2-Methyl-1-phenylsulfanyl-1,2-dicarba-closo-dodecaborane(12)

In the title o-carborane derivative, C₉H₁₈B₁₀S, the methyl and phenyl­sulfanyl groups are connected to the C atoms of the carborane cage. The C_cage-C_cage distance is 1.708 (4) Å.

S1. Comment

In 1,2-dicarba-closo-dodecaboranes, the C_cage—C_cage or C1—C2 bond length is considerably influenced by the number of substituents and atom species connected to the cluster C atoms. These distances are shortest for the 1,2-H₂ compounds [1.57 (1)–1.634 (3) Å; Šubrtová et al., 1980; Novák et al., 1983], while much longer distances [1.799 (3)–1.858 (5) Å] are observed for the 1,2-S₂-substituted compounds (Llop et al., 2002; Teixidor, Romerosa et al., 1990; Teixidor, Viñas et al., 1990). Continuing our studies of the elongation of the C1—C2 distance caused by different C_cage substituents (Kivekäs et al., 1994, 1995, 1998; Sillanpää et al., 1996), and in order to prepare new ligands or ligand precursors for complexation, we have now synthesized and characterized the title compound, (I), and determined its crystal structure. \sch

In (I), the phenylsulfanyl and methyl groups are connected to the cluster C atoms of the 1,2-dicarba-closo-dodecaborane moiety. The phenyl group is oriented away from atom B3, and in order to reduce the repulsion between the phenyl group and the carborane cage, the S atom is moved slightly from its idealized radial position towards atom B3. As a consequence, the B3—C1—S angle is significantly smaller [113.19 (18)°] than the B6—C1—S angle [122.48 (19)°], and the C13—C2—C1—S torsion angle is -5.3 (3)°. Thus, variation of the C13—C2—X angles [116.8 (3)–121.7 (3)°] (X is C_cage or B) is less than that of the S—C1—X angles. The contribution of the phenylsulfanyl and methyl substituents on the cluster C atoms to the C1—C2 bond is indicated by the bond distance of 1.708 (4) Å.

Comparison of (I) with the relevant sulfido-substituted monoanion [2-Me-1-S—C₂B₁₀H₁₀]^- (Kivekäs et al., 1999) reveals two marked differences. The C1—C2 distance is significantly shorter in (I) than in the latter compound [1.792 (5) Å], but the C1—S distance in (I) [1.784 (3) Å] is significantly longer than in the latter compound [1.735 (4) Å].

The observed C1—C2 distance in (I) is in line with our earlier results obtained for neutral 1,2-disubstituted o-carboranes. The distance is slightly longer than that in compounds with aliphatic C atoms connected to both cluster C atoms [1.670 (3) and 1.684 (6) Å; Kivekäs et al., 1998; Holbray et al., 1993], but is much shorter than the corresponding distance in 1,2-S₂ substituted closo compounds [1.799 (3)–1.858 (5) Å; Llop et al., 2002; Teixidor, Romerosa et al., 1990; Teixidor, Viñas et al., 1990].

The C1—C2 distance in (I) is comparable with the corresponding distance of 1.702 (6) Å in 1-Me-2-PPh₂—C₂B₁₀H₁₀ (Kivekäs et al., 1994), thus indicating that the contribution of one Me and one SPh substitutent to the lengthening of the C1—C2 distance is equivalent to that of Me and PPh₂ substituents.

S2. Experimental

Reaction of 1-Me-1,2-C₂B₁₀H₁₁ in diethyl ether with a solution of n-butyllithium in hexane, and subsequent reaction with phenyldisulfide in diethyl ether, resulted a white solid. After purification, the solid was recrystallized from dichloromethane-n-hexane and pale-yellow crystals of (I) were obtained. Full details of the synthesis, and the spectral data and elemental analysis, are given in the archived CIF.

