Diammonium 1,1',3,3'-tetra-methyl-2,2',4,4',6,6'-hexa-oxoperhydro-5,5'-bipyrimidine-5,5'-diide monohydrate.

In the title hydrated salt, 2NH(4) (+)·C(12)H(12)N(4)O(6) (2-)·H(2)O, the two hexa-hydro-pyrimidine rings in the dianion are inclined to one another at a dihedral angle of 62.76 (5)°. In the crystal structure, the anions and water mol-ecules are linked into sheets parallel to the bc plane by inter-molecular O-H⋯O hydrogen bonds and sustained by C-H⋯O contacts. The linking of the anions and water mol-ecules with the cations by N-H⋯O hydrogen bonds creates a three-dimensional extended network. The crystal structure is further stabilized by very weak C-H⋯π inter-actions.

Related literature

For general background to and applications of barbituric acid derivatives, see: Negwer (2001 ▶). For related structures, see: Rezende et al. (2005 ▶); da Silva et al. (2005 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

2NH4 +·C12H12N4O6 2−·H2O

M = 362.36

Monoclinic,

a = 8.5345 (1) Å

b = 12.1579 (2) Å

c = 7.7482 (1) Å

β = 100.595 (1)°

V = 790.26 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.46 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.945, T max = 0.975

15091 measured reflections

3387 independent reflections

3237 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.083

S = 1.05

3387 reflections

270 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039968/tk2548sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039968/tk2548Isup2.hkl

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

2NH4+·C12H12N4O62−·H2O	F(000) = 384
Mr = 362.36	Dx = 1.523 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 9975 reflections
a = 8.5345 (1) Å	θ = 3.0–34.6°
b = 12.1579 (2) Å	µ = 0.13 mm−1
c = 7.7482 (1) Å	T = 100 K
β = 100.595 (1)°	Block, yellow
V = 790.26 (2) Å3	0.46 × 0.24 × 0.20 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	3387 independent reflections
Radiation source: fine-focus sealed tube	3237 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 34.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.945, Tmax = 0.975	k = −19→19
15091 measured reflections	l = −12→12

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.0092P] where P = (Fo2 + 2Fc2)/3
3387 reflections	(Δ/σ)max < 0.001
270 parameters	Δρmax = 0.41 e Å−3
2 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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 > 2sigma(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
O1	1.03560 (11)	0.14592 (7)	1.07661 (12)	0.01241 (15)
O2	1.29186 (11)	0.47147 (8)	1.22084 (12)	0.01554 (17)
O3	0.81723 (11)	0.48152 (7)	0.83916 (11)	0.01375 (16)
O4	0.58471 (11)	0.32057 (7)	0.97921 (12)	0.01402 (16)
O5	0.41464 (11)	0.06573 (8)	0.55640 (12)	0.01527 (17)
O6	0.94414 (10)	0.14952 (7)	0.66677 (12)	0.01358 (16)
N1	1.16599 (12)	0.30914 (8)	1.13935 (13)	0.01118 (16)
N2	1.05010 (13)	0.47550 (7)	1.03408 (14)	0.01113 (16)
N3	0.50054 (11)	0.19796 (8)	0.76033 (12)	0.01090 (16)
N4	0.67803 (12)	0.11318 (8)	0.60677 (13)	0.01124 (16)
C1	1.03474 (13)	0.24831 (9)	1.05040 (14)	0.00980 (17)
C2	1.17569 (14)	0.42182 (9)	1.13520 (15)	0.01120 (18)
C3	0.92023 (13)	0.42115 (9)	0.93130 (15)	0.01017 (17)
C4	0.91423 (13)	0.30599 (9)	0.93888 (15)	0.00967 (17)
C5	0.77985 (13)	0.24525 (9)	0.83177 (14)	0.00979 (18)
C6	0.62473 (13)	0.25855 (9)	0.86409 (14)	0.01016 (17)
C7	0.52552 (13)	0.12277 (9)	0.63627 (15)	0.01075 (18)
C8	0.80944 (13)	0.17050 (9)	0.70160 (15)	0.01024 (17)
C9	1.29964 (15)	0.25137 (11)	1.24737 (16)	0.0154 (2)
H9A	1.3982	0.2837	1.2299	0.023*
H9B	1.2972	0.1752	1.2142	0.023*
H9C	1.2912	0.2573	1.3689	0.023*
C10	1.04993 (17)	0.59583 (9)	1.03645 (19)	0.0170 (2)
H10A	1.1471	0.6218	1.1073	0.025*
H10B	0.9608	0.6216	1.0848	0.025*
H10C	1.0418	0.6231	0.9189	0.025*
C11	0.34045 (15)	0.20432 (11)	0.80192 (18)	0.0174 (2)
H11A	0.2627	0.1952	0.6964	0.026*
H11B	0.3261	0.2747	0.8530	0.026*
H11C	0.3274	0.1472	0.8837	0.026*
C12	0.70481 (16)	0.04107 (12)	0.46407 (19)	0.0201 (2)
H12A	0.6055	0.0087	0.4092	0.030*
H12B	0.7785	−0.0159	0.5103	0.030*
H12C	0.7480	0.0831	0.3789	0.030*
N5	0.08583 (12)	0.04901 (9)	0.41174 (14)	0.01257 (17)
H1N5	0.061 (3)	−0.020 (2)	0.410 (3)	0.027 (6)*
H2N5	0.067 (3)	0.083 (2)	0.315 (3)	0.029 (5)*
H3N5	0.195 (3)	0.0572 (17)	0.456 (3)	0.020 (5)*
H4N5	0.035 (3)	0.0832 (18)	0.486 (3)	0.025 (5)*
N6	0.56158 (13)	0.46002 (9)	0.56578 (14)	0.01434 (18)
H1N6	0.566 (3)	0.4075 (16)	0.488 (3)	0.016 (4)*
H2N6	0.465 (3)	0.4638 (17)	0.604 (3)	0.022 (5)*
H3N6	0.568 (3)	0.5221 (19)	0.520 (3)	0.023 (5)*
H4N6	0.641 (3)	0.4479 (18)	0.654 (3)	0.023 (5)*
O1W	0.69194 (13)	0.30906 (8)	0.33669 (14)	0.01932 (18)
H1W1	0.753 (3)	0.364 (2)	0.346 (3)	0.026 (5)*
H2W1	0.667 (3)	0.297 (2)	0.236 (4)	0.033 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0146 (4)	0.0091 (3)	0.0126 (3)	0.0000 (3)	0.0001 (3)	0.0007 (3)
O2	0.0123 (4)	0.0164 (4)	0.0170 (4)	−0.0048 (3)	0.0002 (3)	−0.0031 (3)
O3	0.0144 (4)	0.0107 (3)	0.0147 (4)	0.0010 (3)	−0.0010 (3)	0.0005 (3)
O4	0.0141 (4)	0.0137 (4)	0.0147 (4)	0.0001 (3)	0.0039 (3)	−0.0042 (3)
O5	0.0098 (3)	0.0165 (4)	0.0179 (4)	−0.0020 (3)	−0.0017 (3)	−0.0043 (3)
O6	0.0096 (3)	0.0153 (4)	0.0158 (4)	0.0003 (3)	0.0024 (3)	−0.0037 (3)
N1	0.0091 (4)	0.0118 (4)	0.0117 (4)	−0.0009 (3)	−0.0005 (3)	−0.0001 (3)
N2	0.0107 (4)	0.0087 (3)	0.0133 (4)	−0.0016 (3)	0.0002 (3)	−0.0012 (3)
N3	0.0081 (4)	0.0126 (4)	0.0119 (4)	0.0000 (3)	0.0016 (3)	−0.0014 (3)
N4	0.0092 (4)	0.0112 (4)	0.0128 (4)	−0.0003 (3)	0.0009 (3)	−0.0041 (3)
C1	0.0086 (4)	0.0109 (4)	0.0098 (4)	−0.0006 (3)	0.0014 (3)	−0.0008 (3)
C2	0.0105 (4)	0.0122 (4)	0.0110 (4)	−0.0027 (4)	0.0025 (3)	−0.0010 (3)
C3	0.0098 (4)	0.0103 (4)	0.0102 (4)	−0.0009 (3)	0.0015 (3)	−0.0010 (3)
C4	0.0090 (4)	0.0090 (4)	0.0104 (4)	−0.0004 (3)	0.0001 (3)	−0.0015 (3)
C5	0.0097 (4)	0.0089 (4)	0.0102 (4)	−0.0004 (3)	0.0002 (3)	−0.0011 (3)
C6	0.0100 (4)	0.0092 (4)	0.0107 (4)	−0.0006 (3)	0.0004 (3)	0.0001 (3)
C7	0.0096 (4)	0.0095 (4)	0.0124 (4)	−0.0003 (3)	0.0001 (3)	−0.0002 (3)
C8	0.0101 (4)	0.0090 (4)	0.0109 (4)	−0.0009 (3)	0.0001 (3)	−0.0003 (3)
C9	0.0112 (4)	0.0172 (5)	0.0160 (5)	0.0002 (4)	−0.0023 (4)	0.0023 (4)
C10	0.0188 (5)	0.0099 (4)	0.0211 (5)	−0.0024 (4)	0.0004 (4)	−0.0014 (4)
C11	0.0102 (5)	0.0222 (6)	0.0204 (5)	−0.0007 (4)	0.0044 (4)	−0.0033 (4)
C12	0.0133 (5)	0.0243 (6)	0.0224 (6)	−0.0025 (4)	0.0027 (4)	−0.0145 (5)
N5	0.0120 (4)	0.0126 (4)	0.0130 (4)	−0.0014 (3)	0.0018 (3)	0.0006 (3)
N6	0.0141 (4)	0.0137 (4)	0.0147 (4)	−0.0007 (3)	0.0013 (3)	0.0008 (3)
O1W	0.0220 (5)	0.0170 (4)	0.0176 (4)	−0.0044 (3)	0.0001 (3)	−0.0003 (3)

O1—C1	1.2611 (14)	C9—H9A	0.9600
O2—C2	1.2433 (14)	C9—H9B	0.9600
O3—C3	1.2611 (14)	C9—H9C	0.9600
O4—C6	1.2620 (14)	C10—H10A	0.9600
O5—C7	1.2427 (13)	C10—H10B	0.9600
O6—C8	1.2544 (14)	C10—H10C	0.9600
N1—C2	1.3733 (15)	C11—H11A	0.9600
N1—C1	1.4117 (14)	C11—H11B	0.9600
N1—C9	1.4642 (15)	C11—H11C	0.9600
N2—C2	1.3710 (15)	C12—H12A	0.9600
N2—C3	1.4052 (15)	C12—H12B	0.9600
N2—C10	1.4631 (14)	C12—H12C	0.9600
N3—C7	1.3713 (15)	N5—H1N5	0.86 (2)
N3—C6	1.4139 (14)	N5—H2N5	0.85 (3)
N3—C11	1.4623 (15)	N5—H3N5	0.94 (2)
N4—C7	1.3672 (15)	N5—H4N5	0.89 (2)
N4—C8	1.4072 (14)	N6—H1N6	0.88 (2)
N4—C12	1.4616 (16)	N6—H2N6	0.93 (2)
C1—C4	1.4033 (15)	N6—H3N6	0.84 (2)
C3—C4	1.4028 (15)	N6—H4N6	0.88 (2)
C4—C5	1.4830 (15)	O1W—H1W1	0.84 (3)
C5—C6	1.4013 (15)	O1W—H2W1	0.79 (3)
C5—C8	1.4143 (15)
C2—N1—C1	123.86 (10)	N1—C9—H9B	109.5
C2—N1—C9	116.61 (10)	H9A—C9—H9B	109.5
C1—N1—C9	119.51 (10)	N1—C9—H9C	109.5
C2—N2—C3	123.53 (9)	H9A—C9—H9C	109.5
C2—N2—C10	118.11 (10)	H9B—C9—H9C	109.5
C3—N2—C10	118.34 (10)	N2—C10—H10A	109.5
C7—N3—C6	123.30 (9)	N2—C10—H10B	109.5
C7—N3—C11	117.50 (10)	H10A—C10—H10B	109.5
C6—N3—C11	118.70 (9)	N2—C10—H10C	109.5
C7—N4—C8	124.21 (9)	H10A—C10—H10C	109.5
C7—N4—C12	117.63 (10)	H10B—C10—H10C	109.5
C8—N4—C12	118.14 (10)	N3—C11—H11A	109.5
O1—C1—C4	125.05 (10)	N3—C11—H11B	109.5
O1—C1—N1	117.25 (10)	H11A—C11—H11B	109.5
C4—C1—N1	117.69 (9)	N3—C11—H11C	109.5
O2—C2—N2	122.47 (10)	H11A—C11—H11C	109.5
O2—C2—N1	121.16 (11)	H11B—C11—H11C	109.5
N2—C2—N1	116.36 (10)	N4—C12—H12A	109.5
O3—C3—C4	125.29 (10)	N4—C12—H12B	109.5
O3—C3—N2	116.25 (10)	H12A—C12—H12B	109.5
C4—C3—N2	118.46 (10)	N4—C12—H12C	109.5
C3—C4—C1	119.76 (10)	H12A—C12—H12C	109.5
C3—C4—C5	120.26 (9)	H12B—C12—H12C	109.5
C1—C4—C5	119.97 (9)	H1N5—N5—H2N5	117 (2)
C6—C5—C8	120.00 (9)	H1N5—N5—H3N5	109.6 (19)
C6—C5—C4	120.09 (9)	H2N5—N5—H3N5	107 (2)
C8—C5—C4	119.86 (10)	H1N5—N5—H4N5	108 (2)
O4—C6—C5	125.63 (10)	H2N5—N5—H4N5	108 (2)
O4—C6—N3	116.18 (10)	H3N5—N5—H4N5	107 (2)
C5—C6—N3	118.19 (9)	H1N6—N6—H2N6	113.9 (19)
O5—C7—N4	122.03 (11)	H1N6—N6—H3N6	110.3 (19)
O5—C7—N3	121.25 (10)	H2N6—N6—H3N6	103 (2)
N4—C7—N3	116.71 (10)	H1N6—N6—H4N6	106.3 (19)
O6—C8—N4	117.44 (10)	H2N6—N6—H4N6	111 (2)
O6—C8—C5	125.09 (10)	H3N6—N6—H4N6	112 (2)
N4—C8—C5	117.44 (10)	H1W1—O1W—H2W1	106 (3)
N1—C9—H9A	109.5
C2—N1—C1—O1	−174.49 (10)	C3—C4—C5—C8	117.68 (12)
C9—N1—C1—O1	3.76 (15)	C1—C4—C5—C8	−63.31 (14)
C2—N1—C1—C4	5.98 (15)	C8—C5—C6—O4	178.22 (11)
C9—N1—C1—C4	−175.76 (10)	C4—C5—C6—O4	0.76 (17)
C3—N2—C2—O2	177.67 (11)	C8—C5—C6—N3	−1.73 (15)
C10—N2—C2—O2	−3.67 (17)	C4—C5—C6—N3	−179.19 (9)
C3—N2—C2—N1	−3.18 (16)	C7—N3—C6—O4	−176.44 (10)
C10—N2—C2—N1	175.47 (10)	C11—N3—C6—O4	−4.80 (15)
C1—N1—C2—O2	177.56 (10)	C7—N3—C6—C5	3.52 (15)
C9—N1—C2—O2	−0.74 (16)	C11—N3—C6—C5	175.16 (10)
C1—N1—C2—N2	−1.60 (16)	C8—N4—C7—O5	−175.66 (11)
C9—N1—C2—N2	−179.90 (10)	C12—N4—C7—O5	6.19 (17)
C2—N2—C3—O3	−176.92 (10)	C8—N4—C7—N3	3.66 (16)
C10—N2—C3—O3	4.43 (16)	C12—N4—C7—N3	−174.49 (11)
C2—N2—C3—C4	3.31 (17)	C6—N3—C7—O5	174.96 (10)
C10—N2—C3—C4	−175.34 (10)	C11—N3—C7—O5	3.22 (16)
O3—C3—C4—C1	−178.39 (11)	C6—N3—C7—N4	−4.37 (15)
N2—C3—C4—C1	1.36 (16)	C11—N3—C7—N4	−176.11 (10)
O3—C3—C4—C5	0.63 (18)	C7—N4—C8—O6	176.38 (10)
N2—C3—C4—C5	−179.62 (9)	C12—N4—C8—O6	−5.48 (16)
O1—C1—C4—C3	174.85 (11)	C7—N4—C8—C5	−2.08 (16)
N1—C1—C4—C3	−5.66 (15)	C12—N4—C8—C5	176.06 (11)
O1—C1—C4—C5	−4.17 (17)	C6—C5—C8—O6	−177.28 (11)
N1—C1—C4—C5	175.32 (9)	C4—C5—C8—O6	0.18 (17)
C3—C4—C5—C6	−64.86 (14)	C6—C5—C8—N4	1.05 (15)
C1—C4—C5—C6	114.15 (12)	C4—C5—C8—N4	178.51 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H1N5···O1i	0.87 (2)	2.04 (2)	2.7629 (14)	141 (2)
N5—H1N5···O6i	0.87 (2)	2.52 (2)	3.1697 (14)	132.9 (19)
N5—H2N5···O1ii	0.85 (2)	1.97 (2)	2.8116 (14)	173 (2)
N5—H3N5···O5	0.94 (3)	1.90 (3)	2.8312 (14)	176.1 (19)
N5—H4N5···O6iii	0.89 (2)	1.90 (2)	2.7819 (14)	173 (2)
N6—H1N6···O1W	0.88 (2)	2.10 (2)	2.9126 (15)	152 (2)
N6—H2N6···O2iv	0.93 (3)	2.03 (2)	2.9074 (15)	157.8 (19)
N6—H3N6···O4v	0.84 (2)	1.95 (2)	2.7665 (14)	164 (2)
N6—H4N6···O3	0.88 (2)	1.92 (2)	2.7597 (14)	158 (2)
O1W—H1W1···O3v	0.84 (3)	1.96 (2)	2.7602 (13)	158 (2)
O1W—H2W1···O4vi	0.78 (3)	2.01 (3)	2.7563 (14)	161 (3)
C9—H9A···O1Wvii	0.96	2.51	3.3658 (17)	148
C10—H10C···Cg1v	0.96	2.96	3.8822 (15)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H1N5⋯O1i	0.87 (2)	2.04 (2)	2.7629 (14)	141 (2)
N5—H1N5⋯O6i	0.87 (2)	2.52 (2)	3.1697 (14)	132.9 (19)
N5—H2N5⋯O1ii	0.85 (2)	1.97 (2)	2.8116 (14)	173 (2)
N5—H3N5⋯O5	0.94 (3)	1.90 (3)	2.8312 (14)	176.1 (19)
N5—H4N5⋯O6iii	0.89 (2)	1.90 (2)	2.7819 (14)	173 (2)
N6—H1N6⋯O1W	0.88 (2)	2.10 (2)	2.9126 (15)	152 (2)
N6—H2N6⋯O2iv	0.93 (3)	2.03 (2)	2.9074 (15)	157.8 (19)
N6—H3N6⋯O4v	0.84 (2)	1.95 (2)	2.7665 (14)	164 (2)
N6—H4N6⋯O3	0.88 (2)	1.92 (2)	2.7597 (14)	158 (2)
O1W—H1W1⋯O3v	0.84 (3)	1.96 (2)	2.7602 (13)	158 (2)
O1W—H2W1⋯O4vi	0.78 (3)	2.01 (3)	2.7563 (14)	161 (3)
C9—H9A⋯O1Wvii	0.96	2.51	3.3658 (17)	148
C10—H10C⋯Cg1v	0.96	2.96	3.8822 (15)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) . Cg1 is the centroid the the C1/N1/C2/N2/C3/C4 ring.