Poly[diaqua-bis(μ(2)-5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ato-κN,O:O)lead(II)].

In the title complex, [Pb(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)](n), the eight-coordinate Pb(II) atom lies on a twofold rotation axis and adopts a slightly distorted square-anti-prismatic N(2)O(6) coordination geometry. The ligand donor atoms are the tertiary N atoms of the imidazole rings and the carboxyl-ate O atoms of two chelating 5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ate ligands, the carb-oxy O atoms of two additional imidazole ligands and two water O atoms. The carb-oxy O and the N,O-chelate systems also link adjacent Pb(II) atoms, forming a two-dimensional layer structure, with four individual Pb(II) atoms located at the corners of a square. These layers are further inter-connected by an extensive array of O-H⋯O and N-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For the properties and uses of imidazole­dicarboxyl­ate complexes, see: Cao et al. (2002 ▶); Rajendiran et al. (2003 ▶).

Experimental

Crystal data

[Pb(C8H9N2O4)2(H2O)2]

M = 637.57

Monoclinic,

a = 13.1201 (15) Å

b = 13.2929 (16) Å

c = 11.5910 (13) Å

β = 98.531 (2)°

V = 1999.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 8.50 mm−1

T = 293 K

0.45 × 0.17 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.114, T max = 0.404

4884 measured reflections

1751 independent reflections

1640 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.039

S = 1.02

1751 reflections

143 parameters

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.69 e Å−3

Data collection: SMART (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 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013735/sj2771sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013735/sj2771Isup2.hkl

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

[Pb(C8H9N2O4)2(H2O)2]	F(000) = 1232
Mr = 637.57	Dx = 2.118 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2051 reflections
a = 13.1201 (15) Å	θ = 2.5–23.9°
b = 13.2929 (16) Å	µ = 8.50 mm−1
c = 11.5910 (13) Å	T = 293 K
β = 98.531 (2)°	Block, colorless
V = 1999.2 (4) Å3	0.45 × 0.17 × 0.13 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	1751 independent reflections
Radiation source: fine-focus sealed tube	1640 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→15
Tmin = 0.114, Tmax = 0.404	k = −15→15
4884 measured reflections	l = −10→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019	H-atom parameters constrained
wR(F2) = 0.039	w = 1/[σ2(Fo2) + 0.170P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.002
1751 reflections	Δρmax = 0.82 e Å−3
143 parameters	Δρmin = −0.69 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00501 (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 > 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.

	x	y	z	Uiso*/Ueq
Pb1	0.5000	0.585420 (12)	0.7500	0.02187 (10)
N1	0.36101 (17)	0.72953 (19)	0.7416 (2)	0.0206 (6)
N2	0.26176 (19)	0.8636 (2)	0.7255 (2)	0.0245 (6)
H2	0.2380	0.9221	0.7040	0.029*
O1	0.33533 (16)	0.55121 (18)	0.8607 (2)	0.0288 (6)
O2	0.20043 (17)	0.61233 (19)	0.9317 (2)	0.0346 (6)
O3	0.09662 (17)	0.7669 (2)	0.9230 (2)	0.0400 (7)
H3	0.1304	0.7149	0.9245	0.060*
O4	0.0980 (2)	0.9168 (2)	0.8428 (3)	0.0521 (9)
O5	0.43915 (18)	0.6096 (2)	0.5232 (2)	0.0374 (6)
H5C	0.4120	0.5656	0.4750	0.045*
H5D	0.4830	0.6427	0.4915	0.045*
C1	0.2736 (2)	0.6209 (3)	0.8716 (3)	0.0240 (7)
C2	0.2842 (2)	0.7169 (2)	0.8095 (3)	0.0204 (7)
C3	0.2221 (2)	0.8003 (3)	0.7997 (3)	0.0228 (8)
C4	0.1323 (3)	0.8316 (3)	0.8572 (3)	0.0314 (9)
C5	0.3450 (2)	0.8188 (2)	0.6912 (3)	0.0230 (8)
C6	0.4039 (2)	0.8661 (3)	0.6046 (3)	0.0285 (8)
H6A	0.4688	0.8309	0.6062	0.034*
H6B	0.4193	0.9353	0.6274	0.034*
C7	0.3461 (3)	0.8646 (3)	0.4806 (3)	0.0355 (9)
H7A	0.3380	0.7954	0.4541	0.043*
H7B	0.2779	0.8928	0.4803	0.043*
C8	0.4016 (3)	0.9236 (3)	0.3967 (4)	0.0408 (10)
H8A	0.4129	0.9913	0.4246	0.061*
H8B	0.3604	0.9245	0.3210	0.061*
H8C	0.4667	0.8923	0.3914	0.061*

	U11	U22	U33	U12	U13	U23
Pb1	0.02470 (12)	0.01520 (13)	0.02690 (14)	0.000	0.00777 (7)	0.000
N1	0.0251 (13)	0.0146 (16)	0.0229 (15)	0.0002 (11)	0.0059 (11)	0.0026 (13)
N2	0.0337 (15)	0.0126 (15)	0.0273 (16)	0.0049 (12)	0.0047 (12)	0.0059 (14)
O1	0.0343 (13)	0.0162 (13)	0.0375 (15)	0.0015 (10)	0.0110 (10)	0.0029 (12)
O2	0.0376 (14)	0.0306 (14)	0.0396 (16)	−0.0018 (11)	0.0191 (11)	0.0072 (13)
O3	0.0354 (13)	0.0414 (18)	0.0474 (17)	0.0086 (12)	0.0203 (11)	0.0008 (15)
O4	0.0632 (18)	0.046 (2)	0.051 (2)	0.0373 (14)	0.0236 (15)	0.0114 (15)
O5	0.0407 (14)	0.0395 (16)	0.0338 (16)	−0.0070 (12)	0.0115 (11)	−0.0025 (13)
C1	0.0266 (17)	0.0222 (19)	0.0236 (19)	−0.0044 (15)	0.0049 (14)	−0.0031 (17)
C2	0.0235 (15)	0.0163 (18)	0.0212 (18)	−0.0013 (13)	0.0026 (13)	−0.0018 (15)
C3	0.0264 (16)	0.022 (2)	0.0198 (18)	0.0019 (14)	0.0022 (13)	−0.0012 (16)
C4	0.0335 (19)	0.035 (2)	0.027 (2)	0.0074 (17)	0.0083 (15)	−0.0017 (19)
C5	0.0244 (16)	0.0178 (19)	0.0266 (19)	−0.0001 (14)	0.0030 (13)	0.0008 (16)
C6	0.0286 (18)	0.025 (2)	0.033 (2)	−0.0009 (15)	0.0050 (14)	0.0066 (18)
C7	0.0365 (19)	0.037 (2)	0.033 (2)	−0.0111 (17)	0.0026 (15)	0.003 (2)
C8	0.049 (2)	0.042 (3)	0.031 (2)	−0.0065 (18)	0.0058 (18)	0.0088 (19)

Pb1—N1	2.637 (2)	O4—C4	1.221 (4)
Pb1—N1i	2.637 (2)	O4—Pb1iv	2.725 (3)
Pb1—O5i	2.651 (3)	O5—H5C	0.8500
Pb1—O5	2.652 (3)	O5—H5D	0.8500
Pb1—O1	2.710 (2)	C1—C2	1.481 (5)
Pb1—O1i	2.710 (2)	C2—C3	1.370 (4)
Pb1—O4ii	2.725 (3)	C3—C4	1.496 (5)
Pb1—O4iii	2.725 (3)	C5—C6	1.494 (5)
N1—C5	1.326 (4)	C6—C7	1.522 (4)
N1—C2	1.377 (4)	C6—H6A	0.9700
N2—C5	1.354 (4)	C6—H6B	0.9700
N2—C3	1.361 (5)	C7—C8	1.517 (5)
N2—H2	0.8600	C7—H7A	0.9700
O1—C1	1.249 (4)	C7—H7B	0.9700
O2—C1	1.273 (4)	C8—H8A	0.9600
O3—C4	1.284 (4)	C8—H8B	0.9600
O3—H3	0.8200	C8—H8C	0.9600
N1—Pb1—N1i	86.81 (11)	Pb1—O5—H5C	127.1
N1—Pb1—O5i	93.06 (8)	Pb1—O5—H5D	111.6
N1i—Pb1—O5i	76.75 (8)	H5C—O5—H5D	108.5
N1—Pb1—O5	76.75 (8)	O1—C1—O2	122.8 (3)
N1i—Pb1—O5	93.06 (8)	O1—C1—C2	118.7 (3)
O5i—Pb1—O5	166.09 (11)	O2—C1—C2	118.4 (3)
N1—Pb1—O1	62.85 (7)	C3—C2—N1	109.3 (3)
N1i—Pb1—O1	134.44 (7)	C3—C2—C1	129.8 (3)
O5i—Pb1—O1	72.23 (7)	N1—C2—C1	120.8 (3)
O5—Pb1—O1	110.24 (7)	N2—C3—C2	106.0 (3)
N1—Pb1—O1i	134.44 (7)	N2—C3—C4	120.6 (3)
N1i—Pb1—O1i	62.85 (7)	C2—C3—C4	133.3 (3)
O5i—Pb1—O1i	110.23 (7)	O4—C4—O3	122.8 (3)
O5—Pb1—O1i	72.23 (7)	O4—C4—C3	119.8 (4)
O1—Pb1—O1i	160.68 (10)	O3—C4—C3	117.3 (3)
N1—Pb1—O4ii	153.57 (9)	N1—C5—N2	110.3 (3)
N1i—Pb1—O4ii	107.45 (9)	N1—C5—C6	127.6 (3)
O5i—Pb1—O4ii	69.71 (9)	N2—C5—C6	122.1 (3)
O5—Pb1—O4ii	123.10 (9)	C5—C6—C7	113.2 (3)
O1—Pb1—O4ii	92.16 (8)	C5—C6—H6A	108.9
O1i—Pb1—O4ii	71.71 (8)	C7—C6—H6A	108.9
N1—Pb1—O4iii	107.46 (9)	C5—C6—H6B	108.9
N1i—Pb1—O4iii	153.56 (9)	C7—C6—H6B	108.9
O5i—Pb1—O4iii	123.10 (9)	H6A—C6—H6B	107.8
O5—Pb1—O4iii	69.70 (9)	C8—C7—C6	112.3 (3)
O1—Pb1—O4iii	71.72 (8)	C8—C7—H7A	109.1
O1i—Pb1—O4iii	92.16 (8)	C6—C7—H7A	109.1
O4ii—Pb1—O4iii	69.29 (14)	C8—C7—H7B	109.1
C5—N1—C2	106.2 (3)	C6—C7—H7B	109.1
C5—N1—Pb1	136.9 (2)	H7A—C7—H7B	107.9
C2—N1—Pb1	116.79 (19)	C7—C8—H8A	109.5
C5—N2—C3	108.3 (3)	C7—C8—H8B	109.5
C5—N2—H2	125.9	H8A—C8—H8B	109.5
C3—N2—H2	125.9	C7—C8—H8C	109.5
C1—O1—Pb1	119.8 (2)	H8A—C8—H8C	109.5
C4—O3—H3	109.5	H8B—C8—H8C	109.5
C4—O4—Pb1iv	163.7 (3)
N1i—Pb1—N1—C5	39.1 (3)	Pb1—N1—C2—C1	−7.6 (3)
O5i—Pb1—N1—C5	115.6 (3)	O1—C1—C2—C3	174.0 (3)
O5—Pb1—N1—C5	−54.8 (3)	O2—C1—C2—C3	−4.4 (5)
O1—Pb1—N1—C5	−176.2 (3)	O1—C1—C2—N1	−0.5 (4)
O1i—Pb1—N1—C5	−6.9 (3)	O2—C1—C2—N1	−178.9 (3)
O4ii—Pb1—N1—C5	163.3 (3)	C5—N2—C3—C2	0.4 (4)
O4iii—Pb1—N1—C5	−118.2 (3)	C5—N2—C3—C4	176.8 (3)
N1i—Pb1—N1—C2	−137.1 (2)	N1—C2—C3—N2	0.0 (3)
O5i—Pb1—N1—C2	−60.6 (2)	C1—C2—C3—N2	−175.0 (3)
O5—Pb1—N1—C2	129.0 (2)	N1—C2—C3—C4	−175.8 (3)
O1—Pb1—N1—C2	7.63 (19)	C1—C2—C3—C4	9.3 (6)
O1i—Pb1—N1—C2	176.89 (18)	Pb1iv—O4—C4—O3	−108.0 (9)
O4ii—Pb1—N1—C2	−12.9 (3)	Pb1iv—O4—C4—C3	74.0 (10)
O4iii—Pb1—N1—C2	65.6 (2)	N2—C3—C4—O4	−4.3 (5)
N1—Pb1—O1—C1	−8.6 (2)	C2—C3—C4—O4	171.0 (4)
N1i—Pb1—O1—C1	45.2 (3)	N2—C3—C4—O3	177.7 (3)
O5i—Pb1—O1—C1	94.6 (2)	C2—C3—C4—O3	−7.1 (6)
O5—Pb1—O1—C1	−70.9 (2)	C2—N1—C5—N2	0.7 (3)
O1i—Pb1—O1—C1	−164.9 (2)	Pb1—N1—C5—N2	−175.8 (2)
O4ii—Pb1—O1—C1	162.5 (2)	C2—N1—C5—C6	−176.9 (3)
O4iii—Pb1—O1—C1	−130.2 (2)	Pb1—N1—C5—C6	6.7 (5)
Pb1—O1—C1—O2	−173.4 (2)	C3—N2—C5—N1	−0.7 (4)
Pb1—O1—C1—C2	8.3 (4)	C3—N2—C5—C6	177.0 (3)
C5—N1—C2—C3	−0.4 (3)	N1—C5—C6—C7	105.0 (4)
Pb1—N1—C2—C3	176.90 (19)	N2—C5—C6—C7	−72.3 (4)
C5—N1—C2—C1	175.1 (3)	C5—C6—C7—C8	173.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5D···O4v	0.85	2.58	3.182 (4)	129
O5—H5D···O3v	0.85	2.16	3.004 (3)	176
O5—H5C···O1vi	0.85	2.19	3.035 (3)	176
O3—H3···O2	0.82	1.64	2.459 (3)	178
N2—H2···O1vii	0.86	2.05	2.909 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5D⋯O4i	0.85	2.58	3.182 (4)	129
O5—H5D⋯O3i	0.85	2.16	3.004 (3)	176
O5—H5C⋯O1ii	0.85	2.19	3.035 (3)	176
O3—H3⋯O2	0.82	1.64	2.459 (3)	178
N2—H2⋯O1iii	0.86	2.05	2.909 (4)	172

Symmetry codes: (i) ; (ii) ; (iii) .