2-Methyl-1,2,4-triazolo[4,3-a]pyridin-2-ium tetra-fluoroborate.

In the title salt, C7H8N3 (+)·BF4 (-), the 1,2,4-triazolo[4,3-a]pyridinium cation is planar [maximum deviation of 0.016 (2) Å for all non-H atoms]. The cation and anion constitute a tight ionic pair with an F⋯N [2.911 (4) Å] inter-molecular attractive inter-action. The ionic pairs form dimers via stacking inter-actions between inversion-related cations, the normal distance between the cation planes being 3.376 (5) Å. The dimers are packed in stacks along the a axis and linked via C-H⋯F hydrogen bond, forming a three-dimensional network.

Related literature

For catalytic applications of triazoliums, see: Fisher et al. (2006 ▶); Enders et al. (2006 ▶); Wurz et al. (2012 ▶). For the synthesis of a related compound and for related structures, see: Ma et al. (2008 ▶); Wei et al. (2009 ▶).

Experimental

Crystal data

C7H8N3 +·BF4 −

M = 220.97

Orthorhombic,

a = 7.1508 (10) Å

b = 12.3070 (18) Å

c = 21.431 (3) Å

V = 1886.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.15 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.956, T max = 0.970

14891 measured reflections

1903 independent reflections

1616 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.245

S = 1.05

1903 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) luo7, I. DOI: 10.1107/S1600536813015535/kq2005sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015535/kq2005Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015535/kq2005Isup3.cml

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

C7H8N3+·BF4−	F(000) = 896
Mr = 220.97	Dx = 1.556 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 7.1508 (10) Å	µ = 0.15 mm−1
b = 12.3070 (18) Å	T = 296 K
c = 21.431 (3) Å	Block, colourless
V = 1886.0 (5) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Oxford Diffraction Xcalibur Eos diffractometer	1903 independent reflections
Radiation source: fine-focus sealed tube	1616 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 1.9°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −15→15
Tmin = 0.956, Tmax = 0.970	l = −26→26
14891 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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1597P)2 + 1.099P] where P = (Fo2 + 2Fc2)/3
1903 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

Experimental. Absorption correction: CrysAlis PRO, Agilent Technologies, Version 1.171.35.19, empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.7647 (5)	0.2546 (3)	0.66913 (12)	0.1094 (10)
F2	0.5247 (4)	0.3344 (2)	0.61787 (11)	0.1026 (10)
F3	0.7464 (5)	0.4320 (3)	0.66199 (16)	0.1321 (13)
F4	0.5444 (4)	0.3483 (3)	0.72252 (10)	0.1119 (10)
N1	0.1517 (3)	0.41555 (15)	0.59033 (9)	0.0398 (5)
N2	0.3053 (3)	0.57217 (18)	0.59455 (10)	0.0500 (6)
N3	0.2503 (3)	0.53825 (19)	0.65195 (10)	0.0500 (6)
C1	0.1599 (4)	0.4458 (2)	0.65054 (11)	0.0476 (6)
H1	0.1110	0.4084	0.6845	0.057*
C2	0.2444 (3)	0.49487 (18)	0.55689 (11)	0.0395 (6)
C3	0.2603 (3)	0.4838 (2)	0.49127 (12)	0.0486 (7)
H3	0.3203	0.5364	0.4674	0.058*
C4	0.1859 (4)	0.3948 (2)	0.46456 (13)	0.0564 (8)
H4	0.1952	0.3859	0.4216	0.068*
C5	0.0940 (5)	0.3147 (2)	0.50043 (15)	0.0599 (8)
H5	0.0454	0.2538	0.4805	0.072*
C6	0.0751 (4)	0.3243 (2)	0.56234 (15)	0.0544 (7)
H6	0.0130	0.2718	0.5856	0.065*
C7	0.2944 (6)	0.6039 (3)	0.70666 (15)	0.0775 (10)
H7A	0.2205	0.6690	0.7061	0.116*
H7B	0.4247	0.6227	0.7061	0.116*
H7C	0.2671	0.5632	0.7438	0.116*
B1	0.6389 (4)	0.3369 (3)	0.66829 (12)	0.0498 (7)

