1,2-Bis(dimethyl­amino)-1,2-bis­(2,4,6-triisopropyl­phen­yl)diborane(4)

Braunschweig, H.; Damme, A.

doi:10.1107/S1600536810049500

organic compounds

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Volume 66| Part 12| December 2010| Page o3367

https://doi.org/10.1107/S1600536810049500

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1,2-Bis(dimethylamino)-1,2-bis(2,4,6-triisopropylphenyl)diborane(4)

Holger Braunschweig ^a ^* and Alexander Damme ^a

^aInstitut fuer Anorganische Chemie, Universitaet Wuerzburg, Am Hubland, D-97074 Wuerzburg, Germany
^*Correspondence e-mail: h.braunschweig@mail.uni-wuerzburg.de

(Received 12 November 2010; accepted 26 November 2010; online 30 November 2010)

In the molecular structure of the title compound, C₃₄H₅₈B₂N₂, each B atom of the diborane(4) is connected to one dimethylamino group and one Tip ligand (Tip = 2,4,6-triisopropylphenyl). These findings indicate that the increased steric demand of the Tip groups exerts influence solely on the B—B separation but not on the overall geometry of the title compound.

Related literature

For the synthesis of the title compound with 1,2-bis(dimethylamino)-1,2-dichlorodiborane(4) as starting material, see: Hunold (1988 ). For 1,2-diaryl-1,2-bis(dimethylamino)diboranes(4) (aryl = phenyl or mesityl), see: Moezzi et al. (1992 ) and for dimesityldiboranes(4), see: Hommer et al. (1998 ).

Experimental

Crystal data

C₃₄H₅₈B₂N₂
M_r = 516.44
Triclinic, $[P \overline 1]$
a = 9.6066 (19) Å
b = 13.919 (3) Å
c = 14.015 (3) Å
α = 82.983 (3)°
β = 71.549 (3)°
γ = 78.300 (3)°
V = 1737.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 171 K
0.40 × 0.17 × 0.12 mm

Data collection

Bruker APEXI CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.494, T_max = 0.745
19559 measured reflections
7202 independent reflections
5554 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.173
S = 1.03
7202 reflections
359 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART-NT (Bruker, 1997 ); cell refinement: SAINT-Plus-NT (Bruker, 1997); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1997); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810049500/br2151sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810049500/br2151Isup2.hkl

checkCIF report

Comment top

The B–B bond of 1,2-bis(dimethylamino)-1,2-bis(2,4,6-triisopropylphenyl)diborane(4) is with 1.731 (2) Å slightly longer with respect to those reported previously for phenyl (1.714 (4) Å) and mesityl (1.717 (15) Å) substituted 1,2-bis(dimethylamino)diboranes(4) (Moezzi et al., 1992), but the B–N (about 1.40 Å) and B–C_i (about 1.59 Å) bonds are comparable to the corresponding bond lengths of the afore mentioned compounds.

In the case of 1,2-bis(dimethylamino)-1,2-bis(2,4,6-trimethylphenyl)diborane(4) a reaction with MeOH and etheric HCl leads to 1,2-bis(2,4,6-trimethylphenyl)-1,2-di(methoxy)diborane(4), this is not possible with 1,2-bis(dimethylamino)-1,2-bis(2,4,6-triisopropylphenyl)diborane(4) (Hunold, 1988).

Related literature top

For the synthesis of the title compound with 1,2-bis(dimethylamino)-1,2-dichlorodiborane(4) as starting material, see: Hunold (1988). For 1,2-diaryl-1,2-bis(dimethylamino)diboranes(4) (aryl = phenyl or mesityl), see: Moezzi et al. (1992) and for dimesityldiboranes(4), see: Hommer et al. (1998).

Experimental top

A solution of 2,4,6-triisopropylphenyllithium (2.09 g, 7.34 mmol, 2.18 eq) in Et₂O (25 ml) was added to 1,2-bis(dimethylamino)-1,2-dibromodiborane(4) (0.908 g, 3.36 mmol) dissolved in Et₂O (15 ml). The reaction mixture was refluxed for 16 h. All volatiles were removed under reduced pressure. The crude product was crystallized from hexane to yield 60% 1,2-bis(dimethylamino)-1,2-bis(2,4,6-triisopropylphenyl)diborane(4) as colourless crystals (1.04 g, 2.01 mmol).

NMR: ¹H NMR (300.0 K, 500.13 MHz, CDCl₃): δ = 0.02 (d, ³J_H–H = 6.70 Hz, 6H, CH₃), 0.92 (d, ³J_H–H = 6.85 Hz, 6H, CH₃), 1.12–1.18 (m, 18H, CH₃), 1.22 (d, ³J_H–H = 6.85 Hz, 6H, CH₃), 2.15–2.23 (m, 2H, CH), 2.70–2.78 (m, 2H, CH), 2.78–2.85 (m, 2H, CH), 2.64 (s, 6H, NCH₃), 3.12 (s, 6H, NCH₃), 6.62–6.65 (m, 2H, CH_arom.), 6.81–6.83 p.p.m. (m, 2H, CH_arom.); ¹¹B NMR (296.1 K, 160.46 MHz, CDCl₃): δ = 49.6 p.p.m.; ¹³C NMR (300.0 K, 160.46 MHz, CDCl₃): δ = 149.15 (s, C_i), 148.17 (s, C_i), 146.66 (s, C_i), 142.00 (s, C_i), 120.11 (s, CH_arom.), 119.41 (s, CH_arom.), 43.94 (s, NCH₃), 42.29 (s, NCH₃), 34.36 (s, CH), 34.16 (s, CH), 33.98 (s, CH), 25.35 (s, CH₃), 25.27 (s, CH₃), 24.41 (s, CH₃), 24.13 (s, CH₃), 22.64 p.p.m. (s, CH₃).

Analysis calcd. for C₃₄H₅₈B₂N₂: C, 79.07; H, 11.32; N, 5.42%. Found: C, 78.79; H, 11.21; N, 5.20%.

Structure description top

For the synthesis of the title compound with 1,2-bis(dimethylamino)-1,2-dichlorodiborane(4) as starting material, see: Hunold (1988). For 1,2-diaryl-1,2-bis(dimethylamino)diboranes(4) (aryl = phenyl or mesityl), see: Moezzi et al. (1992) and for dimesityldiboranes(4), see: Hommer et al. (1998).

Computing details top

Data collection: SMART-NT (Bruker, 1997); cell refinement: SAINT-Plus-NT (Bruker, 1997); data reduction: SAINT-Plus-NT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atom numbering scheme and displacement ellipsoids for the non-H atoms at the 50% probability level. Hydrogen atoms are omitted for clarity.

1,2-Bis(dimethylamino)-1,2-bis(2,4,6-triisopropylphenyl)diborane(4) top

Crystal data top

C₃₄H₅₈B₂N₂	Z = 2
M_r = 516.44	F(000) = 572
Triclinic, P1	D_x = 0.987 Mg m⁻³
Hall symbol: -P 1	Melting point: 192.11 K
a = 9.6066 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.919 (3) Å	Cell parameters from 5619 reflections
c = 14.015 (3) Å	θ = 2.2–26.5°
α = 82.983 (3)°	µ = 0.06 mm⁻¹
β = 71.549 (3)°	T = 171 K
γ = 78.300 (3)°	Block, colourless
V = 1737.4 (6) Å³	0.40 × 0.17 × 0.12 mm

Data collection top

Bruker APEXI CCD diffractometer	7202 independent reflections
Radiation source: sealed tube	5554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
φ and ω scans	θ_max = 26.6°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
T_min = 0.494, T_max = 0.745	k = −17→17
19559 measured reflections	l = −17→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0841P)² + 0.3205P] where P = (F_o² + 2F_c²)/3
7202 reflections	(Δ/σ)_max < 0.001
359 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₃₄H₅₈B₂N₂	γ = 78.300 (3)°
M_r = 516.44	V = 1737.4 (6) Å³
Triclinic, P1	Z = 2
a = 9.6066 (19) Å	Mo Kα radiation
b = 13.919 (3) Å	µ = 0.06 mm⁻¹
c = 14.015 (3) Å	T = 171 K
α = 82.983 (3)°	0.40 × 0.17 × 0.12 mm
β = 71.549 (3)°

Data collection top

Bruker APEXI CCD diffractometer	7202 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	5554 reflections with I > 2σ(I)
T_min = 0.494, T_max = 0.745	R_int = 0.062
19559 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
7202 reflections	Δρ_min = −0.24 e Å⁻³
359 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	0.51577 (18)	0.82586 (12)	0.21886 (12)	0.0269 (3)
B2	0.54148 (19)	0.73592 (12)	0.31158 (12)	0.0280 (3)
N1	0.57731 (15)	0.91179 (9)	0.20047 (9)	0.0333 (3)
C1	0.5537 (2)	0.99154 (13)	0.12572 (14)	0.0497 (5)
H1A	0.4878	0.9756	0.0912	0.057 (6)*
H1B	0.6496	0.9996	0.0764	0.061 (6)*
H1C	0.5078	1.0528	0.1596	0.066 (6)*
C2	0.6729 (2)	0.93496 (13)	0.25401 (13)	0.0430 (4)
H2A	0.6851	0.8820	0.3052	0.043 (5)*
H2B	0.6272	0.9969	0.2867	0.057 (6)*
H2C	0.7705	0.9416	0.2062	0.057 (6)*
N2	0.68120 (15)	0.68380 (10)	0.31429 (10)	0.0366 (3)
C3	0.82264 (19)	0.69513 (15)	0.23912 (14)	0.0482 (4)
H3A	0.8059	0.7490	0.1898	0.042 (5)*
H3B	0.8663	0.6340	0.2047	0.058 (6)*
H3C	0.8909	0.7100	0.2723	0.067 (6)*
C4	0.7037 (2)	0.60721 (15)	0.39242 (15)	0.0552 (5)
H4A	0.6078	0.6021	0.4433	0.054 (6)*
H4B	0.7718	0.6243	0.4244	0.088 (8)*
H4C	0.7466	0.5441	0.3617	0.070 (7)*
C5	0.41071 (16)	0.81281 (10)	0.15445 (10)	0.0274 (3)
C6	0.46957 (17)	0.75872 (11)	0.06756 (11)	0.0318 (3)
C7	0.37787 (19)	0.74638 (12)	0.01237 (12)	0.0375 (4)
H7	0.4199	0.7105	−0.0466	0.045*
C8	0.22699 (19)	0.78480 (12)	0.04069 (12)	0.0375 (4)
C9	0.16922 (18)	0.83731 (12)	0.12656 (12)	0.0365 (4)
H9	0.0660	0.8645	0.1471	0.044*
C10	0.25752 (17)	0.85167 (10)	0.18397 (11)	0.0308 (3)
C11	0.63496 (18)	0.71524 (12)	0.03242 (12)	0.0389 (4)
H11	0.6743	0.7153	0.0905	0.047*
C12	0.1276 (2)	0.76690 (14)	−0.01881 (14)	0.0464 (4)
H12	0.0228	0.7963	0.0175	0.056*
C13	0.18586 (18)	0.90841 (12)	0.27877 (12)	0.0375 (4)
H13	0.2637	0.9040	0.3133	0.045*
C14	0.7191 (2)	0.77944 (16)	−0.05258 (18)	0.0640 (6)
H14A	0.6975	0.8471	−0.0321	0.096*
H14B	0.6878	0.7782	−0.1125	0.096*
H14C	0.8263	0.7545	−0.0681	0.096*
C15	0.6675 (2)	0.60935 (14)	0.00323 (18)	0.0636 (6)
H15A	0.6134	0.5688	0.0595	0.095*
H15B	0.7748	0.5844	−0.0125	0.095*
H15C	0.6354	0.6067	−0.0560	0.095*
C16	0.1325 (3)	0.65785 (16)	−0.02416 (18)	0.0636 (6)
H16A	0.0668	0.6491	−0.0624	0.095*
H16B	0.0990	0.6275	0.0442	0.095*
H16C	0.2348	0.6266	−0.0578	0.095*
C17	0.1674 (3)	0.8170 (2)	−0.12350 (19)	0.0882 (9)
H17A	0.1013	0.8044	−0.1596	0.132*
H17B	0.2710	0.7912	−0.1602	0.132*
H17C	0.1557	0.8880	−0.1185	0.132*
C18	0.1340 (3)	1.01727 (14)	0.25493 (18)	0.0669 (6)
H18A	0.0888	1.0508	0.3179	0.100*
H18B	0.0603	1.0242	0.2185	0.100*
H18C	0.2196	1.0467	0.2131	0.100*
C19	0.05621 (19)	0.86431 (14)	0.35297 (13)	0.0449 (4)
H19A	0.0904	0.7946	0.3685	0.067*
H19B	−0.0246	0.8708	0.3228	0.067*
H19C	0.0199	0.8993	0.4151	0.067*
C20	0.39744 (16)	0.70813 (10)	0.39634 (10)	0.0284 (3)
C21	0.33107 (17)	0.76128 (11)	0.48375 (11)	0.0309 (3)
C22	0.20580 (18)	0.73635 (11)	0.55681 (11)	0.0350 (4)
H22	0.1638	0.7726	0.6155	0.042*
C23	0.13993 (18)	0.65943 (11)	0.54635 (11)	0.0348 (4)
C24	0.20400 (19)	0.60811 (11)	0.45993 (11)	0.0356 (4)
H24	0.1604	0.5555	0.4514	0.043*
C25	0.33014 (18)	0.63093 (11)	0.38507 (11)	0.0319 (3)
C26	0.3937 (2)	0.57152 (12)	0.29141 (12)	0.0417 (4)
H26	0.4759	0.6032	0.2437	0.050*
C27	−0.0016 (2)	0.63573 (14)	0.62444 (13)	0.0469 (4)
H27	−0.0167	0.5707	0.6097	0.056*
C28	0.39924 (19)	0.84595 (12)	0.49932 (12)	0.0382 (4)
H28	0.4714	0.8629	0.4333	0.046*
C29	0.4616 (3)	0.46551 (14)	0.31668 (17)	0.0662 (6)
H29A	0.5352	0.4662	0.3515	0.099*
H29B	0.5103	0.4315	0.2543	0.099*
H29C	0.3827	0.4312	0.3604	0.099*
C30	0.2782 (3)	0.57269 (15)	0.23764 (13)	0.0536 (5)
H30A	0.2367	0.6409	0.2217	0.080*
H30B	0.1981	0.5394	0.2814	0.080*
H30C	0.3255	0.5386	0.1752	0.080*
C31	−0.1356 (2)	0.7113 (2)	0.6151 (2)	0.0797 (7)
H31A	−0.2258	0.6945	0.6656	0.120*
H31B	−0.1453	0.7116	0.5475	0.120*
H31C	−0.1221	0.7765	0.6261	0.120*
C32	0.0069 (3)	0.62659 (18)	0.73136 (14)	0.0639 (6)
H32A	0.0942	0.5780	0.7361	0.096*
H32B	−0.0835	0.6055	0.7775	0.096*
H32C	0.0154	0.6904	0.7497	0.096*
C33	0.4866 (3)	0.81472 (16)	0.5746 (2)	0.0688 (6)
H33A	0.5601	0.7554	0.5531	0.103*
H33B	0.4181	0.8009	0.6412	0.103*
H33C	0.5379	0.8677	0.5781	0.103*
C34	0.2852 (2)	0.93833 (13)	0.53104 (17)	0.0562 (5)
H34A	0.2298	0.9578	0.4818	0.084*
H34B	0.3364	0.9915	0.5342	0.084*
H34C	0.2158	0.9253	0.5975	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0259 (8)	0.0282 (8)	0.0253 (8)	−0.0020 (6)	−0.0074 (6)	−0.0024 (6)
B2	0.0348 (9)	0.0261 (8)	0.0258 (8)	−0.0041 (6)	−0.0128 (7)	−0.0033 (6)
N1	0.0410 (7)	0.0300 (6)	0.0346 (7)	−0.0105 (5)	−0.0184 (6)	0.0034 (5)
C1	0.0680 (13)	0.0368 (9)	0.0545 (11)	−0.0206 (9)	−0.0322 (10)	0.0147 (8)
C2	0.0491 (10)	0.0434 (10)	0.0461 (10)	−0.0187 (8)	−0.0225 (8)	0.0009 (8)
N2	0.0356 (7)	0.0375 (7)	0.0340 (7)	0.0011 (6)	−0.0132 (6)	0.0026 (5)
C3	0.0330 (9)	0.0562 (11)	0.0502 (11)	0.0012 (8)	−0.0116 (8)	−0.0012 (9)
C4	0.0545 (12)	0.0535 (12)	0.0497 (11)	0.0102 (9)	−0.0223 (9)	0.0120 (9)
C5	0.0316 (8)	0.0258 (7)	0.0262 (7)	−0.0060 (6)	−0.0115 (6)	0.0027 (5)
C6	0.0369 (8)	0.0313 (8)	0.0276 (7)	−0.0051 (6)	−0.0121 (6)	0.0013 (6)
C7	0.0458 (9)	0.0415 (9)	0.0286 (8)	−0.0067 (7)	−0.0153 (7)	−0.0053 (6)
C8	0.0429 (9)	0.0414 (9)	0.0347 (8)	−0.0104 (7)	−0.0197 (7)	0.0007 (7)
C9	0.0329 (8)	0.0380 (9)	0.0416 (9)	−0.0043 (7)	−0.0169 (7)	−0.0011 (7)
C10	0.0331 (8)	0.0277 (7)	0.0333 (8)	−0.0052 (6)	−0.0132 (6)	−0.0001 (6)
C11	0.0393 (9)	0.0453 (9)	0.0318 (8)	0.0012 (7)	−0.0135 (7)	−0.0081 (7)
C12	0.0492 (10)	0.0537 (11)	0.0471 (10)	−0.0122 (8)	−0.0278 (8)	−0.0025 (8)
C13	0.0336 (8)	0.0389 (9)	0.0417 (9)	−0.0008 (7)	−0.0142 (7)	−0.0107 (7)
C14	0.0422 (11)	0.0548 (12)	0.0795 (15)	−0.0053 (9)	0.0015 (10)	−0.0042 (11)
C15	0.0574 (13)	0.0438 (11)	0.0723 (14)	0.0034 (9)	−0.0005 (11)	−0.0108 (10)
C16	0.0714 (14)	0.0623 (13)	0.0758 (15)	−0.0225 (11)	−0.0409 (12)	−0.0053 (11)
C17	0.119 (2)	0.108 (2)	0.0763 (16)	−0.0654 (18)	−0.0728 (16)	0.0400 (15)
C18	0.0763 (15)	0.0375 (10)	0.0713 (14)	−0.0027 (10)	−0.0018 (12)	−0.0118 (10)
C19	0.0394 (9)	0.0502 (10)	0.0413 (9)	−0.0012 (8)	−0.0090 (7)	−0.0076 (8)
C20	0.0355 (8)	0.0241 (7)	0.0269 (7)	−0.0026 (6)	−0.0137 (6)	0.0009 (5)
C21	0.0369 (8)	0.0275 (7)	0.0298 (8)	−0.0050 (6)	−0.0120 (6)	−0.0026 (6)
C22	0.0412 (9)	0.0355 (8)	0.0288 (8)	−0.0079 (7)	−0.0081 (7)	−0.0083 (6)
C23	0.0392 (9)	0.0358 (8)	0.0306 (8)	−0.0107 (7)	−0.0093 (7)	−0.0022 (6)
C24	0.0473 (9)	0.0303 (8)	0.0331 (8)	−0.0142 (7)	−0.0134 (7)	−0.0011 (6)
C25	0.0427 (9)	0.0260 (7)	0.0277 (7)	−0.0056 (6)	−0.0117 (6)	−0.0020 (6)
C26	0.0572 (11)	0.0342 (8)	0.0316 (8)	−0.0152 (8)	−0.0041 (7)	−0.0069 (7)
C27	0.0484 (10)	0.0499 (10)	0.0416 (10)	−0.0225 (8)	−0.0006 (8)	−0.0117 (8)
C28	0.0440 (9)	0.0371 (8)	0.0348 (8)	−0.0148 (7)	−0.0067 (7)	−0.0078 (7)
C29	0.0898 (17)	0.0394 (10)	0.0592 (13)	0.0027 (10)	−0.0113 (12)	−0.0176 (9)
C30	0.0842 (15)	0.0497 (11)	0.0352 (9)	−0.0282 (10)	−0.0178 (9)	−0.0072 (8)
C31	0.0397 (12)	0.1007 (19)	0.0950 (18)	−0.0201 (12)	−0.0103 (12)	−0.0055 (15)
C32	0.0706 (14)	0.0744 (14)	0.0379 (10)	−0.0280 (11)	0.0071 (9)	−0.0076 (9)
C33	0.0684 (14)	0.0534 (12)	0.1082 (19)	−0.0114 (10)	−0.0560 (14)	−0.0135 (12)
C34	0.0718 (14)	0.0369 (9)	0.0727 (13)	−0.0073 (9)	−0.0361 (11)	−0.0159 (9)

Geometric parameters (Å, º) top

B1—N1	1.401 (2)	C16—H16C	0.9800
B1—C5	1.599 (2)	C17—H17A	0.9800
B1—B2	1.731 (2)	C17—H17B	0.9800
B2—N2	1.400 (2)	C17—H17C	0.9800
B2—C20	1.594 (2)	C18—H18A	0.9800
N1—C2	1.458 (2)	C18—H18B	0.9800
N1—C1	1.465 (2)	C18—H18C	0.9800
C1—H1A	0.9800	C19—H19A	0.9800
C1—H1B	0.9800	C19—H19B	0.9800
C1—H1C	0.9800	C19—H19C	0.9800
C2—H2A	0.9800	C20—C25	1.409 (2)
C2—H2B	0.9800	C20—C21	1.411 (2)
C2—H2C	0.9800	C21—C22	1.386 (2)
N2—C3	1.456 (2)	C21—C28	1.527 (2)
N2—C4	1.468 (2)	C22—C23	1.393 (2)
C3—H3A	0.9800	C22—H22	0.9500
C3—H3B	0.9800	C23—C24	1.385 (2)
C3—H3C	0.9800	C23—C27	1.519 (2)
C4—H4A	0.9800	C24—C25	1.393 (2)
C4—H4B	0.9800	C24—H24	0.9500
C4—H4C	0.9800	C25—C26	1.527 (2)
C5—C10	1.406 (2)	C26—C30	1.523 (3)
C5—C6	1.409 (2)	C26—C29	1.535 (3)
C6—C7	1.389 (2)	C26—H26	1.0000
C6—C11	1.523 (2)	C27—C32	1.515 (3)
C7—C8	1.385 (2)	C27—C31	1.518 (3)
C7—H7	0.9500	C27—H27	1.0000
C8—C9	1.385 (2)	C28—C33	1.519 (3)
C8—C12	1.523 (2)	C28—C34	1.520 (3)
C9—C10	1.395 (2)	C28—H28	1.0000
C9—H9	0.9500	C29—H29A	0.9800
C10—C13	1.523 (2)	C29—H29B	0.9800
C11—C14	1.515 (3)	C29—H29C	0.9800
C11—C15	1.522 (3)	C30—H30A	0.9800
C11—H11	1.0000	C30—H30B	0.9800
C12—C17	1.513 (3)	C30—H30C	0.9800
C12—C16	1.519 (3)	C31—H31A	0.9800
C12—H12	1.0000	C31—H31B	0.9800
C13—C18	1.527 (3)	C31—H31C	0.9800
C13—C19	1.531 (2)	C32—H32A	0.9800
C13—H13	1.0000	C32—H32B	0.9800
C14—H14A	0.9800	C32—H32C	0.9800
C14—H14B	0.9800	C33—H33A	0.9800
C14—H14C	0.9800	C33—H33B	0.9800
C15—H15A	0.9800	C33—H33C	0.9800
C15—H15B	0.9800	C34—H34A	0.9800
C15—H15C	0.9800	C34—H34B	0.9800
C16—H16A	0.9800	C34—H34C	0.9800
C16—H16B	0.9800

N1—B1—C5	118.26 (12)	C12—C17—H17A	109.5
N1—B1—B2	123.11 (13)	C12—C17—H17B	109.5
C5—B1—B2	118.57 (12)	H17A—C17—H17B	109.5
N2—B2—C20	118.14 (13)	C12—C17—H17C	109.5
N2—B2—B1	123.73 (13)	H17A—C17—H17C	109.5
C20—B2—B1	118.08 (12)	H17B—C17—H17C	109.5
B1—N1—C2	124.67 (13)	C13—C18—H18A	109.5
B1—N1—C1	124.99 (13)	C13—C18—H18B	109.5
C2—N1—C1	110.35 (13)	H18A—C18—H18B	109.5
N1—C1—H1A	109.5	C13—C18—H18C	109.5
N1—C1—H1B	109.5	H18A—C18—H18C	109.5
H1A—C1—H1B	109.5	H18B—C18—H18C	109.5
N1—C1—H1C	109.5	C13—C19—H19A	109.5
H1A—C1—H1C	109.5	C13—C19—H19B	109.5
H1B—C1—H1C	109.5	H19A—C19—H19B	109.5
N1—C2—H2A	109.5	C13—C19—H19C	109.5
N1—C2—H2B	109.5	H19A—C19—H19C	109.5
H2A—C2—H2B	109.5	H19B—C19—H19C	109.5
N1—C2—H2C	109.5	C25—C20—C21	117.84 (13)
H2A—C2—H2C	109.5	C25—C20—B2	120.87 (12)
H2B—C2—H2C	109.5	C21—C20—B2	121.27 (13)
B2—N2—C3	125.20 (13)	C22—C21—C20	120.65 (13)
B2—N2—C4	124.01 (14)	C22—C21—C28	119.45 (13)
C3—N2—C4	110.75 (14)	C20—C21—C28	119.89 (13)
N2—C3—H3A	109.5	C21—C22—C23	121.62 (14)
N2—C3—H3B	109.5	C21—C22—H22	119.2
H3A—C3—H3B	109.5	C23—C22—H22	119.2
N2—C3—H3C	109.5	C24—C23—C22	117.69 (14)
H3A—C3—H3C	109.5	C24—C23—C27	121.01 (14)
H3B—C3—H3C	109.5	C22—C23—C27	121.24 (14)
N2—C4—H4A	109.5	C23—C24—C25	122.26 (14)
N2—C4—H4B	109.5	C23—C24—H24	118.9
H4A—C4—H4B	109.5	C25—C24—H24	118.9
N2—C4—H4C	109.5	C24—C25—C20	119.92 (13)
H4A—C4—H4C	109.5	C24—C25—C26	119.26 (13)
H4B—C4—H4C	109.5	C20—C25—C26	120.82 (13)
C10—C5—C6	118.13 (13)	C30—C26—C25	112.10 (15)
C10—C5—B1	121.56 (13)	C30—C26—C29	110.65 (16)
C6—C5—B1	120.28 (13)	C25—C26—C29	111.51 (14)
C7—C6—C5	120.25 (14)	C30—C26—H26	107.4
C7—C6—C11	119.63 (14)	C25—C26—H26	107.4
C5—C6—C11	120.11 (13)	C29—C26—H26	107.4
C8—C7—C6	121.97 (15)	C32—C27—C31	110.46 (18)
C8—C7—H7	119.0	C32—C27—C23	113.23 (16)
C6—C7—H7	119.0	C31—C27—C23	110.64 (16)
C7—C8—C9	117.65 (14)	C32—C27—H27	107.4
C7—C8—C12	120.96 (15)	C31—C27—H27	107.4
C9—C8—C12	121.36 (15)	C23—C27—H27	107.4
C8—C9—C10	122.21 (15)	C33—C28—C34	110.25 (15)
C8—C9—H9	118.9	C33—C28—C21	110.89 (14)
C10—C9—H9	118.9	C34—C28—C21	113.31 (14)
C9—C10—C5	119.79 (14)	C33—C28—H28	107.4
C9—C10—C13	119.37 (14)	C34—C28—H28	107.4
C5—C10—C13	120.84 (13)	C21—C28—H28	107.4
C14—C11—C15	110.69 (15)	C26—C29—H29A	109.5
C14—C11—C6	111.02 (14)	C26—C29—H29B	109.5
C15—C11—C6	113.97 (15)	H29A—C29—H29B	109.5
C14—C11—H11	106.9	C26—C29—H29C	109.5
C15—C11—H11	106.9	H29A—C29—H29C	109.5
C6—C11—H11	106.9	H29B—C29—H29C	109.5
C17—C12—C16	110.57 (19)	C26—C30—H30A	109.5
C17—C12—C8	111.54 (16)	C26—C30—H30B	109.5
C16—C12—C8	111.67 (15)	H30A—C30—H30B	109.5
C17—C12—H12	107.6	C26—C30—H30C	109.5
C16—C12—H12	107.6	H30A—C30—H30C	109.5
C8—C12—H12	107.6	H30B—C30—H30C	109.5
C10—C13—C18	112.27 (15)	C27—C31—H31A	109.5
C10—C13—C19	112.46 (13)	C27—C31—H31B	109.5
C18—C13—C19	109.82 (15)	H31A—C31—H31B	109.5
C10—C13—H13	107.3	C27—C31—H31C	109.5
C18—C13—H13	107.3	H31A—C31—H31C	109.5
C19—C13—H13	107.3	H31B—C31—H31C	109.5
C11—C14—H14A	109.5	C27—C32—H32A	109.5
C11—C14—H14B	109.5	C27—C32—H32B	109.5
H14A—C14—H14B	109.5	H32A—C32—H32B	109.5
C11—C14—H14C	109.5	C27—C32—H32C	109.5
H14A—C14—H14C	109.5	H32A—C32—H32C	109.5
H14B—C14—H14C	109.5	H32B—C32—H32C	109.5
C11—C15—H15A	109.5	C28—C33—H33A	109.5
C11—C15—H15B	109.5	C28—C33—H33B	109.5
H15A—C15—H15B	109.5	H33A—C33—H33B	109.5
C11—C15—H15C	109.5	C28—C33—H33C	109.5
H15A—C15—H15C	109.5	H33A—C33—H33C	109.5
H15B—C15—H15C	109.5	H33B—C33—H33C	109.5
C12—C16—H16A	109.5	C28—C34—H34A	109.5
C12—C16—H16B	109.5	C28—C34—H34B	109.5
H16A—C16—H16B	109.5	H34A—C34—H34B	109.5
C12—C16—H16C	109.5	C28—C34—H34C	109.5
H16A—C16—H16C	109.5	H34A—C34—H34C	109.5
H16B—C16—H16C	109.5	H34B—C34—H34C	109.5

N1—B1—B2—N2	−60.4 (2)	C7—C8—C12—C16	57.7 (2)
C5—B1—B2—N2	122.56 (16)	C9—C8—C12—C16	−120.30 (19)
N1—B1—B2—C20	121.99 (16)	C9—C10—C13—C18	−68.8 (2)
C5—B1—B2—C20	−55.08 (17)	C5—C10—C13—C18	111.88 (18)
C5—B1—N1—C2	178.94 (14)	C9—C10—C13—C19	55.62 (19)
B2—B1—N1—C2	1.9 (2)	C5—C10—C13—C19	−123.66 (15)
C5—B1—N1—C1	−0.3 (2)	N2—B2—C20—C25	−85.40 (18)
B2—B1—N1—C1	−177.42 (15)	B1—B2—C20—C25	92.38 (16)
C20—B2—N2—C3	175.60 (15)	N2—B2—C20—C21	96.14 (17)
B1—B2—N2—C3	−2.0 (2)	B1—B2—C20—C21	−86.08 (17)
C20—B2—N2—C4	−2.1 (2)	C25—C20—C21—C22	1.4 (2)
B1—B2—N2—C4	−179.74 (15)	B2—C20—C21—C22	179.95 (13)
N1—B1—C5—C10	−85.85 (18)	C25—C20—C21—C28	−179.70 (14)
B2—B1—C5—C10	91.36 (16)	B2—C20—C21—C28	−1.2 (2)
N1—B1—C5—C6	96.22 (17)	C20—C21—C22—C23	−0.8 (2)
B2—B1—C5—C6	−86.57 (17)	C28—C21—C22—C23	−179.69 (15)
C10—C5—C6—C7	1.2 (2)	C21—C22—C23—C24	0.0 (2)
B1—C5—C6—C7	179.19 (14)	C21—C22—C23—C27	−177.07 (15)
C10—C5—C6—C11	179.92 (13)	C22—C23—C24—C25	0.2 (2)
B1—C5—C6—C11	−2.1 (2)	C27—C23—C24—C25	177.26 (15)
C5—C6—C7—C8	−0.9 (2)	C23—C24—C25—C20	0.5 (2)
C11—C6—C7—C8	−179.67 (15)	C23—C24—C25—C26	−179.50 (15)
C6—C7—C8—C9	0.4 (2)	C21—C20—C25—C24	−1.3 (2)
C6—C7—C8—C12	−177.61 (15)	B2—C20—C25—C24	−179.78 (13)
C7—C8—C9—C10	−0.2 (2)	C21—C20—C25—C26	178.71 (14)
C12—C8—C9—C10	177.80 (15)	B2—C20—C25—C26	0.2 (2)
C8—C9—C10—C5	0.5 (2)	C24—C25—C26—C30	56.03 (19)
C8—C9—C10—C13	−178.74 (14)	C20—C25—C26—C30	−123.95 (16)
C6—C5—C10—C9	−1.0 (2)	C24—C25—C26—C29	−68.7 (2)
B1—C5—C10—C9	−178.97 (13)	C20—C25—C26—C29	111.36 (18)
C6—C5—C10—C13	178.28 (13)	C24—C23—C27—C32	133.00 (18)
B1—C5—C10—C13	0.3 (2)	C22—C23—C27—C32	−50.0 (2)
C7—C6—C11—C14	79.3 (2)	C24—C23—C27—C31	−102.4 (2)
C5—C6—C11—C14	−99.42 (18)	C22—C23—C27—C31	74.6 (2)
C7—C6—C11—C15	−46.5 (2)	C22—C21—C28—C33	76.2 (2)
C5—C6—C11—C15	134.77 (16)	C20—C21—C28—C33	−102.66 (18)
C7—C8—C12—C17	−66.6 (2)	C22—C21—C28—C34	−48.4 (2)
C9—C8—C12—C17	115.4 (2)	C20—C21—C28—C34	132.74 (16)

Experimental details

Crystal data
Chemical formula	C₃₄H₅₈B₂N₂
M_r	516.44
Crystal system, space group	Triclinic, P1
Temperature (K)	171
a, b, c (Å)	9.6066 (19), 13.919 (3), 14.015 (3)
α, β, γ (°)	82.983 (3), 71.549 (3), 78.300 (3)
V (Å³)	1737.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.40 × 0.17 × 0.12

Data collection
Diffractometer	Bruker APEXI CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.494, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	19559, 7202, 5554
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.173, 1.03
No. of reflections	7202
No. of parameters	359
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.24

Computer programs: SMART-NT (Bruker, 1997), SAINT-Plus-NT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 1997).

Acknowledgements

Financial support by the DFG is gratefully acknowlegded.

References

Bruker (1997). SMART-NT, SAINT-Plus-NT and XP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hommer, H., Knizek, J., Nöth, H., Ponikwar, W. & Schwenk-Kircher, H. (1998). Eur. J. Inorg. Chem. pp. 1519–1527. CrossRef Google Scholar
Hunold, R. (1988). PhD thesis, Philipps-University Marburg, Germany. Google Scholar
Moezzi, A., Olmstead, M. M. & Power, P. P. (1992). J. Chem. Soc. Dalton Trans. pp. 2429–2434. CSD CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar