Poly[[[aqua(2,2′-bipyridine-κ2N,N′)zinc(II)]-μ-2-nitroterephthalato-κ2O1:O4] monohydrate]

Li, H.-M.; Yuan, H.-B.; Yang, S.-Y.; Huang, R.-B.

doi:10.1107/S1600536810023615

Poly[[[aqua(2,2′-bipyridine-κ²N,N′)zinc(II)]-μ-2-nitroterephthalato-κ²O¹:O⁴] monohydrate]

H.-M. Li, H.-B. Yuan, S.-Y. Yang and R.-B. Huang

In the title compound, {[Zn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]·H₂O}_n, the Zn^II ion is square-pyramidally coordinated, and bridged by 2-nitro-terephthalate ligands, forming a chain running along [1 $\overline{1}$ 0]. Intramolecular hydrogen bonds are formed between the coordinated water molecules and the nitro O atoms. Adjacent chains are linked by hydrogen bonds between the coordinated water molecules and the O atoms of the monodentate carboxyl groups.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810023615/kp2266sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810023615/kp2266Isup2.hkl Contains datablock I

CCDC reference: 788258

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Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.004 Å
R factor = 0.041
wR factor = 0.119
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        107
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        446

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        100 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Benzne polycarboxylic acids and nitrogen hetero aromatic ligands have been used to construct Zn^II coordination polymers by hydrothermal syntheses. (Huang et al., 2008; Ma et al., 2005; Song et al., 2006; Wang et al., 2005; Yang et al., 2002; Yang et al., 2003a,b,c; Zhang et al., 2007; Zhang et al., 2003; Zhou et al., 2009a) In some of the researches, the substituents on the benzne polycarboxylic acids have been found to play important roles in determining the structures of the coordination polymers (Prajapati et al., 2009; Zhou et al., 2009b) In this paper, we would like to report a coordination polymer, {[Zn(ntp)(H₂O)(2,2'-bpy)](H₂O)}_n, 1 (ntp = 2-nitro-terephthalate, 2,2'-bpy = 2,2'-bipyridine) synthesized by hydrothermal reaction.

In the structure of I, the asymmetric unit contains one Zn^II ion, one ntp ligand, one coordinated water molecule, one 2,2'-bpy and one solvent water molecule. (Fig. 1, Table 1) The Zn^II ion is in a distorted square pyramidal geometry, coordinated by two carboxylate oxygen atoms from two ntp briding ligands, one oxygen atom from water molecule and two nitrogen atoms from 2,2'-bpy. In ntp, the carboxyl in the ortho position of nitro substituent adopts monodentate coordination mode, and the dihedral angle between it and the benzene ring is 45.96 °; the other carboxyl adopts semi-chelating mode, the dihedral angle is 11.35 °. In the semi-chelating mode, one of the coordination bond is very long and weak and is almost neglectable. (Zn1-O3ⁱ = 2.859 Å, ⁱ x - 1, y + 1, z) The Zn^II ion is bridged by ntp ligands to form a one dimensional chain running along [1 -1 0] direction (Fig. 2). Intramolecular hydrogen bonds are formed between the coordinated water molecules and the nitro oxygen atoms. Adjacent chains also form intermolecular hydrogen bonds between the coordinated water molecules and the oxygen atoms of the monodentate carboxyl groups (Table 2).

Related literature top

Benzene polycarboxylic acids and nitrogen hetero aromatic ligands have been used to construct Zn^II coordination polymers by hydrothermal synthesis, see: Huang et al. (2008); Ma et al. (2005); Song et al. (2006); Wang et al. (2005); Yang et al. (2002, 2003a,b,c); Zhang et al. (2003, 2007); Zhou et al. (2009a) The substituents on the benzene polycarboxylic acids have been found to play important roles in determining the structures of the coordination polymers, see: Prajapati et al. (2009); Zhou et al. (2009b).

