2-Cyano-1-methyl-pyridinium iodide.

The cation in the title compound, C7H7N2 (+)·I(-), is planar (r.m.s. deviation for the nine fitted non-H atoms = 0.040 Å). The crystal packing is best described as undulating layers of cations and anions associated via C-H⋯I inter-actions.

Related literature

For the structure of 2-cyano-N-methyl­pyridinium nitrate, see: Koplitz et al. (2012 ▶). For structures of 3-cyano-N-methyl­pyridinium salts, see: Koplitz et al. (2003 ▶); Mague et al. (2005 ▶). For structures of 4-cyano-N-methyl­pyridinium salts, see: Kammer, Koplitz & Mague (2012 ▶); Kammer, Mague & Koplitz (2012 ▶).

Experimental

Crystal data

C7H7N2 +·I−

M = 246.05

Orthorhombic,

a = 9.5785 (6) Å

b = 8.5687 (5) Å

c = 20.2229 (13) Å

V = 1659.80 (18) Å3

Z = 8

Mo Kα radiation

μ = 3.79 mm−1

T = 100 K

0.16 × 0.14 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (TWINABS; Sheldrick, 2009 ▶) T min = 0.58, T max = 0.77

58292 measured reflections

53390 independent reflections

40858 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.091

S = 1.03

53390 reflections

93 parameters

H-atom parameters constrained

Δρmax = 1.14 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL and CELL_NOW (Sheldrick, 2008b ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019302/tk5240sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019302/tk5240Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019302/tk5240Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H7N2+·I−	Dx = 1.969 Mg m−3
Mr = 246.05	Melting point: 146 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 9.5785 (6) Å	Cell parameters from 4287 reflections
b = 8.5687 (5) Å	θ = 2.9–28.7°
c = 20.2229 (13) Å	µ = 3.79 mm−1
V = 1659.80 (18) Å3	T = 100 K
Z = 8	Slab, yellow
F(000) = 928	0.16 × 0.14 × 0.07 mm

Bruker SMART APEX CCD diffractometer	53390 independent reflections
Radiation source: fine-focus sealed tube	40858 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 8.3660 pixels mm-1	θmax = 28.7°, θmin = 2.0°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −11→11
Tmin = 0.58, Tmax = 0.77	l = −26→27
58292 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0143P)2 + 0.7747P] where P = (Fo2 + 2Fc2)/3
53390 reflections	(Δ/σ)max < 0.001
93 parameters	Δρmax = 1.14 e Å−3
0 restraints	Δρmin = −0.43 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.

	x	y	z	Uiso*/Ueq
I1	0.41161 (3)	0.07802 (3)	0.10870 (2)	0.01550 (12)
N1	0.9765 (4)	1.0275 (5)	0.1442 (2)	0.0135 (9)
N2	0.7422 (4)	0.7530 (5)	0.2022 (2)	0.0205 (10)
C1	1.0446 (5)	0.9818 (6)	0.2072 (3)	0.0187 (11)
H1A	1.1337	1.0371	0.2116	0.028*
H1B	1.0615	0.8690	0.2072	0.028*
H1C	0.9837	1.0092	0.2443	0.028*
C2	0.8562 (5)	0.9559 (6)	0.1244 (3)	0.0142 (10)
C3	0.7917 (5)	0.9967 (6)	0.0661 (3)	0.0158 (11)
H3	0.7074	0.9471	0.0530	0.019*
C4	0.8517 (5)	1.1118 (6)	0.0268 (3)	0.0168 (11)
H4	0.8105	1.1395	−0.0143	0.020*
C5	0.9713 (5)	1.1848 (6)	0.0481 (3)	0.0166 (11)
H5	1.0122	1.2648	0.0220	0.020*
C6	1.0321 (5)	1.1424 (5)	0.1070 (3)	0.0149 (10)
H6	1.1140	1.1945	0.1216	0.018*
C7	0.7957 (5)	0.8415 (6)	0.1685 (3)	0.0165 (11)

	U11	U22	U33	U12	U13	U23
I1	0.01513 (19)	0.01697 (18)	0.01439 (19)	0.00131 (12)	−0.00021 (13)	−0.00058 (13)
N1	0.013 (2)	0.014 (2)	0.014 (2)	0.0017 (16)	0.0001 (18)	−0.0019 (17)
N2	0.022 (2)	0.020 (2)	0.019 (2)	−0.0019 (19)	0.001 (2)	−0.0010 (19)
C1	0.020 (3)	0.022 (3)	0.014 (3)	−0.001 (2)	−0.004 (2)	0.001 (2)
C2	0.012 (2)	0.014 (2)	0.016 (3)	−0.0010 (19)	0.003 (2)	−0.003 (2)
C3	0.013 (3)	0.016 (2)	0.018 (3)	0.0006 (19)	0.000 (2)	−0.003 (2)
C4	0.019 (3)	0.017 (2)	0.014 (3)	0.004 (2)	−0.001 (2)	−0.002 (2)
C5	0.017 (3)	0.014 (2)	0.020 (3)	0.0014 (19)	0.003 (2)	0.000 (2)
C6	0.012 (2)	0.011 (2)	0.021 (3)	0.0023 (18)	0.003 (2)	−0.002 (2)
C7	0.015 (2)	0.019 (3)	0.016 (3)	0.001 (2)	−0.001 (2)	−0.006 (2)

N1—C6	1.348 (6)	C2—C7	1.446 (7)
N1—C2	1.366 (6)	C3—C4	1.391 (7)
N1—C1	1.484 (6)	C3—H3	0.9500
N2—C7	1.141 (6)	C4—C5	1.375 (7)
C1—H1A	0.9800	C4—H4	0.9500
C1—H1B	0.9800	C5—C6	1.375 (7)
C1—H1C	0.9800	C5—H5	0.9500
C2—C3	1.375 (7)	C6—H6	0.9500
C6—N1—C2	119.8 (4)	C2—C3—H3	120.5
C6—N1—C1	119.9 (4)	C4—C3—H3	120.5
C2—N1—C1	120.3 (4)	C5—C4—C3	119.1 (5)
N1—C1—H1A	109.5	C5—C4—H4	120.4
N1—C1—H1B	109.5	C3—C4—H4	120.4
H1A—C1—H1B	109.5	C6—C5—C4	120.3 (5)
N1—C1—H1C	109.5	C6—C5—H5	119.8
H1A—C1—H1C	109.5	C4—C5—H5	119.8
H1B—C1—H1C	109.5	N1—C6—C5	120.6 (5)
N1—C2—C3	121.1 (4)	N1—C6—H6	119.7
N1—C2—C7	117.5 (4)	C5—C6—H6	119.7
C3—C2—C7	121.4 (5)	N2—C7—C2	176.9 (6)
C2—C3—C4	119.0 (5)
C6—N1—C2—C3	1.3 (7)	C2—C3—C4—C5	−2.0 (7)
C1—N1—C2—C3	−180.0 (5)	C3—C4—C5—C6	1.2 (7)
C6—N1—C2—C7	−175.6 (4)	C2—N1—C6—C5	−2.2 (7)
C1—N1—C2—C7	3.1 (7)	C1—N1—C6—C5	179.1 (4)
N1—C2—C3—C4	0.7 (7)	C4—C5—C6—N1	0.9 (7)
C7—C2—C3—C4	177.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···I1i	0.98	3.20	4.014 (5)	141
C1—H1C···I1ii	0.98	3.11	4.021 (5)	156
C5—H5···I1iii	0.95	3.12	3.810 (5)	131
C6—H6···I1iv	0.95	3.03	3.677 (5)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯I1i	0.98	3.20	4.014 (5)	141
C1—H1C⋯I1ii	0.98	3.11	4.021 (5)	156
C5—H5⋯I1iii	0.95	3.12	3.810 (5)	131
C6—H6⋯I1iv	0.95	3.03	3.677 (5)	126

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