Acta Cryst. (2009). E65, o229 [ doi:10.1107/S1600536808043717 ]
In the title compound, C12H11N2+·I-, the aromatic rings are oriented at a dihedral angle of 73.40 (3)°. In the crystal structure, ![[pi]](/logos/entities/pi_rmgif.gif)
- contacts between the pyridine rings and the benzene and pyridine rings [centroid-centroid distances = 3.548 (3) and 4.211 (3) Å] may stabilize the structure.
For the preparation of the title compound, 1-aminopyridinium iodide (22.2 g, 0.10 mol) was dissolved in ethanol (20 ml), benzaldehyde(10.6 g, 0.10 mol) was added with stirring, and then the mixture was heated at reflux for 5 h. Upon cooling to room temperature, a precipitate formed, which was collected by filtration and washed with cold ethanol (2 X 10 ml) to obtain a yellow solid (yield; 21.7 g, 70%). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.
H atoms were positioned geometrically, with C-H = 0.93 Å for aromatic and methine H and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./hk2601fig1thm.gif)
| Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
| C12H11N2+·I− | F(000) = 600 |
| Mr = 310.13 | Dx = 1.706 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
| a = 10.5722 (17) Å | θ = 2.1–25.3° |
| b = 7.8219 (13) Å | µ = 2.62 mm−1 |
| c = 15.386 (3) Å | T = 291 K |
| β = 108.354 (2)° | Block, yellow |
| V = 1207.6 (4) Å3 | 0.13 × 0.12 × 0.10 mm |
| Z = 4 |
| Enraf–Nonius CAD-4 diffractometer | 1713 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.067 |
| graphite | θmax = 25.0°, θmin = 2.8° |
| ω/2θ scans | h = −12→12 |
| Absorption correction: ψ scan (North et al., 1968) | k = −9→7 |
| Tmin = 0.727, Tmax = 0.780 | l = −18→18 |
| 5768 measured reflections | 3 standard reflections every 120 min |
| 2133 independent reflections | intensity decay: none |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.075 | H-atom parameters constrained |
| S = 0.94 | w = 1/[σ2(Fo2) + (0.0365P)2] where P = (Fo2 + 2Fc2)/3 |
| 2133 reflections | (Δ/σ)max = 0.001 |
| 136 parameters | Δρmax = 0.50 e Å−3 |
| 0 restraints | Δρmin = −0.52 e Å−3 |
| C12H11N2+·I− | V = 1207.6 (4) Å3 |
| Mr = 310.13 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 10.5722 (17) Å | µ = 2.62 mm−1 |
| b = 7.8219 (13) Å | T = 291 K |
| c = 15.386 (3) Å | 0.13 × 0.12 × 0.10 mm |
| β = 108.354 (2)° |
| Enraf–Nonius CAD-4 diffractometer | 1713 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.067 |
| Tmin = 0.727, Tmax = 0.780 | θmax = 25.0° |
| 5768 measured reflections | 3 standard reflections every 120 min |
| 2133 independent reflections | intensity decay: none |
