Poly[(μ(5)-2,2'-bipyridine-5,5'-dicarboxyl-ato)lead(II)].

In the title polymeric compound, [Pb(C(12)H(6)N(2)O(4))](n), the Pb(II) cation, located on a mirror plane, is N,N'-chelated by a 2-2'-bipyridine-5,5'-dicarboxyl-ate (bpdc) anion and is further coordinated by six O atoms from four carboxyl groups of bpdc anions in an irregular N(2)O(6) geometry. The carboxylate groups bridge the Pb(II) cations, forming a three-dimensional polymeric structure. The carboxyl-ate group is twisted away from the attached pyridine ring by 11.4 (3)°.

Related literature

For background to niacin, see: Krishnamachari (1974 ▶) and to N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Greenaway et al. (1984 ▶); Hökelek & Necefoğlu (1996 ▶); Hökelek et al. (2009 ▶, 2010 ▶, 2011 ▶).

Experimental

Crystal data

[Pb(C12H6N2O4)]

M = 449.39

Orthorhombic,

a = 13.6224 (3) Å

b = 4.1923 (2) Å

c = 10.2180 (3) Å

V = 583.54 (3) Å3

Z = 2

Mo Kα radiation

μ = 14.47 mm−1

T = 100 K

0.32 × 0.18 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.055, T max = 0.235

9729 measured reflections

1542 independent reflections

1511 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.055

S = 1.24

1542 reflections

90 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.53 e Å−3

Δρmin = −0.75 e Å−3

Absolute structure: Flack (1983 ▶), 728 Friedel pairs

Flack parameter: 0.497 (14)

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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035647/xu5606sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035647/xu5606Isup2.hkl

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

[Pb(C12H6N2O4)]	F(000) = 412
Mr = 449.39	Dx = 2.558 Mg m−3
Orthorhombic, Pmn21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac -2	Cell parameters from 8915 reflections
a = 13.6224 (3) Å	θ = 2.5–28.5°
b = 4.1923 (2) Å	µ = 14.47 mm−1
c = 10.2180 (3) Å	T = 100 K
V = 583.54 (3) Å3	Prism, colorless
Z = 2	0.32 × 0.18 × 0.10 mm

Bruker Kappa APEXII CCD area-detector diffractometer	1542 independent reflections
Radiation source: fine-focus sealed tube	1511 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 28.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −18→17
Tmin = 0.055, Tmax = 0.235	k = −5→5
9729 measured reflections	l = −13→13

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.019	w = 1/[σ2(Fo2) + (0.0212P)2 + 3.443P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.055	(Δ/σ)max < 0.001
S = 1.24	Δρmax = 1.53 e Å−3
1542 reflections	Δρmin = −0.75 e Å−3
90 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0097 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 728 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.497 (14)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Pb1	0.0000	0.81379 (5)	0.6243	0.00544 (10)
O1	0.3476 (4)	0.2412 (13)	0.9391 (5)	0.0145 (9)
O2	0.3886 (3)	0.6151 (12)	1.0873 (4)	0.0136 (9)
N1	0.0870 (4)	0.7262 (14)	0.8556 (5)	0.0134 (11)
C1	0.1730 (4)	0.5765 (15)	0.8787 (5)	0.0099 (11)
H1	0.1929	0.4075	0.8227	0.012*
C2	0.2338 (4)	0.6648 (14)	0.9835 (6)	0.0091 (11)
C3	0.2044 (5)	0.9052 (17)	1.0680 (6)	0.0138 (11)
H3	0.2446	0.9677	1.1395	0.017*
C4	0.1157 (5)	1.0506 (17)	1.0457 (6)	0.0149 (12)
H4	0.0926	1.2117	1.1034	0.018*
C5	0.0596 (5)	0.9597 (17)	0.9373 (6)	0.0160 (12)
C6	0.3296 (4)	0.4896 (16)	1.0016 (5)	0.0127 (12)

	U11	U22	U33	U12	U13	U23
Pb1	0.00259 (13)	0.00704 (13)	0.00668 (12)	0.000	0.000	0.00030 (19)
O1	0.009 (2)	0.022 (2)	0.013 (2)	0.0027 (19)	−0.0030 (18)	−0.0058 (18)
O2	0.007 (2)	0.018 (2)	0.015 (2)	−0.0035 (17)	−0.0056 (13)	−0.0002 (15)
N1	0.009 (3)	0.022 (3)	0.009 (2)	0.000 (2)	−0.001 (2)	−0.002 (2)
C1	0.009 (3)	0.013 (3)	0.008 (2)	0.004 (2)	−0.0023 (19)	0.004 (2)
C2	0.003 (3)	0.014 (3)	0.011 (3)	−0.001 (2)	−0.002 (2)	0.0008 (19)
C3	0.010 (3)	0.025 (3)	0.006 (2)	0.001 (3)	0.000 (2)	0.000 (3)
C4	0.010 (3)	0.018 (3)	0.017 (3)	0.003 (2)	−0.001 (2)	−0.004 (2)
C5	0.012 (3)	0.020 (3)	0.016 (3)	0.005 (2)	−0.002 (2)	0.004 (2)
C6	0.003 (2)	0.029 (4)	0.006 (2)	−0.004 (2)	−0.0017 (18)	0.006 (2)

Pb1—O1i	2.819 (5)	C1—C2	1.403 (8)
Pb1—O2i	2.383 (5)	C1—H1	0.9500
Pb1—O2ii	2.383 (5)	C2—C3	1.386 (9)
Pb1—O2iii	2.860 (5)	C2—C6	1.509 (8)
Pb1—N1	2.669 (5)	C3—C4	1.373 (9)
Pb1—N1iv	2.669 (5)	C3—H3	0.9500
O1—C6	1.245 (8)	C4—C5	1.398 (9)
O2—Pb1v	2.383 (5)	C4—H4	0.9500
N1—C1	1.350 (8)	C5—C5iv	1.623 (13)
N1—C5	1.340 (9)	C6—O2	1.300 (7)
O2ii—Pb1—O2i	79.1 (2)	C3—C2—C1	119.8 (6)
O2i—Pb1—N1iv	108.61 (16)	C3—C2—C6	121.8 (5)
O2ii—Pb1—N1	108.61 (17)	C2—C3—H3	120.9
O2i—Pb1—N1	75.73 (16)	C4—C3—C2	118.3 (6)
O2ii—Pb1—N1iv	75.73 (16)	C4—C3—H3	120.9
N1—Pb1—N1iv	52.7 (3)	C3—C4—C5	119.4 (6)
C6—O2—Pb1v	101.2 (4)	C3—C4—H4	120.3
C1—N1—Pb1	127.2 (4)	C5—C4—H4	120.3
C5—N1—Pb1	109.1 (4)	N1—C5—C4	122.7 (6)
C5—N1—C1	118.2 (6)	N1—C5—C5iv	106.2 (4)
N1—C1—C2	121.5 (6)	C4—C5—C5iv	123.1 (4)
N1—C1—H1	119.2	O1—C6—O2	124.2 (6)
C2—C1—H1	119.2	O1—C6—C2	120.9 (5)
C1—C2—C6	118.4 (5)	O2—C6—C2	114.8 (6)
O2i—Pb1—N1—C1	19.7 (5)	N1—C1—C2—C6	−179.0 (5)
O2ii—Pb1—N1—C1	92.8 (5)	C1—C2—C3—C4	−0.1 (10)
O2i—Pb1—N1—C5	172.7 (5)	C6—C2—C3—C4	−179.3 (6)
O2ii—Pb1—N1—C5	−114.2 (5)	C1—C2—C6—O1	−11.3 (9)
N1iv—Pb1—N1—C1	147.1 (5)	C1—C2—C6—O2	169.9 (5)
N1iv—Pb1—N1—C5	−59.9 (5)	C3—C2—C6—O1	167.9 (6)
Pb1—N1—C1—C2	149.5 (5)	C3—C2—C6—O2	−10.9 (8)
C5—N1—C1—C2	−1.3 (9)	C2—C3—C4—C5	−1.9 (10)
Pb1—N1—C5—C4	−156.5 (5)	C3—C4—C5—N1	2.5 (11)
Pb1—N1—C5—C5iv	53.8 (3)	C3—C4—C5—C5iv	147.0 (5)
C1—N1—C5—C4	−0.8 (10)	O1—C6—O2—Pb1v	−14.7 (7)
C1—N1—C5—C5iv	−150.5 (5)	C2—C6—O2—Pb1v	164.0 (4)
N1—C1—C2—C3	1.8 (9)

Table 1

Selected bond lengths (Å)

Pb1—O1i	2.819 (5)
Pb1—O2i	2.383 (5)
Pb1—O2ii	2.860 (5)
Pb1—N1	2.669 (5)

Symmetry codes: (i) ; (ii) .