Bis[4-oxido-2-oxo-2,3-di­hydro­pyrimidin-1-ium-5-carboxyl­ato(1.5−)-κ2O4,O5]bis­(1,10-phenanthroline-κ2N,N′)dysprosium(III) dihydrate

Liu, X.; Xing, H.; Miao, J.; Jia, M.; Chen, Z.

doi:10.1107/S1600536809036848

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages m1224-m1225

doi:10.1107/S1600536809036848

Open

access

Bis[4-oxido-2-oxo-2,3-dihydropyrimidin-1-ium-5-carboxylato(1.5−)-κ²O⁴,O⁵]bis(1,10-phenanthroline-κ²N,N′)dysprosium(III) dihydrate

Xianlin Liu,^a Huihui Xing,^a Jing Miao,^a Maomao Jia ^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 25 August 2009; accepted 11 September 2009; online 19 September 2009)

In the title compound, [Dy(C₅H_2.5N₂O₄)₂(C₁₂H₈N₂)₂]·2H₂O, the Dy^III ion is located on a twofold rotation axis and is coordinated in a square-antiprismatic geometry by two chelating 1,10-phenanthroline molecules as well as two 4-oxido-2-oxo-2,3-dihydropyrimidin-1-ium-5-carboxylato(1.5−) anions. N—H⋯O and O—H⋯O hydrogen bonds help to stabilize the crystal structure. The H atom involved in an N—H⋯N hydrogen bond is disordered around a twofold rotation axis.

Related literature

For isostructural lanthanide complexes with 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid, see: Sun & Jin (2004a ,b ); Xing et al. (2008a ); Xiong et al. (2008a ,b ). For other metal complexes of 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid, see: Hueso-Ureña et al. (1993 , 1996 ); Baran et al. (1996 ); Luo et al. (2002 ); Maistralis et al. (1991 , 1992 ); Xing et al. (2008b ). For the role played by hydrogen bonds in stabilizing structures, see: Chen et al. (2006 ); Arora et al. (2009 ); Jagan & Sivakumar (2009 ).

Experimental

Crystal data

[Dy(C₅H_2.5N₂O₄)₂(C₁₂H₈N₂)₂]·2H₂O
M_r = 868.12
Monoclinic, C 2/c
a = 17.143 (2) Å
b = 14.4470 (17) Å
c = 13.2211 (16) Å
β = 100.613 (2)°
V = 3218.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.40 mm⁻¹
T = 295 K
0.10 × 0.03 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.796, T_max = 0.954
11116 measured reflections
2842 independent reflections
2619 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.068
S = 1.06
2842 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.93 e Å⁻³
Δρ_min = −1.22 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Dy—O2	2.256 (3)
Dy—O1	2.313 (2)
Dy—N2	2.554 (3)
Dy—N1	2.576 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N3ⁱⁱ	0.86	1.80	2.659 (7)	174
N4—H4⋯O3ⁱⁱⁱ	0.86	2.01	2.867 (4)	178
N4—H4⋯O2ⁱⁱⁱ	0.86	2.62	3.183 (4)	124
O5—H51⋯O3^iv	0.85	2.15	2.993 (5)	175
O5—H52⋯O4^v	0.85	2.15	2.960 (5)	160
Symmetry codes: (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (v) x, y, z-1.

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/S1600536809036848/pb2007sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036848/pb2007Isup2.hkl

checkCIF report

Comment top

2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid has been extensively used in the preparation of robust networks or some porous coordination polymers because of its versatile coordination modes. For further investigation of its coordination behavior to lanthanide(III) ions, we report here a new Dy^III complex of 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid, which turned out to be isostructural with the analogues Eu^III, Tb^III, Yb^III (2004a,b), Er^III (Xing et al., 2008a) and Y^III, Gd^III (Xiong et al., 2008a,b) complexes.

In the title complex, (I), the Dy^III ion is located on a twofold rotation axis and coordinated in square-antiprismatic geometry completed by four N atoms from two chelating phenanthroline molecules, four O atoms from two chelating 4-oxido-2-oxo-2,3-dihydropyrimidin-1-ium-5-carboxylate(1.5-) anions. The distances of Dy—O are 2.256 (3) and 2.313 (2)Å, and those of Dy—N are 2.554 (3) and 2.576 (3)Å. The averge distance of Dy—O is 2.285Å, which is much shorter than that of Dy—N (2.565Å). The dihedral angle between two phen molecules is 37.726°. As shown in Table 2 and Fig. 2, each coordination unit [Dy(C₅H₃N₂O₄)(C₅H₂N₂O₄)(C₁₂H₈N₂)₂)] interacts with another four via intermolecular N—H···O and N—H···N hydrogen bonds. Each lattice water molecule links two coordination units mentioned above via O—H···O hydrogen bonds. As a result, these hydrogen bonds link the title complex units and lattice water molecules into a three-dimensional supramolecular network as shown in the packing diagram (Fig. 2). The H atom involved in an N—H···N hydrogen bond is disordered around a twofold rotation axis with half occupancy.

Related literature top

For isostructural lanthanide complexes with 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid, see: Sun & Jin (2004a,b); Xing et al. (2008a); Xiong et al. (2008a,b). For related literature [on what subject?], see: Hueso-Ureña et al. (1993, 1996); Baran et al. (1996); Luo et al. (2002); Maistralis et al. (1991, 1992); Xing et al. (2008b). For the role played by hydrogen bonds in stabilizing structures, see: Chen et al. (2006); Arora et al. (2009); Jagan & Sivakumar (2009).

Experimental top

A mixture of 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (0.0312 g, 0.2 mmol), DyCl₃.6H₂O (0.0754 g, 0.2 mmol), Phen.H₂O (0.0396 g, 0.2 mmol), NaOH (0.00800 g, 0.2 mmol), 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, light yellow crystals were isolated in 80% yield. Elemental analysis for C₃₄H₂₅DyN₈O₁₀, calculated: C 47.04, H 2.90, N 12.91%; found: C 47.49, H 2.96, N 13.24%.

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.
	Fig. 2. A view of the packing diagram of the title compound viewed down the c axis. H atoms not involving in hydrogen bonds are omitted for clarity.

Bis[4-oxido-2-oxo-2,3-dihydropyrimidin-1-ium-5-carboxylato(1.5-)- κ²O⁵,O⁶]bis(1,10-phenanthroline- κ²N,N')dysprosium(III) dihydrate top

Crystal data top

[Dy(C₅H_2.5N₂O₄)₂(C₁₂H₈N₂)₂]·2H₂O	F(000) = 1724
M_r = 868.12	D_x = 1.792 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4430 reflections
a = 17.143 (2) Å	θ = 2.3–26.9°
b = 14.4470 (17) Å	µ = 2.40 mm⁻¹
c = 13.2211 (16) Å	T = 295 K
β = 100.613 (2)°	Prism, yellow
V = 3218.3 (7) Å³	0.10 × 0.03 × 0.02 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2842 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −20→20
T_min = 0.796, T_max = 0.954	k = −17→17
11116 measured reflections	l = −15→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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0366P)² + 4.1092P] where P = (F_o² + 2F_c²)/3
2842 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.93 e Å⁻³
0 restraints	Δρ_min = −1.22 e Å⁻³

Crystal data top

[Dy(C₅H_2.5N₂O₄)₂(C₁₂H₈N₂)₂]·2H₂O	V = 3218.3 (7) Å³
M_r = 868.12	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.143 (2) Å	µ = 2.40 mm⁻¹
b = 14.4470 (17) Å	T = 295 K
c = 13.2211 (16) Å	0.10 × 0.03 × 0.02 mm
β = 100.613 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2842 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2619 reflections with I > 2σ(I)
T_min = 0.796, T_max = 0.954	R_int = 0.037
11116 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.068	H-atom parameters constrained
S = 1.06	Δρ_max = 0.93 e Å⁻³
2842 reflections	Δρ_min = −1.22 e Å⁻³
240 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)
Dy	0.0000	0.612148 (16)	0.7500	0.02165 (10)
N1	0.03494 (19)	0.6959 (2)	0.5922 (2)	0.0299 (7)
N2	0.09455 (19)	0.7496 (2)	0.7881 (3)	0.0318 (8)
N3	0.2176 (2)	0.3312 (2)	0.9692 (2)	0.0379 (9)
H3	0.2412	0.2796	0.9869	0.046*	0.50
N4	0.16685 (19)	0.4740 (2)	1.0061 (2)	0.0295 (8)
H4	0.1617	0.5157	1.0509	0.035*
O1	0.09579 (16)	0.56623 (18)	0.88770 (19)	0.0302 (6)
O2	0.07048 (16)	0.50051 (18)	0.68831 (19)	0.0327 (6)
O3	0.15320 (18)	0.38990 (19)	0.6597 (2)	0.0362 (7)
O4	0.2306 (2)	0.38078 (19)	1.1355 (2)	0.0437 (8)
C1	0.1236 (2)	0.4394 (3)	0.7192 (3)	0.0278 (9)
C2	0.1504 (2)	0.4274 (3)	0.8320 (3)	0.0262 (8)
C3	0.1915 (3)	0.3504 (3)	0.8700 (3)	0.0363 (10)
H3A	0.2025	0.3072	0.8224	0.044*
C4	0.2065 (3)	0.3940 (3)	1.0424 (3)	0.0326 (9)
C5	0.1350 (2)	0.4930 (2)	0.9059 (3)	0.0240 (8)
C6	0.1293 (2)	0.7739 (3)	0.8822 (3)	0.0362 (10)
H6	0.1307	0.7310	0.9350	0.043*
C7	0.1639 (3)	0.8606 (3)	0.9064 (4)	0.0479 (12)
H7	0.1875	0.8750	0.9736	0.057*
C8	0.1626 (3)	0.9232 (3)	0.8298 (4)	0.0507 (13)
H8	0.1847	0.9815	0.8448	0.061*
C9	0.1283 (3)	0.9012 (3)	0.7289 (4)	0.0416 (11)
C10	0.0959 (2)	0.8115 (3)	0.7112 (3)	0.0303 (9)
C11	0.0644 (2)	0.7832 (3)	0.6071 (3)	0.0315 (9)
C12	0.0658 (3)	0.8453 (3)	0.5253 (4)	0.0451 (11)
C13	0.0962 (3)	0.9367 (4)	0.5480 (4)	0.0622 (15)
H13	0.0954	0.9786	0.4945	0.075*
C14	0.1256 (3)	0.9631 (3)	0.6439 (5)	0.0610 (15)
H14	0.1449	1.0231	0.6559	0.073*
C15	0.0367 (3)	0.8133 (4)	0.4259 (4)	0.0577 (14)
H15	0.0352	0.8526	0.3699	0.069*
C16	0.0108 (3)	0.7253 (4)	0.4111 (3)	0.0514 (13)
H16	−0.0064	0.7029	0.3448	0.062*
C17	0.0099 (2)	0.6686 (3)	0.4955 (3)	0.0384 (10)
H17	−0.0091	0.6085	0.4839	0.046*
O5	0.3087 (3)	0.3123 (3)	0.3401 (3)	0.0926 (15)
H51	0.3201	0.2551	0.3440	0.139*
H52	0.2760	0.3253	0.2854	0.139*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Dy	0.02842 (15)	0.01487 (14)	0.01945 (14)	0.000	−0.00135 (10)	0.000
N1	0.0310 (18)	0.0264 (18)	0.0312 (18)	−0.0013 (14)	0.0023 (14)	−0.0005 (14)
N2	0.0311 (19)	0.0288 (19)	0.0350 (19)	−0.0034 (15)	0.0049 (15)	−0.0040 (15)
N3	0.060 (2)	0.0248 (18)	0.0264 (18)	0.0105 (17)	−0.0002 (16)	0.0024 (15)
N4	0.042 (2)	0.0245 (17)	0.0195 (16)	0.0066 (15)	0.0000 (14)	−0.0021 (13)
O1	0.0425 (16)	0.0218 (14)	0.0224 (13)	0.0096 (13)	−0.0044 (12)	−0.0024 (11)
O2	0.0439 (17)	0.0310 (15)	0.0209 (13)	0.0115 (13)	−0.0003 (12)	0.0015 (12)
O3	0.0519 (18)	0.0361 (16)	0.0211 (14)	0.0150 (14)	0.0079 (13)	−0.0015 (12)
O4	0.060 (2)	0.0342 (17)	0.0305 (16)	0.0059 (15)	−0.0095 (14)	0.0031 (13)
C1	0.036 (2)	0.021 (2)	0.025 (2)	−0.0020 (18)	0.0015 (17)	0.0014 (17)
C2	0.032 (2)	0.024 (2)	0.0217 (19)	0.0052 (17)	0.0024 (16)	0.0012 (16)
C3	0.053 (3)	0.025 (2)	0.029 (2)	0.010 (2)	0.0043 (19)	−0.0041 (18)
C4	0.039 (2)	0.028 (2)	0.028 (2)	−0.0024 (18)	−0.0028 (17)	0.0038 (17)
C5	0.029 (2)	0.021 (2)	0.0211 (19)	−0.0003 (16)	0.0017 (15)	0.0000 (15)
C6	0.038 (2)	0.033 (2)	0.035 (2)	−0.0083 (19)	0.0024 (19)	−0.0072 (19)
C7	0.043 (3)	0.048 (3)	0.052 (3)	−0.014 (2)	0.009 (2)	−0.024 (2)
C8	0.051 (3)	0.034 (3)	0.068 (3)	−0.016 (2)	0.013 (3)	−0.019 (3)
C9	0.042 (3)	0.024 (2)	0.061 (3)	−0.0076 (19)	0.014 (2)	−0.006 (2)
C10	0.025 (2)	0.026 (2)	0.040 (2)	−0.0013 (16)	0.0070 (17)	−0.0005 (18)
C11	0.029 (2)	0.029 (2)	0.037 (2)	0.0015 (17)	0.0071 (18)	0.0051 (18)
C12	0.044 (3)	0.041 (3)	0.052 (3)	−0.003 (2)	0.012 (2)	0.014 (2)
C13	0.077 (4)	0.044 (3)	0.066 (4)	−0.014 (3)	0.013 (3)	0.022 (3)
C14	0.070 (4)	0.028 (3)	0.088 (4)	−0.015 (2)	0.022 (3)	0.005 (3)
C15	0.067 (4)	0.066 (4)	0.038 (3)	−0.010 (3)	0.007 (2)	0.024 (3)
C16	0.056 (3)	0.070 (4)	0.028 (2)	−0.013 (3)	0.007 (2)	0.005 (2)
C17	0.037 (2)	0.042 (3)	0.036 (2)	−0.004 (2)	0.0056 (19)	−0.005 (2)
O5	0.142 (4)	0.047 (2)	0.070 (3)	0.003 (3)	−0.027 (3)	−0.010 (2)

Geometric parameters (Å, º) top

Dy—O2ⁱ	2.256 (3)	C2—C5	1.420 (5)
Dy—O2	2.256 (3)	C3—H3A	0.9300
Dy—O1ⁱ	2.313 (2)	C6—C7	1.398 (6)
Dy—O1	2.313 (2)	C6—H6	0.9300
Dy—N2	2.554 (3)	C7—C8	1.355 (7)
Dy—N2ⁱ	2.554 (3)	C7—H7	0.9300
Dy—N1ⁱ	2.576 (3)	C8—C9	1.392 (7)
Dy—N1	2.576 (3)	C8—H8	0.9300
N1—C17	1.331 (5)	C9—C10	1.412 (5)
N1—C11	1.360 (5)	C9—C14	1.431 (7)
N2—C6	1.324 (5)	C10—C11	1.442 (6)
N2—C10	1.358 (5)	C11—C12	1.408 (6)
N3—C3	1.335 (5)	C12—C15	1.397 (7)
N3—C4	1.364 (5)	C12—C13	1.430 (7)
N3—H3	0.8600	C13—C14	1.331 (8)
N4—C5	1.365 (5)	C13—H13	0.9300
N4—C4	1.382 (5)	C14—H14	0.9300
N4—H4	0.8600	C15—C16	1.349 (7)
O1—C5	1.253 (4)	C15—H15	0.9300
O2—C1	1.279 (4)	C16—C17	1.386 (6)
O3—C1	1.239 (5)	C16—H16	0.9300
O4—C4	1.239 (5)	C17—H17	0.9300
C1—C2	1.488 (5)	O5—H51	0.8483
C2—C3	1.363 (6)	O5—H52	0.8510

O2ⁱ—Dy—O2	88.73 (14)	C5—C2—C1	123.4 (3)
O2ⁱ—Dy—O1ⁱ	74.32 (9)	N3—C3—C2	126.1 (4)
O2—Dy—O1ⁱ	81.97 (10)	N3—C3—H3A	117.0
O2ⁱ—Dy—O1	81.97 (10)	C2—C3—H3A	117.0
O2—Dy—O1	74.32 (9)	O4—C4—N3	122.5 (4)
O1ⁱ—Dy—O1	146.67 (13)	O4—C4—N4	121.7 (4)
O2ⁱ—Dy—N2	147.90 (10)	N3—C4—N4	115.8 (3)
O2—Dy—N2	105.34 (10)	O1—C5—N4	117.4 (3)
O1ⁱ—Dy—N2	135.32 (10)	O1—C5—C2	126.3 (3)
O1—Dy—N2	74.62 (10)	N4—C5—C2	116.3 (3)
O2ⁱ—Dy—N2ⁱ	105.34 (10)	N2—C6—C7	123.4 (4)
O2—Dy—N2ⁱ	147.90 (10)	N2—C6—H6	118.3
O1ⁱ—Dy—N2ⁱ	74.62 (10)	C7—C6—H6	118.3
O1—Dy—N2ⁱ	135.32 (10)	C8—C7—C6	118.7 (4)
N2—Dy—N2ⁱ	77.95 (15)	C8—C7—H7	120.6
O2ⁱ—Dy—N1ⁱ	79.80 (10)	C6—C7—H7	120.6
O2—Dy—N1ⁱ	148.05 (10)	C7—C8—C9	120.6 (4)
O1ⁱ—Dy—N1ⁱ	122.34 (10)	C7—C8—H8	119.7
O1—Dy—N1ⁱ	74.60 (9)	C9—C8—H8	119.7
N2—Dy—N1ⁱ	73.07 (10)	C8—C9—C10	116.9 (4)
N2ⁱ—Dy—N1ⁱ	63.96 (10)	C8—C9—C14	123.8 (4)
O2ⁱ—Dy—N1	148.05 (10)	C10—C9—C14	119.3 (4)
O2—Dy—N1	79.80 (10)	N2—C10—C9	122.7 (4)
O1ⁱ—Dy—N1	74.60 (9)	N2—C10—C11	118.3 (3)
O1—Dy—N1	122.34 (10)	C9—C10—C11	119.0 (4)
N2—Dy—N1	63.96 (10)	N1—C11—C12	122.6 (4)
N2ⁱ—Dy—N1	73.07 (10)	N1—C11—C10	117.7 (3)
N1ⁱ—Dy—N1	123.98 (14)	C12—C11—C10	119.8 (4)
C17—N1—C11	117.3 (4)	C15—C12—C11	117.2 (4)
C17—N1—Dy	123.9 (3)	C15—C12—C13	123.8 (4)
C11—N1—Dy	117.0 (2)	C11—C12—C13	118.9 (4)
C6—N2—C10	117.6 (3)	C14—C13—C12	121.6 (5)
C6—N2—Dy	123.4 (3)	C14—C13—H13	119.2
C10—N2—Dy	117.5 (2)	C12—C13—H13	119.2
C3—N3—C4	119.6 (3)	C13—C14—C9	121.3 (5)
C3—N3—H3	120.2	C13—C14—H14	119.3
C4—N3—H3	120.2	C9—C14—H14	119.3
C5—N4—C4	126.0 (3)	C16—C15—C12	120.0 (4)
C5—N4—H4	117.0	C16—C15—H15	120.0
C4—N4—H4	117.0	C12—C15—H15	120.0
C5—O1—Dy	132.2 (2)	C15—C16—C17	119.4 (4)
C1—O2—Dy	140.8 (2)	C15—C16—H16	120.3
O3—C1—O2	123.1 (3)	C17—C16—H16	120.3
O3—C1—C2	118.8 (3)	N1—C17—C16	123.3 (4)
O2—C1—C2	118.1 (3)	N1—C17—H17	118.3
C3—C2—C5	116.1 (3)	C16—C17—H17	118.3
C3—C2—C1	120.5 (3)	H51—O5—H52	112.0

O2ⁱ—Dy—N1—C17	−6.9 (4)	C1—C2—C3—N3	−178.9 (4)
O2—Dy—N1—C17	63.8 (3)	C3—N3—C4—O4	−178.8 (4)
O1ⁱ—Dy—N1—C17	−20.6 (3)	C3—N3—C4—N4	1.0 (6)
O1—Dy—N1—C17	127.8 (3)	C5—N4—C4—O4	−176.8 (4)
N2—Dy—N1—C17	176.6 (3)	C5—N4—C4—N3	3.4 (6)
N2ⁱ—Dy—N1—C17	−98.8 (3)	Dy—O1—C5—N4	−158.4 (3)
N1ⁱ—Dy—N1—C17	−139.5 (3)	Dy—O1—C5—C2	22.1 (6)
O2ⁱ—Dy—N1—C11	157.4 (2)	C4—N4—C5—O1	174.7 (4)
O2—Dy—N1—C11	−132.0 (3)	C4—N4—C5—C2	−5.7 (6)
O1ⁱ—Dy—N1—C11	143.6 (3)	C3—C2—C5—O1	−177.0 (4)
O1—Dy—N1—C11	−68.0 (3)	C1—C2—C5—O1	2.6 (6)
N2—Dy—N1—C11	−19.2 (3)	C3—C2—C5—N4	3.4 (5)
N2ⁱ—Dy—N1—C11	65.4 (3)	C1—C2—C5—N4	−177.0 (3)
N1ⁱ—Dy—N1—C11	24.7 (2)	C10—N2—C6—C7	2.7 (6)
O2ⁱ—Dy—N2—C6	8.4 (4)	Dy—N2—C6—C7	−162.9 (3)
O2—Dy—N2—C6	−104.8 (3)	N2—C6—C7—C8	−0.4 (7)
O1ⁱ—Dy—N2—C6	161.1 (3)	C6—C7—C8—C9	−0.9 (7)
O1—Dy—N2—C6	−36.2 (3)	C7—C8—C9—C10	−0.2 (7)
N2ⁱ—Dy—N2—C6	108.1 (3)	C7—C8—C9—C14	−179.1 (5)
N1ⁱ—Dy—N2—C6	42.0 (3)	C6—N2—C10—C9	−3.9 (6)
N1—Dy—N2—C6	−175.0 (3)	Dy—N2—C10—C9	162.6 (3)
O2ⁱ—Dy—N2—C10	−157.3 (3)	C6—N2—C10—C11	174.8 (4)
O2—Dy—N2—C10	89.6 (3)	Dy—N2—C10—C11	−18.7 (5)
O1ⁱ—Dy—N2—C10	−4.5 (3)	C8—C9—C10—N2	2.7 (6)
O1—Dy—N2—C10	158.1 (3)	C14—C9—C10—N2	−178.4 (4)
N2ⁱ—Dy—N2—C10	−57.6 (2)	C8—C9—C10—C11	−176.0 (4)
N1ⁱ—Dy—N2—C10	−123.7 (3)	C14—C9—C10—C11	2.9 (6)
N1—Dy—N2—C10	19.3 (3)	C17—N1—C11—C12	2.9 (6)
O2ⁱ—Dy—O1—C5	68.0 (3)	Dy—N1—C11—C12	−162.4 (3)
O2—Dy—O1—C5	−22.9 (3)	C17—N1—C11—C10	−176.5 (4)
O1ⁱ—Dy—O1—C5	23.4 (3)	Dy—N1—C11—C10	18.3 (4)
N2—Dy—O1—C5	−134.2 (4)	N2—C10—C11—N1	0.1 (5)
N2ⁱ—Dy—O1—C5	171.7 (3)	C9—C10—C11—N1	178.8 (4)
N1ⁱ—Dy—O1—C5	149.6 (4)	N2—C10—C11—C12	−179.3 (4)
N1—Dy—O1—C5	−89.6 (3)	C9—C10—C11—C12	−0.6 (6)
O2ⁱ—Dy—O2—C1	−72.1 (4)	N1—C11—C12—C15	−1.3 (7)
O1ⁱ—Dy—O2—C1	−146.4 (4)	C10—C11—C12—C15	178.1 (4)
O1—Dy—O2—C1	9.9 (4)	N1—C11—C12—C13	178.6 (4)
N2—Dy—O2—C1	78.7 (4)	C10—C11—C12—C13	−2.0 (6)
N2ⁱ—Dy—O2—C1	170.4 (4)	C15—C12—C13—C14	−177.8 (6)
N1ⁱ—Dy—O2—C1	−3.8 (5)	C11—C12—C13—C14	2.3 (8)
N1—Dy—O2—C1	137.9 (4)	C12—C13—C14—C9	0.1 (9)
Dy—O2—C1—O3	−176.1 (3)	C8—C9—C14—C13	176.1 (5)
Dy—O2—C1—C2	4.2 (6)	C10—C9—C14—C13	−2.8 (8)
O3—C1—C2—C3	−15.5 (6)	C11—C12—C15—C16	−1.7 (8)
O2—C1—C2—C3	164.1 (4)	C13—C12—C15—C16	178.4 (5)
O3—C1—C2—C5	164.9 (4)	C12—C15—C16—C17	2.9 (8)
O2—C1—C2—C5	−15.4 (6)	C11—N1—C17—C16	−1.7 (6)
C4—N3—C3—C2	−3.0 (7)	Dy—N1—C17—C16	162.5 (3)
C5—C2—C3—N3	0.7 (7)	C15—C16—C17—N1	−1.2 (8)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N3ⁱⁱ	0.86	1.80	2.659 (7)	174
N4—H4···O3ⁱⁱⁱ	0.86	2.01	2.867 (4)	178
N4—H4···O2ⁱⁱⁱ	0.86	2.62	3.183 (4)	124
O5—H51···O3^iv	0.85	2.15	2.993 (5)	175
O5—H52···O4^v	0.85	2.15	2.960 (5)	160

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

Experimental details

Crystal data
Chemical formula	[Dy(C₅H_2.5N₂O₄)₂(C₁₂H₈N₂)₂]·2H₂O
M_r	868.12
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	17.143 (2), 14.4470 (17), 13.2211 (16)
β (°)	100.613 (2)
V (Å³)	3218.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.40
Crystal size (mm)	0.10 × 0.03 × 0.02

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.796, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	11116, 2842, 2619
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.068, 1.06
No. of reflections	2842
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.93, −1.22

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

Selected geometric parameters (Å, º) top

Dy—O2	2.256 (3)	Dy—N2	2.554 (3)
Dy—O1	2.313 (2)	Dy—N1	2.576 (3)

O2ⁱ—Dy—O2	88.73 (14)	N2—Dy—N2ⁱ	77.95 (15)
O2—Dy—O1ⁱ	81.97 (10)	O2—Dy—N1ⁱ	148.05 (10)
O2—Dy—O1	74.32 (9)	O1—Dy—N1ⁱ	74.60 (9)
O1ⁱ—Dy—O1	146.67 (13)	N2—Dy—N1ⁱ	73.07 (10)
O2ⁱ—Dy—N2	147.90 (10)	O2—Dy—N1	79.80 (10)
O2—Dy—N2	105.34 (10)	O1—Dy—N1	122.34 (10)
O1ⁱ—Dy—N2	135.32 (10)	N2—Dy—N1	63.96 (10)
O1—Dy—N2	74.62 (10)	N1ⁱ—Dy—N1	123.98 (14)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N3ⁱⁱ	0.86	1.80	2.659 (7)	174.2
N4—H4···O3ⁱⁱⁱ	0.86	2.01	2.867 (4)	177.5
N4—H4···O2ⁱⁱⁱ	0.86	2.62	3.183 (4)	124.4
O5—H51···O3^iv	0.85	2.15	2.993 (5)	175.4
O5—H52···O4^v	0.85	2.15	2.960 (5)	159.8

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

Acknowledgements

The authors are grateful for financial support from the Guangxi Natural Science Foundation (grant No. 0991008) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, China (grant No. [2006]331).

References

Arora, K. K., Talwelkar, M. S. & Pedireddi, V. R. (2009). New J. Chem. 33, 57–63. Web of Science CSD CrossRef CAS Google Scholar
Baran, E., Mercaser, R. C., Hueso-Ureña, F., Moreno-Carretero, M. N., Quiros-Olozabal, M. & Salas-Peregrin, J. M. (1996). Polyhedron, 15, 1717–1724. CSD CrossRef CAS Web of Science Google Scholar
Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-L., Zhang, Y.-Z. & Liang, F.-P. (2006). Acta Cryst. E62, m1296–m1297. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hueso-Ureña, F., Moreno-Carretero, M. N., Romero-Molina, M. A., Salas-Peregrin, J. M., Sanchez-Sanchez, M. P., Alvarez de Cienfuegos-Lopez, G. & Faure, R. (1993). J. Inorg. Biochem. 51, 613–632. CSD CrossRef Web of Science Google Scholar
Hueso-Ureña, F., Moreno-Carretero, M. N., Quirós-Olozábal, M., Salas-Peregrín, J. M., Faure, R. & Cienfuegos-López, G. A. (1996). Inorg. Chim. Acta, 241, 61–69. CSD CrossRef Web of Science Google Scholar
Jagan, R. & Sivakumar, K. (2009). Acta Cryst. C65, o414–o418. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Luo, J.-H., Hong, M.-C., Zhao, Y.-J., Cao, R. & Weng, J.-B. (2002). Chin. J. Struct. Chem. 21, 392–395. CAS Google Scholar
Maistralis, G., Katsaros, N., Mentzafos, D. & Terzis, A. (1991). Acta Cryst. C47, 740–743. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Maistralis, G., Katsaros, N., Perlepes, S. P. & Kovala-Demertzi, D. (1992). J. Inorg. Biochem. 45, 1–12. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, C.-Y. & Jin, L.-P. (2004a). Polyhedron, 23, 2085–2093. Web of Science CSD CrossRef CAS Google Scholar
Sun, C.-Y. & Jin, L.-P. (2004b). Polyhedron, 23, 2227–2233. Web of Science CSD CrossRef CAS Google Scholar
Xing, H.-H., Chen, Z.-L. & Ng, S. W. (2008a). Acta Cryst. E64, m418. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xing, H.-H., Chen, Z.-L. & Ng, S. W. (2008b). Acta Cryst. E64, m419–m420. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Xiong, W., Xing, H., Su, Y. & Chen, Z. (2008a). Acta Cryst. E64, m1166–m1167. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xiong, W., Xing, H., Su, Y. & Chen, Z. (2008b). Acta Cryst. E64, m1168–m1169. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.