Bis(μ-5-chloro­quinolin-8-olato)-κ3N,O:O;κ3O:N,O-bis­[(acetato-κ2O,O′)lead(II)]

Mohammadnezhad Sh., G.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536809003559

metal-organic compounds

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Volume 65| Part 3| March 2009| Page m261

doi:10.1107/S1600536809003559

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Bis(μ-5-chloroquinolin-8-olato)-κ³N,O:O;κ³O:N,O-bis[(acetato-κ²O,O′)lead(II)]

Gholamhossein Mohammadnezhad Sh.,^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 27 January 2009; accepted 29 January 2009; online 11 February 2009)

The molecule of the title compound, [Pb₂(C₉H₅ClNO)₂(C₂H₃O₂)₂], lies about a center of inversion. The Pb^II atom is chelated by acetate and substituted quinolin-8-olate anions; the O atoms of the quinolin-8-olates also bridge to confer a five-coordinate status to each metal center. The geometry approximates a distorted Ψ-fac octahedron in which one of the sites is occupied by a stereochemically active lone pair.

Related literature

The structural chemistry of lead(II) 8-hydroxyquinolinates has been reviewed, including bis(μ-acetato)diacetatotetrakis(μ-quinolin-8-olato)tetralead dihydrate (Shahverdizadeh et al., 2008 ).

Experimental

Crystal data

[Pb₂(C₉H₅ClNO)₂(C₂H₃O₂)₂]
M_r = 889.65
Monoclinic, P 2₁ /n
a = 5.3049 (1) Å
b = 11.8200 (3) Å
c = 17.4928 (3) Å
β = 94.569 (1)°
V = 1093.38 (4) Å³
Z = 2
Mo Kα radiation
μ = 15.67 mm⁻¹
T = 100 (2) K
0.10 × 0.03 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.303, T_max = 0.745
7713 measured reflections
1925 independent reflections
1655 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.00
1925 reflections
155 parameters
72 restraints
H-atom parameters constrained
Δρ_max = 5.25 e Å⁻³
Δρ_min = −3.38 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003559/tk2365sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003559/tk2365Isup2.hkl

checkCIF report

Related literature top

The structural chemistry of lead(II) 8-hydroxyquinolinates has been reviewed; for bis(µ-acetato)diacetatotetrakis(µ-quinolin-8-olato)tetralead dihydrate in particular, see: Shahverdizadeh et al. (2008).

Experimental top

Lead acetate (0.38 g, 1 mmol) and 5-chloro-8-hydroxyquinoline (0.32 g, 2 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 1 day.

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 Pb₂(CH₃CO₂)₂(C₉H₅ClNO)₂; ellipsoids are drawn at the 70% probability level and H atoms of arbitrary radius. Unlabelled atoms are related by 1-x, 1-y, 1-z.

Bis(µ-5-chloroquinolin-8-οlato)- κ³N,O:O;κ³O:N,O- bis[(acetato-κ²O,O')lead(II)] top

Crystal data top

[Pb₂(C₉H₅ClNO)₂(C₂H₃O₂)₂]	F(000) = 816
M_r = 889.65	D_x = 2.702 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4123 reflections
a = 5.3049 (1) Å	θ = 2.9–28.3°
b = 11.8200 (3) Å	µ = 15.67 mm⁻¹
c = 17.4928 (3) Å	T = 100 K
β = 94.569 (1)°	Yellow, prism
V = 1093.38 (4) Å³	0.10 × 0.03 × 0.02 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	1925 independent reflections
Radiation source: fine-focus sealed tube	1655 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.303, T_max = 0.745	k = −13→14
7713 measured reflections	l = −20→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0761P)²] where P = (F_o² + 2F_c²)/3
1925 reflections	(Δ/σ)_max = 0.001
155 parameters	Δρ_max = 5.25 e Å⁻³
72 restraints	Δρ_min = −3.38 e Å⁻³

Crystal data top

[Pb₂(C₉H₅ClNO)₂(C₂H₃O₂)₂]	V = 1093.38 (4) Å³
M_r = 889.65	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.3049 (1) Å	µ = 15.67 mm⁻¹
b = 11.8200 (3) Å	T = 100 K
c = 17.4928 (3) Å	0.10 × 0.03 × 0.02 mm
β = 94.569 (1)°

