Poly[[hexa­aqua­(μ2-oxalato-κ4O1,O2:O1′,O2′)bis­(μ3-pyridine-2,4-dicarboxyl­ato-κ4N,O2:O2′:O4)dilanthanum(III)] monohydrate]

Shen, F.M.; Lush, S.F.

doi:10.1107/S160053681104668X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1731-m1732

https://doi.org/10.1107/S160053681104668X

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Poly[[hexaaqua(μ₂-oxalato-κ⁴O¹,O²:O^1′,O^2′)bis(μ₃-pyridine-2,4-dicarboxylato-κ⁴N,O²:O^2′:O⁴)dilanthanum(III)] monohydrate]

Fwu Ming Shen ^a and Shie Fu Lush ^b ^*

^aDepartment of Biotechnology, Yuanpei University, HsinChu 30015, Taiwan, and ^bDepartment of General Education Center, Yuanpei University, HsinChu 30015, Taiwan
^*Correspondence e-mail: lush@mail.ypu.edu.tw

(Received 30 October 2011; accepted 5 November 2011; online 9 November 2011)

In the polymeric title compound, {[La₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O}_n, the La³⁺ cation is nine-coordinated in a distorted LaNO₈ tricapped trigonal–prismatic geometry formed by three pyridinedicarboxylate anions, one oxalate anion and three water molecules. The oxalate anion is located on an inversion center. The oxalate and pyridinedicarboxylate anions bridge the La³⁺ cations, forming a two-dimensional polymeric complex parallel to (010). Intermolecular O—H⋯O hydrogen bonding and weak C—H⋯O hydrogen bonding is present in the crystal structure and π–π stacking [centroid–centroid distance = 3.571 (3) Å] is observed between parallel pyridine rings of adjacent molecules. The uncoordinated water molecule shows an occupancy of 0.5.

Related literature

For related structures, see: Aghabozorg et al. (2011 ); Li et al. (2007 ); Wang et al. (2009 ).

Experimental

Crystal data

[La₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O
M_r = 822.16
Triclinic, $[P \overline 1]$
a = 6.4614 (8) Å
b = 6.6844 (8) Å
c = 14.0796 (17) Å
α = 89.735 (2)°
β = 85.266 (2)°
γ = 73.135 (2)°
V = 579.85 (12) Å³
Z = 1
Mo Kα radiation
μ = 3.73 mm⁻¹
T = 295 K
0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.686, T_max = 0.950
5023 measured reflections
2046 independent reflections
1795 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.093
S = 1.09
2046 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 2.14 e Å⁻³
Δρ_min = −2.13 e Å⁻³

Table 1
Selected bond lengths (Å)

La1—N1	2.726 (4)
La1—O1ⁱ	2.454 (4)
La1—O3ⁱⁱ	2.541 (5)
La1—O4	2.551 (5)
La1—O5	2.543 (4)
La1—O6ⁱⁱⁱ	2.550 (5)
La1—O7	2.604 (7)
La1—O8	2.553 (5)
La1—O9	2.612 (7)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O4ⁱⁱ	0.84	2.08	2.911 (8)	168
O7—H7B⋯O10^iv	0.83	1.71	2.533 (12)	168
O8—H8A⋯O2^v	0.83	1.83	2.660 (7)	173
O8—H8B⋯O6^vi	0.96	2.03	2.914 (7)	153
O9—H9A⋯O6^vi	0.88	2.27	2.987 (8)	138
O9—H9B⋯O10	0.85	1.73	2.390 (14)	133
O10—H10A⋯O5ⁱⁱ	0.83	2.24	2.885 (12)	135
O10—H10A⋯O8ⁱⁱ	0.83	2.29	2.924 (15)	133
O10—H10B⋯O9^vii	0.85	1.77	2.591 (17)	163
C5—H5A⋯O3ⁱⁱ	0.93	2.49	3.164 (7)	130
Symmetry codes: (ii) x-1, y, z; (iv) x, y+1, z; (v) -x+2, -y, -z+1; (vi) -x+1, -y, -z+2; (vii) -x, -y, -z+2.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681104668X/xu5376sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104668X/xu5376Isup2.hkl

checkCIF report

Comment top

The pyridine-2,4-dicarboxylic acid (pdcH2) has important coordination functions to metals by either carboxylate bridges between metal centers, to form dimeric complexes or tridentate (O, N, O') chelation to metal ions. Some pydc complexes have been reported (Li et al., 2007; Wang et al., 2009; Aghabozorg et al., 2011).

