Bis[4-oxido-2-oxo-2,3-di-hydro-pyrimidin-1-ium-5-carboxyl-ato(1.5-)-κO,O]bis-(1,10-phenanthroline-κN,N')dysprosium(III) dihydrate.

In the title compound, [Dy(C(5)H(2.5)N(2)O(4))(2)(C(12)H(8)N(2))(2)]·2H(2)O, the Dy(III) ion is located on a twofold rotation axis and is coordinated in a square-anti-prismatic geometry by two chelating 1,10-phenanthroline mol-ecules as well as two 4-oxido-2-oxo-2,3-di-hydro-pyrimidin-1-ium-5-carboxyl-ato(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(C5H2.5N2O4)2(C12H8N2)2]·2H2O

M = 868.12

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.068

S = 1.06

2842 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.93 e Å−3

Δρmin = −1.22 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036848/pb2007sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Dy(C5H2.5N2O4)2(C12H8N2)2]·2H2O	F(000) = 1724
Mr = 868.12	Dx = 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

Bruker APEXII CCD area-detector diffractometer	2842 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −20→20
Tmin = 0.796, Tmax = 0.954	k = −17→17
11116 measured reflections	l = −15→15

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(Fo2) + (0.0366P)2 + 4.1092P] where P = (Fo2 + 2Fc2)/3
2842 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.93 e Å−3
0 restraints	Δρmin = −1.22 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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···O3iv	0.85	2.15	2.993 (5)	175
O5—H52···O4v	0.85	2.15	2.960 (5)	160

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⋯O3iv	0.85	2.15	2.993 (5)	175
O5—H52⋯O4v	0.85	2.15	2.960 (5)	160

Symmetry codes: (ii) ; (iii) ; (iv) ; (v) .