Tetra­butyl­ammonium tris­(methyl­sulfanylmeth­yl)phenyl­borate

Tillmann, J.; Lerner, H.-W.; Bolte, M.

doi:10.1107/S1600536809054026

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o203

doi:10.1107/S1600536809054026

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Tetrabutylammonium tris(methylsulfanylmethyl)phenylborate

Jan Tillmann,^a Hans-Wolfram Lerner ^a and Michael Bolte ^a ^*

^aInstitut für Anorganische Chemie der Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 11 December 2009; accepted 15 December 2009; online 19 December 2009)

In the title molecular salt, C₁₆H₃₆N⁺·C₁₂H₂₀BS₃⁻, three of the four n-butyl chains show a trans conformation, whereas the fourth has the C—C—C—C torsion angle in a gauche conformation [−77.8 (5)°]. In the crystal, molecules are packed in layers parallel to the (101) plane.

Related literature

For the synthesis and properties of complexes with [(methylthio)methyl]borate ligands, see: Ohrenberg et al. (1996 ); Ruth et al. (2008 ).

Experimental

Crystal data

C₁₆H₃₆N⁺·C₁₂H₂₀BS₃⁻
M_r = 513.73
Monoclinic, P 2₁ /n
a = 9.8449 (8) Å
b = 15.6802 (9) Å
c = 20.8870 (17) Å
β = 92.215 (7)°
V = 3221.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.42 × 0.39 × 0.38 mm

Data collection

Stoe IPDS-II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995 ) T_min = 0.904, T_max = 0.912
17239 measured reflections
5999 independent reflections
4342 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.155
S = 1.01
5999 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054026/vm2016sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054026/vm2016Isup2.hkl

checkCIF report

Comment top

Recently we have described the synthesis and properties of complexes with [(methylthio)methyl]borate ligands (C₆H₅)Bpz_x(CH₂SMe)_3-_x (Ruth et al., 2008). It is interesting to note that these ligands facilitate an evaluation of the influence of gradual changes in the donor set of tripods on the chemical properties of the coordinated metal ion. Herein we report the crystal structure of the tetrabutylamonium [tris(methylthio)methyl]phenylborate [n-Bu₄N][(C₆H₅)B(CH₂SMe)₃] (I). According to a literature procedure (Ohrenberg et al., 1996), the tetrabutylamonium [tris(methylthio)methyl]phenylborate [n-Bu₄N][(C₆H₅)B(CH₂SMe)₃] was easily accessible from the reaction of PhBCl₂ with Li(TMEDA)CH₂SMe (TMEDA: N,N,N',N'-tetramethylethylenediamine) and a subsequent cation exchange, as shown in equation below.

The title compound (Figs. 1 and 2) features discrete cations and anions. Three of the four n-butyl chains show an all trans conformation whereas the forth has one torsion angle in a gauche conformation. In the crystal the molecules are packed in layers parallel to the (1 0 1) plane (Figure 3).

Related literature top

For the synthesis and properties of complexes with

[(methylthio)methyl]borate ligands, see: Ohrenberg et al. (1996); Ruth et al. (2008).

Experimental top

(CH₃)₂S (19 mL, 259 mmol) and TMEDA (24 mL,160 mmol) were combined under a N₂ atmosphere. n-BuLi (60 mL, 1.6 M in hexane) was added dropwise at -78°C. After 1 h at 25°C, the solution was heated at 45°C for 30 min to drive off unreacted (CH₃)₂S. The solution was again cooled to -78°C and (C₆H₅)BCl₂ (3.3 mL, 25 mmol) was added dropwise. The mixture was allowed to warm to 25°C and was then stirred for 48 h. After the reaction was terminated all volatiles were removed in vacuo and the residue was treated with 200 mL of H₂O and 70 mL of CH₂Cl₂. The aqueous solution was filtered, and the product (I) was precipitated by addition of aqueous [n-Bu₄N]Br. The flocculent white product was isolated by filtration, washed with Et₂O (2 x 10 mL), and dried under vacuum. Single crystals were obtained by recrystallisation from Et₂O. ¹H NMR (CDCl₃): δ 8.09 (d, CH, 2 H), 7.27 (t, CH, 2 H), 7.05 (t, CH, 1 H), 2.57 -2.48 (m, BCH₂ / NCH₂, 14H ), 2.28 (s, SCH₃, 9 H), 1.20 -1.17 (m, NCH₂CH₂CH₂CH₃, 16 H), 1.35 (m, CH₂, 16 H), 0.87 (t, CH3, 12 H). ¹¹B{¹H} NMR (CDCl₃): δ -14.4. Yield: 8.0 g (63%).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the anion of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of the cation of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. Crystal packing of the title compound with view along the b axis. H atoms are omitted for clarity.
	Fig. 4. The formation of the title compound.

