8-Iodo-quinolinium triiodide tetra-hydro-furan solvate.

The title compound, C(9)H(7)IN(+)·I(3) (-)·C(4)H(8)O, was synthesized from 8-amino-quinoline using the Sandmeyer reaction. The 8-iodo-quinolinium cation is essentially planar and the triiodide ion is almost linear. N-H⋯O hydrogen bonds, and inter-molecular I⋯I [3.7100 (5) Å] and I⋯H inter-actions, between the cation, anion and solvent mol-ecules result in the formation of sheets oriented parallel to the (03) plane. Between the sheets, 8-iodo-quinolinium and triiodide ions are stacked alternately, with I⋯C distances in the range ∼3.8-4.0 Å.

Related literature

For the synthesis, see: Lucas & Kennedy (1943 ▶); Sandmeyer (1884 ▶). For related structures, see: Son & Hoefelmeyer (2008 ▶); Svensson & Kloo (2003 ▶).

Experimental

Crystal data

C9H7IN+·I3 −·C4H8O

M = 708.86

Monoclinic,

a = 7.8674 (4) Å

b = 17.6510 (9) Å

c = 13.1465 (7) Å

β = 90.343 (1)°

V = 1825.59 (16) Å3

Z = 4

Mo Kα radiation

μ = 6.82 mm−1

T = 100 (2) K

0.57 × 0.36 × 0.27 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: numerical (XPREP in SHELXTL; Sheldrick, 2008 ▶), T min = 0.111, T max = 0.262

18253 measured reflections

3363 independent reflections

3291 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.111

S = 0.97

3363 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −2.63 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031516/ci2653sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031516/ci2653Isup2.hkl

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

C9H7IN+·I3−·C4H8O	F(000) = 1280
Mr = 708.86	Dx = 2.579 Mg m−3
Monoclinic, P21/n	Melting point: 367 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.8674 (4) Å	Cell parameters from 9984 reflections
b = 17.6510 (9) Å	θ = 2.8–25.4°
c = 13.1465 (7) Å	µ = 6.82 mm−1
β = 90.343 (1)°	T = 100 K
V = 1825.59 (16) Å3	Block, metallic violet
Z = 4	0.57 × 0.36 × 0.27 mm

Bruker SMART APEXII diffractometer	3363 independent reflections
Radiation source: fine-focus sealed tube	3291 reflections with I > 2σ(I)
graphite	Rint = 0.079
ω scans	θmax = 25.4°, θmin = 1.9°
Absorption correction: numerical (XPREP in SHELXTL; Sheldrick, 2008) or (SADABS; Bruker, 2003)???	h = −9→9
Tmin = 0.111, Tmax = 0.262	k = −21→21
18253 measured reflections	l = −15→15

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) = 0.111	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0437P)2 + 2.836P] where P = (Fo2 + 2Fc2)/3
3363 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −2.63 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
C2	0.2020 (7)	0.3301 (2)	0.9044 (4)	0.0231 (10)
H2	0.2425	0.3807	0.9094	0.028*
C3	0.0503 (6)	0.3161 (3)	0.8562 (4)	0.0265 (10)
H3	−0.0138	0.3565	0.8275	0.032*
C4	−0.0077 (5)	0.2427 (3)	0.8500 (3)	0.0229 (9)
H4	−0.1134	0.2322	0.8177	0.027*
C5	0.0356 (6)	0.1062 (3)	0.8839 (3)	0.0234 (9)
H5	−0.0706	0.0943	0.8531	0.028*
C6	0.1379 (6)	0.0497 (3)	0.9214 (3)	0.0231 (9)
H6	0.1035	−0.0017	0.9155	0.028*
C7	0.2952 (6)	0.0678 (3)	0.9690 (3)	0.0221 (9)
H7	0.3640	0.0281	0.9954	0.027*
C8	0.3493 (5)	0.1402 (3)	0.9775 (3)	0.0181 (8)
C9	0.2463 (5)	0.1992 (3)	0.9385 (3)	0.0167 (8)
C10	0.0900 (6)	0.1829 (3)	0.8917 (3)	0.0197 (9)
C11	0.5434 (6)	0.3891 (3)	0.1252 (3)	0.0233 (9)
H11A	0.6024	0.3486	0.1637	0.028*
H11B	0.4297	0.3972	0.1551	0.028*
C12	0.6463 (6)	0.4619 (3)	0.1272 (4)	0.0250 (9)
H12A	0.7212	0.4638	0.1879	0.030*
H12B	0.5708	0.5068	0.1275	0.030*
C13	0.7520 (6)	0.4587 (3)	0.0285 (3)	0.0243 (9)
H13A	0.7269	0.5028	−0.0158	0.029*
H13B	0.8753	0.4578	0.0439	0.029*
C14	0.6948 (5)	0.3849 (3)	−0.0216 (3)	0.0237 (9)
H14A	0.6885	0.3907	−0.0965	0.028*
H14B	0.7749	0.3433	−0.0052	0.028*
I1	0.58420 (4)	0.162595 (15)	1.04875 (2)	0.02127 (14)
I2	−0.00026 (4)	0.166821 (16)	0.18354 (2)	0.02404 (14)
I3	0.05172 (4)	0.330240 (15)	0.21544 (2)	0.01836 (14)
I4	0.11961 (4)	0.488485 (17)	0.25933 (2)	0.02294 (14)
N1	0.2941 (4)	0.2734 (2)	0.9445 (3)	0.0182 (7)
H1	0.3897	0.2845	0.9762	0.022*
O1	0.5292 (4)	0.36930 (18)	0.0195 (2)	0.0210 (6)

	U11	U22	U33	U12	U13	U23
C2	0.026 (3)	0.017 (2)	0.027 (2)	−0.0006 (16)	0.003 (2)	0.0016 (16)
C3	0.022 (2)	0.034 (3)	0.023 (2)	0.012 (2)	0.0013 (18)	0.005 (2)
C4	0.015 (2)	0.035 (3)	0.018 (2)	−0.0014 (18)	−0.0022 (15)	−0.0022 (18)
C5	0.022 (2)	0.029 (2)	0.020 (2)	−0.0101 (19)	0.0027 (16)	−0.0036 (18)
C6	0.030 (2)	0.017 (2)	0.022 (2)	−0.0091 (18)	0.0006 (17)	−0.0029 (17)
C7	0.025 (2)	0.021 (2)	0.020 (2)	0.0005 (17)	0.0047 (17)	−0.0024 (17)
C8	0.0144 (19)	0.025 (2)	0.0151 (19)	0.0012 (18)	0.0005 (15)	−0.0010 (17)
C9	0.0149 (19)	0.022 (2)	0.0128 (17)	0.0022 (17)	0.0027 (14)	0.0011 (16)
C10	0.022 (2)	0.022 (2)	0.014 (2)	−0.0064 (17)	0.0038 (16)	−0.0040 (17)
C11	0.022 (2)	0.029 (2)	0.019 (2)	−0.0016 (18)	0.0018 (16)	−0.0011 (18)
C12	0.022 (2)	0.023 (2)	0.030 (2)	−0.0029 (18)	−0.0053 (18)	−0.0038 (19)
C13	0.020 (2)	0.026 (2)	0.027 (2)	−0.0063 (19)	−0.0055 (17)	0.0035 (19)
C14	0.017 (2)	0.032 (3)	0.022 (2)	−0.0001 (18)	0.0041 (17)	0.0014 (18)
I1	0.0187 (2)	0.0219 (2)	0.0232 (2)	0.00115 (10)	−0.00448 (14)	0.00111 (10)
I2	0.0264 (2)	0.0248 (2)	0.0209 (2)	−0.00137 (10)	0.00150 (15)	−0.00241 (10)
I3	0.0143 (2)	0.0245 (2)	0.0163 (2)	0.00172 (9)	−0.00029 (13)	0.00112 (9)
I4	0.0240 (2)	0.0216 (2)	0.0232 (2)	0.00220 (10)	−0.00198 (14)	0.00159 (10)
N1	0.0137 (17)	0.024 (2)	0.0172 (17)	0.0021 (14)	0.0010 (13)	−0.0015 (14)
O1	0.0182 (15)	0.0214 (16)	0.0233 (15)	−0.0030 (12)	0.0010 (12)	−0.0034 (13)

C2—N1	1.343 (6)	C9—C10	1.401 (7)
C2—C3	1.370 (8)	C11—O1	1.436 (5)
C2—H2	0.95	C11—C12	1.519 (6)
C3—C4	1.375 (7)	C11—H11A	0.99
C3—H3	0.95	C11—H11B	0.99
C4—C10	1.415 (7)	C12—C13	1.547 (6)
C4—H4	0.95	C12—H12A	0.99
C5—C6	1.372 (7)	C12—H12B	0.99
C5—C10	1.423 (6)	C13—C14	1.527 (6)
C5—H5	0.95	C13—H13A	0.99
C6—C7	1.419 (7)	C13—H13B	0.99
C6—H6	0.95	C14—O1	1.440 (5)
C7—C8	1.352 (6)	C14—H14A	0.99
C7—H7	0.95	C14—H14B	0.99
C8—C9	1.413 (6)	I2—I3	2.9430 (4)
C8—I1	2.104 (4)	I3—I4	2.9011 (4)
C9—N1	1.364 (6)	N1—H1	0.88
N1—C2—C3	120.9 (4)	O1—C11—H11A	110.7
N1—C2—H2	119.5	C12—C11—H11A	110.7
C3—C2—H2	119.5	O1—C11—H11B	110.7
C2—C3—C4	119.0 (4)	C12—C11—H11B	110.7
C2—C3—H3	120.5	H11A—C11—H11B	108.8
C4—C3—H3	120.5	C11—C12—C13	104.1 (4)
C3—C4—C10	120.0 (4)	C11—C12—H12A	110.9
C3—C4—H4	120.0	C13—C12—H12A	110.9
C10—C4—H4	120.0	C11—C12—H12B	110.9
C6—C5—C10	119.4 (4)	C13—C12—H12B	110.9
C6—C5—H5	120.3	H12A—C12—H12B	109.0
C10—C5—H5	120.3	C14—C13—C12	103.6 (3)
C5—C6—C7	120.1 (4)	C14—C13—H13A	111.0
C5—C6—H6	119.9	C12—C13—H13A	111.0
C7—C6—H6	119.9	C14—C13—H13B	111.0
C8—C7—C6	121.6 (4)	C12—C13—H13B	111.0
C8—C7—H7	119.2	H13A—C13—H13B	109.0
C6—C7—H7	119.2	O1—C14—C13	105.4 (3)
C7—C8—C9	119.1 (4)	O1—C14—H14A	110.7
C7—C8—I1	119.3 (3)	C13—C14—H14A	110.7
C9—C8—I1	121.6 (3)	O1—C14—H14B	110.7
N1—C9—C10	117.6 (4)	C13—C14—H14B	110.7
N1—C9—C8	121.9 (4)	H14A—C14—H14B	108.8
C10—C9—C8	120.5 (4)	I4—I3—I2	175.753 (14)
C9—C10—C4	119.4 (4)	C2—N1—C9	123.0 (4)
C9—C10—C5	119.3 (5)	C2—N1—H1	118.5
C4—C10—C5	121.3 (4)	C9—N1—H1	118.5
O1—C11—C12	105.2 (3)	C11—O1—C14	104.5 (3)
N1—C2—C3—C4	0.5 (7)	C8—C9—C10—C5	0.1 (6)
C2—C3—C4—C10	−0.9 (7)	C3—C4—C10—C9	−0.4 (7)
C10—C5—C6—C7	1.1 (7)	C3—C4—C10—C5	−178.2 (4)
C5—C6—C7—C8	−0.9 (7)	C6—C5—C10—C9	−0.7 (6)
C6—C7—C8—C9	0.3 (6)	C6—C5—C10—C4	177.1 (4)
C6—C7—C8—I1	−179.9 (3)	O1—C11—C12—C13	−25.5 (4)
C7—C8—C9—N1	−179.8 (4)	C11—C12—C13—C14	1.4 (5)
I1—C8—C9—N1	0.4 (5)	C12—C13—C14—O1	23.0 (4)
C7—C8—C9—C10	0.0 (6)	C3—C2—N1—C9	1.4 (7)
I1—C8—C9—C10	−179.8 (3)	C10—C9—N1—C2	−2.7 (6)
N1—C9—C10—C4	2.2 (6)	C8—C9—N1—C2	177.1 (4)
C8—C9—C10—C4	−177.7 (4)	C12—C11—O1—C14	41.1 (4)
N1—C9—C10—C5	−180.0 (4)	C13—C14—O1—C11	−40.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1	0.88	2.80	3.297 (4)	117
N1—H1···O1i	0.88	1.94	2.690 (5)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯I1	0.88	2.80	3.297 (4)	117
N1—H1⋯O1i	0.88	1.94	2.690 (5)	142

Symmetry code: (i) .