


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808021569/hk2492sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808021569/hk2492Isup2.hkl |
CCDC reference: 700521
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean
(C-C) = 0.017 Å
- R factor = 0.049
- wR factor = 0.125
- Data-to-parameter ratio = 9.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.05 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 17
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.27 From the CIF: _reflns_number_total 1408 Count of symmetry unique reflns 1413 Completeness (_total/calc) 99.65% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the preparation of the title compound, 1-aminopyridinium iodide (22.2 g, 0.10 mol) was dissolved in ethanol (20 ml). 4-Methylbenzaldehyde (32.4 g, 0.1 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; 38 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 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C13H13N2+·I− | F(000) = 632 |
Mr = 324.15 | Dx = 1.612 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 7.1690 (14) Å | θ = 2.1–25.3° |
b = 12.399 (3) Å | µ = 2.37 mm−1 |
c = 15.026 (3) Å | T = 291 K |
V = 1335.6 (5) Å3 | Block, yellow |
Z = 4 | 0.30 × 0.10 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 1015 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.3°, θmin = 2.1° |
ω/2θ scans | h = 0→8 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→14 |
Tmin = 0.536, Tmax = 0.797 | l = 0→18 |
1408 measured reflections | 3 standard reflections every 120 min |
1408 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.581P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1408 reflections | Δρmax = 1.10 e Å−3 |
146 parameters | Δρmin = −0.54 e Å−3 |
0 restraints | Absolute structure: Flack (1983), with no Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (10) |
C13H13N2+·I− | V = 1335.6 (5) Å3 |
Mr = 324.15 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.1690 (14) Å | µ = 2.37 mm−1 |
b = 12.399 (3) Å | T = 291 K |
c = 15.026 (3) Å | 0.30 × 0.10 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 1015 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.000 |
Tmin = 0.536, Tmax = 0.797 | 3 standard reflections every 120 min |
1408 measured reflections | intensity decay: none |
1408 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.125 | Δρmax = 1.10 e Å−3 |
S = 1.08 | Δρmin = −0.54 e Å−3 |
1408 reflections | Absolute structure: Flack (1983), with no Friedel pairs |
146 parameters | Absolute structure parameter: 0.05 (10) |
0 restraints |
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 > 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. |
x | y | z | Uiso*/Ueq | ||
I | 0.63765 (9) | 0.75120 (8) | 0.67606 (4) | 0.0632 (3) | |
N1 | 0.1554 (13) | 0.6174 (7) | 0.7189 (6) | 0.049 (2) | |
N2 | 0.1485 (13) | 0.6612 (8) | 0.8065 (6) | 0.051 (2) | |
C1 | 0.241 (2) | 1.0008 (11) | 1.1391 (8) | 0.068 (4) | |
H1A | 0.3685 | 1.0169 | 1.1541 | 0.102* | |
H1B | 0.1854 | 0.9596 | 1.1862 | 0.102* | |
H1C | 0.1735 | 1.0669 | 1.1313 | 0.102* | |
C2 | 0.2358 (15) | 0.9358 (10) | 1.0529 (7) | 0.053 (3) | |
C3 | 0.1465 (17) | 0.8349 (9) | 1.0519 (7) | 0.055 (3) | |
H3 | 0.0964 | 0.8069 | 1.1041 | 0.065* | |
C4 | 0.1329 (14) | 0.7771 (8) | 0.9731 (7) | 0.048 (3) | |
H4 | 0.0746 | 0.7101 | 0.9727 | 0.058* | |
C5 | 0.2057 (14) | 0.8187 (9) | 0.8955 (7) | 0.044 (3) | |
C6 | 0.2865 (17) | 0.9199 (8) | 0.8960 (8) | 0.055 (3) | |
H6 | 0.3312 | 0.9490 | 0.8431 | 0.066* | |
C7 | 0.3023 (16) | 0.9792 (10) | 0.9746 (8) | 0.059 (3) | |
H7 | 0.3570 | 1.0472 | 0.9742 | 0.071* | |
C8 | 0.2037 (13) | 0.7578 (10) | 0.8115 (6) | 0.051 (3) | |
H8 | 0.2447 | 0.7918 | 0.7599 | 0.062* | |
C9 | 0.2109 (17) | 0.5139 (9) | 0.7163 (9) | 0.061 (3) | |
H9 | 0.2361 | 0.4769 | 0.7688 | 0.073* | |
C10 | 0.230 (2) | 0.4624 (11) | 0.6341 (12) | 0.081 (5) | |
H10 | 0.2715 | 0.3914 | 0.6305 | 0.097* | |
C11 | 0.1874 (17) | 0.5193 (13) | 0.5595 (9) | 0.072 (4) | |
H11 | 0.1953 | 0.4859 | 0.5042 | 0.087* | |
C12 | 0.1332 (19) | 0.6237 (12) | 0.5642 (8) | 0.070 (4) | |
H12 | 0.1104 | 0.6627 | 0.5125 | 0.084* | |
C13 | 0.1126 (18) | 0.6708 (11) | 0.6443 (8) | 0.065 (3) | |
H13 | 0.0681 | 0.7411 | 0.6478 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.078 (10) | 0.073 (8) | 0.054 (7) | 0.006 (8) | −0.006 (8) | −0.019 (7) |
C2 | 0.046 (7) | 0.058 (8) | 0.055 (7) | 0.013 (6) | −0.012 (6) | 0.001 (6) |
C3 | 0.068 (8) | 0.046 (6) | 0.050 (7) | 0.009 (7) | 0.016 (6) | 0.011 (5) |
C4 | 0.052 (6) | 0.044 (7) | 0.048 (5) | 0.002 (5) | −0.007 (5) | 0.001 (5) |
C5 | 0.033 (5) | 0.060 (7) | 0.038 (6) | 0.007 (5) | 0.006 (5) | 0.006 (5) |
C6 | 0.059 (7) | 0.043 (6) | 0.062 (7) | −0.007 (6) | 0.020 (6) | 0.001 (6) |
C7 | 0.054 (7) | 0.064 (8) | 0.059 (7) | 0.007 (6) | 0.002 (7) | 0.000 (7) |
C8 | 0.039 (4) | 0.073 (8) | 0.042 (5) | 0.013 (8) | 0.001 (4) | 0.011 (8) |
C9 | 0.068 (8) | 0.055 (8) | 0.061 (7) | −0.011 (7) | −0.013 (7) | 0.007 (6) |
C10 | 0.070 (10) | 0.064 (9) | 0.108 (12) | −0.016 (9) | 0.011 (10) | −0.026 (10) |
C11 | 0.046 (8) | 0.117 (13) | 0.053 (8) | −0.017 (9) | 0.015 (6) | −0.025 (9) |
C12 | 0.072 (9) | 0.094 (11) | 0.044 (7) | −0.016 (9) | −0.018 (7) | 0.001 (7) |
C13 | 0.064 (8) | 0.075 (8) | 0.054 (7) | 0.010 (8) | 0.007 (7) | 0.009 (7) |
I | 0.0631 (5) | 0.0721 (5) | 0.0544 (4) | 0.0063 (8) | 0.0064 (4) | −0.0020 (6) |
N1 | 0.044 (5) | 0.050 (5) | 0.053 (5) | 0.000 (5) | 0.006 (5) | 0.001 (5) |
N2 | 0.049 (5) | 0.054 (5) | 0.049 (5) | −0.012 (5) | 0.021 (5) | −0.005 (4) |
C1—C2 | 1.526 (15) | C8—N2 | 1.264 (13) |
C1—H1A | 0.9600 | C8—H8 | 0.9300 |
C1—H1B | 0.9600 | C9—N1 | 1.344 (13) |
C1—H1C | 0.9600 | C9—C10 | 1.398 (17) |
C2—C7 | 1.379 (15) | C9—H9 | 0.9300 |
C2—C3 | 1.405 (16) | C10—C11 | 1.360 (19) |
C3—C4 | 1.387 (15) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—C12 | 1.353 (17) |
C4—C5 | 1.379 (13) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C12—C13 | 1.345 (16) |
C5—C6 | 1.382 (14) | C12—H12 | 0.9300 |
C5—C8 | 1.471 (13) | C13—N1 | 1.338 (14) |
C6—C7 | 1.396 (15) | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | N1—N2 | 1.425 (11) |
C7—H7 | 0.9300 | ||
C2—C1—H1A | 109.5 | C6—C7—H7 | 120.4 |
C2—C1—H1B | 109.5 | N2—C8—C5 | 122.7 (9) |
H1A—C1—H1B | 109.5 | N2—C8—H8 | 118.6 |
C2—C1—H1C | 109.5 | C5—C8—H8 | 118.6 |
H1A—C1—H1C | 109.5 | N1—C9—C10 | 119.4 (12) |
H1B—C1—H1C | 109.5 | N1—C9—H9 | 120.3 |
C7—C2—C3 | 119.7 (11) | C10—C9—H9 | 120.3 |
C7—C2—C1 | 120.6 (12) | C11—C10—C9 | 118.0 (12) |
C3—C2—C1 | 119.4 (12) | C11—C10—H10 | 121.0 |
C4—C3—C2 | 120.1 (10) | C9—C10—H10 | 121.0 |
C4—C3—H3 | 120.0 | C12—C11—C10 | 121.2 (13) |
C2—C3—H3 | 120.0 | C12—C11—H11 | 119.4 |
C5—C4—C3 | 120.2 (10) | C10—C11—H11 | 119.4 |
C5—C4—H4 | 119.9 | C13—C12—C11 | 119.6 (13) |
C3—C4—H4 | 119.9 | C13—C12—H12 | 120.2 |
C4—C5—C6 | 119.6 (10) | C11—C12—H12 | 120.2 |
C4—C5—C8 | 122.0 (10) | N1—C13—C12 | 120.6 (12) |
C6—C5—C8 | 118.4 (10) | N1—C13—H13 | 119.7 |
C5—C6—C7 | 121.1 (11) | C12—C13—H13 | 119.7 |
C5—C6—H6 | 119.4 | C13—N1—C9 | 121.1 (11) |
C7—C6—H6 | 119.4 | C13—N1—N2 | 125.3 (9) |
C2—C7—C6 | 119.2 (11) | C9—N1—N2 | 113.6 (10) |
C2—C7—H7 | 120.4 | C8—N2—N1 | 113.9 (9) |
C7—C2—C3—C4 | 2.9 (16) | N1—C9—C10—C11 | −2 (2) |
C1—C2—C3—C4 | 177.1 (11) | C9—C10—C11—C12 | 2 (2) |
C2—C3—C4—C5 | −0.5 (17) | C10—C11—C12—C13 | −3 (2) |
C3—C4—C5—C6 | −2.2 (16) | C11—C12—C13—N1 | 4 (2) |
C3—C4—C5—C8 | 176.6 (10) | C12—C13—N1—C9 | −3.4 (19) |
C4—C5—C6—C7 | 2.5 (17) | C12—C13—N1—N2 | 176.5 (11) |
C8—C5—C6—C7 | −176.3 (10) | C10—C9—N1—C13 | 2.3 (18) |
C3—C2—C7—C6 | −2.6 (17) | C10—C9—N1—N2 | −177.6 (11) |
C1—C2—C7—C6 | −176.7 (12) | C5—C8—N2—N1 | 179.2 (9) |
C5—C6—C7—C2 | 0.0 (18) | C13—N1—N2—C8 | −38.8 (15) |
C4—C5—C8—N2 | −5.4 (16) | C9—N1—N2—C8 | 141.1 (10) |
C6—C5—C8—N2 | 173.3 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Ii | 0.93 | 3.06 | 3.795 (12) | 138 |
C12—H12···Iii | 0.93 | 3.03 | 3.929 (13) | 162 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H13N2+·I− |
Mr | 324.15 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 291 |
a, b, c (Å) | 7.1690 (14), 12.399 (3), 15.026 (3) |
V (Å3) | 1335.6 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.37 |
Crystal size (mm) | 0.30 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.536, 0.797 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1408, 1408, 1015 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.125, 1.08 |
No. of reflections | 1408 |
No. of parameters | 146 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.10, −0.54 |
Absolute structure | Flack (1983), with no Friedel pairs |
Absolute structure parameter | 0.05 (10) |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Ii | 0.93 | 3.06 | 3.795 (12) | 138.00 |
C12—H12···Iii | 0.93 | 3.03 | 3.929 (13) | 162.00 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, −z+1. |
Some derivatives of 1-aminopyidinium iodide is 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 (C2-C7) and B (N1/C9-C13) are, of course, planar and they are oriented at a dihedral angle of A/B = 45.78 (3)°.
In the crystal structure, weak intermolecular C-H···I hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.