Poly[[chloridodimethanol(μ3-pyridine-2,3-dicarboxyl­ato)europium(III)] methanol monosolvate]

Wu, D.; Chen, L.; Wu, G.

doi:10.1107/S1600536812017862

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m682

doi:10.1107/S1600536812017862

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Poly[[chloridodimethanol(μ₃-pyridine-2,3-dicarboxylato)europium(III)] methanol monosolvate]

Dayu Wu,^a Liyang Chen ^a and Genhua Wu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Anqing Teachers College, Anqing 246011, People's Republic of China
^*Correspondence e-mail: wudayu_nju@yahoo.com.cn

(Received 10 March 2012; accepted 21 April 2012; online 28 April 2012)

The asymmetric unit of the title compound, {[Eu(C₇H₃NO₄)Cl(CH₃OH)₂]·CH₃OH}_n, contains one Eu^III ion, one pyridine 2,3-dicarboxylate dianion (PDC), two CH₃OH molecules coordinating to the metal atom, one coordinating chloride and one lattice occluded CH₃OH molecule. In the crystal, each PDC anion coordinates to three adjacent Eu^III ions by the pyridine N and O atoms of the carboxylate groups. The Eu^III cation is eightfold coordinated by four carboxylate O atoms, one pyridine N atom, two MeOH and one chloride anion in the form of a distorted polyhedron. Extended coordination of the PDC ligand lead to the formation of a two-dimensional coordination polymer parallel to (10-1).

Related literature

For related work on pyridine-carboxylate transition-metal compounds, see: Swamy et al. (1998 ); Zhong et al. (1994 ); Zhang et al. (2003 ); Wu et al. (2003 ); Tong et al. (2000 ). For work on lanthanide compounds, see, for example: Zhao et al. (2004 ).

Experimental

Crystal data

[Eu(C₇H₃NO₄)Cl(CH₄O)₂]·CH₄O
M_r = 448.64
Monoclinic, P 2₁ /n
a = 10.4870 (3) Å
b = 10.9123 (3) Å
c = 12.9248 (3) Å
β = 99.694 (2)°
V = 1457.96 (7) Å³
Z = 4
Mo Kα radiation
μ = 4.51 mm⁻¹
T = 150 K
0.20 × 0.15 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.448, T_max = 0.532
7658 measured reflections
2550 independent reflections
2260 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.057
S = 1.02
2550 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 1.34 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Selected bond lengths (Å)

Eu1—O3ⁱ	2.344 (3)
Eu1—O4	2.346 (3)
Eu1—O2	2.354 (3)
Eu1—O1ⁱⁱ	2.373 (3)
Eu1—O5	2.450 (3)
Eu1—O6	2.490 (3)
Eu1—N1ⁱ	2.655 (3)
Eu1—Cl1	2.7723 (11)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812017862/ds2185sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017862/ds2185Isup2.hkl

checkCIF report

Comment top

The pyridine dicarboxylic acid (H₂pydc) is a diverse bridging ligand and has drawn some attention in photochemistry and crystal engineering. In case of pyridine-2,3-dicarboxylate functional groups, pydc exhibits bis(monodentate) (Swamy et al.,1998), tridentate(Zhong et al., 1994; Zhang et al., 2003), bis(bidentate) (Wu et al., 2003; Tong et al., 2000) coordination modes to form a few transition metal coordination polymers. It should display high reactivity to the lanthanide, since the oxygen atom of carboxylate group has a strong affinity to Ln³⁺ ions (Zhao et al.,2004). In this work, we selected pyridine-2,3-dicarboxylate and lanthanide ions to assemble coordination polymer under hydrothermal conditions, forming two-dimensional network structures. As depicted in Figure 1, the asymmetric unit contains one europium ion, one deprotonated pyridine 2,3-dicarboxylate ligand (PDC), two CH₃OH molecules coordinated to the metal center, one coordinated chloride and one lattice occluded CH₃OH molecule. In the crystal structure, each PDC ligand coordinates to three adjacent Eu ions by the pyridyl N and O atoms of the carboxylate moieties. Eu is coordinated by four O atoms of carboxylate, one pyridyl N, two MeOH and one chloride dispaying eight-coordinated environment with average Eu—O bond length of being 2.3825 Å, obviously shorter than that of Eu—Cl 2.7724 Å (Table 1). Extended coordination of PDC ligand lead to the formation of a 2D coordination polymer (Figure 2). π···π stacking interactions were found to stabilize two-dimensional structure with the shortest carbon···carbon distance of 3.487 Å in the plan.

Related literature top

For related work on pyridine-carboxylate transition-metal compounds, see: Swamy et al. (1998); Zhong et al. (1994); Zhang et al. (2003); Wu et al. (2003); Tong et al. (2000). For work on lanthanide compounds, see, for example: Zhao et al. (2004).

Experimental top

A mixture of EuCl₃^.6H₂O (0.037 g, 0.1 mmol), H₂pydc (0.017 g, 0.1 mmol) in 8 mL H₂O was stirred at room temperature for 30 min, the solution was put into a 25 mL Teflon-lined stainless-steel container, heated to 165 ^oC and maintained for 48 h, and then cooled to room temperature in 45 h. The colorless block crystal was obtained by filtration, washed with water and ethanol in 67% yield (based on Eu). Anal. Calc. for C₁₀ H₁₅ Cl Eu N O₇ : C, 26.77; H, 3.37; N, 3.12. Found: C, 27.05; H, 3.47; N, 3.16%. IR (KBr pellet): 3407(m), 1698(m), 1594(s), 1565(s), 1442(m), 1381(s), 1254(m), 1095(m), 758(m) cm^-1.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, the thermal ellipsoids were drawn at 50% probability level.
	Fig. 2. The 2-D packing structure of the title compound.

Poly[[chloridodimethanol(µ₃-pyridine-2,3-dicarboxylato)europium(III)] methanol monosolvate] top

Crystal data top

[Eu(C₇H₃NO₄)Cl(CH₄O)₂]·CH₄O	F(000) = 872
M_r = 448.64	D_x = 2.044 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5415 reflections
a = 10.4870 (3) Å	θ = 3.0–29.1°
b = 10.9123 (3) Å	µ = 4.51 mm⁻¹
c = 12.9248 (3) Å	T = 150 K
β = 99.694 (2)°	Block, white
V = 1457.96 (7) Å³	0.20 × 0.15 × 0.14 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2550 independent reflections
Radiation source: fine-focus sealed tube	2260 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
phi and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→11
T_min = 0.448, T_max = 0.532	k = −12→12
7658 measured reflections	l = −14→15

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0287P)² + 1.5721P] where P = (F_o² + 2F_c²)/3
2550 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 1.34 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Eu(C₇H₃NO₄)Cl(CH₄O)₂]·CH₄O	V = 1457.96 (7) Å³
M_r = 448.64	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.4870 (3) Å	µ = 4.51 mm⁻¹
b = 10.9123 (3) Å	T = 150 K
c = 12.9248 (3) Å	0.20 × 0.15 × 0.14 mm
β = 99.694 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2550 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2260 reflections with I > 2σ(I)
T_min = 0.448, T_max = 0.532	R_int = 0.029
7658 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.02	Δρ_max = 1.34 e Å⁻³
2550 reflections	Δρ_min = −0.56 e Å⁻³
184 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
Eu1	0.19538 (2)	0.471828 (18)	0.142087 (15)	0.01375 (8)
C1	0.1686 (5)	1.0083 (4)	−0.0245 (4)	0.0217 (10)
H1A	0.1752	1.0679	−0.0747	0.026*
C2	0.1143 (4)	0.8967 (4)	−0.0540 (3)	0.0204 (10)
H2A	0.0830	0.8801	−0.1243	0.024*
C3	0.1066 (4)	0.8081 (4)	0.0227 (3)	0.0152 (9)
C4	0.1520 (4)	0.8388 (4)	0.1267 (3)	0.0141 (9)
C5	0.2135 (4)	1.0315 (4)	0.0803 (3)	0.0187 (9)
H5A	0.2508	1.1073	0.0992	0.022*
C6	0.1440 (4)	0.7542 (4)	0.2180 (3)	0.0142 (9)
C7	0.0458 (4)	0.6855 (4)	−0.0113 (3)	0.0149 (9)
C8	−0.0245 (5)	0.4395 (4)	0.3294 (4)	0.0309 (12)
H8A	−0.1158	0.4238	0.3164	0.046*
H8B	−0.0096	0.5262	0.3342	0.046*
H8C	0.0137	0.4012	0.3942	0.046*
C9	0.2592 (5)	0.3714 (5)	−0.1019 (4)	0.0298 (12)
H9A	0.3221	0.3790	−0.1476	0.045*
H9B	0.1840	0.4189	−0.1292	0.045*
H9C	0.2353	0.2869	−0.0974	0.045*
C10	0.6250 (6)	0.3148 (5)	0.1466 (4)	0.0437 (14)
H10A	0.7143	0.3136	0.1383	0.066*
H10B	0.6088	0.2489	0.1919	0.066*
H10C	0.6057	0.3915	0.1769	0.066*
Cl1	0.41214 (10)	0.62123 (9)	0.17815 (8)	0.0207 (2)
N1	0.2053 (3)	0.9493 (3)	0.1559 (3)	0.0161 (8)
O1	−0.0723 (3)	0.6882 (2)	−0.0493 (2)	0.0201 (7)
O2	0.1171 (3)	0.5928 (2)	−0.0058 (2)	0.0189 (7)
O3	0.1826 (3)	0.7950 (2)	0.3084 (2)	0.0180 (7)
O4	0.0993 (3)	0.6474 (2)	0.2001 (2)	0.0154 (6)
O5	0.3136 (3)	0.4156 (3)	0.0010 (2)	0.0222 (7)
O6	0.0332 (3)	0.3900 (3)	0.2445 (2)	0.0235 (7)
O7	0.5459 (4)	0.3005 (4)	0.0477 (3)	0.0470 (10)
H7A	0.5784	0.3203	−0.0159	0.056*
H5B	0.3905	0.3848	0.0202	0.056*
H6B	0.0268	0.3152	0.2582	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.01652 (13)	0.00914 (13)	0.01382 (12)	−0.00020 (9)	−0.00258 (8)	0.00020 (8)
C1	0.029 (3)	0.013 (2)	0.021 (2)	0.0009 (19)	0.001 (2)	0.0053 (18)
C2	0.024 (3)	0.019 (2)	0.015 (2)	−0.0010 (19)	−0.0036 (18)	0.0026 (18)
C3	0.012 (2)	0.016 (2)	0.017 (2)	0.0029 (18)	−0.0012 (16)	−0.0021 (17)
C4	0.011 (2)	0.011 (2)	0.018 (2)	0.0013 (17)	−0.0040 (17)	−0.0012 (17)
C5	0.024 (3)	0.011 (2)	0.019 (2)	−0.0006 (19)	−0.0025 (18)	−0.0003 (18)
C6	0.008 (2)	0.015 (2)	0.018 (2)	0.0021 (17)	−0.0011 (17)	0.0019 (17)
C7	0.021 (3)	0.015 (2)	0.007 (2)	0.0018 (19)	−0.0006 (17)	0.0021 (16)
C8	0.036 (3)	0.029 (3)	0.031 (3)	0.005 (2)	0.017 (2)	0.003 (2)
C9	0.031 (3)	0.033 (3)	0.024 (3)	−0.004 (2)	0.002 (2)	−0.008 (2)
C10	0.030 (3)	0.052 (4)	0.050 (4)	0.001 (3)	0.006 (3)	0.012 (3)
Cl1	0.0198 (6)	0.0199 (5)	0.0212 (6)	−0.0041 (4)	0.0000 (4)	−0.0028 (4)
N1	0.017 (2)	0.0103 (18)	0.0194 (19)	0.0012 (14)	−0.0013 (15)	−0.0002 (14)
O1	0.0193 (18)	0.0143 (15)	0.0243 (17)	−0.0021 (13)	−0.0027 (13)	−0.0026 (12)
O2	0.0263 (18)	0.0117 (15)	0.0163 (15)	0.0037 (14)	−0.0034 (13)	−0.0013 (12)
O3	0.0208 (18)	0.0147 (15)	0.0166 (16)	−0.0028 (13)	−0.0024 (13)	−0.0004 (12)
O4	0.0181 (17)	0.0090 (14)	0.0177 (15)	−0.0007 (12)	−0.0006 (12)	−0.0019 (12)
O5	0.0222 (18)	0.0244 (17)	0.0182 (16)	0.0044 (14)	−0.0019 (13)	−0.0003 (13)
O6	0.0294 (19)	0.0183 (16)	0.0224 (17)	−0.0005 (14)	0.0032 (14)	0.0033 (13)
O7	0.043 (3)	0.067 (3)	0.034 (2)	0.018 (2)	0.0145 (19)	0.0166 (19)

Geometric parameters (Å, º) top

Eu1—O3ⁱ	2.344 (3)	C7—O1	1.253 (5)
Eu1—O4	2.346 (3)	C7—O2	1.253 (5)
Eu1—O2	2.354 (3)	C8—O6	1.445 (5)
Eu1—O1ⁱⁱ	2.373 (3)	C8—H8A	0.9600
Eu1—O5	2.450 (3)	C8—H8B	0.9600
Eu1—O6	2.490 (3)	C8—H8C	0.9600
Eu1—N1ⁱ	2.655 (3)	C9—O5	1.438 (5)
Eu1—Cl1	2.7723 (11)	C9—H9A	0.9600
C1—C2	1.371 (6)	C9—H9B	0.9600
C1—C5	1.380 (6)	C9—H9C	0.9600
C1—H1A	0.9300	C10—O7	1.410 (7)
C2—C3	1.397 (6)	C10—H10A	0.9600
C2—H2A	0.9300	C10—H10B	0.9600
C3—C4	1.389 (6)	C10—H10C	0.9600
C3—C7	1.515 (6)	N1—Eu1ⁱⁱⁱ	2.655 (3)
C4—N1	1.355 (5)	O1—Eu1ⁱⁱ	2.373 (3)
C4—C6	1.512 (6)	O3—Eu1ⁱⁱⁱ	2.344 (3)
C5—N1	1.340 (5)	O5—H5B	0.8701
C5—H5A	0.9300	O6—H6B	0.8404
C6—O3	1.253 (5)	O7—H7A	0.9656
C6—O4	1.262 (5)

O3ⁱ—Eu1—O4	146.02 (10)	N1—C5—H5A	118.7
O3ⁱ—Eu1—O2	141.52 (10)	C1—C5—H5A	118.7
O4—Eu1—O2	72.05 (9)	O3—C6—O4	123.4 (4)
O3ⁱ—Eu1—O1ⁱⁱ	75.98 (10)	O3—C6—C4	117.3 (3)
O4—Eu1—O1ⁱⁱ	122.41 (10)	O4—C6—C4	119.2 (3)
O2—Eu1—O1ⁱⁱ	85.21 (10)	O1—C7—O2	125.6 (4)
O3ⁱ—Eu1—O5	71.06 (10)	O1—C7—C3	115.6 (4)
O4—Eu1—O5	137.83 (10)	O2—C7—C3	118.6 (4)
O2—Eu1—O5	71.76 (10)	O6—C8—H8A	109.5
O1ⁱⁱ—Eu1—O5	74.93 (10)	O6—C8—H8B	109.5
O3ⁱ—Eu1—O6	87.13 (10)	H8A—C8—H8B	109.5
O4—Eu1—O6	75.79 (10)	O6—C8—H8C	109.5
O2—Eu1—O6	117.19 (10)	H8A—C8—H8C	109.5
O1ⁱⁱ—Eu1—O6	69.05 (10)	H8B—C8—H8C	109.5
O5—Eu1—O6	141.48 (10)	O5—C9—H9A	109.5
O3ⁱ—Eu1—N1ⁱ	63.22 (10)	O5—C9—H9B	109.5
O4—Eu1—N1ⁱ	83.10 (10)	H9A—C9—H9B	109.5
O2—Eu1—N1ⁱ	151.18 (10)	O5—C9—H9C	109.5
O1ⁱⁱ—Eu1—N1ⁱ	121.25 (10)	H9A—C9—H9C	109.5
O5—Eu1—N1ⁱ	123.02 (10)	H9B—C9—H9C	109.5
O6—Eu1—N1ⁱ	68.52 (10)	O7—C10—H10A	109.5
O3ⁱ—Eu1—Cl1	92.51 (7)	O7—C10—H10B	109.5
O4—Eu1—Cl1	81.38 (7)	H10A—C10—H10B	109.5
O2—Eu1—Cl1	88.32 (8)	O7—C10—H10C	109.5
O1ⁱⁱ—Eu1—Cl1	151.46 (8)	H10A—C10—H10C	109.5
O5—Eu1—Cl1	76.64 (7)	H10B—C10—H10C	109.5
O6—Eu1—Cl1	137.37 (7)	C5—N1—C4	117.8 (4)
N1ⁱ—Eu1—Cl1	73.41 (8)	C5—N1—Eu1ⁱⁱⁱ	126.3 (3)
C2—C1—C5	119.5 (4)	C4—N1—Eu1ⁱⁱⁱ	115.6 (2)
C2—C1—H1A	120.2	C7—O1—Eu1ⁱⁱ	126.7 (3)
C5—C1—H1A	120.2	C7—O2—Eu1	128.4 (2)
C1—C2—C3	119.2 (4)	C6—O3—Eu1ⁱⁱⁱ	128.6 (3)
C1—C2—H2A	120.4	C6—O4—Eu1	130.2 (3)
C3—C2—H2A	120.4	C9—O5—Eu1	126.9 (3)
C4—C3—C2	117.9 (4)	C9—O5—H5B	109.8
C4—C3—C7	123.5 (4)	Eu1—O5—H5B	116.4
C2—C3—C7	118.5 (4)	C8—O6—Eu1	132.9 (3)
N1—C4—C3	122.8 (4)	C8—O6—H6B	98.2
N1—C4—C6	113.6 (3)	Eu1—O6—H6B	123.2
C3—C4—C6	123.6 (4)	C10—O7—H7A	120.6
N1—C5—C1	122.6 (4)

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

Experimental details

Crystal data
Chemical formula	[Eu(C₇H₃NO₄)Cl(CH₄O)₂]·CH₄O
M_r	448.64
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	10.4870 (3), 10.9123 (3), 12.9248 (3)
β (°)	99.694 (2)
V (Å³)	1457.96 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.51
Crystal size (mm)	0.20 × 0.15 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.448, 0.532
No. of measured, independent and observed [I > 2σ(I)] reflections	7658, 2550, 2260
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.057, 1.02
No. of reflections	2550
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.34, −0.56

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Eu1—O3ⁱ	2.344 (3)	Eu1—O5	2.450 (3)
Eu1—O4	2.346 (3)	Eu1—O6	2.490 (3)
Eu1—O2	2.354 (3)	Eu1—N1ⁱ	2.655 (3)
Eu1—O1ⁱⁱ	2.373 (3)	Eu1—Cl1	2.7723 (11)

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 21001007, 21171008 and 21001008).

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