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ISSN: 2056-9890

4-Meth­­oxy­anilinium iodide

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

(Received 1 July 2010; accepted 16 November 2010; online 27 November 2010)

The crystal structure of the title compound, C7H10NO+·I, displays N—H⋯I hydrogen bonds between the 4-meth­oxy­anilinium cations and the iodide anion together with weaker C—H⋯π contacts.

Related literature

The title compound was invesitgated as a potential candidate for having good dielectric properties. For compounds with dielectric–ferroelectric properties, see: Hang et al. (2009[Hang, T., Fu, D. W., Ye, Q. & Xiong, R. G. (2009). Cryst. Growth Des. 5, 2026-2029.]); Li et al. (2008[Li, X. Z., Qu, Z. R. & Xiong, R. G. (2008). Chin. J. Chem. 11, 1959-1962.]).

[Scheme 1]

Experimental

Crystal data
  • C7H10NO+·I

  • Mr = 251.06

  • Orthorhombic, P b c a

  • a = 12.290 (3) Å

  • b = 7.1302 (14) Å

  • c = 20.304 (4) Å

  • V = 1779.2 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.54 mm−1

  • T = 298 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.291, Tmax = 0.493

  • 16921 measured reflections

  • 2040 independent reflections

  • 1803 reflections with I > 2σ(I)

  • Rint = 0.052

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.065

  • S = 1.25

  • 2040 reflections

  • 104 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1D⋯I1i 0.86 (3) 2.67 (2) 3.503 (3) 165 (5)
N1—H1F⋯I1ii 0.86 (1) 2.75 (2) 3.566 (3) 159 (3)
N1—H1E⋯I1 0.86 (4) 2.75 (4) 3.568 (3) 159 (4)
C4—H4⋯Cg1iii 0.93 2.87 3.627 (4) 140
C7—H7⋯Cg1iv 0.93 2.62 3.483 (4) 155
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) -x+1, -y+1, -z+1; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

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: SHELXL97.

Supporting information


Comment top

Dielectric-ferroelectric constitute an interesting class of materials, comprising organic ligands (Li et al., 2008), metal-organic coordination compounds (Hang et al., 2009) and organic-inorganic hybrids. We were interested in the title compound as a potential candidate for having good dielectric properties. Unfortunately, the capacitance and dielectric loss measurements did not show any distinct anomaly when observed from 93 K to 455 K (its sublimation temperaure). Regarding its crystal structure, the asymmetric unit of the title compound contains a (4-methoxyanilinium) cation and a iodide anion (Fig.1). The structure is stabilized by C—H···π interactions (C4—H4···Cg1 3.627 (4) Å and C7—H7···Cg1 3.483 (4) Å) as well as weak N—H···I hydrogen bonds involving the NH3 group and linking the cations and anions into a 3D structure (Fig. 2 and Tab. 1).

Related literature top

The title compound was invesitgated as a potential candidate for having good dielectric properties. For compounds with dielectric–ferroelectric properties, see: Hang et al. (2009); Li et al. (2008)

Experimental top

The title compound was obtained by the addition of hydriodic acid (4.12 ml, 0.022 mol) to a solution of 4-methoxyanilin (2.26 g, 0.02 mol) in ethanol, in the stoichiometric ratio 1.1:1. Good quality single crystals were obtained by slow evaporation after two weeks.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and the H atoms were set to ride on the C and N atoms to which they are bonded, with Uiso(H) = 1.2Ueq(C or N).

Structure description top

Dielectric-ferroelectric constitute an interesting class of materials, comprising organic ligands (Li et al., 2008), metal-organic coordination compounds (Hang et al., 2009) and organic-inorganic hybrids. We were interested in the title compound as a potential candidate for having good dielectric properties. Unfortunately, the capacitance and dielectric loss measurements did not show any distinct anomaly when observed from 93 K to 455 K (its sublimation temperaure). Regarding its crystal structure, the asymmetric unit of the title compound contains a (4-methoxyanilinium) cation and a iodide anion (Fig.1). The structure is stabilized by C—H···π interactions (C4—H4···Cg1 3.627 (4) Å and C7—H7···Cg1 3.483 (4) Å) as well as weak N—H···I hydrogen bonds involving the NH3 group and linking the cations and anions into a 3D structure (Fig. 2 and Tab. 1).

The title compound was invesitgated as a potential candidate for having good dielectric properties. For compounds with dielectric–ferroelectric properties, see: Hang et al. (2009); Li et al. (2008)

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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the packing of the title compound, stacking along the b axis. Dashed lines indicate hydrogen bonds.
4-Methoxyanilinium iodide top
Crystal data top
C7H10NO+·IF(000) = 960
Mr = 251.06Dx = 1.875 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 7161 reflections
a = 12.290 (3) Åθ = 3.0–27.7°
b = 7.1302 (14) ŵ = 3.54 mm1
c = 20.304 (4) ÅT = 298 K
V = 1779.2 (6) Å3Prism, colourless
Z = 80.40 × 0.30 × 0.20 mm
Data collection top
Rigaku SCXmini
diffractometer
2040 independent reflections
Radiation source: fine-focus sealed tube1803 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.3°
ω scansh = 1515
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 99
Tmin = 0.291, Tmax = 0.493l = 2626
16921 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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065 w = 1/[σ2(Fo2) + (0.0154P)2 + 1.2835P]
where P = (Fo2 + 2Fc2)/3
S = 1.25(Δ/σ)max < 0.001
2040 reflectionsΔρmax = 0.51 e Å3
104 parametersΔρmin = 0.45 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0053 (2)
Crystal data top
C7H10NO+·IV = 1779.2 (6) Å3
Mr = 251.06Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.290 (3) ŵ = 3.54 mm1
b = 7.1302 (14) ÅT = 298 K
c = 20.304 (4) Å0.40 × 0.30 × 0.20 mm
Data collection top
Rigaku SCXmini
diffractometer
2040 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1803 reflections with I > 2σ(I)
Tmin = 0.291, Tmax = 0.493Rint = 0.052
16921 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0323 restraints
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 1.25Δρmax = 0.51 e Å3
2040 reflectionsΔρmin = 0.45 e Å3
104 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.613461 (19)0.22260 (3)0.471872 (12)0.04311 (12)
C10.3182 (4)0.1321 (6)0.88673 (18)0.0580 (11)
H1A0.33210.07240.92830.087*
H1B0.24440.10830.87360.087*
H1C0.32930.26480.89090.087*
C20.3836 (3)0.1268 (4)0.77653 (15)0.0332 (7)
C30.3010 (3)0.2400 (4)0.75290 (18)0.0347 (7)
H30.24480.27780.78060.042*
C40.3024 (3)0.2967 (4)0.68761 (16)0.0327 (7)
H40.24720.37280.67130.039*
C50.3856 (2)0.2399 (4)0.64723 (16)0.0303 (7)
C60.4686 (3)0.1275 (5)0.67025 (17)0.0377 (8)
H60.52440.08960.64230.045*
C70.4676 (3)0.0724 (5)0.73515 (18)0.0425 (8)
H70.52370.00190.75140.051*
N10.3861 (3)0.2978 (5)0.57794 (16)0.0402 (7)
H1F0.400 (3)0.4157 (18)0.5742 (18)0.041 (10)*
H1E0.438 (3)0.248 (5)0.5554 (19)0.059 (13)*
H1D0.324 (2)0.281 (6)0.559 (2)0.077 (16)*
O10.3897 (2)0.0598 (4)0.83889 (12)0.0517 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.04084 (17)0.04212 (17)0.04635 (17)0.00309 (9)0.01153 (9)0.00348 (10)
C10.078 (3)0.064 (3)0.032 (2)0.008 (2)0.0061 (19)0.0060 (18)
C20.041 (2)0.0286 (17)0.0296 (17)0.0015 (14)0.0032 (13)0.0018 (12)
C30.0360 (17)0.0326 (17)0.0354 (18)0.0031 (13)0.0052 (14)0.0018 (13)
C40.0299 (16)0.0293 (16)0.0388 (18)0.0051 (13)0.0023 (13)0.0015 (13)
C50.0321 (17)0.0284 (16)0.0303 (16)0.0021 (12)0.0010 (12)0.0009 (12)
C60.0309 (17)0.042 (2)0.0404 (19)0.0093 (14)0.0065 (14)0.0018 (15)
C70.040 (2)0.043 (2)0.044 (2)0.0164 (16)0.0033 (15)0.0045 (16)
N10.0400 (18)0.0456 (19)0.0352 (16)0.0018 (15)0.0045 (13)0.0085 (14)
O10.0712 (19)0.0532 (16)0.0307 (13)0.0172 (13)0.0012 (12)0.0097 (11)
Geometric parameters (Å, º) top
C1—O11.407 (4)C4—H40.9300
C1—H1A0.9600C5—C61.380 (4)
C1—H1B0.9600C5—N11.466 (4)
C1—H1C0.9600C6—C71.375 (5)
C2—O11.355 (4)C6—H60.9300
C2—C31.383 (5)C7—H70.9300
C2—C71.386 (5)N1—H1F0.860 (10)
C3—C41.386 (5)N1—H1E0.86 (4)
C3—H30.9300N1—H1D0.86 (3)
C4—C51.371 (4)
O1—C1—H1A109.5C4—C5—N1119.6 (3)
O1—C1—H1B109.5C6—C5—N1119.0 (3)
H1A—C1—H1B109.5C7—C6—C5119.0 (3)
O1—C1—H1C109.5C7—C6—H6120.5
H1A—C1—H1C109.5C5—C6—H6120.5
H1B—C1—H1C109.5C6—C7—C2120.5 (3)
O1—C2—C3124.8 (3)C6—C7—H7119.8
O1—C2—C7115.2 (3)C2—C7—H7119.8
C3—C2—C7120.0 (3)C5—N1—H1F111 (3)
C2—C3—C4119.5 (3)C5—N1—H1E113 (3)
C2—C3—H3120.3H1F—N1—H1E102 (3)
C4—C3—H3120.3C5—N1—H1D113 (4)
C5—C4—C3119.7 (3)H1F—N1—H1D105 (4)
C5—C4—H4120.1H1E—N1—H1D111 (5)
C3—C4—H4120.1C2—O1—C1118.8 (3)
C4—C5—C6121.3 (3)
O1—C2—C3—C4178.6 (3)N1—C5—C6—C7179.6 (3)
C7—C2—C3—C40.6 (5)C5—C6—C7—C20.9 (5)
C2—C3—C4—C50.0 (5)O1—C2—C7—C6178.2 (3)
C3—C4—C5—C60.2 (5)C3—C2—C7—C61.1 (5)
C3—C4—C5—N1179.1 (3)C3—C2—O1—C110.9 (5)
C4—C5—C6—C70.3 (5)C7—C2—O1—C1169.8 (4)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C2–C7 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1D···I1i0.86 (3)2.67 (2)3.503 (3)165 (5)
N1—H1F···I1ii0.86 (1)2.75 (2)3.566 (3)159 (3)
N1—H1E···I10.86 (4)2.75 (4)3.568 (3)159 (4)
C4—H4···Cg1iii0.932.873.627 (4)140
C7—H7···Cg1iv0.932.623.483 (4)155
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1, y+1, z+1; (iii) x+1/2, y+1/2, z; (iv) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC7H10NO+·I
Mr251.06
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)12.290 (3), 7.1302 (14), 20.304 (4)
V3)1779.2 (6)
Z8
Radiation typeMo Kα
µ (mm1)3.54
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerRigaku SCXmini
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.291, 0.493
No. of measured, independent and
observed [I > 2σ(I)] reflections
16921, 2040, 1803
Rint0.052
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.065, 1.25
No. of reflections2040
No. of parameters104
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.51, 0.45

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

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C2–C7 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1D···I1i0.86 (3)2.665 (17)3.503 (3)165 (5)
N1—H1F···I1ii0.860 (10)2.748 (16)3.566 (3)159 (3)
N1—H1E···I10.86 (4)2.75 (4)3.568 (3)159 (4)
C4—H4···Cg1iii0.932.873.627 (4)140
C7—H7···Cg1iv0.932.623.483 (4)155
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1, y+1, z+1; (iii) x+1/2, y+1/2, z; (iv) x+1, y1/2, z+3/2.
 

Acknowledgements

The author thanks Southeast University for financial support of this research and is very grateful for the guidance of Professor Wen Zhang.

References

First citationHang, T., Fu, D. W., Ye, Q. & Xiong, R. G. (2009). Cryst. Growth Des. 5, 2026–2029.  Web of Science CSD CrossRef Google Scholar
First citationLi, X. Z., Qu, Z. R. & Xiong, R. G. (2008). Chin. J. Chem. 11, 1959–1962.  Web of Science CSD CrossRef 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

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ISSN: 2056-9890
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