The symmetric unit of the title compound,{[(LaC₇H₃NO₄)(C₂O₄)_0.5(H₂O)₃]₂.(H₂O)}_n, contains two La^III atoms, two pyridine-2,4-dicarboxylate(pydc) ligands, one oxalate ligand and six coordinated water molecules. The oxalate ligand are both chelating and bridging, forming an oxalate-bridged dinuclear complex. The La^III is nine-coordinated in a distorted tricapped trigonal prismatic geometry by N,O atom from a pydc ligand, two O atoms from two pydc ligands, two O atoms from one oxalate ligand and three O atoms from coordinated water molecules (shown as Fig. 1, Table 1). The geometric center of the dimer lies on an inversion center.

The crystal structure contains weak O—H···O and non-classical C—H···O hydrogen bonds. The π-π stacking between two pyridine rings of (pydc) anion fragments with distances of 3.570 (3) Å (1 - x, 1 - y,1 - z) are observed (Fig. 3). The uncoordinated water molecule shows half-occupation.

Related literature top

For related structures, see: Aghabozorg et al. (2011); Li et al. (2007); Wang et al. (2009).

Experimental top

La(NO₃)₃.6H2O (0.1096 g, 0.25 mmole), pydridine-2,4-dicarboxylic acid (0.0418 g, 0.25 mmol) and 4,4'-dipyridine (0.0464 g, 0.25 mmol) were mixed in 10 ml of deionized water. After stirring for 30 min, the mixture was placed in a 23 ml Teflon-lined reactor which was heated under autogenous pressure to 418 K for 48 h and then allowed to cool to room temperature. The brown transparent single crystals were obtained in 41.3% yield (based on La).

Structure description top

For related structures, see: Aghabozorg et al. (2011); Li et al. (2007); Wang et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. All H atoms have been omitted for clarity. [Symmetry code: (i) -1 + x, y, z; (ii) 1 - x, 1 - y, 1 - z; (iv)1+x, y, z.]
	Fig. 2. The molecular packing for the title compound. Hydrogen bonds are shown as dashed lines.
	Fig. 3. π-π Stacking between pyridine rings [symmetry code: (ii) 1 - x, 1 - y,1 - z.]

Poly[[hexaaqua(µ₂-oxalato- κ⁴O¹,O²:O^1',O^2')bis(µ₃-pyridine-2,4- dicarboxylato-κ⁴N,O²:O^2':O⁴) dilanthanum(III)] monohydrate] top

Crystal data top

[La₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O	Z = 1
M_r = 822.16	F(000) = 396
Triclinic, P1	D_x = 2.355 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4614 (8) Å	Cell parameters from 3390 reflections
b = 6.6844 (8) Å	θ = 2.5–25.0°
c = 14.0796 (17) Å	µ = 3.73 mm⁻¹
α = 89.735 (2)°	T = 295 K
β = 85.266 (2)°	Columnar, brown
γ = 73.135 (2)°	0.30 × 0.10 × 0.10 mm
V = 579.85 (12) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2046 independent reflections
Radiation source: fine-focus sealed tube	1795 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 1.5°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −7→7
T_min = 0.686, T_max = 0.950	l = −16→16
5023 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0639P)²] where P = (F_o² + 2F_c²)/3
2046 reflections	(Δ/σ)_max = 0.001
175 parameters	Δρ_max = 2.14 e Å⁻³
0 restraints	Δρ_min = −2.13 e Å⁻³

Crystal data top

[La₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O	γ = 73.135 (2)°
M_r = 822.16	V = 579.85 (12) Å³
Triclinic, P1	Z = 1
a = 6.4614 (8) Å	Mo Kα radiation
b = 6.6844 (8) Å	µ = 3.73 mm⁻¹
c = 14.0796 (17) Å	T = 295 K
α = 89.735 (2)°	0.30 × 0.10 × 0.10 mm
β = 85.266 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2046 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1795 reflections with I > 2σ(I)
T_min = 0.686, T_max = 0.950	R_int = 0.035
5023 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.09	Δρ_max = 2.14 e Å⁻³
2046 reflections	Δρ_min = −2.13 e Å⁻³
175 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	Occ. (<1)
La1	0.36051 (5)	0.32815 (5)	0.80389 (2)	0.0265 (1)
O1	0.7674 (8)	0.3427 (7)	0.2806 (3)	0.0392 (16)
O2	1.0913 (8)	0.2154 (8)	0.3384 (3)	0.0525 (19)
O3	1.0788 (7)	0.2730 (8)	0.6993 (3)	0.0396 (16)
O4	0.7592 (7)	0.3177 (9)	0.7799 (3)	0.0521 (18)
O5	0.5103 (8)	0.2478 (6)	0.9657 (3)	0.0423 (14)
O6	0.5841 (9)	0.3677 (7)	1.1030 (3)	0.0485 (18)
O7	−0.0071 (10)	0.5171 (10)	0.8990 (5)	0.0863 (19)
O8	0.5618 (9)	−0.0608 (7)	0.7835 (4)	0.0542 (19)
O9	0.1731 (10)	0.0871 (10)	0.9025 (5)	0.0863 (19)
N1	0.5725 (7)	0.2598 (7)	0.6261 (3)	0.0249 (14)
C1	0.7769 (9)	0.2729 (9)	0.6137 (4)	0.0257 (17)
C2	0.5722 (10)	0.2408 (9)	0.4559 (4)	0.0294 (17)
C3	0.7801 (9)	0.2612 (8)	0.4439 (4)	0.0260 (17)
C4	0.8843 (9)	0.2739 (9)	0.5250 (4)	0.0285 (17)
C5	0.4771 (9)	0.2395 (9)	0.5474 (4)	0.0291 (17)
C6	0.8914 (10)	0.2739 (9)	0.3464 (4)	0.0301 (17)
C7	0.8804 (10)	0.2893 (10)	0.7040 (4)	0.0341 (19)
C8	0.5274 (10)	0.3885 (9)	1.0197 (4)	0.0288 (17)
O10	−0.1015 (18)	−0.0885 (16)	0.9137 (11)	0.072 (5)	0.500
H2A	0.49810	0.22820	0.40340	0.0350*
H4A	1.02570	0.28300	0.51960	0.0340*
H5A	0.33850	0.22340	0.55470	0.0350*
H7A	−0.08470	0.47740	0.86270	0.0800*
H7B	−0.05250	0.64720	0.89900	0.0800*
H8A	0.67010	−0.11890	0.74700	0.0800*
H8B	0.55880	−0.18960	0.81340	0.0800*
H9A	0.29540	−0.01320	0.89080	0.0800*
H9B	0.07450	0.05280	0.87580	0.0800*
H10A	−0.22390	−0.01980	0.89910	0.0800*	0.500
H10B	−0.11240	−0.06870	0.97360	0.0800*	0.500

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.0283 (2)	0.0378 (2)	0.0187 (2)	−0.0182 (2)	−0.0020 (1)	0.0042 (1)
O1	0.043 (3)	0.047 (3)	0.025 (2)	−0.009 (2)	−0.004 (2)	0.0078 (19)
O2	0.033 (3)	0.074 (4)	0.039 (3)	−0.001 (2)	0.009 (2)	0.014 (2)
O3	0.028 (2)	0.060 (3)	0.038 (3)	−0.022 (2)	−0.0100 (19)	0.002 (2)
O4	0.037 (3)	0.112 (4)	0.023 (2)	−0.046 (3)	−0.005 (2)	0.007 (2)
O5	0.067 (3)	0.029 (2)	0.032 (2)	−0.013 (2)	−0.015 (2)	0.0013 (19)
O6	0.079 (4)	0.038 (2)	0.036 (3)	−0.022 (2)	−0.030 (3)	0.013 (2)
O7	0.059 (3)	0.072 (3)	0.113 (4)	−0.008 (2)	0.037 (3)	0.026 (3)
O8	0.071 (4)	0.034 (3)	0.053 (3)	−0.016 (2)	0.023 (3)	0.001 (2)
O9	0.059 (3)	0.072 (3)	0.113 (4)	−0.008 (2)	0.037 (3)	0.026 (3)
N1	0.020 (2)	0.029 (2)	0.027 (3)	−0.0093 (19)	−0.0018 (19)	0.002 (2)
C1	0.018 (3)	0.029 (3)	0.031 (3)	−0.008 (2)	−0.003 (2)	0.006 (2)
C2	0.030 (3)	0.037 (3)	0.023 (3)	−0.011 (3)	−0.009 (2)	0.002 (2)
C3	0.025 (3)	0.027 (3)	0.024 (3)	−0.005 (2)	−0.001 (2)	0.004 (2)
C4	0.019 (3)	0.039 (3)	0.027 (3)	−0.008 (2)	−0.002 (2)	0.008 (3)
C5	0.023 (3)	0.036 (3)	0.030 (3)	−0.011 (2)	−0.004 (2)	0.003 (2)
C6	0.033 (3)	0.032 (3)	0.023 (3)	−0.007 (3)	0.001 (2)	0.000 (2)
C7	0.030 (3)	0.046 (4)	0.033 (3)	−0.021 (3)	−0.006 (3)	0.011 (3)
C8	0.032 (3)	0.030 (3)	0.022 (3)	−0.006 (2)	0.000 (2)	0.003 (2)
O10	0.044 (6)	0.044 (6)	0.135 (12)	−0.014 (5)	−0.036 (7)	0.007 (7)

Geometric parameters (Å, º) top

La1—N1	2.726 (4)	O8—H8B	0.9600
La1—O1ⁱ	2.454 (4)	O9—H9B	0.8500
La1—O3ⁱⁱ	2.541 (5)	O9—H9A	0.8800
La1—O4	2.551 (5)	O10—H10A	0.8300
La1—O5	2.543 (4)	O10—H10B	0.8500
La1—O6ⁱⁱⁱ	2.550 (5)	N1—C5	1.338 (7)
La1—O7	2.604 (7)	N1—C1	1.346 (8)
La1—O8	2.553 (5)	C1—C4	1.379 (8)
La1—O9	2.612 (7)	C1—C7	1.503 (8)
O1—C6	1.271 (8)	C2—C3	1.386 (9)
O2—C6	1.232 (9)	C2—C5	1.382 (8)
O3—C7	1.251 (8)	C3—C6	1.510 (8)
O4—C7	1.253 (7)	C3—C4	1.388 (8)
O5—C8	1.247 (7)	C8—C8ⁱⁱⁱ	1.541 (8)
O6—C8	1.253 (7)	C2—H2A	0.9300
O7—H7B	0.8300	C4—H4A	0.9300
O7—H7A	0.8400	C5—H5A	0.9300
O8—H8A	0.8300

O4—La1—O5	73.91 (15)	La1—O5—C8	121.8 (4)
O4—La1—O7	143.20 (19)	La1ⁱⁱⁱ—O6—C8	121.6 (4)
O4—La1—O8	76.08 (19)	La1—O7—H7B	119.00
O4—La1—O9	130.46 (19)	H7A—O7—H7B	105.00
O4—La1—N1	60.09 (14)	La1—O7—H7A	96.00
O3ⁱⁱ—La1—O4	136.05 (14)	La1—O8—H8A	129.00
O1ⁱ—La1—O4	94.15 (17)	H8A—O8—H8B	93.00
O4—La1—O6ⁱⁱⁱ	71.03 (17)	La1—O8—H8B	138.00
O5—La1—O7	85.94 (19)	La1—O9—H9A	87.00
O5—La1—O8	78.78 (15)	H9A—O9—H9B	108.00
O5—La1—O9	68.31 (19)	La1—O9—H9B	116.00
O5—La1—N1	129.55 (15)	H10A—O10—H10B	102.00
O3ⁱⁱ—La1—O5	143.58 (15)	La1—N1—C5	123.7 (4)
O1ⁱ—La1—O5	131.93 (14)	La1—N1—C1	118.9 (3)
O5—La1—O6ⁱⁱⁱ	62.98 (13)	C1—N1—C5	116.8 (5)
O7—La1—O8	130.39 (19)	N1—C1—C4	122.9 (5)
O7—La1—O9	64.2 (2)	N1—C1—C7	115.1 (5)
O7—La1—N1	143.97 (18)	C4—C1—C7	121.9 (6)
O3ⁱⁱ—La1—O7	76.45 (18)	C3—C2—C5	118.7 (5)
O1ⁱ—La1—O7	76.62 (19)	C2—C3—C6	122.0 (5)
O6ⁱⁱⁱ—La1—O7	72.42 (19)	C4—C3—C6	120.1 (5)
O8—La1—O9	66.27 (19)	C2—C3—C4	117.9 (5)
O8—La1—N1	71.47 (16)	C1—C4—C3	119.6 (6)
O3ⁱⁱ—La1—O8	88.67 (17)	N1—C5—C2	123.9 (6)
O1ⁱ—La1—O8	144.45 (16)	O1—C6—O2	126.8 (6)
O6ⁱⁱⁱ—La1—O8	134.78 (18)	O2—C6—C3	117.2 (5)
O9—La1—N1	128.72 (18)	O1—C6—C3	116.1 (6)
O3ⁱⁱ—La1—O9	75.33 (18)	O4—C7—C1	116.7 (6)
O1ⁱ—La1—O9	135.03 (19)	O3—C7—C1	119.0 (5)
O6ⁱⁱⁱ—La1—O9	115.40 (18)	O3—C7—O4	124.3 (6)
O3ⁱⁱ—La1—N1	76.02 (14)	O5—C8—O6	126.8 (5)
O1ⁱ—La1—N1	74.06 (14)	O5—C8—C8ⁱⁱⁱ	116.9 (5)
O6ⁱⁱⁱ—La1—N1	114.76 (15)	O6—C8—C8ⁱⁱⁱ	116.4 (5)
O1ⁱ—La1—O3ⁱⁱ	74.77 (16)	C5—C2—H2A	121.00
O3ⁱⁱ—La1—O6ⁱⁱⁱ	136.50 (17)	C3—C2—H2A	121.00
O1ⁱ—La1—O6ⁱⁱⁱ	69.06 (15)	C1—C4—H4A	120.00
La1ⁱ—O1—C6	137.1 (4)	C3—C4—H4A	120.00
La1^iv—O3—C7	139.6 (4)	N1—C5—H5A	118.00
La1—O4—C7	128.4 (4)	C2—C5—H5A	118.00

O5—La1—O4—C7	158.8 (6)	N1—La1—O1ⁱ—C6ⁱ	73.1 (6)
O7—La1—O4—C7	−141.7 (5)	O4—La1—O6ⁱⁱⁱ—C8ⁱⁱⁱ	−86.9 (5)
O8—La1—O4—C7	76.7 (6)	O5—La1—O6ⁱⁱⁱ—C8ⁱⁱⁱ	−5.7 (5)
O9—La1—O4—C7	117.6 (6)	O7—La1—O6ⁱⁱⁱ—C8ⁱⁱⁱ	88.8 (5)
N1—La1—O4—C7	0.3 (5)	O8—La1—O6ⁱⁱⁱ—C8ⁱⁱⁱ	−41.2 (6)
O3ⁱⁱ—La1—O4—C7	3.7 (7)	O9—La1—O6ⁱⁱⁱ—C8ⁱⁱⁱ	39.8 (6)
O1ⁱ—La1—O4—C7	−68.6 (6)	N1—La1—O6ⁱⁱⁱ—C8ⁱⁱⁱ	−129.2 (5)
O6ⁱⁱⁱ—La1—O4—C7	−134.8 (6)	La1ⁱ—O1—C6—C3	102.3 (6)
O4—La1—O5—C8	82.1 (5)	La1ⁱ—O1—C6—O2	−78.5 (8)
O7—La1—O5—C8	−66.7 (5)	La1^iv—O3—C7—O4	−11.4 (11)
O8—La1—O5—C8	160.7 (5)	La1^iv—O3—C7—C1	169.0 (4)
O9—La1—O5—C8	−130.5 (5)	La1—O4—C7—C1	4.4 (9)
N1—La1—O5—C8	106.5 (5)	La1—O4—C7—O3	−175.2 (5)
O3ⁱⁱ—La1—O5—C8	−127.3 (5)	La1—O5—C8—O6	174.5 (5)
O1ⁱ—La1—O5—C8	1.2 (6)	La1—O5—C8—C8ⁱⁱⁱ	−5.3 (8)
O6ⁱⁱⁱ—La1—O5—C8	5.6 (5)	La1ⁱⁱⁱ—O6—C8—O5	174.7 (5)
O4—La1—N1—C1	−5.7 (4)	La1ⁱⁱⁱ—O6—C8—C8ⁱⁱⁱ	−5.5 (8)
O4—La1—N1—C5	−177.0 (5)	C5—N1—C1—C4	2.4 (8)
O5—La1—N1—C1	−32.9 (5)	La1—N1—C1—C7	9.8 (6)
O5—La1—N1—C5	155.9 (4)	C1—N1—C5—C2	−3.0 (8)
O7—La1—N1—C1	135.5 (4)	C5—N1—C1—C7	−178.3 (5)
O7—La1—N1—C5	−35.7 (6)	La1—N1—C5—C2	168.4 (4)
O8—La1—N1—C1	−90.0 (4)	La1—N1—C1—C4	−169.4 (4)
O8—La1—N1—C5	98.8 (4)	N1—C1—C7—O3	170.2 (6)
O9—La1—N1—C1	−125.6 (4)	N1—C1—C7—O4	−9.4 (8)
O9—La1—N1—C5	63.2 (5)	C4—C1—C7—O3	−10.5 (9)
O3ⁱⁱ—La1—N1—C1	176.7 (4)	C4—C1—C7—O4	169.9 (6)
O3ⁱⁱ—La1—N1—C5	5.4 (4)	N1—C1—C4—C3	0.1 (9)
O1ⁱ—La1—N1—C1	98.8 (4)	C7—C1—C4—C3	−179.1 (5)
O1ⁱ—La1—N1—C5	−72.4 (4)	C5—C2—C3—C4	1.6 (8)
O6ⁱⁱⁱ—La1—N1—C1	41.6 (4)	C3—C2—C5—N1	1.0 (9)
O6ⁱⁱⁱ—La1—N1—C5	−129.7 (4)	C5—C2—C3—C6	−177.2 (5)
O4—La1—O3ⁱⁱ—C7ⁱⁱ	−173.4 (6)	C2—C3—C6—O1	25.5 (8)
O5—La1—O3ⁱⁱ—C7ⁱⁱ	49.4 (8)	C6—C3—C4—C1	176.7 (5)
O7—La1—O3ⁱⁱ—C7ⁱⁱ	−13.9 (7)	C4—C3—C6—O2	27.4 (8)
O8—La1—O3ⁱⁱ—C7ⁱⁱ	118.3 (7)	C2—C3—C6—O2	−153.9 (6)
O9—La1—O3ⁱⁱ—C7ⁱⁱ	52.5 (7)	C4—C3—C6—O1	−153.3 (5)
N1—La1—O3ⁱⁱ—C7ⁱⁱ	−170.5 (7)	C2—C3—C4—C1	−2.1 (8)
O4—La1—O1ⁱ—C6ⁱ	130.4 (6)	O5—C8—C8ⁱⁱⁱ—O5ⁱⁱⁱ	−180.0 (6)
O5—La1—O1ⁱ—C6ⁱ	−157.6 (6)	O5—C8—C8ⁱⁱⁱ—O6ⁱⁱⁱ	−0.2 (9)
O7—La1—O1ⁱ—C6ⁱ	−85.8 (6)	O6—C8—C8ⁱⁱⁱ—O5ⁱⁱⁱ	0.2 (9)
O8—La1—O1ⁱ—C6ⁱ	58.6 (7)	O6—C8—C8ⁱⁱⁱ—O6ⁱⁱⁱ	180.0 (6)
O9—La1—O1ⁱ—C6ⁱ	−56.3 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱⁱ	0.84	2.08	2.911 (8)	168
O7—H7B···O10^v	0.83	1.71	2.533 (12)	168
O8—H8A···O2^vi	0.83	1.83	2.660 (7)	173
O8—H8B···O6^vii	0.96	2.03	2.914 (7)	153
O9—H9A···O6^vii	0.88	2.27	2.987 (8)	138
O9—H9B···O10	0.85	1.73	2.390 (14)	133
O10—H10A···O5ⁱⁱ	0.83	2.24	2.885 (12)	135
O10—H10A···O8ⁱⁱ	0.83	2.29	2.924 (15)	133
O10—H10B···O9^viii	0.85	1.77	2.591 (17)	163
C5—H5A···O3ⁱⁱ	0.93	2.49	3.164 (7)	130

Symmetry codes: (ii) x−1, y, z; (v) x, y+1, z; (vi) −x+2, −y, −z+1; (vii) −x+1, −y, −z+2; (viii) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[La₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O
M_r	822.16
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.4614 (8), 6.6844 (8), 14.0796 (17)
α, β, γ (°)	89.735 (2), 85.266 (2), 73.135 (2)
V (Å³)	579.85 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.73
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.686, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	5023, 2046, 1795
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.093, 1.09
No. of reflections	2046
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.14, −2.13

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top

La1—N1	2.726 (4)	La1—O6ⁱⁱⁱ	2.550 (5)
La1—O1ⁱ	2.454 (4)	La1—O7	2.604 (7)
La1—O3ⁱⁱ	2.541 (5)	La1—O8	2.553 (5)
La1—O4	2.551 (5)	La1—O9	2.612 (7)
La1—O5	2.543 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱⁱ	0.84	2.08	2.911 (8)	168
O7—H7B···O10^iv	0.83	1.71	2.533 (12)	168
O8—H8A···O2^v	0.83	1.83	2.660 (7)	173
O8—H8B···O6^vi	0.96	2.03	2.914 (7)	153
O9—H9A···O6^vi	0.88	2.27	2.987 (8)	138
O9—H9B···O10	0.85	1.73	2.390 (14)	133
O10—H10A···O5ⁱⁱ	0.83	2.24	2.885 (12)	135
O10—H10A···O8ⁱⁱ	0.83	2.29	2.924 (15)	133
O10—H10B···O9^vii	0.85	1.77	2.591 (17)	163
C5—H5A···O3ⁱⁱ	0.93	2.49	3.164 (7)	130

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

Acknowledgements

This work was supported financially by Yuanpei University, Taiwan.

References

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