	U11	U22	U33	U12	U13	U23
F1	0.126 (2)	0.124 (2)	0.0777 (16)	0.0613 (17)	−0.0112 (13)	0.0018 (12)
F2	0.0934 (17)	0.150 (2)	0.0640 (13)	0.0390 (15)	−0.0291 (11)	−0.0343 (13)
F3	0.121 (3)	0.133 (2)	0.142 (3)	−0.044 (2)	−0.0029 (18)	0.0240 (19)
F4	0.0957 (18)	0.191 (3)	0.0492 (12)	−0.0054 (18)	0.0215 (11)	−0.0277 (13)
N1	0.0366 (10)	0.0397 (10)	0.0431 (10)	0.0044 (8)	0.0029 (7)	0.0056 (7)
N2	0.0533 (12)	0.0509 (12)	0.0456 (12)	−0.0067 (9)	0.0023 (9)	0.0053 (9)
N3	0.0536 (13)	0.0574 (13)	0.0389 (11)	0.0006 (10)	0.0010 (8)	0.0016 (9)
C1	0.0477 (14)	0.0564 (14)	0.0386 (12)	0.0048 (11)	0.0060 (9)	0.0102 (10)
C2	0.0329 (10)	0.0455 (12)	0.0401 (13)	0.0038 (8)	0.0022 (8)	0.0082 (9)
C3	0.0420 (13)	0.0621 (15)	0.0416 (13)	0.0070 (11)	0.0045 (10)	0.0087 (11)
C4	0.0525 (15)	0.0716 (18)	0.0452 (14)	0.0193 (13)	0.0003 (11)	−0.0086 (12)
C5	0.0613 (17)	0.0502 (15)	0.0682 (18)	0.0065 (12)	−0.0054 (14)	−0.0129 (12)
C6	0.0544 (15)	0.0413 (12)	0.0674 (17)	−0.0007 (11)	0.0006 (13)	0.0023 (11)
C7	0.096 (3)	0.088 (2)	0.0488 (16)	−0.0100 (19)	−0.0080 (17)	−0.0151 (15)
B1	0.0478 (16)	0.0710 (19)	0.0305 (12)	0.0042 (13)	0.0016 (10)	0.0002 (11)

F1—B1	1.356 (4)	C2—C3	1.418 (4)
F2—B1	1.355 (3)	C3—C4	1.345 (4)
F3—B1	1.407 (5)	C3—H3	0.9300
F4—B1	1.352 (3)	C4—C5	1.412 (5)
N1—C1	1.344 (3)	C4—H4	0.9300
N1—C2	1.380 (3)	C5—C6	1.339 (4)
N1—C6	1.386 (3)	C5—H5	0.9300
N2—C2	1.322 (3)	C6—H6	0.9300
N2—N3	1.357 (3)	C7—H7A	0.9600
N3—C1	1.309 (4)	C7—H7B	0.9600
N3—C7	1.459 (4)	C7—H7C	0.9600
C1—H1	0.9300
C1—N1—C2	106.3 (2)	C6—C5—C4	121.7 (3)
C1—N1—C6	131.1 (2)	C6—C5—H5	119.2
C2—N1—C6	122.5 (2)	C4—C5—H5	119.2
C2—N2—N3	103.7 (2)	C5—C6—N1	117.4 (2)
C1—N3—N2	112.9 (2)	C5—C6—H6	121.3
C1—N3—C7	127.4 (2)	N1—C6—H6	121.3
N2—N3—C7	119.7 (3)	N3—C7—H7A	109.5
N3—C1—N1	106.5 (2)	N3—C7—H7B	109.5
N3—C1—H1	126.7	H7A—C7—H7B	109.5
N1—C1—H1	126.7	N3—C7—H7C	109.5
N2—C2—N1	110.5 (2)	H7A—C7—H7C	109.5
N2—C2—C3	130.4 (2)	H7B—C7—H7C	109.5
N1—C2—C3	119.1 (2)	F4—B1—F2	112.8 (3)
C4—C3—C2	118.0 (2)	F4—B1—F1	113.4 (3)
C4—C3—H3	121.0	F2—B1—F1	113.2 (3)
C2—C3—H3	121.0	F4—B1—F3	105.6 (3)
C3—C4—C5	121.4 (3)	F2—B1—F3	105.8 (3)
C3—C4—H4	119.3	F1—B1—F3	105.1 (3)
C5—C4—H4	119.3
C2—N2—N3—C1	−0.2 (3)	C1—N1—C2—C3	179.2 (2)
C2—N2—N3—C7	179.7 (3)	C6—N1—C2—C3	0.8 (3)
N2—N3—C1—N1	−0.3 (3)	N2—C2—C3—C4	179.2 (3)
C7—N3—C1—N1	179.8 (3)	N1—C2—C3—C4	−0.9 (3)
C2—N1—C1—N3	0.7 (3)	C2—C3—C4—C5	0.2 (4)
C6—N1—C1—N3	179.0 (2)	C3—C4—C5—C6	0.7 (4)
N3—N2—C2—N1	0.7 (3)	C4—C5—C6—N1	−0.9 (4)
N3—N2—C2—C3	−179.5 (2)	C1—N1—C6—C5	−177.9 (3)
C1—N1—C2—N2	−0.9 (2)	C2—N1—C6—C5	0.1 (4)
C6—N1—C2—N2	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F4i	0.93	2.18	3.086 (3)	165
C5—H5···F2ii	0.93	2.38	3.169 (4)	143
C6—H6···F1iii	0.93	2.53	3.301 (5)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯F4i	0.93	2.18	3.086 (3)	165
C5—H5⋯F2ii	0.93	2.38	3.169 (4)	143
C6—H6⋯F1iii	0.93	2.53	3.301 (5)	141

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