Data collection top

Bruker SMART APEX diffractometer	1925 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1655 reflections with I > 2σ(I)
T_min = 0.303, T_max = 0.745	R_int = 0.063
7713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	72 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.00	Δρ_max = 5.25 e Å⁻³
1925 reflections	Δρ_min = −3.38 e Å⁻³
155 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Pb1	0.63668 (6)	0.60161 (3)	0.421032 (17)	0.01511 (18)
Cl1	−0.4232 (4)	0.30986 (19)	0.20373 (12)	0.0219 (5)
O1	0.3463 (11)	0.4603 (5)	0.4439 (3)	0.0175 (13)
O2	0.2902 (11)	0.7164 (6)	0.4314 (4)	0.0244 (14)
O3	0.6097 (12)	0.8054 (6)	0.4933 (4)	0.0318 (16)
N1	0.3482 (13)	0.5526 (6)	0.3014 (4)	0.0164 (15)
C1	0.1685 (16)	0.4300 (8)	0.3908 (5)	0.0149 (17)
C2	−0.0268 (17)	0.3547 (8)	0.4053 (5)	0.0186 (18)
H2	−0.0351	0.3259	0.4557	0.022*
C3	−0.2105 (16)	0.3205 (7)	0.3474 (5)	0.0186 (19)
H3	−0.3392	0.2691	0.3594	0.022*
C4	−0.2057 (16)	0.3610 (8)	0.2735 (5)	0.0154 (17)
C5	−0.0195 (16)	0.4416 (7)	0.2573 (5)	0.0143 (18)
C6	0.1645 (16)	0.4747 (7)	0.3134 (5)	0.0179 (18)
C7	−0.0074 (17)	0.4913 (8)	0.1825 (5)	0.0203 (19)
H7	−0.1270	0.4707	0.1416	0.024*
C8	0.1763 (17)	0.5679 (8)	0.1710 (5)	0.0193 (19)
H8	0.1863	0.6018	0.1221	0.023*
C9	0.3506 (19)	0.5960 (7)	0.2321 (6)	0.021 (2)
H9	0.4784	0.6497	0.2232	0.025*
C10	0.3841 (15)	0.7984 (8)	0.4697 (5)	0.0172 (18)
C11	0.202 (2)	0.8912 (7)	0.4903 (6)	0.025 (2)
H11A	0.1228	0.8698	0.5369	0.037*
H11B	0.0713	0.9013	0.4481	0.037*
H11C	0.2953	0.9622	0.4992	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.0176 (2)	0.0145 (2)	0.0126 (2)	−0.00021 (12)	−0.00237 (15)	0.00053 (12)
Cl1	0.0203 (10)	0.0240 (11)	0.0198 (11)	−0.0012 (9)	−0.0085 (9)	−0.0023 (9)
O1	0.021 (3)	0.014 (3)	0.017 (3)	−0.005 (2)	−0.005 (3)	0.001 (3)
O2	0.022 (3)	0.027 (4)	0.023 (3)	0.006 (3)	−0.007 (3)	−0.005 (3)
O3	0.026 (4)	0.027 (4)	0.041 (4)	0.000 (3)	−0.004 (3)	−0.012 (3)
N1	0.022 (4)	0.012 (4)	0.015 (4)	−0.003 (3)	−0.002 (3)	0.000 (3)
C1	0.017 (3)	0.017 (3)	0.010 (3)	0.002 (3)	−0.005 (3)	−0.002 (3)
C2	0.021 (4)	0.021 (4)	0.013 (4)	−0.001 (4)	−0.003 (4)	0.003 (4)
C3	0.019 (4)	0.016 (4)	0.020 (4)	−0.001 (3)	−0.004 (3)	0.004 (3)
C4	0.016 (3)	0.015 (3)	0.013 (3)	−0.001 (3)	−0.008 (3)	−0.006 (3)
C5	0.020 (4)	0.013 (4)	0.009 (4)	0.003 (3)	−0.002 (3)	−0.001 (3)
C6	0.018 (4)	0.014 (4)	0.021 (4)	0.003 (3)	0.000 (3)	−0.001 (3)
C7	0.026 (4)	0.021 (4)	0.013 (4)	0.007 (4)	−0.006 (3)	0.001 (4)
C8	0.024 (4)	0.021 (4)	0.012 (4)	0.001 (4)	0.000 (4)	0.002 (4)
C9	0.025 (5)	0.017 (4)	0.022 (5)	0.000 (3)	0.008 (4)	0.006 (4)
C10	0.018 (4)	0.023 (4)	0.010 (4)	−0.005 (4)	−0.005 (3)	0.010 (4)
C11	0.031 (5)	0.020 (5)	0.022 (5)	0.003 (4)	−0.003 (4)	−0.004 (4)

Geometric parameters (Å, º) top

Pb1—O2	2.303 (6)	C2—H2	0.9500
Pb1—O1	2.328 (6)	C3—C4	1.380 (13)
Pb1—O1ⁱ	2.469 (6)	C3—H3	0.9500
Pb1—N1	2.559 (7)	C4—C5	1.417 (13)
Pb1—O3	2.729 (7)	C5—C6	1.384 (13)
Pb1—C10	2.848 (9)	C5—C7	1.441 (12)
Cl1—C4	1.722 (9)	C7—C8	1.356 (13)
O1—C1	1.319 (11)	C7—H7	0.9500
O1—Pb1ⁱ	2.469 (6)	C8—C9	1.397 (15)
O2—C10	1.257 (11)	C8—H8	0.9500
O3—C10	1.237 (10)	C9—H9	0.9500
N1—C9	1.317 (12)	C10—C11	1.524 (13)
N1—C6	1.370 (11)	C11—H11A	0.9800
C1—C2	1.404 (13)	C11—H11B	0.9800
C1—C6	1.451 (13)	C11—H11C	0.9800
C2—C3	1.407 (13)

O2—Pb1—O1	82.3 (2)	C2—C3—H3	119.6
O2—Pb1—O1ⁱ	93.9 (2)	C3—C4—C5	119.1 (8)
O1—Pb1—O1ⁱ	66.3 (2)	C3—C4—Cl1	118.8 (7)
O2—Pb1—N1	76.6 (2)	C5—C4—Cl1	122.2 (7)
O1—Pb1—N1	67.5 (2)	C6—C5—C4	120.7 (8)
O1ⁱ—Pb1—N1	133.6 (2)	C6—C5—C7	116.7 (8)
O2—Pb1—O3	51.1 (2)	C4—C5—C7	122.6 (8)
O1—Pb1—O3	119.6 (2)	N1—C6—C5	123.4 (8)
O1ⁱ—Pb1—O3	79.5 (2)	N1—C6—C1	115.5 (8)
N1—Pb1—O3	121.9 (2)	C5—C6—C1	121.0 (8)
O2—Pb1—C10	25.6 (2)	C8—C7—C5	119.4 (9)
O1—Pb1—C10	101.6 (2)	C8—C7—H7	120.3
O1ⁱ—Pb1—C10	86.5 (2)	C5—C7—H7	120.3
N1—Pb1—C10	99.5 (2)	C7—C8—C9	119.0 (8)
O3—Pb1—C10	25.5 (2)	C7—C8—H8	120.5
C1—O1—Pb1	121.3 (5)	C9—C8—H8	120.5
C1—O1—Pb1ⁱ	124.2 (5)	N1—C9—C8	123.9 (8)
Pb1—O1—Pb1ⁱ	113.7 (2)	N1—C9—H9	118.1
C10—O2—Pb1	102.2 (5)	C8—C9—H9	118.1
C10—O3—Pb1	82.6 (5)	O3—C10—O2	124.1 (9)
C9—N1—C6	117.6 (8)	O3—C10—C11	119.2 (8)
C9—N1—Pb1	128.0 (6)	O2—C10—C11	116.7 (8)
C6—N1—Pb1	114.4 (6)	O3—C10—Pb1	71.9 (5)
O1—C1—C2	122.8 (8)	O2—C10—Pb1	52.2 (4)
O1—C1—C6	120.9 (8)	C11—C10—Pb1	168.8 (6)
C2—C1—C6	116.3 (8)	C10—C11—H11A	109.5
C1—C2—C3	122.1 (8)	C10—C11—H11B	109.5
C1—C2—H2	119.0	H11A—C11—H11B	109.5
C3—C2—H2	119.0	C10—C11—H11C	109.5
C4—C3—C2	120.7 (8)	H11A—C11—H11C	109.5
C4—C3—H3	119.6	H11B—C11—H11C	109.5

O2—Pb1—O1—C1	73.2 (6)	Cl1—C4—C5—C6	−175.1 (6)
O1ⁱ—Pb1—O1—C1	170.9 (8)	C3—C4—C5—C7	−177.6 (8)
N1—Pb1—O1—C1	−5.5 (6)	Cl1—C4—C5—C7	3.6 (12)
O3—Pb1—O1—C1	109.5 (6)	C9—N1—C6—C5	−1.4 (12)
C10—Pb1—O1—C1	90.1 (6)	Pb1—N1—C6—C5	176.2 (6)
O2—Pb1—O1—Pb1ⁱ	−97.7 (3)	C9—N1—C6—C1	−179.6 (8)
O1ⁱ—Pb1—O1—Pb1ⁱ	0.0	Pb1—N1—C6—C1	−2.0 (9)
N1—Pb1—O1—Pb1ⁱ	−176.4 (3)	C4—C5—C6—N1	−179.6 (8)
O3—Pb1—O1—Pb1ⁱ	−61.4 (3)	C7—C5—C6—N1	1.7 (12)
C10—Pb1—O1—Pb1ⁱ	−80.8 (3)	C4—C5—C6—C1	−1.5 (12)
O1—Pb1—O2—C10	138.8 (5)	C7—C5—C6—C1	179.8 (8)
O1ⁱ—Pb1—O2—C10	73.4 (5)	O1—C1—C6—N1	−2.8 (12)
N1—Pb1—O2—C10	−152.6 (6)	C2—C1—C6—N1	176.6 (8)
O3—Pb1—O2—C10	0.3 (5)	O1—C1—C6—C5	179.0 (8)
O2—Pb1—O3—C10	−0.3 (5)	C2—C1—C6—C5	−1.6 (12)
O1—Pb1—O3—C10	−49.2 (6)	C6—C5—C7—C8	−1.2 (12)
O1ⁱ—Pb1—O3—C10	−104.0 (5)	C4—C5—C7—C8	−179.9 (8)
N1—Pb1—O3—C10	31.3 (6)	C5—C7—C8—C9	0.4 (13)
O2—Pb1—N1—C9	93.9 (7)	C6—N1—C9—C8	0.6 (13)
O1—Pb1—N1—C9	−179.0 (8)	Pb1—N1—C9—C8	−176.6 (6)
O1ⁱ—Pb1—N1—C9	176.4 (6)	C7—C8—C9—N1	−0.1 (14)
O3—Pb1—N1—C9	69.1 (8)	Pb1—O3—C10—O2	0.4 (8)
C10—Pb1—N1—C9	82.3 (7)	Pb1—O3—C10—C11	177.7 (7)
O2—Pb1—N1—C6	−83.4 (6)	Pb1—O2—C10—O3	−0.5 (10)
O1—Pb1—N1—C6	3.7 (5)	Pb1—O2—C10—C11	−177.9 (6)
O1ⁱ—Pb1—N1—C6	−0.9 (7)	O2—Pb1—C10—O3	179.5 (8)
O3—Pb1—N1—C6	−108.1 (6)	O1—Pb1—C10—O3	137.8 (5)
C10—Pb1—N1—C6	−95.0 (6)	O1ⁱ—Pb1—C10—O3	72.9 (5)
Pb1—O1—C1—C2	−172.5 (7)	N1—Pb1—C10—O3	−153.5 (5)
Pb1ⁱ—O1—C1—C2	−2.6 (11)	O1—Pb1—C10—O2	−41.8 (6)
Pb1—O1—C1—C6	6.8 (10)	O1ⁱ—Pb1—C10—O2	−106.7 (5)
Pb1ⁱ—O1—C1—C6	176.8 (6)	N1—Pb1—C10—O2	27.0 (6)
O1—C1—C2—C3	−178.1 (8)	O3—Pb1—C10—O2	−179.5 (8)
C6—C1—C2—C3	2.6 (13)	O2—Pb1—C10—C11	10 (3)
C1—C2—C3—C4	−0.4 (14)	O1—Pb1—C10—C11	−32 (3)
C2—C3—C4—C5	−2.8 (13)	O1ⁱ—Pb1—C10—C11	−97 (3)
C2—C3—C4—Cl1	176.0 (7)	N1—Pb1—C10—C11	37 (3)
C3—C4—C5—C6	3.7 (13)	O3—Pb1—C10—C11	−170 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Pb₂(C₉H₅ClNO)₂(C₂H₃O₂)₂]
M_r	889.65
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	5.3049 (1), 11.8200 (3), 17.4928 (3)
β (°)	94.569 (1)
V (Å³)	1093.38 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	15.67
Crystal size (mm)	0.10 × 0.03 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.303, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	7713, 1925, 1655
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.00
No. of reflections	1925
No. of parameters	155
No. of restraints	72
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	5.25, −3.38

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

Acknowledgements

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

References

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