S3. Refinement

The methyl group was refined as a rotating group, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C). The other H atoms were refined using a riding model, with B—H = 1.10 Å and C—H = 0.93 Å, and with U_iso(H) = 1.2U_eq(B or C), starting from idealized positions.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1995); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990b); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. A view of the structure of (I) with displacement ellipsoids at the 20% probability level. H atoms are shown as small spheres of arbitrary radii.

2-Methyl-1-phenylsulfanyl-1,2-dicarba-closo-dodecaborane(12)

Crystal data

C9H18B10S	F(000) = 552
Mr = 266.39	Dx = 1.162 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 7.2391 (14) Å	θ = 10.1–15.9°
b = 17.2093 (11) Å	µ = 0.19 mm^−1
c = 12.3461 (10) Å	T = 296 K
β = 98.066 (10)°	Prism, pale yellow
V = 1522.9 (3) Å^3	0.38 × 0.26 × 0.24 mm
Z = 4

Data collection

Rigaku AFC-5S diffractometer	1708 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→20
Tmin = 0.943, Tmax = 0.956	l = −14→14
2906 measured reflections	3 standard reflections every 150 reflections
2681 independent reflections	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 0.458P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2681 reflections	Δρmax = 0.20 e Å^−3
183 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0060 (16)

Special details

Experimental. Before use, 1-Me-1,2-C₂B₁₀H₁₁ (Katchem) was sublimed. A 1.7 M solution of n-butyllithium in hexane (Aldrich) was used as recieved. Diethyl ether was distilled from sodium benzophenone prior to use. A solution containing diethyl ether (30 ml) and 1-Me-1,2-C₂B₁₀H₁₁ (1.0 g, 6.5 mmol) was cooled to 273 K during the addition (10 min, dropwise) of n-butyllitium (4.2 ml, 6.5 mmol). After stirring for 30 min at 273 K, the mixture was left to stand at room temperature for 30 min, then cooled again to 273 K before adding a diethyl ether solution (10 ml) of phenyldisulfide (1.4 g, 6.5 mmol). A white solid precipitated. The ice-bath was removed and the mixture was stirred for 30 min at room temperature. The ether mixture was washed twice with water containing KCl (50 ml). The organic layer was dried (anhydrous MgSO₄, 24 h) and evaporated to yield the analytically pure white solid, (I) (yield 0.95 g, 76%). Recrystallization from dichloromethane-n-hexane (1/1) gave pale-yellow crystals of (I). Analysis calculated for C₉H₁₈B₁₀S: C 40.58, H 6.81, S 12.03%; found: C 40.76, H 6.51, S 11.62%. Spectroscopic data: IR (KBr, ν, cm^-1): 3064 (C—H_aryl), 2939 (C—H_alkyl), 2615, 2603, 2571, 2547 (B—H); ¹H NMR (250.13 MHz, CDCl₃, 298 K, TMS, δ, p.p.m.): 7.57–7.40 (m, 5H, C—H_aryl), 3.50–0.50 (b s, B—H), 2.22 (s, 3H, CH₃); ¹¹B NMR (128.40 MHz, CDCl₃, 298 K, BF₃·OEt₂, δ, p.p.m.): -3.8 [d, ¹J(B, H) = 150 Hz, 1B], -5.0 [d, ¹J(B, H) = 150 Hz, 1B], -8.8 (d, 2B), -10.0 [d, ¹J(B, H) = 155 Hz, 6B]; ¹³C{¹H} NMR (62.90 MHz, CDCl₃, 298 K, TMS, δ, p.p.m.): 137.2, 131.3, 130.0, 129.5 (C_aryl), 81.8 (C_cage), 79.4 (C_cage), 23.5 (CH₃).

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 (Ų)

	x	y	z	Uiso*/Ueq
S	0.81260 (11)	0.15674 (4)	0.46626 (6)	0.0456 (3)
C1	0.7989 (4)	0.24702 (15)	0.5357 (2)	0.0355 (7)
C2	0.9208 (4)	0.32538 (16)	0.4988 (2)	0.0425 (7)
B3	0.6860 (5)	0.3186 (2)	0.4538 (3)	0.0483 (9)
H3	0.6276	0.3092	0.3676	0.058*
B4	0.5835 (5)	0.2773 (2)	0.5623 (3)	0.0494 (9)
H4	0.4561	0.2418	0.5469	0.059*
B5	0.7670 (5)	0.2550 (2)	0.6692 (3)	0.0467 (9)
H5	0.7585	0.2051	0.7239	0.056*
B6	0.9812 (5)	0.2832 (2)	0.6255 (3)	0.0422 (8)
H6	1.1122	0.2514	0.6498	0.051*
B7	0.7926 (5)	0.4079 (2)	0.5015 (3)	0.0518 (9)
H7	0.8011	0.4577	0.4465	0.062*
B8	0.5795 (5)	0.3791 (2)	0.5436 (3)	0.0542 (10)
H8	0.4486	0.4103	0.5164	0.065*
B9	0.6298 (5)	0.3397 (2)	0.6766 (3)	0.0554 (10)
H9	0.5318	0.3455	0.7367	0.066*
B10	0.8761 (5)	0.3426 (2)	0.7162 (3)	0.0518 (9)
H10	0.9386	0.3499	0.8020	0.062*
B11	0.9764 (5)	0.3850 (2)	0.6076 (3)	0.0507 (9)
H11	1.1052	0.4197	0.6221	0.061*
B12	0.7593 (5)	0.4202 (2)	0.6385 (3)	0.0510 (9)
H12	0.7458	0.4783	0.6737	0.061*
C13	1.0507 (5)	0.3138 (2)	0.4143 (3)	0.0656 (10)
H13A	0.9979	0.2763	0.3612	0.098*
H13B	1.1692	0.2953	0.4496	0.098*
H13C	1.0675	0.3623	0.3786	0.098*
C14	1.0032 (4)	0.10757 (15)	0.5436 (2)	0.0386 (7)
C15	1.1771 (4)	0.10842 (17)	0.5087 (2)	0.0492 (8)
H15	1.1948	0.1357	0.4460	0.059*
C16	1.3237 (5)	0.06863 (19)	0.5674 (3)	0.0617 (9)
H16	1.4406	0.0694	0.5443	0.074*
C17	1.2979 (5)	0.02790 (19)	0.6596 (3)	0.0670 (11)
H17	1.3977	0.0019	0.6994	0.080*
C18	1.1253 (5)	0.02547 (19)	0.6930 (3)	0.0649 (10)
H18	1.1076	−0.0031	0.7547	0.078*
C19	0.9777 (5)	0.06527 (17)	0.6356 (3)	0.0513 (8)
H19	0.8609	0.0637	0.6587	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0470 (4)	0.0381 (4)	0.0479 (4)	0.0022 (4)	−0.0064 (3)	−0.0083 (4)
C1	0.0334 (15)	0.0341 (14)	0.0381 (15)	−0.0041 (12)	0.0020 (12)	0.0003 (12)
C2	0.0462 (17)	0.0389 (16)	0.0437 (16)	−0.0070 (13)	0.0104 (13)	−0.0017 (13)
B3	0.054 (2)	0.0411 (19)	0.046 (2)	0.0039 (17)	−0.0098 (17)	0.0015 (15)
B4	0.0349 (19)	0.0402 (18)	0.074 (3)	0.0008 (15)	0.0100 (18)	0.0009 (18)
B5	0.054 (2)	0.048 (2)	0.0409 (19)	0.0078 (17)	0.0148 (17)	0.0082 (16)
B6	0.0347 (18)	0.0478 (19)	0.0410 (19)	−0.0004 (16)	−0.0052 (15)	−0.0051 (16)
B7	0.064 (2)	0.0344 (18)	0.057 (2)	−0.0001 (17)	0.0057 (19)	0.0037 (16)
B8	0.042 (2)	0.043 (2)	0.075 (3)	0.0074 (17)	−0.0014 (19)	−0.0023 (18)
B9	0.056 (2)	0.054 (2)	0.061 (2)	0.008 (2)	0.0235 (19)	0.0004 (19)
B10	0.060 (2)	0.054 (2)	0.0402 (19)	0.005 (2)	0.0025 (17)	−0.0093 (17)
B11	0.048 (2)	0.042 (2)	0.061 (2)	−0.0116 (17)	0.0017 (18)	−0.0136 (17)
B12	0.055 (2)	0.0406 (19)	0.057 (2)	0.0040 (17)	0.0051 (18)	−0.0097 (17)
C13	0.074 (3)	0.064 (2)	0.066 (2)	−0.008 (2)	0.036 (2)	0.0005 (18)
C14	0.0429 (17)	0.0313 (14)	0.0401 (15)	0.0022 (12)	0.0008 (13)	−0.0019 (12)
C15	0.0510 (19)	0.0426 (17)	0.055 (2)	0.0044 (15)	0.0102 (16)	0.0050 (14)
C16	0.0434 (19)	0.048 (2)	0.093 (3)	0.0040 (16)	0.0052 (18)	−0.0012 (19)
C17	0.064 (2)	0.0403 (18)	0.088 (3)	0.0073 (18)	−0.021 (2)	0.0053 (18)
C18	0.083 (3)	0.0464 (19)	0.062 (2)	0.002 (2)	−0.003 (2)	0.0138 (16)
C19	0.058 (2)	0.0407 (17)	0.0564 (19)	−0.0033 (16)	0.0119 (16)	0.0014 (15)

Geometric parameters (Å, º)

S—C1	1.784 (3)	B7—B11	1.776 (5)
S—C14	1.778 (3)	B7—H7	1.1000
C1—C2	1.708 (4)	B8—B9	1.767 (5)
C1—B3	1.726 (4)	B8—B12	1.772 (5)
C1—B4	1.718 (4)	B8—H8	1.1000
C1—B5	1.702 (4)	B9—B12	1.772 (5)
C1—B6	1.717 (4)	B9—B10	1.782 (5)
C2—C13	1.513 (4)	B9—H9	1.1000
C2—B11	1.694 (4)	B10—B11	1.769 (5)
C2—B7	1.699 (4)	B10—B12	1.785 (5)
C2—B3	1.716 (5)	B10—H10	1.1000
C2—B6	1.724 (4)	B11—B12	1.775 (5)
B3—B4	1.769 (5)	B11—H11	1.1000
B3—B8	1.774 (5)	B12—H12	1.1000
B3—B7	1.781 (5)	C13—H13A	0.9600
B3—H3	1.1000	C13—H13B	0.9600
B4—B8	1.768 (5)	C13—H13C	0.9600
B4—B9	1.769 (5)	C14—C19	1.383 (4)
B4—B5	1.778 (5)	C14—C15	1.387 (4)
B4—H4	1.1000	C15—C16	1.380 (4)
B5—B10	1.761 (5)	C15—H15	0.9300
B5—B9	1.774 (5)	C16—C17	1.371 (5)
B5—B6	1.779 (5)	C16—H16	0.9300
B5—H5	1.1000	C17—C18	1.371 (5)
B6—B10	1.765 (5)	C17—H17	0.9300
B6—B11	1.766 (5)	C18—C19	1.379 (4)
B6—H6	1.1000	C18—H18	0.9300
B7—B12	1.755 (5)	C19—H19	0.9300
B7—B8	1.766 (5)
C14—S—C1	104.33 (12)	B8—B7—H7	121.8
B5—C1—C2	109.9 (2)	B11—B7—H7	121.8
B5—C1—B6	62.72 (19)	B3—B7—H7	121.8
C2—C1—B6	60.45 (17)	B7—B8—B9	107.9 (3)
B5—C1—B4	62.7 (2)	B7—B8—B4	108.5 (2)
C2—C1—B4	109.2 (2)	B9—B8—B4	60.1 (2)
B6—C1—B4	113.7 (2)	B7—B8—B12	59.5 (2)
B5—C1—B3	113.1 (2)	B9—B8—B12	60.1 (2)
C2—C1—B3	59.97 (18)	B4—B8—B12	108.2 (3)
B6—C1—B3	112.2 (2)	B7—B8—B3	60.4 (2)
B4—C1—B3	61.8 (2)	B9—B8—B3	107.8 (3)
C2—C1—S	119.59 (18)	B4—B8—B3	60.0 (2)
B3—C1—S	113.19 (18)	B12—B8—B3	107.7 (3)
B5—C1—S	124.1 (2)	B7—B8—H8	121.6
B4—C1—S	117.93 (19)	B9—B8—H8	121.8
B6—C1—S	122.48 (19)	B4—B8—H8	121.4
C13—C2—C1	118.3 (2)	B12—B8—H8	121.9
C13—C2—B3	116.8 (3)	B3—B8—H8	121.8
C13—C2—B6	117.8 (3)	B8—B9—B4	60.0 (2)
C13—C2—B7	121.2 (3)	B8—B9—B12	60.1 (2)
C13—C2—B11	121.7 (3)	B4—B9—B12	108.1 (3)
B11—C2—B7	63.1 (2)	B8—B9—B5	108.1 (3)
B11—C2—C1	109.9 (2)	B4—B9—B5	60.3 (2)
B7—C2—C1	110.5 (2)	B12—B9—B5	107.9 (3)
B11—C2—B3	114.4 (2)	B8—B9—B10	108.2 (3)
B7—C2—B3	62.9 (2)	B4—B9—B10	107.8 (2)
C1—C2—B3	60.53 (17)	B12—B9—B10	60.3 (2)
B11—C2—B6	62.19 (19)	B5—B9—B10	59.4 (2)
B7—C2—B6	113.8 (2)	B8—B9—H9	121.6
C1—C2—B6	60.03 (17)	B4—B9—H9	121.7
B3—C2—B6	112.3 (2)	B12—B9—H9	121.6
C2—B3—C1	59.50 (17)	B5—B9—H9	121.9
C2—B3—B4	106.5 (2)	B10—B9—H9	121.9
C1—B3—B4	58.88 (18)	B5—B10—B6	60.6 (2)
C2—B3—B8	104.8 (2)	B5—B10—B11	108.5 (2)
C1—B3—B8	105.3 (2)	B6—B10—B11	59.9 (2)
B4—B3—B8	59.9 (2)	B5—B10—B9	60.1 (2)
C2—B3—B7	58.09 (19)	B6—B10—B9	108.3 (2)
C1—B3—B7	105.9 (2)	B11—B10—B9	107.8 (3)
B4—B3—B7	107.8 (3)	B5—B10—B12	107.9 (2)
B8—B3—B7	59.6 (2)	B6—B10—B12	107.8 (2)
C2—B3—H3	123.5	B11—B10—B12	59.9 (2)
C1—B3—H3	123.2	B9—B10—B12	59.6 (2)
B4—B3—H3	121.8	B5—B10—H10	121.3
B8—B3—H3	123.3	B6—B10—H10	121.5
B7—B3—H3	122.5	B11—B10—H10	121.7
C1—B4—B8	105.9 (2)	B9—B10—H10	121.8
C1—B4—B9	105.1 (2)	B12—B10—H10	122.1
B8—B4—B9	60.0 (2)	C2—B11—B6	59.74 (18)
C1—B4—B3	59.30 (18)	C2—B11—B10	105.9 (2)
B8—B4—B3	60.2 (2)	B6—B11—B10	59.9 (2)
B9—B4—B3	107.9 (3)	C2—B11—B12	104.9 (2)
C1—B4—B5	58.23 (18)	B6—B11—B12	108.3 (3)
B8—B4—B5	107.9 (3)	B10—B11—B12	60.5 (2)
B9—B4—B5	60.0 (2)	C2—B11—B7	58.58 (19)
B3—B4—B5	107.5 (2)	B6—B11—B7	108.2 (2)
C1—B4—H4	124.1	B10—B11—B7	107.8 (3)
B8—B4—H4	121.9	B12—B11—B7	59.2 (2)
B9—B4—H4	122.3	C2—B11—H11	124.0
B3—B4—H4	121.5	B6—B11—H11	121.1
B5—B4—H4	122.0	B10—B11—H11	122.0
C1—B5—B10	105.8 (2)	B12—B11—H11	122.4
C1—B5—B9	105.6 (2)	B7—B11—H11	122.0
B10—B5—B9	60.5 (2)	B7—B12—B8	60.1 (2)
C1—B5—B4	59.12 (18)	B7—B12—B9	108.1 (3)
B10—B5—B4	108.3 (2)	B8—B12—B9	59.8 (2)
B9—B5—B4	59.7 (2)	B7—B12—B11	60.4 (2)
C1—B5—B6	59.05 (17)	B8—B12—B11	108.2 (3)
B10—B5—B6	59.8 (2)	B9—B12—B11	108.0 (2)
B9—B5—B6	108.0 (3)	B7—B12—B10	108.0 (2)
B4—B5—B6	107.9 (2)	B8—B12—B10	107.8 (3)
C1—B5—H5	123.9	B9—B12—B10	60.1 (2)
B10—B5—H5	121.9	B11—B12—B10	59.6 (2)
B9—B5—H5	122.1	B7—B12—H12	121.5
B4—B5—H5	121.6	B8—B12—H12	121.8
B6—B5—H5	121.7	B9—B12—H12	121.7
C1—B6—C2	59.52 (17)	B11—B12—H12	121.7
C1—B6—B10	105.0 (2)	B10—B12—H12	121.9
C2—B6—B10	104.8 (2)	C2—C13—H13A	109.5
C1—B6—B11	106.2 (2)	C2—C13—H13B	109.5
C2—B6—B11	58.06 (19)	H13A—C13—H13B	109.5
B10—B6—B11	60.2 (2)	C2—C13—H13C	109.5
C1—B6—B5	58.23 (18)	H13A—C13—H13C	109.5
C2—B6—B5	105.6 (2)	H13B—C13—H13C	109.5
B10—B6—B5	59.6 (2)	C19—C14—C15	119.5 (3)
B11—B6—B5	107.8 (3)	C19—C14—S	120.6 (2)
C1—B6—H6	123.4	C15—C14—S	119.9 (2)
C2—B6—H6	123.8	C16—C15—C14	119.8 (3)
B10—B6—H6	123.2	C16—C15—H15	120.1
B11—B6—H6	122.0	C14—C15—H15	120.1
B5—B6—H6	122.4	C17—C16—C15	120.3 (3)
C2—B7—B12	105.6 (2)	C17—C16—H16	119.8
C2—B7—B8	105.9 (2)	C15—C16—H16	119.8
B12—B7—B8	60.4 (2)	C18—C17—C16	120.1 (3)
C2—B7—B11	58.30 (19)	C18—C17—H17	119.9
B12—B7—B11	60.3 (2)	C16—C17—H17	119.9
B8—B7—B11	108.4 (3)	C17—C18—C19	120.2 (3)
C2—B7—B3	59.03 (18)	C17—C18—H18	119.9
B12—B7—B3	108.1 (3)	C19—C18—H18	119.9
B8—B7—B3	60.0 (2)	C18—C19—C14	120.1 (3)
B11—B7—B3	107.3 (2)	C18—C19—H19	120.0
C2—B7—H7	124.1	C14—C19—H19	120.0
B12—B7—H7	121.9
C13—C2—C1—S	−5.3 (3)	C1—S—C14—C15	−99.0 (2)
C2—C1—S—C14	90.4 (2)	C1—S—C14—C19	84.2 (2)