4-Iodo­anilinium perchlorate

SiMa, W.

doi:10.1107/S1600536810009347

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o895

doi:10.1107/S1600536810009347

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4-Iodoanilinium perchlorate

Weiwei SiMa ^a ^*

^aOrdered Matter Science Researcch Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: nysima@126.com

(Received 27 July 2009; accepted 12 March 2010; online 20 March 2010)

In the crystal structure of the title compound, C₆H₇IN⁺·ClO₄⁻, 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_r = 319.48
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.071
S = 1.11
2180 reflections
119 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.60 e Å⁻³

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) x-1, y-1, z; (ii) -x+1, -y+1, -z; (iii) x-1, y, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

To the present day a lot of structures of phenylamine perchlorate have been reported (Paixao, et al., (1999); Wiedenfeld, et al., (2004); Bendjeddou, et al., 2003; Kapoor, et al., (2008))). As part of our on-going studies on new anilinium perchloratecompounds, the crystal structure of the title compound (I) is reported herein.

The molecular structure of the title compound is shown in Figure 1. The asymmetric unit consists of one protonated 4-iodobenzenamine cation and one perchlorate anion. All bond lengths and bond angles correspond to the geometry parameters expected for atom types and the type of hybirdization (Allen et al., 1987).

The ions are connected in three-dimensional hydrogen-bonded network via N—H···O hydrogen bonds. All ammonium group H atoms are involved in the hydrogen bonding with three O-atoms of neighbouring perchlorate anion and O-atom of carbonyl group of neighbouring cation (Figure 2).

Related literature top

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 et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The preparation of 4-iodoanilinium perchlorateis analogous to that of the compound 4-acetylanilinium perchlorate (Cinčić & Kaitner, 2007). Perchloric acid (3ml,0.16mol/L) was added to a solution of 4-iodobenzenamine (100mg) in ethanol (10ml) and the mixture was stirred for 30 min at room temperature. Colourless crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the mixed solution at room temperature after 3 days.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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).

Figures top

	Fig. 1. A partial packing diagram of the title compound, with the displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound viewed along the a axis. Intermolecular N—H···O hydrogen bonds are shown as dashed lines.

4-Iodoanilinium perchlorate top

Crystal data top

C₆H₇IN⁺·ClO₄⁻	Z = 2
M_r = 319.48	F(000) = 304
Triclinic, P1	D_x = 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

Data collection top

Rigaku SCXmini diffractometer	2180 independent reflections
Radiation source: fine-focus sealed tube	1956 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
CCD_Profile_fitting scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
T_min = 0.484, T_max = 0.489	l = −17→17
4945 measured reflections

Refinement top

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(F_o²) + (0.0248P)² + 0.188P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
2180 reflections	Δρ_max = 0.56 e Å⁻³
119 parameters	Δρ_min = −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)

Crystal data top

C₆H₇IN⁺·ClO₄⁻	γ = 74.61 (3)°
M_r = 319.48	V = 476.22 (17) Å³
Triclinic, P1	Z = 2
a = 5.105 (1) Å	Mo Kα radiation
b = 7.2445 (14) Å	µ = 3.63 mm⁻¹
c = 13.359 (3) Å	T = 298 K
α = 89.47 (3)°	0.20 × 0.20 × 0.20 mm
β = 88.74 (3)°

Data collection top

Rigaku SCXmini diffractometer	2180 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1956 reflections with I > 2σ(I)
T_min = 0.484, T_max = 0.489	R_int = 0.034
4945 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.11	Δρ_max = 0.56 e Å⁻³
2180 reflections	Δρ_min = −0.60 e Å⁻³
119 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 > 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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y−1, z; (ii) −x+1, −y+1, −z; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₆H₇IN⁺·ClO₄⁻
M_r	319.48
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.105 (1), 7.2445 (14), 13.359 (3)
α, β, γ (°)	89.47 (3), 88.74 (3), 74.61 (3)
V (Å³)	476.22 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.63
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.484, 0.489
No. of measured, independent and observed [I > 2σ(I)] reflections	4945, 2180, 1956
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.071, 1.11
No. of reflections	2180
No. of parameters	119
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.60

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.89	2.12	3.002 (4)	173.5
N1—H1B···O3ⁱⁱ	0.89	2.17	2.911 (4)	140.5
N1—H1C···O3ⁱⁱⁱ	0.89	2.21	3.069 (4)	162.1

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

Acknowledgements

This work was supported by a start-up grant from Southeast University.

References

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