8-Iodo-quinolinium chloride dihydrate.

The title compound, C(9)H(7)IN(+)·Cl(-)·2H(2)O, was obtained during the synthesis of 8-iodo-quinoline from 8-amino-quinoline using the Sandmeyer reaction. The 8-iodo-quinolinium ion is almost planar. Solvent water mol-ecules and chloride ions form a hydrogen-bonded chain along the c axis via O-H⋯Cl links. The 8-iodo-quinolinium ions, which are packed along the c axis with cationic aromatic π-π stacking (centroid-centroid distance = 3.624 Å), are linked to the chain via N-H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Lucas & Kennedy (1943 ▶); Sandmeyer (1884 ▶). For a related structure, see: Son & Hoefelmeyer (2008 ▶). For related literature, see: Janiak (2000 ▶).

Experimental

Crystal data

C9H7IN+·Cl−·2H2O

M = 327.54

Monoclinic,

a = 8.9600 (18) Å

b = 17.580 (4) Å

c = 7.1700 (14) Å

β = 97.13 (3)°

V = 1120.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.07 mm−1

T = 100 (2) K

0.71 × 0.67 × 0.54 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.219, T max = 0.288 (expected range = 0.145–0.190)

10655 measured reflections

2045 independent reflections

2040 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.046

S = 1.25

2045 reflections

143 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.79 e Å−3

Δρmin = −0.65 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/S1600536808031528/ci2652sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031528/ci2652Isup2.hkl

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

C9H7IN+·Cl−·2H2O	F(000) = 632
Mr = 327.54	Dx = 1.941 Mg m−3
Monoclinic, P21/c	Melting point: 388 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.9600 (18) Å	Cell parameters from 9991 reflections
b = 17.580 (4) Å	θ = 2.3–28.6°
c = 7.1700 (14) Å	µ = 3.07 mm−1
β = 97.13 (3)°	T = 100 K
V = 1120.7 (4) Å3	Block, brown
Z = 4	0.71 × 0.67 × 0.54 mm

Bruker SMART APEXII diffractometer	2045 independent reflections
Radiation source: fine-focus sealed tube	2040 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 25.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→10
Tmin = 0.219, Tmax = 0.288	k = −21→21
10655 measured reflections	l = −8→8

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046	H atoms treated by a mixture of independent and constrained refinement
S = 1.25	w = 1/[σ2(Fo2) + (0.0437P)2 + 2.836P] where P = (Fo2 + 2Fc2)/3
2045 reflections	(Δ/σ)max = 0.001
143 parameters	Δρmax = 0.79 e Å−3
6 restraints	Δρmin = −0.65 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	0.1207 (3)	0.35738 (15)	−0.0118 (4)	0.0175 (6)
H2	0.0968	0.4100	−0.0215	0.021*
C3	0.0078 (3)	0.30408 (17)	−0.0595 (4)	0.0187 (6)
H3	−0.0918	0.3199	−0.1035	0.022*
C4	0.0429 (3)	0.22795 (15)	−0.0418 (4)	0.0155 (5)
H4	−0.0333	0.1909	−0.0724	0.019*
C5	0.2333 (3)	0.12642 (15)	0.0433 (4)	0.0170 (5)
H5	0.1591	0.0881	0.0155	0.020*
C6	0.3795 (3)	0.10627 (15)	0.1040 (4)	0.0190 (6)
H6	0.4053	0.0541	0.1199	0.023*
C7	0.4923 (3)	0.16273 (16)	0.1430 (4)	0.0169 (5)
H7	0.5932	0.1477	0.1821	0.020*
C8	0.4574 (3)	0.23944 (15)	0.1248 (4)	0.0134 (5)
C9	0.3060 (3)	0.26110 (14)	0.0660 (3)	0.0115 (5)
C10	0.1928 (3)	0.20430 (15)	0.0220 (4)	0.0132 (5)
N1	0.2614 (3)	0.33639 (13)	0.0471 (3)	0.0143 (5)
H1	0.326 (4)	0.369 (2)	0.080 (5)	0.029 (10)*
Cl1	0.12024 (7)	0.54723 (4)	0.76556 (9)	0.01743 (14)
I1	0.629687 (18)	0.321563 (10)	0.17166 (2)	0.01562 (7)
O1	0.3734 (3)	0.48091 (13)	0.1171 (4)	0.0404 (6)
H1A	0.320 (4)	0.506 (2)	0.183 (5)	0.061*
H1B	0.363 (5)	0.498 (2)	0.008 (3)	0.061*
O2	0.1749 (2)	0.55620 (12)	0.3282 (3)	0.0240 (4)
H2A	0.183 (4)	0.559 (2)	0.4461 (15)	0.036*
H2B	0.104 (3)	0.5262 (17)	0.294 (4)	0.036*

	U11	U22	U33	U12	U13	U23
C2	0.0231 (14)	0.0138 (13)	0.0161 (13)	0.0066 (11)	0.0044 (11)	0.0019 (10)
C3	0.0122 (13)	0.0270 (15)	0.0173 (14)	0.0054 (11)	0.0034 (11)	0.0065 (11)
C4	0.0139 (13)	0.0186 (13)	0.0138 (12)	−0.0033 (10)	0.0014 (10)	−0.0002 (10)
C5	0.0197 (14)	0.0140 (13)	0.0177 (13)	−0.0021 (11)	0.0034 (11)	−0.0005 (10)
C6	0.0231 (15)	0.0126 (13)	0.0217 (14)	0.0031 (11)	0.0041 (11)	0.0006 (11)
C7	0.0141 (13)	0.0192 (13)	0.0174 (13)	0.0039 (11)	0.0024 (10)	0.0004 (11)
C8	0.0121 (12)	0.0158 (13)	0.0124 (12)	−0.0034 (10)	0.0016 (10)	−0.0024 (10)
C9	0.0130 (12)	0.0124 (12)	0.0099 (11)	−0.0005 (10)	0.0041 (9)	0.0003 (9)
C10	0.0143 (13)	0.0149 (12)	0.0111 (12)	−0.0022 (10)	0.0041 (10)	−0.0005 (10)
N1	0.0153 (12)	0.0110 (11)	0.0172 (12)	−0.0028 (9)	0.0043 (9)	0.0004 (9)
Cl1	0.0163 (3)	0.0132 (3)	0.0221 (3)	−0.0013 (2)	0.0002 (2)	−0.0013 (2)
I1	0.01147 (10)	0.01954 (11)	0.01569 (11)	−0.00378 (6)	0.00106 (7)	−0.00135 (6)
O1	0.0416 (15)	0.0188 (12)	0.0660 (18)	−0.0115 (10)	0.0268 (14)	−0.0137 (11)
O2	0.0235 (11)	0.0214 (11)	0.0267 (11)	−0.0048 (8)	0.0017 (9)	−0.0003 (9)

C2—N1	1.331 (4)	C7—C8	1.387 (4)
C2—C3	1.390 (4)	C7—H7	0.95
C2—H2	0.95	C8—C9	1.421 (4)
C3—C4	1.377 (4)	C8—I1	2.110 (3)
C3—H3	0.95	C9—N1	1.384 (3)
C4—C10	1.426 (4)	C9—C10	1.430 (4)
C4—H4	0.95	N1—H1	0.82 (4)
C5—C6	1.374 (4)	O1—H1A	0.836 (10)
C5—C10	1.420 (4)	O1—H1B	0.834 (10)
C5—H5	0.95	O2—H2A	0.840 (10)
C6—C7	1.419 (4)	O2—H2B	0.841 (10)
C6—H6	0.95
N1—C2—C3	121.5 (2)	C8—C7—H7	119.5
N1—C2—H2	119.2	C6—C7—H7	119.5
C3—C2—H2	119.2	C7—C8—C9	119.0 (2)
C4—C3—C2	118.8 (2)	C7—C8—I1	119.89 (19)
C4—C3—H3	120.6	C9—C8—I1	121.09 (19)
C2—C3—H3	120.6	N1—C9—C8	122.6 (2)
C3—C4—C10	120.6 (2)	N1—C9—C10	117.2 (2)
C3—C4—H4	119.7	C8—C9—C10	120.2 (2)
C10—C4—H4	119.7	C5—C10—C4	122.3 (2)
C6—C5—C10	120.2 (2)	C5—C10—C9	119.0 (2)
C6—C5—H5	119.9	C4—C10—C9	118.8 (2)
C10—C5—H5	119.9	C2—N1—C9	123.1 (2)
C5—C6—C7	120.6 (3)	C2—N1—H1	120 (3)
C5—C6—H6	119.7	C9—N1—H1	117 (3)
C7—C6—H6	119.7	H1A—O1—H1B	110 (2)
C8—C7—C6	121.0 (2)	H2A—O2—H2B	107 (2)
N1—C2—C3—C4	1.1 (4)	C6—C5—C10—C9	−0.5 (4)
C2—C3—C4—C10	−0.8 (4)	C3—C4—C10—C5	179.6 (3)
C10—C5—C6—C7	−1.1 (4)	C3—C4—C10—C9	−0.4 (4)
C5—C6—C7—C8	1.4 (4)	N1—C9—C10—C5	−178.7 (2)
C6—C7—C8—C9	0.0 (4)	C8—C9—C10—C5	1.8 (4)
C6—C7—C8—I1	−177.1 (2)	N1—C9—C10—C4	1.3 (3)
C7—C8—C9—N1	179.0 (2)	C8—C9—C10—C4	−178.2 (2)
I1—C8—C9—N1	−3.9 (3)	C3—C2—N1—C9	−0.2 (4)
C7—C8—C9—C10	−1.6 (4)	C8—C9—N1—C2	178.4 (2)
I1—C8—C9—C10	175.50 (18)	C10—C9—N1—C2	−1.0 (4)
C6—C5—C10—C4	179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.82 (4)	2.03 (4)	2.755 (3)	147 (3)
N1—H1···I1	0.82 (4)	2.85 (4)	3.320 (2)	119 (3)
O1—H1A···O2	0.84 (1)	1.98 (1)	2.807 (3)	173 (5)
O1—H1B···Cl1i	0.83 (1)	2.75 (3)	3.382 (3)	134 (4)
O2—H2A···Cl1	0.84 (1)	2.44 (2)	3.237 (2)	160 (3)
O2—H2B···Cl1ii	0.84 (1)	2.38 (1)	3.211 (2)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.82 (4)	2.03 (4)	2.755 (3)	147 (3)
N1—H1⋯I1	0.82 (4)	2.85 (4)	3.320 (2)	119 (3)
O1—H1A⋯O2	0.84 (1)	1.975 (12)	2.807 (3)	173 (5)
O1—H1B⋯Cl1i	0.83 (1)	2.75 (3)	3.382 (3)	134 (4)
O2—H2A⋯Cl1	0.84 (1)	2.435 (16)	3.237 (2)	160 (3)
O2—H2B⋯Cl1ii	0.84 (1)	2.379 (12)	3.211 (2)	170 (3)

Symmetry codes: (i) ; (ii) .