Tetra­ethyl­ammonium 12-phenyl­ethynylcarba-closo-dodeca­borate, [Et4N][12-PhCC-closo-CB11H11]

Finze, M.; Reiss, G.J.

doi:10.1107/S1600536809013300

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1048

doi:10.1107/S1600536809013300

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Tetraethylammonium 12-phenylethynylcarba-closo-dodecaborate, [Et₄N][12-PhCC-closo-CB₁₁H₁₁]

Maik Finze ^a ^* and Guido J. Reiss ^a

^aInstitut für Anorganische Chemie und Strukturchemie II, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany
^*Correspondence e-mail: maik.finze@uni-duesseldorf.de

(Received 23 March 2009; accepted 7 April 2009; online 18 April 2009)

The asymmetric unit of the title compound, C₈H₂₀N⁺·C₉H₁₆B₁₁⁻ or [Et₄N][12-PhCC-closo-CB₁₁H₁₁], consists of one cation and one anion. The [12-PhCC-closo-CB₁₁H₁₁]⁻ anion is close to possessing a non-crystallographic plane of mirror symmetry with a nearly linear B—C≡C—C group, with B—C≡C and C≡C—C angles of 177.15 (16) and 176.64 (17)°, respectively.

Related literature

Carba-closo-dodecaborate anions with functional groups are potential building blocks for a variety of applications, for example ionic liquids and liquid crystals, see: Körbe et al. (2006 ). Recently, we have shown that {closo-CB₁₁} clusters with one or two alkynyl groups bonded to boron are accessible by Pd-catalysed Kumada-type cross-coupling reactions starting from the corresponding mono- and diiodinated clusters, see: Finze (2008 , 2009 ).

Experimental

Crystal data

C₈H₂₀N⁺·C₉H₁₆B₁₁⁻
M_r = 373.38
Triclinic, $[P \overline 1]$
a = 8.8201 (6) Å
b = 12.0929 (11) Å
c = 12.1858 (11) Å
α = 81.032 (7)°
β = 79.899 (7)°
γ = 71.553 (7)°
V = 1206.82 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.05 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Stoe Stadi CCD diffractometer
Absorption correction: none
17081 measured reflections
4219 independent reflections
3228 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.101
S = 1.00
4219 reflections
363 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis CCD (Kuma, 2000 $[Kuma (2000). CrysAlis CCD and CrysAlis RED. Kuma Diffraction, Wrocław, Poland.]$ ); cell refinement: CrysAlis RED (Kuma, 2000 $[Kuma (2000). CrysAlis CCD and CrysAlis RED. Kuma Diffraction, Wrocław, Poland.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013300/br2103sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013300/br2103Isup2.hkl

checkCIF report

Comment top

Carba-closo-dodecaborate anions with functional groups are potential building blocks for a variety of applications, for example ionic liquids and liquid crystals (Körbe, 2006). Recently, we have shown that {closo-CB₁₁} clusters with one or two alkynyl groups bonded to boron are accessible by Pd-catalyzed Kumada-type cross-coupling reactions starting from the corresponding mono- and diiodinated clusters, respectively (Finze, 2008, 2009). The title compound [Et₄N][12-PhCC-closo-CB₁₁H₁₁] crystallizes in the triclinic centrosymmetric space group P1 with one formula unit in the asymmetric unit. The bond lengths and angles in the [12-PhCC-closo-CB₁₁H₁₁]^- anion in its [Et₄N]⁺ salt are close to the values reported for the respective Cs⁺ salt (Finze, 2008). However, the quality of the data for the [Et₄N]⁺ salt described herein is significantly better than the quality of the data obtained for the Cs⁺ salt. The thermal properties of [Et₄N][12-PhCC-closo-CB₁₁H₁₁] were studied by differential scanning calorimetry (DSC). The salt melts at 433 K and is thermally stable up to 518 K.

