5-Methyl-3,6,7,8a-tetra­hydro-2H-diimidazo[1,2-c:1′,2′-e]pyrido[1,2-a][1,3,5]triazin-5-ium iodide

Wasilewska, A.; Sączewski, F.; Gdaniec, M.

doi:10.1107/S1600536810019495

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1486

https://doi.org/10.1107/S1600536810019495

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5-Methyl-3,6,7,8a-tetrahydro-2H-diimidazo[1,2-c:1′,2′-e]pyrido[1,2-a][1,3,5]triazin-5-ium iodide

Aleksandra Wasilewska,^a Franciszek Sączewski ^a and Maria Gdaniec ^b ^*

^aDepartment of Chemical Technology of Drugs, Medical University of Gdańsk, 80-416 Gdańsk, Poland, and ^bFaculty of Chemistry, Adam Mickiewicz University, 60-780 Poznań, Poland
^*Correspondence e-mail: magdan@amu.edu.pl

(Received 11 May 2010; accepted 24 May 2010; online 29 May 2010)

The structure of the title compound, C₁₂H₁₆N₅⁺·I⁻, shows that the methylation reaction with CH₃I occurred at the imine N atom at position 5 of the 3,6,7,8a-tetrahydro-2H-diimidazo[1,2-c:1′,2′-e]pyrido[1,2-a][1,3,5]triazine system. In the cation, the sp³-hybridized C atom belonging to the fused dihydropyrine and dihydro-1,3,5-triazine rings deviates by 0.514 (3) Å from the best plane defined by the remaining cationic non-H atoms. The fused dihydropyridine and dihydro-1,3,5-triazine rings are each in a half-chair conformation with the sp³-hybridized C atom as a flap. The iodide anion is 3.573 (2) Å from the methylated N atom and exhibits five short C—H⋯I⁻ contacts with distances less than 3.16 Å. The structure has been determined from a non-merohedral twin with twin law [−1 0 0 0 − 1 0 0.115 0 1], minor domain = 0.1559 (12).

Related literature

For the synthesis and data reported earlier for the title compound, see: Sączewski & Foks (1981 ). For the programs used to derive the twin law, see: Cooper et al.(2002 ); Farrugia (1999 ).

Experimental

Crystal data

C₁₂H₁₆N₅⁺·I⁻
M_r = 357.20
Monoclinic, P 2₁ /n
a = 7.6299 (2) Å
b = 15.3939 (4) Å
c = 11.4503 (3) Å
β = 92.204 (2)°
V = 1343.89 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.37 mm⁻¹
T = 100 K
0.2 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur-E CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.496, T_max = 0.789
25955 measured reflections
4406 independent reflections
4018 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.070
S = 1.20
4406 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 1.74 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯I1ⁱ	0.99	3.15	4.007 (3)	145
C6—H6A⋯I1ⁱⁱ	0.99	3.05	4.010 (3)	163
C9—H9⋯I1ⁱⁱⁱ	0.95	3.08	4.025 (3)	172
C12—H12⋯I1^iv	0.95	3.14	3.887 (3)	137
C17—H17C⋯I1ⁱ	0.98	3.16	4.025 (3)	148
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810019495/tk2676sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810019495/tk2676Isup2.hkl

checkCIF report

Comment top

Biguanide derivatives are known to possess diverse biological activities, including antidiabetic, antibacterial, germicidic, antiviral and antimalarial. On the other hand, quaternary ammonium salts constitute a well known class of bacteriostatic agents. Therefore, we have decided to synthesize some N-alkylated cyclic biguanide derivatives for biological testing, based on the previously described procedure (Sączewski & Foks, 1981) which consists in the reaction of 2,3,6,7,8a,13-hexahydropyrido[1,2-a]diimidazo[1',2'-c:1'',2''-e]-1,3,5-triazine (1) with an alkyl halide. As shown in Fig. 1, the course of the reaction of 1 with methyl iodide has not been established and two products, 2 or 3, arising from either N1 or N5 alkylation have been proposed. In this work, based on X-ray structure analysis (Fig. 2) and hetero-correlation NMR experiments (HSQC and HMBC), the structure of the title compound (2) is determined unambiguously. Regioselectivity of N-alkylation of the cyclic biguanide derivative 1 could not be predicted on the basis of calculated electrostatic potential and charge distribution. The structure of the N5 alkylated product 2 was also confirmed by 2D NMR spectroscopic data. Thus, assignment of signals observed in ¹H and ¹³C-NMR spectra was possible using HSQC spectrum (see numbering scheme in Fig. 3). The crucial signals of quaternary carbon atoms C13a and C4a were found at 145.7 and 152.6 p.p.m., respectively. 3-Bond correlation from the latter carbon to a singlet of three protons at 3.26 p.p.m. observed in the HMBC spectrum (Fig. 4) indicated the placement of methyl group at the N5 nitrogen atom.

Related literature top

For the synthesis and data reported earlier for the title compound, see: Sączewski & Foks (1981). For the programs used to derive the twin law, see: Cooper et al.(2002); Farrugia (1999).

Experimental top

1D and 2D NMR spectra were recorded on a Varian Unity 500 spectrometer. The title compound was prepared according to the previously described procedure (Sączewski & Foks, 1981); m.p. 492–494 K (decomp.); ¹H NMR (500 MHz, DMSO-d₆, see Fig. 3 for numbering scheme) δ_H6.94 (1H, d, J = 7.2 Hz, H12), 6.22–6.19 (1H, ddd, J=9.8, 6.8, ~1 Hz, H10), 5.86 (1H, t, J = 1 Hz, H8a), 5.67 (1H, dd, J = 9.8, ~1 Hz, H9), 5.41–5.38 (1H, dd, J = 7.2, 6.8 Hz, H11), 4.42 (1H, dt, J = 9.3, 6.8 Hz, H2), 4.20 (1H, dt, J = 9.3, 6.8 Hz, H2), 4.01–3.83 (4H, m, H7, H6, 2xH3),3.78–3.71 (1H, m, H6), 3.49–3.43 (1H, m, H7), 3.26 (3H, s, CH₃); ¹³C NMR (125 MHz, DMSO-d₆, see Fig. 3 for numbering scheme) δ_C 152.6 (C4a), 145.7 (C13a), 125.4 (C12), 124.8 (C10), 113.6 (C9), 103.4 (C11), 67.0 (C8a), 51.7 (C3), 50.7 (C6), 46.6 (C2), 43.3 (C7), 33.7 (C14); IR (KBr, cm^–1): 3090, 3079, 3025, 2936, 2880, 1684, 1661, 1550, 1429, 1321, 1301, 1186, 677.

Structure description top

For the synthesis and data reported earlier for the title compound, see: Sączewski & Foks (1981). For the programs used to derive the twin law, see: Cooper et al.(2002); Farrugia (1999).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Reaction of 2,3,6,7,8a,13-hexahydropyrido[1,2-a]diimidazo[1',2',-c:1",2"-e]-1,3,5-triazine (1) with methyl iodide.
	Fig. 2. Asymmetric unit for the title salt with displacement ellipsoids shown at the 50% probability level.
	Fig. 3. HSQC spectrum of the title compound 2
	Fig. 4. HMBC spectrum of the title compound 2

5-Methyl-3,6,7,8a-tetrahydro-2H- diimidazo[1,2-c:1',2'-e]pyrido[1,2-a][1,3,5]triazin-5-ium iodide top

Crystal data top

C₁₂H₁₆N₅⁺·I⁻	F(000) = 704
M_r = 357.20	D_x = 1.765 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19213 reflections
a = 7.6299 (2) Å	θ = 2.7–32.3°
b = 15.3939 (4) Å	µ = 2.37 mm⁻¹
c = 11.4503 (3) Å	T = 100 K
β = 92.204 (2)°	Block, colourless
V = 1343.89 (6) Å³	0.2 × 0.2 × 0.1 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur-E CCD diffractometer	4406 independent reflections
Radiation source: fine-focus sealed tube	4018 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scan	θ_max = 32.4°, θ_min = 4.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→11
T_min = 0.496, T_max = 0.789	k = −23→23
25955 measured reflections	l = 0→16

Refinement top

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) = 0.070	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.0196P)² + 3.1405P] where P = (F_o² + 2F_c²)/3
4406 reflections	(Δ/σ)_max = 0.001
165 parameters	Δρ_max = 1.74 e Å⁻³
0 restraints	Δρ_min = −1.24 e Å⁻³

Crystal data top

C₁₂H₁₆N₅⁺·I⁻	V = 1343.89 (6) Å³
M_r = 357.20	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6299 (2) Å	µ = 2.37 mm⁻¹
b = 15.3939 (4) Å	T = 100 K
c = 11.4503 (3) Å	0.2 × 0.2 × 0.1 mm
β = 92.204 (2)°

Data collection top

Oxford Diffraction Xcalibur-E CCD diffractometer	4406 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	4018 reflections with I > 2σ(I)
T_min = 0.496, T_max = 0.789	R_int = 0.026
25955 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.20	Δρ_max = 1.74 e Å⁻³
4406 reflections	Δρ_min = −1.24 e Å⁻³
165 parameters

Special details top

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.04305 (2)	0.194494 (11)	0.473423 (14)	0.01657 (5)
N1	0.1806 (3)	0.53774 (16)	0.3251 (2)	0.0209 (5)
C2	0.2057 (4)	0.4944 (2)	0.2120 (2)	0.0222 (5)
H2A	0.2910	0.5272	0.1660	0.027*
H2B	0.0931	0.4914	0.1663	0.027*
C3	0.2755 (4)	0.40179 (19)	0.2385 (2)	0.0206 (5)
H3A	0.1869	0.3569	0.2173	0.025*
H3B	0.3846	0.3898	0.1973	0.025*
N4	0.3083 (3)	0.40681 (15)	0.36610 (19)	0.0155 (4)
N5	0.4690 (3)	0.27675 (15)	0.4159 (2)	0.0162 (4)
C6	0.5326 (4)	0.23510 (18)	0.5250 (2)	0.0189 (5)
H6A	0.6623	0.2316	0.5289	0.023*
H6B	0.4837	0.1759	0.5322	0.023*
C7	0.4659 (4)	0.29506 (18)	0.6205 (2)	0.0201 (5)
H7A	0.3677	0.2679	0.6613	0.024*
H7B	0.5609	0.3097	0.6785	0.024*
N8	0.4068 (3)	0.37245 (14)	0.55467 (19)	0.0147 (4)
C9	0.3144 (4)	0.4560 (2)	0.7238 (2)	0.0202 (5)
H9	0.3752	0.4175	0.7759	0.024*
C10	0.2718 (4)	0.5354 (2)	0.7605 (3)	0.0237 (6)
H10	0.2938	0.5510	0.8400	0.028*
C11	0.1922 (4)	0.59810 (19)	0.6798 (3)	0.0237 (6)
H11	0.1462	0.6510	0.7082	0.028*
C12	0.1842 (4)	0.58081 (18)	0.5651 (3)	0.0197 (5)
H12	0.1363	0.6226	0.5118	0.024*
N13	0.2459 (3)	0.50171 (14)	0.5233 (2)	0.0162 (4)
C14	0.2675 (3)	0.42666 (17)	0.6013 (2)	0.0151 (4)
H14	0.1556	0.3928	0.6010	0.018*
C15	0.3916 (3)	0.35088 (16)	0.4392 (2)	0.0136 (4)
C16	0.2403 (3)	0.48697 (17)	0.4045 (2)	0.0156 (5)
C17	0.4863 (4)	0.2302 (2)	0.3064 (3)	0.0242 (6)
H17A	0.3854	0.1916	0.2934	0.036*
H17B	0.5944	0.1957	0.3102	0.036*
H17C	0.4909	0.2719	0.2420	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01712 (8)	0.01865 (8)	0.01406 (7)	0.00055 (6)	0.00212 (5)	−0.00050 (6)
N1	0.0239 (12)	0.0181 (11)	0.0207 (11)	0.0010 (9)	−0.0007 (9)	0.0040 (9)
C2	0.0251 (14)	0.0244 (14)	0.0170 (12)	0.0007 (11)	−0.0009 (10)	0.0062 (11)
C3	0.0271 (15)	0.0233 (14)	0.0114 (11)	0.0015 (11)	−0.0001 (9)	0.0007 (10)
N4	0.0198 (11)	0.0150 (10)	0.0117 (9)	0.0004 (8)	0.0010 (7)	0.0016 (8)
N5	0.0174 (11)	0.0158 (9)	0.0155 (9)	0.0029 (8)	0.0033 (8)	0.0009 (8)
C6	0.0189 (13)	0.0187 (12)	0.0191 (12)	0.0056 (10)	0.0012 (9)	0.0035 (9)
C7	0.0245 (13)	0.0194 (12)	0.0161 (11)	0.0044 (10)	−0.0008 (9)	0.0045 (9)
N8	0.0157 (10)	0.0150 (9)	0.0134 (9)	0.0007 (8)	−0.0001 (7)	0.0017 (7)
C9	0.0213 (13)	0.0242 (13)	0.0152 (11)	−0.0016 (10)	0.0003 (9)	−0.0024 (10)
C10	0.0223 (14)	0.0297 (15)	0.0191 (13)	−0.0052 (11)	0.0023 (10)	−0.0092 (11)
C11	0.0241 (15)	0.0162 (12)	0.0312 (15)	−0.0029 (10)	0.0048 (11)	−0.0088 (11)
C12	0.0178 (13)	0.0126 (11)	0.0289 (14)	−0.0021 (9)	0.0045 (10)	−0.0026 (10)
N13	0.0212 (11)	0.0111 (9)	0.0164 (10)	0.0001 (8)	0.0001 (8)	−0.0002 (8)
C14	0.0166 (12)	0.0152 (11)	0.0135 (11)	−0.0006 (9)	0.0001 (8)	−0.0001 (9)
C15	0.0113 (11)	0.0147 (11)	0.0148 (10)	−0.0024 (8)	0.0022 (8)	0.0012 (8)
C16	0.0157 (12)	0.0130 (11)	0.0181 (11)	−0.0021 (9)	0.0012 (9)	0.0011 (9)
C17	0.0316 (16)	0.0213 (13)	0.0201 (12)	0.0047 (11)	0.0075 (11)	−0.0047 (10)

Geometric parameters (Å, º) top

N1—C16	1.270 (3)	C7—H7B	0.9900
N1—C2	1.476 (4)	N8—C15	1.364 (3)
C2—C3	1.547 (4)	N8—C14	1.468 (3)
C2—H2A	0.9900	C9—C10	1.336 (4)
C2—H2B	0.9900	C9—C14	1.504 (4)
C3—N4	1.475 (3)	C9—H9	0.9500
C3—H3A	0.9900	C10—C11	1.453 (5)
C3—H3B	0.9900	C10—H10	0.9500
N4—C15	1.344 (3)	C11—C12	1.340 (4)
N4—C16	1.415 (3)	C11—H11	0.9500
N5—C15	1.317 (3)	C12—N13	1.397 (3)
N5—C17	1.455 (4)	C12—H12	0.9500
N5—C6	1.470 (3)	N13—C16	1.378 (3)
C6—C7	1.533 (4)	N13—C14	1.466 (3)
C6—H6A	0.9900	C14—H14	1.0000
C6—H6B	0.9900	C17—H17A	0.9800
C7—N8	1.471 (3)	C17—H17B	0.9800
C7—H7A	0.9900	C17—H17C	0.9800

C16—N1—C2	107.1 (2)	C10—C9—C14	121.1 (3)
N1—C2—C3	107.4 (2)	C10—C9—H9	119.4
N1—C2—H2A	110.2	C14—C9—H9	119.4
C3—C2—H2A	110.2	C9—C10—C11	120.5 (3)
N1—C2—H2B	110.2	C9—C10—H10	119.7
C3—C2—H2B	110.2	C11—C10—H10	119.7
H2A—C2—H2B	108.5	C12—C11—C10	119.6 (3)
N4—C3—C2	101.0 (2)	C12—C11—H11	120.2
N4—C3—H3A	111.6	C10—C11—H11	120.2
C2—C3—H3A	111.6	C11—C12—N13	120.4 (3)
N4—C3—H3B	111.6	C11—C12—H12	119.8
C2—C3—H3B	111.6	N13—C12—H12	119.8
H3A—C3—H3B	109.4	C16—N13—C12	118.9 (2)
C15—N4—C16	122.4 (2)	C16—N13—C14	118.1 (2)
C15—N4—C3	129.9 (2)	C12—N13—C14	120.6 (2)
C16—N4—C3	107.6 (2)	N13—C14—N8	107.0 (2)
C15—N5—C17	131.1 (2)	N13—C14—C9	110.4 (2)
C15—N5—C6	110.0 (2)	N8—C14—C9	111.1 (2)
C17—N5—C6	118.7 (2)	N13—C14—H14	109.4
N5—C6—C7	103.6 (2)	N8—C14—H14	109.4
N5—C6—H6A	111.0	C9—C14—H14	109.4
C7—C6—H6A	111.0	N5—C15—N4	129.4 (2)
N5—C6—H6B	111.0	N5—C15—N8	112.7 (2)
C7—C6—H6B	111.0	N4—C15—N8	117.9 (2)
H6A—C6—H6B	109.0	N1—C16—N13	127.0 (3)
N8—C7—C6	103.0 (2)	N1—C16—N4	116.1 (2)
N8—C7—H7A	111.2	N13—C16—N4	116.9 (2)
C6—C7—H7A	111.2	N5—C17—H17A	109.5
N8—C7—H7B	111.2	N5—C17—H17B	109.5
C6—C7—H7B	111.2	H17A—C17—H17B	109.5
H7A—C7—H7B	109.1	N5—C17—H17C	109.5
C15—N8—C14	117.1 (2)	H17A—C17—H17C	109.5
C15—N8—C7	108.2 (2)	H17B—C17—H17C	109.5
C14—N8—C7	119.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···I1ⁱ	0.99	3.15	4.007 (3)	145
C6—H6A···I1ⁱⁱ	0.99	3.05	4.010 (3)	163
C9—H9···I1ⁱⁱⁱ	0.95	3.08	4.025 (3)	172
C12—H12···I1^iv	0.95	3.14	3.887 (3)	137
C17—H17C···I1ⁱ	0.98	3.16	4.025 (3)	148

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x+1, y, z; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₅⁺·I⁻
M_r	357.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.6299 (2), 15.3939 (4), 11.4503 (3)
β (°)	92.204 (2)
V (Å³)	1343.89 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.37
Crystal size (mm)	0.2 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur-E CCD
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.496, 0.789
No. of measured, independent and observed [I > 2σ(I)] reflections	25955, 4406, 4018
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.753

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.070, 1.20
No. of reflections	4406
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.74, −1.24

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···I1ⁱ	0.99	3.15	4.007 (3)	145
C6—H6A···I1ⁱⁱ	0.99	3.05	4.010 (3)	163
C9—H9···I1ⁱⁱⁱ	0.95	3.08	4.025 (3)	172
C12—H12···I1^iv	0.95	3.14	3.887 (3)	137
C17—H17C···I1ⁱ	0.98	3.16	4.025 (3)	148

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x+1, y, z; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x, −y+1, −z+1.

References

Cooper, R. I., Gould, R. O., Parsons, S. & Watkin, D. J. (2002). J. Appl. Cryst. 35, 168–174. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sączewski, F. & Foks, H. (1981). Synthesis, pp. 151–152. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-Methyl-3,6,7,8a-tetra­hydro-2H-diimidazo[1,2-c:1′,2′-e]pyrido[1,2-a][1,3,5]triazin-5-ium iodide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

5-Methyl-3,6,7,8a-tetrahydro-2H-diimidazo[1,2-c:1′,2′-e]pyrido[1,2-a][1,3,5]triazin-5-ium iodide