organic compounds
1,4-Dimethylpyridinium iodide
a325 Science Center, Fredonia State University of New York, Fredonia 14063, USA
*Correspondence e-mail: cardenas@fredonia.edu
The title organic salt, C7H10N+·I−, was synthesized from a mixture of 4-methylpyridine and iodomethane in 2-propanol. It crystallized with three independent 1,4-dimethylpyridinium cations and three independent iodide anions in the In the crystal, there are no significant intermolecular interactions present.
Keywords: crystal structure; organic salt; pyridinium; iodide.
CCDC reference: 1533238
Structure description
The title organic salt was synthesized from a mixture of 4-methylpyridine and iodomethane in 2-propanol. It crystallized with three independent 1,4-dimethylpyridinium cations and three independent iodide anions in the ). In the crystal (Fig. 2), there are no significant intermolecular interactions present. The H⋯I distances vary between ca 3.06 and 3.16 Å.
(Fig. 1The crystal structures of the triiodide (Tan et al., 2005) and the heptaiodide (Herbstein et al., 1985) salts of 1,4-dimethylpyridinium have been reported.
Synthesis and crystallization
The title molecular salt was synthesized (Ault, 1997) from a mixture of 4-methylpyridine (0.10 mol, 10.0 mL) and iodomethane (0.10 mol, 6.2 mL) in 2-propanol (20 mL) (Fig. 3). The solution was heated to 323 K using a water bath to initiate the reaction. Upon reaching 323 K, the solution was removed from the water bath and allowed to cool to room temperature. After 30 min, the colorless block-like crystals that formed were collected by vacuum filtration (yield: 21.0 g, 89%).
Refinement
Crystal data, data collection and .
details are summarized in Table 1Structural data
CCDC reference: 1533238
https://doi.org/10.1107/S2414314617002693/su4130sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002693/su4130Isup2.hkl
Data collection: APEX2 (Bruker, 2015); cell
SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C7H10N+·I− | F(000) = 1344 |
Mr = 235.06 | Dx = 1.786 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8301 (6) Å | Cell parameters from 9919 reflections |
b = 19.7170 (9) Å | θ = 3.0–27.9° |
c = 10.2121 (5) Å | µ = 3.59 mm−1 |
β = 109.642 (1)° | T = 150 K |
V = 2622.7 (2) Å3 | Block, clear colourless |
Z = 12 | 0.5 × 0.5 × 0.3 mm |
Bruker APEX-II CCD diffractometer | 5401 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.019 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | θmax = 27.9°, θmin = 3.0° |
Tmin = 0.476, Tmax = 0.746 | h = −18→16 |
16106 measured reflections | k = −25→22 |
5933 independent reflections | l = −10→13 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.021 | w = 1/[σ2(Fo2) + (0.013P)2 + 2.567P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.048 | (Δ/σ)max = 0.002 |
S = 1.14 | Δρmax = 0.51 e Å−3 |
5933 reflections | Δρmin = −0.49 e Å−3 |
251 parameters | Extinction correction: (SHELXL2014; Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00371 (9) |
Primary atom site location: heavy-atom method |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.17247 (17) | 0.06045 (10) | 0.8272 (2) | 0.0280 (4) | |
C2A | 0.26459 (19) | 0.04078 (13) | 0.9118 (3) | 0.0293 (5) | |
H2A | 0.3244 | 0.0639 | 0.9101 | 0.035* | |
C3A | 0.27371 (19) | −0.01251 (13) | 1.0013 (3) | 0.0282 (5) | |
H3A | 0.3399 | −0.0261 | 1.0603 | 0.034* | |
C4A | 0.18709 (19) | −0.04710 (12) | 1.0073 (3) | 0.0254 (5) | |
C5A | 0.09273 (19) | −0.02508 (13) | 0.9167 (3) | 0.0323 (6) | |
H5A | 0.0316 | −0.0474 | 0.9156 | 0.039* | |
C6A | 0.0873 (2) | 0.02837 (14) | 0.8291 (3) | 0.0343 (6) | |
H6A | 0.0221 | 0.0431 | 0.7686 | 0.041* | |
C7A | 0.1643 (3) | 0.11948 (14) | 0.7343 (3) | 0.0425 (7) | |
H7AA | 0.2303 | 0.1269 | 0.7208 | 0.064* | |
H7AB | 0.1458 | 0.1599 | 0.7765 | 0.064* | |
H7AC | 0.1112 | 0.1107 | 0.6443 | 0.064* | |
C8A | 0.1962 (2) | −0.10450 (14) | 1.1067 (3) | 0.0385 (6) | |
H8AA | 0.1373 | −0.1350 | 1.0699 | 0.058* | |
H8AB | 0.1974 | −0.0865 | 1.1967 | 0.058* | |
H8AC | 0.2597 | −0.1296 | 1.1187 | 0.058* | |
N1B | 0.34851 (16) | 0.14589 (11) | 0.3646 (2) | 0.0282 (4) | |
C2B | 0.37389 (18) | 0.17934 (12) | 0.2661 (3) | 0.0282 (5) | |
H2B | 0.3472 | 0.2235 | 0.2388 | 0.034* | |
C3B | 0.43849 (18) | 0.15008 (12) | 0.2045 (3) | 0.0265 (5) | |
H3B | 0.4561 | 0.1743 | 0.1353 | 0.032* | |
C4B | 0.47783 (18) | 0.08550 (11) | 0.2429 (2) | 0.0228 (5) | |
C5B | 0.4466 (2) | 0.05136 (13) | 0.3414 (3) | 0.0320 (6) | |
H5B | 0.4693 | 0.0062 | 0.3669 | 0.038* | |
C6B | 0.3831 (2) | 0.08253 (14) | 0.4018 (3) | 0.0351 (6) | |
H6B | 0.3636 | 0.0592 | 0.4704 | 0.042* | |
C7B | 0.2809 (2) | 0.17861 (17) | 0.4316 (3) | 0.0432 (7) | |
H7BA | 0.2236 | 0.1483 | 0.4262 | 0.065* | |
H7BB | 0.2542 | 0.2212 | 0.3837 | 0.065* | |
H7BC | 0.3202 | 0.1880 | 0.5293 | 0.065* | |
C8B | 0.5518 (2) | 0.05338 (13) | 0.1828 (3) | 0.0299 (5) | |
H8BA | 0.5324 | 0.0059 | 0.1595 | 0.045* | |
H8BB | 0.6213 | 0.0554 | 0.2510 | 0.045* | |
H8BC | 0.5501 | 0.0779 | 0.0985 | 0.045* | |
N1C | 0.89692 (15) | 0.18673 (9) | 0.2697 (2) | 0.0235 (4) | |
C2C | 0.91494 (19) | 0.24514 (12) | 0.2131 (3) | 0.0261 (5) | |
H2C | 0.9836 | 0.2584 | 0.2264 | 0.031* | |
C3C | 0.83548 (19) | 0.28570 (12) | 0.1369 (3) | 0.0260 (5) | |
H3C | 0.8496 | 0.3266 | 0.0977 | 0.031* | |
C4C | 0.73442 (19) | 0.26743 (12) | 0.1164 (3) | 0.0258 (5) | |
C5C | 0.7189 (2) | 0.20670 (15) | 0.1763 (3) | 0.0397 (7) | |
H5C | 0.6509 | 0.1923 | 0.1642 | 0.048* | |
C6C | 0.8000 (2) | 0.16742 (14) | 0.2523 (3) | 0.0348 (6) | |
H6C | 0.7878 | 0.1264 | 0.2929 | 0.042* | |
C7C | 0.9849 (2) | 0.14490 (13) | 0.3522 (3) | 0.0309 (5) | |
H7CA | 0.9597 | 0.1042 | 0.3854 | 0.046* | |
H7CB | 1.0280 | 0.1712 | 0.4320 | 0.046* | |
H7CC | 1.0255 | 0.1316 | 0.2940 | 0.046* | |
C8C | 0.6457 (2) | 0.31053 (14) | 0.0333 (3) | 0.0365 (6) | |
H8CA | 0.6045 | 0.3231 | 0.0911 | 0.055* | |
H8CB | 0.6030 | 0.2850 | −0.0479 | 0.055* | |
H8CC | 0.6715 | 0.3517 | 0.0024 | 0.055* | |
I1 | 0.10438 (2) | 0.18819 (2) | 0.05002 (2) | 0.02898 (5) | |
I2 | 0.48598 (2) | 0.14790 (2) | 0.80737 (2) | 0.03174 (5) | |
I3 | 0.82578 (2) | 0.01901 (2) | 0.52125 (2) | 0.02898 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0402 (12) | 0.0249 (10) | 0.0194 (10) | 0.0074 (9) | 0.0107 (10) | −0.0014 (8) |
C2A | 0.0261 (12) | 0.0309 (12) | 0.0334 (14) | −0.0016 (10) | 0.0133 (11) | −0.0008 (10) |
C3A | 0.0203 (11) | 0.0326 (13) | 0.0291 (13) | 0.0001 (9) | 0.0049 (11) | 0.0024 (10) |
C4A | 0.0277 (12) | 0.0249 (11) | 0.0243 (12) | −0.0017 (9) | 0.0097 (11) | −0.0063 (9) |
C5A | 0.0222 (12) | 0.0360 (14) | 0.0376 (15) | −0.0056 (10) | 0.0088 (12) | −0.0090 (11) |
C6A | 0.0251 (12) | 0.0395 (14) | 0.0298 (14) | 0.0071 (10) | −0.0021 (12) | −0.0059 (11) |
C7A | 0.070 (2) | 0.0321 (14) | 0.0283 (14) | 0.0153 (14) | 0.0203 (15) | 0.0070 (11) |
C8A | 0.0462 (17) | 0.0357 (14) | 0.0347 (14) | −0.0042 (12) | 0.0151 (14) | 0.0045 (11) |
N1B | 0.0221 (10) | 0.0379 (12) | 0.0217 (10) | 0.0014 (8) | 0.0036 (9) | −0.0037 (8) |
C2B | 0.0226 (11) | 0.0247 (12) | 0.0354 (14) | −0.0015 (9) | 0.0072 (11) | 0.0010 (10) |
C3B | 0.0233 (11) | 0.0236 (11) | 0.0321 (13) | −0.0038 (9) | 0.0088 (11) | 0.0060 (9) |
C4B | 0.0222 (11) | 0.0227 (11) | 0.0197 (11) | −0.0042 (8) | 0.0020 (10) | −0.0017 (8) |
C5B | 0.0381 (14) | 0.0269 (12) | 0.0308 (13) | 0.0049 (10) | 0.0113 (12) | 0.0085 (10) |
C6B | 0.0377 (15) | 0.0409 (15) | 0.0284 (13) | 0.0040 (11) | 0.0132 (13) | 0.0112 (11) |
C7B | 0.0339 (15) | 0.068 (2) | 0.0291 (14) | 0.0137 (14) | 0.0118 (13) | −0.0059 (13) |
C8B | 0.0298 (12) | 0.0278 (12) | 0.0321 (13) | 0.0022 (10) | 0.0102 (11) | −0.0001 (10) |
N1C | 0.0248 (10) | 0.0216 (9) | 0.0220 (10) | −0.0003 (7) | 0.0050 (9) | 0.0002 (7) |
C2C | 0.0267 (12) | 0.0240 (11) | 0.0299 (12) | −0.0033 (9) | 0.0124 (11) | 0.0010 (9) |
