N-[Amino(imino)methyl]uronium tetrafluoroborate.

In the title compound, C(2)H(7)N(4)O(+)·BF(4) (-), inter-molecular N-H⋯O hydrogen bonds connect the cations into chains parallel to the c axis, with graph-set motif C(4). These chains are in turn connected into a three-dimensional network by inter-molecular N-H⋯F hydrogen bonds. The B-F distances distances in the anion are not equal.

Related literature

For the non-centrosymmetric structure, containing a 2-carbamoylguanidinium cation, that is promising for applications in non-linear optics, see: Fridrichová, Němec, Císařová & Chvostová (2010 ▶); Fridrichová, Němec, Císařová & Němec (2010 ▶); Kroupa & Fridrichová (2011 ▶). For related stuctures and a detailed description of the preparation of the title cation, see: Fábry et al. (2012a ▶,b ▶,c ▶). For structures with rather strong N—H⋯F hydrogen bonds, see: Ali et al. (2007 ▶); Bardaji et al. (2002 ▶); Blue et al. (2003 ▶); Byrne et al. (2008 ▶); Zhao & Betley (2011 ▶). For information on fluorine as acceptor in organic hydrogen bonds, see: Dunitz & Taylor (1997 ▶). For hydrogen-bond classification and graph-set motifs, see: Desiraju & Steiner (1999 ▶); Etter et al. (1990 ▶). For a description of the Cambridge Structural Database (CSD), see: Allen (2002 ▶). For the extinction correction, see: Becker & Coppens (1974 ▶).

Experimental

Crystal data

C2H7N4O+·BF4 −

M = 189.9

Monoclinic,

a = 7.8409 (3) Å

b = 9.6373 (4) Å

c = 9.5199 (4) Å

β = 105.689 (3)°

V = 692.57 (5) Å3

Z = 4

Cu Kα radiation

μ = 1.86 mm−1

T = 120 K

0.51 × 0.30 × 0.17 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.534, T max = 0.733

7265 measured reflections

1230 independent reflections

1189 reflections with I > 3σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.081

S = 1.74

1230 reflections

131 parameters

Only H-atom coordinates refined

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1997 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2007 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010665/lh5427sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010665/lh5427Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010665/lh5427Isup4.smi

Supplementary material file. DOI: 10.1107/S1600536812010665/lh5427Isup4.cml

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

C2H7N4O+·BF4−	F(000) = 384
Mr = 189.9	Dx = 1.821 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 5746 reflections
a = 7.8409 (3) Å	θ = 4.6–67°
b = 9.6373 (4) Å	µ = 1.86 mm−1
c = 9.5199 (4) Å	T = 120 K
β = 105.689 (3)°	Irregular shape, colourless
V = 692.57 (5) Å3	0.51 × 0.30 × 0.17 mm
Z = 4

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1230 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1189 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.020
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 5.9°
Rotation method data acquisition using ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.534, Tmax = 0.733	l = −11→10
7265 measured reflections

Refinement on F2	Only H-atom coordinates refined
R[F2 > 2σ(F2)] = 0.024	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
wR(F2) = 0.081	(Δ/σ)max = 0.006
S = 1.74	Δρmax = 0.13 e Å−3
1230 reflections	Δρmin = −0.15 e Å−3
131 parameters	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 1600 (300)
7 constraints

Experimental. CrysAlisPro (Agilent Technologies, 2010) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
B1	0.66007 (15)	0.44707 (12)	0.78507 (13)	0.0190 (4)
F1	0.54351 (8)	0.40448 (7)	0.86358 (7)	0.0295 (3)
F2	0.83067 (8)	0.45670 (7)	0.87576 (7)	0.0254 (2)
F3	0.65411 (9)	0.35814 (7)	0.67085 (7)	0.0304 (3)
F4	0.60448 (8)	0.58120 (6)	0.72842 (7)	0.0242 (2)
N1	1.29213 (13)	0.25144 (10)	0.99490 (11)	0.0230 (3)
H1n1	1.3573 (19)	0.2796 (14)	1.0783 (17)	0.0276*
H2n1	1.3380 (19)	0.2346 (15)	0.9280 (17)	0.0276*
C1	1.12706 (13)	0.21215 (10)	0.98698 (11)	0.0180 (3)
O1	1.05904 (10)	0.21991 (8)	1.08889 (8)	0.0212 (3)
N2	1.03592 (11)	0.16014 (9)	0.85077 (9)	0.0183 (3)
H1n2	1.0786 (18)	0.1719 (14)	0.7805 (17)	0.022*
C2	0.86829 (13)	0.10769 (10)	0.81483 (11)	0.0179 (3)
N3	0.77643 (12)	0.10138 (10)	0.91111 (10)	0.0211 (3)
H1n3	0.666 (2)	0.0746 (14)	0.8846 (15)	0.0253*
H2n3	0.8179 (18)	0.1386 (15)	0.9944 (17)	0.0253*
N4	0.80477 (13)	0.06150 (10)	0.68075 (11)	0.0221 (3)
H1n4	0.702 (2)	0.0267 (15)	0.6529 (15)	0.0265*
H2n4	0.8632 (19)	0.0642 (14)	0.6222 (16)	0.0265*

	U11	U22	U33	U12	U13	U23
B1	0.0181 (6)	0.0208 (6)	0.0181 (6)	0.0008 (4)	0.0052 (5)	0.0009 (4)
F1	0.0255 (4)	0.0333 (4)	0.0341 (4)	0.0011 (3)	0.0155 (3)	0.0082 (3)
F2	0.0189 (4)	0.0318 (4)	0.0229 (4)	0.0015 (2)	0.0015 (3)	0.0031 (2)
F3	0.0343 (4)	0.0309 (4)	0.0255 (4)	0.0008 (3)	0.0074 (3)	−0.0079 (3)
F4	0.0228 (4)	0.0227 (4)	0.0254 (4)	0.0021 (2)	0.0033 (3)	0.0046 (2)
N1	0.0199 (5)	0.0296 (5)	0.0203 (5)	−0.0050 (4)	0.0070 (4)	−0.0057 (4)
C1	0.0203 (5)	0.0156 (5)	0.0177 (5)	0.0015 (4)	0.0048 (4)	0.0008 (3)
O1	0.0222 (4)	0.0257 (4)	0.0165 (4)	−0.0024 (3)	0.0065 (3)	−0.0025 (3)
N2	0.0188 (5)	0.0231 (5)	0.0141 (5)	−0.0012 (3)	0.0060 (4)	0.0003 (3)
C2	0.0181 (5)	0.0162 (5)	0.0183 (5)	0.0030 (4)	0.0031 (4)	0.0021 (4)
N3	0.0174 (5)	0.0262 (5)	0.0196 (5)	−0.0025 (3)	0.0052 (4)	−0.0031 (4)
N4	0.0202 (5)	0.0273 (5)	0.0178 (5)	−0.0020 (4)	0.0038 (4)	−0.0029 (4)

B1—F1	1.3899 (15)	C2—N4	1.3159 (14)
B1—F2	1.3852 (12)	N1—H1n1	0.863 (14)
B1—F3	1.3754 (14)	N1—H2n1	0.828 (18)
B1—F4	1.4229 (13)	N2—H1n2	0.833 (17)
N1—C1	1.3309 (15)	N3—H1n3	0.873 (15)
C1—O1	1.2293 (14)	N3—H2n3	0.850 (15)
C1—N2	1.3936 (12)	N4—H1n4	0.844 (15)
N2—C2	1.3627 (13)	N4—H2n4	0.812 (17)
C2—N3	1.3113 (16)
F1—B1—F2	110.44 (9)	N3—C2—N4	121.80 (10)
F1—B1—F3	110.76 (9)	H1n1—N1—H2n1	119.8 (15)
F1—B1—F4	107.07 (9)	H1n3—N3—H2n3	119.6 (15)
F2—B1—F3	110.80 (9)	H1n4—N4—H2n4	117.5 (14)
F2—B1—F4	108.70 (8)	H1n1—N1—C1	117.8 (11)
F3—B1—F4	108.97 (9)	H2n1—N1—C1	121.3 (9)
N1—C1—O1	124.11 (9)	C1—N2—H1n2	118.8 (9)
N1—C1—N2	113.66 (10)	H1n2—N2—C2	114.7 (9)
O1—C1—N2	122.24 (9)	C2—N3—H1n3	120.0 (10)
C1—N2—C2	125.74 (10)	C2—N3—H2n3	119.2 (11)
N2—C2—N3	121.10 (9)	C2—N4—H1n4	121.2 (11)
N2—C2—N4	117.09 (11)	C2—N4—H2n4	121.3 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n1···F4i	0.863 (14)	2.231 (16)	3.0069 (12)	149.5 (13)
N1—H2n1···F4ii	0.828 (18)	2.230 (16)	2.9666 (13)	148.5 (14)
N2—H1n2···O1iii	0.833 (17)	2.070 (15)	2.7981 (12)	145.7 (12)
N3—H1n3···F4iv	0.873 (15)	2.104 (14)	2.9286 (11)	157.4 (13)
N3—H2n3···F3v	0.850 (15)	2.375 (17)	2.9102 (13)	121.5 (12)
N3—H2n3···O1	0.850 (15)	2.020 (13)	2.6555 (11)	130.9 (15)
N4—H1n4···F1iv	0.844 (15)	2.229 (16)	3.0499 (12)	164.5 (13)
N4—H2n4···F2iii	0.812 (17)	2.299 (15)	2.9700 (13)	140.4 (12)
N1—H2n1···F1vi	0.828 (18)	2.488 (16)	2.9927 (13)	120.4 (12)
N3—H2n3···F3v	0.850 (15)	2.375 (17)	2.9102 (13)	121.5 (12)
N4—H2n4···O1iii	0.812 (17)	2.655 (15)	3.1813 (13)	123.9 (11)

Table 1

Selected bond lengths (Å)

B1—F1	1.3899 (15)
B1—F2	1.3852 (12)
B1—F3	1.3754 (14)
B1—F4	1.4229 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n1⋯F4i	0.863 (14)	2.231 (16)	3.0069 (12)	149.5 (13)
N1—H2n1⋯F4ii	0.828 (18)	2.230 (16)	2.9666 (13)	148.5 (14)
N2—H1n2⋯O1iii	0.833 (17)	2.070 (15)	2.7981 (12)	145.7 (12)
N3—H1n3⋯F4iv	0.873 (15)	2.104 (14)	2.9286 (11)	157.4 (13)
N3—H2n3⋯F3v	0.850 (15)	2.375 (17)	2.9102 (13)	121.5 (12)
N3—H2n3⋯O1	0.850 (15)	2.020 (13)	2.6555 (11)	130.9 (15)
N4—H1n4⋯F1iv	0.844 (15)	2.229 (16)	3.0499 (12)	164.5 (13)
N4—H2n4⋯F2iii	0.812 (17)	2.299 (15)	2.9700 (13)	140.4 (12)
N1—H2n1⋯F1vi	0.828 (18)	2.488 (16)	2.9927 (13)	120.4 (12)
N3—H2n3⋯F3v	0.850 (15)	2.375 (17)	2.9102 (13)	121.5 (12)
N4—H2n4⋯O1iii	0.812 (17)	2.655 (15)	3.1813 (13)	123.9 (11)

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