4-Iodo-anilinium perchlorate.

In the crystal structure of the title compound, C(6)H(7)IN(+)·ClO(4) (-), the ions are connected in a three-dimensional hydrogen-bonded network via N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Paixao et al. (1999 ▶); Wiedenfeld et al. (2004 ▶); Bendjeddou et al. (2003 ▶); Kapoor et al. (2008 ▶). For the synthetic strategy, see: Cinčić & Kaitner (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H7IN+·ClO4 −

M = 319.48

Triclinic,

a = 5.105 (1) Å

b = 7.2445 (14) Å

c = 13.359 (3) Å

α = 89.47 (3)°

β = 88.74 (3)°

γ = 74.61 (3)°

V = 476.22 (17) Å3

Z = 2

Mo Kα radiation

μ = 3.63 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.484, T max = 0.489

4945 measured reflections

2180 independent reflections

1956 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.071

S = 1.11

2180 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.60 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009347/fi2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009347/fi2083Isup2.hkl

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

C6H7IN+·ClO4−	Z = 2
Mr = 319.48	F(000) = 304
Triclinic, P1	Dx = 2.228 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.105 (1) Å	Cell parameters from 2239 reflections
b = 7.2445 (14) Å	θ = 2.6–27.5°
c = 13.359 (3) Å	µ = 3.63 mm−1
α = 89.47 (3)°	T = 298 K
β = 88.74 (3)°	Prism, colourless
γ = 74.61 (3)°	0.20 × 0.20 × 0.20 mm
V = 476.22 (17) Å3

Rigaku SCXmini diffractometer	2180 independent reflections
Radiation source: fine-focus sealed tube	1956 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.484, Tmax = 0.489	l = −17→17
4945 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.071	w = 1/[σ2(Fo2) + (0.0248P)2 + 0.188P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2180 reflections	Δρmax = 0.56 e Å−3
119 parameters	Δρmin = −0.60 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.081 (3)

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 > 2sigma(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	0.32432 (5)	0.26989 (3)	0.544100 (17)	0.05266 (14)
N1	−0.0662 (6)	0.2407 (4)	0.1042 (2)	0.0407 (6)
H1A	−0.1590	0.1529	0.1007	0.061*
H1B	0.0748	0.2111	0.0615	0.061*
H1C	−0.1738	0.3550	0.0885	0.061*
C4	0.0315 (6)	0.2457 (4)	0.2062 (2)	0.0323 (6)
C3	−0.0309 (7)	0.1257 (5)	0.2764 (3)	0.0436 (8)
H3A	−0.1318	0.0410	0.2600	0.052*
C1	0.2064 (7)	0.2578 (5)	0.3963 (2)	0.0371 (7)
C6	0.2694 (7)	0.3764 (5)	0.3249 (3)	0.0458 (8)
H6A	0.3722	0.4600	0.3410	0.055*
C5	0.1789 (7)	0.3708 (5)	0.2285 (3)	0.0418 (8)
H5A	0.2182	0.4518	0.1793	0.050*
C2	0.0591 (8)	0.1326 (5)	0.3724 (3)	0.0482 (9)
H2A	0.0193	0.0515	0.4214	0.058*
Cl1	0.53128 (14)	0.77646 (10)	0.10960 (6)	0.03387 (18)
O1	0.5785 (6)	0.6817 (5)	0.2029 (2)	0.0789 (10)
O2	0.6164 (6)	0.9461 (4)	0.1103 (2)	0.0662 (8)
O3	0.6814 (6)	0.6528 (4)	0.0338 (2)	0.0713 (9)
O4	0.2516 (5)	0.8204 (4)	0.0874 (2)	0.0545 (7)

	U11	U22	U33	U12	U13	U23
I1	0.0751 (2)	0.04546 (18)	0.03956 (17)	−0.01822 (13)	−0.01787 (12)	−0.00395 (11)
N1	0.0449 (15)	0.0431 (15)	0.0372 (15)	−0.0169 (13)	−0.0061 (12)	0.0021 (12)
C4	0.0333 (15)	0.0308 (15)	0.0315 (15)	−0.0063 (12)	−0.0031 (12)	−0.0006 (12)
C3	0.054 (2)	0.0471 (19)	0.0392 (18)	−0.0294 (17)	−0.0100 (15)	0.0040 (15)
C1	0.0432 (17)	0.0353 (16)	0.0326 (16)	−0.0092 (14)	−0.0074 (13)	−0.0042 (13)
C6	0.058 (2)	0.0442 (19)	0.0445 (19)	−0.0295 (17)	−0.0065 (16)	−0.0043 (15)
C5	0.056 (2)	0.0386 (17)	0.0366 (17)	−0.0218 (16)	−0.0043 (15)	0.0026 (14)
C2	0.066 (2)	0.050 (2)	0.0378 (18)	−0.0307 (19)	−0.0082 (17)	0.0097 (16)
Cl1	0.0339 (4)	0.0333 (4)	0.0364 (4)	−0.0124 (3)	−0.0025 (3)	0.0032 (3)
O1	0.078 (2)	0.098 (3)	0.0568 (18)	−0.0186 (19)	−0.0113 (16)	0.0420 (18)
O2	0.0738 (18)	0.0503 (16)	0.088 (2)	−0.0392 (15)	−0.0154 (16)	0.0023 (15)
O3	0.0726 (19)	0.0593 (18)	0.078 (2)	−0.0115 (15)	0.0276 (17)	−0.0246 (16)
O4	0.0369 (13)	0.0721 (18)	0.0562 (16)	−0.0164 (12)	−0.0093 (11)	−0.0044 (14)

I1—C1	2.086 (3)	C1—C6	1.368 (4)
N1—C4	1.465 (4)	C6—C5	1.382 (5)
N1—H1A	0.8900	C6—H6A	0.9300
N1—H1B	0.8900	C5—H5A	0.9300
N1—H1C	0.8900	C2—H2A	0.9300
C4—C5	1.361 (4)	Cl1—O2	1.408 (2)
C4—C3	1.362 (4)	Cl1—O1	1.412 (3)
C3—C2	1.377 (5)	Cl1—O4	1.416 (2)
C3—H3A	0.9300	Cl1—O3	1.426 (3)
C1—C2	1.366 (5)
C4—N1—H1A	109.5	C1—C6—C5	119.4 (3)
C4—N1—H1B	109.5	C1—C6—H6A	120.3
H1A—N1—H1B	109.5	C5—C6—H6A	120.3
C4—N1—H1C	109.5	C4—C5—C6	119.3 (3)
H1A—N1—H1C	109.5	C4—C5—H5A	120.3
H1B—N1—H1C	109.5	C6—C5—H5A	120.3
C5—C4—C3	121.9 (3)	C1—C2—C3	120.6 (3)
C5—C4—N1	119.4 (3)	C1—C2—H2A	119.7
C3—C4—N1	118.7 (3)	C3—C2—H2A	119.7
C4—C3—C2	118.4 (3)	O2—Cl1—O1	110.7 (2)
C4—C3—H3A	120.8	O2—Cl1—O4	109.57 (18)
C2—C3—H3A	120.8	O1—Cl1—O4	110.10 (18)
C2—C1—C6	120.4 (3)	O2—Cl1—O3	108.95 (19)
C2—C1—I1	118.9 (2)	O1—Cl1—O3	108.8 (2)
C6—C1—I1	120.6 (2)	O4—Cl1—O3	108.73 (19)
C5—C4—C3—C2	0.0 (5)	N1—C4—C5—C6	179.6 (3)
N1—C4—C3—C2	−179.3 (3)	C1—C6—C5—C4	−0.8 (5)
C2—C1—C6—C5	1.1 (5)	C6—C1—C2—C3	−0.8 (6)
I1—C1—C6—C5	−177.3 (3)	I1—C1—C2—C3	177.6 (3)
C3—C4—C5—C6	0.3 (5)	C4—C3—C2—C1	0.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.89	2.12	3.002 (4)	174
N1—H1B···O3ii	0.89	2.17	2.911 (4)	141
N1—H1C···O3iii	0.89	2.21	3.069 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.89	2.12	3.002 (4)	174
N1—H1B⋯O3ii	0.89	2.17	2.911 (4)	141
N1—H1C⋯O3iii	0.89	2.21	3.069 (4)	162

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