C3C | 0.0295 (12) | 0.0220 (11) | 0.0276 (12) | −0.0015 (9) | 0.0110 (11) | 0.0023 (9) |
C4C | 0.0264 (12) | 0.0247 (11) | 0.0237 (12) | −0.0003 (9) | 0.0051 (10) | −0.0026 (9) |
C5C | 0.0230 (12) | 0.0405 (15) | 0.0497 (18) | −0.0088 (11) | 0.0044 (13) | 0.0111 (13) |
C6C | 0.0273 (13) | 0.0316 (13) | 0.0406 (15) | −0.0098 (10) | 0.0049 (12) | 0.0105 (11) |
C7C | 0.0270 (12) | 0.0280 (12) | 0.0332 (14) | 0.0030 (10) | 0.0042 (11) | 0.0055 (10) |
C8C | 0.0286 (13) | 0.0349 (14) | 0.0394 (15) | 0.0040 (11) | 0.0026 (13) | 0.0035 (11) |
I1 | 0.03136 (9) | 0.03198 (9) | 0.02415 (9) | −0.00129 (6) | 0.01007 (7) | −0.00118 (6) |
I2 | 0.03101 (9) | 0.02680 (9) | 0.03405 (10) | 0.00249 (6) | 0.00652 (8) | 0.00621 (6) |
I3 | 0.03280 (9) | 0.02248 (8) | 0.02966 (9) | 0.00116 (6) | 0.00787 (7) | −0.00018 (6) |
N1A—C2A | 1.334 (3) | C5B—H5B | 0.9500 |
N1A—C6A | 1.343 (4) | C5B—C6B | 1.376 (4) |
N1A—C7A | 1.481 (3) | C6B—H6B | 0.9500 |
C2A—H2A | 0.9500 | C7B—H7BA | 0.9800 |
C2A—C3A | 1.370 (4) | C7B—H7BB | 0.9800 |
C3A—H3A | 0.9500 | C7B—H7BC | 0.9800 |
C3A—C4A | 1.397 (3) | C8B—H8BA | 0.9800 |
C4A—C5A | 1.391 (4) | C8B—H8BB | 0.9800 |
C4A—C8A | 1.498 (4) | C8B—H8BC | 0.9800 |
C5A—H5A | 0.9500 | N1C—C2C | 1.349 (3) |
C5A—C6A | 1.368 (4) | N1C—C6C | 1.347 (3) |
C6A—H6A | 0.9500 | N1C—C7C | 1.477 (3) |
C7A—H7AA | 0.9800 | C2C—H2C | 0.9500 |
C7A—H7AB | 0.9800 | C2C—C3C | 1.371 (3) |
C7A—H7AC | 0.9800 | C3C—H3C | 0.9500 |
C8A—H8AA | 0.9800 | C3C—C4C | 1.389 (3) |
C8A—H8AB | 0.9800 | C4C—C5C | 1.394 (4) |
C8A—H8AC | 0.9800 | C4C—C8C | 1.500 (3) |
N1B—C2B | 1.344 (3) | C5C—H5C | 0.9500 |
N1B—C6B | 1.346 (3) | C5C—C6C | 1.369 (4) |
N1B—C7B | 1.480 (3) | C6C—H6C | 0.9500 |
C2B—H2B | 0.9500 | C7C—H7CA | 0.9800 |
C2B—C3B | 1.381 (4) | C7C—H7CB | 0.9800 |
C3B—H3B | 0.9500 | C7C—H7CC | 0.9800 |
C3B—C4B | 1.389 (3) | C8C—H8CA | 0.9800 |
C4B—C5B | 1.394 (3) | C8C—H8CB | 0.9800 |
C4B—C8B | 1.499 (3) | C8C—H8CC | 0.9800 |
C2A—N1A—C6A | 120.3 (2) | N1B—C6B—C5B | 120.5 (2) |
C2A—N1A—C7A | 119.6 (2) | N1B—C6B—H6B | 119.7 |
C6A—N1A—C7A | 120.0 (2) | C5B—C6B—H6B | 119.7 |
N1A—C2A—H2A | 119.7 | N1B—C7B—H7BA | 109.5 |
N1A—C2A—C3A | 120.6 (2) | N1B—C7B—H7BB | 109.5 |
C3A—C2A—H2A | 119.7 | N1B—C7B—H7BC | 109.5 |
C2A—C3A—H3A | 119.5 | H7BA—C7B—H7BB | 109.5 |
C2A—C3A—C4A | 121.0 (2) | H7BA—C7B—H7BC | 109.5 |
C4A—C3A—H3A | 119.5 | H7BB—C7B—H7BC | 109.5 |
C3A—C4A—C8A | 121.4 (2) | C4B—C8B—H8BA | 109.5 |
C5A—C4A—C3A | 116.4 (2) | C4B—C8B—H8BB | 109.5 |
C5A—C4A—C8A | 122.2 (2) | C4B—C8B—H8BC | 109.5 |
C4A—C5A—H5A | 119.7 | H8BA—C8B—H8BB | 109.5 |
C6A—C5A—C4A | 120.6 (2) | H8BA—C8B—H8BC | 109.5 |
C6A—C5A—H5A | 119.7 | H8BB—C8B—H8BC | 109.5 |
N1A—C6A—C5A | 121.1 (2) | C2C—N1C—C7C | 119.0 (2) |
N1A—C6A—H6A | 119.5 | C6C—N1C—C2C | 120.3 (2) |
C5A—C6A—H6A | 119.5 | C6C—N1C—C7C | 120.7 (2) |
N1A—C7A—H7AA | 109.5 | N1C—C2C—H2C | 119.6 |
N1A—C7A—H7AB | 109.5 | N1C—C2C—C3C | 120.9 (2) |
N1A—C7A—H7AC | 109.5 | C3C—C2C—H2C | 119.6 |
H7AA—C7A—H7AB | 109.5 | C2C—C3C—H3C | 119.7 |
H7AA—C7A—H7AC | 109.5 | C2C—C3C—C4C | 120.5 (2) |
H7AB—C7A—H7AC | 109.5 | C4C—C3C—H3C | 119.7 |
C4A—C8A—H8AA | 109.5 | C3C—C4C—C5C | 116.9 (2) |
C4A—C8A—H8AB | 109.5 | C3C—C4C—C8C | 121.9 (2) |
C4A—C8A—H8AC | 109.5 | C5C—C4C—C8C | 121.2 (2) |
H8AA—C8A—H8AB | 109.5 | C4C—C5C—H5C | 119.4 |
H8AA—C8A—H8AC | 109.5 | C6C—C5C—C4C | 121.2 (2) |
H8AB—C8A—H8AC | 109.5 | C6C—C5C—H5C | 119.4 |
C2B—N1B—C6B | 120.6 (2) | N1C—C6C—C5C | 120.3 (2) |
C2B—N1B—C7B | 119.8 (2) | N1C—C6C—H6C | 119.9 |
C6B—N1B—C7B | 119.6 (2) | C5C—C6C—H6C | 119.9 |
N1B—C2B—H2B | 119.7 | N1C—C7C—H7CA | 109.5 |
N1B—C2B—C3B | 120.5 (2) | N1C—C7C—H7CB | 109.5 |
C3B—C2B—H2B | 119.7 | N1C—C7C—H7CC | 109.5 |
C2B—C3B—H3B | 119.8 | H7CA—C7C—H7CB | 109.5 |
C2B—C3B—C4B | 120.4 (2) | H7CA—C7C—H7CC | 109.5 |
C4B—C3B—H3B | 119.8 | H7CB—C7C—H7CC | 109.5 |
C3B—C4B—C5B | 117.4 (2) | C4C—C8C—H8CA | 109.5 |
C3B—C4B—C8B | 121.9 (2) | C4C—C8C—H8CB | 109.5 |
C5B—C4B—C8B | 120.7 (2) | C4C—C8C—H8CC | 109.5 |
C4B—C5B—H5B | 119.8 | H8CA—C8C—H8CB | 109.5 |
C6B—C5B—C4B | 120.5 (2) | H8CA—C8C—H8CC | 109.5 |
C6B—C5B—H5B | 119.8 | H8CB—C8C—H8CC | 109.5 |
N1A—C2A—C3A—C4A | −0.6 (4) | C4B—C5B—C6B—N1B | 1.5 (4) |
C2A—N1A—C6A—C5A | −0.4 (4) | C6B—N1B—C2B—C3B | −2.0 (4) |
C2A—C3A—C4A—C5A | 0.9 (4) | C7B—N1B—C2B—C3B | 178.7 (2) |
C2A—C3A—C4A—C8A | −178.8 (2) | C7B—N1B—C6B—C5B | −179.6 (3) |
C3A—C4A—C5A—C6A | −0.9 (4) | C8B—C4B—C5B—C6B | 176.4 (2) |
C4A—C5A—C6A—N1A | 0.7 (4) | N1C—C2C—C3C—C4C | 0.1 (4) |
C6A—N1A—C2A—C3A | 0.3 (4) | C2C—N1C—C6C—C5C | 0.4 (4) |
C7A—N1A—C2A—C3A | 178.2 (2) | C2C—C3C—C4C—C5C | −0.1 (4) |
C7A—N1A—C6A—C5A | −178.2 (2) | C2C—C3C—C4C—C8C | −179.9 (2) |
C8A—C4A—C5A—C6A | 178.7 (3) | C3C—C4C—C5C—C6C | 0.3 (4) |
N1B—C2B—C3B—C4B | 0.3 (4) | C4C—C5C—C6C—N1C | −0.5 (5) |
C2B—N1B—C6B—C5B | 1.1 (4) | C6C—N1C—C2C—C3C | −0.2 (4) |
C2B—C3B—C4B—C5B | 2.2 (4) | C7C—N1C—C2C—C3C | −179.4 (2) |
C2B—C3B—C4B—C8B | −177.2 (2) | C7C—N1C—C6C—C5C | 179.6 (3) |
C3B—C4B—C5B—C6B | −3.0 (4) | C8C—C4C—C5C—C6C | −179.9 (3) |
Acknowledgements
The authors would like to thank the Chemistry and Biochemistry Department of Fredonia State Univeristy of New York for funding the study and for the purchase of the diffractometer.
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