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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): m1128.
Published online 2008 August 6. doi:  10.1107/S1600536808024549
PMCID: PMC2960502

Hexa-μ2-acetato-1:2κ4 O:O′;1:2κ2 O:O;2:3κ4 O:O′;2:3κ2 O:O-bis­(2-amino-7-chloro-5-methyl-1,8-naphthyridine)-1κN 1,3κN 1-trizinc(II)

Abstract

The title complex, [Zn3(C2H3O2)6(C9H8ClN3)2], contains three ZnII atoms bridged by six acetate ligands. The central ZnII ion, located on an inversion centre, is surrounded by six O atoms from acetate ligands in a distorted octa­hedral geometry [Zn—O = 1.9588 (12)–2.1237 (12) Å]. The terminal ZnII ions are coordinated by one N atom of 2-amino-7-chloro-5-methyl-1,8-naphthyridine and three O atoms of three acetate ligands in a distorted tetra­hedral geometry. The separation between the central and terminal ZnII ions is 3.245 (3) Å.

Related literature

For related literature, see: Baker & Norman (2004 [triangle]); Lis et al. (2005 [triangle]); Stadie et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1128-scheme1.jpg

Experimental

Crystal data

  • [Zn3(C2H3O2)6(C9H8ClN3)2]
  • M r = 937.64
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1128-efi1.jpg
  • a = 9.1978 (12) Å
  • b = 9.2108 (13) Å
  • c = 12.0457 (16) Å
  • α = 93.602 (3)°
  • β = 91.685 (2)°
  • γ = 118.247 (2)°
  • V = 895.2 (2) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 2.21 mm−1
  • T = 113 (2) K
  • 0.12 × 0.08 × 0.02 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.782, T max = 0.956
  • 11008 measured reflections
  • 4221 independent reflections
  • 3495 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.065
  • S = 1.01
  • 4221 reflections
  • 253 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.65 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: XP in SHELXTL.

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024549/hg2413sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024549/hg2413Isup2.hkl

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

Acknowledgments

We thank Henan Agricultural University for the generous support of this study.

supplementary crystallographic information

Comment

Acetic acid is versatile ligand which can function in monodentate or bidentate modes in metal complexes (Baker & Norman, 2004; Lis et al., 2005; Stadie et al., 2007). Here, we report the crystal structure of the title compound, (I), in which three ZnII ions are bridged by three acetic acid ligands.

The middle Zn atom in (I) (Fig. 1) has a distorted octahedral coordination geometry involving six O atoms of six acetic acid ligands. The Zn—O bonds lengths are between 1.9588 (12) and 2.1237 (12)Å (Table 1). The End ZnII ion is coordinated by one N atom of 2-amino-4-methyl-7-chloro-1,8-naphthyridine and three O atoms of three acetic acid ligands, and has a distorted tetrahedron coordination geometry. The distance of two neighboring ZnII ions separated by two O atoms of each two acetate bridging ligands and one O atoms of one acetate bridging ligand is 3.245 (3) Å.

Experimental

A 10 ml dichloromethane solution of 2-amino-5-methyl-7-chloro-1,8-naphthyridine (0.039 g, 0.2 mmol) was added to a 20 mL dichloromethane solution of Zn(CH3COO)2 (0.055 g, 0.3 mmol) under an N2 atmosphere. The mixture was stirred for 10 h. Colorless crystals suitable for X-ray diffraction were formed by vapour diffusion of diethyl ethyl ether into dichloromethane solution.

Refinement

All hydrogen atoms were generated geometrically (C—H bond lengths of methyl group fixed at 0.98 Å, C—H bond lengths of naphthyridine fixed at 0.95 Å), assigned appropriated isotropic thermal parameters, Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound showing the atom-numbering scheme and displacement ellipsoids drawn at the 40% probability level. (Symmetry code: 1 - x, 1 - y, 1 - z).

Crystal data

[Zn3(C2H3O2)6(C9H8ClN3)2]Z = 1
Mr = 937.64F000 = 476
Triclinic, P1Dx = 1.739 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71070 Å
a = 9.1978 (12) ÅCell parameters from 2625 reflections
b = 9.2108 (13) Åθ = 2.5–25.0º
c = 12.0457 (16) ŵ = 2.21 mm1
α = 93.602 (3)ºT = 113 (2) K
β = 91.685 (2)ºPrism, colorless
γ = 118.247 (2)º0.12 × 0.08 × 0.02 mm
V = 895.2 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer4221 independent reflections
Radiation source: fine-focus sealed tube3495 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
T = 113(2) Kθmax = 27.9º
[var phi] and ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.782, Tmax = 0.956k = −12→12
11008 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065  w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4221 reflectionsΔρmax = 0.36 e Å3
253 parametersΔρmin = −0.65 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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*/Ueq
Zn10.50000.50000.50000.01215 (8)
Zn20.81766 (2)0.76297 (2)0.660723 (16)0.01398 (7)
Cl10.47109 (6)0.69320 (6)0.93855 (4)0.03122 (13)
N10.75010 (17)0.85718 (17)0.85071 (12)0.0158 (3)
N20.97997 (17)0.97283 (17)0.75522 (12)0.0136 (3)
N31.20715 (19)1.0819 (2)0.64915 (13)0.0181 (3)
H3A1.299 (3)1.168 (3)0.6360 (17)0.024 (6)*
H3B1.164 (2)0.998 (2)0.6007 (17)0.018 (5)*
C10.6629 (2)0.8670 (2)0.93115 (15)0.0179 (4)
C20.7103 (2)1.0020 (2)1.01047 (15)0.0182 (4)
H20.63940.99991.06690.022*
C30.8637 (2)1.1386 (2)1.00414 (14)0.0163 (4)
C40.9626 (2)1.1348 (2)0.91812 (14)0.0143 (3)
C50.8998 (2)0.9917 (2)0.84338 (14)0.0138 (3)
C61.1288 (2)1.0979 (2)0.73619 (14)0.0140 (4)
C71.2028 (2)1.2477 (2)0.80965 (15)0.0174 (4)
H71.30841.33500.79620.021*
C81.1228 (2)1.2645 (2)0.89753 (15)0.0170 (4)
H81.17311.36320.94620.020*
C90.9208 (2)1.2883 (2)1.08722 (16)0.0222 (4)
H9A0.92061.37971.04990.033*
H9B1.03311.32131.11780.033*
H9C0.84581.26081.14780.033*
C100.8902 (2)0.6534 (2)0.45903 (14)0.0152 (4)
C111.0029 (2)0.6306 (2)0.38019 (16)0.0206 (4)
H11A1.06540.58490.41870.031*
H11B1.07990.73760.35450.031*
H11C0.93690.55430.31600.031*
C120.5768 (2)0.8498 (2)0.60578 (15)0.0195 (4)
C130.4045 (2)0.8233 (3)0.59278 (19)0.0314 (5)
H13A0.39860.91770.63030.047*
H13B0.32980.72200.62610.047*
H13C0.37140.81280.51340.047*
C140.3533 (2)0.5867 (2)0.29542 (14)0.0132 (3)
C150.3642 (2)0.7221 (2)0.22734 (15)0.0200 (4)
H15A0.35240.80540.27530.030*
H15B0.27550.67550.16770.030*
H15C0.47160.77380.19460.030*
O10.73730 (14)0.56434 (14)0.44255 (10)0.0174 (3)
O20.95980 (15)0.76262 (15)0.54110 (10)0.0191 (3)
O30.59970 (14)0.72059 (14)0.60042 (10)0.0170 (3)
O40.69633 (18)0.98977 (17)0.62159 (15)0.0385 (4)
O50.46887 (14)0.62359 (14)0.36908 (10)0.0165 (3)
O60.22937 (14)0.44604 (14)0.27489 (10)0.0178 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.01022 (14)0.01115 (14)0.01260 (15)0.00360 (11)−0.00109 (10)−0.00257 (11)
Zn20.01081 (11)0.01109 (11)0.01601 (12)0.00248 (8)−0.00174 (8)−0.00236 (8)
Cl10.0224 (2)0.0204 (2)0.0333 (3)−0.0039 (2)0.0130 (2)−0.0047 (2)
N10.0152 (7)0.0122 (7)0.0145 (8)0.0023 (6)−0.0001 (6)−0.0009 (6)
N20.0133 (7)0.0104 (7)0.0141 (7)0.0034 (6)0.0006 (6)0.0003 (6)
N30.0130 (8)0.0141 (8)0.0220 (9)0.0021 (7)0.0041 (6)0.0008 (7)
C10.0159 (9)0.0140 (9)0.0173 (9)0.0017 (7)0.0027 (7)0.0013 (7)
C20.0204 (9)0.0165 (9)0.0155 (9)0.0070 (8)0.0031 (7)0.0012 (7)
C30.0204 (9)0.0144 (9)0.0145 (9)0.0091 (8)−0.0036 (7)−0.0009 (7)
C40.0143 (8)0.0112 (8)0.0153 (9)0.0049 (7)−0.0038 (7)−0.0006 (6)
C50.0134 (8)0.0128 (8)0.0135 (9)0.0051 (7)−0.0013 (7)0.0009 (7)
C60.0128 (8)0.0110 (8)0.0170 (9)0.0049 (7)−0.0020 (7)0.0011 (7)
C70.0118 (8)0.0103 (8)0.0248 (10)0.0012 (7)−0.0015 (7)0.0002 (7)
C80.0159 (9)0.0097 (8)0.0214 (9)0.0036 (7)−0.0039 (7)−0.0024 (7)
C90.0241 (10)0.0176 (9)0.0215 (10)0.0081 (8)−0.0021 (8)−0.0053 (8)
C100.0165 (8)0.0127 (8)0.0164 (9)0.0065 (7)0.0019 (7)0.0038 (7)
C110.0164 (9)0.0215 (9)0.0231 (10)0.0083 (8)0.0052 (7)0.0011 (8)
C120.0227 (9)0.0160 (9)0.0190 (10)0.0091 (8)−0.0009 (7)−0.0018 (7)
C130.0235 (10)0.0231 (11)0.0490 (14)0.0136 (9)−0.0034 (10)−0.0060 (9)
C140.0136 (8)0.0141 (8)0.0128 (8)0.0073 (7)0.0042 (6)−0.0010 (7)
C150.0206 (9)0.0181 (9)0.0201 (10)0.0078 (8)0.0021 (7)0.0058 (7)
O10.0117 (6)0.0176 (6)0.0191 (7)0.0044 (5)0.0018 (5)−0.0026 (5)
O20.0139 (6)0.0172 (6)0.0195 (7)0.0027 (5)0.0008 (5)−0.0041 (5)
O30.0150 (6)0.0134 (6)0.0223 (7)0.0079 (5)−0.0053 (5)−0.0076 (5)
O40.0261 (8)0.0178 (7)0.0673 (11)0.0077 (6)−0.0081 (7)0.0025 (7)
O50.0133 (6)0.0132 (6)0.0179 (7)0.0022 (5)−0.0016 (5)0.0020 (5)
O60.0151 (6)0.0125 (6)0.0214 (7)0.0037 (5)−0.0038 (5)−0.0014 (5)

Geometric parameters (Å, °)

Zn1—O32.0724 (12)C7—C81.349 (2)
Zn1—O3i2.0724 (12)C7—H70.9500
Zn1—O5i2.0910 (12)C8—H80.9500
Zn1—O52.0910 (12)C9—H9A0.9800
Zn1—O1i2.1237 (12)C9—H9B0.9800
Zn1—O12.1237 (12)C9—H9C0.9800
Zn2—O31.9588 (12)C10—O11.249 (2)
Zn2—O21.9748 (12)C10—O21.275 (2)
Zn2—O6i1.9783 (12)C10—C111.504 (2)
Zn2—N22.0379 (14)C11—H11A0.9800
Cl1—C11.7428 (18)C11—H11B0.9800
N1—C11.302 (2)C11—H11C0.9800
N1—C51.358 (2)C12—O41.234 (2)
N2—C61.346 (2)C12—O31.301 (2)
N2—C51.359 (2)C12—C131.487 (2)
N3—C61.329 (2)C13—H13A0.9800
N3—H3A0.87 (2)C13—H13B0.9800
N3—H3B0.85 (2)C13—H13C0.9800
C1—C21.401 (2)C14—O61.259 (2)
C2—C31.385 (2)C14—O51.264 (2)
C2—H20.9500C14—C151.502 (2)
C3—C41.408 (2)C15—H15A0.9800
C3—C91.512 (2)C15—H15B0.9800
C4—C51.407 (2)C15—H15C0.9800
C4—C81.433 (2)O6—Zn2i1.9783 (12)
C6—C71.439 (2)
O3—Zn1—O3i180.0C8—C7—C6120.23 (16)
O3—Zn1—O5i91.21 (5)C8—C7—H7119.9
O3i—Zn1—O5i88.79 (5)C6—C7—H7119.9
O3—Zn1—O588.79 (5)C7—C8—C4120.55 (16)
O3i—Zn1—O591.21 (5)C7—C8—H8119.7
O5i—Zn1—O5180.000 (1)C4—C8—H8119.7
O3—Zn1—O1i89.96 (5)C3—C9—H9A109.5
O3i—Zn1—O1i90.04 (5)C3—C9—H9B109.5
O5i—Zn1—O1i86.79 (5)H9A—C9—H9B109.5
O5—Zn1—O1i93.21 (5)C3—C9—H9C109.5
O3—Zn1—O190.04 (5)H9A—C9—H9C109.5
O3i—Zn1—O189.96 (5)H9B—C9—H9C109.5
O5i—Zn1—O193.21 (5)O1—C10—O2124.22 (16)
O5—Zn1—O186.79 (5)O1—C10—C11119.27 (15)
O1i—Zn1—O1180.0O2—C10—C11116.48 (15)
O3—Zn2—O2111.65 (5)C10—C11—H11A109.5
O3—Zn2—O6i103.18 (5)C10—C11—H11B109.5
O2—Zn2—O6i100.45 (5)H11A—C11—H11B109.5
O3—Zn2—N2124.29 (5)C10—C11—H11C109.5
O2—Zn2—N299.92 (5)H11A—C11—H11C109.5
O6i—Zn2—N2115.01 (6)H11B—C11—H11C109.5
C1—N1—C5116.26 (15)O4—C12—O3120.09 (17)
C6—N2—C5118.94 (14)O4—C12—C13121.64 (17)
C6—N2—Zn2132.49 (12)O3—C12—C13118.27 (16)
C5—N2—Zn2107.49 (10)C12—C13—H13A109.5
C6—N3—H3A117.2 (13)C12—C13—H13B109.5
C6—N3—H3B122.8 (13)H13A—C13—H13B109.5
H3A—N3—H3B119.2 (19)C12—C13—H13C109.5
N1—C1—C2125.99 (16)H13A—C13—H13C109.5
N1—C1—Cl1115.41 (13)H13B—C13—H13C109.5
C2—C1—Cl1118.60 (14)O6—C14—O5125.42 (16)
C3—C2—C1117.92 (16)O6—C14—C15117.28 (16)
C3—C2—H2121.0O5—C14—C15117.30 (15)
C1—C2—H2121.0C14—C15—H15A109.5
C2—C3—C4118.36 (16)C14—C15—H15B109.5
C2—C3—C9120.18 (16)H15A—C15—H15B109.5
C4—C3—C9121.44 (16)C14—C15—H15C109.5
C5—C4—C3118.00 (15)H15A—C15—H15C109.5
C5—C4—C8115.72 (15)H15B—C15—H15C109.5
C3—C4—C8126.28 (16)C10—O1—Zn1146.79 (11)
N1—C5—N2112.32 (14)C10—O2—Zn2116.68 (11)
N1—C5—C4123.46 (15)C12—O3—Zn2114.47 (11)
N2—C5—C4124.21 (15)C12—O3—Zn1134.69 (11)
N3—C6—N2119.47 (15)Zn2—O3—Zn1107.19 (5)
N3—C6—C7120.21 (16)C14—O5—Zn1133.41 (11)
N2—C6—C7120.32 (15)C14—O6—Zn2i128.40 (12)
O3—Zn2—N2—C6−112.51 (15)C11—C10—O1—Zn1177.44 (14)
O2—Zn2—N2—C612.43 (16)O3—Zn1—O1—C1018.1 (2)
O6i—Zn2—N2—C6118.98 (15)O3i—Zn1—O1—C10−161.9 (2)
O3—Zn2—N2—C555.10 (13)O5i—Zn1—O1—C10−73.1 (2)
O2—Zn2—N2—C5−179.96 (11)O5—Zn1—O1—C10106.9 (2)
O6i—Zn2—N2—C5−73.41 (12)O1—C10—O2—Zn210.3 (2)
C5—N1—C1—C2−0.7 (3)C11—C10—O2—Zn2−168.04 (12)
C5—N1—C1—Cl1179.79 (13)O3—Zn2—O2—C10−39.80 (14)
N1—C1—C2—C3−0.1 (3)O6i—Zn2—O2—C1069.02 (13)
Cl1—C1—C2—C3179.40 (14)N2—Zn2—O2—C10−173.03 (12)
C1—C2—C3—C40.5 (3)O4—C12—O3—Zn216.8 (2)
C1—C2—C3—C9179.64 (16)C13—C12—O3—Zn2−163.00 (14)
C2—C3—C4—C5−0.1 (2)O4—C12—O3—Zn1−138.26 (16)
C9—C3—C4—C5−179.27 (16)C13—C12—O3—Zn141.9 (3)
C2—C3—C4—C8179.11 (17)O2—Zn2—O3—C12−106.56 (12)
C9—C3—C4—C80.0 (3)O6i—Zn2—O3—C12146.38 (12)
C1—N1—C5—N2−178.05 (15)N2—Zn2—O3—C1213.12 (15)
C1—N1—C5—C41.1 (3)O2—Zn2—O3—Zn155.16 (7)
C6—N2—C5—N1178.72 (15)O6i—Zn2—O3—Zn1−51.90 (7)
Zn2—N2—C5—N19.14 (17)N2—Zn2—O3—Zn1174.84 (5)
C6—N2—C5—C4−0.5 (2)O5i—Zn1—O3—C12−148.65 (17)
Zn2—N2—C5—C4−170.03 (14)O5—Zn1—O3—C1231.35 (17)
C3—C4—C5—N1−0.7 (3)O1i—Zn1—O3—C12−61.86 (17)
C8—C4—C5—N1179.97 (16)O1—Zn1—O3—C12118.14 (17)
C3—C4—C5—N2178.36 (15)O5i—Zn1—O3—Zn255.03 (6)
C8—C4—C5—N2−1.0 (3)O5—Zn1—O3—Zn2−124.97 (6)
C5—N2—C6—N3−178.89 (16)O1i—Zn1—O3—Zn2141.82 (6)
Zn2—N2—C6—N3−12.4 (2)O1—Zn1—O3—Zn2−38.18 (6)
C5—N2—C6—C71.3 (2)O6—C14—O5—Zn1−10.3 (3)
Zn2—N2—C6—C7167.75 (12)C15—C14—O5—Zn1169.19 (11)
N3—C6—C7—C8179.50 (17)O3—Zn1—O5—C14−137.70 (15)
N2—C6—C7—C8−0.7 (3)O3i—Zn1—O5—C1442.30 (15)
C6—C7—C8—C4−0.8 (3)O1i—Zn1—O5—C14−47.81 (15)
C5—C4—C8—C71.6 (3)O1—Zn1—O5—C14132.19 (15)
C3—C4—C8—C7−177.70 (17)O5—C14—O6—Zn2i−5.4 (3)
O2—C10—O1—Zn1−0.9 (3)C15—C14—O6—Zn2i175.15 (11)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3B···O20.85 (2)2.15 (2)2.921 (2)150.0 (17)
N3—H3A···O5ii0.87 (2)2.09 (2)2.958 (2)171.0 (19)

Symmetry codes: (ii) −x+2, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2413).

References

  • Baker, R. S. & Norman, R. E. (2004). Acta Cryst. E60, m1761–m1763.
  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Lis, T., Kinzhybalo, V. & Zieba, K. (2005). Acta Cryst. E61, m2382–m2384.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stadie, N. P., Sanchez-Smith, R. & Groy, T. L. (2007). Acta Cryst. E63, m2153–m2154.

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