catena-Poly[[lead(II)-bis­(μ2-quinolin-8-ol­ato)-κ3N,O:O;κ3O:N,O] N,N-di­methyl­formamide hemisolvate]

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

doi:10.1107/S1600536812002796

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m210

doi:10.1107/S1600536812002796

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catena-Poly[[lead(II)-bis(μ₂-quinolin-8-olato)-κ³N,O:O;κ³O:N,O] N,N-dimethylformamide hemisolvate]

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

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

(Received 21 January 2012; accepted 23 January 2012; online 31 January 2012)

The asymmetric unit of the title compound, {[Pb(C₉H₆NO)₂]·0.5C₃H₇NO}_n, comprises Pb(quinolate)₂ and half a dimethylformamide molecule (which is disordered about a centre of inversion). The quinolate ligands N,O-chelate to a Pb^II ion and simultaneously bridge a neighbouring Pb^II ion to form a polymeric chain along [100] comprising Pb-linked Pb₂O₂ distorted rhombi. These chains pack to form a square grid, with the channels thus defined occupied by the disordered solvent molecules.

Related literature

For a recent Pb^II mixed quinolate carboxylate structure, see: Ghaemi et al. (2012 ). For the structure of the solvent-free Pb^II quinolate, see: Zhu et al. (2005 ).

Experimental

Crystal data

[Pb(C₉H₆NO)₂]·0.5C₃H₇NO
M_r = 532.04
Triclinic, $[P \overline 1]$
a = 8.1841 (2) Å
b = 9.6606 (3) Å
c = 10.8619 (3) Å
α = 96.683 (3)°
β = 98.277 (2)°
γ = 94.225 (3)°
V = 840.48 (4) Å³
Z = 2
Mo Kα radiation
μ = 10.06 mm⁻¹
T = 100 K
0.30 × 0.08 × 0.04 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.152, T_max = 0.689
13299 measured reflections
3866 independent reflections
3613 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.049
S = 1.01
3866 reflections
272 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 1.23 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb—O2	2.408 (2)
Pb—O1	2.468 (2)
Pb—N2	2.470 (3)
Pb—N1	2.566 (3)
Pb—O1ⁱ	2.618 (2)
Pb—O2ⁱⁱ	2.812 (2)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -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/S1600536812002796/hg5166sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002796/hg5166Isup2.hkl

checkCIF report

Comment top

During the course of recent studies into the structural chemistry of mixed Pb^II quinolate carboxylates (Ghaemi et al., 2012), the title binary Pb^II quinolate was isolated as a DMF hemi-solvate, (I), from an attempted reaction with maleic acid. The crystal structure of the solvent free and polymeric Pb(quinolate)₂ has been described (Zhu et al., 2005).

The asymmetric unit of (I) comprises Pb(quinolate)₂ and half a solvent DMF molecule (this is disordered over a centre of inversion), Fig. 1. Each quinolate anion N,O-chelates a Pb^II atom and at the same time bridges a neighbouring Pb^II atom via the carbonyl-O atom. The result is a polymeric chain comprising alternating Pb₂O₂ rhombi, Fig. 2. The degree in asymmetry in the Pb—O bridges varies, Table 1. The coordination geometry of the Pb^II atom is based on a distorted pentagonal bipyramid with one N atom occupying an axial site. The lone pair of electrons occupies the second axial position. It is noted that the O3 and O3' atoms (each with a 0.25 site occupancy factor) of disordered DMF molecule approach the Pb^II at distances 2.903 (12) and 2.977 (12) Å, respectively. These are not trans to the axial N atom forming angles of approximately 140°. If one of the DMF-O atoms is included as part of the coordination sphere, the coordination geometry would be described as ψ-dodecahedral.

In the crystal packing, the polymeric chains pack into a square grid which defines channels in which reside the disordered solvent molecules, Fig. 3. The aforementioned weak Pb···O(DMF) interactions serve to connect the polymeric chains into a layer in the ab plane.

Related literature top

For a recent Pb^II mixed quinolate carboxylate structure, see: Ghaemi et al. (2012). For the structure of the binary Pb^II quinolate, see: Zhu et al. (2005).

Experimental top

The title complex was obtained by the following method. 8-Hydroxyquinoline (0.036 g, 0.25 mmol) was added to an aqueous solution (5 ml) of Pb(NO₃)₂ (0.082 g, 0.25 mmol). The mixture was stirred for 15 min. Then to this solution, a DMF solution (5 ml) of maleic acid (0.029 g, 0.25 mmol) which with triethylamine neutralized was added slowly at room temperature. This mixture was filtered. After keeping the filtrate in air, crystals were formed at the bottom of the vessel on slow evaporation of the solvents at room temperature. M.p. 590 K. 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 polymeric chain along [100] in (I).
	Fig. 3. A view in projection down the a axis of the unit-cell contents of (I) highlighting the square grid defined by the polymeric chains and the inclusion of the solvent molecules (shown in space-filling mode) in the channels.

catena-Poly[[lead(II)-bis(µ₂-quinolin-8-olato)- κ³N,O:O;κ³O:N,O] N,N-dimethylformamide hemisolvate] top

Crystal data top

[Pb(C₉H₆NO)₂]·0.5C₃H₇NO	Z = 2
M_r = 532.04	F(000) = 504
Triclinic, P1	D_x = 2.102 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1841 (2) Å	Cell parameters from 8798 reflections
b = 9.6606 (3) Å	θ = 2.5–27.5°
c = 10.8619 (3) Å	µ = 10.06 mm⁻¹
α = 96.683 (3)°	T = 100 K
β = 98.277 (2)°	Block, yellow
γ = 94.225 (3)°	0.30 × 0.08 × 0.04 mm
V = 840.48 (4) Å³

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3866 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3613 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→12
T_min = 0.152, T_max = 0.689	l = −14→14
13299 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-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0245P)² + 0.0115P] where P = (F_o² + 2F_c²)/3
3866 reflections	(Δ/σ)_max = 0.002
272 parameters	Δρ_max = 1.23 e Å⁻³
36 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

[Pb(C₉H₆NO)₂]·0.5C₃H₇NO	γ = 94.225 (3)°
M_r = 532.04	V = 840.48 (4) Å³
Triclinic, P1	Z = 2
a = 8.1841 (2) Å	Mo Kα radiation
b = 9.6606 (3) Å	µ = 10.06 mm⁻¹
c = 10.8619 (3) Å	T = 100 K
α = 96.683 (3)°	0.30 × 0.08 × 0.04 mm
β = 98.277 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3866 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3613 reflections with I > 2σ(I)
T_min = 0.152, T_max = 0.689	R_int = 0.036
13299 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	36 restraints
wR(F²) = 0.049	H-atom parameters constrained
S = 1.01	Δρ_max = 1.23 e Å⁻³
3866 reflections	Δρ_min = −0.71 e Å⁻³
272 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pb	0.758370 (14)	0.465630 (13)	0.543410 (11)	0.01554 (5)
O1	1.0552 (3)	0.4449 (3)	0.6130 (2)	0.0232 (6)
O2	0.5307 (3)	0.5563 (3)	0.6350 (2)	0.0180 (5)
N1	0.8296 (3)	0.4221 (3)	0.7727 (3)	0.0162 (6)
N2	0.8215 (4)	0.7122 (3)	0.6385 (3)	0.0249 (7)
C1	0.7215 (4)	0.4163 (4)	0.8528 (3)	0.0206 (8)
H1	0.6154	0.4481	0.8308	0.025*
C2	0.7575 (5)	0.3651 (4)	0.9686 (3)	0.0248 (8)
H2	0.6775	0.3630	1.0238	0.030*
C3	0.9089 (5)	0.3184 (4)	1.0005 (3)	0.0247 (8)
H3	0.9344	0.2833	1.0784	0.030*
C4	1.0284 (4)	0.3217 (4)	0.9190 (3)	0.0204 (8)
C5	1.1862 (5)	0.2725 (4)	0.9433 (4)	0.0259 (8)
H5	1.2177	0.2343	1.0190	0.031*
C6	1.2937 (5)	0.2792 (4)	0.8591 (4)	0.0296 (9)
H6	1.3985	0.2434	0.8756	0.036*
C7	1.2512 (4)	0.3389 (4)	0.7477 (4)	0.0253 (8)
H7	1.3301	0.3448	0.6920	0.030*
C8	1.0982 (4)	0.3891 (4)	0.7165 (3)	0.0193 (7)
C9	0.9830 (4)	0.3776 (4)	0.8040 (3)	0.0178 (7)
C10	0.9624 (5)	0.7881 (5)	0.6391 (6)	0.0462 (14)
H10	1.0427	0.7492	0.5938	0.055*
C11	0.9986 (6)	0.9237 (5)	0.7038 (7)	0.071 (2)
H11	1.1016	0.9753	0.7023	0.086*
C12	0.8836 (6)	0.9807 (5)	0.7689 (6)	0.0586 (17)
H12	0.9070	1.0722	0.8134	0.070*
C13	0.7312 (5)	0.9046 (4)	0.7703 (4)	0.0306 (9)
C14	0.6057 (5)	0.9570 (4)	0.8344 (4)	0.0311 (9)
H14	0.6214	1.0486	0.8795	0.037*
C15	0.4614 (5)	0.8749 (4)	0.8309 (4)	0.0299 (9)
H15	0.3775	0.9103	0.8744	0.036*
C16	0.4342 (5)	0.7391 (4)	0.7644 (4)	0.0263 (9)
H16	0.3319	0.6856	0.7640	0.032*
C17	0.5523 (4)	0.6806 (4)	0.6993 (3)	0.0188 (7)
C18	0.7048 (4)	0.7676 (4)	0.7030 (3)	0.0199 (7)
O3	0.5643 (14)	0.2137 (13)	0.5793 (11)	0.0316 (18)	0.25
N3	0.476 (2)	−0.011 (2)	0.4938 (14)	0.0236 (17)	0.25
C19	0.588 (2)	0.1025 (17)	0.5172 (12)	0.031 (4)	0.25
H19	0.6900	0.0971	0.4850	0.037*	0.25
C20	0.319 (3)	−0.009 (3)	0.540 (2)	0.026 (4)	0.25
H20A	0.3237	−0.0606	0.6134	0.039*	0.25
H20B	0.2305	−0.0539	0.4745	0.039*	0.25
H20C	0.2977	0.0877	0.5650	0.039*	0.25
C21	0.557 (2)	−0.112 (2)	0.4205 (18)	0.026 (4)	0.25
H21A	0.4848	−0.1461	0.3412	0.039*	0.25
H21B	0.5803	−0.1910	0.4675	0.039*	0.25
H21C	0.6618	−0.0679	0.4030	0.039*	0.25
O3'	0.7253 (14)	0.1552 (12)	0.5310 (11)	0.0316 (18)	0.25
N3'	0.492 (3)	0.0002 (19)	0.4949 (14)	0.0236 (17)	0.25
C19'	0.5783 (18)	0.124 (2)	0.5450 (16)	0.031 (4)	0.25
H19'	0.5247	0.1905	0.5929	0.037*	0.25
C20'	0.511 (3)	−0.130 (2)	0.4189 (19)	0.026 (4)	0.25
H20D	0.4190	−0.1498	0.3493	0.039*	0.25
H20E	0.5115	−0.2068	0.4708	0.039*	0.25
H20F	0.6162	−0.1220	0.3856	0.039*	0.25
C21'	0.323 (3)	−0.023 (3)	0.518 (2)	0.026 (4)	0.25
H21D	0.3170	−0.0921	0.5772	0.039*	0.25
H21E	0.2505	−0.0590	0.4388	0.039*	0.25
H21F	0.2859	0.0649	0.5533	0.039*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb	0.01436 (7)	0.01590 (8)	0.01590 (8)	0.00224 (5)	0.00048 (5)	0.00189 (5)
O1	0.0172 (12)	0.0320 (15)	0.0241 (14)	0.0070 (11)	0.0044 (10)	0.0146 (12)
O2	0.0180 (12)	0.0203 (13)	0.0154 (13)	0.0008 (10)	0.0042 (10)	−0.0007 (10)
N1	0.0178 (14)	0.0164 (15)	0.0138 (15)	0.0004 (11)	0.0001 (11)	0.0032 (12)
N2	0.0189 (16)	0.0168 (16)	0.040 (2)	0.0027 (12)	0.0041 (14)	0.0068 (15)
C1	0.0215 (18)	0.0200 (19)	0.0199 (19)	−0.0006 (14)	0.0047 (14)	−0.0002 (15)
C2	0.034 (2)	0.024 (2)	0.0167 (19)	−0.0017 (16)	0.0065 (16)	0.0016 (16)
C3	0.039 (2)	0.0175 (19)	0.0156 (18)	0.0003 (16)	−0.0020 (16)	0.0022 (15)
C4	0.0273 (19)	0.0124 (17)	0.0176 (18)	−0.0047 (14)	−0.0054 (14)	0.0012 (14)
C5	0.028 (2)	0.021 (2)	0.025 (2)	−0.0033 (15)	−0.0080 (16)	0.0071 (16)
C6	0.0201 (19)	0.022 (2)	0.047 (3)	0.0030 (15)	−0.0066 (17)	0.0151 (19)
C7	0.0186 (18)	0.025 (2)	0.034 (2)	0.0006 (15)	0.0031 (16)	0.0136 (18)
C8	0.0185 (17)	0.0180 (18)	0.0213 (19)	−0.0001 (14)	−0.0001 (14)	0.0072 (15)
C9	0.0184 (17)	0.0130 (17)	0.0195 (18)	−0.0032 (13)	−0.0028 (13)	0.0019 (14)
C10	0.021 (2)	0.024 (2)	0.095 (4)	0.0009 (17)	0.013 (2)	0.005 (3)
C11	0.031 (3)	0.021 (2)	0.158 (7)	−0.003 (2)	0.015 (3)	−0.003 (3)
C12	0.041 (3)	0.014 (2)	0.113 (5)	−0.0008 (19)	−0.002 (3)	−0.007 (3)
C13	0.035 (2)	0.0173 (19)	0.036 (2)	0.0053 (16)	−0.0092 (18)	0.0034 (18)
C14	0.048 (3)	0.019 (2)	0.024 (2)	0.0141 (18)	−0.0063 (18)	−0.0012 (17)
C15	0.049 (3)	0.031 (2)	0.0136 (19)	0.0164 (19)	0.0081 (17)	0.0035 (17)
C16	0.034 (2)	0.029 (2)	0.0175 (19)	0.0051 (17)	0.0097 (16)	0.0032 (17)
C17	0.0270 (19)	0.0208 (18)	0.0089 (16)	0.0056 (15)	0.0017 (14)	0.0023 (14)
C18	0.0213 (18)	0.0189 (18)	0.0193 (19)	0.0062 (14)	−0.0017 (14)	0.0044 (15)
O3	0.036 (4)	0.026 (3)	0.031 (4)	−0.003 (3)	0.005 (3)	0.003 (3)
N3	0.025 (4)	0.023 (3)	0.025 (3)	−0.001 (3)	0.012 (2)	0.007 (2)
C19	0.029 (5)	0.031 (8)	0.035 (8)	0.001 (5)	0.006 (5)	0.017 (7)
C20	0.024 (5)	0.031 (6)	0.025 (5)	0.000 (4)	0.007 (4)	0.007 (4)
C21	0.029 (5)	0.026 (6)	0.026 (6)	0.005 (4)	0.012 (4)	0.003 (4)
O3'	0.036 (4)	0.026 (3)	0.031 (4)	−0.003 (3)	0.005 (3)	0.003 (3)
N3'	0.025 (4)	0.023 (3)	0.025 (3)	−0.001 (3)	0.012 (2)	0.007 (2)
C19'	0.029 (5)	0.031 (8)	0.035 (8)	0.001 (5)	0.006 (5)	0.017 (7)
C20'	0.024 (5)	0.031 (6)	0.025 (5)	0.000 (4)	0.007 (4)	0.007 (4)
C21'	0.029 (5)	0.026 (6)	0.026 (6)	0.005 (4)	0.012 (4)	0.003 (4)

