Poly[(μ-1H-benzimidazole-5,6-dicarboxyl-ato)lead(II)].

The crystal structure of the two-dimensional polymeric title compound, [Pb(C(9)H(4)N(2)O(4))](n), comprises one crystallo-graphic-ally independent Pb(II) atom and one fully deprotonated 1H-benzimidazole-5,6-dicarboxyl-ate (H(2)L) ligand. The Pb(II) atom is seven-coordinated by six O atoms and one N atom from the H(2)L ligands, giving a capped octa-hedral coordination geometry. The structure is a layered two-dimensional coordination polymer extending parallel to (100) with N-H⋯O hydrogen bonds inter-actions between the layers, stabilizing the crystal structure.

Related literature

For applications of metal-organic frameworks, see: Li et al. (2007 ▶). For related structures, see: Gao et al. (2008 ▶); Lo et al.. (2007 ▶); Wang et al. (2009 ▶); Wei et al. (2008 ▶);Yao et al. (2008 ▶); Zhai (2009 ▶).

Experimental

Crystal data

[Pb(C9H4N2O4)]

M = 411.34

Monoclinic,

a = 13.127 (2) Å

b = 9.5571 (14) Å

c = 6.7557 (10) Å

β = 99.587 (2)°

V = 835.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 20.19 mm−1

T = 273 K

0.30 × 0.30 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.003, T max = 0.004

3954 measured reflections

1458 independent reflections

1273 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.08

1458 reflections

133 parameters

12 restraints

H-atom parameters constrained

Δρmax = 3.24 e Å−3

Δρmin = −2.83 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017065/go2009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017065/go2009Isup2.hkl

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

[Pb(C9H4N2O4)]	F(000) = 744.0
Mr = 411.34	Dx = 3.269 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2747 reflections
a = 13.127 (2) Å	θ = 2.7–28.4°
b = 9.5571 (14) Å	µ = 20.19 mm−1
c = 6.7557 (10) Å	T = 273 K
β = 99.587 (2)°	Block, yellow
V = 835.7 (2) Å3	0.30 × 0.30 × 0.27 mm
Z = 4

Bruker APEXII CCD diffractometer	1458 independent reflections
Radiation source: fine-focus sealed tube	1273 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→15
Tmin = 0.003, Tmax = 0.004	k = −11→8
3954 measured reflections	l = −7→8

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0814P)2] where P = (Fo2 + 2Fc2)/3
1458 reflections	(Δ/σ)max = 0.001
133 parameters	Δρmax = 3.24 e Å−3
12 restraints	Δρmin = −2.83 e Å−3

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. The number of independent reflections and the number of reflections used in the refinement are not the same, because we use 'omit -3 50' to enhance the'_diffrn_measured_fraction_theta_full'.

	x	y	z	Uiso*/Ueq
C4	0.7560 (4)	0.3072 (4)	0.2539 (9)	0.019 (2)
C5	0.6729 (3)	0.2152 (5)	0.2241 (10)	0.0164 (19)
H5	0.6058	0.2496	0.1959	0.020*
C6	0.6901 (4)	0.0717 (4)	0.2362 (9)	0.0152 (18)
C9	0.7904 (4)	0.0203 (4)	0.2783 (9)	0.0169 (19)
C1	0.8736 (3)	0.1123 (6)	0.3081 (9)	0.025 (3)
H1	0.9407	0.0779	0.3363	0.030*
C2	0.8564 (4)	0.2558 (5)	0.2959 (9)	0.021 (2)
Pb1	0.62381 (3)	0.62780 (3)	0.17812 (5)	0.0172 (2)
N1	0.7597 (7)	0.4523 (8)	0.2560 (13)	0.0252 (19)
C3	0.8566 (8)	0.4844 (11)	0.2927 (15)	0.025 (2)
H3	0.8810	0.5759	0.3003	0.029*
N2	0.9199 (8)	0.3693 (7)	0.3195 (14)	0.021 (2)
H2	0.9863	0.3690	0.3459	0.025*
C8	0.8123 (9)	−0.1314 (8)	0.3226 (17)	0.020 (2)
O4	0.8944 (6)	−0.1832 (8)	0.2949 (13)	0.036 (2)
C7	0.6000 (7)	−0.0282 (8)	0.1935 (12)	0.0146 (19)
O2	0.5921 (6)	−0.1031 (6)	0.0387 (11)	0.0220 (16)
O1	0.5389 (5)	−0.0325 (6)	0.3196 (9)	0.0184 (14)
O3	0.7406 (4)	−0.2011 (6)	0.3876 (9)	0.0167 (13)

	U11	U22	U33	U12	U13	U23
C4	0.024 (5)	0.013 (4)	0.019 (5)	−0.001 (4)	0.002 (4)	0.001 (3)
C5	0.006 (4)	0.021 (4)	0.022 (4)	0.005 (3)	0.002 (3)	0.002 (3)
C6	0.014 (5)	0.012 (4)	0.021 (5)	−0.003 (3)	0.007 (4)	0.000 (3)
C9	0.018 (5)	0.017 (4)	0.017 (5)	−0.003 (4)	0.007 (4)	−0.001 (3)
C1	0.030 (6)	0.017 (5)	0.030 (6)	0.005 (3)	0.011 (5)	0.001 (3)
C2	0.033 (6)	0.015 (5)	0.016 (5)	−0.006 (4)	0.008 (4)	−0.002 (4)
Pb1	0.0188 (3)	0.0151 (3)	0.0172 (3)	−0.00085 (11)	0.0019 (2)	−0.00061 (10)
N1	0.026 (5)	0.021 (4)	0.029 (5)	0.001 (4)	0.008 (4)	−0.003 (3)
C3	0.029 (6)	0.016 (5)	0.028 (6)	−0.004 (4)	0.003 (5)	−0.001 (4)
N2	0.016 (5)	0.019 (4)	0.031 (5)	−0.004 (3)	0.010 (4)	−0.001 (3)
C8	0.013 (6)	0.019 (5)	0.027 (6)	0.001 (3)	0.003 (5)	−0.006 (3)
O4	0.021 (4)	0.021 (4)	0.066 (6)	0.000 (3)	0.011 (4)	0.004 (4)
C7	0.013 (5)	0.014 (4)	0.014 (5)	0.004 (3)	−0.006 (4)	0.005 (3)
O2	0.030 (4)	0.017 (3)	0.021 (4)	0.003 (3)	0.010 (3)	−0.003 (3)
O1	0.010 (3)	0.032 (3)	0.013 (3)	−0.001 (2)	0.003 (3)	0.002 (2)
O3	0.010 (3)	0.018 (3)	0.021 (3)	0.001 (2)	0.000 (3)	0.003 (2)

C4—N1	1.387 (8)	Pb1—O1iv	2.653 (6)
C4—C5	1.389 (7)	Pb1—O2i	2.746 (6)
C4—C2	1.391 (7)	N1—C3	1.292 (13)
C5—C6	1.390 (7)	C3—N2	1.371 (13)
C5—H5	0.9300	C3—H3	0.9300
C6—C9	1.390 (7)	N2—H2	0.8600
C6—C7	1.510 (10)	C8—O4	1.228 (13)
C9—C1	1.390 (7)	C8—O3	1.289 (11)
C9—C8	1.498 (9)	C7—O2	1.258 (11)
C1—C2	1.390 (7)	C7—O1	1.265 (11)
C1—H1	0.9300	O2—Pb1iv	2.549 (7)
C2—N2	1.362 (9)	O2—Pb1v	2.746 (6)
Pb1—N1	2.442 (8)	O1—Pb1vi	2.630 (6)
Pb1—O3i	2.511 (6)	O1—Pb1ii	2.653 (6)
Pb1—O2ii	2.549 (7)	O3—Pb1v	2.511 (6)
Pb1—O1iii	2.630 (6)
N1—C4—C5	131.3 (5)	N1—Pb1—O2i	141.3 (2)
N1—C4—C2	108.7 (5)	O3i—Pb1—O2i	68.1 (2)
C5—C4—C2	120.0 (4)	O2ii—Pb1—O2i	112.01 (18)
C4—C5—C6	120.0 (4)	O1iii—Pb1—O2i	118.1 (2)
C6—C5—H5	120.0	O1iv—Pb1—O2i	89.52 (19)
C4—C5—H5	120.0	C3—N1—C4	105.7 (7)
C9—C6—C5	120.0 (4)	C3—N1—Pb1	122.6 (6)
C9—C6—C7	120.0 (4)	C4—N1—Pb1	131.4 (5)
C5—C6—C7	119.9 (4)	N1—C3—N2	113.0 (9)
C1—C9—C6	120.1 (4)	N1—C3—H3	123.5
C1—C9—C8	117.6 (5)	N2—C3—H3	123.5
C6—C9—C8	121.8 (5)	C2—N2—C3	106.1 (8)
C2—C1—H1	120.0	C2—N2—H2	126.9
C9—C1—H1	120.0	C3—N2—H2	126.9
C9—C1—C2	120.0 (4)	O4—C8—O3	123.6 (8)
N2—C2—C1	133.6 (5)	O4—C8—C9	120.2 (8)
N2—C2—C4	106.4 (5)	O3—C8—C9	116.2 (8)
C1—C2—C4	120.0 (4)	O2—C7—O1	124.6 (8)
N1—Pb1—O3i	88.3 (2)	O2—C7—C6	118.2 (8)
N1—Pb1—O2ii	87.7 (2)	O1—C7—C6	117.2 (7)
O3i—Pb1—O2ii	72.7 (2)	C7—O2—Pb1iv	147.5 (6)
N1—Pb1—O1iii	99.4 (2)	C7—O2—Pb1v	105.1 (5)
O3i—Pb1—O1iii	142.76 (18)	Pb1iv—O2—Pb1v	101.6 (2)
O2ii—Pb1—O1iii	71.3 (2)	C7—O1—Pb1vi	126.3 (5)
N1—Pb1—O1iv	98.2 (2)	C7—O1—Pb1ii	114.1 (5)
O3i—Pb1—O1iv	149.59 (19)	Pb1vi—O1—Pb1ii	114.4 (2)
O2ii—Pb1—O1iv	136.9 (2)	C8—O3—Pb1v	123.8 (6)
O1iii—Pb1—O1iv	65.6 (2)
N1—C4—C5—C6	−177.8 (6)	O1iii—Pb1—N1—C4	14.3 (7)
C2—C4—C5—C6	0.0	O1iv—Pb1—N1—C4	−52.2 (7)
C4—C5—C6—C9	0.0	O2i—Pb1—N1—C4	−151.8 (5)
C4—C5—C6—C7	−176.9 (6)	C4—N1—C3—N2	−1.0 (11)
C5—C6—C9—C1	0.0	Pb1—N1—C3—N2	−175.9 (7)
C7—C6—C9—C1	176.9 (6)	C1—C2—N2—C3	−178.7 (6)
C5—C6—C9—C8	170.9 (7)	C4—C2—N2—C3	0.4 (9)
C7—C6—C9—C8	−12.2 (8)	N1—C3—N2—C2	0.4 (12)
C6—C9—C1—C2	0.0	C1—C9—C8—O4	−32.8 (12)
C8—C9—C1—C2	−171.2 (7)	C6—C9—C8—O4	156.1 (8)
C9—C1—C2—N2	179.1 (9)	C1—C9—C8—O3	147.9 (7)
C9—C1—C2—C4	0.0	C6—C9—C8—O3	−23.2 (11)
N1—C4—C2—N2	−1.1 (7)	C5—C6—C7—O2	112.1 (7)
C5—C4—C2—N2	−179.3 (6)	C9—C6—C7—O2	−64.9 (8)
N1—C4—C2—C1	178.2 (5)	C5—C6—C7—O1	−69.5 (8)
C5—C4—C2—C1	0.0	C9—C6—C7—O1	113.6 (7)
C5—C4—N1—C3	179.3 (6)	O1—C7—O2—Pb1iv	150.4 (8)
C2—C4—N1—C3	1.3 (8)	C6—C7—O2—Pb1iv	−31.3 (15)
C5—C4—N1—Pb1	−6.5 (9)	O1—C7—O2—Pb1v	−65.2 (9)
C2—C4—N1—Pb1	175.5 (5)	C6—C7—O2—Pb1v	113.1 (6)
O3i—Pb1—N1—C3	−29.0 (8)	O2—C7—O1—Pb1vi	−94.0 (9)
O2ii—Pb1—N1—C3	−101.8 (8)	C6—C7—O1—Pb1vi	87.7 (7)
O1iii—Pb1—N1—C3	−172.4 (7)	O2—C7—O1—Pb1ii	113.2 (8)
O1iv—Pb1—N1—C3	121.2 (8)	C6—C7—O1—Pb1ii	−65.2 (7)
O2i—Pb1—N1—C3	21.6 (10)	O4—C8—O3—Pb1v	−74.3 (13)
O3i—Pb1—N1—C4	157.6 (7)	C9—C8—O3—Pb1v	105.0 (7)
O2ii—Pb1—N1—C4	84.8 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4vii	0.86	2.02	2.723 (12)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.86	2.02	2.723 (12)	138

Symmetry code: (i) .