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Acta Cryst. (2009). E65, m554    [ doi:10.1107/S1600536809014214 ]

Bis([mu]-2-methylquinolin-8-olato)-[kappa]3N,O:O;[kappa]3O:N,O-bis[(acetato-[kappa]O)(methanol-[kappa]O)zinc(II)]

E. Sattarzadeh, G. Mohammadnezhad, M. M. Amini and S. W. Ng

Abstract top

The reaction of zinc acetate and 2-methyl-8-hydroxyquinoline in methanol yielded the centrosymmetric dinuclear title compound, [Zn2(C10H8NO)2(CH3CO2)2(CH3OH)2], which has the Zn atom within a distorted NO4 trigonal-bipyramidal coordination geometry. Methanol-acetate O-H...O hydrogen bonds link the dinculear units into a linear supramolecular chain extending parallel to [100].

Related literature top

Unlike 8-hydroxyquinoline, which yields a large number of metal derivatives, 2-methyl-8-hydroxyquinoline forms only a small number of metal chelates. There is only one crystal structure report of a zinc derivative; for aquabis(2-methylquinolin-8-ato)zinc, see: da Silva et al. (2007).

Experimental top

Zinc acetate (0.17 g, 0.75 mmol) and 2-methyl-8-hydroxyquinoline (0.24 g, 1.5 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Crystals were collected from the side arm after several days. Although well formed, all specimens had a slightly blemished interior.

Refinement top

The crystal used in the study was a multiply twinned crystal. The diffraction intensities were separated with the RLATT routine of the data collection software, and that component that diffracted to the highest 2θ limit was selected for integration. Although the specimen diffracted strongly, with a high proportion of 'observeds', there was serious overlapping between the main component and the minor components, particularly at low angles.

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å; O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C, O).