Related literature top

Carba-closo-dodecaborate anions with functional groups are potential building blocks for a variety of applications, for example ionic liquids and liquid crystals, see: Körbe et al. (2006). Recently, we have shown that {closo-CB₁₁} clusters with one or two alkynyl groups bonded to boron are accessible by Pd-catalysed Kumada-type cross-coupling reactions starting from the corresponding mono- and diiodinated clusters, see: Finze (2008, 2009).

Experimental top

[Et₄N][12-PhCC-closo-CB₁₁H₁₁] was synthesized according to a published procedure (Finze, 2008). The spectroscopic data have been reported earlier (Finze, 2008). The salt was dissolved in acetonitrile and slow evaporation of the solvent resulted in colorless crystals.

Structure description top

Carba-closo-dodecaborate anions with functional groups are potential building blocks for a variety of applications, for example ionic liquids and liquid crystals, see: Körbe et al. (2006). Recently, we have shown that {closo-CB₁₁} clusters with one or two alkynyl groups bonded to boron are accessible by Pd-catalysed Kumada-type cross-coupling reactions starting from the corresponding mono- and diiodinated clusters, see: Finze (2008, 2009).

Computing details top

Data collection: CrysAlis CCD (Kuma, 2000); cell refinement: CrysAlis RED (Kuma, 2000); data reduction: CrysAlis RED (Kuma, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. : The 12-phenylethinylcarba-closo-dodecaborate cation in [Et₄N][12-PhCC-closo-CB₁₁H₁₁]. Hydrogen atoms are drawn with an arbitrary radius and the displacement ellipsoids are shown at the 40% probability level.
	Fig. 2. : The tetraethylammonium cation in [Et₄N][12-PhCC-closo-CB₁₁H₁₁]. Hydrogen atoms are drawn with an arbitrary radius and the displacement ellipsoids are shown at the 40% probability level.

Tetraethylammonium 12-phenylethynylcarba-closo-dodecaborate top

Crystal data top

C₈H₂₀N⁺·C₉H₁₆B₁₁⁻	Z = 2
M_r = 373.38	F(000) = 400
Triclinic, P1	D_x = 1.031 Mg m⁻³
Hall symbol: -P 1	Melting point: 433 K
a = 8.8201 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.0929 (11) Å	Cell parameters from 4623 reflections
c = 12.1858 (11) Å	θ = 6.8–20.7°
α = 81.032 (7)°	µ = 0.05 mm⁻¹
β = 79.899 (7)°	T = 293 K
γ = 71.553 (7)°	Block, colourless
V = 1206.82 (18) Å³	0.3 × 0.25 × 0.2 mm

Data collection top

Stoe Stadi CCD diffractometer	3228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.051
Graphite monochromator	θ_max = 25.0°, θ_min = 5.1°
ω scans	h = −10→10
17081 measured reflections	k = −14→14
4219 independent reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.01P)² + 0.45P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4219 reflections	Δρ_max = 0.16 e Å⁻³
363 parameters	Δρ_min = −0.16 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: 0.037 (3)

Crystal data top

C₈H₂₀N⁺·C₉H₁₆B₁₁⁻	γ = 71.553 (7)°
M_r = 373.38	V = 1206.82 (18) Å³
Triclinic, P1	Z = 2
a = 8.8201 (6) Å	Mo Kα radiation
b = 12.0929 (11) Å	µ = 0.05 mm⁻¹
c = 12.1858 (11) Å	T = 293 K
α = 81.032 (7)°	0.3 × 0.25 × 0.2 mm
β = 79.899 (7)°

Data collection top

Stoe Stadi CCD diffractometer	3228 reflections with I > 2σ(I)
17081 measured reflections	R_int = 0.051
4219 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.16 e Å⁻³
4219 reflections	Δρ_min = −0.16 e Å⁻³
363 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.02767 (14)	0.15270 (10)	0.23820 (10)	0.0443 (3)
C11	0.1693 (2)	0.11482 (16)	0.30484 (17)	0.0572 (4)
H11A	0.145 (2)	0.1795 (17)	0.3523 (15)	0.075 (6)*
H11B	0.264 (2)	0.1153 (15)	0.2471 (15)	0.067 (5)*
C12	0.1927 (2)	−0.00116 (17)	0.37487 (17)	0.0756 (6)
H12A	0.0981	0.0009	0.4282	0.115 (5)*
H12B	0.2842	−0.0170	0.4139	0.115 (5)*
H12C	0.2110	−0.0617	0.3274	0.115 (5)*
C13	0.0403 (3)	0.06144 (18)	0.16256 (17)	0.0621 (5)
H13A	0.034 (2)	−0.0082 (16)	0.2173 (15)	0.071 (5)*
H13B	−0.055 (2)	0.0949 (16)	0.1246 (15)	0.074 (6)*
C14	0.1930 (3)	0.0312 (2)	0.08048 (18)	0.0937 (7)
H14A	0.1895	−0.0262	0.0355	0.149 (6)*
H14B	0.2844	0.0001	0.1208	0.149 (6)*
H14C	0.2024	0.1005	0.0329	0.149 (6)*
C15	0.0310 (3)	0.26924 (16)	0.17111 (18)	0.0655 (5)
H15A	0.021 (2)	0.3226 (17)	0.2329 (15)	0.074 (6)*
H15B	0.140 (2)	0.2534 (16)	0.1284 (16)	0.075 (6)*
C16	−0.0984 (3)	0.32222 (19)	0.09677 (17)	0.0891 (7)
H16A	−0.0897	0.2691	0.0434	0.126 (5)*
H16B	−0.0861	0.3948	0.0577	0.126 (5)*
H16C	−0.2023	0.3366	0.1416	0.126 (5)*
C17	−0.12997 (19)	0.16523 (15)	0.31589 (15)	0.0494 (4)
H17A	−0.119 (2)	0.0852 (16)	0.3536 (14)	0.062 (5)*
H17B	−0.207 (2)	0.1839 (14)	0.2658 (14)	0.060 (5)*
C18	−0.1717 (2)	0.25361 (16)	0.39823 (15)	0.0660 (5)
H18A	−0.1861	0.3305	0.3586	0.101 (4)*
H18B	−0.0860	0.2361	0.4430	0.101 (4)*
H18C	−0.2697	0.2509	0.4459	0.101 (4)*
C1	0.8578 (2)	−0.42097 (13)	0.37589 (14)	0.0537 (4)
H1	0.905 (2)	−0.5044 (15)	0.4091 (13)	0.064 (5)*
B2	0.7262 (3)	−0.39328 (16)	0.28148 (17)	0.0561 (5)
H2	0.6959 (19)	−0.4675 (14)	0.2554 (13)	0.064 (5)*
B3	0.9243 (2)	−0.38352 (16)	0.23998 (17)	0.0555 (5)
