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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3367.
Published online 2010 November 30. doi:  10.1107/S1600536810049500
PMCID: PMC3011803

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

Abstract

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 [triangle]). For 1,2-diaryl-1,2-bis­(dimethyl­amino)­di­boranes(4) (aryl = phenyl or mesit­yl), see: Moezzi et al. (1992 [triangle]) and for dimesityldiboranes(4), see: Hommer et al. (1998 [triangle]).

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Object name is e-66-o3367-scheme1.jpg

Experimental

Crystal data

  • C34H58B2N2
  • M r = 516.44
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3367-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.173
  • S = 1.03
  • 7202 reflections
  • 359 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.24 e Å−3

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

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049500/br2151Isup2.hkl

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

Acknowledgments

Financial support by the DFG is gratefully acknowlegded.

supplementary crystallographic information

Comment

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–Ci (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).

Experimental

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, 3JH–H = 6.70 Hz, 6H, CH3), 0.92 (d, 3JH–H = 6.85 Hz, 6H, CH3), 1.12–1.18 (m, 18H, CH3), 1.22 (d, 3JH–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, CHarom.), 6.81–6.83 p.p.m. (m, 2H, CHarom.); 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, Ci), 148.17 (s, Ci), 146.66 (s, Ci), 142.00 (s, Ci), 120.11 (s, CHarom.), 119.41 (s, CHarom.), 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%.

Refinement

The H atoms were placed at idealized positions and treated as riding atoms with C–H = 0.98 Å (CH3), 1.00 Å (aliphatic CH) and 0.95 Å (aromatic CH). Uiso(H) values were fixed at 1.5 times (for primary H atoms) and 1.2 times (tertiary or aromatic H atoms) Ueq of the attached C atoms.

Figures

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.

Crystal data

C34H58B2N2Z = 2
Mr = 516.44F(000) = 572
Triclinic, P1Dx = 0.987 Mg m3
Hall symbol: -P 1Melting point: 192.11 K
a = 9.6066 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.919 (3) ÅCell parameters from 5619 reflections
c = 14.015 (3) Åθ = 2.2–26.5°
α = 82.983 (3)°µ = 0.06 mm1
β = 71.549 (3)°T = 171 K
γ = 78.300 (3)°Block, colourless
V = 1737.4 (6) Å30.40 × 0.17 × 0.12 mm

Data collection

Bruker APEXI CCD diffractometer7202 independent reflections
Radiation source: sealed tube5554 reflections with I > 2σ(I)
graphiteRint = 0.062
[var phi] and ω scansθmax = 26.6°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −12→12
Tmin = 0.494, Tmax = 0.745k = −17→17
19559 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0841P)2 + 0.3205P] where P = (Fo2 + 2Fc2)/3
7202 reflections(Δ/σ)max < 0.001
359 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.24 e Å3

Special details

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)

xyzUiso*/Ueq
B10.51577 (18)0.82586 (12)0.21886 (12)0.0269 (3)
B20.54148 (19)0.73592 (12)0.31158 (12)0.0280 (3)
N10.57731 (15)0.91179 (9)0.20047 (9)0.0333 (3)
C10.5537 (2)0.99154 (13)0.12572 (14)0.0497 (5)
H1A0.48780.97560.09120.057 (6)*
H1B0.64960.99960.07640.061 (6)*
H1C0.50781.05280.15960.066 (6)*
C20.6729 (2)0.93496 (13)0.25401 (13)0.0430 (4)
H2A0.68510.88200.30520.043 (5)*
H2B0.62720.99690.28670.057 (6)*
H2C0.77050.94160.20620.057 (6)*
N20.68120 (15)0.68380 (10)0.31429 (10)0.0366 (3)
C30.82264 (19)0.69513 (15)0.23912 (14)0.0482 (4)
H3A0.80590.74900.18980.042 (5)*
H3B0.86630.63400.20470.058 (6)*
H3C0.89090.71000.27230.067 (6)*
C40.7037 (2)0.60721 (15)0.39242 (15)0.0552 (5)
H4A0.60780.60210.44330.054 (6)*
H4B0.77180.62430.42440.088 (8)*
H4C0.74660.54410.36170.070 (7)*
C50.41071 (16)0.81281 (10)0.15445 (10)0.0274 (3)
C60.46957 (17)0.75872 (11)0.06756 (11)0.0318 (3)
C70.37787 (19)0.74638 (12)0.01237 (12)0.0375 (4)
H70.41990.7105−0.04660.045*
C80.22699 (19)0.78480 (12)0.04069 (12)0.0375 (4)
C90.16922 (18)0.83731 (12)0.12656 (12)0.0365 (4)
H90.06600.86450.14710.044*
C100.25752 (17)0.85167 (10)0.18397 (11)0.0308 (3)
C110.63496 (18)0.71524 (12)0.03242 (12)0.0389 (4)
H110.67430.71530.09050.047*
C120.1276 (2)0.76690 (14)−0.01881 (14)0.0464 (4)
H120.02280.79630.01750.056*
C130.18586 (18)0.90841 (12)0.27877 (12)0.0375 (4)
H130.26370.90400.31330.045*
C140.7191 (2)0.77944 (16)−0.05258 (18)0.0640 (6)
H14A0.69750.8471−0.03210.096*
H14B0.68780.7782−0.11250.096*
H14C0.82630.7545−0.06810.096*
C150.6675 (2)0.60935 (14)0.00323 (18)0.0636 (6)
H15A0.61340.56880.05950.095*
H15B0.77480.5844−0.01250.095*
H15C0.63540.6067−0.05600.095*
C160.1325 (3)0.65785 (16)−0.02416 (18)0.0636 (6)
H16A0.06680.6491−0.06240.095*
H16B0.09900.62750.04420.095*
H16C0.23480.6266−0.05780.095*
C170.1674 (3)0.8170 (2)−0.12350 (19)0.0882 (9)
H17A0.10130.8044−0.15960.132*
H17B0.27100.7912−0.16020.132*
H17C0.15570.8880−0.11850.132*
C180.1340 (3)1.01727 (14)0.25493 (18)0.0669 (6)
H18A0.08881.05080.31790.100*
H18B0.06031.02420.21850.100*
H18C0.21961.04670.21310.100*
C190.05621 (19)0.86431 (14)0.35297 (13)0.0449 (4)
H19A0.09040.79460.36850.067*
H19B−0.02460.87080.32280.067*
H19C0.01990.89930.41510.067*
C200.39744 (16)0.70813 (10)0.39634 (10)0.0284 (3)
C210.33107 (17)0.76128 (11)0.48375 (11)0.0309 (3)
C220.20580 (18)0.73635 (11)0.55681 (11)0.0350 (4)
H220.16380.77260.61550.042*
C230.13993 (18)0.65943 (11)0.54635 (11)0.0348 (4)
C240.20400 (19)0.60811 (11)0.45993 (11)0.0356 (4)
H240.16040.55550.45140.043*
C250.33014 (18)0.63093 (11)0.38507 (11)0.0319 (3)
C260.3937 (2)0.57152 (12)0.29141 (12)0.0417 (4)
H260.47590.60320.24370.050*
C27−0.0016 (2)0.63573 (14)0.62444 (13)0.0469 (4)
H27−0.01670.57070.60970.056*
C280.39924 (19)0.84595 (12)0.49932 (12)0.0382 (4)
H280.47140.86290.43330.046*
C290.4616 (3)0.46551 (14)0.31668 (17)0.0662 (6)
H29A0.53520.46620.35150.099*
H29B0.51030.43150.25430.099*
H29C0.38270.43120.36040.099*
C300.2782 (3)0.57269 (15)0.23764 (13)0.0536 (5)
H30A0.23670.64090.22170.080*
H30B0.19810.53940.28140.080*
H30C0.32550.53860.17520.080*
C31−0.1356 (2)0.7113 (2)0.6151 (2)0.0797 (7)
H31A−0.22580.69450.66560.120*
H31B−0.14530.71160.54750.120*
H31C−0.12210.77650.62610.120*
C320.0069 (3)0.62659 (18)0.73136 (14)0.0639 (6)
H32A0.09420.57800.73610.096*
H32B−0.08350.60550.77750.096*
H32C0.01540.69040.74970.096*
C330.4866 (3)0.81472 (16)0.5746 (2)0.0688 (6)
H33A0.56010.75540.55310.103*
H33B0.41810.80090.64120.103*
H33C0.53790.86770.57810.103*
C340.2852 (2)0.93833 (13)0.53104 (17)0.0562 (5)
H34A0.22980.95780.48180.084*
H34B0.33640.99150.53420.084*
H34C0.21580.92530.59750.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
B10.0259 (8)0.0282 (8)0.0253 (8)−0.0020 (6)−0.0074 (6)−0.0024 (6)
B20.0348 (9)0.0261 (8)0.0258 (8)−0.0041 (6)−0.0128 (7)−0.0033 (6)
N10.0410 (7)0.0300 (6)0.0346 (7)−0.0105 (5)−0.0184 (6)0.0034 (5)
C10.0680 (13)0.0368 (9)0.0545 (11)−0.0206 (9)−0.0322 (10)0.0147 (8)
C20.0491 (10)0.0434 (10)0.0461 (10)−0.0187 (8)−0.0225 (8)0.0009 (8)
N20.0356 (7)0.0375 (7)0.0340 (7)0.0011 (6)−0.0132 (6)0.0026 (5)
C30.0330 (9)0.0562 (11)0.0502 (11)0.0012 (8)−0.0116 (8)−0.0012 (9)
C40.0545 (12)0.0535 (12)0.0497 (11)0.0102 (9)−0.0223 (9)0.0120 (9)
C50.0316 (8)0.0258 (7)0.0262 (7)−0.0060 (6)−0.0115 (6)0.0027 (5)
C60.0369 (8)0.0313 (8)0.0276 (7)−0.0051 (6)−0.0121 (6)0.0013 (6)
C70.0458 (9)0.0415 (9)0.0286 (8)−0.0067 (7)−0.0153 (7)−0.0053 (6)
C80.0429 (9)0.0414 (9)0.0347 (8)−0.0104 (7)−0.0197 (7)0.0007 (7)
C90.0329 (8)0.0380 (9)0.0416 (9)−0.0043 (7)−0.0169 (7)−0.0011 (7)
C100.0331 (8)0.0277 (7)0.0333 (8)−0.0052 (6)−0.0132 (6)−0.0001 (6)
C110.0393 (9)0.0453 (9)0.0318 (8)0.0012 (7)−0.0135 (7)−0.0081 (7)
C120.0492 (10)0.0537 (11)0.0471 (10)−0.0122 (8)−0.0278 (8)−0.0025 (8)
C130.0336 (8)0.0389 (9)0.0417 (9)−0.0008 (7)−0.0142 (7)−0.0107 (7)
C140.0422 (11)0.0548 (12)0.0795 (15)−0.0053 (9)0.0015 (10)−0.0042 (11)
C150.0574 (13)0.0438 (11)0.0723 (14)0.0034 (9)−0.0005 (11)−0.0108 (10)
C160.0714 (14)0.0623 (13)0.0758 (15)−0.0225 (11)−0.0409 (12)−0.0053 (11)
C170.119 (2)0.108 (2)0.0763 (16)−0.0654 (18)−0.0728 (16)0.0400 (15)
C180.0763 (15)0.0375 (10)0.0713 (14)−0.0027 (10)−0.0018 (12)−0.0118 (10)
C190.0394 (9)0.0502 (10)0.0413 (9)−0.0012 (8)−0.0090 (7)−0.0076 (8)
C200.0355 (8)0.0241 (7)0.0269 (7)−0.0026 (6)−0.0137 (6)0.0009 (5)
C210.0369 (8)0.0275 (7)0.0298 (8)−0.0050 (6)−0.0120 (6)−0.0026 (6)
C220.0412 (9)0.0355 (8)0.0288 (8)−0.0079 (7)−0.0081 (7)−0.0083 (6)
C230.0392 (9)0.0358 (8)0.0306 (8)−0.0107 (7)−0.0093 (7)−0.0022 (6)
C240.0473 (9)0.0303 (8)0.0331 (8)−0.0142 (7)−0.0134 (7)−0.0011 (6)
C250.0427 (9)0.0260 (7)0.0277 (7)−0.0056 (6)−0.0117 (6)−0.0020 (6)
C260.0572 (11)0.0342 (8)0.0316 (8)−0.0152 (8)−0.0041 (7)−0.0069 (7)
C270.0484 (10)0.0499 (10)0.0416 (10)−0.0225 (8)−0.0006 (8)−0.0117 (8)
C280.0440 (9)0.0371 (8)0.0348 (8)−0.0148 (7)−0.0067 (7)−0.0078 (7)
C290.0898 (17)0.0394 (10)0.0592 (13)0.0027 (10)−0.0113 (12)−0.0176 (9)
C300.0842 (15)0.0497 (11)0.0352 (9)−0.0282 (10)−0.0178 (9)−0.0072 (8)
C310.0397 (12)0.1007 (19)0.0950 (18)−0.0201 (12)−0.0103 (12)−0.0055 (15)
C320.0706 (14)0.0744 (14)0.0379 (10)−0.0280 (11)0.0071 (9)−0.0076 (9)
C330.0684 (14)0.0534 (12)0.1082 (19)−0.0114 (10)−0.0560 (14)−0.0135 (12)
C340.0718 (14)0.0369 (9)0.0727 (13)−0.0073 (9)−0.0361 (11)−0.0159 (9)

