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Acta Cryst. (2010). E66, o610    [ doi:10.1107/S1600536810004988 ]

{N',N''-Bis[2,6-bis(1-methylethyl)phenyl]-N,N-dimethylguanidinato-[kappa]2N',N''}dibromidoborane

H. Braunschweig, R. D. Dewhurst, K. Schwab and K. Wagner

Abstract top

In the molecular structure of the title compound, C27H40N3BBr2, the B atom is connected to two bromide substituents and a guanidinate scaffold, forming a four-membered ring. An aryl group is connected to each N atom in the ring that contains two isopropyl groups in positions 2 and 6.

Comment top

The title compound is a new congener of a boron amidinate and was prepared by an insertion reaction of bis(2,6-diisopropylphenyl)carbodiimide into the B—N bond of 1,1-dibromo-N,N-dimethylboramine.

Findlater et al. (2006) reported the first example of the insertion of a carbodiimide into a boron–nitrogen bond to generate [(Me3Si)2NC{NCy}2]BCl2 that has a boron–halide bond. Before this, their preparation was only known via salt metathesis reactions of the appropriate lithium amidinates with haloboranes.

As shown in Fig. 1, the B—Br distances and the B—N distances are comparable with those found in [(Me3Si)2NC{NCy}2]BCl2 (Findlater et al., 2006). The angles Br1—B1—Br2 and N1—B1—N3 are smaller than the corresponding angles in [(Me3Si)2NC{NCy}2]BCl2 (Findlater et al., 2006). This could be due to the higher steric hindrance of the substituted aryl group than the cyclohexyl group in the reference substance.

Related literature top

For the synthesis of a similar compound, see: Findlater et al. (2006).

Experimental top

To prepare the title compound, bis(2,6-diiso-propylphenyl)carbodiimide (0.50 g, 1.38 mmol) dissolved in 2 ml toluene, and 1,1-dibromo-N,N-dimethylaminoborane (0.23 g, 1.08 mmol) dissolved in 2 ml toluene were combined and stirred for 20 h at ambient temperature. After a few minutes a precipitate was noticed. All volatiles were removed under reduced pressure. Recrystallization at ambient temperature from benzene gave colourless crystals of title compound (0.51 g, 0.88 mmol, yield 81%).

Refinement top

The H atoms were placed at idealized positions and treated as riding atoms with C—H = 0.96 Å (CH3), 0.98 Å (aliphatic CH) and 0.93 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.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound. Displacement ellipsoids are drawn at the 30% probability level. The H atoms are presented as a small spheres of arbitrary radius.
{N',N''-Bis[2,6-bis(1-methylethyl)phenyl]-N,N-dimethylguanidinato-κ2N',N''}dibromidoborane top
Crystal data top
C27H40BBr2N3F(000) = 1192
Mr = 577.23Dx = 1.294 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8028 reflections
a = 9.996 (3) Åθ = 2.3–28.3°
b = 16.080 (5) ŵ = 2.76 mm−1
c = 18.464 (6) ÅT = 166 K
β = 93.505 (5)°Plate, colourless
V = 2962.3 (16) Å30.95 × 0.34 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		7424 independent reflections
Radiation source: sealed tube6550 reflections with I > 2σ(I)
graphiteRint = 0.030
φ and ω scansθmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −13→13
Tmin = 0.260, Tmax = 0.609k = −21→21
79220 measured reflectionsl = −24→24
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0374P)2 + 1.1023P]
where P = (Fo2 + 2Fc2)/3
7424 reflections(Δ/σ)max = 0.001
308 parametersΔρmax = 0.63 e Å−3
0 restraintsΔρmin = −0.52 e Å−3
Crystal data top
C27H40BBr2N3V = 2962.3 (16) Å3
Mr = 577.23Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.996 (3) ŵ = 2.76 mm−1
b = 16.080 (5) ÅT = 166 K
c = 18.464 (6) Å0.95 × 0.34 × 0.18 mm
β = 93.505 (5)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		7424 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		6550 reflections with I > 2σ(I)
Tmin = 0.260, Tmax = 0.609Rint = 0.030
79220 measured reflectionsθmax = 28.4°
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.069Δρmax = 0.63 e Å−3
S = 1.04Δρmin = −0.52 e Å−3
7424 reflectionsAbsolute structure: ?
308 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
xyzUiso*/Ueq
B10.01926 (15)0.04337 (9)0.24662 (9)0.0231 (3)
Br1−0.131845 (15)0.011137 (10)0.306711 (9)0.03424 (5)
Br20.046698 (17)−0.047479 (10)0.174634 (9)0.03696 (5)
C300.27818 (13)0.03635 (8)0.30412 (8)0.0223 (3)
C310.37833 (14)0.03839 (9)0.25355 (8)0.0264 (3)
C320.50122 (15)0.00155 (10)0.27394 (9)0.0323 (3)
H32A0.56980.00340.24210.039*
C330.52377 (15)−0.03759 (10)0.34008 (9)0.0336 (3)
H33A0.6065−0.06190.35230.040*
C350.29912 (14)−0.00356 (9)0.37141 (8)0.0244 (3)
C360.19185 (16)−0.00687 (10)0.42605 (8)0.0313 (3)
H36A0.11500.02570.40640.038*
C390.36010 (16)0.07683 (11)0.17835 (9)0.0339 (3)
H39A0.26700.09560.17110.041*
C10.12374 (14)0.15035 (8)0.26028 (7)0.0229 (3)
C30.28701 (19)0.22944 (11)0.33429 (10)0.0426 (4)
H3A0.27690.18380.36710.064*
H3B0.27070.28080.35870.064*
H3C0.37640.22950.31810.064*
C20.17392 (19)0.29175 (10)0.22274 (11)0.0417 (4)
H2A0.12200.27530.17970.063*
H2B0.26020.31100.20990.063*
H2C0.12840.33560.24650.063*
C10−0.09603 (14)0.19049 (8)0.19551 (8)0.0240 (3)
C11−0.12695 (15)0.19503 (9)0.12043 (8)0.0297 (3)
C12−0.22852 (18)0.24924 (11)0.09581 (10)0.0383 (4)
H12A−0.25110.25300.04630.046*
C19−0.05507 (19)0.14327 (12)0.06641 (9)0.0406 (4)
H19A0.01290.10990.09360.049*
C200.0170 (3)0.19737 (19)0.01262 (13)0.0737 (7)
H20A0.08140.23220.03870.111*
H20B−0.04730.2315−0.01430.111*
H20C0.06200.1623−0.02020.111*
C21−0.1521 (3)0.08357 (17)0.02629 (13)0.0664 (7)
H21A−0.19240.04810.06070.100*
H21B−0.10440.0503−0.00670.100*
H21C−0.22070.1147−0.00030.100*
C15−0.16645 (15)0.23739 (9)0.24479 (8)0.0287 (3)
C16−0.14292 (19)0.23165 (11)0.32672 (9)0.0383 (4)
H16A−0.07680.18770.33770.046*
C18−0.0876 (3)0.31294 (14)0.35935 (12)0.0603 (6)
H18A−0.00520.32660.33800.090*
H18B−0.07140.30650.41080.090*
H18C−0.15150.35670.34970.090*
C17−0.2733 (2)0.20788 (15)0.36188 (12)0.0553 (5)
H17A−0.30880.15760.34020.083*
H17B−0.33760.25190.35440.083*
H17C−0.25490.19930.41300.083*
N10.14975 (11)0.07362 (7)0.28819 (6)0.0218 (2)
N20.19091 (13)0.22050 (8)0.27179 (7)0.0300 (3)
N30.00984 (11)0.13479 (7)0.21945 (6)0.0226 (2)
C13−0.29584 (17)0.29719 (10)0.14300 (11)0.0399 (4)
H13A−0.36230.33370.12530.048*
C14−0.26533 (17)0.29146 (10)0.21643 (10)0.0367 (4)
H14A−0.31170.32440.24790.044*
C400.3863 (2)0.01302 (14)0.11895 (10)0.0483 (5)
H40A0.36370.03700.07220.072*
H40B0.3324−0.03550.12540.072*
H40C0.4793−0.00230.12220.072*
C410.4512 (2)0.15212 (14)0.17041 (12)0.0533 (5)
H41A0.43350.19250.20690.080*
H41B0.43400.17630.12320.080*
H41C0.54320.13490.17620.080*
C370.1445 (2)−0.09584 (15)0.43660 (14)0.0613 (6)
H37A0.1082−0.11750.39110.092*
H37B0.0765−0.09650.47120.092*
H37C0.2188−0.12960.45420.092*
C380.2403 (3)0.0318 (2)0.49769 (12)0.0706 (7)
H38A0.27040.08750.48960.106*
H38B0.3131−0.00050.51920.106*
H38C0.16820.03290.52970.106*
C340.42350 (15)−0.04071 (10)0.38811 (9)0.0308 (3)
H34A0.4389−0.06790.43230.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0203 (7)0.0207 (7)0.0278 (7)−0.0006 (5)−0.0025 (6)0.0013 (6)
Br10.02314 (8)0.03269 (9)0.04722 (10)−0.00460 (6)0.00494 (6)0.00839 (6)
Br20.04139 (10)0.02723 (8)0.04154 (10)0.00203 (6)−0.00325 (7)−0.00983 (6)
C300.0186 (6)0.0207 (6)0.0270 (6)−0.0008 (5)−0.0026 (5)−0.0007 (5)
C310.0221 (6)0.0269 (7)0.0300 (7)−0.0030 (5)0.0010 (5)0.0006 (5)
C320.0208 (7)0.0386 (8)0.0378 (8)−0.0010 (6)0.0042 (6)−0.0018 (6)
C330.0208 (7)0.0371 (8)0.0420 (9)0.0045 (6)−0.0049 (6)−0.0013 (7)