Tetrabutylammonium tris(methylsulfanylmethyl)phenylborate top

Crystal data top

C₁₆H₃₆N⁺·C₁₂H₂₀BS₃⁻	F(000) = 1136
M_r = 513.73	D_x = 1.059 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 13831 reflections
a = 9.8449 (8) Å	θ = 3.5–25.9°
b = 15.6802 (9) Å	µ = 0.25 mm⁻¹
c = 20.8870 (17) Å	T = 173 K
β = 92.215 (7)°	Block, colourless
V = 3221.9 (4) Å³	0.42 × 0.39 × 0.38 mm
Z = 4

Data collection top

Stoe IPDS-II two-circle diffractometer	5999 independent reflections
Radiation source: fine-focus sealed tube	4342 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ω scans	θ_max = 25.8°, θ_min = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −10→11
T_min = 0.904, T_max = 0.912	k = −16→19
17239 measured reflections	l = −25→25

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0983P)²] where P = (F_o² + 2F_c²)/3
5999 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₃₆N⁺·C₁₂H₂₀BS₃⁻	V = 3221.9 (4) Å³
M_r = 513.73	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8449 (8) Å	µ = 0.25 mm⁻¹
b = 15.6802 (9) Å	T = 173 K
c = 20.8870 (17) Å	0.42 × 0.39 × 0.38 mm
β = 92.215 (7)°

Data collection top

Stoe IPDS-II two-circle diffractometer	5999 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	4342 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.912	R_int = 0.066
17239 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	Δρ_max = 0.72 e Å⁻³
5999 reflections	Δρ_min = −0.32 e Å⁻³
298 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
B1	0.4152 (3)	0.77978 (17)	0.68202 (11)	0.0359 (5)
S1	0.56606 (7)	0.65306 (4)	0.61210 (3)	0.04352 (18)
S2	0.51768 (7)	0.83143 (4)	0.80904 (3)	0.04459 (19)
S3	0.46045 (9)	0.89280 (6)	0.57424 (4)	0.0682 (3)
C1	0.5653 (2)	0.73852 (16)	0.66989 (10)	0.0383 (5)
H1A	0.6039	0.7169	0.7112	0.046*
H1B	0.6260	0.7844	0.6554	0.046*
C2	0.7422 (3)	0.6237 (2)	0.61991 (13)	0.0580 (7)
H2A	0.7602	0.5766	0.5906	0.087*
H2B	0.7639	0.6059	0.6641	0.087*
H2C	0.7988	0.6728	0.6093	0.087*
C3	0.4401 (3)	0.86025 (15)	0.73206 (11)	0.0397 (5)
H3A	0.3514	0.8877	0.7392	0.048*
H3B	0.4986	0.9029	0.7116	0.048*
C4	0.5650 (3)	0.9351 (2)	0.83934 (14)	0.0584 (7)
H4A	0.6092	0.9291	0.8820	0.088*
H4B	0.4835	0.9706	0.8423	0.088*
H4C	0.6280	0.9620	0.8103	0.088*
C5	0.3466 (3)	0.8213 (2)	0.61550 (12)	0.0547 (7)
H5A	0.2636	0.8532	0.6262	0.066*
H5B	0.3188	0.7744	0.5861	0.066*
C6	0.3446 (5)	0.9760 (2)	0.54940 (17)	0.0845 (12)
H6A	0.3936	1.0197	0.5260	0.127*
H6B	0.3050	1.0016	0.5872	0.127*
H6C	0.2721	0.9520	0.5215	0.127*
C11	0.3093 (2)	0.71146 (14)	0.71190 (9)	0.0348 (5)
C12	0.3530 (3)	0.64613 (18)	0.75270 (13)	0.0515 (6)
H12	0.4479	0.6392	0.7611	0.062*
C13	0.2638 (4)	0.59029 (19)	0.78188 (15)	0.0620 (8)
H13	0.2981	0.5471	0.8100	0.074*
C14	0.1245 (3)	0.59827 (18)	0.76956 (14)	0.0593 (8)
H14	0.0629	0.5601	0.7886	0.071*
C15	0.0777 (3)	0.6619 (2)	0.72964 (13)	0.0573 (7)
H15	−0.0173	0.6683	0.7212	0.069*
C16	0.1677 (3)	0.71714 (18)	0.70135 (11)	0.0449 (6)
H16	0.1322	0.7606	0.6737	0.054*
N1	0.5861 (2)	0.65794 (14)	0.39600 (8)	0.0396 (5)
C21	0.5628 (3)	0.6327 (2)	0.32574 (10)	0.0531 (7)
H21A	0.5438	0.6850	0.3005	0.064*
H21B	0.6480	0.6078	0.3104	0.064*
C22	0.4488 (4)	0.5700 (3)	0.31219 (14)	0.0858 (12)
H22A	0.3639	0.5933	0.3291	0.103*
H22B	0.4698	0.5161	0.3352	0.103*
C23	0.4255 (5)	0.5507 (3)	0.24087 (17)	0.1044 (16)
H23A	0.5147	0.5425	0.2215	0.125*
H23B	0.3743	0.4966	0.2361	0.125*
C24	0.3540 (5)	0.6152 (3)	0.20706 (19)	0.1017 (14)
H24A	0.3438	0.5994	0.1617	0.153*
H24B	0.4045	0.6690	0.2111	0.153*
H24C	0.2640	0.6223	0.2248	0.153*
C31	0.4585 (2)	0.69867 (18)	0.42244 (10)	0.0432 (6)
H31A	0.3856	0.6552	0.4219	0.052*
H31B	0.4785	0.7144	0.4677	0.052*
C32	0.4051 (3)	0.7766 (2)	0.38756 (12)	0.0551 (7)
H32A	0.3894	0.7630	0.3416	0.066*
H32B	0.4734	0.8228	0.3911	0.066*
C33	0.2732 (3)	0.8065 (2)	0.41532 (13)	0.0550 (7)
H33A	0.2051	0.7602	0.4115	0.066*
H33B	0.2891	0.8192	0.4614	0.066*
C34	0.2171 (4)	0.8853 (3)	0.38171 (17)	0.0761 (10)
H34A	0.1329	0.9029	0.4015	0.114*
H34B	0.1982	0.8725	0.3363	0.114*
H34C	0.2839	0.9315	0.3856	0.114*
C41	0.6161 (2)	0.58012 (17)	0.43699 (10)	0.0404 (5)
H41A	0.5374	0.5410	0.4325	0.048*
H41B	0.6234	0.5985	0.4823	0.048*
C42	0.7434 (3)	0.53021 (17)	0.42250 (11)	0.0441 (6)
H42A	0.8242	0.5673	0.4287	0.053*
H42B	0.7385	0.5110	0.3773	0.053*
C43	0.7567 (3)	0.45311 (17)	0.46679 (11)	0.0464 (6)
H43A	0.7564	0.4729	0.5118	0.056*
H43B	0.6767	0.4157	0.4593	0.056*
C44	0.8850 (3)	0.40157 (19)	0.45726 (13)	0.0570 (7)
H44A	0.8882	0.3533	0.4871	0.086*
H44B	0.9648	0.4379	0.4654	0.086*
H44C	0.8848	0.3802	0.4132	0.086*
C51	0.7038 (3)	0.72033 (18)	0.39848 (11)	0.0454 (6)
H51A	0.6781	0.7702	0.3716	0.054*
H51B	0.7824	0.6927	0.3788	0.054*
C52	0.7496 (3)	0.7524 (2)	0.46443 (13)	0.0550 (7)
H52A	0.6735	0.7825	0.4843	0.066*
H52B	0.7762	0.7035	0.4921	0.066*
C53	0.8687 (3)	0.8124 (2)	0.45910 (16)	0.0638 (8)
H53A	0.8417	0.8602	0.4304	0.077*
H53B	0.9442	0.7816	0.4394	0.077*
C54	0.9186 (5)	0.8482 (3)	0.5233 (2)	0.0880 (12)
H54A	0.9946	0.8873	0.5169	0.132*
H54B	0.9490	0.8014	0.5515	0.132*
H54C	0.8445	0.8791	0.5431	0.132*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0354 (13)	0.0366 (14)	0.0357 (11)	−0.0025 (12)	0.0024 (10)	0.0031 (10)
S1	0.0477 (4)	0.0445 (4)	0.0385 (3)	−0.0020 (3)	0.0025 (2)	−0.0098 (2)
S2	0.0522 (4)	0.0429 (4)	0.0391 (3)	−0.0079 (3)	0.0075 (2)	−0.0054 (2)
S3	0.0601 (5)	0.0804 (6)	0.0645 (4)	−0.0095 (4)	0.0053 (3)	0.0372 (4)
C1	0.0387 (13)	0.0389 (13)	0.0375 (10)	−0.0030 (11)	0.0055 (9)	−0.0081 (9)
C2	0.0628 (19)	0.0598 (18)	0.0513 (14)	0.0236 (15)	−0.0014 (12)	−0.0098 (12)
C3	0.0382 (13)	0.0340 (12)	0.0474 (12)	0.0010 (10)	0.0069 (10)	0.0019 (9)
C4	0.0533 (17)	0.0574 (18)	0.0649 (16)	−0.0126 (14)	0.0093 (13)	−0.0234 (13)
C5	0.0454 (15)	0.0674 (19)	0.0512 (14)	−0.0094 (14)	−0.0001 (11)	0.0208 (13)
C6	0.117 (3)	0.057 (2)	0.082 (2)	0.017 (2)	0.044 (2)	0.0157 (17)
C11	0.0393 (12)	0.0332 (12)	0.0320 (10)	−0.0026 (10)	0.0050 (8)	−0.0060 (8)
C12	0.0507 (16)	0.0463 (15)	0.0587 (14)	0.0045 (13)	0.0155 (12)	0.0108 (12)
C13	0.079 (2)	0.0410 (15)	0.0687 (17)	0.0040 (15)	0.0302 (15)	0.0095 (13)
C14	0.073 (2)	0.0422 (15)	0.0654 (16)	−0.0237 (15)	0.0324 (15)	−0.0152 (13)
C15	0.0453 (15)	0.071 (2)	0.0565 (15)	−0.0218 (15)	0.0073 (12)	−0.0138 (14)
C16	0.0412 (14)	0.0538 (15)	0.0399 (11)	−0.0074 (12)	0.0029 (10)	−0.0045 (10)
N1	0.0335 (10)	0.0543 (13)	0.0313 (9)	0.0039 (9)	0.0056 (7)	0.0103 (8)
C21	0.0553 (16)	0.0746 (19)	0.0297 (11)	0.0172 (15)	0.0045 (10)	0.0087 (11)
C22	0.098 (3)	0.110 (3)	0.0477 (16)	−0.026 (3)	−0.0208 (16)	−0.0047 (17)
C23	0.108 (3)	0.134 (4)	0.068 (2)	0.052 (3)	−0.033 (2)	−0.039 (2)
C24	0.099 (3)	0.130 (4)	0.075 (2)	0.010 (3)	−0.016 (2)	0.010 (2)
C31	0.0317 (12)	0.0621 (16)	0.0362 (11)	0.0033 (12)	0.0072 (9)	0.0077 (10)
C32	0.0435 (15)	0.073 (2)	0.0490 (13)	0.0127 (14)	0.0092 (11)	0.0139 (13)
C33	0.0408 (15)	0.0704 (19)	0.0537 (14)	0.0105 (14)	0.0023 (11)	0.0007 (13)
C34	0.059 (2)	0.088 (3)	0.082 (2)	0.0294 (19)	0.0013 (16)	0.0093 (18)
C41	0.0369 (13)	0.0511 (14)	0.0333 (10)	−0.0015 (11)	0.0025 (9)	0.0089 (9)
C42	0.0432 (14)	0.0498 (15)	0.0395 (11)	0.0011 (12)	0.0024 (10)	0.0050 (10)
C43	0.0500 (15)	0.0467 (15)	0.0421 (12)	−0.0023 (12)	−0.0018 (10)	0.0039 (10)
C44	0.069 (2)	0.0479 (16)	0.0543 (14)	0.0092 (15)	−0.0008 (13)	−0.0012 (12)
C51	0.0364 (13)	0.0525 (15)	0.0481 (12)	0.0035 (12)	0.0133 (10)	0.0163 (11)
C52	0.0457 (16)	0.0625 (18)	0.0573 (15)	−0.0082 (14)	0.0094 (12)	0.0043 (13)
C53	0.0512 (18)	0.0590 (19)	0.082 (2)	−0.0114 (15)	0.0116 (15)	0.0012 (15)
C54	0.082 (3)	0.081 (3)	0.101 (3)	−0.024 (2)	0.003 (2)	−0.019 (2)

Geometric parameters (Å, º) top

B1—C11	1.635 (3)	C22—H22A	0.9900
B1—C1	1.642 (4)	C22—H22B	0.9900
B1—C3	1.651 (3)	C23—C24	1.406 (6)
B1—C5	1.655 (3)	C23—H23A	0.9900
S1—C2	1.796 (3)	C23—H23B	0.9900
S1—C1	1.804 (2)	C24—H24A	0.9800
S2—C4	1.799 (3)	C24—H24B	0.9800
S2—C3	1.811 (2)	C24—H24C	0.9800
S3—C6	1.796 (4)	C31—C32	1.507 (4)
S3—C5	1.825 (3)	C31—H31A	0.9900
C1—H1A	0.9900	C31—H31B	0.9900
C1—H1B	0.9900	C32—C33	1.517 (4)
C2—H2A	0.9800	C32—H32A	0.9900
C2—H2B	0.9800	C32—H32B	0.9900
C2—H2C	0.9800	C33—C34	1.514 (4)
C3—H3A	0.9900	C33—H33A	0.9900
C3—H3B	0.9900	C33—H33B	0.9900
C4—H4A	0.9800	C34—H34A	0.9800
C4—H4B	0.9800	C34—H34B	0.9800
C4—H4C	0.9800	C34—H34C	0.9800
C5—H5A	0.9900	C41—C42	1.518 (4)
C5—H5B	0.9900	C41—H41A	0.9900
C6—H6A	0.9800	C41—H41B	0.9900
C6—H6B	0.9800	C42—C43	1.525 (3)
C6—H6C	0.9800	C42—H42A	0.9900
C11—C12	1.390 (4)	C42—H42B	0.9900
C11—C16	1.406 (3)	C43—C44	1.519 (4)
C12—C13	1.396 (4)	C43—H43A	0.9900
C12—H12	0.9500	C43—H43B	0.9900
C13—C14	1.391 (5)	C44—H44A	0.9800
C13—H13	0.9500	C44—H44B	0.9800
C14—C15	1.369 (5)	C44—H44C	0.9800
C14—H14	0.9500	C51—C52	1.518 (4)
C15—C16	1.387 (4)	C51—H51A	0.9900
C15—H15	0.9500	C51—H51B	0.9900
C16—H16	0.9500	C52—C53	1.510 (4)
N1—C41	1.513 (3)	C52—H52A	0.9900
N1—C51	1.516 (3)	C52—H52B	0.9900
N1—C21	1.529 (3)	C53—C54	1.519 (5)
N1—C31	1.531 (3)	C53—H53A	0.9900
C21—C22	1.511 (5)	C53—H53B	0.9900
C21—H21A	0.9900	C54—H54A	0.9800
C21—H21B	0.9900	C54—H54B	0.9800
C22—C23	1.529 (4)	C54—H54C	0.9800

