PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1326.
Published online 2010 May 12. doi:  10.1107/S1600536810016740
PMCID: PMC2979466

4-Iodo­anilinium nitrate

Abstract

In the title compound, C6H7IN+·NO3 , π–π stacking inter­actions [centroid–centroid distances = 4.014 (4) and 4.029 (4) Å] stabilize the crystal structure and strong N—H(...)O and N—H(...)N hydrogen bonds link the cations and anions into zigzag chains running parallel to the c axis. The asymmetric unit contains two unique cations and anions

Related literature

For background to phase-transition materials, see: Li et al. (2008 [triangle]); Zhang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1326-scheme1.jpg

Experimental

Crystal data

  • C6H7IN+·NO3
  • M r = 282.04
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1326-efi1.jpg
  • a = 21.847 (4) Å
  • b = 5.6103 (11) Å
  • c = 15.928 (3) Å
  • β = 110.11 (3)°
  • V = 1833.2 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.47 mm−1
  • T = 298 K
  • 0.40 × 0.30 × 0.20 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.5, T max = 0.5
  • 17732 measured reflections
  • 4196 independent reflections
  • 3075 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.112
  • S = 1.13
  • 4196 reflections
  • 217 parameters
  • H-atom parameters constrained
  • Δρmax = 1.07 e Å−3
  • Δρmin = −0.78 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016740/jh2153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016740/jh2153Isup2.hkl

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

Acknowledgments

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

supplementary crystallographic information

Comment

As a continuation of our study of phase transition materials, including organic ligands (Li et al., 2008), metal-organic coordination compounds (Zhang et al., 2009 ), organic-inorganic hybrids, we studied the dielectric properties of the title compound, unfortunately, there was no distinct anomaly observed from 93 K to 380 K, (m.p. 408 K-410 K). In this article, the crystal structure of (I) has been presented.

The asymmetric unit of the title compound is built up from two 4-iodobenzenammnium cations wherein the dihedral angle between plans formed by non-hydrogen atoms is 15.3 (2)°,and two nitrate radical anions (Fig.1). The π-π packing interaction of adjacent benzene rings with Cg(1)—Cg(1), 4.029 (4)Å; Cg(2)—Cg(2), 4.014 (4)Å [Cg(1) and Cg(2) are the centroids of benzene rings, where Cg(1): C(1) to C(6); Cg(2): C(7) to C(12)], make great contribution to the stability of the crystal structure. The strong intermolecular N—H···O (N···O distances 2.795 (7)-3.264 (8)Å) and N—H···N (N···N distances 3.372 (8)-3.459 (9)Å) hydrogen bonding link cations and anions into zigzag chains along c axis.

Experimental

Single crystals of 4-iodoanilinium nitrate were prepared by slow evaporation at room temperature of an ethanol solution of equal molar 4-iodobenzenamine and nitrate acid.

Refinement

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

Uiso(H) = 1.2Ueq(N).

Figures

Fig. 1.
The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level, and all H atoms have been omitted for clarity.
Fig. 2.
A view of the packing of the title compound, stacking along the c axis. Dashed lines indicate hydrogen bonds.

Crystal data

C6H7IN+·NO3F(000) = 1072
Mr = 282.04Dx = 2.044 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7323 reflections
a = 21.847 (4) Åθ = 3.2–27.6°
b = 5.6103 (11) ŵ = 3.47 mm1
c = 15.928 (3) ÅT = 298 K
β = 110.11 (3)°Prism, colourless
V = 1833.2 (6) Å30.40 × 0.30 × 0.20 mm
Z = 8

Data collection

Rigaku SCXmini diffractometer4196 independent reflections
Radiation source: fine-focus sealed tube3075 reflections with I > 2σ(I)
graphiteRint = 0.041
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = −28→28
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −7→7
Tmin = 0.5, Tmax = 0.5l = −20→20
17732 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.13w = 1/[σ2(Fo2) + (0.0174P)2 + 9.5262P] where P = (Fo2 + 2Fc2)/3
4196 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 1.07 e Å3
0 restraintsΔρmin = −0.78 e Å3

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 > 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)

xyzUiso*/Ueq
I20.38469 (2)0.37839 (12)0.76874 (3)0.0735 (2)
C100.5931 (3)0.3846 (12)0.9095 (4)0.0471 (15)
H10A0.62810.28740.91200.056*
N20.6682 (3)0.6372 (10)1.0215 (4)0.0513 (14)
H2B0.66780.77091.05130.062*
H2C0.69470.65500.99010.062*
H2D0.68230.51741.05990.062*
C110.5297 (3)0.3288 (13)0.8534 (4)0.0507 (16)
H11A0.52240.19260.81810.061*
C90.6020 (3)0.5850 (11)0.9604 (4)0.0412 (14)
C80.5520 (3)0.7336 (12)0.9573 (4)0.0503 (16)
H8A0.55960.87060.99230.060*
C120.4790 (3)0.4729 (12)0.8504 (4)0.0448 (15)
C70.4894 (3)0.6768 (13)0.9008 (5)0.0514 (16)
H7A0.45460.77690.89730.062*
I10.11990 (2)0.89729 (11)0.38039 (3)0.06947 (19)
C3−0.1001 (3)1.0935 (11)0.3605 (4)0.0424 (14)
N1−0.1670 (2)1.1490 (10)0.3549 (4)0.0528 (14)
H1B−0.19411.03910.32180.063*
H1C−0.17831.29160.32990.063*
H1D−0.16941.14990.40960.063*
C60.0249 (3)0.9855 (12)0.3725 (4)0.0451 (15)
C2−0.0884 (3)0.8935 (12)0.3196 (4)0.0520 (16)
H2A−0.12280.79440.28830.062*
C4−0.0498 (3)1.2412 (12)0.4073 (4)0.0497 (16)
H4A−0.05811.37740.43490.060*
C50.0135 (3)1.1858 (13)0.4131 (5)0.0543 (17)
H5A0.04791.28500.44450.065*
C1−0.0264 (3)0.8386 (12)0.3247 (4)0.0511 (16)
H1A−0.01850.70330.29620.061*
O60.3304 (2)−0.1221 (9)0.9162 (3)0.0657 (14)
N40.2778 (3)−0.1278 (12)0.8524 (4)0.0553 (15)
O50.2512 (3)−0.3234 (10)0.8268 (4)0.0745 (16)
O40.2531 (3)0.0559 (11)0.8148 (4)0.0826 (18)
N30.2248 (3)0.3536 (11)0.5730 (4)0.0560 (15)
O30.2487 (3)0.1485 (9)0.5783 (4)0.0686 (15)
O20.1727 (3)0.3781 (10)0.5883 (4)0.0749 (16)
O10.2517 (3)0.5249 (11)0.5535 (5)0.0885 (19)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I20.0463 (3)0.1119 (5)0.0590 (3)−0.0160 (3)0.0141 (2)−0.0082 (3)
C100.044 (3)0.054 (4)0.045 (3)0.005 (3)0.017 (3)−0.002 (3)
N20.048 (3)0.054 (4)0.053 (3)−0.010 (3)0.019 (3)−0.005 (3)
C110.059 (4)0.054 (4)0.040 (3)−0.003 (3)0.019 (3)−0.009 (3)
C90.038 (3)0.048 (4)0.038 (3)−0.005 (3)0.013 (3)0.002 (3)
C80.060 (4)0.042 (4)0.051 (4)−0.005 (3)0.021 (3)−0.005 (3)
C120.043 (3)0.059 (4)0.035 (3)−0.004 (3)0.017 (3)0.002 (3)
C70.045 (4)0.053 (4)0.059 (4)0.007 (3)0.021 (3)0.002 (3)
I10.0449 (3)0.0962 (4)0.0641 (3)0.0188 (3)0.0146 (2)−0.0032 (3)
C30.043 (3)0.047 (4)0.040 (3)0.003 (3)0.017 (3)0.000 (3)
N10.043 (3)0.060 (4)0.055 (3)0.006 (3)0.016 (3)−0.003 (3)
C60.044 (3)0.056 (4)0.036 (3)0.014 (3)0.013 (3)0.005 (3)
C20.051 (4)0.056 (4)0.049 (4)−0.007 (3)0.017 (3)−0.012 (3)
C40.055 (4)0.040 (4)0.052 (4)0.004 (3)0.016 (3)−0.009 (3)
C50.047 (4)0.056 (4)0.054 (4)0.000 (3)0.009 (3)−0.014 (3)
C10.059 (4)0.052 (4)0.045 (4)−0.001 (3)0.021 (3)−0.014 (3)
O60.058 (3)0.069 (4)0.056 (3)0.000 (3)0.002 (2)−0.001 (3)
N40.044 (3)0.061 (4)0.061 (4)−0.004 (3)0.017 (3)−0.005 (3)
O50.063 (3)0.063 (3)0.099 (4)−0.019 (3)0.030 (3)−0.016 (3)
O40.069 (4)0.069 (4)0.085 (4)0.000 (3)−0.006 (3)0.009 (3)
N30.046 (3)0.058 (4)0.062 (4)0.005 (3)0.016 (3)−0.007 (3)
O30.061 (3)0.057 (3)0.095 (4)0.015 (3)0.037 (3)−0.001 (3)
O20.055 (3)0.071 (4)0.114 (5)0.008 (3)0.048 (3)−0.007 (3)
O10.070 (4)0.063 (4)0.143 (6)0.001 (3)0.050 (4)0.010 (4)

Geometric parameters (Å, °)

I2—C122.091 (6)C3—N11.467 (7)
C10—C91.360 (9)N1—H1B0.8900
C10—C111.401 (9)N1—H1C0.8900
C10—H10A0.9300N1—H1D0.8900
N2—C91.469 (7)C6—C51.361 (9)
N2—H2B0.8900C6—C11.389 (9)
N2—H2C0.8900C2—C11.365 (9)
N2—H2D0.8900C2—H2A0.9300
C11—C121.359 (9)C4—C51.390 (9)
C11—H11A0.9300C4—H4A0.9300
C9—C81.361 (9)C5—H5A0.9300
C8—C71.392 (9)C1—H1A0.9300
C8—H8A0.9300O6—N41.246 (7)
C12—C71.371 (9)N4—O41.221 (8)
C7—H7A0.9300N4—O51.243 (7)
I1—C62.095 (6)N3—O11.220 (8)
C3—C21.365 (9)N3—O21.253 (7)
C3—C41.373 (9)N3—O31.254 (7)
C9—C10—C11118.2 (6)C3—N1—H1B109.5
C9—C10—H10A120.9C3—N1—H1C109.5
C11—C10—H10A120.9H1B—N1—H1C109.5
C9—N2—H2B109.5C3—N1—H1D109.5
C9—N2—H2C109.5H1B—N1—H1D109.5
H2B—N2—H2C109.5H1C—N1—H1D109.5
C9—N2—H2D109.5C5—C6—C1120.4 (6)
H2B—N2—H2D109.5C5—C6—I1120.4 (5)
H2C—N2—H2D109.5C1—C6—I1119.2 (5)
C12—C11—C10120.3 (6)C3—C2—C1120.2 (6)
C12—C11—H11A119.8C3—C2—H2A119.9
C10—C11—H11A119.8C1—C2—H2A119.9
C10—C9—C8122.4 (6)C3—C4—C5119.6 (6)
C10—C9—N2117.7 (6)C3—C4—H4A120.2
C8—C9—N2119.8 (6)C5—C4—H4A120.2
C9—C8—C7118.8 (6)C6—C5—C4119.6 (6)
C9—C8—H8A120.6C6—C5—H5A120.2
C7—C8—H8A120.6C4—C5—H5A120.2
C11—C12—C7120.5 (6)C2—C1—C6119.7 (6)
C11—C12—I2119.2 (5)C2—C1—H1A120.1
C7—C12—I2120.3 (5)C6—C1—H1A120.1
C12—C7—C8119.8 (6)O4—N4—O5120.4 (6)
C12—C7—H7A120.1O4—N4—O6120.4 (6)
C8—C7—H7A120.1O5—N4—O6119.1 (7)
C2—C3—C4120.6 (6)O1—N3—O2120.8 (6)
C2—C3—N1119.4 (6)O1—N3—O3121.0 (6)
C4—C3—N1120.0 (6)O2—N3—O3118.1 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O4i0.892.182.945 (8)144
N1—H1C···O2ii0.892.242.819 (8)122
N1—H1C···O5i0.892.463.010 (8)120
N1—H1D···O3i0.892.462.898 (8)111
N1—H1D···I1ii0.893.153.990 (6)157
N2—H2B···O6iii0.892.032.892 (8)162
N2—H2B···O4iii0.892.443.104 (8)132
N2—H2B···N4iii0.892.553.372 (8)153
N2—H2C···O3iv0.891.912.795 (7)173
N2—H2C···N3iv0.892.563.407 (8)159
N2—H2C···O1iv0.892.593.264 (8)133
N2—H2D···O5v0.892.183.018 (8)157
N2—H2D···O6v0.892.283.053 (8)145
N2—H2D···N4v0.892.583.459 (9)170

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2153).

References

  • Ferguson, G. (1999). PRPKAPPA University of Guelph, Canada.
  • Li, X. Z., Qu, Z. R. & Xiong, R. G. (2008). Chin. J. Chem 11, 1959–1962
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, W., Chen, L. Z., Xiong, R. G., Nakamura, T. & Huang, S. D. (2009). J. Am. Chem. Soc.131, 12544–12545 [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography