Triaqua­(2,2′-bipyridine N,N′-dioxide-κ2O,O′)(5-nitro­benzene-1,3-dicarboxyl­ato-κO1)zinc(II)

Lu, H.-J.; Wang, F.-M.

doi:10.1107/S1600536809015451

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m660

doi:10.1107/S1600536809015451

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Triaqua(2,2′-bipyridine N,N′-dioxide-κ²O,O′)(5-nitrobenzene-1,3-dicarboxylato-κO¹)zinc(II)

Hui-Juan Lu ^a ^* and Fang-Ming Wang ^b

^aDepartment of Chemical Engineering, Wuhan University of Science and Engineering, Wuhan, Hubei 430073, People's Republic of China, and ^bSchool of Materials Science and Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, People's Republic of China
^*Correspondence e-mail: carpo1978@163.com

(Received 16 April 2009; accepted 24 April 2009; online 20 May 2009)

In the title compound, [Zn(C₈H₃NO₆)(C₁₀H₈N₂O₂)(H₂O)₃], the Zn^II ion is coordinated in a distorted octahedral geometry by three water molecules, one O atom from a 5-nitrobenzene-1,3-dicarboxylate ligand and two O atoms from a chelating 2,2′-bipyridine N,N′-dioxide ligand. An extensive network of O—H⋯O hydrogen bonds is formed between the water molecules and the carboxylate groups. C—H⋯O interactions are also present.

Related literature

For metal complexes containing the 2,2′-bipyridine-N,N′-dioxide ligand, see: Hill et al. (2004 ); Long et al. (2001 ); Ma et al. (2003 ).

Experimental

Crystal data

[Zn(C₈H₃NO₆)(C₁₀H₈N₂O₂)(H₂O)₃]
M_r = 516.72
Triclinic, $[P \overline 1]$
a = 8.3040 (14) Å
b = 10.7036 (18) Å
c = 11.6546 (19) Å
α = 87.217 (3)°
β = 88.436 (3)°
γ = 87.006 (3)°
V = 1032.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.26 mm⁻¹
T = 294 K
0.20 × 0.19 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.778, T_max = 0.828
6281 measured reflections
3604 independent reflections
2737 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.143
S = 1.05
3604 reflections
316 parameters
15 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Selected bond lengths (Å)

O1—Zn1	2.094 (3)
O2—Zn1	2.144 (3)
O3—Zn1	2.043 (3)
O9—Zn1	2.125 (3)
O10—Zn1	2.067 (3)
O11—Zn1	2.054 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9A⋯O5ⁱ	0.82 (3)	2.08 (4)	2.773 (5)	143 (5)
O9—H9B⋯O4	0.83 (3)	1.83 (3)	2.635 (5)	164 (4)
O10—H10A⋯O6ⁱⁱ	0.81 (5)	1.96 (5)	2.735 (5)	161 (6)
O10—H10B⋯O6ⁱⁱⁱ	0.82 (5)	2.03 (5)	2.702 (5)	139 (5)
O11—H11A⋯O2^iv	0.82 (3)	1.95 (3)	2.687 (5)	149 (5)
O11—H11B⋯O5ⁱⁱ	0.83 (3)	1.87 (4)	2.692 (5)	169 (4)
C2—H2⋯O8^v	0.93	2.59	3.229 (8)	126
C3—H3⋯O6^vi	0.93	2.49	3.269 (7)	141
C4—H4⋯O3^vii	0.93	2.46	3.358 (7)	162
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y, z-1; (iii) -x+1, -y+2, -z+2; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y+2, -z+1; (vi) x-1, y, z-1; (vii) x-1, y, z.

Data collection: SMART (Bruker, 2001 ); 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 I, global. DOI: 10.1107/S1600536809015451/gk2207sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015451/gk2207Isup2.hkl

checkCIF report

Comment top

Herein we report the crystal structure of a novel compound, [Zn(C₁₀H₈N₂O₂)(C₈H₃NO₆)(H₂O)₃](I). As shown in Fig.1, the central Zn atom is coordinated by three O atoms from three water molecules, one O atom from 5-nitrobenzene-1,3-dicarboxylate ligand and two O atoms from 2,2'-bipyridine-N,N'-dioxide ligand in a distorted octahedral geometry. The 2,2'-bipyridine-N,N'-dioxide coordinated to the Zn atom forms a seven-membered chalate ring. O1, O2, O3 and O11 atoms lie in the equatorial plane, with the O3—O1—O2—O11 torsional angle of 0.51°, while the Zn atom deviates from the equatorial plane by 0.026 Å. O9 and O10 atoms occupy the axial sites, with O9—Zn1—O10 angle of 173.04°) (distances to the equatorial plane are 2.143 and 2.040 Å). Among the distances of Zn—O, the distance of Zn(1)—O(2) is the longest, (see Table 2). The neighboring molecules in the crystal are linked by a series of O—H···O and C—H ···O intermolecular hydrogen bonds.

Related literature top

For metal complexes containing the 2,2'-bipyridine-N,N'-dioxide ligand, see: Hill et al. (2004); Long et al. (2001); Ma et al. (2003).

Experimental top

A mixture of ZnSO₄(0.50 mmol),5-nitrobenzene-1,3-dicarboxylic acid (0.50 mmol), 2,2'-bipyridine-N,N'-dioxide (0.50 mmol), and H₂O (3.00 ml), was placed in a Parr Teflon-lined stainless steel vessel (10 mL), and then the vessel was sealed and heated at 393 K for 3 days. After the mixture was slowly cooled to room temperature, several colourless crystals of the title compound were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); 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. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Part of the crystal structure showing hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

Triaqua(2,2'-bipyridine N,N'-dioxide-κ²O,O')(5-nitrobenzene-1,3- dicarboxylato-κO¹)zinc(II) top

