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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041657/bx2104sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041657/bx2104Isup2.hkl
Contains datablock I

CCDC reference: 1140996

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.038
  • wR factor = 0.122
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.97 Deg. PLAT417_ALERT_2_B Short Inter D-H..H-D H2 .. H5W .. 1.90 Ang. PLAT420_ALERT_2_B D-H Without Acceptor O10 - H4W ... ? PLAT420_ALERT_2_B D-H Without Acceptor O11 - H5W ... ?
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.84 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.87 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.81 Ratio PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9 PLAT417_ALERT_2_C Short Inter D-H..H-D H4W .. H12W .. 2.12 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3W .. O12 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4W .. O11 .. 2.68 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for O10 .. O11 .. 90.00 Deg. PLAT756_ALERT_4_C H...A Calc 1.70000, Rep 1.700(10) ...... Senseless su H2 -O11 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.837 Tmax scaled 0.355 Tmin scaled 0.296 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Ho1 (3) 1.88 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 18
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

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.

Structure description 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).

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).

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)]-\m-pyridine-2,6-dicarboxylato] tetrahydrate] top
Crystal data top
[Ho(C7H3NO4)(C7H4NO4)(H2O)2]·4H2OF(000) = 1184
Mr = 604.24Dx = 1.979 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3546 reflections
a = 14.1227 (5) Åθ = 2.3–25.0°
b = 11.2565 (4) ŵ = 3.98 mm1
c = 13.0342 (5) ÅT = 293 K
β = 101.892 (1)°Block, 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)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1616
Tmin = 0.354, Tmax = 0.424k = 1313
7113 measured reflectionsl = 715
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.098P)2 + 5.4784P]
where P = (Fo2 + 2Fc2)/3
3546 reflections(Δ/σ)max < 0.001
317 parametersΔρmax = 1.28 e Å3
18 restraintsΔρmin = 1.07 e Å3
Crystal data top
[Ho(C7H3NO4)(C7H4NO4)(H2O)2]·4H2OV = 2027.60 (13) Å3
Mr = 604.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.1227 (5) ŵ = 3.98 mm1
b = 11.2565 (4) ÅT = 293 K
c = 13.0342 (5) Å0.33 × 0.30 × 0.26 mm
β = 101.892 (1)°
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)] = 0.03818 restraints
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 1.28 e Å3
3546 reflectionsΔρmin = 1.07 e Å3
317 parameters
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, º) 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, z1/2.
Hydrogen-bond geometry (Å, º) 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···O9i0.82 (1)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+1/2, z+1/2; (ii) x, y+1/2, z1/2; (iii) x, y+1, z+1; (iv) x, y+1, z; (v) x, y1/2, z+3/2; (vi) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Ho(C7H3NO4)(C7H4NO4)(H2O)2]·4H2O
Mr604.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.1227 (5), 11.2565 (4), 13.0342 (5)
β (°) 101.892 (1)
V3)2027.60 (13)
Z4
Radiation typeMo Kα
µ (mm1)3.98
Crystal size (mm)0.33 × 0.30 × 0.26
Data collection
DiffractometerBruker APEX II CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.354, 0.424
No. of measured, independent and
observed [I > 2σ(I)] reflections
7113, 3546, 3213
Rint0.022
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.122, 1.00
No. of reflections3546
No. of parameters317
No. of restraints18
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.28, 1.07

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) 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 (0)1.70 (1)2.491 (9)160.22 (0)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1/2, z1/2; (iii) x, y+1, z; (iv) x, y1/2, z+3/2; (v) x+1, y+1/2, z+3/2; (vi) x, y+1/2, z+1/2.
 

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