organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

9-[(E)-2-(4,4,5,5-Tetra­methyl-1,3,2-dioxa­borolan-2-yl)ethen­yl]-9H-carbazole

aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan
*Correspondence e-mail: okuno@center.wakayama-u.ac.jp

(Received 30 November 2011; accepted 6 December 2011; online 10 December 2011)

The title compound, C20H22BNO2, is a simple olefinic compound which carries both B and N atoms that are trans to one another. The π-conjugated system of the compound is considered to be isoelectronic with 1,3-butadiene. There are two independent mol­ecules in the asymmetric unit in which the environments around the boron atoms are essentially planar (r.m.s. deviations of 0.0032 and 0.0021 Å for the BO2C planes). The dihedral angles of the olefinic planes with the boron planes are 5.70 (11) and 9.74 (9)°, respectively, while the dihedral angles of the olefinic planes with the carbazole planes are 19.37 (3) and 10.74 (6)°. These dihedral angles are consistent with those in 9-ethenylcarbazole and an ethenylboronic ester derivative. The N—Csp2, B—Csp2 and C=C bond lengths suggest that the contribution of the canonical structure can be described as N+=C—C=B.

Related literature

For the related structure of 9-ethenylcarbazole, see: Tsutsui et al. (1976[Tsutsui, K., Hirotsu, K., Umesaki, M., Kurahashi, M., Shimada, A. & Higuchi, T. (1976). Acta Cryst. B32, 3049-3053.]); Tian et al. (2006[Tian, X., Shi, W., Shen, K., Li, C., Lin, J., Che, Y. & Zhang, P. (2006). J. Organomet. Chem. 691, 994-1006.]). For the related structure of a ethenyl-boronic ester derivative, see: Clark et al. (2004[Clark, J. S., Freeman, R. P., Cacho, M., Thomas, A. W., Swallow, S. & Wilson, C. (2004). Tetrahedron Lett. 45, 8639-8642.]). For the preparation of the title compound, see: Geier et al. (2009[Geier, M. J., Vogels, C. M., Decken, A. & Westcott, S. A. (2009). J. Organomet. Chem. 694, 3154-3159.]).

[Scheme 1]

Experimental

Crystal data
  • C20H22BNO2

  • Mr = 319.21

  • Triclinic, [P \overline 1]

  • a = 11.616 (3) Å

  • b = 12.962 (3) Å

  • c = 12.990 (3) Å

  • α = 83.620 (11)°

  • β = 85.632 (11)°

  • γ = 64.647 (6)°

  • V = 1755.6 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 93 K

  • 0.19 × 0.07 × 0.03 mm

Data collection
  • Rigaku Saturn724+ diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.990, Tmax = 0.998

  • 12732 measured reflections

  • 6408 independent reflections

  • 4117 reflections with F2 > 2σ(F2)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.137

  • S = 1.01

  • 6406 reflections

  • 433 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Selected bond lengths (Å)

B1—C14 1.537 (3)
B2—C34 1.537 (4)
N1—C13 1.396 (3)
N2—C33 1.392 (3)
C13—C14 1.336 (4)
C33—C34 1.334 (4)

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Comment top

Boron and nitrogen atoms are known to be isoelectronic with carbocation and carbanion, respectively. Several isoelectronic structures have been prepared by replacing C=C bond of aromatic systems with B—N bond. In order to expand the varieties of isoelectronic structures by utilizing combination of boron and nitrogen atoms, an insertion of C=C bond into B—N bond is quite important. The title compound, C20H22BNO2, is a simple olefinic compound which carries both boron and nitrogen atoms in a trans position. The π-conjugated system is considered to be isoelectronic with 1,3-butadiene.

There are two independent molecules in the asymmetric unit and their structures are similar (Fig.1). The environments around the boron atoms, the B1/O1/O2/C14 plane (r.m.s. deviation 0.0032 Å and the B2/O3/O4/C34 plane (r.m.s. deviation 0.0021 Å), are planar. The dihedral angles of the C13/H13/C14/H14 plane (r.m.s. deviation 0.0095 Å with the N1/C1—C12 plane (r.m.s. deviation 0.0191 Å and the B1/O1/O2/C14 plane are 19.37 (3)° and 5.70 (11)°, respectively. The dihedral angles of the C33/H33/C34/H34 plane (r.m.s. deviation 0.0111 Å with the N2/C21—C32 plane (r.m.s. deviation 0.0376 Å and the B2/O3/O4/C34 plane are 10.74 (6)° and 9.74 (9)°, respectively. These dihedral angles are consistent with those in 9-ethenylcarbazole (Tsutsui et al., 1976; Tian et al., 2006) and a ethenylboronic ester derivative (Clark et al., 2004). The bond distances of N1—C13 and N2—C33 show a tendency to be shorten compared with N-Csp2 distance of 9-ethenylcarbazole (1.398 (8)–1.425 (7) Å). The bond distances of B1—C14 and B2—C34 are also tend to be short compared with B-Csp2 distance of the reported ethenylboronic ester derivative (1.544 (5) Å). The bond distances of C13—C14 and C33—C34 display a tendency to be elongated compared with C=C bond distances of 9-ethenylcarbazole (1.231 (8)–1.2861 (3) Å or a ethenylboronic ester derivative (1.325 (5) Å). These tendencies were well explained by considering the canonical structure of the π-conjugated system such as N+=C—C=B-.

Although a boron atom without steric protection shows intermolecular contact with a lone pair of another atom in many cases, the spatial contact between the compounds could not be detected. This is presumably because the vacant p-orbital of boron atom is satisfied with the lone pairs of oxygen atoms and/or π electrons of the C=C bond.

Related literature top

For the related structure of 9-ethenylcarbazole, see: Tsutsui et al. (1976); Tian et al. (2006). For the related structure of a ethenyl-boronic ester derivative, see: Clark et al. (2004). For the preparation of the title compound, see: Geier et al. (2009).

Experimental top

The title compound was prepared according to a published procedure (Geier et al., 2009). The purification of the compound was performed by gel permeation chromatography (GPC). The single crystals with sufficient quality for X-ray analysis were obtained by concentration of a hexane solution in a refrigerator.

Refinement top

The C-bound H atoms were placed at ideal positions and were refined as riding on their parent C atoms. Uiso(H) values of the H atoms were set at 1.2Ueq(parent atom).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres.
9-[(E)-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]- 9H-carbazole top
Crystal data top
C20H22BNO2Z = 4
Mr = 319.21F(000) = 680.00
Triclinic, P1Dx = 1.208 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 11.616 (3) ÅCell parameters from 4367 reflections
b = 12.962 (3) Åθ = 1.7–30.9°
c = 12.990 (3) ŵ = 0.08 mm1
α = 83.620 (11)°T = 93 K
β = 85.632 (11)°Prism, colourless
γ = 64.647 (6)°0.19 × 0.07 × 0.03 mm
V = 1755.6 (8) Å3
Data collection top
Rigaku Saturn724+
diffractometer
4117 reflections with F2 > 2σ(F2)
Detector resolution: 29.257 pixels mm-1Rint = 0.035
ω scansθmax = 25.5°
Absorption correction: numerical
(NUMABS; Rigaku, 1999)
h = 149
Tmin = 0.990, Tmax = 0.998k = 1515
12732 measured reflectionsl = 1415
6408 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.068P)2]
where P = (Fo2 + 2Fc2)/3
6406 reflections(Δ/σ)max < 0.001
433 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.22 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C20H22BNO2γ = 64.647 (6)°
Mr = 319.21V = 1755.6 (8) Å3
Triclinic, P1Z = 4
a = 11.616 (3) ÅMo Kα radiation
b = 12.962 (3) ŵ = 0.08 mm1
c = 12.990 (3) ÅT = 93 K
α = 83.620 (11)°0.19 × 0.07 × 0.03 mm
β = 85.632 (11)°
Data collection top
Rigaku Saturn724+
diffractometer
6408 independent reflections
Absorption correction: numerical
(NUMABS; Rigaku, 1999)
4117 reflections with F2 > 2σ(F2)
Tmin = 0.990, Tmax = 0.998Rint = 0.035
12732 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.01Δρmax = 0.23 e Å3
6406 reflectionsΔρmin = 0.22 e Å3
433 parameters
Special details top

Refinement. Refinement was performed using all reflections except for 2 with very negative F2. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.19650 (14)0.80244 (12)0.27030 (11)0.0288 (4)
O21.05702 (13)0.72769 (12)0.23902 (11)0.0276 (4)
O30.73428 (13)0.89367 (12)0.10030 (10)0.0267 (4)
O40.65878 (15)0.75895 (15)0.08875 (13)0.0446 (5)
N10.89819 (16)1.15426 (15)0.21620 (13)0.0266 (5)
N20.45751 (16)1.05543 (15)0.34418 (12)0.0251 (4)
C10.7867 (2)1.20195 (18)0.15851 (16)0.0266 (5)
C20.7364 (2)1.15124 (19)0.09656 (16)0.0296 (6)
C30.6224 (2)1.22080 (19)0.04871 (17)0.0336 (6)
C40.5611 (3)1.3375 (2)0.06069 (18)0.0381 (6)
C50.6129 (3)1.3884 (2)0.11964 (18)0.0359 (6)
C60.7264 (2)1.32114 (18)0.16925 (16)0.0296 (6)
C70.8042 (2)1.34695 (18)0.23469 (17)0.0300 (6)
C80.7935 (3)1.4481 (2)0.27136 (18)0.0380 (6)
C90.8881 (3)1.4439 (2)0.33207 (19)0.0407 (6)
C100.9931 (3)1.3404 (2)0.35646 (18)0.0373 (6)
C111.0044 (3)1.2395 (2)0.32233 (17)0.0325 (6)
C120.9099 (2)1.24341 (18)0.26120 (16)0.0274 (5)
C130.9859 (2)1.03972 (18)0.23079 (15)0.0263 (5)
C140.9701 (2)0.94585 (18)0.21762 (15)0.0260 (5)
C151.2589 (2)0.68006 (18)0.30464 (17)0.0293 (5)
C161.1828 (2)0.63081 (18)0.24721 (17)0.0301 (6)
C171.2405 (3)0.6684 (2)0.42173 (17)0.0405 (7)
C181.3987 (2)0.6370 (2)0.27360 (19)0.0364 (6)
C191.2325 (3)0.6055 (2)0.13647 (18)0.0359 (6)
C201.1668 (3)0.52875 (19)0.30432 (19)0.0400 (6)
C210.35972 (19)1.03528 (18)0.40093 (15)0.0259 (5)
C220.3077 (2)0.95879 (19)0.38847 (16)0.0283 (5)
C230.2077 (2)0.9603 (2)0.45537 (17)0.0333 (6)
C240.1605 (3)1.0353 (2)0.53272 (17)0.0367 (6)
C250.2107 (2)1.1126 (2)0.54471 (17)0.0333 (6)
C260.3101 (2)1.11383 (18)0.47789 (15)0.0263 (5)
C270.3769 (2)1.18617 (18)0.46632 (15)0.0256 (5)
C280.3674 (2)1.27887 (19)0.51777 (17)0.0318 (6)
C290.4455 (3)1.33272 (19)0.48543 (17)0.0338 (6)
C300.5321 (3)1.2958 (2)0.40222 (17)0.0332 (6)
C310.5438 (2)1.20373 (19)0.35044 (17)0.0305 (6)
C320.4653 (2)1.14974 (18)0.38344 (15)0.0253 (5)
C330.54010 (19)0.99494 (19)0.26653 (15)0.0264 (5)
C340.5570 (2)0.89644 (18)0.23134 (16)0.0292 (5)
C350.7890 (2)0.84178 (19)0.00247 (15)0.0292 (5)
C360.7708 (3)0.7292 (3)0.01803 (19)0.0399 (6)
C370.7120 (3)0.9265 (3)0.08385 (18)0.0499 (8)
C380.9265 (2)0.8232 (2)0.00862 (17)0.0326 (6)
C390.8800 (3)0.6309 (2)0.0738 (3)0.0529 (8)
C400.7429 (3)0.6927 (3)0.0810 (3)0.0710 (10)
B11.0760 (3)0.8250 (2)0.24176 (18)0.0263 (6)
B20.6507 (3)0.8488 (3)0.1401 (2)0.0285 (6)
H20.77851.07170.08730.0355*
H30.58561.18790.00690.0403*
H40.48261.38280.02790.0457*
H50.57151.46860.12620.0430*
H80.72221.51860.25480.0456*
H90.88171.51220.35760.0488*
H101.05791.33970.39730.0448*
H111.07521.16910.34030.0390*
H131.06741.02690.25290.0316*
H140.89160.95390.19280.0312*
H17A1.14920.69980.44010.0486*
H17B1.27950.71040.45330.0486*
H17C1.28100.58720.44730.0486*
H18A1.43630.67910.30700.0437*
H18B1.40790.64910.19820.0437*
H18C1.44260.55510.29550.0437*
H19A1.23870.67330.09960.0430*
H19B1.17380.58630.10090.0430*
H19C1.31700.54090.13780.0430*
H20A1.11060.50930.26570.0480*
H20B1.12920.54810.37360.0480*
H20C1.25020.46310.31050.0480*
H220.33950.90720.33590.0339*
H230.17090.90880.44800.0399*
H240.09301.03350.57790.0441*
H250.17801.16400.59750.0399*
H280.30811.30440.57420.0382*
H290.44021.39550.52010.0405*
H300.58411.33460.38060.0399*
H310.60361.17840.29430.0366*
H330.59261.02910.23340.0317*
H340.51080.85540.26300.0351*
H37A0.71860.99920.08230.0598*
H37B0.62250.93950.07420.0598*
H37C0.74520.89550.15080.0598*
H38A0.97370.77210.05000.0391*
H38B0.93140.89700.00970.0391*
H38C0.96380.78850.07340.0391*
H39A0.85810.56570.09000.0635*
H39B0.89510.65550.13810.0635*
H39C0.95720.60810.02910.0635*
H40A0.66930.75580.11380.0852*
H40B0.72390.62580.06430.0852*
H40C0.81730.67280.12860.0852*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0296 (9)0.0213 (8)0.0343 (9)0.0095 (7)0.0038 (7)0.0006 (7)
O20.0256 (8)0.0199 (8)0.0345 (9)0.0073 (7)0.0004 (7)0.0021 (7)
O30.0296 (9)0.0262 (8)0.0223 (8)0.0095 (7)0.0040 (6)0.0065 (6)
O40.0408 (10)0.0484 (11)0.0571 (11)0.0285 (9)0.0249 (8)0.0320 (9)
N10.0274 (11)0.0209 (10)0.0293 (10)0.0089 (8)0.0045 (8)0.0031 (8)
N20.0243 (10)0.0263 (10)0.0227 (10)0.0088 (8)0.0027 (8)0.0052 (8)
C10.0229 (12)0.0233 (12)0.0290 (12)0.0070 (10)0.0068 (10)0.0000 (10)
C20.0292 (13)0.0242 (12)0.0307 (12)0.0081 (10)0.0011 (10)0.0015 (10)
C30.0308 (14)0.0309 (13)0.0365 (13)0.0120 (11)0.0013 (11)0.0018 (11)
C40.0288 (13)0.0353 (14)0.0404 (14)0.0071 (12)0.0030 (11)0.0053 (12)
C50.0311 (14)0.0244 (13)0.0412 (14)0.0039 (11)0.0072 (11)0.0023 (11)
C60.0278 (13)0.0235 (12)0.0332 (13)0.0085 (10)0.0098 (10)0.0021 (10)
C70.0294 (13)0.0230 (12)0.0355 (13)0.0107 (10)0.0111 (10)0.0038 (10)
C80.0392 (15)0.0267 (13)0.0451 (15)0.0128 (12)0.0122 (12)0.0057 (11)
C90.0479 (16)0.0291 (14)0.0484 (15)0.0198 (13)0.0125 (13)0.0115 (12)
C100.0398 (15)0.0365 (15)0.0400 (14)0.0201 (12)0.0047 (11)0.0081 (11)
C110.0356 (14)0.0287 (13)0.0335 (13)0.0151 (11)0.0059 (11)0.0032 (10)
C120.0319 (13)0.0245 (12)0.0274 (12)0.0144 (11)0.0082 (10)0.0044 (10)
C130.0243 (12)0.0249 (12)0.0257 (12)0.0074 (10)0.0011 (9)0.0004 (9)
C140.0265 (12)0.0236 (12)0.0260 (12)0.0088 (10)0.0010 (9)0.0032 (9)
C150.0290 (13)0.0192 (11)0.0371 (13)0.0075 (10)0.0036 (10)0.0016 (10)
C160.0247 (12)0.0188 (11)0.0426 (14)0.0050 (10)0.0029 (10)0.0028 (10)
C170.0459 (16)0.0348 (14)0.0376 (14)0.0137 (13)0.0070 (12)0.0006 (11)
C180.0304 (13)0.0275 (13)0.0482 (15)0.0086 (11)0.0053 (11)0.0036 (11)
C190.0299 (13)0.0299 (13)0.0462 (14)0.0091 (11)0.0004 (11)0.0124 (11)
C200.0401 (15)0.0267 (13)0.0546 (16)0.0161 (12)0.0084 (12)0.0045 (12)
C210.0199 (11)0.0299 (12)0.0239 (11)0.0075 (10)0.0004 (9)0.0006 (10)
C220.0267 (12)0.0278 (12)0.0274 (12)0.0089 (10)0.0013 (10)0.0032 (10)
C230.0319 (13)0.0362 (14)0.0316 (13)0.0152 (11)0.0014 (11)0.0009 (11)
C240.0331 (14)0.0463 (16)0.0288 (13)0.0170 (12)0.0098 (10)0.0010 (11)
C250.0340 (14)0.0374 (14)0.0252 (12)0.0123 (12)0.0035 (10)0.0049 (10)
C260.0262 (12)0.0264 (12)0.0211 (11)0.0060 (10)0.0029 (9)0.0009 (9)
C270.0250 (12)0.0254 (12)0.0216 (11)0.0058 (10)0.0044 (9)0.0010 (9)
C280.0317 (13)0.0283 (13)0.0287 (12)0.0052 (11)0.0046 (10)0.0044 (10)
C290.0383 (14)0.0272 (13)0.0335 (13)0.0093 (11)0.0110 (11)0.0052 (10)
C300.0366 (14)0.0323 (14)0.0337 (13)0.0173 (12)0.0074 (11)0.0012 (11)
C310.0284 (13)0.0327 (13)0.0287 (12)0.0115 (11)0.0021 (10)0.0036 (10)
C320.0255 (12)0.0250 (12)0.0237 (11)0.0081 (10)0.0034 (9)0.0036 (9)
C330.0218 (12)0.0315 (13)0.0229 (11)0.0089 (10)0.0008 (9)0.0020 (10)
C340.0282 (13)0.0270 (13)0.0310 (12)0.0110 (10)0.0047 (10)0.0037 (10)
C350.0307 (13)0.0331 (13)0.0222 (11)0.0114 (11)0.0043 (10)0.0082 (10)
C360.0369 (14)0.0416 (15)0.0479 (15)0.0214 (12)0.0202 (12)0.0250 (12)
C370.0461 (17)0.0581 (18)0.0305 (14)0.0076 (14)0.0037 (12)0.0037 (13)
C380.0333 (13)0.0388 (14)0.0266 (12)0.0167 (11)0.0081 (10)0.0069 (10)
C390.0555 (18)0.0281 (14)0.0670 (19)0.0143 (13)0.0294 (14)0.0077 (13)
C400.065 (2)0.096 (3)0.080 (3)0.054 (2)0.0319 (17)0.063 (2)
B10.0312 (15)0.0260 (14)0.0221 (13)0.0129 (12)0.0029 (11)0.0027 (11)
B20.0243 (14)0.0281 (14)0.0330 (14)0.0108 (12)0.0003 (11)0.0041 (11)
Geometric parameters (Å, º) top
O1—C151.466 (3)C35—C361.551 (5)
O1—B11.373 (4)C35—C371.517 (3)
O2—C161.465 (3)C35—C381.507 (4)
O2—B11.376 (4)C36—C391.519 (4)
O3—C351.474 (3)C36—C401.522 (5)
O3—B21.374 (4)C2—H20.950
O4—C361.467 (3)C3—H30.950
O4—B21.371 (4)C4—H40.950
N1—C11.407 (3)C5—H50.950
N1—C121.412 (4)C8—H80.950
N1—C131.396 (3)C9—H90.950
N2—C211.409 (3)C10—H100.950
N2—C321.415 (4)C11—H110.950
N2—C331.392 (3)C13—H130.950
C1—C21.393 (4)C14—H140.950
C1—C61.415 (3)C17—H17A0.980
C2—C31.390 (3)C17—H17B0.980
C3—C41.391 (4)C17—H17C0.980
C4—C51.381 (5)C18—H18A0.980
C5—C61.391 (3)C18—H18B0.980
C6—C71.446 (4)C18—H18C0.980
C7—C81.397 (4)C19—H19A0.980
C7—C121.406 (3)C19—H19B0.980
C8—C91.380 (5)C19—H19C0.980
C9—C101.397 (3)C20—H20A0.980
C10—C111.378 (4)C20—H20B0.980
C11—C121.383 (4)C20—H20C0.980
C13—C141.336 (4)C22—H220.950
C14—B11.537 (3)C23—H230.950
C15—C161.560 (4)C24—H240.950
C15—C171.520 (3)C25—H250.950
C15—C181.512 (4)C28—H280.950
C16—C191.525 (4)C29—H290.950
C16—C201.519 (4)C30—H300.950
C21—C221.392 (4)C31—H310.950
C21—C261.416 (3)C33—H330.950
C22—C231.391 (4)C34—H340.950
C23—C241.390 (4)C37—H37A0.980
C24—C251.385 (5)C37—H37B0.980
C25—C261.395 (4)C37—H37C0.980
C26—C271.442 (4)C38—H38A0.980
C27—C281.399 (4)C38—H38B0.980
C27—C321.402 (3)C38—H38C0.980
C28—C291.380 (4)C39—H39A0.980
C29—C301.395 (3)C39—H39B0.980
C30—C311.385 (4)C39—H39C0.980
C31—C321.388 (4)C40—H40A0.980
C33—C341.334 (4)C40—H40B0.980
C34—B21.537 (4)C40—H40C0.980
O1···C133.017 (3)C26···H10iv3.2689
O1···C193.110 (4)C26···H11iv3.1521
O2···C173.119 (3)C27···H10iv3.5052
O3···C332.971 (3)C28···H9xi3.4471
O3···C393.134 (3)C28···H18Ax3.5790
O4···C373.159 (4)C28···H20Cviii3.3390
N1···C53.598 (3)C28···H34iii3.2475
C1···C42.764 (3)C29···H17Bx3.1483
C1···C143.126 (3)C29···H17Cviii3.0266
C2···C52.822 (4)C29···H18Ax3.0783
C2···C133.187 (3)C29···H18Cviii3.5697
C2···C143.235 (3)C29···H20Cviii3.1325
C3···C62.773 (4)C30···H17Bx2.9601
C5···C83.353 (5)C30···H18Cviii3.2391
C7···C102.768 (4)C30···H20Cviii3.2835
C8···C112.816 (3)C33···H25iii3.5184
C9···C122.756 (4)C33···H37Bv3.0667
C11···C133.060 (4)C33···H37Cv3.3930
C17···C202.911 (5)C33···H40Av3.5877
C17···B13.089 (4)C34···H28iii3.3559
C18···C192.903 (4)C34···H37Av3.5331
C18···C203.513 (5)C34···H37Bv2.9875
C18···B13.514 (4)C34···H37Cv3.5375
C19···B13.054 (4)C35···H23.2424
C20···B13.534 (4)C35···H143.5176
C21···C242.772 (4)C37···H23.3948
C21···C343.150 (3)C37···H33.3753
C22···C252.827 (4)C37···H13ii3.4537
C22···C333.207 (4)C38···H23.2725
C22···C343.266 (3)C38···H13ii3.5449
C23···C262.769 (5)C38···H143.1802
C25···C283.343 (5)C38···H19B3.4358
C27···C302.768 (4)C39···H8vi3.4457
C28···C312.820 (3)C39···H19B3.2488
C29···C322.760 (4)C39···H20A3.5219
C31···C333.046 (4)C39···H39Cxiii3.2368
C37···C402.892 (6)C40···H3v3.5481
C37···B23.103 (4)C40···H4v3.1717
C38···C392.850 (5)C40···H19Bxiii3.3541
C38···C403.471 (6)C40···H19Cxiii3.5448
C38···B23.521 (4)C40···H20Axiii3.5302
C39···B23.093 (4)B1···H23i3.4196
C40···B23.529 (5)B1···H24iii3.1429
O1···C22i3.372 (4)B1···H25iii3.4434
O1···C23i3.370 (4)B1···H38A3.1009
O2···C383.526 (3)B2···H37Bv3.2813
O3···C23.344 (4)H2···O32.5567
O3···C143.569 (4)H2···C353.2424
N1···C38ii3.317 (3)H2···C373.3948
N2···C26iii3.492 (3)H2···C383.2725
C2···O33.344 (4)H2···H313.2950
C11···C24i3.578 (3)H2···H332.9556
C13···C38ii3.533 (4)H2···H37A2.7348
C14···O33.569 (4)H2···H38B2.5925
C14···C24iii3.462 (3)H3···O33.5567
C21···C27iii3.572 (3)H3···O4v2.9576
C21···C32iii3.596 (3)H3···C373.3753
C22···O1iv3.372 (4)H3···C40v3.5481
C23···O1iv3.370 (4)H3···H18Bii3.2288
C24···C11iv3.578 (3)H3···H19Aii3.3887
C24···C14iii3.462 (3)H3···H333.3831
C26···N2iii3.492 (3)H3···H37A2.6147
C27···C21iii3.572 (3)H3···H37B3.3418
C32···C21iii3.596 (3)H3···H37Bv3.4791
C34···C37v3.535 (4)H3···H40Av2.9959
C37···C34v3.535 (4)H3···H40Bv3.4447
C38···O23.526 (3)H4···O4v3.4571
C38···N1ii3.317 (3)H4···C4vii3.5083
C38···C13ii3.533 (4)H4···C5vii3.1527
O1···H132.6326H4···C19viii3.4437
O1···H143.4004H4···C40v3.1717
O1···H17A2.5927H4···H4vii3.2307
O1···H17B2.5956H4···H5vii2.5326
O1···H17C3.2569H4···H18Bii3.1088
O1···H18A2.6000H4···H19Aii3.3451
O1···H18B2.5969H4···H19Bviii3.5571
O1···H18C3.2583H4···H19Cviii2.6059
O1···H19A2.8139H4···H19Cii3.4309
O2···H142.7591H4···H40Av3.0916
O2···H17A2.8254H4···H40Bv2.4566
O2···H19A2.5804H5···C4vii3.2378
O2···H19B2.5790H5···C18viii3.0086
O2···H19C3.2483H5···C19viii3.5579
O2···H20A2.6133H5···H4vii2.5326
O2···H20B2.6130H5···H18Aviii3.5520
O2···H20C3.2682H5···H18Bviii2.5229
O3···H332.5590H5···H18Cviii2.6356
O3···H343.3888H5···H19Cviii2.6893
O3···H37A2.5809H5···H19Cii3.5690
O3···H37B2.5816H5···H303.5397
O3···H37C3.2528H8···O4ix3.4179
O3···H38A2.6159H8···C18viii3.3972
O3···H38B2.6184H8···C39ix3.4457
O3···H38C3.2734H8···H18Aviii3.1419
O3···H39B2.8506H8···H18Bviii3.4023
O4···H342.7989H8···H18Cviii3.0879
O4···H37B2.8849H8···H28xi3.2629
O4···H39A2.5820H8···H29xi3.3817
O4···H39B2.5823H8···H303.5972
O4···H39C3.2502H8···H39Aix2.7319
O4···H40A2.6288H8···H39Bix3.3861
O4···H40B2.6302H9···C20ix3.4233
O4···H40C3.2800H9···C28xi3.4471
N1···H22.8113H9···H17Cx3.5047
N1···H112.7883H9···H20Aix2.8175
N1···H142.6814H9···H20Bix3.1279
N2···H222.8125H9···H20Bx3.4972
N2···H312.7862H9···H28xi2.6427
N2···H342.7119H9···H39Aix3.4756
C1···H33.2430H9···H39Bix3.2565
C1···H53.2876H10···C20ix3.2907
C1···H133.3075H10···C25i3.2043
C1···H142.9029H10···C26i3.2689
C2···H43.2747H10···C27i3.5052
C2···H142.6526H10···H17Ax3.2488
C3···H53.2678H10···H20Aix2.8790
C4···H23.2842H10···H20Bix3.1254
C5···H33.2595H10···H20Cix3.3305
C5···H83.2208H10···H25i3.2265
C6···H23.3074H11···C21i3.1201
C6···H43.2492H11···C22i2.9476
C6···H82.8819H11···C23i2.7948
C7···H52.8662H11···C24i2.8600
C7···H93.2514H11···C25i3.0466
C7···H113.2934H11···C26i3.1521
C8···H53.2121H11···H22i3.4705
C8···H103.2630H11···H23i3.2479
C9···H113.2784H11···H24i3.3524
C10···H83.2728H11···H37Cii3.0481
C11···H93.2680H11···H38Cii3.4828
C11···H132.7690H13···C22i3.1563
C12···H83.2843H13···C23i3.0430
C12···H103.2294H13···C37ii3.4537
C12···H132.6224H13···C38ii3.5449
C13···H23.0174H13···H22i3.0827
C13···H112.8553H13···H23i2.8696
C14···H22.7073H13···H24iii3.0257
C15···H19A2.7060H13···H37Aii3.1325
C15···H19B3.4063H13···H37Cii2.9407
C15···H19C2.8307H13···H38Bii3.2048
C15···H20A3.4310H13···H38Cii3.0730
C15···H20B2.7680H14···O32.6754
C15···H20C2.8499H14···C24iii3.5794
C16···H17A2.6979H14···C353.5176
C16···H17B3.3999H14···C383.1802
C16···H17C2.8198H14···H24iii3.0246
C16···H18A3.4202H14···H25iii3.1952
C16···H18B2.7461H14···H333.1980
C16···H18C2.8420H14···H38A2.9460
C17···H18A2.6686H14···H38B2.7622
C17···H18B3.3409H17A···C9x3.4193
C17···H18C2.7106H17A···C10x3.1239
C17···H20B2.5614H17A···C11x3.4394
C17···H20C3.1232H17A···H10x3.2488
C18···H17A3.3396H17A···H23i2.8395
C18···H17B2.6731H17A···H24iii3.3931
C18···H17C2.7096H17A···H25iii3.4855
C18···H19A2.9053H17B···C22i3.3821
C18···H19C2.7068H17B···C23i2.9814
C18···H20C3.3551H17B···C29x3.1483
C19···H18B2.5385H17B···C30x2.9601
C19···H18C3.1228H17B···H22i3.1321
C19···H20A2.6581H17B···H23i2.3248
C19···H20B3.3434H17B···H29x2.9741
C19···H20C2.7170H17B···H30x2.6374
C20···H17A2.9148H17C···C9x3.4345
C20···H17C2.7084H17C···C29xii3.0266
C20···H18C3.3563H17C···H9x3.5047
C20···H19A3.3428H17C···H29xii2.5097
C20···H19B2.6698H17C···H29x3.4017
C20···H19C2.7078H17C···H30x3.2977
C21···H233.2440H18A···C22i3.5314
C21···H253.2966H18A···C28x3.5790
C21···H333.3191H18A···C29x3.0783
C21···H342.9454H18A···H5xii3.5520
C22···H243.2770H18A···H8xii3.1419
C22···H342.6857H18A···H22i2.7350
C23···H253.2714H18A···H28x3.5441
C24···H223.2856H18A···H29x2.6193
C25···H233.2619H18A···H34i2.7615
C25···H283.2083H18B···C3ii3.4227
C26···H223.3037H18B···C4ii3.3475
C26···H243.2527H18B···C5xii3.4101
C26···H282.8811H18B···H3ii3.2288
C27···H252.8609H18B···H4ii3.1088
C27···H293.2550H18B···H5xii2.5229
C27···H313.2964H18B···H8xii3.4023
C28···H253.2015H18B···H34i3.5610
C28···H303.2594H18C···C5xii3.2483
C29···H313.2864H18C···C29xii3.5697
C30···H283.2694H18C···C30xii3.2391
C31···H293.2762H18C···H5xii2.6356
C31···H332.6998H18C···H8xii3.0879
C32···H283.2817H18C···H29xii3.3891
C32···H303.2340H18C···H29x3.0961
C32···H332.5860H18C···H30xii2.7643
C33···H223.0430H19A···C1ii3.5328
C33···H312.8401H19A···C2ii3.3037
C34···H222.7325H19A···C3ii3.0062
C35···H39A3.3943H19A···C4ii2.9686
C35···H39B2.7001H19A···C5ii3.2092
C35···H39C2.8132H19A···C6ii3.4812
C35···H40A2.7344H19A···H3ii3.3887
C35···H40B3.4078H19A···H4ii3.3451
C35···H40C2.8162H19A···H38A2.8762
C36···H37A3.4058H19B···C383.4358
C36···H37B2.7197H19B···C393.2488
C36···H37C2.8365H19B···C40xiii3.3541
C36···H38A2.7127H19B···H4xii3.5571
C36···H38B3.3958H19B···H38A2.5937
C36···H38C2.8100H19B···H38C3.4631
C37···H38A3.3303H19B···H39Axiii3.4666
C37···H38B2.6499H19B···H39B2.9822
C37···H38C2.7018H19B···H39C2.6398
C37···H40A2.5399H19B···H40Bxiii2.5695
C37···H40C3.0849H19B···H40Cxiii3.2955
C38···H37A2.6644H19C···C4xii3.1214
C38···H37B3.3290H19C···C4ii3.4047
C38···H37C2.6915H19C···C5xii3.1528
C38···H39B2.8542H19C···C5ii3.4970
C38···H39C2.6485H19C···C40xiii3.5448
C38···H40C3.3064H19C···H4xii2.6059
C39···H38A2.4819H19C···H4ii3.4309
C39···H38C3.0545H19C···H5xii2.6893
C39···H40A3.3444H19C···H5ii3.5690
C39···H40B2.6705H19C···H40Bxiii2.6852
C39···H40C2.7152H20A···C9vi3.0849
C40···H37B2.8996H20A···C10vi3.1275
C40···H37C2.6953H20A···C393.5219
C40···H38C3.3073H20A···C40xiii3.5302
C40···H39A2.6815H20A···H9vi2.8175
C40···H39B3.3453H20A···H10vi2.8790
C40···H39C2.7026H20A···H39B2.9115
B1···H132.5945H20A···H39C3.5019
B1···H17A2.8662H20A···H40Bxiii3.3125
B1···H17B3.5240H20A···H40Cxiii2.9080
B1···H18B3.5789H20B···H9vi3.1279
B1···H19A2.8185H20B···H9x3.4972
B1···H19B3.4857H20B···H10vi3.1254
B2···H332.5578H20C···C28xii3.3390
B2···H37A3.5330H20C···C29xii3.1325
B2···H37B2.8836H20C···C30xii3.2835
B2···H38A3.5819H20C···H10vi3.3305
B2···H39A3.5239H20C···H29xii3.4322
B2···H39B2.8724H20C···H40Bxiii3.4672
B2···H40A3.5954H20C···H40Cxiii3.4191
H2···H32.3452H22···O1iv2.7802
H2···H142.0058H22···C15iv3.5198
H3···H42.3245H22···C18iv3.4450
H4···H52.3305H22···H11iv3.4705
H5···H82.8167H22···H13iv3.0827
H8···H92.3326H22···H17Biv3.1321
H9···H102.3327H22···H18Aiv2.7350
H10···H112.3325H22···H37Av3.3954
H11···H132.3058H22···H37Cv3.1823
H13···H142.7814H23···O1iv2.7517
H17A···H18A3.5549H23···C13iv3.4922
H17A···H20B2.3387H23···C15iv3.4131
H17A···H20C3.3752H23···C17iv2.9194
H17B···H18A2.4713H23···C24xiv3.5932
H17B···H18B3.5581H23···B1iv3.4196
H17B···H18C2.9835H23···H11iv3.2479
H17B···H20B3.5293H23···H13iv2.8696
H17C···H18A2.9753H23···H17Aiv2.8395
H17C···H18C2.5558H23···H17Biv2.3248
H17C···H20B2.3273H23···H24xiv2.8649
H17C···H20C2.6650H24···N1iii3.3862
H18B···H19A2.3166H24···C13iii2.7911
H18B···H19B3.5070H24···C14iii2.7126
H18B···H19C2.3103H24···C23xiv3.5183
H18C···H19A3.3732H24···B1iii3.1429
H18C···H19C2.6708H24···H11iv3.3524
H18C···H20C2.9358H24···H13iii3.0257
H19A···H20A3.5480H24···H14iii3.0246
H19B···H20A2.4559H24···H17Aiii3.3931
H19B···H20B3.5520H24···H23xiv2.8649
H19B···H20C2.9901H24···H24xiv3.4897
H19C···H20A2.9590H25···O2iii3.2299
H19C···H20C2.5602H25···C14iii3.3856
H22···H232.3440H25···C33iii3.5184
H22···H342.0045H25···B1iii3.4434
H23···H242.3228H25···H10iv3.2265
H24···H252.3380H25···H14iii3.1952
H25···H282.8023H25···H17Aiii3.4855
H28···H292.3329H25···H33iii3.4850
H29···H302.3303H28···C9xi3.3784
H30···H312.3407H28···C34iii3.3559
H31···H332.2260H28···H8xi3.2629
H33···H342.7762H28···H9xi2.6427
H37A···H38A3.5468H28···H18Ax3.5441
H37A···H38B2.4544H28···H34iii3.0271
H37A···H38C2.9837H29···C17viii3.4562
H37A···H40A3.5092H29···C17x3.5597
H37B···H38B3.5410H29···C18x3.2710
H37B···H38C3.5927H29···H8xi3.3817
H37B···H40A2.3124H29···H17Bx2.9741
H37B···H40C3.3416H29···H17Cviii2.5097
H37C···H38A3.5922H29···H17Cx3.4017
H37C···H38B2.9467H29···H18Ax2.6193
H37C···H38C2.5394H29···H18Cviii3.3891
H37C···H40A2.3229H29···H18Cx3.0961
H37C···H40C2.6265H29···H20Cviii3.4322
H38A···H39A3.4490H29···H29xi3.5140
H38A···H39B2.2510H30···C53.4040
H38A···H39C2.2617H30···C63.0763
H38C···H39B3.3096H30···C73.1137
H38C···H39C2.5874H30···C83.4874
H38C···H40C2.8757H30···C17x3.3842
H39A···H40A3.5637H30···H53.5397
H39A···H40B2.4788H30···H83.5972
H39A···H40C2.9976H30···H17Bx2.6374
H39B···H40B3.5624H30···H17Cx3.2977
H39C···H40B2.9623H30···H18Cviii2.7643
H39C···H40C2.5497H31···N13.3851
O1···H22i2.7802H31···C12.7556
O1···H23i2.7517H31···C22.8692
O2···H25iii3.2299H31···C33.1833
O2···H38A2.6201H31···C43.4162
O2···H39B2.8790H31···C53.3778
O3···H22.5567H31···C63.0548
O3···H33.5567H31···H23.2950
O3···H142.6754H33···C23.1050
O4···H3v2.9576H33···C33.3666
O4···H4v3.4571H33···H22.9556
O4···H8vi3.4179H33···H33.3831
N1···H24iii3.3862H33···H143.1980
N1···H313.3851H33···H25iii3.4850
N1···H38Bii3.1651H33···H37Bv3.2274
N1···H38Cii2.6113H33···H40Av3.4549
N2···H37Cv3.3943H34···C18iv3.5729
C1···H19Aii3.5328H34···C28iii3.2475
C1···H312.7556H34···H18Aiv2.7615
C1···H38Bii3.4777H34···H18Biv3.5610
C1···H38Cii3.0690H34···H28iii3.0271
C2···H19Aii3.3037H34···H37Av3.4395
C2···H312.8692H34···H37Bv3.3294
C2···H333.1050H34···H37Cv3.5750
C2···H37A3.2809H37A···C23.2809
C2···H38B3.4697H37A···C33.2319
C3···H18Bii3.4227H37A···C34v3.5331
C3···H19Aii3.0062H37A···H22.7348
C3···H313.1833H37A···H32.6147
C3···H333.3666H37A···H13ii3.1325
C3···H37A3.2319H37A···H22v3.3954
C3···H40Av3.3213H37A···H34v3.4395
C4···H4vii3.5083H37B···C33v3.0667
C4···H5vii3.2378H37B···C34v2.9875
C4···H18Bii3.3475H37B···B2v3.2813
C4···H19Aii2.9686H37B···H33.3418
C4···H19Cviii3.1214H37B···H3v3.4791
C4···H19Cii3.4047H37B···H33v3.2274
C4···H313.4162H37B···H34v3.3294
C4···H40Av3.3780H37B···H37Bv3.2079
C4···H40Bv3.1340H37C···N2v3.3943
C5···H4vii3.1527H37C···C11ii3.4647
C5···H18Bviii3.4101H37C···C21v3.4444
C5···H18Cviii3.2483H37C···C22v3.3871
C5···H19Aii3.2092H37C···C33v3.3930
C5···H19Cviii3.1528H37C···C34v3.5375
C5···H19Cii3.4970H37C···H11ii3.0481
C5···H303.4040H37C···H13ii2.9407
C5···H313.3778H37C···H22v3.1823
C6···H19Aii3.4812H37C···H34v3.5750
C6···H303.0763H38A···O22.6201
C6···H313.0548H38A···C143.2875
C6···H38Cii3.4422H38A···C163.4510
C7···H303.1137H38A···C193.0622
C7···H38Cii3.2615H38A···B13.1009
C7···H39Aix3.4810H38A···H142.9460
C8···H303.4874H38A···H19A2.8762
C8···H39Aix2.8891H38A···H19B2.5937
C9···H17Ax3.4193H38B···N1ii3.1651
C9···H17Cx3.4345H38B···C1ii3.4777
C9···H20Aix3.0849H38B···C23.4697
C9···H28xi3.3784H38B···C13ii3.0944
C9···H39Aix3.3302H38B···C143.1916
C9···H39Bix3.5354H38B···H22.5925
C10···H17Ax3.1239H38B···H13ii3.2048
C10···H20Aix3.1275H38B···H142.7622
C10···H40Cii3.5263H38C···N1ii2.6113
C11···H17Ax3.4394H38C···C1ii3.0690
C11···H37Cii3.4647H38C···C6ii3.4422
C11···H38Cii3.2691H38C···C7ii3.2615
C11···H40Cii3.5352H38C···C11ii3.2691
C12···H38Cii2.7261H38C···C12ii2.7261
C13···H23i3.4922H38C···C13ii3.0653
C13···H24iii2.7911H38C···H11ii3.4828
C13···H38Bii3.0944H38C···H13ii3.0730
C13···H38Cii3.0653H38C···H19B3.4631
C14···H24iii2.7126H39A···C7vi3.4810
C14···H25iii3.3856H39A···C8vi2.8891
C14···H38A3.2875H39A···C9vi3.3302
C14···H38B3.1916H39A···H8vi2.7319
C15···H22i3.5198H39A···H9vi3.4756
C15···H23i3.4131H39A···H19Bxiii3.4666
C16···H38A3.4510H39A···H39Cxiii2.8638
C17···H23i2.9194H39B···O22.8790
C17···H29xii3.4562H39B···C9vi3.5354
C17···H29x3.5597H39B···H8vi3.3861
C17···H30x3.3842H39B···H9vi3.2565
C18···H5xii3.0086H39B···H19B2.9822
C18···H8xii3.3972H39B···H20A2.9115
C18···H22i3.4450H39C···C193.5707
C18···H29x3.2710H39C···C39xiii3.2368
C18···H34i3.5729H39C···H19B2.6398
C19···H4xii3.4437H39C···H20A3.5019
C19···H5xii3.5579H39C···H39Axiii2.8638
C19···H38A3.0622H39C···H39Cxiii2.7173
C19···H39C3.5707H40A···C3v3.3213
C19···H40Bxiii3.0629H40A···C4v3.3780
C20···H9vi3.4233H40A···C33v3.5877
C20···H10vi3.2907H40A···H3v2.9959
C20···H40Cxiii3.5942H40A···H4v3.0916
C21···H11iv3.1201H40A···H33v3.4549
C21···H37Cv3.4444H40B···C4v3.1340
C22···H11iv2.9476H40B···C19xiii3.0629
C22···H13iv3.1563H40B···H3v3.4447
C22···H17Biv3.3821H40B···H4v2.4566
C22···H18Aiv3.5314H40B···H19Bxiii2.5695
C22···H37Cv3.3871H40B···H19Cxiii2.6852
C23···H11iv2.7948H40B···H20Axiii3.3125
C23···H13iv3.0430H40B···H20Cxiii3.4672
C23···H17Biv2.9814H40C···C10ii3.5263
C23···H24xiv3.5183H40C···C11ii3.5352
C24···H11iv2.8600H40C···C20xiii3.5942
C24···H14iii3.5794H40C···H19Bxiii3.2955
C24···H23xiv3.5932H40C···H20Axiii2.9080
C25···H10iv3.2043H40C···H20Cxiii3.4191
C25···H11iv3.0466
C15—O1—B1107.1 (2)C2—C3—H3119.303
C16—O2—B1106.48 (19)C4—C3—H3119.295
C35—O3—B2107.2 (2)C3—C4—H4119.591
C36—O4—B2107.2 (3)C5—C4—H4119.600
C1—N1—C12108.38 (17)C4—C5—H5120.374
C1—N1—C13128.6 (3)C6—C5—H5120.367
C12—N1—C13122.97 (19)C7—C8—H8120.545
C21—N2—C32107.63 (17)C9—C8—H8120.546
C21—N2—C33129.5 (3)C8—C9—H9119.646
C32—N2—C33122.8 (2)C10—C9—H9119.648
N1—C1—C2130.62 (19)C9—C10—H10119.380
N1—C1—C6108.2 (3)C11—C10—H10119.379
C2—C1—C6121.11 (19)C10—C11—H11120.911
C1—C2—C3117.8 (2)C12—C11—H11120.902
C2—C3—C4121.4 (3)N1—C13—H13115.810
C3—C4—C5120.8 (2)C14—C13—H13115.792
C4—C5—C6119.3 (3)C13—C14—H14119.238
C1—C6—C5119.6 (3)B1—C14—H14119.229
C1—C6—C7107.47 (18)C15—C17—H17A109.471
C5—C6—C7133.0 (3)C15—C17—H17B109.472
C6—C7—C8133.36 (19)C15—C17—H17C109.469
C6—C7—C12107.1 (2)H17A—C17—H17B109.473
C8—C7—C12119.5 (3)H17A—C17—H17C109.467
C7—C8—C9118.9 (2)H17B—C17—H17C109.476
C8—C9—C10120.7 (3)C15—C18—H18A109.475
C9—C10—C11121.2 (3)C15—C18—H18B109.472
C10—C11—C12118.19 (19)C15—C18—H18C109.471
N1—C12—C7108.7 (2)H18A—C18—H18B109.464
N1—C12—C11129.82 (18)H18A—C18—H18C109.477
C7—C12—C11121.4 (3)H18B—C18—H18C109.469
N1—C13—C14128.4 (3)C16—C19—H19A109.472
C13—C14—B1121.5 (3)C16—C19—H19B109.469
O1—C15—C16101.87 (17)C16—C19—H19C109.475
O1—C15—C17107.33 (17)H19A—C19—H19B109.473
O1—C15—C18107.9 (2)H19A—C19—H19C109.468
C16—C15—C17112.8 (3)H19B—C19—H19C109.472
C16—C15—C18115.13 (19)C16—C20—H20A109.472
C17—C15—C18111.0 (2)C16—C20—H20B109.472
O2—C16—C15102.30 (17)C16—C20—H20C109.473
O2—C16—C19106.33 (16)H20A—C20—H20B109.472
O2—C16—C20108.41 (19)H20A—C20—H20C109.471
C15—C16—C19113.0 (2)H20B—C20—H20C109.468
C15—C16—C20115.62 (19)C21—C22—H22121.026
C19—C16—C20110.3 (2)C23—C22—H22121.021
N2—C21—C22130.71 (19)C22—C23—H23119.208
N2—C21—C26108.4 (3)C24—C23—H23119.202
C22—C21—C26120.8 (2)C23—C24—H24119.621
C21—C22—C23118.0 (2)C25—C24—H24119.608
C22—C23—C24121.6 (3)C24—C25—H25120.600
C23—C24—C25120.8 (3)C26—C25—H25120.573
C24—C25—C26118.8 (3)C27—C28—H28120.473
C21—C26—C25120.0 (3)C29—C28—H28120.476
C21—C26—C27107.57 (19)C28—C29—H29119.737
C25—C26—C27132.3 (2)C30—C29—H29119.731
C26—C27—C28133.4 (2)C29—C30—H30119.240
C26—C27—C32107.0 (2)C31—C30—H30119.235
C28—C27—C32119.5 (3)C30—C31—H31121.147
C27—C28—C29119.1 (2)C32—C31—H31121.165
C28—C29—C30120.5 (3)N2—C33—H33114.977
C29—C30—C31121.5 (3)C34—C33—H33114.962
C30—C31—C32117.7 (2)C33—C34—H34119.747
N2—C32—C27109.3 (3)B2—C34—H34119.740
N2—C32—C31129.05 (19)C35—C37—H37A109.473
C27—C32—C31121.7 (3)C35—C37—H37B109.468
N2—C33—C34130.1 (3)C35—C37—H37C109.469
C33—C34—B2120.5 (3)H37A—C37—H37B109.473
O3—C35—C36101.98 (18)H37A—C37—H37C109.473
O3—C35—C37106.51 (16)H37B—C37—H37C109.472
O3—C35—C38108.9 (2)C35—C38—H38A109.469
C36—C35—C37114.3 (3)C35—C38—H38B109.474
C36—C35—C38113.89 (18)C35—C38—H38C109.467
C37—C35—C38110.5 (2)H38A—C38—H38B109.471
O4—C36—C35102.74 (19)H38A—C38—H38C109.475
O4—C36—C39106.7 (2)H38B—C38—H38C109.471
O4—C36—C40109.1 (3)C36—C39—H39A109.468
C35—C36—C39113.0 (3)C36—C39—H39B109.474
C35—C36—C40114.0 (3)C36—C39—H39C109.473
C39—C36—C40110.7 (3)H39A—C39—H39B109.465
O1—B1—O2113.12 (17)H39A—C39—H39C109.464
O1—B1—C14124.6 (3)H39B—C39—H39C109.483
O2—B1—C14122.3 (3)C36—C40—H40A109.473
O3—B2—O4112.9 (2)C36—C40—H40B109.468
O3—B2—C34123.1 (3)C36—C40—H40C109.475
O4—B2—C34124.0 (3)H40A—C40—H40B109.469
C1—C2—H2121.107H40A—C40—H40C109.476
C3—C2—H2121.095H40B—C40—H40C109.466
C15—O1—B1—O28.9 (3)C8—C7—C12—N1179.3 (2)
C15—O1—B1—C14169.59 (18)C8—C7—C12—C110.5 (4)
B1—O1—C15—C1623.79 (19)C12—C7—C8—C90.7 (4)
B1—O1—C15—C1794.9 (2)C7—C8—C9—C100.1 (4)
B1—O1—C15—C18145.40 (17)C8—C9—C10—C111.1 (4)
C16—O2—B1—O111.6 (3)C9—C10—C11—C121.3 (4)
C16—O2—B1—C14169.92 (17)C10—C11—C12—N1179.8 (2)
B1—O2—C16—C1525.37 (19)C10—C11—C12—C70.5 (4)
B1—O2—C16—C1993.4 (2)N1—C13—C14—B1177.40 (17)
B1—O2—C16—C20147.99 (17)C13—C14—B1—O15.3 (4)
C35—O3—B2—O410.1 (2)C13—C14—B1—O2173.09 (19)
C35—O3—B2—C34169.04 (17)O1—C15—C16—O229.61 (19)
B2—O3—C35—C3623.38 (17)O1—C15—C16—C1984.30 (16)
B2—O3—C35—C3796.74 (19)O1—C15—C16—C20147.18 (14)
B2—O3—C35—C38144.05 (16)C17—C15—C16—O285.14 (18)
C36—O4—B2—O39.1 (3)C17—C15—C16—C19160.95 (14)
C36—O4—B2—C34171.82 (18)C17—C15—C16—C2032.4 (2)
B2—O4—C36—C3523.0 (2)C18—C15—C16—O2146.09 (17)
B2—O4—C36—C3996.1 (3)C18—C15—C16—C1932.2 (3)
B2—O4—C36—C40144.28 (18)C18—C15—C16—C2096.3 (2)
C1—N1—C12—C71.7 (3)N2—C21—C22—C23178.07 (16)
C1—N1—C12—C11178.5 (2)N2—C21—C26—C25179.51 (14)
C12—N1—C1—C2176.8 (2)N2—C21—C26—C271.52 (19)
C12—N1—C1—C61.4 (3)C22—C21—C26—C252.2 (3)
C1—N1—C13—C1419.3 (4)C22—C21—C26—C27175.78 (15)
C13—N1—C1—C23.7 (4)C26—C21—C22—C231.4 (3)
C13—N1—C1—C6178.07 (18)C21—C22—C23—C240.1 (3)
C12—N1—C13—C14160.09 (19)C22—C23—C24—C251.0 (3)
C13—N1—C12—C7177.80 (17)C23—C24—C25—C260.2 (3)
C13—N1—C12—C112.0 (4)C24—C25—C26—C211.3 (3)
C21—N2—C32—C272.11 (19)C24—C25—C26—C27176.06 (18)
C21—N2—C32—C31177.67 (16)C21—C26—C27—C28178.48 (17)
C32—N2—C21—C22174.71 (16)C21—C26—C27—C320.22 (19)
C32—N2—C21—C262.23 (18)C25—C26—C27—C280.8 (4)
C21—N2—C33—C346.8 (4)C25—C26—C27—C32177.86 (19)
C33—N2—C21—C228.4 (3)C26—C27—C28—C29178.42 (18)
C33—N2—C21—C26174.70 (16)C26—C27—C32—N21.2 (2)
C32—N2—C33—C34169.73 (17)C26—C27—C32—C31178.64 (15)
C33—N2—C32—C27175.07 (14)C28—C27—C32—N2179.92 (16)
C33—N2—C32—C315.1 (3)C28—C27—C32—C310.3 (3)
N1—C1—C2—C3179.6 (2)C32—C27—C28—C290.1 (3)
N1—C1—C6—C5179.67 (17)C27—C28—C29—C300.4 (3)
N1—C1—C6—C70.6 (3)C28—C29—C30—C310.8 (3)
C2—C1—C6—C51.9 (4)C29—C30—C31—C320.7 (3)
C2—C1—C6—C7177.86 (19)C30—C31—C32—N2179.62 (17)
C6—C1—C2—C32.3 (4)C30—C31—C32—C270.1 (3)
C1—C2—C3—C40.9 (4)N2—C33—C34—B2176.99 (17)
C2—C3—C4—C50.9 (4)C33—C34—B2—O39.9 (3)
C3—C4—C5—C61.4 (4)C33—C34—B2—O4169.14 (19)
C4—C5—C6—C10.0 (4)O3—C35—C36—O427.75 (19)
C4—C5—C6—C7179.7 (2)O3—C35—C36—C3986.81 (19)
C1—C6—C7—C8179.7 (3)O3—C35—C36—C40145.62 (15)
C1—C6—C7—C120.5 (3)C37—C35—C36—O486.7 (2)
C5—C6—C7—C80.0 (5)C37—C35—C36—C39158.70 (17)
C5—C6—C7—C12179.2 (3)C37—C35—C36—C4031.1 (3)
C6—C7—C8—C9178.5 (3)C38—C35—C36—O4144.85 (17)
C6—C7—C12—N11.4 (3)C38—C35—C36—C3930.3 (3)
C6—C7—C12—C11178.84 (18)C38—C35—C36—C4097.3 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+2, z; (iii) x+1, y+2, z+1; (iv) x1, y, z; (v) x+1, y+2, z; (vi) x, y1, z; (vii) x+1, y+3, z; (viii) x1, y+1, z; (ix) x, y+1, z; (x) x+2, y+2, z+1; (xi) x+1, y+3, z+1; (xii) x+1, y1, z; (xiii) x+2, y+1, z; (xiv) x, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC20H22BNO2
Mr319.21
Crystal system, space groupTriclinic, P1
Temperature (K)93
a, b, c (Å)11.616 (3), 12.962 (3), 12.990 (3)
α, β, γ (°)83.620 (11), 85.632 (11), 64.647 (6)
V3)1755.6 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.19 × 0.07 × 0.03
Data collection
DiffractometerRigaku Saturn724+
diffractometer
Absorption correctionNumerical
(NUMABS; Rigaku, 1999)
Tmin, Tmax0.990, 0.998
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
12732, 6408, 4117
Rint0.035
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.137, 1.01
No. of reflections6406
No. of parameters433
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.22

Computer programs: CrystalClear (Rigaku, 2008), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku, 2010).

Selected bond lengths (Å) top
O1—C151.466 (3)N1—C131.396 (3)
O1—B11.373 (4)N2—C331.392 (3)
O2—B11.376 (4)C13—C141.336 (4)
O3—C351.474 (3)C33—C341.334 (4)
O3—B21.374 (4)
 

Acknowledgements

This work was supported by Research for Promoting Technological Seeds from Japan Science and Technology Agency (JST).

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
First citationClark, J. S., Freeman, R. P., Cacho, M., Thomas, A. W., Swallow, S. & Wilson, C. (2004). Tetrahedron Lett. 45, 8639–8642.  Web of Science CSD CrossRef CAS Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationGeier, M. J., Vogels, C. M., Decken, A. & Westcott, S. A. (2009). J. Organomet. Chem. 694, 3154–3159.  Web of Science CSD CrossRef CAS Google Scholar
First citationRigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTian, X., Shi, W., Shen, K., Li, C., Lin, J., Che, Y. & Zhang, P. (2006). J. Organomet. Chem. 691, 994–1006.  Web of Science CSD CrossRef CAS Google Scholar
First citationTsutsui, K., Hirotsu, K., Umesaki, M., Kurahashi, M., Shimada, A. & Higuchi, T. (1976). Acta Cryst. B32, 3049–3053.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds