Poly[[(μ-3-amino­pyrazine-2-carboxyl­ato-κ3N1,O:O′)diaqua­(μ-oxalato-κ4O1,O2:O1′,O2′)lanthanum(III)] monohydrate]

Gao, S.; Ng, S.W.

doi:10.1107/S1600536811034404

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1301

doi:10.1107/S1600536811034404

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Poly[[(μ-3-aminopyrazine-2-carboxylato-κ³N¹,O:O′)diaqua(μ-oxalato-κ⁴O¹,O²:O^1′,O^2′)lanthanum(III)] monohydrate]

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 1 July 2011; accepted 22 August 2011; online 27 August 2011)

The water-coordinated La^III atom in the title compound, {[La(C₅H₄N₃O₂)(C₂O₄)(H₂O)₂]·H₂O}_n, is N,O-chelated by a 3-aminopyrazine-2-carboxylate ion; this ion links adjacent metal atoms to form a chain parallel to [010]. The oxalate ion serves as a bis-bidentate chelate that links adjacent metal atoms to form a chain parallel to [001]. The two bridging ions give rise to a layer motif parallel to (100) in which the La^III atom exists in a distorted tricapped trigonal prismatic geometry. Extensive hydrogen bonding between the constituents stabilizes the structure.

Related literature

For a related structure, see: Leciejewicz et al. (2004 ). For pyrazinecarboxylic acid decomposition with subsequent oxalate formation, which has been documented in other lanthanum systems, see: Li et al. (2006 ).

Experimental

Crystal data

[La(C₅H₄N₃O₂)(C₂O₄)(H₂O)₂]·H₂O
M_r = 419.09
Monoclinic, C 2/c
a = 18.2193 (5) Å
b = 10.5507 (3) Å
c = 13.1307 (5) Å
β = 105.292 (1)°
V = 2434.70 (13) Å³
Z = 8
Mo Kα radiation
μ = 3.56 mm⁻¹
T = 293 K
0.14 × 0.12 × 0.08 mm

Data collection

Rigaku RAXIS-RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.636, T_max = 0.764
11571 measured reflections
2780 independent reflections
2408 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.064
S = 1.03
2780 reflections
213 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.19 e Å⁻³
Δρ_min = −0.90 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11⋯O6ⁱ	0.84 (1)	1.89 (1)	2.720 (3)	169 (3)
O1W—H12⋯N2ⁱⁱ	0.84 (1)	2.00 (1)	2.842 (3)	175 (3)
O2W—H21⋯O5ⁱⁱⁱ	0.84 (1)	1.95 (1)	2.787 (3)	175 (4)
O2W—H22⋯O3W	0.84 (1)	2.16 (2)	2.908 (4)	148 (4)
O3W—H31⋯O2W^iv	0.84 (1)	2.19 (1)	3.017 (4)	165 (4)
O3W—H32⋯N3ⁱⁱⁱ	0.84 (1)	2.33 (2)	3.152 (5)	165 (4)
N3—H1⋯O2	0.88 (1)	2.06 (3)	2.711 (3)	130 (3)
N3—H2⋯O3^v	0.88 (1)	2.10 (1)	2.967 (3)	167 (3)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iv) $[-x+2, y, -z+{\script{3\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034404/qk2018sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034404/qk2018Isup2.hkl

checkCIF report

Comment top

The chelating ability of the 3-aminopyrazine-2-carboxylate anion is probably similar to that of the pyrazine-2-carboxylate anion, and the crystal structures of a number of lanthanum carboxylates have been reported. Hydrated lanthanum tris(pyrazine-2-carboxylate) adopts a chain motif (Leciejewicz et al., 2004). The additional amino substitution in the 3-aminopyrazine-2-carboxylate should be expected to consolidate the crystal structure of the title lanthanum derivative through extensive hydrogen bonding. The water-coordinated La^III atom in La(H₂O)₂(C₂O₄)(C₅H₄N₃O₂).H₂O (Scheme I, Fig. 1) is N,O-chelated by an 3-aminopyrazine-2-carboxylate ion; this ion links adjacent metal atoms to form a chain parallel to [010]. The presence of an oxalate ion is explained by the decomposition of 3-aminopyrazine-2-carboxylic acid; the oxalate ion serves as a bis-bidentate chelate that links adjacent metal atoms. The two bridging ions give rise to a layer motif parallel to [100] in which the La^III atom exists in a nine-coordinate environment. The geometry is best described as a distorted tricapped trigonal prism. The upper prism triangle is made up of the atoms O1, O4 and O2w, and the lower prism triangle by the atoms O2, O5 and O1w.

The layers interact with the lattice water molecules to generate a three-dimensional hydrogen-bonded network (Table 1).

Related literature top

For a related structure, see: Leciejewicz et al. (2004). For pyrazinecarboxylic acid decomposition with subsequent oxalate formation, which has been documented in other lanthanum systems; see: Li et al. (2006).

Experimental top

Lanthanum nitrate hexahydrate (0.5 mmol) and 3-aminopyrazine-2-carboxylic acid (2 mmol) were dissolved in water (15 ml). The solution was sealed in a 25 ml Teflon-lined stainless steel bomb and held at 443 K for 3 d. The bomb was gradually cooled to room temperature, and colorless prismatic crystals were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of the layer structure of La(H₂O)₂(C₂O₄)(C₅H₄N₃O₂).H₂O at the 50% probability level; H atoms are drawn as spheres of arbitrary radius.

Poly[[(µ-3-aminopyrazine-2-carboxylato- κ³N¹,O:O')diaqua(µ-oxalato- κ⁴O¹,O²:O^1',O^2')lanthanum(III)] monohydrate] top

Crystal data top

[La(C₅H₄N₃O₂)(C₂O₄)(H₂O)₂]·H₂O	F(000) = 1616
M_r = 419.09	D_x = 2.287 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8439 reflections
a = 18.2193 (5) Å	θ = 3.2–27.4°
b = 10.5507 (3) Å	µ = 3.56 mm⁻¹
c = 13.1307 (5) Å	T = 293 K
β = 105.292 (1)°	Prism, colourless
V = 2434.70 (13) Å³	0.14 × 0.12 × 0.08 mm
Z = 8

Data collection top

Rigaku RAXIS-RAPID IP diffractometer	2780 independent reflections
Radiation source: fine-focus sealed tube	2408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 27.4°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −22→23
T_min = 0.636, T_max = 0.764	k = −13→11
11571 measured reflections	l = −17→17

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) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0366P)² + 0.9654P] where P = (F_o² + 2F_c²)/3
2780 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 1.19 e Å⁻³
11 restraints	Δρ_min = −0.90 e Å⁻³

Crystal data top

[La(C₅H₄N₃O₂)(C₂O₄)(H₂O)₂]·H₂O	V = 2434.70 (13) Å³
M_r = 419.09	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.2193 (5) Å	µ = 3.56 mm⁻¹
b = 10.5507 (3) Å	T = 293 K
c = 13.1307 (5) Å	0.14 × 0.12 × 0.08 mm
β = 105.292 (1)°

Data collection top

Rigaku RAXIS-RAPID IP diffractometer	2780 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2408 reflections with I > 2σ(I)
T_min = 0.636, T_max = 0.764	R_int = 0.038
11571 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	11 restraints
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 1.19 e Å⁻³
2780 reflections	Δρ_min = −0.90 e Å⁻³
213 parameters

