2-Isopropyl-6-methyl-4-oxo-3,4-dihydro-pyrimidin-1-ium 2-carb-oxy-4,6-dinitro-phenolate monohydrate.

In the title mol-ecular salt, C(8)H(13)N(2)O(+)·C(7)H(3)N(2)O(7) (-)·H(2)O, the pyrimidinium cation is essentially planar, with a maximum deviation of 0.009 (1) Å. The cation undergoes an enol-keto tautomerism during the crystallization. In the crystal, the ion pairs and water mol-ecules are connected via O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, forming two-dimensional networks parallel to the bc plane. There is an intra-molecular O-H⋯O hydrogen bond in the 3,5-dinitro-salicylate anion, which generates an S(6) ring motif.

Related literature

For applications of pyrimidine derivaties, see: Condon et al. (1993 ▶); Maeno et al. (1990 ▶); Gilchrist (1997 ▶). For a related structure, see: Hemamalini & Fun (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C8H13N2O+·C7H3N2O7 −·H2O

M = 398.33

Triclinic,

a = 6.6691 (3) Å

b = 11.3831 (4) Å

c = 12.2900 (5) Å

α = 89.727 (2)°

β = 76.771 (2)°

γ = 76.930 (2)°

V = 883.62 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.52 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.937, T max = 0.987

17014 measured reflections

4061 independent reflections

3279 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.03

4061 reflections

273 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810042571/fj2355sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042571/fj2355Isup2.hkl