Crystal data top

[Zn(C₈H₃NO₆)(C₁₀H₈N₂O₂)(H₂O)₃]	Z = 2
M_r = 516.72	F(000) = 528
Triclinic, P1	D_x = 1.661 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3040 (14) Å	Cell parameters from 1831 reflections
b = 10.7036 (18) Å	θ = 2.5–25.8°
c = 11.6546 (19) Å	µ = 1.26 mm⁻¹
α = 87.217 (3)°	T = 294 K
β = 88.436 (3)°	Plate, colourless
γ = 87.006 (3)°	0.20 × 0.19 × 0.15 mm
V = 1032.9 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3604 independent reflections
Radiation source: fine-focus sealed tube	2737 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
T_min = 0.778, T_max = 0.828	l = −13→12
6281 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0678P)²] where P = (F_o² + 2F_c²)/3
3604 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.62 e Å⁻³
15 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Zn(C₈H₃NO₆)(C₁₀H₈N₂O₂)(H₂O)₃]	γ = 87.006 (3)°
M_r = 516.72	V = 1032.9 (3) Å³
Triclinic, P1	Z = 2
a = 8.3040 (14) Å	Mo Kα radiation
b = 10.7036 (18) Å	µ = 1.26 mm⁻¹
c = 11.6546 (19) Å	T = 294 K
α = 87.217 (3)°	0.20 × 0.19 × 0.15 mm
β = 88.436 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3604 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2737 reflections with I > 2σ(I)
T_min = 0.778, T_max = 0.828	R_int = 0.075
6281 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	15 restraints
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.62 e Å⁻³
3604 reflections	Δρ_min = −0.52 e Å⁻³
316 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	0.1974 (7)	0.7637 (5)	0.4162 (4)	0.0393 (13)
H1	0.2819	0.7530	0.3629	0.047*
C2	0.0764 (7)	0.8456 (5)	0.3923 (5)	0.0501 (15)
H2	0.0790	0.8941	0.3239	0.060*
C3	−0.0552 (7)	0.8599 (5)	0.4689 (5)	0.0422 (14)
H3	−0.1426	0.9146	0.4510	0.051*
C4	−0.0514 (7)	0.7907 (5)	0.5715 (5)	0.0419 (13)
H4	−0.1365	0.7988	0.6245	0.050*
C5	0.0808 (6)	0.7082 (4)	0.5958 (4)	0.0291 (11)
C6	0.0829 (6)	0.6224 (4)	0.6979 (4)	0.0316 (11)
C7	−0.0296 (7)	0.5359 (5)	0.7202 (5)	0.0446 (14)
H7	−0.1152	0.5322	0.6710	0.054*
C8	−0.0185 (7)	0.4531 (5)	0.8157 (5)	0.0467 (15)
H8	−0.0946	0.3931	0.8298	0.056*
C9	0.1038 (7)	0.4616 (5)	0.8867 (5)	0.0437 (14)
H9	0.1116	0.4074	0.9514	0.052*
C10	0.2200 (6)	0.5500 (5)	0.8659 (4)	0.0383 (12)
H10	0.3051	0.5543	0.9155	0.046*
C11	0.6375 (6)	0.7121 (4)	0.8717 (4)	0.0319 (11)
C12	0.6641 (6)	0.8090 (4)	0.9588 (4)	0.0294 (11)
C13	0.6310 (6)	0.7849 (4)	1.0732 (4)	0.0315 (12)
H13	0.5928	0.7074	1.0966	0.038*
C14	0.6522 (6)	0.8719 (4)	1.1562 (4)	0.0279 (11)
C15	0.6128 (6)	0.8387 (4)	1.2805 (4)	0.0313 (12)
C16	0.7084 (6)	0.9882 (4)	1.1206 (4)	0.0308 (11)
H16	0.7229	1.0490	1.1732	0.037*
C17	0.7419 (6)	1.0105 (4)	1.0055 (4)	0.0305 (11)
C18	0.7202 (6)	0.9267 (5)	0.9228 (4)	0.0345 (12)
H18	0.7417	0.9469	0.8456	0.041*
N1	0.1998 (5)	0.6958 (4)	0.5163 (3)	0.0334 (10)
N2	0.2069 (5)	0.6291 (4)	0.7726 (3)	0.0337 (10)
N3	0.8039 (6)	1.1326 (4)	0.9671 (4)	0.0534 (14)
O1	0.3113 (4)	0.7178 (3)	0.7539 (3)	0.0333 (8)
O2	0.3271 (4)	0.6146 (3)	0.5377 (3)	0.0321 (8)
O3	0.6489 (4)	0.7466 (3)	0.7662 (3)	0.0352 (8)
O4	0.6108 (5)	0.6041 (3)	0.9116 (3)	0.0420 (9)
O5	0.5983 (5)	0.7257 (3)	1.3088 (3)	0.0444 (10)
O6	0.5973 (5)	0.9246 (3)	1.3487 (3)	0.0473 (10)
O7	0.8838 (7)	1.1868 (4)	1.0367 (4)	0.0822 (16)
O8	0.7846 (7)	1.1702 (4)	0.8683 (4)	0.0804 (16)
O9	0.5579 (5)	0.4929 (3)	0.7204 (3)	0.0339 (8)
H9A	0.546 (7)	0.418 (2)	0.732 (4)	0.051*
H9B	0.562 (7)	0.518 (4)	0.786 (2)	0.051*
O10	0.4917 (6)	0.8518 (3)	0.5648 (3)	0.0561 (12)
H10A	0.544 (7)	0.872 (6)	0.509 (4)	0.084*
H10B	0.421 (6)	0.904 (5)	0.583 (5)	0.084*
O11	0.6736 (4)	0.6260 (3)	0.5182 (3)	0.0326 (8)
H11A	0.640 (6)	0.556 (2)	0.514 (4)	0.049*
H11B	0.644 (6)	0.664 (4)	0.458 (3)	0.049*
Zn1	0.50994 (7)	0.67555 (5)	0.64551 (4)	0.0280 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.045 (3)	0.047 (3)	0.025 (3)	0.002 (3)	0.001 (2)	0.001 (2)
C2	0.064 (4)	0.049 (4)	0.036 (3)	−0.006 (3)	−0.001 (3)	0.014 (3)
C3	0.039 (3)	0.034 (3)	0.053 (4)	−0.002 (2)	−0.009 (3)	0.005 (3)
C4	0.049 (3)	0.033 (3)	0.045 (3)	−0.016 (3)	0.003 (3)	−0.002 (3)
C5	0.025 (3)	0.031 (3)	0.032 (3)	−0.003 (2)	0.002 (2)	0.000 (2)
C6	0.032 (3)	0.031 (3)	0.031 (3)	−0.005 (2)	0.005 (2)	0.005 (2)
C7	0.055 (4)	0.039 (3)	0.041 (3)	−0.012 (3)	0.003 (3)	0.004 (3)
C8	0.051 (4)	0.037 (3)	0.052 (4)	−0.015 (3)	0.011 (3)	0.007 (3)
C9	0.059 (4)	0.035 (3)	0.035 (3)	−0.002 (3)	0.009 (3)	0.011 (2)
C10	0.041 (3)	0.042 (3)	0.032 (3)	0.003 (2)	0.003 (2)	−0.002 (2)
C11	0.039 (3)	0.032 (3)	0.026 (3)	−0.004 (2)	0.001 (2)	−0.007 (2)
C12	0.040 (3)	0.025 (3)	0.022 (3)	−0.003 (2)	0.001 (2)	0.000 (2)
C13	0.053 (3)	0.017 (2)	0.024 (3)	−0.004 (2)	0.005 (2)	−0.004 (2)
C14	0.036 (3)	0.027 (3)	0.020 (2)	−0.002 (2)	0.003 (2)	0.000 (2)
C15	0.046 (3)	0.021 (3)	0.027 (3)	−0.006 (2)	0.005 (2)	−0.007 (2)
C16	0.036 (3)	0.027 (3)	0.029 (3)	−0.005 (2)	0.004 (2)	−0.004 (2)
C17	0.037 (3)	0.021 (2)	0.034 (3)	−0.010 (2)	0.009 (2)	−0.002 (2)
C18	0.045 (3)	0.038 (3)	0.021 (3)	−0.011 (2)	0.008 (2)	0.005 (2)
N1	0.049 (3)	0.028 (2)	0.024 (2)	−0.0079 (19)	−0.001 (2)	−0.0047 (18)
N2	0.048 (3)	0.028 (2)	0.025 (2)	−0.0071 (19)	0.012 (2)	0.0035 (18)
N3	0.083 (4)	0.034 (3)	0.043 (3)	−0.021 (3)	0.028 (3)	−0.007 (2)
O1	0.0317 (18)	0.035 (2)	0.0343 (19)	−0.0105 (15)	0.0064 (15)	−0.0039 (15)
O2	0.0346 (19)	0.0302 (19)	0.0315 (19)	0.0060 (15)	−0.0029 (15)	−0.0078 (15)
O3	0.056 (2)	0.035 (2)	0.0162 (17)	−0.0189 (17)	0.0065 (16)	−0.0040 (14)
O4	0.075 (3)	0.027 (2)	0.0250 (19)	−0.0127 (18)	−0.0032 (18)	−0.0032 (15)
O5	0.089 (3)	0.0219 (19)	0.0234 (19)	−0.0153 (18)	0.0033 (19)	0.0003 (14)
O6	0.089 (3)	0.028 (2)	0.0233 (19)	−0.0018 (19)	0.0155 (19)	−0.0030 (16)
O7	0.141 (5)	0.055 (3)	0.056 (3)	−0.055 (3)	0.033 (3)	−0.023 (2)
O8	0.136 (5)	0.056 (3)	0.051 (3)	−0.041 (3)	0.012 (3)	0.019 (2)
O9	0.054 (2)	0.0217 (18)	0.0266 (19)	−0.0063 (17)	−0.0021 (17)	−0.0016 (15)
O10	0.118 (4)	0.021 (2)	0.028 (2)	−0.003 (2)	0.026 (2)	−0.0001 (16)
O11	0.048 (2)	0.0273 (19)	0.0229 (19)	−0.0100 (17)	0.0039 (16)	0.0005 (15)
Zn1	0.0418 (4)	0.0228 (3)	0.0197 (3)	−0.0056 (2)	0.0028 (2)	−0.0024 (2)

Geometric parameters (Å, º) top

C1—C2	1.325 (7)	C13—H13	0.9300
C1—N1	1.344 (6)	C14—C16	1.393 (6)
C1—H1	0.9300	C14—C15	1.507 (6)
C2—C3	1.399 (8)	C15—O6	1.243 (5)
C2—H2	0.9300	C15—O5	1.249 (5)
C3—C4	1.375 (7)	C16—C17	1.374 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.398 (7)	C17—C18	1.370 (6)
C4—H4	0.9300	C17—N3	1.475 (6)
C5—N1	1.342 (6)	C18—H18	0.9300
C5—C6	1.468 (6)	N1—O2	1.353 (5)
C6—C7	1.361 (7)	N2—O1	1.325 (5)
C6—N2	1.374 (6)	N3—O8	1.214 (6)
C7—C8	1.390 (7)	N3—O7	1.244 (6)
C7—H7	0.9300	O1—Zn1	2.094 (3)
C8—C9	1.338 (7)	O2—Zn1	2.144 (3)
C8—H8	0.9300	O3—Zn1	2.043 (3)
C9—C10	1.394 (7)	O9—Zn1	2.125 (3)
C9—H9	0.9300	O9—H9A	0.816 (19)
C10—N2	1.349 (6)	O9—H9B	0.821 (19)
C10—H10	0.9300	O10—Zn1	2.067 (3)
C11—O4	1.254 (5)	O10—H10A	0.80 (2)
C11—O3	1.268 (5)	O10—H10B	0.818 (19)
C11—C12	1.514 (6)	O11—Zn1	2.054 (4)
C12—C13	1.370 (6)	O11—H11A	0.814 (19)
C12—C18	1.407 (6)	O11—H11B	0.833 (19)
C13—C14	1.395 (6)

C2—C1—N1	120.9 (5)	C17—C16—C14	118.1 (4)
C2—C1—H1	119.5	C17—C16—H16	121.0
N1—C1—H1	119.5	C14—C16—H16	121.0
C1—C2—C3	120.7 (5)	C18—C17—C16	124.3 (4)
C1—C2—H2	119.7	C18—C17—N3	117.2 (4)
C3—C2—H2	119.7	C16—C17—N3	118.6 (4)
C4—C3—C2	118.0 (5)	C17—C18—C12	117.7 (4)
C4—C3—H3	121.0	C17—C18—H18	121.2
C2—C3—H3	121.0	C12—C18—H18	121.2
C3—C4—C5	119.9 (5)	C5—N1—C1	121.6 (5)
C3—C4—H4	120.1	C5—N1—O2	119.5 (4)
C5—C4—H4	120.1	C1—N1—O2	118.9 (4)
N1—C5—C4	118.8 (5)	O1—N2—C10	120.1 (4)
N1—C5—C6	118.7 (4)	O1—N2—C6	118.9 (4)
C4—C5—C6	122.0 (4)	C10—N2—C6	121.0 (4)
C7—C6—N2	119.1 (5)	O8—N3—O7	123.8 (5)
C7—C6—C5	123.2 (5)	O8—N3—C17	118.8 (5)
N2—C6—C5	117.8 (4)	O7—N3—C17	117.2 (5)
C6—C7—C8	121.0 (5)	N2—O1—Zn1	116.6 (3)
C6—C7—H7	119.5	N1—O2—Zn1	117.1 (2)
C8—C7—H7	119.5	C11—O3—Zn1	121.9 (3)
C9—C8—C7	118.6 (5)	Zn1—O9—H9A	157 (4)
C9—C8—H8	120.7	Zn1—O9—H9B	93 (3)
C7—C8—H8	120.7	H9A—O9—H9B	102 (4)
C8—C9—C10	121.4 (5)	Zn1—O10—H10A	124 (4)
C8—C9—H9	119.3	Zn1—O10—H10B	122 (4)
C10—C9—H9	119.3	H10A—O10—H10B	114 (5)
N2—C10—C9	119.0 (5)	Zn1—O11—H11A	94 (4)
N2—C10—H10	120.5	Zn1—O11—H11B	107 (4)
C9—C10—H10	120.5	H11A—O11—H11B	104 (4)
O4—C11—O3	126.4 (4)	O3—Zn1—O11	103.59 (13)
O4—C11—C12	116.2 (4)	O3—Zn1—O10	88.62 (16)
O3—C11—C12	117.4 (4)	O11—Zn1—O10	87.49 (15)
C13—C12—C18	118.8 (4)	O3—Zn1—O1	86.88 (13)
C13—C12—C11	120.9 (4)	O11—Zn1—O1	169.46 (12)
C18—C12—C11	120.3 (4)	O10—Zn1—O1	91.57 (15)
C12—C13—C14	122.7 (4)	O3—Zn1—O9	89.47 (13)
C12—C13—H13	118.6	O11—Zn1—O9	86.47 (13)
C14—C13—H13	118.6	O10—Zn1—O9	173.05 (17)
C16—C14—C13	118.4 (4)	O1—Zn1—O9	95.00 (13)
C16—C14—C15	121.9 (4)	O3—Zn1—O2	169.33 (13)
C13—C14—C15	119.7 (4)	O11—Zn1—O2	86.92 (12)
O6—C15—O5	124.0 (5)	O10—Zn1—O2	90.04 (16)
O6—C15—C14	118.4 (4)	O1—Zn1—O2	82.58 (12)
O5—C15—C14	117.6 (4)	O9—Zn1—O2	93.05 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O5ⁱ	0.82 (3)	2.08 (4)	2.773 (5)	143 (5)
O9—H9B···O4	0.83 (3)	1.83 (3)	2.635 (5)	164 (4)
O10—H10A···O6ⁱⁱ	0.81 (5)	1.96 (5)	2.735 (5)	161 (6)
O10—H10B···O6ⁱⁱⁱ	0.82 (5)	2.03 (5)	2.702 (5)	139 (5)
O11—H11A···O2^iv	0.82 (3)	1.95 (3)	2.687 (5)	149 (5)
O11—H11B···O5ⁱⁱ	0.83 (3)	1.87 (4)	2.692 (5)	169 (4)
C2—H2···O8^v	0.93	2.59	3.229 (8)	126
C3—H3···O6^vi	0.93	2.49	3.269 (7)	141
C4—H4···O3^vii	0.93	2.46	3.358 (7)	162
C13—H13···O4	0.93	2.47	2.780 (6)	100

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₃NO₆)(C₁₀H₈N₂O₂)(H₂O)₃]
M_r	516.72
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.3040 (14), 10.7036 (18), 11.6546 (19)
α, β, γ (°)	87.217 (3), 88.436 (3), 87.006 (3)
V (Å³)	1032.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.26
Crystal size (mm)	0.20 × 0.19 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.778, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections	6281, 3604, 2737
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.143, 1.05
No. of reflections	3604
No. of parameters	316
No. of restraints	15
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.52

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

O1—Zn1	2.094 (3)	O9—Zn1	2.125 (3)
O2—Zn1	2.144 (3)	O10—Zn1	2.067 (3)
O3—Zn1	2.043 (3)	O11—Zn1	2.054 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O5ⁱ	0.82 (3)	2.08 (4)	2.773 (5)	143 (5)
O9—H9B···O4	0.83 (3)	1.83 (3)	2.635 (5)	164 (4)
O10—H10A···O6ⁱⁱ	0.81 (5)	1.96 (5)	2.735 (5)	161 (6)
O10—H10B···O6ⁱⁱⁱ	0.82 (5)	2.03 (5)	2.702 (5)	139 (5)
O11—H11A···O2^iv	0.82 (3)	1.95 (3)	2.687 (5)	149 (5)
O11—H11B···O5ⁱⁱ	0.83 (3)	1.87 (4)	2.692 (5)	169 (4)
C2—H2···O8^v	0.93	2.59	3.229 (8)	126
C3—H3···O6^vi	0.93	2.49	3.269 (7)	141
C4—H4···O3^vii	0.93	2.46	3.358 (7)	162

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

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hill, R. J., Long, D. L., Turvey, M. S., Blake, A. J., Champness, N. R., Hubberstey, P., Wilson, C. & Schröder, M. (2004). Chem. Commun. pp. 1792–1793. Web of Science CSD CrossRef Google Scholar
Long, D. L., Blake, A. J., Champness, N. R., Wilson, C. & Schröder, M. (2001). Angew. Chem. Int. Ed. 40, 2443–2447. CrossRef Google Scholar
Ma, B. Q., Sun, H. L. & Gao, S. (2003). Chem. Commun. pp. 2164–2165. Web of Science CSD CrossRef 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

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Volume 65| Part 6| June 2009| Page m660

doi:10.1107/S1600536809015451

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