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Acta Cryst. (2011). E67, o1919    [ doi:10.1107/S1600536811025645 ]

9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

W. Wu and J. Tang

Abstract top

In the title compound, C30H35B2NO4, the carbazole skeleton is essentially planar (r.m.s. deviation for all non-H atoms = 0.035 Å), and is oriented at a dihedral angle of 65.0 (3)° with respect to the adjacent phenyl ring.

Comment top

Carbazole - based materials have been investigated for their electrical and optical properties. Especially, introduction of substituents on the 3, 6-positions of carbazole represents a possible approach for designing carbazole-based materials with electrogenerated chemiluminescence. The title compound is a key intermediates, which can be used to synthesize 9-phenylcarbazole derivatives with substituents at 3, 6-positions (Wong et al., 2005, 2006; Rashidnadimi et al., 2008).

The central structural element of the title compound is a carbazole moiety substituted with two pinacolbronic ester at 3, 6-positions and a phenyl attached to atom N9. The carbazole moiety is essentially planar (maximum deviation=0.057 Å). The carbazole plane is inclined to the phenyl ring planes at dihedral angle of 115.0 (3)°. The C—B distances fall in the range to 1.550 (4) Å, consistent with the literature (Allen et al., 1987).The crystal packing is stabilized by van der Waals forces.

Related literature top

The title compound is an intermediate in the synthesis of 9-phenylcarbazole-based optic materials, see: Oliveira et al. (2005). For the synthesis of the title compound, see: Wong et al. (2005, 2006); Rashidnadimi et al. (2008). For related structures, see: Xu et al. (2010); Cui et al. (2009); Saeed et al. (2010). For standard bond lengths, see: Allen et al. (1987).

Experimental top

To a solution of 5,8-dibromo-1-phenylcarbazole (400 mg, 1 mmol) in THF (15 ml) at -78°C was added 1.87 ml (3 mmol) of n-butyllithium (1.6 M in hexane). The mixture was stirred at -78°C for 2 h. 0.4 ml (2 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane was added rapidly to the solution, and the resulting mixture was warmed to room temperature and stirred for 8 h. The mixture was poured into water and extracted with dichloromethane. The organic extracts were washed with brine and dried over magnesium sulfate. The solvent was removed by rotary evaporation, and recrystallization was made in a mixture of n-pentane/hexane to afford 356 mg (72%) of product as a whitesolid. The structure was confirmed by FTIR, 1H NMR and MS. Single crystals suitable for crystallographic analysis were obtained by slow evaporation of a ethanol/dichloromethane (1:1v/v) solution.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.96 Å(methyl) and C—H = 0.93 Å (aromatic) with Uĩso~(H) = 1.2U~eq~(aromatic) and Uĩso~(H) = 1.5U~eq~(methyl).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.
9-Phenyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H- carbazole top
Crystal data top
C30H35B2NO4Dx = 1.143 Mg m−3
Mr = 495.21Melting point: 476 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 10558 reflections
a = 13.974 (6) Åθ = 2.1–27.5°
b = 11.935 (5) ŵ = 0.07 mm−1
c = 34.494 (14) ÅT = 298 K
V = 5753 (4) Å3Block, colourless
Z = 80.3 × 0.2 × 0.1 mm
F(000) = 2112
Data collection top
Rigaku Mercury2
diffractometer		6553 independent reflections
Radiation source: fine-focus sealed tube5170 reflections with I > 2σ(I)
graphiteRint = 0.062
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 1.9°
ω scansh = −18→18
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −15→15
Tmin = 0.9, Tmax = 1l = −44→44
49645 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.093H-atom parameters constrained
wR(F2) = 0.242 w = 1/[σ2(Fo2) + (0.0908P)2 + 3.0388P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max < 0.001
6553 reflectionsΔρmax = 0.72 e Å−3
342 parametersΔρmin = −0.52 e Å−3
15 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0056 (14)
Crystal data top
C30H35B2NO4V = 5753 (4) Å3
Mr = 495.21Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.974 (6) ŵ = 0.07 mm−1
b = 11.935 (5) ÅT = 298 K
c = 34.494 (14) Å0.3 × 0.2 × 0.1 mm
Data collection top
Rigaku Mercury2
diffractometer		6553 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		5170 reflections with I > 2σ(I)
Tmin = 0.9, Tmax = 1Rint = 0.062
49645 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.093H-atom parameters constrained
wR(F2) = 0.242Δρmax = 0.72 e Å−3
S = 1.16Δρmin = −0.52 e Å−3
6553 reflectionsAbsolute structure: ?
342 parametersFlack parameter: ?
15 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
O10.14754 (13)0.80983 (19)0.06118 (6)0.0611 (6)
O20.16305 (13)0.7395 (2)0.12237 (6)0.0644 (6)
C30.47750 (18)0.7413 (2)0.11098 (7)0.0454 (6)
N10.61593 (15)0.8121 (2)0.08578 (6)0.0517 (6)
C50.64049 (18)0.7510 (2)0.11878 (7)0.0475 (6)
C60.51688 (17)0.8061 (2)0.08084 (7)0.0461 (6)
C70.68001 (18)0.8756 (2)0.06208 (7)0.0465 (6)
C80.31920 (18)0.7794 (2)0.08579 (8)0.0506 (6)
C90.6547 (2)0.6093 (3)0.18283 (8)0.0533 (7)
C100.56499 (19)0.6321 (2)0.16660 (7)0.0499 (6)
H10A0.51050.59940.17710.060*
C110.36216 (19)0.8401 (3)0.05558 (8)0.0562 (7)
H11A0.32300.87160.03670.067*
C120.55668 (17)0.7033 (2)0.13485 (7)0.0448 (6)
C130.37813 (18)0.7292 (2)0.11331 (8)0.0491 (6)
H13A0.35130.68740.13330.059*
C140.7359 (2)0.6605 (3)0.16612 (8)0.0607 (7)
H14A0.79560.64630.17690.073*
C150.7300 (2)0.9648 (3)0.07770 (9)0.0603 (7)
H15A0.72320.98290.10380.072*
C160.73053 (19)0.7308 (3)0.13444 (8)0.0587 (7)
H16A0.78510.76340.12390.070*
C170.45997 (19)0.8554 (2)0.05254 (8)0.0544 (7)
H17A0.48650.89680.03240.065*
C180.6916 (2)0.8491 (2)0.02336 (8)0.0557 (7)
H18A0.65900.78850.01270.067*
C190.05223 (19)0.8181 (3)0.07865 (9)0.0611 (8)
O30.59377 (17)0.4625 (2)0.23038 (7)0.0892 (7)
C210.0605 (2)0.7369 (3)0.11389 (9)0.0630 (8)
C220.7514 (2)0.9128 (3)0.00057 (8)0.0645 (8)
H22A0.75840.8952−0.02550.077*
B10.2088 (2)0.7751 (3)0.08979 (9)0.0516 (7)
O40.74200 (18)0.5255 (2)0.24089 (7)0.0907 (7)
C250.7291 (3)0.4402 (3)0.27042 (9)0.0707 (9)
B20.6640 (3)0.5314 (4)0.21859 (12)0.0801 (8)
C270.8004 (2)1.0010 (3)0.01569 (9)0.0668 (8)
H27A0.84051.04360.00000.080*
C28−0.0211 (2)0.7866 (4)0.04848 (10)0.0865 (12)
H28A−0.01350.70910.04170.130*
H28B−0.01230.83220.02580.130*
H28C−0.08420.79840.05870.130*
C290.6219 (3)0.4071 (3)0.26585 (8)0.0664 (8)
C300.7904 (2)1.0269 (3)0.05424 (10)0.0719 (9)
H30A0.82441.08670.06470.086*
C310.0404 (3)0.9398 (3)0.09067 (14)0.0974 (13)
H31A0.04370.98690.06810.146*
H31B0.09050.95990.10840.146*
H31C−0.02050.94950.10310.146*
C320.0087 (3)0.7720 (5)0.15013 (10)0.1018 (15)
H32A0.01960.71760.17020.153*
H32B−0.05870.77700.14490.153*
H32C0.03200.84370.15850.153*
C330.7992 (4)0.3483 (5)0.26240 (19)0.142 (2)
H33A0.86310.37750.26380.212*
H33B0.78800.31840.23700.212*
H33C0.79160.28990.28130.212*
C340.5556 (4)0.4521 (6)0.29700 (15)0.155 (3)
H34A0.56920.52980.30140.232*
H34B0.56510.41080.32060.232*
H34C0.49040.44400.28870.232*
C350.0369 (3)0.6160 (4)0.10317 (14)0.1071 (15)
H35A0.05810.56690.12350.161*
H35B0.06880.59670.07940.161*
H35C−0.03090.60820.09980.161*
C360.6025 (4)0.2839 (4)0.26109 (18)0.1287 (19)
H36A0.53530.27240.25690.193*
H36B0.62190.24480.28410.193*
H36C0.63770.25580.23930.193*
C370.7538 (4)0.4952 (5)0.30874 (14)0.135 (2)
H37A0.71560.56130.31210.202*
H37B0.82030.51520.30890.202*
H37C0.74110.44390.32950.202*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0418 (10)0.0836 (14)0.0579 (11)0.0092 (9)−0.0044 (8)0.0047 (10)
O20.0427 (10)0.0916 (16)0.0588 (12)0.0036 (10)−0.0048 (8)0.0047 (11)
C30.0420 (13)0.0488 (14)0.0454 (12)0.0058 (11)−0.0023 (10)−0.0002 (10)
N10.0401 (11)0.0684 (15)0.0465 (11)−0.0006 (10)−0.0049 (9)0.0088 (10)
C50.0423 (13)0.0583 (15)0.0418 (12)0.0012 (11)−0.0031 (10)0.0024 (11)
C60.0404 (13)0.0523 (14)0.0455 (12)0.0026 (11)−0.0039 (10)0.0000 (11)
C70.0415 (13)0.0520 (14)0.0462 (13)0.0027 (11)−0.0034 (10)0.0052 (11)
C80.0408 (13)0.0582 (16)0.0528 (14)0.0048 (11)−0.0060 (11)−0.0011 (12)
C90.0506 (15)0.0639 (17)0.0455 (13)0.0036 (13)−0.0062 (11)0.0035 (12)
C100.0455 (14)0.0585 (16)0.0456 (13)0.0022 (12)−0.0009 (11)0.0037 (11)
C110.0454 (14)0.0678 (17)0.0554 (15)0.0095 (13)−0.0103 (12)0.0044 (13)
C120.0391 (12)0.0517 (14)0.0435 (12)0.0031 (10)−0.0028 (10)−0.0026 (10)
C130.0406 (13)0.0564 (15)0.0502 (13)0.0029 (11)0.0003 (10)0.0002 (12)
C140.0456 (15)0.083 (2)0.0539 (15)0.0019 (14)−0.0129 (12)0.0097 (15)
C150.0638 (18)0.0629 (18)0.0543 (15)−0.0040 (14)−0.0014 (13)−0.0069 (13)
C160.0425 (15)0.082 (2)0.0520 (14)−0.0036 (13)−0.0061 (11)0.0098 (14)
C170.0473 (15)0.0645 (17)0.0514 (14)0.0036 (12)−0.0037 (11)0.0093 (13)
C180.0602 (17)0.0594 (16)0.0476 (14)−0.0033 (13)−0.0051 (12)−0.0003 (12)
C190.0394 (14)0.080 (2)0.0637 (17)0.0072 (14)−0.0045 (12)−0.0096 (15)
O30.0719 (13)0.1128 (17)0.0830 (14)−0.0171 (11)−0.0228 (11)0.0454 (13)
C210.0415 (14)0.087 (2)0.0602 (16)−0.0044 (14)−0.0053 (12)−0.0049 (15)
C220.0708 (19)0.075 (2)0.0473 (14)−0.0034 (16)0.0023 (14)0.0065 (14)
B10.0449 (16)0.0575 (18)0.0523 (16)0.0068 (13)−0.0057 (13)−0.0075 (14)
O40.0729 (13)0.1150 (17)0.0841 (14)−0.0185 (12)−0.0307 (11)0.0455 (13)
C250.085 (2)0.0637 (19)0.0635 (18)−0.0032 (16)−0.0241 (16)0.0160 (15)
B20.0655 (14)0.1032 (17)0.0718 (15)−0.0136 (13)−0.0238 (12)0.0382 (14)
C270.0590 (17)0.073 (2)0.0681 (19)−0.0026 (16)0.0018 (14)0.0218 (16)
C280.0530 (19)0.132 (3)0.074 (2)0.008 (2)−0.0207 (16)−0.007 (2)
C290.081 (2)0.0681 (19)0.0498 (15)0.0003 (16)−0.0061 (14)0.0114 (14)
C300.072 (2)0.0597 (18)0.084 (2)−0.0156 (16)−0.0073 (17)0.0009 (16)
C310.078 (2)0.083 (3)0.131 (4)0.026 (2)−0.009 (2)−0.018 (2)
C320.0523 (19)0.184 (5)0.069 (2)0.003 (2)0.0066 (16)−0.007 (3)
C330.094 (3)0.110 (4)0.221 (7)0.029 (3)−0.006 (4)−0.002 (4)
C340.122 (4)0.234 (8)0.107 (4)−0.007 (5)0.032 (3)−0.037 (4)
C350.102 (3)0.087 (3)0.132 (4)−0.027 (2)−0.024 (3)0.007 (3)
C360.115 (4)0.081 (3)0.190 (6)−0.020 (3)−0.015 (4)0.004 (3)
C370.161 (5)0.153 (5)0.090 (3)−0.037 (4)−0.045 (3)−0.014 (3)
Geometric parameters (Å, °) top
O1—B11.371 (4)C21—C321.504 (4)
O1—C191.465 (3)C21—C351.526 (5)
O2—B11.361 (4)C22—C271.361 (5)
O2—C211.463 (3)C22—H22A0.9300
C3—C131.398 (4)O4—B21.336 (4)
C3—C61.408 (4)O4—C251.452 (4)
C3—C121.452 (3)C25—C331.497 (6)
N1—C51.395 (3)C25—C371.516 (5)
N1—C61.396 (3)C25—C291.556 (5)
N1—C71.429 (3)C27—C301.373 (5)
C5—C161.390 (4)C27—H27A0.9300
C5—C121.415 (4)C28—H28A0.9600
C6—C171.389 (3)C28—H28B0.9600
C7—C181.382 (4)C28—H28C0.9600
C7—C151.383 (4)C29—C361.505 (6)
C8—C131.392 (4)C29—C341.517 (6)
C8—C111.404 (4)C30—H30A0.9300
C8—B11.550 (4)C31—H31A0.9600
C9—C101.399 (4)C31—H31B0.9600
C9—C141.412 (4)C31—H31C0.9600
C9—B21.550 (4)C32—H32A0.9600
C10—C121.391 (4)C32—H32B0.9600
C10—H10A0.9300C32—H32C0.9600
C11—C171.383 (4)C33—H33A0.9600
C11—H11A0.9300C33—H33B0.9600
C13—H13A0.9300C33—H33C0.9600
C14—C161.379 (4)C34—H34A0.9600
C14—H14A0.9300C34—H34B0.9600
C15—C301.384 (4)C34—H34C0.9600
C15—H15A0.9300C35—H35A0.9600
C16—H16A0.9300C35—H35B0.9600
C17—H17A0.9300C35—H35C0.9600
C18—C221.376 (4)C36—H36A0.9600
C18—H18A0.9300C36—H36B0.9600
C19—C281.508 (4)C36—H36C0.9600
C19—C311.519 (5)C37—H37A0.9600
C19—C211.559 (5)C37—H37B0.9600
O3—B21.343 (5)C37—H37C0.9600
O3—C291.445 (4)
B1—O1—C19107.0 (2)O4—C25—C33107.6 (4)
B1—O2—C21107.6 (2)O4—C25—C37106.2 (3)
C13—C3—C6119.2 (2)C33—C25—C37109.2 (4)
C13—C3—C12133.8 (2)O4—C25—C29103.1 (2)
C6—C3—C12107.0 (2)C33—C25—C29115.2 (3)
C5—N1—C6108.4 (2)C37—C25—C29114.7 (4)
C5—N1—C7126.1 (2)O4—B2—O3113.0 (3)
C6—N1—C7125.3 (2)O4—B2—C9123.9 (3)
C16—C5—N1129.1 (2)O3—B2—C9123.1 (3)
C16—C5—C12121.8 (2)C22—C27—C30119.6 (3)
N1—C5—C12109.0 (2)C22—C27—H27A120.2
C17—C6—N1129.1 (2)C30—C27—H27A120.2
C17—C6—C3121.8 (2)C19—C28—H28A109.5
N1—C6—C3109.0 (2)C19—C28—H28B109.5
C18—C7—C15119.6 (3)H28A—C28—H28B109.5
C18—C7—N1120.3 (2)C19—C28—H28C109.5
C15—C7—N1120.1 (2)H28A—C28—H28C109.5
C13—C8—C11118.4 (2)H28B—C28—H28C109.5
C13—C8—B1120.9 (3)O3—C29—C36107.8 (3)
C11—C8—B1120.6 (2)O3—C29—C34105.7 (4)
C10—C9—C14118.2 (2)C36—C29—C34108.2 (4)
C10—C9—B2120.7 (3)O3—C29—C25103.4 (2)
C14—C9—B2121.1 (3)C36—C29—C25115.6 (3)
C12—C10—C9120.6 (3)C34—C29—C25115.3 (3)
C12—C10—H10A119.7C27—C30—C15120.5 (3)
C9—C10—H10A119.7C27—C30—H30A119.7
C17—C11—C8123.1 (2)C15—C30—H30A119.7
C17—C11—H11A118.4C19—C31—H31A109.5
C8—C11—H11A118.4C19—C31—H31B109.5
C10—C12—C5119.0 (2)H31A—C31—H31B109.5
C10—C12—C3134.5 (2)C19—C31—H31C109.5
C5—C12—C3106.5 (2)H31A—C31—H31C109.5
C8—C13—C3120.3 (2)H31B—C31—H31C109.5
C8—C13—H13A119.9C21—C32—H32A109.5
C3—C13—H13A119.9C21—C32—H32B109.5
C16—C14—C9122.9 (3)H32A—C32—H32B109.5
C16—C14—H14A118.6C21—C32—H32C109.5
C9—C14—H14A118.6H32A—C32—H32C109.5
C7—C15—C30119.5 (3)H32B—C32—H32C109.5
C7—C15—H15A120.2C25—C33—H33A109.5
C30—C15—H15A120.2C25—C33—H33B109.5
C14—C16—C5117.5 (3)H33A—C33—H33B109.5
C14—C16—H16A121.2C25—C33—H33C109.5
C5—C16—H16A121.2H33A—C33—H33C109.5
C11—C17—C6117.2 (3)H33B—C33—H33C109.5
C11—C17—H17A121.4C29—C34—H34A109.5
C6—C17—H17A121.4C29—C34—H34B109.5
C22—C18—C7119.8 (3)H34A—C34—H34B109.5
C22—C18—H18A120.1C29—C34—H34C109.5
C7—C18—H18A120.1H34A—C34—H34C109.5
O1—C19—C28108.5 (3)H34B—C34—H34C109.5
O1—C19—C31106.0 (3)C21—C35—H35A109.5
C28—C19—C31110.7 (3)C21—C35—H35B109.5
O1—C19—C21102.2 (2)H35A—C35—H35B109.5
C28—C19—C21115.7 (3)C21—C35—H35C109.5
C31—C19—C21112.9 (3)H35A—C35—H35C109.5
B2—O3—C29109.7 (3)H35B—C35—H35C109.5
O2—C21—C32107.4 (2)C29—C36—H36A109.5
O2—C21—C35106.2 (3)C29—C36—H36B109.5
C32—C21—C35111.1 (3)H36A—C36—H36B109.5
O2—C21—C19102.5 (2)C29—C36—H36C109.5
C32—C21—C19116.1 (3)H36A—C36—H36C109.5
C35—C21—C19112.5 (3)H36B—C36—H36C109.5
C27—C22—C18121.0 (3)C25—C37—H37A109.5
C27—C22—H22A119.5C25—C37—H37B109.5
C18—C22—H22A119.5H37A—C37—H37B109.5
O2—B1—O1113.3 (3)C25—C37—H37C109.5
O2—B1—C8123.5 (2)H37A—C37—H37C109.5
O1—B1—C8123.2 (3)H37B—C37—H37C109.5
B2—O4—C25109.8 (3)
C6—N1—C5—C16178.1 (3)B1—O1—C19—C21−23.4 (3)
C7—N1—C5—C16−5.1 (5)B1—O2—C21—C32−143.9 (3)
C6—N1—C5—C121.1 (3)B1—O2—C21—C3597.0 (3)
C7—N1—C5—C12177.9 (2)B1—O2—C21—C19−21.2 (3)
C5—N1—C6—C17178.7 (3)O1—C19—C21—O226.7 (3)
C7—N1—C6—C171.9 (4)C28—C19—C21—O2144.4 (3)
C5—N1—C6—C30.3 (3)C31—C19—C21—O2−86.7 (3)
C7—N1—C6—C3−176.5 (2)O1—C19—C21—C32143.5 (3)
C13—C3—C6—C17−2.2 (4)C28—C19—C21—C32−98.9 (4)
C12—C3—C6—C17179.9 (2)C31—C19—C21—C3230.1 (4)
C13—C3—C6—N1176.3 (2)O1—C19—C21—C35−87.0 (3)
C12—C3—C6—N1−1.6 (3)C28—C19—C21—C3530.7 (4)
C5—N1—C7—C18119.4 (3)C31—C19—C21—C35159.6 (3)
C6—N1—C7—C18−64.3 (4)C7—C18—C22—C270.7 (5)
C5—N1—C7—C15−61.3 (4)C21—O2—B1—O17.2 (3)
C6—N1—C7—C15115.0 (3)C21—O2—B1—C8−174.5 (3)
C14—C9—C10—C120.1 (4)C19—O1—B1—O211.4 (3)
B2—C9—C10—C12179.1 (3)C19—O1—B1—C8−166.9 (3)
C13—C8—C11—C17−2.1 (4)C13—C8—B1—O210.8 (4)
B1—C8—C11—C17174.0 (3)C11—C8—B1—O2−165.2 (3)
C9—C10—C12—C51.0 (4)C13—C8—B1—O1−171.1 (3)
C9—C10—C12—C3177.9 (3)C11—C8—B1—O112.9 (4)
C16—C5—C12—C10−1.6 (4)B2—O4—C25—C33113.9 (4)
N1—C5—C12—C10175.6 (2)B2—O4—C25—C37−129.2 (4)
C16—C5—C12—C3−179.3 (3)B2—O4—C25—C29−8.3 (4)
N1—C5—C12—C3−2.1 (3)C25—O4—B2—O33.3 (5)
C13—C3—C12—C107.6 (5)C25—O4—B2—C9−176.8 (4)
C6—C3—C12—C10−174.9 (3)C29—O3—B2—O43.8 (5)
C13—C3—C12—C5−175.2 (3)C29—O3—B2—C9−176.1 (4)
C6—C3—C12—C52.2 (3)C10—C9—B2—O4−164.1 (4)
C11—C8—C13—C31.1 (4)C14—C9—B2—O414.9 (6)
B1—C8—C13—C3−174.9 (2)C10—C9—B2—O315.8 (6)
C6—C3—C13—C80.9 (4)C14—C9—B2—O3−165.3 (4)
C12—C3—C13—C8178.1 (3)C18—C22—C27—C300.2 (5)
C10—C9—C14—C16−0.7 (5)B2—O3—C29—C36−131.5 (4)
B2—C9—C14—C16−179.7 (3)B2—O3—C29—C34113.0 (4)
C18—C7—C15—C300.6 (4)B2—O3—C29—C25−8.6 (4)
N1—C7—C15—C30−178.7 (3)O4—C25—C29—O39.9 (3)
C9—C14—C16—C50.1 (5)C33—C25—C29—O3−107.1 (4)
N1—C5—C16—C14−175.6 (3)C37—C25—C29—O3124.8 (4)
C12—C5—C16—C141.0 (4)O4—C25—C29—C36127.5 (4)
C8—C11—C17—C60.8 (4)C33—C25—C29—C3610.5 (5)
N1—C6—C17—C11−176.8 (3)C37—C25—C29—C36−117.6 (4)
C3—C6—C17—C111.4 (4)O4—C25—C29—C34−105.0 (4)
C15—C7—C18—C22−1.1 (4)C33—C25—C29—C34138.0 (5)
N1—C7—C18—C22178.1 (3)C37—C25—C29—C349.9 (5)
B1—O1—C19—C28−146.1 (3)C22—C27—C30—C15−0.7 (5)
B1—O1—C19—C3195.0 (3)C7—C15—C30—C270.4 (5)
Acknowledgements top

The authors are grateful for financial support from the National Natural Science Foundation of China (No. 30972321) and the Basic Research Project of the Natural Science Foundation of Jiangsu Provincial Universities (10KJB53007).

references
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