Acta Crystallographica Section E: Structure Reports Online

Acta Crystallogr Sect E Struct Rep Online. 66(Pt 1): o203-o203

Tetrabutylammonium tris(methylsulfanylmethyl)phenylborate

Jan Tillmanna, Hans-Wolfram Lernera, Michael Boltea*

a. Institut 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

© Tillmann et al. 2010

DOI: 10.1107/S1600536809054026

Published online: 19 December 2009

Abstract

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,

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[F ² > 2σ(F ²)] = 0.055

wR(F ²) = 0.155

S = 1.01

5999 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å⁻³

Δρmin = −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.

Supplementary Material

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2016).

supplementary crystallographic information

Comment

Recently we have described the synthesis and properties of complexes with [(methylthio)methyl]borate ligands (C₆H₅)Bpzx(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).

Experimental

(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%).

Refinement

Hydrogen atoms were located in a difference Fourier map but they were included in calculated positions [C—H = 0.95 - 0.99 Å] and refined as riding [Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl)].

Figures

Fig. 1.View larger versionFig. 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.View larger versionFig. 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.View larger versionFig. 3. Crystal packing of the title compound with view along the b axis. H atoms are omitted for clarity.

Fig. 4.View larger versionFig. 4. The formation of the title compound.

Crystal data

See full table

Data collection

See full table

Refinement

See full table

Special details

See full table

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

See full table

Atomic displacement parameters (Å²)

See full table

Geometric parameters (Å, °)

See full table

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References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Ohrenberg, C., Ge, P., Schebler, P. C. G., Riordan, C. G., Yap, G. P. A. & Rheingold, A. L. (1996). Inorg. Chem.35, 749–754.

Ruth, K., Tüllmann, S., Vitze, H., Bolte, M., Lerner, H.-W., Holthausen, M. C. & Wagner, M. (2008). Chem. Eur. J.14, 6754–6770.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Stoe & Cie (2001). X-AREA and X-RED Stoe & Cie, Darmstadt, Germany.

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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.

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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.

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Fig. 3.

Crystal packing of the title compound with view along the b axis. H atoms are omitted for clarity.

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Fig. 4.

The formation of the title compound.

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C₁₆H₃₆N⁺·C₁₂H₂₀BS₃⁻ | F(000) = 1136
Mr = 513.73 | Dx = 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 |

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

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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(Fo²) + (0.0983P)²] where P = (Fo² + 2Fc²)/3
5999 reflections | (Δ/σ)max = 0.001
298 parameters | Δρmax = 0.72 e Å⁻³
0 restraints | Δρmin = −0.32 e Å⁻³

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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.

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| x | y | z | Uiso*/Ueq |
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* |

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| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
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)

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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)

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