Rubidium 2,4,6-trioxo-1,3-diazinan-5-ide–1,3-diazinane-2,4,6-trione–water (1/1/1)

Gryl, M.; Stadnicka, K.

doi:10.1107/S1600536811012657

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages m571-m572

doi:10.1107/S1600536811012657

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Rubidium 2,4,6-trioxo-1,3-diazinan-5-ide–1,3-diazinane-2,4,6-trione–water (1/1/1)

Marlena Gryl ^a ^* and Katarzyna Stadnicka ^a

^aFaculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Kraków, Poland
^*Correspondence e-mail: gryl@chemia.uj.edu.pl

(Received 21 March 2011; accepted 5 April 2011; online 13 April 2011)

The asymmetric unit of the title compound, Rb⁺·C₄H₃N₂O₃⁻·C₄H₄N₂O₃·H₂O, consists of one rubidium cation, a barbituric acid molecule, a barbiturate anion and one water molecule. The rubidium ion has seven close-contact interactions with O atoms, with Rb⋯O distances ranging from 2.8594 (16) to 3.2641 (14) Å. These seven O atoms together with an eighth O atom at 3.492 (2) Å away from Rb form a distorted polyhedron with shape intermediate between an antiprism and a dodecahedron. The Rb⁺ ions connect layers built of organic components and water molecules linked via N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the crystal structures of selected barbiturates, see: Xiong et al. (2003 ); Gryl et al. (2008 , 2011 ); Braga et al. (2010 ); Garcia et al. (2010 ); Ivanova & Spiteller (2010 ) and for those of rubidium salts, see: Clegg & Liddle (2004 ); Yıldırım et al. (2008 ). For classification of hydrogen-bond systems according to graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

Rb⁺·C₄H₃N₂O₃⁻·C₄H₄N₂O₃·H₂O
M_r = 358.66
Monoclinic, P 2₁ /c
a = 9.8810 (1) Å
b = 19.6790 (5) Å
c = 6.4530 (3) Å
β = 108.26 (2)°
V = 1191.59 (15) Å³
Z = 4
Mo Kα radiation
μ = 4.20 mm⁻¹
T = 293 K
0.43 × 0.23 × 0.21 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.266, T_max = 0.473
17623 measured reflections
2555 independent reflections
2239 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.059
S = 1.03
2555 reflections
199 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O6Bⁱ	0.88 (1)	1.90 (1)	2.769 (2)	172 (2)
N3A—H3A⋯O4B	0.86 (1)	1.84 (1)	2.694 (2)	175 (2)
N1B—H1B⋯O2Aⁱⁱ	0.88 (1)	1.94 (1)	2.820 (2)	175 (2)
N3B—H3B⋯O4A	0.87 (1)	2.12 (1)	2.975 (2)	169 (2)
O1W—H1W⋯O6Bⁱⁱⁱ	0.84 (1)	1.87 (1)	2.700 (2)	171 (2)
O1W—H2W⋯O4A^iv	0.83 (1)	2.08 (1)	2.898 (2)	170 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y, -z; (iv) -x+1, -y, -z.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Mercury (Macrae et al., 2006 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012657/vm2087sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012657/vm2087Isup2.hkl

checkCIF report

Comment top

Recently we have reported structures for three polymorphic forms of barbituric acid and urea addition compounds (Gryl et al., 2008) for two of which a charge density analysis was also performed (Gryl et al., 2011). Barbituric acid appeared as a valuable component in designing new, functional materials and in particular polar materials (Xiong, et al., 2003). However many attempts to design and obtain polar barbiturates failed (see for example Ivanova & Spiteller, 2010). Herein we report the structure of the title addition compound (I), the asymmetric unit of which is comprised of a rubidium cation, barbiturate anion, barbituric acid molecule and one water molecule (Fig. 1). Unfortunately, like for many barbiturates, the structure is centrosymmetric (space group P2₁/c). Each Rb1 cation is surrounded by seven oxygen atoms and bridged by O6a (x - 1, y, z) and O2b (-x + 1, y + 1/2, -z + 1/2) to Rb1 (x, -y+1/2, z + 1/2) and by O2b (x, -y + 1/2, z - 1/2) and O6a (x-1, -y + 1/2, z - 1/2) to Rb1 (x, -y + 1/2, z - 1/2) (Fig. 2).

All barbiturate NH groups and water molecules act as hydrogen bond donors. The hydrogen bond geometry is given in Table 1. There are considerable differences in the accepting properties of the carbonyl oxygen atoms. In the barbituric acid molecule, only atom O4a is a hydrogen bond acceptor from O1W, whereas atoms O2a and O6a interact with Rb ions. A different situation is observed in the barbituriate ion: atom O6b is an acceptor of two hydrogen bonds from O1W and N1a whereas atoms O2b and O4b are both involved in interactions with rubidium ions. The structure is comprised of layers built of barbituric acid molecules and barbiturate anions connected by hydrogen bonds (Fig. 3). Graph-set descriptors R₂²(8) and R₈⁶(28) were assigned to the hydrogen bonds according to Bernstein et al., (1995). The two ring systems of R₂²(8) are formed between barbiturate anions and barbituric acid molecules by crystallographically different hydrogen bonds. In the R₈⁶(28) ring formation additionally two water molecules act as hydrogen bond donors. The layers, parallel to ab, are joined together into a three dimensional structure due to interactions of Rb1 cations with oxygen atoms from barbiturate anions, barbituric acid molecules and water molecules (Fig. 4).

Related literature top

For the crystal structures of selected barbiturates, see: Xiong et al. (2003); Gryl et al. (2008, 2011); Braga et al. (2010); Garcia et al. (2010); Ivanova & Spiteller (2010) and for those of rubidium salts, see: Clegg & Liddle (2004); Yıldırım et al. (2008). For classification of hydrogen-bond systems according to graph-set theory see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by mixing aqueous solutions of barbituric acid and rubidium carbonate prepared at 323 K using a water bath. Single crystals suitable for X-ray diffraction were obtained from ethanol solution by slow evaporation at ambient conditions.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Asymmetric unit of the title addition compound showing displacement ellipsoids drawn at the 50% probability level (H atoms are shown as spheres of arbitrary radii). The atoms of barbituric acid molecule are marked by the letter a, whereas those of barbiturate anion with the letter b.
	Fig. 2. Rubidium polyhedra of Rb1^v, Rb1 and Rb1^viii joined by edges O6aⁱⁱ, O2b^ix and O2b^vii, O6a^iv with Rb—Rb distance of 4.1988 (3) Å. Symmetry codes: (i) x - 1, -y + 1/2, z + 1/2; (ii) x - 1, y, z; (iii) -x + 1, -y, -z + 1; (iv) x - 1, -y + 1/2, z - 1/2; (v) x, -y + 1/2, z + 1/2; (vi) x - 1, y, z - 1; (vii) -x + 1, -y, -z; (viii) x, -y + 1/2, z - 1/2; (ix) -x + 1, y + 1/2, -z + 1/2; (x) -x + 1, y + 1/2, -z - 1/2.
	Fig. 3. Hydrogen bond scheme in the organic layer parallel to ab at z = 0.25. Hydrogen bond graph-set descriptors R₂²(8) (two kinds) and R₈⁶(28) are given according to Bernstein et al., (1995).
	Fig. 4. View of the packing along [100] showing the Rb cations in between the layers of organic components and water molecules.

Rubidium 2,4,6-trioxo-1,3-diazinan-5-ide–1,3-diazinane-2,4,6-trione–water (1/1/1) top

Crystal data top

Rb⁺·C₄H₄N₂O₃⁻·C₄H₅N₂O₃·H₂O	F(000) = 712
M_r = 358.66	D_x = 1.999 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3522 reflections
a = 9.8810 (1) Å	θ = 1.0–30.0°
b = 19.6790 (5) Å	µ = 4.20 mm⁻¹
c = 6.4530 (3) Å	T = 293 K
β = 108.26 (2)°	Block, colorless
V = 1191.59 (15) Å³	0.43 × 0.23 × 0.21 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2555 independent reflections
Radiation source: fine-focus sealed tube	2239 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.037
Detector resolution: 9 pixels mm^-1	θ_max = 27.0°, θ_min = 3.5°
ϕ and ω scans to fill Ewald sphere	h = −12→11
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	k = 0→25
T_min = 0.266, T_max = 0.473	l = 0→8
17623 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.0308P)² + 0.3427P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2555 reflections	Δρ_max = 0.27 e Å⁻³
199 parameters	Δρ_min = −0.30 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
0 constraints	Extinction coefficient: 0
Primary atom site location: difference Fourier map

Crystal data top

Rb⁺·C₄H₄N₂O₃⁻·C₄H₅N₂O₃·H₂O	V = 1191.59 (15) Å³
M_r = 358.66	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8810 (1) Å	µ = 4.20 mm⁻¹
b = 19.6790 (5) Å	T = 293 K
c = 6.4530 (3) Å	0.43 × 0.23 × 0.21 mm
β = 108.26 (2)°

Data collection top

Nonius KappaCCD diffractometer	2555 independent reflections
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	2239 reflections with I > 2σ(I)
T_min = 0.266, T_max = 0.473	R_int = 0.037
17623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	6 restraints
wR(F²) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.27 e Å⁻³
2555 reflections	Δρ_min = −0.30 e Å⁻³
199 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.

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

	x	y	z	U_iso*/U_eq
Rb1	0.291837 (19)	0.181732 (10)	0.12045 (3)	0.03861 (8)
N1A	0.83901 (16)	0.22220 (7)	0.3062 (2)	0.0284 (3)
H1A	0.830 (2)	0.2666 (5)	0.295 (3)	0.034*
C2A	0.71713 (19)	0.18635 (8)	0.2905 (3)	0.0262 (4)
O2A	0.60363 (14)	0.21479 (6)	0.2672 (2)	0.0390 (3)
N3A	0.72641 (16)	0.11731 (7)	0.2984 (2)	0.0267 (3)
H3A	0.6475 (14)	0.0959 (9)	0.281 (3)	0.032*
C4A	0.84786 (19)	0.08055 (9)	0.3319 (3)	0.0269 (4)
O4A	0.84464 (14)	0.01867 (6)	0.3376 (2)	0.0368 (3)
C5A	0.98315 (19)	0.11930 (9)	0.3628 (3)	0.0310 (4)
H5A1	1.0442	0.1123	0.5115	0.037*
H5A2	1.0314	0.0999	0.2670	0.037*
C6A	0.96859 (19)	0.19423 (9)	0.3212 (3)	0.0272 (4)
O6A	1.06609 (14)	0.22942 (7)	0.3061 (2)	0.0375 (3)
N1B	0.42573 (15)	−0.14265 (7)	0.2580 (2)	0.0289 (3)
H1B	0.417 (2)	−0.1870 (5)	0.259 (3)	0.035*
C2B	0.55857 (18)	−0.11709 (8)	0.2913 (3)	0.0280 (4)
O2B	0.66394 (15)	−0.15406 (7)	0.3276 (3)	0.0447 (4)
N3B	0.56512 (15)	−0.04808 (7)	0.2804 (2)	0.0267 (3)
H3B	0.6520 (12)	−0.0339 (10)	0.304 (3)	0.032*
C4B	0.44849 (18)	−0.00466 (8)	0.2415 (3)	0.0246 (3)
O4B	0.47093 (14)	0.05801 (6)	0.2357 (2)	0.0325 (3)
C5B	0.31602 (18)	−0.03460 (8)	0.2126 (3)	0.0266 (4)
H5B	0.2358	−0.0073	0.1893	0.032*
C6B	0.30235 (18)	−0.10459 (9)	0.2180 (3)	0.0256 (3)
O6B	0.18751 (13)	−0.13782 (6)	0.1870 (2)	0.0378 (3)
O1W	0.07639 (16)	0.08325 (8)	−0.0724 (3)	0.0478 (4)
H1W	−0.0078 (14)	0.0973 (12)	−0.120 (4)	0.057*
H2W	0.090 (3)	0.0514 (9)	−0.147 (4)	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Rb1	0.02804 (11)	0.03333 (12)	0.05520 (14)	0.00282 (7)	0.01410 (9)	0.00032 (8)
N1A	0.0278 (8)	0.0187 (7)	0.0413 (8)	−0.0023 (6)	0.0148 (6)	−0.0005 (6)
C2A	0.0261 (9)	0.0205 (8)	0.0338 (9)	−0.0004 (6)	0.0120 (7)	−0.0006 (7)
O2A	0.0269 (7)	0.0209 (6)	0.0718 (9)	0.0017 (5)	0.0194 (6)	0.0009 (6)
N3A	0.0232 (7)	0.0176 (7)	0.0412 (8)	−0.0019 (6)	0.0127 (6)	−0.0002 (6)
C4A	0.0291 (9)	0.0251 (8)	0.0274 (8)	0.0020 (7)	0.0102 (7)	0.0018 (7)
O4A	0.0335 (7)	0.0198 (6)	0.0569 (8)	0.0035 (5)	0.0138 (6)	0.0021 (6)
C5A	0.0260 (9)	0.0284 (9)	0.0394 (9)	0.0028 (7)	0.0115 (7)	0.0047 (7)
C6A	0.0253 (9)	0.0282 (9)	0.0289 (8)	−0.0017 (7)	0.0098 (7)	−0.0009 (7)
O6A	0.0288 (7)	0.0344 (7)	0.0528 (8)	−0.0062 (6)	0.0177 (6)	0.0006 (6)
N1B	0.0239 (7)	0.0164 (7)	0.0452 (8)	0.0016 (6)	0.0093 (6)	0.0015 (6)
C2B	0.0240 (9)	0.0223 (8)	0.0376 (9)	0.0012 (7)	0.0095 (7)	0.0010 (7)
O2B	0.0271 (7)	0.0270 (7)	0.0791 (10)	0.0074 (6)	0.0152 (7)	0.0045 (7)
N3B	0.0218 (7)	0.0217 (7)	0.0373 (8)	−0.0005 (6)	0.0102 (6)	0.0007 (6)
C4B	0.0276 (9)	0.0208 (8)	0.0245 (8)	0.0013 (6)	0.0071 (6)	0.0010 (6)
O4B	0.0317 (7)	0.0185 (6)	0.0468 (7)	−0.0007 (5)	0.0115 (6)	0.0031 (5)
C5B	0.0232 (8)	0.0205 (8)	0.0342 (9)	0.0042 (6)	0.0061 (7)	0.0004 (7)
C6B	0.0229 (8)	0.0223 (8)	0.0293 (8)	0.0005 (6)	0.0050 (6)	−0.0011 (7)
O6B	0.0221 (6)	0.0215 (6)	0.0661 (9)	−0.0010 (5)	0.0085 (6)	−0.0024 (6)
O1W	0.0315 (8)	0.0473 (9)	0.0610 (10)	0.0102 (7)	0.0094 (7)	−0.0118 (7)

Geometric parameters (Å, º) top

Rb1—O1W	2.8594 (16)	O6A—Rb1^v	2.9942 (13)
Rb1—O4B	2.9645 (12)	O6A—Rb1^vi	3.0517 (13)
Rb1—O6Aⁱ	2.9942 (13)	N1B—C2B	1.358 (2)
Rb1—O2A	2.9972 (13)	N1B—C6B	1.384 (2)
Rb1—O6Aⁱⁱ	3.0517 (13)	N1B—H1B	0.878 (9)
Rb1—O2Bⁱⁱⁱ	3.1049 (16)	C2B—O2B	1.231 (2)
Rb1—O2B^iv	3.2641 (14)	C2B—N3B	1.363 (2)
N1A—C6A	1.369 (2)	O2B—Rb1ⁱⁱⁱ	3.1049 (16)
N1A—C2A	1.372 (2)	O2B—Rb1^vii	3.2641 (14)
N1A—H1A	0.879 (9)	O2B—Rb1^viii	3.4923 (16)
C2A—O2A	1.220 (2)	N3B—C4B	1.393 (2)
C2A—N3A	1.362 (2)	N3B—H3B	0.870 (9)
N3A—C4A	1.359 (2)	C4B—O4B	1.256 (2)
N3A—H3A	0.862 (9)	C4B—C5B	1.394 (2)
C4A—O4A	1.219 (2)	C5B—C6B	1.386 (2)
C4A—C5A	1.497 (2)	C5B—H5B	0.9300
C5A—C6A	1.498 (2)	C6B—O6B	1.270 (2)
C5A—H5A1	0.9700	O1W—H1W	0.839 (10)
C5A—H5A2	0.9700	O1W—H2W	0.828 (10)
C6A—O6A	1.215 (2)

O1W—Rb1—O4B	81.78 (4)	C6A—N1A—H1A	118.1 (14)
O1W—Rb1—O6Aⁱ	80.80 (4)	C2A—N1A—H1A	116.4 (14)
O4B—Rb1—O6Aⁱ	128.17 (4)	O2A—C2A—N3A	120.73 (16)
O1W—Rb1—O2A	146.72 (4)	O2A—C2A—N1A	121.67 (15)
O4B—Rb1—O2A	68.00 (3)	N3A—C2A—N1A	117.59 (15)
O6Aⁱ—Rb1—O2A	128.79 (4)	C2A—O2A—Rb1	138.91 (11)
O1W—Rb1—O6Aⁱⁱ	79.02 (4)	C4A—N3A—C2A	125.64 (15)
O4B—Rb1—O6Aⁱⁱ	153.12 (4)	C4A—N3A—H3A	118.6 (14)
O6Aⁱ—Rb1—O6Aⁱⁱ	66.76 (3)	C2A—N3A—H3A	115.8 (14)
O2A—Rb1—O6Aⁱⁱ	123.40 (4)	O4A—C4A—N3A	120.43 (16)
O1W—Rb1—O2Bⁱⁱⁱ	77.21 (4)	O4A—C4A—C5A	122.37 (16)
O4B—Rb1—O2Bⁱⁱⁱ	80.94 (4)	N3A—C4A—C5A	117.20 (15)
O6Aⁱ—Rb1—O2Bⁱⁱⁱ	140.12 (4)	C6A—C5A—C4A	116.49 (15)
O2A—Rb1—O2Bⁱⁱⁱ	84.36 (4)	C6A—C5A—H5A1	108.2
O6Aⁱⁱ—Rb1—O2Bⁱⁱⁱ	76.60 (4)	C4A—C5A—H5A1	108.2
O1W—Rb1—O2B^iv	140.64 (4)	C6A—C5A—H5A2	108.2
O4B—Rb1—O2B^iv	137.49 (4)	C4A—C5A—H5A2	108.2
O6Aⁱ—Rb1—O2B^iv	75.00 (4)	H5A1—C5A—H5A2	107.3
O2A—Rb1—O2B^iv	70.21 (3)	O6A—C6A—N1A	120.85 (16)
O6Aⁱⁱ—Rb1—O2B^iv	63.09 (4)	O6A—C6A—C5A	122.79 (16)
O2Bⁱⁱⁱ—Rb1—O2B^iv	102.47 (4)	N1A—C6A—C5A	116.33 (15)
O1W—Rb1—O2B^viii	100.15 (4)	C6A—O6A—Rb1^v	124.21 (12)
O4B—Rb1—O2B^viii	75.04 (3)	C6A—O6A—Rb1^vi	134.92 (12)
O6Aⁱ—Rb1—O2B^viii	60.78 (3)	Rb1^v—O6A—Rb1^vi	87.97 (3)
O2A—Rb1—O2B^viii	85.63 (4)	C2B—N1B—C6B	125.45 (15)
O6Aⁱⁱ—Rb1—O2B^viii	126.81 (3)	C2B—N1B—H1B	117.6 (15)
O2Bⁱⁱⁱ—Rb1—O2B^viii	155.95 (5)	C6B—N1B—H1B	116.9 (15)
O2B^iv—Rb1—O2B^viii	94.58 (4)	O2B—C2B—N1B	121.94 (16)
O1W—Rb1—C2Bⁱⁱⁱ	82.13 (4)	O2B—C2B—N3B	123.22 (16)
O4B—Rb1—C2Bⁱⁱⁱ	63.29 (4)	N1B—C2B—N3B	114.84 (15)
O6Aⁱ—Rb1—C2Bⁱⁱⁱ	157.33 (4)	O2B—C2B—Rb1ⁱⁱⁱ	54.65 (10)
O2A—Rb1—C2Bⁱⁱⁱ	72.24 (4)	N1B—C2B—Rb1ⁱⁱⁱ	110.33 (11)
O6Aⁱⁱ—Rb1—C2Bⁱⁱⁱ	95.40 (4)	N3B—C2B—Rb1ⁱⁱⁱ	105.84 (11)
O2Bⁱⁱⁱ—Rb1—C2Bⁱⁱⁱ	18.87 (4)	C2B—O2B—Rb1ⁱⁱⁱ	106.49 (12)
O2B^iv—Rb1—C2Bⁱⁱⁱ	110.36 (4)	C2B—O2B—Rb1^vii	133.05 (12)
O2B^viii—Rb1—C2Bⁱⁱⁱ	137.58 (4)	Rb1ⁱⁱⁱ—O2B—Rb1^vii	82.45 (3)
O1W—Rb1—Rb1^ix	126.08 (3)	C2B—O2B—Rb1^viii	96.57 (11)
O4B—Rb1—Rb1^ix	118.45 (2)	Rb1ⁱⁱⁱ—O2B—Rb1^viii	155.95 (5)
O6Aⁱ—Rb1—Rb1^ix	46.58 (3)	Rb1^vii—O2B—Rb1^viii	76.76 (3)
O2A—Rb1—Rb1^ix	82.29 (3)	C2B—N3B—C4B	124.81 (15)
O6Aⁱⁱ—Rb1—Rb1^ix	88.18 (3)	C2B—N3B—H3B	111.8 (14)
O2Bⁱⁱⁱ—Rb1—Rb1^ix	149.52 (3)	C4B—N3B—H3B	123.4 (14)
O2B^iv—Rb1—Rb1^ix	47.14 (3)	O4B—C4B—N3B	117.65 (15)
O2B^viii—Rb1—Rb1^ix	49.18 (2)	O4B—C4B—C5B	125.34 (16)
C2Bⁱⁱⁱ—Rb1—Rb1^ix	151.63 (3)	N3B—C4B—C5B	117.01 (15)
O1W—Rb1—Rb1^x	106.17 (3)	C4B—O4B—Rb1	135.81 (11)
O4B—Rb1—Rb1^x	125.08 (2)	C6B—C5B—C4B	120.79 (15)
O6Aⁱ—Rb1—Rb1^x	106.63 (3)	C6B—C5B—H5B	119.6
O2A—Rb1—Rb1^x	81.74 (3)	C4B—C5B—H5B	119.6
O6Aⁱⁱ—Rb1—Rb1^x	45.45 (3)	O6B—C6B—C5B	126.67 (16)
O2Bⁱⁱⁱ—Rb1—Rb1^x	50.41 (3)	O6B—C6B—N1B	116.23 (15)
O2B^iv—Rb1—Rb1^x	54.06 (3)	C5B—C6B—N1B	117.09 (15)
O2B^viii—Rb1—Rb1^x	148.58 (2)	Rb1—O1W—H1W	117.0 (18)
C2Bⁱⁱⁱ—Rb1—Rb1^x	64.29 (3)	Rb1—O1W—H2W	122.1 (19)
Rb1^ix—Rb1—Rb1^x	100.428 (8)	H1W—O1W—H2W	111 (3)
C6A—N1A—C2A	125.34 (15)

C6A—N1A—C2A—O2A	−176.43 (17)	C6B—N1B—C2B—O2B	179.49 (17)
C6A—N1A—C2A—N3A	2.6 (3)	C6B—N1B—C2B—N3B	−0.8 (3)
O2A—C2A—N3A—C4A	−177.35 (17)	O2B—C2B—N3B—C4B	−179.42 (17)
N1A—C2A—N3A—C4A	3.6 (3)	N1B—C2B—N3B—C4B	0.8 (2)
C2A—N3A—C4A—O4A	179.49 (17)	C2B—N3B—C4B—O4B	−179.93 (16)
C2A—N3A—C4A—C5A	0.0 (2)	C2B—N3B—C4B—C5B	0.2 (2)
O4A—C4A—C5A—C6A	171.78 (16)	O4B—C4B—C5B—C6B	178.77 (16)
N3A—C4A—C5A—C6A	−8.7 (2)	N3B—C4B—C5B—C6B	−1.4 (2)
C2A—N1A—C6A—O6A	170.35 (17)	C4B—C5B—C6B—O6B	−177.57 (17)
C2A—N1A—C6A—C5A	−11.3 (2)	C4B—C5B—C6B—N1B	1.4 (2)
C4A—C5A—C6A—O6A	−167.85 (17)	C2B—N1B—C6B—O6B	178.77 (17)
C4A—C5A—C6A—N1A	13.8 (2)	C2B—N1B—C6B—C5B	−0.3 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O6B^iv	0.88 (1)	1.90 (1)	2.769 (2)	172 (2)
N3A—H3A···O4B	0.86 (1)	1.84 (1)	2.694 (2)	175 (2)
N1B—H1B···O2A^vii	0.88 (1)	1.94 (1)	2.820 (2)	175 (2)
N3B—H3B···O4A	0.87 (1)	2.12 (1)	2.975 (2)	169 (2)
O1W—H1W···O6B^xi	0.84 (1)	1.87 (1)	2.700 (2)	171 (2)
O1W—H2W···O4Aⁱⁱⁱ	0.83 (1)	2.08 (1)	2.898 (2)	170 (3)

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

Experimental details

Crystal data
Chemical formula	Rb⁺·C₄H₄N₂O₃⁻·C₄H₅N₂O₃·H₂O
M_r	358.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.8810 (1), 19.6790 (5), 6.4530 (3)
β (°)	108.26 (2)
V (Å³)	1191.59 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.20
Crystal size (mm)	0.43 × 0.23 × 0.21

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.266, 0.473
No. of measured, independent and observed [I > 2σ(I)] reflections	17623, 2555, 2239
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.059, 1.03
No. of reflections	2555
No. of parameters	199
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.30

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), Mercury (Macrae et al., 2006) and ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O6Bⁱ	0.88 (1)	1.90 (1)	2.769 (2)	172 (2)
N3A—H3A···O4B	0.86 (1)	1.84 (1)	2.694 (2)	175 (2)
N1B—H1B···O2Aⁱⁱ	0.88 (1)	1.94 (1)	2.820 (2)	175 (2)
N3B—H3B···O4A	0.87 (1)	2.12 (1)	2.975 (2)	169 (2)
O1W—H1W···O6Bⁱⁱⁱ	0.84 (1)	1.87 (1)	2.700 (2)	171 (2)
O1W—H2W···O4A^iv	0.83 (1)	2.08 (1)	2.898 (2)	170 (3)

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

Acknowledgements

The authors thank the X-ray Diffraction Laboratory. Faculty of Chemistry, Jagiellonian University, for making the Nonius KappaCCD diffractometer available. This work was partially supported by the Polish Ministry of Science and Higher Education: grant No. N N204 316537.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Braga, D., Grepioni, F., Maini, L., Prosperi, S., Gobetto, R. & Chierotti, M. R. (2010). Chem. Commun. 46, 7715–7717. Web of Science CSD CrossRef CAS Google Scholar
Clegg, W. & Liddle, S. T. (2004). Acta Cryst. E60, m1492–m1494. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Garcia, H. C., Diniz, R., Yoshida, M. I. & Oliveira, L. F. C. (2010). J. Mol. Struct. 978, 79–85. CrossRef CAS Google Scholar
Gryl, M., Krawczuk, A. & Stadnicka, K. (2008). Acta Cryst. B64, 623–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gryl, M., Krawczuk-Pantula, A. & Stadnicka, K. (2011). Acta Cryst. B67, 144–154. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ivanova, B. B. & Spiteller, M. (2010). Cryst. Growth Des. 10, 2470–2474. Web of Science CSD CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xiong, Y., He, C., An, T.-C., Cha, C.-H., Zhu, X.-H. & Jiang, S. (2003). Transition Met. Chem. 28, 69–73. CrossRef CAS Google Scholar
Yıldırım, S. Ö., McKee, V., Khardli, F.-Z., Mimouni, M. & Hadda, T. B. (2008). Acta Cryst. E64, m154–m155. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Pages m571-m572

doi:10.1107/S1600536811012657

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Rubidium 2,4,6-trioxo-1,3-diazinan-5-ide–1,3-diazinane-2,4,6-trione–water (1/1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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metal-organic compounds