An OBONC five-membered heterocycle

Kliegel, W.; Metge, J.; Patrick, B.O.; Rettig, S.J.; Trotter, J.

doi:10.1107/S1600536801018037

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An OBONC five-membered heterocycle

W. Kliegel, J. Metge, B. O. Patrick, S. J. Rettig and J. Trotter

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).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018037/cf6117sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018037/cf6117Isup2.hkl Contains datablock I

CCDC reference: 176042

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (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


 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).


 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—N═C 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 C═N double bond, with perhaps a minor contribution from the resonance structure with a C═O 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 (C═O/C═C). 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 (w_1/2 = 428 Hz), 45.3 (w_1/2 = 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.

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

Fig. 1. View of the structure of (II)·EtOH with 50% probability ellipsoids.

(I) top

Crystal data top

C₃₀H₂₄BNO₃·C₂H₆O	Z = 2
M_r = 503.40	F(000) = 532
Triclinic, P1	D_x = 1.234 Mg m⁻³
a = 11.5792 (6) Å	Cu Kα radiation, λ = 1.5418 Å
b = 13.0972 (8) Å	Cell parameters from 25 reflections
c = 9.0779 (5) Å	θ = 43.8–54.4°
α = 96.780 (5)°	µ = 0.64 mm⁻¹
β = 93.245 (4)°	T = 294 K
γ = 82.833 (4)°	Prism, colorless
V = 1355.18 (13) Å³	0.35 × 0.35 × 0.25 mm

Data collection top

Rigaku AFC-6S diffractometer	3873 reflections with I > 3σ(I)
Radiation source: X-ray tube	R_int = 0.014
Graphite monochromator	θ_max = 77.5°, θ_min = 3.4°
ω–2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = −16→16
T_min = 0.73, T_max = 0.85	l = −11→11
5819 measured reflections	3 standard reflections every 200 reflections
5525 independent reflections	intensity decay: 5.7%

Refinement top

Refinement on F	0 constraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.040	Weighting scheme based on measured s.u.'s w = 1/σ²(F_o)
wR(F²) = 0.038	(Δ/σ)_max = 0.02
S = 0.97	Δρ_max = 0.12 e Å⁻³
3873 reflections	Δρ_min = −0.14 e Å⁻³
374 parameters	Extinction correction: Zachariasen (1967), equ(3) Acta Cryst. (1968) A24, p. 213.
0 restraints	Extinction coefficient: 3.12 (3)e-5

