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1,2-Bis­[2,2-di­phenyl-4-(2-propyl)-1,3-dioxa-4-azonia-2-borata­­cyclo-4-pentyl]­ethane, C34H42B2N2O4, crystallizes with the mol­ecules lying on crystallographic inversion centres. The five-membered COBON ring has a half-chair conformation, with about 25% double-bond character for the C-O bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802005391/cf6158sup1.cif
Contains datablocks wk147A5, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802005391/cf61583sup2.hkl
Contains datablock 3

CCDC reference: 185765

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.051
  • Data-to-parameter ratio = 10.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 77.40 From the CIF: _reflns_number_total 2975 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3455 Completeness (_total/calc) 86.11% Alert B: < 90% complete (theta max?)
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Comment top

From the reaction of substituted ethylenebishydroxylamines and organoboron compounds, some different types of boron complexes have been obtained and structurally established by X-ray crystallography (Amt et al., 1988, 1990a,b). In the course of these investigations, the reaction of a series of N,N'-dialkylethylenebishydroxylamines, (2) [which can be synthesized by reduction of glyoxalbisnitrones, (1)], with formaldehyde and diphenylborinic acid (anhydride) resulted in the incorporation of two molecules each of formaldehyde and diphenylborinic acid into (2) (Amt, 1990). The elemental analyses and 1H NMR spectra of the crystalline compounds are consistent with at least three symmetrical structural alternatives, two ethylene-linked five-membered diphenylboron chelates, (3) and (4), and an eight-membered bicyclic product (5). Since spectroscopic data were not sufficient for distinction among the isomeric structures, an X-ray analysis of the N,N'-diisopropyl derivative, which gave the best single crystals in the series of homologous compounds, was carried out.

The structure analysis establishes the molecular constitution (3) (R = 2-C3H7), generated by an electrophilic attack of formaldehyde at the hydroxylamine N atom and subsequent (or simultaneous) chelate formation with diphenylborinic acid. Analogous COBON chelate ring systems have been found in the diphenylboron complexes of the reaction products from N,N-dimethylhydroxylamine and formaldehyde (Rettig et al., 1974) or acetone (Kliegel et al., 1984), acetone oxime and formaldehyde (Kliegel et al., 1995), and also, as part of a polycyclic ring system, from phenylboronic acid, N-hydroxypiperidine and salicyladehyde (Kliegel et al., 1990).

The molecule of (3) (Fig. 1) lies on a crystallographic inversion centre. The five-membered ring has a half-chair conformation, with C1 and O2 lying on opposite sides of the B—O1—N plane. The dihedral angles in the ring are almost identical with those in compounds with the same ring system studied previously (e.g. Rettig et al., 1974).

Bond lengths and angles are also close to those in related molecules. The C1—O2 bond in the COBON ring [1.360 (2) Å] has considerable double-bond character (about 25%) (retained from the carbonyl moiety of the formaldehyde from which it derives); this results from back donation from oxygen to carbon The calculated bond order (Paolini, 1990) is 1.24, while that estimated from a bond-length versus bond-order plot (Häfelinger, 1970) is 1.27. This double-bond character in the C1—O2 bond of (3) is slightly greater than those of the corresponding C—O bonds in the COBON rings of the other compounds reported: 1.378 Å (Rettig et al., 1974) 1.387 Å (Kliegel et al., 1984), 1.380 Å (Kliegel et al., 1995), and 1.382 Å (Kliegel et al., 1990). In spite of the partially retained carbonyl π-bond, all these compounds exhibit shorter (stronger) B—O(C) bonds and longer (weaker) B—O(N) bonds, the differences ranging from 0.03 to 0.08 Å [for (3), B–O2(C1) = 1.487 (3) Å and B—O1(N) = 1.555 (2) Å].

