catena-Poly[[[aqua­pyridine­zinc(II)]-μ2-3,3′-(p-phenyl­ene)diacrylato] pyridine solvate]

Su, D.; Song, D.; Fu, Z.

doi:10.1107/S1600536810033167

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1163

https://doi.org/10.1107/S1600536810033167

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catena-Poly[[[aquapyridinezinc(II)]-μ₂-3,3′-(p-phenylene)diacrylato] pyridine solvate]

Dongpo Su,^a Desheng Song ^a and Zhiyong Fu ^a ^*

^aSchool of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, People's Republic of China
^*Correspondence e-mail: zyfu@scut.edu.cn

(Received 27 July 2010; accepted 17 August 2010; online 28 August 2010)

The title compound, {[Zn(C₁₂H₈O₄)(C₅H₅N)(H₂O)]·C₅H₅N}_n, has been prepared by hydrothermal reaction. The Zn^II atom is six-coordinated by four carboxylate O atoms of two p-phenylenediacrylate (ppda²⁻) ligands, one N atom of a pyridine molecule and one O atom of a water molecule in a distorted octahedral environment. The carboxylate groups of the ppda²⁻ anions are in a bridging–chelating mode, in which two O atoms chelate one Zn²⁺ ion. These connections result in an extended chain structure. Parallel packing of the chains forms a two-dimensional network with intermolecular edge-to-face interactions. Further linkages between the layers through O—H⋯O hydrogen-bonding interactions result in a three-dimensional supramolecular architecture with one-dimensional rectanglar channels.

Related literature

For the applications of metal-organic frameworks, see: Li et al. (2009 ); Zhang et al. (2010 ). For the rational design and synthesis of coordination polymers by covalent interactions or supramolecular contacts, see: Jose et al. (2010 ); Zeng et al. (2010 ). For a similar complex, see: Sun et al. (2009 ).

Experimental

Crystal data

[Zn(C₁₂H₈O₄)(C₅H₅N)(H₂O)]·C₅H₅N
M_r = 457.77
Monoclinic, P 2₁ /c
a = 10.2132 (15) Å
b = 17.375 (3) Å
c = 12.8144 (19) Å
β = 112.360 (2)°
V = 2103.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 110 K
0.30 × 0.16 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.74, T_max = 0.85
9012 measured reflections
3657 independent reflections
2923 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.088
S = 1.05
3657 reflections
267 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.91 e Å⁻³
Δρ_min = −0.81 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N1	2.093 (2)
Zn1—O5	2.0288 (19)
Zn1—O4	2.0324 (18)
Zn1—O2ⁱ	2.0368 (18)
Zn1—O1ⁱ	2.3019 (18)
Zn1—O3	2.4099 (19)
Symmetry code: (i) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1⋯O4ⁱⁱ	0.80 (4)	1.94 (4)	2.743 (4)	172 (4)
Symmetry code: (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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: https://doi.org/10.1107/S1600536810033167/pb2038sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033167/pb2038Isup2.hkl

checkCIF report

Comment top

Metal-organic frameworks (MOFs) became one of the most active research areas in chemistry and materials in recent years due to their intriguing variety of architectures as well as promising applications as functional materials (Li et al., 2009; Zhang et al., 2010). One of the current interesting topics is to rationally design and synthesize coordination polymers and supramolecular organization by coordinated covalent bonds or supramolecular contacts (Zeng et al., 2010; Jose et al., 2010). Herein, we report the synthesis and characterization of a new metal organic framework with three-dimensional supramolecular structural motif. In the title compound, the Zn^II center is six-coordinated in a distorted octahedral geometry (Figure 1), surrounded by O1, O2, O4 from two ppda^2- ligand and O5 from a water molecule in the equatorial plane, and N1, O3 of pyridine molecule and ppda^2- ligand respectively in the axial position. The ppda^2- anion adopts a bridging coordination mode, interconnect with the zinc ions forming a 1-D infinite chain. The shortest distance between the neighbour zinc centers is 15.26 Å. The parallel chains are arranged into a two-dimensional network by intermolecular edge-to-face C—H···pi interactions (Figure 2). Two neighboring pyridine molecules from adjacent chains are parallel and form a dihedral angle of 58.1° with the plane of uncoordinated pyridine molecule. C—H···pi interactions exist between uncoordinated pyridine molecule and coordinated pyridine molecules. The C19—H19A and C22—H22A groups point to the center of adjacent pyridine rings, with H···centroid distances 2.9408 (3) and 3.3096 (5) Å. These two-dimensional networks are further linked via interlayer strong O—H···O hydrogen-bonding interactions, forming a three-dimensional supramolecular architecture with one-dimensional rectangle-shaped channels along the a direction (Figure 3). The H1···O4 distance is 1.8628Å and the O5—H1···O4 bond angle is 171.58°. Guest pyridine molecules are situated in the cavities.

Related literature top

For the applications of metal-organic frameworks, see: Li et al. (2009); Zhang et al. (2010). For the rational design and synthesis of coordination polymers by coordinated covalent bonds or supramolecular contacts, see: Jose et al. (2010); Zeng et al. (2010). For a similar complex, see: Sun et al. (2009).

Experimental top

A mixture of H₂ppda (0.0218 g, 0.1 mmol), Zn(OAc)₂.2H₂O (0.0219 g, 0.1 mmol), 4,4,-bpy (0.0156 g, 0.1 mmol), and py/H₂O (1:3, 12 ml) was sealed in a 25 ml Teflon-lined bomb and heated at 353 K for 48 h. The reaction mixture was then allowed to cool to room temperature at a rate of 3 K/h. Colorless block-shape crystals were obtained.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Sheldrick, 2008); 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 (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. View of the two-dimensional supramolecular layer of the title compound.
	Fig. 3. Three-dimensional supramolecular network of the title complex.

catena-Poly[[[aquapyridinezinc(II)]-µ₂-3,3'-(p-phenylene)diacrylato] pyridine solvate] top

Crystal data top

[Zn(C₁₂H₈O₄)(C₅H₅N)(H₂O)]·C₅H₅N	F(000) = 944
M_r = 457.77	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3657 reflections
a = 10.2132 (15) Å	θ = 2.9–25.0°
b = 17.375 (3) Å	µ = 1.20 mm⁻¹
c = 12.8144 (19) Å	T = 110 K
β = 112.360 (2)°	Block, colorless
V = 2103.0 (5) Å³	0.30 × 0.16 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3657 independent reflections
Radiation source: fine-focus sealed tube	2923 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.74, T_max = 0.85	k = −20→15
9012 measured reflections	l = −11→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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.044P)² + 1.4847P] where P = (F_o² + 2F_c²)/3
3657 reflections	(Δ/σ)_max < 0.001
267 parameters	Δρ_max = 0.91 e Å⁻³
1 restraint	Δρ_min = −0.81 e Å⁻³

Crystal data top

[Zn(C₁₂H₈O₄)(C₅H₅N)(H₂O)]·C₅H₅N	V = 2103.0 (5) Å³
M_r = 457.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2132 (15) Å	µ = 1.20 mm⁻¹
b = 17.375 (3) Å	T = 110 K
c = 12.8144 (19) Å	0.30 × 0.16 × 0.15 mm
β = 112.360 (2)°

Data collection top

Bruker SMART CCD diffractometer	3657 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2923 reflections with I > 2σ(I)
T_min = 0.74, T_max = 0.85	R_int = 0.026
9012 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.91 e Å⁻³
3657 reflections	Δρ_min = −0.81 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
N1	0.5178 (2)	−0.01394 (13)	0.75537 (18)	0.0163 (5)
C18	0.9544 (3)	0.03667 (18)	0.3132 (2)	0.0260 (7)
H18A	0.9348	0.0054	0.3663	0.031*
Zn1	0.41999 (3)	0.072906 (17)	0.63842 (2)	0.01285 (11)
C1	1.3097 (3)	0.35091 (15)	0.2483 (2)	0.0145 (6)
O1	1.44021 (18)	0.34052 (11)	0.27971 (15)	0.0177 (4)
O2	1.24483 (18)	0.39778 (11)	0.16907 (14)	0.0149 (4)
O3	0.40900 (19)	0.18631 (11)	0.52712 (15)	0.0193 (4)
O4	0.58751 (18)	0.10624 (10)	0.60053 (14)	0.0148 (4)
O5	0.3145 (2)	0.00368 (12)	0.50538 (16)	0.0183 (4)
H2	0.239 (3)	0.0196 (18)	0.451 (2)	0.031 (9)*
H1	0.351 (4)	−0.026 (2)	0.476 (3)	0.030 (10)*
C2	1.2295 (3)	0.30907 (16)	0.3060 (2)	0.0155 (6)
H2A	1.2736	0.2670	0.3539	0.019*
C3	1.0980 (3)	0.32845 (15)	0.2929 (2)	0.0146 (6)
H3A	1.0559	0.3692	0.2417	0.018*
C4	1.0110 (3)	0.29379 (15)	0.3489 (2)	0.0144 (6)
C5	0.8720 (3)	0.31994 (16)	0.3217 (2)	0.0167 (6)
H5A	0.8369	0.3606	0.2688	0.020*
C6	0.7854 (3)	0.28786 (16)	0.3702 (2)	0.0158 (6)
H6A	0.6909	0.3058	0.3489	0.019*
C7	0.8350 (3)	0.22904 (15)	0.4506 (2)	0.0137 (5)
C8	0.9737 (3)	0.20268 (15)	0.4779 (2)	0.0137 (6)
H8A	1.0089	0.1623	0.5313	0.016*
C9	1.0604 (3)	0.23431 (15)	0.4286 (2)	0.0141 (5)
H9A	1.1543	0.2157	0.4489	0.017*
C10	0.7473 (3)	0.19340 (15)	0.5051 (2)	0.0138 (6)
H10A	0.7887	0.1517	0.5548	0.017*
C11	0.6165 (3)	0.21278 (15)	0.4930 (2)	0.0152 (6)
H11A	0.5755	0.2576	0.4507	0.018*
C12	0.5322 (3)	0.16709 (15)	0.5429 (2)	0.0141 (6)
C13	0.6192 (3)	0.00035 (18)	0.8551 (2)	0.0309 (5)
H13A	0.6482	0.0522	0.8739	0.037*
C14	0.6844 (4)	−0.05630 (18)	0.9326 (3)	0.0360 (6)
H14A	0.7576	−0.0436	1.0027	0.043*
C15	0.6423 (4)	−0.13168 (19)	0.9073 (3)	0.0345 (8)
H15A	0.6827	−0.1715	0.9607	0.041*
C16	0.5408 (4)	−0.14810 (19)	0.8033 (3)	0.0360 (6)
H16A	0.5118	−0.1996	0.7817	0.043*
C17	0.4820 (4)	−0.08740 (17)	0.7307 (3)	0.0309 (5)
H17A	0.4116	−0.0988	0.6588	0.037*
N2	1.0893 (3)	0.05277 (14)	0.3312 (2)	0.0227 (6)
C19	1.1138 (3)	0.09713 (18)	0.2556 (3)	0.0296 (7)
H19A	1.2093	0.1091	0.2676	0.035*
C20	1.0086 (4)	0.12641 (19)	0.1615 (3)	0.0344 (8)
H20A	1.0309	0.1575	0.1095	0.041*
C21	0.8701 (3)	0.1097 (2)	0.1440 (3)	0.0330 (8)
H21A	0.7946	0.1296	0.0802	0.040*
C22	0.8431 (3)	0.0636 (2)	0.2209 (3)	0.0343 (8)
H22A	0.7485	0.0505	0.2102	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0178 (12)	0.0153 (12)	0.0166 (11)	0.0013 (10)	0.0073 (9)	0.0012 (9)
C18	0.0300 (17)	0.0237 (16)	0.0258 (16)	−0.0048 (13)	0.0123 (14)	0.0010 (13)
Zn1	0.01274 (17)	0.01317 (17)	0.01527 (17)	0.00028 (13)	0.00828 (12)	0.00003 (13)
C1	0.0161 (14)	0.0127 (14)	0.0160 (13)	−0.0010 (11)	0.0075 (11)	−0.0045 (11)
O1	0.0132 (10)	0.0198 (10)	0.0219 (10)	0.0013 (8)	0.0088 (8)	0.0035 (8)
O2	0.0149 (9)	0.0156 (9)	0.0166 (9)	−0.0006 (8)	0.0087 (8)	0.0029 (8)
O3	0.0166 (10)	0.0215 (11)	0.0244 (10)	0.0026 (8)	0.0130 (8)	0.0056 (8)
O4	0.0153 (9)	0.0145 (10)	0.0174 (9)	0.0008 (8)	0.0093 (8)	0.0014 (8)
O5	0.0181 (11)	0.0179 (11)	0.0179 (10)	0.0039 (9)	0.0058 (9)	−0.0049 (9)
C2	0.0159 (14)	0.0166 (14)	0.0161 (13)	0.0002 (11)	0.0084 (11)	0.0021 (11)
C3	0.0156 (13)	0.0154 (14)	0.0128 (13)	−0.0010 (11)	0.0055 (11)	0.0009 (11)
C4	0.0127 (13)	0.0178 (14)	0.0131 (13)	−0.0024 (11)	0.0056 (11)	−0.0018 (11)
C5	0.0175 (14)	0.0161 (14)	0.0157 (13)	−0.0014 (11)	0.0056 (11)	0.0032 (11)
C6	0.0107 (13)	0.0206 (15)	0.0170 (13)	0.0012 (11)	0.0063 (11)	−0.0006 (11)
C7	0.0124 (13)	0.0158 (14)	0.0134 (13)	−0.0030 (11)	0.0053 (10)	−0.0021 (11)
C8	0.0174 (14)	0.0106 (13)	0.0106 (12)	−0.0006 (11)	0.0024 (11)	0.0009 (10)
C9	0.0110 (13)	0.0157 (14)	0.0157 (13)	0.0002 (11)	0.0054 (10)	−0.0028 (11)
C10	0.0155 (13)	0.0143 (14)	0.0104 (12)	−0.0027 (11)	0.0038 (10)	−0.0003 (10)
C11	0.0190 (14)	0.0118 (13)	0.0163 (13)	−0.0007 (11)	0.0082 (11)	0.0016 (11)
C12	0.0141 (14)	0.0162 (14)	0.0138 (13)	−0.0026 (11)	0.0073 (11)	−0.0051 (11)
C13	0.0386 (13)	0.0196 (12)	0.0240 (11)	−0.0022 (10)	0.0002 (10)	−0.0009 (9)
C14	0.0455 (14)	0.0231 (12)	0.0272 (12)	−0.0026 (11)	0.0000 (11)	−0.0008 (10)
C15	0.047 (2)	0.0245 (17)	0.0240 (16)	0.0069 (15)	0.0042 (15)	0.0071 (13)
C16	0.0455 (14)	0.0231 (12)	0.0272 (12)	−0.0026 (11)	0.0000 (11)	−0.0008 (10)
C17	0.0386 (13)	0.0196 (12)	0.0240 (11)	−0.0022 (10)	0.0002 (10)	−0.0009 (9)
N2	0.0251 (14)	0.0194 (13)	0.0230 (13)	0.0037 (10)	0.0084 (11)	−0.0013 (10)
C19	0.0239 (16)	0.0305 (18)	0.0362 (18)	−0.0024 (14)	0.0135 (14)	0.0017 (14)
C20	0.039 (2)	0.0326 (19)	0.0330 (18)	0.0029 (15)	0.0154 (15)	0.0118 (15)
C21	0.0267 (17)	0.0352 (19)	0.0313 (17)	0.0053 (15)	0.0042 (14)	0.0083 (15)
C22	0.0227 (17)	0.039 (2)	0.0382 (19)	−0.0055 (15)	0.0081 (15)	0.0018 (16)

