Poly[zinc(II)-[μ-1,4-bis­(imidazol-1-yl­methyl)benzene]-μ-4,4′-oxydibenzoato]

Yu, C.-H.

doi:10.1107/S1600536808023982

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1106

doi:10.1107/S1600536808023982

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Poly[zinc(II)-[μ-1,4-bis(imidazol-1-ylmethyl)benzene]-μ-4,4′-oxydibenzoato]

Chun-Hui Yu ^a ^*

^aDepartment of Chemistry, College of Chemistry and Biology, Beihua University, Jilin City 132013, People's Republic of China
^*Correspondence e-mail: jlschy@126.com

(Received 23 July 2008; accepted 29 July 2008; online 6 August 2008)

In the title compound, [Zn(C₁₄H₈O₅)(C₁₄H₁₄N₄)]_n, the coordination polyhedron around each Zn^II atom is a distorted tetrahedron. The ligands bridge the Zn atoms to form a two-dimensional (4,4)-network.

Related literature

For related literature, see Batten & Robson (1998 ); Ma et al. (2003 ).

Experimental

Crystal data

[Zn(C₁₄H₈O₅)(C₁₄H₁₄N₄)]
M_r = 559.87
Monoclinic, P 2₁ /c
a = 6.1608 (9) Å
b = 25.811 (4) Å
c = 16.185 (3) Å
β = 92.503 (2)°
V = 2571.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 293 (2) K
0.33 × 0.25 × 0.19 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.718, T_max = 0.826
14194 measured reflections
5057 independent reflections
3906 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.159
S = 1.07
5057 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 1.43 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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: 10.1107/S1600536808023982/bt2755sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023982/bt2755Isup2.hkl

checkCIF report

Comment top

Metal–organic frameworks is currently of great interest because of their interesting structures and potential applications. As a good candidate for rigid rod-like spacers in the construction of metal–organic polymers, 4,4'-bipyridine has been relatively well known and has shown hundreds of interesting supramolecular architectures (Batten & Robson, 1998). However, the flexible ligands such as 1,4-bis(imidazol-1-ylmethyl)benzene (L) has not been well explored to date (Ma et al., 2003). In this work, I selected 4,4'-oxybis(benzoic acid) (H₂oba) and L as linkers, generating a new coordination polymer, [Zn(oba)(L)], (I), which is reported here.

In compound (I) each Zn^II atom is four-coordinated by two N atoms from one L ligand, and two O atoms from two oba carboxylate anions in a distorted tetrahedral coordination sphere (Fig. 1). The two neighbouring Zn^II atoms are bridged by the oba and L ligands to form a two-dimensional (4,4) network (Fig. 2).

Related literature top

For related literature, see Batten & Robson (1998); Ma et al. (2003).

Experimental top

A mixture of H₂oba (0.5 mmol), L (0.5 mmol), NaOH (1 mmol) and ZnCl₂.6H₂O (0.5 mmol) was suspended in 12 ml of deionized water and sealed in a 20 ml Teflon-lined autoclave. Upon heating at 170°C for one week, the autoclave was slowly cooled to room temperature. The crystals were collected, washed with deionized water and dried.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) -1 - x, 1/2 + y, 1/2 - z; (ii) x, 1/2 - y, 1/2 + z.
	Fig. 2. View of the chain structure of (I).

Poly[zinc(II)-[µ-1,4-bis(imidazol-1-ylmethyl)benzene]-µ-4,4'-oxydibenzoato] top

Crystal data top

[Zn(C₁₄H₈O₅)(C₁₄H₁₄N₄)]	F(000) = 1152
M_r = 559.87	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5057 reflections
a = 6.1608 (9) Å	θ = 1.9–26.1°
b = 25.811 (4) Å	µ = 1.00 mm⁻¹
c = 16.185 (3) Å	T = 293 K
β = 92.503 (2)°	Block, colourless
V = 2571.2 (7) Å³	0.33 × 0.25 × 0.19 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	5057 independent reflections
Radiation source: fine-focus sealed tube	3906 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 26.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −7→6
T_min = 0.718, T_max = 0.826	k = −31→27
14194 measured reflections	l = −19→19

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0761P)² + 2.2361P] where P = (F_o² + 2F_c²)/3
5057 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 1.43 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Zn(C₁₄H₈O₅)(C₁₄H₁₄N₄)]	V = 2571.2 (7) Å³
M_r = 559.87	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.1608 (9) Å	µ = 1.00 mm⁻¹
b = 25.811 (4) Å	T = 293 K
c = 16.185 (3) Å	0.33 × 0.25 × 0.19 mm
β = 92.503 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	5057 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3906 reflections with I > 2σ(I)
T_min = 0.718, T_max = 0.826	R_int = 0.047
14194 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.07	Δρ_max = 1.43 e Å⁻³
5057 reflections	Δρ_min = −0.31 e Å⁻³
343 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	0.1661 (7)	0.04984 (15)	0.0495 (3)	0.0273 (9)
H1	0.0525	0.0275	0.0603	0.033*
C2	0.3029 (7)	0.04487 (16)	−0.0136 (3)	0.0284 (9)
H2	0.3004	0.0190	−0.0537	0.034*
C3	0.3919 (7)	0.11368 (15)	0.0599 (3)	0.0281 (9)
H3	0.4643	0.1434	0.0784	0.034*
C4	0.6352 (8)	0.09401 (17)	−0.0563 (3)	0.0384 (11)
H4A	0.6121	0.0764	−0.1089	0.046*
H4B	0.7623	0.0789	−0.0283	0.046*
C5	0.6768 (7)	0.15040 (16)	−0.0719 (3)	0.0312 (10)
C6	0.5194 (8)	0.18139 (19)	−0.1091 (3)	0.0416 (12)
H6	0.3861	0.1668	−0.1251	0.050*
C7	0.5531 (8)	0.23363 (19)	−0.1233 (3)	0.0440 (12)
H7	0.4425	0.2537	−0.1476	0.053*
C8	0.7516 (7)	0.25584 (16)	−0.1014 (3)	0.0274 (9)
C9	0.9128 (7)	0.22467 (18)	−0.0648 (3)	0.0355 (11)
H9	1.0479	0.2388	−0.0502	0.043*
C10	0.8738 (8)	0.17265 (18)	−0.0500 (3)	0.0379 (11)
H10	0.9828	0.1524	−0.0249	0.045*
C11	0.8036 (7)	0.31222 (17)	−0.1168 (3)	0.0333 (10)
H11A	0.8759	0.3266	−0.0675	0.040*
H11B	0.9032	0.3145	−0.1614	0.040*
C12	0.4828 (8)	0.36811 (18)	−0.0836 (3)	0.0393 (12)
H12	0.5095	0.3720	−0.0269	0.047*
C13	0.3094 (8)	0.38615 (17)	−0.1294 (3)	0.0349 (11)
H13	0.1968	0.4057	−0.1091	0.042*
C14	0.5102 (7)	0.34527 (16)	−0.2128 (3)	0.0272 (9)
H14	0.5639	0.3306	−0.2603	0.033*
C15	−0.2311 (7)	0.04825 (15)	0.2220 (3)	0.0269 (9)
C16	−0.3735 (7)	0.01450 (15)	0.2723 (3)	0.0272 (9)
C17	−0.5687 (7)	−0.00464 (16)	0.2373 (3)	0.0312 (10)
H17	−0.6076	0.0032	0.1826	0.037*
C18	−0.7053 (7)	−0.03508 (17)	0.2825 (3)	0.0332 (10)
H18	−0.8353	−0.0475	0.2587	0.040*
C19	−0.6446 (7)	−0.04668 (15)	0.3635 (3)	0.0301 (10)
C20	−0.4550 (8)	−0.02835 (16)	0.4000 (3)	0.0322 (10)
H20	−0.4174	−0.0366	0.4547	0.039*
C21	−0.3190 (7)	0.00262 (16)	0.3547 (3)	0.0305 (10)
H21	−0.1910	0.0155	0.3795	0.037*
C22	−0.8501 (7)	−0.12400 (15)	0.3885 (3)	0.0291 (9)
C23	−0.7128 (7)	−0.15793 (17)	0.3502 (3)	0.0370 (11)
H23	−0.5768	−0.1471	0.3344	0.044*
C24	−0.7814 (7)	−0.20848 (16)	0.3356 (3)	0.0350 (11)
H24	−0.6888	−0.2318	0.3111	0.042*
C25	−0.9857 (7)	−0.22472 (15)	0.3571 (3)	0.0268 (9)
C26	−1.0669 (7)	−0.27912 (16)	0.3427 (3)	0.0294 (10)
C27	−1.1208 (7)	−0.18936 (16)	0.3946 (3)	0.0333 (10)
H27	−1.2587	−0.1997	0.4090	0.040*
C28	−1.0534 (7)	−0.13930 (17)	0.4106 (3)	0.0340 (10)
H28	−1.1446	−0.1161	0.4360	0.041*
N1	0.2223 (6)	0.09330 (12)	0.0948 (2)	0.0258 (8)
N2	0.4459 (6)	0.08575 (13)	−0.0061 (2)	0.0270 (8)
N3	0.6107 (6)	0.34292 (13)	−0.1381 (2)	0.0281 (8)
N4	0.3250 (6)	0.37110 (13)	−0.2109 (2)	0.0282 (8)
O1	−0.0854 (5)	0.07421 (11)	0.26198 (18)	0.0326 (7)
O2	−0.2634 (5)	0.05027 (12)	0.14567 (18)	0.0353 (7)
O3	−1.2588 (5)	−0.28926 (12)	0.3550 (2)	0.0393 (8)
O4	−0.9314 (5)	−0.31274 (11)	0.31674 (19)	0.0331 (7)
O5	−0.7843 (5)	−0.07438 (11)	0.41306 (19)	0.0380 (8)
Zn1	0.09373 (8)	0.120902 (17)	0.19746 (3)	0.02586 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.028 (2)	0.022 (2)	0.032 (2)	−0.0029 (17)	−0.0013 (18)	−0.0012 (17)
C2	0.030 (2)	0.026 (2)	0.029 (2)	0.0022 (18)	−0.0012 (18)	−0.0039 (17)
C3	0.032 (2)	0.020 (2)	0.032 (2)	0.0034 (17)	0.0039 (19)	−0.0014 (17)
C4	0.039 (3)	0.028 (2)	0.049 (3)	0.004 (2)	0.023 (2)	0.004 (2)
C5	0.036 (3)	0.029 (2)	0.030 (2)	0.0011 (19)	0.011 (2)	0.0031 (18)
C6	0.030 (3)	0.042 (3)	0.052 (3)	−0.008 (2)	−0.004 (2)	0.011 (2)
C7	0.032 (3)	0.040 (3)	0.059 (3)	−0.003 (2)	−0.005 (2)	0.021 (2)
C8	0.026 (2)	0.031 (2)	0.026 (2)	0.0028 (18)	0.0033 (17)	0.0044 (17)
C9	0.025 (2)	0.038 (3)	0.044 (3)	0.001 (2)	−0.003 (2)	0.001 (2)
C10	0.032 (3)	0.035 (3)	0.047 (3)	0.008 (2)	−0.001 (2)	0.008 (2)
C11	0.024 (2)	0.037 (3)	0.038 (3)	−0.0009 (19)	−0.0014 (19)	0.005 (2)
C12	0.052 (3)	0.035 (3)	0.031 (2)	0.001 (2)	0.003 (2)	−0.003 (2)
C13	0.040 (3)	0.029 (2)	0.036 (3)	0.003 (2)	0.010 (2)	−0.0047 (19)
C14	0.026 (2)	0.029 (2)	0.027 (2)	0.0018 (18)	0.0003 (18)	0.0035 (17)
C15	0.027 (2)	0.017 (2)	0.037 (3)	0.0043 (17)	0.0066 (19)	0.0005 (17)
C16	0.032 (2)	0.018 (2)	0.033 (2)	0.0043 (17)	0.0065 (19)	−0.0012 (17)
C17	0.040 (3)	0.026 (2)	0.028 (2)	−0.0034 (19)	0.000 (2)	0.0000 (18)
C18	0.030 (3)	0.032 (2)	0.037 (3)	−0.009 (2)	−0.001 (2)	−0.0031 (19)
C19	0.040 (3)	0.016 (2)	0.034 (2)	−0.0043 (18)	0.009 (2)	−0.0005 (17)
C20	0.048 (3)	0.024 (2)	0.025 (2)	−0.001 (2)	0.003 (2)	0.0018 (17)
C21	0.032 (2)	0.025 (2)	0.033 (2)	−0.0044 (18)	−0.0035 (19)	−0.0005 (18)
C22	0.041 (3)	0.021 (2)	0.026 (2)	−0.0033 (19)	0.0050 (19)	0.0005 (17)
C23	0.031 (3)	0.033 (2)	0.048 (3)	−0.011 (2)	0.013 (2)	0.000 (2)
C24	0.035 (3)	0.024 (2)	0.047 (3)	0.0005 (19)	0.019 (2)	−0.0029 (19)
C25	0.028 (2)	0.022 (2)	0.031 (2)	−0.0032 (17)	0.0027 (18)	0.0014 (17)
C26	0.035 (3)	0.021 (2)	0.032 (2)	−0.0009 (18)	0.0055 (19)	0.0008 (17)
C27	0.030 (2)	0.027 (2)	0.043 (3)	−0.0020 (19)	0.009 (2)	−0.0003 (19)
C28	0.036 (3)	0.025 (2)	0.042 (3)	0.0024 (19)	0.013 (2)	−0.0013 (19)
N1	0.030 (2)	0.0206 (17)	0.0268 (18)	0.0008 (15)	0.0026 (15)	−0.0004 (14)
N2	0.029 (2)	0.0230 (18)	0.0299 (18)	0.0035 (15)	0.0051 (15)	0.0005 (14)
N3	0.029 (2)	0.0268 (19)	0.0286 (19)	−0.0002 (15)	0.0015 (16)	0.0065 (15)
N4	0.030 (2)	0.0240 (18)	0.0303 (19)	0.0032 (15)	0.0033 (15)	0.0039 (15)
O1	0.0351 (18)	0.0278 (16)	0.0354 (17)	−0.0094 (13)	0.0073 (14)	0.0003 (13)
O2	0.0397 (19)	0.0369 (18)	0.0300 (17)	−0.0037 (14)	0.0068 (14)	0.0024 (13)
O3	0.0345 (19)	0.0294 (17)	0.055 (2)	−0.0072 (14)	0.0087 (16)	−0.0032 (15)
O4	0.0340 (18)	0.0234 (15)	0.0426 (18)	−0.0012 (13)	0.0088 (14)	−0.0021 (13)
O5	0.053 (2)	0.0251 (16)	0.0375 (18)	−0.0140 (14)	0.0200 (16)	−0.0062 (13)
Zn1	0.0284 (3)	0.0203 (3)	0.0292 (3)	−0.0010 (2)	0.0048 (2)	−0.00183 (19)

Geometric parameters (Å, º) top

C1—C2	1.357 (6)	C15—O2	1.243 (5)
C1—N1	1.376 (5)	C15—O1	1.274 (5)
C1—H1	0.9300	C15—C16	1.502 (6)
C2—N2	1.377 (5)	C16—C21	1.395 (6)
C2—H2	0.9300	C16—C17	1.397 (6)
C3—N1	1.319 (5)	C17—C18	1.383 (6)
C3—N2	1.342 (5)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.381 (6)
C4—N2	1.466 (5)	C18—H18	0.9300
C4—C5	1.501 (6)	C19—C20	1.370 (6)
C4—H4A	0.9700	C19—O5	1.398 (5)
C4—H4B	0.9700	C20—C21	1.389 (6)
C5—C6	1.375 (6)	C20—H20	0.9300
C5—C10	1.375 (6)	C21—H21	0.9300
C6—C7	1.385 (6)	C22—C28	1.375 (6)
C6—H6	0.9300	C22—C23	1.383 (6)
C7—C8	1.383 (6)	C22—O5	1.396 (5)
C7—H7	0.9300	C23—C24	1.389 (6)
C8—C9	1.390 (6)	C23—H23	0.9300
C8—C11	1.513 (6)	C24—C25	1.385 (6)
C9—C10	1.387 (6)	C24—H24	0.9300
C9—H9	0.9300	C25—C27	1.392 (6)
C10—H10	0.9300	C25—C26	1.505 (6)
C11—N3	1.457 (5)	C26—O3	1.236 (5)
C11—H11A	0.9700	C26—O4	1.288 (5)
C11—H11B	0.9700	C27—C28	1.378 (6)
C12—C13	1.356 (7)	C27—H27	0.9300
C12—N3	1.372 (6)	C28—H28	0.9300
C12—H12	0.9300	N1—Zn1	2.002 (3)
C13—N4	1.383 (5)	N4—Zn1ⁱ	2.021 (4)
C13—H13	0.9300	O1—Zn1	1.965 (3)
C14—N4	1.323 (5)	O4—Zn1ⁱⁱ	1.992 (3)
C14—N3	1.336 (5)	Zn1—O4ⁱⁱⁱ	1.992 (3)
C14—H14	0.9300	Zn1—N4^iv	2.021 (4)

C2—C1—N1	109.1 (4)	C16—C17—H17	119.3
C2—C1—H1	125.4	C19—C18—C17	118.6 (4)
N1—C1—H1	125.4	C19—C18—H18	120.7
C1—C2—N2	106.1 (4)	C17—C18—H18	120.7
C1—C2—H2	126.9	C20—C19—C18	121.6 (4)
N2—C2—H2	126.9	C20—C19—O5	117.7 (4)
N1—C3—N2	110.8 (4)	C18—C19—O5	120.5 (4)
N1—C3—H3	124.6	C19—C20—C21	119.6 (4)
N2—C3—H3	124.6	C19—C20—H20	120.2
N2—C4—C5	112.3 (3)	C21—C20—H20	120.2
N2—C4—H4A	109.1	C20—C21—C16	120.3 (4)
C5—C4—H4A	109.1	C20—C21—H21	119.8
N2—C4—H4B	109.1	C16—C21—H21	119.8
C5—C4—H4B	109.1	C28—C22—C23	121.1 (4)
H4A—C4—H4B	107.9	C28—C22—O5	116.5 (4)
C6—C5—C10	117.9 (4)	C23—C22—O5	122.2 (4)
C6—C5—C4	121.0 (4)	C22—C23—C24	118.9 (4)
C10—C5—C4	121.1 (4)	C22—C23—H23	120.5
C5—C6—C7	122.1 (4)	C24—C23—H23	120.5
C5—C6—H6	119.0	C25—C24—C23	121.0 (4)
C7—C6—H6	119.0	C25—C24—H24	119.5
C8—C7—C6	119.9 (4)	C23—C24—H24	119.5
C8—C7—H7	120.1	C24—C25—C27	118.6 (4)
C6—C7—H7	120.1	C24—C25—C26	122.9 (4)
C7—C8—C9	118.5 (4)	C27—C25—C26	118.5 (4)
C7—C8—C11	123.2 (4)	O3—C26—O4	123.3 (4)
C9—C8—C11	118.3 (4)	O3—C26—C25	119.1 (4)
C10—C9—C8	120.5 (4)	O4—C26—C25	117.6 (4)
C10—C9—H9	119.7	C28—C27—C25	121.0 (4)
C8—C9—H9	119.7	C28—C27—H27	119.5
C5—C10—C9	121.2 (4)	C25—C27—H27	119.5
C5—C10—H10	119.4	C22—C28—C27	119.4 (4)
C9—C10—H10	119.4	C22—C28—H28	120.3
N3—C11—C8	112.7 (4)	C27—C28—H28	120.3
N3—C11—H11A	109.1	C3—N1—C1	106.4 (3)
C8—C11—H11A	109.1	C3—N1—Zn1	124.3 (3)
N3—C11—H11B	109.1	C1—N1—Zn1	129.2 (3)
C8—C11—H11B	109.1	C3—N2—C2	107.5 (3)
H11A—C11—H11B	107.8	C3—N2—C4	126.4 (4)
C13—C12—N3	105.8 (4)	C2—N2—C4	125.8 (4)
C13—C12—H12	127.1	C14—N3—C12	107.7 (4)
N3—C12—H12	127.1	C14—N3—C11	125.4 (4)
C12—C13—N4	109.9 (4)	C12—N3—C11	126.2 (4)
C12—C13—H13	125.1	C14—N4—C13	105.0 (4)
N4—C13—H13	125.1	C14—N4—Zn1ⁱ	128.0 (3)
N4—C14—N3	111.6 (4)	C13—N4—Zn1ⁱ	126.5 (3)
N4—C14—H14	124.2	C15—O1—Zn1	116.9 (3)
N3—C14—H14	124.2	C26—O4—Zn1ⁱⁱ	106.7 (3)
O2—C15—O1	124.1 (4)	C22—O5—C19	119.0 (3)
O2—C15—C16	119.5 (4)	O1—Zn1—O4ⁱⁱⁱ	107.32 (12)
O1—C15—C16	116.4 (4)	O1—Zn1—N1	118.32 (13)
C21—C16—C17	118.5 (4)	O4ⁱⁱⁱ—Zn1—N1	115.16 (13)
C21—C16—C15	121.6 (4)	O1—Zn1—N4^iv	93.85 (13)
C17—C16—C15	119.9 (4)	O4ⁱⁱⁱ—Zn1—N4^iv	109.34 (13)
C18—C17—C16	121.3 (4)	N1—Zn1—N4^iv	110.68 (14)
C18—C17—H17	119.3

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₄H₈O₅)(C₁₄H₁₄N₄)]
M_r	559.87
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.1608 (9), 25.811 (4), 16.185 (3)
β (°)	92.503 (2)
V (Å³)	2571.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.33 × 0.25 × 0.19

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.718, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	14194, 5057, 3906
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.159, 1.07
No. of reflections	5057
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.43, −0.31

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

Acknowledgements

The author thanks Beihua University for supporting this work.

References

Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460–1494. Web of Science CrossRef Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar