catena-Poly[[[tetra­aqua­neodymium(III)]-di-μ-isonicotinato] chloride]

Xue, J.-H.; Hua, X.-H.; Li, C.-P.; Xu, Y.-Z.; Wu, J.-G.

doi:10.1107/S1600536811055619

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m170-m171

doi:10.1107/S1600536811055619

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catena-Poly[[[tetraaquaneodymium(III)]-di-μ-isonicotinato] chloride]

Jun-Hui Xue,^a Xiao-Hui Hua,^b Chun-Ping Li,^a ^* Yi-Zhuang Xu ^b and Jin-Guang Wu ^b

^aChemical Engineering College, Inner Mongolia University of Technology, People's Republic of China, and ^bThe State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, People's Republic of China
^*Correspondence e-mail: cp_li@yahoo.cn

(Received 24 October 2011; accepted 25 December 2011; online 18 January 2012)

In the title complex, {[Nd(C₆H₄NO₂)₂(H₂O)₄]Cl}_n, the Nd^III cation is located on a twofold rotation axis and coordinated by four isonicotiniate anions and four water molecules in a distorted square-antiprismatic geometry. The carboxylate groups of the isonicotinate anions bridge the Nd^III cations, forming polymeric chains running along the c axis. The Cl⁻ anion is located on a twofold rotation axis and is linked to the polymeric chains via O—H⋯Cl hydrogen bonding. Intermolecular O—H⋯O and O—H⋯N hydrogen bonds are also present in the crystal structure.

Related literature

For some crystal structures of related lanthanide-isonicotinic acid complexes, see: Chen & Fukuzumi (2009 ); Ma et al. (1999 ); Han et al. (2010 ); Kay et al. (1972 ); Duan et al. (2010 ); Jia et al. (2008 ); Cheng et al. (2007 ); Liu et al. (2006 ); Chai et al. (2010 ).

Experimental

Crystal data

[Nd(C₆H₄NO₂)₂(H₂O)₄]Cl
M_r = 495.96
Orthorhombic, P b c n
a = 8.9223 (18) Å
b = 19.684 (4) Å
c = 10.151 (2) Å
V = 1782.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 3.10 mm⁻¹
T = 173 K
0.18 × 0.17 × 0.15 mm

Data collection

Rigaku Saturn724+ CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.49, T_max = 0.63
9085 measured reflections
2056 independent reflections
1764 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.190
S = 1.33
2056 reflections
122 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.12 e Å⁻³
Δρ_min = −1.06 e Å⁻³

Table 1
Selected bond lengths (Å)

Nd1—O1ⁱ	2.425 (6)
Nd1—O2	2.385 (5)
Nd1—O3	2.544 (6)
Nd1—O4	2.480 (6)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H6⋯Cl2ⁱⁱ	0.95 (6)	2.29 (6)	3.211 (7)	163 (6)
O3—H7⋯N1ⁱⁱⁱ	0.97 (4)	1.72 (4)	2.685 (10)	174 (9)
O4—H8⋯Cl2ⁱ	0.96 (4)	2.15 (5)	3.041 (6)	155 (6)
O4—H9⋯O3^iv	0.95 (2)	1.93 (3)	2.841 (8)	160 (8)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055619/xu5361sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055619/xu5361Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536811055619/xu5361Isup5.cdx

checkCIF report

Comment top

In the synthesis of prepare a lanthanide-isonicotinamide complex, the isonicotinamide changed to isonicotinic acid, resulting in the title complex.

Among aromatic carboxylic acids, isonicotinic acid has a conjugated structural motif and can be used to construct extended structures because it is unsymmetrical divergent ligand. Isonicotinic acid with metal ions may have various coordination modes (Chen et al., 2009). The molecular structure of the title compound is shown in Fig. 1. Nd(III) is 8-coordinated to four oxygen atoms from four isonicotinic acid molecules and four water molecules. Each ligand is coordinated to two metal ions as bidentate ligands via two oxygen atoms of carboxyl group. One metal ion is connected to four ligands, thus an extensive network form. Nd(III) is located at the center of a slightly distorted square antiprism. Nd-O distances are from 2.385 to 2.544 Å. The mean Nd-O bond lengths, 2.4585 Å is larger than the mean Sm-O bond lengths (2.426 Å), which is consistent with the lanthanide contraction. The O—H···Cl, O—H···O and O—H···N hydrogen bonds form a three-dimensional network.

For lanthanide-isonicotinate complexes, several structures have been observed. For example, Ln(III) ions can coordinate to six carboxylate oxygen atoms of bridging isonicotinate groups and to two water molecules (Ma et al., 1999); or may coordinate to four carboxylate oxygen atoms of bridging isonicotinate groups, two carboxylate oxygen atoms of the chelating isonicotinate group, and two water molecules (Ma et al., 1999; Han et al., 2010; Kay et al., 1972); or have structure similar to the NdCl-isonicotinic acid complex reported here (Chen et al., 2009). Because Cl^- or NO₃^- does not coordinate to lanthanide ions, so Nd(III) chloride or nitrate ion-isonicotinic acid complexes have the similar coordination sphere (Duan et al., 2010; Jia et al., 2008). When oxalate ligands, chromate ions or other ligands are involved, the coordination situations are a little different (Cheng et al., 2007; Liu et al., 2006; Chai et al., 2010) because oxalate ligand, chromate ions or other ligands also coordinate to metal ions.

Related literature top

For some crystal structures of related lanthanide-isonicotinic acid complexes, see: Chen et al. (2009); Ma et al. (1999); Han et al. (2010); Kay et al. (1972); Duan et al. (2010); Jia et al. (2008); Cheng et al. (2007); Liu et al. (2006); Chai et al. (2010).

Experimental top

NdCl₃ (1 mmol) and isonicotinamide (3 mmol) were dissolved in 3ml water and 6 ml ethanol. The solution was put on a water bath, temperature was raised to 80°C. Small aliquots of EtOH were periodically added to the solution during the heating process to prolong the reaction time. The resulting mixtures were filtered and left for crystallization in room temperature, the suitable crystals for X-ray diffraction measuraments were obtained in two weeks.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, displacement ellipsoids drawn at 30% probability level. The Hydrogen atoms have been omitted for clarity.

catena-Poly[[[tetraaquaneodymium(III)]-di-µ-isonicotinato] chloride] top

Crystal data top

[Nd(C₆H₄NO₂)₂(H₂O)₄]Cl	F(000) = 972
M_r = 495.96	D_x = 1.848 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4581 reflections
a = 8.9223 (18) Å	θ = 2.0–27.5°
b = 19.684 (4) Å	µ = 3.10 mm⁻¹
c = 10.151 (2) Å	T = 173 K
V = 1782.9 (6) Å³	Block, blue
Z = 4	0.18 × 0.17 × 0.15 mm

Data collection top

Rigaku Saturn724+ CCD diffractometer	2056 independent reflections
Radiation source: fine-focus sealed tube	1764 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
ω scans at fixed χ = 45°	h = −11→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −25→23
T_min = 0.49, T_max = 0.63	l = −12→13
9085 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.33	w = 1/[σ²(F_o²) + (0.0763P)² + 8.5206P] where P = (F_o² + 2F_c²)/3
2056 reflections	(Δ/σ)_max = 0.004
122 parameters	Δρ_max = 1.12 e Å⁻³
6 restraints	Δρ_min = −1.06 e Å⁻³

Crystal data top

[Nd(C₆H₄NO₂)₂(H₂O)₄]Cl	V = 1782.9 (6) Å³
M_r = 495.96	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 8.9223 (18) Å	µ = 3.10 mm⁻¹
b = 19.684 (4) Å	T = 173 K
c = 10.151 (2) Å	0.18 × 0.17 × 0.15 mm

Data collection top

Rigaku Saturn724+ CCD diffractometer	2056 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	1764 reflections with I > 2σ(I)
T_min = 0.49, T_max = 0.63	R_int = 0.071
9085 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	6 restraints
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.33	Δρ_max = 1.12 e Å⁻³
2056 reflections	Δρ_min = −1.06 e Å⁻³
122 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Nd1	0.5000	0.51140 (3)	0.2500	0.0166 (3)
Cl2	0.0000	0.55946 (19)	0.7500	0.0334 (8)
O4	0.6995 (7)	0.4591 (3)	0.1133 (5)	0.0263 (13)
H8	0.802 (4)	0.448 (5)	0.131 (7)	0.032*
H9	0.694 (9)	0.459 (5)	0.020 (2)	0.032*
O1	0.5450 (7)	0.3957 (3)	0.5981 (6)	0.0250 (13)
O2	0.6051 (7)	0.4301 (3)	0.3977 (5)	0.0225 (12)
O3	0.2471 (7)	0.5501 (3)	0.1620 (6)	0.0242 (13)
H6	0.163 (6)	0.526 (3)	0.195 (10)	0.029*
H7	0.211 (8)	0.5964 (15)	0.157 (9)	0.029*
C6	0.5817 (8)	0.3855 (4)	0.4827 (8)	0.0164 (15)
C3	0.6021 (10)	0.3129 (4)	0.4415 (8)	0.0217 (17)
C2	0.6744 (10)	0.2956 (4)	0.3247 (8)	0.0261 (19)
H2	0.7100	0.3295	0.2691	0.031*
C4	0.5480 (12)	0.2591 (4)	0.5189 (10)	0.030 (2)
H4	0.4971	0.2678	0.5970	0.035*
N1	0.6459 (9)	0.1776 (4)	0.3683 (7)	0.0286 (17)
C5	0.5713 (12)	0.1933 (4)	0.4775 (9)	0.030 (2)
H5	0.5329	0.1581	0.5285	0.036*
C1	0.6936 (11)	0.2279 (4)	0.2911 (10)	0.030 (2)
H1	0.7412	0.2173	0.2123	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Nd1	0.0210 (4)	0.0139 (4)	0.0148 (4)	0.000	−0.0010 (2)	0.000
Cl2	0.0240 (15)	0.0327 (18)	0.043 (2)	0.000	−0.0092 (13)	0.000
O4	0.025 (3)	0.040 (4)	0.014 (3)	0.008 (3)	0.001 (2)	−0.002 (3)
O1	0.034 (3)	0.019 (3)	0.022 (3)	−0.002 (3)	0.007 (3)	−0.005 (2)
O2	0.025 (3)	0.016 (3)	0.026 (3)	−0.001 (2)	−0.006 (3)	0.007 (2)
O3	0.022 (3)	0.015 (3)	0.035 (3)	0.005 (2)	0.005 (3)	0.005 (2)
C6	0.006 (4)	0.018 (4)	0.025 (4)	0.000 (3)	−0.008 (3)	0.000 (3)
C3	0.023 (4)	0.022 (4)	0.021 (4)	0.000 (3)	0.002 (3)	0.001 (3)
C2	0.026 (5)	0.026 (4)	0.027 (4)	−0.003 (4)	0.006 (4)	0.002 (4)
C4	0.037 (5)	0.020 (4)	0.032 (5)	−0.005 (4)	0.003 (4)	0.002 (4)
N1	0.040 (4)	0.021 (4)	0.025 (4)	0.002 (3)	−0.009 (3)	−0.009 (3)
C5	0.040 (6)	0.015 (4)	0.035 (5)	0.000 (4)	0.006 (4)	0.004 (3)
C1	0.035 (5)	0.023 (5)	0.031 (5)	0.005 (4)	−0.003 (4)	−0.008 (4)

Geometric parameters (Å, º) top

Nd1—O1ⁱ	2.425 (6)	O3—H6	0.95 (2)
Nd1—O1ⁱⁱ	2.425 (6)	O3—H7	0.97 (2)
Nd1—O2ⁱⁱⁱ	2.385 (5)	C6—C3	1.501 (10)
Nd1—O2	2.385 (5)	C3—C2	1.392 (11)
Nd1—O3ⁱⁱⁱ	2.544 (6)	C3—C4	1.404 (12)
Nd1—O3	2.544 (6)	C2—C1	1.385 (12)
Nd1—O4ⁱⁱⁱ	2.480 (6)	C2—H2	0.9300
Nd1—O4	2.480 (6)	C4—C5	1.377 (12)
O4—H8	0.96 (2)	C4—H4	0.9300
O4—H9	0.95 (2)	N1—C5	1.330 (12)
O1—C6	1.234 (9)	N1—C1	1.332 (12)
O1—Nd1ⁱ	2.425 (6)	C5—H5	0.9300
O2—C6	1.248 (9)	C1—H1	0.9300

O2ⁱⁱⁱ—Nd1—O2	95.7 (3)	Nd1—O4—H8	132 (5)
O2ⁱⁱⁱ—Nd1—O1ⁱ	147.2 (2)	Nd1—O4—H9	121 (5)
O2—Nd1—O1ⁱ	99.8 (2)	H8—O4—H9	104 (3)
O2ⁱⁱⁱ—Nd1—O1ⁱⁱ	99.8 (2)	C6—O1—Nd1ⁱ	140.4 (5)
O2—Nd1—O1ⁱⁱ	147.2 (2)	C6—O2—Nd1	147.2 (5)
O1ⁱ—Nd1—O1ⁱⁱ	82.1 (3)	Nd1—O3—H6	115 (5)
O2ⁱⁱⁱ—Nd1—O4ⁱⁱⁱ	78.0 (2)	Nd1—O3—H7	127 (5)
O2—Nd1—O4ⁱⁱⁱ	69.63 (19)	H6—O3—H7	103 (3)
O1ⁱ—Nd1—O4ⁱⁱⁱ	80.7 (2)	O1—C6—O2	125.9 (7)
O1ⁱⁱ—Nd1—O4ⁱⁱⁱ	141.9 (2)	O1—C6—C3	116.9 (7)
O2ⁱⁱⁱ—Nd1—O4	69.63 (19)	O2—C6—C3	117.2 (7)
O2—Nd1—O4	78.0 (2)	C2—C3—C4	116.8 (8)
O1ⁱ—Nd1—O4	141.9 (2)	C2—C3—C6	121.8 (7)
O1ⁱⁱ—Nd1—O4	80.7 (2)	C4—C3—C6	121.4 (7)
O4ⁱⁱⁱ—Nd1—O4	131.0 (3)	C1—C2—C3	120.2 (8)
O2ⁱⁱⁱ—Nd1—O3ⁱⁱⁱ	140.41 (19)	C1—C2—H2	119.9
O2—Nd1—O3ⁱⁱⁱ	68.36 (19)	C3—C2—H2	119.9
O1ⁱ—Nd1—O3ⁱⁱⁱ	72.4 (2)	C5—C4—C3	119.1 (9)
O1ⁱⁱ—Nd1—O3ⁱⁱⁱ	81.4 (2)	C5—C4—H4	120.4
O4ⁱⁱⁱ—Nd1—O3ⁱⁱⁱ	124.35 (18)	C3—C4—H4	120.4
O4—Nd1—O3ⁱⁱⁱ	71.60 (19)	C5—N1—C1	118.5 (7)
O2ⁱⁱⁱ—Nd1—O3	68.36 (19)	N1—C5—C4	123.2 (8)
O2—Nd1—O3	140.41 (19)	N1—C5—H5	118.4
O1ⁱ—Nd1—O3	81.4 (2)	C4—C5—H5	118.4
O1ⁱⁱ—Nd1—O3	72.4 (2)	N1—C1—C2	122.0 (9)
O4ⁱⁱⁱ—Nd1—O3	71.60 (19)	N1—C1—H1	119.0
O4—Nd1—O3	124.35 (18)	C2—C1—H1	119.0
O3ⁱⁱⁱ—Nd1—O3	145.1 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1, z−1/2; (iii) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H6···Cl2^iv	0.95 (6)	2.29 (6)	3.211 (7)	163 (6)
O3—H7···N1^v	0.97 (4)	1.72 (4)	2.685 (10)	174 (9)
O4—H8···Cl2ⁱ	0.96 (4)	2.15 (5)	3.041 (6)	155 (6)
O4—H9···O3^vi	0.95 (2)	1.93 (3)	2.841 (8)	160 (8)

Symmetry codes: (i) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1; (v) x−1/2, y+1/2, −z+1/2; (vi) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Nd(C₆H₄NO₂)₂(H₂O)₄]Cl
M_r	495.96
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	173
a, b, c (Å)	8.9223 (18), 19.684 (4), 10.151 (2)
V (Å³)	1782.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.10
Crystal size (mm)	0.18 × 0.17 × 0.15

Data collection
Diffractometer	Rigaku Saturn724+ CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.49, 0.63
No. of measured, independent and observed [I > 2σ(I)] reflections	9085, 2056, 1764
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.190, 1.33
No. of reflections	2056
No. of parameters	122
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.12, −1.06

Computer programs: CrystalClear (Rigaku, 2007), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Nd1—O1ⁱ	2.425 (6)	Nd1—O3	2.544 (6)
Nd1—O2	2.385 (5)	Nd1—O4	2.480 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H6···Cl2ⁱⁱ	0.95 (6)	2.29 (6)	3.211 (7)	163 (6)
O3—H7···N1ⁱⁱⁱ	0.97 (4)	1.72 (4)	2.685 (10)	174 (9)
O4—H8···Cl2ⁱ	0.96 (4)	2.15 (5)	3.041 (6)	155 (6)
O4—H9···O3^iv	0.95 (2)	1.93 (3)	2.841 (8)	160 (8)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x−1/2, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z.

Acknowledgements

The work was supported financially by the National Natural Science Foundation of China (grant Nos. 50973003 and 21001009), the National High-Tech R&D Program of China (863 Program) and of MOST (No. 2010 A A03A406). Special thanks are due to Dr X. Hao, L. Wang and T.-L. Liang for their assistance in the data collection.

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