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

C8H13N2O+·C7H3N2O7−·H2O	Z = 2
Mr = 398.33	F(000) = 416
Triclinic, P1	Dx = 1.497 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6691 (3) Å	Cell parameters from 6994 reflections
b = 11.3831 (4) Å	θ = 2.4–31.6°
c = 12.2900 (5) Å	µ = 0.13 mm−1
α = 89.727 (2)°	T = 100 K
β = 76.771 (2)°	Block, yellow
γ = 76.930 (2)°	0.52 × 0.13 × 0.10 mm
V = 883.62 (6) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4061 independent reflections
Radiation source: fine-focus sealed tube	3279 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.937, Tmax = 0.987	k = −14→12
17014 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.3946P] where P = (Fo2 + 2Fc2)/3
4061 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.30537 (18)	−0.17099 (10)	0.14974 (9)	0.0223 (2)
O2	0.5667 (2)	−0.35714 (10)	0.01344 (10)	0.0310 (3)
O3	0.4865 (2)	−0.36692 (10)	−0.14689 (10)	0.0308 (3)
O4	0.36257 (17)	−0.00307 (10)	−0.33888 (9)	0.0231 (3)
O5	0.23770 (18)	0.16989 (10)	−0.24573 (9)	0.0251 (3)
O6	0.07237 (17)	0.19149 (9)	0.16326 (9)	0.0200 (2)
O7	0.14505 (18)	0.02269 (10)	0.25242 (9)	0.0213 (2)
H7	0.1960	−0.0493	0.2360	0.032*
O8	0.31892 (18)	0.38518 (9)	0.41955 (9)	0.0220 (2)
N1	0.30166 (19)	0.05932 (11)	−0.25097 (10)	0.0182 (3)
N2	0.4862 (2)	−0.31082 (11)	−0.06121 (11)	0.0206 (3)
N3	0.11901 (19)	0.64262 (11)	0.66450 (10)	0.0148 (3)
N4	0.23843 (18)	0.58272 (10)	0.47925 (10)	0.0144 (3)
C1	0.3103 (2)	−0.11927 (13)	0.05577 (12)	0.0151 (3)
C2	0.3897 (2)	−0.18173 (13)	−0.05146 (12)	0.0156 (3)
C3	0.3840 (2)	−0.12442 (13)	−0.15046 (12)	0.0158 (3)
H3A	0.4330	−0.1682	−0.2188	0.019*
C4	0.3044 (2)	−0.00117 (13)	−0.14625 (12)	0.0153 (3)
C5	0.2283 (2)	0.06623 (13)	−0.04535 (12)	0.0150 (3)
H5A	0.1774	0.1494	−0.0446	0.018*
C6	0.2289 (2)	0.00879 (13)	0.05385 (12)	0.0139 (3)
C7	0.1427 (2)	0.08136 (13)	0.16144 (12)	0.0157 (3)
C8	0.2598 (2)	0.45827 (13)	0.49893 (12)	0.0158 (3)
C9	0.2071 (2)	0.43350 (13)	0.61585 (12)	0.0159 (3)
H9A	0.2214	0.3538	0.6364	0.019*
C10	0.1374 (2)	0.52333 (13)	0.69601 (12)	0.0159 (3)
C11	0.1694 (2)	0.67070 (13)	0.55878 (12)	0.0142 (3)
C12	0.1447 (2)	0.80024 (12)	0.52940 (12)	0.0151 (3)
H12A	0.1079	0.8501	0.5990	0.018*
C13	−0.0376 (2)	0.83580 (14)	0.47027 (14)	0.0221 (3)
H13A	−0.1654	0.8227	0.5181	0.033*
H13B	−0.0048	0.7874	0.4020	0.033*
H13C	−0.0568	0.9195	0.4537	0.033*
C14	0.3510 (2)	0.82287 (13)	0.45724 (13)	0.0192 (3)
H14A	0.4628	0.7980	0.4955	0.029*
H14B	0.3331	0.9073	0.4438	0.029*
H14C	0.3864	0.7774	0.3871	0.029*
C15	0.0772 (3)	0.50606 (14)	0.81836 (13)	0.0215 (3)
H15A	0.0965	0.4214	0.8310	0.032*
H15B	−0.0686	0.5459	0.8474	0.032*
H15C	0.1647	0.5398	0.8555	0.032*
O1W	0.3284 (2)	0.60970 (11)	0.25362 (10)	0.0271 (3)
H1N3	0.066 (3)	0.7030 (18)	0.7187 (16)	0.028 (5)*
H1N4	0.271 (3)	0.5992 (18)	0.4063 (17)	0.032 (5)*
H2W1	0.339 (3)	0.667 (2)	0.2096 (17)	0.035 (5)*
H1W1	0.377 (4)	0.544 (2)	0.2154 (19)	0.044 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0296 (6)	0.0173 (5)	0.0173 (5)	−0.0039 (5)	−0.0015 (4)	0.0032 (4)
O2	0.0424 (7)	0.0207 (6)	0.0229 (6)	0.0050 (5)	−0.0056 (5)	0.0036 (5)
O3	0.0487 (8)	0.0171 (6)	0.0231 (6)	−0.0034 (5)	−0.0054 (5)	−0.0076 (5)
O4	0.0289 (6)	0.0268 (6)	0.0137 (5)	−0.0082 (5)	−0.0031 (4)	−0.0002 (5)
O5	0.0344 (6)	0.0173 (6)	0.0230 (6)	−0.0043 (5)	−0.0075 (5)	0.0060 (5)
O6	0.0244 (6)	0.0138 (5)	0.0183 (5)	−0.0014 (4)	−0.0006 (4)	−0.0027 (4)
O7	0.0287 (6)	0.0153 (5)	0.0149 (5)	−0.0002 (5)	0.0004 (4)	−0.0004 (4)
O8	0.0323 (6)	0.0137 (5)	0.0175 (6)	−0.0029 (5)	−0.0031 (5)	−0.0019 (4)
N1	0.0184 (6)	0.0198 (7)	0.0179 (7)	−0.0074 (5)	−0.0047 (5)	0.0035 (5)
N2	0.0240 (7)	0.0153 (6)	0.0186 (7)	−0.0035 (5)	0.0018 (5)	0.0001 (5)
N3	0.0166 (6)	0.0122 (6)	0.0140 (6)	−0.0024 (5)	−0.0017 (5)	−0.0006 (5)
N4	0.0171 (6)	0.0116 (6)	0.0130 (6)	−0.0026 (5)	−0.0013 (5)	0.0010 (5)
C1	0.0136 (7)	0.0169 (7)	0.0151 (7)	−0.0059 (5)	−0.0014 (5)	0.0016 (6)
C2	0.0161 (7)	0.0122 (7)	0.0174 (7)	−0.0032 (5)	−0.0020 (5)	−0.0006 (5)
C3	0.0166 (7)	0.0179 (7)	0.0137 (7)	−0.0072 (6)	−0.0016 (5)	−0.0019 (6)
C4	0.0152 (7)	0.0195 (7)	0.0130 (7)	−0.0076 (6)	−0.0032 (5)	0.0034 (6)
C5	0.0132 (7)	0.0135 (7)	0.0186 (7)	−0.0046 (5)	−0.0028 (5)	0.0008 (6)
C6	0.0116 (6)	0.0149 (7)	0.0151 (7)	−0.0043 (5)	−0.0014 (5)	−0.0007 (5)
C7	0.0134 (7)	0.0169 (7)	0.0159 (7)	−0.0047 (5)	−0.0003 (5)	−0.0009 (6)
C8	0.0156 (7)	0.0132 (7)	0.0182 (7)	−0.0028 (5)	−0.0035 (5)	0.0004 (6)
C9	0.0178 (7)	0.0112 (7)	0.0181 (7)	−0.0030 (5)	−0.0036 (6)	0.0036 (6)
C10	0.0147 (7)	0.0157 (7)	0.0175 (7)	−0.0039 (6)	−0.0041 (5)	0.0033 (6)
C11	0.0117 (6)	0.0143 (7)	0.0163 (7)	−0.0028 (5)	−0.0027 (5)	−0.0001 (5)
C12	0.0183 (7)	0.0105 (7)	0.0154 (7)	−0.0033 (5)	−0.0019 (5)	−0.0001 (5)
C13	0.0222 (8)	0.0136 (7)	0.0319 (9)	−0.0033 (6)	−0.0099 (7)	0.0055 (6)
C14	0.0203 (7)	0.0138 (7)	0.0221 (8)	−0.0051 (6)	−0.0008 (6)	0.0007 (6)
C15	0.0267 (8)	0.0189 (8)	0.0176 (8)	−0.0048 (6)	−0.0031 (6)	0.0021 (6)
O1W	0.0475 (8)	0.0128 (6)	0.0158 (6)	−0.0038 (5)	−0.0005 (5)	0.0009 (5)

O1—C1	1.2909 (17)	C5—C6	1.3811 (19)
O2—N2	1.2250 (17)	C5—H5A	0.9300
O3—N2	1.2334 (17)	C6—C7	1.486 (2)
O4—N1	1.2299 (16)	C8—C9	1.441 (2)
O5—N1	1.2311 (16)	C9—C10	1.348 (2)
O6—C7	1.2335 (17)	C9—H9A	0.9300
O7—C7	1.3010 (17)	C10—C15	1.489 (2)
O7—H7	0.8200	C11—C12	1.4981 (19)
O8—C8	1.2177 (18)	C12—C14	1.5314 (19)
N1—C4	1.4586 (18)	C12—C13	1.533 (2)
N2—C2	1.4581 (18)	C12—H12A	0.9800
N3—C11	1.3221 (18)	C13—H13A	0.9600
N3—C10	1.3965 (18)	C13—H13B	0.9600
N3—H1N3	0.91 (2)	C13—H13C	0.9600
N4—C11	1.3285 (19)	C14—H14A	0.9600
N4—C8	1.4166 (18)	C14—H14B	0.9600
N4—H1N4	0.90 (2)	C14—H14C	0.9600
C1—C2	1.429 (2)	C15—H15A	0.9600
C1—C6	1.438 (2)	C15—H15B	0.9600
C2—C3	1.382 (2)	C15—H15C	0.9600
C3—C4	1.380 (2)	O1W—H2W1	0.85 (2)
C3—H3A	0.9300	O1W—H1W1	0.84 (2)
C4—C5	1.389 (2)
C7—O7—H7	109.5	N4—C8—C9	113.61 (12)
O4—N1—O5	124.05 (12)	C10—C9—C8	121.41 (13)
O4—N1—C4	118.14 (12)	C10—C9—H9A	119.3
O5—N1—C4	117.81 (12)	C8—C9—H9A	119.3
O2—N2—O3	123.54 (13)	C9—C10—N3	118.94 (13)
O2—N2—C2	119.12 (12)	C9—C10—C15	124.98 (13)
O3—N2—C2	117.31 (12)	N3—C10—C15	116.08 (13)
C11—N3—C10	122.35 (13)	N3—C11—N4	119.11 (13)
C11—N3—H1N3	119.1 (12)	N3—C11—C12	120.22 (13)
C10—N3—H1N3	118.5 (12)	N4—C11—C12	120.66 (12)
C11—N4—C8	124.54 (12)	C11—C12—C14	111.37 (12)
C11—N4—H1N4	121.1 (12)	C11—C12—C13	109.34 (11)
C8—N4—H1N4	114.3 (12)	C14—C12—C13	111.33 (12)
O1—C1—C2	124.18 (13)	C11—C12—H12A	108.2
O1—C1—C6	120.48 (13)	C14—C12—H12A	108.2
C2—C1—C6	115.33 (12)	C13—C12—H12A	108.2
C3—C2—C1	122.73 (13)	C12—C13—H13A	109.5
C3—C2—N2	116.52 (13)	C12—C13—H13B	109.5
C1—C2—N2	120.74 (12)	H13A—C13—H13B	109.5
C4—C3—C2	118.90 (13)	C12—C13—H13C	109.5
C4—C3—H3A	120.5	H13A—C13—H13C	109.5
C2—C3—H3A	120.5	H13B—C13—H13C	109.5
C3—C4—C5	121.76 (13)	C12—C14—H14A	109.5
C3—C4—N1	118.76 (13)	C12—C14—H14B	109.5
C5—C4—N1	119.48 (13)	H14A—C14—H14B	109.5
C6—C5—C4	119.48 (13)	C12—C14—H14C	109.5
C6—C5—H5A	120.3	H14A—C14—H14C	109.5
C4—C5—H5A	120.3	H14B—C14—H14C	109.5
C5—C6—C1	121.77 (13)	C10—C15—H15A	109.5
C5—C6—C7	119.05 (13)	C10—C15—H15B	109.5
C1—C6—C7	119.18 (12)	H15A—C15—H15B	109.5
O6—C7—O7	122.30 (13)	C10—C15—H15C	109.5
O6—C7—C6	121.12 (13)	H15A—C15—H15C	109.5
O7—C7—C6	116.58 (12)	H15B—C15—H15C	109.5
O8—C8—N4	119.20 (13)	H2W1—O1W—H1W1	108 (2)
O8—C8—C9	127.19 (13)
O1—C1—C2—C3	177.02 (13)	O1—C1—C6—C7	1.1 (2)
C6—C1—C2—C3	−1.7 (2)	C2—C1—C6—C7	179.94 (12)
O1—C1—C2—N2	−4.3 (2)	C5—C6—C7—O6	−0.5 (2)
C6—C1—C2—N2	176.93 (12)	C1—C6—C7—O6	179.66 (13)
O2—N2—C2—C3	153.14 (14)	C5—C6—C7—O7	179.34 (12)
O3—N2—C2—C3	−24.99 (19)	C1—C6—C7—O7	−0.53 (19)
O2—N2—C2—C1	−25.6 (2)	C11—N4—C8—O8	177.87 (13)
O3—N2—C2—C1	156.26 (13)	C11—N4—C8—C9	−2.37 (19)
C1—C2—C3—C4	2.0 (2)	O8—C8—C9—C10	−178.07 (15)
N2—C2—C3—C4	−176.69 (12)	N4—C8—C9—C10	2.18 (19)
C2—C3—C4—C5	−0.6 (2)	C8—C9—C10—N3	−0.8 (2)
C2—C3—C4—N1	179.06 (12)	C8—C9—C10—C15	179.28 (13)
O4—N1—C4—C3	2.98 (19)	C11—N3—C10—C9	−0.6 (2)
O5—N1—C4—C3	−177.24 (13)	C11—N3—C10—C15	179.26 (13)
O4—N1—C4—C5	−177.33 (12)	C10—N3—C11—N4	0.5 (2)
O5—N1—C4—C5	2.45 (19)	C10—N3—C11—C12	179.41 (12)
C3—C4—C5—C6	−1.0 (2)	C8—N4—C11—N3	1.1 (2)
N1—C4—C5—C6	179.34 (12)	C8—N4—C11—C12	−177.78 (12)
C4—C5—C6—C1	1.2 (2)	N3—C11—C12—C14	126.27 (14)
C4—C5—C6—C7	−178.63 (12)	N4—C11—C12—C14	−54.87 (17)
O1—C1—C6—C5	−178.73 (13)	N3—C11—C12—C13	−110.27 (15)
C2—C1—C6—C5	0.07 (19)	N4—C11—C12—C13	68.59 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O6i	0.91 (2)	1.817 (19)	2.7180 (16)	170 (2)
N4—H1N4···O1W	0.90 (2)	1.84 (2)	2.7309 (17)	171 (2)
O1W—H2W1···O1ii	0.85 (2)	1.97 (2)	2.7878 (16)	162 (2)
O1W—H1W1···O3iii	0.84 (2)	2.11 (2)	2.9381 (17)	170 (2)
O7—H7···O1	0.82	1.67	2.4370 (16)	156
C9—H9A···O5iv	0.93	2.54	3.4312 (18)	161
C12—H12A···O7i	0.98	2.41	3.3023 (18)	152
C14—H14B···O4v	0.96	2.60	3.2318 (19)	124
C15—H15C···O3vi	0.96	2.60	3.471 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O6i	0.91 (2)	1.817 (19)	2.7180 (16)	170 (2)
N4—H1N4⋯O1W	0.90 (2)	1.84 (2)	2.7309 (17)	171 (2)
O1W—H2W1⋯O1ii	0.85 (2)	1.97 (2)	2.7878 (16)	162 (2)
O1W—H1W1⋯O3iii	0.84 (2)	2.11 (2)	2.9381 (17)	170 (2)
O7—H7⋯O1	0.82	1.67	2.4370 (16)	156
C9—H9A⋯O5iv	0.93	2.54	3.4312 (18)	161
C12—H12A⋯O7i	0.98	2.41	3.3023 (18)	152
C14—H14B⋯O4v	0.96	2.60	3.2318 (19)	124
C15—H15C⋯O3vi	0.96	2.60	3.471 (2)	152

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