Geometric parameters (Å, º) top

N1—C13	1.327 (4)	C5—H5A	0.9500
N1—C17	1.332 (4)	C6—C7	1.402 (4)
Zn1—N1	2.093 (2)	C6—H6A	0.9500
C18—N2	1.336 (4)	C7—C8	1.401 (4)
C18—C22	1.374 (4)	C7—C10	1.466 (4)
C18—H18A	0.9500	C8—C9	1.382 (4)
Zn1—O5	2.0288 (19)	C8—H8A	0.9500
Zn1—O4	2.0324 (18)	C9—H9A	0.9500
Zn1—O2ⁱ	2.0368 (18)	C10—C11	1.328 (4)
Zn1—O1ⁱ	2.3019 (18)	C10—H10A	0.9500
Zn1—O3	2.4099 (19)	C11—C12	1.484 (4)
Zn1—C1ⁱ	2.492 (3)	C11—H11A	0.9500
Zn1—C12	2.560 (3)	C13—C14	1.377 (4)
C1—O1	1.250 (3)	C13—H13A	0.9500
C1—O2	1.273 (3)	C14—C15	1.378 (4)
C1—C2	1.485 (4)	C14—H14A	0.9500
C1—Zn1ⁱⁱ	2.492 (3)	C15—C16	1.371 (4)
O1—Zn1ⁱⁱ	2.3019 (18)	C15—H15A	0.9500
O2—Zn1ⁱⁱ	2.0368 (18)	C16—C17	1.383 (4)
O3—C12	1.241 (3)	C16—H16A	0.9500
O4—C12	1.291 (3)	C17—H17A	0.9500
O5—H2	0.864 (18)	N2—C19	1.334 (4)
O5—H1	0.80 (4)	C19—C20	1.372 (4)
C2—C3	1.333 (4)	C19—H19A	0.9500
C2—H2A	0.9500	C20—C21	1.377 (5)
C3—C4	1.466 (4)	C20—H20A	0.9500
C3—H3A	0.9500	C21—C22	1.377 (5)
C4—C5	1.403 (4)	C21—H21A	0.9500
C4—C9	1.405 (4)	C22—H22A	0.9500
C5—C6	1.377 (4)

C13—N1—C17	116.8 (2)	C6—C5—C4	121.3 (2)
C13—N1—Zn1	122.7 (2)	C6—C5—H5A	119.3
C17—N1—Zn1	120.53 (19)	C4—C5—H5A	119.3
N2—C18—C22	122.6 (3)	C5—C6—C7	120.8 (2)
N2—C18—H18A	118.7	C5—C6—H6A	119.6
C22—C18—H18A	118.7	C7—C6—H6A	119.6
O5—Zn1—O4	101.20 (8)	C8—C7—C6	118.0 (2)
O5—Zn1—O2ⁱ	94.92 (8)	C8—C7—C10	119.1 (2)
O4—Zn1—O2ⁱ	148.85 (8)	C6—C7—C10	122.9 (2)
N1—Zn1—O5	97.50 (9)	C9—C8—C7	121.3 (2)
O4—Zn1—N1	99.25 (8)	C9—C8—H8A	119.4
O2ⁱ—Zn1—N1	104.90 (8)	C7—C8—H8A	119.4
O5—Zn1—O1ⁱ	155.29 (8)	C8—C9—C4	120.6 (2)
O4—Zn1—O1ⁱ	99.78 (7)	C8—C9—H9A	119.7
O1ⁱ—Zn1—O2ⁱ	60.49 (7)	C4—C9—H9A	119.7
N1—Zn1—O1ⁱ	91.86 (8)	C11—C10—C7	127.3 (2)
O5—Zn1—O3	95.57 (7)	C11—C10—H10A	116.3
O3—Zn1—O4	58.64 (7)	C7—C10—H10A	116.3
O2ⁱ—Zn1—O3	93.61 (7)	C10—C11—C12	122.5 (2)
N1—Zn1—O3	156.24 (8)	C10—C11—H11A	118.8
O1ⁱ—Zn1—O3	84.33 (7)	C12—C11—H11A	118.8
O5—Zn1—C1ⁱ	125.46 (8)	O3—C12—O4	120.6 (2)
O4—Zn1—C1ⁱ	125.88 (8)	O3—C12—C11	120.3 (2)
O2ⁱ—Zn1—C1ⁱ	30.61 (8)	O4—C12—C11	119.0 (2)
N1—Zn1—C1ⁱ	99.99 (8)	O3—C12—Zn1	68.89 (14)
O1ⁱ—Zn1—C1ⁱ	29.89 (7)	O4—C12—Zn1	51.76 (12)
O3—Zn1—C1ⁱ	88.32 (7)	C11—C12—Zn1	170.73 (19)
O5—Zn1—C12	99.68 (8)	N1—C13—C14	123.2 (3)
O4—Zn1—C12	29.91 (8)	N1—C13—H13A	118.4
O2ⁱ—Zn1—C12	121.19 (8)	C14—C13—H13A	118.4
N1—Zn1—C12	128.66 (9)	C13—C14—C15	119.1 (3)
O1ⁱ—Zn1—C12	92.05 (7)	C13—C14—H14A	120.4
O3—Zn1—C12	28.72 (7)	C15—C14—H14A	120.4
C1ⁱ—Zn1—C12	108.13 (8)	C16—C15—C14	118.7 (3)
O1—C1—O2	121.1 (2)	C16—C15—H15A	120.7
O1—C1—C2	119.4 (2)	C14—C15—H15A	120.7
O2—C1—C2	119.4 (2)	C15—C16—C17	118.0 (3)
O1—C1—Zn1ⁱⁱ	66.61 (14)	C15—C16—H16A	121.0
O2—C1—Zn1ⁱⁱ	54.53 (12)	C17—C16—H16A	121.0
C2—C1—Zn1ⁱⁱ	173.96 (19)	N1—C17—C16	124.2 (3)
C1—O1—Zn1ⁱⁱ	83.50 (15)	N1—C17—H17A	117.9
C1—O2—Zn1ⁱⁱ	94.86 (15)	C16—C17—H17A	117.9
C12—O3—Zn1	82.39 (15)	C19—N2—C18	117.5 (3)
C12—O4—Zn1	98.33 (15)	N2—C19—C20	123.5 (3)
Zn1—O5—H2	121 (2)	N2—C19—H19A	118.3
Zn1—O5—H1	125 (2)	C20—C19—H19A	118.3
H2—O5—H1	105 (3)	C19—C20—C21	118.5 (3)
C3—C2—C1	122.3 (3)	C19—C20—H20A	120.7
C3—C2—H2A	118.8	C21—C20—H20A	120.7
C1—C2—H2A	118.8	C20—C21—C22	118.7 (3)
C2—C3—C4	127.2 (3)	C20—C21—H21A	120.7
C2—C3—H3A	116.4	C22—C21—H21A	120.7
C4—C3—H3A	116.4	C21—C22—C18	119.2 (3)
C5—C4—C9	117.9 (2)	C21—C22—H22A	120.4
C5—C4—C3	119.3 (2)	C18—C22—H22A	120.4
C9—C4—C3	122.8 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O4ⁱⁱⁱ	0.80 (4)	1.94 (4)	2.743 (4)	172 (4)

Symmetry code: (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₂H₈O₄)(C₅H₅N)(H₂O)]·C₅H₅N
M_r	457.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	110
a, b, c (Å)	10.2132 (15), 17.375 (3), 12.8144 (19)
β (°)	112.360 (2)
V (Å³)	2103.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.30 × 0.16 × 0.15

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.74, 0.85
No. of measured, independent and observed [I > 2σ(I)] reflections	9012, 3657, 2923
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.088, 1.05
No. of reflections	3657
No. of parameters	267
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.91, −0.81

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—N1	2.093 (2)	Zn1—O1ⁱ	2.3019 (18)
Zn1—O5	2.0288 (19)	Zn1—O3	2.4099 (19)
Zn1—O4	2.0324 (18)	Zn1—C1ⁱ	2.492 (3)
Zn1—O2ⁱ	2.0368 (18)	Zn1—C12	2.560 (3)

N1—Zn1—O5	97.50 (9)	O3—Zn1—O4	58.64 (7)
O1ⁱ—Zn1—O2ⁱ	60.49 (7)

Symmetry code: (i) x−1, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O4ⁱⁱ	0.80 (4)	1.94 (4)	2.743 (4)	172 (4)

Symmetry code: (ii) −x+1, −y, −z+1.

Acknowledgements

The authors thank the NNSFC (No. 20701014), the Fundamental Research Funds for the Central Universities (2009ZM0030) and the SRP program of the SCUT for financial support.

References

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