catena-Poly[bis(μ3-3-aminobenzoato-κ4N:O:O,O′)bis(μ2-3-aminobenzoato-κ3O,O′:O)dilead(II)]

Shen, F.M.; Lush, S.F.

doi:10.1107/S1600536810041322

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1427

https://doi.org/10.1107/S1600536810041322

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catena-Poly[bis(μ₃-3-aminobenzoato-κ⁴N:O:O,O′)bis(μ₂-3-aminobenzoato-κ³O,O′:O)dilead(II)]

Fwu Ming Shen ^a and Shie Fu Lush ^b ^*

^aDepartment of Biotechnology, Yuanpei University, HsinChu, 30015 Taiwan, and ^bDepartment of General Education Center, Yuanpei University, No. 306 Yuanpei St, HsinChu, 30015 Taiwan
^*Correspondence e-mail: lush@mail.ypu.edu.tw

(Received 14 August 2010; accepted 14 October 2010; online 23 October 2010)

The Pb^IIatom in the title compound, {[Pb₂(C₇H₆NO₂)₄]}_n, is chelated by two 3-aminobenzoato ligands in a distorted pentagonal-bipyramidal coordination geometry with five oxygen donors in the equatorial positions, one nitrogen donor and one oxygen donor in the axial positions. Two molecules are linked through a centre of inversion, forming a dinuclear entity. These entities are linked in a μ₃-bridging mode through the amino N atom and two carboxylate O atoms into a chain along the b axis. Classical intermolecular N—H⋯O hydrogen bonding is observed in the structure. The supramolecular structure is consolidated by π–π stacking interactions with centroid–centroid distances between benzene rings of 3.837 (8) Å.

Related literature

For related structures, see: Tan et al. (2006 ); Wang et al. (2004 , 2006 ); Wei et al. (2006 ).

Experimental

Crystal data

[Pb₂(C₇H₆NO₂)₄]
M_r = 958.92
Triclinic, $[P \overline 1]$
a = 6.8610 (3) Å
b = 7.8943 (3) Å
c = 13.9022 (8) Å
α = 76.030 (2)°
β = 88.103 (2)°
γ = 70.154 (2)°
V = 686.33 (6) Å³
Z = 1
Mo Kα radiation
μ = 12.31 mm⁻¹
T = 295 K
0.18 × 0.16 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.215, T_max = 0.791
5451 measured reflections
2470 independent reflections
2218 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.169
S = 1.05
2470 reflections
190 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 3.23 e Å⁻³
Δρ_min = −5.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4ⁱ	0.86	2.52	3.037 (12)	119
N2—H2B⋯O1ⁱ	0.86	2.32	2.936 (12)	129
Symmetry code: (i) -x+2, -y-1, -z.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810041322/rk2229sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041322/rk2229Isup2.hkl

checkCIF report

Comment top

In the last few years, much research on metal–organic framework has mostly focused on coordination polymer with rigid organic ligands containing either N– or O–atom donors, such as 3–aminobenzoic acid. Up to now, only few examples of coordination polymer with 3–aminobenzoic acid have been reported (Wang et al., 2004, 2006; Tan et al., 2006; Wei et al., 2006.), and the polymeric complexes of non–transition metal with 3–aminobenzoic acid have not yet been found.

Herein we report the syntheses and crystal structure of Pb(II) coordination polymer with µ3–bridged 3–aminobenzoic acid (Fig.1). The title compound is a one–dimensional coordination polymer based on infinite µ3–bridging chains along b axial direction. The Pb···Pb distances are 4.118 (3)Å and 4.491 (3)Å. The Pb^II ion is a pentagonal–bipyramidal coordination environment and is coordinated by five carboxyl oxygen atoms comprise the equatorial plane, one nitrogen and one oxygen atom occupies the axial positions. The classic N—H···O hydrogen–bondings are observed in the structure (full details and symmetry codes shown as Table 1).

The supramolecular structure is also consolidated by π—π stacking interaction. The distance between Cg1 (C2–C7)···Cg2ⁱⁱ (C9–C14) is 3.842 (8)Å and dihedral angle between two benzene rings is 4.6 (7)°. Symmetry code: (ii) 1-x, -y, -y.

Related literature top

For related structures, see: Tan et al. (2006); Wang et al. (2004, 2006); Wei et al. (2006).

Experimental top

A solution of 3-aminobenzoic acid (0.0683 g, 0.50 mmol) in 5 ml deionized water was slowly added to a stirring solution of Pb(NO₃)₂^.6H₂O (0.1670 g, 0.50 mmol) and 1,2–bis(4–pyridyl)ethane (0.0926 g, 0.50 mmol) in 5 ml deionized water. The mixture solution was seal in 25 ml stainless steel reactor with a teflon liner, heat to 423 K for 24 hr, and then slowly cooled to room temperature. The pink single crystals of the title compound were obtained in 56.45% yield. (Based on Pb).

Structure description top

For related structures, see: Tan et al. (2006); Wang et al. (2004, 2006); Wei et al. (2006).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

catena-Poly[bis(µ₃-3-aminobenzoato- κ⁴N:O:O,O')bis(µ₂-3-aminobenzoato- κ³O,O':O)dilead(II)] top

Crystal data top

[Pb₂(C₇H₆NO₂)₄]	Z = 1
M_r = 958.92	F(000) = 448
Triclinic, P1	D_x = 2.320 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8610 (3) Å	Cell parameters from 12232 reflections
b = 7.8943 (3) Å	θ = 2.0–25.4°
c = 13.9022 (8) Å	µ = 12.31 mm⁻¹
α = 76.030 (2)°	T = 295 K
β = 88.103 (2)°	Prism, pink
γ = 70.154 (2)°	0.18 × 0.16 × 0.02 mm
V = 686.33 (6) Å³

Data collection top

Nonius KappaCCD diffractometer	2470 independent reflections
Radiation source: fine–focus sealed tube	2218 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
Detector resolution: 9 pixels mm^-1	θ_max = 25.3°, θ_min = 2.8°
CCD rotation images, thick slices scans	h = −7→8
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −7→9
T_min = 0.215, T_max = 0.791	l = −16→16
5451 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1239P)² + 1.1995P] where P = (F_o² + 2F_c²)/3
2470 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 3.23 e Å⁻³
12 restraints	Δρ_min = −5.12 e Å⁻³

Crystal data top

[Pb₂(C₇H₆NO₂)₄]	γ = 70.154 (2)°
M_r = 958.92	V = 686.33 (6) Å³
Triclinic, P1	Z = 1
a = 6.8610 (3) Å	Mo Kα radiation
b = 7.8943 (3) Å	µ = 12.31 mm⁻¹
c = 13.9022 (8) Å	T = 295 K
α = 76.030 (2)°	0.18 × 0.16 × 0.02 mm
β = 88.103 (2)°

Data collection top

Nonius KappaCCD diffractometer	2470 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	2218 reflections with I > 2σ(I)
T_min = 0.215, T_max = 0.791	R_int = 0.103
5451 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	12 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.05	Δρ_max = 3.23 e Å⁻³
2470 reflections	Δρ_min = −5.12 e Å⁻³
190 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

The residual peaks show two relatively high peaks of 3.19 eÅ^-3 at 0.405, 0.645, 0.123 and 3.13 eÅ^-3 at 0.566, 0.080, 0.038, and the distances to the nearest Pb atoms are 1.26Å and 1.50Å, respectively.

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

	x	y	z	U_iso*/U_eq
Pb1	0.57722 (5)	0.23064 (4)	−0.04961 (3)	0.0375 (1)
O1	0.7342 (13)	0.0825 (10)	0.1159 (6)	0.051 (3)
O2	0.6749 (13)	0.3823 (11)	0.0817 (6)	0.051 (3)
O3	0.6695 (17)	0.0912 (11)	−0.2133 (6)	0.058 (3)
O4	0.7229 (12)	−0.0859 (9)	−0.0620 (5)	0.040 (2)
N1	0.655 (3)	0.555 (2)	0.4054 (11)	0.092 (6)
N2	0.9270 (14)	−0.7459 (12)	−0.0976 (7)	0.038 (3)
C1	0.7141 (15)	0.2286 (15)	0.1435 (8)	0.037 (3)
C2	0.7253 (16)	0.2209 (16)	0.2521 (9)	0.043 (3)
C3	0.6951 (19)	0.3817 (19)	0.2811 (9)	0.054 (4)
C4	0.696 (2)	0.383 (2)	0.3805 (10)	0.065 (4)
C5	0.733 (2)	0.212 (3)	0.4500 (10)	0.076 (5)
C6	0.768 (3)	0.050 (3)	0.4203 (11)	0.079 (5)
C7	0.766 (2)	0.056 (2)	0.3199 (10)	0.057 (4)
C8	0.7220 (17)	−0.0662 (14)	−0.1556 (8)	0.039 (3)
C9	0.7796 (14)	−0.2349 (13)	−0.1927 (8)	0.035 (3)
C10	0.8350 (14)	−0.4092 (14)	−0.1314 (8)	0.035 (3)
C11	0.8749 (15)	−0.5654 (13)	−0.1674 (7)	0.029 (3)
C12	0.8668 (17)	−0.5505 (15)	−0.2690 (8)	0.037 (3)
C13	0.8113 (19)	−0.3757 (16)	−0.3344 (8)	0.043 (3)
C14	0.7646 (16)	−0.2166 (14)	−0.2971 (8)	0.040 (3)
H1A	0.63110	0.65490	0.35920	0.1100*
H1B	0.65500	0.55860	0.46660	0.1100*
H2A	0.93270	−0.75440	−0.03490	0.0460*
H2B	0.95220	−0.84430	−0.11910	0.0460*
H3	0.67370	0.49200	0.23310	0.0660*
H5	0.73270	0.20860	0.51740	0.0920*
H6	0.79390	−0.06200	0.46730	0.0940*
H7	0.79250	−0.05300	0.29910	0.0690*
H10	0.84610	−0.42310	−0.06320	0.0420*
H12	0.89830	−0.65640	−0.29310	0.0450*
H13	0.80500	−0.36400	−0.40250	0.0510*
H14	0.72400	−0.09940	−0.34050	0.0480*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.0414 (2)	0.0231 (2)	0.0487 (3)	−0.0120 (2)	0.0023 (2)	−0.0088 (2)
O1	0.056 (5)	0.034 (4)	0.065 (5)	−0.015 (4)	0.007 (4)	−0.019 (4)
O2	0.061 (5)	0.035 (4)	0.059 (5)	−0.020 (4)	−0.004 (4)	−0.010 (4)
O3	0.094 (6)	0.034 (4)	0.051 (5)	−0.028 (4)	0.010 (4)	−0.013 (4)
O4	0.058 (5)	0.023 (3)	0.043 (4)	−0.013 (3)	0.007 (3)	−0.015 (3)
N1	0.113 (11)	0.118 (11)	0.067 (7)	−0.049 (10)	0.027 (7)	−0.054 (8)
N2	0.046 (5)	0.026 (4)	0.048 (5)	−0.016 (4)	0.005 (4)	−0.014 (4)
C1	0.027 (4)	0.038 (5)	0.046 (5)	−0.009 (4)	0.010 (4)	−0.014 (4)
C2	0.029 (5)	0.046 (6)	0.051 (6)	−0.009 (4)	0.004 (4)	−0.015 (4)
C3	0.050 (6)	0.063 (7)	0.055 (6)	−0.022 (6)	−0.003 (5)	−0.019 (6)
C4	0.044 (7)	0.091 (8)	0.066 (7)	−0.015 (7)	0.012 (6)	−0.041 (6)
C5	0.065 (8)	0.123 (11)	0.044 (6)	−0.032 (9)	0.013 (6)	−0.027 (6)
C6	0.081 (10)	0.080 (9)	0.053 (7)	−0.010 (9)	0.003 (7)	−0.001 (7)
C7	0.048 (7)	0.053 (7)	0.059 (7)	−0.008 (6)	0.008 (6)	−0.006 (6)
C8	0.046 (5)	0.023 (5)	0.053 (6)	−0.018 (4)	0.006 (5)	−0.012 (4)
C9	0.025 (4)	0.022 (4)	0.056 (6)	−0.011 (4)	0.007 (4)	0.000 (4)
C10	0.021 (4)	0.030 (5)	0.049 (5)	0.003 (4)	−0.002 (4)	−0.018 (4)
C11	0.027 (4)	0.024 (4)	0.042 (5)	−0.013 (4)	0.007 (4)	−0.013 (4)
C12	0.048 (6)	0.036 (5)	0.041 (5)	−0.024 (4)	0.012 (4)	−0.021 (4)
C13	0.058 (6)	0.040 (6)	0.038 (5)	−0.024 (5)	0.005 (5)	−0.014 (4)
C14	0.044 (5)	0.029 (5)	0.050 (6)	−0.016 (4)	0.003 (5)	−0.010 (4)

Geometric parameters (Å, º) top

Pb1—O1	2.415 (8)	C3—C4	1.385 (18)
Pb1—O2	2.626 (8)	C4—C5	1.41 (2)
Pb1—O3	2.726 (8)	C5—C6	1.38 (3)
Pb1—O4	2.403 (7)	C6—C7	1.39 (2)
Pb1—N2ⁱ	2.525 (10)	C8—C9	1.469 (15)
Pb1—O4ⁱⁱ	2.913 (8)	C9—C10	1.365 (15)
Pb1—O2ⁱⁱⁱ	2.887 (8)	C9—C14	1.427 (15)
O1—C1	1.264 (14)	C10—C11	1.380 (15)
O2—C1	1.254 (14)	C11—C12	1.390 (14)
O3—C8	1.246 (14)	C12—C13	1.392 (16)
O4—C8	1.273 (13)	C13—C14	1.407 (16)
N1—C4	1.42 (2)	C3—H3	0.9300
N2—C11	1.452 (13)	C5—H5	0.9300
N1—H1B	0.8600	C6—H6	0.9300
N1—H1A	0.8600	C7—H7	0.9300
N2—H2B	0.8600	C10—H10	0.9300
N2—H2A	0.8600	C12—H12	0.9300
C1—C2	1.500 (16)	C13—H13	0.9300
C2—C7	1.356 (19)	C14—H14	0.9300
C2—C3	1.371 (19)

Pb1···C3ⁱⁱⁱ	3.870 (13)	C3···C13ⁱⁱ	3.542 (19)
Pb1···C10ⁱⁱ	3.854 (11)	C3···C14^vi	3.482 (18)
Pb1···H3ⁱⁱⁱ	3.0500	C4···C13^vi	3.40 (2)
Pb1···H10ⁱⁱ	3.3300	C4···C13ⁱⁱ	3.58 (2)
O1···O2	2.193 (11)	C7···C14ⁱⁱ	3.422 (19)
O1···O4	3.092 (11)	C8···Pb1ⁱⁱ	3.698 (11)
O1···C2	2.394 (15)	C9···C1ⁱⁱ	3.419 (15)
O1···N2^iv	2.936 (12)	C9···C1^vi	3.582 (15)
O1···C8ⁱⁱ	3.200 (15)	C9···C2^vi	3.501 (16)
O1···O4ⁱⁱ	3.238 (13)	C9···C2ⁱⁱ	3.547 (16)
O2···N2ⁱ	3.158 (13)	C10···O2^v	3.369 (14)
O2···C2	2.378 (15)	C10···Pb1ⁱⁱ	3.854 (11)
O2···O1	2.193 (11)	C10···C1ⁱⁱ	3.540 (15)
O2···O2ⁱⁱⁱ	3.109 (12)	C13···C3ⁱⁱ	3.542 (19)
O2···C10ⁱ	3.369 (14)	C13···C3^vi	3.473 (19)
O3···C9	2.370 (13)	C13···C4^vi	3.40 (2)
O3···O4	2.190 (11)	C13···C4ⁱⁱ	3.58 (2)
O3···N2ⁱ	3.177 (14)	C14···C3^vi	3.482 (18)
O4···O1	3.092 (11)	C14···C2^vi	3.563 (17)
O4···C9	2.348 (12)	C14···C2ⁱⁱ	3.409 (17)
O4···O1ⁱⁱ	3.238 (13)	C14···C7ⁱⁱ	3.422 (19)
O4···N2^iv	3.037 (12)	C1···H2Aⁱ	2.8500
O4···O3	2.190 (11)	C5···H1B^vii	3.0400
O1···H7	2.5000	C8···H2Bⁱ	2.8600
O1···H2B^iv	2.3200	H1A···H3	2.3700
O1···H2Aⁱ	2.7600	H1A···O3ⁱⁱⁱ	2.8100
O2···H10ⁱ	2.7200	H1B···H5	2.5500
O2···H2Aⁱ	2.5100	H1B···H13^viii	2.4100
O2···H3	2.4600	H1B···C5^vii	3.0400
O3···H2Bⁱ	2.6300	H2A···H10	2.4100
O3···H1Aⁱⁱⁱ	2.8100	H2A···O4^iv	2.5200
O3···H14	2.5300	H2B···H12	2.4800
O4···H10	2.5100	H2B···O1^iv	2.3200
O4···H2Bⁱ	2.8200	H3···O2	2.4600
O4···H2A^iv	2.5200	H3···H1A	2.3700
N2···O2^v	3.158 (13)	H3···Pb1ⁱⁱⁱ	3.0500
N2···O3^v	3.177 (14)	H5···H1B	2.5500
N2···O1^iv	2.936 (12)	H7···O1	2.5000
N2···O4^iv	3.037 (12)	H7···H12^iv	2.5600
C1···C10ⁱⁱ	3.540 (15)	H10···O2^v	2.7200
C1···C9ⁱⁱ	3.419 (15)	H10···O4	2.5100
C1···C9^vi	3.582 (15)	H10···H2A	2.4100
C2···C14^vi	3.563 (17)	H10···Pb1ⁱⁱ	3.3300
C2···C9ⁱⁱ	3.547 (16)	H10···H10^iv	2.5500
C2···C9^vi	3.501 (16)	H12···H2B	2.4800
C2···C14ⁱⁱ	3.409 (17)	H12···H7^iv	2.5600
C3···C13^vi	3.473 (19)	H13···H1B^ix	2.4100
C3···Pb1ⁱⁱⁱ	3.870 (13)	H14···O3	2.5300

