2-Cyano-anilinium perchlorate.

In the title compound, C(7)H(7)N(2) (+)·ClO(4) (-), the cation is almost planar (r.m.s. deviation = 0.042 Å). In the crystal structure, the cations and anions are linked into a two-dimensional network parallel to (100) by N-H⋯O hydrogen bonds.

Related literature

For the crystal structure of 2-cyano­anilinium chloride, see: Oueslati et al. (2005 ▶). For Cl—O distances, see: Messai et al. (2009 ▶).

Experimental

Crystal data

C7H7N2 +·ClO4 −

M = 218.60

Monoclinic,

a = 11.089 (2) Å

b = 7.4561 (15) Å

c = 13.872 (5) Å

β = 128.454 (18)°

V = 898.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 298 K

0.40 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.90, T max = 1.00

9026 measured reflections

2070 independent reflections

1761 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.117

S = 1.11

2070 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.30 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003077/ci5023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003077/ci5023Isup2.hkl

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

C7H7N2+·ClO4−	F(000) = 448
Mr = 218.60	Dx = 1.617 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1761 reflections
a = 11.089 (2) Å	θ = 3.3–27.5°
b = 7.4561 (15) Å	µ = 0.42 mm−1
c = 13.872 (5) Å	T = 298 K
β = 128.454 (18)°	Needle, colourless
V = 898.2 (4) Å3	0.40 × 0.05 × 0.05 mm
Z = 4

Rigaku Mercury2 diffractometer	2070 independent reflections
Radiation source: fine-focus sealed tube	1761 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.3°
CCD profile fitting scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.90, Tmax = 1.00	l = −18→18
9026 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.522P] where P = (Fo2 + 2Fc2)/3
2070 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N2	0.10356 (18)	0.1622 (2)	0.40630 (16)	0.0351 (4)
H2A	0.0666	0.0523	0.3784	0.053*
H2B	0.0743	0.2332	0.3435	0.053*
H2C	0.0675	0.2053	0.4438	0.053*
N1	0.2247 (3)	0.4407 (3)	0.2725 (2)	0.0647 (7)
C7	0.2722 (2)	0.1553 (3)	0.49390 (19)	0.0327 (4)
C1	0.2853 (3)	0.3504 (3)	0.3573 (2)	0.0472 (6)
C5	0.5007 (3)	0.0559 (4)	0.6835 (2)	0.0629 (8)
H5	0.5493	−0.0064	0.7572	0.075*
C2	0.3588 (2)	0.2429 (3)	0.4665 (2)	0.0386 (5)
C6	0.3415 (3)	0.0628 (3)	0.6013 (2)	0.0469 (6)
H6	0.2827	0.0054	0.6189	0.056*
C4	0.5883 (3)	0.1403 (4)	0.6574 (3)	0.0662 (8)
H4	0.6952	0.1343	0.7133	0.079*
C3	0.5183 (3)	0.2326 (4)	0.5496 (3)	0.0547 (7)
H3	0.5775	0.2886	0.5320	0.066*
Cl1	0.91401 (6)	0.33466 (7)	0.57188 (4)	0.03477 (17)
O4	0.8898 (2)	0.2197 (2)	0.64175 (15)	0.0471 (4)
O3	0.7769 (2)	0.4305 (3)	0.48297 (16)	0.0681 (6)
O2	1.0336 (2)	0.4577 (2)	0.65476 (18)	0.0610 (5)
O1	0.9559 (2)	0.2236 (3)	0.51274 (17)	0.0574 (5)

	U11	U22	U33	U12	U13	U23
N2	0.0340 (9)	0.0349 (9)	0.0403 (10)	−0.0018 (7)	0.0250 (8)	−0.0023 (7)
N1	0.0733 (16)	0.0653 (15)	0.0617 (14)	−0.0195 (13)	0.0451 (13)	−0.0017 (12)
C7	0.0326 (10)	0.0306 (10)	0.0365 (10)	−0.0049 (8)	0.0223 (9)	−0.0081 (8)
C1	0.0499 (13)	0.0460 (13)	0.0576 (15)	−0.0166 (11)	0.0393 (13)	−0.0111 (12)
C5	0.0518 (15)	0.0571 (16)	0.0415 (13)	0.0008 (13)	0.0101 (12)	−0.0004 (12)
C2	0.0391 (11)	0.0351 (11)	0.0491 (12)	−0.0064 (9)	0.0311 (10)	−0.0094 (9)
C6	0.0476 (13)	0.0474 (13)	0.0384 (12)	−0.0070 (11)	0.0232 (11)	−0.0029 (10)
C4	0.0314 (12)	0.0587 (16)	0.0718 (19)	−0.0030 (12)	0.0140 (13)	−0.0145 (15)
C3	0.0393 (13)	0.0495 (14)	0.0762 (18)	−0.0111 (11)	0.0364 (14)	−0.0166 (13)
Cl1	0.0407 (3)	0.0312 (3)	0.0334 (3)	0.0017 (2)	0.0235 (2)	−0.00068 (19)
O4	0.0561 (10)	0.0436 (9)	0.0532 (10)	−0.0028 (8)	0.0397 (9)	0.0023 (8)
O3	0.0669 (12)	0.0745 (14)	0.0424 (10)	0.0332 (11)	0.0238 (9)	0.0151 (9)
O2	0.0660 (12)	0.0423 (10)	0.0638 (11)	−0.0212 (9)	0.0349 (10)	−0.0126 (8)
O1	0.0724 (12)	0.0587 (11)	0.0635 (11)	0.0041 (9)	0.0534 (11)	−0.0085 (9)

N2—C7	1.466 (2)	C5—H5	0.93
N2—H2A	0.89	C2—C3	1.388 (3)
N2—H2B	0.89	C6—H6	0.93
N2—H2C	0.89	C4—C3	1.367 (4)
N1—C1	1.143 (3)	C4—H4	0.93
C7—C6	1.364 (3)	C3—H3	0.93
C7—C2	1.396 (3)	Cl1—O3	1.4181 (18)
C1—C2	1.437 (4)	Cl1—O2	1.4233 (18)
C5—C4	1.381 (4)	Cl1—O1	1.4315 (17)
C5—C6	1.385 (4)	Cl1—O4	1.4385 (17)
C7—N2—H2A	109.5	C7—C6—C5	118.8 (2)
C7—N2—H2B	109.5	C7—C6—H6	120.6
H2A—N2—H2B	109.5	C5—C6—H6	120.6
C7—N2—H2C	109.5	C3—C4—C5	120.2 (2)
H2A—N2—H2C	109.5	C3—C4—H4	119.9
H2B—N2—H2C	109.5	C5—C4—H4	119.9
C6—C7—C2	121.2 (2)	C4—C3—C2	120.0 (2)
C6—C7—N2	118.99 (19)	C4—C3—H3	120.0
C2—C7—N2	119.78 (19)	C2—C3—H3	120.0
N1—C1—C2	177.1 (3)	O3—Cl1—O2	109.53 (13)
C4—C5—C6	120.8 (3)	O3—Cl1—O1	110.35 (12)
C4—C5—H5	119.6	O2—Cl1—O1	111.38 (12)
C6—C5—H5	119.6	O3—Cl1—O4	109.75 (12)
C3—C2—C7	119.0 (2)	O2—Cl1—O4	108.07 (11)
C3—C2—C1	120.1 (2)	O1—Cl1—O4	107.72 (11)
C7—C2—C1	120.8 (2)
C6—C7—C2—C3	1.0 (3)	C4—C5—C6—C7	−0.3 (4)
N2—C7—C2—C3	−179.0 (2)	C6—C5—C4—C3	0.2 (4)
C6—C7—C2—C1	−175.6 (2)	C5—C4—C3—C2	0.5 (4)
N2—C7—C2—C1	4.4 (3)	C7—C2—C3—C4	−1.1 (4)
C2—C7—C6—C5	−0.3 (4)	C1—C2—C3—C4	175.5 (2)
N2—C7—C6—C5	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4i	0.89	2.14	2.936 (2)	148
N2—H2B···O4ii	0.89	2.24	3.007 (3)	144
N2—H2C···O1iii	0.89	1.98	2.842 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4i	0.89	2.14	2.936 (2)	148
N2—H2B⋯O4ii	0.89	2.24	3.007 (3)	144
N2—H2C⋯O1iii	0.89	1.98	2.842 (2)	161

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