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ISSN: 2056-9890

4-Iodo­anilinium perchlorate

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[Paixao, J. A., Matos Bejia, A., Ramos Silva, M., Alte da Veiga, L. & Martin-Gil, J. (1999). Z. Kristallogr. New Cryst. Struct. 214, 85-86.]); Wiedenfeld et al. (2004[Wiedenfeld, D., Minton, M., Nesterov, V. & Montoya, C. (2004). J. Chem. Crystallogr. 34, 95-101.]); Bendjeddou et al. (2003[Bendjeddou, L., Cherouana, A., Berrah, F. & Benali-Cherif, N. (2003). Acta Cryst. E59, o574-o576.]); Kapoor et al. (2008[Kapoor, I. P. S., Srivastava, P., Singh, G. & Frohlich, R. (2008). J. Phys. Chem. A, 112, 652-659.]). For the synthetic strategy, see: Cinčić & Kaitner (2007[Cinčić, D. & Kaitner, B. (2007). Acta Cryst. E63, o4672.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C6H7IN+·ClO4

  • Mr = 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.484, Tmax = 0.489

  • 4945 measured reflections

  • 2180 independent reflections

  • 1956 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information


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.

Refinement top

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 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
[Figure 1] Fig. 1. A partial packing diagram of the title compound, with the displacement ellipsoids were drawn at the 30% probability level.
[Figure 2] 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+·ClO4Z = 2
Mr = 319.48F(000) = 304
Triclinic, P1Dx = 2.228 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.105 (1) ÅCell parameters from 2239 reflections
b = 7.2445 (14) Åθ = 2.6–27.5°
c = 13.359 (3) ŵ = 3.63 mm1
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 tube1956 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scansh = 66
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 99
Tmin = 0.484, Tmax = 0.489l = 1717
4945 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-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 reflectionsΔρmax = 0.56 e Å3
119 parametersΔρmin = 0.60 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.081 (3)
Crystal data top
C6H7IN+·ClO4γ = 74.61 (3)°
Mr = 319.48V = 476.22 (17) Å3
Triclinic, P1Z = 2
a = 5.105 (1) ÅMo Kα radiation
b = 7.2445 (14) ŵ = 3.63 mm1
c = 13.359 (3) ÅT = 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)
Tmin = 0.484, Tmax = 0.489Rint = 0.034
4945 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.071H-atom parameters constrained
S = 1.11Δρmax = 0.56 e Å3
2180 reflectionsΔρmin = 0.60 e Å3
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
xyzUiso*/Ueq
I10.32432 (5)0.26989 (3)0.544100 (17)0.05266 (14)
N10.0662 (6)0.2407 (4)0.1042 (2)0.0407 (6)
H1A0.15900.15290.10070.061*
H1B0.07480.21110.06150.061*
H1C0.17380.35500.08850.061*
C40.0315 (6)0.2457 (4)0.2062 (2)0.0323 (6)
C30.0309 (7)0.1257 (5)0.2764 (3)0.0436 (8)
H3A0.13180.04100.26000.052*
C10.2064 (7)0.2578 (5)0.3963 (2)0.0371 (7)
C60.2694 (7)0.3764 (5)0.3249 (3)0.0458 (8)
H6A0.37220.46000.34100.055*
C50.1789 (7)0.3708 (5)0.2285 (3)0.0418 (8)
H5A0.21820.45180.17930.050*
C20.0591 (8)0.1326 (5)0.3724 (3)0.0482 (9)
H2A0.01930.05150.42140.058*
Cl10.53128 (14)0.77646 (10)0.10960 (6)0.03387 (18)
O10.5785 (6)0.6817 (5)0.2029 (2)0.0789 (10)
O20.6164 (6)0.9461 (4)0.1103 (2)0.0662 (8)
O30.6814 (6)0.6528 (4)0.0338 (2)0.0713 (9)
O40.2516 (5)0.8204 (4)0.0874 (2)0.0545 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0751 (2)0.04546 (18)0.03956 (17)0.01822 (13)0.01787 (12)0.00395 (11)
N10.0449 (15)0.0431 (15)0.0372 (15)0.0169 (13)0.0061 (12)0.0021 (12)
C40.0333 (15)0.0308 (15)0.0315 (15)0.0063 (12)0.0031 (12)0.0006 (12)
C30.054 (2)0.0471 (19)0.0392 (18)0.0294 (17)0.0100 (15)0.0040 (15)
C10.0432 (17)0.0353 (16)0.0326 (16)0.0092 (14)0.0074 (13)0.0042 (13)
C60.058 (2)0.0442 (19)0.0445 (19)0.0295 (17)0.0065 (16)0.0043 (15)
C50.056 (2)0.0386 (17)0.0366 (17)0.0218 (16)0.0043 (15)0.0026 (14)
C20.066 (2)0.050 (2)0.0378 (18)0.0307 (19)0.0082 (17)0.0097 (16)
Cl10.0339 (4)0.0333 (4)0.0364 (4)0.0124 (3)0.0025 (3)0.0032 (3)
O10.078 (2)0.098 (3)0.0568 (18)0.0186 (19)0.0113 (16)0.0420 (18)
O20.0738 (18)0.0503 (16)0.088 (2)0.0392 (15)0.0154 (16)0.0023 (15)
O30.0726 (19)0.0593 (18)0.078 (2)0.0115 (15)0.0276 (17)0.0246 (16)
O40.0369 (13)0.0721 (18)0.0562 (16)0.0164 (12)0.0093 (11)0.0044 (14)
Geometric parameters (Å, º) top
I1—C12.086 (3)C1—C61.368 (4)
N1—C41.465 (4)C6—C51.382 (5)
N1—H1A0.8900C6—H6A0.9300
N1—H1B0.8900C5—H5A0.9300
N1—H1C0.8900C2—H2A0.9300
C4—C51.361 (4)Cl1—O21.408 (2)
C4—C31.362 (4)Cl1—O11.412 (3)
C3—C21.377 (5)Cl1—O41.416 (2)
C3—H3A0.9300Cl1—O31.426 (3)
C1—C21.366 (5)
C4—N1—H1A109.5C1—C6—C5119.4 (3)
C4—N1—H1B109.5C1—C6—H6A120.3
H1A—N1—H1B109.5C5—C6—H6A120.3
C4—N1—H1C109.5C4—C5—C6119.3 (3)
H1A—N1—H1C109.5C4—C5—H5A120.3
H1B—N1—H1C109.5C6—C5—H5A120.3
C5—C4—C3121.9 (3)C1—C2—C3120.6 (3)
C5—C4—N1119.4 (3)C1—C2—H2A119.7
C3—C4—N1118.7 (3)C3—C2—H2A119.7
C4—C3—C2118.4 (3)O2—Cl1—O1110.7 (2)
C4—C3—H3A120.8O2—Cl1—O4109.57 (18)
C2—C3—H3A120.8O1—Cl1—O4110.10 (18)
C2—C1—C6120.4 (3)O2—Cl1—O3108.95 (19)
C2—C1—I1118.9 (2)O1—Cl1—O3108.8 (2)
C6—C1—I1120.6 (2)O4—Cl1—O3108.73 (19)
C5—C4—C3—C20.0 (5)N1—C4—C5—C6179.6 (3)
N1—C4—C3—C2179.3 (3)C1—C6—C5—C40.8 (5)
C2—C1—C6—C51.1 (5)C6—C1—C2—C30.8 (6)
I1—C1—C6—C5177.3 (3)I1—C1—C2—C3177.6 (3)
C3—C4—C5—C60.3 (5)C4—C3—C2—C10.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.892.123.002 (4)174
N1—H1B···O3ii0.892.172.911 (4)141
N1—H1C···O3iii0.892.213.069 (4)162
Symmetry codes: (i) x1, y1, z; (ii) x+1, y+1, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC6H7IN+·ClO4
Mr319.48
Crystal system, space groupTriclinic, 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)
V3)476.22 (17)
Z2
Radiation typeMo Kα
µ (mm1)3.63
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.484, 0.489
No. of measured, independent and
observed [I > 2σ(I)] reflections
4945, 2180, 1956
Rint0.034
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.071, 1.11
No. of reflections2180
No. of parameters119
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1A···O2i0.892.123.002 (4)173.5
N1—H1B···O3ii0.892.172.911 (4)140.5
N1—H1C···O3iii0.892.213.069 (4)162.1
Symmetry codes: (i) x1, y1, z; (ii) x+1, y+1, z; (iii) x1, y, z.
 

Acknowledgements

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

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBendjeddou, L., Cherouana, A., Berrah, F. & Benali-Cherif, N. (2003). Acta Cryst. E59, o574–o576.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationCinčić, D. & Kaitner, B. (2007). Acta Cryst. E63, o4672.  Web of Science CrossRef IUCr Journals Google Scholar
First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
First citationKapoor, I. P. S., Srivastava, P., Singh, G. & Frohlich, R. (2008). J. Phys. Chem. A, 112, 652–659.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationPaixao, J. A., Matos Bejia, A., Ramos Silva, M., Alte da Veiga, L. & Martin-Gil, J. (1999). Z. Kristallogr. New Cryst. Struct. 214, 85–86.  CAS Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWiedenfeld, D., Minton, M., Nesterov, V. & Montoya, C. (2004). J. Chem. Crystallogr. 34, 95–101.  Web of Science CSD CrossRef CAS Google Scholar

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