Tetra-aqua-bis(orotato-κO)cobalt(II) dihydrate.

In the title Co(II) complex, [Co(C(5)H(3)N(2)O(4))(2)(H(2)O)(4)]·2H(2)O, the Co(II) ion is located on an inversion center and is coordinated by two orotate (2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate) anions and four water mol-ecules in a slightly distorted octa-hedral geometry. The dihedral angle between the carboxyl-ate group and the attached orotate ring is 1.2 (3)°. In the crystal structure, inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. π-π contacts between the orotate rings [centroid-centroid distances = 3.439 (2) and 3.438 (2) Å] further stabilize the structure.

Related literature

For orotic acid, see: Doody et al. (1996 ▶); Köse et al. (2008 ▶); Levine et al. (1974 ▶); Nelson & Michael (2000 ▶); Smith & Baker (1959 ▶). For applications of metal–orotate complexes and their derivatives, see: Schmidbaur et al. (1990 ▶); Castan et al. (1990 ▶); Köse et al. (2006 ▶). For related structures, see: Ha et al. (1999 ▶); Icbudak et al. (2003 ▶); Karipides & Thomas (1986 ▶); Kumberger et al. (1991 ▶); Mutikainen (1987 ▶); Mutikainen et al. (1996 ▶); Nepveu et al. (1995 ▶); Platter et al. (2002 ▶); Sabat et al. (1980 ▶); Solbakk (1971 ▶); Sun et al. (2002 ▶).

Experimental

Crystal data

[Co(C5H3N2O4)2(H2O)4]·2H2O

M = 477.21

Monoclinic,

a = 9.8715 (5) Å

b = 13.1514 (7) Å

c = 6.7281 (3) Å

β = 92.224 (3)°

V = 872.81 (8) Å3

Z = 2

Mo Kα radiation

μ = 1.07 mm−1

T = 100 K

0.35 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.775, T max = 0.851

6413 measured reflections

2006 independent reflections

1905 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.168

S = 1.11

2006 reflections

164 parameters

11 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.99 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015837/xu2754sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015837/xu2754Isup2.hkl

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

[Co(C5H3N2O4)2(H2O)4]·2H2O	F(000) = 490
Mr = 477.21	Dx = 1.816 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2967 reflections
a = 9.8715 (5) Å	θ = 2.2–24.3°
b = 13.1514 (7) Å	µ = 1.07 mm−1
c = 6.7281 (3) Å	T = 100 K
β = 92.224 (3)°	Block, pink
V = 872.81 (8) Å3	0.35 × 0.20 × 0.15 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	2006 independent reflections
Radiation source: fine-focus sealed tube	1905 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→11
Tmin = 0.775, Tmax = 0.851	k = −17→12
6413 measured reflections	l = −8→8

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.106P)2 + 1.3319P] where P = (Fo2 + 2Fc2)/3
2006 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 1.99 e Å−3
11 restraints	Δρmin = −0.49 e Å−3

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 > 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
Co1	0.0000	0.0000	0.0000	0.0219 (3)
O1	−0.1500 (2)	0.0836 (2)	0.1269 (4)	0.0294 (6)
O2	−0.3106 (3)	−0.0336 (2)	0.1649 (5)	0.0388 (7)
O3	−0.3502 (3)	0.4086 (2)	0.1788 (5)	0.0387 (7)
O4	−0.7136 (3)	0.2040 (2)	0.2605 (5)	0.0388 (7)
O5	−0.0640 (3)	−0.1370 (2)	0.1312 (4)	0.0310 (6)
H51	−0.158 (2)	−0.137 (5)	0.127 (9)	0.067*
H52	−0.038 (7)	−0.200 (3)	0.092 (12)	0.09 (3)*
O6	0.1274 (3)	0.0294 (2)	0.2535 (4)	0.0319 (6)
H61	0.175 (5)	0.092 (2)	0.259 (8)	0.060 (18)*
H62	0.191 (5)	−0.021 (3)	0.278 (9)	0.057 (18)*
O7	0.0502 (4)	0.6880 (2)	0.0068 (5)	0.0399 (7)
H71	0.010 (7)	0.656 (5)	−0.106 (6)	0.08 (2)*
H72	0.047 (8)	0.639 (4)	0.114 (7)	0.09 (3)*
N1	−0.3185 (3)	0.2368 (2)	0.1577 (5)	0.0251 (6)
H1	−0.240 (3)	0.250 (5)	0.127 (9)	0.053 (16)*
N2	−0.5297 (3)	0.3038 (2)	0.2173 (5)	0.0269 (6)
H2	−0.573 (7)	0.358 (4)	0.229 (12)	0.09 (3)*
C1	−0.2701 (3)	0.0542 (3)	0.1553 (5)	0.0224 (7)
C2	−0.3695 (3)	0.1405 (3)	0.1770 (5)	0.0216 (6)
C3	−0.3958 (3)	0.3223 (3)	0.1841 (5)	0.0248 (7)
C4	−0.5914 (3)	0.2099 (3)	0.2312 (5)	0.0243 (7)
C5	−0.5017 (3)	0.1247 (3)	0.2120 (5)	0.0226 (7)
H5	−0.5345	0.0588	0.2236	0.027*

	U11	U22	U33	U12	U13	U23
Co1	0.0145 (4)	0.0152 (4)	0.0363 (4)	0.00237 (19)	0.0044 (3)	−0.0016 (2)
O1	0.0167 (11)	0.0196 (12)	0.0525 (16)	0.0007 (9)	0.0096 (10)	−0.0062 (10)
O2	0.0304 (15)	0.0164 (14)	0.071 (2)	−0.0017 (11)	0.0170 (13)	0.0004 (13)
O3	0.0296 (14)	0.0192 (13)	0.0672 (19)	−0.0064 (11)	0.0013 (12)	−0.0018 (12)
O4	0.0164 (12)	0.0321 (15)	0.068 (2)	−0.0008 (10)	0.0099 (12)	−0.0026 (13)
O5	0.0220 (12)	0.0229 (13)	0.0488 (16)	0.0000 (10)	0.0085 (10)	0.0044 (11)
O6	0.0227 (13)	0.0267 (14)	0.0460 (15)	0.0023 (11)	−0.0015 (10)	−0.0024 (12)
O7	0.0453 (18)	0.0282 (15)	0.0462 (17)	0.0016 (13)	0.0007 (13)	0.0015 (12)
N1	0.0180 (13)	0.0189 (15)	0.0389 (16)	−0.0018 (11)	0.0071 (11)	−0.0014 (11)
N2	0.0189 (14)	0.0178 (14)	0.0441 (17)	0.0032 (11)	0.0045 (11)	−0.0049 (12)
C1	0.0147 (14)	0.0176 (15)	0.0351 (16)	0.0007 (12)	0.0038 (11)	−0.0011 (12)
C2	0.0180 (14)	0.0195 (16)	0.0276 (15)	0.0025 (12)	0.0042 (11)	−0.0022 (12)
C3	0.0203 (16)	0.0181 (16)	0.0359 (17)	−0.0002 (12)	0.0001 (12)	−0.0027 (12)
C4	0.0157 (14)	0.0205 (16)	0.0369 (17)	−0.0008 (12)	0.0046 (12)	−0.0051 (13)
C5	0.0165 (14)	0.0159 (15)	0.0358 (17)	0.0006 (11)	0.0055 (12)	0.0000 (12)

Co1—O1	2.056 (2)	O6—H62	0.92 (5)
Co1—O1i	2.056 (2)	O7—H71	0.94 (5)
Co1—O5	2.113 (3)	O7—H72	0.97 (5)
Co1—O5i	2.113 (3)	N1—C2	1.371 (4)
Co1—O6	2.115 (3)	N1—C3	1.374 (5)
Co1—O6i	2.115 (3)	N1—H1	0.83 (2)
O1—C1	1.269 (4)	N2—C3	1.371 (4)
O2—C1	1.224 (5)	N2—C4	1.382 (4)
O3—C3	1.222 (5)	N2—H2	0.84 (6)
O4—C4	1.232 (4)	C2—C1	1.510 (4)
O5—H51	0.93 (2)	C2—C5	1.351 (4)
O5—H52	0.91 (5)	C5—C4	1.437 (5)
O6—H61	0.95 (2)	C5—H5	0.9300
O1—Co1—O1i	180.00 (14)	H71—O7—H72	107 (4)
O1—Co1—O5	92.89 (10)	C2—N1—C3	122.5 (3)
O1i—Co1—O5	87.11 (10)	C2—N1—H1	124 (4)
O1—Co1—O5i	87.11 (10)	C3—N1—H1	113 (4)
O1i—Co1—O5i	92.89 (10)	C3—N2—C4	126.8 (3)
O1—Co1—O6	89.00 (11)	C3—N2—H2	112 (6)
O1i—Co1—O6	91.00 (11)	C4—N2—H2	121 (6)
O1—Co1—O6i	91.00 (11)	O1—C1—C2	113.6 (3)
O1i—Co1—O6i	89.00 (11)	O2—C1—O1	127.2 (3)
O5i—Co1—O5	180.00 (19)	O2—C1—C2	119.2 (3)
O5—Co1—O6	89.84 (11)	N1—C2—C1	116.3 (3)
O5i—Co1—O6	90.16 (11)	C5—C2—N1	121.3 (3)
O5—Co1—O6i	90.16 (11)	C5—C2—C1	122.4 (3)
O5i—Co1—O6i	89.84 (11)	O3—C3—N1	123.4 (3)
O6i—Co1—O6	180.00 (10)	O3—C3—N2	121.8 (3)
C1—O1—Co1	126.3 (2)	N2—C3—N1	114.8 (3)
Co1—O5—H51	108 (4)	O4—C4—N2	120.2 (3)
Co1—O5—H52	124 (5)	O4—C4—C5	125.2 (3)
H52—O5—H51	107 (4)	N2—C4—C5	114.6 (3)
Co1—O6—H61	118 (3)	C2—C5—C4	119.9 (3)
Co1—O6—H62	113 (4)	C2—C5—H5	120.0
H61—O6—H62	107 (4)	C4—C5—H5	120.0
O5—Co1—O1—C1	−36.3 (3)	C4—N2—C3—N1	1.7 (5)
O5i—Co1—O1—C1	143.7 (3)	C3—N2—C4—O4	−179.6 (4)
O6—Co1—O1—C1	−126.1 (3)	C3—N2—C4—C5	1.3 (5)
O6i—Co1—O1—C1	53.9 (3)	N1—C2—C1—O1	1.8 (5)
Co1—O1—C1—O2	21.4 (5)	N1—C2—C1—O2	−177.8 (3)
Co1—O1—C1—C2	−158.2 (2)	C5—C2—C1—O1	−178.7 (3)
C3—N1—C2—C1	−176.5 (3)	C5—C2—C1—O2	1.8 (5)
C3—N1—C2—C5	3.9 (5)	N1—C2—C5—C4	−0.5 (5)
C2—N1—C3—O3	175.6 (4)	C1—C2—C5—C4	180.0 (3)
C2—N1—C3—N2	−4.4 (5)	C2—C5—C4—O4	179.0 (4)
C4—N2—C3—O3	−178.3 (4)	C2—C5—C4—N2	−1.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O7ii	0.83 (4)	2.26 (4)	3.073 (4)	167 (5)
N2—H2···O2iii	0.84 (6)	1.98 (6)	2.790 (4)	162 (7)
O5—H51···O2	0.93 (2)	2.05 (5)	2.805 (4)	137 (5)
O5—H52···O7iv	0.91 (5)	1.82 (5)	2.710 (4)	167 (6)
O6—H61···O4v	0.95 (3)	1.84 (4)	2.781 (4)	173 (5)
O6—H62···O3vi	0.92 (5)	1.84 (5)	2.737 (4)	164 (4)
O7—H71···O5vii	0.94 (5)	1.90 (5)	2.808 (4)	160 (6)
O7—H72···O1viii	0.97 (5)	2.11 (5)	2.957 (4)	145 (6)
O7—H72···O6viii	0.97 (5)	2.44 (7)	3.201 (4)	135 (6)
C5—H5···O3ix	0.93	2.38	3.292 (5)	165

Table 1

Selected bond lengths (Å)

Co1—O1	2.056 (2)
Co1—O5	2.113 (3)
Co1—O6	2.115 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O7	0.83 (4)	2.26 (4)	3.073 (4)	167 (5)
N2—H2⋯O2	0.84 (6)	1.98 (6)	2.790 (4)	162 (7)
O5—H51⋯O2	0.93 (2)	2.05 (5)	2.805 (4)	137 (5)
O5—H52⋯O7	0.91 (5)	1.82 (5)	2.710 (4)	167 (6)
O6—H61⋯O4i	0.95 (3)	1.84 (4)	2.781 (4)	173 (5)
O6—H62⋯O3ii	0.92 (5)	1.84 (5)	2.737 (4)	164 (4)
O7—H71⋯O5	0.94 (5)	1.90 (5)	2.808 (4)	160 (6)
O7—H72⋯O1	0.97 (5)	2.11 (5)	2.957 (4)	145 (6)
O7—H72⋯O6	0.97 (5)	2.44 (7)	3.201 (4)	135 (6)
C5—H5⋯O3	0.93	2.38	3.292 (5)	165

Symmetry codes: (i) ; (ii) .