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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1608–m1609.
Published online 2009 November 21. doi:  10.1107/S1600536809048089
PMCID: PMC2971791

Bis(μ-2-fluoro­benzoato-1:2κ2 O:O′)(2-fluoro­benzoato-1κ2 O,O′)(2-fluoro­benzoato-2κO)dinicotinamide-1κN 1,2κN 1-dizinc(II)–2-fluoro­benzoic acid (1/1)

Abstract

The asymmetric unit of the title compound, [Zn2(C7H4FO2)4(C6H6N2O)2]·C7H5FO2, consists of a binuclear ZnII 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 [triangle]); Krishnamachari (1974 [triangle]). For related structures, see: Hökelek & Necefoğlu (1996 [triangle]); Hökelek et al. (2009a [triangle],b [triangle],c [triangle],d [triangle]); Greenaway et al. (1984 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1608-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C7H4FO2)4(C6H6N2O)2]·C7H5FO2
  • M r = 1071.55
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1608-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.097
  • S = 1.01
  • 10696 reflections
  • 659 parameters
  • 10 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.39 e Å−3
  • Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048089/xu2668sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048089/xu2668Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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).

supplementary crystallographic information

Comment

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 ZnII 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 ZnII atoms are surrounded by three FB groups and one NA ligand. The NA ligands are coordinated to ZnII ions through pyridine N atoms only. Two FB groups act as bridging ligands, while the other two FB groups are coordinated to ZnII 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.

Experimental

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.

Refinement

Atoms H2A, H2B, H4A and H4B (for NH2) and H121 (for OH) were located in a difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically with C—H = 0.93 Å for aromatic H atoms and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). The F2 and H14 atoms attached at C10 and C14, and the F4 and H28 atoms attached at C24 and C28, respectively, are disordered over two orientations. During the refinement process, the disordered F2, F4, H14, H28 and F2', F4', H14', H28' atoms were refined with occupancies of 0.7 and 0.3, respectively.

Figures

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.

Crystal data

[Zn2(C7H4FO2)4(C6H6N2O)2]·C7H5FO2F(000) = 2176
Mr = 1071.55Dx = 1.649 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9923 reflections
a = 12.5143 (2) Åθ = 2.3–28.1°
b = 16.7106 (3) ŵ = 1.21 mm1
c = 20.6673 (4) ÅT = 100 K
β = 92.929 (2)°Block, colorless
V = 4316.33 (13) Å30.29 × 0.25 × 0.14 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer10696 independent reflections
Radiation source: fine-focus sealed tube7459 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] and ω scansθmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −16→13
Tmin = 0.710, Tmax = 0.840k = −22→22
37814 measured reflectionsl = −26→27

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0383P)2 + 3.8099P] where P = (Fo2 + 2Fc2)/3
10696 reflections(Δ/σ)max = 0.001
659 parametersΔρmax = 1.39 e Å3
10 restraintsΔρmin = −0.59 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Zn10.17153 (4)0.67257 (3)0.24483 (2)0.01406 (14)
Zn20.31257 (4)0.51261 (3)0.29078 (3)0.01641 (14)
F1−0.0139 (2)0.6414 (2)0.02860 (15)0.0383 (8)
F20.1234 (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)
F40.6020 (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
F50.4883 (2)0.73739 (19)0.00733 (15)0.0377 (8)
O10.0703 (3)0.6540 (2)0.15019 (15)0.0240 (8)
O20.2346 (2)0.6999 (2)0.16036 (14)0.0199 (7)
O30.2399 (2)0.5160 (2)0.20262 (16)0.0270 (8)
O40.4067 (2)0.5492 (2)0.19029 (16)0.0242 (8)
O50.0874 (2)0.60130 (18)0.29767 (14)0.0163 (7)
O60.1828 (2)0.49874 (19)0.34017 (15)0.0199 (7)
O70.3061 (2)0.6981 (2)0.29769 (14)0.0182 (7)
O80.4007 (2)0.59306 (19)0.33526 (16)0.0211 (7)
O90.2568 (3)0.9875 (2)0.26713 (19)0.0319 (9)
O100.2451 (2)0.2018 (2)0.27913 (16)0.0228 (8)
O110.6174 (3)0.9659 (2)0.0211 (2)0.0380 (10)
O120.4706 (3)0.8936 (2)0.00208 (19)0.0331 (9)
H1210.443 (5)0.943 (5)−0.008 (3)0.07 (2)*
N10.0910 (3)0.7776 (2)0.26319 (17)0.0148 (8)
N20.1202 (4)1.0617 (3)0.3008 (2)0.0235 (10)
H2A0.058 (4)1.063 (3)0.310 (2)0.022 (14)*
H2B0.158 (4)1.102 (3)0.296 (3)0.030 (16)*
N30.4006 (3)0.4123 (2)0.30545 (17)0.0142 (8)
N40.3912 (4)0.1241 (3)0.2944 (2)0.0209 (9)
H4A0.454 (4)0.120 (3)0.304 (2)0.024 (15)*
H4B0.347 (5)0.082 (4)0.284 (3)0.06 (2)*
C10.1502 (4)0.6839 (3)0.1255 (2)0.0172 (10)
C20.1499 (3)0.7054 (3)0.0554 (2)0.0163 (10)
C30.0668 (4)0.6878 (3)0.0113 (2)0.0203 (10)
C40.0640 (4)0.7140 (3)−0.0521 (2)0.0273 (12)
H40.00600.7019−0.08030.033*
C50.1486 (4)0.7584 (3)−0.0729 (2)0.0290 (12)
H50.14720.7774−0.11520.035*
C60.2351 (4)0.7745 (3)−0.0310 (2)0.0255 (12)
H60.29310.8030−0.04550.031*
C70.2356 (4)0.7483 (3)0.0323 (2)0.0196 (10)
H70.29440.75950.06020.023*
C80.3164 (3)0.5334 (3)0.1666 (2)0.0179 (10)
C90.2958 (3)0.5326 (3)0.0950 (2)0.0169 (10)
C100.2015 (4)0.5058 (3)0.0629 (2)0.0230 (11)
H14'0.14730.48530.08720.028*0.30
C110.1859 (4)0.5086 (3)−0.0046 (3)0.0282 (12)
H110.12220.4903−0.02460.034*
C120.2649 (4)0.5383 (3)−0.0407 (3)0.0312 (13)
H120.25430.5405−0.08550.037*
C130.3598 (4)0.5651 (3)−0.0124 (2)0.0306 (13)
H130.41320.5850−0.03770.037*
C140.3749 (4)0.5620 (3)0.0552 (2)0.0234 (11)
H140.43940.57990.07440.028*0.70
C150.0994 (3)0.5414 (3)0.3341 (2)0.0145 (9)
C160.0079 (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)
H18−0.21760.57540.43010.034*
C19−0.1571 (4)0.4659 (4)0.4501 (3)0.0362 (14)
H19−0.21190.44890.47560.043*
C20−0.0727 (4)0.4155 (3)0.4393 (3)0.0367 (14)
H20−0.07000.36470.45760.044*
C210.0082 (4)0.4410 (3)0.4010 (2)0.0258 (12)
H210.06440.40640.39340.031*
C220.3881 (3)0.6668 (3)0.3252 (2)0.0158 (10)
C230.4772 (3)0.7209 (3)0.3453 (2)0.0141 (9)
C240.5816 (3)0.6927 (3)0.3596 (2)0.0174 (10)
H28'0.59400.63780.36050.021*0.30
C250.6675 (4)0.7452 (3)0.3726 (2)0.0216 (11)
H250.73620.72530.38110.026*
C260.6492 (4)0.8258 (3)0.3728 (2)0.0216 (11)
H260.70640.86050.38120.026*
C270.5482 (4)0.8570 (3)0.3608 (2)0.0214 (11)
H270.53640.91190.36210.026*
C280.4637 (3)0.8040 (3)0.3467 (2)0.0186 (10)
H280.39570.82480.33780.022*0.70
C290.1429 (3)0.8473 (3)0.2675 (2)0.0146 (9)
H290.21620.84720.26200.018*
C300.0941 (3)0.9198 (3)0.2797 (2)0.0150 (10)
C31−0.0155 (3)0.9193 (3)0.2884 (2)0.0168 (10)
H31−0.05150.96650.29720.020*
C32−0.0698 (3)0.8475 (3)0.2837 (2)0.0181 (10)
H32−0.14300.84590.28950.022*
C33−0.0157 (3)0.7782 (3)0.2707 (2)0.0168 (10)
H33−0.05360.73040.26680.020*
C340.1630 (3)0.9929 (3)0.2819 (2)0.0187 (10)
C350.3537 (3)0.3409 (3)0.2987 (2)0.0142 (9)
H350.27990.33930.29060.017*
C360.4082 (3)0.2690 (3)0.3032 (2)0.0133 (9)
C370.5183 (3)0.2716 (3)0.3166 (2)0.0170 (10)
H370.55790.22460.32040.020*
C380.5676 (3)0.3453 (3)0.3241 (2)0.0184 (10)
H380.64090.34830.33360.022*
C390.5075 (3)0.4143 (3)0.3175 (2)0.0174 (10)
H390.54180.46360.32140.021*
C400.3426 (3)0.1945 (3)0.2915 (2)0.0169 (10)
C410.7570 (4)0.6917 (3)0.0614 (3)0.0303 (12)
H410.79900.64690.07090.036*
C420.6512 (4)0.6824 (3)0.0410 (2)0.0269 (12)
H420.62150.63160.03670.032*
C430.5899 (4)0.7494 (3)0.0272 (2)0.0225 (11)
C440.6319 (4)0.8263 (3)0.0324 (2)0.0195 (10)
C450.7393 (4)0.8332 (3)0.0534 (2)0.0268 (12)
H450.76990.88380.05780.032*
C460.8006 (4)0.7669 (3)0.0677 (3)0.0329 (13)
H460.87190.77290.08170.039*
C470.5720 (4)0.9010 (3)0.0178 (2)0.0214 (11)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0128 (2)0.0158 (3)0.0136 (3)−0.0009 (2)0.00059 (19)0.0017 (2)
Zn20.0136 (2)0.0104 (3)0.0248 (3)0.0005 (2)−0.0018 (2)0.0001 (2)
F10.0310 (16)0.042 (2)0.0416 (19)−0.0084 (15)−0.0021 (14)−0.0026 (16)
F20.0158 (18)0.029 (2)0.026 (2)−0.0116 (17)0.0042 (16)0.0000 (18)
F30.0401 (17)0.0233 (17)0.0473 (19)0.0134 (14)0.0224 (15)0.0138 (15)
F40.025 (2)0.018 (2)0.044 (3)0.0016 (18)−0.0054 (18)0.003 (2)
F50.0316 (16)0.0317 (19)0.049 (2)−0.0060 (14)−0.0037 (14)0.0023 (16)
O10.0318 (18)0.021 (2)0.0194 (17)−0.0047 (16)0.0082 (14)0.0002 (15)
O20.0195 (15)0.0255 (19)0.0146 (16)0.0056 (15)−0.0014 (13)0.0000 (15)
O30.0132 (15)0.044 (2)0.0240 (18)0.0029 (16)0.0032 (13)0.0131 (17)
O40.0199 (16)0.024 (2)0.0287 (19)−0.0058 (15)−0.0002 (14)−0.0004 (16)
O50.0183 (15)0.0118 (17)0.0189 (16)−0.0005 (13)0.0019 (13)0.0034 (14)
O60.0169 (15)0.0185 (19)0.0246 (18)0.0032 (14)0.0033 (13)0.0032 (14)
O70.0148 (15)0.0205 (18)0.0189 (17)−0.0008 (14)−0.0040 (13)−0.0011 (14)
O80.0203 (16)0.0134 (18)0.0292 (19)−0.0025 (14)−0.0035 (14)−0.0016 (15)
O90.0190 (16)0.0164 (19)0.061 (3)−0.0025 (15)0.0111 (17)−0.0072 (18)
O100.0151 (15)0.0142 (18)0.039 (2)0.0004 (14)−0.0032 (14)0.0005 (16)
O110.0239 (18)0.022 (2)0.068 (3)−0.0010 (17)0.0012 (18)0.005 (2)
O120.0241 (18)0.025 (2)0.050 (3)0.0028 (17)−0.0048 (17)0.0043 (19)
N10.0137 (17)0.017 (2)0.0136 (19)−0.0028 (16)−0.0004 (14)0.0001 (16)
N20.015 (2)0.015 (2)0.040 (3)0.001 (2)−0.0005 (19)0.000 (2)
N30.0141 (17)0.013 (2)0.0158 (19)0.0004 (16)0.0007 (14)−0.0001 (16)
N40.017 (2)0.013 (2)0.032 (2)0.0016 (19)−0.0005 (18)−0.0005 (19)
C10.024 (2)0.012 (2)0.016 (2)0.005 (2)0.0054 (19)−0.001 (2)
C20.018 (2)0.015 (2)0.016 (2)0.003 (2)0.0017 (18)−0.002 (2)
C30.022 (2)0.018 (3)0.021 (2)−0.003 (2)0.0013 (19)−0.001 (2)
C40.035 (3)0.027 (3)0.019 (3)0.003 (2)−0.010 (2)−0.004 (2)
C50.048 (3)0.026 (3)0.013 (2)0.006 (3)0.004 (2)0.001 (2)
C60.029 (3)0.026 (3)0.022 (3)0.000 (2)0.010 (2)0.002 (2)
C70.021 (2)0.019 (3)0.019 (2)0.003 (2)0.0038 (19)−0.001 (2)
C80.018 (2)0.011 (2)0.024 (3)0.0041 (19)0.0036 (19)0.003 (2)
C90.017 (2)0.011 (2)0.023 (2)0.0040 (19)0.0033 (18)0.003 (2)
C100.023 (2)0.013 (3)0.033 (3)0.001 (2)0.003 (2)0.001 (2)
C110.031 (3)0.016 (3)0.036 (3)−0.001 (2)−0.011 (2)−0.006 (2)
C120.047 (3)0.024 (3)0.022 (3)0.000 (3)−0.001 (2)−0.003 (2)
C130.038 (3)0.031 (3)0.024 (3)−0.004 (3)0.012 (2)0.002 (2)
C140.021 (2)0.023 (3)0.027 (3)−0.001 (2)0.006 (2)0.000 (2)
C150.016 (2)0.013 (2)0.015 (2)−0.0024 (19)−0.0026 (17)−0.003 (2)
C160.016 (2)0.015 (2)0.017 (2)0.000 (2)−0.0012 (17)0.001 (2)
C170.025 (2)0.017 (3)0.024 (3)0.003 (2)0.003 (2)0.005 (2)
C180.023 (2)0.030 (3)0.033 (3)0.009 (2)0.010 (2)0.009 (3)
C190.025 (3)0.035 (3)0.049 (4)0.001 (3)0.015 (2)0.018 (3)
C200.030 (3)0.024 (3)0.058 (4)0.000 (2)0.014 (3)0.021 (3)
C210.019 (2)0.017 (3)0.041 (3)0.002 (2)0.003 (2)0.006 (2)
C220.018 (2)0.017 (3)0.012 (2)−0.002 (2)0.0047 (17)−0.003 (2)
C230.019 (2)0.013 (2)0.010 (2)−0.0023 (19)0.0013 (17)−0.0009 (19)
C240.019 (2)0.015 (3)0.018 (2)−0.002 (2)−0.0016 (18)0.002 (2)
C250.018 (2)0.025 (3)0.022 (3)−0.002 (2)−0.0028 (19)0.003 (2)
C260.021 (2)0.021 (3)0.023 (2)−0.011 (2)0.0035 (19)−0.003 (2)
C270.028 (2)0.014 (3)0.023 (3)−0.004 (2)0.009 (2)−0.003 (2)
C280.019 (2)0.019 (3)0.018 (2)0.000 (2)0.0037 (18)−0.001 (2)
C290.0118 (19)0.016 (3)0.015 (2)−0.0012 (19)−0.0009 (17)0.0019 (19)
C300.014 (2)0.015 (2)0.016 (2)0.0012 (19)−0.0018 (17)0.0013 (19)
C310.017 (2)0.019 (3)0.015 (2)0.004 (2)0.0007 (18)0.002 (2)
C320.0097 (19)0.027 (3)0.018 (2)0.001 (2)0.0000 (17)0.005 (2)
C330.015 (2)0.019 (3)0.016 (2)−0.004 (2)−0.0022 (17)0.004 (2)
C340.018 (2)0.015 (3)0.022 (2)0.003 (2)−0.0029 (19)0.000 (2)
C350.0138 (19)0.014 (2)0.015 (2)0.0004 (19)−0.0006 (17)0.0002 (19)
C360.016 (2)0.012 (2)0.012 (2)0.0012 (19)0.0012 (17)−0.0001 (18)
C370.017 (2)0.017 (3)0.016 (2)0.005 (2)0.0019 (18)0.002 (2)
C380.013 (2)0.021 (3)0.021 (2)0.000 (2)−0.0008 (18)0.001 (2)
C390.017 (2)0.016 (3)0.019 (2)−0.004 (2)−0.0001 (18)−0.001 (2)
C400.018 (2)0.015 (3)0.018 (2)0.002 (2)0.0024 (18)0.000 (2)
C410.033 (3)0.027 (3)0.032 (3)0.007 (2)0.006 (2)0.001 (2)
C420.040 (3)0.018 (3)0.024 (3)−0.004 (2)0.010 (2)−0.001 (2)
C430.022 (2)0.028 (3)0.018 (2)−0.004 (2)0.0018 (19)−0.001 (2)
C440.021 (2)0.022 (3)0.016 (2)0.001 (2)0.0037 (18)−0.001 (2)
C450.025 (2)0.023 (3)0.033 (3)0.000 (2)0.002 (2)0.000 (2)
C460.027 (3)0.029 (3)0.042 (3)0.003 (3)0.000 (2)−0.001 (3)
C470.023 (2)0.023 (3)0.018 (2)0.000 (2)0.0057 (19)0.000 (2)

Geometric parameters (Å, °)

Zn1—O12.296 (3)C13—H130.9300
Zn1—O22.006 (3)C14—C131.402 (7)
Zn1—O51.958 (3)C14—H140.9300
Zn1—O72.005 (3)C16—C151.496 (6)
Zn1—N12.068 (4)C16—C171.389 (6)
Zn2—O31.995 (3)C16—C211.387 (7)
Zn2—O61.975 (3)C18—C171.375 (6)
Zn2—O81.940 (3)C18—C191.378 (7)
Zn2—N32.021 (4)C18—H180.9300
F1—C31.338 (5)C19—C201.378 (7)
F3—C171.353 (6)C19—H190.9300
F5—C431.331 (5)C20—H200.9300
O1—C11.250 (5)C21—C201.384 (7)
O2—C11.276 (5)C21—H210.9300
O3—C81.276 (5)C22—C231.479 (6)
O4—C81.237 (5)C24—C231.406 (6)
O5—C151.256 (5)C24—H28'0.9300
O6—C151.266 (5)C25—C241.403 (6)
O7—C221.261 (5)C25—H250.9300
O8—C221.259 (5)C26—C251.367 (7)
O9—C341.231 (5)C26—C271.378 (7)
O10—C401.240 (5)C26—H260.9300
O11—C471.225 (6)C27—C281.398 (6)
O12—C471.301 (6)C27—H270.9300
O12—H1210.92 (8)C28—C231.398 (6)
N1—C291.335 (6)C28—H280.9300
N1—C331.353 (5)C29—C301.387 (6)
N2—C341.335 (6)C29—H290.9300
N2—H2A0.82 (5)C31—C301.392 (6)
N2—H2B0.84 (6)C31—C321.380 (7)
N3—C351.335 (6)C31—H310.9300
N3—C391.349 (5)C32—H320.9300
N4—C401.324 (6)C33—C321.374 (6)
N4—H4A0.81 (5)C33—H330.9300
N4—H4B0.92 (7)C34—C301.494 (6)
C2—C11.494 (6)C35—H350.9300
C2—C31.379 (6)C36—C351.382 (6)
C2—C71.394 (6)C36—C371.391 (6)
C3—C41.379 (7)C36—C401.504 (6)
C4—H40.9300C37—C381.382 (6)
C5—C41.379 (7)C37—H370.9300
C5—H50.9300C38—H380.9300
C6—C51.378 (7)C39—C381.380 (6)
C6—H60.9300C39—H390.9300
C7—C61.380 (6)C41—C461.374 (8)
C7—H70.9300C41—H410.9300
C8—C91.490 (6)C42—C411.377 (7)
C9—C141.407 (6)C42—H420.9300
C10—C91.398 (6)C43—C421.379 (7)
C10—C111.398 (7)C44—C431.391 (7)
C10—H14'0.9300C44—C471.479 (7)
C11—H110.9300C45—C441.395 (6)
C12—C111.363 (7)C45—C461.371 (7)
C12—H120.9300C45—H450.9300
C13—C121.372 (7)C46—H460.9300
O2—Zn1—O160.92 (12)C19—C18—H18120.4
O2—Zn1—N1100.57 (14)C18—C19—C20120.1 (5)
O5—Zn1—O195.98 (12)C18—C19—H19120.0
O5—Zn1—O2150.56 (13)C20—C19—H19120.0
O5—Zn1—O7106.60 (12)C19—C20—C21119.6 (5)
O5—Zn1—N197.64 (13)C19—C20—H20120.2
O7—Zn1—O1154.68 (12)C21—C20—H20120.2
O7—Zn1—O293.94 (12)C16—C21—H21119.0
O7—Zn1—N197.05 (13)C20—C21—C16121.9 (5)
N1—Zn1—O191.04 (13)C20—C21—H21119.0
O3—Zn2—N3112.33 (15)O7—C22—C23117.3 (4)
O6—Zn2—O397.28 (12)O8—C22—O7124.9 (4)
O6—Zn2—N3106.36 (14)O8—C22—C23117.7 (4)
O8—Zn2—O3129.40 (14)C24—C23—C22122.2 (4)
O8—Zn2—O6107.39 (13)C28—C23—C22121.5 (4)
O8—Zn2—N3102.19 (14)C28—C23—C24116.2 (4)
C1—O1—Zn182.8 (3)C23—C24—H28'119.2
C1—O2—Zn195.3 (3)C25—C24—C23121.6 (4)
C8—O3—Zn2102.6 (3)C25—C24—H28'119.2
C15—O5—Zn1140.1 (3)C24—C25—H25120.3
C15—O6—Zn2125.3 (3)C26—C25—C24119.4 (4)
C22—O7—Zn1143.0 (3)C26—C25—H25120.3
C22—O8—Zn2122.4 (3)C25—C26—C27121.6 (4)
C47—O12—H121109 (4)C25—C26—H26119.2
C29—N1—Zn1120.9 (3)C27—C26—H26119.2
C29—N1—C33117.7 (4)C26—C27—C28118.4 (4)
C33—N1—Zn1121.4 (3)C26—C27—H27120.8
C34—N2—H2A120 (4)C28—C27—H27120.8
C34—N2—H2B115 (4)C23—C28—C27122.8 (4)
H2A—N2—H2B124 (5)C23—C28—H28118.6
C35—N3—Zn2119.5 (3)C27—C28—H28118.6
C35—N3—C39118.0 (4)N1—C29—C30123.9 (4)
C39—N3—Zn2122.4 (3)N1—C29—H29118.0
C40—N4—H4A122 (4)C30—C29—H29118.0
C40—N4—H4B114 (4)C29—C30—C31117.7 (4)
H4A—N4—H4B124 (5)C29—C30—C34117.4 (4)
O1—C1—O2120.7 (4)C31—C30—C34124.9 (4)
O1—C1—C2122.0 (4)C30—C31—H31120.6
O2—C1—C2117.3 (4)C32—C31—C30118.7 (4)
C3—C2—C1123.7 (4)C32—C31—H31120.6
C3—C2—C7116.8 (4)C31—C32—H32120.0
C7—C2—C1119.5 (4)C33—C32—C31120.1 (4)
F1—C3—C2120.1 (4)C33—C32—H32120.0
F1—C3—C4117.1 (4)N1—C33—C32121.9 (4)
C4—C3—C2122.8 (4)N1—C33—H33119.1
C3—C4—H4120.5C32—C33—H33119.1
C5—C4—C3118.9 (5)O9—C34—N2122.5 (4)
C5—C4—H4120.5O9—C34—C30119.3 (4)
C4—C5—H5120.0N2—C34—C30118.3 (4)
C6—C5—C4120.1 (5)N3—C35—C36123.8 (4)
C6—C5—H5120.0N3—C35—H35118.1
C5—C6—C7119.9 (5)C36—C35—H35118.1
C5—C6—H6120.1C35—C36—C37117.9 (4)
C7—C6—H6120.1C35—C36—C40116.4 (4)
C2—C7—H7119.3C37—C36—C40125.7 (4)
C6—C7—C2121.4 (4)C36—C37—H37120.6
C6—C7—H7119.3C38—C37—C36118.8 (4)
O3—C8—C9118.7 (4)C38—C37—H37120.6
O4—C8—O3121.1 (4)C37—C38—H38120.1
O4—C8—C9120.2 (4)C39—C38—C37119.8 (4)
C10—C9—C8125.0 (4)C39—C38—H38120.1
C14—C9—C10115.9 (4)N3—C39—C38121.8 (4)
C14—C9—C8119.1 (4)N3—C39—H39119.1
C9—C10—H14'118.9C38—C39—H39119.1
C11—C10—C9122.3 (4)O10—C40—N4122.8 (4)
C11—C10—H14'118.9O10—C40—C36118.3 (4)
C10—C11—H11120.3N4—C40—C36118.9 (4)
C12—C11—C10119.4 (5)C42—C41—H41119.9
C12—C11—H11120.3C46—C41—C42120.2 (5)
C11—C12—C13121.5 (5)C46—C41—H41119.9
C11—C12—H12119.3C41—C42—C43119.2 (5)
C13—C12—H12119.3C41—C42—H42120.4
C12—C13—C14118.9 (5)C43—C42—H42120.4
C12—C13—H13120.6F5—C43—C42117.0 (5)
C14—C13—H13120.6F5—C43—C44121.0 (4)
C9—C14—C13122.2 (4)C42—C43—C44122.0 (4)
C9—C14—H14118.9C43—C44—C45117.1 (5)
C13—C14—H14118.9C43—C44—C47125.3 (4)
O5—C15—O6125.5 (4)C45—C44—C47117.6 (4)
O5—C15—C16118.4 (4)C44—C45—H45119.4
O6—C15—C16116.1 (4)C46—C45—C44121.3 (5)
C17—C16—C15124.3 (4)C46—C45—H45119.4
C21—C16—C15119.2 (4)C41—C46—H46119.9
C21—C16—C17116.4 (4)C45—C46—C41120.3 (5)
F3—C17—C16120.6 (4)C45—C46—H46119.9
F3—C17—C18116.6 (4)O11—C47—O12122.8 (5)
C18—C17—C16122.8 (5)O11—C47—C44120.5 (4)
C17—C18—C19119.1 (5)O12—C47—C44116.7 (5)
C17—C18—H18120.4
O2—Zn1—O1—C1−3.1 (3)C2—C7—C6—C50.0 (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—C14171.5 (4)
N1—Zn1—O1—C198.4 (3)O4—C8—C9—C10171.3 (4)
O1—Zn1—O2—C13.0 (2)O4—C8—C9—C14−9.7 (7)
O5—Zn1—O2—C145.1 (4)C10—C9—C14—C130.8 (7)
O7—Zn1—O2—C1179.9 (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—C15125.1 (5)C11—C10—C9—C8178.3 (5)
O2—Zn1—O5—C1589.0 (5)C9—C10—C11—C120.1 (8)
O7—Zn1—O5—C15−43.3 (5)C13—C12—C11—C100.4 (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—C2260.6 (5)C17—C16—C15—O6163.6 (4)
N1—Zn1—O7—C22160.8 (5)C21—C16—C15—O5163.9 (4)
O1—Zn1—N1—C29−118.6 (3)C21—C16—C15—O6−15.4 (6)
O1—Zn1—N1—C3360.8 (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—C33121.4 (3)C21—C16—C17—F3178.2 (4)
O5—Zn1—N1—C29145.2 (3)C21—C16—C17—C180.2 (7)
O5—Zn1—N1—C33−35.4 (3)C17—C16—C21—C20−0.8 (7)
O7—Zn1—N1—C2937.3 (3)C15—C16—C21—C20178.3 (5)
O7—Zn1—N1—C33−143.2 (3)C19—C18—C17—F3−177.8 (5)
O8—Zn2—O3—C853.8 (3)C19—C18—C17—C160.3 (8)
O6—Zn2—O3—C8173.4 (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—C190.9 (9)
O8—Zn2—O6—C1584.8 (4)O7—C22—C23—C24−162.1 (4)
N3—Zn2—O6—C15−166.4 (3)O7—C22—C23—C2813.1 (6)
O3—Zn2—O8—C2229.6 (4)O8—C22—C23—C2416.2 (6)
O6—Zn2—O8—C22−85.8 (3)O8—C22—C23—C28−168.5 (4)
N3—Zn2—O8—C22162.5 (3)C25—C24—C23—C28−1.8 (6)
O3—Zn2—N3—C35−57.3 (3)C25—C24—C23—C22173.8 (4)
O3—Zn2—N3—C39117.9 (3)C26—C25—C24—C231.4 (7)
O6—Zn2—N3—C3548.0 (3)C27—C26—C25—C240.3 (7)
O6—Zn2—N3—C39−136.8 (3)C25—C26—C27—C28−1.6 (7)
O8—Zn2—N3—C35160.4 (3)C26—C27—C28—C231.1 (7)
O8—Zn2—N3—C39−24.3 (4)C27—C28—C23—C240.5 (6)
Zn1—O1—C1—O25.0 (4)C27—C28—C23—C22−175.1 (4)
Zn1—O1—C1—C2−172.5 (4)N1—C29—C30—C310.5 (7)
Zn1—O2—C1—O1−5.7 (5)N1—C29—C30—C34−178.9 (4)
Zn1—O2—C1—C2171.9 (3)C32—C31—C30—C29−0.8 (6)
Zn2—O3—C8—O4−5.4 (5)C32—C31—C30—C34178.7 (4)
Zn2—O3—C8—C9173.4 (3)C30—C31—C32—C33−0.1 (6)
Zn1—O5—C15—O6−11.4 (8)N1—C33—C32—C311.3 (7)
Zn1—O5—C15—C16169.4 (3)N2—C34—C30—C29−172.6 (4)
Zn2—O6—C15—O5−3.1 (6)N2—C34—C30—C318.0 (7)
Zn2—O6—C15—C16176.2 (3)O9—C34—C30—C296.7 (7)
Zn1—O7—C22—O8−12.9 (7)O9—C34—C30—C31−172.8 (4)
Zn1—O7—C22—C23165.3 (3)C37—C36—C35—N31.1 (6)
Zn2—O8—C22—O716.4 (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—C38177.9 (4)
C33—N1—C29—C300.6 (6)C35—C36—C40—O10−0.5 (6)
Zn1—N1—C33—C32179.1 (3)C37—C36—C40—O10−179.0 (4)
C29—N1—C33—C32−1.5 (6)C35—C36—C40—N4179.2 (4)
Zn2—N3—C35—C36175.3 (3)C37—C36—C40—N40.7 (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—C371.8 (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—O2176.3 (4)F5—C43—C42—C41179.6 (4)
C7—C2—C1—O1171.4 (4)C44—C43—C42—C410.8 (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—C4174.4 (5)C47—C44—C43—F50.5 (7)
C7—C2—C3—F1174.6 (4)C47—C44—C43—C42179.2 (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—O123.8 (7)
C3—C2—C7—C62.5 (7)C45—C44—C47—O113.5 (7)
F1—C3—C4—C5−176.5 (4)C45—C44—C47—O12−176.0 (4)
C2—C3—C4—C51.3 (8)C46—C45—C44—C430.5 (7)
C6—C5—C4—C31.4 (8)C46—C45—C44—C47−179.7 (5)
C7—C6—C5—C4−2.0 (8)C44—C45—C46—C410.2 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.82 (5)2.39 (5)3.056 (6)140 (5)
N2—H2B···O10ii0.84 (6)2.03 (5)2.863 (6)176.4 (5)
N4—H4A···O4iii0.81 (5)2.11 (5)2.825 (5)149 (5)
N4—H4B···O9iv0.92 (7)1.96 (7)2.874 (6)176 (7)
O12—H121···O11v0.92 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2668).

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