H3	1.012 (2)	−0.4499 (15)	0.1888 (13)	0.065 (5)*
B4	0.9825 (2)	−0.33524 (16)	0.35199 (17)	0.0535 (5)
H4	1.108 (2)	−0.3739 (14)	0.3728 (13)	0.064 (5)*
B5	0.8195 (2)	−0.31531 (15)	0.46186 (16)	0.0516 (5)
H5	0.8448 (19)	−0.3415 (14)	0.5490 (14)	0.062 (5)*
B6	0.6607 (2)	−0.35139 (16)	0.41916 (17)	0.0560 (5)
H6	0.588 (2)	−0.3994 (14)	0.4814 (13)	0.065 (5)*
B7	0.7589 (2)	−0.27118 (15)	0.19136 (16)	0.0503 (4)
H7	0.7377 (18)	−0.2580 (13)	0.1044 (13)	0.057 (4)*
B8	0.5950 (2)	−0.25187 (16)	0.30200 (17)	0.0523 (5)
H8	0.465 (2)	−0.2256 (14)	0.2866 (13)	0.067 (5)*
B9	0.6529 (2)	−0.20266 (15)	0.41506 (16)	0.0496 (4)
H9	0.5641 (19)	−0.1430 (14)	0.4736 (13)	0.057 (4)*
B10	0.8521 (2)	−0.19299 (14)	0.37266 (15)	0.0463 (4)
H10	0.8952 (18)	−0.1288 (13)	0.4032 (12)	0.054 (4)*
B11	0.9180 (2)	−0.23517 (15)	0.23469 (16)	0.0486 (4)
H11	1.002 (2)	−0.1994 (14)	0.1743 (13)	0.063 (5)*
B12	0.7131 (2)	−0.15303 (14)	0.27349 (14)	0.0436 (4)
C2	0.64183 (18)	−0.02308 (13)	0.22826 (12)	0.0467 (4)
C3	0.58462 (17)	0.07904 (13)	0.19784 (12)	0.0446 (4)
C4	0.51356 (16)	0.20251 (12)	0.16824 (12)	0.0420 (3)
C5	0.46196 (19)	0.27790 (14)	0.25139 (15)	0.0503 (4)
H5A	0.4757 (19)	0.2488 (14)	0.3277 (14)	0.059 (5)*
C6	0.3917 (2)	0.39677 (15)	0.22449 (18)	0.0633 (5)
H6A	0.357 (2)	0.4489 (17)	0.2854 (16)	0.078 (6)*
C7	0.3720 (2)	0.44060 (16)	0.11525 (18)	0.0662 (5)
H7A	0.318 (2)	0.5237 (19)	0.0958 (16)	0.089 (6)*
C8	0.4210 (2)	0.36716 (16)	0.03291 (18)	0.0647 (5)
H8A	0.408 (2)	0.3951 (16)	−0.0451 (16)	0.074 (5)*
C9	0.4921 (2)	0.24830 (15)	0.05830 (15)	0.0536 (4)
H9A	0.530 (2)	0.1947 (15)	−0.0011 (14)	0.062 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0430 (7)	0.0412 (7)	0.0525 (7)	−0.0178 (6)	−0.0068 (6)	−0.0043 (5)
C11	0.0394 (9)	0.0633 (11)	0.0709 (12)	−0.0172 (8)	−0.0107 (9)	−0.0057 (9)
C12	0.0600 (12)	0.0723 (13)	0.0766 (13)	0.0020 (10)	−0.0135 (10)	0.0039 (10)
C13	0.0695 (13)	0.0592 (11)	0.0616 (11)	−0.0210 (10)	−0.0051 (10)	−0.0189 (9)
