Literature DB >> 22904952

4-Cyano-1-methyl-pyridinium iodide.

Michael N Kammer, Lynn V Koplitz, Joel T Mague.

Abstract

In the crystal structure of the title compound, C(7)H(7)N(2) (+)·I(-), the cations form inversion-related dimers via weak pairwise C-H⋯N hydrogen bonds. In the dimers, the pyridinium rings are parallel to one another with their mean planes separated by a normal distance of ca 0.28 Å. Weak C-H⋯N inter-actions between adjacent dimers generate a layer lying parallel to (10-1). The remaining H atoms form C-H⋯I inter-actions, which link the layers into a three-dimensional structure.

Entities: Chemical Disease Species

Year: 2012 PMID： 22904952 PMCID： PMC3414965 DOI： 10.1107/S1600536812032230

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the structure of 3-cyano-1-methylpyridinium iodide, see: Koplitz et al. (2003 ▶). For the structure of 1-methylpyridinium iodide, see: Lalancette et al. (1978 ▶). For related structures see: Mague et al. (2005 ▶); Koplitz et al. (2012 ▶).

Experimental

Crystal data

C7H7N2 +·I− M = 246.05 Monoclinic, a = 5.0734 (3) Å b = 11.4528 (7) Å c = 15.0751 (9) Å β = 99.679 (1)° V = 863.46 (9) Å3 Z = 4 Mo Kα radiation μ = 3.64 mm−1 T = 100 K 0.14 × 0.07 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.614, T max = 0.836 12786 measured reflections 1792 independent reflections 1572 reflections with I > 2σ(I) R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.020 wR(F 2) = 0.048 S = 1.07 1792 reflections 92 parameters H-atom parameters constrained Δρmax = 0.88 e Å−3 Δρmin = −0.47 e Å−3 Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032230/su2473sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032230/su2473Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812032230/su2473Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₇H₇N₂⁺·I⁻	F(000) = 464
M_r = 246.05	D_x = 1.893 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8899 reflections
a = 5.0734 (3) Å	θ = 2.3–28.6°
b = 11.4528 (7) Å	µ = 3.64 mm⁻¹
c = 15.0751 (9) Å	T = 100 K
β = 99.679 (1)°	Plates, yellow
V = 863.46 (9) Å³	0.14 × 0.07 × 0.05 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1792 independent reflections
Radiation source: fine-focus sealed tube	1572 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 26.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.614, T_max = 0.836	k = −14→14
12786 measured reflections	l = −18→18

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.048	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0159P)² + 1.1195P] where P = (F_o² + 2F_c²)/3
1792 reflections	(Δ/σ)_max = 0.002
92 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

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. H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms.

	x	y	z	U_iso*/U_eq
I1	0.95185 (3)	0.378404 (15)	0.854589 (12)	0.02114 (7)
N1	0.6792 (5)	0.3458 (2)	0.18850 (15)	0.0201 (5)
N2	0.7382 (5)	0.0466 (2)	−0.07663 (17)	0.0307 (6)
C1	0.6477 (6)	0.4209 (3)	0.26587 (19)	0.0233 (6)
H1A	0.5052	0.4779	0.2472	0.035*
H1B	0.8159	0.4621	0.2871	0.035*
H1C	0.6013	0.3726	0.3146	0.035*
C2	0.8704 (6)	0.2626 (3)	0.19989 (19)	0.0218 (6)
H2	0.9858	0.2554	0.2562	0.026*
C3	0.8996 (6)	0.1883 (3)	0.13096 (19)	0.0219 (6)
H3	1.0361	0.1306	0.1387	0.026*
C4	0.7265 (6)	0.1986 (2)	0.04961 (18)	0.0207 (6)
C5	0.5356 (6)	0.2869 (3)	0.03797 (19)	0.0243 (6)
H5	0.4201	0.2965	−0.0181	0.029*
C6	0.5167 (6)	0.3604 (3)	0.10929 (19)	0.0223 (6)
H6	0.3883	0.4215	0.1023	0.027*
C7	0.7369 (6)	0.1158 (3)	−0.0225 (2)	0.0244 (6)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01891 (11)	0.02214 (12)	0.02205 (11)	0.00126 (7)	0.00256 (7)	0.00040 (7)
N1	0.0211 (12)	0.0212 (12)	0.0191 (12)	0.0000 (9)	0.0065 (9)	0.0021 (9)
N2	0.0343 (15)	0.0328 (15)	0.0257 (14)	0.0058 (12)	0.0071 (11)	−0.0015 (12)
C1	0.0265 (15)	0.0239 (15)	0.0201 (14)	0.0037 (12)	0.0055 (12)	0.0008 (11)
C2	0.0190 (14)	0.0260 (15)	0.0204 (14)	0.0032 (11)	0.0035 (11)	0.0053 (11)
C3	0.0197 (14)	0.0238 (15)	0.0237 (15)	0.0060 (11)	0.0078 (11)	0.0048 (11)
C4	0.0250 (15)	0.0217 (14)	0.0171 (14)	0.0001 (11)	0.0082 (11)	0.0021 (11)
C5	0.0229 (15)	0.0301 (17)	0.0190 (14)	0.0041 (12)	0.0010 (11)	0.0021 (12)
C6	0.0219 (14)	0.0228 (15)	0.0219 (14)	0.0053 (11)	0.0029 (11)	0.0033 (11)
C7	0.0253 (15)	0.0256 (16)	0.0234 (15)	0.0017 (12)	0.0073 (12)	0.0027 (12)

N1—C6	1.343 (4)	C2—H2	0.9500
N1—C2	1.350 (4)	C3—C4	1.388 (4)
N1—C1	1.480 (4)	C3—H3	0.9500
N2—C7	1.139 (4)	C4—C5	1.390 (4)
C1—H1A	0.9800	C4—C7	1.451 (4)
C1—H1B	0.9800	C5—C6	1.381 (4)
C1—H1C	0.9800	C5—H5	0.9500
C2—C3	1.370 (4)	C6—H6	0.9500

C6—N1—C2	121.4 (2)	C2—C3—H3	120.5
C6—N1—C1	119.8 (2)	C4—C3—H3	120.5
C2—N1—C1	118.7 (2)	C3—C4—C5	119.8 (3)
N1—C1—H1A	109.5	C3—C4—C7	120.6 (3)
N1—C1—H1B	109.5	C5—C4—C7	119.5 (3)
H1A—C1—H1B	109.5	C6—C5—C4	118.8 (3)
N1—C1—H1C	109.5	C6—C5—H5	120.6
H1A—C1—H1C	109.5	C4—C5—H5	120.6
H1B—C1—H1C	109.5	N1—C6—C5	120.3 (3)
N1—C2—C3	120.6 (3)	N1—C6—H6	119.9
N1—C2—H2	119.7	C5—C6—H6	119.9
C3—C2—H2	119.7	N2—C7—C4	176.3 (3)
C2—C3—C4	119.0 (3)

C6—N1—C2—C3	−1.6 (4)	C7—C4—C5—C6	175.8 (3)
C1—N1—C2—C3	177.5 (3)	C2—N1—C6—C5	2.4 (4)
N1—C2—C3—C4	−1.1 (4)	C1—N1—C6—C5	−176.7 (3)
C2—C3—C4—C5	2.9 (4)	C4—C5—C6—N1	−0.5 (4)
C2—C3—C4—C7	−175.0 (3)	C3—C4—C7—N2	76 (5)
C3—C4—C5—C6	−2.2 (4)	C5—C4—C7—N2	−102 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2ⁱ	0.95	2.58	3.434 (4)	149
C1—H1B···N2ⁱⁱ	0.98	2.71	3.513 (4)	140
C1—H1A···I1ⁱⁱⁱ	0.98	3.04	3.999 (3)	166
C1—H1C···I1^iv	0.98	3.06	3.870 (3)	141
C2—H2···I1^v	0.95	2.99	3.796 (3)	144
C5—H5···I1^vi	0.95	2.94	3.839 (3)	158
C6—H6···I1ⁱⁱⁱ	0.95	3.01	3.916 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N2ⁱ	0.95	2.58	3.434 (4)	149
C1—H1B⋯N2ⁱⁱ	0.98	2.71	3.513 (4)	140
C1—H1A⋯I1ⁱⁱⁱ	0.98	3.04	3.999 (3)	166
C1—H1C⋯I1^iv	0.98	3.06	3.870 (3)	141
C2—H2⋯I1^v	0.95	2.99	3.796 (3)	144
C5—H5⋯I1^vi	0.95	2.94	3.839 (3)	158
C6—H6⋯I1ⁱⁱⁱ	0.95	3.01	3.916 (3)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

1 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

1 in total

4 in total

4. Crystal structures of the hexa-fluorido-phosphate salts of the isomeric 2-, 3- and 4-cyano-1-methyl-pyridinium cations and determination of solid-state inter-action energies.

Authors: Joel T Mague; Erin Larrabee; David Olivier; Francesca Vaccaro; Kevin E Riley; Lynn V Koplitz
Journal: Acta Crystallogr E Crystallogr Commun Date: 2018-08-24