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

Hökelek, T.; Dal, H.; Tercan, B.; Aybirdi, Ö.; Necefoğlu, H.

doi:10.1107/S1600536809047473

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1582-m1583

doi:10.1107/S1600536809047473

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

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

^aDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, ^bDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey, ^cDepartment of Physics, Karabük University, 78050 Karabük, Turkey, and ^dDepartment of Chemistry, Kafkas University, 63100 Kars, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 5 November 2009; accepted 10 November 2009; online 14 November 2009)

The title molecule, [Zn₂(C₉H₁₀NO₂)₄(C₁₀H₁₄N₂O)₂], is a centrosymmetric binuclear complex, with Zn atoms [Zn⋯Zn′ = 2.8927 (4) Å] bridged by four carboxylate groups from the dimethylaminobenzoate (DMAB) ligands. The four carboxyl O atoms around the Zn atom form a distorted square-planar arrangement; the distorted square-pyramidal coordination geometry is completed by the pyridine N atom of the N,N-diethylnicotinamide (DENA) ligand. The Zn atom is displaced by 0.3326 (2) Å from the plane of the four O atoms, with an average Zn—O distance of 2.0416 (12) Å. The dihedral angles between the carboxylate groups and the adjacent benzene rings are 5.31 (8) and 11.00 (9)°, while the pyridine ring is oriented at dihedral angles of 66.26 (6) and 37.88 (7)° with respect to the benzene rings. Weak intramolecular C—H⋯O and intermolecular C—H⋯π interactions are present.

Related literature

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

Experimental

Crystal data

[Zn₂(C₉H₁₀NO₂)₄(C₁₀H₁₄N₂O)₂]
M_r = 1143.96
Triclinic, $[P \overline 1]$
a = 9.2731 (6) Å
b = 13.2340 (8) Å
c = 13.4756 (8) Å
α = 112.348 (3)°
β = 109.236 (2)°
γ = 95.728 (2)°
V = 1395.33 (16) Å³
Z = 1
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 294 K
0.52 × 0.35 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.681, T_max = 0.791
24970 measured reflections
6877 independent reflections
5749 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.090
S = 1.06
6877 reflections
349 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.0265 (12)
Zn1—O2	2.0269 (12)
Zn1—O4	2.0669 (12)
Zn1—O5	2.0459 (12)
Zn1—N3	2.0446 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O5	0.93	2.54	3.122 (2)	121
C8—H8A⋯Cg3ⁱ	0.96	2.77	3.629 (3)	150
Symmetry code: (i) -x+1, -y, -z+1. Cg3 is the centroid of the N3/C19–C23 ring.

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/S1600536809047473/xu2669sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047473/xu2669Isup2.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 dimethylaminobenzoate (DMAB) 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), [Zn₂(C₁₁H₁₄NO₂)₄(C₁₀H₁₄N₂O)₂] (Hökelek et al., 2009a) and [Zn₂(C₈H₈NO₂)₄(C₁₀H₁₄N₂O)₂].2H₂O (Hökelek et al., 2009b) have also been determined. In these structures, the benzoate ion acts as a bidentate ligand.

The title dimeric complex, [Zn₂(DMAB)₄(DENA)₂], has a centre of symmetry and two Zn^II atoms surrounded by four DMAB groups and two DENA ligands (Fig. 1). The DENA ligands are coordinated to Zn atoms through pyridine N atoms only. The DMAB groups act as bridging ligands. The Zn···Zn' distance is 2.8927 (4) Å. The average Zn—O distance is 2.0416 (12) Å (Table 1), and four O atoms of the bridging DMAB ligands around each Zn atom form a distorted square plane. The Zn atom lies 0.3326 (2) Å below the least-squares plane. The average O—Zn—O bond angle is 88.48 (6)°. A distorted square-pyramidal arrangement around each Zn atom is completed by the pyridine N atom of DENA ligand at 2.0446 (13) Å from the Zn atom. The N3—Zn1···Zn1' angle is 163.64 (6)° and the dihedral angle between plane through Zn1, O1, O4, C1, Zn1', O1', O4', C1' and the plane through Zn1, O2, O5, C10, Zn1', O2', O5', C10' is 89.47 (7)°. The dihedral angles between the planar carboxylate groups and the adjacent benzene rings A (C2—C7) and B (C11—C16) are 5.31 (8)° and 11.00 (9)°, respectively, while that between rings A and B is A/B = 83.70 (6)°. Ring C (N3/C19—C23) is oriented with respect to rings A and B at dihedral angles A/C = 66.26 (6) and B/C = 37.88 (7) °.

Weak intramolecular C—H···O and C—H···π interactions (Table 2) are present, in which they may be effective in the stabilization of the structure.

Related literature top

For general background to niacin and the nicotinic acid derivative N,N-diethylnicotinamide (DENA), see: Bigoli et al. (1972); Krishnamachari (1974). For related structures, see: Hökelek et al. (1995, 2009a,b); Speier & Fulop (1989); Usubaliev et al. (1980). Cg3 is the centroid of the N3/C19–C23 ring.

Experimental top

The title compound was prepared by the reaction of ZnSO₄.H₂O (0.9 g, 5 mmol) in H₂O (50 ml) and DENA (1.78 g, 10 mmol) in H₂O (50 ml) with sodium p-dimethylaminobenzoate (1.88 g, 10 mmol) in H₂O (100 ml). The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving colorless 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 15% probability level. Primed atoms are generated by the symmetry operator:(') 1-x, 1-y, 1-z.

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

Crystal data top

[Zn₂(C₉H₁₀NO₂)₄(C₁₀H₁₄N₂O)₂]	Z = 1
M_r = 1143.96	F(000) = 600
Triclinic, P1	D_x = 1.361 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2731 (6) Å	Cell parameters from 9870 reflections
b = 13.2340 (8) Å	θ = 2.4–28.3°
c = 13.4756 (8) Å	µ = 0.92 mm⁻¹
α = 112.348 (3)°	T = 294 K
β = 109.236 (2)°	Block, colorless
γ = 95.728 (2)°	0.52 × 0.35 × 0.25 mm
V = 1395.33 (16) Å³

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	6877 independent reflections
Radiation source: fine-focus sealed tube	5749 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.681, T_max = 0.791	k = −16→17
24970 measured reflections	l = −17→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0476P)² + 0.2013P] where P = (F_o² + 2F_c²)/3
6877 reflections	(Δ/σ)_max = 0.001
349 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Zn₂(C₉H₁₀NO₂)₄(C₁₀H₁₄N₂O)₂]	γ = 95.728 (2)°
M_r = 1143.96	V = 1395.33 (16) Å³
Triclinic, P1	Z = 1
a = 9.2731 (6) Å	Mo Kα radiation
b = 13.2340 (8) Å	µ = 0.92 mm⁻¹
c = 13.4756 (8) Å	T = 294 K
α = 112.348 (3)°	0.52 × 0.35 × 0.25 mm
β = 109.236 (2)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	6877 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5749 reflections with I > 2σ(I)
T_min = 0.681, T_max = 0.791	R_int = 0.029
24970 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.06	Δρ_max = 0.24 e Å⁻³
6877 reflections	Δρ_min = −0.43 e Å⁻³
349 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
Zn1	0.647429 (19)	0.587023 (15)	0.565621 (14)	0.03318 (7)
N1	0.0447 (2)	0.97057 (18)	0.3697 (2)	0.0740 (6)
N2	0.3784 (2)	0.63356 (17)	1.11287 (14)	0.0626 (5)
N3	0.88138 (15)	0.67128 (11)	0.64273 (11)	0.0336 (3)
N4	1.16916 (19)	0.90139 (14)	1.01779 (14)	0.0529 (4)
O1	0.52598 (14)	0.69380 (11)	0.52284 (11)	0.0495 (3)
O2	0.58984 (16)	0.62604 (11)	0.70601 (11)	0.0514 (3)
O3	1.2203 (3)	1.00113 (14)	0.92564 (15)	0.0984 (7)
O4	0.69851 (15)	0.44310 (11)	0.57910 (12)	0.0515 (3)
O5	0.63255 (15)	0.51278 (12)	0.39761 (10)	0.0542 (3)
C1	0.3792 (2)	0.65704 (15)	0.46130 (14)	0.0387 (4)
C2	0.29154 (19)	0.73827 (14)	0.43619 (14)	0.0375 (4)
C3	0.1306 (2)	0.70435 (16)	0.36591 (16)	0.0466 (4)
H3	0.0769	0.6287	0.3333	0.056*
C4	0.0491 (2)	0.77940 (18)	0.34350 (18)	0.0533 (5)
H4	−0.0584	0.7536	0.2961	0.064*
C5	0.1243 (2)	0.89438 (17)	0.39039 (18)	0.0499 (4)
C6	0.2864 (2)	0.92796 (17)	0.46138 (18)	0.0512 (5)
H6	0.3409	1.0035	0.4947	0.061*
C7	0.3659 (2)	0.85148 (16)	0.48263 (16)	0.0453 (4)
H7	0.4734	0.8767	0.5299	0.054*
C8	0.1256 (3)	1.0887 (2)	0.4196 (2)	0.0767 (7)
H8A	0.0508	1.1301	0.3992	0.115*
H8B	0.2045	1.0961	0.3895	0.115*
H8C	0.1752	1.1183	0.5032	0.115*
C9	−0.1234 (3)	0.9381 (2)	0.3032 (2)	0.0778 (7)
H9A	−0.1586	1.0036	0.3019	0.117*
H9B	−0.1759	0.9056	0.3388	0.117*
H9C	−0.1478	0.8836	0.2247	0.117*
C10	0.4677 (2)	0.56674 (16)	0.69715 (14)	0.0418 (4)
C11	0.43798 (19)	0.58899 (15)	0.80439 (14)	0.0398 (4)
C12	0.3197 (2)	0.51570 (17)	0.80381 (15)	0.0486 (4)
H12	0.2529	0.4548	0.7334	0.058*
C13	0.2979 (2)	0.53000 (18)	0.90376 (17)	0.0531 (5)
H13	0.2169	0.4791	0.8997	0.064*
C14	0.3962 (2)	0.62048 (17)	1.01199 (15)	0.0478 (4)
C15	0.5102 (2)	0.69743 (18)	1.01119 (15)	0.0530 (5)
H15	0.5735	0.7608	1.0805	0.064*
C16	0.5308 (2)	0.68143 (17)	0.91032 (15)	0.0474 (4)
H16	0.6087	0.7337	0.9131	0.057*
C17	0.4929 (3)	0.7180 (2)	1.22593 (18)	0.0795 (7)
H17A	0.4760	0.7042	1.2867	0.119*
H17B	0.4808	0.7918	1.2350	0.119*
H17C	0.5977	0.7140	1.2310	0.119*
C18	0.2607 (3)	0.5536 (2)	1.1128 (2)	0.0754 (7)
H18A	0.2701	0.5743	1.1916	0.113*
H18B	0.2763	0.4793	1.0808	0.113*
H18C	0.1572	0.5539	1.0661	0.113*
C19	0.94694 (19)	0.75356 (14)	0.75189 (14)	0.0369 (4)
H19	0.8823	0.7750	0.7921	0.044*
C20	1.1054 (2)	0.80823 (15)	0.80792 (15)	0.0427 (4)
C21	1.2004 (2)	0.77375 (18)	0.74711 (18)	0.0539 (5)
H21	1.3080	0.8089	0.7816	0.065*
C22	1.1348 (2)	0.68765 (18)	0.63601 (18)	0.0537 (5)
H22	1.1976	0.6621	0.5951	0.064*
C23	0.9753 (2)	0.63968 (15)	0.58606 (15)	0.0416 (4)
H23	0.9305	0.5829	0.5097	0.050*
C24	1.1705 (2)	0.91161 (17)	0.92357 (17)	0.0536 (5)
C25	1.2270 (3)	1.0051 (2)	1.1274 (2)	0.0837 (8)
H25A	1.1758	0.9954	1.1766	0.100*
H25B	1.1973	1.0667	1.1101	0.100*
C26	1.4002 (4)	1.0362 (3)	1.1927 (3)	0.1230 (13)
H26A	1.4314	1.1060	1.2619	0.184*
H26B	1.4518	1.0449	1.1442	0.184*
H26C	1.4299	0.9777	1.2144	0.184*
C27	1.1366 (3)	0.79420 (19)	1.02381 (18)	0.0609 (5)
H27A	1.2212	0.7969	1.0912	0.073*
H27B	1.1368	0.7341	0.9545	0.073*
C28	0.9820 (4)	0.7661 (3)	1.0327 (3)	0.0990 (9)
H28A	0.9775	0.7036	1.0522	0.149*
H28B	0.8967	0.7463	0.9591	0.149*
H28C	0.9729	0.8306	1.0926	0.149*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02904 (10)	0.03429 (12)	0.03032 (10)	0.00543 (7)	0.01153 (7)	0.00929 (8)
N1	0.0647 (12)	0.0723 (13)	0.1079 (16)	0.0331 (10)	0.0319 (11)	0.0608 (12)
N2	0.0671 (11)	0.0820 (13)	0.0420 (9)	0.0147 (10)	0.0313 (8)	0.0238 (9)
N3	0.0325 (6)	0.0324 (7)	0.0342 (7)	0.0087 (5)	0.0142 (5)	0.0120 (6)
N4	0.0554 (10)	0.0441 (9)	0.0426 (8)	0.0082 (7)	0.0161 (7)	0.0065 (7)
O1	0.0403 (7)	0.0488 (8)	0.0577 (8)	0.0151 (6)	0.0144 (6)	0.0253 (6)
O2	0.0586 (8)	0.0561 (8)	0.0402 (7)	0.0107 (6)	0.0297 (6)	0.0145 (6)
O3	0.1420 (17)	0.0466 (10)	0.0616 (10)	−0.0197 (10)	0.0089 (10)	0.0166 (8)
O4	0.0514 (7)	0.0395 (7)	0.0664 (8)	0.0141 (6)	0.0237 (6)	0.0253 (6)
O5	0.0479 (7)	0.0726 (9)	0.0298 (6)	0.0141 (7)	0.0151 (5)	0.0108 (6)
C1	0.0444 (9)	0.0414 (10)	0.0387 (9)	0.0150 (7)	0.0233 (7)	0.0191 (8)
C2	0.0395 (8)	0.0417 (9)	0.0381 (8)	0.0118 (7)	0.0197 (7)	0.0202 (7)
C3	0.0426 (9)	0.0424 (10)	0.0513 (10)	0.0073 (8)	0.0159 (8)	0.0204 (8)
C4	0.0403 (9)	0.0593 (13)	0.0585 (12)	0.0129 (9)	0.0130 (8)	0.0296 (10)
C5	0.0522 (11)	0.0547 (12)	0.0596 (12)	0.0221 (9)	0.0271 (9)	0.0358 (10)
C6	0.0538 (11)	0.0411 (10)	0.0640 (12)	0.0108 (8)	0.0240 (9)	0.0284 (9)
C7	0.0398 (9)	0.0465 (10)	0.0510 (10)	0.0085 (8)	0.0173 (8)	0.0241 (9)
C8	0.0995 (19)	0.0644 (16)	0.0989 (19)	0.0435 (14)	0.0491 (16)	0.0549 (15)
C9	0.0682 (15)	0.104 (2)	0.0950 (19)	0.0481 (15)	0.0366 (14)	0.0672 (17)
C10	0.0423 (9)	0.0517 (11)	0.0345 (8)	0.0217 (8)	0.0190 (7)	0.0166 (8)
C11	0.0367 (8)	0.0509 (10)	0.0323 (8)	0.0161 (7)	0.0164 (7)	0.0153 (7)
C12	0.0471 (10)	0.0517 (11)	0.0359 (9)	0.0081 (8)	0.0150 (8)	0.0107 (8)
C13	0.0522 (11)	0.0602 (12)	0.0469 (10)	0.0069 (9)	0.0250 (9)	0.0210 (9)
C14	0.0488 (10)	0.0608 (12)	0.0391 (9)	0.0194 (9)	0.0243 (8)	0.0203 (9)
C15	0.0483 (10)	0.0634 (13)	0.0322 (9)	0.0059 (9)	0.0166 (8)	0.0075 (9)
C16	0.0410 (9)	0.0574 (12)	0.0374 (9)	0.0070 (8)	0.0191 (7)	0.0128 (8)
C17	0.0939 (18)	0.100 (2)	0.0390 (11)	0.0174 (15)	0.0317 (12)	0.0223 (12)
C18	0.0869 (17)	0.0942 (19)	0.0689 (15)	0.0242 (14)	0.0474 (14)	0.0456 (15)
C19	0.0358 (8)	0.0342 (9)	0.0345 (8)	0.0068 (7)	0.0140 (6)	0.0097 (7)
C20	0.0384 (9)	0.0404 (10)	0.0390 (9)	0.0039 (7)	0.0071 (7)	0.0160 (8)
C21	0.0300 (8)	0.0586 (12)	0.0637 (12)	0.0058 (8)	0.0136 (8)	0.0234 (10)
C22	0.0401 (9)	0.0651 (13)	0.0621 (12)	0.0180 (9)	0.0298 (9)	0.0249 (10)
C23	0.0402 (9)	0.0431 (10)	0.0391 (9)	0.0123 (7)	0.0197 (7)	0.0122 (8)
C24	0.0504 (11)	0.0419 (11)	0.0454 (10)	0.0019 (8)	0.0044 (8)	0.0113 (8)
C25	0.108 (2)	0.0578 (15)	0.0513 (13)	0.0038 (14)	0.0278 (13)	−0.0016 (11)
C26	0.110 (3)	0.107 (3)	0.0625 (17)	−0.029 (2)	−0.0102 (16)	0.0001 (16)
C27	0.0666 (13)	0.0592 (13)	0.0478 (11)	0.0142 (10)	0.0150 (10)	0.0215 (10)
C28	0.100 (2)	0.110 (2)	0.110 (2)	0.0161 (18)	0.0574 (19)	0.061 (2)

Geometric parameters (Å, º) top

Zn1—Zn1ⁱ	2.8927 (4)	C11—C16	1.388 (2)
Zn1—O1	2.0265 (12)	C12—C13	1.373 (3)
Zn1—O2	2.0269 (12)	C12—H12	0.9300
Zn1—O4	2.0669 (12)	C13—H13	0.9300
Zn1—O5	2.0459 (12)	C14—N2	1.371 (2)
Zn1—N3	2.0446 (13)	C14—C13	1.404 (3)
O1—C1	1.263 (2)	C14—C15	1.399 (3)
O2—C10	1.255 (2)	C15—C16	1.374 (2)
O4—C1ⁱ	1.255 (2)	C15—H15	0.9300
O5—C10ⁱ	1.266 (2)	C16—H16	0.9300
N1—C9	1.438 (3)	C17—H17A	0.9600
N1—C8	1.447 (3)	C17—H17B	0.9600
N2—C18	1.443 (3)	C17—H17C	0.9600
N2—C17	1.449 (3)	C18—H18A	0.9600
N3—C19	1.334 (2)	C18—H18B	0.9600
N3—C23	1.336 (2)	C18—H18C	0.9600
N4—C25	1.463 (3)	C19—C20	1.377 (2)
N4—C27	1.459 (3)	C19—H19	0.9300
C1—O4ⁱ	1.255 (2)	C20—C21	1.388 (3)
C2—C1	1.484 (2)	C20—C24	1.503 (2)
C2—C3	1.392 (2)	C21—H21	0.9300
C2—C7	1.381 (2)	C22—C21	1.369 (3)
C3—C4	1.369 (3)	C22—H22	0.9300
C3—H3	0.9300	C23—C22	1.370 (2)
C4—C5	1.403 (3)	C23—H23	0.9300
C4—H4	0.9300	C24—O3	1.214 (3)
C5—N1	1.366 (2)	C24—N4	1.331 (3)
C6—C5	1.402 (3)	C25—C26	1.478 (4)
C6—H6	0.9300	C25—H25A	0.9700
C7—C6	1.371 (3)	C25—H25B	0.9700
C7—H7	0.9300	C26—H26A	0.9600
C8—H8A	0.9600	C26—H26B	0.9600
C8—H8B	0.9600	C26—H26C	0.9600
C8—H8C	0.9600	C27—C28	1.500 (3)
C9—H9A	0.9600	C27—H27A	0.9700
C9—H9B	0.9600	C27—H27B	0.9700
C9—H9C	0.9600	C28—H28A	0.9600
C10—O5ⁱ	1.266 (2)	C28—H28B	0.9600
C11—C10	1.485 (2)	C28—H28C	0.9600
C11—C12	1.386 (3)

O1—Zn1—O2	89.01 (6)	C13—C12—H12	118.9
O1—Zn1—O4	161.34 (5)	C12—C13—C14	120.84 (18)
O1—Zn1—O5	88.39 (6)	C12—C13—H13	119.6
O1—Zn1—N3	106.31 (5)	C14—C13—H13	119.6
O2—Zn1—O4	89.28 (6)	N2—C14—C13	121.29 (18)
O2—Zn1—O5	161.09 (6)	N2—C14—C15	121.92 (18)
O2—Zn1—N3	101.76 (5)	C15—C14—C13	116.77 (16)
O5—Zn1—O4	87.23 (6)	C16—C15—C14	121.46 (18)
N3—Zn1—O4	92.23 (5)	C16—C15—H15	119.3
N3—Zn1—O5	96.95 (5)	C14—C15—H15	119.3
C1—O1—Zn1	118.82 (11)	C11—C16—H16	119.2
C10—O2—Zn1	119.77 (11)	C15—C16—C11	121.52 (18)
C1ⁱ—O4—Zn1	135.03 (12)	C15—C16—H16	119.2
C10ⁱ—O5—Zn1	134.43 (12)	N2—C17—H17A	109.5
C5—N1—C8	120.9 (2)	N2—C17—H17B	109.5
C5—N1—C9	121.6 (2)	N2—C17—H17C	109.5
C9—N1—C8	117.41 (19)	H17A—C17—H17B	109.5
C14—N2—C17	120.85 (19)	H17A—C17—H17C	109.5
C14—N2—C18	121.51 (19)	H17B—C17—H17C	109.5
C18—N2—C17	116.96 (18)	N2—C18—H18A	109.5
C19—N3—Zn1	121.99 (11)	N2—C18—H18B	109.5
C19—N3—C23	118.04 (14)	N2—C18—H18C	109.5
C23—N3—Zn1	119.85 (11)	H18A—C18—H18B	109.5
C24—N4—C25	117.08 (19)	H18A—C18—H18C	109.5
C24—N4—C27	124.81 (17)	H18B—C18—H18C	109.5
C27—N4—C25	117.48 (18)	N3—C19—C20	123.28 (15)
O1—C1—C2	117.78 (15)	N3—C19—H19	118.4
O4ⁱ—C1—O1	124.74 (16)	C20—C19—H19	118.4
O4ⁱ—C1—C2	117.47 (15)	C19—C20—C21	117.52 (16)
C3—C2—C1	121.68 (16)	C19—C20—C24	121.55 (16)
C7—C2—C1	121.40 (15)	C21—C20—C24	120.41 (16)
C7—C2—C3	116.92 (16)	C20—C21—H21	120.2
C2—C3—H3	119.1	C22—C21—C20	119.63 (16)
C4—C3—C2	121.76 (17)	C22—C21—H21	120.2
C4—C3—H3	119.1	C21—C22—C23	118.90 (17)
C3—C4—C5	121.46 (18)	C21—C22—H22	120.6
C3—C4—H4	119.3	C23—C22—H22	120.6
C5—C4—H4	119.3	N3—C23—C22	122.60 (16)
N1—C5—C4	122.23 (19)	N3—C23—H23	118.7
N1—C5—C6	121.32 (19)	C22—C23—H23	118.7
C6—C5—C4	116.45 (17)	O3—C24—N4	123.26 (19)
C5—C6—H6	119.4	O3—C24—C20	117.73 (19)
C7—C6—C5	121.22 (18)	N4—C24—C20	119.00 (18)
C7—C6—H6	119.4	N4—C25—C26	113.3 (2)
C2—C7—H7	118.9	N4—C25—H25A	108.9
C6—C7—C2	122.19 (17)	N4—C25—H25B	108.9
C6—C7—H7	118.9	C26—C25—H25A	108.9
N1—C8—H8A	109.5	C26—C25—H25B	108.9
N1—C8—H8B	109.5	H25A—C25—H25B	107.7
N1—C8—H8C	109.5	C25—C26—H26A	109.5
H8A—C8—H8B	109.5	C25—C26—H26B	109.5
H8A—C8—H8C	109.5	C25—C26—H26C	109.5
H8B—C8—H8C	109.5	H26A—C26—H26B	109.5
N1—C9—H9A	109.5	H26A—C26—H26C	109.5
N1—C9—H9B	109.5	H26B—C26—H26C	109.5
N1—C9—H9C	109.5	N4—C27—C28	113.8 (2)
H9A—C9—H9B	109.5	N4—C27—H27A	108.8
H9A—C9—H9C	109.5	N4—C27—H27B	108.8
H9B—C9—H9C	109.5	C28—C27—H27A	108.8
O2—C10—O5ⁱ	124.39 (16)	C28—C27—H27B	108.8
O2—C10—C11	118.63 (15)	H27A—C27—H27B	107.7
O5ⁱ—C10—C11	116.98 (16)	C27—C28—H28A	109.5
C12—C11—C10	121.20 (16)	C27—C28—H28B	109.5
C12—C11—C16	117.10 (16)	C27—C28—H28C	109.5
C16—C11—C10	121.66 (16)	H28A—C28—H28B	109.5
C11—C12—H12	118.9	H28A—C28—H28C	109.5
C13—C12—C11	122.17 (17)	H28B—C28—H28C	109.5

O2—Zn1—O1—C1	−86.30 (13)	C3—C2—C7—C6	0.1 (3)
O4—Zn1—O1—C1	−1.5 (2)	C2—C3—C4—C5	0.0 (3)
O5—Zn1—O1—C1	74.97 (13)	C3—C4—C5—N1	−179.4 (2)
N3—Zn1—O1—C1	171.73 (12)	C3—C4—C5—C6	−0.2 (3)
O1—Zn1—O2—C10	92.13 (14)	C4—C5—N1—C8	179.9 (2)
O4—Zn1—O2—C10	−69.29 (14)	C4—C5—N1—C9	3.2 (3)
O5—Zn1—O2—C10	10.0 (3)	C6—C5—N1—C8	0.7 (3)
N3—Zn1—O2—C10	−161.42 (14)	C6—C5—N1—C9	−176.0 (2)
O1—Zn1—O4—C1ⁱ	4.3 (3)	C7—C6—C5—N1	179.6 (2)
O2—Zn1—O4—C1ⁱ	89.10 (17)	C7—C6—C5—C4	0.3 (3)
O5—Zn1—O4—C1ⁱ	−72.31 (17)	C2—C7—C6—C5	−0.2 (3)
N3—Zn1—O4—C1ⁱ	−169.16 (17)	C12—C11—C10—O2	−169.73 (18)
O1—Zn1—O5—C10ⁱ	−88.02 (18)	C12—C11—C10—O5ⁱ	9.4 (3)
O2—Zn1—O5—C10ⁱ	−5.8 (3)	C16—C11—C10—O2	7.8 (3)
O4—Zn1—O5—C10ⁱ	73.84 (18)	C16—C11—C10—O5ⁱ	−173.06 (17)
N3—Zn1—O5—C10ⁱ	165.75 (17)	C10—C11—C12—C13	175.00 (17)
O1—Zn1—N3—C19	75.41 (13)	C16—C11—C12—C13	−2.7 (3)
O1—Zn1—N3—C23	−108.69 (13)	C10—C11—C16—C15	−175.32 (17)
O2—Zn1—N3—C19	−17.02 (14)	C12—C11—C16—C15	2.3 (3)
O2—Zn1—N3—C23	158.88 (13)	C11—C12—C13—C14	−0.2 (3)
O4—Zn1—N3—C19	−106.75 (13)	C13—C14—N2—C17	171.8 (2)
O4—Zn1—N3—C23	69.15 (13)	C13—C14—N2—C18	1.6 (3)
O5—Zn1—N3—C19	165.77 (13)	C15—C14—N2—C17	−9.6 (3)
O5—Zn1—N3—C23	−18.33 (14)	C15—C14—N2—C18	−179.8 (2)
Zn1—O1—C1—O4ⁱ	−2.1 (2)	N2—C14—C13—C12	−178.00 (19)
Zn1—O1—C1—C2	176.98 (10)	C15—C14—C13—C12	3.3 (3)
Zn1—O2—C10—O5ⁱ	−5.9 (3)	N2—C14—C15—C16	177.68 (19)
Zn1—O2—C10—C11	173.11 (11)	C13—C14—C15—C16	−3.7 (3)
Zn1—N3—C19—C20	176.95 (13)	C14—C15—C16—C11	0.9 (3)
Zn1—N3—C23—C22	−175.48 (15)	N3—C19—C20—C21	−1.0 (3)
C19—N3—C23—C22	0.6 (3)	N3—C19—C20—C24	170.73 (17)
C23—N3—C19—C20	1.0 (2)	C19—C20—C21—C22	−0.5 (3)
C24—N4—C25—C26	−86.0 (3)	C24—C20—C21—C22	−172.34 (19)
C27—N4—C25—C26	85.3 (3)	C19—C20—C24—O3	−111.7 (2)
C24—N4—C27—C28	−110.6 (2)	C19—C20—C24—N4	67.5 (2)
C25—N4—C27—C28	78.8 (3)	C21—C20—C24—O3	59.8 (3)
C3—C2—C1—O1	177.84 (16)	C21—C20—C24—N4	−121.0 (2)
C3—C2—C1—O4ⁱ	−3.0 (2)	C23—C22—C21—C20	2.0 (3)
C7—C2—C1—O1	−2.8 (2)	N3—C23—C22—C21	−2.0 (3)
C7—C2—C1—O4ⁱ	176.30 (16)	O3—C24—N4—C25	1.9 (3)
C1—C2—C3—C4	179.40 (17)	O3—C24—N4—C27	−168.7 (2)
C7—C2—C3—C4	0.1 (3)	C20—C24—N4—C25	−177.29 (19)
C1—C2—C7—C6	−179.29 (17)	C20—C24—N4—C27	12.1 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O5	0.93	2.54	3.122 (2)	121
C8—H8A···Cg3ⁱⁱ	0.96	2.77	3.629 (3)	150

Symmetry code: (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₉H₁₀NO₂)₄(C₁₀H₁₄N₂O)₂]
M_r	1143.96
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	9.2731 (6), 13.2340 (8), 13.4756 (8)
α, β, γ (°)	112.348 (3), 109.236 (2), 95.728 (2)
V (Å³)	1395.33 (16)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.52 × 0.35 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.681, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	24970, 6877, 5749
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.090, 1.06
No. of reflections	6877
No. of parameters	349
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.43

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—O1	2.0265 (12)	Zn1—O5	2.0459 (12)
Zn1—O2	2.0269 (12)	Zn1—N3	2.0446 (13)
Zn1—O4	2.0669 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O5	0.93	2.54	3.122 (2)	121
C8—H8A···Cg3ⁱ	0.96	2.77	3.629 (3)	150

Symmetry code: (i) −x+1, −y, −z+1.

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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