Cyanomethanaminium tetra-fluoro-borate.

In the title compound, C(2)H(5)N(2) (+)·BF(4) (-), the cations and anions are connected via inter-molecular N-H⋯F and C-H⋯F hydrogen bonds, forming a three-dimensional network.

Related literature

For background to the development of ferroelectric pure organic or inorganic compounds, see: Haertling (1999 ▶); Homes et al. (2001 ▶). For thesynthesis of a variety of compounds with potential piezoelectric and ferroelectric properties, see: Fu et al. (2009 ▶); Hang et al. (2009 ▶). For comparison bond lengths and bond angles, see: Wishkerman & Bernstein (2006 ▶).

Experimental

Crystal data

C2H5N2 +·BF4 −

M = 143.89

Orthorhombic,

a = 9.790 (2) Å

b = 10.204 (2) Å

c = 11.057 (2) Å

V = 1104.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.815, T max = 1.000

8605 measured reflections

969 independent reflections

891 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.097

S = 0.74

969 reflections

95 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 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/S1600536810025857/pv2302sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025857/pv2302Isup2.hkl

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

C2H5N2+·BF4−	F(000) = 576
Mr = 143.89	Dx = 1.730 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 970 reflections
a = 9.790 (2) Å	θ = 2.6–25.0°
b = 10.204 (2) Å	µ = 0.20 mm−1
c = 11.057 (2) Å	T = 293 K
V = 1104.6 (4) Å3	Prism, colorless
Z = 8	0.20 × 0.20 × 0.20 mm

Rigaku Mercury2 (2x2 bin mode) diffractometer	969 independent reflections
Radiation source: fine-focus sealed tube	891 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 13.6612 pixels mm-1	θmax = 25.0°, θmin = 3.4°
CCD_Profile_fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.815, Tmax = 1.000	l = −13→13
8605 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0711P)2 + 0.9831P] where P = (Fo2 + 2Fc2)/3
S = 0.74	(Δ/σ)max < 0.001
969 reflections	Δρmax = 0.21 e Å−3
95 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (4)

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
F1	0.20443 (11)	0.51691 (10)	0.27959 (10)	0.0507 (4)
F3	0.25530 (11)	0.69102 (10)	0.39731 (9)	0.0482 (4)
F4	0.39397 (10)	0.51360 (11)	0.39567 (11)	0.0536 (4)
N2	0.11384 (16)	0.80444 (15)	0.59675 (13)	0.0363 (4)
F2	0.18692 (13)	0.50016 (11)	0.48270 (11)	0.0586 (4)
C1	0.05747 (17)	0.69059 (16)	0.66197 (16)	0.0380 (4)
H1A	−0.0034	0.6428	0.6086	0.046*
H1B	0.1315	0.6323	0.6844	0.046*
C2	−0.01713 (15)	0.72917 (17)	0.77058 (14)	0.0363 (4)
N1	−0.07586 (17)	0.75568 (18)	0.85538 (14)	0.0553 (5)
B1	0.25945 (17)	0.55466 (18)	0.38936 (15)	0.0305 (4)
H2C	0.052 (3)	0.861 (3)	0.574 (2)	0.079 (8)*
H2B	0.170 (3)	0.852 (2)	0.645 (2)	0.079 (8)*
H2A	0.165 (3)	0.778 (2)	0.535 (2)	0.070 (7)*

	U11	U22	U33	U12	U13	U23
F1	0.0617 (7)	0.0499 (6)	0.0406 (6)	−0.0010 (5)	−0.0146 (5)	−0.0072 (4)
F3	0.0601 (7)	0.0311 (6)	0.0535 (7)	0.0006 (4)	0.0087 (5)	−0.0054 (4)
F4	0.0367 (6)	0.0529 (7)	0.0713 (8)	0.0075 (4)	−0.0063 (5)	−0.0017 (5)
N2	0.0375 (8)	0.0398 (8)	0.0314 (8)	0.0024 (6)	0.0054 (6)	0.0001 (6)
F2	0.0686 (8)	0.0589 (7)	0.0483 (7)	−0.0096 (6)	0.0185 (6)	0.0086 (5)
C1	0.0442 (9)	0.0329 (8)	0.0369 (9)	0.0026 (6)	0.0089 (7)	−0.0006 (7)
C2	0.0333 (8)	0.0423 (9)	0.0333 (9)	0.0022 (7)	0.0001 (7)	0.0032 (7)
N1	0.0533 (9)	0.0722 (12)	0.0404 (9)	0.0060 (8)	0.0127 (7)	−0.0008 (9)
B1	0.0320 (9)	0.0299 (9)	0.0296 (9)	−0.0005 (7)	0.0005 (7)	−0.0006 (6)

F1—B1	1.3828 (19)	N2—H2A	0.89 (3)
F3—B1	1.395 (2)	F2—B1	1.371 (2)
F4—B1	1.384 (2)	C1—C2	1.460 (2)
N2—C1	1.475 (2)	C1—H1A	0.9700
N2—H2C	0.87 (3)	C1—H1B	0.9700
N2—H2B	0.91 (3)	C2—N1	1.133 (2)
C1—N2—H2C	113.4 (17)	N2—C1—H1B	109.2
C1—N2—H2B	111.3 (16)	H1A—C1—H1B	107.9
H2C—N2—H2B	104 (2)	N1—C2—C1	178.16 (19)
C1—N2—H2A	110.3 (16)	F2—B1—F1	110.25 (14)
H2C—N2—H2A	112 (2)	F2—B1—F4	109.41 (14)
H2B—N2—H2A	106 (2)	F1—B1—F4	109.31 (14)
C2—C1—N2	112.16 (14)	F2—B1—F3	110.01 (13)
C2—C1—H1A	109.2	F1—B1—F3	108.78 (13)
N2—C1—H1A	109.2	F4—B1—F3	109.06 (13)
C2—C1—H1B	109.2

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···F2i	0.97	2.53	3.474 (2)	166
C1—H1B···F1ii	0.97	2.45	3.407 (2)	169
N2—H2A···F3	0.89 (2)	1.97 (2)	2.850 (2)	169 (2)
N2—H2B···F1iii	0.91 (3)	2.03 (3)	2.863 (2)	152 (2)
N2—H2C···F4iv	0.87 (3)	2.04 (3)	2.844 (2)	154 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯F2i	0.97	2.53	3.474 (2)	166
C1—H1B⋯F1ii	0.97	2.45	3.407 (2)	169
N2—H2A⋯F3	0.89 (2)	1.97 (2)	2.850 (2)	169 (2)
N2—H2B⋯F1iii	0.91 (3)	2.03 (3)	2.863 (2)	152 (2)
N2—H2C⋯F4iv	0.87 (3)	2.04 (3)	2.844 (2)	154 (2)

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