(2,2'-Bipyridine-κN,N')bis-(4-methyl-benzoato-κO,O')lead(II).

In the title compound, [Pb(C(8)H(7)O(2))(2)(C(10)H(8)N(2))], the Pb(II) ion is coordinated by two N atoms from one 2,2'-bipyridine ligand and four O atoms from two 4-methyl-benzoate anions in a distorted pseudo-square-pyramidal environment, considering one of the carboxyl-ate anions as an apical ligand. Pairs of complex mol-ecules related by inversion centers are organized into dimers via pairs of Pb⋯O inter-actions [3.185 (2) Å] and stacking interactions between 2,2'-bipyridine and 4-methyl-benzoate ligands, with a mean distance between their planes of 3.491 Å.

Related literature

For potential applications of lead compounds, see: Fan & Zhu (2006 ▶); Hamilton et al. (2004 ▶). For the use of aromatic carboxyl­ates and 2,2′-bipyridine-type ligands in the preparation of metal complexes, see: Wang et al. (2006 ▶); Masaoka et al. (2001 ▶).

Experimental

Crystal data

[Pb(C8H7O2)2(C10H8N2)]

M = 633.65

Triclinic,

a = 9.5510 (11) Å

b = 10.0805 (12) Å

c = 13.2483 (15) Å

α = 109.865 (1)°

β = 97.322 (1)°

γ = 90.643 (1)°

V = 1187.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 7.14 mm−1

T = 296 K

0.35 × 0.26 × 0.18 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.124, T max = 0.277

14285 measured reflections

5555 independent reflections

4965 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.051

S = 1.02

5555 reflections

300 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.76 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005544/gk2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005544/gk2256Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Pb(C8H7O2)2(C10H8N2)]	Z = 2
Mr = 633.65	F(000) = 612
Triclinic, P1	Dx = 1.772 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5510 (11) Å	Cell parameters from 7017 reflections
b = 10.0805 (12) Å	θ = 2.2–26.6°
c = 13.2483 (15) Å	µ = 7.14 mm−1
α = 109.865 (1)°	T = 296 K
β = 97.322 (1)°	Prism, colorless
γ = 90.643 (1)°	0.35 × 0.26 × 0.18 mm
V = 1187.8 (2) Å3

Bruker APEXII CCD area detector diffractometer	5555 independent reflections
Radiation source: fine-focus sealed tube	4965 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 27.8°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.124, Tmax = 0.277	k = −13→13
14285 measured reflections	l = −17→17

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0227P)2 + 0.140P] where P = (Fo2 + 2Fc2)/3
5555 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.77 e Å−3
2 restraints	Δρmin = −0.76 e Å−3

	x	y	z	Uiso*/Ueq
Pb1	0.010726 (12)	0.117736 (12)	0.677133 (9)	0.03988 (5)
O1	0.2108 (2)	0.1792 (2)	0.80800 (18)	0.0483 (5)
O2	0.0648 (2)	0.3523 (2)	0.84728 (18)	0.0543 (6)
O3	0.1789 (3)	0.0320 (3)	0.5511 (2)	0.0601 (6)
O4	0.1595 (3)	0.2603 (2)	0.58236 (19)	0.0556 (6)
N1	−0.0850 (3)	0.0481 (3)	0.8332 (2)	0.0468 (6)
N2	0.0489 (3)	−0.1362 (3)	0.6814 (2)	0.0454 (6)
C1	0.1748 (3)	0.2982 (3)	0.8699 (3)	0.0413 (7)
C2	0.2682 (3)	0.3698 (3)	0.9753 (3)	0.0409 (7)
C3	0.4063 (3)	0.3339 (3)	0.9934 (3)	0.0488 (8)
H3A	0.4430	0.2632	0.9395	0.059*
C4	0.4895 (4)	0.4025 (4)	1.0911 (3)	0.0586 (10)
H4A	0.5825	0.3781	1.1016	0.070*
C5	0.4386 (4)	0.5062 (4)	1.1735 (3)	0.0559 (9)
C6	0.3003 (4)	0.5395 (4)	1.1556 (3)	0.0576 (9)
H6A	0.2630	0.6076	1.2108	0.069*
C7	0.2156 (4)	0.4740 (3)	1.0576 (3)	0.0470 (7)
H7A	0.1233	0.5000	1.0470	0.056*
C8	0.5337 (5)	0.5824 (5)	1.2781 (4)	0.0861 (15)
H8A	0.5932	0.5164	1.2977	0.129*
H8B	0.4770	0.6244	1.3343	0.129*
H8C	0.5913	0.6548	1.2687	0.129*
C9	0.2085 (3)	0.1461 (4)	0.5346 (3)	0.0449 (7)
C10	0.3033 (3)	0.1363 (3)	0.4516 (2)	0.0413 (7)
C11	0.3697 (4)	0.0135 (4)	0.4040 (3)	0.0522 (8)
H11A	0.3569	−0.0640	0.4254	0.063*
C12	0.4548 (4)	0.0043 (4)	0.3251 (3)	0.0571 (9)
H12A	0.4985	−0.0792	0.2947	0.068*
C13	0.4757 (4)	0.1168 (4)	0.2909 (3)	0.0532 (8)
C14	0.4090 (4)	0.2395 (4)	0.3393 (3)	0.0662 (11)
H14A	0.4209	0.3168	0.3173	0.079*
C15	0.3258 (4)	0.2498 (4)	0.4188 (3)	0.0584 (9)
H15A	0.2844	0.3342	0.4508	0.070*
C16	0.5663 (5)	0.1044 (5)	0.2032 (3)	0.0709 (11)
H16A	0.6455	0.0495	0.2118	0.106*
H16B	0.5998	0.1970	0.2084	0.106*
H16C	0.5113	0.0589	0.1335	0.106*
C17	−0.1533 (4)	0.1412 (4)	0.9053 (3)	0.0553 (9)
H17A	−0.1560	0.2331	0.9046	0.066*
C18	−0.2200 (4)	0.1079 (4)	0.9806 (3)	0.0599 (10)
H18A	−0.2657	0.1759	1.0301	0.072*
C19	−0.2174 (4)	−0.0266 (4)	0.9810 (3)	0.0640 (10)
H19A	−0.2606	−0.0521	1.0313	0.077*
C20	−0.1495 (4)	−0.1250 (4)	0.9053 (3)	0.0600 (10)
H20A	−0.1487	−0.2182	0.9032	0.072*
C21	−0.0830 (3)	−0.0847 (3)	0.8330 (3)	0.0435 (7)
C22	−0.0052 (3)	−0.1848 (3)	0.7519 (3)	0.0441 (7)
C23	0.0131 (5)	−0.3217 (4)	0.7493 (4)	0.0672 (11)
H23A	−0.0239	−0.3531	0.7993	0.081*
C24	0.0856 (5)	−0.4114 (4)	0.6734 (4)	0.0755 (12)
H24A	0.0987	−0.5035	0.6713	0.091*
C25	0.1376 (5)	−0.3618 (4)	0.6014 (4)	0.0736 (12)
H25A	0.1864	−0.4203	0.5485	0.088*
C26	0.1179 (4)	−0.2249 (4)	0.6073 (3)	0.0600 (9)
H26A	0.1542	−0.1925	0.5575	0.072*

	U11	U22	U33	U12	U13	U23
Pb1	0.04568 (8)	0.03734 (7)	0.03350 (7)	0.00681 (5)	0.00661 (5)	0.00766 (5)
O1	0.0490 (13)	0.0417 (13)	0.0455 (12)	0.0100 (10)	0.0040 (10)	0.0047 (10)
O2	0.0543 (14)	0.0485 (12)	0.0465 (12)	0.0145 (11)	−0.0036 (11)	0.0024 (8)
O3	0.0754 (17)	0.0499 (15)	0.0603 (15)	0.0102 (12)	0.0314 (13)	0.0178 (12)
O4	0.0650 (15)	0.0465 (14)	0.0517 (14)	0.0039 (11)	0.0230 (11)	0.0069 (11)
N1	0.0555 (17)	0.0416 (15)	0.0474 (16)	0.0116 (12)	0.0152 (13)	0.0175 (13)
N2	0.0493 (16)	0.0372 (14)	0.0425 (15)	0.0101 (12)	0.0068 (12)	0.0041 (12)
C1	0.0449 (18)	0.0384 (17)	0.0400 (16)	0.0004 (13)	0.0069 (13)	0.0122 (14)
C2	0.0449 (17)	0.0317 (16)	0.0451 (17)	−0.0002 (13)	0.0026 (13)	0.0132 (13)
C3	0.0450 (18)	0.0385 (18)	0.062 (2)	0.0048 (14)	0.0081 (16)	0.0162 (16)
C4	0.047 (2)	0.045 (2)	0.082 (3)	−0.0008 (16)	−0.0102 (18)	0.025 (2)
C5	0.067 (2)	0.0364 (18)	0.059 (2)	−0.0093 (16)	−0.0156 (18)	0.0191 (17)
C6	0.076 (3)	0.0364 (18)	0.051 (2)	0.0046 (17)	0.0001 (18)	0.0063 (15)
C7	0.0463 (18)	0.0387 (18)	0.0507 (19)	0.0068 (14)	0.0017 (15)	0.0102 (15)
C8	0.100 (4)	0.059 (3)	0.082 (3)	−0.013 (2)	−0.036 (3)	0.019 (2)
C9	0.0417 (17)	0.0466 (19)	0.0370 (16)	0.0020 (14)	0.0028 (13)	0.0035 (14)
C10	0.0392 (16)	0.0446 (18)	0.0352 (15)	0.0013 (13)	0.0022 (12)	0.0084 (13)
C11	0.056 (2)	0.050 (2)	0.055 (2)	0.0112 (16)	0.0145 (16)	0.0217 (17)
C12	0.059 (2)	0.056 (2)	0.059 (2)	0.0196 (17)	0.0222 (18)	0.0187 (19)
C13	0.0469 (19)	0.066 (2)	0.050 (2)	0.0074 (17)	0.0112 (15)	0.0227 (18)
C14	0.076 (3)	0.059 (2)	0.075 (3)	0.009 (2)	0.031 (2)	0.031 (2)
C15	0.066 (2)	0.045 (2)	0.063 (2)	0.0092 (17)	0.0198 (19)	0.0133 (18)
C16	0.065 (2)	0.090 (3)	0.068 (3)	0.015 (2)	0.028 (2)	0.033 (2)
C17	0.068 (2)	0.050 (2)	0.053 (2)	0.0179 (17)	0.0216 (18)	0.0189 (17)
C18	0.066 (2)	0.066 (3)	0.052 (2)	0.0174 (19)	0.0237 (18)	0.0201 (19)
C19	0.066 (2)	0.070 (3)	0.064 (2)	0.004 (2)	0.023 (2)	0.029 (2)
C20	0.071 (2)	0.048 (2)	0.068 (2)	0.0028 (18)	0.018 (2)	0.0268 (19)
C21	0.0435 (18)	0.0357 (17)	0.0495 (18)	0.0037 (13)	0.0053 (14)	0.0129 (14)
C22	0.0453 (18)	0.0346 (17)	0.0486 (18)	0.0016 (13)	0.0036 (14)	0.0105 (14)
C23	0.080 (3)	0.040 (2)	0.082 (3)	0.0076 (19)	0.016 (2)	0.019 (2)
C24	0.089 (3)	0.036 (2)	0.093 (3)	0.015 (2)	0.010 (3)	0.011 (2)
C25	0.087 (3)	0.050 (2)	0.071 (3)	0.030 (2)	0.018 (2)	0.001 (2)
C26	0.069 (2)	0.048 (2)	0.057 (2)	0.0158 (18)	0.0149 (18)	0.0071 (17)

Pb1—O1	2.333 (2)	C10—C11	1.386 (4)
Pb1—O3	2.418 (2)	C11—C12	1.383 (5)
Pb1—N2	2.608 (3)	C11—H11A	0.9300
Pb1—O2	2.644 (2)	C12—C13	1.378 (5)
Pb1—N1	2.656 (3)	C12—H12A	0.9300
Pb1—O4	2.701 (2)	C13—C14	1.389 (5)
O1—C1	1.282 (4)	C13—C16	1.509 (5)
O2—C1	1.239 (4)	C14—C15	1.376 (5)
O3—C9	1.277 (4)	C14—H14A	0.9300
O4—C9	1.240 (4)	C15—H15A	0.9300
N1—C17	1.335 (4)	C16—H16A	0.9600
N1—C21	1.339 (4)	C16—H16B	0.9600
N2—C26	1.333 (4)	C16—H16C	0.9600
N2—C22	1.345 (4)	C17—C18	1.378 (5)
C1—C2	1.500 (4)	C17—H17A	0.9300
C2—C7	1.384 (4)	C18—C19	1.358 (5)
C2—C3	1.385 (4)	C18—H18A	0.9300
C3—C4	1.379 (5)	C19—C20	1.384 (5)
C3—H3A	0.9300	C19—H19A	0.9300
C4—C5	1.375 (5)	C20—C21	1.378 (5)
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.377 (5)	C21—C22	1.486 (5)
C5—C8	1.508 (5)	C22—C23	1.382 (5)
C6—C7	1.383 (5)	C23—C24	1.372 (6)
C6—H6A	0.9300	C23—H23A	0.9300
C7—H7A	0.9300	C24—C25	1.359 (6)
C8—H8A	0.9600	C24—H24A	0.9300
C8—H8B	0.9600	C25—C26	1.372 (5)
C8—H8C	0.9600	C25—H25A	0.9300
C9—C10	1.490 (4)	C26—H26A	0.9300
C10—C15	1.379 (5)
O1—Pb1—O3	84.31 (9)	C15—C10—C11	118.0 (3)
O1—Pb1—N2	83.74 (8)	C15—C10—C9	120.4 (3)
O3—Pb1—N2	77.33 (8)	C11—C10—C9	121.6 (3)
O1—Pb1—O2	52.25 (7)	C12—C11—C10	121.2 (3)
O3—Pb1—O2	121.72 (8)	C12—C11—H11A	119.4
N2—Pb1—O2	124.68 (8)	C10—C11—H11A	119.4
O1—Pb1—N1	79.77 (8)	C13—C12—C11	121.0 (3)
O3—Pb1—N1	137.27 (8)	C13—C12—H12A	119.5
N2—Pb1—N1	61.75 (8)	C11—C12—H12A	119.5
O2—Pb1—N1	77.17 (8)	C12—C13—C14	117.4 (3)
O1—Pb1—O4	82.72 (8)	C12—C13—C16	120.5 (3)
O3—Pb1—O4	50.77 (8)	C14—C13—C16	122.1 (3)
N2—Pb1—O4	127.29 (8)	C15—C14—C13	121.8 (4)
O2—Pb1—O4	83.26 (7)	C15—C14—H14A	119.1
N1—Pb1—O4	159.20 (9)	C13—C14—H14A	119.1
C1—O1—Pb1	99.27 (19)	C14—C15—C10	120.6 (3)
C1—O2—Pb1	85.80 (18)	C14—C15—H15A	119.7
C9—O3—Pb1	99.36 (19)	C10—C15—H15A	119.7
C9—O4—Pb1	87.0 (2)	C13—C16—H16A	109.5
C17—N1—C21	118.3 (3)	C13—C16—H16B	109.5
C17—N1—Pb1	119.9 (2)	H16A—C16—H16B	109.5
C21—N1—Pb1	121.1 (2)	C13—C16—H16C	109.5
C26—N2—C22	118.0 (3)	H16A—C16—H16C	109.5
C26—N2—Pb1	119.3 (2)	H16B—C16—H16C	109.5
C22—N2—Pb1	122.6 (2)	N1—C17—C18	123.3 (3)
O2—C1—O1	122.5 (3)	N1—C17—H17A	118.4
O2—C1—C2	119.8 (3)	C18—C17—H17A	118.4
O1—C1—C2	117.7 (3)	C19—C18—C17	118.5 (4)
C7—C2—C3	118.6 (3)	C19—C18—H18A	120.7
C7—C2—C1	119.6 (3)	C17—C18—H18A	120.7
C3—C2—C1	121.8 (3)	C18—C19—C20	118.9 (3)
C4—C3—C2	120.3 (3)	C18—C19—H19A	120.5
C4—C3—H3A	119.9	C20—C19—H19A	120.5
C2—C3—H3A	119.9	C21—C20—C19	119.8 (3)
C5—C4—C3	121.7 (3)	C21—C20—H20A	120.1
C5—C4—H4A	119.2	C19—C20—H20A	120.1
C3—C4—H4A	119.2	N1—C21—C20	121.1 (3)
C4—C5—C6	117.7 (3)	N1—C21—C22	116.7 (3)
C4—C5—C8	120.4 (4)	C20—C21—C22	122.2 (3)
C6—C5—C8	121.9 (4)	N2—C22—C23	120.9 (3)
C5—C6—C7	121.6 (3)	N2—C22—C21	117.2 (3)
C5—C6—H6A	119.2	C23—C22—C21	121.9 (3)
C7—C6—H6A	119.2	C24—C23—C22	120.4 (4)
C6—C7—C2	120.1 (3)	C24—C23—H23A	119.8
C6—C7—H7A	120.0	C22—C23—H23A	119.8
C2—C7—H7A	120.0	C25—C24—C23	118.1 (4)
C5—C8—H8A	109.5	C25—C24—H24A	120.9
C5—C8—H8B	109.5	C23—C24—H24A	120.9
H8A—C8—H8B	109.5	C24—C25—C26	119.6 (4)
C5—C8—H8C	109.5	C24—C25—H25A	120.2
H8A—C8—H8C	109.5	C26—C25—H25A	120.2
H8B—C8—H8C	109.5	N2—C26—C25	122.9 (4)
O4—C9—O3	122.8 (3)	N2—C26—H26A	118.6
O4—C9—C10	120.4 (3)	C25—C26—H26A	118.6
O3—C9—C10	116.8 (3)

Table 1

Selected bond lengths (Å)

Pb1—O1	2.333 (2)
Pb1—O3	2.418 (2)
Pb1—N2	2.608 (3)
Pb1—O2	2.644 (2)
Pb1—N1	2.656 (3)
Pb1—O4	2.701 (2)