2-Cyano-anilinium tetra-fluoro-borate.

In the title compound, C(7)H(7)N(2) (+)·BF(4) (-), the non-H atoms of the cation are almost coplanar (r.m.s. deviation = 0.035 Å). The cations and anions are connected by inter-molecular N-H⋯F and N-H⋯N hydrogen bonds, forming a two-dimensional network parallel to (10).

Related literature

For the application of metal-organic coordination compounds, see: Fu et al. (2007 ▶); Chen et al. (2000 ▶); Fu & Xiong (2008 ▶); Xiong et al. (1999 ▶); Xie et al. (2003 ▶); Zhang et al. (2001 ▶). For general background to nitrile derivatives, see: Fu et al. (2008 ▶); Wang et al. (2002 ▶).

Experimental

Crystal data

C7H7N2 +·BF4 −

M = 205.96

Monoclinic,

a = 10.971 (2) Å

b = 7.3565 (15) Å

c = 11.022 (2) Å

β = 103.11 (3)°

V = 866.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 298 K

0.30 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.96, T max = 1.00 (expected range = 0.931–0.969)

8625 measured reflections

1978 independent reflections

1417 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.141

S = 1.08

1978 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.32 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/S1600536809032863/ci2881sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032863/ci2881Isup2.hkl

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

C7H7N2+·BF4−	F(000) = 416
Mr = 205.96	Dx = 1.579 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1417 reflections
a = 10.971 (2) Å	θ = 3.4–27.5°
b = 7.3565 (15) Å	µ = 0.16 mm−1
c = 11.022 (2) Å	T = 298 K
β = 103.11 (3)°	Block, colourless
V = 866.4 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	1978 independent reflections
Radiation source: fine-focus sealed tube	1417 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.4°
CCD profile fitting scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.96, Tmax = 1.00	l = −14→14
8625 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.4139P] where P = (Fo2 + 2Fc2)/3
1978 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.32 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
F4	0.36113 (13)	0.72246 (19)	0.25229 (13)	0.0500 (4)
F3	0.48625 (14)	0.7353 (2)	0.44366 (13)	0.0575 (4)
N1	0.59296 (16)	0.6600 (3)	0.69414 (15)	0.0337 (4)
H1A	0.6182	0.5482	0.6812	0.051*
H1B	0.6589	0.7275	0.7293	0.051*
H1C	0.5548	0.7094	0.6218	0.051*
F2	0.34337 (15)	0.9602 (2)	0.37300 (16)	0.0625 (5)
C1	0.50557 (18)	0.6518 (3)	0.77689 (18)	0.0302 (5)
F1	0.51445 (14)	0.9330 (3)	0.29556 (18)	0.0737 (6)
C2	0.5337 (2)	0.7425 (3)	0.89064 (19)	0.0348 (5)
C6	0.3969 (2)	0.5547 (3)	0.7402 (2)	0.0437 (6)
H6	0.3792	0.4939	0.6643	0.052*
N2	0.7317 (2)	0.9429 (3)	0.9488 (2)	0.0586 (6)
C7	0.6444 (2)	0.8517 (3)	0.9248 (2)	0.0428 (6)
B1	0.4282 (2)	0.8402 (3)	0.3425 (2)	0.0359 (6)
C4	0.3405 (3)	0.6365 (4)	0.9311 (3)	0.0580 (8)
H4	0.2840	0.6313	0.9824	0.070*
C3	0.4507 (2)	0.7323 (3)	0.9687 (2)	0.0483 (6)
H3	0.4693	0.7897	1.0458	0.058*
C5	0.3138 (2)	0.5485 (4)	0.8180 (3)	0.0570 (7)
H5	0.2393	0.4842	0.7934	0.068*

	U11	U22	U33	U12	U13	U23
F4	0.0566 (9)	0.0453 (8)	0.0442 (8)	−0.0023 (6)	0.0037 (7)	−0.0056 (6)
F3	0.0587 (9)	0.0613 (10)	0.0455 (8)	0.0069 (7)	−0.0029 (7)	0.0162 (7)
N1	0.0376 (10)	0.0351 (9)	0.0291 (9)	0.0028 (8)	0.0092 (7)	−0.0004 (7)
F2	0.0658 (9)	0.0467 (9)	0.0762 (11)	0.0167 (7)	0.0186 (8)	−0.0097 (8)
C1	0.0324 (10)	0.0288 (10)	0.0303 (10)	0.0072 (8)	0.0091 (8)	0.0036 (8)
F1	0.0435 (8)	0.0830 (12)	0.0922 (13)	−0.0162 (8)	0.0107 (8)	0.0342 (10)
C2	0.0420 (11)	0.0316 (11)	0.0311 (11)	0.0065 (9)	0.0091 (9)	0.0001 (9)
C6	0.0356 (12)	0.0447 (14)	0.0491 (14)	0.0034 (10)	0.0058 (10)	−0.0046 (11)
N2	0.0597 (14)	0.0587 (14)	0.0558 (14)	−0.0010 (12)	0.0095 (11)	−0.0178 (11)
C7	0.0542 (15)	0.0392 (13)	0.0347 (12)	0.0088 (12)	0.0094 (11)	−0.0075 (10)
B1	0.0324 (12)	0.0315 (12)	0.0412 (13)	0.0004 (10)	0.0030 (10)	0.0053 (11)
C4	0.0609 (17)	0.0541 (17)	0.0729 (19)	0.0135 (14)	0.0445 (15)	0.0118 (14)
C3	0.0670 (16)	0.0430 (13)	0.0422 (13)	0.0147 (12)	0.0277 (12)	0.0018 (10)
C5	0.0375 (13)	0.0529 (16)	0.085 (2)	0.0011 (12)	0.0223 (13)	0.0022 (14)

F4—B1	1.396 (3)	C2—C3	1.389 (3)
F3—B1	1.387 (3)	C2—C7	1.434 (3)
N1—C1	1.467 (2)	C6—C5	1.387 (4)
N1—H1A	0.89	C6—H6	0.93
N1—H1B	0.89	N2—C7	1.150 (3)
N1—H1C	0.89	C4—C5	1.376 (4)
F2—B1	1.379 (3)	C4—C3	1.379 (4)
C1—C6	1.370 (3)	C4—H4	0.93
C1—C2	1.392 (3)	C3—H3	0.93
F1—B1	1.361 (3)	C5—H5	0.93
C1—N1—H1A	109.5	F1—B1—F2	109.7 (2)
C1—N1—H1B	109.5	F1—B1—F3	110.68 (19)
H1A—N1—H1B	109.5	F2—B1—F3	111.9 (2)
C1—N1—H1C	109.5	F1—B1—F4	109.9 (2)
H1A—N1—H1C	109.5	F2—B1—F4	107.16 (18)
H1B—N1—H1C	109.5	F3—B1—F4	107.42 (19)
C6—C1—C2	121.1 (2)	C5—C4—C3	120.3 (2)
C6—C1—N1	119.06 (19)	C5—C4—H4	119.9
C2—C1—N1	119.87 (19)	C3—C4—H4	119.9
C3—C2—C1	119.3 (2)	C4—C3—C2	119.7 (2)
C3—C2—C7	120.2 (2)	C4—C3—H3	120.2
C1—C2—C7	120.42 (19)	C2—C3—H3	120.2
C1—C6—C5	119.0 (2)	C4—C5—C6	120.6 (2)
C1—C6—H6	120.5	C4—C5—H5	119.7
C5—C6—H6	120.5	C6—C5—H5	119.7
N2—C7—C2	177.7 (3)
C6—C1—C2—C3	0.8 (3)	C5—C4—C3—C2	1.2 (4)
N1—C1—C2—C3	−179.40 (19)	C1—C2—C3—C4	−1.6 (3)
C6—C1—C2—C7	−176.6 (2)	C7—C2—C3—C4	175.8 (2)
N1—C1—C2—C7	3.2 (3)	C3—C4—C5—C6	0.0 (4)
C2—C1—C6—C5	0.4 (3)	C1—C6—C5—C4	−0.8 (4)
N1—C1—C6—C5	−179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.89	2.54	3.179 (3)	130
N1—H1A···F4ii	0.89	2.12	2.896 (2)	146
N1—H1B···F4iii	0.89	2.21	2.993 (2)	147
N1—H1C···F3	0.89	1.95	2.799 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.89	2.54	3.179 (3)	130
N1—H1A⋯F4ii	0.89	2.12	2.896 (2)	146
N1—H1B⋯F4iii	0.89	2.21	2.993 (2)	147
N1—H1C⋯F3	0.89	1.95	2.799 (2)	160

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