Bis(μ-2-methyl­quinolin-8-olato)-κ3N,O:O;κ3O:N,O-bis­[(acetato-κO)(methanol-κO)zinc(II)]

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

doi:10.1107/S1600536809014214

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m554

doi:10.1107/S1600536809014214

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Bis(μ-2-methylquinolin-8-olato)-κ³N,O:O;κ³O:N,O-bis[(acetato-κO)(methanol-κO)zinc(II)]

Elham Sattarzadeh,^a Gholamhossein Mohammadnezhad,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 April 2009; accepted 16 April 2009; online 22 April 2009)

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

Unlike 8-hydroxyquinoline, which yields a large number of metal derivatives, 2-methyl-8-hydroxyquinoline forms only a small number of metal chelates. Besides a related chloride salt (Sattarzadeh et al., 2009 ), there is only one crystal structure report of another zinc derivative; for aquabis(2-methylquinolin-8-ato)zinc, see: da Silva et al. (2007 ).

Experimental

Crystal data

[Zn₂(C₁₀H₈NO)₂(C₂H₃O₂)₂(CH₄O)₂]
M_r = 629.26
Triclinic, $[P \overline 1]$
a = 6.9496 (1) Å
b = 9.6262 (2) Å
c = 9.8232 (2) Å
α = 75.241 (1)°
β = 89.688 (1)°
γ = 86.596 (1)°
V = 634.32 (2) Å³
Z = 1
Mo Kα radiation
μ = 1.95 mm⁻¹
T = 100 K
0.38 × 0.28 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.525, T_max = 0.721
5601 measured reflections
2855 independent reflections
2534 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.230
S = 1.13
2855 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 3.72 e Å⁻³
Δρ_min = −1.85 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3ⁱ	0.84	1.88	2.602 (6)	143
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014214/tk2424sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014214/tk2424Isup2.hkl

checkCIF report

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.

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

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
M_r = 629.26	F(000) = 324
Triclinic, P1	D_x = 1.647 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9496 (1) Å	Cell parameters from 3551 reflections
b = 9.6262 (2) Å	θ = 2.2–28.3°
c = 9.8232 (2) Å	µ = 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 tube	2534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.525, T_max = 0.721	k = −12→12
5601 measured reflections	l = −12→12

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.230	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.1574P)² + 1.7954P] where P = (F_o² + 2F_c²)/3
2855 reflections	(Δ/σ)_max = 0.001
175 parameters	Δρ_max = 3.72 e Å⁻³
0 restraints	Δρ_min = −1.85 e Å⁻³

