catena-Poly[[(1,10-phenanthroline-κ2N,N′)lead(II)]-di-μ-nitrato-κ3O,O′:O′′;κ3O:O′,O′′-[(1,10-phenanthroline-κ2N,N′)lead(II)]-bis­(μ-2,2,2-trichloro­acetato-κ2O:O′)]

Shahverdizadeh, G.H.; Ng, S.W.; Tiekink, E.R.T.; Mirtamizdoust, B.

doi:10.1107/S1600536812003595

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m237-m238

doi:10.1107/S1600536812003595

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catena-Poly[[(1,10-phenanthroline-κ²N,N′)lead(II)]-di-μ-nitrato-κ³O,O′:O′′;κ³O:O′,O′′-[(1,10-phenanthroline-κ²N,N′)lead(II)]-bis(μ-2,2,2-trichloroacetato-κ²O:O′)]

Gholam Hossein Shahverdizadeh,^a ‡ Seik Weng Ng,^b,^c Edward R. T. Tiekink ^b ^* and Babak Mirtamizdoust ^d

^aDepartment of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, PO Box 1655, Tabriz, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^dDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Tabriz, PO Box 5166616471, Tabriz, Iran
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 26 January 2012; accepted 27 January 2012; online 4 February 2012)

In the title Pb^II complex, [Pb₂(C₂Cl₃O₂)₂(NO₃)₂(C₁₂H₈N₂)₂]_n, the 1,10-phenanthroline ligand is chelating, the nitrate anion chelates one Pb^II ion and simultaneously bridges a neighbouring Pb^II ion via the third O atom, and the trichloroacetate anion is bidentate, bridging two Pb^II ions. The coordination geometry is based on a pentagonal–bipramidal geometry defined by an N₂O₅ donor set with no obvious stereochemical role for the lead-bound lone pair of electrons. The coordination polymer has a zigzag topology along [010] and comprises alternating eight-membered {PbONO}₂ and {PbOCO}₂ rings.

Related literature

On the stereochemical activity of lone pairs of electrons in Pb^II structures, see: Davidovich et al. (2009 ). For recent structural studies of mixed-ligand Pb^II compounds, see: Shahverdizadeh et al. (2008 , 2011a ,b ). For specialized crystallization techniques, see: Harrowfield et al. (1996 ).

Experimental

Crystal data

[Pb₂(C₂Cl₃O₂)₂(NO₃)₂(C₁₂H₈N₂)₂]
M_r = 1223.54
Triclinic, $[P \overline 1]$
a = 8.8852 (3) Å
b = 9.7465 (3) Å
c = 11.1570 (3) Å
α = 109.427 (3)°
β = 99.019 (3)°
γ = 106.199 (3)°
V = 841.13 (4) Å³
Z = 1
Mo Kα radiation
μ = 10.54 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.227, T_max = 0.419
12671 measured reflections
3899 independent reflections
3740 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.017
wR(F²) = 0.038
S = 0.99
3899 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.97 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb—O1	2.410 (2)
Pb—O2ⁱ	2.821 (2)
Pb—O3	2.591 (2)
Pb—O4	2.844 (2)
Pb—O5ⁱⁱ	2.807 (2)
Pb—N1	2.576 (2)
Pb—N2	2.515 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -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: X-SEED (Barbour, 2001 ) 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/S1600536812003595/hg5168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003595/hg5168Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of Pb^II with N– and O-donor ligands has been investigated in the past decade and frequently discussed in regard of the stereochemical activity of the lone pair of electrons (Davidovich et al., 2009). In connection with recent structural studies (Shahverdizadeh et al., 2008, 2011a, 2011b), herein we report the cyrstal and molecular structure of the mixed ligand Pb^II complex containing nitrate, trichloroacetate and 1,10-phenanthroline, (I).

A view of the asymmetic unit is shown in Fig. 1. This comprises a Pb^II atom, a chelating 1,10-phenanthroline molecule, a nitrate anion and a trichloroacetate anion. The nitrate anion chelates one Pb^II atom and at the same time bridges a second Pb^II atom via the third O atom. The trichloroacetate anion is bidentate, bridging two Pb^II atoms. Both bridges are non-symmetric, Table 1. The resulting coordination geometry, Fig. 2, is based on a distorted pentagonal bipyramid with no obvious role for the lead-bound lone pair of electrons.

The resulting polymeric chain along [010] has a zigzag topology with the backbone being defined by alternating eight-membered {PbONO}₂ and {PbOCO}₂ rings, Fig. 3.

Related literature top

On the stereochemical activity of lone pairs of electrons in Pb^II structures, see: Davidovich et al. (2009). For recent structural studies of mixed-ligand Pb^II compounds, see: Shahverdizadeh et al. (2008, 2011a,b). For specialized crystallization techniques, see: Harrowfield et al. (1996).

Experimental top

1,10-Phenanthroline (1 mmol) was placed in one arm of a branched tube (Harrowfield et al., 1996) and a mixture of lead(II) nitrate (1 mmol) and trichloroacetic acid (1 mmol) in the other. Methanol was then added to fill both arms, the tube sealed and the ligand-containing arm immersed in a bath at 333 K, while the other was left at ambient temperature. After two weeks, crystals had deposited in the arm held at ambient temperature. They were filtered off, washed with acetone and ether, and air-dried. Yield: 65%. M.pt. = 491 K.

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: X-SEED (Barbour, 2001) 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 70% probability level.
	Fig. 2. A view of the distorted pentagonal bipyramidal coordination geometry for the lead atom in (I).
	Fig. 3. A view of the zigzag polymeric chain along [010] in (I).

catena-Poly[[(1,10-phenanthroline-κ²N,N')lead(II)]- di-µ-nitrato-κ³O,O':O''; κ³O:O',O''-[(1,10-phenanthroline- κ²N,N')lead(II)]-bis(µ-2,2,2-trichloroacetato- κ²O:O')] top

Crystal data top

[Pb₂(C₂Cl₃O₂)₂(NO₃)₂(C₁₂H₈N₂)₂]	Z = 1
M_r = 1223.54	F(000) = 572
Triclinic, P1	D_x = 2.415 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8852 (3) Å	Cell parameters from 9962 reflections
b = 9.7465 (3) Å	θ = 2.4–27.5°
c = 11.1570 (3) Å	µ = 10.54 mm⁻¹
α = 109.427 (3)°	T = 100 K
β = 99.019 (3)°	Prism, colourless
γ = 106.199 (3)°	0.20 × 0.15 × 0.10 mm
V = 841.13 (4) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3899 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3740 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→12
T_min = 0.227, T_max = 0.419	l = −14→14
12671 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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.038	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0188P)²] where P = (F_o² + 2F_c²)/3
3899 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.84 e Å⁻³
0 restraints	Δρ_min = −0.97 e Å⁻³

Crystal data top

[Pb₂(C₂Cl₃O₂)₂(NO₃)₂(C₁₂H₈N₂)₂]	γ = 106.199 (3)°
M_r = 1223.54	V = 841.13 (4) Å³
Triclinic, P1	Z = 1
a = 8.8852 (3) Å	Mo Kα radiation
b = 9.7465 (3) Å	µ = 10.54 mm⁻¹
c = 11.1570 (3) Å	T = 100 K
α = 109.427 (3)°	0.20 × 0.15 × 0.10 mm
β = 99.019 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3899 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3740 reflections with I > 2σ(I)
T_min = 0.227, T_max = 0.419	R_int = 0.029
12671 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	0 restraints
wR(F²) = 0.038	H-atom parameters constrained
S = 0.99	Δρ_max = 0.84 e Å⁻³
3899 reflections	Δρ_min = −0.97 e Å⁻³
235 parameters