C350.0215 (6)0.0256 (7)0.0257 (7)−0.0002 (5)−0.0021 (5)−0.0010 (5)
C360.0264 (7)0.0422 (9)0.0251 (7)0.0055 (6)0.0002 (6)0.0038 (6)
C390.0294 (7)0.0407 (9)0.0320 (8)−0.0002 (6)0.0060 (6)0.0074 (7)
C10.0228 (6)0.0219 (6)0.0239 (6)0.0001 (5)0.0015 (5)0.0010 (5)
C30.0425 (10)0.0323 (8)0.0507 (10)−0.0078 (7)−0.0158 (8)−0.0042 (7)
C20.0437 (9)0.0254 (8)0.0552 (11)−0.0059 (7)−0.0033 (8)0.0114 (7)
C100.0222 (6)0.0208 (6)0.0286 (7)0.0012 (5)−0.0007 (5)0.0036 (5)
C110.0305 (7)0.0270 (7)0.0309 (7)0.0000 (6)−0.0035 (6)0.0049 (6)
C120.0401 (9)0.0332 (8)0.0395 (9)0.0009 (7)−0.0131 (7)0.0095 (7)
C190.0483 (10)0.0480 (10)0.0251 (8)0.0086 (8)−0.0001 (7)0.0026 (7)
C200.0832 (18)0.0905 (19)0.0501 (13)0.0046 (15)0.0264 (12)0.0144 (13)
C210.0759 (16)0.0676 (15)0.0542 (13)0.0070 (13)−0.0092 (11)−0.0247 (12)
C150.0294 (7)0.0225 (7)0.0343 (8)−0.0006 (5)0.0031 (6)0.0010 (6)
C160.0474 (10)0.0350 (8)0.0331 (8)0.0056 (7)0.0069 (7)−0.0041 (7)
C180.0810 (16)0.0488 (12)0.0508 (12)−0.0019 (11)0.0009 (11)−0.0181 (10)
C170.0622 (13)0.0570 (12)0.0496 (11)0.0110 (10)0.0267 (10)0.0030 (9)
N10.0192 (5)0.0200 (5)0.0256 (5)−0.0007 (4)−0.0018 (4)0.0023 (4)
N20.0299 (6)0.0221 (6)0.0371 (7)−0.0042 (5)−0.0061 (5)0.0024 (5)
N30.0208 (5)0.0205 (5)0.0260 (6)0.0005 (4)−0.0018 (4)0.0017 (4)
C130.0282 (8)0.0291 (8)0.0611 (11)0.0043 (6)−0.0082 (7)0.0092 (7)
C140.0311 (8)0.0252 (7)0.0543 (10)0.0054 (6)0.0067 (7)0.0013 (7)
C400.0492 (11)0.0629 (13)0.0332 (9)0.0031 (9)0.0079 (8)0.0003 (8)
C410.0494 (11)0.0510 (11)0.0609 (12)−0.0096 (9)0.0156 (9)0.0147 (10)
C370.0489 (12)0.0591 (13)0.0782 (16)−0.0029 (10)0.0230 (11)0.0171 (12)
C380.0609 (14)0.112 (2)0.0396 (11)−0.0030 (14)0.0080 (10)−0.0265 (13)
C340.0262 (7)0.0340 (8)0.0313 (7)0.0026 (6)−0.0060 (6)0.0035 (6)
Geometric parameters (Å, °) top
B1—N11.5507 (19)C12—H12A0.9300
B1—N31.5543 (19)C19—C211.524 (3)
B1—Br11.9966 (17)C19—C201.533 (3)
B1—Br22.0050 (16)C19—H19A0.9800
C30—C351.403 (2)C20—H20A0.9600
C30—C311.411 (2)C20—H20B0.9600
C30—N11.4310 (17)C20—H20C0.9600
C31—C321.395 (2)C21—H21A0.9600
C31—C391.520 (2)C21—H21B0.9600
C32—C331.380 (2)C21—H21C0.9600
C32—H32A0.9300C15—C141.394 (2)
C33—C341.379 (2)C15—C161.519 (2)
C33—H33A0.9300C16—C181.529 (3)
C35—C341.397 (2)C16—C171.540 (3)
C35—C361.517 (2)C16—H16A0.9800
C36—C381.514 (3)C18—H18A0.9600
C36—C371.523 (3)C18—H18B0.9600
C36—H36A0.9800C18—H18C0.9600
C39—C411.527 (3)C17—H17A0.9600
C39—C401.536 (3)C17—H17B0.9600
C39—H39A0.9800C17—H17C0.9600
C1—N21.3231 (18)C13—C141.374 (3)
C1—N31.3500 (18)C13—H13A0.9300
C1—N11.3563 (18)C14—H14A0.9300
C3—N21.463 (2)C40—H40A0.9600
C3—H3A0.9600C40—H40B0.9600
C3—H3B0.9600C40—H40C0.9600
C3—H3C0.9600C41—H41A0.9600
C2—N21.464 (2)C41—H41B0.9600
C2—H2A0.9600C41—H41C0.9600
C2—H2B0.9600C37—H37A0.9600
C2—H2C0.9600C37—H37B0.9600
C10—C111.404 (2)C37—H37C0.9600
C10—C151.404 (2)C38—H38A0.9600
C10—N31.4355 (17)C38—H38B0.9600
C11—C121.393 (2)C38—H38C0.9600
C11—C191.514 (2)C34—H34A0.9300
C12—C131.370 (3)
N1—B1—N384.01 (10)H20B—C20—H20C109.5
N1—B1—Br1116.64 (10)C19—C21—H21A109.5
N3—B1—Br1113.07 (10)C19—C21—H21B109.5
N1—B1—Br2114.31 (10)H21A—C21—H21B109.5
N3—B1—Br2118.89 (10)C19—C21—H21C109.5
Br1—B1—Br2108.54 (7)H21A—C21—H21C109.5
C35—C30—C31121.57 (13)H21B—C21—H21C109.5
C35—C30—N1117.20 (12)C14—C15—C10117.62 (15)
C31—C30—N1121.22 (12)C14—C15—C16118.35 (15)
C32—C31—C30117.41 (14)C10—C15—C16124.02 (14)
C32—C31—C39118.27 (14)C15—C16—C18111.76 (16)
C30—C31—C39124.31 (13)C15—C16—C17110.57 (16)
C33—C32—C31121.75 (14)C18—C16—C17109.95 (17)
C33—C32—H32A119.1C15—C16—H16A108.2
C31—C32—H32A119.1C18—C16—H16A108.2
C34—C33—C32119.98 (14)C17—C16—H16A108.2
C34—C33—H33A120.0C16—C18—H18A109.5
C32—C33—H33A120.0C16—C18—H18B109.5
C34—C35—C30118.28 (14)H18A—C18—H18B109.5
C34—C35—C36119.60 (13)C16—C18—H18C109.5
C30—C35—C36122.11 (13)H18A—C18—H18C109.5
C38—C36—C35111.41 (15)H18B—C18—H18C109.5
C38—C36—C37111.05 (19)C16—C17—H17A109.5
C35—C36—C37110.85 (15)C16—C17—H17B109.5
C38—C36—H36A107.8H17A—C17—H17B109.5
C35—C36—H36A107.8C16—C17—H17C109.5
C37—C36—H36A107.8H17A—C17—H17C109.5
C31—C39—C41111.78 (15)H17B—C17—H17C109.5
C31—C39—C40111.36 (15)C1—N1—C30127.43 (12)
C41—C39—C40109.41 (15)C1—N1—B187.79 (10)
C31—C39—H39A108.1C30—N1—B1133.42 (11)
C41—C39—H39A108.1C1—N2—C3120.85 (13)
C40—C39—H39A108.1C1—N2—C2121.96 (13)
N2—C1—N3130.55 (13)C3—N2—C2117.19 (13)
N2—C1—N1129.12 (13)C1—N3—C10129.57 (12)
N3—C1—N1100.31 (11)C1—N3—B187.86 (10)
N2—C1—B1177.85 (13)C10—N3—B1135.94 (11)
N3—C1—B150.24 (8)C12—C13—C14120.09 (15)
N1—C1—B150.08 (8)C12—C13—H13A120.0
N2—C3—H3A109.5C14—C13—H13A120.0
N2—C3—H3B109.5C13—C14—C15121.46 (16)
H3A—C3—H3B109.5C13—C14—H14A119.3
N2—C3—H3C109.5C15—C14—H14A119.3
H3A—C3—H3C109.5C39—C40—H40A109.5
H3B—C3—H3C109.5C39—C40—H40B109.5
N2—C2—H2A109.5H40A—C40—H40B109.5
N2—C2—H2B109.5C39—C40—H40C109.5
H2A—C2—H2B109.5H40A—C40—H40C109.5
N2—C2—H2C109.5H40B—C40—H40C109.5
H2A—C2—H2C109.5C39—C41—H41A109.5
H2B—C2—H2C109.5C39—C41—H41B109.5
C11—C10—C15121.56 (13)H41A—C41—H41B109.5
C11—C10—N3116.76 (13)C39—C41—H41C109.5
C15—C10—N3121.67 (13)H41A—C41—H41C109.5
C12—C11—C10117.82 (15)H41B—C41—H41C109.5
C12—C11—C19119.66 (14)C36—C37—H37A109.5
C10—C11—C19122.51 (13)C36—C37—H37B109.5
C13—C12—C11121.40 (16)H37A—C37—H37B109.5
C13—C12—H12A119.3C36—C37—H37C109.5
C11—C12—H12A119.3H37A—C37—H37C109.5
C11—C19—C21110.66 (17)H37B—C37—H37C109.5
C11—C19—C20112.06 (17)C36—C38—H38A109.5
C21—C19—C20110.67 (19)C36—C38—H38B109.5
C11—C19—H19A107.8H38A—C38—H38B109.5
C21—C19—H19A107.8C36—C38—H38C109.5
C20—C19—H19A107.8H38A—C38—H38C109.5
C19—C20—H20A109.5H38B—C38—H38C109.5
C19—C20—H20B109.5C33—C34—C35120.97 (14)
H20A—C20—H20B109.5C33—C34—H34A119.5
C19—C20—H20C109.5C35—C34—H34A119.5
H20A—C20—H20C109.5
C35—C30—C31—C32−2.1 (2)N2—C1—N1—C30−35.8 (2)
N1—C30—C31—C32179.12 (13)N3—C1—N1—C30145.49 (13)
C35—C30—C31—C39176.93 (14)B1—C1—N1—C30146.78 (17)
N1—C30—C31—C39−1.8 (2)N2—C1—N1—B1177.41 (16)
C30—C31—C32—C331.8 (2)N3—C1—N1—B1−1.29 (12)
C39—C31—C32—C33−177.33 (15)C35—C30—N1—C1133.90 (14)
C31—C32—C33—C34−0.3 (3)C31—C30—N1—C1−47.3 (2)
C31—C30—C35—C341.0 (2)C35—C30—N1—B1−95.00 (18)
N1—C30—C35—C34179.75 (12)C31—C30—N1—B183.80 (19)
C31—C30—C35—C36−179.47 (14)N3—B1—N1—C11.11 (10)
N1—C30—C35—C36−0.7 (2)Br1—B1—N1—C1−111.73 (11)
C34—C35—C36—C3857.9 (2)Br2—B1—N1—C1120.17 (11)
C30—C35—C36—C38−121.71 (19)N3—B1—N1—C30−142.10 (14)
C34—C35—C36—C37−66.3 (2)Br1—B1—N1—C30105.05 (15)
C30—C35—C36—C37114.09 (18)Br2—B1—N1—C30−23.04 (19)
C32—C31—C39—C41−65.9 (2)C1—B1—N1—C30−143.21 (18)
C30—C31—C39—C41115.01 (17)N3—C1—N2—C3160.85 (16)
C32—C31—C39—C4056.8 (2)N1—C1—N2—C3−17.5 (2)
C30—C31—C39—C40−122.28 (17)N3—C1—N2—C2−19.8 (3)
N1—B1—C1—N3178.34 (15)N1—C1—N2—C2161.86 (16)
Br1—B1—C1—N3−87.84 (12)N2—C1—N3—C10−23.0 (3)
Br2—B1—C1—N392.96 (13)N1—C1—N3—C10155.72 (13)
N3—B1—C1—N1−178.34 (15)B1—C1—N3—C10154.42 (18)
Br1—B1—C1—N193.81 (13)N2—C1—N3—B1−177.39 (16)
Br2—B1—C1—N1−85.39 (13)N1—C1—N3—B11.29 (12)
C15—C10—C11—C121.4 (2)C11—C10—N3—C1123.75 (16)
N3—C10—C11—C12−179.42 (13)C15—C10—N3—C1−57.0 (2)
C15—C10—C11—C19−178.23 (15)C11—C10—N3—B1−94.59 (19)
N3—C10—C11—C191.0 (2)C15—C10—N3—B184.6 (2)
C10—C11—C12—C130.4 (2)N1—B1—N3—C1−1.12 (10)
C19—C11—C12—C13−179.94 (16)Br1—B1—N3—C1115.33 (11)
C12—C11—C19—C21−63.0 (2)Br2—B1—N3—C1−115.63 (11)
C10—C11—C19—C21116.55 (19)N1—B1—N3—C10−152.53 (15)
C12—C11—C19—C2061.0 (2)Br1—B1—N3—C10−36.1 (2)
C10—C11—C19—C20−119.40 (19)Br2—B1—N3—C1092.96 (17)
C11—C10—C15—C14−2.5 (2)C1—B1—N3—C10−151.4 (2)
N3—C10—C15—C14178.37 (13)C11—C12—C13—C14−1.1 (3)
C11—C10—C15—C16176.50 (15)C12—C13—C14—C15−0.1 (3)
N3—C10—C15—C16−2.7 (2)C10—C15—C14—C131.8 (2)
C14—C15—C16—C18−66.2 (2)C16—C15—C14—C13−177.22 (16)
C10—C15—C16—C18114.88 (19)C32—C33—C34—C35−1.0 (2)
C14—C15—C16—C1756.7 (2)C30—C35—C34—C330.6 (2)
C10—C15—C16—C17−122.29 (17)C36—C35—C34—C33−178.94 (15)
references
References top

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Findlater, M., Hill, N. J. & Cowley, A. H. (2006). Polyhedron, 25, 983–988.

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