catena-Poly[[bis­(1-allyl­imidazole)zinc(II)]-μ-phthalato-κ2O1:O2]

Li, R.-X.; Wu, Q.-Y.; Liu, F.-Q.

doi:10.1107/S1600536810003892

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m258

doi:10.1107/S1600536810003892

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catena-Poly[[bis(1-allylimidazole)zinc(II)]-μ-phthalato-κ²O¹:O²]

Rong-Xun Li,^a ^* Qi-Ye Wu ^a and Fa-Qian Liu ^a

^aSchool of Materials Science and Engineering, University of Science and Technology Beijing, Beijing 100083, People's Republic of China
^*Correspondence e-mail: lirongxun163@163.com

(Received 29 January 2010; accepted 1 February 2010; online 6 February 2010)

The structure of the title compound, [Zn(C₈H₄O₄)(C₆H₈N₂)₂]_n, exhibits polymeric zigzag chains extended along the c axis. The Zn^II ion is coordinated by two N [Zn—N = 2.008 (6) and 2.012 (6) Å] and two O [Zn—O = 1.959 (5) and 1.985 (5) Å] atoms in a distorted tetrahedral geometry. Weak C—H⋯O interactions contribute to the crystal packing stability.

Related literature

In the corresponding zinc compounds, [Zn(phthalato)(1-H-vinylimidazole)₂] (Li et al., 2007a ) and [Zn(phthalato)(1-H-ethylimidazole)₂] (Li et al., 2007b ), the Zn^II ions also have a distorted tetrahedral environment.

Experimental

Crystal data

[Zn(C₈H₄O₄)(C₆H₈N₂)₂]
M_r = 445.77
Orthorhombic, P c a 2₁
a = 10.675 (2) Å
b = 13.858 (3) Å
c = 13.610 (3) Å
V = 2013.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.25 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.788, T_max = 0.885
3662 measured reflections
3078 independent reflections
2672 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.170
S = 1.01
3078 reflections
262 parameters
21 restraints
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.94 e Å⁻³
Absolute structure: Flack (1983 ), 1148 Friedel pairs
Flack parameter: 0.01 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2ⁱ	0.97	2.56	3.424 (10)	148
C5—H5A⋯O3	0.93	2.43	3.070 (10)	126
C6—H6A⋯O1	0.93	2.38	3.080 (11)	132
C9—H9A⋯O3ⁱⁱ	0.97	2.48	3.317 (11)	144
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+1, z]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003892/hg2640sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003892/hg2640Isup2.hkl

checkCIF report

Comment top

In the title compound,(I)(Fig. 1), The zinc(II) centers are bridged by the carboxylate group of o-phthalate and saturated by 1-allylimidazole. Each Zn^II ion is coordinated by two N [Zn—N2 = 2.012 (6),Zn—N4 = 2.008 (6) Å] and two O [Zn—O2 = 1.959 (5), Zn—O4 = 1.985 (5) Å] atoms in a distorted tetrahedral geometry. All these values agree well with those observed in [Zn(phthalato)(1-H-vinylimidazole)₂] (Li et al., 2007a) and [Zn(phthalato)(1-H-ethylimidazole)₂] (Li et al., 2007b). Each o-phthalate dianion acts as a bidentate ligand to bridge two Zn^II atoms through two monodentate carboxylate groups, building a zigzag infinate chain structure along the c axis. The metal-metal distances across each polymer backbone are 6.908 (6) Å.In the crystal, Weak C—H···O interactions contribute to the crystal packing stability.

In the corresponding zinc compounds, [Zn(phthalato)(1-H-vinylimidazole)₂] (Li, et al., 2007a) and [Zn(phthalato)(1-H-ethylimidazole)₂] (Li, et al., 2007b) the Zn^II ions have a distorted tetrahedral environment.

Related literature top

In the corresponding zinc compounds, [Zn(phthalato)(1-H-vinylimidazole)₂] (Li et al., 2007a) and [Zn(phthalato)(1-H-ethylimidazole)₂] (Li et al., 2007b), the Zn^II ions have a distorted tetrahedral environment.

Experimental top

The reaction of ZnCl₂(0.68 g, 5 mmol) with o-phthalic acid (0.83 g, 5 mmol) in an aqueous-methanol(3:1) solution(40 ml) at 363 K for 30 minutes produced a colorless solution, to which 1-allylimidazole (1.08 g,10 mmol) was added. The reaction solution was kept at room temperature after stirring for an hour at 363 K . Colorless crystals were obtained after a few days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. A portion of the polymeric chain in the title compound showing atomic numbering and 30% probability displacement ellipsoids [symmetry codes: (A) -x+3/2,y,z-1/2.
	Fig. 2. The packing of (I), viewed down the b axis.

catena-Poly[[bis(1-allylimidazole)zinc(II)]-µ-phthalato- κ²O¹:O²] top

Crystal data top

[Zn(C₈H₄O₄)(C₆H₈N₂)₂]	F(000) = 920
M_r = 445.77	D_x = 1.471 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3003 reflections
a = 10.675 (2) Å	θ = 1.5–25.3°
b = 13.858 (3) Å	µ = 1.25 mm⁻¹
c = 13.610 (3) Å	T = 293 K
V = 2013.4 (7) Å³	Block, colorless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3078 independent reflections
Radiation source: fine-focus sealed tube	2672 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
thin–slice ω scans	θ_max = 25.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = 0→12
T_min = 0.788, T_max = 0.885	k = 0→16
3662 measured reflections	l = −16→16

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)] = 0.063	H-atom parameters constrained
wR(F²) = 0.170	w = 1/[σ²(F_o²) + (0.1P)² + 1.7P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3078 reflections	Δρ_max = 0.86 e Å⁻³
262 parameters	Δρ_min = −0.94 e Å⁻³
21 restraints	Absolute structure: Flack (1983), 1148 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (3)

Crystal data top

[Zn(C₈H₄O₄)(C₆H₈N₂)₂]	V = 2013.4 (7) Å³
M_r = 445.77	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 10.675 (2) Å	µ = 1.25 mm⁻¹
b = 13.858 (3) Å	T = 293 K
c = 13.610 (3) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3078 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2672 reflections with I > 2σ(I)
T_min = 0.788, T_max = 0.885	R_int = 0.013
3662 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.170	Δρ_max = 0.86 e Å⁻³
S = 1.01	Δρ_min = −0.94 e Å⁻³
3078 reflections	Absolute structure: Flack (1983), 1148 Friedel pairs
262 parameters	Absolute structure parameter: 0.01 (3)
21 restraints

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 > 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
Zn	0.80554 (7)	0.24867 (6)	0.17695 (11)	0.0404 (2)
O1	0.6427 (6)	0.2741 (4)	0.0031 (4)	0.0527 (14)
O2	0.6618 (4)	0.1729 (4)	0.1314 (3)	0.0460 (12)
O3	1.0107 (5)	0.2747 (4)	0.3026 (4)	0.0499 (13)
O4	0.8498 (5)	0.1737 (4)	0.2963 (3)	0.0475 (12)
N1	1.0272 (6)	0.1987 (5)	−0.0680 (4)	0.0521 (17)
N2	0.9385 (6)	0.2337 (5)	0.0733 (4)	0.0463 (15)
N3	0.7033 (6)	0.5006 (4)	0.3164 (5)	0.0510 (16)
N4	0.7491 (7)	0.3801 (4)	0.2205 (4)	0.0472 (14)
C1	1.1212 (13)	0.2987 (10)	−0.2907 (9)	0.117 (4)
H1A	1.0419	0.3048	−0.3185	0.140*
H1B	1.1873	0.3358	−0.3143	0.140*
C2	1.1396 (16)	0.2381 (9)	−0.2185 (9)	0.108 (4)
H2A	1.2202	0.2342	−0.1927	0.130*
C3	1.0418 (10)	0.1747 (7)	−0.1742 (6)	0.067 (3)
H3A	0.9627	0.1841	−0.2079	0.081*
H3B	1.0659	0.1076	−0.1813	0.081*
C4	1.1200 (8)	0.2010 (7)	0.0013 (6)	0.064 (2)
H4A	1.2048	0.1897	−0.0093	0.077*
C5	1.0653 (8)	0.2229 (8)	0.0875 (6)	0.064 (2)
H5A	1.1067	0.2296	0.1473	0.077*
C6	0.9205 (9)	0.2199 (6)	−0.0230 (6)	0.054 (2)
H6A	0.8433	0.2246	−0.0542	0.064*
C7	0.5349 (13)	0.4544 (10)	0.4792 (11)	0.115 (4)
H7A	0.5376	0.4124	0.4260	0.138*
H7B	0.4812	0.4419	0.5315	0.138*
C8	0.6023 (12)	0.5264 (10)	0.4805 (9)	0.103 (4)
H8A	0.5944	0.5649	0.5361	0.124*
C9	0.6961 (9)	0.5618 (7)	0.4052 (7)	0.071 (3)
H9A	0.6737	0.6269	0.3858	0.085*
H9B	0.7783	0.5644	0.4355	0.085*
C10	0.6367 (8)	0.5131 (6)	0.2322 (6)	0.057 (2)
H10A	0.5824	0.5636	0.2177	0.069*
C11	0.6646 (7)	0.4394 (5)	0.1753 (7)	0.0564 (19)
H11A	0.6315	0.4292	0.1130	0.068*
C12	0.7688 (8)	0.4184 (6)	0.3080 (6)	0.0504 (19)
H12A	0.8203	0.3924	0.3563	0.060*
C13	0.4530 (7)	0.0680 (6)	0.0655 (6)	0.0515 (19)
H13A	0.4738	0.0641	0.1317	0.062*
C14	0.3601 (8)	0.0089 (6)	0.0297 (6)	0.057 (2)
H14A	0.3168	−0.0323	0.0715	0.068*
C15	0.3319 (8)	0.0118 (6)	−0.0695 (7)	0.058 (2)
H15A	0.2695	−0.0281	−0.0945	0.070*
C16	0.3937 (8)	0.0716 (6)	−0.1302 (6)	0.053 (2)
H16A	0.3759	0.0702	−0.1971	0.064*
C17	0.4853 (6)	0.1368 (5)	−0.0948 (5)	0.0379 (16)
C18	0.5166 (6)	0.1329 (5)	0.0063 (5)	0.0386 (15)
C19	0.6122 (7)	0.1995 (6)	0.0472 (5)	0.0424 (17)
C20	0.9526 (7)	0.2027 (6)	0.3316 (5)	0.0380 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0443 (4)	0.0475 (4)	0.0294 (3)	0.0011 (4)	0.0035 (5)	0.0003 (4)
O1	0.056 (3)	0.062 (3)	0.041 (3)	−0.013 (3)	−0.002 (3)	0.002 (3)
O2	0.044 (3)	0.065 (4)	0.029 (2)	0.003 (3)	−0.008 (2)	−0.002 (2)
O3	0.051 (3)	0.057 (3)	0.042 (3)	−0.010 (3)	0.004 (3)	0.005 (3)
O4	0.045 (3)	0.066 (3)	0.032 (3)	−0.007 (3)	−0.008 (2)	0.004 (2)
N1	0.054 (4)	0.077 (5)	0.026 (3)	−0.004 (4)	0.012 (3)	−0.005 (3)
N2	0.039 (3)	0.070 (4)	0.030 (3)	0.003 (3)	0.008 (3)	0.004 (3)
N3	0.061 (4)	0.049 (4)	0.044 (3)	−0.002 (3)	0.002 (3)	−0.005 (3)
N4	0.058 (4)	0.043 (3)	0.040 (3)	0.003 (3)	−0.001 (3)	−0.011 (3)
C1	0.112 (8)	0.128 (8)	0.109 (8)	−0.030 (7)	−0.019 (7)	0.010 (7)
C2	0.134 (8)	0.117 (8)	0.072 (7)	−0.028 (7)	0.021 (7)	−0.005 (6)
C3	0.083 (6)	0.081 (6)	0.038 (4)	−0.016 (5)	0.015 (4)	−0.009 (4)
C4	0.047 (5)	0.092 (6)	0.054 (5)	0.012 (5)	0.016 (4)	−0.014 (5)
C5	0.048 (5)	0.102 (7)	0.041 (5)	0.006 (5)	−0.004 (4)	−0.006 (5)
C6	0.059 (5)	0.064 (5)	0.038 (4)	0.003 (4)	−0.002 (4)	0.003 (4)
C7	0.122 (11)	0.121 (10)	0.101 (10)	0.021 (7)	0.036 (9)	−0.004 (9)
C8	0.101 (9)	0.142 (11)	0.067 (7)	−0.005 (8)	−0.002 (7)	−0.042 (8)
C9	0.082 (7)	0.068 (6)	0.062 (6)	0.007 (5)	−0.013 (5)	−0.030 (5)
C10	0.068 (6)	0.052 (5)	0.052 (5)	0.012 (4)	−0.006 (4)	0.005 (4)
C11	0.072 (5)	0.055 (4)	0.042 (4)	0.010 (4)	−0.007 (5)	0.002 (5)
C12	0.047 (5)	0.057 (5)	0.047 (4)	0.008 (4)	−0.004 (4)	−0.006 (4)
C13	0.053 (5)	0.062 (5)	0.040 (4)	0.001 (4)	0.012 (4)	−0.002 (4)
C14	0.057 (5)	0.052 (5)	0.062 (5)	−0.010 (4)	0.016 (4)	0.003 (4)
C15	0.048 (5)	0.039 (4)	0.087 (7)	−0.009 (4)	−0.009 (4)	−0.009 (4)
C16	0.045 (5)	0.060 (5)	0.054 (5)	−0.001 (4)	−0.012 (4)	−0.003 (4)
C17	0.031 (4)	0.048 (4)	0.035 (4)	0.007 (3)	−0.003 (3)	−0.009 (3)
C18	0.038 (4)	0.044 (4)	0.034 (3)	0.009 (3)	0.003 (3)	0.003 (3)
C19	0.032 (4)	0.061 (5)	0.034 (4)	0.011 (4)	0.002 (3)	−0.011 (4)
C20	0.045 (4)	0.047 (4)	0.022 (3)	0.004 (4)	0.003 (3)	−0.007 (3)

Geometric parameters (Å, º) top

Zn—O2	1.959 (5)	C5—H5A	0.9300
Zn—O4	1.985 (5)	C6—H6A	0.9300
Zn—N4	2.008 (6)	C7—C8	1.230 (17)
Zn—N2	2.012 (6)	C7—H7A	0.9300
O1—C19	1.239 (9)	C7—H7B	0.9300
O2—C19	1.316 (9)	C8—C9	1.515 (16)
O3—C20	1.240 (9)	C8—H8A	0.9300
O4—C20	1.263 (9)	C9—H9A	0.9700
N1—C6	1.327 (11)	C9—H9B	0.9700
N1—C4	1.368 (11)	C10—C11	1.315 (11)
N1—C3	1.491 (9)	C10—H10A	0.9300
N2—C6	1.337 (10)	C11—H11A	0.9300
N2—C5	1.376 (11)	C12—H12A	0.9300
N3—C12	1.342 (9)	C13—C14	1.374 (11)
N3—C10	1.359 (10)	C13—C18	1.385 (10)
N3—C9	1.479 (10)	C13—H13A	0.9300
N4—C12	1.320 (10)	C14—C15	1.384 (12)
N4—C11	1.367 (10)	C14—H14A	0.9300
C1—C2	1.308 (9)	C15—C16	1.344 (12)
C1—H1A	0.9300	C15—H15A	0.9300
C1—H1B	0.9300	C16—C17	1.416 (11)
C2—C3	1.492 (16)	C16—H16A	0.9300
C2—H2A	0.9300	C17—C18	1.417 (9)
C3—H3A	0.9700	C17—C20ⁱ	1.509 (10)
C3—H3B	0.9700	C18—C19	1.483 (10)
C4—C5	1.346 (11)	C20—C17ⁱⁱ	1.509 (10)
C4—H4A	0.9300

O2—Zn—O4	99.5 (2)	H7A—C7—H7B	120.0
O2—Zn—N4	110.1 (2)	C7—C8—C9	129.8 (12)
O4—Zn—N4	107.7 (2)	C7—C8—H8A	115.1
O2—Zn—N2	106.0 (2)	C9—C8—H8A	115.1
O4—Zn—N2	110.6 (2)	N3—C9—C8	113.7 (8)
N4—Zn—N2	120.8 (3)	N3—C9—H9A	108.8
C19—O2—Zn	116.2 (5)	C8—C9—H9A	108.8
C20—O4—Zn	110.6 (5)	N3—C9—H9B	108.8
C6—N1—C4	107.3 (6)	C8—C9—H9B	108.8
C6—N1—C3	125.9 (8)	H9A—C9—H9B	107.7
C4—N1—C3	126.7 (7)	C11—C10—N3	106.2 (7)
C6—N2—C5	105.3 (7)	C11—C10—H10A	126.9
C6—N2—Zn	126.9 (6)	N3—C10—H10A	126.9
C5—N2—Zn	127.3 (5)	C10—C11—N4	110.6 (8)
C12—N3—C10	108.0 (7)	C10—C11—H11A	124.7
C12—N3—C9	125.7 (7)	N4—C11—H11A	124.7
C10—N3—C9	126.1 (7)	N4—C12—N3	109.6 (7)
C12—N4—C11	105.6 (7)	N4—C12—H12A	125.2
C12—N4—Zn	125.7 (5)	N3—C12—H12A	125.2
C11—N4—Zn	127.7 (5)	C14—C13—C18	122.3 (7)
C2—C1—H1A	120.0	C14—C13—H13A	118.8
C2—C1—H1B	120.0	C18—C13—H13A	118.8
H1A—C1—H1B	120.0	C13—C14—C15	119.0 (8)
C1—C2—C3	125.2 (15)	C13—C14—H14A	120.5
C1—C2—H2A	117.4	C15—C14—H14A	120.5
C3—C2—H2A	117.4	C16—C15—C14	120.7 (8)
N1—C3—C2	109.5 (8)	C16—C15—H15A	119.6
N1—C3—H3A	109.8	C14—C15—H15A	119.6
C2—C3—H3A	109.8	C15—C16—C17	121.5 (7)
N1—C3—H3B	109.8	C15—C16—H16A	119.2
C2—C3—H3B	109.8	C17—C16—H16A	119.2
H3A—C3—H3B	108.2	C16—C17—C18	118.0 (7)
C5—C4—N1	107.0 (7)	C16—C17—C20ⁱ	117.6 (6)
C5—C4—H4A	126.5	C18—C17—C20ⁱ	124.4 (6)
N1—C4—H4A	126.5	C13—C18—C17	118.2 (7)
C4—C5—N2	109.2 (8)	C13—C18—C19	121.6 (7)
C4—C5—H5A	125.4	C17—C18—C19	120.1 (6)
N2—C5—H5A	125.4	O1—C19—O2	123.3 (7)
N1—C6—N2	111.1 (8)	O1—C19—C18	121.3 (6)
N1—C6—H6A	124.4	O2—C19—C18	115.4 (7)
N2—C6—H6A	124.4	O3—C20—O4	124.7 (7)
C8—C7—H7A	120.0	O3—C20—C17ⁱⁱ	118.6 (7)
C8—C7—H7B	120.0	O4—C20—C17ⁱⁱ	116.2 (7)

O4—Zn—O2—C19	−175.7 (5)	C10—N3—C9—C8	92.3 (11)
N4—Zn—O2—C19	71.4 (5)	C7—C8—C9—N3	2 (2)
N2—Zn—O2—C19	−60.9 (5)	C12—N3—C10—C11	−0.7 (10)
O2—Zn—O4—C20	171.3 (5)	C9—N3—C10—C11	−175.6 (8)
N4—Zn—O4—C20	−73.9 (5)	N3—C10—C11—N4	−0.7 (10)
N2—Zn—O4—C20	60.1 (5)	C12—N4—C11—C10	1.9 (10)
O2—Zn—N2—C6	30.4 (7)	Zn—N4—C11—C10	170.5 (6)
O4—Zn—N2—C6	137.3 (6)	C11—N4—C12—N3	−2.2 (9)
N4—Zn—N2—C6	−95.6 (7)	Zn—N4—C12—N3	−171.2 (5)
O2—Zn—N2—C5	−140.5 (7)	C10—N3—C12—N4	1.9 (9)
O4—Zn—N2—C5	−33.6 (8)	C9—N3—C12—N4	176.8 (8)
N4—Zn—N2—C5	93.5 (8)	C18—C13—C14—C15	2.4 (12)
O2—Zn—N4—C12	123.9 (7)	C13—C14—C15—C16	−0.3 (13)
O4—Zn—N4—C12	16.3 (7)	C14—C15—C16—C17	−3.0 (13)
N2—Zn—N4—C12	−112.1 (7)	C15—C16—C17—C18	4.2 (11)
O2—Zn—N4—C11	−42.7 (7)	C15—C16—C17—C20ⁱ	−178.6 (8)
O4—Zn—N4—C11	−150.2 (7)	C14—C13—C18—C17	−1.0 (11)
N2—Zn—N4—C11	81.4 (7)	C14—C13—C18—C19	176.9 (7)
C6—N1—C3—C2	127.2 (11)	C16—C17—C18—C13	−2.2 (10)
C4—N1—C3—C2	−54.2 (13)	C20ⁱ—C17—C18—C13	−179.2 (7)
C1—C2—C3—N1	−119.3 (14)	C16—C17—C18—C19	179.9 (7)
C6—N1—C4—C5	0.7 (11)	C20ⁱ—C17—C18—C19	2.8 (10)
C3—N1—C4—C5	−178.1 (9)	Zn—O2—C19—O1	−8.2 (9)
N1—C4—C5—N2	0.4 (12)	Zn—O2—C19—C18	171.1 (4)
C6—N2—C5—C4	−1.4 (11)	C13—C18—C19—O1	−159.2 (7)
Zn—N2—C5—C4	171.1 (7)	C17—C18—C19—O1	18.8 (10)
C4—N1—C6—N2	−1.6 (10)	C13—C18—C19—O2	21.6 (10)
C3—N1—C6—N2	177.2 (8)	C17—C18—C19—O2	−160.5 (6)
C5—N2—C6—N1	1.8 (10)	Zn—O4—C20—O3	7.5 (9)
Zn—N2—C6—N1	−170.7 (5)	Zn—O4—C20—C17ⁱⁱ	−164.5 (4)
C12—N3—C9—C8	−81.8 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.97	2.56	3.424 (10)	148
C5—H5A···O3	0.93	2.43	3.070 (10)	126
C6—H6A···O1	0.93	2.38	3.080 (11)	132
C9—H9A···O3ⁱⁱⁱ	0.97	2.48	3.317 (11)	144

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₄O₄)(C₆H₈N₂)₂]
M_r	445.77
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	10.675 (2), 13.858 (3), 13.610 (3)
V (Å³)	2013.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.25
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.788, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	3662, 3078, 2672
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.170, 1.01
No. of reflections	3078
No. of parameters	262
No. of restraints	21
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.94
Absolute structure	Flack (1983), 1148 Friedel pairs
Absolute structure parameter	0.01 (3)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.97	2.56	3.424 (10)	148
C5—H5A···O3	0.93	2.43	3.070 (10)	126
C6—H6A···O1	0.93	2.38	3.080 (11)	132
C9—H9A···O3ⁱⁱ	0.97	2.48	3.317 (11)	144

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

Acknowledgements

This work was supported by the NSF of China (Nos. 20601015, 20871072) and the Doctoral Science Foundation of Shandong Province (No. 2007BS04023).

References

Bruker (2001). 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
Li, R.-X., Li, S.-X., Liu, L., Liu, G.-Y. & Liu, F.-Q. (2007b). Acta Cryst. E63, m2875. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, R.-X., Li, S.-X., Wu, Q.-Y., Liu, G.-Y. & Liu, F.-Q. (2007a). Acta Cryst. E63, m2874. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). 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