	0.169*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0308 (3)	0.0205 (3)	0.0280 (3)	−0.00584 (19)	0.00216 (18)	−0.00145 (17)
C1	0.0244 (18)	0.0183 (17)	0.0177 (16)	−0.0059 (14)	−0.0015 (14)	−0.0002 (13)
C2	0.0244 (18)	0.0132 (16)	0.0245 (18)	−0.0060 (13)	−0.0034 (14)	0.0019 (13)
C3	0.0185 (17)	0.0152 (16)	0.0220 (17)	−0.0050 (13)	0.0002 (13)	−0.0002 (13)
C4	0.0197 (17)	0.0125 (16)	0.0241 (17)	−0.0019 (13)	−0.0012 (14)	−0.0004 (13)
C5	0.0203 (17)	0.0149 (16)	0.0257 (18)	−0.0037 (13)	0.0036 (14)	0.0015 (13)
C6	0.0199 (17)	0.0101 (16)	0.0322 (19)	−0.0021 (13)	0.0017 (14)	0.0000 (14)
C7	0.0252 (18)	0.0167 (17)	0.0260 (18)	−0.0039 (14)	0.0017 (15)	−0.0051 (14)
C8	0.0234 (19)	0.0114 (16)	0.042 (2)	−0.0038 (14)	0.0057 (16)	−0.0009 (15)
C9	0.042 (2)	0.025 (2)	0.027 (2)	−0.0042 (17)	−0.0037 (17)	0.0066 (16)
C10	0.068 (3)	0.041 (3)	0.023 (2)	−0.016 (2)	−0.006 (2)	0.0102 (18)
C11	0.085 (4)	0.046 (3)	0.019 (2)	−0.023 (3)	0.010 (2)	−0.0022 (19)
C12	0.060 (3)	0.032 (2)	0.024 (2)	−0.010 (2)	0.016 (2)	−0.0078 (17)
C13	0.0265 (19)	0.0175 (17)	0.0211 (17)	−0.0069 (14)	0.0033 (14)	−0.0011 (13)
C14	0.0215 (17)	0.0160 (16)	0.0197 (17)	−0.0053 (13)	−0.0003 (13)	−0.0003 (13)
C15	0.031 (2)	0.0176 (18)	0.032 (2)	−0.0019 (15)	0.0039 (16)	−0.0042 (15)
C16	0.040 (2)	0.0165 (19)	0.048 (3)	−0.0037 (17)	−0.006 (2)	0.0033 (17)
C17	0.038 (2)	0.027 (2)	0.036 (2)	−0.0121 (18)	−0.0078 (18)	0.0127 (17)
C18	0.035 (2)	0.0255 (19)	0.0212 (18)	−0.0117 (16)	0.0004 (15)	0.0040 (15)
N1	0.0378 (19)	0.0274 (17)	0.0202 (15)	−0.0138 (15)	−0.0002 (14)	−0.0003 (13)
N2	0.0273 (16)	0.0189 (15)	0.0186 (14)	−0.0070 (12)	−0.0002 (12)	0.0019 (11)
N3	0.0244 (15)	0.0128 (13)	0.0200 (14)	−0.0045 (11)	−0.0006 (12)	−0.0011 (11)
O1	0.0459 (18)	0.0380 (17)	0.0252 (14)	−0.0082 (14)	0.0138 (13)	−0.0063 (12)
O2	0.075 (2)	0.0262 (16)	0.0294 (16)	−0.0094 (15)	0.0061 (15)	0.0088 (12)
O3	0.0364 (15)	0.0108 (12)	0.0276 (13)	−0.0042 (10)	0.0049 (11)	−0.0013 (10)
O4	0.0486 (18)	0.0168 (13)	0.0314 (15)	−0.0041 (12)	0.0177 (13)	0.0001 (11)
O5	0.0441 (19)	0.0160 (14)	0.095 (3)	−0.0102 (13)	0.0398 (19)	−0.0053 (15)
O6	0.0282 (14)	0.0084 (11)	0.0365 (15)	−0.0011 (10)	0.0110 (11)	−0.0008 (10)
O7	0.0257 (14)	0.0190 (13)	0.0376 (15)	−0.0061 (10)	−0.0077 (11)	0.0022 (11)
O8	0.0232 (13)	0.0186 (13)	0.0402 (15)	−0.0065 (10)	0.0059 (11)	0.0013 (11)
O9	0.065 (2)	0.0230 (14)	0.0190 (13)	−0.0171 (14)	0.0029 (13)	−0.0040 (10)
O10	0.036 (2)	0.074 (3)	0.229 (7)	−0.025 (2)	0.051 (3)	−0.107 (4)

Geometric parameters (Å, º) top

Zn1—O6	2.047 (2)	C11—C12	1.370 (7)
Zn1—O7	2.087 (3)	C11—H11A	0.930
Zn1—N3	2.092 (3)	C12—C13	1.391 (5)
Zn1—O8	2.096 (3)	C12—H12A	0.930
Zn1—N2	2.105 (3)	C13—N2	1.318 (5)
Zn1—O9	2.148 (3)	C13—C14	1.475 (5)
C1—C2	1.368 (5)	C14—N3	1.349 (4)
C1—C7	1.369 (5)	C14—C15	1.371 (5)
C1—N1	1.463 (5)	C15—C16	1.380 (6)
C2—C3	1.386 (5)	C15—H15A	0.930
C2—H2A	0.930	C16—C17	1.370 (6)
C3—C5	1.367 (5)	C16—H16A	0.930
C3—C4	1.497 (5)	C17—C18	1.357 (6)
C4—O4	1.240 (4)	C17—H17A	0.930
C4—O3	1.255 (4)	C18—N3	1.335 (5)
C5—C6	1.380 (5)	C18—H18A	0.930
C5—H5A	0.930	N1—O2	1.204 (5)
C6—C7	1.385 (5)	N1—O1	1.222 (4)
C6—C8	1.486 (5)	O7—H1W	0.840
C7—H7A	0.930	O7—H2W	0.840
C8—O6	1.245 (4)	O8—H3W	0.840
C8—O5	1.256 (5)	O8—H4W	0.840
C9—N2	1.334 (5)	O9—H5W	0.840
C9—C10	1.382 (6)	O9—H6W	0.840
C9—H9A	0.930	O10—H7W	0.840
C10—C11	1.350 (7)	O10—H8W	0.840
C10—H10A	0.930

O6—Zn1—O7	88.46 (11)	C10—C11—C12	119.8 (4)
O6—Zn1—N3	170.99 (11)	C10—C11—H11A	120.1
O7—Zn1—N3	89.04 (11)	C12—C11—H11A	120.1
O6—Zn1—O8	89.13 (10)	C11—C12—C13	119.3 (4)
O7—Zn1—O8	174.03 (10)	C11—C12—H12A	120.4
N3—Zn1—O8	94.16 (11)	C13—C12—H12A	120.4
O6—Zn1—N2	94.11 (11)	N2—C13—C12	121.2 (4)
O7—Zn1—N2	89.58 (11)	N2—C13—C14	115.1 (3)
N3—Zn1—N2	77.22 (11)	C12—C13—C14	123.6 (3)
O8—Zn1—N2	96.04 (11)	N3—C14—C15	121.4 (3)
O6—Zn1—O9	93.40 (11)	N3—C14—C13	115.7 (3)
O7—Zn1—O9	87.99 (12)	C15—C14—C13	122.8 (3)
N3—Zn1—O9	95.16 (11)	C14—C15—C16	118.2 (4)
O8—Zn1—O9	86.70 (12)	C14—C15—H15A	120.9
N2—Zn1—O9	172.05 (11)	C16—C15—H15A	120.9
C2—C1—C7	122.4 (3)	C17—C16—C15	120.4 (4)
C2—C1—N1	118.8 (3)	C17—C16—H16A	119.8
C7—C1—N1	118.8 (3)	C15—C16—H16A	119.8
C1—C2—C3	119.0 (3)	C18—C17—C16	118.4 (4)
C1—C2—H2A	120.5	C18—C17—H17A	120.8
C3—C2—H2A	120.5	C16—C17—H17A	120.8
C5—C3—C2	119.6 (3)	N3—C18—C17	122.5 (4)
C5—C3—C4	119.0 (3)	N3—C18—H18A	118.8
C2—C3—C4	121.3 (3)	C17—C18—H18A	118.8
O4—C4—O3	124.6 (3)	O2—N1—O1	122.8 (3)
O4—C4—C3	118.5 (3)	O2—N1—C1	118.3 (3)
O3—C4—C3	117.0 (3)	O1—N1—C1	118.9 (3)
C3—C5—C6	120.6 (3)	C13—N2—C9	118.5 (3)
C3—C5—H5A	119.7	C13—N2—Zn1	115.1 (2)
C6—C5—H5A	119.7	C9—N2—Zn1	126.0 (3)
C5—C6—C7	120.3 (3)	C18—N3—C14	119.1 (3)
C5—C6—C8	119.9 (3)	C18—N3—Zn1	126.6 (2)
C7—C6—C8	119.8 (3)	C14—N3—Zn1	114.2 (2)
C1—C7—C6	118.0 (3)	C8—O6—Zn1	125.6 (2)
C1—C7—H7A	121.0	Zn1—O7—H1W	110.4
C6—C7—H7A	121.0	Zn1—O7—H2W	116.7
O6—C8—O5	125.9 (3)	H1W—O7—H2W	105.6
O6—C8—C6	117.0 (3)	Zn1—O8—H3W	102.2
O5—C8—C6	117.1 (3)	Zn1—O8—H4W	124.1
N2—C9—C10	123.2 (4)	H3W—O8—H4W	104.6
N2—C9—H9A	118.4	Zn1—O9—H5W	118.6
C10—C9—H9A	118.4	Zn1—O9—H6W	129.1
C11—C10—C9	117.9 (4)	H5W—O9—H6W	112.3
C11—C10—H10A	121.1	H7W—O10—H8W	126.1
C9—C10—H10A	121.1

C7—C1—C2—C3	−0.1 (5)	C2—C1—N1—O1	163.3 (3)
N1—C1—C2—C3	179.8 (3)	C7—C1—N1—O1	−16.8 (5)
C1—C2—C3—C5	−2.6 (5)	C12—C13—N2—C9	3.2 (6)
C1—C2—C3—C4	179.0 (3)	C14—C13—N2—C9	−173.9 (3)
C5—C3—C4—O4	−4.9 (5)	C12—C13—N2—Zn1	−169.7 (3)
C2—C3—C4—O4	173.6 (3)	C14—C13—N2—Zn1	13.2 (4)
C5—C3—C4—O3	175.8 (3)	C10—C9—N2—C13	−0.4 (6)
C2—C3—C4—O3	−5.7 (5)	C10—C9—N2—Zn1	171.7 (3)
C2—C3—C5—C6	2.4 (5)	O6—Zn1—N2—C13	163.0 (3)
C4—C3—C5—C6	−179.1 (3)	O7—Zn1—N2—C13	74.6 (3)
C3—C5—C6—C7	0.4 (6)	N3—Zn1—N2—C13	−14.5 (3)
C3—C5—C6—C8	−177.6 (3)	O8—Zn1—N2—C13	−107.4 (3)
C2—C1—C7—C6	2.9 (5)	O6—Zn1—N2—C9	−9.2 (3)
N1—C1—C7—C6	−177.0 (3)	O7—Zn1—N2—C9	−97.7 (3)
C5—C6—C7—C1	−3.0 (5)	N3—Zn1—N2—C9	173.2 (3)
C8—C6—C7—C1	175.0 (3)	O8—Zn1—N2—C9	80.3 (3)
C5—C6—C8—O6	−152.1 (4)	C17—C18—N3—C14	−0.1 (6)
C7—C6—C8—O6	29.9 (5)	C17—C18—N3—Zn1	−176.3 (3)
C5—C6—C8—O5	27.7 (6)	C15—C14—N3—C18	−2.6 (5)
C7—C6—C8—O5	−150.3 (4)	C13—C14—N3—C18	172.7 (3)
N2—C9—C10—C11	−2.1 (7)	C15—C14—N3—Zn1	174.0 (3)
C9—C10—C11—C12	1.6 (8)	C13—C14—N3—Zn1	−10.7 (4)
C10—C11—C12—C13	1.0 (8)	O7—Zn1—N3—C18	99.8 (3)
C11—C12—C13—N2	−3.6 (7)	O8—Zn1—N3—C18	−75.2 (3)
C11—C12—C13—C14	173.2 (4)	N2—Zn1—N3—C18	−170.4 (3)
N2—C13—C14—N3	−1.7 (5)	O9—Zn1—N3—C18	11.9 (3)
C12—C13—C14—N3	−178.7 (4)	O7—Zn1—N3—C14	−76.5 (2)
N2—C13—C14—C15	173.5 (3)	O8—Zn1—N3—C14	108.5 (2)
C12—C13—C14—C15	−3.5 (6)	N2—Zn1—N3—C14	13.3 (2)
N3—C14—C15—C16	3.0 (6)	O9—Zn1—N3—C14	−164.4 (2)
C13—C14—C15—C16	−171.9 (4)	O5—C8—O6—Zn1	−5.3 (6)
C14—C15—C16—C17	−0.7 (6)	C6—C8—O6—Zn1	174.5 (2)
C15—C16—C17—C18	−1.9 (6)	O7—Zn1—O6—C8	−135.1 (3)
C16—C17—C18—N3	2.4 (6)	O8—Zn1—O6—C8	39.5 (3)
C2—C1—N1—O2	−16.1 (5)	N2—Zn1—O6—C8	135.5 (3)
C7—C1—N1—O2	163.8 (4)	O9—Zn1—O6—C8	−47.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H2W···O3ⁱ	0.84	1.96	2.776 (4)	165
O7—H1W···O10ⁱⁱ	0.84	1.78	2.607 (4)	168
O8—H3W···O5	0.84	1.94	2.715 (4)	153
O8—H4W···O3ⁱⁱⁱ	0.84	1.89	2.721 (4)	172
O9—H5W···O3^iv	0.84	1.94	2.727 (4)	156
O9—H6W···O5^v	0.84	2.57	3.414 (4)	180
O10—H8W···O4^vi	0.84	1.79	2.631 (4)	180
O10—H7W···O5	0.84	1.87	2.713 (5)	180

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O
M_r	502.73
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.520 (1), 10.6700 (15), 12.8300 (15)
α, β, γ (°)	90.024 (10), 87.67 (1), 74.72 (1)
V (Å³)	992.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.32 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.592, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	5594, 3801, 3240
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.147, 1.06
No. of reflections	3801
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.72

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), 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
O7—H2W···O3ⁱ	0.84	1.96	2.776 (4)	165.2
O7—H1W···O10ⁱⁱ	0.84	1.78	2.607 (4)	167.8
O8—H3W···O5	0.84	1.94	2.715 (4)	153.1
O8—H4W···O3ⁱⁱⁱ	0.84	1.89	2.721 (4)	171.9
O9—H5W···O3^iv	0.84	1.94	2.727 (4)	156.2
O9—H6W···O5^v	0.84	2.57	3.414 (4)	179.9
O10—H8W···O4^vi	0.84	1.79	2.631 (4)	179.9
O10—H7W···O5	0.84	1.87	2.713 (5)	179.8

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

Acknowledgements

This work is supported by the Natural Science Foundation of Shandong Province (grant No. Y2007D39).

References

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