1,4-Di­methyl­pyridinium iodide

Deschner, J.; Choczynski, J.M.; Wong, C.Y.; Hayes, K.L.; Crisci, R.R.; Lasher, E.; Dragonette, J.; Cardenas, A.J.P.

doi:10.1107/S2414314617002693

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170269

https://doi.org/10.1107/S2414314617002693

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1,4-Dimethylpyridinium iodide

Joshua Deschner,^a Jack M. Choczynski,^a Calvin Y. Wong,^a Kathleen L. Hayes,^a Ralph R. Crisci,^a Emily M. Lasher,^a Joseph Dragonette ^a and Allan Jay P. Cardenas ^a ^*

^a325 Science Center, Fredonia State University of New York, Fredonia 14063, USA
^*Correspondence e-mail: cardenas@fredonia.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 February 2017; accepted 16 February 2017; online 21 February 2017)

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 asymmetric unit. 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 asymmetric unit (Fig. 1). 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.

Figure 1
A view of the molecular structure of the title compound, showing the atom labeling and 50% probability displacement ellipsoids.

Figure 2
A view along the c axis of the crystal packing of the title compound (color code: I⁻ = violet balls, cation A = blue, cation B = red, and cation C = green).

The 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%).

Figure 3
Synthesis of the title organic salt.

Refinement

Crystal data, data collection and refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₇H₁₀N⁺·I⁻
M_r	235.06
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	13.8301 (6), 19.7170 (9), 10.2121 (5)
β (°)	109.642 (1)
V (Å³)	2622.7 (2)
Z	12
Radiation type	Mo Kα
μ (mm⁻¹)	3.59
Crystal size (mm)	0.5 × 0.5 × 0.3

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2015 )
T_min, T_max	0.476, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	16106, 5933, 5401
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.048, 1.14
No. of reflections	5933
No. of parameters	251
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.49
Computer programs: APEX2 and SAINT (Bruker, 2015), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1533238

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617002693/su4130sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002693/su4130Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: 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).

1,4-Dimethylpyridinium iodide top

Crystal data top

C₇H₁₀N⁺·I⁻	F(000) = 1344
M_r = 235.06	D_x = 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

Data collection top

Bruker APEX-II CCD diffractometer	5401 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.019
Absorption correction: multi-scan (SADABS; Bruker, 2015)	θ_max = 27.9°, θ_min = 3.0°
T_min = 0.476, T_max = 0.746	h = −18→16
16106 measured reflections	k = −25→22
5933 independent reflections	l = −10→13

Refinement top

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(F_o²) + (0.013P)² + 2.567P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.048	(Δ/σ)_max = 0.002
S = 1.14	Δρ_max = 0.51 e Å⁻³
5933 reflections	Δρ_min = −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

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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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