1-Ethyl-3-(2,4,6-trimethyl-phen-yl)imidazolium tetra-fluoro-borate.

The title compound, C(14)H(19)N(2) (+)·BF(4) (-), was obtained by reaction of 1-ethyl-3-(2,4,6-trimethyl-phen-yl)imidazolium tetra-fluoro-borate with sodium tetra-fluoro-borate. The imidazole ring makes a dihedral angle of 78.92 (13)° with the benzene ring.

Related literature

For background, reviews and literature related to N-heterocyclic carbenes, see: Arduengo et al. (1991 ▶); Arduengo (1999 ▶); Wurtz & Glorius (2008 ▶); Haque et al. (2010 ▶).

Experimental

Crystal data

C14H19N2 +·BF4 −

M = 302.12

Monoclinic,

a = 7.7637 (7) Å

b = 9.1625 (9) Å

c = 21.559 (2) Å

β = 91.401 (2)°

V = 1533.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.16 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.983, T max = 0.989

9593 measured reflections

3013 independent reflections

2610 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.181

S = 1.08

3013 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536810027431/jh2177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027431/jh2177Isup2.hkl

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

C14H19N2+·BF4−	F(000) = 632
Mr = 302.12	Dx = 1.309 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3305 reflections
a = 7.7637 (7) Å	θ = 2.4–26.5°
b = 9.1625 (9) Å	µ = 0.11 mm−1
c = 21.559 (2) Å	T = 298 K
β = 91.401 (2)°	Block, colourless
V = 1533.2 (2) Å3	0.16 × 0.15 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3013 independent reflections
Radiation source: fine-focus sealed tube	2610 reflections with I > 2σ(I)
graphite	Rint = 0.026
phi and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.983, Tmax = 0.989	k = −11→9
9593 measured reflections	l = −25→26

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.181	w = 1/[σ2(Fo2) + (0.0826P)2 + 0.7775P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.026
3013 reflections	Δρmax = 0.30 e Å−3
195 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (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
B1	0.3268 (4)	0.6442 (3)	0.16502 (13)	0.0525 (7)
C1	0.7628 (3)	0.8458 (2)	0.04243 (9)	0.0430 (5)
C2	0.7570 (3)	0.7075 (3)	0.01582 (11)	0.0537 (6)
C3	0.7342 (3)	0.7003 (3)	−0.04830 (11)	0.0580 (6)
H3	0.7303	0.6093	−0.0674	0.070*
C4	0.7172 (3)	0.8245 (3)	−0.08467 (10)	0.0506 (6)
C5	0.7239 (3)	0.9592 (3)	−0.05564 (10)	0.0459 (5)
H5	0.7117	1.0429	−0.0797	0.055*
C6	0.7481 (3)	0.9738 (2)	0.00784 (10)	0.0428 (5)
C7	0.7746 (5)	0.5706 (3)	0.05432 (14)	0.0803 (9)
H7A	0.7588	0.4867	0.0281	0.120*
H7B	0.6890	0.5705	0.0857	0.120*
H7C	0.8873	0.5674	0.0736	0.120*
C8	0.6908 (4)	0.8130 (4)	−0.15396 (12)	0.0704 (8)
H8A	0.5704	0.8002	−0.1637	0.106*
H8B	0.7540	0.7308	−0.1691	0.106*
H8C	0.7311	0.9005	−0.1733	0.106*
C9	0.7608 (3)	1.1231 (3)	0.03680 (12)	0.0576 (6)
H9A	0.7485	1.1961	0.0051	0.086*
H9B	0.8709	1.1337	0.0575	0.086*
H9C	0.6710	1.1346	0.0663	0.086*
C10	0.9442 (3)	0.8499 (3)	0.14103 (11)	0.0585 (7)
H10	1.0503	0.8278	0.1243	0.070*
C11	0.9149 (3)	0.8783 (3)	0.20014 (11)	0.0560 (6)
H11	0.9968	0.8806	0.2323	0.067*
C12	0.6688 (3)	0.8903 (2)	0.14954 (10)	0.0432 (5)
H12	0.5519	0.9012	0.1403	0.052*
C13	0.6504 (3)	0.9378 (3)	0.26280 (10)	0.0535 (6)
H13A	0.5305	0.9583	0.2526	0.064*
H13B	0.7004	1.0248	0.2815	0.064*
C14	0.6599 (4)	0.8162 (3)	0.30850 (12)	0.0694 (8)
H14A	0.6102	0.7299	0.2903	0.104*
H14B	0.5974	0.8425	0.3447	0.104*
H14C	0.7781	0.7979	0.3200	0.104*
F1	0.3231 (3)	0.6699 (2)	0.10302 (8)	0.1034 (7)
F2	0.4792 (3)	0.5802 (3)	0.18106 (10)	0.1111 (8)
F3	0.3132 (2)	0.7798 (2)	0.19293 (8)	0.0817 (6)
F4	0.1928 (3)	0.5595 (2)	0.17995 (13)	0.1228 (9)
N1	0.7890 (2)	0.8590 (2)	0.10897 (8)	0.0433 (4)
N2	0.7417 (2)	0.9036 (2)	0.20523 (8)	0.0431 (4)

	U11	U22	U33	U12	U13	U23
B1	0.0531 (15)	0.0509 (15)	0.0534 (15)	0.0004 (12)	0.0011 (12)	0.0059 (12)
C1	0.0453 (11)	0.0476 (12)	0.0360 (10)	0.0015 (9)	0.0028 (8)	0.0006 (9)
C2	0.0673 (15)	0.0429 (13)	0.0512 (13)	0.0039 (11)	0.0072 (11)	0.0013 (10)
C3	0.0739 (17)	0.0475 (13)	0.0527 (14)	0.0036 (12)	0.0044 (11)	−0.0124 (11)
C4	0.0488 (12)	0.0596 (14)	0.0434 (12)	0.0042 (10)	0.0019 (9)	−0.0033 (10)
C5	0.0456 (12)	0.0490 (13)	0.0430 (11)	0.0031 (9)	0.0014 (9)	0.0061 (9)
C6	0.0402 (11)	0.0445 (12)	0.0437 (11)	0.0005 (9)	0.0018 (8)	−0.0006 (9)
C7	0.124 (3)	0.0468 (15)	0.0703 (19)	0.0093 (16)	0.0099 (17)	0.0075 (13)
C8	0.0803 (19)	0.083 (2)	0.0475 (14)	0.0079 (15)	−0.0039 (12)	−0.0100 (13)
C9	0.0716 (16)	0.0459 (13)	0.0553 (14)	−0.0023 (11)	0.0002 (11)	−0.0014 (11)
C10	0.0392 (12)	0.0832 (19)	0.0530 (14)	0.0065 (11)	0.0012 (10)	0.0082 (12)
C11	0.0452 (12)	0.0752 (17)	0.0474 (13)	0.0004 (11)	−0.0066 (10)	0.0069 (12)
C12	0.0388 (11)	0.0475 (12)	0.0432 (11)	0.0033 (9)	0.0008 (8)	0.0009 (9)
C13	0.0626 (14)	0.0561 (14)	0.0421 (12)	0.0027 (11)	0.0047 (10)	−0.0088 (10)
C14	0.0866 (19)	0.0722 (18)	0.0500 (14)	0.0049 (15)	0.0156 (13)	0.0078 (13)
F1	0.1536 (19)	0.0988 (14)	0.0573 (11)	0.0246 (13)	−0.0050 (11)	0.0061 (9)
F2	0.0887 (14)	0.1184 (17)	0.1254 (18)	0.0440 (12)	−0.0116 (12)	0.0259 (14)
F3	0.0730 (11)	0.0778 (12)	0.0940 (13)	−0.0010 (8)	−0.0021 (9)	−0.0243 (9)
F4	0.1021 (16)	0.0805 (14)	0.188 (3)	−0.0268 (11)	0.0534 (16)	0.0061 (14)
N1	0.0427 (9)	0.0483 (10)	0.0390 (9)	0.0030 (8)	0.0015 (7)	0.0027 (8)
N2	0.0475 (10)	0.0443 (10)	0.0375 (9)	0.0014 (8)	0.0010 (7)	0.0009 (7)

