Bis(4′-hy­droxy­biphenyl-4-carboxyl­ato-κO1)(1,10-phenanthroline-κ2N,N′)zinc

Wu, W.-P.; Wang, J.; Lu, L.; He, X.-Y.; Zou, L.-K.

doi:10.1107/S1600536811012244

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m568

doi:10.1107/S1600536811012244

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Bis(4′-hydroxybiphenyl-4-carboxylato-κO¹)(1,10-phenanthroline-κ²N,N′)zinc

Wei-Ping Wu,^a ^* Jun Wang,^a Lu Lu,^a Xi-Yang He ^a and Li-Ke Zou ^a

^aSchool of Chemistry and Pharmaceutical Engineering, Institute of Functionalized Materials, Sichuan University of Science and Engineering, Zigong, Sichuan 643000, People's Republic of China
^*Correspondence e-mail: wuweipingzg@126.com

(Received 30 March 2011; accepted 1 April 2011; online 13 April 2011)

In the title compound, [Zn(C₁₃H₉O₃)₂(C₁₂H₈N₂)], the Zn^II atom is located on a twofold rotation axis and has a distorted tetrahedral coordination with two N atoms from the phenanthroline ligand arranged around the twofold axis and two O atoms from two symmetry-related 4′-hydroxybiphenyl-4-carboxylate ligands. The molecules are linked by O—H⋯O hydrogen bonds, forming a chain developing parallel to [101].

Related literature

For background to crystal engineering, see: Aakeroy & Seddon (1993 ). For the related carboxylic acid, see: Song et al. (2004 ); Liu et al. (2011a ). For the related phenanthroline and its derivative complexes, see: Breneman et al. (1993 ); Liu et al. (2011b ); Zhang et al. (2011 ).

Experimental

Crystal data

[Zn(C₁₃H₉O₃)₂(C₁₂H₈N₂)]
M_r = 671.98
Monoclinic, C 2/c
a = 15.378 (8) Å
b = 10.616 (5) Å
c = 17.816 (9) Å
β = 90.702 (9)°
V = 2908 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.774, T_max = 0.833
10508 measured reflections
2605 independent reflections
2273 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.092
S = 1.06
2605 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱ	0.82	1.81	2.622 (2)	173
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012244/dn2671sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012244/dn2671Isup2.hkl

checkCIF report

Comment top

In the past years, many supramolecular motifs based on hydrogen bonds have been achieved by using transition metal centers and organic ligands (Aakeroy et al., 1993). The 4'-hydroxybiphenyl-4-carboxylic acid (H₂L) has inspired great research interest for assembling coordination architectures. As a versatile ligand, it contains two sulfonic groups and two hydroxyl groups, which may be partially or completely deprotonated and normally serves as linkage to construct diverse metallosupramolecular systems (Song et al., 2004; Liu et al., 2011a). On the other hand, 1, 10-Phenanthroline, as one kind of those ligand, has usually been used to construct a great variety of structurally interesting entities, such as monomers(Breneman et al. 1993; Liu et al., 2011b, Zhang et al., 2011). Herein, we are interested in self-assemblies of Zn^II ion with H₂L and phen, which led to the title compound.

The title compound, {[Zn(L)₂(phen)] (H₂L=4'-hydroxybiphenyl-4-carboxylic acid), is built up from a distorted tetrahedral Zn^IIlocated on a two fold axis and surrounded by two O atoms of two 4'-hydroxybiphenyl-4-carboxylate ligands and the two N atoms of the phenanthroline ligand (Fig. 1).

The molecules are linked by O-H···O hydrogen bonds, forming a one-dimensional chain parallel to the [1 0 1] direction (Fig. 2, Table 1).

Related literature top

For backgroup to crystal engineering, see: Aakeroy & Seddon (1993). For the related carboxylic acid, see Song et al. (2004); Liu et al. (2011a). For the related phenanthroline and its derivative complexes, see Breneman et al. (1993); Liu et al. (2011b); Zhang et al. (2011).

Experimental top

A mixture of Zn(AC)2.H2O(25mg, 0.1mmol), H₂L(26mg, 0.1mmol), phen(19mg, 0.1mmol), NaOH(0.1mmol) and 5mL H₂O and CH₃OH(2mL) was stirred for 3h, and then the mixture was transferred to an 25mL Teflon-lined reactor and kept under autogenous pressure at 423k for 3 days,then cooled down to room temperature. Single crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small sphere of arbitrary radii. [Symmetry code: (i) -x+1, y, -z+1/2]
	Fig. 2. Partial packing view showing the formation of the chain through O-H···O hydrogen bonds which are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry code: (i) x-1/2, -y+3/2, z-1/2]

Bis(4'-hydroxybiphenyl-4-carboxylato-κO¹)(1,10-phenanthroline- κ²N,N')zinc top

Crystal data top

[Zn(C₁₃H₉O₃)₂(C₁₂H₈N₂)]	F(000) = 1384
M_r = 671.98	D_x = 1.535 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2606 reflections
a = 15.378 (8) Å	θ = 2.3–25.2°
b = 10.616 (5) Å	µ = 0.90 mm⁻¹
c = 17.816 (9) Å	T = 298 K
β = 90.702 (9)°	Block, colourless
V = 2908 (2) Å³	0.30 × 0.27 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	2605 independent reflections
Radiation source: fine-focus sealed tube	2273 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→18
T_min = 0.774, T_max = 0.833	k = 0→12
10508 measured reflections	l = 0→21

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0557P)² + 1.3191P] where P = (F_o² + 2F_c²)/3
2605 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Zn(C₁₃H₉O₃)₂(C₁₂H₈N₂)]	V = 2908 (2) Å³
M_r = 671.98	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 15.378 (8) Å	µ = 0.90 mm⁻¹
b = 10.616 (5) Å	T = 298 K
c = 17.816 (9) Å	0.30 × 0.27 × 0.21 mm
β = 90.702 (9)°

Data collection top

Bruker APEXII area-detector diffractometer	2605 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2273 reflections with I > 2σ(I)
T_min = 0.774, T_max = 0.833	R_int = 0.027
10508 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.06	Δρ_max = 0.26 e Å⁻³
2605 reflections	Δρ_min = −0.32 e Å⁻³
214 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	0.5000	0.35249 (3)	0.2500	0.04222 (15)
O1	0.50786 (11)	0.45044 (15)	0.16187 (8)	0.0515 (4)
O2	0.61479 (12)	0.59120 (16)	0.16290 (10)	0.0650 (5)
O3	0.20326 (10)	1.04044 (13)	−0.23778 (9)	0.0462 (4)
H3A	0.1793	0.9948	−0.2689	0.069*
N1	0.56738 (11)	0.20478 (17)	0.29840 (9)	0.0419 (4)
C1	0.49614 (12)	0.62166 (18)	0.07931 (10)	0.0338 (4)
C2	0.53096 (13)	0.73018 (19)	0.04826 (12)	0.0396 (5)
H2	0.5858	0.7577	0.0637	0.047*
C3	0.48521 (12)	0.79735 (19)	−0.00498 (11)	0.0380 (4)
H3	0.5096	0.8700	−0.0249	0.046*
C4	0.40291 (12)	0.75884 (18)	−0.02979 (10)	0.0313 (4)
C5	0.36906 (12)	0.64957 (18)	0.00116 (12)	0.0373 (5)
H5	0.3145	0.6214	−0.0145	0.045*
C6	0.41457 (13)	0.58227 (19)	0.05454 (11)	0.0382 (5)
H6	0.3904	0.5094	0.0744	0.046*
C7	0.35300 (12)	0.83181 (18)	−0.08651 (10)	0.0317 (4)
C8	0.35415 (13)	0.96324 (18)	−0.08772 (11)	0.0392 (5)
H8	0.3889	1.0062	−0.0531	0.047*
C9	0.30532 (13)	1.03091 (19)	−0.13874 (12)	0.0406 (5)
H9	0.3080	1.1184	−0.1387	0.049*
C10	0.25204 (12)	0.96926 (18)	−0.19028 (11)	0.0346 (4)
C11	0.25167 (12)	0.83874 (18)	−0.19150 (11)	0.0349 (4)
H11	0.2178	0.7961	−0.2269	0.042*
C12	0.30139 (12)	0.77208 (18)	−0.14041 (10)	0.0340 (4)
H12	0.3004	0.6845	−0.1420	0.041*
C13	0.54446 (14)	0.55089 (19)	0.13953 (11)	0.0388 (5)
C14	0.53520 (14)	0.09192 (19)	0.27718 (12)	0.0423 (5)
C15	0.56745 (16)	−0.0227 (2)	0.30488 (15)	0.0569 (7)
C16	0.63435 (18)	−0.0157 (3)	0.35882 (16)	0.0687 (8)
H16	0.6568	−0.0889	0.3801	0.082*
C17	0.66621 (18)	0.0979 (3)	0.37981 (15)	0.0672 (8)
H17	0.7113	0.1027	0.4149	0.081*
C18	0.63158 (15)	0.2074 (3)	0.34886 (13)	0.0533 (6)
H18	0.6541	0.2848	0.3640	0.064*
C19	0.53160 (19)	−0.1375 (2)	0.27629 (18)	0.0741 (9)
H19	0.5525	−0.2139	0.2945	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0656 (3)	0.0293 (2)	0.0316 (2)	0.000	−0.00514 (15)	0.000
O1	0.0671 (10)	0.0459 (9)	0.0411 (9)	−0.0079 (8)	−0.0141 (7)	0.0139 (7)
O2	0.0700 (11)	0.0529 (10)	0.0711 (12)	−0.0120 (8)	−0.0427 (9)	0.0165 (9)
O3	0.0560 (9)	0.0363 (8)	0.0458 (9)	0.0032 (7)	−0.0224 (7)	0.0020 (6)
N1	0.0476 (10)	0.0396 (10)	0.0387 (9)	0.0014 (8)	0.0050 (8)	0.0047 (8)
C1	0.0414 (10)	0.0318 (9)	0.0279 (10)	−0.0009 (8)	−0.0060 (8)	−0.0014 (8)
C2	0.0381 (10)	0.0369 (11)	0.0433 (11)	−0.0089 (8)	−0.0153 (9)	0.0021 (9)
C3	0.0393 (10)	0.0346 (10)	0.0399 (11)	−0.0099 (8)	−0.0079 (8)	0.0053 (9)
C4	0.0334 (9)	0.0331 (10)	0.0274 (9)	−0.0019 (7)	−0.0027 (7)	−0.0017 (8)
C5	0.0332 (10)	0.0401 (11)	0.0384 (11)	−0.0093 (8)	−0.0070 (8)	0.0037 (8)
C6	0.0417 (10)	0.0358 (11)	0.0369 (11)	−0.0094 (8)	−0.0014 (8)	0.0051 (9)
C7	0.0322 (9)	0.0335 (10)	0.0293 (9)	−0.0039 (7)	−0.0030 (7)	0.0007 (8)
C8	0.0450 (11)	0.0328 (10)	0.0395 (11)	−0.0068 (8)	−0.0151 (9)	−0.0028 (8)
C9	0.0472 (11)	0.0278 (10)	0.0464 (12)	−0.0025 (8)	−0.0127 (9)	−0.0008 (8)
C10	0.0353 (9)	0.0362 (10)	0.0321 (10)	0.0009 (8)	−0.0045 (8)	0.0013 (8)
C11	0.0372 (10)	0.0350 (10)	0.0323 (10)	−0.0047 (8)	−0.0088 (8)	−0.0038 (8)
C12	0.0381 (10)	0.0283 (10)	0.0355 (10)	−0.0047 (8)	−0.0043 (8)	−0.0016 (8)
C13	0.0508 (12)	0.0327 (10)	0.0328 (10)	0.0023 (9)	−0.0095 (9)	−0.0013 (8)
C14	0.0490 (12)	0.0332 (11)	0.0453 (12)	0.0032 (9)	0.0177 (9)	0.0044 (9)
C15	0.0637 (15)	0.0422 (13)	0.0657 (16)	0.0161 (11)	0.0328 (13)	0.0134 (11)
C16	0.0699 (17)	0.0684 (18)	0.0684 (18)	0.0340 (15)	0.0241 (14)	0.0281 (15)
C17	0.0565 (15)	0.090 (2)	0.0555 (16)	0.0228 (15)	0.0038 (12)	0.0197 (15)
C18	0.0527 (13)	0.0625 (15)	0.0448 (13)	0.0041 (11)	0.0010 (10)	0.0089 (11)
C19	0.088 (2)	0.0331 (12)	0.103 (3)	0.0104 (11)	0.0473 (17)	0.0107 (13)

Geometric parameters (Å, º) top

Zn1—O1ⁱ	1.8884 (16)	C7—C12	1.391 (2)
Zn1—O1	1.8884 (16)	C7—C8	1.396 (3)
Zn1—N1ⁱ	2.0626 (19)	C8—C9	1.375 (3)
Zn1—N1	2.0626 (19)	C8—H8	0.9300
O1—C13	1.272 (3)	C9—C10	1.387 (3)
O2—C13	1.231 (3)	C9—H9	0.9300
O3—C10	1.354 (2)	C10—C11	1.386 (3)
O3—H3A	0.8200	C11—C12	1.377 (3)
N1—C18	1.327 (3)	C11—H11	0.9300
N1—C14	1.349 (3)	C12—H12	0.9300
C1—C2	1.388 (3)	C14—C15	1.401 (3)
C1—C6	1.389 (3)	C14—C14ⁱ	1.444 (5)
C1—C13	1.499 (3)	C15—C16	1.401 (4)
C2—C3	1.374 (3)	C15—C19	1.429 (4)
C2—H2	0.9300	C16—C17	1.352 (4)
C3—C4	1.397 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.390 (4)
C4—C5	1.388 (3)	C17—H17	0.9300
C4—C7	1.480 (3)	C18—H18	0.9300
C5—C6	1.374 (3)	C19—C19ⁱ	1.342 (7)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300

O1ⁱ—Zn1—O1	113.17 (11)	C7—C8—H8	119.1
O1ⁱ—Zn1—N1ⁱ	136.83 (7)	C8—C9—C10	120.30 (19)
O1—Zn1—N1ⁱ	96.20 (7)	C8—C9—H9	119.8
O1ⁱ—Zn1—N1	96.20 (7)	C10—C9—H9	119.8
O1—Zn1—N1	136.83 (7)	O3—C10—C11	123.09 (17)
N1ⁱ—Zn1—N1	81.03 (10)	O3—C10—C9	117.94 (18)
C13—O1—Zn1	139.02 (14)	C11—C10—C9	118.97 (18)
C10—O3—H3A	109.5	C12—C11—C10	120.08 (17)
C18—N1—C14	118.4 (2)	C12—C11—H11	120.0
C18—N1—Zn1	129.27 (17)	C10—C11—H11	120.0
C14—N1—Zn1	112.17 (14)	C11—C12—C7	121.96 (18)
C2—C1—C6	118.32 (17)	C11—C12—H12	119.0
C2—C1—C13	120.73 (17)	C7—C12—H12	119.0
C6—C1—C13	120.93 (18)	O2—C13—O1	125.17 (18)
C3—C2—C1	120.62 (17)	O2—C13—C1	119.56 (18)
C3—C2—H2	119.7	O1—C13—C1	115.27 (17)
C1—C2—H2	119.7	N1—C14—C15	123.1 (2)
C2—C3—C4	121.40 (19)	N1—C14—C14ⁱ	117.24 (12)
C2—C3—H3	119.3	C15—C14—C14ⁱ	119.70 (15)
C4—C3—H3	119.3	C16—C15—C14	116.7 (2)
C5—C4—C3	117.49 (17)	C16—C15—C19	124.5 (2)
C5—C4—C7	120.96 (16)	C14—C15—C19	118.8 (3)
C3—C4—C7	121.54 (17)	C17—C16—C15	119.8 (2)
C6—C5—C4	121.26 (17)	C17—C16—H16	120.1
C6—C5—H5	119.4	C15—C16—H16	120.1
C4—C5—H5	119.4	C16—C17—C18	120.0 (3)
C5—C6—C1	120.90 (18)	C16—C17—H17	120.0
C5—C6—H6	119.5	C18—C17—H17	120.0
C1—C6—H6	119.5	N1—C18—C17	122.0 (3)
C12—C7—C8	116.89 (17)	N1—C18—H18	119.0
C12—C7—C4	121.29 (17)	C17—C18—H18	119.0
C8—C7—C4	121.81 (17)	C19ⁱ—C19—C15	121.45 (16)
C9—C8—C7	121.72 (18)	C19ⁱ—C19—H19	119.3
C9—C8—H8	119.1	C15—C19—H19	119.3

O1ⁱ—Zn1—O1—C13	39.5 (2)	O3—C10—C11—C12	−178.50 (18)
N1ⁱ—Zn1—O1—C13	−172.9 (2)	C9—C10—C11—C12	2.2 (3)
N1—Zn1—O1—C13	−89.4 (3)	C10—C11—C12—C7	0.0 (3)
O1ⁱ—Zn1—N1—C18	−40.1 (2)	C8—C7—C12—C11	−1.7 (3)
O1—Zn1—N1—C18	93.8 (2)	C4—C7—C12—C11	177.16 (18)
N1ⁱ—Zn1—N1—C18	−176.7 (2)	Zn1—O1—C13—O2	31.0 (4)
O1ⁱ—Zn1—N1—C14	135.31 (14)	Zn1—O1—C13—C1	−149.79 (17)
O1—Zn1—N1—C14	−90.72 (16)	C2—C1—C13—O2	1.7 (3)
N1ⁱ—Zn1—N1—C14	−1.20 (10)	C6—C1—C13—O2	−176.6 (2)
C6—C1—C2—C3	0.7 (3)	C2—C1—C13—O1	−177.54 (19)
C13—C1—C2—C3	−177.7 (2)	C6—C1—C13—O1	4.1 (3)
C1—C2—C3—C4	−0.3 (3)	C18—N1—C14—C15	−1.2 (3)
C2—C3—C4—C5	−0.3 (3)	Zn1—N1—C14—C15	−177.23 (17)
C2—C3—C4—C7	179.28 (19)	C18—N1—C14—C14ⁱ	179.4 (2)
C3—C4—C5—C6	0.4 (3)	Zn1—N1—C14—C14ⁱ	3.4 (3)
C7—C4—C5—C6	−179.15 (19)	N1—C14—C15—C16	2.1 (3)
C4—C5—C6—C1	0.0 (3)	C14ⁱ—C14—C15—C16	−178.5 (2)
C2—C1—C6—C5	−0.6 (3)	N1—C14—C15—C19	−177.1 (2)
C13—C1—C6—C5	177.78 (19)	C14ⁱ—C14—C15—C19	2.2 (4)
C5—C4—C7—C12	−36.7 (3)	C14—C15—C16—C17	−2.0 (4)
C3—C4—C7—C12	143.7 (2)	C19—C15—C16—C17	177.2 (3)
C5—C4—C7—C8	142.1 (2)	C15—C16—C17—C18	1.1 (4)
C3—C4—C7—C8	−37.4 (3)	C14—N1—C18—C17	0.2 (3)
C12—C7—C8—C9	1.3 (3)	Zn1—N1—C18—C17	175.43 (18)
C4—C7—C8—C9	−177.63 (19)	C16—C17—C18—N1	−0.2 (4)
C7—C8—C9—C10	0.9 (3)	C16—C15—C19—C19ⁱ	−178.9 (3)
C8—C9—C10—O3	178.0 (2)	C14—C15—C19—C19ⁱ	0.2 (5)
C8—C9—C10—C11	−2.7 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱⁱ	0.82	1.81	2.622 (2)	173

Symmetry code: (ii) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₃H₉O₃)₂(C₁₂H₈N₂)]
M_r	671.98
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	15.378 (8), 10.616 (5), 17.816 (9)
β (°)	90.702 (9)
V (Å³)	2908 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.30 × 0.27 × 0.21

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.774, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	10508, 2605, 2273
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.092, 1.06
No. of reflections	2605
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.82	1.81	2.622 (2)	173

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Acknowledgements

The authors acknowledge financial assistance from Sichuan University of Science and Engineering, the Institute of Functionalized Materials (grant Nos. 2009xjkpL003 and 2010XJKYL005), the Education Committee of Sichuan Province (No. 09ZA057) and the Committee of Science and Technology of Sichuan Province (No. 2010GZ0130).

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