Poly[diaqua­(μ-oxalato)(μ-2-oxidopyridinium-3-carboxyl­ato)lanthanum(III)]

Hu, Z.; Zhu, Z.-B.

doi:10.1107/S1600536809018194

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m682

doi:10.1107/S1600536809018194

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Poly[diaqua(μ-oxalato)(μ-2-oxidopyridinium-3-carboxylato)lanthanum(III)]

Zhen Hu ^a and Zhi-Bo Zhu ^b ^*

^aAcademic Affairs Division, Southern Medical University, Guangzhou, Guangdong 510515, People's Republic of China, and ^bSchool of Pharmaceutical Sciences, Southern Medical University, Guangzhou, Guangdong 510515, People's Republic of China
^*Correspondence e-mail: zzb24@yahoo.com.cn

(Received 3 March 2009; accepted 14 May 2009; online 23 May 2009)

In the title complex, [La(C₆H₄NO₃)(C₂O₄)(H₂O)₂]_n, the La^III ion is coordinated by eight O atoms from two 2-oxidopyridinium-3-carboxylate ligands, two oxalate ligands and two water molecules in a distorted bicapped square-antiprismatic geometry. The carboxylate groups link adjacent La^III ions, forming two-dimensional layers that are further linked by N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For related structures, see: Huang et al. (2009 ); Xu et al. (2009 ).

Experimental

Crystal data

[La(C₆H₄NO₃)(C₂O₄)(H₂O)₂]
M_r = 401.06
Triclinic, $[P \overline 1]$
a = 8.0856 (18) Å
b = 8.5493 (19) Å
c = 9.388 (3) Å
α = 109.281 (3)°
β = 104.702 (3)°
γ = 104.940 (2)°
V = 549.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 3.93 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.460, T_max = 0.512
2843 measured reflections
1946 independent reflections
1870 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.069
S = 1.10
1946 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −1.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.86	1.96	2.789 (5)	162
O1W—H1W⋯O6ⁱ	0.85	2.01	2.805 (5)	155
O2W—H4W⋯O2Wⁱⁱ	0.85	2.00	2.853 (7)	180
O2W—H3W⋯O7ⁱⁱⁱ	0.85	1.97	2.753 (5)	152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018194/bi2356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018194/bi2356Isup2.hkl

checkCIF report

Comment top

Whereas a large number of metal derivatives of oxalic acid have been reported, there are few examples of metal derivatives of 2-oxynicotinic acid and oxalic acid: the crystal structures of praseodymium (Xu et al., 2009) and dysprosium (Huang et al., 2009) derivatives have been reported only. We report here a lanthanum(III) complex formed by reaction of lanthanum nitrate, 2-oxynicotinic acid and oxalic acid under hydrothermal conditions.

As illustrated in Fig. 1, each La^III centre adopts a distorted bicapped square-antiprismatic geometry, defined by eight O atoms from two 2-oxynicotinate ligands, two oxalate ligands, and two water molecules. The 2-oxynicotinate ligands and oxalate ligands link the La^III ions to form layers in the bc plane in which the shortest La···La separation is 4.429 (3) Å. These layers are connected through O—H···O and N—H···O hydrogen bonding (Table 1) involving 2-oxynicotinate ligands, oxalate ligands and the coordinating water molecules, forming a three-dimensional supramolecular network motif (Fig. 2).

Related literature top

For related structures, see: Huang et al. (2009); Xu et al. (2009).

Experimental top

A mixture of La₂O₃ (0.245 g, 0.75 mmol), 2-oxynicotinic acid (0.127 g, 1 mmol), oxalic acid (0.09 g, 1 mmol), water (10 ml) and HNO₃ (0.024 g, 0.385 mmol) was stirred vigorously for 20 min then sealed in a Teflon-lined stainless-steel autoclave (20 ml capacity). The autoclave was heated and maintained at 433 K for 4 days, then cooled to room temperature at 5 K h^-1 to yield colourless block crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure showing displacement ellipsoids at 30% probability for non-H atoms. Symmetry codes: (i) -x, -y, -z; (ii) -x, 1 - y, 1 - z; (iii) -x, -y, 1 - z. The H atoms on O2W are disordered.
	Fig. 2. Packing diagram showing part of the 2-D layers (horizontal).

Poly[diaqua(µ-oxalato)(µ-2-oxidopyridinium-3-carboxylato)lanthanum(III)] top

Crystal data top

[La(C₆H₄NO₃)(C₂O₄)(H₂O)₂]	Z = 2
M_r = 401.06	F(000) = 384
Triclinic, P1	D_x = 2.424 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0856 (18) Å	Cell parameters from 2827 reflections
b = 8.5493 (19) Å	θ = 2.5–28.3°
c = 9.388 (3) Å	µ = 3.93 mm⁻¹
α = 109.281 (3)°	T = 293 K
β = 104.702 (3)°	Block, colourless
γ = 104.940 (2)°	0.20 × 0.18 × 0.17 mm
V = 549.5 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	1946 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→9
T_min = 0.460, T_max = 0.512	k = −10→10
2843 measured reflections	l = −11→11

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0415P)² + 0.4664P] where P = (F_o² + 2F_c²)/3
1946 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.92 e Å⁻³
0 restraints	Δρ_min = −1.37 e Å⁻³

Crystal data top

[La(C₆H₄NO₃)(C₂O₄)(H₂O)₂]	γ = 104.940 (2)°
M_r = 401.06	V = 549.5 (2) Å³
Triclinic, P1	Z = 2
a = 8.0856 (18) Å	Mo Kα radiation
b = 8.5493 (19) Å	µ = 3.93 mm⁻¹
c = 9.388 (3) Å	T = 293 K
α = 109.281 (3)°	0.20 × 0.18 × 0.17 mm
β = 104.702 (3)°

Data collection top

Bruker APEXII CCD diffractometer	1946 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1870 reflections with I > 2σ(I)
T_min = 0.460, T_max = 0.512	R_int = 0.020
2843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.10	Δρ_max = 0.92 e Å⁻³
1946 reflections	Δρ_min = −1.37 e Å⁻³
172 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5156 (6)	0.3528 (6)	0.7873 (5)	0.0193 (9)
C2	0.4448 (6)	0.2225 (6)	0.8439 (5)	0.0190 (9)
C3	0.5510 (7)	0.2276 (6)	0.9869 (5)	0.0278 (10)
H3A	0.5043	0.1411	1.0209	0.033*
C4	0.7265 (7)	0.3590 (7)	1.0820 (6)	0.0340 (12)
H4A	0.7963	0.3617	1.1788	0.041*
C5	0.7924 (6)	0.4829 (7)	1.0291 (6)	0.0310 (11)
H5A	0.9085	0.5728	1.0910	0.037*
C6	0.2549 (6)	0.0837 (6)	0.7555 (5)	0.0195 (9)
C7	0.0124 (6)	0.0944 (6)	0.0035 (5)	0.0209 (9)
C8	0.0714 (6)	0.5526 (5)	0.4754 (5)	0.0180 (8)
La1	0.14649 (3)	0.16626 (3)	0.39929 (2)	0.01432 (11)
N1	0.6911 (5)	0.4769 (5)	0.8873 (5)	0.0253 (8)
H1A	0.7393	0.5561	0.8570	0.030*
O1	0.1395 (4)	0.0964 (4)	0.6424 (3)	0.0215 (7)
O2	0.2093 (4)	−0.0404 (4)	0.7976 (4)	0.0285 (7)
O3	0.4372 (4)	0.3643 (4)	0.6604 (4)	0.0276 (7)
O4	0.1045 (5)	0.2240 (4)	0.1390 (4)	0.0258 (7)
O5	−0.0601 (5)	0.1020 (4)	−0.1273 (4)	0.0275 (7)
O6	0.1897 (4)	0.4906 (4)	0.4461 (4)	0.0238 (7)
O7	0.0581 (4)	0.6932 (4)	0.4686 (4)	0.0263 (7)
O1W	0.4501 (5)	0.2684 (5)	0.3496 (4)	0.0400 (9)
H1W	0.5512	0.3270	0.4309	0.060*
H2W	0.4721	0.1911	0.2808	0.060*
O2W	0.3055 (5)	−0.0633 (5)	0.4169 (4)	0.0329 (8)
H3W	0.2604	−0.1491	0.4396	0.049*
H4W	0.4214	−0.0254	0.4667	0.049*	0.50
H4W'	0.2871	−0.1202	0.3175	0.049*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.018 (2)	0.016 (2)	0.018 (2)	0.0023 (17)	0.0060 (17)	0.0040 (17)
C2	0.017 (2)	0.017 (2)	0.0160 (19)	0.0019 (17)	0.0018 (17)	0.0062 (17)
C3	0.027 (2)	0.023 (2)	0.024 (2)	0.002 (2)	0.000 (2)	0.012 (2)
C4	0.024 (3)	0.034 (3)	0.024 (2)	0.001 (2)	−0.011 (2)	0.012 (2)
C5	0.017 (2)	0.029 (3)	0.029 (2)	0.001 (2)	−0.0042 (19)	0.006 (2)
C6	0.016 (2)	0.020 (2)	0.016 (2)	−0.0004 (17)	0.0025 (17)	0.0074 (17)
C7	0.021 (2)	0.024 (2)	0.017 (2)	0.0035 (18)	0.0066 (18)	0.0103 (18)
C8	0.014 (2)	0.014 (2)	0.017 (2)	0.0005 (17)	−0.0001 (16)	0.0029 (17)
La1	0.01183 (15)	0.01383 (16)	0.01434 (15)	0.00163 (11)	0.00223 (11)	0.00694 (11)
N1	0.0186 (19)	0.022 (2)	0.027 (2)	−0.0013 (16)	0.0045 (16)	0.0110 (17)
O1	0.0154 (15)	0.0253 (17)	0.0172 (15)	0.0003 (13)	−0.0005 (12)	0.0118 (13)
O2	0.0215 (17)	0.0269 (18)	0.0325 (18)	0.0002 (14)	0.0028 (14)	0.0192 (15)
O3	0.0211 (17)	0.0312 (18)	0.0235 (16)	−0.0002 (14)	0.0014 (14)	0.0163 (14)
O4	0.0326 (19)	0.0190 (16)	0.0157 (15)	−0.0002 (14)	0.0040 (14)	0.0068 (13)
O5	0.0369 (19)	0.0238 (16)	0.0163 (15)	0.0085 (15)	0.0030 (14)	0.0093 (13)
O6	0.0193 (16)	0.0192 (16)	0.0336 (17)	0.0070 (13)	0.0107 (14)	0.0116 (14)
O7	0.0294 (18)	0.0209 (16)	0.0373 (18)	0.0110 (14)	0.0169 (15)	0.0177 (14)
O1W	0.0197 (18)	0.057 (2)	0.0307 (19)	0.0001 (17)	0.0090 (15)	0.0158 (18)
O2W	0.0285 (18)	0.040 (2)	0.043 (2)	0.0178 (16)	0.0155 (16)	0.0276 (17)

Geometric parameters (Å, º) top

C1—O3	1.248 (5)	La1—O6	2.574 (3)
C1—N1	1.382 (6)	La1—O5ⁱ	2.582 (3)
C1—C2	1.437 (6)	La1—O3	2.585 (3)
C2—C3	1.377 (6)	La1—O1W	2.598 (3)
C2—C6	1.489 (6)	La1—O4	2.606 (3)
C3—C4	1.395 (7)	La1—O7ⁱⁱ	2.608 (3)
C3—H3A	0.930	La1—O1ⁱⁱⁱ	2.612 (3)
C4—C5	1.357 (7)	La1—O2W	2.634 (3)
C4—H4A	0.930	La1—O2ⁱⁱⁱ	2.691 (3)
C5—N1	1.351 (6)	N1—H1A	0.860
C5—H5A	0.930	O1—La1ⁱⁱⁱ	2.612 (3)
C6—O2	1.252 (5)	O2—La1ⁱⁱⁱ	2.691 (3)
C6—O1	1.279 (5)	O5—La1ⁱ	2.582 (3)
C7—O4	1.250 (5)	O7—La1ⁱⁱ	2.608 (3)
C7—O5	1.251 (5)	O1W—H1W	0.850
C7—C7ⁱ	1.550 (9)	O1W—H2W	0.850
C8—O6	1.253 (5)	O2W—H3W	0.850
C8—O7	1.255 (5)	O2W—H4W	0.850
C8—C8ⁱⁱ	1.537 (8)	O2W—H4W'	0.850
La1—O1	2.553 (3)

O3—C1—N1	118.0 (4)	O1—La1—O1ⁱⁱⁱ	61.92 (11)
O3—C1—C2	127.4 (4)	O6—La1—O1ⁱⁱⁱ	130.59 (10)
N1—C1—C2	114.6 (4)	O5ⁱ—La1—O1ⁱⁱⁱ	70.65 (10)
C3—C2—C1	120.0 (4)	O3—La1—O1ⁱⁱⁱ	127.57 (9)
C3—C2—C6	118.0 (4)	O1W—La1—O1ⁱⁱⁱ	148.31 (12)
C1—C2—C6	121.9 (4)	O4—La1—O1ⁱⁱⁱ	111.41 (10)
C2—C3—C4	121.8 (4)	O7ⁱⁱ—La1—O1ⁱⁱⁱ	72.58 (10)
C2—C3—H3A	119.1	O1—La1—O2W	68.95 (10)
C4—C3—H3A	119.1	O6—La1—O2W	147.03 (10)
C5—C4—C3	118.1 (4)	O5ⁱ—La1—O2W	64.56 (10)
C5—C4—H4A	121.0	O3—La1—O2W	78.73 (11)
C3—C4—H4A	121.0	O1W—La1—O2W	72.87 (12)
N1—C5—C4	120.6 (4)	O4—La1—O2W	115.38 (10)
N1—C5—H5A	119.7	O7ⁱⁱ—La1—O2W	138.08 (10)
C4—C5—H5A	119.7	O1ⁱⁱⁱ—La1—O2W	81.33 (10)
O2—C6—O1	121.1 (4)	O1—La1—O2ⁱⁱⁱ	105.06 (9)
O2—C6—C2	119.0 (4)	O6—La1—O2ⁱⁱⁱ	92.61 (10)
O1—C6—C2	119.8 (4)	O5ⁱ—La1—O2ⁱⁱⁱ	66.21 (10)
O4—C7—O5	126.4 (4)	O3—La1—O2ⁱⁱⁱ	157.15 (11)
O4—C7—C7ⁱ	116.9 (4)	O1W—La1—O2ⁱⁱⁱ	131.48 (11)
O5—C7—C7ⁱ	116.7 (5)	O4—La1—O2ⁱⁱⁱ	67.14 (10)
O6—C8—O7	126.1 (4)	O7ⁱⁱ—La1—O2ⁱⁱⁱ	65.52 (10)
O6—C8—C8ⁱⁱ	117.3 (4)	O1ⁱⁱⁱ—La1—O2ⁱⁱⁱ	49.08 (9)
O7—C8—C8ⁱⁱ	116.6 (4)	O2W—La1—O2ⁱⁱⁱ	118.71 (11)
O1—La1—O6	115.01 (10)	C5—N1—C1	124.9 (4)
O1—La1—O5ⁱ	116.73 (10)	C5—N1—H1A	117.6
O6—La1—O5ⁱ	127.50 (10)	C1—N1—H1A	117.6
O1—La1—O3	65.68 (10)	C6—O1—La1	135.9 (3)
O6—La1—O3	74.38 (10)	C6—O1—La1ⁱⁱⁱ	96.3 (3)
O5ⁱ—La1—O3	136.55 (11)	La1—O1—La1ⁱⁱⁱ	118.08 (11)
O1—La1—O1W	121.99 (10)	C6—O2—La1ⁱⁱⁱ	93.3 (2)
O6—La1—O1W	78.71 (11)	C1—O3—La1	136.4 (3)
O5ⁱ—La1—O1W	81.66 (11)	C7—O4—La1	118.5 (3)
O3—La1—O1W	65.28 (11)	C7—O5—La1ⁱ	119.4 (3)
O1—La1—O4	172.10 (10)	C8—O6—La1	120.7 (3)
O6—La1—O4	65.38 (10)	C8—O7—La1ⁱⁱ	119.8 (3)
O5ⁱ—La1—O4	62.14 (10)	La1—O1W—H1W	118.9
O3—La1—O4	120.98 (10)	La1—O1W—H2W	118.3
O1W—La1—O4	65.90 (11)	H1W—O1W—H2W	105.2
O1—La1—O7ⁱⁱ	69.92 (10)	La1—O2W—H3W	122.1
O6—La1—O7ⁱⁱ	62.13 (9)	La1—O2W—H4W	119.6
O5ⁱ—La1—O7ⁱⁱ	131.12 (11)	H3W—O2W—H4W	105.2
O3—La1—O7ⁱⁱ	91.67 (11)	La1—O2W—H4W'	101.0
O1W—La1—O7ⁱⁱ	139.07 (11)	H3W—O2W—H4W'	100.6
O4—La1—O7ⁱⁱ	104.60 (10)	H4W—O2W—H4W'	105.2

O3—C1—C2—C3	179.2 (4)	N1—C1—O3—La1	168.2 (3)
N1—C1—C2—C3	−0.4 (6)	C2—C1—O3—La1	−11.5 (7)
O3—C1—C2—C6	−3.1 (7)	O1—La1—O3—C1	22.7 (4)
N1—C1—C2—C6	177.2 (4)	O6—La1—O3—C1	150.2 (4)
C1—C2—C3—C4	1.3 (7)	O5ⁱ—La1—O3—C1	−81.2 (4)
C6—C2—C3—C4	−176.5 (4)	O1W—La1—O3—C1	−125.3 (4)
C2—C3—C4—C5	−0.6 (8)	O4—La1—O3—C1	−162.1 (4)
C3—C4—C5—N1	−0.8 (8)	O7ⁱⁱ—La1—O3—C1	89.7 (4)
C3—C2—C6—O2	−11.8 (6)	O1ⁱⁱⁱ—La1—O3—C1	20.6 (5)
C1—C2—C6—O2	170.5 (4)	O2W—La1—O3—C1	−49.1 (4)
C3—C2—C6—O1	165.6 (4)	O2ⁱⁱⁱ—La1—O3—C1	92.9 (5)
C1—C2—C6—O1	−12.0 (6)	O5—C7—O4—La1	160.6 (4)
C4—C5—N1—C1	1.7 (7)	C7ⁱ—C7—O4—La1	−20.2 (6)
O3—C1—N1—C5	179.3 (4)	O6—La1—O4—C7	−157.7 (3)
C2—C1—N1—C5	−1.0 (6)	O5ⁱ—La1—O4—C7	20.9 (3)
O2—C6—O1—La1	−137.1 (4)	O3—La1—O4—C7	150.7 (3)
C2—C6—O1—La1	45.4 (6)	O1W—La1—O4—C7	114.1 (3)
O2—C6—O1—La1ⁱⁱⁱ	5.4 (4)	O7ⁱⁱ—La1—O4—C7	−108.3 (3)
C2—C6—O1—La1ⁱⁱⁱ	−172.0 (3)	O1ⁱⁱⁱ—La1—O4—C7	−31.6 (4)
O6—La1—O1—C6	−98.9 (4)	O2W—La1—O4—C7	58.8 (3)
O5ⁱ—La1—O1—C6	90.3 (4)	O2ⁱⁱⁱ—La1—O4—C7	−53.3 (3)
O3—La1—O1—C6	−41.3 (4)	O4—C7—O5—La1ⁱ	159.7 (4)
O1W—La1—O1—C6	−6.8 (4)	C7ⁱ—C7—O5—La1ⁱ	−19.6 (6)
O7ⁱⁱ—La1—O1—C6	−142.8 (4)	O7—C8—O6—La1	−165.0 (3)
O1ⁱⁱⁱ—La1—O1—C6	136.7 (5)	C8ⁱⁱ—C8—O6—La1	15.1 (6)
O2W—La1—O1—C6	45.5 (4)	O1—La1—O6—C8	−63.1 (3)
O2ⁱⁱⁱ—La1—O1—C6	160.9 (4)	O5ⁱ—La1—O6—C8	106.6 (3)
O6—La1—O1—La1ⁱⁱⁱ	124.39 (13)	O3—La1—O6—C8	−116.0 (3)
O5ⁱ—La1—O1—La1ⁱⁱⁱ	−46.43 (16)	O1W—La1—O6—C8	176.7 (3)
O3—La1—O1—La1ⁱⁱⁱ	−178.07 (17)	O4—La1—O6—C8	108.2 (3)
O1W—La1—O1—La1ⁱⁱⁱ	−143.50 (14)	O7ⁱⁱ—La1—O6—C8	−15.6 (3)
O7ⁱⁱ—La1—O1—La1ⁱⁱⁱ	80.43 (14)	O1ⁱⁱⁱ—La1—O6—C8	10.4 (4)
O1ⁱⁱⁱ—La1—O1—La1ⁱⁱⁱ	0.0	O2W—La1—O6—C8	−152.6 (3)
O2W—La1—O1—La1ⁱⁱⁱ	−91.27 (15)	O2ⁱⁱⁱ—La1—O6—C8	44.9 (3)
O2ⁱⁱⁱ—La1—O1—La1ⁱⁱⁱ	24.16 (15)	O6—C8—O7—La1ⁱⁱ	−165.3 (3)
O1—C6—O2—La1ⁱⁱⁱ	−5.2 (4)	C8ⁱⁱ—C8—O7—La1ⁱⁱ	14.7 (6)
C2—C6—O2—La1ⁱⁱⁱ	172.2 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4^iv	0.86	1.96	2.789 (5)	162
O1W—H1W···O6^iv	0.85	2.01	2.805 (5)	155
O2W—H4W···O2W^v	0.85	2.00	2.853 (7)	180
O2W—H3W···O7^vi	0.85	1.97	2.753 (5)	152

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

Experimental details

Crystal data
Chemical formula	[La(C₆H₄NO₃)(C₂O₄)(H₂O)₂]
M_r	401.06
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.0856 (18), 8.5493 (19), 9.388 (3)
α, β, γ (°)	109.281 (3), 104.702 (3), 104.940 (2)
V (Å³)	549.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.93
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.460, 0.512
No. of measured, independent and observed [I > 2σ(I)] reflections	2843, 1946, 1870
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.069, 1.10
No. of reflections	1946
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −1.37

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.86	1.96	2.789 (5)	162
O1W—H1W···O6ⁱ	0.85	2.01	2.805 (5)	155
O2W—H4W···O2Wⁱⁱ	0.85	2.00	2.853 (7)	180
O2W—H3W···O7ⁱⁱⁱ	0.85	1.97	2.753 (5)	152

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

Acknowledgements

The authors acknowledge Southern Medical University for supporting this work.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huang, C.-D., Huang, J.-X., Wu, Y.-Y., Lian, Y.-Y. & Zeng, R.-H. (2009). Acta Cryst. E65, m177–m178. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, Y.-J., Yang, X.-X. & Zhao, H.-B. (2009). Acta Cryst. E65, m310. Web of Science CSD CrossRef IUCr Journals Google Scholar