Poly[(acetato-κO,O')aqua-(μ(4)-1H-benzimidazole-5,6-dicarboxyl-ato-κN:O,O:O,O:O)praseodymium(III)].

In the title complex, [Pr(C(9)H(4)N(2)O(4))(C(2)H(3)O(2))(H(2)O)](n), the Pr(III) ion is coordinated by five O atoms and one N atom from four benzimidazole-5,6-dicarboxyl-ate ligands, two O atoms from an acetate ligand and one water mol-ecule, giving a tricapped trigonal-prismatic geometry. The benzimidazole-5,6-dicarboxyl-ate and acetate ligands connect the Pr(III) ions, forming a layer in the ac plane; the layers are further linked by N-H⋯O and O-H⋯O hydrogen bonding and π-π stacking inter-actions between neighboring pyridine rings [the centroid-centroid distance is 3.467 (1) Å], assembling a three-dimensional supra-molecular network. The acetate methyl group is disordered over two positions with site-occupancy factors of 0.75 and 0.25.

Related literature

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

[Pr(C9H4N2O4)(C2H3O2)(H2O)]

M = 422.11

Triclinic,

a = 7.4284 (5) Å

b = 9.0109 (7) Å

c = 9.7239 (7) Å

α = 87.075 (1)°

β = 86.498 (1)°

γ = 84.274 (1)°

V = 645.77 (8) Å3

Z = 2

Mo Kα radiation

μ = 3.81 mm−1

T = 296 K

0.26 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.386, T max = 0.485

3963 measured reflections

2327 independent reflections

2184 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.072

S = 1.04

2327 reflections

199 parameters

22 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.23 e Å−3

Δρmin = −1.45 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 I, global. DOI: 10.1107/S1600536810036986/pk2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036986/pk2264Isup2.hkl

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

[Pr(C9H4N2O4)(C2H3O2)(H2O)]	Z = 2
Mr = 422.11	F(000) = 408
Triclinic, P1	Dx = 2.171 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4284 (5) Å	Cell parameters from 2989 reflections
b = 9.0109 (7) Å	θ = 2.3–28.4°
c = 9.7239 (7) Å	µ = 3.81 mm−1
α = 87.075 (1)°	T = 296 K
β = 86.498 (1)°	Block, colourless
γ = 84.274 (1)°	0.26 × 0.22 × 0.19 mm
V = 645.77 (8) Å3

Bruker SMART APEX CCD diffractometer	2327 independent reflections
Radiation source: fine-focus sealed tube	2184 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 25.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.386, Tmax = 0.485	k = −10→10
3963 measured reflections	l = −7→11

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0394P)2 + 1.0511P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2327 reflections	Δρmax = 1.23 e Å−3
199 parameters	Δρmin = −1.45 e Å−3
22 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: 0.0091 (12)

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	Occ. (<1)
Pr1	0.35344 (3)	0.35784 (2)	−0.10574 (2)	0.01137 (13)
O1	0.1245 (4)	0.2800 (3)	0.0551 (3)	0.0171 (6)
O1W	0.6206 (5)	0.2207 (4)	0.0136 (4)	0.0286 (8)
H1W	0.713 (5)	0.260 (5)	0.032 (6)	0.034*
H2W	0.626 (7)	0.135 (3)	0.051 (6)	0.034*
O2	−0.1348 (4)	0.4123 (3)	0.1093 (3)	0.0187 (7)
O3	0.5275 (4)	0.4696 (4)	0.2957 (3)	0.0229 (7)
O4	0.3620 (4)	0.4864 (3)	0.1165 (3)	0.0169 (6)
O5	0.3704 (4)	0.0699 (3)	−0.1295 (3)	0.0213 (7)
O6	0.5234 (4)	0.2005 (3)	−0.2842 (3)	0.0222 (7)
N1	−0.1290 (5)	0.2444 (4)	0.6358 (4)	0.0197 (8)
H1	−0.237 (4)	0.219 (6)	0.642 (6)	0.024*
N2	0.1301 (5)	0.3045 (4)	0.7108 (4)	0.0183 (8)
C1	0.0176 (5)	0.3514 (4)	0.1395 (4)	0.0124 (8)
C2	0.0663 (5)	0.3516 (4)	0.2883 (4)	0.0128 (8)
C3	−0.0669 (6)	0.3032 (5)	0.3815 (5)	0.0179 (9)
H3	−0.1780	0.2820	0.3522	0.021*
C4	−0.0292 (5)	0.2876 (5)	0.5200 (5)	0.0158 (9)
C5	0.1336 (5)	0.3240 (4)	0.5684 (4)	0.0137 (8)
C6	0.2660 (5)	0.3744 (4)	0.4746 (4)	0.0138 (8)
H6	0.3747	0.3995	0.5056	0.017*
C7	0.2352 (5)	0.3872 (4)	0.3345 (4)	0.0121 (8)
C8	0.3828 (5)	0.4492 (4)	0.2436 (4)	0.0117 (8)
C9	−0.0292 (6)	0.2583 (5)	0.7442 (5)	0.0191 (9)
H9	−0.0696	0.2371	0.8348	0.023*
C10	0.4743 (7)	0.0768 (5)	−0.2356 (6)	0.0304 (9)
C11	0.5650 (11)	−0.0621 (7)	−0.2989 (8)	0.0304 (9)	0.75
H11A	0.6777	−0.0907	−0.2569	0.046*	0.75
H11B	0.5877	−0.0431	−0.3961	0.046*	0.75
H11C	0.4876	−0.1412	−0.2840	0.046*	0.75
C11'	0.477 (3)	−0.055 (2)	−0.332 (2)	0.0304 (9)	0.25
H11D	0.5368	−0.1430	−0.2891	0.046*	0.25
H11E	0.5413	−0.0309	−0.4178	0.046*	0.25
H11F	0.3551	−0.0717	−0.3491	0.046*	0.25