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

	x	y	z	U_iso*/U_eq
Pb	0.526354 (11)	0.321866 (10)	0.619700 (8)	0.00914 (4)
Cl1	1.10668 (9)	0.71315 (9)	0.63924 (7)	0.02148 (16)
Cl2	0.92529 (9)	0.85568 (8)	0.80608 (7)	0.01891 (15)
Cl3	0.89253 (10)	0.85230 (9)	0.54481 (7)	0.02467 (17)
O1	0.7927 (2)	0.5079 (2)	0.66123 (18)	0.0146 (4)
O2	0.6722 (3)	0.5436 (2)	0.4883 (2)	0.0231 (5)
O3	0.6734 (2)	0.1262 (2)	0.54516 (18)	0.0148 (4)
O4	0.5454 (2)	0.1386 (2)	0.36793 (18)	0.0157 (4)
O5	0.6385 (3)	−0.0491 (2)	0.35098 (19)	0.0167 (4)
N1	0.5609 (3)	0.5650 (3)	0.8223 (2)	0.0112 (5)
N2	0.6794 (3)	0.3366 (3)	0.8360 (2)	0.0115 (5)
N3	0.6188 (3)	0.0712 (3)	0.4200 (2)	0.0115 (5)
C1	0.5074 (3)	0.6760 (3)	0.8136 (3)	0.0131 (6)
H1	0.4390	0.6586	0.7314	0.016*
C2	0.5473 (4)	0.8182 (3)	0.9205 (3)	0.0163 (6)
H2	0.5091	0.8964	0.9098	0.020*
C3	0.6421 (4)	0.8433 (3)	1.0406 (3)	0.0152 (6)
H3	0.6673	0.9378	1.1147	0.018*
C4	0.7023 (3)	0.7275 (3)	1.0538 (3)	0.0115 (5)
C5	0.6586 (3)	0.5890 (3)	0.9403 (3)	0.0111 (5)
C6	0.7343 (3)	0.2258 (3)	0.8442 (3)	0.0120 (5)
H6	0.7036	0.1326	0.7676	0.014*
C7	0.8356 (4)	0.2399 (3)	0.9606 (3)	0.0154 (6)
H7	0.8731	0.1580	0.9619	0.018*
C8	0.8803 (3)	0.3727 (3)	1.0725 (3)	0.0150 (6)
H8	0.9508	0.3849	1.1517	0.018*
C9	0.8205 (3)	0.4908 (3)	1.0688 (3)	0.0113 (5)
C10	0.7198 (3)	0.4687 (3)	0.9475 (2)	0.0098 (5)
C11	0.8037 (4)	0.7453 (3)	1.1749 (3)	0.0151 (6)
H11	0.8318	0.8382	1.2512	0.018*
C12	0.8606 (3)	0.6330 (3)	1.1830 (3)	0.0147 (6)
H12	0.9277	0.6478	1.2648	0.018*
C13	0.7796 (3)	0.5824 (3)	0.5894 (3)	0.0123 (6)
C14	0.9201 (3)	0.7446 (3)	0.6404 (3)	0.0142 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb	0.01030 (6)	0.00697 (6)	0.00857 (6)	0.00233 (4)	0.00028 (4)	0.00284 (4)
Cl1	0.0130 (3)	0.0269 (4)	0.0277 (4)	0.0043 (3)	0.0084 (3)	0.0157 (3)
Cl2	0.0239 (4)	0.0124 (3)	0.0149 (3)	0.0045 (3)	0.0009 (3)	0.0024 (3)
Cl3	0.0247 (4)	0.0209 (4)	0.0244 (4)	−0.0022 (3)	−0.0044 (3)	0.0178 (3)
O1	0.0157 (10)	0.0124 (10)	0.0149 (10)	0.0008 (8)	0.0043 (8)	0.0080 (8)
O2	0.0218 (12)	0.0128 (10)	0.0234 (11)	0.0013 (9)	−0.0097 (10)	0.0048 (9)
O3	0.0179 (11)	0.0173 (10)	0.0092 (9)	0.0073 (9)	0.0027 (8)	0.0047 (8)
O4	0.0187 (11)	0.0162 (10)	0.0154 (10)	0.0073 (9)	0.0038 (9)	0.0096 (8)
O5	0.0240 (11)	0.0096 (10)	0.0192 (10)	0.0078 (9)	0.0125 (9)	0.0043 (8)
N1	0.0115 (11)	0.0115 (11)	0.0106 (11)	0.0035 (9)	0.0022 (9)	0.0051 (9)
N2	0.0137 (12)	0.0088 (11)	0.0123 (11)	0.0039 (9)	0.0031 (10)	0.0046 (9)
N3	0.0120 (12)	0.0096 (11)	0.0135 (12)	0.0014 (9)	0.0063 (10)	0.0061 (9)
C1	0.0163 (14)	0.0149 (14)	0.0111 (13)	0.0092 (12)	0.0054 (11)	0.0053 (11)
C2	0.0230 (16)	0.0137 (14)	0.0165 (14)	0.0109 (12)	0.0077 (13)	0.0065 (11)
C3	0.0193 (15)	0.0109 (13)	0.0146 (14)	0.0046 (12)	0.0073 (12)	0.0033 (11)
C4	0.0130 (14)	0.0123 (13)	0.0107 (13)	0.0041 (11)	0.0055 (11)	0.0055 (10)
C5	0.0105 (13)	0.0116 (13)	0.0122 (13)	0.0013 (11)	0.0053 (11)	0.0069 (10)
C6	0.0144 (14)	0.0098 (13)	0.0111 (13)	0.0039 (11)	0.0027 (11)	0.0040 (10)
C7	0.0193 (15)	0.0144 (14)	0.0171 (14)	0.0081 (12)	0.0051 (12)	0.0101 (11)
C8	0.0170 (15)	0.0187 (15)	0.0131 (14)	0.0077 (12)	0.0035 (12)	0.0100 (11)
C9	0.0107 (13)	0.0125 (13)	0.0095 (13)	0.0025 (11)	0.0017 (11)	0.0047 (10)
C10	0.0096 (13)	0.0101 (13)	0.0101 (12)	0.0026 (10)	0.0041 (11)	0.0046 (10)
C11	0.0187 (15)	0.0121 (14)	0.0107 (13)	0.0036 (12)	0.0042 (12)	0.0015 (11)
C12	0.0125 (14)	0.0172 (14)	0.0095 (13)	0.0028 (11)	0.0003 (11)	0.0028 (11)
C13	0.0119 (14)	0.0110 (13)	0.0143 (14)	0.0045 (11)	0.0061 (12)	0.0038 (11)
C14	0.0124 (14)	0.0161 (14)	0.0145 (14)	0.0033 (11)	0.0018 (11)	0.0091 (11)

