Bis(μ-2-methyl-quinolin-8-olato)-κN,O:O;κO:N,O-bis-[(acetato-κO)(methanol-κO)zinc(II)].

The reaction of zinc acetate and 2-methyl-8-hydroxy-quinoline in methanol yielded the centrosymmetric dinuclear title compound, [Zn(2)(C(10)H(8)NO)(2)(CH(3)CO(2))(2)(CH(3)OH)(2)], which has the Zn atom within a distorted NO(4) trigonal-bipyramidal coordination geometry. Methanol-acetate O-H⋯O hydrogen bonds link the dinculear units into a linear supra-molecular 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 = 629.26

Triclinic,

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[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.230

S = 1.13

2855 reflections

175 parameters

H-atom parameters constrained

Δρmax = 3.72 e Å−3

Δρmin = −1.85 e Å−3

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 ▶).

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

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

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

[Zn2(C10H8NO)2(C2H3O2)2(CH4O)2]	Z = 1
Mr = 629.26	F(000) = 324
Triclinic, P1	Dx = 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

Bruker SMART APEX diffractometer	2855 independent reflections
Radiation source: fine-focus sealed tube	2534 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.525, Tmax = 0.721	k = −12→12
5601 measured reflections	l = −12→12

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(Fo2) + (0.1574P)2 + 1.7954P] where P = (Fo2 + 2Fc2)/3
2855 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 3.72 e Å−3
0 restraints	Δρmin = −1.85 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .