Poly[[μ2-2,2′-diethyl-1,1′-(butane-1,4-di­yl)diimidazole-κ2N3:N3′](μ2-5-hydroxy­isophthalato-κ2O1:O3)zinc]

Liu, Y.-Y.; Wang, X.; Yan, Y.-S.

doi:10.1107/S1600536811039377

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1477

doi:10.1107/S1600536811039377

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Poly[[μ₂-2,2′-diethyl-1,1′-(butane-1,4-diyl)diimidazole-κ²N³:N^3′](μ₂-5-hydroxyisophthalato-κ²O¹:O³)zinc]

Ying-Ying Liu,^a Xing 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: liuyy21@yahoo.com.cn

(Received 19 September 2011; accepted 26 September 2011; online 5 October 2011)

In the title coordination polymer, [Zn(C₈H₄O₅)(C₁₄H₂₂N₄)]_n, the Zn^II cation is coordinated by an O₂N₂ donor set in a distorted tetrahedral geometry. The Zn^II ions are linked by μ₂-OH-bdc (OH-H₂bdc = 5-hydroxyisophthalic acid) and bbie ligands [bbie = 2,2′-diethyl-1,1′-(butane-1,4-diyl)diimidazole], forming a two-dimensional layer parallel to the ab plane. The layers are further connected through intermolecular C—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional supramolecular structure. In the bbie ligand, the two C atoms in the ethyl group are each disordered over two positions with a site-occupancy ratio of 0.69:0.31.

Related literature

For background information on bis(imidazole) ligands, see: Kan et al. (2011 ); Liu et al. (2007 ).

Experimental

Crystal data

[Zn(C₈H₄O₅)(C₁₄H₂₂N₄)]
M_r = 491.84
Monoclinic, P 2₁ /n
a = 13.5120 (12) Å
b = 12.765 (1) Å
c = 13.5910 (12) Å
β = 103.933 (2)°
V = 2275.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 293 K
0.28 × 0.24 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.73, T_max = 0.79
13890 measured reflections
5467 independent reflections
3988 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.087
S = 1.03
5467 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	1.9662 (15)
Zn1—O4ⁱ	1.9682 (14)
Zn1—N4ⁱⁱ	2.0020 (18)
Zn1—N1	2.0286 (17)

O1—Zn1—O4ⁱ	102.54 (6)
O1—Zn1—N4ⁱⁱ	117.20 (7)
O4ⁱ—Zn1—N4ⁱⁱ	118.18 (7)
O1—Zn1—N1	115.96 (7)
O4ⁱ—Zn1—N1	98.33 (6)
N4ⁱⁱ—Zn1—N1	103.59 (7)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1ⁱⁱⁱ	0.93	2.62	3.417 (3)	144
C14—H14⋯O5ⁱⁱⁱ	0.93	2.49	3.398 (3)	166
O5—H5⋯O2^iv	0.82	1.88	2.697 (2)	171
Symmetry code: (iii) -x+1, -y+1, -z+1; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811039377/fj2452sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039377/fj2452Isup2.hkl

checkCIF report

Comment top

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

As shown in Fig. 1, the Zn^II ions is four-coordinated by two oxygen atoms from two oxygen atoms of two OH-bdc anions and two nitrogen atoms of two bbie ligands. Each carboxylate group of OH-bdc acts in a monodentate mode, and the hydroxyl group is not involved in coordination. The bbie molecule coordinates to two Zn^II cations through its two aromatic N atoms, thus acing as a bridging bidentate ligand. As illustrated in Fig. 2, The Zn^II cations are connected by OH-bdc and bbie ligands to form a layer parallel to the ab plane. There exist hydrogen-binding interactions among adjacent layers. The layers are further connected by these hydrogen bonds to a 3D supramolecular architecture.

Related literature top

For background information on bis(imidazole) ligands, see: Kan et al. (2011); Liu et al. (2007).

Experimental top

The ligand bbie was synthesized according to the literature Liu et al., (2007), but 2-phenylimidazole was replaced by 2-ethylimidazole. A mixture of ZnCO₃ (0.050 g, 0.40 mmol), OH—H²bdc (0.043 g, 0.40 mmol), bbie (0.099 g, 0.40 mmol), and water (8 ml) was sealed in a Teflon reactor (18 ml) and heated at 140 °C for 3 days. After the mixture had been cooled to room temperature at 10 °C.h^-1, colorless crystals of (I) were obtained. Yield: 43%.

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

Figures top

	Fig. 1. A view of the local coordination of the Zn^II cation of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. View of the two-dimensional layer of (I).

Poly[[µ₂-2,2'-diethyl-1,1'-(butane-1,4-diyl)diimidazole- κ²N³:N^3'](µ₂-5-hydroxyisophthalato- κ²O¹:O³)zinc] top

Crystal data top

[Zn(C₈H₄O₅)(C₁₄H₂₂N₄)]	F(000) = 1024
M_r = 491.84	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 3988 reflections
a = 13.5120 (12) Å	θ = 1.9–28.3°
b = 12.765 (1) Å	µ = 1.12 mm⁻¹
c = 13.5910 (12) Å	T = 293 K
β = 103.933 (2)°	Block, colorless
V = 2275.2 (3) Å³	0.28 × 0.24 × 0.21 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5467 independent reflections
Radiation source: fine-focus sealed tube	3988 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→17
T_min = 0.73, T_max = 0.79	k = −14→17
13890 measured reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0374P)² + 0.1596P] where P = (F_o² + 2F_c²)/3
5467 reflections	(Δ/σ)_max = 0.001
309 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Zn(C₈H₄O₅)(C₁₄H₂₂N₄)]	V = 2275.2 (3) Å³
M_r = 491.84	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.5120 (12) Å	µ = 1.12 mm⁻¹
b = 12.765 (1) Å	T = 293 K
c = 13.5910 (12) Å	0.28 × 0.24 × 0.21 mm
β = 103.933 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5467 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3988 reflections with I > 2σ(I)
T_min = 0.73, T_max = 0.79	R_int = 0.034
13890 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.03	Δρ_max = 0.32 e Å⁻³
5467 reflections	Δρ_min = −0.29 e Å⁻³
309 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	Occ. (<1)
Zn1	0.582734 (18)	0.485563 (18)	0.336590 (17)	0.03285 (9)
C1	0.35185 (15)	0.26820 (15)	0.21865 (15)	0.0328 (4)
C2	0.30834 (15)	0.23700 (16)	0.11970 (15)	0.0354 (5)
H2	0.3183	0.2771	0.0658	0.042*
C3	0.24997 (15)	0.14625 (16)	0.10089 (15)	0.0339 (5)
C4	0.23245 (15)	0.08795 (16)	0.18177 (15)	0.0338 (5)
H4	0.1928	0.0276	0.1695	0.041*
C5	0.27431 (15)	0.12020 (16)	0.28070 (15)	0.0349 (5)
C6	0.33484 (16)	0.20925 (16)	0.29951 (15)	0.0358 (5)
H6	0.3640	0.2296	0.3659	0.043*
C7	0.41726 (16)	0.36460 (16)	0.23657 (16)	0.0349 (5)
C8	0.20549 (16)	0.11336 (17)	−0.00696 (16)	0.0368 (5)
C9	0.48306 (15)	0.70092 (16)	0.27233 (15)	0.0355 (5)
C10	0.51820 (17)	0.67354 (18)	0.43504 (16)	0.0414 (5)
H10	0.5403	0.6413	0.4978	0.050*
C11	0.47890 (18)	0.77010 (18)	0.41969 (18)	0.0466 (6)
H11	0.4683	0.8162	0.4691	0.056*
C12	0.46889 (18)	0.68667 (19)	0.16100 (16)	0.0464 (6)
H12A	0.4015	0.7119	0.1275	0.056*
H12B	0.4707	0.6122	0.1472	0.056*
C13	0.5467 (2)	0.7414 (2)	0.1135 (2)	0.0665 (8)
H13A	0.5387	0.7173	0.0451	0.100*
H13B	0.6144	0.7255	0.1521	0.100*
H13C	0.5360	0.8158	0.1134	0.100*
C14	0.7862 (2)	1.0000 (2)	0.4101 (2)	0.0739 (9)
H14	0.7847	0.9867	0.4770	0.089*
C15	0.8584 (2)	0.9700 (2)	0.36442 (19)	0.0632 (7)
H15	0.9166	0.9323	0.3950	0.076*
C16	0.74705 (18)	1.05462 (18)	0.25407 (18)	0.0443 (5)
C17	0.6885 (7)	1.1012 (7)	0.1514 (6)	0.062 (2)	0.688 (10)
H17A	0.7064	1.0627	0.0966	0.074*	0.688 (10)
H17B	0.6158	1.0932	0.1447	0.074*	0.688 (10)
C18	0.7127 (4)	1.2139 (4)	0.1428 (5)	0.097 (2)	0.688 (10)
H18A	0.6750	1.2404	0.0786	0.146*	0.688 (10)
H18B	0.7844	1.2218	0.1479	0.146*	0.688 (10)
H18C	0.6943	1.2523	0.1965	0.146*	0.688 (10)
C18'	0.6330 (13)	1.0952 (16)	0.0904 (14)	0.156 (10)	0.312 (10)
H18D	0.6135	1.1524	0.0439	0.234*	0.312 (10)
H18E	0.5741	1.0694	0.1105	0.234*	0.312 (10)
H18F	0.6617	1.0400	0.0580	0.234*	0.312 (10)
C17'	0.7098 (17)	1.132 (2)	0.1811 (16)	0.099 (10)	0.312 (10)
H17C	0.7669	1.1615	0.1592	0.119*	0.312 (10)
H17D	0.6797	1.1873	0.2129	0.119*	0.312 (10)
C19	0.41398 (18)	0.88519 (17)	0.2671 (2)	0.0536 (6)
H19A	0.3650	0.9129	0.3021	0.064*
H19B	0.3777	0.8693	0.1981	0.064*
C20	0.49432 (19)	0.96907 (18)	0.26511 (19)	0.0514 (6)
H20A	0.5474	0.9382	0.2374	0.062*
H20B	0.4627	1.0245	0.2195	0.062*
C21	0.5432 (2)	1.01699 (19)	0.3666 (2)	0.0540 (7)
H21A	0.5752	0.9619	0.4125	0.065*
H21B	0.4905	1.0484	0.3945	0.065*
C22	0.6228 (2)	1.1000 (2)	0.3613 (2)	0.0618 (7)
H22A	0.5939	1.1500	0.3084	0.074*
H22B	0.6408	1.1377	0.4252	0.074*
N1	0.52069 (13)	0.62938 (13)	0.34288 (12)	0.0348 (4)
N2	0.45730 (14)	0.78804 (13)	0.31714 (14)	0.0407 (4)
N3	0.71500 (15)	1.05383 (16)	0.34053 (15)	0.0490 (5)
N4	0.83402 (14)	1.00315 (13)	0.26584 (13)	0.0379 (4)
O1	0.48724 (12)	0.36689 (12)	0.31780 (11)	0.0484 (4)
O2	0.40181 (12)	0.43621 (12)	0.17278 (11)	0.0460 (4)
O3	0.21788 (14)	0.16868 (13)	−0.07723 (11)	0.0565 (5)
O4	0.15489 (12)	0.02734 (11)	−0.01974 (10)	0.0400 (4)
O5	0.26148 (12)	0.06464 (12)	0.36316 (10)	0.0482 (4)
H5	0.2121	0.0257	0.3459	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03576 (15)	0.03453 (14)	0.02655 (13)	−0.00202 (10)	0.00417 (10)	0.00010 (10)
C1	0.0291 (11)	0.0328 (11)	0.0340 (11)	−0.0004 (8)	0.0028 (9)	−0.0028 (9)
C2	0.0374 (12)	0.0369 (11)	0.0307 (10)	−0.0007 (9)	0.0057 (9)	0.0014 (9)
C3	0.0328 (11)	0.0366 (11)	0.0297 (10)	0.0016 (9)	0.0023 (9)	−0.0023 (9)
C4	0.0302 (11)	0.0338 (11)	0.0350 (11)	−0.0027 (9)	0.0032 (9)	−0.0004 (9)
C5	0.0334 (11)	0.0396 (12)	0.0310 (11)	0.0013 (9)	0.0062 (9)	0.0041 (9)
C6	0.0372 (12)	0.0393 (12)	0.0274 (10)	−0.0012 (9)	0.0006 (9)	−0.0048 (9)
C7	0.0341 (12)	0.0373 (11)	0.0342 (11)	−0.0003 (9)	0.0095 (9)	−0.0065 (9)
C8	0.0360 (12)	0.0382 (12)	0.0326 (11)	0.0019 (9)	0.0014 (9)	−0.0008 (9)
C9	0.0331 (11)	0.0359 (11)	0.0365 (11)	−0.0023 (9)	0.0065 (9)	0.0013 (9)
C10	0.0458 (13)	0.0450 (13)	0.0352 (12)	−0.0027 (10)	0.0130 (10)	−0.0027 (10)
C11	0.0515 (15)	0.0464 (14)	0.0465 (14)	−0.0030 (11)	0.0211 (12)	−0.0109 (11)
C12	0.0518 (14)	0.0470 (14)	0.0370 (12)	0.0041 (11)	0.0042 (11)	0.0047 (10)
C13	0.089 (2)	0.0669 (18)	0.0512 (15)	−0.0035 (16)	0.0321 (15)	0.0076 (13)
C14	0.076 (2)	0.112 (3)	0.0406 (15)	0.0171 (18)	0.0274 (15)	0.0192 (15)
C15	0.0628 (18)	0.088 (2)	0.0404 (14)	0.0194 (15)	0.0163 (13)	0.0225 (14)
C16	0.0472 (14)	0.0423 (13)	0.0471 (13)	0.0010 (11)	0.0186 (11)	0.0030 (11)
C17	0.060 (4)	0.074 (4)	0.044 (4)	0.027 (3)	−0.001 (3)	0.006 (3)
C18	0.090 (4)	0.082 (4)	0.112 (5)	0.013 (3)	0.011 (3)	0.059 (3)
C18'	0.092 (12)	0.26 (2)	0.110 (13)	0.064 (14)	0.018 (10)	0.090 (14)
C17'	0.066 (12)	0.19 (3)	0.055 (12)	0.051 (13)	0.036 (10)	0.035 (12)
C19	0.0472 (15)	0.0385 (13)	0.0748 (18)	0.0058 (11)	0.0140 (13)	0.0050 (12)
C20	0.0549 (16)	0.0382 (13)	0.0642 (17)	0.0024 (11)	0.0202 (13)	0.0052 (12)
C21	0.0518 (15)	0.0517 (15)	0.0673 (17)	−0.0062 (12)	0.0312 (14)	−0.0104 (13)
C22	0.0590 (17)	0.0528 (16)	0.086 (2)	−0.0054 (13)	0.0416 (15)	−0.0192 (14)
N1	0.0374 (10)	0.0359 (10)	0.0310 (9)	−0.0003 (8)	0.0081 (8)	−0.0001 (8)
N2	0.0395 (11)	0.0332 (10)	0.0507 (11)	0.0010 (8)	0.0133 (9)	−0.0009 (8)
N3	0.0498 (12)	0.0519 (12)	0.0509 (12)	−0.0039 (10)	0.0231 (10)	−0.0098 (10)
N4	0.0409 (11)	0.0412 (10)	0.0325 (9)	0.0015 (8)	0.0104 (8)	0.0013 (8)
O1	0.0477 (10)	0.0477 (9)	0.0418 (9)	−0.0153 (8)	−0.0048 (7)	0.0006 (7)
O2	0.0533 (10)	0.0365 (9)	0.0454 (9)	−0.0049 (7)	0.0066 (8)	0.0031 (7)
O3	0.0758 (12)	0.0585 (11)	0.0317 (8)	−0.0190 (9)	0.0063 (8)	0.0016 (8)
O4	0.0453 (9)	0.0381 (8)	0.0312 (8)	−0.0052 (7)	−0.0013 (7)	−0.0039 (6)
O5	0.0563 (10)	0.0549 (10)	0.0313 (8)	−0.0147 (8)	0.0066 (7)	0.0049 (7)

Geometric parameters (Å, º) top

Zn1—O1	1.9662 (15)	C14—H14	0.9300
Zn1—O4ⁱ	1.9682 (14)	C15—N4	1.367 (3)
Zn1—N4ⁱⁱ	2.0020 (18)	C15—H15	0.9300
Zn1—N1	2.0286 (17)	C16—N4	1.322 (3)
C1—C2	1.390 (3)	C16—N3	1.347 (3)
C1—C6	1.396 (3)	C16—C17'	1.40 (3)
C1—C7	1.500 (3)	C16—C17	1.547 (9)
C2—C3	1.390 (3)	C17—C18	1.486 (12)
C2—H2	0.9300	C17—H17A	0.9700
C3—C4	1.394 (3)	C17—H17B	0.9700
C3—C8	1.504 (3)	C18—H18A	0.9600
C4—C5	1.390 (3)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
C5—O5	1.372 (2)	C18'—C17'	1.48 (3)
C5—C6	1.388 (3)	C18'—H18D	0.9600
C6—H6	0.9300	C18'—H18E	0.9600
C7—O2	1.243 (2)	C18'—H18F	0.9600
C7—O1	1.269 (2)	C17'—H17C	0.9700
C8—O3	1.231 (3)	C17'—H17D	0.9700
C8—O4	1.283 (2)	C19—N2	1.467 (3)
C9—N1	1.333 (2)	C19—C20	1.530 (3)
C9—N2	1.353 (3)	C19—H19A	0.9700
C9—C12	1.490 (3)	C19—H19B	0.9700
C10—C11	1.338 (3)	C20—C21	1.508 (3)
C10—N1	1.381 (3)	C20—H20A	0.9700
C10—H10	0.9300	C20—H20B	0.9700
C11—N2	1.373 (3)	C21—C22	1.524 (3)
C11—H11	0.9300	C21—H21A	0.9700
C12—C13	1.530 (3)	C21—H21B	0.9700
C12—H12A	0.9700	C22—N3	1.466 (3)
C12—H12B	0.9700	C22—H22A	0.9700
C13—H13A	0.9600	C22—H22B	0.9700
C13—H13B	0.9600	N4—Zn1ⁱⁱⁱ	2.0020 (18)
C13—H13C	0.9600	O4—Zn1^iv	1.9682 (14)
C14—C15	1.333 (4)	O5—H5	0.8200
C14—N3	1.362 (3)

O1—Zn1—O4ⁱ	102.54 (6)	C18—C17—H17A	109.3
O1—Zn1—N4ⁱⁱ	117.20 (7)	C16—C17—H17A	109.3
O4ⁱ—Zn1—N4ⁱⁱ	118.18 (7)	C18—C17—H17B	109.3
O1—Zn1—N1	115.96 (7)	C16—C17—H17B	109.3
O4ⁱ—Zn1—N1	98.33 (6)	H17A—C17—H17B	108.0
N4ⁱⁱ—Zn1—N1	103.59 (7)	C17—C18—H18A	109.5
C2—C1—C6	119.72 (18)	C17—C18—H18B	109.5
C2—C1—C7	119.17 (18)	H18A—C18—H18B	109.5
C6—C1—C7	121.11 (17)	C17—C18—H18C	109.5
C3—C2—C1	120.38 (19)	H18A—C18—H18C	109.5
C3—C2—H2	119.8	H18B—C18—H18C	109.5
C1—C2—H2	119.8	C17'—C18'—H18D	109.5
C2—C3—C4	119.76 (18)	C17'—C18'—H18E	109.5
C2—C3—C8	119.19 (19)	H18D—C18'—H18E	109.5
C4—C3—C8	121.04 (18)	C17'—C18'—H18F	109.5
C5—C4—C3	119.87 (19)	H18D—C18'—H18F	109.5
C5—C4—H4	120.1	H18E—C18'—H18F	109.5
C3—C4—H4	120.1	C16—C17'—C18'	115 (2)
O5—C5—C6	117.24 (17)	C16—C17'—H17C	108.4
O5—C5—C4	122.36 (19)	C18'—C17'—H17C	108.4
C6—C5—C4	120.36 (19)	C16—C17'—H17D	108.4
C5—C6—C1	119.87 (18)	C18'—C17'—H17D	108.4
C5—C6—H6	120.1	H17C—C17'—H17D	107.5
C1—C6—H6	120.1	N2—C19—C20	113.23 (19)
O2—C7—O1	123.70 (19)	N2—C19—H19A	108.9
O2—C7—C1	119.78 (18)	C20—C19—H19A	108.9
O1—C7—C1	116.52 (18)	N2—C19—H19B	108.9
O3—C8—O4	123.61 (19)	C20—C19—H19B	108.9
O3—C8—C3	119.93 (19)	H19A—C19—H19B	107.7
O4—C8—C3	116.46 (18)	C21—C20—C19	115.1 (2)
N1—C9—N2	109.52 (18)	C21—C20—H20A	108.5
N1—C9—C12	125.47 (19)	C19—C20—H20A	108.5
N2—C9—C12	124.99 (19)	C21—C20—H20B	108.5
C11—C10—N1	109.3 (2)	C19—C20—H20B	108.5
C11—C10—H10	125.4	H20A—C20—H20B	107.5
N1—C10—H10	125.4	C20—C21—C22	113.4 (2)
C10—C11—N2	106.9 (2)	C20—C21—H21A	108.9
C10—C11—H11	126.5	C22—C21—H21A	108.9
N2—C11—H11	126.5	C20—C21—H21B	108.9
C9—C12—C13	116.1 (2)	C22—C21—H21B	108.9
C9—C12—H12A	108.3	H21A—C21—H21B	107.7
C13—C12—H12A	108.3	N3—C22—C21	111.8 (2)
C9—C12—H12B	108.3	N3—C22—H22A	109.3
C13—C12—H12B	108.3	C21—C22—H22A	109.3
H12A—C12—H12B	107.4	N3—C22—H22B	109.3
C12—C13—H13A	109.5	C21—C22—H22B	109.3
C12—C13—H13B	109.5	H22A—C22—H22B	107.9
H13A—C13—H13B	109.5	C9—N1—C10	106.52 (17)
C12—C13—H13C	109.5	C9—N1—Zn1	132.81 (14)
H13A—C13—H13C	109.5	C10—N1—Zn1	120.54 (14)
H13B—C13—H13C	109.5	C9—N2—C11	107.76 (18)
C15—C14—N3	107.1 (2)	C9—N2—C19	127.13 (19)
C15—C14—H14	126.4	C11—N2—C19	125.11 (19)
N3—C14—H14	126.4	C16—N3—C14	106.8 (2)
C14—C15—N4	109.7 (2)	C16—N3—C22	129.2 (2)
C14—C15—H15	125.1	C14—N3—C22	124.1 (2)
N4—C15—H15	125.1	C16—N4—C15	105.6 (2)
N4—C16—N3	110.7 (2)	C16—N4—Zn1ⁱⁱⁱ	127.12 (15)
N4—C16—C17'	126.3 (9)	C15—N4—Zn1ⁱⁱⁱ	127.13 (17)
N3—C16—C17'	119.1 (9)	C7—O1—Zn1	117.32 (14)
N4—C16—C17	123.1 (4)	C8—O4—Zn1^iv	109.05 (13)
N3—C16—C17	126.0 (4)	C5—O5—H5	109.5
C18—C17—C16	111.6 (6)

C6—C1—C2—C3	−1.4 (3)	O1—Zn1—N1—C9	−91.05 (19)
C7—C1—C2—C3	178.03 (18)	O4ⁱ—Zn1—N1—C9	160.56 (18)
C1—C2—C3—C4	1.9 (3)	N4ⁱⁱ—Zn1—N1—C9	38.8 (2)
C1—C2—C3—C8	−178.86 (19)	O1—Zn1—N1—C10	93.79 (16)
C2—C3—C4—C5	−0.7 (3)	O4ⁱ—Zn1—N1—C10	−14.60 (17)
C8—C3—C4—C5	−179.88 (18)	N4ⁱⁱ—Zn1—N1—C10	−136.36 (16)
C3—C4—C5—O5	−178.50 (19)	N1—C9—N2—C11	−0.5 (2)
C3—C4—C5—C6	−1.0 (3)	C12—C9—N2—C11	178.1 (2)
O5—C5—C6—C1	179.13 (18)	N1—C9—N2—C19	179.53 (19)
C4—C5—C6—C1	1.5 (3)	C12—C9—N2—C19	−1.9 (3)
C2—C1—C6—C5	−0.3 (3)	C10—C11—N2—C9	0.7 (2)
C7—C1—C6—C5	−179.75 (19)	C10—C11—N2—C19	−179.3 (2)
C2—C1—C7—O2	28.3 (3)	C20—C19—N2—C9	−95.4 (3)
C6—C1—C7—O2	−152.2 (2)	C20—C19—N2—C11	84.6 (3)
C2—C1—C7—O1	−151.0 (2)	N4—C16—N3—C14	0.6 (3)
C6—C1—C7—O1	28.4 (3)	C17'—C16—N3—C14	−158.6 (11)
C2—C3—C8—O3	−2.7 (3)	C17—C16—N3—C14	176.4 (5)
C4—C3—C8—O3	176.5 (2)	N4—C16—N3—C22	−179.4 (2)
C2—C3—C8—O4	177.98 (19)	C17'—C16—N3—C22	21.4 (12)
C4—C3—C8—O4	−2.8 (3)	C17—C16—N3—C22	−3.7 (6)
N1—C10—C11—N2	−0.7 (3)	C15—C14—N3—C16	0.0 (3)
N1—C9—C12—C13	−104.2 (3)	C15—C14—N3—C22	180.0 (2)
N2—C9—C12—C13	77.4 (3)	C21—C22—N3—C16	105.4 (3)
N3—C14—C15—N4	−0.6 (4)	C21—C22—N3—C14	−74.7 (3)
N4—C16—C17—C18	−96.2 (6)	N3—C16—N4—C15	−1.0 (3)
N3—C16—C17—C18	88.6 (7)	C17'—C16—N4—C15	156.4 (12)
C17'—C16—C17—C18	10 (3)	C17—C16—N4—C15	−176.8 (5)
N4—C16—C17'—C18'	99.1 (17)	N3—C16—N4—Zn1ⁱⁱⁱ	−177.31 (14)
N3—C16—C17'—C18'	−105.3 (15)	C17'—C16—N4—Zn1ⁱⁱⁱ	−19.9 (12)
C17—C16—C17'—C18'	9.4 (19)	C17—C16—N4—Zn1ⁱⁱⁱ	6.8 (5)
N2—C19—C20—C21	−69.9 (3)	C14—C15—N4—C16	0.9 (3)
C19—C20—C21—C22	179.9 (2)	C14—C15—N4—Zn1ⁱⁱⁱ	177.28 (19)
C20—C21—C22—N3	−70.7 (3)	O2—C7—O1—Zn1	−5.3 (3)
N2—C9—N1—C10	0.1 (2)	C1—C7—O1—Zn1	173.94 (13)
C12—C9—N1—C10	−178.5 (2)	O4ⁱ—Zn1—O1—C7	168.10 (15)
N2—C9—N1—Zn1	−175.60 (14)	N4ⁱⁱ—Zn1—O1—C7	−60.73 (17)
C12—C9—N1—Zn1	5.8 (3)	N1—Zn1—O1—C7	62.23 (17)
C11—C10—N1—C9	0.4 (2)	O3—C8—O4—Zn1^iv	−10.2 (3)
C11—C10—N1—Zn1	176.70 (15)	C3—C8—O4—Zn1^iv	169.17 (14)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1^v	0.93	2.62	3.417 (3)	144
C14—H14···O5^v	0.93	2.49	3.398 (3)	166
O5—H5···O2^vi	0.82	1.88	2.697 (2)	171

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₄O₅)(C₁₄H₂₂N₄)]
M_r	491.84
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.5120 (12), 12.765 (1), 13.5910 (12)
β (°)	103.933 (2)
V (Å³)	2275.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.28 × 0.24 × 0.21

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.73, 0.79
No. of measured, independent and observed [I > 2σ(I)] reflections	13890, 5467, 3988
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.087, 1.03
No. of reflections	5467
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.29

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—O1	1.9662 (15)	Zn1—N4ⁱⁱ	2.0020 (18)
Zn1—O4ⁱ	1.9682 (14)	Zn1—N1	2.0286 (17)

O1—Zn1—O4ⁱ	102.54 (6)	O1—Zn1—N1	115.96 (7)
O1—Zn1—N4ⁱⁱ	117.20 (7)	O4ⁱ—Zn1—N1	98.33 (6)
O4ⁱ—Zn1—N4ⁱⁱ	118.18 (7)	N4ⁱⁱ—Zn1—N1	103.59 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱⁱⁱ	0.93	2.62	3.417 (3)	144
C14—H14···O5ⁱⁱⁱ	0.93	2.49	3.398 (3)	166
O5—H5···O2^iv	0.82	1.88	2.697 (2)	171

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

Acknowledgements

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

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kan, W.-Q., Liu, Y.-Y., Yang, J., Liu, Y.-Y. & Ma, J.-F. (2011). CrystEngComm, 13, 4256–4269. Web of Science CSD CrossRef CAS 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
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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