8a-Methyl-5,6,8,8a,9,10-hexa-hydro-10,12a-epoxy-isoindolo[1,2-a]isoquinolinium iodide.

The title compound, C(17)H(18)NO(+)·I(-), is an adduct resulting from an intra-molecular Diels-Alder reaction of methallyl chloride with 3,4-dihydro-1-furylisoquinoline. The cation comprises a fused penta-cyclic system containing three five-membered rings (dihydro-pyrrole, dihydro-furan and tetra-hydro-furan) and two six-membered rings (tetra-hydro-pyridine and benzene). The five-membered rings have the usual envelope conformations, and the central six-membered tetra-hydro-pyridine ring adopts the unsymmetrical half-boat conformation. In the crystal, cations and iodide anions are bound by weak inter-molecular hydrogen-bonding inter-actions into a three-dimensional framework.

Related literature

For general background to the method proposed by our group for obtaining hydrogenated isoindolo[2,1-a]isoquinolines using commercially available furfurals and phenethyl­amines as starting materials, see: Zubkov et al. (2004 ▶); Boltukhina et al. (2006 ▶). For related structures, see: Tagmazyan et al. (1976 ▶, 1977 ▶); Ahmad et al. (1987 ▶); Rasheed et al. (1991 ▶); Zubkov et al. (2009 ▶).

Experimental

Crystal data

C17H18NO+·I−

M = 379.22

Monoclinic,

a = 15.5047 (6) Å

b = 8.0757 (3) Å

c = 25.1874 (12) Å

β = 104.204 (1)°

V = 3057.3 (2) Å3

Z = 8

Mo Kα radiation

μ = 2.09 mm−1

T = 100 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.573, T max = 0.745

18881 measured reflections

4450 independent reflections

4123 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.054

S = 1.00

4450 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.94 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017903/rk2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017903/rk2205Isup2.hkl

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

C17H18NO+·I−	F(000) = 1504
Mr = 379.22	Dx = 1.648 Mg m−3
Monoclinic, C2/c	Melting point: 452 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 15.5047 (6) Å	Cell parameters from 7921 reflections
b = 8.0757 (3) Å	θ = 2.7–32.5°
c = 25.1874 (12) Å	µ = 2.09 mm−1
β = 104.204 (1)°	T = 100 K
V = 3057.3 (2) Å3	Prism, orange
Z = 8	0.30 × 0.20 × 0.15 mm

Bruker APEXII CCD diffractometer	4450 independent reflections
Radiation source: fine-focus sealed tube	4123 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −21→21
Tmin = 0.573, Tmax = 0.745	k = −11→11
18881 measured reflections	l = −35→35

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0195P)2 + 6.6P] where P = (Fo2 + 2Fc2)/3
4450 reflections	(Δ/σ)max = 0.002
182 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.94 e Å−3

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 > 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	0.325921 (8)	0.080703 (16)	0.405918 (5)	0.02178 (4)
O1	0.45929 (8)	0.66340 (17)	0.33020 (5)	0.0191 (3)
C1	0.61820 (12)	0.8559 (2)	0.27922 (7)	0.0184 (3)
H1	0.5871	0.7567	0.2663	0.022*
C1A	0.63271 (12)	0.9011 (2)	0.33406 (7)	0.0165 (3)
C2	0.64969 (13)	0.9574 (2)	0.24349 (8)	0.0206 (4)
H2	0.6392	0.9292	0.2058	0.025*
C3	0.69669 (13)	1.1005 (2)	0.26325 (8)	0.0226 (4)
H3	0.7178	1.1700	0.2387	0.027*
C4	0.71330 (13)	1.1433 (2)	0.31838 (8)	0.0206 (4)
H4	0.7472	1.2395	0.3314	0.025*
C4A	0.68027 (12)	1.0454 (2)	0.35434 (8)	0.0183 (3)
C5	0.69532 (13)	1.0806 (2)	0.41463 (8)	0.0214 (4)
H5A	0.7106	1.1989	0.4217	0.026*
H5B	0.7458	1.0134	0.4353	0.026*
C6	0.61228 (13)	1.0400 (2)	0.43404 (8)	0.0205 (4)
H6A	0.6255	1.0475	0.4745	0.025*
H6B	0.5646	1.1204	0.4184	0.025*
N7	0.58279 (10)	0.8714 (2)	0.41628 (6)	0.0174 (3)
C8	0.52789 (12)	0.7704 (2)	0.44453 (7)	0.0192 (3)
H8A	0.4659	0.8114	0.4365	0.023*
H8B	0.5530	0.7705	0.4847	0.023*
C8A	0.53246 (12)	0.5980 (2)	0.42045 (7)	0.0175 (3)
C9	0.44431 (13)	0.4996 (3)	0.40199 (8)	0.0228 (4)
H9A	0.3945	0.5575	0.4123	0.027*
H9B	0.4501	0.3866	0.4177	0.027*
C10	0.43173 (13)	0.4959 (3)	0.33880 (8)	0.0223 (4)
H10	0.3704	0.4661	0.3174	0.027*
C11	0.50568 (14)	0.3957 (2)	0.32470 (8)	0.0221 (4)
H11	0.5008	0.2876	0.3094	0.027*
C12	0.57905 (12)	0.4890 (2)	0.33795 (7)	0.0187 (3)
H12	0.6365	0.4647	0.3329	0.022*
C12A	0.54908 (11)	0.6422 (2)	0.36281 (7)	0.0158 (3)
C12B	0.59353 (12)	0.8077 (2)	0.37104 (7)	0.0162 (3)
C13	0.60762 (13)	0.4998 (3)	0.45782 (8)	0.0225 (4)
H13A	0.5933	0.4803	0.4931	0.034*
H13B	0.6632	0.5628	0.4637	0.034*
H13C	0.6146	0.3934	0.4406	0.034*

	U11	U22	U33	U12	U13	U23
I1	0.02024 (6)	0.02454 (7)	0.01967 (6)	−0.00275 (5)	0.00320 (4)	−0.00284 (5)
O1	0.0163 (6)	0.0212 (6)	0.0176 (6)	0.0003 (5)	0.0001 (5)	0.0018 (5)
C1	0.0191 (8)	0.0182 (8)	0.0174 (8)	−0.0002 (7)	0.0039 (6)	−0.0004 (7)
C1A	0.0178 (8)	0.0158 (8)	0.0161 (8)	0.0015 (6)	0.0044 (6)	0.0012 (6)
C2	0.0208 (8)	0.0240 (9)	0.0180 (8)	0.0010 (7)	0.0067 (7)	0.0004 (7)
C3	0.0219 (9)	0.0225 (9)	0.0249 (9)	0.0008 (7)	0.0087 (7)	0.0048 (7)
C4	0.0193 (8)	0.0174 (8)	0.0256 (9)	−0.0007 (7)	0.0064 (7)	−0.0006 (7)
C4A	0.0163 (8)	0.0177 (8)	0.0199 (8)	0.0007 (6)	0.0028 (6)	−0.0009 (6)
C5	0.0230 (9)	0.0215 (9)	0.0193 (8)	−0.0031 (7)	0.0043 (7)	−0.0033 (7)
C6	0.0268 (9)	0.0176 (8)	0.0183 (8)	−0.0021 (7)	0.0079 (7)	−0.0035 (7)
N7	0.0200 (7)	0.0164 (7)	0.0162 (7)	−0.0001 (6)	0.0051 (6)	0.0003 (6)
C8	0.0213 (8)	0.0213 (9)	0.0161 (8)	−0.0003 (7)	0.0066 (6)	0.0006 (7)
C8A	0.0178 (8)	0.0191 (8)	0.0157 (8)	−0.0016 (6)	0.0045 (6)	0.0011 (6)
C9	0.0215 (9)	0.0265 (10)	0.0209 (9)	−0.0070 (7)	0.0058 (7)	0.0003 (8)
C10	0.0199 (8)	0.0245 (10)	0.0217 (9)	−0.0063 (7)	0.0032 (7)	−0.0005 (7)
C11	0.0273 (9)	0.0190 (9)	0.0191 (8)	−0.0031 (7)	0.0038 (7)	−0.0008 (7)
C12	0.0206 (8)	0.0184 (8)	0.0172 (8)	0.0014 (7)	0.0046 (7)	−0.0002 (7)
C12A	0.0152 (7)	0.0171 (8)	0.0151 (7)	−0.0011 (6)	0.0034 (6)	0.0010 (6)
C12B	0.0167 (8)	0.0164 (8)	0.0147 (7)	0.0013 (6)	0.0021 (6)	0.0006 (6)
C13	0.0246 (9)	0.0242 (10)	0.0178 (8)	0.0029 (7)	0.0036 (7)	0.0047 (7)

O1—C12A	1.443 (2)	N7—C8	1.481 (2)
O1—C10	1.451 (2)	C8—C8A	1.527 (3)
C1—C2	1.391 (3)	C8—H8A	0.9900
C1—C1A	1.393 (2)	C8—H8B	0.9900
C1—H1	0.9500	C8A—C13	1.528 (3)
C1A—C4A	1.406 (3)	C8A—C9	1.550 (3)
C1A—C12B	1.443 (2)	C8A—C12A	1.576 (2)
C2—C3	1.391 (3)	C9—C10	1.555 (3)
C2—H2	0.9500	C9—H9A	0.9900
C3—C4	1.392 (3)	C9—H9B	0.9900
C3—H3	0.9500	C10—C11	1.515 (3)
C4—C4A	1.392 (3)	C10—H10	1.0000
C4—H4	0.9500	C11—C12	1.337 (3)
C4A—C5	1.506 (3)	C11—H11	0.9500
C5—C6	1.521 (3)	C12—C12A	1.510 (3)
C5—H5A	0.9900	C12—H12	0.9500
C5—H5B	0.9900	C12A—C12B	1.495 (3)
C6—N7	1.470 (2)	C13—H13A	0.9800
C6—H6A	0.9900	C13—H13B	0.9800
C6—H6B	0.9900	C13—H13C	0.9800
N7—C12B	1.298 (2)
C12A—O1—C10	94.73 (13)	C8—C8A—C13	109.33 (15)
C2—C1—C1A	119.36 (18)	C8—C8A—C9	117.58 (16)
C2—C1—H1	120.3	C13—C8A—C9	113.69 (16)
C1A—C1—H1	120.3	C8—C8A—C12A	101.17 (14)
C1—C1A—C4A	121.36 (17)	C13—C8A—C12A	114.35 (15)
C1—C1A—C12B	120.78 (17)	C9—C8A—C12A	99.85 (14)
C4A—C1A—C12B	117.70 (16)	C8A—C9—C10	101.35 (14)
C1—C2—C3	119.60 (18)	C8A—C9—H9A	111.5
C1—C2—H2	120.2	C10—C9—H9A	111.5
C3—C2—H2	120.2	C8A—C9—H9B	111.5
C2—C3—C4	121.04 (18)	C10—C9—H9B	111.5
C2—C3—H3	119.5	H9A—C9—H9B	109.3
C4—C3—H3	119.5	O1—C10—C11	101.25 (15)
C4A—C4—C3	120.02 (18)	O1—C10—C9	99.63 (15)
C4A—C4—H4	120.0	C11—C10—C9	109.76 (16)
C3—C4—H4	120.0	O1—C10—H10	114.8
C4—C4A—C1A	118.58 (18)	C11—C10—H10	114.8
C4—C4A—C5	123.94 (17)	C9—C10—H10	114.8
C1A—C4A—C5	117.44 (17)	C12—C11—C10	106.70 (17)
C4A—C5—C6	110.45 (16)	C12—C11—H11	126.7
C4A—C5—H5A	109.6	C10—C11—H11	126.7
C6—C5—H5A	109.6	C11—C12—C12A	103.62 (16)
C4A—C5—H5B	109.6	C11—C12—H12	128.2
C6—C5—H5B	109.6	C12A—C12—H12	128.2
H5A—C5—H5B	108.1	O1—C12A—C12B	108.67 (14)
N7—C6—C5	109.06 (15)	O1—C12A—C12	102.32 (14)
N7—C6—H6A	109.9	C12B—C12A—C12	127.70 (16)
C5—C6—H6A	109.9	O1—C12A—C8A	101.44 (13)
N7—C6—H6B	109.9	C12B—C12A—C8A	104.40 (14)
C5—C6—H6B	109.9	C12—C12A—C8A	109.46 (15)
H6A—C6—H6B	108.3	N7—C12B—C1A	121.63 (17)
C12B—N7—C6	122.46 (16)	N7—C12B—C12A	108.79 (15)
C12B—N7—C8	114.58 (16)	C1A—C12B—C12A	129.10 (16)
C6—N7—C8	122.45 (15)	C8A—C13—H13A	109.5
N7—C8—C8A	102.91 (14)	C8A—C13—H13B	109.5
N7—C8—H8A	111.2	H13A—C13—H13B	109.5
C8A—C8—H8A	111.2	C8A—C13—H13C	109.5
N7—C8—H8B	111.2	H13A—C13—H13C	109.5
C8A—C8—H8B	111.2	H13B—C13—H13C	109.5
H8A—C8—H8B	109.1
C2—C1—C1A—C4A	−1.4 (3)	C10—C11—C12—C12A	2.8 (2)
C2—C1—C1A—C12B	173.85 (17)	C10—O1—C12A—C12B	−169.84 (14)
C1A—C1—C2—C3	1.3 (3)	C10—O1—C12A—C12	52.90 (15)
C1—C2—C3—C4	0.4 (3)	C10—O1—C12A—C8A	−60.19 (15)
C2—C3—C4—C4A	−2.1 (3)	C11—C12—C12A—O1	−35.95 (18)
C3—C4—C4A—C1A	2.0 (3)	C11—C12—C12A—C12B	−161.61 (17)
C3—C4—C4A—C5	179.45 (18)	C11—C12—C12A—C8A	71.05 (18)
C1—C1A—C4A—C4	−0.2 (3)	C8—C8A—C12A—O1	−86.84 (15)
C12B—C1A—C4A—C4	−175.63 (16)	C13—C8A—C12A—O1	155.78 (15)
C1—C1A—C4A—C5	−177.87 (17)	C9—C8A—C12A—O1	34.03 (17)
C12B—C1A—C4A—C5	6.7 (2)	C8—C8A—C12A—C12B	26.06 (17)
C4—C4A—C5—C6	142.02 (19)	C13—C8A—C12A—C12B	−91.31 (18)
C1A—C4A—C5—C6	−40.5 (2)	C9—C8A—C12A—C12B	146.94 (15)
C4A—C5—C6—N7	51.2 (2)	C8—C8A—C12A—C12	165.56 (14)
C5—C6—N7—C12B	−32.4 (2)	C13—C8A—C12A—C12	48.2 (2)
C5—C6—N7—C8	156.17 (16)	C9—C8A—C12A—C12	−73.57 (17)
C12B—N7—C8—C8A	20.2 (2)	C6—N7—C12B—C1A	−2.2 (3)
C6—N7—C8—C8A	−167.72 (16)	C8—N7—C12B—C1A	169.88 (16)
N7—C8—C8A—C13	94.15 (16)	C6—N7—C12B—C12A	−174.87 (16)
N7—C8—C8A—C9	−134.27 (16)	C8—N7—C12B—C12A	−2.8 (2)
N7—C8—C8A—C12A	−26.83 (17)	C1—C1A—C12B—N7	−158.84 (18)
C8—C8A—C9—C10	112.08 (18)	C4A—C1A—C12B—N7	16.6 (3)
C13—C8A—C9—C10	−118.35 (17)	C1—C1A—C12B—C12A	12.3 (3)
C12A—C8A—C9—C10	3.87 (18)	C4A—C1A—C12B—C12A	−172.30 (17)
C12A—O1—C10—C11	−50.15 (15)	O1—C12A—C12B—N7	92.29 (17)
C12A—O1—C10—C9	62.39 (15)	C12—C12A—C12B—N7	−144.62 (18)
C8A—C9—C10—O1	−40.39 (17)	C8A—C12A—C12B—N7	−15.34 (19)
C8A—C9—C10—C11	65.35 (19)	O1—C12A—C12B—C1A	−79.7 (2)
O1—C10—C11—C12	30.66 (19)	C12—C12A—C12B—C1A	43.4 (3)
C9—C10—C11—C12	−74.0 (2)	C8A—C12A—C12B—C1A	172.67 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···I1i	0.95	3.23	3.999 (2)	139
C6—H6A···I1ii	0.99	3.10	4.028 (2)	157
C8—H8A···I1iii	0.99	3.04	3.942 (2)	153
C8—H8B···I1ii	0.99	3.17	4.072 (2)	153
C9—H9B···I1	0.99	3.10	3.862 (2)	135
C12—H12···I1iv	0.95	3.20	3.862 (2)	128
C13—H13B···I1iv	0.98	3.21	3.970 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯I1i	0.95	3.23	3.999 (2)	139
C6—H6A⋯I1ii	0.99	3.10	4.028 (2)	157
C8—H8A⋯I1iii	0.99	3.04	3.942 (2)	153
C8—H8B⋯I1ii	0.99	3.17	4.072 (2)	153
C9—H9B⋯I1	0.99	3.10	3.862 (2)	135
C12—H12⋯I1iv	0.95	3.20	3.862 (2)	128
C13—H13B⋯I1iv	0.98	3.21	3.970 (2)	136

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