2-Cyano-anilinium iodide.

The solid-state structure of the title salt, C7H7N2 (+.)I(-), consists of cation-anion sheets lying parallel to (110), with the components linked by N-H⋯I hydrogen bonds.

Related literature

For the structure of 2-cyano-1-methyl­pyridinium iodide, see: Kammer et al. (2013 ▶). For structures of other 2-cyano­anilinium salts, see: Cui & Chen (2010 ▶); Zhang (2009 ▶); Cui & Wen (2008 ▶); Oueslati et al. (2005 ▶). For the structures of 4-cyanoanilinium halides, see: Mague et al. (2012 ▶); Vumbaco et al. (2012 ▶); Colapietro et al. (1981 ▶).

Experimental

Crystal data

C7H7N2 +·I−

M = 246.05

Orthorhombic,

a = 10.1474 (15) Å

b = 8.6979 (13) Å

c = 18.073 (3) Å

V = 1595.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 3.94 mm−1

T = 100 K

0.20 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2010 ▶) T min = 0.43, T max = 0.58

25911 measured reflections

2112 independent reflections

2030 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.016

wR(F 2) = 0.041

S = 1.10

2112 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXM (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019314/hb7106sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019314/hb7106Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019314/hb7106Isup3.cml

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

C7H7N2+·I−	Dx = 2.049 Mg m−3
Mr = 246.05	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9853 reflections
a = 10.1474 (15) Å	θ = 2.3–29.1°
b = 8.6979 (13) Å	µ = 3.94 mm−1
c = 18.073 (3) Å	T = 100 K
V = 1595.2 (4) Å3	Block, colourless
Z = 8	0.20 × 0.19 × 0.16 mm
F(000) = 928

Bruker SMART APEX CCD diffractometer	2112 independent reflections
Radiation source: fine-focus sealed tube	2030 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.3660 pixels mm-1	θmax = 29.1°, θmin = 2.3°
φ and ω scans	h = −13→13
Absorption correction: numerical (SADABS; Bruker, 2010)	k = −11→11
Tmin = 0.43, Tmax = 0.58	l = −24→24
25911 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.016	H-atom parameters constrained
wR(F2) = 0.041	w = 1/[σ2(Fo2) + (0.0208P)2 + 0.7585P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.002
2112 reflections	Δρmax = 0.59 e Å−3
92 parameters	Δρmin = −0.58 e Å−3
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00151 (13)

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 10 sec/frame.

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	0.58823 (2)	0.05477 (2)	0.13679 (2)	0.01326 (5)
N1	0.58054 (12)	0.44877 (14)	0.19889 (8)	0.0140 (3)
H1A	0.5870	0.3496	0.1900	0.017*
H1B	0.5590	0.4716	0.2448	0.017*
H1C	0.6593	0.4909	0.1973	0.017*
N2	0.28338 (14)	0.23930 (17)	0.21818 (8)	0.0246 (3)
C1	0.49549 (15)	0.51204 (18)	0.14089 (7)	0.0129 (3)
C2	0.54089 (14)	0.63213 (16)	0.09804 (8)	0.0149 (3)
H2	0.6252	0.6758	0.1071	0.018*
C3	0.46120 (15)	0.68861 (17)	0.04120 (8)	0.0170 (3)
H3	0.4916	0.7711	0.0113	0.020*
C4	0.33787 (15)	0.62516 (17)	0.02809 (8)	0.0183 (3)
H4	0.2854	0.6627	−0.0115	0.022*
C5	0.29073 (15)	0.50692 (19)	0.07257 (8)	0.0172 (3)
H5	0.2054	0.4654	0.0643	0.021*
C6	0.36974 (17)	0.44965 (16)	0.12950 (8)	0.0141 (3)
C7	0.32073 (14)	0.33165 (17)	0.17807 (8)	0.0167 (3)