Experimental top

For the preparation of N N'-ethanediylidenebis(2-propanamine) N,N'-dioxide, (1) (R = 2-C3H7), N-(2-propyl)hydroxylamine (2.25 g, 30 mmol) and glyoxal (0.87 g, 15 mmol, applied as hydrate) were heated in 50 ml of ethanol under reflux conditions for 15 min. After evaporating the solution to one-third of its initial volume, the solution was cooled and yielded 1.62 g (63%) of colourless needles, m.p. 479 K (decomposition) (from ethanol). IR (KBr): 1520 cm-1 (CN). 1H NMR (90 MHz, CDCl3/TMS), δ (p.p.m.): 1.45 (d, J = 6 Hz, 4 CH3), 4.12 (m, J = 6 Hz, 2 N—CH), 7.80 (s, 2 NCH). Analysis calculated for C8H16N2O2: C 55.79, H 9.36, N 16.27%; found: C 55.89, H 9.58, N 16.26%.

For the preparation of N,N'-dihydroxy-N,N'-di(2-propyl)ethylenediamine, (2) (R = 2-C3H7), (1) (R = 2-C3H7) (3.44 g, 20 mmol) was dissolved in 100 ml of methanol/water (1:1). A solution of KBH4 (2.16 g, 40 mmol) in 15 ml water was added. After storing for 24 h at room temperature, the solution was acidified with tartaric acid (20% aqueous solution) and subsequently neutralized with NaHCO3. After evaporation in vacuo, the dry residue was mixed with 50 ml of water and extracted with 3 × 40 ml of chloroform. The combined organic phases were evaporated in vacuo, and the residue recrystallized from chloroform/petroleum ether. Yield: 2.39 g (68%), m.p. 354 K. IR (KBr): 3660–2560 cm-1 (broad curtain, O—H). 1H NMR (90 MHz, DMSO-d6/TMS), δ (p.p.m.): 0.98 (d, J = 6 Hz, 4 CH3), 2.72–2.76 (m, 2 N—CH, CH2CH2), 7.28 (s, broad, exchangeable, 2 OH). Analysis calculated for C8H20N2O2: C 54.51, H 11.44, N 15.89%; found: C 54.63, H 11.70,N 15.80%.

For the preparation of 1,2-bis[2,2-diphenyl-4-(2-propyl)-1,3-dioxa-4-azonia-2- boratacyclo-4-pentyl]ethane, (3) (R = 2-C3H7), (2) (R = 2-C3H7) (0.35 g, 2 mmol) and formaldehyde (0.3 ml of 40% aqueous solution, 4 mmol) were dissolved in 20 ml of ethanol at room temperature under stirring. To the clear solution. oxybis(diphenylborane) (0.69 g, 2 mmol) in 10 ml of ethanol was added and stirring continued until crystallization began. After cooling to 255 K, the crystals were collected and washed with cold ethanol and subsequently with ether. Yield: 0.88 g (79%) of colourless, analytically pure crystals, m.p. 458–459 K (decomposition). 1H NMR (90 MHz, DMSO-d6/TMS), δ (p.p.m.): 0.75 (d, J = 6 Hz, 2 CH3), 1.12 (d, J = 6 Hz, 2 CH3), 3.10–3.72 (m, 2 N—CH, CH2CH2), 4.61 and 5.00 (d and d, AB-system, J = 5 Hz, 2 N—CH2—O), 6.84–7.43 (m, 20 aromatic H). Analysis calculated for C34H42B2N2O4: C 72.62, H 7.53, N 4.98%; found: C 72.56, H 7.61, N 4.99%. The compound gave a blue colour reaction with diphenylcarbazone in methanolic solution, indicating the presence of a diphenylboron moiety (Neu, 1960; Friese & Umland, 1978). Crystals suitable for X-ray crystallography were obtained by slow crystallization from nitroethane.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: MITHRIL (Gilmore, 1984); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (3) (33% probability ellipsoids).
(3) top
Crystal data top
C34H42B2N2O4F(000) = 604
Mr = 564.34Dx = 1.152 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 10.5826 (9) ÅCell parameters from 25 reflections
b = 11.6428 (6) Åθ = 38.4–44.0°
c = 13.3394 (6) ŵ = 0.58 mm1
β = 98.164 (5)°T = 294 K
V = 1626.9 (2) Å3Rhomb, colourless
Z = 20.38 × 0.30 × 0.20 mm
Data collection top
Rigaku AFC-6S
diffractometer
2082 reflections with I > 3σ(I)
Radiation source: X-ray tubeRint = 0.022
Graphite monochromatorθmax = 77.4°, θmin = 0.0°
ω–2θ scansh = 013
Absorption correction: ψ scan
(AFC6; Molecular Structure Corporation, 1989)
k = 014
Tmin = 0.80, Tmax = 0.89l = 1516
3295 measured reflections3 standard reflections every 300 reflections
2975 independent reflections intensity decay: 0.0%
Refinement top
Refinement on F0 constraints
Least-squares matrix: fullH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.038Weighting scheme based on measured s.u.'s 1/[σ2(Fo) + 0.02Fo2]
wR(F2) = 0.051(Δ/σ)max = 0.01
S = 1.79Δρmax = 0.17 e Å3
2082 reflectionsΔρmin = 0.14 e Å3
191 parametersExtinction correction: Molecular Structure Corporation (1989), equ(3) Acta Cryst. (1968), A24, 213
0 restraintsExtinction coefficient: 5.74E-6 (3)
Crystal data top
C34H42B2N2O4V = 1626.9 (2) Å3
Mr = 564.34Z = 2
Monoclinic, P21/nCu Kα radiation
a = 10.5826 (9) ŵ = 0.58 mm1
b = 11.6428 (6) ÅT = 294 K
c = 13.3394 (6) Å0.38 × 0.30 × 0.20 mm
β = 98.164 (5)°
Data collection top
Rigaku AFC-6S
diffractometer
2082 reflections with I > 3σ(I)
Absorption correction: ψ scan
(AFC6; Molecular Structure Corporation, 1989)
Rint = 0.022
Tmin = 0.80, Tmax = 0.893 standard reflections every 300 reflections
3295 measured reflections intensity decay: 0.0%
2975 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.051H-atom parameters not refined
S = 1.79Δρmax = 0.17 e Å3
2082 reflectionsΔρmin = 0.14 e Å3
191 parameters
Special details top

