4-Cyano-anilinium iodide.

In the title compound, C(7)H(7)N(2) (+)·I(-), the cation is located on a site of 4mm symmetry and is thus disordered about the fourfold axis so that there are two perpendicular orientations of the six-membered ring and four rotational orientations of the {-NH(3) (+)} group. In the crystal, there are two layers perpendicular to the c axis, each containing iodide ions and the {-NH(3) (+)} portions of the cations, with the remainder of the cations extending outwards from these layers.

Related literature

For the structure of 4-cyano­anilinium chloride, see: Colapietro et al. (1981 ▶). For the structure of 4-cyano­anilinium bromide, see: Vumbaco et al. (2012 ▶). For the structure of anilinium iodide, see: Fecher & Weiss (1986 ▶).

Experimental

Crystal data

C7H7N2 +·I−

M = 246.05

Tetragonal,

a = 4.9930 (4) Å

c = 16.445 (2) Å

V = 409.98 (8) Å3

Z = 2

Mo Kα radiation

μ = 3.83 mm−1

T = 100 K

0.26 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2009 ▶) T min = 0.362, T max = 0.844

7082 measured reflections

382 independent reflections

381 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.012

wR(F 2) = 0.029

S = 1.14

382 reflections

31 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.56 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/S1600536812033466/rk2373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033466/rk2373Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033466/rk2373Isup3.cml

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

C7H7N2+·I−	Dx = 1.993 Mg m−3
Mr = 246.05	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4/nmm	Cell parameters from 8495 reflections
Hall symbol: -P 4a 2a	θ = 2.5–29.1°
a = 4.9930 (4) Å	µ = 3.83 mm−1
c = 16.445 (2) Å	T = 100 K
V = 409.98 (8) Å3	Plate, colourless
Z = 2	0.26 × 0.20 × 0.05 mm
F(000) = 232

Bruker SMART APEX CCD diffractometer	382 independent reflections
Radiation source: fine–focus sealed tube	381 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 29.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2009)	h = −6→6
Tmin = 0.362, Tmax = 0.844	k = −6→6
7082 measured reflections	l = −22→22

Refinement on F2	Primary atom site location: heavy atom
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.012	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.029	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0165P)2 + 0.1447P] where P = (Fo2 + 2Fc2)/3
382 reflections	(Δ/σ)max = 0.002
31 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F2, conventional R–factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R–factors(gt) etc. and is not relevant to the choice of reflections for refinement. R–factors based on F2 are statistically about twice as large as those based on F, and R–factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.7500	0.7500	0.588552 (10)	0.01472 (8)
N1	0.2500	0.2500	0.62508 (16)	0.0199 (5)
H1	0.3662	0.3662	0.6057	0.024*	0.25
H1A	0.0887	0.2904	0.6073	0.024*	0.125
H1B	0.2904	0.0887	0.6073	0.024*	0.125
N2	0.2500	0.2500	1.03941 (17)	0.0226 (6)
C1	0.2500	0.2500	0.71467 (18)	0.0139 (5)
C2	0.4934 (6)	0.2500	0.75539 (17)	0.0174 (5)	0.50
H2	0.6576	0.2500	0.7262	0.021*	0.50
C3	0.4936 (6)	0.2500	0.84022 (16)	0.0171 (5)	0.50
H3	0.6583	0.2500	0.8692	0.020*	0.50
C4	0.2500	0.2500	0.88189 (18)	0.0143 (5)
C5	0.2500	0.2500	0.97006 (19)	0.0174 (6)

	U11	U22	U33	U12	U13	U23
I1	0.01513 (9)	0.01513 (9)	0.01392 (11)	0.000	0.000	0.000
N1	0.0236 (8)	0.0236 (8)	0.0126 (11)	0.000	0.000	0.000
N2	0.0252 (9)	0.0252 (9)	0.0174 (12)	0.000	0.000	0.000
C1	0.0129 (8)	0.0129 (8)	0.0158 (12)	0.000	0.000	0.000
C2	0.0132 (12)	0.0225 (14)	0.0163 (11)	0.000	0.0020 (10)	0.000
C3	0.0129 (12)	0.0226 (13)	0.0157 (11)	0.000	−0.0022 (11)	0.000
C4	0.0146 (8)	0.0146 (8)	0.0136 (13)	0.000	0.000	0.000
C5	0.0161 (9)	0.0161 (9)	0.0200 (14)	0.000	0.000	0.000

N1—C1	1.473 (4)	C2—C3	1.395 (4)
N1—H1	0.8800	C2—H2	0.9500
N1—H1A	0.8800	C3—C4	1.396 (3)
N1—H1B	0.8800	C3—H3	0.9500
N2—C5	1.141 (4)	C4—C3i	1.396 (3)
C1—C2i	1.388 (3)	C4—C5	1.450 (4)
C1—C2	1.388 (3)
C1—N1—H1	111.2	C1—C2—H2	120.8
C1—N1—H1A	109.4	C3—C2—H2	120.3
H1—N1—H1A	109.4	C2—C3—C4	119.3 (3)
C1—N1—H1B	109.4	C2—C3—H3	120.1
H1—N1—H1B	109.4	C4—C3—H3	120.5
H1A—N1—H1B	108.0	C3i—C4—C3	121.2 (3)
C2i—C1—C2	122.3 (3)	C3i—C4—C5	119.39 (15)
C2i—C1—N1	118.85 (16)	C3—C4—C5	119.39 (15)
C2—C1—N1	118.85 (16)	N2—C5—C4	180.000 (1)
C1—C2—C3	118.9 (3)
C2i—C1—C2—C3	0.000 (2)	C1—C2—C3—C4	0.000 (2)
N1—C1—C2—C3	180.000 (1)	C2—C3—C4—C5	180.000 (1)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1	0.88	2.72	3.5813 (5)	165
N1—H1A···I1ii	0.88	2.87	3.5813 (5)	139
N1—H1B···I1iii	0.88	2.87	3.5813 (5)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯I1	0.88	2.72	3.5813 (5)	165
N1—H1A⋯I1i	0.88	2.87	3.5813 (5)	139
N1—H1B⋯I1ii	0.88	2.87	3.5813 (5)	139

Symmetry codes: (i) ; (ii) .