2-Methyl-sulfan-yl-1H-perimidin-3-ium iodide.

In the structure of the title salt C(12)H(11)N(2)S(+)·I(-), the methyl-sulfanyl group of the cation is nearly coplanar with the perimidine rings, as indicated by the C-S-C-N torsion angles of 2.9 (5) and -177.2 (3)°, respectively. The (S)C-N bond lengths in the heterocyclic ring are approximately equal [1.325 (5) and 1.326 (6) Å] suggesting a degree of delocalization. In the crystal, cations and anions are linked via two discrete N-H⋯I hydrogen bonds, forming chains along the b axis.

Related literature

For synthetic details and applications, see: Liu & Chen (1984 ▶); Herbert et al. (1987 ▶). For the NMR spectra, see Woodgate et al. (1988 ▶). For related structures, see: Molčanov et al. (2012 ▶); Wang (2012 ▶); Tiritiris & Kantlehner (2012 ▶).

Experimental

Crystal data

C12H11N2S+·I−

M = 342.19

Monoclinic,

a = 7.0107 (14) Å

b = 8.8968 (18) Å

c = 19.520 (4) Å

β = 95.90 (3)°

V = 1211.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.79 mm−1

T = 298 K

0.20 × 0.17 × 0.10 mm

Data collection

Stoe IPDS 2T diffractometer

Absorption correction: numerical (X-RED32; Stoe & Cie, 2005 ▶) T min = 0.605, T max = 0.768

8695 measured reflections

3266 independent reflections

2151 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.094

S = 1.11

3266 reflections

152 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.98 e Å−3

Δρmin = −0.47 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033697/sj5260sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033697/sj5260Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033697/sj5260Isup3.cml

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

C12H11N2S+·I−	F(000) = 664
Mr = 342.19	Dx = 1.877 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3266 reflections
a = 7.0107 (14) Å	θ = 2.1–29.2°
b = 8.8968 (18) Å	µ = 2.79 mm−1
c = 19.520 (4) Å	T = 298 K
β = 95.90 (3)°	Plate, green
V = 1211.1 (4) Å3	0.20 × 0.17 × 0.10 mm
Z = 4

Stoe IPDS 2T diffractometer	3266 independent reflections
Radiation source: fine-focus sealed tube	2151 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 0.15 pixels mm-1	θmax = 29.2°, θmin = 2.1°
rotation method scans	h = −9→9
Absorption correction: numerical (X-RED32; Stoe & Cie, 2005)	k = −12→10
Tmin = 0.605, Tmax = 0.768	l = −26→23
8695 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.0203P] where P = (Fo2 + 2Fc2)/3
3266 reflections	(Δ/σ)max = 0.001
152 parameters	Δρmax = 0.98 e Å−3
1 restraint	Δρmin = −0.47 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
I1	0.23717 (5)	0.01191 (3)	0.335840 (18)	0.04724 (12)
S1	0.3337 (2)	0.57350 (14)	0.29413 (7)	0.0475 (3)
N1	0.2710 (5)	0.4113 (4)	0.4069 (2)	0.0308 (8)
N2	0.3149 (6)	0.6660 (4)	0.4194 (2)	0.0341 (9)
C1	0.2992 (8)	0.3909 (6)	0.2564 (3)	0.0481 (13)
H1A	0.3861	0.3211	0.2806	0.072*
H1B	0.3232	0.3950	0.2089	0.072*
H1C	0.1696	0.3588	0.2595	0.072*
C2	0.3031 (6)	0.5445 (5)	0.3799 (2)	0.0304 (9)
C3	0.2384 (6)	0.3919 (5)	0.4769 (2)	0.0295 (9)
C4	0.1976 (7)	0.2561 (5)	0.5032 (3)	0.0376 (11)
H4	0.1910	0.1707	0.4756	0.045*
C5	0.1651 (7)	0.2459 (6)	0.5733 (3)	0.0432 (12)
H5	0.1363	0.1531	0.5916	0.052*
C6	0.1753 (7)	0.3702 (6)	0.6146 (3)	0.0414 (12)
H6	0.1535	0.3607	0.6606	0.050*
C7	0.2184 (6)	0.5129 (5)	0.5885 (2)	0.0344 (9)
C8	0.2492 (5)	0.5236 (5)	0.5181 (2)	0.0295 (8)
C9	0.2892 (6)	0.6642 (5)	0.4898 (2)	0.0299 (9)
C10	0.3011 (7)	0.7923 (5)	0.5285 (3)	0.0406 (11)
H10	0.3295	0.8844	0.5095	0.049*
C11	0.2689 (7)	0.7801 (6)	0.5986 (3)	0.0451 (13)
H11	0.2756	0.8664	0.6257	0.054*
C12	0.2284 (7)	0.6463 (6)	0.6281 (3)	0.0434 (12)
H12	0.2074	0.6427	0.6744	0.052*
H1	0.274 (8)	0.328 (7)	0.387 (3)	0.052*
H2	0.327 (8)	0.746 (4)	0.401 (3)	0.052*

	U11	U22	U33	U12	U13	U23
I1	0.0704 (2)	0.02971 (16)	0.04296 (19)	−0.00194 (17)	0.01260 (14)	0.00215 (16)
S1	0.0825 (10)	0.0347 (6)	0.0260 (6)	−0.0092 (6)	0.0095 (6)	0.0024 (5)
N1	0.036 (2)	0.0292 (18)	0.029 (2)	−0.0009 (15)	0.0099 (16)	−0.0010 (16)
N2	0.046 (2)	0.0261 (18)	0.031 (2)	−0.0010 (16)	0.0056 (18)	0.0030 (15)
C1	0.074 (4)	0.037 (3)	0.034 (3)	−0.008 (2)	0.011 (3)	−0.008 (2)
C2	0.031 (2)	0.032 (2)	0.028 (2)	0.0019 (17)	0.0010 (18)	0.0031 (17)
C3	0.025 (2)	0.035 (2)	0.030 (2)	0.0053 (17)	0.0057 (18)	0.0056 (18)
C4	0.038 (3)	0.036 (2)	0.039 (3)	0.000 (2)	0.007 (2)	0.004 (2)
C5	0.047 (3)	0.044 (3)	0.040 (3)	−0.001 (2)	0.011 (2)	0.011 (2)
C6	0.038 (3)	0.056 (3)	0.030 (3)	0.005 (2)	0.006 (2)	0.009 (2)
C7	0.0287 (19)	0.047 (3)	0.027 (2)	0.006 (2)	0.0014 (16)	0.002 (2)
C8	0.0248 (18)	0.034 (2)	0.029 (2)	0.0038 (17)	0.0010 (16)	−0.0004 (19)
C9	0.027 (2)	0.033 (2)	0.029 (2)	0.0021 (17)	0.0024 (18)	−0.0025 (18)
C10	0.047 (3)	0.033 (2)	0.040 (3)	0.003 (2)	0.003 (2)	−0.005 (2)
C11	0.046 (3)	0.048 (3)	0.040 (3)	0.003 (2)	−0.002 (2)	−0.019 (2)
C12	0.041 (3)	0.062 (3)	0.026 (3)	0.004 (2)	0.001 (2)	−0.007 (2)

S1—C2	1.730 (5)	C4—H4	0.9300
S1—C1	1.789 (5)	C5—C6	1.366 (7)
N1—C2	1.325 (5)	C5—H5	0.9300
N1—C3	1.418 (6)	C6—C7	1.413 (7)
N1—H1	0.85 (6)	C6—H6	0.9300
N2—C2	1.325 (6)	C7—C12	1.415 (7)
N2—C9	1.404 (6)	C7—C8	1.415 (6)
N2—H2	0.811 (19)	C8—C9	1.408 (6)
C1—H1A	0.9600	C9—C10	1.366 (6)
C1—H1B	0.9600	C10—C11	1.414 (7)
C1—H1C	0.9600	C10—H10	0.9300
C3—C4	1.356 (6)	C11—C12	1.365 (8)
C3—C8	1.419 (6)	C11—H11	0.9300
C4—C5	1.412 (7)	C12—H12	0.9300
C2—S1—C1	103.8 (2)	C6—C5—H5	119.5
C2—N1—C3	122.9 (4)	C4—C5—H5	119.5
C2—N1—H1	126 (4)	C5—C6—C7	121.0 (4)
C3—N1—H1	111 (4)	C5—C6—H6	119.5
C2—N2—C9	123.6 (4)	C7—C6—H6	119.5
C2—N2—H2	118 (4)	C6—C7—C12	123.8 (4)
C9—N2—H2	119 (4)	C6—C7—C8	118.0 (4)
S1—C1—H1A	109.5	C12—C7—C8	118.1 (4)
S1—C1—H1B	109.5	C9—C8—C7	119.8 (4)
H1A—C1—H1B	109.5	C9—C8—C3	120.8 (4)
S1—C1—H1C	109.5	C7—C8—C3	119.4 (4)
H1A—C1—H1C	109.5	C10—C9—N2	121.7 (4)
H1B—C1—H1C	109.5	C10—C9—C8	121.8 (4)
N1—C2—N2	120.1 (4)	N2—C9—C8	116.5 (4)
N1—C2—S1	124.2 (3)	C9—C10—C11	117.7 (5)
N2—C2—S1	115.8 (3)	C9—C10—H10	121.1
C4—C3—N1	122.4 (4)	C11—C10—H10	121.1
C4—C3—C8	121.4 (4)	C12—C11—C10	122.4 (5)
N1—C3—C8	116.2 (4)	C12—C11—H11	118.8
C3—C4—C5	119.1 (5)	C10—C11—H11	118.8
C3—C4—H4	120.4	C11—C12—C7	120.1 (5)
C5—C4—H4	120.4	C11—C12—H12	119.9
C6—C5—C4	121.0 (5)	C7—C12—H12	119.9
C3—N1—C2—N2	3.3 (7)	C12—C7—C8—C3	−179.5 (4)
C3—N1—C2—S1	−177.2 (3)	C4—C3—C8—C9	−179.2 (4)
C9—N2—C2—N1	−2.1 (7)	N1—C3—C8—C9	0.3 (6)
C9—N2—C2—S1	178.4 (3)	C4—C3—C8—C7	0.6 (6)
C1—S1—C2—N1	2.9 (5)	N1—C3—C8—C7	−179.9 (4)
C1—S1—C2—N2	−177.7 (4)	C2—N2—C9—C10	−179.5 (4)
C2—N1—C3—C4	177.1 (4)	C2—N2—C9—C8	0.0 (6)
C2—N1—C3—C8	−2.4 (6)	C7—C8—C9—C10	0.5 (6)
N1—C3—C4—C5	−179.4 (4)	C3—C8—C9—C10	−179.7 (4)
C8—C3—C4—C5	0.0 (7)	C7—C8—C9—N2	−179.0 (4)
C3—C4—C5—C6	−0.4 (8)	C3—C8—C9—N2	0.8 (6)
C4—C5—C6—C7	0.1 (8)	N2—C9—C10—C11	178.6 (5)
C5—C6—C7—C12	179.1 (5)	C8—C9—C10—C11	−0.9 (7)
C5—C6—C7—C8	0.5 (7)	C9—C10—C11—C12	0.5 (8)
C6—C7—C8—C9	178.9 (4)	C10—C11—C12—C7	0.3 (8)
C12—C7—C8—C9	0.3 (6)	C6—C7—C12—C11	−179.3 (5)
C6—C7—C8—C3	−0.8 (6)	C8—C7—C12—C11	−0.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···I1i	0.81 (2)	2.72 (3)	3.500 (4)	161 (5)
N1—H1···I1	0.85 (6)	2.98 (6)	3.813 (4)	169 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯I1i	0.81 (2)	2.72 (3)	3.500 (4)	161 (5)
N1—H1⋯I1	0.85 (6)	2.98 (6)	3.813 (4)	169 (5)

Symmetry code: (i) .