B1—F4	1.343 (3)	C8—H8B	0.9600
B1—F1	1.357 (3)	C8—H8C	0.9600
B1—F2	1.358 (3)	C9—H9A	0.9600
B1—F3	1.385 (3)	C9—H9B	0.9600
C1—C2	1.392 (3)	C9—H9C	0.9600
C1—C6	1.393 (3)	C10—C11	1.326 (3)
C1—N1	1.449 (3)	C10—N1	1.377 (3)
C2—C3	1.391 (3)	C10—H10	0.9300
C2—C7	1.509 (4)	C11—N2	1.371 (3)
C3—C4	1.387 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—N2	1.320 (3)
C4—C5	1.384 (3)	C12—N1	1.326 (3)
C4—C8	1.506 (3)	C12—H12	0.9300
C5—C6	1.383 (3)	C13—N2	1.478 (3)
C5—H5	0.9300	C13—C14	1.488 (4)
C6—C9	1.506 (3)	C13—H13A	0.9700
C7—H7A	0.9600	C13—H13B	0.9700
C7—H7B	0.9600	C14—H14A	0.9600
C7—H7C	0.9600	C14—H14B	0.9600
C8—H8A	0.9600	C14—H14C	0.9600
F4—B1—F1	109.8 (2)	H8B—C8—H8C	109.5
F4—B1—F2	111.4 (3)	C6—C9—H9A	109.5
F1—B1—F2	108.9 (2)	C6—C9—H9B	109.5
F4—B1—F3	110.2 (2)	H9A—C9—H9B	109.5
F1—B1—F3	105.8 (2)	C6—C9—H9C	109.5
F2—B1—F3	110.6 (2)	H9A—C9—H9C	109.5
C2—C1—C6	123.0 (2)	H9B—C9—H9C	109.5
C2—C1—N1	119.11 (19)	C11—C10—N1	107.6 (2)
C6—C1—N1	117.87 (19)	C11—C10—H10	126.2
C3—C2—C1	117.1 (2)	N1—C10—H10	126.2
C3—C2—C7	121.0 (2)	C10—C11—N2	107.6 (2)
C1—C2—C7	121.9 (2)	C10—C11—H11	126.2
C4—C3—C2	122.1 (2)	N2—C11—H11	126.2
C4—C3—H3	119.0	N2—C12—N1	109.08 (18)
C2—C3—H3	119.0	N2—C12—H12	125.5
C5—C4—C3	118.3 (2)	N1—C12—H12	125.5
C5—C4—C8	120.9 (2)	N2—C13—C14	112.4 (2)
C3—C4—C8	120.8 (2)	N2—C13—H13A	109.1
C6—C5—C4	122.5 (2)	C14—C13—H13A	109.1
C6—C5—H5	118.8	N2—C13—H13B	109.1
C4—C5—H5	118.8	C14—C13—H13B	109.1
C5—C6—C1	117.1 (2)	H13A—C13—H13B	107.9
C5—C6—C9	120.3 (2)	C13—C14—H14A	109.5
C1—C6—C9	122.62 (19)	C13—C14—H14B	109.5
C2—C7—H7A	109.5	H14A—C14—H14B	109.5
C2—C7—H7B	109.5	C13—C14—H14C	109.5
H7A—C7—H7B	109.5	H14A—C14—H14C	109.5
C2—C7—H7C	109.5	H14B—C14—H14C	109.5
H7A—C7—H7C	109.5	C12—N1—C10	107.65 (18)
H7B—C7—H7C	109.5	C12—N1—C1	125.94 (18)
C4—C8—H8A	109.5	C10—N1—C1	126.31 (18)
C4—C8—H8B	109.5	C12—N2—C11	108.11 (18)
H8A—C8—H8B	109.5	C12—N2—C13	125.41 (19)
C4—C8—H8C	109.5	C11—N2—C13	126.47 (19)
H8A—C8—H8C	109.5
C6—C1—C2—C3	−0.4 (4)	N1—C10—C11—N2	0.6 (3)
N1—C1—C2—C3	−179.0 (2)	N2—C12—N1—C10	1.0 (3)
C6—C1—C2—C7	179.5 (3)	N2—C12—N1—C1	−175.53 (19)
N1—C1—C2—C7	0.9 (4)	C11—C10—N1—C12	−1.0 (3)
C1—C2—C3—C4	−0.3 (4)	C11—C10—N1—C1	175.5 (2)
C7—C2—C3—C4	179.8 (3)	C2—C1—N1—C12	−103.7 (3)
C2—C3—C4—C5	0.2 (4)	C6—C1—N1—C12	77.7 (3)
C2—C3—C4—C8	−179.3 (2)	C2—C1—N1—C10	80.4 (3)
C3—C4—C5—C6	0.5 (3)	C6—C1—N1—C10	−98.3 (3)
C8—C4—C5—C6	−179.9 (2)	N1—C12—N2—C11	−0.7 (3)
C4—C5—C6—C1	−1.1 (3)	N1—C12—N2—C13	−179.9 (2)
C4—C5—C6—C9	177.8 (2)	C10—C11—N2—C12	0.0 (3)
C2—C1—C6—C5	1.1 (3)	C10—C11—N2—C13	179.2 (2)
N1—C1—C6—C5	179.73 (18)	C14—C13—N2—C12	115.6 (3)
C2—C1—C6—C9	−177.8 (2)	C14—C13—N2—C11	−63.4 (3)
N1—C1—C6—C9	0.8 (3)