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

	x	y	z	U_iso*/U_eq
La1	0.753537 (8)	0.505715 (13)	0.708865 (11)	0.01578 (8)
O1	0.70771 (10)	0.72700 (18)	0.73633 (16)	0.0229 (4)
O3	0.82152 (11)	0.4381 (2)	0.56948 (15)	0.0265 (5)
O4	0.70436 (11)	0.60558 (18)	0.52529 (15)	0.0232 (4)
O5	0.70189 (11)	0.59526 (17)	0.35400 (15)	0.0215 (4)
O6	0.81026 (11)	0.41769 (18)	0.39750 (15)	0.0237 (4)
O1W	0.67446 (12)	0.33869 (19)	0.59002 (18)	0.0301 (5)
H11	0.6840 (18)	0.2609 (12)	0.590 (3)	0.046 (11)*
H12	0.6393 (18)	0.356 (3)	0.536 (2)	0.064 (13)*
O2W	0.86289 (12)	0.66714 (19)	0.70250 (17)	0.0273 (5)
H21	0.8424 (19)	0.7373 (19)	0.682 (3)	0.053 (12)*
H22	0.8870 (19)	0.643 (3)	0.660 (2)	0.052 (12)*
O2	0.62477 (11)	0.88451 (18)	0.70103 (17)	0.0283 (5)
O3W	0.99478 (18)	0.6325 (3)	0.6200 (3)	0.0556 (7)
H31	1.0385 (11)	0.644 (4)	0.661 (2)	0.075 (17)*
H32	0.999 (2)	0.628 (4)	0.5577 (12)	0.073 (16)*
N1	0.59859 (12)	0.5541 (2)	0.67230 (18)	0.0188 (5)
N2	0.44670 (13)	0.6197 (2)	0.5937 (2)	0.0241 (5)
N3	0.47703 (15)	0.8320 (3)	0.6050 (3)	0.0338 (7)
H1	0.5096 (15)	0.893 (2)	0.630 (3)	0.033 (10)*
H2	0.4284 (8)	0.851 (3)	0.593 (3)	0.043 (10)*
C1	0.54410 (17)	0.4653 (3)	0.6480 (2)	0.0233 (6)
H1A	0.5572	0.3801	0.6577	0.028*
C2	0.4688 (2)	0.4990 (2)	0.6088 (3)	0.0256 (7)
H2A	0.4321	0.4355	0.5924	0.031*
C3	0.50011 (15)	0.7099 (3)	0.6213 (2)	0.0204 (6)
C4	0.57805 (15)	0.6755 (2)	0.6627 (2)	0.0176 (5)
C5	0.64079 (15)	0.7689 (3)	0.7022 (2)	0.0196 (6)
C6	0.72721 (15)	0.5654 (2)	0.4499 (2)	0.0177 (5)
C7	0.79244 (16)	0.4649 (3)	0.4748 (2)	0.0180 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.01427 (11)	0.02279 (11)	0.00982 (11)	0.00134 (6)	0.00236 (7)	0.00027 (5)
O1	0.0147 (10)	0.0293 (10)	0.0226 (11)	−0.0015 (9)	0.0012 (8)	−0.0039 (8)
O3	0.0269 (11)	0.0386 (12)	0.0137 (10)	0.0120 (10)	0.0048 (8)	0.0028 (9)
O4	0.0259 (10)	0.0301 (10)	0.0150 (10)	0.0091 (9)	0.0081 (8)	0.0023 (8)
O5	0.0249 (10)	0.0275 (10)	0.0117 (10)	0.0057 (8)	0.0038 (8)	0.0036 (8)
O6	0.0312 (11)	0.0256 (10)	0.0149 (10)	0.0068 (9)	0.0072 (8)	0.0002 (8)
O1W	0.0312 (12)	0.0211 (10)	0.0297 (13)	0.0042 (10)	−0.0066 (10)	−0.0027 (9)
O2W	0.0276 (11)	0.0256 (11)	0.0309 (13)	0.0028 (10)	0.0117 (10)	0.0026 (9)
O2	0.0225 (10)	0.0244 (10)	0.0337 (13)	−0.0033 (9)	−0.0001 (9)	−0.0059 (9)
O3W	0.0518 (18)	0.071 (2)	0.0455 (19)	0.0010 (17)	0.0152 (15)	−0.0004 (16)
N1	0.0172 (11)	0.0232 (12)	0.0160 (12)	0.0003 (10)	0.0045 (9)	0.0008 (9)
N2	0.0165 (11)	0.0327 (13)	0.0223 (13)	−0.0017 (11)	0.0038 (10)	−0.0022 (10)
N3	0.0189 (14)	0.0286 (14)	0.0486 (19)	0.0028 (12)	−0.0005 (13)	−0.0035 (13)
C1	0.0224 (15)	0.0234 (13)	0.0242 (16)	−0.0008 (13)	0.0064 (12)	0.0004 (12)
C2	0.0213 (16)	0.0301 (17)	0.0256 (18)	−0.0086 (12)	0.0067 (13)	−0.0006 (11)
C3	0.0184 (13)	0.0275 (14)	0.0150 (14)	0.0026 (12)	0.0038 (11)	−0.0032 (11)
C4	0.0163 (13)	0.0233 (13)	0.0129 (13)	−0.0031 (11)	0.0032 (10)	−0.0025 (10)
C5	0.0195 (14)	0.0264 (14)	0.0133 (14)	0.0007 (12)	0.0049 (11)	−0.0008 (11)
C6	0.0180 (13)	0.0189 (13)	0.0163 (14)	−0.0004 (12)	0.0044 (10)	0.0012 (10)
C7	0.0163 (14)	0.0225 (12)	0.0144 (14)	0.0003 (12)	0.0029 (11)	0.0002 (11)

Geometric parameters (Å, º) top

La1—O1W	2.536 (2)	O2W—H22	0.838 (10)
La1—O1	2.5371 (19)	O2—C5	1.254 (3)
La1—O6ⁱ	2.5507 (19)	O2—La1^iv	2.5627 (19)
La1—O2ⁱⁱ	2.5627 (19)	O3W—H31	0.844 (10)
La1—O4	2.5659 (19)	O3W—H32	0.843 (10)
La1—O3	2.5668 (19)	N1—C4	1.331 (3)
La1—O5ⁱ	2.5687 (18)	N1—C1	1.341 (4)
La1—O2W	2.639 (2)	N2—C2	1.334 (3)
La1—N1	2.783 (2)	N2—C3	1.341 (4)
O1—C5	1.263 (3)	N3—C3	1.355 (4)
O3—C7	1.248 (3)	N3—H1	0.880 (10)
O4—C6	1.246 (3)	N3—H2	0.880 (10)
O5—C6	1.261 (3)	C1—C2	1.379 (5)
O5—La1ⁱⁱⁱ	2.5687 (18)	C1—H1A	0.9300
O6—C7	1.248 (3)	C2—H2A	0.9300
O6—La1ⁱⁱⁱ	2.5507 (19)	C3—C4	1.427 (4)
O1W—H11	0.838 (10)	C4—C5	1.495 (4)
O1W—H12	0.841 (10)	C6—C7	1.561 (4)
O2W—H21	0.842 (10)

O1W—La1—O1	124.90 (6)	C6—O5—La1ⁱⁱⁱ	121.85 (17)
O1W—La1—O6ⁱ	146.79 (7)	C7—O6—La1ⁱⁱⁱ	122.53 (17)
O1—La1—O6ⁱ	68.57 (6)	La1—O1W—H11	126 (2)
O1W—La1—O2ⁱⁱ	102.67 (6)	La1—O1W—H12	123 (2)
O1—La1—O2ⁱⁱ	132.12 (6)	H11—O1W—H12	109.1 (17)
O6ⁱ—La1—O2ⁱⁱ	68.29 (7)	La1—O2W—H21	108 (2)
O1W—La1—O4	72.92 (7)	La1—O2W—H22	111 (3)
O1—La1—O4	73.09 (6)	H21—O2W—H22	108.7 (17)
O6ⁱ—La1—O4	137.21 (6)	C5—O2—La1^iv	108.04 (16)
O2ⁱⁱ—La1—O4	133.14 (6)	H31—O3W—H32	108.1 (17)
O1W—La1—O3	70.77 (7)	C4—N1—C1	118.5 (2)
O1—La1—O3	126.58 (7)	C4—N1—La1	116.11 (17)
O6ⁱ—La1—O3	129.22 (6)	C1—N1—La1	124.51 (19)
O2ⁱⁱ—La1—O3	70.67 (7)	C2—N2—C3	117.9 (2)
O4—La1—O3	63.83 (6)	C3—N3—H1	119 (2)
O1W—La1—O5ⁱ	84.75 (7)	C3—N3—H2	120 (2)
O1—La1—O5ⁱ	94.45 (6)	H1—N3—H2	117 (3)
O6ⁱ—La1—O5ⁱ	62.92 (6)	N1—C1—C2	120.7 (3)
O2ⁱⁱ—La1—O5ⁱ	83.81 (6)	N1—C1—H1A	119.7
O4—La1—O5ⁱ	139.62 (6)	C2—C1—H1A	119.7
O3—La1—O5ⁱ	138.92 (6)	N2—C2—C1	122.2 (3)
O1W—La1—O2W	137.74 (7)	N2—C2—H2A	118.9
O1—La1—O2W	71.95 (6)	C1—C2—H2A	118.9
O6ⁱ—La1—O2W	73.16 (6)	N2—C3—N3	117.4 (2)
O2ⁱⁱ—La1—O2W	76.60 (6)	N2—C3—C4	120.1 (2)
O4—La1—O2W	77.57 (7)	N3—C3—C4	122.6 (3)
O3—La1—O2W	69.30 (7)	N1—C4—C3	120.5 (2)
O5ⁱ—La1—O2W	135.93 (6)	N1—C4—C5	115.5 (2)
O1W—La1—N1	68.62 (7)	C3—C4—C5	123.9 (2)
O1—La1—N1	59.92 (6)	O2—C5—O1	123.0 (2)
O6ⁱ—La1—N1	104.01 (6)	O2—C5—C4	118.9 (2)
O2ⁱⁱ—La1—N1	152.36 (7)	O1—C5—C4	118.1 (2)
O4—La1—N1	71.07 (6)	O4—C6—O5	126.7 (3)
O3—La1—N1	125.89 (6)	O4—C6—C7	117.4 (2)
O5ⁱ—La1—N1	69.55 (6)	O5—C6—C7	115.9 (2)
O2W—La1—N1	128.03 (7)	O3—C7—O6	125.9 (3)
C5—O1—La1	126.49 (17)	O3—C7—C6	117.6 (2)
C7—O3—La1	119.28 (17)	O6—C7—C6	116.5 (2)
C6—O4—La1	120.00 (17)

O1W—La1—O1—C5	7.2 (2)	O3—La1—N1—C1	69.9 (2)
O6ⁱ—La1—O1—C5	−138.1 (2)	O5ⁱ—La1—N1—C1	−66.4 (2)
O2ⁱⁱ—La1—O1—C5	−165.2 (2)	O2W—La1—N1—C1	160.6 (2)
O4—La1—O1—C5	61.3 (2)	C4—N1—C1—C2	3.3 (4)
O3—La1—O1—C5	98.2 (2)	La1—N1—C1—C2	−165.7 (2)
O5ⁱ—La1—O1—C5	−79.5 (2)	C3—N2—C2—C1	−2.2 (5)
O2W—La1—O1—C5	143.4 (2)	N1—C1—C2—N2	−0.3 (5)
N1—La1—O1—C5	−16.2 (2)	C2—N2—C3—N3	179.7 (3)
O1W—La1—O3—C7	67.4 (2)	C2—N2—C3—C4	1.6 (4)
O1—La1—O3—C7	−52.4 (2)	C1—N1—C4—C3	−3.8 (4)
O6ⁱ—La1—O3—C7	−143.4 (2)	La1—N1—C4—C3	166.12 (19)
O2ⁱⁱ—La1—O3—C7	179.0 (2)	C1—N1—C4—C5	173.5 (2)
O4—La1—O3—C7	−12.6 (2)	La1—N1—C4—C5	−16.5 (3)
O5ⁱ—La1—O3—C7	124.2 (2)	N2—C3—C4—N1	1.4 (4)
O2W—La1—O3—C7	−98.5 (2)	N3—C3—C4—N1	−176.6 (3)
N1—La1—O3—C7	24.1 (2)	N2—C3—C4—C5	−175.7 (3)
O1W—La1—O4—C6	−66.9 (2)	N3—C3—C4—C5	6.3 (4)
O1—La1—O4—C6	157.1 (2)	La1^iv—O2—C5—O1	−4.6 (3)
O6ⁱ—La1—O4—C6	130.02 (19)	La1^iv—O2—C5—C4	174.72 (19)
O2ⁱⁱ—La1—O4—C6	24.6 (2)	La1—O1—C5—O2	−166.0 (2)
O3—La1—O4—C6	9.60 (19)	La1—O1—C5—C4	14.7 (3)
O5ⁱ—La1—O4—C6	−126.34 (19)	N1—C4—C5—O2	−176.0 (2)
O2W—La1—O4—C6	82.4 (2)	C3—C4—C5—O2	1.2 (4)
N1—La1—O4—C6	−139.6 (2)	N1—C4—C5—O1	3.3 (4)
O1W—La1—N1—C4	−143.34 (19)	C3—C4—C5—O1	−179.4 (3)
O1—La1—N1—C4	16.16 (17)	La1—O4—C6—O5	171.5 (2)
O6ⁱ—La1—N1—C4	70.73 (18)	La1—O4—C6—C7	−6.8 (3)
O2ⁱⁱ—La1—N1—C4	140.54 (18)	La1ⁱⁱⁱ—O5—C6—O4	−177.5 (2)
O4—La1—N1—C4	−64.83 (18)	La1ⁱⁱⁱ—O5—C6—C7	0.8 (3)
O3—La1—N1—C4	−99.37 (19)	La1—O3—C7—O6	−164.8 (2)
O5ⁱ—La1—N1—C4	124.31 (19)	La1—O3—C7—C6	14.4 (3)
O2W—La1—N1—C4	−8.7 (2)	La1ⁱⁱⁱ—O6—C7—O3	−174.9 (2)
O1W—La1—N1—C1	25.9 (2)	La1ⁱⁱⁱ—O6—C7—C6	5.8 (3)
O1—La1—N1—C1	−174.6 (2)	O4—C6—C7—O3	−5.2 (4)
O6ⁱ—La1—N1—C1	−120.0 (2)	O5—C6—C7—O3	176.4 (2)
O2ⁱⁱ—La1—N1—C1	−50.2 (3)	O4—C6—C7—O6	174.1 (2)
O4—La1—N1—C1	104.4 (2)	O5—C6—C7—O6	−4.3 (4)

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x, −y+1, z−1/2; (iv) −x+3/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O6^v	0.84 (1)	1.89 (1)	2.720 (3)	169 (3)
O1W—H12···N2^vi	0.84 (1)	2.00 (1)	2.842 (3)	175 (3)
O2W—H21···O5^vii	0.84 (1)	1.95 (1)	2.787 (3)	175 (4)
O2W—H22···O3W	0.84 (1)	2.16 (2)	2.908 (4)	148 (4)
O3W—H31···O2W^viii	0.84 (1)	2.19 (1)	3.017 (4)	165 (4)
O3W—H32···N3^vii	0.84 (1)	2.33 (2)	3.152 (5)	165 (4)
N3—H1···O2	0.88 (1)	2.06 (3)	2.711 (3)	130 (3)
N3—H2···O3^ix	0.88 (1)	2.10 (1)	2.967 (3)	167 (3)

Symmetry codes: (v) −x+3/2, −y+1/2, −z+1; (vi) −x+1, −y+1, −z+1; (vii) −x+3/2, −y+3/2, −z+1; (viii) −x+2, y, −z+3/2; (ix) x−1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[La(C₅H₄N₃O₂)(C₂O₄)(H₂O)₂]·H₂O
M_r	419.09
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	18.2193 (5), 10.5507 (3), 13.1307 (5)
β (°)	105.292 (1)
V (Å³)	2434.70 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.56
Crystal size (mm)	0.14 × 0.12 × 0.08

Data collection
Diffractometer	Rigaku RAXIS-RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.636, 0.764
No. of measured, independent and observed [I > 2σ(I)] reflections	11571, 2780, 2408
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.064, 1.03
No. of reflections	2780
No. of parameters	213
No. of restraints	11
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.19, −0.90

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O6ⁱ	0.84 (1)	1.89 (1)	2.720 (3)	169 (3)
O1W—H12···N2ⁱⁱ	0.84 (1)	2.00 (1)	2.842 (3)	175 (3)
O2W—H21···O5ⁱⁱⁱ	0.84 (1)	1.95 (1)	2.787 (3)	175 (4)
O2W—H22···O3W	0.84 (1)	2.16 (2)	2.908 (4)	148 (4)
O3W—H31···O2W^iv	0.84 (1)	2.19 (1)	3.017 (4)	165 (4)
O3W—H32···N3ⁱⁱⁱ	0.84 (1)	2.33 (2)	3.152 (5)	165 (4)
N3—H1···O2	0.88 (1)	2.06 (3)	2.711 (3)	130 (3)
N3—H2···O3^v	0.88 (1)	2.10 (1)	2.967 (3)	167 (3)

Symmetry codes: (i) −x+3/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, −y+3/2, −z+1; (iv) −x+2, y, −z+3/2; (v) x−1/2, y+1/2, z.

Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Heilongjiang Province (grant No. ZD200903), the Innovation Team of the Education Bureau of Heilongjiang Province (grant No. 2010td03), the Key Project of the Education Bureau of Heilongjiang Province (grant No. 12511z023) and the University of Malaya.

References

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