O1—Pb1—O2	51.4 (3)	H2A—N2—H2B	120.00
O1—Pb1—O3	126.6 (3)	Pb1^v—N2—H2B	88.00
O1—Pb1—O4	79.9 (2)	Pb1—C1—O1	56.6 (6)
O1—Pb1—C1	25.9 (3)	O1—C1—O2	121.1 (10)
O1—Pb1—C8	103.8 (3)	Pb1—C1—O2	66.2 (6)
O1—Pb1—N2ⁱ	86.3 (3)	Pb1—C1—C2	163.1 (8)
O1—Pb1—O4ⁱⁱ	74.2 (3)	O1—C1—C2	119.7 (10)
O1—Pb1—O2ⁱⁱⁱ	115.3 (2)	O2—C1—C2	119.1 (10)
O2—Pb1—O3	149.9 (3)	C3—C2—C7	121.1 (12)
O2—Pb1—O4	128.1 (3)	C1—C2—C3	119.1 (11)
O2—Pb1—C1	25.9 (3)	C1—C2—C7	119.8 (11)
O2—Pb1—C8	145.9 (3)	C2—C3—C4	121.3 (13)
O2—Pb1—N2ⁱ	75.6 (3)	N1—C4—C5	124.5 (14)
O2—Pb1—O4ⁱⁱ	98.7 (2)	C3—C4—C5	117.1 (14)
O2—Pb1—O2ⁱⁱⁱ	68.5 (3)	N1—C4—C3	118.4 (13)
O3—Pb1—O4	50.1 (2)	C4—C5—C6	121.4 (13)
O3—Pb1—C1	147.2 (3)	C5—C6—C7	119.4 (16)
O3—Pb1—C8	25.0 (3)	C2—C7—C6	119.8 (15)
O3—Pb1—N2ⁱ	74.3 (3)	Pb1—C8—O3	67.9 (6)
O3—Pb1—O4ⁱⁱ	109.5 (3)	Pb1—C8—O4	53.2 (5)
O2ⁱⁱⁱ—Pb1—O3	117.1 (2)	Pb1—C8—C9	169.2 (8)
O4—Pb1—C1	105.3 (3)	O3—C8—O4	120.9 (10)
O4—Pb1—C8	25.1 (3)	O3—C8—C9	121.5 (10)
O4—Pb1—N2ⁱ	85.9 (3)	O4—C8—C9	117.7 (9)
O4—Pb1—O4ⁱⁱ	81.3 (2)	C8—C9—C10	122.9 (10)
O2ⁱⁱⁱ—Pb1—O4	163.4 (2)	C8—C9—C14	118.9 (9)
C1—Pb1—C8	128.2 (3)	C10—C9—C14	118.1 (9)
N2ⁱ—Pb1—C1	83.5 (3)	C9—C10—C11	122.1 (10)
O4ⁱⁱ—Pb1—C1	83.0 (3)	N2—C11—C12	120.4 (9)
O2ⁱⁱⁱ—Pb1—C1	90.5 (3)	C10—C11—C12	120.5 (10)
N2ⁱ—Pb1—C8	80.2 (3)	N2—C11—C10	119.0 (9)
O4ⁱⁱ—Pb1—C8	94.8 (3)	C11—C12—C13	119.4 (10)
O2ⁱⁱⁱ—Pb1—C8	140.9 (3)	C12—C13—C14	119.8 (10)
O4ⁱⁱ—Pb1—N2ⁱ	158.2 (3)	C9—C14—C13	120.1 (10)
O2ⁱⁱⁱ—Pb1—N2ⁱ	101.2 (3)	C2—C3—H3	119.00
O2ⁱⁱⁱ—Pb1—O4ⁱⁱ	96.0 (2)	C4—C3—H3	119.00
Pb1—O1—C1	97.5 (7)	C4—C5—H5	119.00
Pb1—O2—C1	87.9 (7)	C6—C5—H5	120.00
Pb1—O2—Pb1ⁱⁱⁱ	111.5 (3)	C5—C6—H6	120.00
Pb1ⁱⁱⁱ—O2—C1	142.0 (7)	C7—C6—H6	120.00
Pb1—O3—C8	87.1 (6)	C2—C7—H7	120.00
Pb1—O4—C8	101.8 (6)	C6—C7—H7	120.00
Pb1—O4—Pb1ⁱⁱ	98.7 (3)	C9—C10—H10	119.00
Pb1ⁱⁱ—O4—C8	118.8 (7)	C11—C10—H10	119.00
Pb1^v—N2—C11	103.4 (7)	C11—C12—H12	120.00
H1A—N1—H1B	120.00	C13—C12—H12	120.00
C4—N1—H1A	120.00	C12—C13—H13	120.00
C4—N1—H1B	120.00	C14—C13—H13	120.00
Pb1^v—N2—H2A	78.00	C9—C14—H14	120.00
C11—N2—H2A	120.00	C13—C14—H14	120.00
C11—N2—H2B	120.00

O2—Pb1—O1—C1	8.3 (6)	O2—Pb1—N2ⁱ—C11ⁱ	−90.7 (6)
O3—Pb1—O1—C1	150.1 (7)	O3—Pb1—N2ⁱ—C11ⁱ	88.7 (6)
O4—Pb1—O1—C1	169.3 (7)	O4—Pb1—N2ⁱ—C11ⁱ	138.3 (6)
C8—Pb1—O1—C1	161.8 (7)	C1—Pb1—N2ⁱ—C11ⁱ	−115.8 (6)
N2ⁱ—Pb1—O1—C1	82.8 (7)	C8—Pb1—N2ⁱ—C11ⁱ	113.6 (6)
O4ⁱⁱ—Pb1—O1—C1	−107.0 (7)	O1—Pb1—O4ⁱⁱ—Pb1ⁱⁱ	−81.9 (3)
O2ⁱⁱⁱ—Pb1—O1—C1	−17.8 (8)	O1—Pb1—O4ⁱⁱ—C8ⁱⁱ	26.8 (7)
O1—Pb1—O2—C1	−8.3 (6)	O2—Pb1—O4ⁱⁱ—Pb1ⁱⁱ	−127.4 (3)
O1—Pb1—O2—Pb1ⁱⁱⁱ	−154.7 (5)	O2—Pb1—O4ⁱⁱ—C8ⁱⁱ	−18.8 (8)
O3—Pb1—O2—C1	−106.4 (8)	O3—Pb1—O4ⁱⁱ—Pb1ⁱⁱ	42.0 (3)
O3—Pb1—O2—Pb1ⁱⁱⁱ	107.2 (5)	O3—Pb1—O4ⁱⁱ—C8ⁱⁱ	150.6 (7)
O4—Pb1—O2—C1	−32.3 (8)	O4—Pb1—O4ⁱⁱ—Pb1ⁱⁱ	0.0 (2)
O4—Pb1—O2—Pb1ⁱⁱⁱ	−178.7 (3)	O4—Pb1—O4ⁱⁱ—C8ⁱⁱ	108.6 (7)
C1—Pb1—O2—Pb1ⁱⁱⁱ	−146.4 (8)	C1—Pb1—O4ⁱⁱ—Pb1ⁱⁱ	−106.8 (3)
C8—Pb1—O2—C1	−58.8 (9)	C1—Pb1—O4ⁱⁱ—C8ⁱⁱ	1.9 (7)
C8—Pb1—O2—Pb1ⁱⁱⁱ	154.7 (4)	C8—Pb1—O4ⁱⁱ—Pb1ⁱⁱ	21.2 (3)
N2ⁱ—Pb1—O2—C1	−105.1 (7)	C8—Pb1—O4ⁱⁱ—C8ⁱⁱ	129.8 (7)
N2ⁱ—Pb1—O2—Pb1ⁱⁱⁱ	108.5 (4)	O1—Pb1—O2ⁱⁱⁱ—Pb1ⁱⁱⁱ	21.7 (4)
O4ⁱⁱ—Pb1—O2—C1	53.4 (7)	O1—Pb1—O2ⁱⁱⁱ—C1ⁱⁱⁱ	137.8 (12)
O4ⁱⁱ—Pb1—O2—Pb1ⁱⁱⁱ	−93.1 (3)	O2—Pb1—O2ⁱⁱⁱ—Pb1ⁱⁱⁱ	0.0 (3)
O2ⁱⁱⁱ—Pb1—O2—C1	146.4 (7)	O2—Pb1—O2ⁱⁱⁱ—C1ⁱⁱⁱ	116.1 (13)
O2ⁱⁱⁱ—Pb1—O2—Pb1ⁱⁱⁱ	0.0 (3)	O3—Pb1—O2ⁱⁱⁱ—Pb1ⁱⁱⁱ	−147.5 (3)
O1—Pb1—O3—C8	27.6 (9)	O3—Pb1—O2ⁱⁱⁱ—C1ⁱⁱⁱ	−31.4 (13)
O2—Pb1—O3—C8	101.9 (9)	C1—Pb1—O2ⁱⁱⁱ—Pb1ⁱⁱⁱ	14.0 (4)
O4—Pb1—O3—C8	2.7 (7)	C1—Pb1—O2ⁱⁱⁱ—C1ⁱⁱⁱ	130.1 (12)
C1—Pb1—O3—C8	51.3 (11)	C8—Pb1—O2ⁱⁱⁱ—Pb1ⁱⁱⁱ	−157.7 (4)
N2ⁱ—Pb1—O3—C8	100.6 (8)	C8—Pb1—O2ⁱⁱⁱ—C1ⁱⁱⁱ	−41.6 (14)
O4ⁱⁱ—Pb1—O3—C8	−56.9 (8)	Pb1—O1—C1—O2	−16.0 (12)
O2ⁱⁱⁱ—Pb1—O3—C8	−164.6 (7)	Pb1—O1—C1—C2	160.6 (9)
O1—Pb1—O4—C8	−162.6 (8)	Pb1—O2—C1—O1	14.5 (11)
O1—Pb1—O4—Pb1ⁱⁱ	75.4 (3)	Pb1—O2—C1—C2	−162.0 (9)
O2—Pb1—O4—C8	−143.8 (7)	Pb1ⁱⁱⁱ—O2—C1—Pb1	123.3 (11)
O2—Pb1—O4—Pb1ⁱⁱ	94.2 (3)	Pb1ⁱⁱⁱ—O2—C1—O1	137.8 (10)
O3—Pb1—O4—C8	−2.7 (7)	Pb1ⁱⁱⁱ—O2—C1—C2	−38.8 (18)
O3—Pb1—O4—Pb1ⁱⁱ	−124.7 (5)	Pb1—O3—C8—O4	−4.6 (12)
C1—Pb1—O4—C8	−157.8 (7)	Pb1—O3—C8—C9	173.8 (11)
C1—Pb1—O4—Pb1ⁱⁱ	80.2 (3)	Pb1—O4—C8—O3	5.3 (14)
C8—Pb1—O4—Pb1ⁱⁱ	−122.0 (8)	Pb1—O4—C8—C9	−173.1 (8)
N2ⁱ—Pb1—O4—C8	−75.7 (7)	Pb1ⁱⁱ—O4—C8—Pb1	106.9 (6)
N2ⁱ—Pb1—O4—Pb1ⁱⁱ	162.3 (3)	Pb1ⁱⁱ—O4—C8—O3	112.2 (12)
O4ⁱⁱ—Pb1—O4—C8	122.0 (7)	Pb1ⁱⁱ—O4—C8—C9	−66.2 (12)
O4ⁱⁱ—Pb1—O4—Pb1ⁱⁱ	0.0 (2)	Pb1^v—N2—C11—C12	−96.2 (10)
O1—Pb1—C1—O2	165.1 (11)	Pb1^v—N2—C11—C10	84.2 (10)
O2—Pb1—C1—O1	−165.1 (11)	O1—C1—C2—C7	2.9 (17)
O3—Pb1—C1—O1	−47.5 (10)	O1—C1—C2—C3	−177.5 (12)
O3—Pb1—C1—O2	117.6 (7)	O2—C1—C2—C7	179.5 (12)
O4—Pb1—C1—O1	−11.0 (7)	O2—C1—C2—C3	−0.9 (17)
O4—Pb1—C1—O2	154.1 (6)	C7—C2—C3—C4	−3 (2)
C8—Pb1—C1—O1	−22.7 (8)	C1—C2—C3—C4	177.5 (12)
C8—Pb1—C1—O2	142.4 (6)	C1—C2—C7—C6	−177.4 (15)
N2ⁱ—Pb1—C1—O1	−94.8 (7)	C3—C2—C7—C6	3 (2)
N2ⁱ—Pb1—C1—O2	70.3 (7)	C2—C3—C4—N1	−177.3 (15)
O4ⁱⁱ—Pb1—C1—O1	68.0 (7)	C2—C3—C4—C5	1 (2)
O4ⁱⁱ—Pb1—C1—O2	−126.9 (7)	N1—C4—C5—C6	178.7 (18)
O2ⁱⁱⁱ—Pb1—C1—O1	163.9 (7)	C3—C4—C5—C6	0 (2)
O2ⁱⁱⁱ—Pb1—C1—O2	−31.0 (7)	C4—C5—C6—C7	0 (3)
O1—Pb1—C8—O3	−157.5 (8)	C5—C6—C7—C2	−2 (3)
O1—Pb1—C8—O4	17.6 (8)	O4—C8—C9—C10	−0.6 (17)
O2—Pb1—C8—O3	−119.1 (8)	O3—C8—C9—C10	−179.1 (12)
O2—Pb1—C8—O4	56.0 (10)	O3—C8—C9—C14	−3.2 (17)
O3—Pb1—C8—O4	175.1 (13)	O4—C8—C9—C14	175.2 (10)
O4—Pb1—C8—O3	−175.1 (13)	C14—C9—C10—C11	−0.4 (16)
C1—Pb1—C8—O3	−147.5 (8)	C8—C9—C14—C13	−177.6 (11)
C1—Pb1—C8—O4	27.6 (9)	C8—C9—C10—C11	175.5 (10)
N2ⁱ—Pb1—C8—O3	−73.8 (8)	C10—C9—C14—C13	−1.6 (16)
N2ⁱ—Pb1—C8—O4	101.3 (7)	C9—C10—C11—C12	2.3 (17)
O4ⁱⁱ—Pb1—C8—O3	127.6 (8)	C9—C10—C11—N2	−178.2 (10)
O4ⁱⁱ—Pb1—C8—O4	−57.3 (7)	N2—C11—C12—C13	178.4 (11)
O2ⁱⁱⁱ—Pb1—C8—O3	22.0 (10)	C10—C11—C12—C13	−2.1 (18)
O2ⁱⁱⁱ—Pb1—C8—O4	−162.9 (6)	C11—C12—C13—C14	0.1 (19)
O1—Pb1—N2ⁱ—C11ⁱ	−141.7 (6)	C12—C13—C14—C9	1.7 (18)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4^iv	0.86	2.52	3.037 (12)	119
N2—H2B···O1^iv	0.86	2.32	2.936 (12)	129

Symmetry code: (iv) −x+2, −y−1, −z.

Experimental details

Crystal data
Chemical formula	[Pb₂(C₇H₆NO₂)₄]
M_r	958.92
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.8610 (3), 7.8943 (3), 13.9022 (8)
α, β, γ (°)	76.030 (2), 88.103 (2), 70.154 (2)
V (Å³)	686.33 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	12.31
Crystal size (mm)	0.18 × 0.16 × 0.02

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.215, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	5451, 2470, 2218
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.169, 1.05
No. of reflections	2470
No. of parameters	190
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	3.23, −5.12

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.86	2.52	3.037 (12)	119
N2—H2B···O1ⁱ	0.86	2.32	2.936 (12)	129

Symmetry code: (i) −x+2, −y−1, −z.

Acknowledgements

This work was supported financially by Yuanpei University, Taiwan.

References

Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, A. Z., Wei, Y. H., Chen, Z. L., Ling, F. P. & Hu, R. X. (2006). Chin. J. Struct. Chem. 25, 417–423. CAS Google Scholar
Wang, R. H., Hong, M. C., Luo, J., Jiang, F., Lei, H., Lin, Z. & Cao, R. (2004). Inorg. Chim. Acta, 357, 103–114. Web of Science CSD CrossRef CAS Google Scholar
Wang, R. H., Yuan, D. Q., Jiang, F. L., Lei, H., Gao, S. & Hong, M. C. (2006). Eur. J. Inorg. Chem. pp. 1649–1656. Web of Science CSD CrossRef Google Scholar
Wei, Y. H., Tan, A. Z., Chen, Z. L., Liang, F. P. & Hu, R. X. (2006). Chin. J. Struct. Chem. 25, 343–347. CAS Google Scholar

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