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4-[(2-Hydro­xy-1-naphthyl)­methyl]-2,2,5-tri­phenyl-1,3-dioxa-4-azonia-2-borata­cyclo­pent-4-ene ethanol solvate, C30H24­B­NO3·­C2H6O, contains a five-membered O-B-O-N=C ring, which is nearly planar (slight B-envelope).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018037/cf6117sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018037/cf6117Isup2.hkl
Contains datablock I

CCDC reference: 176042

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • H-atom completeness 95%
  • Disorder in solvent or counterion
  • R factor = 0.040
  • wR factor = 0.038
  • Data-to-parameter ratio = 10.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
PLAT_420 Alert B D-H Without Acceptor >O(4) - >H(30) ?
Author response: The OH group of the disordered ethanol solvent does not appear to act as a hydrogen bond donor (it does act as an acceptor).

Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 43.00 Perc. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C32 H30 B1 N1 O4 Atom count from the _atom_site data: C32 H28.3 B1 N1 O4 CELLZ_01 From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C32 H30 B N O4 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 64.00 64.00 0.00 H 60.00 56.60 3.40 B 2.00 2.00 0.00 N 2.00 2.00 0.00 O 8.00 8.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The synthesis of the hydroxamic acid (I) by monoacylation of the corresponding hydroxylaminomethylnaphthol (Runti & Collino, 1959; Möhrle et al., 1977; Möhrle & Lappenberg, 1978) has not been reported so far, but is now accomplished by application of 2,4,6-trimethylpyridine (2,4,6-collidine) as a sterically hindered base, a method which has been effectively used for monoacylation of mixed diols (Ishihara et al., 1993). Proof of the N-monoacylation of (I) with benzoyl chloride could be furnished by diphenylboron chelate formation of the bidentate hydroxamate ligand moiety. The X-ray analysis establishes the postulated chelate structure (II) and excludes other possible chelate rings involving the phenolic hydroxyl group or formed by one of the possible isomeric O-benzoyl derivatives of (I).

The molecule of (II)·EtOH contains a five-membered O—B—O—NC ring, which is nearly planar [slight B-envelope, with dihedral angles with magnitudes in the range 0.2 to 3.5 (2)°], similar to the geometry in related substances (Rettig et al., 1977, 1978; Kliegel et al., 1983, 1990, 1996; Kliegel, Schumacher et al., 1991; Kliegel, Tajerbashi et al., 1991). The short C—N bond [1.301 (2) Å] indicates that the most important canonical structure is that shown in the chemical diagram, with a CN double bond, with perhaps a minor contribution from the resonance structure with a CO double bond [C—O = 1.294 (2) Å]. The molecule is linked to the disordered ethanol solvent by an O2—H1···O4 (major component) hydrogen bond, O···O = 2.632 (2), H···O = 1.82 (3) Å and O—H···O = 164 (4)°; the ethanol O4—H group does not appear to act as a hydrogen-bond donor. There are also three possibly significant intramolecular C—H···O interactions (Fig. 1), C···O = 2.73–3.10 and H···O = 2.30–2.51 Å.

Experimental top

1-[(N-Benzoyl-N-hydroxyamino)methyl]-2-naphthol (I): 1-[(N-hydroxyamino)methyl]-2-naphthol hydrochloride (Möhrle et al., 1977) (2.26 g, 10 mmol) was suspended in 50 ml of dichloromethane. After addition of 2,4,6-trimethylpyridine (3.64 g, 30 mmol), benzoyl chloride (1.41 g, 10 mmol) was added dropwise under stirring. After 3 h at room temperature, the clear solution was poured into 60 ml of 1 M HCl. At the interface of the solution phases, crystals were formed, which were separated and recrystallized from ethanol/H2O. Yield: 1.70 g (58%) of colorless needles, m.p. 425 K. IR (KBr): 3305–3052 (O—H), 1599 cm-1 (CO/CC). 1H NMR (90 MHz, DMSO-d6-TMS), δ (p.p.m.): 5.36 (s, CH2), 7.20–7.93 (m, 10 aromatic H), 8.16 (d, J = 8 Hz, 1 aromatic H), 9.96 (s, broad, exchangeable, 2 OH). Analysis calculated for C18H15NO3: C 73.71, H 5.15, N 4.78%; found C 73.73, H 5.13, N 4.69%. The compound gives a violet color reaction with FeCl3, indicating the hydroxamic acid function.

4-[(2-Hydroxy-1-naphthyl)methyl]-2,2,5-triphenyl-1,3-dioxa-4-azonia-2- boratacyclopenten-4-ene, (II), ethanol solvate: (I) (0.29 g, 1 mmol) and oxybis(diphenylborane) (0.17 g, 0.5 mmol) were dissolved in 5 ml of ethanol. Cooling yielded 0.37 g (73%) of colorless crystals, m.p. 398 K (from ethanol). IR (KBr): 3528 (O—H), 1632 cm-1 (C=N). 1H NMR (90 MHz, CDCl3—TMS), δ (p.p.m.): 1.20 (t, J = 7 Hz, CH3), 1.50 (s, broad, exchangeable, OH), 3.65 (q, J = 7 Hz, OCH2), 5.52 (s, NCH2), 7.00–7.86 (m, 21 aromatic H). 11B NMR (64 MHz, CDCl3—Et2OBF3), δ (p.p.m.): 14.1 (w1/2 = 428 Hz), 45.3 (w1/2 = 214 Hz): ratio of peak areas 20:1 [the main peak at 14.1 p.p.m. indicates the tetracoordinate boron nucleus in (II), whereas the small signal at 45.3 p.p.m. points to a trigonal Ph2BO moiety, probably arising from partial solvolysis (Kliegel et al., 2000, and references therein)]. EI mass spectrum (70 eV, 498 K), m/z: 457 (63%, M+ - C2H5OH), 380 (22%, M+ - C2H5OH - C6H5), 312 (100%, [PhBO]3). Analysis calculated for C30H24BNO3·C2H5OH: C 76.35, H 6.01, B 2.15, N 2.78%; found: C 75.98, H 5.93, B 2.13, N 2.71%. The compound gives a blue color 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 ethanol.

Refinement top

The ethanol molecule is disordered; the O and β-C atoms were modelled as twofold disordered and the α-C atom as threefold disordered. The low-occupancy ethanol-C atoms (C31a and C31b) and the naphthyl hydroxy-H atom (H1) were refined isotropically; other non-H atoms were refined anisotropically and the other H atoms were fixed in idealized sites (minor component H atoms were not included).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1995); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1992–1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. View of the structure of (II)·EtOH with 50% probability ellipsoids.
(I) top
Crystal data top
C30H24BNO3·C2H6OZ = 2
Mr = 503.40F(000) = 532
Triclinic, P1Dx = 1.234 Mg m3
a = 11.5792 (6) ÅCu Kα radiation, λ = 1.5418 Å
b = 13.0972 (8) ÅCell parameters from 25 reflections
c = 9.0779 (5) Åθ = 43.8–54.4°
α = 96.780 (5)°µ = 0.64 mm1
β = 93.245 (4)°T = 294 K
γ = 82.833 (4)°Prism, colorless
V = 1355.18 (13) Å30.35 × 0.35 × 0.25 mm
Data collection top
Rigaku AFC-6S
diffractometer
3873 reflections with I > 3σ(I)
Radiation source: X-ray tubeRint = 0.014
Graphite monochromatorθmax = 77.5°, θmin = 3.4°
ω–2θ scansh = 014
Absorption correction: ψ scan
(North et al., 1968)
k = 1616
Tmin = 0.73, Tmax = 0.85l = 1111
5819 measured reflections3 standard reflections every 200 reflections
5525 independent reflections intensity decay: 5.7%
Refinement top
Refinement on F0 constraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040Weighting scheme based on measured s.u.'s w = 1/σ2(Fo)
wR(F2) = 0.038(Δ/σ)max = 0.02
S = 0.97Δρmax = 0.12 e Å3
3873 reflectionsΔρmin = 0.14 e Å3
374 parametersExtinction correction: Zachariasen (1967), equ(3) Acta Cryst. (1968) A24, p. 213.
0 restraintsExtinction coefficient: 3.12 (3)e-5
Crystal data top
C30H24BNO3·C2H6Oγ = 82.833 (4)°
Mr = 503.40V = 1355.18 (13) Å3
Triclinic, P1Z = 2
a = 11.5792 (6) ÅCu Kα radiation
b = 13.0972 (8) ŵ = 0.64 mm1
c = 9.0779 (5) ÅT = 294 K
α = 96.780 (5)°0.35 × 0.35 × 0.25 mm
β = 93.245 (4)°
Data collection top
Rigaku AFC-6S
diffractometer
3873 reflections with I > 3σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.014
Tmin = 0.73, Tmax = 0.853 standard reflections every 200 reflections
5819 measured reflections intensity decay: 5.7%
5525 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.038H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.12 e Å3
3873 reflectionsΔρmin = 0.14 e Å3
374 parameters
Special details top

Experimental. The scan width was (1.47 + 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.32892 (10)0.27695 (10)0.66978 (15)0.0604 (4)
O20.53261 (15)0.55445 (13)0.7669 (2)0.0900 (6)
O30.15695 (10)0.37238 (10)0.75914 (15)0.0606 (4)
O40.6272 (3)0.7288 (2)0.8030 (4)0.1111 (12)0.700
O4a0.5797 (7)0.7307 (6)0.6482 (8)0.106 (3)0.300
N10.34582 (12)0.36503 (11)0.7649 (2)0.0463 (4)
C10.55368 (15)0.37424 (15)0.7090 (2)0.0495 (5)
C20.5859 (2)0.4688 (2)0.6879 (2)0.0612 (6)
C30.6734 (2)0.4776 (2)0.5903 (3)0.0722 (8)
C40.7313 (2)0.3920 (2)0.5195 (2)0.0704 (7)
C50.7052 (2)0.2918 (2)0.5392 (2)0.0598 (6)
C60.7694 (2)0.2019 (2)0.4702 (3)0.0780 (8)
C70.7460 (2)0.1068 (2)0.4927 (3)0.0929 (10)
C80.6569 (2)0.0972 (2)0.5850 (3)0.0872 (9)
C90.5925 (2)0.1821 (2)0.6535 (3)0.0671 (7)
C100.6147 (2)0.2828 (2)0.6349 (2)0.0529 (6)
C110.46600 (15)0.37034 (14)0.8233 (2)0.0496 (5)
C120.24801 (15)0.41491 (14)0.8113 (2)0.0469 (5)
C130.23238 (15)0.51235 (14)0.9101 (2)0.0464 (5)
C140.1573 (2)0.5200 (2)1.0253 (2)0.0588 (6)
C150.1336 (2)0.6122 (2)1.1145 (2)0.0700 (7)
C160.1843 (2)0.6972 (2)1.0879 (3)0.0693 (7)
C170.2575 (2)0.6906 (2)0.9733 (3)0.0678 (7)
C180.2829 (2)0.59853 (15)0.8840 (2)0.0576 (6)
C190.14490 (15)0.27566 (14)0.4953 (2)0.0518 (5)
C200.0864 (2)0.3651 (2)0.4456 (3)0.0694 (7)
C210.0431 (2)0.3685 (2)0.3003 (4)0.0913 (10)
C220.0592 (2)0.2828 (3)0.2003 (3)0.0906 (10)
C230.1157 (3)0.1926 (2)0.2441 (3)0.0886 (9)
C240.1575 (2)0.1890 (2)0.3903 (3)0.0711 (7)
C250.1670 (2)0.17198 (15)0.7359 (2)0.0536 (6)
C260.2456 (2)0.1184 (2)0.8300 (3)0.0744 (8)
C270.2175 (3)0.0329 (2)0.8920 (3)0.0874 (9)
C280.1113 (3)0.0007 (2)0.8628 (3)0.0841 (9)
C290.0317 (2)0.0506 (2)0.7724 (3)0.0809 (9)
C300.0597 (2)0.1353 (2)0.7094 (3)0.0651 (7)
C310.5456 (6)0.8085 (4)0.7204 (6)0.110 (2)0.750
C31a0.600 (2)0.821 (2)0.779 (3)0.107 (7)*0.160
C31b0.457 (4)0.800 (4)0.798 (6)0.114 (12)*0.090
C320.5216 (6)0.8964 (5)0.8174 (8)0.155 (3)0.700
C32a0.511 (2)0.8248 (12)0.841 (2)0.162 (8)0.300
B10.1972 (2)0.2694 (2)0.6602 (3)0.0531 (6)
H10.561 (3)0.609 (3)0.761 (4)0.160 (11)*
H20.69210.54620.57380.087*
H30.79290.39910.45290.085*
H40.83180.20870.40480.094*
H50.79130.04490.44440.111*
H60.64010.02800.60120.105*
H70.52960.17280.71680.081*
H80.46670.43280.89420.059*
H90.49010.30900.87480.059*
H100.12070.45941.04370.071*
H110.08090.61711.19630.084*
H120.16800.76281.15130.083*
H130.29230.75200.95430.081*
H140.33630.59420.80280.069*
H150.07530.42820.51560.083*
H160.00090.43280.26990.110*
H170.03040.28560.09700.109*
H180.12680.13040.17250.106*
H190.19710.12360.42020.085*
H200.32260.14150.85310.089*
H210.27480.00340.95720.105*
H220.09200.06110.90630.101*
H230.04550.02750.75200.097*
H240.00150.17050.64390.078*
H250.58410.82510.63440.132*0.750
H260.47310.77980.68710.132*0.750
H270.58360.94080.81620.186*0.700
H280.44700.93390.78730.186*0.700
H290.51700.87720.91780.186*0.700
H300.69870.72970.77910.133*0.700
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0437 (7)0.0580 (8)0.0740 (9)0.0105 (6)0.0073 (6)0.0227 (7)
O20.0707 (11)0.0579 (10)0.144 (2)0.0194 (8)0.0431 (10)0.0097 (10)
O30.0406 (7)0.0584 (8)0.0782 (10)0.0108 (6)0.0087 (6)0.0200 (7)
O40.092 (2)0.074 (2)0.174 (3)0.0334 (15)0.003 (2)0.021 (2)
O4a0.126 (6)0.091 (5)0.111 (5)0.043 (4)0.017 (5)0.011 (4)
N10.0407 (8)0.0481 (8)0.0489 (8)0.0104 (6)0.0058 (6)0.0074 (7)
C10.0386 (10)0.0577 (11)0.0517 (10)0.0093 (8)0.0026 (8)0.0003 (9)
C20.0456 (11)0.0628 (13)0.0752 (14)0.0120 (9)0.0116 (10)0.0019 (11)
C30.0563 (13)0.0764 (15)0.089 (2)0.0181 (11)0.0144 (12)0.0145 (13)
C40.0527 (13)0.098 (2)0.0635 (14)0.0155 (12)0.0129 (10)0.0086 (12)
C50.0470 (11)0.0803 (15)0.0493 (11)0.0059 (10)0.0048 (9)0.0035 (10)
C60.0633 (14)0.100 (2)0.0643 (14)0.0033 (13)0.0149 (11)0.0093 (13)
C70.087 (2)0.086 (2)0.095 (2)0.0171 (15)0.0246 (15)0.0147 (15)
C80.082 (2)0.0654 (15)0.109 (2)0.0055 (13)0.0191 (15)0.0027 (14)
C90.0607 (13)0.0632 (13)0.0756 (15)0.0017 (10)0.0103 (11)0.0023 (11)
C100.0422 (10)0.0638 (12)0.0505 (11)0.0059 (9)0.0002 (8)0.0010 (9)
C110.0408 (10)0.0578 (11)0.0488 (10)0.0087 (8)0.0018 (8)0.0023 (8)
C120.0419 (10)0.0502 (10)0.0487 (10)0.0098 (8)0.0072 (8)0.0021 (8)
C130.0411 (9)0.0501 (10)0.0460 (10)0.0056 (8)0.0025 (8)0.0029 (8)
C140.0586 (12)0.0651 (13)0.0524 (11)0.0088 (10)0.0124 (9)0.0009 (10)
C150.0610 (13)0.090 (2)0.0529 (12)0.0016 (12)0.0107 (10)0.0145 (11)
C160.0572 (13)0.0685 (14)0.0712 (14)0.0021 (11)0.0061 (11)0.0239 (11)
C170.0600 (13)0.0504 (12)0.090 (2)0.0098 (10)0.0001 (12)0.0078 (11)
C180.0510 (11)0.0553 (11)0.0661 (13)0.0101 (9)0.0096 (9)0.0021 (10)
C190.0437 (10)0.0463 (10)0.0667 (12)0.0125 (8)0.0056 (9)0.0029 (9)
C200.0609 (13)0.0613 (13)0.087 (2)0.0024 (10)0.0134 (12)0.0140 (12)
C210.073 (2)0.105 (2)0.101 (2)0.0012 (15)0.0036 (15)0.044 (2)
C220.082 (2)0.125 (3)0.075 (2)0.037 (2)0.0150 (14)0.038 (2)
C230.120 (2)0.089 (2)0.0626 (15)0.045 (2)0.0049 (14)0.0006 (13)
C240.098 (2)0.0523 (12)0.0622 (13)0.0163 (11)0.0053 (12)0.0018 (10)
C250.0531 (11)0.0542 (11)0.0511 (11)0.0066 (9)0.0091 (9)0.0082 (9)
C260.0715 (15)0.082 (2)0.0700 (15)0.0161 (12)0.0076 (12)0.0067 (12)
C270.102 (2)0.090 (2)0.070 (2)0.004 (2)0.0011 (14)0.0205 (14)
C280.100 (2)0.079 (2)0.077 (2)0.0079 (15)0.0321 (15)0.0145 (13)
C290.071 (2)0.078 (2)0.100 (2)0.0189 (13)0.0227 (14)0.0128 (14)
C300.0534 (12)0.0671 (13)0.0771 (15)0.0118 (10)0.0102 (10)0.0094 (11)
C310.124 (4)0.106 (4)0.096 (4)0.020 (3)0.004 (3)0.010 (3)
C320.137 (5)0.128 (5)0.181 (6)0.016 (4)0.018 (4)0.017 (5)
C32a0.25 (2)0.090 (10)0.16 (2)0.086 (13)0.068 (14)0.034 (10)
B10.0418 (11)0.0479 (12)0.0663 (14)0.0073 (9)0.0062 (10)0.0109 (10)
Geometric parameters (Å, º) top
O1—N11.384 (2)C15—H110.98
O1—B11.537 (2)C16—C171.367 (3)
O2—C21.357 (2)C16—H120.98
O2—H10.83 (3)C17—C181.381 (3)
O3—C121.294 (2)C17—H130.98
O3—B11.564 (2)C18—H140.98
O4—C311.551 (6)C19—C201.389 (3)
O4—H300.87C19—C241.392 (3)
O4a—C31a1.61 (3)C19—B11.590 (3)
N1—C111.468 (2)C20—C211.388 (4)
N1—C121.301 (2)C20—H150.98
C1—C21.374 (3)C21—C221.359 (4)
C1—C101.428 (3)C21—H160.98
C1—C111.502 (2)C22—C231.368 (4)
C2—C31.407 (3)C22—H170.98
C3—C41.346 (3)C23—C241.391 (3)
C3—H20.98C23—H180.98
C4—C51.417 (3)C24—H190.98
C4—H30.98C25—C261.395 (3)
C5—C61.411 (3)C25—C301.386 (3)
C5—C101.423 (3)C25—B11.602 (3)
C6—C71.348 (4)C26—C271.391 (3)
C6—H40.98C26—H200.98
C7—C81.392 (4)C27—C281.360 (4)
C7—H50.98C27—H210.98
C8—C91.365 (3)C28—C291.365 (4)
C8—H60.98C28—H220.98
C9—C101.405 (3)C29—C301.387 (3)
C9—H70.98C29—H230.98
C11—H80.98C30—H240.98
C11—H90.98C31—C321.373 (8)
C12—C131.468 (2)C31—H250.98
C13—C141.385 (2)C31—H260.98
C13—C181.385 (3)C31a—C32a1.19 (3)
C14—C151.379 (3)C32—H270.98
C14—H100.98C32—H280.98
C15—C161.372 (3)C32—H290.98
O1···O4ai3.117 (7)O4a···C24i3.390 (7)
O2···O42.632 (3)O4a···C23.482 (8)
O2···O4a2.784 (7)O4a···C19i3.501 (7)
O2···C31b3.21 (5)O4a···C9i3.512 (8)
O2···C313.426 (6)C1···C16iii3.542 (3)
O2···C32a3.505 (15)C4···C15iii3.595 (3)
O3···C15ii3.590 (2)C5···C16iii3.543 (3)
O4···C23i3.334 (4)C6···C31bi3.48 (5)
O4···C24i3.472 (4)C10···C16iii3.339 (3)
O4···C23.525 (3)C17···C31b3.42 (5)
O4a···C10i3.323 (8)C23···C31ai3.29 (3)
O4a···C33.346 (8)C24···C31ai3.26 (3)
N1—O1—B1106.71 (12)C18—C17—H13119.6
C2—O2—H1115 (2)C13—C18—C17119.4 (2)
C12—O3—B1108.85 (13)C13—C18—H14120.3
C31—O4—H30109.5C17—C18—H14120.3
O1—N1—C11115.01 (13)C20—C19—C24115.8 (2)
O1—N1—C12112.05 (13)C20—C19—B1123.7 (2)
C11—N1—C12130.78 (15)C24—C19—B1120.4 (2)
C2—C1—C10118.8 (2)C19—C20—C21122.4 (2)
C2—C1—C11118.5 (2)C19—C20—H15118.8
C10—C1—C11122.3 (2)C21—C20—H15118.8
O2—C2—C1118.1 (2)C20—C21—C22120.0 (3)
O2—C2—C3120.3 (2)C20—C21—H16120.0
C1—C2—C3121.6 (2)C22—C21—H16120.0
C2—C3—C4120.1 (2)C21—C22—C23119.8 (3)
C2—C3—H2120.0C21—C22—H17120.1
C4—C3—H2120.0C23—C22—H17120.1
C3—C4—C5121.4 (2)C22—C23—C24120.0 (2)
C3—C4—H3119.3C22—C23—H18120.0
C5—C4—H3119.3C24—C23—H18120.0
C4—C5—C6121.3 (2)C19—C24—C23121.9 (2)
C4—C5—C10118.6 (2)C19—C24—H19119.0
C6—C5—C10120.0 (2)C23—C24—H19119.0
C5—C6—C7121.0 (2)C26—C25—C30115.9 (2)
C5—C6—H4119.5C26—C25—B1123.0 (2)
C7—C6—H4119.5C30—C25—B1121.1 (2)
C6—C7—C8119.5 (2)C25—C26—C27121.6 (2)
C6—C7—H5120.3C25—C26—H20119.2
C8—C7—H5120.3C27—C26—H20119.2
C7—C8—C9121.4 (2)C26—C27—C28120.6 (2)
C7—C8—H6119.3C26—C27—H21119.7
C9—C8—H6119.3C28—C27—H21119.7
C8—C9—C10121.1 (2)C27—C28—C29119.3 (2)
C8—C9—H7119.4C27—C28—H22120.3
C10—C9—H7119.4C29—C28—H22120.3
C1—C10—C5119.5 (2)C28—C29—C30120.3 (2)
C1—C10—C9123.5 (2)C28—C29—H23119.9
C5—C10—C9117.0 (2)C30—C29—H23119.9
N1—C11—C1115.26 (15)C25—C30—C29122.3 (2)
N1—C11—H8108.0C25—C30—H24118.9
N1—C11—H9108.0C29—C30—H24118.9
C1—C11—H8108.0O4—C31—C32108.1 (5)
C1—C11—H9108.0O4—C31—H25109.8
H8—C11—H9109.5O4—C31—H26109.8
O3—C12—N1113.91 (15)C32—C31—H25109.8
O3—C12—C13119.00 (15)C32—C31—H26109.8
N1—C12—C13127.1 (2)H25—C31—H26109.5
C12—C13—C14118.5 (2)O4—C31a—C32a91 (2)
C12—C13—C18121.9 (2)C31—C32—H27109.5
C14—C13—C18119.4 (2)C31—C32—H28109.5
C13—C14—C15120.5 (2)C31—C32—H29109.5
C13—C14—H10119.7H27—C32—H28109.5
C15—C14—H10119.7H27—C32—H29109.5
C14—C15—C16119.6 (2)H28—C32—H29109.5
C14—C15—H11120.2O1—B1—O398.35 (13)
C16—C15—H11120.2O1—B1—C19111.3 (2)
C15—C16—C17120.3 (2)O1—B1—C25111.5 (2)
C15—C16—H12119.9O3—B1—C19109.6 (2)
C17—C16—H12119.9O3—B1—C25110.2 (2)
C16—C17—C18120.8 (2)C19—B1—C25114.7 (2)
C16—C17—H13119.6
O1—N1—C11—C163.2 (2)C5—C10—C1—C11173.5 (2)
O1—N1—C12—O30.2 (2)C5—C10—C9—C81.4 (3)
O1—N1—C12—C13178.5 (2)C6—C5—C10—C91.1 (3)
O1—B1—O3—C123.5 (2)C6—C7—C8—C90.0 (5)
O1—B1—C19—C2099.6 (2)C7—C6—C5—C100.3 (4)
O1—B1—C19—C2479.5 (2)C7—C8—C9—C100.9 (4)
O1—B1—C25—C2615.2 (3)C9—C10—C1—C114.9 (3)
O1—B1—C25—C30164.2 (2)C11—N1—O1—B1162.9 (2)
O2—C2—C1—C10175.5 (2)C11—N1—C12—C1319.4 (3)
O2—C2—C1—C113.0 (3)C12—O3—B1—C19119.8 (2)
O2—C2—C3—C4175.7 (2)C12—O3—B1—C25113.1 (2)
O3—C12—N1—C11162.3 (2)C12—N1—O1—B12.3 (2)
O3—C12—C13—C1447.0 (3)C12—C13—C14—C15175.4 (2)
O3—C12—C13—C18127.8 (2)C12—C13—C18—C17174.6 (2)
O3—B1—O1—N13.3 (2)C13—C12—O3—B1179.0 (2)
O3—B1—C19—C208.2 (3)C13—C14—C15—C160.5 (3)
O3—B1—C19—C24172.7 (2)C13—C18—C17—C160.8 (3)
O3—B1—C25—C2692.9 (2)C14—C13—C18—C170.1 (3)
O3—B1—C25—C3087.8 (2)C14—C15—C16—C170.3 (3)
N1—O1—B1—C19118.2 (2)C15—C14—C13—C180.6 (3)
N1—O1—B1—C25112.3 (2)C15—C16—C17—C180.9 (4)
N1—C11—C1—C298.6 (2)C19—C20—C21—C221.2 (4)
N1—C11—C1—C1089.2 (2)C19—C24—C23—C220.7 (4)
N1—C12—O3—B12.6 (2)C19—B1—C25—C26142.8 (2)
N1—C12—C13—C14134.9 (2)C19—B1—C25—C3036.5 (3)
N1—C12—C13—C1850.4 (3)C20—C19—C24—C231.0 (3)
C1—C2—C3—C42.9 (4)C20—C19—B1—C25132.7 (2)
C1—C10—C5—C40.5 (3)C20—C21—C22—C231.6 (4)
C1—C10—C5—C6177.4 (2)C21—C20—C19—C240.0 (3)
C1—C10—C9—C8177.1 (2)C21—C20—C19—B1179.1 (2)
C1—C11—N1—C12135.1 (2)C21—C22—C23—C240.6 (4)
C2—C1—C10—C51.3 (3)C23—C24—C19—B1178.2 (2)
C2—C1—C10—C9177.1 (2)C24—C19—B1—C2548.2 (3)
C2—C3—C4—C50.9 (4)C25—C26—C27—C280.4 (4)
C3—C2—C1—C103.0 (3)C25—C30—C29—C280.7 (4)
C3—C2—C1—C11175.5 (2)C26—C25—C30—C290.0 (3)
C3—C4—C5—C6177.2 (2)C26—C27—C28—C290.3 (4)
C3—C4—C5—C100.7 (3)C27—C26—C25—C300.5 (3)
C4—C5—C6—C7178.2 (3)C27—C26—C25—B1178.9 (2)
C4—C5—C10—C9179.1 (2)C27—C28—C29—C300.9 (4)
C5—C6—C7—C80.2 (4)C29—C30—C25—B1179.4 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+2; (iii) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC30H24BNO3·C2H6O
Mr503.40
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)11.5792 (6), 13.0972 (8), 9.0779 (5)
α, β, γ (°)96.780 (5), 93.245 (4), 82.833 (4)
V3)1355.18 (13)
Z2
Radiation typeCu Kα
µ (mm1)0.64
Crystal size (mm)0.35 × 0.35 × 0.25
Data collection
DiffractometerRigaku AFC-6S
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.73, 0.85
No. of measured, independent and
observed [I > 3σ(I)] reflections
5819, 5525, 3873
Rint0.014
(sin θ/λ)max1)0.633
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.038, 0.97
No. of reflections3873
No. of parameters374
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.12, 0.14

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1995), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1992–1997), SIR92 (Altomare et al., 1993), TEXSAN.

Selected geometric parameters (Å, º) top
O1—N11.384 (2)C13—C141.385 (2)
O1—B11.537 (2)C13—C181.385 (3)
O2—C21.357 (2)C14—C151.379 (3)
O3—C121.294 (2)C15—C161.372 (3)
O3—B11.564 (2)C16—C171.367 (3)
N1—C111.468 (2)C17—C181.381 (3)
N1—C121.301 (2)C19—C201.389 (3)
C1—C21.374 (3)C19—C241.392 (3)
C1—C101.428 (3)C19—B11.590 (3)
C1—C111.502 (2)C20—C211.388 (4)
C2—C31.407 (3)C21—C221.359 (4)
C3—C41.346 (3)C22—C231.368 (4)
C4—C51.417 (3)C23—C241.391 (3)
C5—C61.411 (3)C25—C261.395 (3)
C5—C101.423 (3)C25—C301.386 (3)
C6—C71.348 (4)C25—B11.602 (3)
C7—C81.392 (4)C26—C271.391 (3)
C8—C91.365 (3)C27—C281.360 (4)
C9—C101.405 (3)C28—C291.365 (4)
C12—C131.468 (2)C29—C301.387 (3)
N1—O1—B1106.71 (12)C14—C13—C18119.4 (2)
C12—O3—B1108.85 (13)C13—C14—C15120.5 (2)
O1—N1—C11115.01 (13)C14—C15—C16119.6 (2)
O1—N1—C12112.05 (13)C15—C16—C17120.3 (2)
C11—N1—C12130.78 (15)C16—C17—C18120.8 (2)
C2—C1—C10118.8 (2)C13—C18—C17119.4 (2)
C2—C1—C11118.5 (2)C20—C19—C24115.8 (2)
C10—C1—C11122.3 (2)C20—C19—B1123.7 (2)
O2—C2—C1118.1 (2)C24—C19—B1120.4 (2)
O2—C2—C3120.3 (2)C19—C20—C21122.4 (2)
C1—C2—C3121.6 (2)C20—C21—C22120.0 (3)
C2—C3—C4120.1 (2)C21—C22—C23119.8 (3)
C3—C4—C5121.4 (2)C22—C23—C24120.0 (2)
C4—C5—C6121.3 (2)C19—C24—C23121.9 (2)
C4—C5—C10118.6 (2)C26—C25—C30115.9 (2)
C6—C5—C10120.0 (2)C26—C25—B1123.0 (2)
C5—C6—C7121.0 (2)C30—C25—B1121.1 (2)
C6—C7—C8119.5 (2)C25—C26—C27121.6 (2)
C7—C8—C9121.4 (2)C26—C27—C28120.6 (2)
C8—C9—C10121.1 (2)C27—C28—C29119.3 (2)
C1—C10—C5119.5 (2)C28—C29—C30120.3 (2)
C1—C10—C9123.5 (2)C25—C30—C29122.3 (2)
C5—C10—C9117.0 (2)O1—B1—O398.35 (13)
N1—C11—C1115.26 (15)O1—B1—C19111.3 (2)
O3—C12—N1113.91 (15)O1—B1—C25111.5 (2)
O3—C12—C13119.00 (15)O3—B1—C19109.6 (2)
N1—C12—C13127.1 (2)O3—B1—C25110.2 (2)
C12—C13—C14118.5 (2)C19—B1—C25114.7 (2)
C12—C13—C18121.9 (2)
 

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