	U11	U22	U33	U12	U13	U23
Pr1	0.01163 (17)	0.01259 (17)	0.00993 (17)	−0.00185 (9)	0.00044 (10)	−0.00098 (10)
O1	0.0192 (15)	0.0188 (15)	0.0137 (16)	−0.0041 (12)	0.0014 (12)	−0.0035 (12)
O1W	0.0286 (18)	0.0164 (16)	0.042 (2)	−0.0047 (14)	−0.0170 (16)	0.0049 (15)
O2	0.0167 (15)	0.0199 (15)	0.0190 (17)	0.0033 (12)	−0.0052 (13)	−0.0022 (13)
O3	0.0175 (16)	0.0315 (18)	0.0207 (18)	−0.0097 (13)	−0.0023 (13)	0.0039 (14)
O4	0.0200 (15)	0.0180 (15)	0.0131 (16)	−0.0055 (12)	0.0002 (12)	0.0008 (12)
O5	0.0240 (16)	0.0159 (15)	0.0239 (18)	−0.0040 (12)	0.0013 (14)	−0.0006 (13)
O6	0.0206 (16)	0.0198 (16)	0.0252 (18)	−0.0003 (12)	0.0048 (13)	−0.0019 (13)
N1	0.0150 (18)	0.029 (2)	0.016 (2)	−0.0078 (15)	0.0018 (15)	0.0025 (16)
N2	0.0203 (19)	0.0214 (18)	0.0130 (19)	−0.0036 (15)	0.0017 (15)	−0.0006 (15)
C1	0.0136 (19)	0.0106 (18)	0.013 (2)	−0.0035 (15)	0.0002 (16)	0.0017 (16)
C2	0.0128 (19)	0.0126 (19)	0.013 (2)	−0.0012 (15)	−0.0005 (16)	−0.0008 (16)
C3	0.014 (2)	0.022 (2)	0.018 (2)	−0.0019 (17)	−0.0023 (17)	−0.0015 (18)
C4	0.013 (2)	0.019 (2)	0.015 (2)	−0.0007 (16)	0.0010 (17)	−0.0014 (17)
C5	0.015 (2)	0.0135 (19)	0.012 (2)	−0.0001 (15)	0.0013 (16)	−0.0017 (16)
C6	0.0109 (19)	0.0138 (19)	0.017 (2)	−0.0015 (15)	0.0002 (16)	−0.0017 (17)
C7	0.0126 (19)	0.0108 (18)	0.013 (2)	−0.0006 (15)	0.0012 (16)	−0.0015 (16)
C8	0.015 (2)	0.0105 (18)	0.010 (2)	−0.0011 (15)	−0.0008 (16)	−0.0011 (15)
C9	0.022 (2)	0.025 (2)	0.010 (2)	−0.0049 (18)	0.0024 (17)	0.0032 (18)
C10	0.037 (2)	0.0221 (19)	0.031 (2)	0.0040 (18)	0.0026 (19)	−0.0054 (17)
C11	0.037 (2)	0.0221 (19)	0.031 (2)	0.0040 (18)	0.0026 (19)	−0.0054 (17)
C11'	0.037 (2)	0.0221 (19)	0.031 (2)	0.0040 (18)	0.0026 (19)	−0.0054 (17)