Geometric parameters (Å, º) top

Pb—O2	2.408 (2)	C12—C13	1.403 (6)
Pb—O1	2.468 (2)	C12—H12	0.9500
Pb—N2	2.470 (3)	C13—C14	1.413 (6)
Pb—N1	2.566 (3)	C13—C18	1.421 (5)
Pb—O1ⁱ	2.618 (2)	C14—C15	1.366 (6)
Pb—O2ⁱⁱ	2.812 (2)	C14—H14	0.9500
Pb—O3	2.903 (12)	C15—C16	1.408 (6)
Pb—O3'	2.977 (12)	C15—H15	0.9500
O1—C8	1.317 (4)	C16—C17	1.392 (5)
O1—Pbⁱ	2.618 (2)	C16—H16	0.9500
O2—C17	1.304 (4)	C17—C18	1.445 (5)
N1—C1	1.330 (4)	O3—C19	1.244 (10)
N1—C9	1.367 (4)	N3—C19	1.350 (10)
N2—C10	1.319 (5)	N3—C20	1.449 (10)
N2—C18	1.367 (5)	N3—C21	1.448 (10)
C1—C2	1.405 (5)	C19—H19	0.9500
C1—H1	0.9500	C20—H20A	0.9800
C2—C3	1.361 (5)	C20—H20B	0.9800
C2—H2	0.9500	C20—H20C	0.9800
C3—C4	1.412 (5)	C21—H21A	0.9800
C3—H3	0.9500	C21—H21B	0.9800
C4—C5	1.409 (5)	C21—H21C	0.9800
C4—C9	1.429 (5)	O3'—C19'	1.254 (10)
C5—C6	1.361 (6)	N3'—C19'	1.357 (10)
C5—H5	0.9500	N3'—C21'	1.453 (10)
C6—C7	1.410 (5)	N3'—C20'	1.455 (10)
C6—H6	0.9500	C19'—H19'	0.9500
C7—C8	1.387 (5)	C20'—H20D	0.9800
C7—H7	0.9500	C20'—H20E	0.9800
C8—C9	1.439 (5)	C20'—H20F	0.9800
C10—C11	1.402 (7)	C21'—H21D	0.9800
C10—H10	0.9500	C21'—H21E	0.9800
C11—C12	1.366 (8)	C21'—H21F	0.9800
C11—H11	0.9500

O2—Pb—O1	136.81 (8)	C11—C10—H10	118.6
O2—Pb—N2	67.61 (9)	C12—C11—C10	119.0 (4)
O1—Pb—N2	84.94 (9)	C12—C11—H11	120.5
O2—Pb—N1	77.78 (8)	C10—C11—H11	120.5
O1—Pb—N1	65.49 (8)	C11—C12—C13	120.4 (5)
N2—Pb—N1	82.06 (10)	C11—C12—H12	119.8
O2—Pb—O1ⁱ	133.72 (8)	C13—C12—H12	119.8
O1—Pb—O1ⁱ	67.90 (9)	C12—C13—C14	123.6 (4)
N2—Pb—O1ⁱ	80.59 (10)	C12—C13—C18	117.0 (4)
N1—Pb—O1ⁱ	131.30 (8)	C14—C13—C18	119.4 (4)
C8—O1—Pb	118.6 (2)	C15—C14—C13	119.4 (4)
C8—O1—Pbⁱ	129.3 (2)	C15—C14—H14	120.3
Pb—O1—Pbⁱ	112.10 (9)	C13—C14—H14	120.3
C17—O2—Pb	119.0 (2)	C14—C15—C16	121.6 (4)
C1—N1—C9	119.1 (3)	C14—C15—H15	119.2
C1—N1—Pb	124.9 (2)	C16—C15—H15	119.2
C9—N1—Pb	114.9 (2)	C17—C16—C15	122.2 (4)
C10—N2—C18	119.0 (4)	C17—C16—H16	118.9
C10—N2—Pb	124.8 (3)	C15—C16—H16	118.9
C18—N2—Pb	116.1 (2)	O2—C17—C16	124.0 (3)
N1—C1—C2	122.8 (3)	O2—C17—C18	119.8 (3)
N1—C1—H1	118.6	C16—C17—C18	116.2 (3)
C2—C1—H1	118.6	N2—C18—C13	121.8 (3)
C3—C2—C1	118.9 (3)	N2—C18—C17	117.0 (3)
C3—C2—H2	120.5	C13—C18—C17	121.3 (3)
C1—C2—H2	120.5	C19—N3—C20	121.2 (19)
C2—C3—C4	120.7 (3)	C19—N3—C21	103.1 (15)
C2—C3—H3	119.6	C20—N3—C21	135.6 (19)
C4—C3—H3	119.6	O3—C19—N3	122.8 (18)
C3—C4—C5	124.4 (3)	O3—C19—H19	118.6
C3—C4—C9	116.8 (3)	N3—C19—H19	118.6
C5—C4—C9	118.8 (3)	C19'—N3'—C21'	118 (2)
C6—C5—C4	120.5 (4)	C19'—N3'—C20'	141 (2)
C6—C5—H5	119.8	C21'—N3'—C20'	101.4 (16)
C4—C5—H5	119.8	O3'—C19'—N3'	123 (2)
C5—C6—C7	120.7 (3)	O3'—C19'—H19'	118.6
C5—C6—H6	119.6	N3'—C19'—H19'	118.6
C7—C6—H6	119.6	N3'—C20'—H20D	109.5
C8—C7—C6	122.4 (3)	N3'—C20'—H20E	109.5
C8—C7—H7	118.8	H20D—C20'—H20E	109.5
C6—C7—H7	118.8	N3'—C20'—H20F	109.5
O1—C8—C7	123.6 (3)	H20D—C20'—H20F	109.5
O1—C8—C9	119.8 (3)	H20E—C20'—H20F	109.5
C7—C8—C9	116.6 (3)	N3'—C21'—H21D	109.5
N1—C9—C4	121.6 (3)	N3'—C21'—H21E	109.5
N1—C9—C8	117.4 (3)	H21D—C21'—H21E	109.5
C4—C9—C8	120.9 (3)	N3'—C21'—H21F	109.5
N2—C10—C11	122.8 (4)	H21D—C21'—H21F	109.5
N2—C10—H10	118.6	H21E—C21'—H21F	109.5

O2—Pb—O1—C8	50.9 (3)	C6—C7—C8—C9	0.0 (6)
N2—Pb—O1—C8	100.2 (3)	C1—N1—C9—C4	1.6 (5)
N1—Pb—O1—C8	16.6 (2)	Pb—N1—C9—C4	−167.0 (3)
O1ⁱ—Pb—O1—C8	−178.0 (3)	C1—N1—C9—C8	−178.3 (3)
O2—Pb—O1—Pbⁱ	−131.10 (11)	Pb—N1—C9—C8	13.1 (4)
N2—Pb—O1—Pbⁱ	−81.88 (12)	C3—C4—C9—N1	−1.8 (5)
N1—Pb—O1—Pbⁱ	−165.45 (14)	C5—C4—C9—N1	177.5 (3)
O1ⁱ—Pb—O1—Pbⁱ	0.0	C3—C4—C9—C8	178.2 (3)
O1—Pb—O2—C17	48.0 (3)	C5—C4—C9—C8	−2.6 (5)
N2—Pb—O2—C17	−6.7 (2)	O1—C8—C9—N1	2.0 (5)
N1—Pb—O2—C17	79.7 (2)	C7—C8—C9—N1	−177.8 (3)
O1ⁱ—Pb—O2—C17	−57.0 (3)	O1—C8—C9—C4	−177.9 (3)
O2—Pb—N1—C1	20.5 (3)	C7—C8—C9—C4	2.3 (5)
O1—Pb—N1—C1	177.2 (3)	C18—N2—C10—C11	0.3 (8)
N2—Pb—N1—C1	89.2 (3)	Pb—N2—C10—C11	−174.2 (5)
O1ⁱ—Pb—N1—C1	159.2 (2)	N2—C10—C11—C12	−0.2 (10)
O2—Pb—N1—C9	−171.7 (2)	C10—C11—C12—C13	−0.4 (10)
O1—Pb—N1—C9	−14.9 (2)	C11—C12—C13—C14	−179.3 (5)
N2—Pb—N1—C9	−103.0 (2)	C11—C12—C13—C18	0.7 (8)
O1ⁱ—Pb—N1—C9	−33.0 (3)	C12—C13—C14—C15	−179.7 (5)
O2—Pb—N2—C10	−179.4 (4)	C18—C13—C14—C15	0.3 (6)
O1—Pb—N2—C10	34.7 (4)	C13—C14—C15—C16	−0.3 (6)
N1—Pb—N2—C10	100.6 (4)	C14—C15—C16—C17	0.3 (6)
O1ⁱ—Pb—N2—C10	−33.7 (4)	Pb—O2—C17—C16	−174.8 (3)
O2—Pb—N2—C18	6.0 (2)	Pb—O2—C17—C18	6.8 (4)
O1—Pb—N2—C18	−139.9 (3)	C15—C16—C17—O2	−178.8 (3)
N1—Pb—N2—C18	−74.0 (3)	C15—C16—C17—C18	−0.4 (5)
O1ⁱ—Pb—N2—C18	151.7 (3)	C10—N2—C18—C13	0.0 (6)
C9—N1—C1—C2	−0.5 (5)	Pb—N2—C18—C13	175.1 (3)
Pb—N1—C1—C2	166.9 (3)	C10—N2—C18—C17	179.9 (4)
N1—C1—C2—C3	−0.4 (6)	Pb—N2—C18—C17	−5.1 (4)
C1—C2—C3—C4	0.2 (6)	C12—C13—C18—N2	−0.5 (6)
C2—C3—C4—C5	−178.4 (4)	C14—C13—C18—N2	179.5 (3)
C2—C3—C4—C9	0.8 (5)	C12—C13—C18—C17	179.6 (4)
C3—C4—C5—C6	179.7 (4)	C14—C13—C18—C17	−0.3 (6)
C9—C4—C5—C6	0.5 (5)	O2—C17—C18—N2	−0.9 (5)
C4—C5—C6—C7	1.7 (6)	C16—C17—C18—N2	−179.4 (3)
C5—C6—C7—C8	−2.0 (6)	O2—C17—C18—C13	178.9 (3)
Pb—O1—C8—C7	162.6 (3)	C16—C17—C18—C13	0.4 (5)
Pbⁱ—O1—C8—C7	−14.9 (5)	C20—N3—C19—O3	0.0 (3)
Pb—O1—C8—C9	−17.2 (4)	C21—N3—C19—O3	−179.9 (3)
Pbⁱ—O1—C8—C9	165.3 (2)	C21'—N3'—C19'—O3'	179.9 (3)
C6—C7—C8—O1	−179.8 (4)	C20'—N3'—C19'—O3'	0.0 (5)

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

Experimental details

Crystal data
Chemical formula	[Pb(C₉H₆NO)₂]·0.5C₃H₇NO
M_r	532.04
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.1841 (2), 9.6606 (3), 10.8619 (3)
α, β, γ (°)	96.683 (3), 98.277 (2), 94.225 (3)
V (Å³)	840.48 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	10.06
Crystal size (mm)	0.30 × 0.08 × 0.04

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.152, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	13299, 3866, 3613
R_int	0.036
(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	3866
No. of parameters	272
No. of restraints	36
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.23, −0.71

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—O2	2.408 (2)	Pb—N1	2.566 (3)
Pb—O1	2.468 (2)	Pb—O1ⁱ	2.618 (2)
Pb—N2	2.470 (3)	Pb—O2ⁱⁱ	2.812 (2)

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

Footnotes

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

Acknowledgements

The authors gratefully acknowledge practical support of this study by the Islamic Azad University (Saveh Branch), and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM·C/HIR/MOHE/SC/12).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, 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
Ghaemi, A., Dadkhah, Z., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, m97–m98. CrossRef IUCr Journals Google Scholar
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Zhu, L.-H., Zeng, M.-H. & Ng, S. W. (2005). Acta Cryst. E61, m1082–m1084. Web of Science CSD CrossRef IUCr Journals Google Scholar

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