	U11	U22	U33	U12	U13	U23
I1	0.01359 (7)	0.01201 (7)	0.01419 (7)	−0.00040 (3)	−0.00112 (3)	−0.00004 (3)
N1	0.0147 (6)	0.0120 (6)	0.0152 (6)	−0.0004 (4)	−0.0008 (4)	0.0005 (4)
N2	0.0270 (7)	0.0236 (7)	0.0233 (7)	−0.0071 (6)	0.0076 (6)	−0.0023 (6)
C1	0.0145 (7)	0.0117 (7)	0.0126 (6)	0.0012 (5)	0.0003 (5)	−0.0022 (5)
C2	0.0153 (6)	0.0120 (6)	0.0174 (6)	−0.0003 (5)	0.0003 (5)	−0.0002 (5)
C3	0.0210 (7)	0.0127 (7)	0.0174 (7)	0.0019 (6)	0.0010 (5)	0.0009 (5)
C4	0.0213 (7)	0.0163 (7)	0.0174 (6)	0.0050 (6)	−0.0035 (5)	−0.0020 (6)
C5	0.0150 (6)	0.0166 (7)	0.0199 (7)	0.0020 (6)	−0.0011 (5)	−0.0058 (6)
C6	0.0142 (8)	0.0119 (7)	0.0161 (7)	0.0012 (5)	0.0029 (5)	−0.0033 (5)
C7	0.0143 (6)	0.0174 (7)	0.0182 (7)	−0.0017 (5)	0.0023 (5)	−0.0053 (6)

N1—C1	1.4651 (19)	C2—H2	0.9500
N1—H1A	0.8800	C3—C4	1.388 (2)
N1—H1B	0.8800	C3—H3	0.9500
N1—H1C	0.8800	C4—C5	1.390 (2)
N2—C7	1.146 (2)	C4—H4	0.9500
C1—C2	1.380 (2)	C5—C6	1.396 (2)
C1—C6	1.402 (2)	C5—H5	0.9500
C2—C3	1.397 (2)	C6—C7	1.439 (2)
C1—N1—H1A	106.4	C4—C3—H3	119.7
C1—N1—H1B	116.3	C2—C3—H3	119.7
H1A—N1—H1B	114.3	C3—C4—C5	120.37 (14)
C1—N1—H1C	110.8	C3—C4—H4	119.8
H1A—N1—H1C	109.6	C5—C4—H4	119.8
H1B—N1—H1C	99.3	C4—C5—C6	119.51 (14)
C2—C1—C6	120.98 (13)	C4—C5—H5	120.2
C2—C1—N1	119.30 (13)	C6—C5—H5	120.2
C6—C1—N1	119.72 (13)	C5—C6—C1	119.52 (14)
C1—C2—C3	119.07 (14)	C5—C6—C7	120.37 (15)
C1—C2—H2	120.5	C1—C6—C7	120.07 (14)
C3—C2—H2	120.5	N2—C7—C6	178.30 (17)
C4—C3—C2	120.51 (14)
C6—C1—C2—C3	−1.9 (2)	C4—C5—C6—C7	177.45 (14)
N1—C1—C2—C3	177.87 (13)	C2—C1—C6—C5	1.9 (2)
C1—C2—C3—C4	0.2 (2)	N1—C1—C6—C5	−177.89 (13)
C2—C3—C4—C5	1.6 (2)	C2—C1—C6—C7	−175.70 (13)
C3—C4—C5—C6	−1.6 (2)	N1—C1—C6—C7	4.5 (2)
C4—C5—C6—C1	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···I1	0.88	2.74	3.6069 (13)	169
N1—H1B···I1i	0.88	2.71	3.5501 (14)	160
N1—H1C···I1ii	0.88	2.84	3.6615 (13)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯I1	0.88	2.74	3.6069 (13)	169
N1—H1B⋯I1i	0.88	2.71	3.5501 (14)	160
N1—H1C⋯I1ii	0.88	2.84	3.6615 (13)	156

Symmetry codes: (i) ; (ii) .