2-Amino-4,6-dimeth-oxy-pyrimidin-1-ium 2,2-dichloro-acetate.

In the title salt, C(6)H(10)N(3)O(2) (+)·C(2)HCl(2)O(2) (-), two cations and two anions are linked by N-H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For the biological activity of heterocyclic compounds, see: Gilchrist (1998 ▶). For the bioactivity of pyrimidine derivatives, see: Xue et al. (1993 ▶). For a related structure, see: Hemamalini et al. (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H10N3O2 +·C2HCl2O2 −

M = 284.10

Triclinic,

a = 6.8502 (14) Å

b = 8.6667 (17) Å

c = 11.255 (2) Å

α = 67.480 (1)°

β = 87.320 (2)°

γ = 85.970 (2)°

V = 615.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.53 mm−1

T = 293 K

0.45 × 0.43 × 0.35 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.795, T max = 0.835

4710 measured reflections

2173 independent reflections

1806 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.200

S = 1.09

2173 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021496/lh5473sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021496/lh5473Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021496/lh5473Isup3.cml

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

C6H10N3O2+·C2HCl2O2−	Z = 2
Mr = 284.10	F(000) = 292
Triclinic, P1	Dx = 1.533 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8502 (14) Å	Cell parameters from 3794 reflections
b = 8.6667 (17) Å	θ = 3.5–27.5°
c = 11.255 (2) Å	µ = 0.53 mm−1
α = 67.480 (1)°	T = 293 K
β = 87.320 (2)°	Block, colorless
γ = 85.970 (2)°	0.45 × 0.43 × 0.35 mm
V = 615.6 (2) Å3

Bruker SMART CCD diffractometer	2173 independent reflections
Radiation source: fine-focus sealed tube	1806 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.795, Tmax = 0.835	k = −10→10
4710 measured reflections	l = −13→13

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.200	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1265P)2 + 0.3628P] where P = (Fo2 + 2Fc2)/3
2173 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

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
Cl1	0.11057 (16)	0.15674 (13)	0.03526 (9)	0.0641 (4)
Cl2	0.44050 (14)	0.24515 (19)	0.14101 (11)	0.0804 (5)
N1	0.5368 (4)	0.7901 (3)	0.4560 (2)	0.0365 (6)
N2	0.3706 (3)	0.6207 (3)	0.6442 (2)	0.0336 (6)
H2	0.2667	0.6043	0.6924	0.040*
N3	0.2252 (4)	0.8660 (3)	0.5053 (3)	0.0450 (7)
H3A	0.2264	0.9542	0.4356	0.054*
H3B	0.1235	0.8474	0.5555	0.054*
O1	0.4900 (3)	0.3802 (3)	0.7880 (2)	0.0487 (6)
O2	0.8446 (3)	0.7020 (3)	0.4156 (2)	0.0530 (7)
O3	0.0938 (4)	0.1810 (3)	0.3189 (2)	0.0511 (7)
O4	−0.0703 (4)	0.4064 (3)	0.1873 (2)	0.0653 (8)
C1	0.3790 (4)	0.7598 (3)	0.5350 (3)	0.0332 (6)
C2	0.5248 (4)	0.5073 (4)	0.6779 (3)	0.0367 (7)
C3	0.6887 (4)	0.5305 (4)	0.6026 (3)	0.0389 (7)
H3	0.7962	0.4540	0.6232	0.047*
C4	0.6855 (4)	0.6780 (4)	0.4910 (3)	0.0384 (7)
C5	0.6408 (6)	0.2493 (5)	0.8325 (4)	0.0651 (11)
H5A	0.6728	0.2056	0.7670	0.098*
H5B	0.5956	0.1614	0.9089	0.098*
H5C	0.7551	0.2931	0.8514	0.098*
C6	0.8456 (6)	0.8491 (5)	0.3002 (4)	0.0614 (10)
H6A	0.7688	0.8339	0.2367	0.092*
H6B	0.9777	0.8690	0.2682	0.092*
H6C	0.7910	0.9432	0.3181	0.092*
C7	0.0616 (4)	0.2935 (4)	0.2130 (3)	0.0378 (7)
C8	0.1932 (4)	0.2995 (4)	0.0968 (3)	0.0394 (7)
H8	0.1832	0.4127	0.0302	0.047*

	U11	U22	U33	U12	U13	U23
Cl1	0.0840 (8)	0.0668 (7)	0.0495 (6)	−0.0127 (5)	−0.0068 (5)	−0.0292 (5)
Cl2	0.0425 (6)	0.1419 (12)	0.0752 (7)	0.0083 (6)	−0.0034 (5)	−0.0639 (8)
N1	0.0382 (13)	0.0356 (13)	0.0345 (13)	−0.0043 (10)	0.0020 (10)	−0.0121 (10)
N2	0.0329 (12)	0.0350 (13)	0.0292 (12)	0.0017 (10)	0.0014 (9)	−0.0089 (10)
N3	0.0435 (14)	0.0386 (14)	0.0392 (14)	0.0085 (11)	0.0022 (11)	−0.0016 (11)
O1	0.0530 (13)	0.0411 (12)	0.0371 (12)	0.0138 (10)	0.0023 (10)	−0.0015 (9)
O2	0.0392 (12)	0.0607 (16)	0.0543 (14)	−0.0042 (11)	0.0145 (10)	−0.0181 (12)
O3	0.0588 (15)	0.0438 (13)	0.0337 (12)	0.0107 (10)	0.0032 (10)	0.0012 (10)
O4	0.0660 (16)	0.0588 (16)	0.0430 (13)	0.0296 (13)	0.0131 (12)	0.0046 (11)
C1	0.0372 (15)	0.0319 (14)	0.0311 (14)	−0.0031 (11)	−0.0025 (11)	−0.0124 (11)
C2	0.0424 (16)	0.0340 (15)	0.0334 (14)	0.0028 (12)	−0.0045 (12)	−0.0128 (12)
C3	0.0330 (15)	0.0410 (16)	0.0416 (16)	0.0042 (12)	−0.0039 (12)	−0.0152 (13)
C4	0.0348 (15)	0.0445 (17)	0.0396 (16)	−0.0071 (13)	0.0019 (12)	−0.0197 (13)
C5	0.070 (2)	0.059 (2)	0.0451 (19)	0.0295 (19)	−0.0043 (18)	−0.0025 (17)
C6	0.057 (2)	0.068 (3)	0.052 (2)	−0.0141 (18)	0.0182 (17)	−0.0157 (18)
C7	0.0431 (16)	0.0315 (15)	0.0340 (15)	0.0008 (12)	0.0002 (12)	−0.0076 (12)
C8	0.0445 (17)	0.0375 (16)	0.0339 (15)	0.0009 (12)	0.0003 (12)	−0.0116 (12)

Cl1—C8	1.767 (3)	O3—C7	1.234 (4)
Cl2—C8	1.768 (3)	O4—C7	1.241 (4)
N1—C4	1.320 (4)	C2—C3	1.353 (4)
N1—C1	1.342 (4)	C3—C4	1.408 (4)
N2—C2	1.354 (4)	C3—H3	0.9300
N2—C1	1.355 (4)	C5—H5A	0.9600
N2—H2	0.8600	C5—H5B	0.9600
N3—C1	1.315 (4)	C5—H5C	0.9600
N3—H3A	0.8600	C6—H6A	0.9600
N3—H3B	0.8600	C6—H6B	0.9600
O1—C2	1.330 (4)	C6—H6C	0.9600
O1—C5	1.433 (4)	C7—C8	1.539 (4)
O2—C4	1.327 (4)	C8—H8	0.9800
O2—C6	1.430 (5)
C4—N1—C1	116.5 (2)	O1—C5—H5A	109.5
C2—N2—C1	120.4 (2)	O1—C5—H5B	109.5
C2—N2—H2	119.8	H5A—C5—H5B	109.5
C1—N2—H2	119.8	O1—C5—H5C	109.5
C1—N3—H3A	120.0	H5A—C5—H5C	109.5
C1—N3—H3B	120.0	H5B—C5—H5C	109.5
H3A—N3—H3B	120.0	O2—C6—H6A	109.5
C2—O1—C5	117.1 (3)	O2—C6—H6B	109.5
C4—O2—C6	117.9 (3)	H6A—C6—H6B	109.5
N3—C1—N1	119.5 (3)	O2—C6—H6C	109.5
N3—C1—N2	118.4 (3)	H6A—C6—H6C	109.5
N1—C1—N2	122.1 (3)	H6B—C6—H6C	109.5
O1—C2—C3	127.8 (3)	O3—C7—O4	126.9 (3)
O1—C2—N2	111.7 (3)	O3—C7—C8	119.0 (3)
C3—C2—N2	120.5 (3)	O4—C7—C8	114.1 (3)
C2—C3—C4	115.5 (3)	C7—C8—Cl1	108.5 (2)
C2—C3—H3	122.2	C7—C8—Cl2	111.4 (2)
C4—C3—H3	122.2	Cl1—C8—Cl2	109.21 (17)
N1—C4—O2	118.7 (3)	C7—C8—H8	109.3
N1—C4—C3	125.0 (3)	Cl1—C8—H8	109.3
O2—C4—C3	116.3 (3)	Cl2—C8—H8	109.3
C4—N1—C1—N3	−179.5 (3)	C1—N1—C4—O2	179.6 (3)
C4—N1—C1—N2	−0.8 (4)	C1—N1—C4—C3	0.9 (4)
C2—N2—C1—N3	179.4 (3)	C6—O2—C4—N1	0.1 (4)
C2—N2—C1—N1	0.7 (4)	C6—O2—C4—C3	179.0 (3)
C5—O1—C2—C3	−1.4 (5)	C2—C3—C4—N1	−0.7 (5)
C5—O1—C2—N2	178.5 (3)	C2—C3—C4—O2	−179.5 (3)
C1—N2—C2—O1	179.6 (3)	O3—C7—C8—Cl1	81.6 (3)
C1—N2—C2—C3	−0.5 (4)	O4—C7—C8—Cl1	−97.9 (3)
O1—C2—C3—C4	−179.6 (3)	O3—C7—C8—Cl2	−38.6 (4)
N2—C2—C3—C4	0.5 (4)	O4—C7—C8—Cl2	141.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O3i	0.86	1.97	2.822 (3)	173
N3—H3A···O3ii	0.86	2.07	2.848 (3)	149
N2—H2···O4i	0.86	1.85	2.692 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O3i	0.86	1.97	2.822 (3)	173
N3—H3A⋯O3ii	0.86	2.07	2.848 (3)	149
N2—H2⋯O4i	0.86	1.85	2.692 (3)	168

Symmetry codes: (i) ; (ii) .