catena-Poly[[(1,10-phenanthroline)zinc]-μ-2,2′-oxydibenzoato]

Cai, X.

doi:10.1107/S160053681102856X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1157

doi:10.1107/S160053681102856X

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catena-Poly[[(1,10-phenanthroline)zinc]-μ-2,2′-oxydibenzoato]

Xue Cai ^a ^*

^aDepartment of Chemistry, Mudanjiang Normal College, Mudanjiang 157012, Heilongjiang Province, People's Republic of China
^*Correspondence e-mail: xuecai@mail.sdu.edu.cn

(Received 7 July 2011; accepted 16 July 2011; online 30 July 2011)

In the title one-dimensional coordination polymer, [Zn(C₁₄H₈O₅)(C₁₂H₈N₂)]_n, the Zn^II ion is in a distorted octahedral coordination geometry with four O atoms from two carboxylate groups in bidentate chelating modes and two N atoms from a 1,10-phenanthroline ligand. The two terminal carboxylate groups bind the Zn^II ions, leading to a chain along the c axis. Adjacent chains are further linked by intermolecular π–π interactions with a shortest centroid–centroid distance of 3.586 (3) Å, forming a two-dimensional supramolecular architecture with (6,3)-network topology.

Related literature

For related structures and the properties of coordination polymers, see, for example: Evans et al. (1999 ); Yaghi et al. (1998 ); Wang et al. (2005 ); Li et al. (2003 ). For the synthesis of 3-(4-carboxyphenoxy)phthalic acid, see: Wang et al. (2009 ).

Experimental

Crystal data

[Zn(C₁₄H₈O₅)(C₁₂H₈N₂)]
M_r = 501.78
Monoclinic, P 2₁ /n
a = 7.7033 (18) Å
b = 17.403 (4) Å
c = 16.230 (4) Å
β = 90.184 (4)°
V = 2175.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.17 mm⁻¹
T = 293 K
0.15 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.901, T_max = 0.913
10511 measured reflections
3843 independent reflections
2320 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.112
S = 0.94
3843 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O2	2.011 (2)
Zn1—N1	2.114 (3)
Zn1—N2	2.129 (3)
Zn1—O4ⁱ	2.143 (3)
Zn1—O5ⁱ	2.172 (3)
Zn1—O1	2.395 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681102856X/is2747sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102856X/is2747Isup2.hkl

checkCIF report

Comment top

The design and synthesis of coordination polymers in supramolecular chemistry and crystal engineering, have been emerging as an ongoing field owing to their structural aesthetics and topologies as well as diverse functional properties (Evans et al., 1999; Yaghi et al., 1998) The semirigid V-shaped multicarboxylate ligands with two benzene rings bridged by an oxygen atom as central molecular framework are of increasing flexibility and therefore able to lead to metal complexes with diverse structures because of the free rotation of two benzene rings around the bridged atom (Wang et al., 2005).

The compound (I) crystallizes in the monoclinic system. As shown in Fig. 1, the Zn(II) ion is located in a distorted octahedral coordination geometry completed by four oxygen atoms from two carboxyl substituents of organic carboxylic acid in a bidentate chelating mode and two nitrogen atoms from the 1,10-phenanthroline ligand. The head and terminal carboxylate groups bind Zn(II) ions to lead to a one-dimensional chain. The neighboring chains are further linked by an intermolecular π–π interaction between the phenanthroline ring systems with a shortest centroid-centroid distance 3.586 (3) Å, forming a two-dimensional supramolecular architecture (Fig. 2) with 3-connect (6,3) network topology (Li et al., 2003)

Related literature top

For related structures and the properties of coordination polymers, see, for example: Evans et al. (1999); Yaghi et al. (1998); Wang et al. (2005); Li et al. (2003). For the synthesis of 3-(4-carboxyphenoxy)phthalic acid, see: Wang et al. (2009).

Experimental top

The mixture of Zn(OAc)₂.2H₂O (0.044 g, 0.2 mmol), 1,10-phenanthroline (0.0360 g, 0.2 mmol), 3-(4-carboxyphenoxy)phthalic acid (H₃L, 0.0302 g, 0.1 mmol), KOH (0.0168 g, 0.3 mmol) and H₂O (15 ml) was sealed in 25 ml Teflon-lined stainless steel reactor, which was heated to 160 °C. Colourless block-shaped crystals suitable for X-ray diffraction analysis were separated by filtration with the yield of 0.022 g.

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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at 30% probability level. All hydrogen atoms have been omitted. The suffix A corresponds to symmetry code (i) in Table 1.
	Fig. 2. A view of the two-dimensional supramolecular architecture of the title compound.

catena-Poly[[(1,10-phenanthroline)zinc]-µ-2,2'-oxydibenzoato] top

Crystal data top

[Zn(C₁₄H₈O₅)(C₁₂H₈N₂)]	F(000) = 1024
M_r = 501.78	D_x = 1.532 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1776 reflections
a = 7.7033 (18) Å	θ = 2.3–21.9°
b = 17.403 (4) Å	µ = 1.17 mm⁻¹
c = 16.230 (4) Å	T = 293 K
β = 90.184 (4)°	Block, colourless
V = 2175.8 (9) Å³	0.15 × 0.08 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3843 independent reflections
Radiation source: fine-focus sealed tube	2320 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 1.7°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −20→16
T_min = 0.901, T_max = 0.913	l = −18→19
10511 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0558P)²] where P = (F_o² + 2F_c²)/3
3843 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Zn(C₁₄H₈O₅)(C₁₂H₈N₂)]	V = 2175.8 (9) Å³
M_r = 501.78	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.7033 (18) Å	µ = 1.17 mm⁻¹
b = 17.403 (4) Å	T = 293 K
c = 16.230 (4) Å	0.15 × 0.08 × 0.06 mm
β = 90.184 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3843 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2320 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.913	R_int = 0.056
10511 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 0.94	Δρ_max = 0.49 e Å⁻³
3843 reflections	Δρ_min = −0.41 e Å⁻³
307 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
Zn1	0.13817 (6)	0.13631 (3)	0.83696 (3)	0.04575 (18)
O3	−0.2343 (3)	0.10169 (15)	0.42299 (15)	0.0501 (7)
O4	−0.1006 (3)	0.32154 (16)	0.33955 (16)	0.0508 (7)
N1	0.2187 (4)	0.02020 (18)	0.83600 (18)	0.0427 (8)
O5	−0.3157 (3)	0.24285 (15)	0.36218 (17)	0.0576 (8)
O2	−0.0997 (3)	0.14036 (15)	0.78576 (15)	0.0505 (7)
C25	0.2064 (5)	0.0400 (2)	0.9814 (2)	0.0449 (10)
O1	0.1008 (3)	0.14258 (19)	0.69057 (16)	0.0687 (9)
N2	0.1358 (4)	0.1102 (2)	0.96511 (19)	0.0488 (8)
C18	0.3184 (5)	−0.0821 (3)	0.9262 (3)	0.0527 (11)
C26	0.2485 (4)	−0.0083 (2)	0.9126 (2)	0.0431 (10)
C1	−0.0532 (5)	0.1416 (2)	0.7110 (2)	0.0446 (10)
C10	0.2189 (6)	0.0738 (3)	0.3682 (3)	0.0603 (12)
H10	0.2996	0.0340	0.3675	0.072*
C13	−0.0274 (4)	0.1917 (2)	0.3654 (2)	0.0366 (9)
C11	0.2659 (5)	0.1464 (3)	0.3426 (2)	0.0568 (12)
H11	0.3793	0.1561	0.3262	0.068*
C5	−0.4461 (5)	0.1157 (2)	0.5263 (3)	0.0558 (11)
H5	−0.5305	0.1067	0.4864	0.067*
C21	0.2411 (5)	0.0138 (3)	1.0612 (3)	0.0599 (13)
C12	0.1449 (4)	0.2045 (2)	0.3413 (2)	0.0431 (9)
H12	0.1781	0.2533	0.3242	0.052*
C3	−0.1465 (4)	0.1308 (2)	0.5634 (2)	0.0379 (9)
H3	−0.0304	0.1345	0.5483	0.046*
C14	−0.1562 (5)	0.2555 (2)	0.3559 (2)	0.0403 (9)
C2	−0.1942 (4)	0.1381 (2)	0.6454 (2)	0.0369 (8)
C4	−0.2722 (5)	0.1181 (2)	0.5043 (2)	0.0407 (9)
C15	0.2555 (5)	−0.0236 (3)	0.7719 (3)	0.0528 (11)
H15	0.2365	−0.0042	0.7193	0.063*
C9	0.0534 (6)	0.0604 (2)	0.3947 (2)	0.0559 (11)
H9	0.0222	0.0116	0.4127	0.067*
C17	0.3525 (5)	−0.1265 (3)	0.8556 (3)	0.0688 (13)
H17	0.3966	−0.1760	0.8613	0.083*
C22	0.2001 (6)	0.0634 (4)	1.1255 (3)	0.0769 (16)
H22	0.2193	0.0482	1.1797	0.092*
C8	−0.0682 (5)	0.1189 (2)	0.3951 (2)	0.0400 (9)
C16	0.3218 (5)	−0.0979 (3)	0.7799 (3)	0.0649 (13)
H16	0.3446	−0.1274	0.7334	0.078*
C20	0.3170 (6)	−0.0615 (3)	1.0716 (3)	0.0721 (15)
H20	0.3415	−0.0793	1.1244	0.086*
C24	0.0998 (6)	0.1566 (3)	1.0270 (3)	0.0647 (13)
H24	0.0525	0.2048	1.0164	0.078*
C6	−0.4932 (5)	0.1267 (3)	0.6066 (3)	0.0585 (12)
H6	−0.6100	0.1275	0.6208	0.070*
C23	0.1324 (7)	0.1338 (4)	1.1098 (3)	0.0764 (15)
H23	0.1073	0.1671	1.1530	0.092*
C7	−0.3675 (5)	0.1366 (2)	0.6669 (2)	0.0484 (10)
H7	−0.3998	0.1422	0.7218	0.058*
C19	0.3527 (6)	−0.1059 (3)	1.0072 (3)	0.0713 (14)
H19	0.4017	−0.1541	1.0161	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0362 (3)	0.0535 (3)	0.0475 (3)	−0.0081 (2)	−0.0086 (2)	0.0039 (2)
O3	0.0465 (17)	0.0655 (19)	0.0382 (15)	−0.0152 (14)	−0.0071 (13)	0.0035 (13)
O4	0.0418 (16)	0.0465 (17)	0.0641 (18)	0.0019 (13)	0.0034 (13)	0.0047 (14)
N1	0.0335 (17)	0.056 (2)	0.0385 (19)	−0.0111 (15)	−0.0066 (14)	0.0001 (17)
O5	0.0310 (16)	0.0534 (18)	0.088 (2)	0.0039 (13)	−0.0074 (14)	−0.0064 (15)
O2	0.0432 (16)	0.074 (2)	0.0344 (15)	−0.0024 (14)	−0.0046 (12)	−0.0032 (14)
C25	0.031 (2)	0.060 (3)	0.044 (2)	−0.0180 (19)	−0.0070 (18)	0.005 (2)
O1	0.0240 (15)	0.129 (3)	0.0530 (17)	−0.0026 (16)	−0.0029 (13)	−0.0030 (18)
N2	0.042 (2)	0.060 (2)	0.045 (2)	−0.0138 (17)	0.0019 (16)	−0.0062 (18)
C18	0.033 (2)	0.065 (3)	0.060 (3)	−0.008 (2)	−0.009 (2)	0.011 (2)
C26	0.027 (2)	0.057 (3)	0.046 (2)	−0.0136 (18)	−0.0087 (17)	0.007 (2)
C1	0.038 (2)	0.052 (3)	0.044 (2)	0.0057 (19)	−0.0039 (19)	−0.002 (2)
C10	0.055 (3)	0.061 (3)	0.065 (3)	0.025 (2)	−0.017 (2)	−0.012 (3)
C13	0.033 (2)	0.046 (2)	0.030 (2)	0.0025 (17)	−0.0037 (16)	−0.0015 (17)
C11	0.037 (2)	0.084 (4)	0.049 (3)	0.013 (2)	−0.0012 (19)	−0.010 (2)
C5	0.035 (2)	0.081 (3)	0.051 (3)	−0.003 (2)	−0.015 (2)	0.003 (2)
C21	0.037 (2)	0.102 (4)	0.040 (3)	−0.025 (2)	−0.006 (2)	0.009 (3)
C12	0.032 (2)	0.052 (2)	0.045 (2)	−0.002 (2)	0.0015 (17)	0.004 (2)
C3	0.0273 (19)	0.047 (2)	0.039 (2)	0.0002 (17)	−0.0036 (16)	0.0049 (18)
C14	0.035 (2)	0.049 (3)	0.036 (2)	0.0019 (19)	−0.0065 (17)	−0.0057 (18)
C2	0.0287 (19)	0.042 (2)	0.040 (2)	0.0005 (17)	−0.0034 (16)	0.0002 (18)
C4	0.036 (2)	0.047 (2)	0.039 (2)	−0.0042 (17)	−0.0059 (17)	0.0071 (18)
C15	0.040 (2)	0.069 (3)	0.049 (3)	−0.006 (2)	−0.0082 (19)	−0.005 (2)
C9	0.064 (3)	0.051 (3)	0.053 (3)	0.012 (2)	−0.014 (2)	0.001 (2)
C17	0.040 (3)	0.059 (3)	0.107 (4)	0.004 (2)	−0.008 (3)	0.005 (3)
C22	0.058 (3)	0.133 (5)	0.040 (3)	−0.032 (3)	−0.002 (2)	0.007 (3)
C8	0.039 (2)	0.051 (3)	0.030 (2)	−0.0003 (19)	−0.0073 (17)	−0.0003 (18)
C16	0.040 (3)	0.074 (3)	0.081 (3)	0.002 (2)	−0.010 (2)	−0.020 (3)
C20	0.043 (3)	0.111 (5)	0.062 (3)	−0.016 (3)	−0.014 (2)	0.047 (3)
C24	0.053 (3)	0.081 (4)	0.060 (3)	−0.017 (2)	0.008 (2)	−0.012 (3)
C6	0.025 (2)	0.089 (3)	0.062 (3)	−0.001 (2)	−0.004 (2)	−0.002 (3)
C23	0.064 (3)	0.120 (5)	0.045 (3)	−0.028 (3)	0.007 (2)	−0.024 (3)
C7	0.038 (2)	0.063 (3)	0.044 (2)	0.005 (2)	0.0032 (18)	0.001 (2)
C19	0.043 (3)	0.091 (4)	0.080 (4)	−0.005 (3)	−0.009 (3)	0.032 (3)

Geometric parameters (Å, º) top

Zn1—O2	2.011 (2)	C11—H11	0.9300
Zn1—N1	2.114 (3)	C5—C6	1.369 (6)
Zn1—N2	2.129 (3)	C5—C4	1.387 (5)
Zn1—O4ⁱ	2.143 (3)	C5—H5	0.9300
Zn1—O5ⁱ	2.172 (3)	C21—C22	1.391 (7)
Zn1—O1	2.395 (3)	C21—C20	1.446 (7)
O3—C4	1.383 (4)	C12—H12	0.9300
O3—C8	1.392 (4)	C3—C4	1.378 (5)
O4—C14	1.255 (4)	C3—C2	1.389 (5)
N1—C15	1.321 (5)	C3—H3	0.9300
N1—C26	1.358 (4)	C2—C7	1.381 (5)
O5—C14	1.253 (4)	C15—C16	1.396 (6)
O2—C1	1.266 (4)	C15—H15	0.9300
C25—N2	1.362 (5)	C9—C8	1.383 (5)
C25—C21	1.398 (5)	C9—H9	0.9300
C25—C26	1.437 (5)	C17—C16	1.345 (6)
O1—C1	1.233 (4)	C17—H17	0.9300
N2—C24	1.319 (5)	C22—C23	1.355 (7)
C18—C19	1.402 (6)	C22—H22	0.9300
C18—C17	1.407 (6)	C16—H16	0.9300
C18—C26	1.410 (6)	C20—C19	1.329 (6)
C1—C2	1.520 (5)	C20—H20	0.9300
C10—C9	1.367 (6)	C24—C23	1.423 (6)
C10—C11	1.379 (6)	C24—H24	0.9300
C10—H10	0.9300	C6—C7	1.385 (5)
C13—C8	1.393 (5)	C6—H6	0.9300
C13—C12	1.403 (5)	C23—H23	0.9300
C13—C14	1.496 (5)	C7—H7	0.9300
C11—C12	1.375 (5)	C19—H19	0.9300

O2—Zn1—N1	107.31 (11)	C25—C21—C20	118.6 (4)
O2—Zn1—N2	113.60 (11)	C11—C12—C13	121.4 (4)
N1—Zn1—N2	78.85 (13)	C11—C12—H12	119.3
O2—Zn1—O4ⁱ	148.31 (11)	C13—C12—H12	119.3
N1—Zn1—O4ⁱ	92.97 (11)	C4—C3—C2	119.6 (3)
N2—Zn1—O4ⁱ	93.73 (11)	C4—C3—H3	120.2
O2—Zn1—O5ⁱ	101.10 (10)	C2—C3—H3	120.2
N1—Zn1—O5ⁱ	151.55 (10)	O5—C14—O4	120.9 (3)
N2—Zn1—O5ⁱ	91.41 (12)	O5—C14—C13	120.8 (4)
O4ⁱ—Zn1—O5ⁱ	60.75 (10)	O4—C14—C13	118.3 (3)
O2—Zn1—O1	58.81 (10)	O5—C14—Zn1ⁱⁱ	61.1 (2)
N1—Zn1—O1	94.05 (11)	O4—C14—Zn1ⁱⁱ	59.79 (19)
N2—Zn1—O1	167.82 (11)	C13—C14—Zn1ⁱⁱ	177.9 (3)
O4ⁱ—Zn1—O1	96.52 (10)	C7—C2—C3	119.9 (3)
O5ⁱ—Zn1—O1	99.32 (11)	C7—C2—C1	120.9 (3)
C4—O3—C8	117.7 (3)	C3—C2—C1	119.0 (3)
C14—O4—Zn1ⁱⁱ	89.8 (2)	C3—C4—O3	123.2 (3)
C15—N1—C26	118.3 (4)	C3—C4—C5	120.2 (4)
C15—N1—Zn1	128.4 (3)	O3—C4—C5	116.5 (3)
C26—N1—Zn1	113.1 (3)	N1—C15—C16	122.7 (4)
C14—O5—Zn1ⁱⁱ	88.5 (2)	N1—C15—H15	118.6
C1—O2—Zn1	97.8 (2)	C16—C15—H15	118.6
N2—C25—C21	123.2 (4)	C10—C9—C8	120.6 (4)
N2—C25—C26	117.7 (3)	C10—C9—H9	119.7
C21—C25—C26	119.1 (4)	C8—C9—H9	119.7
C1—O1—Zn1	81.1 (2)	C16—C17—C18	120.5 (4)
C24—N2—C25	119.0 (4)	C16—C17—H17	119.8
C24—N2—Zn1	128.0 (3)	C18—C17—H17	119.8
C25—N2—Zn1	112.1 (3)	C23—C22—C21	120.5 (5)
C19—C18—C17	124.5 (5)	C23—C22—H22	119.7
C19—C18—C26	119.1 (4)	C21—C22—H22	119.7
C17—C18—C26	116.5 (4)	C9—C8—O3	117.8 (4)
N1—C26—C18	122.7 (4)	C9—C8—C13	121.0 (4)
N1—C26—C25	117.4 (4)	O3—C8—C13	121.1 (3)
C18—C26—C25	120.0 (4)	C17—C16—C15	119.4 (5)
O1—C1—O2	122.3 (3)	C17—C16—H16	120.3
O1—C1—C2	119.9 (3)	C15—C16—H16	120.3
O2—C1—C2	117.8 (3)	C19—C20—C21	121.4 (4)
O1—C1—Zn1	70.0 (2)	C19—C20—H20	119.3
O2—C1—Zn1	52.30 (17)	C21—C20—H20	119.3
C2—C1—Zn1	169.3 (3)	N2—C24—C23	120.8 (5)
C9—C10—C11	119.8 (4)	N2—C24—H24	119.6
C9—C10—H10	120.1	C23—C24—H24	119.6
C11—C10—H10	120.1	C5—C6—C7	120.3 (4)
C8—C13—C12	117.1 (3)	C5—C6—H6	119.9
C8—C13—C14	124.1 (3)	C7—C6—H6	119.9
C12—C13—C14	118.8 (3)	C22—C23—C24	119.8 (5)
C12—C11—C10	120.0 (4)	C22—C23—H23	120.1
C12—C11—H11	120.0	C24—C23—H23	120.1
C10—C11—H11	120.0	C2—C7—C6	119.9 (4)
C6—C5—C4	120.0 (4)	C2—C7—H7	120.1
C6—C5—H5	120.0	C6—C7—H7	120.1
C4—C5—H5	120.0	C20—C19—C18	121.8 (5)
C22—C21—C25	116.7 (5)	C20—C19—H19	119.1
C22—C21—C20	124.7 (5)	C18—C19—H19	119.1

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₄H₈O₅)(C₁₂H₈N₂)]
M_r	501.78
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.7033 (18), 17.403 (4), 16.230 (4)
β (°)	90.184 (4)
V (Å³)	2175.8 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.17
Crystal size (mm)	0.15 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.901, 0.913
No. of measured, independent and observed [I > 2σ(I)] reflections	10511, 3843, 2320
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.112, 0.94
No. of reflections	3843
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.41

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O2	2.011 (2)	Zn1—O4ⁱ	2.143 (3)
Zn1—N1	2.114 (3)	Zn1—O5ⁱ	2.172 (3)
Zn1—N2	2.129 (3)	Zn1—O1	2.395 (3)

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

Acknowledgements

This project was supported by the Excellent Young Scholars in Higher Universities of Heilongjiang Province, China (1155 G57), the Natural Science Foundation of Heilongjiang Province, China (B201016), the Doctoral Research Fund of Mudanjiang Teachers College, China (MSB: 200902) and the Research Fund of Mudanjiang Teachers College, China (KY: 200902).

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