Geometric parameters (Å, °)

B1—N11.401 (2)C16—H16C0.9800
B1—C51.599 (2)C17—H17A0.9800
B1—B21.731 (2)C17—H17B0.9800
B2—N21.400 (2)C17—H17C0.9800
B2—C201.594 (2)C18—H18A0.9800
N1—C21.458 (2)C18—H18B0.9800
N1—C11.465 (2)C18—H18C0.9800
C1—H1A0.9800C19—H19A0.9800
C1—H1B0.9800C19—H19B0.9800
C1—H1C0.9800C19—H19C0.9800
C2—H2A0.9800C20—C251.409 (2)
C2—H2B0.9800C20—C211.411 (2)
C2—H2C0.9800C21—C221.386 (2)
N2—C31.456 (2)C21—C281.527 (2)
N2—C41.468 (2)C22—C231.393 (2)
C3—H3A0.9800C22—H220.9500
C3—H3B0.9800C23—C241.385 (2)
C3—H3C0.9800C23—C271.519 (2)
C4—H4A0.9800C24—C251.393 (2)
C4—H4B0.9800C24—H240.9500
C4—H4C0.9800C25—C261.527 (2)
C5—C101.406 (2)C26—C301.523 (3)
C5—C61.409 (2)C26—C291.535 (3)
C6—C71.389 (2)C26—H261.0000
C6—C111.523 (2)C27—C321.515 (3)
C7—C81.385 (2)C27—C311.518 (3)
C7—H70.9500C27—H271.0000
C8—C91.385 (2)C28—C331.519 (3)
C8—C121.523 (2)C28—C341.520 (3)
C9—C101.395 (2)C28—H281.0000
C9—H90.9500C29—H29A0.9800
C10—C131.523 (2)C29—H29B0.9800
C11—C141.515 (3)C29—H29C0.9800
C11—C151.522 (3)C30—H30A0.9800
C11—H111.0000C30—H30B0.9800
C12—C171.513 (3)C30—H30C0.9800
C12—C161.519 (3)C31—H31A0.9800
C12—H121.0000C31—H31B0.9800
C13—C181.527 (3)C31—H31C0.9800
C13—C191.531 (2)C32—H32A0.9800
C13—H131.0000C32—H32B0.9800
C14—H14A0.9800C32—H32C0.9800
C14—H14B0.9800C33—H33A0.9800
C14—H14C0.9800C33—H33B0.9800
C15—H15A0.9800C33—H33C0.9800
C15—H15B0.9800C34—H34A0.9800
C15—H15C0.9800C34—H34B0.9800
C16—H16A0.9800C34—H34C0.9800
C16—H16B0.9800
N1—B1—C5118.26 (12)C12—C17—H17A109.5
N1—B1—B2123.11 (13)C12—C17—H17B109.5
C5—B1—B2118.57 (12)H17A—C17—H17B109.5
N2—B2—C20118.14 (13)C12—C17—H17C109.5
N2—B2—B1123.73 (13)H17A—C17—H17C109.5
C20—B2—B1118.08 (12)H17B—C17—H17C109.5
B1—N1—C2124.67 (13)C13—C18—H18A109.5
B1—N1—C1124.99 (13)C13—C18—H18B109.5
C2—N1—C1110.35 (13)H18A—C18—H18B109.5
N1—C1—H1A109.5C13—C18—H18C109.5
N1—C1—H1B109.5H18A—C18—H18C109.5
H1A—C1—H1B109.5H18B—C18—H18C109.5
N1—C1—H1C109.5C13—C19—H19A109.5
H1A—C1—H1C109.5C13—C19—H19B109.5
H1B—C1—H1C109.5H19A—C19—H19B109.5
N1—C2—H2A109.5C13—C19—H19C109.5
N1—C2—H2B109.5H19A—C19—H19C109.5
H2A—C2—H2B109.5H19B—C19—H19C109.5
N1—C2—H2C109.5C25—C20—C21117.84 (13)
H2A—C2—H2C109.5C25—C20—B2120.87 (12)
H2B—C2—H2C109.5C21—C20—B2121.27 (13)
B2—N2—C3125.20 (13)C22—C21—C20120.65 (13)
B2—N2—C4124.01 (14)C22—C21—C28119.45 (13)
C3—N2—C4110.75 (14)C20—C21—C28119.89 (13)
N2—C3—H3A109.5C21—C22—C23121.62 (14)
N2—C3—H3B109.5C21—C22—H22119.2
H3A—C3—H3B109.5C23—C22—H22119.2
N2—C3—H3C109.5C24—C23—C22117.69 (14)
H3A—C3—H3C109.5C24—C23—C27121.01 (14)
H3B—C3—H3C109.5C22—C23—C27121.24 (14)
N2—C4—H4A109.5C23—C24—C25122.26 (14)
N2—C4—H4B109.5C23—C24—H24118.9
H4A—C4—H4B109.5C25—C24—H24118.9
N2—C4—H4C109.5C24—C25—C20119.92 (13)
H4A—C4—H4C109.5C24—C25—C26119.26 (13)
H4B—C4—H4C109.5C20—C25—C26120.82 (13)
C10—C5—C6118.13 (13)C30—C26—C25112.10 (15)
C10—C5—B1121.56 (13)C30—C26—C29110.65 (16)
C6—C5—B1120.28 (13)C25—C26—C29111.51 (14)
C7—C6—C5120.25 (14)C30—C26—H26107.4
C7—C6—C11119.63 (14)C25—C26—H26107.4
C5—C6—C11120.11 (13)C29—C26—H26107.4
C8—C7—C6121.97 (15)C32—C27—C31110.46 (18)
C8—C7—H7119.0C32—C27—C23113.23 (16)
C6—C7—H7119.0C31—C27—C23110.64 (16)
C7—C8—C9117.65 (14)C32—C27—H27107.4
C7—C8—C12120.96 (15)C31—C27—H27107.4
C9—C8—C12121.36 (15)C23—C27—H27107.4
C8—C9—C10122.21 (15)C33—C28—C34110.25 (15)
C8—C9—H9118.9C33—C28—C21110.89 (14)
C10—C9—H9118.9C34—C28—C21113.31 (14)
C9—C10—C5119.79 (14)C33—C28—H28107.4
C9—C10—C13119.37 (14)C34—C28—H28107.4
C5—C10—C13120.84 (13)C21—C28—H28107.4
C14—C11—C15110.69 (15)C26—C29—H29A109.5
C14—C11—C6111.02 (14)C26—C29—H29B109.5
C15—C11—C6113.97 (15)H29A—C29—H29B109.5
C14—C11—H11106.9C26—C29—H29C109.5
C15—C11—H11106.9H29A—C29—H29C109.5
C6—C11—H11106.9H29B—C29—H29C109.5
C17—C12—C16110.57 (19)C26—C30—H30A109.5
C17—C12—C8111.54 (16)C26—C30—H30B109.5
C16—C12—C8111.67 (15)H30A—C30—H30B109.5
C17—C12—H12107.6C26—C30—H30C109.5
C16—C12—H12107.6H30A—C30—H30C109.5
C8—C12—H12107.6H30B—C30—H30C109.5
C10—C13—C18112.27 (15)C27—C31—H31A109.5
C10—C13—C19112.46 (13)C27—C31—H31B109.5
C18—C13—C19109.82 (15)H31A—C31—H31B109.5
C10—C13—H13107.3C27—C31—H31C109.5
C18—C13—H13107.3H31A—C31—H31C109.5
C19—C13—H13107.3H31B—C31—H31C109.5
C11—C14—H14A109.5C27—C32—H32A109.5
C11—C14—H14B109.5C27—C32—H32B109.5
H14A—C14—H14B109.5H32A—C32—H32B109.5
C11—C14—H14C109.5C27—C32—H32C109.5
H14A—C14—H14C109.5H32A—C32—H32C109.5
H14B—C14—H14C109.5H32B—C32—H32C109.5
C11—C15—H15A109.5C28—C33—H33A109.5
C11—C15—H15B109.5C28—C33—H33B109.5
H15A—C15—H15B109.5H33A—C33—H33B109.5
C11—C15—H15C109.5C28—C33—H33C109.5
H15A—C15—H15C109.5H33A—C33—H33C109.5
H15B—C15—H15C109.5H33B—C33—H33C109.5
C12—C16—H16A109.5C28—C34—H34A109.5
C12—C16—H16B109.5C28—C34—H34B109.5
H16A—C16—H16B109.5H34A—C34—H34B109.5
C12—C16—H16C109.5C28—C34—H34C109.5
H16A—C16—H16C109.5H34A—C34—H34C109.5
H16B—C16—H16C109.5H34B—C34—H34C109.5
N1—B1—B2—N2−60.4 (2)C7—C8—C12—C1657.7 (2)
C5—B1—B2—N2122.56 (16)C9—C8—C12—C16−120.30 (19)
N1—B1—B2—C20121.99 (16)C9—C10—C13—C18−68.8 (2)
C5—B1—B2—C20−55.08 (17)C5—C10—C13—C18111.88 (18)
C5—B1—N1—C2178.94 (14)C9—C10—C13—C1955.62 (19)
B2—B1—N1—C21.9 (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—C2592.38 (16)
C20—B2—N2—C3175.60 (15)N2—B2—C20—C2196.14 (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—C221.4 (2)
B1—B2—N2—C4−179.74 (15)B2—C20—C21—C22179.95 (13)
N1—B1—C5—C10−85.85 (18)C25—C20—C21—C28−179.70 (14)
B2—B1—C5—C1091.36 (16)B2—C20—C21—C28−1.2 (2)
N1—B1—C5—C696.22 (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—C71.2 (2)C21—C22—C23—C240.0 (2)
B1—C5—C6—C7179.19 (14)C21—C22—C23—C27−177.07 (15)
C10—C5—C6—C11179.92 (13)C22—C23—C24—C250.2 (2)
B1—C5—C6—C11−2.1 (2)C27—C23—C24—C25177.26 (15)
C5—C6—C7—C8−0.9 (2)C23—C24—C25—C200.5 (2)
C11—C6—C7—C8−179.67 (15)C23—C24—C25—C26−179.50 (15)
C6—C7—C8—C90.4 (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—C26178.71 (14)
C12—C8—C9—C10177.80 (15)B2—C20—C25—C260.2 (2)
C8—C9—C10—C50.5 (2)C24—C25—C26—C3056.03 (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—C29111.36 (18)
C6—C5—C10—C13178.28 (13)C24—C23—C27—C32133.00 (18)
B1—C5—C10—C130.3 (2)C22—C23—C27—C32−50.0 (2)
C7—C6—C11—C1479.3 (2)C24—C23—C27—C31−102.4 (2)
C5—C6—C11—C14−99.42 (18)C22—C23—C27—C3174.6 (2)
C7—C6—C11—C15−46.5 (2)C22—C21—C28—C3376.2 (2)
C5—C6—C11—C15134.77 (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—C17115.4 (2)C20—C21—C28—C34132.74 (16)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BR2151).

References

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

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