Tetra-μ-benzoato-bis­{[trans-1-(2-pyrid­yl)-2-(4-pyrid­yl)ethyl­ene]zinc(II)}

Song, Y.J.; Lee, S.-W.; Jang, K.H.; Kim, C.; Kim, Y.

doi:10.1107/S1600536809045048

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1495-m1496

doi:10.1107/S1600536809045048

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Tetra-μ-benzoato-bis{[trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene]zinc(II)}

Young Joo Song,^a Soo-Won Lee,^b Kyung Hwan Jang,^c Cheal Kim ^a ^* and Youngmee Kim ^d ^*

^aDepartment of Fine Chemistry, and Eco-Product and Materials Education Center, Seoul National University of Technology, Seoul 139-743, Republic of Korea, ^bForest Practice Research Center, Korea Forest Research Institute, Pocheon 487-821, Republic of Korea, ^cKorea Forest Research Institute 44-3, Suwon 441-350, Republic of Korea, and ^dDeaprtment of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea
^*Correspondence e-mail: chealkim@sunt.ac.kr, ymeekim@ewha.ac.kr

(Received 21 October 2009; accepted 28 October 2009; online 4 November 2009)

The paddle-wheel-type centrosymmetric dinuclear title complex, [Zn₂(C₇H₅O₂)₄(C₁₂H₁₀N₂)₂], contains four bridging benzoate groups and two terminal trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene (L) ligands. The inversion center is located between the two Zn^II atoms. The octahedral coordination around the Zn^II atom, with four O atoms in the equatorial plane, is completed by an N atom of the L molecule [Zn—N = 2.0198 (15) Å] and by the second Zn^II atom [Zn⋯Zn = 2.971 (8) Å]. The Zn^II atom is 0.372 Å out of the plane of the four coordinating O atoms.

Related literature

For structures containing [Zn₂(O₂CPh)₄], see: Necefoglu et al. (2002 ); Zeleňák et al. (2004 ); Karmakar et al. (2006 ); Ohmura et al. (2005 ). For the structures of copper(II) and zinc(II) benzoates with quinoxaline, 6-methylquinoline, 3-methylquinoline, and di-2-pyridyl ketone, see: Lee et al. (2008 ); Yu et al. (2008 , 2009 ); Park et al. (2008 ); Shin et al. (2009 ). For transition metal ions as the major cation contributors to the inorganic composition of natural water and biological fluids, see: Daniele et al. (2008 ); Parkin (2004 ); Tshuva & Lippard (2004 ).

Experimental

Crystal data

[Zn₂(C₇H₅O₂)₄(C₁₂H₁₀N₂)₂]
M_r = 979.66
Monoclinic, C 2/c
a = 24.919 (6) Å
b = 12.186 (3) Å
c = 15.742 (4) Å
β = 109.857 (4)°
V = 4496.0 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.816, T_max = 0.884
12326 measured reflections
4416 independent reflections
2947 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.090
S = 1.03
4416 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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 I, global. DOI: 10.1107/S1600536809045048/dn2505sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045048/dn2505Isup2.hkl

checkCIF report

Comment top

A great attention has been paid to transition metal ions as the major cation contributors to the inorganic composition of natural water and biological fluids (Daniele, et al., 2008; Parkin, 2004; Tshuva & Lippard, 2004). While the main attention was focused on the interaction of transition metal ions with biologically active molecules such as amino acids, proteins, sugars, nucleotides etc, the study on the interaction of the transition metal ions with fulvic acids and humic acids, mainly found in soil, is about to start. As models to examine the interaction, therefore, we have previously used copper(II) and zinc(II) benzoates as building blocks and reported the structures of copper(II) and zinc(II) benzoates with quinoxaline, 6-methylquinoline, 3-methylquinoline, and di-2-pyridyl ketone (Lee, et al., 2008; Yu, et al., 2008; Park, et al., 2008; Shin, et al., 2009; Yu, et al., 2009). The related paddle-wheel type structures for Zn complexes have been previouly reported (Necefoglu et al., 2002; Zeleňák, et al., 2004; Karmakar, et al., 2006; Ohmura, et al., 2005). In this work, we have employed zinc(II) benzoate as a building block and trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene as a ligand. We report hereon the structure of new zinc(II) benzoate with trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene.