The final difference Fourier map had a large peak/deep hole in the vicinity of the Zn1 atom. These could not be reduced even with the 2θ maximum was lowered to 50 °.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of dinuclear [Zn(C10H8NO)(CH3OH)(CH3CO2)]2; ellipsoids are drawn at the 70% probability level and H atoms of arbitrary radius. The unlabelled atoms are related by a centre of inversion.
Bis(µ-2-methylquinolin-8-olato)- κ3N,O:O;κ3O:N,O- bis[(acetato-κO)(methanol-κO)zinc(II)] top
Crystal data top
[Zn2(C10H8NO)2(C2H3O2)2(CH4O)2]Z = 1
Mr = 629.26F(000) = 324
Triclinic, P1Dx = 1.647 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9496 (1) ÅCell parameters from 3551 reflections
b = 9.6262 (2) Åθ = 2.2–28.3°
c = 9.8232 (2) ŵ = 1.95 mm−1
α = 75.241 (1)°T = 100 K
β = 89.688 (1)°Block, yellow
γ = 86.596 (1)°0.38 × 0.28 × 0.18 mm
V = 634.32 (2) Å3
Data collection top
Bruker SMART APEX
diffractometer		2855 independent reflections
Radiation source: fine-focus sealed tube2534 reflections with I > 2σ(I)
graphiteRint = 0.042
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.525, Tmax = 0.721k = −12→12
5601 measured reflectionsl = −12→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.1574P)2 + 1.7954P]
where P = (Fo2 + 2Fc2)/3
2855 reflections(Δ/σ)max = 0.001
175 parametersΔρmax = 3.72 e Å−3
0 restraintsΔρmin = −1.85 e Å−3
Crystal data top
[Zn2(C10H8NO)2(C2H3O2)2(CH4O)2]γ = 86.596 (1)°
Mr = 629.26V = 634.32 (2) Å3
Triclinic, P1Z = 1
a = 6.9496 (1) ÅMo Kα radiation
b = 9.6262 (2) ŵ = 1.95 mm−1
c = 9.8232 (2) ÅT = 100 K
α = 75.241 (1)°0.38 × 0.28 × 0.18 mm
β = 89.688 (1)°
Data collection top
Bruker SMART APEX
diffractometer		2855 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2534 reflections with I > 2σ(I)
Tmin = 0.525, Tmax = 0.721Rint = 0.042
5601 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.076H-atom parameters constrained
wR(F2) = 0.230Δρmax = 3.72 e Å−3
S = 1.13Δρmin = −1.85 e Å−3
2855 reflectionsAbsolute structure: ?
175 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.57254 (8)0.63131 (6)0.87572 (5)0.0148 (3)
O10.5349 (5)0.4205 (4)0.9193 (4)0.0174 (8)
O20.4331 (6)0.8211 (4)0.8160 (4)0.0201 (8)
O30.1619 (6)0.7137 (5)0.8017 (4)0.0236 (9)
O40.8356 (6)0.6830 (5)0.9340 (4)0.0233 (9)
H40.90890.72310.86950.028*
N10.6717 (6)0.5859 (5)0.6847 (5)0.0165 (9)
C10.5872 (7)0.3551 (6)0.8200 (5)0.0169 (10)
C20.5764 (8)0.2097 (6)0.8320 (6)0.0184 (10)
H20.53130.14930.91680.022*
C30.6315 (9)0.1497 (6)0.7196 (6)0.0229 (11)
H30.62380.04920.73030.028*
C40.6955 (8)0.2334 (6)0.5956 (6)0.0232 (11)
H4A0.73010.19120.52070.028*
C50.7104 (8)0.3827 (6)0.5786 (6)0.0191 (10)
C60.6596 (7)0.4431 (6)0.6917 (5)0.0150 (9)
C70.7707 (8)0.4776 (6)0.4547 (6)0.0196 (11)
H70.80290.44270.37480.023*
C80.7834 (8)0.6205 (6)0.4485 (5)0.0208 (11)
H80.82480.68460.36460.025*
C90.7341 (8)0.6730 (6)0.5687 (5)0.0178 (10)
C100.7542 (9)0.8281 (6)0.5643 (6)0.0227 (11)
H10A0.73360.84270.65860.034*
H10B0.65820.88790.49880.034*
H10C0.88380.85520.53260.034*
C110.2496 (8)0.8207 (6)0.8104 (5)0.0179 (10)
C120.1384 (9)0.9585 (7)0.8161 (7)0.0297 (13)
H12A0.22441.03810.79390.045*
H12B0.08640.94880.91080.045*
H12C0.03220.97800.74740.045*
C130.9045 (8)0.6565 (7)1.0750 (6)0.0233 (11)
H13A1.04260.62851.07860.035*
H13B0.83500.57871.13560.035*
H13C0.88320.74411.10790.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0190 (4)0.0192 (4)0.0083 (4)−0.0030 (2)0.0016 (2)−0.0068 (2)
O10.027 (2)0.0212 (18)0.0063 (16)−0.0035 (15)0.0078 (14)−0.0071 (14)
O20.025 (2)0.0206 (19)0.0146 (17)−0.0033 (15)0.0021 (15)−0.0033 (14)
O30.023 (2)0.032 (2)0.020 (2)−0.0040 (16)0.0045 (16)−0.0146 (17)
O40.0186 (19)0.041 (2)0.0123 (18)−0.0090 (16)0.0026 (14)−0.0094 (16)
N10.018 (2)0.024 (2)0.0098 (19)−0.0017 (16)−0.0004 (15)−0.0079 (16)
C10.018 (2)0.024 (3)0.012 (2)−0.0030 (19)0.0016 (18)−0.0084 (19)
C20.023 (3)0.019 (2)0.015 (2)−0.0026 (19)0.0028 (19)−0.0058 (19)
C30.030 (3)0.021 (3)0.021 (3)0.001 (2)−0.002 (2)−0.012 (2)
C40.025 (3)0.029 (3)0.020 (3)−0.001 (2)0.000 (2)−0.015 (2)
C50.017 (2)0.027 (3)0.016 (2)0.000 (2)−0.0011 (19)−0.012 (2)
C60.017 (2)0.021 (2)0.008 (2)0.0006 (18)0.0004 (17)−0.0055 (18)
C70.018 (2)0.032 (3)0.012 (2)0.002 (2)0.0005 (19)−0.012 (2)
C80.020 (3)0.033 (3)0.010 (2)−0.001 (2)−0.0003 (19)−0.008 (2)
C90.018 (2)0.027 (3)0.009 (2)−0.003 (2)0.0009 (18)−0.0058 (19)
C100.035 (3)0.023 (3)0.012 (2)−0.006 (2)0.003 (2)−0.006 (2)
C110.020 (2)0.024 (3)0.010 (2)0.0004 (19)0.0012 (18)−0.0057 (19)
C120.027 (3)0.027 (3)0.034 (3)0.002 (2)0.002 (2)−0.006 (2)
C130.023 (3)0.035 (3)0.013 (2)−0.004 (2)0.001 (2)−0.009 (2)
Geometric parameters (Å, °) top
Zn1—O11.997 (4)C4—C51.414 (8)
Zn1—O21.968 (4)C4—H4A0.9500
Zn1—O1i2.092 (3)C5—C71.402 (8)
Zn1—O42.045 (4)C5—C61.413 (7)
Zn1—N12.134 (4)C7—C81.369 (8)
O1—C11.328 (6)C7—H70.9500
O1—Zn1i2.092 (3)C8—C91.431 (7)
O2—C111.277 (7)C8—H80.9500
O3—C111.250 (7)C9—C101.497 (7)
O4—C131.423 (6)C10—H10A0.9800
O4—H40.8400C10—H10B0.9800
N1—C91.319 (7)C10—H10C0.9800
N1—C61.366 (7)C11—C121.508 (8)
C1—C21.381 (7)C12—H12A0.9800
C1—C61.435 (7)C12—H12B0.9800
C2—C31.412 (7)C12—H12C0.9800
C2—H20.9500C13—H13A0.9800
C3—C41.366 (9)C13—H13B0.9800
C3—H30.9500C13—H13C0.9800
O1—Zn1—O1i75.2 (2)C6—C5—C4119.1 (5)
O1—Zn1—O2142.5 (2)N1—C6—C5122.8 (5)
O1—Zn1—O4114.7 (2)N1—C6—C1116.8 (4)
O1—Zn1—N179.8 (2)C5—C6—C1120.4 (5)
O1i—Zn1—O295.8 (2)C8—C7—C5120.2 (5)
O1i—Zn1—O494.5 (2)C8—C7—H7119.9
O1i—Zn1—N1155.0 (2)C5—C7—H7119.9
O2—Zn1—O4102.1 (2)C7—C8—C9119.9 (5)
O2—Zn1—N1104.7 (2)C7—C8—H8120.1
O4—Zn1—N195.0 (2)C9—C8—H8120.1
C1—O1—Zn1116.2 (3)N1—C9—C8120.7 (5)
C1—O1—Zn1i139.0 (3)N1—C9—C10119.2 (5)
Zn1—O1—Zn1i104.81 (16)C8—C9—C10120.1 (5)
C11—O2—Zn1116.0 (3)C9—C10—H10A109.5
C13—O4—Zn1125.3 (3)C9—C10—H10B109.5
C13—O4—H4117.3H10A—C10—H10B109.5
Zn1—O4—H4117.3C9—C10—H10C109.5
C9—N1—C6119.7 (4)H10A—C10—H10C109.5
C9—N1—Zn1130.0 (4)H10B—C10—H10C109.5
C6—N1—Zn1110.3 (3)O3—C11—O2123.5 (5)
O1—C1—C2124.6 (5)O3—C11—C12120.0 (5)
O1—C1—C6117.0 (5)O2—C11—C12116.5 (5)
C2—C1—C6118.4 (5)C11—C12—H12A109.5
C1—C2—C3120.8 (5)C11—C12—H12B109.5
C1—C2—H2119.6H12A—C12—H12B109.5
C3—C2—H2119.6C11—C12—H12C109.5
C4—C3—C2121.2 (5)H12A—C12—H12C109.5
C4—C3—H3119.4H12B—C12—H12C109.5
C2—C3—H3119.4O4—C13—H13A109.5
C3—C4—C5120.1 (5)O4—C13—H13B109.5
C3—C4—H4A119.9H13A—C13—H13B109.5
C5—C4—H4A119.9O4—C13—H13C109.5
C7—C5—C6116.7 (5)H13A—C13—H13C109.5
C7—C5—C4124.2 (5)H13B—C13—H13C109.5
O2—Zn1—O1—C1102.0 (4)C6—C1—C2—C3−1.3 (8)
O4—Zn1—O1—C1−89.7 (4)C1—C2—C3—C4−0.5 (9)
O1i—Zn1—O1—C1−177.9 (5)C2—C3—C4—C50.9 (9)
N1—Zn1—O1—C11.1 (4)C3—C4—C5—C7−178.6 (6)
O2—Zn1—O1—Zn1i−80.1 (3)C3—C4—C5—C60.5 (8)
O4—Zn1—O1—Zn1i88.17 (19)C9—N1—C6—C5−0.4 (8)
O1i—Zn1—O1—Zn1i0.0Zn1—N1—C6—C5178.2 (4)
N1—Zn1—O1—Zn1i179.0 (2)C9—N1—C6—C1−178.9 (5)
O1—Zn1—O2—C117.8 (5)Zn1—N1—C6—C1−0.3 (6)
O4—Zn1—O2—C11−161.4 (4)C7—C5—C6—N1−1.5 (8)
O1i—Zn1—O2—C11−65.4 (4)C4—C5—C6—N1179.3 (5)
N1—Zn1—O2—C11100.1 (4)C7—C5—C6—C1176.9 (5)
O2—Zn1—O4—C13107.2 (4)C4—C5—C6—C1−2.3 (8)
O1—Zn1—O4—C13−65.5 (5)O1—C1—C6—N11.2 (7)
O1i—Zn1—O4—C1310.3 (4)C2—C1—C6—N1−178.8 (5)
N1—Zn1—O4—C13−146.6 (4)O1—C1—C6—C5−177.3 (5)
O2—Zn1—N1—C936.2 (5)C2—C1—C6—C52.7 (8)
O1—Zn1—N1—C9178.0 (5)C6—C5—C7—C81.8 (8)
O4—Zn1—N1—C9−67.7 (5)C4—C5—C7—C8−179.1 (5)
O1i—Zn1—N1—C9−179.6 (4)C5—C7—C8—C9−0.3 (8)
O2—Zn1—N1—C6−142.2 (3)C6—N1—C9—C82.1 (8)
O1—Zn1—N1—C6−0.4 (3)Zn1—N1—C9—C8−176.2 (4)
O4—Zn1—N1—C6113.9 (3)C6—N1—C9—C10−177.6 (5)
O1i—Zn1—N1—C61.9 (6)Zn1—N1—C9—C104.1 (8)
Zn1—O1—C1—C2178.4 (4)C7—C8—C9—N1−1.8 (8)
Zn1i—O1—C1—C21.5 (9)C7—C8—C9—C10177.9 (5)
Zn1—O1—C1—C6−1.6 (6)Zn1—O2—C11—O3−20.5 (7)
Zn1i—O1—C1—C6−178.5 (4)Zn1—O2—C11—C12159.0 (4)
O1—C1—C2—C3178.7 (5)
Symmetry codes: (i) −x+1, −y+1, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3ii0.841.882.602 (6)143
Symmetry codes: (ii) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.841.882.602 (6)143
Symmetry codes: (i) x+1, y, z.
Acknowledgements top

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Silva, L. E. da, Joussef, A. C., Rebelo, R. A., Foro, S. & Schmidt, B. (2007). Acta Cryst. E63, m129–m131.

Westrip, S. P. (2009). publCIF. In preparation.