(2,4-Dioxo-1,2,3,4-tetra­hydro­pyrimi­dine-5-carboxyl­ato-κ2O4,O5)(4-oxido-2-oxo-1,2-dihydro­pyrimidine-5-carboxyl­ato-κ2O4,O5)bis­(1,10-phenanthroline-κ2N,N′)yttrium(III) dihydrate

Xiong, W.; Xing, H.; Su, Y.; Chen, Z.

doi:10.1107/S1600536808025701

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages m1166-m1167

doi:10.1107/S1600536808025701

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(2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylato-κ²O⁴,O⁵)(4-oxido-2-oxo-1,2-dihydropyrimidine-5-carboxylato-κ²O⁴,O⁵)bis(1,10-phenanthroline-κ²N,N′)yttrium(III) dihydrate

Wei Xiong,^a Huihui Xing,^a Yan Su ^a and Zilu Chen ^a ^*

^aCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Yucai Road 15, Guilin 541004, People's Republic of China
^*Correspondence e-mail: chenziluczl@yahoo.co.uk

(Received 22 July 2008; accepted 9 August 2008; online 16 August 2008)

In the title compound, [Y(C₅H₂N₂O₄)(C₅H₃N₂O₄)(C₁₂H₈N₂)₂]·2H₂O, the Y^III ion lies on a twofold rotation axis and exhibits a distorted square-antiprismatic coordination geometry. It is chelated by two 1,10-phenanthroline ligands, a 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate monoanion and a 4-oxido-2-oxo-1,2-dihydropyrimidine-5-carboxylate dianion. The H atom involved in an N—H⋯N hydrogen bond between the 1,2-dihydropyrimidine units has half occupancy and is disordered around a twofold rotation axis.

Related literature

For the crystal structures of the isostructural Er, Eu, Tb and Yb complexes, see: Sun & Jin (2004 ); Xing et al. (2008 ). For other related literature, see: Tobiki et al. (1980 ); Castan et al. (1990 ).

Experimental

Crystal data

[Y(C₅H₂N₂O₄)(C₅H₃N₂O₄)(C₁₂H₈N₂)₂]·2H₂O
M_r = 794.53
Monoclinic, C 2/c
a = 17.1740 (13) Å
b = 14.4385 (11) Å
c = 13.2365 (10) Å
β = 100.881 (1)°
V = 3223.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.89 mm⁻¹
T = 295 (2) K
0.24 × 0.08 × 0.06 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.660, T_max = 0.895
12035 measured reflections
3152 independent reflections
2986 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.096
S = 1.21
3152 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Y1—O2	2.247 (2)
Y1—O1	2.302 (2)
Y1—N1	2.547 (3)
Y1—N2	2.573 (3)

O2ⁱ—Y1—O2	89.15 (13)
O2—Y1—O1ⁱ	81.79 (9)
O2—Y1—O1	74.69 (8)
O1ⁱ—Y1—O1	146.81 (11)
O2ⁱ—Y1—N1	147.62 (8)
O2—Y1—N1	105.31 (9)
O1ⁱ—Y1—N1	135.17 (8)
O1—Y1—N1	74.65 (9)
N1—Y1—N1ⁱ	77.82 (13)
O2—Y1—N2ⁱ	148.38 (8)
O1—Y1—N2ⁱ	74.55 (8)
N1—Y1—N2ⁱ	73.15 (9)
O2—Y1—N2	79.43 (9)
O1—Y1—N2	122.30 (9)
N1—Y1—N2	63.90 (9)
N2ⁱ—Y1—N2	124.07 (12)
Symmetry code: (i) $[-x+2, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱⁱ	0.86	2.04	2.898 (3)	178
N1—H1⋯O1ⁱⁱ	0.86	2.60	3.160 (4)	124
N2—H2⋯N2ⁱⁱⁱ	0.86	1.81	2.669 (5)	174
O5—H5A⋯O4^iv	0.85	2.14	2.970 (4)	164
O5—H5B⋯O2^v	0.85	2.14	2.985 (4)	173
Symmetry codes: (ii) $[x, -y, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ ; (iv) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (v) 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 global, I. DOI: 10.1107/S1600536808025701/gk2161sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025701/gk2161Isup2.hkl

checkCIF report

Comment top

2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid has attracted much attention because of its potential biological activity and pharmaceutical properties, such as anticancer, antibacterial and antihypertensive properties (Tobiki et al., 1980; Castan et al., 1990). Here we report the crystal structure of Y^III complex with 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid and 1,10-phenenthroline as ligands. The title complex turned out to be isostructural with the analogues Eu, Tb, Yb (Sun & Jin, 2004) and Er (Xing et al., 2008) complexes; see Sun & Jin (2004) for their detailed description.

Related literature top

For the crystal structures of the isostructural Er, Eu, Tb and Yb complexes, see: Sun & Jin (2004); Xing et al. (2008). For other related literature, see: Tobiki et al. (1980); Castan et al. (1990).

Experimental top

A mixture of 2,4-dihydroxypyrimidine-5-carboxylic acid (0.0312 g, 0.2 mmol), YCl₃.6H₂O (0.0607 g, 0.2 mmol), phenanthroline dihydrate (0.0396 g, 0.2 mmol), NaOH (0.0160 g, 0.4 mmol) and water (15 ml) was sealed in a 25 ml, Teflon-lined stainless-steel reactor and heated to 383 K for 120 h. It was then cooled over 48 h to give colourless crystals in 70% yield. Elemental analysis calculated for C₃₄H₂₅N₈O₁₀Y: C 51.40, H 3.17, N 14.10%; found: C 51.77, H 3.29, N 14.49%.

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 of the title compound with the atom-numbering scheme and 30% displacement ellipsoids.

(2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylato- κ²O⁴,O⁵)(4-oxido-2-oxo-1,2-dihydropyrimidine-5- carboxylato-κ²O⁴,O⁵)bis(1,10-phenanthroline- κ²N,N')yttrium(III) dihydrate top

Crystal data top

[Y(C₅H₂N₂O₄)(C₅H₃N₂O₄)(C₁₂H₈N₂)₂]·2H₂O	F(000) = 1616
M_r = 794.53	D_x = 1.637 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7855 reflections
a = 17.1740 (13) Å	θ = 2.3–27.9°
b = 14.4385 (11) Å	µ = 1.89 mm⁻¹
c = 13.2365 (10) Å	T = 295 K
β = 100.881 (1)°	Prism, colourless
V = 3223.2 (4) Å³	0.24 × 0.08 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3152 independent reflections
Radiation source: fine-focus sealed tube	2986 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −21→21
T_min = 0.660, T_max = 0.895	k = −17→17
12035 measured reflections	l = −16→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.21	w = 1/[σ²(F_o²) + (0.0141P)² + 9.88P] where P = (F_o² + 2F_c²)/3
3152 reflections	(Δ/σ)_max < 0.001
240 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Y(C₅H₂N₂O₄)(C₅H₃N₂O₄)(C₁₂H₈N₂)₂]·2H₂O	V = 3223.2 (4) Å³
M_r = 794.53	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.1740 (13) Å	µ = 1.89 mm⁻¹
b = 14.4385 (11) Å	T = 295 K
c = 13.2365 (10) Å	0.24 × 0.08 × 0.06 mm
β = 100.881 (1)°

Data collection top

Bruker APEXII diffractometer	3152 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2986 reflections with I > 2σ(I)
T_min = 0.660, T_max = 0.895	R_int = 0.035
12035 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.21	Δρ_max = 0.41 e Å⁻³
3152 reflections	Δρ_min = −0.51 e Å⁻³
240 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	Occ. (<1)
Y1	1.0000	0.88802 (3)	0.2500	0.02339 (12)
N1	0.90591 (16)	0.75076 (19)	0.2117 (2)	0.0324 (6)
N2	0.96510 (16)	0.80446 (19)	0.4073 (2)	0.0304 (6)
N3	0.83326 (16)	1.02589 (19)	−0.0065 (2)	0.0297 (6)
H3	0.8379	0.9842	−0.0514	0.036*
N4	0.78240 (19)	1.1684 (2)	0.0310 (2)	0.0387 (7)
H4	0.7585	1.2199	0.0131	0.046*	0.50
O1	0.90470 (14)	0.93356 (15)	0.11247 (17)	0.0329 (6)
O2	0.93006 (14)	0.99886 (16)	0.31195 (17)	0.0337 (6)
O3	0.84729 (15)	1.10907 (17)	0.34049 (17)	0.0371 (6)
O4	0.76917 (16)	1.11986 (18)	−0.13684 (19)	0.0451 (7)
C1	0.8770 (2)	1.0594 (2)	0.2805 (2)	0.0272 (7)
C2	0.84980 (19)	1.0723 (2)	0.1678 (2)	0.0269 (7)
C3	0.86584 (18)	1.0066 (2)	0.0941 (2)	0.0248 (7)
C4	0.7937 (2)	1.1063 (2)	−0.0423 (3)	0.0324 (7)
C5	0.8085 (2)	1.1498 (2)	0.1311 (3)	0.0358 (8)
H5	0.7976	1.1928	0.1788	0.043*
C6	0.9900 (2)	0.8317 (3)	0.5036 (3)	0.0386 (8)
H6	1.0089	0.8920	0.5148	0.046*
C7	0.9896 (3)	0.7758 (3)	0.5890 (3)	0.0512 (11)
H7	1.0074	0.7982	0.6552	0.061*
C8	0.9624 (3)	0.6872 (3)	0.5735 (3)	0.0599 (12)
H8	0.9626	0.6483	0.6296	0.072*
C9	0.9342 (2)	0.6545 (3)	0.4735 (3)	0.0463 (10)
C10	0.9355 (2)	0.7169 (2)	0.3922 (3)	0.0327 (8)
C11	0.9042 (2)	0.6886 (2)	0.2883 (3)	0.0325 (8)
C12	0.8716 (2)	0.5993 (2)	0.2699 (3)	0.0419 (9)
C13	0.8735 (3)	0.5372 (3)	0.3546 (4)	0.0607 (13)
H13	0.8534	0.4776	0.3423	0.073*
C14	0.9036 (3)	0.5634 (3)	0.4513 (4)	0.0618 (13)
H14	0.9045	0.5215	0.5048	0.074*
C15	0.8370 (2)	0.5768 (3)	0.1686 (4)	0.0510 (11)
H15	0.8148	0.5185	0.1533	0.061*
C16	0.8357 (2)	0.6401 (3)	0.0926 (3)	0.0490 (10)
H16	0.8119	0.6262	0.0252	0.059*
C17	0.8707 (2)	0.7264 (3)	0.1173 (3)	0.0397 (9)
H17	0.8693	0.7693	0.0647	0.048*
O5	0.6925 (3)	0.1887 (2)	0.6600 (3)	0.0956 (14)
H51	0.6793	0.2454	0.6644	0.143*
H52	0.7082	0.1681	0.7208	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Y1	0.0287 (2)	0.0187 (2)	0.0207 (2)	0.000	−0.00062 (16)	0.000
N1	0.0322 (16)	0.0288 (15)	0.0352 (16)	−0.0037 (12)	0.0040 (12)	−0.0035 (12)
N2	0.0318 (15)	0.0294 (15)	0.0297 (15)	−0.0002 (12)	0.0051 (12)	0.0008 (12)
N3	0.0389 (16)	0.0276 (15)	0.0204 (13)	0.0051 (12)	0.0001 (12)	−0.0021 (11)
N4	0.057 (2)	0.0273 (15)	0.0278 (15)	0.0107 (14)	−0.0016 (14)	0.0018 (12)
O1	0.0421 (14)	0.0265 (12)	0.0255 (12)	0.0100 (10)	−0.0052 (10)	−0.0034 (9)
O2	0.0441 (14)	0.0324 (13)	0.0226 (12)	0.0133 (11)	0.0011 (10)	0.0006 (10)
O3	0.0510 (15)	0.0374 (14)	0.0227 (12)	0.0125 (12)	0.0064 (11)	−0.0021 (10)
O4	0.0562 (17)	0.0369 (15)	0.0358 (14)	0.0044 (13)	−0.0074 (12)	0.0002 (12)
C1	0.0345 (18)	0.0240 (16)	0.0224 (16)	−0.0025 (14)	0.0032 (13)	0.0017 (13)
C2	0.0328 (17)	0.0263 (16)	0.0207 (16)	0.0053 (14)	0.0031 (13)	0.0002 (13)
C3	0.0284 (16)	0.0237 (16)	0.0209 (15)	−0.0008 (13)	0.0014 (13)	0.0007 (12)
C4	0.0373 (19)	0.0291 (18)	0.0280 (17)	−0.0006 (15)	−0.0012 (14)	0.0021 (14)
C5	0.050 (2)	0.0292 (18)	0.0263 (18)	0.0094 (16)	0.0031 (16)	−0.0026 (14)
C6	0.039 (2)	0.042 (2)	0.0339 (19)	−0.0026 (17)	0.0042 (16)	−0.0029 (16)
C7	0.056 (3)	0.070 (3)	0.028 (2)	−0.010 (2)	0.0082 (18)	0.0061 (19)
C8	0.066 (3)	0.069 (3)	0.044 (2)	−0.008 (2)	0.009 (2)	0.024 (2)
C9	0.048 (2)	0.043 (2)	0.048 (2)	−0.0034 (19)	0.0101 (19)	0.0158 (19)
C10	0.0306 (18)	0.0296 (18)	0.0384 (19)	−0.0007 (14)	0.0078 (15)	0.0034 (15)
C11	0.0311 (18)	0.0269 (17)	0.0399 (19)	−0.0005 (14)	0.0072 (15)	−0.0017 (15)
C12	0.042 (2)	0.0279 (19)	0.058 (2)	−0.0074 (16)	0.0137 (19)	−0.0027 (17)
C13	0.074 (3)	0.030 (2)	0.080 (3)	−0.018 (2)	0.017 (3)	0.004 (2)
C14	0.076 (3)	0.042 (3)	0.068 (3)	−0.017 (2)	0.016 (3)	0.021 (2)
C15	0.051 (2)	0.035 (2)	0.069 (3)	−0.0161 (19)	0.016 (2)	−0.018 (2)
C16	0.047 (2)	0.050 (2)	0.049 (2)	−0.0137 (19)	0.0063 (19)	−0.022 (2)
C17	0.039 (2)	0.039 (2)	0.040 (2)	−0.0064 (17)	0.0052 (16)	−0.0062 (16)
O5	0.145 (4)	0.059 (2)	0.067 (2)	0.004 (2)	−0.017 (2)	−0.0089 (19)

Geometric parameters (Å, º) top

Y1—O2ⁱ	2.247 (2)	C2—C3	1.423 (4)
Y1—O2	2.247 (2)	C5—H5	0.9300
Y1—O1ⁱ	2.302 (2)	C6—C7	1.391 (5)
Y1—O1	2.302 (2)	C6—H6	0.9300
Y1—N1	2.547 (3)	C7—C8	1.362 (6)
Y1—N1ⁱ	2.547 (3)	C7—H7	0.9300
Y1—N2ⁱ	2.573 (3)	C8—C9	1.403 (6)
Y1—N2	2.573 (3)	C8—H8	0.9300
N1—C17	1.329 (4)	C9—C10	1.407 (5)
N1—C11	1.358 (4)	C9—C14	1.426 (6)
N2—C6	1.326 (4)	C10—C11	1.439 (5)
N2—C10	1.363 (4)	C11—C12	1.408 (5)
N3—C3	1.373 (4)	C12—C15	1.399 (6)
N3—C4	1.383 (4)	C12—C13	1.431 (6)
N3—H3	0.8600	C13—C14	1.342 (6)
N4—C5	1.343 (4)	C13—H13	0.9300
N4—C4	1.362 (4)	C14—H14	0.9300
N4—H4	0.8600	C15—C16	1.355 (6)
O1—C3	1.247 (4)	C15—H15	0.9300
O2—C1	1.275 (4)	C16—C17	1.395 (5)
O3—C1	1.248 (4)	C16—H16	0.9300
O4—C4	1.258 (4)	C17—H17	0.9300
C1—C2	1.489 (4)	O5—H51	0.8533
C2—C5	1.364 (4)	O5—H52	0.8518

O2ⁱ—Y1—O2	89.15 (13)	C3—C2—C1	122.6 (3)
O2ⁱ—Y1—O1ⁱ	74.69 (8)	O1—C3—N3	117.7 (3)
O2—Y1—O1ⁱ	81.79 (9)	O1—C3—C2	126.6 (3)
O2ⁱ—Y1—O1	81.79 (8)	N3—C3—C2	115.7 (3)
O2—Y1—O1	74.69 (8)	O4—C4—N4	122.7 (3)
O1ⁱ—Y1—O1	146.81 (11)	O4—C4—N3	121.5 (3)
O2ⁱ—Y1—N1	147.62 (8)	N4—C4—N3	115.8 (3)
O2—Y1—N1	105.31 (9)	N4—C5—C2	124.8 (3)
O1ⁱ—Y1—N1	135.17 (8)	N4—C5—H5	117.6
O1—Y1—N1	74.65 (9)	C2—C5—H5	117.6
O2ⁱ—Y1—N1ⁱ	105.31 (9)	N2—C6—C7	124.0 (4)
O2—Y1—N1ⁱ	147.62 (8)	N2—C6—H6	118.0
O1ⁱ—Y1—N1ⁱ	74.65 (9)	C7—C6—H6	118.0
O1—Y1—N1ⁱ	135.17 (8)	C8—C7—C6	118.5 (4)
N1—Y1—N1ⁱ	77.82 (13)	C8—C7—H7	120.7
O2ⁱ—Y1—N2ⁱ	79.43 (8)	C6—C7—H7	120.7
O2—Y1—N2ⁱ	148.38 (8)	C7—C8—C9	120.4 (4)
O1ⁱ—Y1—N2ⁱ	122.30 (9)	C7—C8—H8	119.8
O1—Y1—N2ⁱ	74.55 (8)	C9—C8—H8	119.8
N1—Y1—N2ⁱ	73.15 (9)	C8—C9—C10	117.0 (4)
N1ⁱ—Y1—N2ⁱ	63.90 (9)	C8—C9—C14	123.6 (4)
O2ⁱ—Y1—N2	148.38 (8)	C10—C9—C14	119.4 (4)
O2—Y1—N2	79.43 (9)	N2—C10—C9	122.8 (3)
O1ⁱ—Y1—N2	74.55 (8)	N2—C10—C11	117.7 (3)
O1—Y1—N2	122.30 (9)	C9—C10—C11	119.5 (3)
N1—Y1—N2	63.90 (9)	N1—C11—C12	122.7 (3)
N1ⁱ—Y1—N2	73.15 (9)	N1—C11—C10	118.0 (3)
N2ⁱ—Y1—N2	124.07 (12)	C12—C11—C10	119.3 (3)
C17—N1—C11	117.1 (3)	C15—C12—C11	117.5 (4)
C17—N1—Y1	123.5 (2)	C15—C12—C13	123.2 (4)
C11—N1—Y1	117.9 (2)	C11—C12—C13	119.3 (4)
C6—N2—C10	117.4 (3)	C14—C13—C12	121.2 (4)
C6—N2—Y1	123.8 (2)	C14—C13—H13	119.4
C10—N2—Y1	117.0 (2)	C12—C13—H13	119.4
C3—N3—C4	125.9 (3)	C13—C14—C9	121.2 (4)
C3—N3—H3	117.0	C13—C14—H14	119.4
C4—N3—H3	117.0	C9—C14—H14	119.4
C5—N4—C4	120.3 (3)	C16—C15—C12	119.9 (4)
C5—N4—H4	119.9	C16—C15—H15	120.0
C4—N4—H4	119.9	C12—C15—H15	120.0
C3—O1—Y1	132.1 (2)	C15—C16—C17	118.8 (4)
C1—O2—Y1	140.2 (2)	C15—C16—H16	120.6
O3—C1—O2	122.6 (3)	C17—C16—H16	120.6
O3—C1—C2	118.5 (3)	N1—C17—C16	123.9 (4)
O2—C1—C2	118.8 (3)	N1—C17—H17	118.1
C5—C2—C3	117.2 (3)	C16—C17—H17	118.1
C5—C2—C1	120.2 (3)	H51—O5—H52	108.2

O2ⁱ—Y1—N1—C17	−8.9 (4)	C4—N3—C3—O1	−174.8 (3)
O2—Y1—N1—C17	104.9 (3)	C4—N3—C3—C2	6.6 (5)
O1ⁱ—Y1—N1—C17	−161.4 (3)	C5—C2—C3—O1	177.5 (3)
O1—Y1—N1—C17	35.9 (3)	C1—C2—C3—O1	−1.8 (5)
N1ⁱ—Y1—N1—C17	−108.3 (3)	C5—C2—C3—N3	−4.0 (5)
N2ⁱ—Y1—N1—C17	−42.2 (3)	C1—C2—C3—N3	176.7 (3)
N2—Y1—N1—C17	174.6 (3)	C5—N4—C4—O4	178.8 (4)
O2ⁱ—Y1—N1—C11	157.1 (2)	C5—N4—C4—N3	−0.5 (5)
O2—Y1—N1—C11	−89.1 (2)	C3—N3—C4—O4	176.4 (3)
O1ⁱ—Y1—N1—C11	4.6 (3)	C3—N3—C4—N4	−4.3 (5)
O1—Y1—N1—C11	−158.1 (3)	C4—N4—C5—C2	2.7 (6)
N1ⁱ—Y1—N1—C11	57.7 (2)	C3—C2—C5—N4	−0.3 (6)
N2ⁱ—Y1—N1—C11	123.8 (3)	C1—C2—C5—N4	179.0 (3)
N2—Y1—N1—C11	−19.3 (2)	C10—N2—C6—C7	1.8 (5)
O2ⁱ—Y1—N2—C6	7.0 (4)	Y1—N2—C6—C7	−162.4 (3)
O2—Y1—N2—C6	−63.6 (3)	N2—C6—C7—C8	0.4 (6)
O1ⁱ—Y1—N2—C6	20.7 (3)	C6—C7—C8—C9	−1.3 (7)
O1—Y1—N2—C6	−127.8 (3)	C7—C8—C9—C10	0.0 (7)
N1—Y1—N2—C6	−176.6 (3)	C7—C8—C9—C14	−178.8 (5)
N1ⁱ—Y1—N2—C6	99.0 (3)	C6—N2—C10—C9	−3.2 (5)
N2ⁱ—Y1—N2—C6	139.5 (3)	Y1—N2—C10—C9	162.2 (3)
O2ⁱ—Y1—N2—C10	−157.3 (2)	C6—N2—C10—C11	176.5 (3)
O2—Y1—N2—C10	132.1 (2)	Y1—N2—C10—C11	−18.1 (4)
O1ⁱ—Y1—N2—C10	−143.6 (2)	C8—C9—C10—N2	2.3 (6)
O1—Y1—N2—C10	67.9 (2)	C14—C9—C10—N2	−178.8 (4)
N1—Y1—N2—C10	19.1 (2)	C8—C9—C10—C11	−177.4 (4)
N1ⁱ—Y1—N2—C10	−65.3 (2)	C14—C9—C10—C11	1.5 (6)
N2ⁱ—Y1—N2—C10	−24.8 (2)	C17—N1—C11—C12	4.1 (5)
O2ⁱ—Y1—O1—C3	−68.1 (3)	Y1—N1—C11—C12	−162.8 (3)
O2—Y1—O1—C3	23.3 (3)	C17—N1—C11—C10	−174.4 (3)
O1ⁱ—Y1—O1—C3	−23.2 (3)	Y1—N1—C11—C10	18.7 (4)
N1—Y1—O1—C3	134.3 (3)	N2—C10—C11—N1	−0.2 (5)
N1ⁱ—Y1—O1—C3	−171.6 (3)	C9—C10—C11—N1	179.6 (3)
N2ⁱ—Y1—O1—C3	−149.3 (3)	N2—C10—C11—C12	−178.7 (3)
N2—Y1—O1—C3	89.8 (3)	C9—C10—C11—C12	1.1 (5)
O2ⁱ—Y1—O2—C1	72.0 (3)	N1—C11—C12—C15	−2.7 (6)
O1ⁱ—Y1—O2—C1	146.7 (4)	C10—C11—C12—C15	175.7 (3)
O1—Y1—O2—C1	−9.7 (3)	N1—C11—C12—C13	178.8 (4)
N1—Y1—O2—C1	−78.6 (3)	C10—C11—C12—C13	−2.8 (6)
N1ⁱ—Y1—O2—C1	−170.0 (3)	C15—C12—C13—C14	−176.4 (5)
N2ⁱ—Y1—O2—C1	4.0 (4)	C11—C12—C13—C14	2.0 (7)
N2—Y1—O2—C1	−137.6 (4)	C12—C13—C14—C9	0.6 (8)
Y1—O2—C1—O3	176.0 (2)	C8—C9—C14—C13	176.5 (5)
Y1—O2—C1—C2	−4.6 (5)	C10—C9—C14—C13	−2.3 (7)
O3—C1—C2—C5	15.4 (5)	C11—C12—C15—C16	−0.1 (6)
O2—C1—C2—C5	−164.0 (3)	C13—C12—C15—C16	178.4 (4)
O3—C1—C2—C3	−165.3 (3)	C12—C15—C16—C17	1.3 (6)
O2—C1—C2—C3	15.2 (5)	C11—N1—C17—C16	−2.8 (5)
Y1—O1—C3—N3	158.7 (2)	Y1—N1—C17—C16	163.3 (3)
Y1—O1—C3—C2	−22.8 (5)	C15—C16—C17—N1	0.2 (6)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3ⁱⁱ	0.86	1.99	2.853 (4)	178
N3—H3···O2ⁱⁱ	0.86	2.63	3.189 (4)	124
N4—H4···N4ⁱⁱⁱ	0.86	1.81	2.667 (6)	174
O5—H51···O3^iv	0.85	2.15	2.998 (4)	173
O5—H52···O4^v	0.85	2.10	2.935 (4)	169

Symmetry codes: (ii) x, −y+2, z−1/2; (iii) −x+3/2, −y+5/2, −z; (iv) −x+3/2, −y+3/2, −z+1; (v) x, y−1, z+1.

Experimental details

Crystal data
Chemical formula	[Y(C₅H₂N₂O₄)(C₅H₃N₂O₄)(C₁₂H₈N₂)₂]·2H₂O
M_r	794.53
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	17.1740 (13), 14.4385 (11), 13.2365 (10)
β (°)	100.881 (1)
V (Å³)	3223.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.24 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.660, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	12035, 3152, 2986
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.096, 1.21
No. of reflections	3152
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.51

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

Selected geometric parameters (Å, º) top

Y1—O2	2.247 (2)	Y1—N1	2.547 (3)
Y1—O1	2.302 (2)	Y1—N2	2.573 (3)

O2ⁱ—Y1—O2	89.15 (13)	N1—Y1—N1ⁱ	77.82 (13)
O2—Y1—O1ⁱ	81.79 (9)	O2—Y1—N2ⁱ	148.38 (8)
O2—Y1—O1	74.69 (8)	O1—Y1—N2ⁱ	74.55 (8)
O1ⁱ—Y1—O1	146.81 (11)	N1—Y1—N2ⁱ	73.15 (9)
O2ⁱ—Y1—N1	147.62 (8)	O2—Y1—N2	79.43 (9)
O2—Y1—N1	105.31 (9)	O1—Y1—N2	122.30 (9)
O1ⁱ—Y1—N1	135.17 (8)	N1—Y1—N2	63.90 (9)
O1—Y1—N1	74.65 (9)	N2ⁱ—Y1—N2	124.07 (12)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3ⁱⁱ	0.86	1.99	2.853 (4)	177.9
N3—H3···O2ⁱⁱ	0.86	2.63	3.189 (4)	123.8
N4—H4···N4ⁱⁱⁱ	0.86	1.81	2.667 (6)	173.5
O5—H51···O3^iv	0.85	2.15	2.998 (4)	173.1
O5—H52···O4^v	0.85	2.10	2.935 (4)	168.7

Symmetry codes: (ii) x, −y+2, z−1/2; (iii) −x+3/2, −y+5/2, −z; (iv) −x+3/2, −y+3/2, −z+1; (v) x, y−1, z+1.

Acknowledgements

The authors thank the Science Foundation of Guangxi Province, China (Guikeqing 0542021) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, for financial support.

References

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