Crystal data top

C₃₀H₂₄BNO₃·C₂H₆O	γ = 82.833 (4)°
M_r = 503.40	V = 1355.18 (13) Å³
Triclinic, P1	Z = 2
a = 11.5792 (6) Å	Cu Kα radiation
b = 13.0972 (8) Å	µ = 0.64 mm⁻¹
c = 9.0779 (5) Å	T = 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)	R_int = 0.014
T_min = 0.73, T_max = 0.85	3 standard reflections every 200 reflections
5819 measured reflections	intensity decay: 5.7%
5525 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.038	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.12 e Å⁻³
3873 reflections	Δρ_min = −0.14 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.32892 (10)	0.27695 (10)	0.66978 (15)	0.0604 (4)
O2	0.53261 (15)	0.55445 (13)	0.7669 (2)	0.0900 (6)
O3	0.15695 (10)	0.37238 (10)	0.75914 (15)	0.0606 (4)
O4	0.6272 (3)	0.7288 (2)	0.8030 (4)	0.1111 (12)	0.700
O4a	0.5797 (7)	0.7307 (6)	0.6482 (8)	0.106 (3)	0.300
N1	0.34582 (12)	0.36503 (11)	0.7649 (2)	0.0463 (4)
C1	0.55368 (15)	0.37424 (15)	0.7090 (2)	0.0495 (5)
C2	0.5859 (2)	0.4688 (2)	0.6879 (2)	0.0612 (6)
C3	0.6734 (2)	0.4776 (2)	0.5903 (3)	0.0722 (8)
C4	0.7313 (2)	0.3920 (2)	0.5195 (2)	0.0704 (7)
C5	0.7052 (2)	0.2918 (2)	0.5392 (2)	0.0598 (6)
C6	0.7694 (2)	0.2019 (2)	0.4702 (3)	0.0780 (8)
C7	0.7460 (2)	0.1068 (2)	0.4927 (3)	0.0929 (10)
C8	0.6569 (2)	0.0972 (2)	0.5850 (3)	0.0872 (9)
C9	0.5925 (2)	0.1821 (2)	0.6535 (3)	0.0671 (7)
C10	0.6147 (2)	0.2828 (2)	0.6349 (2)	0.0529 (6)
C11	0.46600 (15)	0.37034 (14)	0.8233 (2)	0.0496 (5)
C12	0.24801 (15)	0.41491 (14)	0.8113 (2)	0.0469 (5)
C13	0.23238 (15)	0.51235 (14)	0.9101 (2)	0.0464 (5)
C14	0.1573 (2)	0.5200 (2)	1.0253 (2)	0.0588 (6)
C15	0.1336 (2)	0.6122 (2)	1.1145 (2)	0.0700 (7)
C16	0.1843 (2)	0.6972 (2)	1.0879 (3)	0.0693 (7)
C17	0.2575 (2)	0.6906 (2)	0.9733 (3)	0.0678 (7)
C18	0.2829 (2)	0.59853 (15)	0.8840 (2)	0.0576 (6)
C19	0.14490 (15)	0.27566 (14)	0.4953 (2)	0.0518 (5)
C20	0.0864 (2)	0.3651 (2)	0.4456 (3)	0.0694 (7)
C21	0.0431 (2)	0.3685 (2)	0.3003 (4)	0.0913 (10)
C22	0.0592 (2)	0.2828 (3)	0.2003 (3)	0.0906 (10)
C23	0.1157 (3)	0.1926 (2)	0.2441 (3)	0.0886 (9)
C24	0.1575 (2)	0.1890 (2)	0.3903 (3)	0.0711 (7)
C25	0.1670 (2)	0.17198 (15)	0.7359 (2)	0.0536 (6)
C26	0.2456 (2)	0.1184 (2)	0.8300 (3)	0.0744 (8)
C27	0.2175 (3)	0.0329 (2)	0.8920 (3)	0.0874 (9)
C28	0.1113 (3)	−0.0007 (2)	0.8628 (3)	0.0841 (9)
C29	0.0317 (2)	0.0506 (2)	0.7724 (3)	0.0809 (9)
C30	0.0597 (2)	0.1353 (2)	0.7094 (3)	0.0651 (7)
C31	0.5456 (6)	0.8085 (4)	0.7204 (6)	0.110 (2)	0.750
C31a	0.600 (2)	0.821 (2)	0.779 (3)	0.107 (7)*	0.160
C31b	0.457 (4)	0.800 (4)	0.798 (6)	0.114 (12)*	0.090
C32	0.5216 (6)	0.8964 (5)	0.8174 (8)	0.155 (3)	0.700
C32a	0.511 (2)	0.8248 (12)	0.841 (2)	0.162 (8)	0.300
B1	0.1972 (2)	0.2694 (2)	0.6602 (3)	0.0531 (6)
H1	0.561 (3)	0.609 (3)	0.761 (4)	0.160 (11)*
H2	0.6921	0.5462	0.5738	0.087*
H3	0.7929	0.3991	0.4529	0.085*
H4	0.8318	0.2087	0.4048	0.094*
H5	0.7913	0.0449	0.4444	0.111*
H6	0.6401	0.0280	0.6012	0.105*
H7	0.5296	0.1728	0.7168	0.081*
H8	0.4667	0.4328	0.8942	0.059*
H9	0.4901	0.3090	0.8748	0.059*
H10	0.1207	0.4594	1.0437	0.071*
H11	0.0809	0.6171	1.1963	0.084*
H12	0.1680	0.7628	1.1513	0.083*
H13	0.2923	0.7520	0.9543	0.081*
H14	0.3363	0.5942	0.8028	0.069*
H15	0.0753	0.4282	0.5156	0.083*
H16	0.0009	0.4328	0.2699	0.110*
H17	0.0304	0.2856	0.0970	0.109*
H18	0.1268	0.1304	0.1725	0.106*
H19	0.1971	0.1236	0.4202	0.085*
H20	0.3226	0.1415	0.8531	0.089*
H21	0.2748	−0.0034	0.9572	0.105*
H22	0.0920	−0.0611	0.9063	0.101*
H23	−0.0455	0.0275	0.7520	0.097*
H24	0.0015	0.1705	0.6439	0.078*
H25	0.5841	0.8251	0.6344	0.132*	0.750
H26	0.4731	0.7798	0.6871	0.132*	0.750
H27	0.5836	0.9408	0.8162	0.186*	0.700
H28	0.4470	0.9339	0.7873	0.186*	0.700
H29	0.5170	0.8772	0.9178	0.186*	0.700
H30	0.6987	0.7297	0.7791	0.133*	0.700

