Tetra-ethyl-ammonium 12-phenyl-ethynylcarba-closo-dodeca-borate, [Et(4)N][12-PhCC-closo-CB(11)H(11)].

The asymmetric unit of the title compound, C(8)H(20)N(+)·C(9)H(16)B(11) (-) or [Et(4)N][12-PhCC-closo-CB(11)H(11)], consists of one cation and one anion. The [12-PhCC-closo-CB(11)H(11)](-) 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 = 373.38

Triclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.101

S = 1.00

4219 reflections

363 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Kuma, 2000 ▶); cell refinement: CrysAlis RED (Kuma, 2000 ▶); 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.

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

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

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

C8H20N+·C9H16B11−	Z = 2
Mr = 373.38	F(000) = 400
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.01P)2 + 0.45P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4219 reflections	Δρmax = 0.16 e Å−3
363 parameters	Δρmin = −0.15 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)

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
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)*

	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)

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)