Pr1—O1	2.373 (3)	N2—C9	1.310 (6)
Pr1—O6	2.498 (3)	N2—C5	1.386 (6)
Pr1—O2i	2.501 (3)	N2—Pr1iv	2.603 (4)
Pr1—O4	2.511 (3)	C1—C2	1.512 (6)
Pr1—O3ii	2.528 (3)	C2—C3	1.389 (6)
Pr1—O1W	2.541 (3)	C2—C7	1.429 (6)
Pr1—N2iii	2.603 (4)	C3—C4	1.389 (6)
Pr1—O5	2.606 (3)	C3—H3	0.9300
Pr1—O4ii	2.646 (3)	C4—C5	1.399 (6)
Pr1—C8ii	2.963 (4)	C5—C6	1.394 (6)
O1—C1	1.261 (5)	C6—C7	1.393 (6)
O1W—H1W	0.833 (19)	C6—H6	0.9300
O1W—H2W	0.836 (19)	C7—C8	1.499 (6)
O2—C1	1.253 (5)	C8—Pr1ii	2.963 (4)
O2—Pr1i	2.501 (3)	C9—H9	0.9300
O3—C8	1.250 (5)	C10—C11	1.503 (8)
O3—Pr1ii	2.528 (3)	C10—C11'	1.55 (2)
O4—C8	1.278 (5)	C11—H11A	0.9600
O4—Pr1ii	2.646 (3)	C11—H11B	0.9600
O5—C10	1.253 (6)	C11—H11C	0.9600
O6—C10	1.267 (6)	C11'—H11D	0.9600
N1—C9	1.342 (6)	C11'—H11E	0.9600
N1—C4	1.372 (6)	C11'—H11F	0.9600
N1—H1	0.85 (2)
O1—Pr1—O6	125.76 (10)	C10—O6—Pr1	96.4 (3)
O1—Pr1—O2i	79.97 (10)	C9—N1—C4	107.0 (4)
O6—Pr1—O2i	135.37 (10)	C9—N1—H1	125 (4)
O1—Pr1—O4	69.81 (9)	C4—N1—H1	128 (4)
O6—Pr1—O4	147.25 (10)	C9—N2—C5	104.1 (4)
O2i—Pr1—O4	70.88 (10)	C9—N2—Pr1iv	122.6 (3)
O1—Pr1—O3ii	152.91 (11)	C5—N2—Pr1iv	133.1 (3)
O6—Pr1—O3ii	72.06 (11)	O2—C1—O1	123.2 (4)
O2i—Pr1—O3ii	73.82 (11)	O2—C1—C2	117.7 (4)
O4—Pr1—O3ii	106.94 (10)	O1—C1—C2	118.8 (3)
O1—Pr1—O1W	96.60 (11)	C3—C2—C7	120.7 (4)
O6—Pr1—O1W	74.37 (12)	C3—C2—C1	113.5 (4)
O2i—Pr1—O1W	145.00 (11)	C7—C2—C1	125.7 (4)
O4—Pr1—O1W	75.25 (11)	C2—C3—C4	118.0 (4)
O3ii—Pr1—O1W	108.74 (11)	C2—C3—H3	121.0
O1—Pr1—N2iii	84.24 (11)	C4—C3—H3	121.0
O6—Pr1—N2iii	71.46 (11)	N1—C4—C3	132.5 (4)
O2i—Pr1—N2iii	76.78 (11)	N1—C4—C5	104.9 (4)
O4—Pr1—N2iii	141.25 (11)	C3—C4—C5	122.5 (4)
O3ii—Pr1—N2iii	83.25 (11)	N2—C5—C6	130.8 (4)
O1W—Pr1—N2iii	137.92 (11)	N2—C5—C4	109.9 (4)
O1—Pr1—O5	75.84 (10)	C6—C5—C4	119.3 (4)
O6—Pr1—O5	50.87 (10)	C7—C6—C5	119.8 (4)
O2i—Pr1—O5	141.76 (10)	C7—C6—H6	120.1
O4—Pr1—O5	125.30 (10)	C5—C6—H6	120.1
O3ii—Pr1—O5	122.16 (11)	C6—C7—C2	119.7 (4)
O1W—Pr1—O5	67.81 (10)	C6—C7—C8	115.3 (3)
N2iii—Pr1—O5	71.75 (11)	C2—C7—C8	124.8 (4)
O1—Pr1—O4ii	139.88 (10)	O3—C8—O4	119.5 (4)
O6—Pr1—O4ii	86.63 (10)	O3—C8—C7	118.6 (4)
O2i—Pr1—O4ii	92.78 (10)	O4—C8—C7	121.9 (3)
O4—Pr1—O4ii	70.53 (11)	O3—C8—Pr1ii	57.8 (2)
O3ii—Pr1—O4ii	49.85 (9)	O4—C8—Pr1ii	63.2 (2)
O1W—Pr1—O4ii	67.41 (10)	C7—C8—Pr1ii	165.0 (3)
N2iii—Pr1—O4ii	132.75 (10)	N2—C9—N1	114.0 (4)
O5—Pr1—O4ii	124.59 (9)	N2—C9—H9	123.0
O1—Pr1—C8ii	159.06 (10)	N1—C9—H9	123.0
O6—Pr1—C8ii	75.06 (10)	O5—C10—O6	121.2 (4)
O2i—Pr1—C8ii	85.58 (10)	O5—C10—C11	121.3 (5)
O4—Pr1—C8ii	91.20 (10)	O6—C10—C11	117.1 (5)
O3ii—Pr1—C8ii	24.71 (10)	O5—C10—C11'	115.5 (10)
O1W—Pr1—C8ii	86.57 (11)	O6—C10—C11'	119.2 (10)
N2iii—Pr1—C8ii	107.21 (11)	C10—C11—H11A	109.5
O5—Pr1—C8ii	124.02 (10)	C10—C11—H11B	109.5
O4ii—Pr1—C8ii	25.55 (10)	H11A—C11—H11B	109.5
C1—O1—Pr1	131.7 (3)	C10—C11—H11C	109.5
Pr1—O1W—H1W	124 (3)	H11A—C11—H11C	109.5
Pr1—O1W—H2W	127 (3)	H11B—C11—H11C	109.5
H1W—O1W—H2W	108 (3)	C10—C11'—H11D	109.5
C1—O2—Pr1i	148.2 (3)	C10—C11'—H11E	109.5
C8—O3—Pr1ii	97.5 (2)	H11D—C11'—H11E	109.5
C8—O4—Pr1	137.6 (3)	C10—C11'—H11F	109.5
C8—O4—Pr1ii	91.2 (2)	H11D—C11'—H11F	109.5
Pr1—O4—Pr1ii	109.47 (11)	H11E—C11'—H11F	109.5
C10—O5—Pr1	91.6 (3)
O6—Pr1—O1—C1	−171.8 (3)	O2—C1—C2—C3	49.4 (5)
O2i—Pr1—O1—C1	−32.1 (3)	O1—C1—C2—C3	−124.8 (4)
O4—Pr1—O1—C1	41.1 (3)	O2—C1—C2—C7	−134.6 (4)
O3ii—Pr1—O1—C1	−46.8 (5)	O1—C1—C2—C7	51.3 (6)
O1W—Pr1—O1—C1	112.7 (4)	C7—C2—C3—C4	−1.4 (6)
N2iii—Pr1—O1—C1	−109.6 (4)	C1—C2—C3—C4	174.8 (4)
O5—Pr1—O1—C1	177.8 (4)	C9—N1—C4—C3	−176.2 (5)
O4ii—Pr1—O1—C1	50.3 (4)	C9—N1—C4—C5	1.1 (5)
C8ii—Pr1—O1—C1	15.0 (5)	C2—C3—C4—N1	179.5 (4)
O1—Pr1—O4—C8	58.8 (4)	C2—C3—C4—C5	2.5 (6)
O6—Pr1—O4—C8	−66.6 (4)	C9—N2—C5—C6	178.5 (4)
O2i—Pr1—O4—C8	144.9 (4)	Pr1iv—N2—C5—C6	3.1 (7)
O3ii—Pr1—O4—C8	−149.6 (4)	C9—N2—C5—C4	0.0 (5)
O1W—Pr1—O4—C8	−44.1 (4)	Pr1iv—N2—C5—C4	−175.3 (3)
N2iii—Pr1—O4—C8	109.9 (4)	N1—C4—C5—N2	−0.7 (5)
O5—Pr1—O4—C8	4.3 (4)	C3—C4—C5—N2	177.0 (4)
O4ii—Pr1—O4—C8	−114.9 (4)	N1—C4—C5—C6	−179.3 (4)
C8ii—Pr1—O4—C8	−130.2 (3)	C3—C4—C5—C6	−1.7 (6)
O1—Pr1—O4—Pr1ii	173.75 (13)	N2—C5—C6—C7	−178.6 (4)
O6—Pr1—O4—Pr1ii	48.4 (2)	C4—C5—C6—C7	−0.3 (6)
O2i—Pr1—O4—Pr1ii	−100.20 (12)	C5—C6—C7—C2	1.3 (6)
O3ii—Pr1—O4—Pr1ii	−34.66 (13)	C5—C6—C7—C8	177.3 (4)
O1W—Pr1—O4—Pr1ii	70.84 (12)	C3—C2—C7—C6	−0.4 (6)
N2iii—Pr1—O4—Pr1ii	−135.22 (14)	C1—C2—C7—C6	−176.2 (4)
O5—Pr1—O4—Pr1ii	119.17 (11)	C3—C2—C7—C8	−176.0 (4)
O4ii—Pr1—O4—Pr1ii	0.0	C1—C2—C7—C8	8.2 (6)
C8ii—Pr1—O4—Pr1ii	−15.29 (12)	Pr1ii—O3—C8—O4	14.5 (4)
O1—Pr1—O5—C10	169.4 (3)	Pr1ii—O3—C8—C7	−163.1 (3)
O6—Pr1—O5—C10	0.2 (3)	Pr1—O4—C8—O3	107.5 (4)
O2i—Pr1—O5—C10	117.0 (3)	Pr1ii—O4—C8—O3	−13.7 (4)
O4—Pr1—O5—C10	−138.6 (3)	Pr1—O4—C8—C7	−75.0 (5)
O3ii—Pr1—O5—C10	11.5 (3)	Pr1ii—O4—C8—C7	163.8 (3)
O1W—Pr1—O5—C10	−87.3 (3)	Pr1—O4—C8—Pr1ii	121.2 (3)
N2iii—Pr1—O5—C10	80.8 (3)	C6—C7—C8—O3	7.4 (5)
O4ii—Pr1—O5—C10	−49.0 (3)	C2—C7—C8—O3	−176.9 (4)
C8ii—Pr1—O5—C10	−18.0 (3)	C6—C7—C8—O4	−170.1 (4)
O1—Pr1—O6—C10	−13.2 (3)	C2—C7—C8—O4	5.6 (6)
O2i—Pr1—O6—C10	−128.3 (3)	C6—C7—C8—Pr1ii	−64.3 (11)
O4—Pr1—O6—C10	96.2 (3)	C2—C7—C8—Pr1ii	111.4 (10)
O3ii—Pr1—O6—C10	−170.2 (3)	C5—N2—C9—N1	0.7 (5)
O1W—Pr1—O6—C10	73.6 (3)	Pr1iv—N2—C9—N1	176.7 (3)
N2iii—Pr1—O6—C10	−81.4 (3)	C4—N1—C9—N2	−1.2 (5)
O5—Pr1—O6—C10	−0.2 (3)	Pr1—O5—C10—O6	−0.4 (5)
O4ii—Pr1—O6—C10	141.1 (3)	Pr1—O5—C10—C11	171.3 (5)
C8ii—Pr1—O6—C10	164.2 (3)	Pr1—O5—C10—C11'	−157.3 (10)
Pr1i—O2—C1—O1	−128.3 (5)	Pr1—O6—C10—O5	0.4 (5)
Pr1i—O2—C1—C2	57.8 (7)	Pr1—O6—C10—C11	−171.7 (5)
Pr1—O1—C1—O2	88.8 (5)	Pr1—O6—C10—C11'	156.5 (11)
Pr1—O1—C1—C2	−97.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6v	0.85 (2)	1.90 (3)	2.712 (5)	159 (5)
O1W—H1W···O2vi	0.83 (2)	2.06 (3)	2.854 (4)	159 (6)
O1W—H2W···O5vii	0.84 (2)	1.96 (2)	2.794 (4)	176 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6i	0.85 (2)	1.90 (3)	2.712 (5)	159 (5)
O1W—H1W⋯O2ii	0.83 (2)	2.06 (3)	2.854 (4)	159 (6)
O1W—H2W⋯O5iii	0.84 (2)	1.96 (2)	2.794 (4)	176 (5)

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