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0437 (7)	0.0580 (8)	0.0740 (9)	−0.0105 (6)	0.0073 (6)	−0.0227 (7)
O2	0.0707 (11)	0.0579 (10)	0.144 (2)	−0.0194 (8)	0.0431 (10)	−0.0097 (10)
O3	0.0406 (7)	0.0584 (8)	0.0782 (10)	−0.0108 (6)	0.0087 (6)	−0.0200 (7)
O4	0.092 (2)	0.074 (2)	0.174 (3)	−0.0334 (15)	−0.003 (2)	0.021 (2)
O4a	0.126 (6)	0.091 (5)	0.111 (5)	−0.043 (4)	0.017 (5)	0.011 (4)
N1	0.0407 (8)	0.0481 (8)	0.0489 (8)	−0.0104 (6)	0.0058 (6)	−0.0074 (7)
C1	0.0386 (10)	0.0577 (11)	0.0517 (10)	−0.0093 (8)	0.0026 (8)	−0.0003 (9)
C2	0.0456 (11)	0.0628 (13)	0.0752 (14)	−0.0120 (9)	0.0116 (10)	−0.0019 (11)
C3	0.0563 (13)	0.0764 (15)	0.089 (2)	−0.0181 (11)	0.0144 (12)	0.0145 (13)
C4	0.0527 (13)	0.098 (2)	0.0635 (14)	−0.0155 (12)	0.0129 (10)	0.0086 (12)
C5	0.0470 (11)	0.0803 (15)	0.0493 (11)	−0.0059 (10)	0.0048 (9)	−0.0035 (10)
C6	0.0633 (14)	0.100 (2)	0.0643 (14)	0.0033 (13)	0.0149 (11)	−0.0093 (13)
C7	0.087 (2)	0.086 (2)	0.095 (2)	0.0171 (15)	0.0246 (15)	−0.0147 (15)
C8	0.082 (2)	0.0654 (15)	0.109 (2)	0.0055 (13)	0.0191 (15)	−0.0027 (14)
C9	0.0607 (13)	0.0632 (13)	0.0756 (15)	−0.0017 (10)	0.0103 (11)	0.0023 (11)
C10	0.0422 (10)	0.0638 (12)	0.0505 (11)	−0.0059 (9)	−0.0002 (8)	−0.0010 (9)
C11	0.0408 (10)	0.0578 (11)	0.0488 (10)	−0.0087 (8)	0.0018 (8)	−0.0023 (8)
C12	0.0419 (10)	0.0502 (10)	0.0487 (10)	−0.0098 (8)	0.0072 (8)	−0.0021 (8)
C13	0.0411 (9)	0.0501 (10)	0.0460 (10)	−0.0056 (8)	0.0025 (8)	−0.0029 (8)
C14	0.0586 (12)	0.0651 (13)	0.0524 (11)	−0.0088 (10)	0.0124 (9)	−0.0009 (10)
C15	0.0610 (13)	0.090 (2)	0.0529 (12)	−0.0016 (12)	0.0107 (10)	−0.0145 (11)
C16	0.0572 (13)	0.0685 (14)	0.0712 (14)	0.0021 (11)	−0.0061 (11)	−0.0239 (11)
C17	0.0600 (13)	0.0504 (12)	0.090 (2)	−0.0098 (10)	0.0001 (12)	−0.0078 (11)
C18	0.0510 (11)	0.0553 (11)	0.0661 (13)	−0.0101 (9)	0.0096 (9)	−0.0021 (10)
C19	0.0437 (10)	0.0463 (10)	0.0667 (12)	−0.0125 (8)	0.0056 (9)	0.0029 (9)
C20	0.0609 (13)	0.0613 (13)	0.087 (2)	−0.0024 (10)	0.0134 (12)	0.0140 (12)
C21	0.073 (2)	0.105 (2)	0.101 (2)	0.0012 (15)	0.0036 (15)	0.044 (2)
C22	0.082 (2)	0.125 (3)	0.075 (2)	−0.037 (2)	−0.0150 (14)	0.038 (2)
C23	0.120 (2)	0.089 (2)	0.0626 (15)	−0.045 (2)	−0.0049 (14)	−0.0006 (13)
C24	0.098 (2)	0.0523 (12)	0.0622 (13)	−0.0163 (11)	−0.0053 (12)	0.0018 (10)
C25	0.0531 (11)	0.0542 (11)	0.0511 (11)	−0.0066 (9)	0.0091 (9)	−0.0082 (9)
C26	0.0715 (15)	0.082 (2)	0.0700 (15)	−0.0161 (12)	−0.0076 (12)	0.0067 (12)
C27	0.102 (2)	0.090 (2)	0.070 (2)	−0.004 (2)	0.0011 (14)	0.0205 (14)
C28	0.100 (2)	0.079 (2)	0.077 (2)	−0.0079 (15)	0.0321 (15)	0.0145 (13)
C29	0.071 (2)	0.078 (2)	0.100 (2)	−0.0189 (13)	0.0227 (14)	0.0128 (14)
C30	0.0534 (12)	0.0671 (13)	0.0771 (15)	−0.0118 (10)	0.0102 (10)	0.0094 (11)
C31	0.124 (4)	0.106 (4)	0.096 (4)	−0.020 (3)	−0.004 (3)	−0.010 (3)
C32	0.137 (5)	0.128 (5)	0.181 (6)	0.016 (4)	−0.018 (4)	−0.017 (5)
C32a	0.25 (2)	0.090 (10)	0.16 (2)	−0.086 (13)	0.068 (14)	−0.034 (10)
B1	0.0418 (11)	0.0479 (12)	0.0663 (14)	−0.0073 (9)	0.0062 (10)	−0.0109 (10)

Geometric parameters (Å, º) top

O1—N1	1.384 (2)	C15—H11	0.98
O1—B1	1.537 (2)	C16—C17	1.367 (3)
O2—C2	1.357 (2)	C16—H12	0.98
O2—H1	0.83 (3)	C17—C18	1.381 (3)
O3—C12	1.294 (2)	C17—H13	0.98
O3—B1	1.564 (2)	C18—H14	0.98
O4—C31	1.551 (6)	C19—C20	1.389 (3)
O4—H30	0.87	C19—C24	1.392 (3)
O4a—C31a	1.61 (3)	C19—B1	1.590 (3)
N1—C11	1.468 (2)	C20—C21	1.388 (4)
N1—C12	1.301 (2)	C20—H15	0.98
C1—C2	1.374 (3)	C21—C22	1.359 (4)
C1—C10	1.428 (3)	C21—H16	0.98
C1—C11	1.502 (2)	C22—C23	1.368 (4)
C2—C3	1.407 (3)	C22—H17	0.98
C3—C4	1.346 (3)	C23—C24	1.391 (3)
C3—H2	0.98	C23—H18	0.98
C4—C5	1.417 (3)	C24—H19	0.98
C4—H3	0.98	C25—C26	1.395 (3)
C5—C6	1.411 (3)	C25—C30	1.386 (3)
C5—C10	1.423 (3)	C25—B1	1.602 (3)
C6—C7	1.348 (4)	C26—C27	1.391 (3)
C6—H4	0.98	C26—H20	0.98
C7—C8	1.392 (4)	C27—C28	1.360 (4)
C7—H5	0.98	C27—H21	0.98
C8—C9	1.365 (3)	C28—C29	1.365 (4)
C8—H6	0.98	C28—H22	0.98
C9—C10	1.405 (3)	C29—C30	1.387 (3)
C9—H7	0.98	C29—H23	0.98
C11—H8	0.98	C30—H24	0.98
C11—H9	0.98	C31—C32	1.373 (8)
C12—C13	1.468 (2)	C31—H25	0.98
C13—C14	1.385 (2)	C31—H26	0.98
C13—C18	1.385 (3)	C31a—C32a	1.19 (3)
C14—C15	1.379 (3)	C32—H27	0.98
C14—H10	0.98	C32—H28	0.98
C15—C16	1.372 (3)	C32—H29	0.98

O1···O4aⁱ	3.117 (7)	O4a···C24ⁱ	3.390 (7)
O2···O4	2.632 (3)	O4a···C2	3.482 (8)
O2···O4a	2.784 (7)	O4a···C19ⁱ	3.501 (7)
O2···C31b	3.21 (5)	O4a···C9ⁱ	3.512 (8)
O2···C31	3.426 (6)	C1···C16ⁱⁱⁱ	3.542 (3)
O2···C32a	3.505 (15)	C4···C15ⁱⁱⁱ	3.595 (3)
O3···C15ⁱⁱ	3.590 (2)	C5···C16ⁱⁱⁱ	3.543 (3)
O4···C23ⁱ	3.334 (4)	C6···C31bⁱ	3.48 (5)
O4···C24ⁱ	3.472 (4)	C10···C16ⁱⁱⁱ	3.339 (3)
O4···C2	3.525 (3)	C17···C31b	3.42 (5)
O4a···C10ⁱ	3.323 (8)	C23···C31aⁱ	3.29 (3)
O4a···C3	3.346 (8)	C24···C31aⁱ	3.26 (3)

N1—O1—B1	106.71 (12)	C18—C17—H13	119.6
C2—O2—H1	115 (2)	C13—C18—C17	119.4 (2)
C12—O3—B1	108.85 (13)	C13—C18—H14	120.3
C31—O4—H30	109.5	C17—C18—H14	120.3
O1—N1—C11	115.01 (13)	C20—C19—C24	115.8 (2)
O1—N1—C12	112.05 (13)	C20—C19—B1	123.7 (2)
C11—N1—C12	130.78 (15)	C24—C19—B1	120.4 (2)
C2—C1—C10	118.8 (2)	C19—C20—C21	122.4 (2)
C2—C1—C11	118.5 (2)	C19—C20—H15	118.8
C10—C1—C11	122.3 (2)	C21—C20—H15	118.8
O2—C2—C1	118.1 (2)	C20—C21—C22	120.0 (3)
O2—C2—C3	120.3 (2)	C20—C21—H16	120.0
C1—C2—C3	121.6 (2)	C22—C21—H16	120.0
C2—C3—C4	120.1 (2)	C21—C22—C23	119.8 (3)
C2—C3—H2	120.0	C21—C22—H17	120.1
C4—C3—H2	120.0	C23—C22—H17	120.1
C3—C4—C5	121.4 (2)	C22—C23—C24	120.0 (2)
C3—C4—H3	119.3	C22—C23—H18	120.0
C5—C4—H3	119.3	C24—C23—H18	120.0
C4—C5—C6	121.3 (2)	C19—C24—C23	121.9 (2)
C4—C5—C10	118.6 (2)	C19—C24—H19	119.0
C6—C5—C10	120.0 (2)	C23—C24—H19	119.0
C5—C6—C7	121.0 (2)	C26—C25—C30	115.9 (2)
C5—C6—H4	119.5	C26—C25—B1	123.0 (2)
C7—C6—H4	119.5	C30—C25—B1	121.1 (2)
C6—C7—C8	119.5 (2)	C25—C26—C27	121.6 (2)
C6—C7—H5	120.3	C25—C26—H20	119.2
C8—C7—H5	120.3	C27—C26—H20	119.2
C7—C8—C9	121.4 (2)	C26—C27—C28	120.6 (2)
C7—C8—H6	119.3	C26—C27—H21	119.7
C9—C8—H6	119.3	C28—C27—H21	119.7
C8—C9—C10	121.1 (2)	C27—C28—C29	119.3 (2)
C8—C9—H7	119.4	C27—C28—H22	120.3
C10—C9—H7	119.4	C29—C28—H22	120.3
C1—C10—C5	119.5 (2)	C28—C29—C30	120.3 (2)
C1—C10—C9	123.5 (2)	C28—C29—H23	119.9
C5—C10—C9	117.0 (2)	C30—C29—H23	119.9
N1—C11—C1	115.26 (15)	C25—C30—C29	122.3 (2)
N1—C11—H8	108.0	C25—C30—H24	118.9
N1—C11—H9	108.0	C29—C30—H24	118.9
C1—C11—H8	108.0	O4—C31—C32	108.1 (5)
C1—C11—H9	108.0	O4—C31—H25	109.8
H8—C11—H9	109.5	O4—C31—H26	109.8
O3—C12—N1	113.91 (15)	C32—C31—H25	109.8
O3—C12—C13	119.00 (15)	C32—C31—H26	109.8
N1—C12—C13	127.1 (2)	H25—C31—H26	109.5
C12—C13—C14	118.5 (2)	O4—C31a—C32a	91 (2)
C12—C13—C18	121.9 (2)	C31—C32—H27	109.5
C14—C13—C18	119.4 (2)	C31—C32—H28	109.5
C13—C14—C15	120.5 (2)	C31—C32—H29	109.5
C13—C14—H10	119.7	H27—C32—H28	109.5
C15—C14—H10	119.7	H27—C32—H29	109.5
C14—C15—C16	119.6 (2)	H28—C32—H29	109.5
C14—C15—H11	120.2	O1—B1—O3	98.35 (13)
C16—C15—H11	120.2	O1—B1—C19	111.3 (2)
C15—C16—C17	120.3 (2)	O1—B1—C25	111.5 (2)
C15—C16—H12	119.9	O3—B1—C19	109.6 (2)
C17—C16—H12	119.9	O3—B1—C25	110.2 (2)
C16—C17—C18	120.8 (2)	C19—B1—C25	114.7 (2)
C16—C17—H13	119.6

O1—N1—C11—C1	63.2 (2)	C5—C10—C1—C11	−173.5 (2)
O1—N1—C12—O3	−0.2 (2)	C5—C10—C9—C8	1.4 (3)
O1—N1—C12—C13	−178.5 (2)	C6—C5—C10—C9	−1.1 (3)
O1—B1—O3—C12	−3.5 (2)	C6—C7—C8—C9	0.0 (5)
O1—B1—C19—C20	−99.6 (2)	C7—C6—C5—C10	0.3 (4)
O1—B1—C19—C24	79.5 (2)	C7—C8—C9—C10	−0.9 (4)
O1—B1—C25—C26	15.2 (3)	C9—C10—C1—C11	4.9 (3)
O1—B1—C25—C30	−164.2 (2)	C11—N1—O1—B1	162.9 (2)
O2—C2—C1—C10	−175.5 (2)	C11—N1—C12—C13	19.4 (3)
O2—C2—C1—C11	−3.0 (3)	C12—O3—B1—C19	−119.8 (2)
O2—C2—C3—C4	175.7 (2)	C12—O3—B1—C25	113.1 (2)
O3—C12—N1—C11	−162.3 (2)	C12—N1—O1—B1	−2.3 (2)
O3—C12—C13—C14	47.0 (3)	C12—C13—C14—C15	−175.4 (2)
O3—C12—C13—C18	−127.8 (2)	C12—C13—C18—C17	174.6 (2)
O3—B1—O1—N1	3.3 (2)	C13—C12—O3—B1	−179.0 (2)
O3—B1—C19—C20	8.2 (3)	C13—C14—C15—C16	0.5 (3)
O3—B1—C19—C24	−172.7 (2)	C13—C18—C17—C16	0.8 (3)
O3—B1—C25—C26	−92.9 (2)	C14—C13—C18—C17	−0.1 (3)
O3—B1—C25—C30	87.8 (2)	C14—C15—C16—C17	0.3 (3)
N1—O1—B1—C19	118.2 (2)	C15—C14—C13—C18	−0.6 (3)
N1—O1—B1—C25	−112.3 (2)	C15—C16—C17—C18	−0.9 (4)
N1—C11—C1—C2	98.6 (2)	C19—C20—C21—C22	−1.2 (4)
N1—C11—C1—C10	−89.2 (2)	C19—C24—C23—C22	−0.7 (4)
N1—C12—O3—B1	2.6 (2)	C19—B1—C25—C26	142.8 (2)
N1—C12—C13—C14	−134.9 (2)	C19—B1—C25—C30	−36.5 (3)
N1—C12—C13—C18	50.4 (3)	C20—C19—C24—C23	1.0 (3)
C1—C2—C3—C4	−2.9 (4)	C20—C19—B1—C25	132.7 (2)
C1—C10—C5—C4	−0.5 (3)	C20—C21—C22—C23	1.6 (4)
C1—C10—C5—C6	177.4 (2)	C21—C20—C19—C24	0.0 (3)
C1—C10—C9—C8	−177.1 (2)	C21—C20—C19—B1	179.1 (2)
C1—C11—N1—C12	−135.1 (2)	C21—C22—C23—C24	−0.6 (4)
C2—C1—C10—C5	−1.3 (3)	C23—C24—C19—B1	−178.2 (2)
C2—C1—C10—C9	177.1 (2)	C24—C19—B1—C25	−48.2 (3)
C2—C3—C4—C5	0.9 (4)	C25—C26—C27—C28	−0.4 (4)
C3—C2—C1—C10	3.0 (3)	C25—C30—C29—C28	−0.7 (4)
C3—C2—C1—C11	175.5 (2)	C26—C25—C30—C29	0.0 (3)
C3—C4—C5—C6	−177.2 (2)	C26—C27—C28—C29	−0.3 (4)
C3—C4—C5—C10	0.7 (3)	C27—C26—C25—C30	0.5 (3)
C4—C5—C6—C7	178.2 (3)	C27—C26—C25—B1	−178.9 (2)
C4—C5—C10—C9	−179.1 (2)	C27—C28—C29—C30	0.9 (4)
C5—C6—C7—C8	0.2 (4)	C29—C30—C25—B1	179.4 (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 formula	C₃₀H₂₄BNO₃·C₂H₆O
M_r	503.40
Crystal system, space group	Triclinic, 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)
V (Å³)	1355.18 (13)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.35 × 0.35 × 0.25

Data collection
Diffractometer	Rigaku AFC-6S diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.73, 0.85
No. of measured, independent and observed [I > 3σ(I)] reflections	5819, 5525, 3873
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.038, 0.97
No. of reflections	3873
No. of parameters	374
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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—N1	1.384 (2)	C13—C14	1.385 (2)
O1—B1	1.537 (2)	C13—C18	1.385 (3)
O2—C2	1.357 (2)	C14—C15	1.379 (3)
O3—C12	1.294 (2)	C15—C16	1.372 (3)
O3—B1	1.564 (2)	C16—C17	1.367 (3)
N1—C11	1.468 (2)	C17—C18	1.381 (3)
N1—C12	1.301 (2)	C19—C20	1.389 (3)
C1—C2	1.374 (3)	C19—C24	1.392 (3)
C1—C10	1.428 (3)	C19—B1	1.590 (3)
C1—C11	1.502 (2)	C20—C21	1.388 (4)
C2—C3	1.407 (3)	C21—C22	1.359 (4)
C3—C4	1.346 (3)	C22—C23	1.368 (4)
C4—C5	1.417 (3)	C23—C24	1.391 (3)
C5—C6	1.411 (3)	C25—C26	1.395 (3)
C5—C10	1.423 (3)	C25—C30	1.386 (3)
C6—C7	1.348 (4)	C25—B1	1.602 (3)
C7—C8	1.392 (4)	C26—C27	1.391 (3)
C8—C9	1.365 (3)	C27—C28	1.360 (4)
C9—C10	1.405 (3)	C28—C29	1.365 (4)
C12—C13	1.468 (2)	C29—C30	1.387 (3)

N1—O1—B1	106.71 (12)	C14—C13—C18	119.4 (2)
C12—O3—B1	108.85 (13)	C13—C14—C15	120.5 (2)
O1—N1—C11	115.01 (13)	C14—C15—C16	119.6 (2)
O1—N1—C12	112.05 (13)	C15—C16—C17	120.3 (2)
C11—N1—C12	130.78 (15)	C16—C17—C18	120.8 (2)
C2—C1—C10	118.8 (2)	C13—C18—C17	119.4 (2)
C2—C1—C11	118.5 (2)	C20—C19—C24	115.8 (2)
C10—C1—C11	122.3 (2)	C20—C19—B1	123.7 (2)
O2—C2—C1	118.1 (2)	C24—C19—B1	120.4 (2)
O2—C2—C3	120.3 (2)	C19—C20—C21	122.4 (2)
C1—C2—C3	121.6 (2)	C20—C21—C22	120.0 (3)
C2—C3—C4	120.1 (2)	C21—C22—C23	119.8 (3)
C3—C4—C5	121.4 (2)	C22—C23—C24	120.0 (2)
C4—C5—C6	121.3 (2)	C19—C24—C23	121.9 (2)
C4—C5—C10	118.6 (2)	C26—C25—C30	115.9 (2)
C6—C5—C10	120.0 (2)	C26—C25—B1	123.0 (2)
C5—C6—C7	121.0 (2)	C30—C25—B1	121.1 (2)
C6—C7—C8	119.5 (2)	C25—C26—C27	121.6 (2)
C7—C8—C9	121.4 (2)	C26—C27—C28	120.6 (2)
C8—C9—C10	121.1 (2)	C27—C28—C29	119.3 (2)
C1—C10—C5	119.5 (2)	C28—C29—C30	120.3 (2)
C1—C10—C9	123.5 (2)	C25—C30—C29	122.3 (2)
C5—C10—C9	117.0 (2)	O1—B1—O3	98.35 (13)
N1—C11—C1	115.26 (15)	O1—B1—C19	111.3 (2)
O3—C12—N1	113.91 (15)	O1—B1—C25	111.5 (2)
O3—C12—C13	119.00 (15)	O3—B1—C19	109.6 (2)
N1—C12—C13	127.1 (2)	O3—B1—C25	110.2 (2)
C12—C13—C14	118.5 (2)	C19—B1—C25	114.7 (2)
C12—C13—C18	121.9 (2)

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