C11—B1—C1	113.1 (2)	C22—C23—H23A	108.8
C11—B1—C3	109.90 (17)	C24—C23—H23B	108.8
C1—B1—C3	106.64 (19)	C22—C23—H23B	108.8
C11—B1—C5	109.4 (2)	H23A—C23—H23B	107.7
C1—B1—C5	111.48 (19)	C23—C24—H24A	109.5
C3—B1—C5	106.1 (2)	C23—C24—H24B	109.5
C2—S1—C1	99.11 (13)	H24A—C24—H24B	109.5
C4—S2—C3	100.46 (13)	C23—C24—H24C	109.5
C6—S3—C5	100.82 (16)	H24A—C24—H24C	109.5
B1—C1—S1	115.02 (16)	H24B—C24—H24C	109.5
B1—C1—H1A	108.5	C32—C31—N1	116.09 (18)
S1—C1—H1A	108.5	C32—C31—H31A	108.3
B1—C1—H1B	108.5	N1—C31—H31A	108.3
S1—C1—H1B	108.5	C32—C31—H31B	108.3
H1A—C1—H1B	107.5	N1—C31—H31B	108.3
S1—C2—H2A	109.5	H31A—C31—H31B	107.4
S1—C2—H2B	109.5	C31—C32—C33	110.8 (2)
H2A—C2—H2B	109.5	C31—C32—H32A	109.5
S1—C2—H2C	109.5	C33—C32—H32A	109.5
H2A—C2—H2C	109.5	C31—C32—H32B	109.5
H2B—C2—H2C	109.5	C33—C32—H32B	109.5
B1—C3—S2	114.75 (16)	H32A—C32—H32B	108.1
B1—C3—H3A	108.6	C34—C33—C32	112.2 (2)
S2—C3—H3A	108.6	C34—C33—H33A	109.2
B1—C3—H3B	108.6	C32—C33—H33A	109.2
S2—C3—H3B	108.6	C34—C33—H33B	109.2
H3A—C3—H3B	107.6	C32—C33—H33B	109.2
S2—C4—H4A	109.5	H33A—C33—H33B	107.9
S2—C4—H4B	109.5	C33—C34—H34A	109.5
H4A—C4—H4B	109.5	C33—C34—H34B	109.5
S2—C4—H4C	109.5	H34A—C34—H34B	109.5
H4A—C4—H4C	109.5	C33—C34—H34C	109.5
H4B—C4—H4C	109.5	H34A—C34—H34C	109.5
B1—C5—S3	113.57 (18)	H34B—C34—H34C	109.5
B1—C5—H5A	108.9	N1—C41—C42	116.60 (18)
S3—C5—H5A	108.9	N1—C41—H41A	108.1
B1—C5—H5B	108.9	C42—C41—H41A	108.1
S3—C5—H5B	108.9	N1—C41—H41B	108.1
H5A—C5—H5B	107.7	C42—C41—H41B	108.1
S3—C6—H6A	109.5	H41A—C41—H41B	107.3
S3—C6—H6B	109.5	C41—C42—C43	109.9 (2)
H6A—C6—H6B	109.5	C41—C42—H42A	109.7
S3—C6—H6C	109.5	C43—C42—H42A	109.7
H6A—C6—H6C	109.5	C41—C42—H42B	109.7
H6B—C6—H6C	109.5	C43—C42—H42B	109.7
C12—C11—C16	115.1 (2)	H42A—C42—H42B	108.2
C12—C11—B1	122.0 (2)	C44—C43—C42	113.2 (2)
C16—C11—B1	122.8 (2)	C44—C43—H43A	108.9
C11—C12—C13	123.0 (3)	C42—C43—H43A	108.9
C11—C12—H12	118.5	C44—C43—H43B	108.9
C13—C12—H12	118.5	C42—C43—H43B	108.9
C14—C13—C12	119.6 (3)	H43A—C43—H43B	107.7
C14—C13—H13	120.2	C43—C44—H44A	109.5
C12—C13—H13	120.2	C43—C44—H44B	109.5
C15—C14—C13	119.0 (3)	H44A—C44—H44B	109.5
C15—C14—H14	120.5	C43—C44—H44C	109.5
C13—C14—H14	120.5	H44A—C44—H44C	109.5
C14—C15—C16	120.6 (3)	H44B—C44—H44C	109.5
C14—C15—H15	119.7	N1—C51—C52	116.39 (18)
C16—C15—H15	119.7	N1—C51—H51A	108.2
C15—C16—C11	122.6 (3)	C52—C51—H51A	108.2
C15—C16—H16	118.7	N1—C51—H51B	108.2
C11—C16—H16	118.7	C52—C51—H51B	108.2
C41—N1—C51	111.63 (18)	H51A—C51—H51B	107.3
C41—N1—C21	110.7 (2)	C53—C52—C51	110.1 (2)
C51—N1—C21	106.63 (18)	C53—C52—H52A	109.6
C41—N1—C31	106.10 (16)	C51—C52—H52A	109.6
C51—N1—C31	110.8 (2)	C53—C52—H52B	109.6
C21—N1—C31	111.09 (18)	C51—C52—H52B	109.6
C22—C21—N1	115.5 (2)	H52A—C52—H52B	108.2
C22—C21—H21A	108.4	C52—C53—C54	113.0 (3)
N1—C21—H21A	108.4	C52—C53—H53A	109.0
C22—C21—H21B	108.4	C54—C53—H53A	109.0
N1—C21—H21B	108.4	C52—C53—H53B	109.0
H21A—C21—H21B	107.5	C54—C53—H53B	109.0
C21—C22—C23	113.2 (3)	H53A—C53—H53B	107.8
C21—C22—H22A	108.9	C53—C54—H54A	109.5
C23—C22—H22A	108.9	C53—C54—H54B	109.5
C21—C22—H22B	108.9	H54A—C54—H54B	109.5
C23—C22—H22B	108.9	C53—C54—H54C	109.5
H22A—C22—H22B	107.8	H54A—C54—H54C	109.5
C24—C23—C22	113.6 (4)	H54B—C54—H54C	109.5
C24—C23—H23A	108.8

C11—B1—C1—S1	63.1 (2)	C14—C15—C16—C11	−0.2 (4)
C3—B1—C1—S1	−176.06 (15)	C12—C11—C16—C15	0.2 (3)
C5—B1—C1—S1	−60.7 (3)	B1—C11—C16—C15	−176.3 (2)
C2—S1—C1—B1	−175.47 (18)	C41—N1—C21—C22	58.3 (3)
C11—B1—C3—S2	62.7 (2)	C51—N1—C21—C22	179.9 (3)
C1—B1—C3—S2	−60.2 (2)	C31—N1—C21—C22	−59.3 (3)
C5—B1—C3—S2	−179.10 (16)	N1—C21—C22—C23	177.0 (3)
C4—S2—C3—B1	166.25 (18)	C21—C22—C23—C24	−77.8 (5)
C11—B1—C5—S3	−175.62 (18)	C41—N1—C31—C32	−177.9 (2)
C1—B1—C5—S3	−49.8 (3)	C51—N1—C31—C32	60.7 (3)
C3—B1—C5—S3	65.9 (2)	C21—N1—C31—C32	−57.6 (3)
C6—S3—C5—B1	−139.8 (2)	N1—C31—C32—C33	175.7 (2)
C1—B1—C11—C12	31.9 (3)	C31—C32—C33—C34	179.5 (3)
C3—B1—C11—C12	−87.1 (3)	C51—N1—C41—C42	−56.3 (3)
C5—B1—C11—C12	156.8 (2)	C21—N1—C41—C42	62.3 (3)
C1—B1—C11—C16	−151.8 (2)	C31—N1—C41—C42	−177.1 (2)
C3—B1—C11—C16	89.2 (3)	N1—C41—C42—C43	−178.7 (2)
C5—B1—C11—C16	−26.9 (3)	C41—C42—C43—C44	−177.6 (2)
C16—C11—C12—C13	−0.6 (4)	C41—N1—C51—C52	−56.9 (3)
B1—C11—C12—C13	176.0 (2)	C21—N1—C51—C52	−177.9 (2)
C11—C12—C13—C14	1.0 (4)	C31—N1—C51—C52	61.1 (3)
C12—C13—C14—C15	−1.0 (4)	N1—C51—C52—C53	178.9 (2)
C13—C14—C15—C16	0.6 (4)	C51—C52—C53—C54	179.1 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₃₆N⁺·C₁₂H₂₀BS₃⁻
M_r	513.73
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.8449 (8), 15.6802 (9), 20.8870 (17)
β (°)	92.215 (7)
V (Å³)	3221.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.42 × 0.39 × 0.38

Data collection
Diffractometer	Stoe IPDS-II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.904, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	17239, 5999, 4342
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.155, 1.01
No. of reflections	5999
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.32

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ohrenberg, C., Ge, P., Schebler, P. C. G., Riordan, C. G., Yap, G. P. A. & Rheingold, A. L. (1996). Inorg. Chem. 35, 749–754. CSD CrossRef CAS Web of Science Google Scholar
Ruth, K., Tüllmann, S., Vitze, H., Bolte, M., Lerner, H.-W., Holthausen, M. C. & Wagner, M. (2008). Chem. Eur. J. 14, 6754–6770. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar