4-Iodo­anilinium perchlorate

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.030
• wR factor = 0.071
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

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Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          7

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety         N1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

H atoms were placed at calculated position and were allowed to ride on the respective carrier atom with C—H = 0.93 Å, N—H = 0.86 Å.

Computing details

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

	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

Crystal data

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) Å^3

Data collection

Rigaku SCXmini diffractometer	2180 independent reflections
Radiation source: fine-focus sealed tube	1956 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.071	w = 1/[σ^2(Fo^2) + (0.0248P)^2 + 0.188P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.081 (3)

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^i	0.89	2.12	3.002 (4)	174
N1—H1B···O3^ii	0.89	2.17	2.911 (4)	141
N1—H1C···O3^iii	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.