| R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
| wR(F2) = 0.075 | Δρmax = 0.50 e Å−3 |
| S = 0.94 | Δρmin = −0.52 e Å−3 |
| 2133 reflections | Absolute structure: ? |
| 136 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| I1 | 0.36542 (2) | 0.37261 (3) | 0.175113 (16) | 0.05509 (13) | |
| N1 | 0.2501 (3) | 0.8944 (3) | 0.03899 (19) | 0.0462 (7) | |
| N2 | 0.1744 (3) | 0.8956 (3) | 0.10105 (19) | 0.0482 (7) | |
| C1 | 0.3602 (4) | 0.7989 (5) | 0.0544 (3) | 0.0543 (9) | |
| H1 | 0.3942 | 0.7393 | 0.1091 | 0.065* | |
| C2 | 0.4222 (4) | 0.7904 (5) | −0.0117 (3) | 0.0597 (10) | |
| H2 | 0.4975 | 0.7225 | −0.0024 | 0.072* | |
| C3 | 0.3734 (4) | 0.8812 (5) | −0.0909 (3) | 0.0586 (10) | |
| H3 | 0.4162 | 0.8775 | −0.1353 | 0.070* | |
| C4 | 0.2612 (4) | 0.9776 (6) | −0.1045 (2) | 0.0633 (10) | |
| H4 | 0.2274 | 1.0402 | −0.1582 | 0.076* | |
| C5 | 0.1982 (4) | 0.9821 (5) | −0.0388 (2) | 0.0617 (10) | |
| H5 | 0.1205 | 1.0454 | −0.0484 | 0.074* | |
| C6 | 0.2447 (3) | 0.9324 (4) | 0.1829 (2) | 0.0439 (8) | |
| H6 | 0.3347 | 0.9579 | 0.1961 | 0.053* | |
| C7 | 0.1831 (3) | 0.9341 (5) | 0.2553 (2) | 0.0447 (8) | |
| C8 | 0.2456 (4) | 1.0226 (5) | 0.3354 (2) | 0.0584 (9) | |
| H8 | 0.3250 | 1.0802 | 0.3419 | 0.070* | |
| C9 | 0.0654 (4) | 0.8452 (5) | 0.2465 (3) | 0.0566 (10) | |
| H9 | 0.0240 | 0.7838 | 0.1934 | 0.068* | |
| C10 | 0.0110 (4) | 0.8488 (5) | 0.3166 (3) | 0.0687 (12) | |
| H10 | −0.0678 | 0.7902 | 0.3109 | 0.082* | |
| C11 | 0.0729 (5) | 0.9391 (6) | 0.3955 (3) | 0.0748 (13) | |
| H11 | 0.0352 | 0.9419 | 0.4425 | 0.090* | |
| C12 | 0.1899 (5) | 1.0252 (6) | 0.4051 (3) | 0.0716 (12) | |
| H12 | 0.2315 | 1.0851 | 0.4588 | 0.086* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| I1 | 0.05786 (18) | 0.0622 (2) | 0.04976 (17) | −0.00118 (11) | 0.02344 (12) | 0.00535 (11) |
| N1 | 0.0537 (16) | 0.0507 (17) | 0.0363 (15) | −0.0039 (13) | 0.0172 (13) | −0.0040 (13) |
| N2 | 0.0509 (16) | 0.0610 (18) | 0.0355 (15) | −0.0047 (13) | 0.0176 (13) | −0.0016 (14) |
| C1 | 0.064 (2) | 0.050 (2) | 0.052 (2) | 0.0022 (18) | 0.0222 (18) | 0.0048 (18) |
| C2 | 0.066 (2) | 0.055 (2) | 0.067 (3) | 0.0024 (19) | 0.034 (2) | −0.005 (2) |
| C3 | 0.069 (2) | 0.066 (2) | 0.050 (2) | −0.012 (2) | 0.0314 (19) | −0.013 (2) |
| C4 | 0.067 (2) | 0.082 (3) | 0.0402 (19) | 0.001 (2) | 0.0172 (18) | 0.010 (2) |
| C5 | 0.061 (2) | 0.083 (3) | 0.043 (2) | 0.010 (2) | 0.0183 (17) | 0.004 (2) |
| C6 | 0.0466 (18) | 0.0441 (19) | 0.0398 (19) | 0.0008 (14) | 0.0118 (15) | 0.0004 (15) |
| C7 | 0.0471 (19) | 0.0505 (19) | 0.0351 (18) | 0.0047 (15) | 0.0107 (15) | 0.0027 (16) |
| C8 | 0.061 (2) | 0.070 (3) | 0.0405 (19) | 0.0007 (19) | 0.0111 (17) | −0.0024 (19) |
| C9 | 0.054 (2) | 0.068 (3) | 0.050 (2) | −0.0020 (17) | 0.0190 (18) | 0.0039 (18) |
| C10 | 0.067 (3) | 0.078 (3) | 0.074 (3) | 0.003 (2) | 0.040 (2) | 0.012 (2) |
| C11 | 0.097 (3) | 0.082 (3) | 0.062 (3) | 0.033 (3) | 0.049 (3) | 0.019 (3) |
| C12 | 0.098 (3) | 0.078 (3) | 0.039 (2) | 0.015 (3) | 0.022 (2) | −0.004 (2) |
| N1—N2 | 1.426 (4) | C6—C7 | 1.457 (4) |
| C1—N1 | 1.340 (4) | C6—H6 | 0.9300 |
| C1—C2 | 1.375 (5) | C7—C8 | 1.385 (5) |
| C1—H1 | 0.9300 | C7—C9 | 1.394 (5) |
| C2—C3 | 1.364 (5) | C8—C12 | 1.377 (5) |
| C2—H2 | 0.9300 | C8—H8 | 0.9300 |
| C3—C4 | 1.365 (5) | C9—C10 | 1.374 (6) |
| C3—H3 | 0.9300 | C9—H9 | 0.9300 |
| C4—C5 | 1.374 (5) | C10—C11 | 1.378 (7) |
| C4—H4 | 0.9300 | C10—H10 | 0.9300 |
| C5—N1 | 1.339 (4) | C11—C12 | 1.375 (6) |
| C5—H5 | 0.9300 | C11—H11 | 0.9300 |
| C6—N2 | 1.277 (4) | C12—H12 | 0.9300 |
| C5—N1—C1 | 122.2 (3) | N2—C6—H6 | 120.2 |
| C5—N1—N2 | 116.0 (3) | C7—C6—H6 | 120.2 |
| C1—N1—N2 | 121.6 (3) | C8—C7—C9 | 119.8 (3) |
| C6—N2—N1 | 112.8 (3) | C8—C7—C6 | 118.8 (3) |
| N1—C1—C2 | 119.1 (4) | C9—C7—C6 | 121.4 (3) |
| N1—C1—H1 | 120.4 | C12—C8—C7 | 120.0 (4) |
| C2—C1—H1 | 120.4 | C12—C8—H8 | 120.0 |
| C3—C2—C1 | 120.1 (4) | C7—C8—H8 | 120.0 |
| C3—C2—H2 | 119.9 | C10—C9—C7 | 119.7 (4) |
| C1—C2—H2 | 119.9 | C10—C9—H9 | 120.1 |
| C2—C3—C4 | 119.3 (4) | C7—C9—H9 | 120.1 |
| C2—C3—H3 | 120.3 | C9—C10—C11 | 120.1 (4) |
| C4—C3—H3 | 120.3 | C9—C10—H10 | 120.0 |
| C3—C4—C5 | 120.1 (4) | C11—C10—H10 | 120.0 |
| C3—C4—H4 | 119.9 | C12—C11—C10 | 120.5 (4) |
| C5—C4—H4 | 119.9 | C12—C11—H11 | 119.7 |
| N1—C5—C4 | 119.2 (4) | C10—C11—H11 | 119.7 |
| N1—C5—H5 | 120.4 | C11—C12—C8 | 119.9 (4) |
| C4—C5—H5 | 120.4 | C11—C12—H12 | 120.0 |
| N2—C6—C7 | 119.7 (3) | C8—C12—H12 | 120.0 |
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
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Some derivatives of 1-aminopyidium iodide are important chemical materials. We report herein the crystal structure of the title compound.
In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N1/C1-C5) and B (C7-C12) are, of course, planar, and they are oriented at a dihedral angle of 73.40 (3)°.
In the crystal structure, π-π contacts between the pyridine and the benzene rings and the pyridine rings, Cg1—Cg2i and Cg1—Cg1ii [symmetry codes: (i) x, 3/2 - y, z - 1/2; (ii) 1 - x, 2 - y, -z, where Cg1 and Cg2 are centroids of the rings A (N1/C1-C5) and B (C7-C12) , respectively] may stabilize the structure, with centroid-centroid distances of 3.548 (3) Å and 4.211 (3) Å.