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

The asymmetric unit of the title compound, Rb(+)·C(4)H(3)N(2)O(3) (-)·C(4)H(4)N(2)O(3)·H(2)O, consists of one rubidium cation, a barbituric acid mol-ecule, a barbiturate anion and one water mol-ecule. The rubidium ion has seven close-contact inter-actions 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 inter-mediate between an anti-prism and a dodeca-hedron. The Rb(+) ions connect layers built of organic components and water mol-ecules 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 = 358.66

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.059

S = 1.03

2555 reflections

199 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.30 e Å−3

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 ▶).

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

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

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

Rb+·C4H4N2O3−·C4H5N2O3·H2O	F(000) = 712
Mr = 358.66	Dx = 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

Nonius KappaCCD diffractometer	2555 independent reflections
Radiation source: fine-focus sealed tube	2239 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.037
Detector resolution: 9 pixels mm-1	θmax = 27.0°, θmin = 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
Tmin = 0.266, Tmax = 0.473	l = 0→8
17623 measured reflections

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(Fo2) + (0.0308P)2 + 0.3427P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2555 reflections	Δρmax = 0.27 e Å−3
199 parameters	Δρmin = −0.30 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
0 constraints	Extinction coefficient: 0
Primary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
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*

	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)

Rb1—O1W	2.8594 (16)	O6A—Rb1v	2.9942 (13)
Rb1—O4B	2.9645 (12)	O6A—Rb1vi	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—O2Biv	3.2641 (14)	C2B—N3B	1.363 (2)
N1A—C6A	1.369 (2)	O2B—Rb1iii	3.1049 (16)
N1A—C2A	1.372 (2)	O2B—Rb1vii	3.2641 (14)
N1A—H1A	0.879 (9)	O2B—Rb1viii	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—O2Biv	140.64 (4)	C6A—C5A—H5A2	108.2
O4B—Rb1—O2Biv	137.49 (4)	C4A—C5A—H5A2	108.2
O6Ai—Rb1—O2Biv	75.00 (4)	H5A1—C5A—H5A2	107.3
O2A—Rb1—O2Biv	70.21 (3)	O6A—C6A—N1A	120.85 (16)
O6Aii—Rb1—O2Biv	63.09 (4)	O6A—C6A—C5A	122.79 (16)
O2Biii—Rb1—O2Biv	102.47 (4)	N1A—C6A—C5A	116.33 (15)
O1W—Rb1—O2Bviii	100.15 (4)	C6A—O6A—Rb1v	124.21 (12)
O4B—Rb1—O2Bviii	75.04 (3)	C6A—O6A—Rb1vi	134.92 (12)
O6Ai—Rb1—O2Bviii	60.78 (3)	Rb1v—O6A—Rb1vi	87.97 (3)
O2A—Rb1—O2Bviii	85.63 (4)	C2B—N1B—C6B	125.45 (15)
O6Aii—Rb1—O2Bviii	126.81 (3)	C2B—N1B—H1B	117.6 (15)
O2Biii—Rb1—O2Bviii	155.95 (5)	C6B—N1B—H1B	116.9 (15)
O2Biv—Rb1—O2Bviii	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)
O2Biv—Rb1—C2Biii	110.36 (4)	C2B—O2B—Rb1vii	133.05 (12)
O2Bviii—Rb1—C2Biii	137.58 (4)	Rb1iii—O2B—Rb1vii	82.45 (3)
O1W—Rb1—Rb1ix	126.08 (3)	C2B—O2B—Rb1viii	96.57 (11)
O4B—Rb1—Rb1ix	118.45 (2)	Rb1iii—O2B—Rb1viii	155.95 (5)
O6Ai—Rb1—Rb1ix	46.58 (3)	Rb1vii—O2B—Rb1viii	76.76 (3)
O2A—Rb1—Rb1ix	82.29 (3)	C2B—N3B—C4B	124.81 (15)
O6Aii—Rb1—Rb1ix	88.18 (3)	C2B—N3B—H3B	111.8 (14)
O2Biii—Rb1—Rb1ix	149.52 (3)	C4B—N3B—H3B	123.4 (14)
O2Biv—Rb1—Rb1ix	47.14 (3)	O4B—C4B—N3B	117.65 (15)
O2Bviii—Rb1—Rb1ix	49.18 (2)	O4B—C4B—C5B	125.34 (16)
C2Biii—Rb1—Rb1ix	151.63 (3)	N3B—C4B—C5B	117.01 (15)
O1W—Rb1—Rb1x	106.17 (3)	C4B—O4B—Rb1	135.81 (11)
O4B—Rb1—Rb1x	125.08 (2)	C6B—C5B—C4B	120.79 (15)
O6Ai—Rb1—Rb1x	106.63 (3)	C6B—C5B—H5B	119.6
O2A—Rb1—Rb1x	81.74 (3)	C4B—C5B—H5B	119.6
O6Aii—Rb1—Rb1x	45.45 (3)	O6B—C6B—C5B	126.67 (16)
O2Biii—Rb1—Rb1x	50.41 (3)	O6B—C6B—N1B	116.23 (15)
O2Biv—Rb1—Rb1x	54.06 (3)	C5B—C6B—N1B	117.09 (15)
O2Bviii—Rb1—Rb1x	148.58 (2)	Rb1—O1W—H1W	117.0 (18)
C2Biii—Rb1—Rb1x	64.29 (3)	Rb1—O1W—H2W	122.1 (19)
Rb1ix—Rb1—Rb1x	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)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O6Biv	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···O2Avii	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···O6Bxi	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)

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⋯O4Aiv	0.83 (1)	2.08 (1)	2.898 (2)	170 (3)

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