Geometric parameters (Å, º) top

Pb—O1	2.410 (2)	C1—H1	0.9500
Pb—O2ⁱ	2.821 (2)	C2—C3	1.371 (4)
Pb—O3	2.591 (2)	C2—H2	0.9500
Pb—O4	2.844 (2)	C3—C4	1.415 (4)
Pb—O5ⁱⁱ	2.807 (2)	C3—H3	0.9500
Pb—N1	2.576 (2)	C4—C5	1.412 (4)
Pb—N2	2.515 (2)	C4—C11	1.429 (4)
Cl1—C14	1.770 (3)	C5—C10	1.442 (4)
Cl2—C14	1.790 (3)	C6—C7	1.401 (4)
Cl3—C14	1.762 (3)	C6—H6	0.9500
O1—C13	1.260 (3)	C7—C8	1.369 (4)
O2—C13	1.226 (3)	C7—H7	0.9500
O3—N3	1.272 (3)	C8—C9	1.405 (4)
O4—N3	1.252 (3)	C8—H8	0.9500
O5—N3	1.247 (3)	C9—C10	1.413 (4)
N1—C1	1.322 (3)	C9—C12	1.442 (4)
N1—C5	1.366 (3)	C11—C12	1.350 (4)
N2—C6	1.326 (3)	C11—H11	0.9500
N2—C10	1.368 (3)	C12—H12	0.9500
C1—C2	1.401 (4)	C13—C14	1.568 (4)

O1—Pb—N2	77.20 (7)	C2—C3—C4	119.6 (2)
O1—Pb—N1	73.51 (7)	C2—C3—H3	120.2
N2—Pb—N1	65.43 (7)	C4—C3—H3	120.2
O1—Pb—O3	82.13 (6)	C5—C4—C3	117.2 (2)
N2—Pb—O3	77.41 (6)	C5—C4—C11	119.6 (2)
N1—Pb—O3	138.96 (6)	C3—C4—C11	123.2 (2)
O1—Pb—O5ⁱⁱ	143.59 (6)	N1—C5—C4	122.1 (2)
N2—Pb—O5ⁱⁱ	72.82 (7)	N1—C5—C10	118.4 (2)
N1—Pb—O5ⁱⁱ	110.82 (6)	C4—C5—C10	119.5 (2)
O3—Pb—O5ⁱⁱ	71.66 (6)	N2—C6—C7	123.0 (2)
O1—Pb—O2ⁱ	100.42 (6)	N2—C6—H6	118.5
N2—Pb—O2ⁱ	142.33 (6)	C7—C6—H6	118.5
N1—Pb—O2ⁱ	77.74 (6)	C8—C7—C6	119.4 (3)
O3—Pb—O2ⁱ	140.08 (6)	C8—C7—H7	120.3
O5ⁱⁱ—Pb—O2ⁱ	115.93 (6)	C6—C7—H7	120.3
O1—Pb—O4	90.38 (6)	C7—C8—C9	119.2 (2)
N2—Pb—O4	124.31 (6)	C7—C8—H8	120.4
N1—Pb—O4	159.41 (7)	C9—C8—H8	120.4
O3—Pb—O4	46.99 (5)	C8—C9—C10	118.1 (2)
O5ⁱⁱ—Pb—O4	89.76 (5)	C8—C9—C12	122.3 (2)
O2ⁱ—Pb—O4	93.09 (6)	C10—C9—C12	119.6 (2)
C13—O1—Pb	107.77 (17)	N2—C10—C9	121.8 (2)
N3—O3—Pb	101.84 (14)	N2—C10—C5	118.8 (2)
N3—O4—Pb	90.19 (14)	C9—C10—C5	119.3 (2)
C1—N1—C5	118.9 (2)	C12—C11—C4	121.5 (2)
C1—N1—Pb	123.02 (17)	C12—C11—H11	119.3
C5—N1—Pb	117.39 (16)	C4—C11—H11	119.3
C6—N2—C10	118.3 (2)	C11—C12—C9	120.6 (3)
C6—N2—Pb	122.22 (17)	C11—C12—H12	119.7
C10—N2—Pb	119.21 (16)	C9—C12—H12	119.7
O5—N3—O4	121.0 (2)	O2—C13—O1	128.1 (3)
O5—N3—O3	119.6 (2)	O2—C13—C14	118.2 (2)
O4—N3—O3	119.4 (2)	O1—C13—C14	113.8 (2)
N1—C1—C2	122.7 (2)	C13—C14—Cl3	113.04 (19)
N1—C1—H1	118.6	C13—C14—Cl1	108.31 (18)
C2—C1—H1	118.6	Cl3—C14—Cl1	109.62 (15)
C3—C2—C1	119.3 (3)	C13—C14—Cl2	108.31 (19)
C3—C2—H2	120.4	Cl3—C14—Cl2	107.89 (15)
C1—C2—H2	120.4	Cl1—C14—Cl2	109.62 (14)

N2—Pb—O1—C13	−162.22 (17)	C5—N1—C1—C2	0.3 (4)
N1—Pb—O1—C13	−94.40 (17)	Pb—N1—C1—C2	−170.2 (2)
O3—Pb—O1—C13	118.98 (17)	N1—C1—C2—C3	−1.8 (5)
O5ⁱⁱ—Pb—O1—C13	162.70 (14)	C1—C2—C3—C4	2.0 (4)
O2ⁱ—Pb—O1—C13	−20.64 (17)	C2—C3—C4—C5	−0.8 (4)
O4—Pb—O1—C13	72.57 (17)	C2—C3—C4—C11	179.0 (3)
O1—Pb—O3—N3	−105.10 (16)	C1—N1—C5—C4	1.0 (4)
N2—Pb—O3—N3	176.34 (16)	Pb—N1—C5—C4	172.0 (2)
N1—Pb—O3—N3	−158.57 (14)	C1—N1—C5—C10	−178.3 (2)
O5ⁱⁱ—Pb—O3—N3	100.50 (16)	Pb—N1—C5—C10	−7.3 (3)
O2ⁱ—Pb—O3—N3	−8.3 (2)	C3—C4—C5—N1	−0.7 (4)
O4—Pb—O3—N3	−7.15 (13)	C11—C4—C5—N1	179.4 (3)
O1—Pb—O4—N3	85.95 (15)	C3—C4—C5—C10	178.5 (2)
N2—Pb—O4—N3	11.24 (17)	C11—C4—C5—C10	−1.3 (4)
N1—Pb—O4—N3	123.84 (19)	C10—N2—C6—C7	−2.0 (4)
O3—Pb—O4—N3	7.11 (13)	Pb—N2—C6—C7	172.4 (2)
O5ⁱⁱ—Pb—O4—N3	−57.64 (15)	N2—C6—C7—C8	0.6 (4)
O2ⁱ—Pb—O4—N3	−173.59 (15)	C6—C7—C8—C9	1.3 (4)
O1—Pb—N1—C1	94.8 (2)	C7—C8—C9—C10	−1.8 (4)
N2—Pb—N1—C1	177.9 (2)	C7—C8—C9—C12	179.2 (3)
O3—Pb—N1—C1	150.9 (2)	C6—N2—C10—C9	1.5 (4)
O5ⁱⁱ—Pb—N1—C1	−123.5 (2)	Pb—N2—C10—C9	−173.1 (2)
O2ⁱ—Pb—N1—C1	−10.2 (2)	C6—N2—C10—C5	−179.0 (2)
O4—Pb—N1—C1	54.9 (3)	Pb—N2—C10—C5	6.4 (3)
O1—Pb—N1—C5	−75.88 (19)	C8—C9—C10—N2	0.4 (4)
N2—Pb—N1—C5	7.30 (18)	C12—C9—C10—N2	179.4 (2)
O3—Pb—N1—C5	−19.8 (2)	C8—C9—C10—C5	−179.1 (2)
O5ⁱⁱ—Pb—N1—C5	65.9 (2)	C12—C9—C10—C5	−0.1 (4)
O2ⁱ—Pb—N1—C5	179.2 (2)	N1—C5—C10—N2	0.7 (4)
O4—Pb—N1—C5	−115.7 (2)	C4—C5—C10—N2	−178.6 (2)
O1—Pb—N2—C6	−103.8 (2)	N1—C5—C10—C9	−179.7 (2)
N1—Pb—N2—C6	178.6 (2)	C4—C5—C10—C9	1.0 (4)
O3—Pb—N2—C6	−19.2 (2)	C5—C4—C11—C12	0.7 (4)
O5ⁱⁱ—Pb—N2—C6	55.2 (2)	C3—C4—C11—C12	−179.1 (3)
O2ⁱ—Pb—N2—C6	165.63 (18)	C4—C11—C12—C9	0.1 (4)
O4—Pb—N2—C6	−22.3 (2)	C8—C9—C12—C11	178.5 (3)
O1—Pb—N2—C10	70.51 (19)	C10—C9—C12—C11	−0.4 (4)
N1—Pb—N2—C10	−7.01 (18)	Pb—O1—C13—O2	−21.3 (3)
O3—Pb—N2—C10	155.2 (2)	Pb—O1—C13—C14	158.09 (17)
O5ⁱⁱ—Pb—N2—C10	−130.4 (2)	O2—C13—C14—Cl3	3.3 (3)
O2ⁱ—Pb—N2—C10	−20.0 (3)	O1—C13—C14—Cl3	−176.12 (19)
O4—Pb—N2—C10	152.07 (17)	O2—C13—C14—Cl1	−118.3 (2)
Pb—O4—N3—O5	167.5 (2)	O1—C13—C14—Cl1	62.2 (3)
Pb—O4—N3—O3	−12.2 (2)	O2—C13—C14—Cl2	122.8 (2)
Pb—O3—N3—O5	−165.96 (19)	O1—C13—C14—Cl2	−56.6 (3)
Pb—O3—N3—O4	13.7 (3)

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

Experimental details

Crystal data
Chemical formula	[Pb₂(C₂Cl₃O₂)₂(NO₃)₂(C₁₂H₈N₂)₂]
M_r	1223.54
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.8852 (3), 9.7465 (3), 11.1570 (3)
α, β, γ (°)	109.427 (3), 99.019 (3), 106.199 (3)
V (Å³)	841.13 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	10.54
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.227, 0.419
No. of measured, independent and observed [I > 2σ(I)] reflections	12671, 3899, 3740
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.038, 0.99
No. of reflections	3899
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.97

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Pb—O1	2.410 (2)	Pb—O5ⁱⁱ	2.807 (2)
Pb—O2ⁱ	2.821 (2)	Pb—N1	2.576 (2)
Pb—O3	2.591 (2)	Pb—N2	2.515 (2)
Pb—O4	2.844 (2)

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

Footnotes

‡Additional correspondence author, e-mail: shahverdizadeh@iaut.ac.ir.

Acknowledgements

We gratefully acknowledge support of this study by Tabriz Azad University, 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).

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