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Acta Cryst. (2007). E63, m2438-m2439    [ doi:10.1107/S1600536807041657 ]

catena-Poly[[[diaqua(6-carboxypyridine-2-carboxylato)holmium(III)]-[mu]-pyridine-2,6-dicarboxylato] tetrahydrate]

Z. Li, S. Wang, Q. Zhang and X. Yu

Abstract top

The title compound, {[Ho(C7H3NO4)(C7H4NO4)(H2O)2]·4H2O}n, prepared by hydrothermal synthesis, is isostructural with its LaIII-, CeIII-, PrIII-, NdIII-, SmIII-, GdIII- and TbIII-containing analogues. The HoIII ion is nine-coordinated by four O and two N atoms from two independent pyridine-2,6-dicarboxylate groups, one carboxylate O atom belonging to a neighboring pyridine-2,6-dicarboxylate ligand and two water molecules. The bridging pyridine-2,6-dicarboxylate ligand gives rise to infinite chains. The crystal structure contains O-H...O hydrogen bonds, which connect the chains into a three-dimensional network.

Comment top

Complexes containing carboxyl acids have been the interest of chemists these years due to their potential applications, such as catalysis, optics, information storage, medicine, molecular electrochemistry, biochemistry and biological pharmaceutics (Li et al. (1993); Gao et al. (2004); Go et al. (2004)) Thus far, N-containing aromatic carboxyl acid has been widely used in dye intermediate, organic synthesis, sensitization material, functional pigment, adipiodone and acetrizoic acid (An et al. (2000). Pyridine carboxylic acid is also a good ligand in coordination chemistry due to its strong coordination ability and versatile coordination modes, so much attention has been paid to it in these decades (Baroni et al. (1996); Hundal et al. (2002)). Herein, we report the new complex, catena-Poly[[[diaqua(6-carboxypyridine-2-carboxylato)Holmium(III)]- µ-pyridine-2,6-dicarboxylato] tetrahydrate].

In the title compound, HoIII is of nona-coordination, chelated by two independent 2, 6-pyridine dicarboxylate, and further coordinated by two water molecules (Fig. 1). The unit is linked by one carboxylate oxygen of neighboring 2, 6-pyridine dicarboxylate forming infinite chains (Fig. 2). Extensive hydrogen bonding (Table 2) via hydrogen bonds between carboxylate oxygen atoms of 2,6-pyridinedicarboxylate and lattice water molecules or coordinated aqua ligands gives rise to three dimensional network (Fig. 3).

Related literature top

For related literature, see: Li et al. (1993); Gao et al. (2004); Go et al. (2004); An et al. (2000); Baroni et al. (1996); Hundal et al. (2002). Isostructural lanthanide compounds have been reported with LaIII (Guerriero et al., 1987; Ghosh & Bharadwaj, 2005), CeIII (Okabe et al., 2002; Ghosh & Bharadwaj, 2003; Rafizadeh et al., 2005; Ramezanipour et al., 2005), PrIII (Ghosh & Bharadwaj, 2003; Zhao et al., 2005), NdIII (Miao et al., 1992), SmIII (Liu et al., 2005, 2006; Rafizadeh et al., 2005; Song et al., 2005), EuIII (Brayshaw et al., 2005), GdIII (Hao & Yu, 2007a) and TbIII (Hao & Yu, 2007b).

Experimental top

A mixture of Holmium oxide (0.1 mmol, 0.38 g), pyridine-2,6-dicarboxylic acid (0.2 mmol, 0.33 g), H2O (16 ml) in a 25 ml Teflon-lined stainless steel autoclave was kept at 473 K for three days. Colorless crystals were obtained after cooling to room temperature with a yield of 6%. Anal. Calc. for C14H19HoN2O14: C 28.43, H 3.21, N 4.74%; Found: C 28.38, H 3.23, N 4.71%.

Refinement top

The H atoms of the water molecule were located from difference density maps and were refined with distance restraints of d(H—H) = 1.38 (2) Å and d(O—H) = 0.82 (2) Å. All other H atoms were placed in calculated positions with a C—H bond distance of 0.93%A and Uiso(H) = 1.2Ueq of the respective carrier atom.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. The coordination of the Ho atom in the title structure, drawn with 30% probability displacement ellipsoids. Atoms labeled with i at the symmetry positions (x,-y + 1/2,z + 1/2).
[Figure 2] Fig. 2. Chains of the title compound along [010] direction. The balls represent holmium (green), C (gray), N (blue) and O (red)·For clarity all H atoms have been omitted.
[Figure 3] Fig. 3. A view of the packing structure of the title compound. The balls represent holmium (green), C (gray), N (blue) and O (red).
catena-Poly[[[diaqua(6-carboxypyridine-2-carboxylato)holmium(III)]-\ µ-pyridine-2,6-dicarboxylato] tetrahydrate] top
Crystal data top
[Ho(C7H3NO4)(C7H4NO4)(H2O)2]·4H2OF000 = 1184
Mr = 604.24Dx = 1.979 Mg m−3
Monoclinic, P2(1)/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3546 reflections
a = 14.1227 (5) Åθ = 2.3–25.0º
b = 11.2565 (4) ŵ = 3.98 mm−1
c = 13.0342 (5) ÅT = 293 (2) K
β = 101.8920 (10)ºBlock, colorless
V = 2027.60 (13) Å30.33 × 0.30 × 0.26 mm
Z = 4
Data collection top
Bruker APEX II CCD area-detector
diffractometer		3546 independent reflections
Radiation source: fine-focus sealed tube3213 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
T = 293(2) Kθmax = 25.0º
φ and ω scansθmin = 2.3º
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −16→16
Tmin = 0.354, Tmax = 0.424k = −13→13
7113 measured reflectionsl = −7→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.122  w = 1/[σ2(Fo2) + (0.098P)2 + 5.4784P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3546 reflectionsΔρmax = 1.28 e Å−3
317 parametersΔρmin = −1.07 e Å−3
18 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ho(C7H3NO4)(C7H4NO4)(H2O)2]·4H2OV = 2027.60 (13) Å3
Mr = 604.24Z = 4
Monoclinic, P2(1)/cMo Kα
a = 14.1227 (5) ŵ = 3.98 mm−1
b = 11.2565 (4) ÅT = 293 (2) K
c = 13.0342 (5) Å0.33 × 0.30 × 0.26 mm
β = 101.8920 (10)º
Data collection top
Bruker APEX II CCD area-detector
diffractometer		3546 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3213 reflections with I > 2σ(I)
Tmin = 0.354, Tmax = 0.424Rint = 0.022
7113 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.122Δρmax = 1.28 e Å−3
S = 1.00Δρmin = −1.07 e Å−3
3546 reflectionsAbsolute structure: ?
317 parametersFlack parameter: ?
18 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4422 (5)0.4997 (5)0.6323 (5)0.0266 (13)
C20.4323 (4)0.0766 (5)0.6274 (5)0.0218 (12)
C30.2257 (4)0.3472 (4)0.3809 (4)0.0139 (10)
C40.1196 (4)0.5249 (5)0.6731 (4)0.0167 (11)
C50.5032 (5)0.3901 (6)0.6334 (5)0.0279 (13)
C60.6008 (5)0.3890 (8)0.6347 (7)0.0314 (8)
H60.63460.46000.63510.058*
C70.6479 (7)0.2832 (8)0.6354 (10)0.0366 (11)
H70.71440.28110.63890.076*
C80.5951 (6)0.1783 (8)0.6309 (8)0.0378 (11)
H80.62510.10500.62850.060*
C90.4969 (5)0.1852 (6)0.6301 (5)0.0245 (13)
C100.1738 (3)0.4516 (4)0.4171 (4)0.0121 (10)
C110.1380 (4)0.5471 (5)0.3507 (4)0.0174 (11)
H110.14130.54670.28010.021*
C120.0980 (4)0.6409 (5)0.3942 (4)0.0223 (12)
H120.07500.70630.35300.027*
C130.0916 (4)0.6390 (5)0.4995 (4)0.0206 (11)
H130.06480.70260.52920.025*
C140.1266 (3)0.5392 (4)0.5595 (4)0.0112 (9)
Ho10.269861 (18)0.29481 (2)0.648479 (18)0.01835 (15)
H1W0.020 (8)0.259 (4)0.338 (7)0.080*
H2W0.066 (7)0.163 (8)0.305 (5)0.080*
H3W0.216 (8)0.960 (5)0.619 (6)0.080*
H4W0.220 (9)0.900 (8)0.528 (5)0.080*
H5W0.330 (5)0.729 (8)0.608 (8)0.080*
H6W0.378 (7)0.820 (8)0.569 (6)0.080*
H7W0.135 (8)0.192 (8)0.505 (3)0.080*
H8W0.088 (6)0.131 (7)0.572 (7)0.080*
H9W0.418 (3)0.315 (9)0.852 (7)0.080*
H10W0.326 (5)0.342 (10)0.863 (6)0.080*
H11W0.025 (6)0.4863 (18)0.891 (8)0.080*
H12W0.083 (3)0.584 (7)0.926 (8)0.080*
N10.1688 (3)0.4484 (3)0.5189 (3)0.0102 (8)
N20.4520 (4)0.2880 (4)0.6325 (4)0.0196 (11)
O10.3567 (3)0.4920 (3)0.6354 (3)0.0243 (9)
O20.4875 (4)0.6000 (4)0.6264 (5)0.0454 (13)
H20.45370.65540.63840.068*
O30.4692 (3)−0.0218 (4)0.6230 (4)0.0385 (12)
O40.3442 (3)0.0968 (3)0.6298 (3)0.0215 (8)
O50.2737 (3)0.2818 (3)0.4533 (3)0.0158 (8)
O60.2188 (3)0.3335 (3)0.2838 (3)0.0182 (8)
O70.1549 (3)0.4294 (3)0.7180 (3)0.0209 (8)
O80.0792 (3)0.6042 (4)0.7147 (3)0.0291 (10)
O90.0416 (3)0.1919 (4)0.3505 (3)0.0238 (9)
O100.2016 (6)0.9006 (6)0.5839 (7)0.083 (2)
O110.3770 (6)0.7738 (6)0.6176 (8)0.086 (3)
O120.1248 (3)0.1839 (4)0.5634 (3)0.0250 (9)
O130.3662 (4)0.3461 (5)0.8260 (3)0.0356 (11)
O140.0295 (3)0.5577 (4)0.9011 (4)0.0317 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.035 (4)0.017 (3)0.026 (3)−0.008 (2)0.001 (3)0.002 (2)
C20.013 (3)0.028 (3)0.024 (3)−0.001 (2)0.001 (2)0.000 (2)
C30.016 (3)0.014 (2)0.013 (2)0.003 (2)0.0043 (19)0.000 (2)
C40.016 (3)0.018 (3)0.017 (3)0.001 (2)0.004 (2)−0.001 (2)
C50.026 (3)0.028 (3)0.030 (3)−0.013 (3)0.006 (2)0.002 (3)
C60.0177 (15)0.0427 (19)0.0322 (19)0.002 (2)−0.0009 (13)0.000 (2)
C70.026 (2)0.050 (3)0.033 (3)0.005 (2)0.0015 (19)−0.001 (2)
C80.031 (2)0.043 (2)0.038 (3)0.003 (2)0.0025 (19)0.003 (2)
C90.015 (3)0.028 (3)0.030 (3)−0.003 (2)0.002 (2)0.001 (2)
C100.013 (2)0.013 (2)0.009 (2)−0.0024 (19)0.0009 (18)−0.0014 (18)
C110.025 (3)0.017 (3)0.009 (2)0.007 (2)0.001 (2)0.0026 (19)
C120.032 (3)0.018 (3)0.014 (3)0.009 (2)−0.002 (2)0.005 (2)
C130.027 (3)0.016 (3)0.020 (3)0.007 (2)0.007 (2)0.001 (2)
C140.013 (2)0.009 (2)0.012 (2)0.0019 (18)0.0023 (18)−0.0009 (18)
Ho10.0194 (2)0.0194 (2)0.0157 (2)0.00111 (8)0.00213 (13)0.00128 (8)
N10.011 (2)0.0103 (19)0.0092 (19)0.0014 (15)0.0026 (15)0.0016 (15)
N20.016 (3)0.026 (3)0.016 (2)0.0007 (18)0.001 (2)−0.0005 (17)
O10.024 (2)0.0156 (19)0.031 (2)−0.0079 (16)0.0020 (17)0.0028 (16)
O20.047 (3)0.026 (2)0.062 (3)−0.015 (2)0.009 (3)0.004 (2)
O30.028 (2)0.019 (2)0.065 (3)0.0107 (19)0.002 (2)−0.002 (2)
O40.020 (2)0.0129 (18)0.031 (2)0.0005 (15)0.0038 (16)0.0016 (15)
O50.020 (2)0.0185 (18)0.0081 (17)0.0112 (14)0.0008 (15)0.0013 (13)
O60.026 (2)0.0183 (18)0.0084 (18)0.0066 (16)−0.0004 (15)−0.0025 (15)
O70.033 (2)0.0191 (19)0.0123 (17)0.0125 (16)0.0085 (16)0.0044 (14)
O80.049 (3)0.020 (2)0.023 (2)0.0165 (19)0.0192 (19)0.0009 (16)
O90.024 (2)0.028 (2)0.019 (2)0.0023 (16)0.0023 (18)−0.0009 (16)
O100.065 (5)0.035 (3)0.132 (7)−0.013 (3)−0.017 (5)0.001 (4)
O110.066 (5)0.035 (3)0.152 (8)−0.004 (3)0.013 (5)0.012 (4)
O120.028 (2)0.035 (2)0.0105 (19)−0.0128 (18)0.0000 (17)0.0046 (16)
O130.037 (3)0.054 (3)0.014 (2)−0.029 (2)−0.0008 (18)0.000 (2)
O140.040 (3)0.030 (2)0.030 (2)0.011 (2)0.019 (2)−0.0005 (19)
Geometric parameters (Å, °) top
C1—O11.219 (8)C13—C141.399 (7)
C1—O21.307 (8)C13—H130.9300
C1—C51.503 (9)C14—N11.345 (6)
C2—O31.231 (7)Ho1—O122.460 (4)
C2—O41.271 (7)Ho1—O42.497 (4)
C2—C91.521 (8)Ho1—O6i2.499 (4)
C3—O61.259 (6)Ho1—O132.499 (4)
C3—O51.276 (6)Ho1—O72.522 (4)
C3—C101.511 (7)Ho1—O12.559 (4)
C4—O81.241 (7)Ho1—O52.559 (4)
C4—O71.275 (6)Ho1—N22.625 (5)
C4—C141.514 (7)Ho1—N12.623 (4)
C5—N21.357 (7)O2—H20.8200
C5—C61.376 (10)O6—Ho1ii2.499 (4)
C6—C71.364 (12)O9—H1W0.82 (5)
C6—H60.9300O9—H2W0.81 (8)
C7—C81.391 (12)O10—H3W0.81 (7)
C7—H70.9300O10—H4W0.82 (9)
C8—C91.387 (10)O11—H5W0.82 (8)
C8—H80.9300O11—H6W0.82 (9)
C9—N21.323 (8)O12—H7W0.81 (6)
C10—N11.345 (6)O12—H8W0.81 (8)
C10—C111.407 (7)O13—H9W0.82 (7)
C11—C121.374 (8)O13—H10W0.82 (7)
C11—H110.9300O14—H11W0.815 (11)
C12—C131.395 (8)O14—H12W0.81 (7)
C12—H120.9300
O1—C1—O2124.3 (6)O6i—Ho1—O778.04 (12)
O1—C1—C5120.7 (5)O13—Ho1—O778.27 (16)
O2—C1—C5115.0 (6)O12—Ho1—O1140.95 (13)
O3—C2—O4126.0 (6)O4—Ho1—O1123.42 (14)
O3—C2—C9117.8 (5)O6i—Ho1—O1139.51 (13)
O4—C2—C9116.2 (5)O13—Ho1—O171.59 (14)
O6—C3—O5126.4 (5)O7—Ho1—O181.70 (13)
O6—C3—C10117.8 (4)O12—Ho1—O573.07 (13)
O5—C3—C10115.8 (4)O4—Ho1—O575.91 (12)
O8—C4—O7125.3 (5)O6i—Ho1—O5137.46 (12)
O8—C4—C14118.6 (5)O13—Ho1—O5144.57 (14)
O7—C4—C14116.1 (4)O7—Ho1—O5122.56 (11)
N2—C5—C6121.5 (7)O1—Ho1—O582.82 (13)
N2—C5—C1113.1 (5)O12—Ho1—N2133.50 (15)
C6—C5—C1125.4 (6)O4—Ho1—N261.78 (13)
C7—C6—C5119.6 (7)O6i—Ho1—N2117.99 (14)
C7—C6—H6120.2O13—Ho1—N274.01 (16)
C5—C6—H6120.2O7—Ho1—N2139.50 (14)
C6—C7—C8119.0 (8)O1—Ho1—N261.90 (13)
C6—C7—H7120.5O5—Ho1—N272.42 (14)
C8—C7—H7120.5O12—Ho1—N175.65 (13)
C9—C8—C7118.6 (8)O4—Ho1—N1135.17 (13)
C9—C8—H8120.7O6i—Ho1—N1129.61 (13)
C7—C8—H8120.7O13—Ho1—N1124.34 (16)
N2—C9—C8122.2 (6)O7—Ho1—N161.97 (11)
N2—C9—C2114.5 (5)O1—Ho1—N165.81 (13)
C8—C9—C2123.3 (6)O5—Ho1—N161.19 (11)
N1—C10—C11122.9 (4)N2—Ho1—N1112.35 (13)
N1—C10—C3114.5 (4)C14—N1—C10119.0 (4)
C11—C10—C3122.6 (4)C14—N1—Ho1118.3 (3)
C12—C11—C10117.3 (5)C10—N1—Ho1121.4 (3)
C12—C11—H11121.3C9—N2—C5119.0 (6)
C10—C11—H11121.3C9—N2—Ho1120.7 (4)
C11—C12—C13120.7 (5)C5—N2—Ho1120.2 (4)
C11—C12—H12119.6C1—O1—Ho1123.7 (4)
C13—C12—H12119.7C1—O2—H2109.5
C12—C13—C14118.4 (5)C2—O4—Ho1126.6 (4)
C12—C13—H13120.8C3—O5—Ho1125.9 (3)
C14—C13—H13120.8C3—O6—Ho1ii143.8 (3)
N1—C14—C13121.7 (4)C4—O7—Ho1124.2 (3)
N1—C14—C4115.3 (4)H1W—O9—H2W115 (9)
C13—C14—C4123.0 (4)H3W—O10—H4W115 (9)
O12—Ho1—O480.27 (15)H5W—O11—H6W114 (10)
O12—Ho1—O6i71.96 (12)Ho1—O12—H7W94 (7)
O4—Ho1—O6i75.01 (13)Ho1—O12—H8W144 (6)
O12—Ho1—O13141.17 (13)H7W—O12—H8W117 (9)
O4—Ho1—O1397.86 (16)Ho1—O13—H9W123 (8)
O6i—Ho1—O1370.18 (13)Ho1—O13—H10W103 (7)
O12—Ho1—O785.92 (15)H9W—O13—H10W114 (8)
O4—Ho1—O7152.41 (12)H11W—O14—H12W117 (8)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O9—H1W···O8iii0.82 (5)2.10 (4)2.882 (6)160 (12)
O9—H2W···O7ii0.81 (8)2.13 (9)2.924 (6)166 (9)
O10—H3W···O12iv0.81 (7)2.85 (10)3.361 (8)123 (10)
O10—H4W···O110.82 (9)2.68 (13)2.813 (11)90 (9)
O11—H6W···O3iv0.82 (9)2.23 (9)2.638 (8)111 (8)
O12—H7W···O90.81 (6)2.16 (7)2.782 (6)133 (10)
O12—H8W···O14v0.81 (8)1.95 (9)2.720 (6)158 (11)
O13—H9W···O3vi0.82 (7)2.41 (10)2.724 (6)104 (8)
O13—H10W···O5i0.82 (7)2.06 (7)2.725 (5)139 (10)
O14—H11W···O9i0.815 (11)2.10 (3)2.899 (6)168 (10)
O2—H2···O110.82 (1)1.70 (1)2.491 (9)160 (1)
Symmetry codes: (iii) −x, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iv) x, y+1, z; (v) −x, y−1/2, −z+3/2; (vi) −x+1, y+1/2, −z+3/2; (i) x, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O9—H1W···O8i0.82 (5)2.10 (4)2.882 (6)160 (12)
O9—H2W···O7ii0.81 (8)2.13 (9)2.924 (6)166 (9)
O10—H3W···O12iii0.81 (7)2.85 (10)3.361 (8)123 (10)
O10—H4W···O110.82 (9)2.68 (13)2.813 (11)90 (9)
O11—H6W···O3iii0.82 (9)2.23 (9)2.638 (8)111 (8)
O12—H7W···O90.81 (6)2.16 (7)2.782 (6)133 (10)
O12—H8W···O14iv0.81 (8)1.95 (9)2.720 (6)158 (11)
O13—H9W···O3v0.82 (7)2.41 (10)2.724 (6)104 (8)
O13—H10W···O5vi0.82 (7)2.06 (7)2.725 (5)139 (10)
O14—H11W···O9vi0.815 (11)2.10 (3)2.899 (6)168 (10)
O2—H2···O110.82 (1)1.70 (1)2.491 (9)160 (1)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) x, y+1, z; (iv) −x, y−1/2, −z+3/2; (v) −x+1, y+1/2, −z+3/2; (vi) x, −y+1/2, z+1/2.
references
References top

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