Experimental. The scan width was (1.10 + 0.20tanθ)° with an ω scan speed of 32° per minute (up to 10 scans to achieve I/σ(I) > 40). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. Three standard reflections remained constant in intensity for about 80% of the data collection, but decreased gradually in intensity by about 15% in the last 20% of the measurements; a linear decay correction was applied to the latter data.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5723 (1)0.6146 (1)0.65669 (8)0.0415 (6)
O20.7292 (1)0.4748 (1)0.64301 (9)0.0434 (6)
N0.5145 (1)0.5047 (1)0.6445 (1)0.0393 (7)
C10.6267 (2)0.4207 (1)0.6726 (1)0.0448 (9)
C20.4520 (2)0.4939 (1)0.5365 (1)0.0494 (9)
C30.4188 (2)0.4946 (2)0.7193 (1)0.054 (1)
C40.3148 (2)0.5841 (2)0.7001 (2)0.072 (1)
C50.3668 (2)0.3730 (2)0.7223 (2)0.077 (1)
C60.7845 (2)0.6784 (1)0.5981 (1)0.0424 (9)
C70.7566 (2)0.7946 (2)0.5888 (1)0.049 (1)
C80.8189 (2)0.8673 (2)0.5296 (2)0.062 (1)
C90.9117 (2)0.8244 (2)0.4781 (2)0.073 (1)
C100.9404 (2)0.7087 (2)0.4840 (2)0.076 (1)
C110.8776 (2)0.6377 (2)0.5436 (2)0.061 (1)
C120.7766 (2)0.6204 (1)0.7903 (1)0.0412 (9)
C130.9039 (2)0.5927 (2)0.8241 (1)0.056 (1)
C140.9601 (2)0.6149 (2)0.9224 (2)0.067 (1)
C150.8908 (2)0.6645 (2)0.9903 (2)0.067 (1)
C160.7656 (2)0.6927 (2)0.9599 (1)0.061 (1)
C170.7098 (2)0.6714 (2)0.8604 (1)0.049 (1)
B0.7195 (2)0.5972 (2)0.6728 (1)0.0394 (9)
H10.61020.34770.63650.053*
H20.64080.40630.74570.053*
H30.41130.41830.52700.053*
H40.38720.55400.52230.053*
H50.46570.51040.78660.063*
H60.25990.56680.63630.086*
H70.26370.58340.75580.086*
H80.35340.66010.69560.086*
H90.43800.31870.73470.092*
H100.31480.35520.65740.092*
H110.31410.36690.77690.092*
H120.69040.82640.62530.058*
H130.79670.94900.52470.075*
H140.95750.87550.43730.089*
H151.00510.67710.44590.091*
H160.89960.55580.54760.072*
H170.95500.55660.77690.067*
H181.04990.59500.94350.081*
H190.93060.67971.05990.080*
H200.71520.72781.00800.072*
H210.62050.69330.83960.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0390 (6)0.0350 (6)0.0472 (7)0.0016 (5)0.0053 (5)0.0056 (5)
O20.0427 (6)0.0379 (6)0.0469 (7)0.0012 (5)0.0027 (5)0.0053 (5)
N0.0424 (8)0.0383 (8)0.0344 (7)0.0048 (6)0.0035 (6)0.0018 (6)
C10.052 (1)0.037 (1)0.043 (1)0.0018 (8)0.0041 (8)0.0003 (7)
C20.044 (1)0.054 (1)0.0320 (8)0.0088 (8)0.0053 (7)0.0034 (8)
C30.055 (1)0.064 (1)0.038 (1)0.005 (1)0.0069 (8)0.0002 (9)
C40.059 (1)0.095 (2)0.065 (1)0.010 (1)0.018 (1)0.000 (1)
C50.083 (2)0.081 (2)0.071 (2)0.025 (1)0.022 (1)0.011 (1)
C60.041 (1)0.045 (1)0.0387 (9)0.0014 (7)0.0056 (7)0.0031 (7)
C70.049 (1)0.049 (1)0.047 (1)0.0027 (8)0.0014 (8)0.0013 (8)
C80.067 (1)0.053 (1)0.065 (1)0.004 (1)0.000 (1)0.014 (1)
C90.074 (2)0.077 (2)0.072 (2)0.010 (1)0.018 (1)0.018 (1)
C100.073 (1)0.079 (2)0.084 (2)0.001 (1)0.035 (1)0.001 (1)
C110.061 (1)0.053 (1)0.069 (1)0.001 (1)0.019 (1)0.001 (1)
C120.044 (1)0.0353 (9)0.0406 (9)0.0050 (7)0.0058 (7)0.0015 (7)
C130.051 (1)0.053 (1)0.057 (1)0.006 (1)0.0128 (9)0.0034 (9)
C140.067 (1)0.060 (1)0.065 (1)0.005 (1)0.029 (1)0.001 (1)
C150.089 (2)0.054 (1)0.047 (1)0.007 (1)0.023 (1)0.000 (1)
C160.077 (1)0.059 (1)0.042 (1)0.012 (1)0.000 (1)0.006 (1)
C170.051 (1)0.050 (1)0.043 (1)0.0068 (9)0.0028 (8)0.0044 (8)
B0.037 (1)0.037 (1)0.041 (1)0.0021 (8)0.0039 (8)0.0053 (8)
Geometric parameters (Å, º) top
O1—N1.418 (2)C6—B1.598 (2)
O1—B1.555 (2)C7—C81.387 (3)
O2—C11.360 (2)C7—H120.98
O2—B1.487 (3)C8—C91.370 (4)
N—C11.543 (2)C8—H130.98
N—C21.503 (2)C9—C101.381 (3)
N—C31.524 (2)C9—H140.98
C1—H10.98C10—C111.381 (4)
C1—H20.98C10—H150.98
C2—C2i1.510 (4)C11—H160.98
C2—H30.98C12—C131.396 (3)
C2—H40.98C12—C171.384 (3)
C3—C41.511 (3)C12—B1.620 (2)
C3—C51.521 (3)C13—C141.385 (3)
C3—H50.98C13—H170.98
C4—H60.98C14—C151.371 (4)
C4—H70.98C14—H180.98
C4—H80.98C15—C161.369 (3)
C5—H90.98C15—H190.98
C5—H100.98C16—C171.396 (2)
C5—H110.98C16—H200.98
C6—C71.387 (3)C17—H210.98
C6—C111.388 (3)
O2···C16ii3.563 (2)C1···C16ii3.470 (3)
O2···C17ii3.592 (3)C1···C7ii3.563 (2)
C1···C17ii3.439 (3)C14···C14iii3.415 (5)
N—O1—B107.8 (1)C11—C6—B121.7 (2)
C1—O2—B106.1 (1)C6—C7—C8122.3 (2)
O1—N—C1103.9 (1)C6—C7—H12118.8
O1—N—C2108.0 (1)C8—C7—H12118.9
O1—N—C3108.1 (1)C7—C8—C9119.7 (2)
C1—N—C2113.5 (1)C7—C8—H13120.1
C1—N—C3110.6 (1)C9—C8—H13120.2
C2—N—C3112.2 (1)C8—C9—C10119.6 (2)
O2—C1—N104.7 (1)C8—C9—H14120.2
O2—C1—H1110.7C10—C9—H14120.1
O2—C1—H2110.7C9—C10—C11119.8 (2)
N—C1—H1110.7C9—C10—H15120.0
N—C1—H2110.7C11—C10—H15120.2
H1—C1—H2109.4C6—C11—C10122.2 (2)
N—C2—C2i111.4 (2)C6—C11—H16118.9
N—C2—H3108.9C10—C11—H16118.9
N—C2—H4109.1C13—C12—C17116.3 (1)
C2i—C2—H3108.9C13—C12—B118.9 (2)
C2i—C2—H4109.0C17—C12—B124.7 (2)
H3—C2—H4109.5C12—C13—C14121.8 (2)
N—C3—C4111.8 (2)C12—C13—H17119.1
N—C3—C5111.4 (2)C14—C13—H17119.1
N—C3—H5106.8C13—C14—C15120.4 (2)
C4—C3—C5112.9 (2)C13—C14—H18119.8
C4—C3—H5106.7C15—C14—H18119.8
C5—C3—H5106.8C14—C15—C16119.4 (2)
C3—C4—H6109.4C14—C15—H19120.3
C3—C4—H7109.5C16—C15—H19120.3
C3—C4—H8109.5C15—C16—C17120.0 (2)
H6—C4—H7109.5C15—C16—H20120.0
H6—C4—H8109.4C17—C16—H20120.0
H7—C4—H8109.5C12—C17—C16122.1 (2)
C3—C5—H9109.4C12—C17—H21119.0
C3—C5—H10109.5C16—C17—H21118.9
C3—C5—H11109.4O1—B—O2101.2 (1)
H9—C5—H10109.6O1—B—C6110.4 (1)
H9—C5—H11109.4O1—B—C12109.9 (1)
H10—C5—H11109.5O2—B—C6110.4 (1)
C7—C6—C11116.4 (2)O2—B—C12112.8 (1)
C7—C6—B121.9 (2)C6—B—C12111.7 (1)
O1—N—C1—O232.2 (1)C2—N—O1—B110.9 (1)
O1—N—C2—C2i60.0 (2)C2—N—C3—C457.9 (2)
O1—N—C3—C461.1 (2)C2—N—C3—C569.4 (2)
O1—N—C3—C5171.5 (1)C2—C2i—Ni—C3i179.1 (1)
O1—B—O2—C134.4 (1)C3—N—O1—B127.4 (1)
O1—B—C6—C749.3 (2)C6—C7—C8—C90.1 (3)
O1—B—C6—C11134.7 (2)C6—C11—C10—C90.5 (3)
O1—B—C12—C13170.5 (2)C6—B—C12—C1366.7 (2)
O1—B—C12—C1712.7 (2)C6—B—C12—C17110.2 (2)
O2—C1—N—C284.8 (1)C7—C6—C11—C100.6 (3)
O2—C1—N—C3148.0 (1)C7—C6—B—C1273.4 (2)
O2—B—O1—N13.1 (1)C7—C8—C9—C101.3 (3)
O2—B—C6—C7160.3 (1)C8—C7—C6—C110.8 (3)
O2—B—C6—C1123.7 (2)C8—C7—C6—B175.4 (2)
O2—B—C12—C1358.4 (2)C8—C9—C10—C111.5 (3)
O2—B—C12—C17124.8 (2)C10—C11—C6—B175.7 (2)
N—O1—B—C6129.9 (1)C11—C6—B—C12102.7 (2)
N—O1—B—C12106.4 (1)C12—C13—C14—C150.6 (3)
N—C1—O2—B41.8 (1)C12—C17—C16—C151.0 (3)
N—C2—C2i—Ni180.0000C13—C12—C17—C160.9 (3)
C1—O2—B—C6151.2 (1)C13—C14—C15—C160.5 (4)
C1—O2—B—C1283.0 (2)C14—C13—C12—C170.1 (3)
C1—N—O1—B9.9 (1)C14—C13—C12—B177.2 (2)
C1—N—C2—C2i54.6 (2)C14—C15—C16—C170.3 (3)
C1—N—C3—C4174.2 (1)C16—C17—C12—B177.8 (2)
C1—N—C3—C558.4 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+3/2, y1/2, z+3/2; (iii) x+2, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC34H42B2N2O4
Mr564.34
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)10.5826 (9), 11.6428 (6), 13.3394 (6)
β (°) 98.164 (5)
V3)1626.9 (2)
Z2
Radiation typeCu Kα
µ (mm1)0.58
Crystal size (mm)0.38 × 0.30 × 0.20
Data collection
DiffractometerRigaku AFC-6S
diffractometer
Absorption correctionψ scan
(AFC6; Molecular Structure Corporation, 1989)
Tmin, Tmax0.80, 0.89
No. of measured, independent and
observed [I > 3σ(I)] reflections
3295, 2975, 2082
Rint0.022
(sin θ/λ)max1)0.633
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.051, 1.79
No. of reflections2082
No. of parameters191
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.17, 0.14

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1989), MITHRIL (Gilmore, 1984), TEXSAN.

Selected geometric parameters (Å, º) top
O1—N1.418 (2)C6—B1.598 (2)
O1—B1.555 (2)C7—C81.387 (3)
O2—C11.360 (2)C8—C91.370 (4)
O2—B1.487 (3)C9—C101.381 (3)
N—C11.543 (2)C10—C111.381 (4)
N—C21.503 (2)C12—C131.396 (3)
N—C31.524 (2)C12—C171.384 (3)
C2—C2i1.510 (4)C12—B1.620 (2)
C3—C41.511 (3)C13—C141.385 (3)
C3—C51.521 (3)C14—C151.371 (4)
C6—C71.387 (3)C15—C161.369 (3)
C6—C111.388 (3)C16—C171.396 (2)
N—O1—B107.8 (1)C8—C9—C10119.6 (2)
C1—O2—B106.1 (1)C9—C10—C11119.8 (2)
O1—N—C1103.9 (1)C6—C11—C10122.2 (2)
O1—N—C2108.0 (1)C13—C12—C17116.3 (1)
O1—N—C3108.1 (1)C13—C12—B118.9 (2)
C1—N—C2113.5 (1)C17—C12—B124.7 (2)
C1—N—C3110.6 (1)C12—C13—C14121.8 (2)
C2—N—C3112.2 (1)C13—C14—C15120.4 (2)
O2—C1—N104.7 (1)C14—C15—C16119.4 (2)
N—C2—C2i111.4 (2)C15—C16—C17120.0 (2)
N—C3—C4111.8 (2)C12—C17—C16122.1 (2)
N—C3—C5111.4 (2)O1—B—O2101.2 (1)
C4—C3—C5112.9 (2)O1—B—C6110.4 (1)
C7—C6—C11116.4 (2)O1—B—C12109.9 (1)
C7—C6—B121.9 (2)O2—B—C6110.4 (1)
C11—C6—B121.7 (2)O2—B—C12112.8 (1)
C6—C7—C8122.3 (2)C6—B—C12111.7 (1)
C7—C8—C9119.7 (2)
Symmetry code: (i) x+1, y+1, z+1.
 

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