Bis(μ-2-fluoro­benzoato-1:2κ2O:O′)(2-fluoro­benzoato-1κ2O,O′)(2-fluoro­benzoato-2κO)dinicotinamide-1κN1,2κN1-dizinc(II)–2-fluoro­benzoic acid (1/1)

Hökelek, T.; Yılmaz, F.; Tercan, B.; Özbek, F.E.; Necefoğlu, H.

doi:10.1107/S1600536809048089

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1608-m1609

doi:10.1107/S1600536809048089

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Bis(μ-2-fluorobenzoato-1:2κ²O:O′)(2-fluorobenzoato-1κ²O,O′)(2-fluorobenzoato-2κO)dinicotinamide-1κN¹,2κN¹-dizinc(II)–2-fluorobenzoic acid (1/1)

Tuncer Hökelek,^a ^* Filiz Yılmaz,^b Barış Tercan,^c F. Elif Özbek ^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 12 November 2009; online 21 November 2009)

The asymmetric unit of the title compound, [Zn₂(C₇H₄FO₂)₄(C₆H₆N₂O)₂]·C₇H₅FO₂, consists of a binuclear Zn^II complex bridged by two carboxyl groups of 2-fluorobenzoate (FB) anions and a 2-fluorobenzoic acid molecule. The two bridging FB anions, one chelating FB anion and one nicotinamide (NA) ligand coordinate to one Zn cation with a distorted square-pyramidal geometry, while the two bridging FB anions, one monodentate FB anion and one NA ligand coordinate to the other Zn cation with a distorted tetrahedral geometry. Within the binuclear molecule, the pyridine rings are oriented at a dihedral angle of 19.41 (14)°. In the crystal structure, the uncoordinated 2-fluorobenzoic acid molecules are linked by O—H⋯O hydrogen bonding, forming centrosymmetric supramolecular dimers. Intermolecular N—H⋯O hydrogen bonds link the complex molecules into a three-dimensional network. The π–π contacts between nearly parallel pyridine and benzene rings [dihedral angles of 19.41 (14) and 12.72 (16)°, respectively, centroid–centroid distances = 3.701 (2) and 3.857 (3) Å] may further stabilize the crystal structure. The fluorine atoms in two FB ligands are disordered over two positions, with occupancy ratios of 0.70:0.30.

Related literature

For general background to nicotinamide and the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972 ); Krishnamachari (1974 ). For related structures, see: Hökelek & Necefoğlu (1996 ); Hökelek et al. (2009a ,b ,c ,d ); Greenaway et al. (1984 ).

Experimental

Crystal data

[Zn₂(C₇H₄FO₂)₄(C₆H₆N₂O)₂]·C₇H₅FO₂
M_r = 1071.55
Monoclinic, P 2₁ /c
a = 12.5143 (2) Å
b = 16.7106 (3) Å
c = 20.6673 (4) Å
β = 92.929 (2)°
V = 4316.33 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 100 K
0.29 × 0.25 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.710, T_max = 0.840
37814 measured reflections
10696 independent reflections
7459 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.097
S = 1.01
10696 reflections
659 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.39 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.296 (3)
Zn1—O2	2.006 (3)
Zn1—O5	1.958 (3)
Zn1—O7	2.005 (3)
Zn1—N1	2.068 (4)
Zn2—O3	1.995 (3)
Zn2—O6	1.975 (3)
Zn2—O8	1.940 (3)
Zn2—N3	2.021 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.82 (5)	2.39 (5)	3.056 (6)	140 (5)
N2—H2B⋯O10ⁱⁱ	0.84 (6)	2.03 (5)	2.863 (6)	176.4 (5)
N4—H4A⋯O4ⁱⁱⁱ	0.81 (5)	2.11 (5)	2.825 (5)	149 (5)
N4—H4B⋯O9^iv	0.92 (7)	1.96 (7)	2.874 (6)	176 (7)
O12—H121⋯O11^v	0.92 (8)	1.71 (8)	2.626 (5)	174 (6)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y-1, z; (v) -x+1, -y+2, -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/S1600536809048089/xu2668sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048089/xu2668Isup2.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 nicotinamide (NA), four 2-fluorobenzoate (FB) ligands and one 2-fluorobenzoic acid molecule. The structures of some DENA and/or NA complexes of Zn^II ion, [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 the title dimeric complex, [Zn₂(C₇H₄FO₂)₄(C₆H₆N₂O)₂].(C₇H₅FO₂), two Zn^II atoms are surrounded by three FB groups and one NA ligand. The NA ligands are coordinated to Zn^II ions through pyridine N atoms only. Two FB groups act as bridging ligands, while the other two FB groups are coordinated to Zn^II ions bidentately and monodentately. The Zn1···Zn2 distance is 3.315 (3) Å. Atom Zn1 lies 0.2403 (5) Å below the best least-squares plane of the four O atoms (O1, O2, O5 and O7) [with a maximum deviation of 0.119 (3) Å for atom O2], while atom Zn2 lies 0.5735 (5) Å below the least-squares plane of the three O atoms (O3, O6 and O8). The four O atoms around the Zn1 atom form a distorted square-planar arrangement with an average Zn1—O bond length of 2.06625 (30) Å. The distorted square-pyramidal coordination is completed by the pyridine N1 atom of the NA ligand at a distance of 2.068 (4) Å (Table 1, Fig. 1). The three nearest O atoms arrangement [with an average Zn2—O bond length of 1.970 (3) Å] around Zn2 atom is completed by the pyridine N3 atom of the NA ligand at a distance of 2.021 (4) Å to form a tetrahedral coordinaton (Table 1, Fig. 1).

The N1—Zn1···Zn2 and N3—Zn2···Zn1 angles are 152.72 (3) and 171.99 (3) °, respectively. The dihedral angle between the best least-squares planes through Zn1, O5, C15, O6, Zn2 [with a maximum deviation of 0.115 (3) Å for atom O5] and Zn1, O7, C22, O8, Zn2 [with a maximum deviation of -0.089 (3) Å for atom O8] is 115.74 (5)°. The dihedral angles between the planar carboxylate groups (O1/O2/C1),(O3/O4/C8), (O5/O6/C15), (O7/O8/C22) and the adjacent benzene rings A (C2—C7), B (C9—C14), C (C16—C21), D (C23—C28) are 10.2 (5)°, 7.65 (17)°, 16.03 (30)° and 16.21 (35)°, respectively, while those between rings A, B, C and D are A/B = 12.72 (16), A/C = 71.97 (15), A/D = 71.15 (14), B/C = 78.14 (15), B/D = 83.60 (16) and C/D = 47.65 (13) °. The pyridine rings E (N1/C29—C33) and F (N3/C35—C39) are oriented at a dihedral angle of 19.41 (14)°. The O1—Zn1—O2 angle is 60.92 (12)°. The corresponding O—M—O (where M is a metal) angles are 58.3 (3)° in [Zn₂(C₁₀H₁₄N₂O)₂(C₇H₅O₃)₄].2H₂O (Hökelek & Necefoğlu, 1996), 60.03 (6)° in [Zn(C₉H₁₀NO₂)₂(C₆H₆N₂O)(H₂O)₂] (Hökelek et al., 2009c), 52.91 (4) and 53.96 (4) ° in [Cd(C₈H₅O₃)₂(C₆H₆N₂O)₂(H₂O)].H₂O (Hökelek et al., 2009d) and 55.2 (1)° in [Cu(Asp)₂(py)₂] (where Asp is acetylsalicylate and py is pyridine) (Greenaway et al., 1984).

In the crystal structure, N—H···O and O—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 and benzene rings, benzene and pyridine rings, pyridine and H (Zn1/O1/O2/C1) rings and pyridine and benzene rings, Cg1—Cg2, Cg4—Cg6ⁱ, Cg5—Cg8 and Cg6—Cg7ⁱ [symmetry code: (i) 1 - x, y - 1/2, 1/2 - z, where Cg1, Cg2, Cg4, Cg5, Cg6, Cg7 and Cg8 are centroids of the rings A (C2—C7), B (C9—C14), D (C23—C28), E (N1/C29—C33), F (N3/C35—C39), G (C41—C46) and H (Zn1/O1/O2/C1), respectively] may further stabilize the structure, with centroid-centroid distances of 3.716 (3), 3.701 (2), 3.926 (2) and 3.857 (3) Å, respectively.

Related literature top

For general background to nicotinamide and the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972); Krishnamachari (1974). For related structures, see: Hökelek & Necefoğlu (1996); Hökelek et al. (2009a,b,c,d); Greenaway et al. (1984).

Experimental top

The title compound was prepared by the reaction of ZnSO₄.H₂O (0.89 g, 5 mmol) in H₂O (20 ml) and NA (1.22 g, 10 mmol) in H₂O (20 ml) with sodium 2-fluorobenzoate (1.62 g, 10 mmol) in H₂O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for two days, 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 20% probability level. Hydrogen atoms have been omitted for clarity.

Bis(µ-2-fluorobenzoato-1:2κ²O:O')(2-fluorobenzoato- 1κ²O,O')(2-fluorobenzoato-2κO)dinicotinamide- 1κN¹,2κN¹-dizinc(II)–2-fluorobenzoic acid (1/1) top

Crystal data top

[Zn₂(C₇H₄FO₂)₄(C₆H₆N₂O)₂]·C₇H₅FO₂	F(000) = 2176
M_r = 1071.55	D_x = 1.649 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9923 reflections
a = 12.5143 (2) Å	θ = 2.3–28.1°
b = 16.7106 (3) Å	µ = 1.21 mm⁻¹
c = 20.6673 (4) Å	T = 100 K
β = 92.929 (2)°	Block, colorless
V = 4316.33 (13) Å³	0.29 × 0.25 × 0.14 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	10696 independent reflections
Radiation source: fine-focus sealed tube	7459 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→13
T_min = 0.710, T_max = 0.840	k = −22→22
37814 measured reflections	l = −26→27

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0383P)² + 3.8099P] where P = (F_o² + 2F_c²)/3
10696 reflections	(Δ/σ)_max = 0.001
659 parameters	Δρ_max = 1.39 e Å⁻³
10 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Zn₂(C₇H₄FO₂)₄(C₆H₆N₂O)₂]·C₇H₅FO₂	V = 4316.33 (13) Å³
M_r = 1071.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.5143 (2) Å	µ = 1.21 mm⁻¹
b = 16.7106 (3) Å	T = 100 K
c = 20.6673 (4) Å	0.29 × 0.25 × 0.14 mm
β = 92.929 (2)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	10696 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	7459 reflections with I > 2σ(I)
T_min = 0.710, T_max = 0.840	R_int = 0.036
37814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	10 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 1.39 e Å⁻³
10696 reflections	Δρ_min = −0.59 e Å⁻³
659 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	0.17153 (4)	0.67257 (3)	0.24483 (2)	0.01406 (14)
Zn2	0.31257 (4)	0.51261 (3)	0.29078 (3)	0.01641 (14)
F1	−0.0139 (2)	0.6414 (2)	0.02860 (15)	0.0383 (8)
F2	0.1234 (3)	0.4736 (2)	0.09432 (18)	0.0236 (9)	0.70
F2'	0.4720 (5)	0.5834 (7)	0.0809 (5)	0.054 (3)*	0.30
F3	−0.0844 (2)	0.64099 (18)	0.36234 (15)	0.0362 (8)
F4	0.6020 (3)	0.6154 (2)	0.3631 (2)	0.0291 (10)	0.70
F4'	0.3673 (4)	0.8400 (4)	0.3434 (4)	0.0138 (17)*	0.30
F5	0.4883 (2)	0.73739 (19)	0.00733 (15)	0.0377 (8)
O1	0.0703 (3)	0.6540 (2)	0.15019 (15)	0.0240 (8)
O2	0.2346 (2)	0.6999 (2)	0.16036 (14)	0.0199 (7)
O3	0.2399 (2)	0.5160 (2)	0.20262 (16)	0.0270 (8)
O4	0.4067 (2)	0.5492 (2)	0.19029 (16)	0.0242 (8)
O5	0.0874 (2)	0.60130 (18)	0.29767 (14)	0.0163 (7)
O6	0.1828 (2)	0.49874 (19)	0.34017 (15)	0.0199 (7)
O7	0.3061 (2)	0.6981 (2)	0.29769 (14)	0.0182 (7)
O8	0.4007 (2)	0.59306 (19)	0.33526 (16)	0.0211 (7)
O9	0.2568 (3)	0.9875 (2)	0.26713 (19)	0.0319 (9)
O10	0.2451 (2)	0.2018 (2)	0.27913 (16)	0.0228 (8)
O11	0.6174 (3)	0.9659 (2)	0.0211 (2)	0.0380 (10)
O12	0.4706 (3)	0.8936 (2)	0.00208 (19)	0.0331 (9)
H121	0.443 (5)	0.943 (5)	−0.008 (3)	0.07 (2)*
N1	0.0910 (3)	0.7776 (2)	0.26319 (17)	0.0148 (8)
N2	0.1202 (4)	1.0617 (3)	0.3008 (2)	0.0235 (10)
H2A	0.058 (4)	1.063 (3)	0.310 (2)	0.022 (14)*
H2B	0.158 (4)	1.102 (3)	0.296 (3)	0.030 (16)*
N3	0.4006 (3)	0.4123 (2)	0.30545 (17)	0.0142 (8)
N4	0.3912 (4)	0.1241 (3)	0.2944 (2)	0.0209 (9)
H4A	0.454 (4)	0.120 (3)	0.304 (2)	0.024 (15)*
H4B	0.347 (5)	0.082 (4)	0.284 (3)	0.06 (2)*
C1	0.1502 (4)	0.6839 (3)	0.1255 (2)	0.0172 (10)
C2	0.1499 (3)	0.7054 (3)	0.0554 (2)	0.0163 (10)
C3	0.0668 (4)	0.6878 (3)	0.0113 (2)	0.0203 (10)
C4	0.0640 (4)	0.7140 (3)	−0.0521 (2)	0.0273 (12)
H4	0.0060	0.7019	−0.0803	0.033*
C5	0.1486 (4)	0.7584 (3)	−0.0729 (2)	0.0290 (12)
H5	0.1472	0.7774	−0.1152	0.035*
C6	0.2351 (4)	0.7745 (3)	−0.0310 (2)	0.0255 (12)
H6	0.2931	0.8030	−0.0455	0.031*
C7	0.2356 (4)	0.7483 (3)	0.0323 (2)	0.0196 (10)
H7	0.2944	0.7595	0.0602	0.023*
C8	0.3164 (3)	0.5334 (3)	0.1666 (2)	0.0179 (10)
C9	0.2958 (3)	0.5326 (3)	0.0950 (2)	0.0169 (10)
C10	0.2015 (4)	0.5058 (3)	0.0629 (2)	0.0230 (11)
H14'	0.1473	0.4853	0.0872	0.028*	0.30
C11	0.1859 (4)	0.5086 (3)	−0.0046 (3)	0.0282 (12)
H11	0.1222	0.4903	−0.0246	0.034*
C12	0.2649 (4)	0.5383 (3)	−0.0407 (3)	0.0312 (13)
H12	0.2543	0.5405	−0.0855	0.037*
C13	0.3598 (4)	0.5651 (3)	−0.0124 (2)	0.0306 (13)
H13	0.4132	0.5850	−0.0377	0.037*
C14	0.3749 (4)	0.5620 (3)	0.0552 (2)	0.0234 (11)
H14	0.4394	0.5799	0.0744	0.028*	0.70
C15	0.0994 (3)	0.5414 (3)	0.3341 (2)	0.0145 (9)
C16	0.0079 (3)	0.5168 (3)	0.3735 (2)	0.0164 (10)
C17	−0.0787 (4)	0.5654 (3)	0.3857 (2)	0.0218 (11)
C18	−0.1606 (4)	0.5413 (3)	0.4231 (2)	0.0286 (12)
H18	−0.2176	0.5754	0.4301	0.034*
C19	−0.1571 (4)	0.4659 (4)	0.4501 (3)	0.0362 (14)
H19	−0.2119	0.4489	0.4756	0.043*
C20	−0.0727 (4)	0.4155 (3)	0.4393 (3)	0.0367 (14)
H20	−0.0700	0.3647	0.4576	0.044*
C21	0.0082 (4)	0.4410 (3)	0.4010 (2)	0.0258 (12)
H21	0.0644	0.4064	0.3934	0.031*
C22	0.3881 (3)	0.6668 (3)	0.3252 (2)	0.0158 (10)
C23	0.4772 (3)	0.7209 (3)	0.3453 (2)	0.0141 (9)
C24	0.5816 (3)	0.6927 (3)	0.3596 (2)	0.0174 (10)
H28'	0.5940	0.6378	0.3605	0.021*	0.30
C25	0.6675 (4)	0.7452 (3)	0.3726 (2)	0.0216 (11)
H25	0.7362	0.7253	0.3811	0.026*
C26	0.6492 (4)	0.8258 (3)	0.3728 (2)	0.0216 (11)
H26	0.7064	0.8605	0.3812	0.026*
C27	0.5482 (4)	0.8570 (3)	0.3608 (2)	0.0214 (11)
H27	0.5364	0.9119	0.3621	0.026*
C28	0.4637 (3)	0.8040 (3)	0.3467 (2)	0.0186 (10)
H28	0.3957	0.8248	0.3378	0.022*	0.70
C29	0.1429 (3)	0.8473 (3)	0.2675 (2)	0.0146 (9)
H29	0.2162	0.8472	0.2620	0.018*
C30	0.0941 (3)	0.9198 (3)	0.2797 (2)	0.0150 (10)
C31	−0.0155 (3)	0.9193 (3)	0.2884 (2)	0.0168 (10)
H31	−0.0515	0.9665	0.2972	0.020*
C32	−0.0698 (3)	0.8475 (3)	0.2837 (2)	0.0181 (10)
H32	−0.1430	0.8459	0.2895	0.022*
C33	−0.0157 (3)	0.7782 (3)	0.2707 (2)	0.0168 (10)
H33	−0.0536	0.7304	0.2668	0.020*
C34	0.1630 (3)	0.9929 (3)	0.2819 (2)	0.0187 (10)
C35	0.3537 (3)	0.3409 (3)	0.2987 (2)	0.0142 (9)
H35	0.2799	0.3393	0.2906	0.017*
C36	0.4082 (3)	0.2690 (3)	0.3032 (2)	0.0133 (9)
C37	0.5183 (3)	0.2716 (3)	0.3166 (2)	0.0170 (10)
H37	0.5579	0.2246	0.3204	0.020*
C38	0.5676 (3)	0.3453 (3)	0.3241 (2)	0.0184 (10)
H38	0.6409	0.3483	0.3336	0.022*
C39	0.5075 (3)	0.4143 (3)	0.3175 (2)	0.0174 (10)
H39	0.5418	0.4636	0.3214	0.021*
C40	0.3426 (3)	0.1945 (3)	0.2915 (2)	0.0169 (10)
C41	0.7570 (4)	0.6917 (3)	0.0614 (3)	0.0303 (12)
H41	0.7990	0.6469	0.0709	0.036*
C42	0.6512 (4)	0.6824 (3)	0.0410 (2)	0.0269 (12)
H42	0.6215	0.6316	0.0367	0.032*
C43	0.5899 (4)	0.7494 (3)	0.0272 (2)	0.0225 (11)
C44	0.6319 (4)	0.8263 (3)	0.0324 (2)	0.0195 (10)
C45	0.7393 (4)	0.8332 (3)	0.0534 (2)	0.0268 (12)
H45	0.7699	0.8838	0.0578	0.032*
C46	0.8006 (4)	0.7669 (3)	0.0677 (3)	0.0329 (13)
H46	0.8719	0.7729	0.0817	0.039*
C47	0.5720 (4)	0.9010 (3)	0.0178 (2)	0.0214 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0128 (2)	0.0158 (3)	0.0136 (3)	−0.0009 (2)	0.00059 (19)	0.0017 (2)
Zn2	0.0136 (2)	0.0104 (3)	0.0248 (3)	0.0005 (2)	−0.0018 (2)	0.0001 (2)
F1	0.0310 (16)	0.042 (2)	0.0416 (19)	−0.0084 (15)	−0.0021 (14)	−0.0026 (16)
F2	0.0158 (18)	0.029 (2)	0.026 (2)	−0.0116 (17)	0.0042 (16)	0.0000 (18)
F3	0.0401 (17)	0.0233 (17)	0.0473 (19)	0.0134 (14)	0.0224 (15)	0.0138 (15)
F4	0.025 (2)	0.018 (2)	0.044 (3)	0.0016 (18)	−0.0054 (18)	0.003 (2)
F5	0.0316 (16)	0.0317 (19)	0.049 (2)	−0.0060 (14)	−0.0037 (14)	0.0023 (16)
O1	0.0318 (18)	0.021 (2)	0.0194 (17)	−0.0047 (16)	0.0082 (14)	0.0002 (15)
O2	0.0195 (15)	0.0255 (19)	0.0146 (16)	0.0056 (15)	−0.0014 (13)	0.0000 (15)
O3	0.0132 (15)	0.044 (2)	0.0240 (18)	0.0029 (16)	0.0032 (13)	0.0131 (17)
O4	0.0199 (16)	0.024 (2)	0.0287 (19)	−0.0058 (15)	−0.0002 (14)	−0.0004 (16)
O5	0.0183 (15)	0.0118 (17)	0.0189 (16)	−0.0005 (13)	0.0019 (13)	0.0034 (14)
O6	0.0169 (15)	0.0185 (19)	0.0246 (18)	0.0032 (14)	0.0033 (13)	0.0032 (14)
O7	0.0148 (15)	0.0205 (18)	0.0189 (17)	−0.0008 (14)	−0.0040 (13)	−0.0011 (14)
O8	0.0203 (16)	0.0134 (18)	0.0292 (19)	−0.0025 (14)	−0.0035 (14)	−0.0016 (15)
O9	0.0190 (16)	0.0164 (19)	0.061 (3)	−0.0025 (15)	0.0111 (17)	−0.0072 (18)
O10	0.0151 (15)	0.0142 (18)	0.039 (2)	0.0004 (14)	−0.0032 (14)	0.0005 (16)
O11	0.0239 (18)	0.022 (2)	0.068 (3)	−0.0010 (17)	0.0012 (18)	0.005 (2)
O12	0.0241 (18)	0.025 (2)	0.050 (3)	0.0028 (17)	−0.0048 (17)	0.0043 (19)
N1	0.0137 (17)	0.017 (2)	0.0136 (19)	−0.0028 (16)	−0.0004 (14)	0.0001 (16)
N2	0.015 (2)	0.015 (2)	0.040 (3)	0.001 (2)	−0.0005 (19)	0.000 (2)
N3	0.0141 (17)	0.013 (2)	0.0158 (19)	0.0004 (16)	0.0007 (14)	−0.0001 (16)
N4	0.017 (2)	0.013 (2)	0.032 (2)	0.0016 (19)	−0.0005 (18)	−0.0005 (19)
C1	0.024 (2)	0.012 (2)	0.016 (2)	0.005 (2)	0.0054 (19)	−0.001 (2)
C2	0.018 (2)	0.015 (2)	0.016 (2)	0.003 (2)	0.0017 (18)	−0.002 (2)
C3	0.022 (2)	0.018 (3)	0.021 (2)	−0.003 (2)	0.0013 (19)	−0.001 (2)
C4	0.035 (3)	0.027 (3)	0.019 (3)	0.003 (2)	−0.010 (2)	−0.004 (2)
C5	0.048 (3)	0.026 (3)	0.013 (2)	0.006 (3)	0.004 (2)	0.001 (2)
C6	0.029 (3)	0.026 (3)	0.022 (3)	0.000 (2)	0.010 (2)	0.002 (2)
C7	0.021 (2)	0.019 (3)	0.019 (2)	0.003 (2)	0.0038 (19)	−0.001 (2)
C8	0.018 (2)	0.011 (2)	0.024 (3)	0.0041 (19)	0.0036 (19)	0.003 (2)
C9	0.017 (2)	0.011 (2)	0.023 (2)	0.0040 (19)	0.0033 (18)	0.003 (2)
C10	0.023 (2)	0.013 (3)	0.033 (3)	0.001 (2)	0.003 (2)	0.001 (2)
C11	0.031 (3)	0.016 (3)	0.036 (3)	−0.001 (2)	−0.011 (2)	−0.006 (2)
C12	0.047 (3)	0.024 (3)	0.022 (3)	0.000 (3)	−0.001 (2)	−0.003 (2)
C13	0.038 (3)	0.031 (3)	0.024 (3)	−0.004 (3)	0.012 (2)	0.002 (2)
C14	0.021 (2)	0.023 (3)	0.027 (3)	−0.001 (2)	0.006 (2)	0.000 (2)
C15	0.016 (2)	0.013 (2)	0.015 (2)	−0.0024 (19)	−0.0026 (17)	−0.003 (2)
C16	0.016 (2)	0.015 (2)	0.017 (2)	0.000 (2)	−0.0012 (17)	0.001 (2)
C17	0.025 (2)	0.017 (3)	0.024 (3)	0.003 (2)	0.003 (2)	0.005 (2)
C18	0.023 (2)	0.030 (3)	0.033 (3)	0.009 (2)	0.010 (2)	0.009 (3)
C19	0.025 (3)	0.035 (3)	0.049 (4)	0.001 (3)	0.015 (2)	0.018 (3)
C20	0.030 (3)	0.024 (3)	0.058 (4)	0.000 (2)	0.014 (3)	0.021 (3)
C21	0.019 (2)	0.017 (3)	0.041 (3)	0.002 (2)	0.003 (2)	0.006 (2)
C22	0.018 (2)	0.017 (3)	0.012 (2)	−0.002 (2)	0.0047 (17)	−0.003 (2)
C23	0.019 (2)	0.013 (2)	0.010 (2)	−0.0023 (19)	0.0013 (17)	−0.0009 (19)
C24	0.019 (2)	0.015 (3)	0.018 (2)	−0.002 (2)	−0.0016 (18)	0.002 (2)
C25	0.018 (2)	0.025 (3)	0.022 (3)	−0.002 (2)	−0.0028 (19)	0.003 (2)
C26	0.021 (2)	0.021 (3)	0.023 (2)	−0.011 (2)	0.0035 (19)	−0.003 (2)
C27	0.028 (2)	0.014 (3)	0.023 (3)	−0.004 (2)	0.009 (2)	−0.003 (2)
C28	0.019 (2)	0.019 (3)	0.018 (2)	0.000 (2)	0.0037 (18)	−0.001 (2)
C29	0.0118 (19)	0.016 (3)	0.015 (2)	−0.0012 (19)	−0.0009 (17)	0.0019 (19)
C30	0.014 (2)	0.015 (2)	0.016 (2)	0.0012 (19)	−0.0018 (17)	0.0013 (19)
C31	0.017 (2)	0.019 (3)	0.015 (2)	0.004 (2)	0.0007 (18)	0.002 (2)
C32	0.0097 (19)	0.027 (3)	0.018 (2)	0.001 (2)	0.0000 (17)	0.005 (2)
C33	0.015 (2)	0.019 (3)	0.016 (2)	−0.004 (2)	−0.0022 (17)	0.004 (2)
C34	0.018 (2)	0.015 (3)	0.022 (2)	0.003 (2)	−0.0029 (19)	0.000 (2)
C35	0.0138 (19)	0.014 (2)	0.015 (2)	0.0004 (19)	−0.0006 (17)	0.0002 (19)
C36	0.016 (2)	0.012 (2)	0.012 (2)	0.0012 (19)	0.0012 (17)	−0.0001 (18)
C37	0.017 (2)	0.017 (3)	0.016 (2)	0.005 (2)	0.0019 (18)	0.002 (2)
C38	0.013 (2)	0.021 (3)	0.021 (2)	0.000 (2)	−0.0008 (18)	0.001 (2)
C39	0.017 (2)	0.016 (3)	0.019 (2)	−0.004 (2)	−0.0001 (18)	−0.001 (2)
C40	0.018 (2)	0.015 (3)	0.018 (2)	0.002 (2)	0.0024 (18)	0.000 (2)
C41	0.033 (3)	0.027 (3)	0.032 (3)	0.007 (2)	0.006 (2)	0.001 (2)
C42	0.040 (3)	0.018 (3)	0.024 (3)	−0.004 (2)	0.010 (2)	−0.001 (2)
C43	0.022 (2)	0.028 (3)	0.018 (2)	−0.004 (2)	0.0018 (19)	−0.001 (2)
C44	0.021 (2)	0.022 (3)	0.016 (2)	0.001 (2)	0.0037 (18)	−0.001 (2)
C45	0.025 (2)	0.023 (3)	0.033 (3)	0.000 (2)	0.002 (2)	0.000 (2)
C46	0.027 (3)	0.029 (3)	0.042 (3)	0.003 (3)	0.000 (2)	−0.001 (3)
C47	0.023 (2)	0.023 (3)	0.018 (2)	0.000 (2)	0.0057 (19)	0.000 (2)

Geometric parameters (Å, º) top

Zn1—O1	2.296 (3)	C13—H13	0.9300
Zn1—O2	2.006 (3)	C14—C13	1.402 (7)
Zn1—O5	1.958 (3)	C14—H14	0.9300
Zn1—O7	2.005 (3)	C16—C15	1.496 (6)
Zn1—N1	2.068 (4)	C16—C17	1.389 (6)
Zn2—O3	1.995 (3)	C16—C21	1.387 (7)
Zn2—O6	1.975 (3)	C18—C17	1.375 (6)
Zn2—O8	1.940 (3)	C18—C19	1.378 (7)
Zn2—N3	2.021 (4)	C18—H18	0.9300
F1—C3	1.338 (5)	C19—C20	1.378 (7)
F3—C17	1.353 (6)	C19—H19	0.9300
F5—C43	1.331 (5)	C20—H20	0.9300
O1—C1	1.250 (5)	C21—C20	1.384 (7)
O2—C1	1.276 (5)	C21—H21	0.9300
O3—C8	1.276 (5)	C22—C23	1.479 (6)
O4—C8	1.237 (5)	C24—C23	1.406 (6)
O5—C15	1.256 (5)	C24—H28'	0.9300
O6—C15	1.266 (5)	C25—C24	1.403 (6)
O7—C22	1.261 (5)	C25—H25	0.9300
O8—C22	1.259 (5)	C26—C25	1.367 (7)
O9—C34	1.231 (5)	C26—C27	1.378 (7)
O10—C40	1.240 (5)	C26—H26	0.9300
O11—C47	1.225 (6)	C27—C28	1.398 (6)
O12—C47	1.301 (6)	C27—H27	0.9300
O12—H121	0.92 (8)	C28—C23	1.398 (6)
N1—C29	1.335 (6)	C28—H28	0.9300
N1—C33	1.353 (5)	C29—C30	1.387 (6)
N2—C34	1.335 (6)	C29—H29	0.9300
N2—H2A	0.82 (5)	C31—C30	1.392 (6)
N2—H2B	0.84 (6)	C31—C32	1.380 (7)
N3—C35	1.335 (6)	C31—H31	0.9300
N3—C39	1.349 (5)	C32—H32	0.9300
N4—C40	1.324 (6)	C33—C32	1.374 (6)
N4—H4A	0.81 (5)	C33—H33	0.9300
N4—H4B	0.92 (7)	C34—C30	1.494 (6)
C2—C1	1.494 (6)	C35—H35	0.9300
C2—C3	1.379 (6)	C36—C35	1.382 (6)
C2—C7	1.394 (6)	C36—C37	1.391 (6)
C3—C4	1.379 (7)	C36—C40	1.504 (6)
C4—H4	0.9300	C37—C38	1.382 (6)
C5—C4	1.379 (7)	C37—H37	0.9300
C5—H5	0.9300	C38—H38	0.9300
C6—C5	1.378 (7)	C39—C38	1.380 (6)
C6—H6	0.9300	C39—H39	0.9300
C7—C6	1.380 (6)	C41—C46	1.374 (8)
C7—H7	0.9300	C41—H41	0.9300
C8—C9	1.490 (6)	C42—C41	1.377 (7)
C9—C14	1.407 (6)	C42—H42	0.9300
C10—C9	1.398 (6)	C43—C42	1.379 (7)
C10—C11	1.398 (7)	C44—C43	1.391 (7)
C10—H14'	0.9300	C44—C47	1.479 (7)
C11—H11	0.9300	C45—C44	1.395 (6)
C12—C11	1.363 (7)	C45—C46	1.371 (7)
C12—H12	0.9300	C45—H45	0.9300
C13—C12	1.372 (7)	C46—H46	0.9300

O2—Zn1—O1	60.92 (12)	C19—C18—H18	120.4
O2—Zn1—N1	100.57 (14)	C18—C19—C20	120.1 (5)
O5—Zn1—O1	95.98 (12)	C18—C19—H19	120.0
O5—Zn1—O2	150.56 (13)	C20—C19—H19	120.0
O5—Zn1—O7	106.60 (12)	C19—C20—C21	119.6 (5)
O5—Zn1—N1	97.64 (13)	C19—C20—H20	120.2
O7—Zn1—O1	154.68 (12)	C21—C20—H20	120.2
O7—Zn1—O2	93.94 (12)	C16—C21—H21	119.0
O7—Zn1—N1	97.05 (13)	C20—C21—C16	121.9 (5)
N1—Zn1—O1	91.04 (13)	C20—C21—H21	119.0
O3—Zn2—N3	112.33 (15)	O7—C22—C23	117.3 (4)
O6—Zn2—O3	97.28 (12)	O8—C22—O7	124.9 (4)
O6—Zn2—N3	106.36 (14)	O8—C22—C23	117.7 (4)
O8—Zn2—O3	129.40 (14)	C24—C23—C22	122.2 (4)
O8—Zn2—O6	107.39 (13)	C28—C23—C22	121.5 (4)
O8—Zn2—N3	102.19 (14)	C28—C23—C24	116.2 (4)
C1—O1—Zn1	82.8 (3)	C23—C24—H28'	119.2
C1—O2—Zn1	95.3 (3)	C25—C24—C23	121.6 (4)
C8—O3—Zn2	102.6 (3)	C25—C24—H28'	119.2
C15—O5—Zn1	140.1 (3)	C24—C25—H25	120.3
C15—O6—Zn2	125.3 (3)	C26—C25—C24	119.4 (4)
C22—O7—Zn1	143.0 (3)	C26—C25—H25	120.3
C22—O8—Zn2	122.4 (3)	C25—C26—C27	121.6 (4)
C47—O12—H121	109 (4)	C25—C26—H26	119.2
C29—N1—Zn1	120.9 (3)	C27—C26—H26	119.2
C29—N1—C33	117.7 (4)	C26—C27—C28	118.4 (4)
C33—N1—Zn1	121.4 (3)	C26—C27—H27	120.8
C34—N2—H2A	120 (4)	C28—C27—H27	120.8
C34—N2—H2B	115 (4)	C23—C28—C27	122.8 (4)
H2A—N2—H2B	124 (5)	C23—C28—H28	118.6
C35—N3—Zn2	119.5 (3)	C27—C28—H28	118.6
C35—N3—C39	118.0 (4)	N1—C29—C30	123.9 (4)
C39—N3—Zn2	122.4 (3)	N1—C29—H29	118.0
C40—N4—H4A	122 (4)	C30—C29—H29	118.0
C40—N4—H4B	114 (4)	C29—C30—C31	117.7 (4)
H4A—N4—H4B	124 (5)	C29—C30—C34	117.4 (4)
O1—C1—O2	120.7 (4)	C31—C30—C34	124.9 (4)
O1—C1—C2	122.0 (4)	C30—C31—H31	120.6
O2—C1—C2	117.3 (4)	C32—C31—C30	118.7 (4)
C3—C2—C1	123.7 (4)	C32—C31—H31	120.6
C3—C2—C7	116.8 (4)	C31—C32—H32	120.0
C7—C2—C1	119.5 (4)	C33—C32—C31	120.1 (4)
F1—C3—C2	120.1 (4)	C33—C32—H32	120.0
F1—C3—C4	117.1 (4)	N1—C33—C32	121.9 (4)
C4—C3—C2	122.8 (4)	N1—C33—H33	119.1
C3—C4—H4	120.5	C32—C33—H33	119.1
C5—C4—C3	118.9 (5)	O9—C34—N2	122.5 (4)
C5—C4—H4	120.5	O9—C34—C30	119.3 (4)
C4—C5—H5	120.0	N2—C34—C30	118.3 (4)
C6—C5—C4	120.1 (5)	N3—C35—C36	123.8 (4)
C6—C5—H5	120.0	N3—C35—H35	118.1
C5—C6—C7	119.9 (5)	C36—C35—H35	118.1
C5—C6—H6	120.1	C35—C36—C37	117.9 (4)
C7—C6—H6	120.1	C35—C36—C40	116.4 (4)
C2—C7—H7	119.3	C37—C36—C40	125.7 (4)
C6—C7—C2	121.4 (4)	C36—C37—H37	120.6
C6—C7—H7	119.3	C38—C37—C36	118.8 (4)
O3—C8—C9	118.7 (4)	C38—C37—H37	120.6
O4—C8—O3	121.1 (4)	C37—C38—H38	120.1
O4—C8—C9	120.2 (4)	C39—C38—C37	119.8 (4)
C10—C9—C8	125.0 (4)	C39—C38—H38	120.1
C14—C9—C10	115.9 (4)	N3—C39—C38	121.8 (4)
C14—C9—C8	119.1 (4)	N3—C39—H39	119.1
C9—C10—H14'	118.9	C38—C39—H39	119.1
C11—C10—C9	122.3 (4)	O10—C40—N4	122.8 (4)
C11—C10—H14'	118.9	O10—C40—C36	118.3 (4)
C10—C11—H11	120.3	N4—C40—C36	118.9 (4)
C12—C11—C10	119.4 (5)	C42—C41—H41	119.9
C12—C11—H11	120.3	C46—C41—C42	120.2 (5)
C11—C12—C13	121.5 (5)	C46—C41—H41	119.9
C11—C12—H12	119.3	C41—C42—C43	119.2 (5)
C13—C12—H12	119.3	C41—C42—H42	120.4
C12—C13—C14	118.9 (5)	C43—C42—H42	120.4
C12—C13—H13	120.6	F5—C43—C42	117.0 (5)
C14—C13—H13	120.6	F5—C43—C44	121.0 (4)
C9—C14—C13	122.2 (4)	C42—C43—C44	122.0 (4)
C9—C14—H14	118.9	C43—C44—C45	117.1 (5)
C13—C14—H14	118.9	C43—C44—C47	125.3 (4)
O5—C15—O6	125.5 (4)	C45—C44—C47	117.6 (4)
O5—C15—C16	118.4 (4)	C44—C45—H45	119.4
O6—C15—C16	116.1 (4)	C46—C45—C44	121.3 (5)
C17—C16—C15	124.3 (4)	C46—C45—H45	119.4
C21—C16—C15	119.2 (4)	C41—C46—H46	119.9
C21—C16—C17	116.4 (4)	C45—C46—C41	120.3 (5)
F3—C17—C16	120.6 (4)	C45—C46—H46	119.9
F3—C17—C18	116.6 (4)	O11—C47—O12	122.8 (5)
C18—C17—C16	122.8 (5)	O11—C47—C44	120.5 (4)
C17—C18—C19	119.1 (5)	O12—C47—C44	116.7 (5)
C17—C18—H18	120.4

O2—Zn1—O1—C1	−3.1 (3)	C2—C7—C6—C5	0.0 (7)
O5—Zn1—O1—C1	−163.8 (3)	O3—C8—C9—C10	−7.4 (7)
O7—Zn1—O1—C1	−10.6 (4)	O3—C8—C9—C14	171.5 (4)
N1—Zn1—O1—C1	98.4 (3)	O4—C8—C9—C10	171.3 (4)
O1—Zn1—O2—C1	3.0 (2)	O4—C8—C9—C14	−9.7 (7)
O5—Zn1—O2—C1	45.1 (4)	C10—C9—C14—C13	0.8 (7)
O7—Zn1—O2—C1	179.9 (3)	C8—C9—C14—C13	−178.3 (5)
N1—Zn1—O2—C1	−82.2 (3)	C11—C10—C9—C14	−0.7 (7)
O1—Zn1—O5—C15	125.1 (5)	C11—C10—C9—C8	178.3 (5)
O2—Zn1—O5—C15	89.0 (5)	C9—C10—C11—C12	0.1 (8)
O7—Zn1—O5—C15	−43.3 (5)	C13—C12—C11—C10	0.4 (8)
N1—Zn1—O5—C15	−143.1 (5)	C14—C13—C12—C11	−0.4 (8)
O1—Zn1—O7—C22	−91.5 (5)	C9—C14—C13—C12	−0.3 (8)
O2—Zn1—O7—C22	−98.0 (5)	C17—C16—C15—O5	−17.1 (7)
O5—Zn1—O7—C22	60.6 (5)	C17—C16—C15—O6	163.6 (4)
N1—Zn1—O7—C22	160.8 (5)	C21—C16—C15—O5	163.9 (4)
O1—Zn1—N1—C29	−118.6 (3)	C21—C16—C15—O6	−15.4 (6)
O1—Zn1—N1—C33	60.8 (3)	C15—C16—C17—F3	−0.8 (7)
O2—Zn1—N1—C29	−58.0 (3)	C15—C16—C17—C18	−178.8 (5)
O2—Zn1—N1—C33	121.4 (3)	C21—C16—C17—F3	178.2 (4)
O5—Zn1—N1—C29	145.2 (3)	C21—C16—C17—C18	0.2 (7)
O5—Zn1—N1—C33	−35.4 (3)	C17—C16—C21—C20	−0.8 (7)
O7—Zn1—N1—C29	37.3 (3)	C15—C16—C21—C20	178.3 (5)
O7—Zn1—N1—C33	−143.2 (3)	C19—C18—C17—F3	−177.8 (5)
O8—Zn2—O3—C8	53.8 (3)	C19—C18—C17—C16	0.3 (8)
O6—Zn2—O3—C8	173.4 (3)	C17—C18—C19—C20	−0.3 (9)
N3—Zn2—O3—C8	−75.5 (3)	C18—C19—C20—C21	−0.3 (9)
O3—Zn2—O6—C15	−50.5 (4)	C16—C21—C20—C19	0.9 (9)
O8—Zn2—O6—C15	84.8 (4)	O7—C22—C23—C24	−162.1 (4)
N3—Zn2—O6—C15	−166.4 (3)	O7—C22—C23—C28	13.1 (6)
O3—Zn2—O8—C22	29.6 (4)	O8—C22—C23—C24	16.2 (6)
O6—Zn2—O8—C22	−85.8 (3)	O8—C22—C23—C28	−168.5 (4)
N3—Zn2—O8—C22	162.5 (3)	C25—C24—C23—C28	−1.8 (6)
O3—Zn2—N3—C35	−57.3 (3)	C25—C24—C23—C22	173.8 (4)
O3—Zn2—N3—C39	117.9 (3)	C26—C25—C24—C23	1.4 (7)
O6—Zn2—N3—C35	48.0 (3)	C27—C26—C25—C24	0.3 (7)
O6—Zn2—N3—C39	−136.8 (3)	C25—C26—C27—C28	−1.6 (7)
O8—Zn2—N3—C35	160.4 (3)	C26—C27—C28—C23	1.1 (7)
O8—Zn2—N3—C39	−24.3 (4)	C27—C28—C23—C24	0.5 (6)
Zn1—O1—C1—O2	5.0 (4)	C27—C28—C23—C22	−175.1 (4)
Zn1—O1—C1—C2	−172.5 (4)	N1—C29—C30—C31	0.5 (7)
Zn1—O2—C1—O1	−5.7 (5)	N1—C29—C30—C34	−178.9 (4)
Zn1—O2—C1—C2	171.9 (3)	C32—C31—C30—C29	−0.8 (6)
Zn2—O3—C8—O4	−5.4 (5)	C32—C31—C30—C34	178.7 (4)
Zn2—O3—C8—C9	173.4 (3)	C30—C31—C32—C33	−0.1 (6)
Zn1—O5—C15—O6	−11.4 (8)	N1—C33—C32—C31	1.3 (7)
Zn1—O5—C15—C16	169.4 (3)	N2—C34—C30—C29	−172.6 (4)
Zn2—O6—C15—O5	−3.1 (6)	N2—C34—C30—C31	8.0 (7)
Zn2—O6—C15—C16	176.2 (3)	O9—C34—C30—C29	6.7 (7)
Zn1—O7—C22—O8	−12.9 (7)	O9—C34—C30—C31	−172.8 (4)
Zn1—O7—C22—C23	165.3 (3)	C37—C36—C35—N3	1.1 (6)
Zn2—O8—C22—O7	16.4 (6)	C40—C36—C35—N3	−177.4 (4)
Zn2—O8—C22—C23	−161.8 (3)	C35—C36—C37—C38	−0.6 (6)
Zn1—N1—C29—C30	−180.0 (3)	C40—C36—C37—C38	177.9 (4)
C33—N1—C29—C30	0.6 (6)	C35—C36—C40—O10	−0.5 (6)
Zn1—N1—C33—C32	179.1 (3)	C37—C36—C40—O10	−179.0 (4)
C29—N1—C33—C32	−1.5 (6)	C35—C36—C40—N4	179.2 (4)
Zn2—N3—C35—C36	175.3 (3)	C37—C36—C40—N4	0.7 (7)
C39—N3—C35—C36	−0.2 (6)	C36—C37—C38—C39	−0.8 (6)
Zn2—N3—C39—C38	−176.6 (3)	N3—C39—C38—C37	1.8 (7)
C35—N3—C39—C38	−1.3 (6)	C42—C41—C46—C45	−0.4 (8)
C3—C2—C1—O1	−6.1 (7)	C43—C42—C41—C46	−0.1 (8)
C3—C2—C1—O2	176.3 (4)	F5—C43—C42—C41	179.6 (4)
C7—C2—C1—O1	171.4 (4)	C44—C43—C42—C41	0.8 (7)
C7—C2—C1—O2	−6.2 (6)	C45—C44—C43—F5	−179.7 (4)
C1—C2—C3—F1	−7.9 (7)	C45—C44—C43—C42	−0.9 (7)
C1—C2—C3—C4	174.4 (5)	C47—C44—C43—F5	0.5 (7)
C7—C2—C3—F1	174.6 (4)	C47—C44—C43—C42	179.2 (4)
C7—C2—C3—C4	−3.2 (7)	C43—C44—C47—O11	−176.7 (5)
C1—C2—C7—C6	−175.2 (4)	C43—C44—C47—O12	3.8 (7)
C3—C2—C7—C6	2.5 (7)	C45—C44—C47—O11	3.5 (7)
F1—C3—C4—C5	−176.5 (4)	C45—C44—C47—O12	−176.0 (4)
C2—C3—C4—C5	1.3 (8)	C46—C45—C44—C43	0.5 (7)
C6—C5—C4—C3	1.4 (8)	C46—C45—C44—C47	−179.7 (5)
C7—C6—C5—C4	−2.0 (8)	C44—C45—C46—C41	0.2 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.82 (5)	2.39 (5)	3.056 (6)	140 (5)
N2—H2B···O10ⁱⁱ	0.84 (6)	2.03 (5)	2.863 (6)	176.4 (5)
N4—H4A···O4ⁱⁱⁱ	0.81 (5)	2.11 (5)	2.825 (5)	149 (5)
N4—H4B···O9^iv	0.92 (7)	1.96 (7)	2.874 (6)	176 (7)
O12—H121···O11^v	0.92 (8)	1.71 (8)	2.626 (5)	174 (6)

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

Experimental details

Crystal data
Chemical formula	[Zn₂(C₇H₄FO₂)₄(C₆H₆N₂O)₂]·C₇H₅FO₂
M_r	1071.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.5143 (2), 16.7106 (3), 20.6673 (4)
β (°)	92.929 (2)
V (Å³)	4316.33 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.29 × 0.25 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.710, 0.840
No. of measured, independent and observed [I > 2σ(I)] reflections	37814, 10696, 7459
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.097, 1.01
No. of reflections	10696
No. of parameters	659
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.39, −0.59

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	2.296 (3)	Zn2—O3	1.995 (3)
Zn1—O2	2.006 (3)	Zn2—O6	1.975 (3)
Zn1—O5	1.958 (3)	Zn2—O8	1.940 (3)
Zn1—O7	2.005 (3)	Zn2—N3	2.021 (4)
Zn1—N1	2.068 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.82 (5)	2.39 (5)	3.056 (6)	140 (5)
N2—H2B···O10ⁱⁱ	0.84 (6)	2.03 (5)	2.863 (6)	176.4 (5)
N4—H4A···O4ⁱⁱⁱ	0.81 (5)	2.11 (5)	2.825 (5)	149 (5)
N4—H4B···O9^iv	0.92 (7)	1.96 (7)	2.874 (6)	176 (7)
O12—H121···O11^v	0.92 (8)	1.71 (8)	2.626 (5)	174 (6)

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+1/2; (iv) x, y−1, z; (v) −x+1, −y+2, −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 Kafkas University Research Fund (grant No. 2009-FEF-03).

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