C14	0.1051 (18)	0.0901 (16)	0.0746 (14)	−0.0207 (13)	0.0179 (13)	−0.0270 (12)
C15	0.0741 (13)	0.0518 (10)	0.0705 (12)	−0.0272 (10)	−0.0061 (11)	0.0080 (9)
C16	0.1112 (18)	0.0705 (13)	0.0693 (13)	−0.0084 (12)	−0.0202 (13)	0.0107 (10)
C17	0.0387 (9)	0.0518 (10)	0.0590 (10)	−0.0155 (7)	−0.0070 (8)	−0.0048 (8)
C18	0.0640 (12)	0.0628 (11)	0.0675 (11)	−0.0110 (9)	−0.0052 (9)	−0.0162 (9)
C1	0.0603 (10)	0.0321 (8)	0.0662 (10)	−0.0067 (7)	−0.0200 (8)	−0.0001 (7)
B2	0.0654 (13)	0.0385 (9)	0.0701 (12)	−0.0170 (9)	−0.0233 (10)	−0.0037 (9)
B3	0.0587 (12)	0.0423 (10)	0.0620 (12)	−0.0061 (9)	−0.0080 (10)	−0.0137 (9)
B4	0.0475 (11)	0.0417 (9)	0.0684 (12)	−0.0036 (8)	−0.0184 (9)	−0.0056 (8)
B5	0.0625 (12)	0.0394 (9)	0.0506 (10)	−0.0089 (8)	−0.0179 (9)	0.0007 (8)
B6	0.0575 (12)	0.0431 (10)	0.0645 (12)	−0.0158 (9)	−0.0070 (10)	0.0033 (9)
B7	0.0608 (12)	0.0420 (9)	0.0505 (10)	−0.0138 (8)	−0.0177 (9)	−0.0041 (8)
B8	0.0461 (11)	0.0437 (10)	0.0675 (12)	−0.0125 (8)	−0.0165 (9)	0.0008 (8)
B9	0.0509 (11)	0.0395 (9)	0.0523 (10)	−0.0063 (8)	−0.0056 (9)	−0.0030 (8)
B10	0.0515 (10)	0.0353 (8)	0.0540 (10)	−0.0106 (8)	−0.0171 (8)	−0.0035 (7)
B11	0.0454 (10)	0.0439 (9)	0.0554 (11)	−0.0124 (8)	−0.0055 (8)	−0.0056 (8)
B12	0.0453 (10)	0.0358 (8)	0.0496 (10)	−0.0092 (7)	−0.0126 (8)	−0.0035 (7)
C2	0.0472 (9)	0.0422 (9)	0.0512 (9)	−0.0130 (7)	−0.0127 (7)	−0.0004 (7)
C3	0.0393 (8)	0.0413 (8)	0.0530 (9)	−0.0125 (7)	−0.0115 (7)	0.0025 (7)
C4	0.0329 (7)	0.0374 (7)	0.0552 (9)	−0.0127 (6)	−0.0097 (6)	0.0057 (7)
C5	0.0447 (9)	0.0457 (9)	0.0557 (10)	−0.0120 (7)	−0.0045 (7)	0.0034 (7)
C6	0.0558 (11)	0.0453 (9)	0.0826 (13)	−0.0113 (8)	−0.0001 (10)	−0.0065 (9)
C7	0.0557 (11)	0.0400 (9)	0.0959 (15)	−0.0129 (8)	−0.0150 (10)	0.0160 (10)
C8	0.0676 (12)	0.0563 (11)	0.0693 (12)	−0.0228 (9)	−0.0242 (10)	0.0227 (10)
C9	0.0554 (10)	0.0491 (9)	0.0581 (10)	−0.0189 (8)	−0.0156 (8)	0.0055 (8)

Geometric parameters (Å, º) top

N1—C13	1.511 (2)	B3—H3	1.106 (17)
N1—C17	1.5173 (19)	B4—B5	1.767 (3)
N1—C11	1.519 (2)	B4—B10	1.768 (2)
N1—C15	1.521 (2)	B4—B11	1.772 (3)
C11—C12	1.498 (2)	B4—H4	1.112 (17)
C11—H11A	0.991 (19)	B5—B10	1.764 (2)
C11—H11B	0.996 (19)	B5—B9	1.768 (3)
C12—H12A	0.9600	B5—B6	1.771 (3)
C12—H12B	0.9600	B5—H5	1.101 (16)
C12—H12C	0.9600	B6—B8	1.771 (3)
C13—C14	1.509 (3)	B6—B9	1.771 (3)
C13—H13A	1.000 (19)	B6—H6	1.117 (17)
C13—H13B	0.973 (19)	B7—B12	1.773 (2)
C14—H14A	0.9600	B7—B11	1.777 (3)
C14—H14B	0.9600	B7—B8	1.778 (3)
C14—H14C	0.9600	B7—H7	1.087 (15)
C15—C16	1.501 (3)	B8—B12	1.779 (2)
C15—H15A	1.041 (19)	B8—B9	1.791 (3)
C15—H15B	0.98 (2)	B8—H8	1.127 (17)
C16—H16A	0.9600	B9—B10	1.778 (3)
C16—H16B	0.9600	B9—B12	1.782 (3)
C16—H16C	0.9600	B9—H9	1.118 (16)
C17—C18	1.497 (2)	B10—B12	1.777 (2)
C17—H17A	0.987 (17)	B10—B11	1.778 (3)
C17—H17B	0.942 (17)	B10—H10	1.101 (15)
C18—H18A	0.9600	B11—B12	1.785 (3)
C18—H18B	0.9600	B11—H11	1.092 (16)
C18—H18C	0.9600	B12—C2	1.548 (2)
C1—B5	1.692 (2)	C2—C3	1.202 (2)
C1—B4	1.698 (3)	C3—C4	1.4393 (19)
C1—B2	1.698 (2)	C4—C5	1.389 (2)
C1—B3	1.699 (3)	C4—C9	1.389 (2)
C1—B6	1.703 (3)	C5—C6	1.385 (2)
C1—H1	1.010 (17)	C5—H5A	0.956 (16)
B2—B8	1.762 (3)	C6—C7	1.373 (3)
B2—B7	1.767 (3)	C6—H6A	0.993 (19)
B2—B3	1.767 (3)	C7—C8	1.366 (3)
B2—B6	1.773 (3)	C7—H7A	0.98 (2)
B2—H2	1.118 (16)	C8—C9	1.383 (2)
B3—B7	1.767 (3)	C8—H8A	0.973 (18)
B3—B11	1.769 (3)	C9—H9A	0.990 (17)
B3—B4	1.775 (3)

C13—N1—C17	106.34 (12)	C3—C2—B12	177.15 (16)
C13—N1—C11	110.83 (14)	C2—C3—C4	176.64 (17)
C17—N1—C11	110.72 (13)	C5—C4—C9	118.84 (14)
C13—N1—C15	111.48 (14)	C5—C4—C3	119.59 (14)
C17—N1—C15	111.00 (13)	C9—C4—C3	121.55 (14)
C11—N1—C15	106.54 (13)	C6—C5—C4	120.32 (16)
C12—C11—N1	115.71 (14)	C7—C6—C5	120.04 (19)
C14—C13—N1	115.43 (16)	C8—C7—C6	120.15 (17)
C16—C15—N1	115.55 (16)	C7—C8—C9	120.53 (18)
C18—C17—N1	116.43 (13)	C8—C9—C4	120.11 (18)

C2—C3—C4—C5	8 (3)	C5—C6—C7—C8	0.2 (3)
C2—C3—C4—C9	−171 (3)	C6—C7—C8—C9	−0.5 (3)
C9—C4—C5—C6	−0.6 (2)	C7—C8—C9—C4	0.2 (3)
C3—C4—C5—C6	−179.29 (14)	C5—C4—C9—C8	0.3 (2)
C4—C5—C6—C7	0.4 (3)	C3—C4—C9—C8	178.98 (15)

Experimental details

Crystal data
Chemical formula	C₈H₂₀N⁺·C₉H₁₆B₁₁⁻
M_r	373.38
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.8201 (6), 12.0929 (11), 12.1858 (11)
α, β, γ (°)	81.032 (7), 79.899 (7), 71.553 (7)
V (Å³)	1206.82 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.05
Crystal size (mm)	0.3 × 0.25 × 0.2

Data collection
Diffractometer	Stoe Stadi CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17081, 4219, 3228
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.101, 1.00
No. of reflections	4219
No. of parameters	363
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: CrysAlis CCD (Kuma, 2000), CrysAlis RED (Kuma, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2008).

Acknowledgements

Financial support from the Fonds der Chemischen Industrie (FCI) is gratefully acknowledged.

References

Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Finze, M. (2008). Inorg. Chem. 47, 11857–11867. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Kuma (2000). CrysAlis CCD and CrysAlis RED. Kuma Diffraction, Wrocław, Poland. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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