metal-organic compounds
Poly[(acetato-κ2O,O′)aqua(μ4-1H-benzimidazole-5,6-dicarboxylato-κ5N3:O5,O5′:O5,O6:O6′)praseodymium(III)]
aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
*Correspondence e-mail: xuxuan2004@yahoo.com.cn
In the title complex, [Pr(C9H4N2O4)(C2H3O2)(H2O)]n, the PrIII ion is coordinated by five O atoms and one N atom from four benzimidazole-5,6-dicarboxylate ligands, two O atoms from an acetate ligand and one water molecule, giving a tricapped trigonal-prismatic geometry. The benzimidazole-5,6-dicarboxylate and acetate ligands connect the PrIII 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 interactions between neighboring pyridine rings [the centroid–centroid distance is 3.467 (1) Å], assembling a three-dimensional supramolecular 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
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell 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.
Supporting information
10.1107/S1600536810036986/pk2264sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810036986/pk2264Isup2.hkl
A mixture of Pr6O11 (0.170 g; 0.17 mmol), benzimidazole-5,6-dicarboxylic acid (0.206 g; 1 mmol), acetic acid (0.06 g; 1 mmol), water (10 ml) was stirred vigorously for 30 min and then sealed in a teflon-lined stainless-steel autoclave (20 ml, capacity). The autoclave was heated and maintained at 423 K for 3 days, and then cooled to room temperature at 5 K h-1, which produced colorless block-shaped crystals.
Water H atoms were tentatively located in difference Fourier maps and were refined with distance restraints of O–H = 0.84 Å and H···H = 1.35 Å, and with Uiso(H) = 1.5 Ueq(O). The H atom bound to the N1 nitrogen atom was refined with distance restraints of N–H = 0.86 Å, and with Uiso(H) = 1.2 Ueq(O). All other H atoms were placed at calculated positions and treated as riding on the parent atoms, with C—H = 0.93 Å or 0.96 Å, and with Uiso(H) = 1.2 or 1.5 Ueq(C).
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).[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 monochromator | 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) |
[Pr(C9H4N2O4)(C2H3O2)(H2O)] | γ = 84.274 (1)° |
Mr = 422.11 | V = 645.77 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4284 (5) Å | Mo Kα radiation |
b = 9.0109 (7) Å | µ = 3.81 mm−1 |
c = 9.7239 (7) Å | T = 296 K |
α = 87.075 (1)° | 0.26 × 0.22 × 0.19 mm |
β = 86.498 (1)° |
Bruker SMART APEX CCD diffractometer | 2327 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2184 reflections with I > 2σ(I) |
Tmin = 0.386, Tmax = 0.485 | Rint = 0.028 |
3963 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 22 restraints |
wR(F2) = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 1.23 e Å−3 |
2327 reflections | Δρmin = −1.45 e Å−3 |
199 parameters |
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) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z; (iii) x, y, z−1; (iv) x, y, z+1. |
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) |
Symmetry codes: (v) x−1, y, z+1; (vi) x+1, y, z; (vii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Pr(C9H4N2O4)(C2H3O2)(H2O)] |
Mr | 422.11 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.4284 (5), 9.0109 (7), 9.7239 (7) |
α, β, γ (°) | 87.075 (1), 86.498 (1), 84.274 (1) |
V (Å3) | 645.77 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 3.81 |
Crystal size (mm) | 0.26 × 0.22 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.386, 0.485 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3963, 2327, 2184 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.072, 1.04 |
No. of reflections | 2327 |
No. of parameters | 199 |
No. of restraints | 22 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.23, −1.45 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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 | 0.833 (19) | 2.06 (3) | 2.854 (4) | 159 (6) |
O1W—H2W···O5iii | 0.836 (19) | 1.959 (19) | 2.794 (4) | 176 (5) |
Symmetry codes: (i) x−1, y, z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z. |
Acknowledgements
The authors acknowledge the Natural Science Foundation of Guangdong Province (No. 9151063101000037) for supporting this work.
References
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In recent years, studies of coordination polymers built using metals and multifunctional organic ligands, has been a rapidly expanding field. This has been due to their intriguing structural motifs and functional properties, such as molecular adsorption, magnetism, and luminescence. Benzimidazole-5,6-dicarboxylic acid (H2L) is such a multifuctional ligand with both nitrogen and oxygen donor atoms (Gao et al., 2008; Lo et al., 2007; Wang et al., 2009; Wei et al., 2008; Yao et al., 2008; Zhai et al., 2009). For example, Yao and co-workers have successfully synthesized six novel two-dimensional coordination polymers based on this ligand, namely, [MnL]n (1), {[Ni2L2(H2O)4].(H2O)3}n (2), {[Tb(L)(HL)(H2O)].(H2O)}n (3) and {[Ln2L2(HL)2(H2O)2]}n (Ln=Ho (4), Er (5), Lu (6)) (Yao et al., 2008). Wei et al. also obtained a novel five coordinated Mn(II) polymer ([Mn(HL)])n possessing abundant hydrogen bonds and π-π stacking interactions (Wei et al., 2008). Herein, we report the hydrothermal synthesis, structure of the novel coordination polymer.
In the structure of the title compound (Fig. 1), each PrIII centre is nine-coordinated by five oxygen atoms and one N atom from four benzimidazole-5,6-dicarboxylato ligands, two oxygen atoms from an acetate ligand, and one water molecule. The structure can described as having a bicapped trigonal prismatic geometry with Pr···O distances and O···Pr···O angles ranging from 2.373 (3) Å to 2.645 (3) Å and 69.84 (9) ° to 152.88 (1) °, respectively. The benzimidazole-5,6-dicarboxylate and acetate ligands, act as bridging ligands, linking the PrIII metal centres into a layer parallel to the ac plane (Fig. 2). Those layers are further connected via O—H···O and N—H···O hydrogen bonding interactions (Table 1) to form a three-dimensional supramolecular motif, which is stabilized by π-π stacking interactions between neighboring pyridyl rings (the centroid···centroid distance is 3.467 (1) Å).