4-Cyano-anilinium perchlorate.

The title compound, C(7)H(7)N(2) (+)·ClO(4) (-), comprises discrete ions which are inter-connected by N-H⋯O hydrogen bonds, leading to a neutral one-dimensional network along the [100] direction.

Related literature

For the chemistry of nitrile derivatives, see: Xiong et al. (2002 ▶); Jin et al. (1994 ▶); Brewis et al. (2003 ▶); Fu et al. (2008 ▶); Duncia et al. (1991 ▶); Fu & Zhao (2007 ▶); Dai & Fu (2008 ▶); Smith et al. (2000 ▶).

Experimental

Crystal data

C7H7N2 +·ClO4 −

M = 218.60

Triclinic,

a = 4.9905 (10) Å

b = 6.9465 (14) Å

c = 13.998 (3) Å

α = 94.87 (3)°

β = 95.68 (3)°

γ = 103.99 (3)°

V = 465.57 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 298 (2) K

0.25 × 0.15 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.941, T max = 1.000 (expected range = 0.886–0.942)

4861 measured reflections

2126 independent reflections

1851 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.05

2126 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030687/bx2181sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030687/bx2181Isup2.hkl

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

C7H7N2+·ClO4−	Z = 2
Mr = 218.60	F(000) = 224
Triclinic, P1	Dx = 1.559 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9905 (10) Å	Cell parameters from 1806 reflections
b = 6.9465 (14) Å	θ = 3.0–27.5°
c = 13.998 (3) Å	µ = 0.40 mm−1
α = 94.87 (3)°	T = 298 K
β = 95.68 (3)°	Block, colourless
γ = 103.99 (3)°	0.25 × 0.15 × 0.15 mm
V = 465.57 (17) Å3

Rigaku Mercury2 diffractometer	2126 independent reflections
Radiation source: fine-focus sealed tube	1851 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −8→8
Tmin = 0.941, Tmax = 1.000	l = −18→18
4861 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) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0483P)2 + 0.1253P] where P = (Fo2 + 2Fc2)/3
2126 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.34 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. 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
N1	0.6157 (3)	0.2508 (2)	0.12597 (11)	0.0399 (4)
H1A	0.4771	0.2405	0.0791	0.048*
H1B	0.6876	0.1460	0.1180	0.048*
H1C	0.7468	0.3623	0.1238	0.048*
N2	0.0727 (7)	0.2647 (4)	0.5503 (2)	0.1058 (10)
C1	0.1672 (6)	0.2642 (4)	0.47983 (19)	0.0743 (8)
C2	0.2877 (5)	0.2620 (3)	0.38998 (16)	0.0549 (5)
C3	0.2722 (5)	0.4100 (3)	0.33016 (17)	0.0557 (5)
H3	0.1860	0.5101	0.3478	0.067*
C4	0.3859 (4)	0.4064 (3)	0.24466 (15)	0.0458 (4)
H4	0.3789	0.5049	0.2041	0.055*
C5	0.5097 (3)	0.2566 (3)	0.21961 (13)	0.0362 (4)
C6	0.5293 (4)	0.1094 (3)	0.27829 (14)	0.0464 (5)
H6	0.6169	0.0104	0.2604	0.056*
C7	0.4158 (5)	0.1127 (4)	0.36408 (16)	0.0574 (6)
H7	0.4252	0.0145	0.4046	0.069*
Cl1	−0.00044 (8)	0.22266 (6)	0.91125 (3)	0.03315 (14)
O1	−0.2849 (3)	0.1812 (2)	0.92711 (11)	0.0552 (4)
O2	0.1712 (3)	0.3237 (2)	0.99794 (12)	0.0598 (4)
O3	0.0665 (3)	0.0398 (2)	0.88369 (13)	0.0593 (4)
O4	0.0420 (4)	0.3478 (2)	0.83610 (12)	0.0668 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0442 (8)	0.0392 (8)	0.0403 (9)	0.0162 (7)	0.0100 (6)	0.0048 (6)
N2	0.141 (3)	0.0996 (19)	0.0746 (17)	0.0122 (17)	0.0625 (17)	−0.0038 (14)
C1	0.0839 (18)	0.0741 (17)	0.0597 (16)	0.0059 (14)	0.0296 (13)	−0.0047 (13)
C2	0.0545 (12)	0.0599 (13)	0.0450 (12)	0.0039 (10)	0.0167 (9)	−0.0053 (10)
C3	0.0560 (13)	0.0514 (12)	0.0617 (14)	0.0159 (10)	0.0210 (10)	−0.0056 (10)
C4	0.0485 (11)	0.0424 (10)	0.0506 (12)	0.0168 (8)	0.0126 (9)	0.0046 (8)
C5	0.0328 (8)	0.0375 (9)	0.0366 (9)	0.0068 (7)	0.0046 (7)	0.0004 (7)
C6	0.0547 (11)	0.0455 (10)	0.0441 (11)	0.0205 (9)	0.0097 (9)	0.0072 (8)
C7	0.0714 (15)	0.0609 (13)	0.0425 (12)	0.0163 (11)	0.0126 (10)	0.0140 (10)
Cl1	0.0306 (2)	0.0284 (2)	0.0426 (3)	0.00948 (15)	0.00733 (15)	0.00697 (15)
O1	0.0333 (7)	0.0667 (9)	0.0627 (10)	0.0079 (6)	0.0146 (6)	−0.0046 (7)
O2	0.0531 (9)	0.0534 (9)	0.0661 (10)	0.0147 (7)	−0.0150 (7)	−0.0090 (7)
O3	0.0595 (9)	0.0396 (7)	0.0839 (12)	0.0271 (7)	0.0058 (8)	−0.0036 (7)
O4	0.0880 (12)	0.0539 (9)	0.0623 (11)	0.0127 (8)	0.0217 (9)	0.0293 (8)

N1—C5	1.462 (2)	C4—C5	1.371 (3)
N1—H1A	0.8900	C4—H4	0.9300
N1—H1B	0.8900	C5—C6	1.380 (3)
N1—H1C	0.8900	C6—C7	1.378 (3)
N2—C1	1.135 (3)	C6—H6	0.9300
C1—C2	1.447 (3)	C7—H7	0.9300
C2—C7	1.385 (3)	Cl1—O4	1.4202 (15)
C2—C3	1.392 (3)	Cl1—O3	1.4215 (14)
C3—C4	1.375 (3)	Cl1—O1	1.4222 (14)
C3—H3	0.9300	Cl1—O2	1.4346 (16)
C5—N1—H1A	109.5	C4—C5—C6	122.22 (18)
C5—N1—H1B	109.5	C4—C5—N1	118.25 (16)
H1A—N1—H1B	109.5	C6—C5—N1	119.50 (16)
C5—N1—H1C	109.5	C7—C6—C5	118.39 (19)
H1A—N1—H1C	109.5	C7—C6—H6	120.8
H1B—N1—H1C	109.5	C5—C6—H6	120.8
N2—C1—C2	179.6 (3)	C6—C7—C2	120.1 (2)
C7—C2—C3	120.66 (19)	C6—C7—H7	120.0
C7—C2—C1	119.9 (2)	C2—C7—H7	120.0
C3—C2—C1	119.4 (2)	O4—Cl1—O3	109.51 (11)
C4—C3—C2	119.1 (2)	O4—Cl1—O1	109.25 (11)
C4—C3—H3	120.4	O3—Cl1—O1	108.89 (10)
C2—C3—H3	120.4	O4—Cl1—O2	109.01 (11)
C5—C4—C3	119.54 (19)	O3—Cl1—O2	110.69 (10)
C5—C4—H4	120.2	O1—Cl1—O2	109.47 (10)
C3—C4—H4	120.2
C7—C2—C3—C4	0.0 (3)	C4—C5—C6—C7	1.1 (3)
C1—C2—C3—C4	−179.7 (2)	N1—C5—C6—C7	−176.89 (19)
C2—C3—C4—C5	0.6 (3)	C5—C6—C7—C2	−0.4 (3)
C3—C4—C5—C6	−1.2 (3)	C3—C2—C7—C6	−0.1 (4)
C3—C4—C5—N1	176.83 (18)	C1—C2—C7—C6	179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.89	2.04	2.881 (2)	158.
N1—H1B···O3ii	0.89	1.98	2.855 (2)	166.
N1—H1C···O4iii	0.89	2.04	2.871 (2)	156.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.89	2.04	2.881 (2)	158
N1—H1B⋯O3ii	0.89	1.98	2.855 (2)	166
N1—H1C⋯O4iii	0.89	2.04	2.871 (2)	156

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