Experimental top

The suspension of 2-nitro-terephthalic acid (0.042 g, 0.20 mmol) and 2,2'-bipyridine (0.033 g, 0.20 mmol) in H₂O (10 mL) was vigorously stirred, aqueous solution of sodium hydroxide (2 mol/L) was slowly added until the pH value was adjusted to 7, and then ZnCl₂ (0.027 g, 0.20 mmol) was added. The solution was placed in a 20 mL Teflon-lined vessel, heated to 453 K at the rate of 0.2 K/min, and kept at 453 K for 3 days, and then slowly cooled down to room temperature at the rate of 0.1 K/min. Yellow block crystals (0.035 g, yield 38%) were separated by filtration, washed with deionized water and dried in air. Elemental Analysis: C₁₈H₁₅N₃O₈Zn, found (calc.) C 47.23 (46.32), H 3.30 (3.24), N 9.18 (9.00).

Structure description top

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 coordination environment of zinc ion in I with the atom labeling scheme. Ellipsoids are drawn at the 50% probability level. Hydrogen bonds are showm in green dashed line. Symmetry codes: (i) x - 1, y + 1, z.
	Fig. 2. A perspective view of the one-dimensional chain of I.

Poly[[[aqua(2,2'-bipyridine-κ²N,N')zinc(II)]-µ- 2-nitroterephthalato-κ²O¹:O⁴] monohydrate] top

Crystal data top

[Zn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]·H₂O	Z = 2
M_r = 466.70	F(000) = 476
Triclinic, P1	D_x = 1.744 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5570 (5) Å	Cell parameters from 4213 reflections
b = 9.1074 (5) Å	θ = 2.3–28.5°
c = 12.2060 (7) Å	µ = 1.44 mm⁻¹
α = 84.558 (1)°	T = 297 K
β = 76.863 (1)°	Block, yellow
γ = 73.692 (1)°	0.41 × 0.36 × 0.33 mm
V = 888.58 (9) Å³

Data collection top

Bruker SMART APEX area-detector diffractometer	3915 independent reflections
Radiation source: fine-focus sealed tube	3739 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scan	θ_max = 28.6°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
T_min = 0.590, T_max = 0.648	k = −11→11
5326 measured reflections	l = −15→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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0588P)² + 0.302P] where P = (F_o² + 2F_c²)/3
3915 reflections	(Δ/σ)_max = 0.001
285 parameters	Δρ_max = 0.65 e Å⁻³
4 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Zn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]·H₂O	γ = 73.692 (1)°
M_r = 466.70	V = 888.58 (9) Å³
Triclinic, P1	Z = 2
a = 8.5570 (5) Å	Mo Kα radiation
b = 9.1074 (5) Å	µ = 1.44 mm⁻¹
c = 12.2060 (7) Å	T = 297 K
α = 84.558 (1)°	0.41 × 0.36 × 0.33 mm
β = 76.863 (1)°

Data collection top

Bruker SMART APEX area-detector diffractometer	3915 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3739 reflections with I > 2σ(I)
T_min = 0.590, T_max = 0.648	R_int = 0.028
5326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	4 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.65 e Å⁻³
3915 reflections	Δρ_min = −0.39 e Å⁻³
285 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	0.10197 (3)	0.50965 (3)	0.27688 (2)	0.02770 (12)
O1	0.3177 (2)	0.3927 (2)	0.31591 (17)	0.0375 (4)
O1W	−0.0424 (3)	0.4071 (2)	0.40216 (18)	0.0373 (4)
H1A	−0.131 (3)	0.463 (3)	0.440 (3)	0.043 (10)*
H1B	−0.003 (4)	0.340 (3)	0.448 (2)	0.043 (10)*
O2	0.3290 (3)	0.4075 (3)	0.49422 (19)	0.0493 (6)
O2W	0.4501 (5)	0.3808 (4)	0.6976 (2)	0.0700 (8)
H2A	0.425 (6)	0.386 (6)	0.634 (2)	0.084*
H2B	0.547 (3)	0.392 (6)	0.673 (4)	0.084*
O3	1.0362 (3)	−0.2228 (3)	0.4031 (2)	0.0547 (6)
O4	0.9149 (3)	−0.3030 (2)	0.2882 (2)	0.0460 (5)
O5	0.2308 (3)	0.1110 (3)	0.3586 (2)	0.0519 (6)
O6	0.3909 (4)	0.0225 (4)	0.2029 (3)	0.0690 (8)
N1	0.2312 (3)	0.6052 (2)	0.12874 (19)	0.0302 (4)
N2	0.0999 (3)	0.3715 (2)	0.15004 (19)	0.0306 (5)
N3	0.3663 (3)	0.0691 (3)	0.2970 (2)	0.0368 (5)
C1	0.5136 (3)	0.2006 (3)	0.3915 (2)	0.0258 (5)
C2	0.5128 (3)	0.0739 (3)	0.3376 (2)	0.0274 (5)
C3	0.6443 (3)	−0.0554 (3)	0.3223 (2)	0.0317 (5)
H3A	0.6396	−0.1378	0.2847	0.038*
C4	0.7833 (3)	−0.0609 (3)	0.3636 (2)	0.0304 (5)
C5	0.7895 (3)	0.0643 (3)	0.4159 (2)	0.0343 (6)
H5A	0.8840	0.0619	0.4422	0.041*
C6	0.6559 (3)	0.1934 (3)	0.4294 (2)	0.0318 (5)
H6A	0.6621	0.2771	0.4648	0.038*
C7	0.3725 (3)	0.3455 (3)	0.4030 (2)	0.0283 (5)
C8	0.9233 (4)	−0.2058 (3)	0.3517 (2)	0.0376 (6)
C9	0.2869 (4)	0.7290 (3)	0.1244 (3)	0.0378 (6)
H9A	0.2710	0.7795	0.1904	0.045*
C10	0.3665 (4)	0.7837 (3)	0.0258 (3)	0.0440 (7)
H10A	0.4041	0.8703	0.0248	0.053*
C11	0.3905 (4)	0.7090 (4)	−0.0723 (3)	0.0448 (7)
H11A	0.4457	0.7438	−0.1402	0.054*
C12	0.3314 (4)	0.5822 (3)	−0.0682 (2)	0.0395 (6)
H12A	0.3454	0.5303	−0.1333	0.047*
C13	0.2514 (3)	0.5336 (3)	0.0338 (2)	0.0302 (5)
C14	0.1825 (3)	0.3991 (3)	0.0464 (2)	0.0306 (5)
C15	0.1997 (4)	0.3087 (4)	−0.0424 (3)	0.0438 (7)
H15A	0.2559	0.3304	−0.1140	0.053*
C16	0.1324 (5)	0.1859 (4)	−0.0232 (3)	0.0510 (8)
H16A	0.1440	0.1225	−0.0816	0.061*
C17	0.0489 (4)	0.1579 (4)	0.0818 (3)	0.0464 (7)
H17A	0.0020	0.0757	0.0960	0.056*
C18	0.0344 (4)	0.2527 (3)	0.1669 (3)	0.0389 (6)
H18A	−0.0231	0.2332	0.2387	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02659 (18)	0.02438 (17)	0.02802 (18)	0.00097 (12)	−0.00622 (12)	−0.00332 (11)
O1	0.0309 (10)	0.0370 (10)	0.0351 (10)	0.0057 (8)	−0.0081 (8)	0.0037 (8)
O1W	0.0307 (10)	0.0347 (10)	0.0358 (11)	0.0018 (8)	0.0006 (8)	0.0006 (8)
O2	0.0432 (12)	0.0515 (12)	0.0397 (12)	0.0159 (10)	−0.0096 (10)	−0.0196 (10)
O2W	0.096 (2)	0.088 (2)	0.0453 (15)	−0.0528 (19)	−0.0214 (15)	0.0056 (14)
O3	0.0361 (12)	0.0516 (13)	0.0633 (16)	0.0094 (10)	−0.0150 (11)	0.0090 (11)
O4	0.0421 (12)	0.0311 (10)	0.0485 (13)	0.0097 (9)	0.0000 (10)	−0.0035 (9)
O5	0.0312 (11)	0.0619 (14)	0.0611 (15)	−0.0123 (10)	−0.0113 (10)	0.0092 (12)
O6	0.0621 (17)	0.0779 (18)	0.0722 (18)	−0.0005 (14)	−0.0334 (15)	−0.0364 (15)
N1	0.0317 (11)	0.0271 (10)	0.0298 (11)	−0.0043 (8)	−0.0068 (9)	−0.0017 (8)
N2	0.0302 (11)	0.0288 (10)	0.0323 (11)	−0.0032 (8)	−0.0101 (9)	−0.0032 (8)
N3	0.0367 (13)	0.0285 (11)	0.0477 (14)	−0.0062 (9)	−0.0173 (11)	0.0000 (10)
C1	0.0237 (11)	0.0238 (10)	0.0248 (11)	0.0002 (9)	−0.0033 (9)	0.0002 (9)
C2	0.0265 (12)	0.0262 (11)	0.0287 (12)	−0.0051 (9)	−0.0073 (9)	0.0015 (9)
C3	0.0350 (14)	0.0240 (11)	0.0329 (13)	−0.0027 (10)	−0.0055 (11)	−0.0049 (9)
C4	0.0285 (12)	0.0254 (11)	0.0293 (12)	0.0010 (9)	−0.0016 (10)	0.0027 (9)
C5	0.0259 (12)	0.0378 (13)	0.0365 (14)	−0.0012 (10)	−0.0106 (11)	0.0001 (11)
C6	0.0300 (13)	0.0291 (12)	0.0356 (14)	−0.0027 (10)	−0.0103 (11)	−0.0057 (10)
C7	0.0232 (11)	0.0246 (11)	0.0319 (13)	−0.0003 (9)	−0.0028 (10)	−0.0009 (9)
C8	0.0333 (14)	0.0281 (12)	0.0368 (15)	0.0039 (11)	0.0036 (11)	0.0064 (11)
C9	0.0405 (15)	0.0309 (13)	0.0417 (16)	−0.0078 (11)	−0.0087 (12)	−0.0047 (11)
C10	0.0459 (17)	0.0334 (14)	0.0508 (18)	−0.0131 (13)	−0.0053 (14)	0.0033 (12)
C11	0.0468 (17)	0.0478 (17)	0.0371 (16)	−0.0145 (14)	−0.0038 (13)	0.0054 (13)
C12	0.0451 (16)	0.0413 (15)	0.0301 (14)	−0.0093 (12)	−0.0055 (12)	−0.0035 (11)
C13	0.0278 (12)	0.0287 (11)	0.0310 (13)	−0.0008 (10)	−0.0074 (10)	−0.0037 (10)
C14	0.0297 (12)	0.0288 (11)	0.0317 (13)	−0.0017 (10)	−0.0096 (10)	−0.0039 (10)
C15	0.0501 (18)	0.0452 (16)	0.0371 (15)	−0.0095 (14)	−0.0110 (13)	−0.0125 (13)
C16	0.063 (2)	0.0447 (17)	0.053 (2)	−0.0159 (16)	−0.0197 (17)	−0.0158 (14)
C17	0.0522 (19)	0.0402 (15)	0.0542 (19)	−0.0177 (14)	−0.0179 (15)	−0.0055 (14)
C18	0.0406 (15)	0.0386 (14)	0.0385 (15)	−0.0108 (12)	−0.0105 (12)	0.0001 (12)

Geometric parameters (Å, º) top

Zn1—O1	1.9922 (19)	C3—C4	1.381 (4)
Zn1—O1W	2.063 (2)	C3—H3A	0.9300
Zn1—O4ⁱ	1.976 (2)	C4—C5	1.377 (4)
Zn1—N1	2.141 (2)	C4—C8	1.506 (3)
Zn1—N2	2.091 (2)	C5—C6	1.383 (4)
O1—C7	1.249 (3)	C5—H5A	0.9300
O1W—H1A	0.85 (3)	C6—H6A	0.9300
O1W—H1B	0.84 (3)	C9—C10	1.366 (4)
O2—C7	1.230 (3)	C9—H9A	0.9300
O2W—H2A	0.85 (3)	C10—C11	1.379 (5)
O2W—H2B	0.85 (3)	C10—H10A	0.9300
O3—C8	1.234 (4)	C11—C12	1.377 (4)
O4—C8	1.257 (4)	C11—H11A	0.9300
O4—Zn1ⁱⁱ	1.976 (2)	C12—C13	1.376 (4)
O5—N3	1.210 (3)	C12—H12A	0.9300
O6—N3	1.215 (3)	C13—C14	1.483 (4)
N1—C9	1.334 (4)	C14—C15	1.380 (4)
N1—C13	1.337 (3)	C15—C16	1.374 (5)
N2—C18	1.332 (4)	C15—H15A	0.9300
N2—C14	1.340 (4)	C16—C17	1.357 (5)
N3—C2	1.461 (3)	C16—H16A	0.9300
C1—C6	1.381 (4)	C17—C18	1.375 (4)
C1—C2	1.384 (3)	C17—H17A	0.9300
C1—C7	1.510 (3)	C18—H18A	0.9300
C2—C3	1.375 (3)

O1—Zn1—O1W	95.05 (8)	C1—C6—C5	121.3 (2)
O1—Zn1—N1	90.59 (8)	C1—C6—H6A	119.3
O1—Zn1—N2	98.69 (9)	C5—C6—H6A	119.3
O1W—Zn1—N1	170.66 (9)	O2—C7—O1	127.0 (2)
O1W—Zn1—N2	94.61 (9)	O2—C7—C1	117.3 (2)
O4ⁱ—Zn1—O1	149.63 (10)	O1—C7—C1	115.6 (2)
O4ⁱ—Zn1—O1W	89.11 (9)	O3—C8—O4	124.5 (3)
O4ⁱ—Zn1—N1	89.79 (9)	O3—C8—C4	119.8 (3)
O4ⁱ—Zn1—N2	110.97 (10)	O4—C8—C4	115.8 (3)
N1—Zn1—N2	77.14 (9)	N1—C9—C10	121.9 (3)
C7—O1—Zn1	137.57 (18)	N1—C9—H9A	119.1
Zn1—O1W—H1A	118 (2)	C10—C9—H9A	119.1
Zn1—O1W—H1B	124 (2)	C9—C10—C11	119.2 (3)
H1A—O1W—H1B	106 (3)	C9—C10—H10A	120.4
H2A—O2W—H2B	96 (5)	C11—C10—H10A	120.4
C8—O4—Zn1ⁱⁱ	113.6 (2)	C12—C11—C10	119.0 (3)
C9—N1—C13	119.3 (2)	C12—C11—H11A	120.5
C9—N1—Zn1	125.6 (2)	C10—C11—H11A	120.5
C13—N1—Zn1	115.06 (17)	C13—C12—C11	118.9 (3)
C18—N2—C14	118.6 (2)	C13—C12—H12A	120.6
C18—N2—Zn1	124.7 (2)	C11—C12—H12A	120.6
C14—N2—Zn1	116.48 (18)	N1—C13—C12	121.7 (3)
O5—N3—O6	124.9 (3)	N1—C13—C14	115.5 (2)
O5—N3—C2	118.3 (3)	C12—C13—C14	122.8 (2)
O6—N3—C2	116.7 (3)	N2—C14—C15	121.7 (3)
C6—C1—C2	116.8 (2)	N2—C14—C13	115.6 (2)
C6—C1—C7	120.2 (2)	C15—C14—C13	122.7 (3)
C2—C1—C7	122.9 (2)	C16—C15—C14	118.9 (3)
C3—C2—C1	123.1 (2)	C16—C15—H15A	120.5
C3—C2—N3	116.1 (2)	C14—C15—H15A	120.5
C1—C2—N3	120.8 (2)	C17—C16—C15	119.4 (3)
C2—C3—C4	118.9 (2)	C17—C16—H16A	120.3
C2—C3—H3A	120.6	C15—C16—H16A	120.3
C4—C3—H3A	120.6	C16—C17—C18	119.2 (3)
C5—C4—C3	119.6 (2)	C16—C17—H17A	120.4
C5—C4—C8	121.8 (3)	C18—C17—H17A	120.4
C3—C4—C8	118.6 (3)	N2—C18—C17	122.3 (3)
C4—C5—C6	120.4 (3)	N2—C18—H18A	118.9
C4—C5—H5A	119.8	C17—C18—H18A	118.9
C6—C5—H5A	119.8

O4ⁱ—Zn1—O1—C7	58.0 (4)	C6—C1—C7—O2	−46.1 (4)
O1W—Zn1—O1—C7	−38.9 (3)	C2—C1—C7—O2	137.9 (3)
N2—Zn1—O1—C7	−134.3 (3)	C6—C1—C7—O1	130.8 (3)
N1—Zn1—O1—C7	148.6 (3)	C2—C1—C7—O1	−45.1 (3)
O4ⁱ—Zn1—N1—C9	64.9 (2)	Zn1ⁱⁱ—O4—C8—O3	0.0 (4)
O1—Zn1—N1—C9	−84.8 (2)	Zn1ⁱⁱ—O4—C8—C4	−179.80 (17)
N2—Zn1—N1—C9	176.5 (2)	C5—C4—C8—O3	10.4 (4)
O4ⁱ—Zn1—N1—C13	−113.31 (19)	C3—C4—C8—O3	−168.5 (3)
O1—Zn1—N1—C13	97.06 (19)	C5—C4—C8—O4	−169.8 (3)
N2—Zn1—N1—C13	−1.72 (18)	C3—C4—C8—O4	11.3 (4)
O4ⁱ—Zn1—N2—C18	−96.8 (2)	C13—N1—C9—C10	−1.0 (4)
O1—Zn1—N2—C18	89.8 (2)	Zn1—N1—C9—C10	−179.1 (2)
O1W—Zn1—N2—C18	−6.0 (2)	N1—C9—C10—C11	−0.1 (5)
N1—Zn1—N2—C18	178.4 (2)	C9—C10—C11—C12	0.8 (5)
O4ⁱ—Zn1—N2—C14	88.66 (19)	C10—C11—C12—C13	−0.4 (5)
O1—Zn1—N2—C14	−84.70 (19)	C9—N1—C13—C12	1.4 (4)
O1W—Zn1—N2—C14	179.47 (18)	Zn1—N1—C13—C12	179.7 (2)
N1—Zn1—N2—C14	3.91 (18)	C9—N1—C13—C14	−178.8 (2)
C6—C1—C2—C3	0.8 (4)	Zn1—N1—C13—C14	−0.5 (3)
C7—C1—C2—C3	176.8 (2)	C11—C12—C13—N1	−0.7 (4)
C6—C1—C2—N3	178.4 (2)	C11—C12—C13—C14	179.5 (3)
C7—C1—C2—N3	−5.5 (4)	C18—N2—C14—C15	0.5 (4)
O5—N3—C2—C3	132.7 (3)	Zn1—N2—C14—C15	175.4 (2)
O6—N3—C2—C3	−47.2 (4)	C18—N2—C14—C13	179.7 (2)
O5—N3—C2—C1	−45.1 (3)	Zn1—N2—C14—C13	−5.4 (3)
O6—N3—C2—C1	135.0 (3)	N1—C13—C14—N2	3.8 (3)
C1—C2—C3—C4	0.8 (4)	C12—C13—C14—N2	−176.4 (2)
N3—C2—C3—C4	−176.9 (2)	N1—C13—C14—C15	−176.9 (3)
C2—C3—C4—C5	−2.0 (4)	C12—C13—C14—C15	2.9 (4)
C2—C3—C4—C8	177.0 (2)	N2—C14—C15—C16	−1.0 (5)
C3—C4—C5—C6	1.5 (4)	C13—C14—C15—C16	179.8 (3)
C8—C4—C5—C6	−177.4 (2)	C14—C15—C16—C17	0.9 (5)
C2—C1—C6—C5	−1.2 (4)	C15—C16—C17—C18	−0.4 (5)
C7—C1—C6—C5	−177.4 (2)	C14—N2—C18—C17	0.1 (4)
C4—C5—C6—C1	0.1 (4)	Zn1—N2—C18—C17	−174.4 (2)
Zn1—O1—C7—O2	−33.2 (5)	C16—C17—C18—N2	−0.1 (5)
Zn1—O1—C7—C1	150.2 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2ⁱⁱⁱ	0.85 (3)	1.83 (3)	2.670 (3)	174 (4)
O1W—H1B···O3^iv	0.84 (3)	2.02 (2)	2.779 (3)	150 (3)
O1W—H1B···O5	0.84 (3)	2.58 (3)	3.031 (3)	115 (3)
O2W—H2A···O2	0.85 (3)	2.03 (3)	2.865 (4)	171 (5)
O2W—H2B···O1^v	0.85 (3)	2.57 (4)	3.213 (4)	134 (4)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]·H₂O
M_r	466.70
Crystal system, space group	Triclinic, P1
Temperature (K)	297
a, b, c (Å)	8.5570 (5), 9.1074 (5), 12.2060 (7)
α, β, γ (°)	84.558 (1), 76.863 (1), 73.692 (1)
V (Å³)	888.58 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.44
Crystal size (mm)	0.41 × 0.36 × 0.33

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.590, 0.648
No. of measured, independent and observed [I > 2σ(I)] reflections	5326, 3915, 3739
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.674

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.119, 1.10
No. of reflections	3915
No. of parameters	285
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.39

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Selected geometric parameters (Å, º) top

Zn1—O1	1.9922 (19)	Zn1—N1	2.141 (2)
Zn1—O1W	2.063 (2)	Zn1—N2	2.091 (2)
Zn1—O4ⁱ	1.976 (2)

O1—Zn1—O1W	95.05 (8)	O4ⁱ—Zn1—O1	149.63 (10)
O1—Zn1—N1	90.59 (8)	O4ⁱ—Zn1—O1W	89.11 (9)
O1—Zn1—N2	98.69 (9)	O4ⁱ—Zn1—N1	89.79 (9)
O1W—Zn1—N1	170.66 (9)	O4ⁱ—Zn1—N2	110.97 (10)
O1W—Zn1—N2	94.61 (9)	N1—Zn1—N2	77.14 (9)

Symmetry code: (i) x−1, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2ⁱⁱ	0.85 (3)	1.83 (3)	2.670 (3)	174 (4)
O1W—H1B···O3ⁱⁱⁱ	0.84 (3)	2.02 (2)	2.779 (3)	150 (3)
O1W—H1B···O5	0.84 (3)	2.58 (3)	3.031 (3)	115 (3)
O2W—H2A···O2	0.85 (3)	2.03 (3)	2.865 (4)	171 (5)
O2W—H2B···O1^iv	0.85 (3)	2.57 (4)	3.213 (4)	134 (4)

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

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