Crystal data top

[Zn₂(C₁₀H₈NO)₂(C₂H₃O₂)₂(CH₄O)₂]	γ = 86.596 (1)°
M_r = 629.26	V = 634.32 (2) Å³
Triclinic, P1	Z = 1
a = 6.9496 (1) Å	Mo Kα radiation
b = 9.6262 (2) Å	µ = 1.95 mm⁻¹
c = 9.8232 (2) Å	T = 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)
T_min = 0.525, T_max = 0.721	R_int = 0.042
5601 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.230	H-atom parameters constrained
S = 1.13	Δρ_max = 3.72 e Å⁻³
2855 reflections	Δρ_min = −1.85 e Å⁻³
175 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.57254 (8)	0.63131 (6)	0.87572 (5)	0.0148 (3)
O1	0.5349 (5)	0.4205 (4)	0.9193 (4)	0.0174 (8)
O2	0.4331 (6)	0.8211 (4)	0.8160 (4)	0.0201 (8)
O3	0.1619 (6)	0.7137 (5)	0.8017 (4)	0.0236 (9)
O4	0.8356 (6)	0.6830 (5)	0.9340 (4)	0.0233 (9)
H4	0.9089	0.7231	0.8695	0.028*
N1	0.6717 (6)	0.5859 (5)	0.6847 (5)	0.0165 (9)
C1	0.5872 (7)	0.3551 (6)	0.8200 (5)	0.0169 (10)
C2	0.5764 (8)	0.2097 (6)	0.8320 (6)	0.0184 (10)
H2	0.5313	0.1493	0.9168	0.022*
C3	0.6315 (9)	0.1497 (6)	0.7196 (6)	0.0229 (11)
H3	0.6238	0.0492	0.7303	0.028*
C4	0.6955 (8)	0.2334 (6)	0.5956 (6)	0.0232 (11)
H4A	0.7301	0.1912	0.5207	0.028*
C5	0.7104 (8)	0.3827 (6)	0.5786 (6)	0.0191 (10)
C6	0.6596 (7)	0.4431 (6)	0.6917 (5)	0.0150 (9)
C7	0.7707 (8)	0.4776 (6)	0.4547 (6)	0.0196 (11)
H7	0.8029	0.4427	0.3748	0.023*
C8	0.7834 (8)	0.6205 (6)	0.4485 (5)	0.0208 (11)
H8	0.8248	0.6846	0.3646	0.025*
C9	0.7341 (8)	0.6730 (6)	0.5687 (5)	0.0178 (10)
C10	0.7542 (9)	0.8281 (6)	0.5643 (6)	0.0227 (11)
H10A	0.7336	0.8427	0.6586	0.034*
H10B	0.6582	0.8879	0.4988	0.034*
H10C	0.8838	0.8552	0.5326	0.034*
C11	0.2496 (8)	0.8207 (6)	0.8104 (5)	0.0179 (10)
C12	0.1384 (9)	0.9585 (7)	0.8161 (7)	0.0297 (13)
H12A	0.2244	1.0381	0.7939	0.045*
H12B	0.0864	0.9488	0.9108	0.045*
H12C	0.0322	0.9780	0.7474	0.045*
C13	0.9045 (8)	0.6565 (7)	1.0750 (6)	0.0233 (11)
H13A	1.0426	0.6285	1.0786	0.035*
H13B	0.8350	0.5787	1.1356	0.035*
H13C	0.8832	0.7441	1.1079	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0190 (4)	0.0192 (4)	0.0083 (4)	−0.0030 (2)	0.0016 (2)	−0.0068 (2)
O1	0.027 (2)	0.0212 (18)	0.0063 (16)	−0.0035 (15)	0.0078 (14)	−0.0071 (14)
O2	0.025 (2)	0.0206 (19)	0.0146 (17)	−0.0033 (15)	0.0021 (15)	−0.0033 (14)
O3	0.023 (2)	0.032 (2)	0.020 (2)	−0.0040 (16)	0.0045 (16)	−0.0146 (17)
O4	0.0186 (19)	0.041 (2)	0.0123 (18)	−0.0090 (16)	0.0026 (14)	−0.0094 (16)
N1	0.018 (2)	0.024 (2)	0.0098 (19)	−0.0017 (16)	−0.0004 (15)	−0.0079 (16)
C1	0.018 (2)	0.024 (3)	0.012 (2)	−0.0030 (19)	0.0016 (18)	−0.0084 (19)
C2	0.023 (3)	0.019 (2)	0.015 (2)	−0.0026 (19)	0.0028 (19)	−0.0058 (19)
C3	0.030 (3)	0.021 (3)	0.021 (3)	0.001 (2)	−0.002 (2)	−0.012 (2)
C4	0.025 (3)	0.029 (3)	0.020 (3)	−0.001 (2)	0.000 (2)	−0.015 (2)
C5	0.017 (2)	0.027 (3)	0.016 (2)	0.000 (2)	−0.0011 (19)	−0.012 (2)
C6	0.017 (2)	0.021 (2)	0.008 (2)	0.0006 (18)	0.0004 (17)	−0.0055 (18)
C7	0.018 (2)	0.032 (3)	0.012 (2)	0.002 (2)	0.0005 (19)	−0.012 (2)
C8	0.020 (3)	0.033 (3)	0.010 (2)	−0.001 (2)	−0.0003 (19)	−0.008 (2)
C9	0.018 (2)	0.027 (3)	0.009 (2)	−0.003 (2)	0.0009 (18)	−0.0058 (19)
C10	0.035 (3)	0.023 (3)	0.012 (2)	−0.006 (2)	0.003 (2)	−0.006 (2)
C11	0.020 (2)	0.024 (3)	0.010 (2)	0.0004 (19)	0.0012 (18)	−0.0057 (19)
C12	0.027 (3)	0.027 (3)	0.034 (3)	0.002 (2)	0.002 (2)	−0.006 (2)
C13	0.023 (3)	0.035 (3)	0.013 (2)	−0.004 (2)	0.001 (2)	−0.009 (2)

Geometric parameters (Å, º) top

Zn1—O1	1.997 (4)	C4—C5	1.414 (8)
Zn1—O2	1.968 (4)	C4—H4A	0.9500
Zn1—O1ⁱ	2.092 (3)	C5—C7	1.402 (8)
Zn1—O4	2.045 (4)	C5—C6	1.413 (7)
Zn1—N1	2.134 (4)	C7—C8	1.369 (8)
O1—C1	1.328 (6)	C7—H7	0.9500
O1—Zn1ⁱ	2.092 (3)	C8—C9	1.431 (7)
O2—C11	1.277 (7)	C8—H8	0.9500
O3—C11	1.250 (7)	C9—C10	1.497 (7)
O4—C13	1.423 (6)	C10—H10A	0.9800
O4—H4	0.8400	C10—H10B	0.9800
N1—C9	1.319 (7)	C10—H10C	0.9800
N1—C6	1.366 (7)	C11—C12	1.508 (8)
C1—C2	1.381 (7)	C12—H12A	0.9800
C1—C6	1.435 (7)	C12—H12B	0.9800
C2—C3	1.412 (7)	C12—H12C	0.9800
C2—H2	0.9500	C13—H13A	0.9800
C3—C4	1.366 (9)	C13—H13B	0.9800
C3—H3	0.9500	C13—H13C	0.9800

O1—Zn1—O1ⁱ	75.2 (2)	C6—C5—C4	119.1 (5)
O1—Zn1—O2	142.5 (2)	N1—C6—C5	122.8 (5)
O1—Zn1—O4	114.7 (2)	N1—C6—C1	116.8 (4)
O1—Zn1—N1	79.8 (2)	C5—C6—C1	120.4 (5)
O1ⁱ—Zn1—O2	95.8 (2)	C8—C7—C5	120.2 (5)
O1ⁱ—Zn1—O4	94.5 (2)	C8—C7—H7	119.9
O1ⁱ—Zn1—N1	155.0 (2)	C5—C7—H7	119.9
O2—Zn1—O4	102.1 (2)	C7—C8—C9	119.9 (5)
O2—Zn1—N1	104.7 (2)	C7—C8—H8	120.1
O4—Zn1—N1	95.0 (2)	C9—C8—H8	120.1
C1—O1—Zn1	116.2 (3)	N1—C9—C8	120.7 (5)
C1—O1—Zn1ⁱ	139.0 (3)	N1—C9—C10	119.2 (5)
Zn1—O1—Zn1ⁱ	104.81 (16)	C8—C9—C10	120.1 (5)
C11—O2—Zn1	116.0 (3)	C9—C10—H10A	109.5
C13—O4—Zn1	125.3 (3)	C9—C10—H10B	109.5
C13—O4—H4	117.3	H10A—C10—H10B	109.5
Zn1—O4—H4	117.3	C9—C10—H10C	109.5
C9—N1—C6	119.7 (4)	H10A—C10—H10C	109.5
C9—N1—Zn1	130.0 (4)	H10B—C10—H10C	109.5
C6—N1—Zn1	110.3 (3)	O3—C11—O2	123.5 (5)
O1—C1—C2	124.6 (5)	O3—C11—C12	120.0 (5)
O1—C1—C6	117.0 (5)	O2—C11—C12	116.5 (5)
C2—C1—C6	118.4 (5)	C11—C12—H12A	109.5
C1—C2—C3	120.8 (5)	C11—C12—H12B	109.5
C1—C2—H2	119.6	H12A—C12—H12B	109.5
C3—C2—H2	119.6	C11—C12—H12C	109.5
C4—C3—C2	121.2 (5)	H12A—C12—H12C	109.5
C4—C3—H3	119.4	H12B—C12—H12C	109.5
C2—C3—H3	119.4	O4—C13—H13A	109.5
C3—C4—C5	120.1 (5)	O4—C13—H13B	109.5
C3—C4—H4A	119.9	H13A—C13—H13B	109.5
C5—C4—H4A	119.9	O4—C13—H13C	109.5
C7—C5—C6	116.7 (5)	H13A—C13—H13C	109.5
C7—C5—C4	124.2 (5)	H13B—C13—H13C	109.5

O2—Zn1—O1—C1	102.0 (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—C5	0.9 (9)
N1—Zn1—O1—C1	1.1 (4)	C3—C4—C5—C7	−178.6 (6)
O2—Zn1—O1—Zn1ⁱ	−80.1 (3)	C3—C4—C5—C6	0.5 (8)
O4—Zn1—O1—Zn1ⁱ	88.17 (19)	C9—N1—C6—C5	−0.4 (8)
O1ⁱ—Zn1—O1—Zn1ⁱ	0.0	Zn1—N1—C6—C5	178.2 (4)
N1—Zn1—O1—Zn1ⁱ	179.0 (2)	C9—N1—C6—C1	−178.9 (5)
O1—Zn1—O2—C11	7.8 (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—N1	179.3 (5)
N1—Zn1—O2—C11	100.1 (4)	C7—C5—C6—C1	176.9 (5)
O2—Zn1—O4—C13	107.2 (4)	C4—C5—C6—C1	−2.3 (8)
O1—Zn1—O4—C13	−65.5 (5)	O1—C1—C6—N1	1.2 (7)
O1ⁱ—Zn1—O4—C13	10.3 (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—C9	36.2 (5)	C2—C1—C6—C5	2.7 (8)
O1—Zn1—N1—C9	178.0 (5)	C6—C5—C7—C8	1.8 (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—C8	2.1 (8)
O1—Zn1—N1—C6	−0.4 (3)	Zn1—N1—C9—C8	−176.2 (4)
O4—Zn1—N1—C6	113.9 (3)	C6—N1—C9—C10	−177.6 (5)
O1ⁱ—Zn1—N1—C6	1.9 (6)	Zn1—N1—C9—C10	4.1 (8)
Zn1—O1—C1—C2	178.4 (4)	C7—C8—C9—N1	−1.8 (8)
Zn1ⁱ—O1—C1—C2	1.5 (9)	C7—C8—C9—C10	177.9 (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—C12	159.0 (4)
O1—C1—C2—C3	178.7 (5)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3ⁱⁱ	0.84	1.88	2.602 (6)	143

Symmetry code: (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₁₀H₈NO)₂(C₂H₃O₂)₂(CH₄O)₂]
M_r	629.26
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.9496 (1), 9.6262 (2), 9.8232 (2)
α, β, γ (°)	75.241 (1), 89.688 (1), 86.596 (1)
V (Å³)	634.32 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.95
Crystal size (mm)	0.38 × 0.28 × 0.18

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.525, 0.721
No. of measured, independent and observed [I > 2σ(I)] reflections	5601, 2855, 2534
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.230, 1.13
No. of reflections	2855
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	3.72, −1.85

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3ⁱ	0.84	1.88	2.602 (6)	143

Symmetry code: (i) x+1, y, z.

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sattarzadeh, E., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2009). Acta Cryst. E65, m553. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Silva, L. E. da, Joussef, A. C., Rebelo, R. A., Foro, S. & Schmidt, B. (2007). Acta Cryst. E63, m129–m131. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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