Poly[[μ-2,2′-diethyl-1,1′-(propane-1,3-di­yl)di-1H-imidazole-κ2N3:N3′](μ-5-hy­droxy­isophthalato-κ2O1:O3)zinc]

Liu, Y.-Y.; Wang, C.-J.; Yan, Y.-S.

doi:10.1107/S1600536811041456

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1544

doi:10.1107/S1600536811041456

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Poly[[μ-2,2′-diethyl-1,1′-(propane-1,3-diyl)di-1H-imidazole-κ²N³:N^3′](μ-5-hydroxyisophthalato-κ²O¹:O³)zinc]

Ying-Ying Liu,^a Chun-Jie Wang ^a and Yong-Sheng Yan ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China
^*Correspondence e-mail: yys@ujs.edu.cn

(Received 16 September 2011; accepted 8 October 2011; online 22 October 2011)

In the title coordination polymer, [Zn(C₈H₄O₅)(C₁₃H₂₀N₄)]_n, the Zn^II ion is coordinated by an O₂N₂ donor set in a distorted tetrahedral geometry. The Zn^II ions are connected by 5-hydroxyisophthalate (hbdc) and 2,2′-diethyl-1,1′-(propane-1,3-diyl)di-1H-imidazole (pbie) ligands, forming a threefold interpenetrating diamondoid framework. In the pbie ligand, one of the ethylimidazole groups is disordered over two positions, with a site-occupancy ratio of 0.670 (9):0.330 (9). An intermolecular O—H⋯O hydrogen bond is formed between the hydroxy and carboxylate groups of the hbdc ligands.

Related literature

For background to bis(imidazole) ligands, see: Liu et al. (2007 , 2011 ).

Experimental

Crystal data

[Zn(C₈H₄O₅)(C₁₃H₂₀N₄)]
M_r = 477.83
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.476 (2) Å
b = 14.846 (4) Å
c = 15.724 (4) Å
V = 2212.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 293 K
0.35 × 0.28 × 0.22 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.68, T_max = 0.78
21558 measured reflections
5031 independent reflections
4372 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.136
S = 1.05
5031 reflections
309 parameters
15 restraints
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.46 e Å⁻³
Absolute structure: Flack (1983 ), 2190 Friedel pairs
Flack parameter: −0.006 (19)

Table 1
Selected bond lengths (Å)

Zn1—O1	1.992 (3)
Zn1—O4ⁱ	1.950 (3)
Zn1—N1	2.021 (5)
Zn1—N1′	2.047 (13)
Zn1—N4ⁱⁱ	2.055 (4)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O1ⁱⁱⁱ	0.82	1.97	2.741 (5)	156
Symmetry code: (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041456/hy2473sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041456/hy2473Isup2.hkl

checkCIF report

Comment top

As part of an investigation of the applications of transition metal complexes, there is a need to prepare further examples of these compounds. In this paper, the structure of the title compound is described.

As shown in Fig. 1, the Zn^II ion is four-coordinated by two O atoms from two bridging 5-hydroxyisophthalate (hbdc) ligands and two N atoms from two bridging 1,1'-(1,3-propanediyl)bis(imidazole-2-ethyl) (pbie) ligands (Liu et al., 2007, 2011). The carboxylate groups of the hbdc ligand act in a monodentate mode and the hydroxyl group is not involved in coordination. The pbie ligand coordinates to two Zn^II ions through its two aromatic N atoms. As illustrated in Fig. 2, the Zn^II ions are connected by the hbdc and pbie ligands into a diamondiod framework. To minimize the big void cavity in the diamondiod cage, a threefold interpenetrating net is generated (Fig. 3).

Related literature top

For background to bis(imidazole) ligands, see: Liu et al. (2007, 2011).

Experimental top

The pbie ligand was synthesized according to literature (Liu et al., 2007) but 2-phenylimidazole and 1,4-dichlorobutane were replaced by 2-ethylimidazole and 1,3-dichloropropane. A mixture of ZnCO₃ (0.050 g, 0.40 mmol), 5-hydroxyisophthalic acid (0.043 g, 0.40 mmol), pbie (0.093 g, 0.40 mmol) and water (8 ml) was sealed in a Teflon-lined reactor (15 ml) and heated at 150 °C for 3 d. After the mixture was cooled to room temperature at 10°C h^-1, colorless crystals of the title compound were obtained (yield: 38%).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) -x, 1/2 + y, 3/2 - z; (ii) 3/2 - x, 1 - y, 1/2 + z.]
	Fig. 2. View of a single diamondiod motif.
	Fig. 3. View of the threefold interpenetrating net.

Poly[[µ-2,2'-diethyl-1,1'-(propane-1,3-diyl)di-1H-imidazole- κ²N³:N^3'](µ-5-hydroxyisophthalato- κ²O¹:O³)zinc] top

Crystal data top

[Zn(C₈H₄O₅)(C₁₃H₂₀N₄)]	F(000) = 992
M_r = 477.83	D_x = 1.435 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4372 reflections
a = 9.476 (2) Å	θ = 3.0–27.5°
b = 14.846 (4) Å	µ = 1.15 mm⁻¹
c = 15.724 (4) Å	T = 293 K
V = 2212.1 (9) Å³	Block, colorless
Z = 4	0.35 × 0.28 × 0.22 mm

Data collection top

Bruker APEX CCD diffractometer	5031 independent reflections
Radiation source: fine-focus sealed tube	4372 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.68, T_max = 0.78	k = −19→19
21558 measured reflections	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0827P)² + 0.6158P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
5031 reflections	Δρ_max = 0.76 e Å⁻³
309 parameters	Δρ_min = −0.46 e Å⁻³
15 restraints	Absolute structure: Flack (1983), 2190 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.006 (19)

Crystal data top

[Zn(C₈H₄O₅)(C₁₃H₂₀N₄)]	V = 2212.1 (9) Å³
M_r = 477.83	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.476 (2) Å	µ = 1.15 mm⁻¹
b = 14.846 (4) Å	T = 293 K
c = 15.724 (4) Å	0.35 × 0.28 × 0.22 mm

Data collection top

Bruker APEX CCD diffractometer	5031 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4372 reflections with I > 2σ(I)
T_min = 0.68, T_max = 0.78	R_int = 0.047
21558 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.136	Δρ_max = 0.76 e Å⁻³
S = 1.05	Δρ_min = −0.46 e Å⁻³
5031 reflections	Absolute structure: Flack (1983), 2190 Friedel pairs
309 parameters	Absolute structure parameter: −0.006 (19)
15 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.35630 (4)	0.49008 (3)	0.79285 (2)	0.03541 (14)
C1	0.1051 (4)	0.2692 (3)	0.8438 (2)	0.0387 (9)
C2	0.0416 (4)	0.2035 (3)	0.7938 (3)	0.0440 (8)
H2	0.0685	0.1960	0.7373	0.053*
C3	−0.0616 (5)	0.1496 (3)	0.8286 (3)	0.0433 (9)
C4	−0.0976 (5)	0.1572 (3)	0.9142 (3)	0.0461 (10)
H4	−0.1669	0.1203	0.9374	0.055*
C5	−0.0298 (5)	0.2199 (3)	0.9643 (3)	0.0483 (10)
C6	0.0707 (4)	0.2769 (3)	0.9292 (3)	0.0433 (9)
H6	0.1147	0.3202	0.9627	0.052*
C7	0.2047 (4)	0.3346 (3)	0.8022 (3)	0.0431 (9)
C8	−0.1388 (5)	0.0841 (3)	0.7711 (3)	0.0500 (10)
C9	0.6553 (7)	0.4354 (5)	0.7377 (5)	0.0501 (18)	0.670 (9)
C10	0.6928 (9)	0.5229 (7)	0.6298 (6)	0.074 (3)	0.670 (9)
H10	0.7355	0.5526	0.5845	0.089*	0.670 (9)
C11	0.5662 (9)	0.5394 (7)	0.6600 (6)	0.073 (3)	0.670 (9)
H11	0.5036	0.5821	0.6388	0.088*	0.670 (9)
C12	0.6801 (12)	0.3705 (7)	0.8109 (6)	0.076 (3)	0.670 (9)
H12A	0.5913	0.3418	0.8254	0.091*	0.670 (9)
H12B	0.7447	0.3238	0.7923	0.091*	0.670 (9)
C13	0.7361 (17)	0.4124 (11)	0.8850 (9)	0.125 (5)	0.670 (9)
H13A	0.7485	0.3680	0.9288	0.188*	0.670 (9)
H13B	0.6720	0.4580	0.9044	0.188*	0.670 (9)
H13C	0.8255	0.4393	0.8717	0.188*	0.670 (9)
N1	0.5406 (5)	0.4827 (5)	0.7285 (4)	0.0485 (15)	0.670 (9)
N2	0.7509 (6)	0.4549 (6)	0.6763 (5)	0.0596 (19)	0.670 (9)
C9'	0.6253 (19)	0.4478 (11)	0.6920 (11)	0.055 (4)*	0.330 (9)
C10'	0.759 (2)	0.3791 (11)	0.7897 (13)	0.065 (4)*	0.330 (9)
H10'	0.8319	0.3473	0.8158	0.078*	0.330 (9)
C11'	0.632 (2)	0.4049 (13)	0.8242 (13)	0.065 (5)*	0.330 (9)
H11'	0.6055	0.3970	0.8806	0.078*	0.330 (9)
C12'	0.582 (2)	0.4836 (13)	0.6092 (12)	0.072 (5)*	0.330 (9)
H12C	0.4805	0.4924	0.6089	0.086*	0.330 (9)
H12D	0.6050	0.4403	0.5652	0.086*	0.330 (9)
C13'	0.654 (5)	0.572 (3)	0.590 (3)	0.190 (18)*	0.330 (9)
H13D	0.6254	0.5924	0.5350	0.285*	0.330 (9)
H13E	0.7542	0.5631	0.5912	0.285*	0.330 (9)
H13F	0.6276	0.6153	0.6323	0.285*	0.330 (9)
N1'	0.5536 (13)	0.4425 (9)	0.7646 (9)	0.048 (3)*	0.330 (9)
N2'	0.7539 (16)	0.4120 (11)	0.7057 (11)	0.064 (4)*	0.330 (9)
C14	1.0407 (5)	0.3771 (3)	0.4292 (3)	0.0562 (11)
C15	1.1817 (6)	0.3995 (4)	0.5348 (3)	0.0669 (13)
H15	1.2243	0.3984	0.5880	0.080*
C16	1.2190 (6)	0.4502 (4)	0.4687 (3)	0.0604 (12)
H16	1.2954	0.4895	0.4674	0.073*
C17	0.9295 (7)	0.3325 (5)	0.3727 (5)	0.0909 (17)
H17A	0.8679	0.2959	0.4079	0.109*
H17B	0.8724	0.3788	0.3461	0.109*
C18	0.9932 (11)	0.2750 (7)	0.3056 (6)	0.131 (3)
H18A	0.9196	0.2485	0.2719	0.196*
H18B	1.0482	0.2282	0.3316	0.196*
H18C	1.0528	0.3111	0.2699	0.196*
C19	0.8787 (5)	0.4029 (5)	0.6543 (4)	0.0755 (17)
H19A	0.9249	0.3857	0.7068	0.091*
H19B	0.9426	0.4426	0.6240	0.091*
C20	0.8589 (6)	0.3184 (5)	0.6009 (4)	0.0743 (15)
H20A	0.8199	0.2713	0.6367	0.089*
H20B	0.7908	0.3309	0.5564	0.089*
C21	0.9938 (6)	0.2838 (4)	0.5604 (3)	0.0610 (13)
H21A	1.0570	0.2639	0.6051	0.073*
H21B	0.9711	0.2318	0.5256	0.073*
N3	1.0663 (5)	0.3485 (3)	0.5086 (3)	0.0614 (10)
N4	1.1266 (5)	0.4352 (3)	0.4023 (2)	0.0554 (9)
O1	0.2832 (3)	0.3822 (2)	0.85403 (19)	0.0452 (7)
O2	0.2081 (4)	0.3430 (3)	0.7259 (2)	0.0658 (10)
O3	−0.0846 (5)	0.0604 (3)	0.7040 (3)	0.0904 (13)
O4	−0.2584 (3)	0.0565 (2)	0.7965 (2)	0.0586 (8)
O5	−0.0558 (4)	0.2318 (3)	1.0491 (2)	0.0723 (11)
H5	−0.1164	0.1961	1.0647	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0326 (2)	0.0447 (2)	0.0290 (2)	0.00247 (17)	0.00191 (16)	0.00315 (17)
C1	0.040 (2)	0.043 (2)	0.0338 (18)	−0.0005 (16)	−0.0058 (15)	0.0043 (15)
C2	0.049 (2)	0.048 (2)	0.0351 (18)	−0.0036 (17)	−0.0031 (19)	0.0034 (19)
C3	0.044 (2)	0.047 (2)	0.039 (2)	−0.0027 (18)	−0.0130 (18)	0.0045 (17)
C4	0.042 (2)	0.054 (2)	0.042 (2)	−0.0125 (19)	−0.0049 (17)	0.0052 (18)
C5	0.046 (2)	0.064 (3)	0.035 (2)	−0.012 (2)	−0.0022 (18)	0.0027 (19)
C6	0.042 (2)	0.054 (2)	0.0337 (19)	−0.0073 (19)	−0.0050 (17)	0.0015 (17)
C7	0.0355 (18)	0.050 (2)	0.044 (2)	0.0016 (16)	0.0002 (18)	0.0066 (19)
C8	0.057 (2)	0.053 (2)	0.040 (2)	−0.009 (2)	−0.009 (2)	−0.0020 (17)
C9	0.029 (3)	0.071 (4)	0.051 (4)	0.017 (3)	0.019 (3)	0.002 (3)
C10	0.067 (5)	0.094 (6)	0.060 (5)	0.009 (5)	0.023 (4)	0.029 (5)
C11	0.061 (5)	0.099 (7)	0.060 (5)	0.016 (5)	0.003 (4)	0.040 (5)
C12	0.085 (7)	0.084 (6)	0.059 (5)	0.027 (5)	0.026 (5)	0.028 (5)
C13	0.125 (5)	0.125 (5)	0.125 (5)	0.0007 (10)	−0.0007 (10)	0.0000 (10)
N1	0.036 (2)	0.069 (4)	0.040 (3)	0.011 (3)	0.010 (2)	0.004 (3)
N2	0.035 (3)	0.083 (5)	0.060 (4)	0.013 (3)	0.022 (3)	0.016 (4)
C14	0.057 (3)	0.055 (3)	0.057 (3)	0.008 (2)	0.017 (2)	0.003 (2)
C15	0.066 (3)	0.092 (4)	0.043 (2)	0.004 (2)	0.007 (2)	−0.001 (2)
C16	0.061 (3)	0.061 (3)	0.059 (3)	−0.006 (2)	−0.016 (2)	0.003 (2)
C17	0.070 (4)	0.103 (5)	0.100 (4)	−0.031 (3)	−0.032 (3)	−0.002 (3)
C18	0.131 (3)	0.131 (3)	0.131 (3)	0.0004 (10)	0.0001 (10)	−0.0026 (10)
C19	0.041 (3)	0.101 (4)	0.084 (4)	0.015 (3)	0.029 (3)	0.004 (3)
C20	0.050 (3)	0.108 (4)	0.066 (3)	−0.007 (3)	0.015 (3)	0.017 (3)
C21	0.061 (3)	0.067 (3)	0.055 (3)	0.001 (3)	0.011 (2)	0.021 (2)
N3	0.054 (2)	0.067 (3)	0.062 (3)	0.0094 (18)	0.0164 (19)	0.015 (2)
N4	0.061 (2)	0.060 (2)	0.0451 (19)	0.005 (2)	0.0057 (18)	0.0053 (16)
O1	0.0416 (15)	0.0460 (16)	0.0479 (16)	−0.0031 (13)	−0.0066 (13)	0.0051 (13)
O2	0.070 (2)	0.089 (3)	0.0385 (18)	−0.025 (2)	−0.0001 (15)	0.0103 (16)
O3	0.097 (3)	0.109 (3)	0.066 (2)	−0.037 (3)	−0.003 (2)	−0.034 (3)
O4	0.0601 (19)	0.0649 (19)	0.0510 (18)	−0.0178 (15)	−0.0119 (16)	−0.0059 (18)
O5	0.080 (2)	0.104 (3)	0.0330 (16)	−0.041 (2)	0.0058 (16)	−0.0058 (17)

Geometric parameters (Å, º) top

Zn1—O1	1.992 (3)	C10'—C11'	1.38 (3)
Zn1—O4ⁱ	1.950 (3)	C10'—N2'	1.41 (3)
Zn1—N1	2.021 (5)	C10'—H10'	0.9300
Zn1—N1'	2.047 (13)	C11'—N1'	1.32 (2)
Zn1—N4ⁱⁱ	2.055 (4)	C11'—H11'	0.9300
C1—C6	1.386 (6)	C12'—C13'	1.50 (5)
C1—C2	1.390 (6)	C12'—H12C	0.9700
C1—C7	1.504 (6)	C12'—H12D	0.9700
C2—C3	1.378 (6)	C13'—H13D	0.9600
C2—H2	0.9300	C13'—H13E	0.9600
C3—C4	1.393 (6)	C13'—H13F	0.9600
C3—C8	1.517 (6)	N2'—C19	1.439 (16)
C4—C5	1.377 (6)	C14—N4	1.258 (6)
C4—H4	0.9300	C14—N3	1.341 (6)
C5—O5	1.367 (5)	C14—C17	1.529 (8)
C5—C6	1.390 (6)	C15—C16	1.331 (8)
C6—H6	0.9300	C15—N3	1.393 (7)
C7—O2	1.206 (5)	C15—H15	0.9300
C7—O1	1.311 (5)	C16—N4	1.380 (6)
C8—O3	1.225 (6)	C16—H16	0.9300
C8—O4	1.269 (6)	C17—C18	1.486 (11)
C9—N1	1.302 (9)	C17—H17A	0.9700
C9—N2	1.355 (9)	C17—H17B	0.9700
C9—C12	1.520 (11)	C18—H18A	0.9600
C10—C11	1.314 (12)	C18—H18B	0.9600
C10—N2	1.362 (12)	C18—H18C	0.9600
C10—H10	0.9300	C19—C20	1.520 (9)
C11—N1	1.388 (10)	C19—H19A	0.9700
C11—H11	0.9300	C19—H19B	0.9700
C12—C13	1.423 (17)	C20—C21	1.518 (8)
C12—H12A	0.9700	C20—H20A	0.9700
C12—H12B	0.9700	C20—H20B	0.9700
C13—H13A	0.9600	C21—N3	1.434 (6)
C13—H13B	0.9600	C21—H21A	0.9700
C13—H13C	0.9600	C21—H21B	0.9700
N2—C19	1.477 (8)	N4—Zn1ⁱⁱⁱ	2.055 (4)
C9'—N1'	1.33 (2)	O4—Zn1^iv	1.950 (3)
C9'—N2'	1.35 (2)	O5—H5	0.8200
C9'—C12'	1.46 (2)

O4ⁱ—Zn1—O1	126.04 (14)	C9'—C12'—C13'	111 (2)
O4ⁱ—Zn1—N1	94.5 (2)	C9'—C12'—H12C	109.3
O1—Zn1—N1	119.9 (2)	C13'—C12'—H12C	109.3
O4ⁱ—Zn1—N1'	116.9 (4)	C9'—C12'—H12D	109.3
O1—Zn1—N1'	98.3 (4)	C13'—C12'—H12D	109.3
O4ⁱ—Zn1—N4ⁱⁱ	111.58 (15)	H12C—C12'—H12D	108.0
O1—Zn1—N4ⁱⁱ	93.26 (15)	C12'—C13'—H13D	109.5
N1—Zn1—N4ⁱⁱ	112.4 (2)	C12'—C13'—H13E	109.5
N1'—Zn1—N4ⁱⁱ	107.2 (4)	H13D—C13'—H13E	109.5
C6—C1—C2	120.3 (4)	C12'—C13'—H13F	109.5
C6—C1—C7	121.0 (4)	H13D—C13'—H13F	109.5
C2—C1—C7	118.6 (4)	H13E—C13'—H13F	109.5
C3—C2—C1	119.3 (4)	C11'—N1'—C9'	110.2 (15)
C3—C2—H2	120.3	C11'—N1'—Zn1	120.5 (13)
C1—C2—H2	120.3	C9'—N1'—Zn1	129.2 (13)
C2—C3—C4	120.7 (4)	C9'—N2'—C10'	108.6 (16)
C2—C3—C8	118.5 (4)	C9'—N2'—C19	133.6 (17)
C4—C3—C8	120.7 (4)	C10'—N2'—C19	117.7 (14)
C5—C4—C3	119.6 (4)	N4—C14—N3	114.4 (5)
C5—C4—H4	120.2	N4—C14—C17	123.3 (5)
C3—C4—H4	120.2	N3—C14—C17	121.8 (5)
O5—C5—C4	124.2 (4)	C16—C15—N3	106.6 (5)
O5—C5—C6	115.6 (4)	C16—C15—H15	126.7
C4—C5—C6	120.2 (4)	N3—C15—H15	126.7
C1—C6—C5	119.7 (4)	C15—C16—N4	109.3 (5)
C1—C6—H6	120.1	C15—C16—H16	125.4
C5—C6—H6	120.1	N4—C16—H16	125.4
O2—C7—O1	123.2 (4)	C18—C17—C14	112.4 (6)
O2—C7—C1	121.1 (4)	C18—C17—H17A	109.1
O1—C7—C1	115.7 (4)	C14—C17—H17A	109.1
O3—C8—O4	123.6 (4)	C18—C17—H17B	109.1
O3—C8—C3	119.7 (4)	C14—C17—H17B	109.1
O4—C8—C3	116.8 (4)	H17A—C17—H17B	107.8
N1—C9—N2	111.3 (8)	C17—C18—H18A	109.5
N1—C9—C12	123.7 (7)	C17—C18—H18B	109.5
N2—C9—C12	124.9 (7)	H18A—C18—H18B	109.5
C11—C10—N2	108.2 (7)	C17—C18—H18C	109.5
C11—C10—H10	125.9	H18A—C18—H18C	109.5
N2—C10—H10	125.9	H18B—C18—H18C	109.5
C10—C11—N1	109.1 (8)	N2'—C19—C20	106.6 (7)
C10—C11—H11	125.4	N2—C19—C20	117.4 (5)
N1—C11—H11	125.4	N2'—C19—H19A	85.2
C13—C12—C9	113.6 (10)	N2—C19—H19A	108.0
C13—C12—H12A	108.9	C20—C19—H19A	108.0
C9—C12—H12A	108.9	N2'—C19—H19B	137.0
C13—C12—H12B	108.9	N2—C19—H19B	108.0
C9—C12—H12B	108.9	C20—C19—H19B	108.0
H12A—C12—H12B	107.7	H19A—C19—H19B	107.2
C12—C13—H13A	109.5	C21—C20—C19	114.0 (5)
C12—C13—H13B	109.5	C21—C20—H20A	108.7
H13A—C13—H13B	109.5	C19—C20—H20A	108.7
C12—C13—H13C	109.5	C21—C20—H20B	108.7
H13A—C13—H13C	109.5	C19—C20—H20B	108.7
H13B—C13—H13C	109.5	H20A—C20—H20B	107.6
C9—N1—C11	105.5 (6)	N3—C21—C20	114.6 (4)
C9—N1—Zn1	134.0 (6)	N3—C21—H21A	108.6
C11—N1—Zn1	120.5 (5)	C20—C21—H21A	108.6
C9—N2—C10	105.7 (6)	N3—C21—H21B	108.6
C9—N2—C19	127.1 (8)	C20—C21—H21B	108.6
C10—N2—C19	126.3 (6)	H21A—C21—H21B	107.6
N1'—C9'—N2'	107.5 (18)	C14—N3—C15	104.2 (4)
N1'—C9'—C12'	129.8 (18)	C14—N3—C21	130.9 (5)
N2'—C9'—C12'	122.7 (17)	C15—N3—C21	124.9 (5)
C11'—C10'—N2'	103.9 (16)	C14—N4—C16	105.5 (4)
C11'—C10'—H10'	128.0	C14—N4—Zn1ⁱⁱⁱ	134.6 (4)
N2'—C10'—H10'	128.0	C16—N4—Zn1ⁱⁱⁱ	119.7 (3)
N1'—C11'—C10'	109.4 (18)	C7—O1—Zn1	109.3 (3)
N1'—C11'—H11'	125.3	C8—O4—Zn1^iv	111.2 (3)
C10'—C11'—H11'	125.3	C5—O5—H5	109.5

C6—C1—C2—C3	3.6 (6)	C12'—C9'—N1'—Zn1	−5 (3)
C7—C1—C2—C3	−172.8 (4)	O4ⁱ—Zn1—N1'—C11'	173.2 (12)
C1—C2—C3—C4	−3.2 (6)	O1—Zn1—N1'—C11'	−49.0 (13)
C1—C2—C3—C8	174.6 (4)	N1—Zn1—N1'—C11'	153.7 (19)
C2—C3—C4—C5	0.5 (7)	N4ⁱⁱ—Zn1—N1'—C11'	47.1 (14)
C8—C3—C4—C5	−177.3 (4)	O4ⁱ—Zn1—N1'—C9'	−2.2 (15)
C3—C4—C5—O5	−179.0 (5)	O1—Zn1—N1'—C9'	135.6 (13)
C3—C4—C5—C6	2.0 (7)	N1—Zn1—N1'—C9'	−21.7 (11)
C2—C1—C6—C5	−1.3 (6)	N4ⁱⁱ—Zn1—N1'—C9'	−128.3 (13)
C7—C1—C6—C5	175.1 (4)	N1'—C9'—N2'—C10'	2.9 (19)
O5—C5—C6—C1	179.3 (4)	C12'—C9'—N2'—C10'	−176.5 (16)
C4—C5—C6—C1	−1.6 (7)	N1'—C9'—N2'—C19	−176.2 (15)
C6—C1—C7—O2	−161.1 (4)	C12'—C9'—N2'—C19	4 (3)
C2—C1—C7—O2	15.2 (6)	C11'—C10'—N2'—C9'	−4.8 (19)
C6—C1—C7—O1	17.3 (6)	C11'—C10'—N2'—C19	174.5 (13)
C2—C1—C7—O1	−166.3 (4)	N3—C15—C16—N4	2.4 (6)
C2—C3—C8—O3	21.4 (7)	N4—C14—C17—C18	65.8 (8)
C4—C3—C8—O3	−160.7 (5)	N3—C14—C17—C18	−105.1 (7)
C2—C3—C8—O4	−158.8 (4)	C9'—N2'—C19—N2	31.4 (15)
C4—C3—C8—O4	19.0 (6)	C10'—N2'—C19—N2	−148 (2)
N2—C10—C11—N1	1.1 (12)	C9'—N2'—C19—C20	−84.1 (19)
N1—C9—C12—C13	−85.8 (13)	C10'—N2'—C19—C20	96.9 (14)
N2—C9—C12—C13	90.9 (13)	C9—N2—C19—N2'	1.7 (13)
N2—C9—N1—C11	−3.2 (10)	C10—N2—C19—N2'	−166.2 (18)
C12—C9—N1—C11	173.9 (9)	C9—N2—C19—C20	78.4 (10)
N2—C9—N1—Zn1	179.5 (6)	C10—N2—C19—C20	−89.5 (10)
C12—C9—N1—Zn1	−3.4 (12)	N2'—C19—C20—C21	−164.5 (8)
C10—C11—N1—C9	1.3 (11)	N2—C19—C20—C21	163.6 (5)
C10—C11—N1—Zn1	179.0 (7)	C19—C20—C21—N3	−55.8 (7)
O4ⁱ—Zn1—N1—C9	−165.9 (7)	N4—C14—N3—C15	2.7 (6)
O1—Zn1—N1—C9	−29.4 (8)	C17—C14—N3—C15	174.3 (5)
N1'—Zn1—N1—C9	−3.3 (10)	N4—C14—N3—C21	−179.8 (5)
N4ⁱⁱ—Zn1—N1—C9	78.6 (7)	C17—C14—N3—C21	−8.2 (8)
O4ⁱ—Zn1—N1—C11	17.1 (7)	C16—C15—N3—C14	−3.0 (6)
O1—Zn1—N1—C11	153.7 (6)	C16—C15—N3—C21	179.3 (5)
N1'—Zn1—N1—C11	179.7 (13)	C20—C21—N3—C14	−78.2 (7)
N4ⁱⁱ—Zn1—N1—C11	−98.4 (7)	C20—C21—N3—C15	98.8 (6)
N1—C9—N2—C10	3.9 (10)	N3—C14—N4—C16	−1.2 (6)
C12—C9—N2—C10	−173.2 (9)	C17—C14—N4—C16	−172.7 (5)
N1—C9—N2—C19	−166.0 (7)	N3—C14—N4—Zn1ⁱⁱⁱ	−176.4 (3)
C12—C9—N2—C19	17.0 (14)	C17—C14—N4—Zn1ⁱⁱⁱ	12.0 (8)
C11—C10—N2—C9	−3.0 (11)	C15—C16—N4—C14	−0.8 (6)
C11—C10—N2—C19	167.0 (9)	C15—C16—N4—Zn1ⁱⁱⁱ	175.3 (4)
N2'—C10'—C11'—N1'	4.9 (19)	O2—C7—O1—Zn1	17.5 (5)
N1'—C9'—C12'—C13'	108 (3)	C1—C7—O1—Zn1	−161.0 (3)
N2'—C9'—C12'—C13'	−73 (3)	O4ⁱ—Zn1—O1—C7	33.0 (3)
C10'—C11'—N1'—C9'	−3 (2)	N1—Zn1—O1—C7	−89.0 (3)
C10'—C11'—N1'—Zn1	−179.6 (11)	N1'—Zn1—O1—C7	−99.2 (4)
N2'—C9'—N1'—C11'	0.3 (19)	N4ⁱⁱ—Zn1—O1—C7	152.8 (3)
C12'—C9'—N1'—C11'	179.6 (18)	O3—C8—O4—Zn1^iv	−10.0 (6)
N2'—C9'—N1'—Zn1	176.1 (11)	C3—C8—O4—Zn1^iv	170.2 (3)

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+3/2, −y+1, z+1/2; (iii) −x+3/2, −y+1, z−1/2; (iv) −x, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1^v	0.82	1.97	2.741 (5)	156

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₄O₅)(C₁₃H₂₀N₄)]
M_r	477.83
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.476 (2), 14.846 (4), 15.724 (4)
V (Å³)	2212.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.35 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.68, 0.78
No. of measured, independent and observed [I > 2σ(I)] reflections	21558, 5031, 4372
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.136, 1.05
No. of reflections	5031
No. of parameters	309
No. of restraints	15
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.46
Absolute structure	Flack (1983), 2190 Friedel pairs
Absolute structure parameter	−0.006 (19)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O1	1.992 (3)	Zn1—N1'	2.047 (13)
Zn1—O4ⁱ	1.950 (3)	Zn1—N4ⁱⁱ	2.055 (4)
Zn1—N1	2.021 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1ⁱⁱⁱ	0.82	1.97	2.741 (5)	156

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

Acknowledgements

We thank the China Postdoctoral Science Foundation (20100471379) for support.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, Y.-Y., Ma, J.-F. & Zhang, L.-P. (2007). Acta Cryst. E63, m2317. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, Y.-Y., Wang, Z.-H., Yang, J., Liu, B., Liu, Y.-Y. & Ma, J.-F. (2011). CrystEngComm, 13, 3811–3821. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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