Asymmetric unit contains half of whole molecule, and there is an inversion center in the middle of Zn···Zn bond. Symmetric operation (1-x, 1-y , 1-z) produces a paddle-wheel type dinuclear zinc-benzoate complex (Fig. 1). The paddle-wheel type dinuclear complex is constructed by four bridging benzoate groups and two terminal L ligands (L = trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene). The octahedral coordination around the zinc atom, with four O atoms in the equatorial plane, is completed by nitrogen atom of L molecule (Zn—N 2.0198 (15) Å) and by the second zinc atom (Zn···Zn 2.971 (8) Å). The zinc atom is 0.372 Å out of the plane of the four oxygen atoms.

Related literature top

For structures containing [Zn₂(O₂CPh)₄], see: Necefoglu et al. (2002); Zeleňák et al. (2004); Karmakar et al. (2006); Ohmura et al. (2005). For the structures of copper(II) and zinc(II) benzoates with quinoxaline, 6-methylquinoline, 3-methylquinoline, and di-2-pyridyl ketone, see: Lee et al. (2008); Yu et al. (2008, 2009); Park et al. (2008); Shin et al. (2009). For transition metal ions as the major cation contributors to the inorganic composition of natural water and biological fluids, see: Daniele et al. (2008); Parkin (2004); Tshuva & Lippard (2004);

Experimental top

30.4 mg (0.1 mmol) of Zn(NO₃)₂^.6H₂O and 28.0 mg (0.2 mmol) of C₆H₅COONH₄ were dissolved in 4 ml H₂O and carefully layered by 4 ml me thanol solution of trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene (37.6 mg, 0.2 mmol). Suitable crystals of the title compound for X-ray analysis were obtained in a few weeks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 the title compound showing the atom-labeling scheme. Displacement ellipsoids are shown at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) -x+1, -y+1, -z+1].

Tetra-µ-benzoato-bis{[trans-1-(2-pyridyl)-2-(4- pyridyl)ethylene]zinc(II)} top

Crystal data top

[Zn₂(C₇H₅O₂)₄(C₁₂H₁₀N₂)₂]	F(000) = 2016
M_r = 979.66	D_x = 1.447 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1818 reflections
a = 24.919 (6) Å	θ = 2.5–19.6°
b = 12.186 (3) Å	µ = 1.13 mm⁻¹
c = 15.742 (4) Å	T = 293 K
β = 109.857 (4)°	Block, colorless
V = 4496.0 (19) Å³	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4416 independent reflections
Radiation source: fine-focus sealed tube	2947 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −20→30
T_min = 0.816, T_max = 0.884	k = −15→15
12326 measured reflections	l = −19→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0205P)² + 1.48P] where P = (F_o² + 2F_c²)/3
4416 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Zn₂(C₇H₅O₂)₄(C₁₂H₁₀N₂)₂]	V = 4496.0 (19) Å³
M_r = 979.66	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 24.919 (6) Å	µ = 1.13 mm⁻¹
b = 12.186 (3) Å	T = 293 K
c = 15.742 (4) Å	0.20 × 0.15 × 0.15 mm
β = 109.857 (4)°

Data collection top

Bruker SMART CCD diffractometer	4416 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2947 reflections with I > 2σ(I)
T_min = 0.816, T_max = 0.884	R_int = 0.039
12326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
4416 reflections	Δρ_min = −0.27 e Å⁻³
298 parameters

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 > 2sigma(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	0.545232 (12)	0.50480 (2)	0.590326 (19)	0.03852 (11)
O11	0.48081 (8)	0.42174 (16)	0.61458 (13)	0.0536 (5)
O12	0.58816 (8)	0.58560 (17)	0.51974 (13)	0.0589 (5)
O21	0.56818 (8)	0.35925 (15)	0.54865 (13)	0.0549 (5)
O22	0.50102 (8)	0.64874 (15)	0.58505 (13)	0.0581 (6)
N31	0.60407 (9)	0.52228 (16)	0.71558 (14)	0.0391 (5)
N32	0.75201 (11)	0.7049 (2)	1.18938 (17)	0.0710 (8)
C11	0.43281 (12)	0.3906 (2)	0.56234 (19)	0.0420 (7)
C12	0.39861 (11)	0.3173 (2)	0.60095 (18)	0.0399 (6)
C13	0.41930 (13)	0.2875 (3)	0.6908 (2)	0.0584 (8)
H13	0.4539	0.3159	0.7282	0.070*
C14	0.38945 (18)	0.2165 (3)	0.7258 (3)	0.0805 (11)
H14	0.4041	0.1973	0.7865	0.097*
C15	0.33831 (18)	0.1736 (3)	0.6724 (3)	0.0803 (11)
H15	0.3184	0.1251	0.6963	0.096*
C16	0.31681 (14)	0.2032 (3)	0.5828 (3)	0.0747 (10)
H16	0.2821	0.1745	0.5459	0.090*
C17	0.34645 (12)	0.2755 (2)	0.5472 (2)	0.0563 (8)
H17	0.3312	0.2962	0.4869	0.068*
C21	0.53915 (12)	0.3100 (2)	0.47807 (19)	0.0423 (6)
C22	0.55306 (11)	0.1917 (2)	0.46933 (19)	0.0450 (7)
C23	0.51906 (15)	0.1303 (3)	0.3980 (3)	0.0773 (11)
H23	0.4894	0.1636	0.3525	0.093*
C24	0.5289 (2)	0.0196 (3)	0.3940 (4)	0.1091 (17)
H24	0.5051	−0.0218	0.3464	0.131*
C25	0.5726 (2)	−0.0295 (3)	0.4583 (4)	0.1087 (17)
H25	0.5786	−0.1044	0.4551	0.130*
C26	0.6079 (2)	0.0306 (3)	0.5279 (3)	0.0902 (13)
H26	0.6384	−0.0034	0.5714	0.108*
C27	0.59863 (14)	0.1418 (3)	0.5344 (2)	0.0628 (9)
H27	0.6228	0.1826	0.5820	0.075*
C31	0.65674 (12)	0.4837 (2)	0.73577 (19)	0.0531 (8)
H31	0.6658	0.4437	0.6922	0.064*
C32	0.69861 (12)	0.5004 (2)	0.81848 (19)	0.0568 (8)
H32	0.7351	0.4728	0.8292	0.068*
C33	0.68646 (11)	0.5579 (2)	0.88547 (17)	0.0412 (7)
C34	0.63111 (11)	0.5948 (2)	0.86490 (17)	0.0473 (7)
H34	0.6203	0.6323	0.9080	0.057*
C35	0.59211 (11)	0.5760 (2)	0.78060 (17)	0.0456 (7)
H35	0.5552	0.6024	0.7681	0.055*
C36	0.73130 (12)	0.5774 (2)	0.97322 (18)	0.0505 (7)
H36	0.7680	0.5540	0.9794	0.061*
C37	0.72419 (12)	0.6248 (2)	1.04352 (18)	0.0509 (8)
H37	0.6872	0.6455	1.0378	0.061*
C38	0.76886 (13)	0.6485 (2)	1.13035 (18)	0.0473 (7)
C39	0.82430 (14)	0.6161 (3)	1.1499 (2)	0.0647 (9)
H39	0.8352	0.5770	1.1077	0.078*
C310	0.86366 (15)	0.6418 (3)	1.2323 (2)	0.0819 (12)
H310	0.9014	0.6194	1.2467	0.098*
C311	0.84732 (15)	0.7006 (3)	1.2933 (2)	0.0639 (9)
H311	0.8735	0.7201	1.3491	0.077*
C312	0.79166 (16)	0.7295 (3)	1.2699 (2)	0.0722 (10)
H312	0.7802	0.7684	1.3116	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03822 (19)	0.04063 (17)	0.03006 (17)	−0.00220 (15)	0.00295 (12)	−0.00148 (14)
O11	0.0470 (12)	0.0593 (12)	0.0528 (12)	−0.0127 (10)	0.0146 (10)	−0.0025 (10)
O12	0.0622 (13)	0.0699 (13)	0.0446 (12)	−0.0098 (11)	0.0180 (10)	0.0091 (11)
O21	0.0599 (13)	0.0486 (11)	0.0522 (13)	0.0073 (10)	0.0140 (10)	−0.0082 (10)
O22	0.0580 (13)	0.0474 (11)	0.0584 (14)	0.0102 (10)	0.0063 (11)	0.0015 (10)
N31	0.0405 (13)	0.0400 (12)	0.0331 (12)	−0.0012 (10)	0.0078 (10)	−0.0030 (9)
N32	0.0614 (18)	0.105 (2)	0.0411 (15)	−0.0057 (16)	0.0108 (13)	−0.0143 (15)
C11	0.0491 (18)	0.0344 (14)	0.0460 (17)	0.0026 (13)	0.0207 (14)	−0.0019 (13)
C12	0.0426 (16)	0.0373 (14)	0.0431 (16)	0.0024 (12)	0.0190 (13)	−0.0015 (12)
C13	0.062 (2)	0.0643 (19)	0.052 (2)	−0.0050 (17)	0.0227 (16)	0.0023 (16)
C14	0.100 (3)	0.086 (3)	0.066 (2)	0.002 (2)	0.042 (2)	0.022 (2)
C15	0.094 (3)	0.057 (2)	0.111 (3)	−0.002 (2)	0.062 (3)	0.015 (2)
C16	0.056 (2)	0.069 (2)	0.102 (3)	−0.0149 (18)	0.031 (2)	−0.007 (2)
C17	0.0473 (19)	0.0579 (18)	0.062 (2)	−0.0040 (15)	0.0168 (16)	−0.0014 (16)
C21	0.0444 (17)	0.0416 (14)	0.0452 (17)	0.0015 (13)	0.0206 (14)	0.0010 (13)
C22	0.0479 (17)	0.0401 (14)	0.0545 (18)	0.0015 (13)	0.0270 (14)	−0.0016 (13)
C23	0.068 (2)	0.059 (2)	0.097 (3)	−0.0027 (18)	0.016 (2)	−0.0217 (19)
C24	0.103 (4)	0.063 (3)	0.163 (5)	−0.014 (2)	0.046 (3)	−0.050 (3)
C25	0.123 (4)	0.042 (2)	0.192 (6)	0.007 (2)	0.094 (4)	−0.003 (3)
C26	0.103 (3)	0.064 (2)	0.121 (4)	0.035 (2)	0.061 (3)	0.034 (2)
C27	0.071 (2)	0.061 (2)	0.062 (2)	0.0168 (17)	0.0303 (18)	0.0140 (16)
C31	0.0490 (18)	0.0643 (19)	0.0413 (16)	0.0072 (15)	0.0093 (13)	−0.0153 (14)
C32	0.0391 (16)	0.074 (2)	0.0488 (18)	0.0100 (16)	0.0043 (13)	−0.0124 (17)
C33	0.0440 (17)	0.0416 (15)	0.0331 (15)	−0.0033 (13)	0.0067 (12)	−0.0023 (12)
C34	0.0447 (17)	0.0595 (17)	0.0356 (15)	0.0031 (14)	0.0110 (13)	−0.0087 (13)
C35	0.0360 (16)	0.0582 (17)	0.0374 (16)	0.0044 (14)	0.0056 (12)	−0.0004 (14)
C36	0.0397 (17)	0.0608 (18)	0.0410 (17)	0.0010 (14)	0.0009 (13)	−0.0077 (14)
C37	0.0445 (18)	0.0638 (19)	0.0371 (16)	−0.0022 (14)	0.0045 (13)	−0.0036 (14)
C38	0.0547 (19)	0.0500 (16)	0.0324 (16)	−0.0109 (14)	0.0083 (14)	−0.0012 (13)
C39	0.059 (2)	0.077 (2)	0.0444 (18)	0.0088 (17)	0.0002 (16)	−0.0159 (16)
C310	0.062 (2)	0.099 (3)	0.062 (2)	0.005 (2)	−0.0074 (19)	−0.013 (2)
C311	0.071 (2)	0.069 (2)	0.0367 (18)	−0.0147 (19)	−0.0020 (16)	−0.0016 (16)
C312	0.079 (3)	0.096 (3)	0.0382 (18)	−0.009 (2)	0.0162 (17)	−0.0134 (18)

Geometric parameters (Å, º) top

Zn1—N31	2.029 (2)	C23—C24	1.376 (5)
Zn1—O12	2.039 (2)	C23—H23	0.9300
Zn1—O21	2.0392 (19)	C24—C25	1.349 (6)
Zn1—O11	2.0407 (19)	C24—H24	0.9300
Zn1—O22	2.0580 (19)	C25—C26	1.362 (6)
Zn1—Zn1ⁱ	2.9711 (8)	C25—H25	0.9300
O11—C11	1.258 (3)	C26—C27	1.385 (4)
O12—C11ⁱ	1.252 (3)	C26—H26	0.9300
O21—C21	1.254 (3)	C27—H27	0.9300
O22—C21ⁱ	1.251 (3)	C31—C32	1.379 (4)
N31—C31	1.327 (3)	C31—H31	0.9300
N31—C35	1.331 (3)	C32—C33	1.383 (4)
N32—C38	1.333 (4)	C32—H32	0.9300
N32—C312	1.350 (4)	C33—C34	1.381 (3)
C11—O12ⁱ	1.252 (3)	C33—C36	1.471 (3)
C11—C12	1.498 (4)	C34—C35	1.372 (3)
C12—C13	1.380 (4)	C34—H34	0.9300
C12—C17	1.385 (4)	C35—H35	0.9300
C13—C14	1.372 (4)	C36—C37	1.313 (4)
C13—H13	0.9300	C36—H36	0.9300
C14—C15	1.370 (5)	C37—C38	1.468 (3)
C14—H14	0.9300	C37—H37	0.9300
C15—C16	1.375 (5)	C38—C39	1.368 (4)
C15—H15	0.9300	C39—C310	1.371 (4)
C16—C17	1.385 (4)	C39—H39	0.9300
C16—H16	0.9300	C310—C311	1.366 (5)
C17—H17	0.9300	C310—H310	0.9300
C21—O22ⁱ	1.251 (3)	C311—C312	1.355 (4)
C21—C22	1.500 (4)	C311—H311	0.9300
C22—C23	1.375 (4)	C312—H312	0.9300
C22—C27	1.385 (4)

N31—Zn1—O12	98.00 (8)	C24—C23—H23	120.0
N31—Zn1—O21	102.41 (8)	C22—C23—H23	120.0
O12—Zn1—O21	89.34 (8)	C25—C24—C23	120.7 (4)
N31—Zn1—O11	103.00 (8)	C25—C24—H24	119.7
O12—Zn1—O11	158.97 (8)	C23—C24—H24	119.7
O21—Zn1—O11	87.31 (8)	C24—C25—C26	120.1 (4)
N31—Zn1—O22	98.62 (8)	C24—C25—H25	119.9
O12—Zn1—O22	86.52 (9)	C26—C25—H25	119.9
O21—Zn1—O22	158.93 (8)	C25—C26—C27	120.4 (4)
O11—Zn1—O22	89.19 (8)	C25—C26—H26	119.8
N31—Zn1—Zn1ⁱ	175.50 (6)	C27—C26—H26	119.8
O12—Zn1—Zn1ⁱ	82.26 (6)	C26—C27—C22	119.4 (3)
O21—Zn1—Zn1ⁱ	82.08 (6)	C26—C27—H27	120.3
O11—Zn1—Zn1ⁱ	76.71 (6)	C22—C27—H27	120.3
O22—Zn1—Zn1ⁱ	76.89 (5)	N31—C31—C32	122.9 (3)
C11—O11—Zn1	131.38 (19)	N31—C31—H31	118.5
C11ⁱ—O12—Zn1	124.19 (18)	C32—C31—H31	118.5
C21—O21—Zn1	124.11 (17)	C31—C32—C33	120.2 (3)
C21ⁱ—O22—Zn1	130.32 (18)	C31—C32—H32	119.9
C31—N31—C35	116.8 (2)	C33—C32—H32	119.9
C31—N31—Zn1	121.66 (18)	C34—C33—C32	116.5 (2)
C35—N31—Zn1	121.47 (18)	C34—C33—C36	123.2 (2)
C38—N32—C312	117.7 (3)	C32—C33—C36	120.3 (3)
O12ⁱ—C11—O11	125.1 (3)	C35—C34—C33	119.7 (3)
O12ⁱ—C11—C12	117.5 (2)	C35—C34—H34	120.1
O11—C11—C12	117.4 (3)	C33—C34—H34	120.1
C13—C12—C17	118.4 (3)	N31—C35—C34	123.8 (3)
C13—C12—C11	120.5 (2)	N31—C35—H35	118.1
C17—C12—C11	121.1 (3)	C34—C35—H35	118.1
C14—C13—C12	120.8 (3)	C37—C36—C33	125.9 (3)
C14—C13—H13	119.6	C37—C36—H36	117.1
C12—C13—H13	119.6	C33—C36—H36	117.1
C15—C14—C13	120.8 (3)	C36—C37—C38	126.5 (3)
C15—C14—H14	119.6	C36—C37—H37	116.8
C13—C14—H14	119.6	C38—C37—H37	116.8
C14—C15—C16	119.1 (3)	N32—C38—C39	121.7 (3)
C14—C15—H15	120.4	N32—C38—C37	115.6 (3)
C16—C15—H15	120.4	C39—C38—C37	122.8 (3)
C15—C16—C17	120.4 (3)	C38—C39—C310	119.3 (3)
C15—C16—H16	119.8	C38—C39—H39	120.3
C17—C16—H16	119.8	C310—C39—H39	120.3
C16—C17—C12	120.4 (3)	C311—C310—C39	119.8 (3)
C16—C17—H17	119.8	C311—C310—H310	120.1
C12—C17—H17	119.8	C39—C310—H310	120.1
O22ⁱ—C21—O21	125.2 (2)	C312—C311—C310	117.8 (3)
O22ⁱ—C21—C22	117.4 (2)	C312—C311—H311	121.1
O21—C21—C22	117.3 (2)	C310—C311—H311	121.1
C23—C22—C27	119.2 (3)	N32—C312—C311	123.6 (3)
C23—C22—C21	120.0 (3)	N32—C312—H312	118.2
C27—C22—C21	120.8 (3)	C311—C312—H312	118.2
C24—C23—C22	120.1 (4)

O12ⁱ—C11—C12—C13	179.8 (3)	C21—C22—C27—C26	175.3 (3)
O11—C11—C12—C13	1.0 (4)	C35—N31—C31—C32	−2.1 (4)
O12ⁱ—C11—C12—C17	1.5 (4)	N31—C31—C32—C33	1.1 (5)
O11—C11—C12—C17	−177.2 (3)	C31—C32—C33—C34	0.9 (4)
C17—C12—C13—C14	1.3 (5)	C31—C32—C33—C36	−178.9 (3)
C11—C12—C13—C14	−177.0 (3)	C32—C33—C34—C35	−1.7 (4)
C12—C13—C14—C15	−0.1 (5)	C36—C33—C34—C35	178.1 (3)
C13—C14—C15—C16	−0.5 (6)	C31—N31—C35—C34	1.3 (4)
C14—C15—C16—C17	−0.1 (6)	C33—C34—C35—N31	0.7 (4)
C15—C16—C17—C12	1.2 (5)	C34—C33—C36—C37	4.5 (5)
C13—C12—C17—C16	−1.8 (4)	C32—C33—C36—C37	−175.6 (3)
C11—C12—C17—C16	176.5 (3)	C33—C36—C37—C38	−177.6 (3)
O22ⁱ—C21—C22—C23	−5.7 (4)	C312—N32—C38—C39	0.0 (5)
O21—C21—C22—C23	173.3 (3)	C312—N32—C38—C37	−179.4 (3)
O22ⁱ—C21—C22—C27	176.9 (3)	C36—C37—C38—N32	175.1 (3)
O21—C21—C22—C27	−4.1 (4)	C36—C37—C38—C39	−4.4 (5)
C27—C22—C23—C24	2.9 (6)	N32—C38—C39—C310	0.2 (5)
C21—C22—C23—C24	−174.5 (4)	C37—C38—C39—C310	179.6 (3)
C22—C23—C24—C25	−1.6 (7)	C38—C39—C310—C311	−0.9 (5)
C23—C24—C25—C26	−0.5 (8)	C39—C310—C311—C312	1.3 (5)
C24—C25—C26—C27	1.4 (7)	C38—N32—C312—C311	0.4 (5)
C25—C26—C27—C22	0.0 (6)	C310—C311—C312—N32	−1.1 (5)
C23—C22—C27—C26	−2.1 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₇H₅O₂)₄(C₁₂H₁₀N₂)₂]
M_r	979.66
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	24.919 (6), 12.186 (3), 15.742 (4)
β (°)	109.857 (4)
V (Å³)	4496.0 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.816, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	12326, 4416, 2947
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.090, 1.03
No. of reflections	4416
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.27

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

Financial support from the Korean Ministry of the Environment "ET-Human resource development Project" and the Cooperative Research Program for Agricultural Science & Technology Development (20070301–036-019–02) is gratefully acknowledged.

References

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