Acta Cryst. (2008). E64, o591 [ doi:10.1107/S1600536808004145 ]
In the molecule of the title compound, C7H8IN, the methyl C, I and N atoms lie in the benzene ring plane. In the crystal structure, intermolecular N-H
N hydrogen bonds link the molecules in a stacked arrangement along the a axis.
The title compound, (I), was prepared by the literature method (Kajigaeshi et al., 1988). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in hexane (20 ml) and evaporating the solvent slowly at room temperature for about 7 d.
H atoms were positioned geometrically, with N—H = 0.86 Å (for NH2) and C—H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x= 1.2 for all other H atoms.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON10M (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2000).
![[Figure 1]](./hk2418fig1thm.gif)
| Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./hk2418fig2thm.gif)
| Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines. |
| C7H8IN | Dx = 1.976 Mg m−3 |
| Mr = 233.04 | Melting point: 360 K |
| Orthorhombic, P212121 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
| a = 5.5910 (11) Å | θ = 10–14º |
| b = 8.9410 (18) Å | µ = 4.00 mm−1 |
| c = 15.674 (3) Å | T = 294 (2) K |
| V = 783.5 (3) Å3 | Block, purple |
| Z = 4 | 0.20 × 0.10 × 0.10 mm |
| F000 = 440 |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.012 |
| Radiation source: fine-focus sealed tube | θmax = 26.0º |
| Monochromator: graphite | θmin = 2.6º |
| T = 294(2) K | h = 0→6 |
| ω/2θ scans | k = 0→11 |
| Absorption correction: ψ scan (North et al., 1968) | l = 0→19 |
| Tmin = 0.487, Tmax = 0.670 | 3 standard reflections |
| 917 measured reflections | every 120 min |
| 917 independent reflections | intensity decay: none |
| 737 reflections with I > 2σ(I) |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.1P)2 + 1.P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.151 | (Δ/σ)max < 0.001 |
| S = 1.04 | Δρmax = 0.51 e Å−3 |
| 917 reflections | Δρmin = −0.96 e Å−3 |
| 82 parameters | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with no Friedel pairs |
| Secondary atom site location: difference Fourier map | Flack parameter: −0.29 (13) |
| C7H8IN | V = 783.5 (3) Å3 |
| Mr = 233.04 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα |
| a = 5.5910 (11) Å | µ = 4.00 mm−1 |
| b = 8.9410 (18) Å | T = 294 (2) K |
| c = 15.674 (3) Å | 0.20 × 0.10 × 0.10 mm |
| Enraf–Nonius CAD-4 diffractometer | 737 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.012 |
| Tmin = 0.487, Tmax = 0.670 | 3 standard reflections |
| 917 measured reflections | every 120 min |
| 917 independent reflections | intensity decay: none |
| R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
| wR(F2) = 0.151 | Δρmax = 0.51 e Å−3 |
| S = 1.04 | Δρmin = −0.96 e Å−3 |
| 917 reflections | Absolute structure: Flack (1983), with no Friedel pairs |
| 82 parameters | Flack parameter: −0.29 (13) |
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. |
| x | y | z | Uiso*/Ueq | ||
| I | 0.01067 (18) | 0.20097 (9) | 0.23728 (5) | 0.0696 (4) | |
| N | 0.407 (2) | 0.6567 (10) | −0.0309 (8) | 0.063 (3) | |
| H0A | 0.3335 | 0.6711 | −0.0784 | 0.076* | |
| H0B | 0.5326 | 0.7081 | −0.0188 | 0.076* | |
| C1 | 0.1534 (18) | 0.3484 (11) | 0.1464 (7) | 0.044 (2) | |
| C2 | 0.360 (2) | 0.4273 (12) | 0.1643 (8) | 0.053 (3) | |
| H2A | 0.4425 | 0.4137 | 0.2152 | 0.063* | |
| C3 | 0.439 (2) | 0.5276 (13) | 0.1030 (7) | 0.054 (3) | |
| H3A | 0.5772 | 0.5825 | 0.1139 | 0.064* | |
| C4 | 0.322 (2) | 0.5491 (11) | 0.0269 (7) | 0.042 (2) | |
| C5 | 0.122 (2) | 0.4658 (11) | 0.0088 (7) | 0.045 (2) | |
| C6 | 0.028 (2) | 0.3671 (11) | 0.0701 (7) | 0.051 (3) | |
| H6A | −0.1143 | 0.3158 | 0.0601 | 0.062* | |
| C7 | −0.011 (2) | 0.4852 (13) | −0.0736 (7) | 0.059 (3) | |
| H7A | −0.1480 | 0.4207 | −0.0741 | 0.089* | |
| H7B | 0.0924 | 0.4599 | −0.1204 | 0.089* | |
| H7C | −0.0615 | 0.5873 | −0.0791 | 0.089* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| I | 0.0908 (7) | 0.0662 (5) | 0.0517 (5) | −0.0067 (5) | 0.0050 (5) | 0.0104 (3) |
| N | 0.061 (6) | 0.051 (5) | 0.078 (7) | −0.004 (5) | 0.007 (6) | 0.012 (5) |
| C1 | 0.048 (6) | 0.044 (5) | 0.038 (5) | 0.002 (5) | 0.011 (5) | −0.001 (4) |
| C2 | 0.056 (7) | 0.052 (6) | 0.050 (6) | −0.005 (5) | −0.005 (6) | −0.005 (5) |
| C3 | 0.041 (6) | 0.055 (7) | 0.064 (7) | −0.001 (5) | 0.001 (5) | −0.010 (6) |
| C4 | 0.040 (6) | 0.043 (6) | 0.043 (5) | 0.006 (4) | 0.009 (5) | −0.002 (4) |
| C5 | 0.058 (7) | 0.036 (5) | 0.040 (5) | 0.005 (5) | 0.002 (5) | 0.001 (4) |
| C6 | 0.056 (7) | 0.044 (5) | 0.054 (6) | −0.005 (6) | −0.001 (6) | −0.006 (4) |
| C7 | 0.063 (7) | 0.065 (6) | 0.050 (5) | 0.013 (9) | −0.009 (8) | −0.006 (5) |
| I—C1 | 2.099 (10) | C4—C5 | 1.374 (16) |
| N—H0A | 0.8600 | C4—N | 1.403 (13) |
| N—H0B | 0.8600 | C5—C6 | 1.408 (15) |
| C1—C2 | 1.383 (15) | C6—H6A | 0.9300 |
| C1—C6 | 1.397 (15) | C7—C5 | 1.500 (15) |
| C2—C3 | 1.386 (16) | C7—H7A | 0.9600 |
| C2—H2A | 0.9300 | C7—H7B | 0.9600 |
| C3—C4 | 1.375 (16) | C7—H7C | 0.9600 |
| C3—H3A | 0.9300 | ||
| C4—N—H0A | 120.0 | C3—C4—N | 119.7 (11) |
| C4—N—H0B | 120.0 | C4—C5—C6 | 120.3 (10) |
| H0A—N—H0B | 120.0 | C4—C5—C7 | 121.2 (10) |
| C2—C1—C6 | 122.2 (10) | C6—C5—C7 | 118.3 (11) |
| C2—C1—I | 120.0 (8) | C1—C6—C5 | 118.1 (10) |
| C6—C1—I | 117.7 (8) | C1—C6—H6A | 121.0 |
| C1—C2—C3 | 117.2 (10) | C5—C6—H6A | 121.0 |
| C1—C2—H2A | 121.4 | C5—C7—H7A | 109.5 |
| C3—C2—H2A | 121.4 | C5—C7—H7B | 109.5 |
| C4—C3—C2 | 122.7 (10) | H7A—C7—H7B | 109.5 |
| C4—C3—H3A | 118.6 | C5—C7—H7C | 109.5 |
| C2—C3—H3A | 118.6 | H7A—C7—H7C | 109.5 |
| C5—C4—C3 | 119.4 (10) | H7B—C7—H7C | 109.5 |
| C5—C4—N | 120.9 (11) | ||
| C6—C1—C2—C3 | 0.2 (16) | C3—C4—C5—C6 | 4.6 (16) |
| I—C1—C2—C3 | −177.3 (8) | N—C4—C5—C6 | −174.8 (9) |
| C2—C1—C6—C5 | 2.5 (16) | C3—C4—C5—C7 | −179.8 (10) |
| I—C1—C6—C5 | 180.0 (7) | N—C4—C5—C7 | 0.8 (15) |
| C1—C2—C3—C4 | −0.5 (17) | C4—C5—C6—C1 | −4.9 (16) |
| C2—C3—C4—C5 | −1.8 (17) | C7—C5—C6—C1 | 179.4 (10) |
| C2—C3—C4—N | 177.5 (10) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N—H0B···Ni | 0.86 | 2.54 | 3.397 (15) | 174 |
| Symmetry codes: (i) x+1/2, −y+3/2, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N—H0B···Ni | 0.86 | 2.54 | 3.397 (15) | 174 |
| Symmetry codes: (i) x+1/2, −y+3/2, −z. |
The authors thank the Center for Testing and Analysis, Nanjing University, for support.
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.
Bruker (2000). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.
Enraf–Nonius (1989). CAD-4 Software. Version 5.0. Enraf–Nonius, Delft, The Netherlands.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Kajigaeshi, S., Kakinami, T., Yamasaki, H., Fujisaki, S. & Okamoto, T. (1988). Bull. Chem. Soc. Jpn, 61, 600–602.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
The title compound, (I), contains amino and halogen groups, which can react with different groups to prepare various function organic compounds. It is a kind of aromatic organic intermediate that can be used for many fields such as aromatic conductive polymer, organometallic chemistry etc. (Kajigaeshi et al., 1988). We report herein its crystal structure.
In the molecule of (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The atoms I, N and C7 lie in the benzene ring plane.
In the crystal structure, intermolecular N—H···N hydrogen bonds (Table 1) link the molecules stacked along the a axis, (Fig. 2), in which they may be effective in the stabilization of the structure.