Poly[(μ4-3-carb­oxy­benzoato-κ5O1:O1,O1′:O1′:O3)(quinolin-8-olato-κ2N,O)lead(II)]

Ghaemi, A.; Dadkhah, Z.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681105495X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m97-m98

doi:10.1107/S160053681105495X

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Poly[(μ₄-3-carboxybenzoato-κ⁵O¹:O¹,O^1′:O^1′:O³)(quinolin-8-olato-κ²N,O)lead(II)]

Akbar Ghaemi,^a ‡ Zohreh Dadkhah,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Saveh Branch, Islamic Azad University, Saveh, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of, Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 19 December 2011; accepted 21 December 2011; online 7 January 2012)

The asymmetric unit of the title complex, [Pb(C₈H₅O₄)(C₉H₆NO)]_n, comprises a Pb^II cation, a quinolin-8-olate anion and a 3-carboxybenzoate anion. The coordination geometry of the Pb^II atom is defined by one N and six O atoms, as well as a stereochemically active lone pair of electrons, and is based on a Ψ-dodecahedron. The quinolin-8-olate is chelating and the 3-carboxybenzoate anion forms bonds to four different Pb^II atoms. The benzoate end of the 3-carboxybenzoate ligand chelates one Pb^II atom and simultaneously bridges two Pb^II atoms on either side, forming a chain along the b axis. The carboxyl end of the 3-carboxybenzoate connects to a neighbouring chain by employing its carbonyl atom to form a bond to a Pb^II atom and the hydroxyl group to form a hydrogen bond to a quinolin-8-olate O atom. Thereby, a layer is formed in the bc plane.

Related literature

For background to Pb^II mixed quinolate carboxylate structures, see: Shahverdizadeh et al. (2008 ).

Experimental

Crystal data

[Pb(C₈H₅O₄)(C₉H₆NO)]
M_r = 516.46
Monoclinic, P 2₁ /c
a = 9.0746 (2) Å
b = 7.0262 (2) Å
c = 22.6919 (6) Å
β = 93.185 (3)°
V = 1444.60 (6) Å³
Z = 4
Mo Kα radiation
μ = 11.71 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.158, T_max = 0.273
9690 measured reflections
3325 independent reflections
3035 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.049
S = 1.01
3325 reflections
221 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.92 e Å⁻³
Δρ_min = −1.27 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb—O1	2.608 (2)
Pb—O1ⁱ	2.746 (2)
Pb—O2ⁱⁱ	2.578 (2)
Pb—O2ⁱ	2.809 (2)
Pb—O3ⁱⁱⁱ	2.840 (3)
Pb—O5	2.318 (2)
Pb—N1	2.468 (3)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1⋯O5ⁱⁱⁱ	0.84 (1)	1.74 (3)	2.539 (4)	158 (6)
Symmetry code: (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681105495X/qm2046sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105495X/qm2046Isup2.hkl

checkCIF report

Comment top

Mixed lead(II) complexes of quinolin-8-olate and monofunctional carboxylates have displayed a variety of structural motifs (Shahverdizadeh et al., 2008). In the present report, a 1:1 structure containing quinolin-8-olate and 3-carboxybenzoate is described, (I).

The asymmetric unit of (I) comprises a Pb^II cation, a quinolin-8-olate anion and a 3-carboxybenzoate anion, Fig. 1. The coordination geometry of the Pb^II atom is defined by a N and six O atoms as well as a stereochemically active lone pair of electrons, and is based on a Ψ-dodecahedron. The quinolin-8-olate anion is chelating, whereas the 3-carboxybenzoate anion is pentadentate, forming bonds to four different Pb^II atoms, Table 1. The benzoate group chelates one Pb^II atom and each of these O atoms forms a bond to a neighbouring Pb^II to form a chain along the b axis. Adjacent chains, along the c axis, are connected by Pb—O(carbonyl) bonds. The hydroxyl group forms a hydrogen bond to the quinolin-8-olate-O atom, Table 2. The result is a layer in the bc plane. Layers stack along the a axis, Fig. 3, with no specific intermolecular interactions between them.

Related literature top

For background to Pb^II mixed quinolate carboxylate structures, see: Shahverdizadeh et al. (2008).

Experimental top

The title complex was obtained by the following method. A methanol solution (10 ml) of 8-hydroxyquinoline (0.145 g, 1 mmol) was added to an aqueous solution (2 ml) of Pb(NO₃)₂ (0.331 g, 1 mmol). The mixture was stirred for 10 min. To this solution, was added a DMF solution (5 ml) of isophthalic acid (0.084 g, 0.5 mmol) slowly at room temperature. This mixture was filtered. After keeping the filtrate in air, crystals were formed at the bottom of the vessel upon slow evaporation of the solvents at room temperature. M.pt. 558 K (dec.). Yield: 65%.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The asymmetric unit of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the layer in the bc plane in (I).
	Fig. 3. A view in projection down the c axis of the unit-cell contents of (I) highlighting the stacking of layers.

Poly[(µ₄-3-carboxybenzoato- κ⁵O¹:O¹,O^1':O^1':O³)(quinolin- 8-olato-κ²N,O)lead(II)] top

Crystal data top

[Pb(C₈H₅O₄)(C₉H₆NO)]	F(000) = 968
M_r = 516.46	D_x = 2.375 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6118 reflections
a = 9.0746 (2) Å	θ = 2.2–27.5°
b = 7.0262 (2) Å	µ = 11.71 mm⁻¹
c = 22.6919 (6) Å	T = 100 K
β = 93.185 (3)°	Block, yellow
V = 1444.60 (6) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3325 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3035 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.8°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→8
T_min = 0.158, T_max = 0.273	l = −29→27
9690 measured reflections

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0237P)² + 0.5749P] where P = (F_o² + 2F_c²)/3
3325 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.92 e Å⁻³
1 restraint	Δρ_min = −1.27 e Å⁻³

Crystal data top

[Pb(C₈H₅O₄)(C₉H₆NO)]	V = 1444.60 (6) Å³
M_r = 516.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0746 (2) Å	µ = 11.71 mm⁻¹
b = 7.0262 (2) Å	T = 100 K
c = 22.6919 (6) Å	0.25 × 0.20 × 0.15 mm
β = 93.185 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3325 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3035 reflections with I > 2σ(I)
T_min = 0.158, T_max = 0.273	R_int = 0.029
9690 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	1 restraint
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.92 e Å⁻³
3325 reflections	Δρ_min = −1.27 e Å⁻³
221 parameters

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

	x	y	z	U_iso*/U_eq
Pb	0.513121 (14)	0.057458 (17)	0.305356 (5)	0.00777 (5)
O1	0.5980 (3)	0.4114 (3)	0.30020 (11)	0.0123 (5)
O2	0.4886 (3)	0.6925 (3)	0.31117 (10)	0.0107 (5)
O3	0.6052 (3)	0.7915 (4)	0.59124 (11)	0.0160 (6)
O4	0.4185 (3)	0.8397 (4)	0.52393 (12)	0.0141 (5)
H1	0.365 (6)	0.890 (8)	0.549 (2)	0.08 (2)*
O5	0.6896 (3)	0.0346 (3)	0.38285 (11)	0.0111 (5)
N1	0.7528 (4)	−0.0485 (4)	0.27073 (13)	0.0104 (6)
C1	0.5716 (4)	0.5570 (5)	0.33079 (16)	0.0099 (7)
C2	0.6368 (4)	0.5693 (4)	0.39260 (16)	0.0084 (7)
C3	0.7672 (4)	0.4692 (5)	0.40797 (16)	0.0112 (7)
H3	0.8141	0.3966	0.3791	0.013*
C4	0.8270 (4)	0.4767 (5)	0.46522 (17)	0.0136 (8)
H4	0.9160	0.4104	0.4754	0.016*
C5	0.7586 (4)	0.5801 (5)	0.50806 (17)	0.0140 (8)
H5	0.8006	0.5848	0.5473	0.017*
C6	0.6275 (4)	0.6774 (5)	0.49317 (15)	0.0111 (7)
C7	0.5672 (4)	0.6744 (5)	0.43551 (15)	0.0100 (7)
H7	0.4794	0.7432	0.4253	0.012*
C8	0.5498 (4)	0.7761 (5)	0.54049 (16)	0.0109 (7)
C9	0.7848 (4)	−0.0880 (5)	0.21594 (16)	0.0116 (8)
H9	0.7081	−0.0799	0.1858	0.014*
C10	0.9255 (4)	−0.1409 (5)	0.19995 (17)	0.0149 (8)
H10	0.9432	−0.1670	0.1599	0.018*
C11	1.0383 (4)	−0.1548 (5)	0.24300 (16)	0.0140 (8)
H11	1.1352	−0.1870	0.2327	0.017*
C12	1.0090 (4)	−0.1206 (5)	0.30261 (16)	0.0117 (8)
C13	1.1178 (4)	−0.1327 (5)	0.34965 (17)	0.0148 (8)
H13	1.2155	−0.1707	0.3422	0.018*
C14	1.0821 (4)	−0.0899 (5)	0.40557 (18)	0.0156 (8)
H14	1.1558	−0.0983	0.4369	0.019*
C15	0.9372 (4)	−0.0329 (5)	0.41800 (18)	0.0144 (8)
H15	0.9155	−0.0037	0.4575	0.017*
C16	0.8271 (4)	−0.0193 (5)	0.37373 (17)	0.0106 (7)
C17	0.8635 (4)	−0.0657 (4)	0.31489 (16)	0.0098 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb	0.00854 (8)	0.00841 (7)	0.00647 (8)	0.00005 (5)	0.00123 (5)	−0.00047 (5)
O1	0.0151 (14)	0.0122 (12)	0.0097 (13)	−0.0020 (11)	0.0002 (11)	−0.0010 (10)
O2	0.0123 (13)	0.0092 (12)	0.0107 (13)	0.0024 (10)	0.0018 (10)	−0.0005 (10)
O3	0.0171 (14)	0.0249 (14)	0.0061 (13)	−0.0028 (12)	0.0007 (11)	−0.0049 (11)
O4	0.0134 (14)	0.0197 (13)	0.0093 (13)	0.0005 (12)	0.0022 (11)	−0.0020 (11)
O5	0.0098 (13)	0.0145 (13)	0.0089 (13)	−0.0005 (10)	0.0005 (10)	−0.0008 (10)
N1	0.0118 (16)	0.0112 (15)	0.0080 (16)	−0.0034 (12)	−0.0002 (13)	−0.0007 (11)
C1	0.0112 (18)	0.0116 (17)	0.0072 (18)	−0.0050 (14)	0.0035 (14)	0.0023 (13)
C2	0.0123 (18)	0.0057 (15)	0.0074 (17)	−0.0025 (14)	0.0017 (14)	0.0017 (12)
C3	0.0126 (19)	0.0089 (16)	0.0123 (19)	−0.0005 (15)	0.0036 (15)	−0.0008 (14)
C4	0.0088 (18)	0.0169 (18)	0.015 (2)	0.0027 (15)	−0.0003 (15)	0.0001 (15)
C5	0.013 (2)	0.0189 (18)	0.0094 (19)	−0.0046 (16)	−0.0021 (15)	−0.0007 (15)
C6	0.0154 (19)	0.0104 (16)	0.0080 (18)	−0.0011 (15)	0.0045 (14)	0.0004 (14)
C7	0.0110 (18)	0.0084 (16)	0.0103 (18)	0.0000 (14)	−0.0031 (14)	−0.0012 (13)
C8	0.0120 (18)	0.0099 (16)	0.0108 (18)	−0.0054 (15)	0.0015 (14)	−0.0001 (14)
C9	0.0149 (19)	0.0112 (16)	0.0087 (18)	−0.0008 (15)	−0.0008 (15)	−0.0019 (14)
C10	0.020 (2)	0.0126 (18)	0.0129 (19)	−0.0008 (16)	0.0050 (15)	−0.0023 (14)
C11	0.0153 (19)	0.0098 (16)	0.017 (2)	0.0002 (15)	0.0062 (15)	0.0008 (14)
C12	0.0111 (19)	0.0068 (16)	0.017 (2)	−0.0019 (14)	0.0016 (15)	−0.0027 (14)
C13	0.0078 (18)	0.0150 (17)	0.021 (2)	0.0017 (15)	0.0003 (15)	0.0032 (15)
C14	0.012 (2)	0.0176 (18)	0.017 (2)	−0.0007 (16)	−0.0034 (16)	−0.0005 (15)
C15	0.014 (2)	0.0127 (18)	0.017 (2)	0.0015 (15)	0.0002 (16)	−0.0009 (15)
C16	0.0125 (19)	0.0031 (15)	0.016 (2)	0.0012 (14)	0.0022 (15)	0.0027 (13)
C17	0.0106 (18)	0.0071 (16)	0.0116 (19)	−0.0027 (14)	−0.0006 (15)	−0.0003 (13)

Geometric parameters (Å, º) top

Pb—O1	2.608 (2)	C4—C5	1.388 (5)
Pb—O1ⁱ	2.746 (2)	C4—H4	0.9500
Pb—O2ⁱⁱ	2.578 (2)	C5—C6	1.397 (5)
Pb—O2ⁱ	2.809 (2)	C5—H5	0.9500
Pb—O3ⁱⁱⁱ	2.840 (3)	C6—C7	1.390 (5)
Pb—O5	2.318 (2)	C6—C8	1.489 (5)
Pb—N1	2.468 (3)	C7—H7	0.9500
O1—C1	1.267 (4)	C9—C10	1.397 (5)
O1—Pb^iv	2.746 (2)	C9—H9	0.9500
O2—C1	1.278 (4)	C10—C11	1.379 (5)
O2—Pb^v	2.578 (2)	C10—H10	0.9500
O3—C8	1.235 (4)	C11—C12	1.414 (5)
O4—C8	1.308 (4)	C11—H11	0.9500
O4—H1	0.840 (10)	C12—C13	1.416 (5)
O5—C16	1.331 (4)	C12—C17	1.418 (5)
N1—C9	1.322 (5)	C13—C14	1.360 (5)
N1—C17	1.385 (4)	C13—H13	0.9500
C1—C2	1.494 (5)	C14—C15	1.418 (6)
C2—C3	1.403 (5)	C14—H14	0.9500
C2—C7	1.400 (5)	C15—C16	1.380 (5)
C3—C4	1.381 (5)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.431 (5)

O5—Pb—N1	68.69 (10)	C6—C5—H5	120.2
O5—Pb—O2ⁱⁱ	87.14 (7)	C7—C6—C5	120.4 (3)
N1—Pb—O2ⁱⁱ	78.24 (8)	C7—C6—C8	120.6 (3)
O5—Pb—O1	84.66 (8)	C5—C6—C8	119.0 (3)
N1—Pb—O1	90.33 (9)	C6—C7—C2	119.6 (3)
O2ⁱⁱ—Pb—O1	167.78 (8)	C6—C7—H7	120.2
O5—Pb—O1ⁱ	147.23 (8)	C2—C7—H7	120.2
N1—Pb—O1ⁱ	84.08 (9)	O3—C8—O4	123.7 (3)
O2ⁱⁱ—Pb—O1ⁱ	69.16 (7)	O3—C8—C6	121.9 (3)
O1—Pb—O1ⁱ	114.35 (6)	O4—C8—C6	114.4 (3)
O5—Pb—O3ⁱⁱⁱ	71.10 (8)	N1—C9—C10	123.5 (3)
N1—Pb—O3ⁱⁱⁱ	139.12 (8)	N1—C9—H9	118.2
O2ⁱⁱ—Pb—O3ⁱⁱⁱ	106.98 (8)	C10—C9—H9	118.2
O1—Pb—O3ⁱⁱⁱ	78.86 (8)	C11—C10—C9	119.2 (4)
O1ⁱ—Pb—O3ⁱⁱⁱ	136.32 (8)	C11—C10—H10	120.4
C1—O1—Pb	132.9 (2)	C9—C10—H10	120.4
C1—O1—Pb^iv	96.0 (2)	C10—C11—C12	119.6 (4)
Pb—O1—Pb^iv	107.49 (8)	C10—C11—H11	120.2
C1—O2—Pb^v	135.0 (2)	C12—C11—H11	120.2
C8—O4—H1	120 (4)	C11—C12—C13	123.4 (4)
C16—O5—Pb	121.1 (2)	C11—C12—C17	117.5 (3)
C9—N1—C17	118.3 (3)	C13—C12—C17	119.1 (3)
C9—N1—Pb	127.4 (2)	C14—C13—C12	119.9 (4)
C17—N1—Pb	114.4 (2)	C14—C13—H13	120.1
O1—C1—O2	122.4 (3)	C12—C13—H13	120.1
O1—C1—C2	118.9 (3)	C13—C14—C15	121.3 (4)
O2—C1—C2	118.6 (3)	C13—C14—H14	119.4
C3—C2—C7	119.9 (3)	C15—C14—H14	119.4
C3—C2—C1	119.3 (3)	C16—C15—C14	121.1 (4)
C7—C2—C1	120.9 (3)	C16—C15—H15	119.5
C4—C3—C2	119.8 (4)	C14—C15—H15	119.5
C4—C3—H3	120.1	O5—C16—C15	123.6 (4)
C2—C3—H3	120.1	O5—C16—C17	118.5 (3)
C3—C4—C5	120.7 (4)	C15—C16—C17	117.9 (3)
C3—C4—H4	119.6	N1—C17—C12	121.9 (3)
C5—C4—H4	119.6	N1—C17—C16	117.4 (3)
C4—C5—C6	119.7 (3)	C12—C17—C16	120.7 (3)
C4—C5—H5	120.2

O5—Pb—O1—C1	−77.9 (3)	C3—C4—C5—C6	0.2 (6)
N1—Pb—O1—C1	−146.5 (3)	C4—C5—C6—C7	−1.4 (5)
O2ⁱⁱ—Pb—O1—C1	−125.9 (4)	C4—C5—C6—C8	175.7 (3)
O1ⁱ—Pb—O1—C1	129.9 (3)	C5—C6—C7—C2	1.5 (5)
O3ⁱⁱⁱ—Pb—O1—C1	−6.2 (3)	C8—C6—C7—C2	−175.5 (3)
O5—Pb—O1—Pb^iv	165.82 (11)	C3—C2—C7—C6	−0.5 (5)
N1—Pb—O1—Pb^iv	97.27 (11)	C1—C2—C7—C6	177.6 (3)
O2ⁱⁱ—Pb—O1—Pb^iv	117.8 (3)	C7—C6—C8—O3	−175.3 (3)
O1ⁱ—Pb—O1—Pb^iv	13.62 (6)	C5—C6—C8—O3	7.6 (5)
O3ⁱⁱⁱ—Pb—O1—Pb^iv	−122.43 (10)	C7—C6—C8—O4	6.3 (5)
N1—Pb—O5—C16	0.4 (2)	C5—C6—C8—O4	−170.8 (3)
O2ⁱⁱ—Pb—O5—C16	78.9 (2)	C17—N1—C9—C10	−1.9 (5)
O1—Pb—O5—C16	−92.1 (2)	Pb—N1—C9—C10	177.7 (3)
O1ⁱ—Pb—O5—C16	36.2 (3)	N1—C9—C10—C11	0.4 (5)
O3ⁱⁱⁱ—Pb—O5—C16	−172.1 (2)	C9—C10—C11—C12	1.8 (5)
O5—Pb—N1—C9	−179.4 (3)	C10—C11—C12—C13	179.6 (3)
O2ⁱⁱ—Pb—N1—C9	89.1 (3)	C10—C11—C12—C17	−2.4 (5)
O1—Pb—N1—C9	−95.3 (3)	C11—C12—C13—C14	177.2 (3)
O1ⁱ—Pb—N1—C9	19.2 (3)	C17—C12—C13—C14	−0.7 (5)
O3ⁱⁱⁱ—Pb—N1—C9	−168.5 (2)	C12—C13—C14—C15	0.0 (6)
O5—Pb—N1—C17	0.1 (2)	C13—C14—C15—C16	0.1 (6)
O2ⁱⁱ—Pb—N1—C17	−91.4 (2)	Pb—O5—C16—C15	179.1 (3)
O1—Pb—N1—C17	84.3 (2)	Pb—O5—C16—C17	−0.9 (4)
O1ⁱ—Pb—N1—C17	−161.3 (2)	C14—C15—C16—O5	−179.5 (3)
O3ⁱⁱⁱ—Pb—N1—C17	11.0 (3)	C14—C15—C16—C17	0.4 (5)
Pb—O1—C1—O2	−108.0 (4)	C9—N1—C17—C12	1.1 (5)
Pb^iv—O1—C1—O2	12.7 (4)	Pb—N1—C17—C12	−178.5 (3)
Pb—O1—C1—C2	70.5 (4)	C9—N1—C17—C16	179.0 (3)
Pb^iv—O1—C1—C2	−168.8 (3)	Pb—N1—C17—C16	−0.6 (4)
Pb^v—O2—C1—O1	−129.2 (3)	C11—C12—C17—N1	1.0 (5)
Pb^v—O2—C1—C2	52.3 (5)	C13—C12—C17—N1	179.0 (3)
O1—C1—C2—C3	25.8 (5)	C11—C12—C17—C16	−176.8 (3)
O2—C1—C2—C3	−155.6 (3)	C13—C12—C17—C16	1.2 (5)
O1—C1—C2—C7	−152.3 (3)	O5—C16—C17—N1	1.0 (5)
O2—C1—C2—C7	26.2 (5)	C15—C16—C17—N1	−179.0 (3)
C7—C2—C3—C4	−0.7 (5)	O5—C16—C17—C12	178.9 (3)
C1—C2—C3—C4	−178.9 (3)	C15—C16—C17—C12	−1.1 (5)
C2—C3—C4—C5	0.9 (6)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, y+1/2, −z+1/2; (v) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···O5ⁱⁱⁱ	0.84 (1)	1.74 (3)	2.539 (4)	158 (6)

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

Experimental details

Crystal data
Chemical formula	[Pb(C₈H₅O₄)(C₉H₆NO)]
M_r	516.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.0746 (2), 7.0262 (2), 22.6919 (6)
β (°)	93.185 (3)
V (Å³)	1444.60 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	11.71
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.158, 0.273
No. of measured, independent and observed [I > 2σ(I)] reflections	9690, 3325, 3035
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.049, 1.01
No. of reflections	3325
No. of parameters	221
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.92, −1.27

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Pb—O1	2.608 (2)	Pb—O3ⁱⁱⁱ	2.840 (3)
Pb—O1ⁱ	2.746 (2)	Pb—O5	2.318 (2)
Pb—O2ⁱⁱ	2.578 (2)	Pb—N1	2.468 (3)
Pb—O2ⁱ	2.809 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···O5ⁱⁱⁱ	0.84 (1)	1.74 (3)	2.539 (4)	158 (6)

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

Footnotes

‡Additional correspondence author, e-mail: akbarghaemi@yahoo.com.

Acknowledgements

We gratefully acknowledge practical support of this study by the Islamic Azad University (Saveh Branch), and thank the University of Malaya for supporting the crystallographic facility.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Shahverdizadeh, G. H., Soudi, A. A., Morsali, A. & Retailleau, P. (2008). Inorg. Chim. Acta, 361, 1875–1884. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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