4,6-Dimeth-oxy-2-(methyl-sulfan-yl)pyrimidinium chloride.

In the title compound, C(7)H(11)N(2)O(2)S(+)·Cl(-), the 4,6-dimeth-oxy-2-(methyl-sulfan-yl)pyrimidinium cation is essentially planar (r.m.s. deviation = 0.043 Å). In the crystal, the anions and cations are connected by inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds, forming a two-dimensional network parallel to (011). Adjacent networks are cross-linked via π-π inter-actions involving the pyrimidinium ring [centroid-centroid distance = 3.5501 (8) Å].

Related literature

For general background to substituted pyrimidines, see: Salas et al. (1995 ▶); Holy et al. (1974 ▶); Hunt et al. (1980 ▶); Baker & Santi (1965 ▶); Balasubramani & Fun (2009 ▶); For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C7H11N2O2S+·Cl−

M = 222.69

Triclinic,

a = 6.6934 (2) Å

b = 8.4713 (2) Å

c = 8.8123 (2) Å

α = 79.774 (1)°

β = 87.294 (1)°

γ = 84.494 (1)°

V = 489.24 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.57 mm−1

T = 100 K

0.32 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.836, T max = 0.922

9438 measured reflections

2126 independent reflections

1889 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.078

S = 1.03

2126 reflections

125 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.31 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/S1600536809055779/ci5011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055779/ci5011Isup2.hkl

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

C7H11N2O2S+·Cl−	Z = 2
Mr = 222.69	F(000) = 232
Triclinic, P1	Dx = 1.512 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6934 (2) Å	Cell parameters from 6382 reflections
b = 8.4713 (2) Å	θ = 2.4–30.1°
c = 8.8123 (2) Å	µ = 0.57 mm−1
α = 79.774 (1)°	T = 100 K
β = 87.294 (1)°	Block, colourless
γ = 84.494 (1)°	0.32 × 0.22 × 0.14 mm
V = 489.24 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2126 independent reflections
Radiation source: fine-focus sealed tube	1889 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→8
Tmin = 0.836, Tmax = 0.922	k = −9→10
9438 measured reflections	l = −11→11

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.2271P] where P = (Fo2 + 2Fc2)/3
2126 reflections	(Δ/σ)max = 0.001
125 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.31 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 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
S1	−0.25972 (5)	0.07775 (4)	0.60806 (4)	0.01603 (11)
O1	0.34406 (15)	0.34047 (13)	0.69667 (11)	0.0171 (2)
O2	0.07854 (16)	0.42350 (13)	0.19722 (11)	0.0174 (2)
N1	0.06343 (18)	0.22322 (15)	0.65196 (14)	0.0143 (3)
N2	−0.05961 (19)	0.27213 (15)	0.40095 (14)	0.0145 (3)
C1	0.2115 (2)	0.31501 (18)	0.59794 (17)	0.0146 (3)
C2	0.2360 (2)	0.38881 (18)	0.44398 (17)	0.0154 (3)
H2A	0.3426	0.4501	0.4099	0.018*
C3	0.0918 (2)	0.36459 (17)	0.34645 (16)	0.0144 (3)
C4	−0.0672 (2)	0.20134 (17)	0.55095 (16)	0.0140 (3)
C5	0.3256 (2)	0.2515 (2)	0.85378 (17)	0.0187 (3)
H5A	0.4342	0.2717	0.9131	0.028*
H5B	0.3305	0.1384	0.8513	0.028*
H5C	0.2001	0.2860	0.9002	0.028*
C6	0.2314 (2)	0.52752 (19)	0.12795 (18)	0.0192 (3)
H6A	0.2041	0.5656	0.0211	0.029*
H6B	0.3610	0.4679	0.1365	0.029*
H6C	0.2299	0.6176	0.1806	0.029*
C7	−0.1949 (2)	0.0026 (2)	0.80670 (17)	0.0189 (3)
H7A	−0.2778	−0.0817	0.8498	0.028*
H7B	−0.2161	0.0886	0.8650	0.028*
H7C	−0.0563	−0.0391	0.8106	0.028*
Cl1	0.63752 (5)	0.19691 (4)	0.19642 (4)	0.01942 (12)
H2	−0.160 (4)	0.258 (3)	0.331 (3)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0151 (2)	0.0185 (2)	0.01466 (19)	−0.00449 (14)	−0.00315 (13)	−0.00105 (14)
O1	0.0169 (5)	0.0222 (6)	0.0127 (5)	−0.0044 (4)	−0.0054 (4)	−0.0020 (4)
O2	0.0207 (6)	0.0205 (6)	0.0106 (5)	−0.0057 (4)	−0.0044 (4)	0.0016 (4)
N1	0.0147 (6)	0.0160 (6)	0.0125 (6)	−0.0012 (5)	−0.0023 (5)	−0.0030 (5)
N2	0.0153 (6)	0.0164 (6)	0.0123 (6)	−0.0027 (5)	−0.0045 (5)	−0.0018 (5)
C1	0.0148 (7)	0.0156 (7)	0.0141 (7)	0.0013 (6)	−0.0044 (5)	−0.0048 (5)
C2	0.0155 (7)	0.0171 (7)	0.0136 (7)	−0.0037 (6)	−0.0020 (5)	−0.0016 (6)
C3	0.0166 (7)	0.0140 (7)	0.0123 (7)	0.0000 (6)	−0.0018 (5)	−0.0019 (5)
C4	0.0139 (7)	0.0144 (7)	0.0136 (7)	0.0007 (5)	−0.0026 (5)	−0.0029 (5)
C5	0.0201 (8)	0.0244 (8)	0.0115 (7)	−0.0044 (6)	−0.0058 (6)	−0.0001 (6)
C6	0.0225 (8)	0.0189 (8)	0.0157 (7)	−0.0048 (6)	−0.0003 (6)	0.0002 (6)
C7	0.0208 (8)	0.0216 (8)	0.0137 (7)	−0.0049 (6)	−0.0026 (6)	0.0007 (6)
Cl1	0.0191 (2)	0.0229 (2)	0.01680 (19)	−0.00531 (15)	−0.00808 (14)	−0.00133 (14)

S1—C4	1.7380 (16)	C2—C3	1.375 (2)
S1—C7	1.8113 (15)	C2—H2A	0.93
O1—C1	1.3292 (17)	C5—H5A	0.96
O1—C5	1.4598 (18)	C5—H5B	0.96
O2—C3	1.3251 (17)	C5—H5C	0.96
O2—C6	1.4556 (19)	C6—H6A	0.96
N1—C4	1.3244 (18)	C6—H6B	0.96
N1—C1	1.336 (2)	C6—H6C	0.96
N2—C4	1.3519 (19)	C7—H7A	0.96
N2—C3	1.358 (2)	C7—H7B	0.96
N2—H2	0.97 (3)	C7—H7C	0.96
C1—C2	1.399 (2)
C4—S1—C7	99.97 (7)	O1—C5—H5A	109.5
C1—O1—C5	116.16 (12)	O1—C5—H5B	109.5
C3—O2—C6	116.90 (12)	H5A—C5—H5B	109.5
C4—N1—C1	116.84 (13)	O1—C5—H5C	109.5
C4—N2—C3	120.03 (13)	H5A—C5—H5C	109.5
C4—N2—H2	121.1 (14)	H5B—C5—H5C	109.5
C3—N2—H2	118.8 (14)	O2—C6—H6A	109.5
O1—C1—N1	118.30 (13)	O2—C6—H6B	109.5
O1—C1—C2	117.18 (13)	H6A—C6—H6B	109.5
N1—C1—C2	124.51 (13)	O2—C6—H6C	109.5
C3—C2—C1	115.49 (14)	H6A—C6—H6C	109.5
C3—C2—H2A	122.3	H6B—C6—H6C	109.5
C1—C2—H2A	122.3	S1—C7—H7A	109.5
O2—C3—N2	112.49 (12)	S1—C7—H7B	109.5
O2—C3—C2	127.29 (14)	H7A—C7—H7B	109.5
N2—C3—C2	120.22 (13)	S1—C7—H7C	109.5
N1—C4—N2	122.85 (14)	H7A—C7—H7C	109.5
N1—C4—S1	120.43 (11)	H7B—C7—H7C	109.5
N2—C4—S1	116.73 (11)
C5—O1—C1—N1	5.85 (19)	C4—N2—C3—C2	−1.1 (2)
C5—O1—C1—C2	−175.01 (13)	C1—C2—C3—O2	178.56 (14)
C4—N1—C1—O1	179.41 (12)	C1—C2—C3—N2	−1.0 (2)
C4—N1—C1—C2	0.3 (2)	C1—N1—C4—N2	−2.6 (2)
O1—C1—C2—C3	−177.67 (13)	C1—N1—C4—S1	177.53 (10)
N1—C1—C2—C3	1.4 (2)	C3—N2—C4—N1	3.0 (2)
C6—O2—C3—N2	178.64 (12)	C3—N2—C4—S1	−177.09 (10)
C6—O2—C3—C2	−0.9 (2)	C7—S1—C4—N1	−4.31 (13)
C4—N2—C3—O2	179.30 (12)	C7—S1—C4—N2	175.82 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl1i	0.96 (3)	2.00 (3)	2.9606 (13)	172 (2)
C6—H6A···Cl1ii	0.96	2.77	3.4896 (16)	132
C6—H6B···Cl1	0.96	2.80	3.7002 (15)	157
C7—H7A···Cl1iii	0.96	2.76	3.5524 (15)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl1i	0.96 (3)	2.00 (3)	2.9606 (13)	172 (2)
C6—H6A⋯Cl1ii	0.96	2.77	3.4896 (16)	132
C6—H6B⋯Cl1	0.96	2.80	3.7002 (15)	157
C7—H7A⋯Cl1iii	0.96	2.76	3.5524 (15)	141

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