Tetra­kis(μ-4-methyl­benzoato-κ2O:O′)bis­[(N,N-diethyl­nicotinamide-κN1)zinc(II)]

Necefoğlu, H.; Çimen, E.; Tercan, B.; Dal, H.; Hökelek, T.

doi:10.1107/S1600536810011517

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m485-m486

doi:10.1107/S1600536810011517

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Tetrakis(μ-4-methylbenzoato-κ²O:O′)bis[(N,N-diethylnicotinamide-κN¹)zinc(II)]

Hacali Necefoğlu,^a Efdal Çimen,^a Barış Tercan,^b Hakan Dal ^c and Tuncer Hökelek ^d ^*

^aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, ^bDepartment of Physics, Karabük University, 78050 Karabük, Turkey, ^cDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey, and ^dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 24 March 2010; accepted 26 March 2010; online 31 March 2010)

In the centrosymmetric binuclear title complex, [Zn₂(C₈H₇O₂)₄(C₁₀H₁₄N₂O)₂], the Zn atoms [Zn⋯Zn′ = 2.9494 (3) Å] are bridged by four 4-methylbenzoate (PMB) anions. The four nearest O atoms around each Zn^II ion form a distorted square-planar arrangement, the octahedral coordination being completed by the pyridine N atom of the N,N-diethylnicotinamide (DENA) ligand. Each Zn^II ion is displaced by 0.3530 (1) Å from the plane of the four O atoms. The dihedral angles between carboxylate groups and their adjacent benzene rings are 5.88 (10) and 11.89 (9)°, while the benzene rings are oriented at a dihedral angle of 75.19 (4)°. The pyridine ring is oriented at dihedral angles of 38.28 (4) and 49.17 (4)° with respect to the benzene rings. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. π–π contacts between parallel benzene rings [centroid–centroid distance = 3.8388 (8) Å] and between parallel pyridine rings [centroid–centroid distance = 3.4855 (7) Å] may further stabilize the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974 ) and for the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972 ). For related structures, see: Hökelek et al. (1995 ); Hökelek et al. (2009a ,b ,c ); Necefoğlu et al. (2010 ); Speier & Fulop (1989 ); Usubaliev et al. (1980 ).

Experimental

Crystal data

[Zn₂(C₈H₇O₂)₄(C₁₀H₁₄N₂O)₂]
M_r = 1027.82
Triclinic, $[P \overline 1]$
a = 9.8603 (2) Å
b = 10.5272 (2) Å
c = 12.3514 (3) Å
α = 97.346 (3)°
β = 93.525 (3)°
γ = 106.342 (5)°
V = 1213.78 (6) Å³
Z = 1
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 100 K
0.45 × 0.35 × 0.34 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.649, T_max = 0.698
22051 measured reflections
6067 independent reflections
5604 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.065
S = 1.06
6067 reflections
311 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1ⁱ	2.0420 (9)
Zn1—O2	2.0264 (9)
Zn1—O3ⁱ	2.1196 (9)
Zn1—O4	2.0235 (9)
Zn1—N1	2.0340 (10)
Symmetry code: (i) -x+1, -y, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O4ⁱⁱ	0.93	2.55	3.4601 (18)	166
C16—H16C⋯O4ⁱⁱⁱ	0.96	2.59	3.542 (2)	174
C19—H19⋯O2^iv	0.93	2.57	3.4013 (15)	149
Symmetry codes: (ii) x+1, y, z; (iii) -x+1, -y, -z+1; (iv) -x+1, -y+1, -z.

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011517/xu2740sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011517/xu2740Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The title compound is a binuclear compound, consisting of two DENA and four 4-methylbenzoate (PMB) ligands. The crystal structures of similar complexes of Cu²⁺ and Zn²⁺ ions, [Cu(C₆H₅COO)₂(C₅H₅N)]₂ (Usubaliev et al., 1980); [Cu(C₆H₅CO₂)₂(Py)]₂ (Speier & Fulop, 1989), [Cu₂(C₆H₅COO)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 1995), [Cu₂(C₈H₇O₂)₄(C₆H₆N₂O)₂] (Necefoğlu et al., 2010), [Zn₂(C₁₁H₁₄NO₂)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 2009a), [Zn₂(C₈H₈NO₂)₄(C₁₀H₁₄N₂O)₂].2H₂O (Hökelek et al., 2009b) and [Zn₂(C₉H₁₀NO₂)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 2009c) have also been reported. In these structures, the benzoate ion acts as a bidentate ligand.

The title dimeric complex, [Zn₂(PMB)₄(DENA)₂], has a centre of symmetry and two Zn^II ions are surrounded by four PMB groups and two DENA ligands (Fig. 1). The DENA ligands are coordinated to Zn^II ions through pyridine N atoms only. The PMB groups act as bridging ligands. The Zn···Zn' distance is 2.9494 (3) Å. The average Zn—O distance is 2.0529 (9) Å (Table 1), and four O atoms of the bridging PMB ligands around each Zn^II ion form a distorted square plane. The Zn^II ion lies 0.3530 (1) Å above the least-squares plane. The average O—Zn—O bond angle is 88.30 (4)°. A distorted square-pyramidal arrangement around each Zn^II ion is completed by the pyridine N atom of DENA ligand at 2.034 (1) Å (Table 1) from the Zn atom. The N1—Zn1···Zn1' angle is 156.05 (4)° and the dihedral angle between plane through atoms Zn1, O1, O2, C1, Zn1', O1', O2', C1' and the plane through Zn1, O3, O4, C9, Zn1', O3', O4' and C9' atoms is 88.08 (9)°. The dihedral angles between the planar carboxylate groups [(O1/O2/C1) and (O3/O4/C9)] and the adjacent benzene rings A (C2—C7) and B (C10—C15) are 5.88 (10) and 11.89 (9) °, respectively, while that between rings A and B is A/B = 75.19 (4)°. Ring C (N1/C17—C21) is oriented with respect to rings A and B at dihedral angles A/C = 38.28 (4) and B/C = 49.17 (4) °.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 2) link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the structure. The π–π contacts between the benzene rings and between the pyridine rings, Cg2—Cg2ⁱ and Cg3—Cg3ⁱⁱ, [symmetry codes: (i) 1 - x, -y, 1 - z; (ii) 1 - x, 1 - y, 2 - z, where Cg2 and Cg3 are centroids of the rings B (C10—C15) and C (N1/C17—C21)] may further stabilize the structure, with centroid-centroid distances of 3.8388 (8) and 3.4855 (7) Å, respectively.

Related literature top

For niacin, see: Krishnamachari (1974) and for the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek et al. (1995); Hökelek et al. (2009a,b,c); Necefoğlu et al. (2010); Speier & Fulop (1989); Usubaliev et al. (1980).

Experimental top

The title compound was prepared by the reaction of ZnSO₄.H₂O (0.90 g, 5 mmol) in H₂O (40 ml) and DENA (1.78 g, 10 mmol) in H₂O (10 ml) with sodium 4-methylbenzoate (1.58 g, 10 mmol) in H₂O (250 ml). The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving colourless single crystals.

Computing details top

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Primed atoms are generated by the symmetry operator:(') 1 - x, -y, -z.

Tetrakis(µ-4-methylbenzoato-κ²O:O')bis[(N,N- diethylnicotinamide-κN¹)zinc(II)] top

Crystal data top

[Zn₂(C₈H₇O₂)₄(C₁₀H₁₄N₂O)₂]	Z = 1
M_r = 1027.82	F(000) = 536
Triclinic, P1	D_x = 1.406 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8603 (2) Å	Cell parameters from 9897 reflections
b = 10.5272 (2) Å	θ = 2.4–28.4°
c = 12.3514 (3) Å	µ = 1.05 mm⁻¹
α = 97.346 (3)°	T = 100 K
β = 93.525 (3)°	Block, colourless
γ = 106.342 (5)°	0.45 × 0.35 × 0.34 mm
V = 1213.78 (6) Å³

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	6067 independent reflections
Radiation source: fine-focus sealed tube	5604 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 28.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.649, T_max = 0.698	k = −14→14
22051 measured reflections	l = −16→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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0311P)² + 0.5069P] where P = (F_o² + 2F_c²)/3
6067 reflections	(Δ/σ)_max < 0.001
311 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Zn₂(C₈H₇O₂)₄(C₁₀H₁₄N₂O)₂]	γ = 106.342 (5)°
M_r = 1027.82	V = 1213.78 (6) Å³
Triclinic, P1	Z = 1
a = 9.8603 (2) Å	Mo Kα radiation
b = 10.5272 (2) Å	µ = 1.05 mm⁻¹
c = 12.3514 (3) Å	T = 100 K
α = 97.346 (3)°	0.45 × 0.35 × 0.34 mm
β = 93.525 (3)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	6067 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5604 reflections with I > 2σ(I)
T_min = 0.649, T_max = 0.698	R_int = 0.024
22051 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.06	Δρ_max = 0.50 e Å⁻³
6067 reflections	Δρ_min = −0.25 e Å⁻³
311 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 > 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
Zn1	0.450815 (15)	0.115632 (13)	0.040631 (11)	0.01383 (5)
O1	0.73414 (10)	0.02215 (9)	0.02905 (8)	0.01896 (19)
O2	0.65938 (9)	0.19668 (9)	0.09519 (8)	0.01795 (18)
O3	0.49245 (10)	−0.10996 (10)	0.12229 (8)	0.0210 (2)
O4	0.41059 (10)	0.05856 (9)	0.18860 (8)	0.01957 (19)
O5	0.30214 (10)	0.44313 (10)	−0.27313 (8)	0.0239 (2)
N1	0.37721 (11)	0.27588 (10)	0.02830 (9)	0.0147 (2)
N2	0.08512 (11)	0.30568 (11)	−0.25343 (9)	0.0175 (2)
C1	0.75162 (13)	0.13428 (12)	0.08691 (10)	0.0154 (2)
C2	0.89284 (13)	0.19728 (12)	0.15322 (10)	0.0158 (2)
C3	0.92011 (14)	0.31934 (13)	0.22226 (11)	0.0184 (2)
H3	0.8532	0.3665	0.2228	0.022*
C4	1.04631 (14)	0.37058 (13)	0.29001 (12)	0.0212 (3)
H4	1.0628	0.4518	0.3359	0.025*
C5	1.14912 (14)	0.30273 (14)	0.29080 (11)	0.0205 (3)
C6	1.12308 (14)	0.18255 (14)	0.21929 (12)	0.0210 (3)
H6	1.1913	0.1369	0.2171	0.025*
C7	0.99677 (14)	0.13047 (13)	0.15144 (11)	0.0193 (3)
H7	0.9812	0.0503	0.1043	0.023*
C8	1.28449 (15)	0.35768 (16)	0.36690 (13)	0.0282 (3)
H8A	1.3353	0.2920	0.3650	0.042*
H8B	1.2620	0.3787	0.4403	0.042*
H8C	1.3424	0.4373	0.3439	0.042*
C9	0.44426 (13)	−0.04751 (13)	0.19693 (10)	0.0165 (2)
C10	0.42490 (13)	−0.10307 (12)	0.30249 (10)	0.0162 (2)
C11	0.34787 (14)	−0.05492 (13)	0.38074 (11)	0.0189 (2)
H11	0.3120	0.0156	0.3692	0.023*
C12	0.32480 (14)	−0.11202 (15)	0.47572 (11)	0.0224 (3)
H12	0.2727	−0.0796	0.5270	0.027*
C13	0.37825 (15)	−0.21695 (14)	0.49557 (11)	0.0235 (3)
C14	0.45906 (15)	−0.26154 (14)	0.41892 (11)	0.0219 (3)
H14	0.4984	−0.3294	0.4320	0.026*
C15	0.48161 (14)	−0.20583 (13)	0.32319 (11)	0.0189 (2)
H15	0.5350	−0.2373	0.2725	0.023*
C16	0.34955 (19)	−0.28015 (19)	0.59785 (13)	0.0360 (4)
H16A	0.3701	−0.3646	0.5892	0.054*
H16B	0.2515	−0.2941	0.6100	0.054*
H16C	0.4088	−0.2220	0.6596	0.054*
C17	0.40194 (13)	0.38549 (13)	0.10388 (10)	0.0160 (2)
H17	0.4491	0.3876	0.1719	0.019*
C18	0.35931 (13)	0.49579 (13)	0.08359 (11)	0.0181 (2)
H18	0.3738	0.5689	0.1384	0.022*
C19	0.29485 (13)	0.49579 (12)	−0.01931 (11)	0.0173 (2)
H19	0.2696	0.5704	−0.0357	0.021*
C20	0.26868 (12)	0.38185 (12)	−0.09764 (10)	0.0152 (2)
C21	0.30915 (13)	0.27380 (12)	−0.06968 (10)	0.0151 (2)
H21	0.2883	0.1964	−0.1209	0.018*
C22	0.21826 (13)	0.37980 (12)	−0.21572 (11)	0.0162 (2)
C23	−0.01970 (14)	0.23617 (13)	−0.18488 (11)	0.0199 (3)
H23A	0.0297	0.2137	−0.1231	0.024*
H23B	−0.0793	0.1532	−0.2275	0.024*
C24	−0.11255 (15)	0.32037 (15)	−0.14258 (13)	0.0270 (3)
H24A	−0.1828	0.2694	−0.1020	0.041*
H24B	−0.1588	0.3458	−0.2034	0.041*
H24C	−0.0549	0.3993	−0.0955	0.041*
C25	0.03872 (15)	0.29558 (14)	−0.37030 (11)	0.0218 (3)
H25A	0.0906	0.3760	−0.3974	0.026*
H25B	−0.0615	0.2891	−0.3790	0.026*
C26	0.06320 (19)	0.17447 (16)	−0.43724 (13)	0.0321 (3)
H26A	0.0298	0.1694	−0.5128	0.048*
H26B	0.0124	0.0948	−0.4102	0.048*
H26C	0.1629	0.1824	−0.4311	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01471 (8)	0.01387 (7)	0.01481 (8)	0.00699 (5)	0.00123 (5)	0.00289 (5)
O1	0.0180 (4)	0.0163 (4)	0.0221 (5)	0.0056 (3)	−0.0003 (4)	0.0008 (4)
O2	0.0162 (4)	0.0170 (4)	0.0215 (5)	0.0064 (3)	0.0004 (4)	0.0035 (3)
O3	0.0231 (5)	0.0281 (5)	0.0161 (4)	0.0131 (4)	0.0043 (4)	0.0052 (4)
O4	0.0229 (5)	0.0208 (4)	0.0177 (4)	0.0093 (4)	0.0027 (4)	0.0058 (4)
O5	0.0200 (5)	0.0275 (5)	0.0235 (5)	0.0030 (4)	0.0020 (4)	0.0110 (4)
N1	0.0133 (5)	0.0147 (5)	0.0172 (5)	0.0053 (4)	0.0026 (4)	0.0034 (4)
N2	0.0164 (5)	0.0186 (5)	0.0176 (5)	0.0053 (4)	0.0009 (4)	0.0031 (4)
C1	0.0160 (6)	0.0156 (5)	0.0155 (6)	0.0045 (4)	0.0029 (5)	0.0061 (4)
C2	0.0150 (5)	0.0159 (6)	0.0173 (6)	0.0045 (4)	0.0025 (5)	0.0047 (5)
C3	0.0180 (6)	0.0174 (6)	0.0215 (6)	0.0070 (5)	0.0038 (5)	0.0046 (5)
C4	0.0215 (6)	0.0177 (6)	0.0223 (6)	0.0038 (5)	0.0015 (5)	0.0002 (5)
C5	0.0167 (6)	0.0226 (6)	0.0211 (6)	0.0029 (5)	0.0010 (5)	0.0057 (5)
C6	0.0166 (6)	0.0239 (6)	0.0249 (7)	0.0087 (5)	0.0026 (5)	0.0051 (5)
C7	0.0180 (6)	0.0179 (6)	0.0225 (6)	0.0068 (5)	0.0022 (5)	0.0017 (5)
C8	0.0199 (7)	0.0332 (8)	0.0278 (7)	0.0037 (6)	−0.0026 (6)	0.0028 (6)
C9	0.0137 (5)	0.0203 (6)	0.0154 (6)	0.0046 (5)	0.0005 (4)	0.0030 (5)
C10	0.0156 (5)	0.0178 (6)	0.0137 (6)	0.0026 (4)	0.0000 (4)	0.0026 (4)
C11	0.0160 (6)	0.0216 (6)	0.0179 (6)	0.0044 (5)	0.0007 (5)	0.0018 (5)
C12	0.0171 (6)	0.0306 (7)	0.0161 (6)	0.0020 (5)	0.0030 (5)	0.0021 (5)
C13	0.0208 (6)	0.0271 (7)	0.0172 (6)	−0.0027 (5)	−0.0018 (5)	0.0071 (5)
C14	0.0242 (7)	0.0197 (6)	0.0198 (6)	0.0031 (5)	−0.0038 (5)	0.0052 (5)
C15	0.0201 (6)	0.0187 (6)	0.0167 (6)	0.0048 (5)	0.0000 (5)	0.0016 (5)
C16	0.0350 (8)	0.0474 (10)	0.0245 (8)	0.0041 (7)	0.0042 (7)	0.0185 (7)
C17	0.0144 (5)	0.0188 (6)	0.0152 (6)	0.0056 (4)	0.0020 (4)	0.0020 (5)
C18	0.0178 (6)	0.0152 (6)	0.0211 (6)	0.0058 (5)	0.0041 (5)	−0.0012 (5)
C19	0.0165 (6)	0.0145 (5)	0.0233 (6)	0.0073 (4)	0.0048 (5)	0.0041 (5)
C20	0.0116 (5)	0.0162 (5)	0.0185 (6)	0.0045 (4)	0.0023 (4)	0.0043 (5)
C21	0.0142 (5)	0.0137 (5)	0.0173 (6)	0.0045 (4)	0.0011 (4)	0.0014 (4)
C22	0.0171 (6)	0.0135 (5)	0.0201 (6)	0.0078 (4)	0.0009 (5)	0.0031 (5)
C23	0.0152 (6)	0.0200 (6)	0.0231 (6)	0.0025 (5)	0.0012 (5)	0.0051 (5)
C24	0.0217 (7)	0.0266 (7)	0.0328 (8)	0.0061 (5)	0.0088 (6)	0.0040 (6)
C25	0.0214 (6)	0.0239 (6)	0.0184 (6)	0.0056 (5)	−0.0026 (5)	0.0019 (5)
C26	0.0409 (9)	0.0295 (8)	0.0242 (7)	0.0105 (7)	0.0035 (7)	−0.0026 (6)

Geometric parameters (Å, º) top

Zn1—Zn1ⁱ	2.9494 (3)	C10—C15	1.3934 (18)
Zn1—O1ⁱ	2.0420 (9)	C11—H11	0.9300
Zn1—O2	2.0264 (9)	C12—C11	1.3876 (19)
Zn1—O3ⁱ	2.1196 (9)	C12—C13	1.393 (2)
Zn1—O4	2.0235 (9)	C12—H12	0.9300
Zn1—N1	2.0340 (10)	C13—C14	1.393 (2)
O1—Zn1ⁱ	2.0420 (9)	C13—C16	1.507 (2)
O1—C1	1.2604 (15)	C14—C15	1.3884 (19)
O2—C1	1.2648 (15)	C14—H14	0.9300
O3—Zn1ⁱ	2.1196 (9)	C15—H15	0.9300
O3—C9	1.2580 (16)	C16—H16A	0.9600
O4—C9	1.2654 (16)	C16—H16B	0.9600
O5—C22	1.2305 (16)	C16—H16C	0.9600
N1—C17	1.3419 (16)	C17—C18	1.3871 (18)
N1—C21	1.3418 (16)	C17—H17	0.9300
N2—C22	1.3433 (16)	C18—H18	0.9300
N2—C23	1.4700 (17)	C19—C18	1.3857 (19)
N2—C25	1.4685 (17)	C19—H19	0.9300
C1—C2	1.5002 (17)	C20—C19	1.3927 (17)
C2—C7	1.3963 (18)	C20—C21	1.3824 (17)
C3—C2	1.3957 (18)	C20—C22	1.5071 (18)
C3—C4	1.3851 (19)	C21—H21	0.9300
C3—H3	0.9300	C23—C24	1.5146 (19)
C4—H4	0.9300	C23—H23A	0.9700
C5—C4	1.3950 (19)	C23—H23B	0.9700
C5—C6	1.3965 (19)	C24—H24A	0.9600
C5—C8	1.5073 (19)	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
C7—C6	1.3870 (19)	C25—C26	1.515 (2)
C7—H7	0.9300	C25—H25A	0.9700
C8—H8A	0.9600	C25—H25B	0.9700
C8—H8B	0.9600	C26—H26A	0.9600
C8—H8C	0.9600	C26—H26B	0.9600
C9—C10	1.4971 (18)	C26—H26C	0.9600
C10—C11	1.3963 (18)

O1ⁱ—Zn1—O3ⁱ	84.43 (4)	C13—C12—H12	119.4
O2—Zn1—O1ⁱ	159.97 (4)	C12—C13—C14	118.42 (13)
O2—Zn1—O3ⁱ	88.67 (4)	C12—C13—C16	120.61 (14)
O2—Zn1—N1	104.57 (4)	C14—C13—C16	120.97 (14)
O4—Zn1—O1ⁱ	89.88 (4)	C13—C14—H14	119.6
O4—Zn1—O2	90.22 (4)	C15—C14—C13	120.78 (13)
O4—Zn1—O3ⁱ	159.93 (4)	C15—C14—H14	119.6
O4—Zn1—N1	107.92 (4)	C10—C15—H15	119.7
N1—Zn1—O1ⁱ	94.43 (4)	C14—C15—C10	120.52 (13)
N1—Zn1—O3ⁱ	91.72 (4)	C14—C15—H15	119.7
C1—O1—Zn1ⁱ	128.83 (8)	C13—C16—H16A	109.5
C1—O2—Zn1	124.35 (8)	C13—C16—H16B	109.5
C9—O3—Zn1ⁱ	145.07 (9)	C13—C16—H16C	109.5
C9—O4—Zn1	110.41 (8)	H16A—C16—H16B	109.5
C17—N1—Zn1	126.21 (9)	H16A—C16—H16C	109.5
C21—N1—Zn1	114.90 (8)	H16B—C16—H16C	109.5
C21—N1—C17	118.59 (11)	N1—C17—C18	122.00 (12)
C22—N2—C23	124.41 (11)	N1—C17—H17	119.0
C22—N2—C25	118.33 (11)	C18—C17—H17	119.0
C25—N2—C23	117.24 (11)	C17—C18—H18	120.4
O1—C1—O2	125.48 (12)	C19—C18—C17	119.26 (12)
O1—C1—C2	117.03 (11)	C19—C18—H18	120.4
O2—C1—C2	117.47 (11)	C18—C19—C20	118.68 (12)
C3—C2—C1	120.98 (11)	C18—C19—H19	120.7
C3—C2—C7	118.75 (12)	C20—C19—H19	120.7
C7—C2—C1	120.17 (11)	C19—C20—C22	122.14 (11)
C2—C3—H3	119.9	C21—C20—C19	118.57 (12)
C4—C3—C2	120.29 (12)	C21—C20—C22	118.65 (11)
C4—C3—H3	119.9	N1—C21—C20	122.78 (11)
C3—C4—C5	121.29 (12)	N1—C21—H21	118.6
C3—C4—H4	119.4	C20—C21—H21	118.6
C5—C4—H4	119.4	O5—C22—N2	123.51 (12)
C4—C5—C6	118.19 (12)	O5—C22—C20	118.39 (11)
C4—C5—C8	120.84 (13)	N2—C22—C20	118.08 (11)
C6—C5—C8	120.97 (13)	N2—C23—C24	112.25 (11)
C5—C6—H6	119.6	N2—C23—H23A	109.2
C7—C6—C5	120.82 (12)	N2—C23—H23B	109.2
C7—C6—H6	119.6	C24—C23—H23A	109.2
C2—C7—H7	119.7	C24—C23—H23B	109.2
C6—C7—C2	120.62 (12)	H23A—C23—H23B	107.9
C6—C7—H7	119.7	C23—C24—H24A	109.5
C5—C8—H8A	109.5	C23—C24—H24B	109.5
C5—C8—H8B	109.5	C23—C24—H24C	109.5
C5—C8—H8C	109.5	H24A—C24—H24B	109.5
H8A—C8—H8B	109.5	H24A—C24—H24C	109.5
H8A—C8—H8C	109.5	H24B—C24—H24C	109.5
H8B—C8—H8C	109.5	N2—C25—C26	111.44 (12)
O3—C9—O4	124.45 (12)	N2—C25—H25A	109.3
O3—C9—C10	117.63 (11)	N2—C25—H25B	109.3
O4—C9—C10	117.92 (11)	C26—C25—H25A	109.3
C11—C10—C9	120.82 (12)	C26—C25—H25B	109.3
C15—C10—C9	120.25 (12)	H25A—C25—H25B	108.0
C15—C10—C11	118.92 (12)	C25—C26—H26A	109.5
C10—C11—H11	119.9	C25—C26—H26B	109.5
C12—C11—C10	120.13 (13)	C25—C26—H26C	109.5
C12—C11—H11	119.9	H26A—C26—H26B	109.5
C11—C12—C13	121.17 (13)	H26A—C26—H26C	109.5
C11—C12—H12	119.4	H26B—C26—H26C	109.5

O1ⁱ—Zn1—O2—C1	0.43 (18)	O1—C1—C2—C7	−1.65 (18)
O3ⁱ—Zn1—O2—C1	−69.26 (10)	O2—C1—C2—C3	0.75 (18)
O4—Zn1—O2—C1	90.70 (10)	O2—C1—C2—C7	177.09 (12)
N1—Zn1—O2—C1	−160.69 (10)	C1—C2—C7—C6	−174.62 (12)
O1ⁱ—Zn1—O4—C9	80.22 (9)	C3—C2—C7—C6	1.8 (2)
O2—Zn1—O4—C9	−79.75 (9)	C4—C3—C2—C1	174.42 (12)
O3ⁱ—Zn1—O4—C9	6.98 (16)	C4—C3—C2—C7	−2.0 (2)
N1—Zn1—O4—C9	174.84 (8)	C2—C3—C4—C5	0.3 (2)
O1ⁱ—Zn1—N1—C17	139.95 (10)	C6—C5—C4—C3	1.5 (2)
O1ⁱ—Zn1—N1—C21	−46.58 (9)	C8—C5—C4—C3	−178.45 (13)
O2—Zn1—N1—C17	−46.43 (11)	C4—C5—C6—C7	−1.6 (2)
O2—Zn1—N1—C21	127.04 (9)	C8—C5—C6—C7	178.28 (13)
O3ⁱ—Zn1—N1—C17	−135.50 (10)	C2—C7—C6—C5	0.0 (2)
O3ⁱ—Zn1—N1—C21	37.97 (9)	O3—C9—C10—C11	−167.82 (12)
O4—Zn1—N1—C17	48.64 (11)	O3—C9—C10—C15	10.99 (18)
O4—Zn1—N1—C21	−137.89 (8)	O4—C9—C10—C11	11.89 (18)
Zn1ⁱ—O1—C1—O2	−15.50 (19)	O4—C9—C10—C15	−169.31 (12)
Zn1ⁱ—O1—C1—C2	163.13 (8)	C9—C10—C11—C12	176.76 (11)
Zn1—O2—C1—O1	12.25 (18)	C15—C10—C11—C12	−2.06 (19)
Zn1—O2—C1—C2	−166.37 (8)	C9—C10—C15—C14	−177.34 (12)
Zn1ⁱ—O3—C9—O4	−1.2 (2)	C11—C10—C15—C14	1.49 (19)
Zn1ⁱ—O3—C9—C10	178.47 (10)	C13—C12—C11—C10	0.5 (2)
Zn1—O4—C9—O3	−1.70 (16)	C11—C12—C13—C14	1.6 (2)
Zn1—O4—C9—C10	178.62 (8)	C11—C12—C13—C16	−178.59 (13)
Zn1—N1—C17—C18	173.27 (9)	C12—C13—C14—C15	−2.2 (2)
C21—N1—C17—C18	0.02 (18)	C16—C13—C14—C15	178.01 (13)
Zn1—N1—C21—C20	−171.23 (9)	C13—C14—C15—C10	0.7 (2)
C17—N1—C21—C20	2.77 (18)	N1—C17—C18—C19	−2.94 (19)
C23—N2—C22—O5	−175.96 (12)	C20—C19—C18—C17	3.09 (19)
C23—N2—C22—C20	5.98 (18)	C21—C20—C19—C18	−0.49 (18)
C25—N2—C22—O5	2.33 (19)	C22—C20—C19—C18	−171.23 (11)
C25—N2—C22—C20	−175.72 (11)	C19—C20—C22—O5	70.73 (16)
C22—N2—C23—C24	92.91 (15)	C19—C20—C22—N2	−111.12 (14)
C25—N2—C23—C24	−85.40 (14)	C21—C20—C22—O5	−100.01 (14)
C22—N2—C25—C26	92.54 (15)	C21—C20—C22—N2	78.14 (15)
C23—N2—C25—C26	−89.04 (15)	C19—C20—C21—N1	−2.52 (18)
O1—C1—C2—C3	−178.00 (12)	C22—C20—C21—N1	168.55 (11)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4ⁱⁱ	0.93	2.55	3.4601 (18)	166
C16—H16C···O4ⁱⁱⁱ	0.96	2.59	3.542 (2)	174
C19—H19···O2^iv	0.93	2.57	3.4013 (15)	149

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

Experimental details

Crystal data
Chemical formula	[Zn₂(C₈H₇O₂)₄(C₁₀H₁₄N₂O)₂]
M_r	1027.82
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.8603 (2), 10.5272 (2), 12.3514 (3)
α, β, γ (°)	97.346 (3), 93.525 (3), 106.342 (5)
V (Å³)	1213.78 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.45 × 0.35 × 0.34

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.649, 0.698
No. of measured, independent and observed [I > 2σ(I)] reflections	22051, 6067, 5604
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.065, 1.06
No. of reflections	6067
No. of parameters	311
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Zn1—O1ⁱ	2.0420 (9)	Zn1—O4	2.0235 (9)
Zn1—O2	2.0264 (9)	Zn1—N1	2.0340 (10)
Zn1—O3ⁱ	2.1196 (9)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4ⁱⁱ	0.93	2.55	3.4601 (18)	166.00
C16—H16C···O4ⁱⁱⁱ	0.96	2.59	3.542 (2)	174.00
C19—H19···O2^iv	0.93	2.57	3.4013 (15)	149.00

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

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of X-ray diffractometer. This work was supported financially by the Scientific and Technological Research Council of Turkey (grant No. 108 T657).

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