A di­phenyl­boron chelate of an N-alkyl-2,2-di­aryl­glycolo­hydro­xamic acid

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

doi:10.1107/S1600536802016124

A diphenylboron chelate of an N-alkyl-2,2-diarylglycolohydroxamic acid

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

4-Cyclohexyl-5-[hydroxy-bis(4-methoxyphenyl)methyl]-2,2-diphenyl-1,3-dioxa-4-azonia-2-borata-4-cyclopentene, C₃₄H₃₆BNO₅, contains a five-membered heterocyclic ring with a B-envelope conformation. Bond lengths and angles are similar to those in related hydroxamatoboron chelates.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016124/cf6204sup1.cif Contains datablocks global, II
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016124/cf6204IIsup2.hkl Contains datablock II

CCDC reference: 198955

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Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R factor = 0.040
wR factor = 0.038
Data-to-parameter ratio = 10.0

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No syntax errors found

ADDSYM reports no extra symmetry

Comment top

In the course of our investigations of hydroxamic acids as bi- or polydentate ligands in the formation of boron complexes (Kliegel et al., 1996, and references therein; Kliegel et al., 2001), we chose the 2,2-diaryl derivative of an N-alkyl glycolohydroxamic acid, (I), for the chelatization of the diphenylborenium (Ph₂B⁺) ion. The crystalline compound obtained from the reaction of (I) with diphenylborinic acid (anhydride) shows an elemental composition and spectroscopic data corresponding with any of the structural alternatives (II)–(IV). In the ¹H NMR spectrum of the colorless substance, however, the chemical shift of the OH-proton signal at relatively high field (δ = 3.15 p.p.m.) points to an alcoholic hydroxy group [as in (II)], rather than to hydroxamic acid moieties [as in (III) or (IV)], which normally give OH signals at a lower field. The molecular structure (II) would harmonize with the five-membered BONCO chelate ring systems established for the diphenylboron chelate of an N-unsubstituted 2,2-dialkylglycolohydroxamic acid and other hydroxamatoboron complexes (Kliegel et al., 1996, and references therein; Kliegel et al., 2001). A six-membered BONCCO ring, as in the possible structure (III), had been found in the difluoroboron chelate of an N,O-disubstituted 2,2-diphenylglycolohydroxamic acid (Kliegel, Schumacher, Rettig & Trotter, 1991), and the five-membered BOCCO ring system, as in the alternative structure (IV), is realised in the difluoroboron chelates of other derivatives of 2,2-diary1glycolohydroxamic acids (Kliegel et al., 1992). The X-ray analysis confirms the molecular structure (II), a typical hydroxamatoboron complex, the general geometry of which is very similar to that of related compounds (Kliegel et al., 1996, and references therein; Kliegel et al., 2001). The preference of the hydroxamate group as the ligand for the Ph₂B⁺ ion is in agreement with the findings for the diphenylboron chelates of hydroxamic acids containing additional 2-hydroxy groups as possible nucleophilic ligands in the carbonic acid part (Kliegel et al., 1996) or in the hydroxylamine part (Kliegel, Schumacher, Tajerbashi et al., 1991).

The five-membered BONCO ring has a pronounced B-envelope conformation with approximate planarity of the ONCO ring portion [dihedral angle 4.2 (2)°]. A considerable double-bond character of the C1—N1 bond [1.299 (3) Å], with an estimated (Häfelinger, 1970) and calculated (Paolini, 1990) π-bond order of 0.77 and 0.82, respectively, justifies the depicted chemical formula (II), with a predominant C=N double bond, representing the most important canonical structure. However, the C1—O2 bond [1.292 (2) Å] retains about 55% of its double-bond character. The two O—B bonds show an abnormally large difference of 0.083 Å [B—O(N) = 1.515 (3), B—O(C) = 1.598 (3) Å], compared to other hydroxamatoboron complexes, where differences are between 0.001 and 0.035 Å (Kliegel et al., 1996, and references therein; Kliegel et al., 2001). The considerably longer (C)O—B bond [1.598 (3) Å] points to the weaker donor property of the carbonyl group in this O,O-bidentate hydroxamate ligand.

Molecules of the chelate (II) are linked along a glide plane by O3—H1···O5 hydrogen bonds (Table 2).

Experimental top

N-Cyclohexyl-2,2-bis(4-methoxyphenyl)glycolohydroxamic acid (Geffken & Lauterbach, 1985) (1.16 g, 3 mmol) and diphenylborinic acid anhydride [oxybis(diphenylborane)] (0.52 g, 1.5 mmol) were dissolved in a small amount of absolute ethanol by slight heating. During cooling of the solution crystallization commenced spontaneously or after addition of petroleum ether. Yield of (II): 1.18 g (72%) of colorless crystals (with nacrous lustre), m.p. 417–419 K (from ethanol). IR (KBr): 3450 (O—H), 1610, 1595, 1585 (C=N/C=O, C=C). ¹H NMR (90 MHz, CDCl₃—TMS), δ (p.p.m.): 0.75–2.25 (m, (CH₂)₅), 3.15 (s, exchangeable, OH), 3.78 (s, 2 OCH₃), 3.75–4.30 (m, N—CH), 6.73–6.97 (m, 4 aromatic H), 7.12–7.60 (m, 14 aromatic H). Analysis calculated for C₃₄H₃₆BNO₅: C 74.32, H 6.60, N 2.55%; found: C 74.25, H 6.65, N 2.65%. 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: CAD-4 Diffractometer Control Software (Enraf-Nonius, 1978); cell refinement: CAD-4 Diffractometer Control Software; data reduction: local programs (Rettig, 1978); program(s) used to solve structure: MULTAN80 (Main et al., 1980); program(s) used to refine structure: ORFLS (Busing et al., 1962); software used to prepare material for publication: TEXSAN (Molecular Structure Corporation, 1989).

Figures top

Fig. 1. View of the molecule (33% displacement ellipsoids).

(II) top

Crystal data top

C₃₄H₃₆BNO₅	D_x = 1.234 Mg m⁻³
M_r = 549.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 25 reflections
a = 24.106 (2) Å	θ = 18.0–21.4°
b = 20.763 (2) Å	µ = 0.08 mm⁻¹
c = 11.8193 (7) Å	T = 294 K
V = 5915.7 (8) Å³	Prism, colorless
Z = 8	0.30 × 0.30 × 0.20 mm
F(000) = 2336

Data collection top

Enraf-Nonius CAD-4 diffractometer	3752 reflections with I > 3σ(I)
Radiation source: X-ray tube	R_int = 0.0
Graphite monochromator	θ_max = 27.5°, θ_min = 0.0°
ω–2θ scans	h = 0→31
Absorption correction: ψ scan (Rettig, 1978)	k = 0→27
T_min = 0.97, T_max = 0.98	l = 0→15
6740 measured reflections	3 standard reflections every 150 reflections
6740 independent reflections	intensity decay: 1.4%

Refinement top

Refinement on F	0 restraints
Least-squares matrix: full	0 constraints
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.038	Weighting scheme based on measured s.u.'s w = 1/[σ²(F_o) + 0.0004F_o²]
S = 1.96	(Δ/σ)_max = 0.03
3752 reflections	Δρ_max = 0.16 e Å⁻³
375 parameters	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₃₄H₃₆BNO₅	V = 5915.7 (8) Å³
M_r = 549.45	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 24.106 (2) Å	µ = 0.08 mm⁻¹
b = 20.763 (2) Å	T = 294 K
c = 11.8193 (7) Å	0.30 × 0.30 × 0.20 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	3752 reflections with I > 3σ(I)
Absorption correction: ψ scan (Rettig, 1978)	R_int = 0.0
T_min = 0.97, T_max = 0.98	3 standard reflections every 150 reflections
6740 measured reflections	intensity decay: 1.4%
6740 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 = 1.96	Δρ_max = 0.16 e Å⁻³
3752 reflections	Δρ_min = −0.22 e Å⁻³
375 parameters

Special details top

Experimental. The scan width was (0.75 + 0.35tanθ)° with a variable ω scan speed (1.5–10°/min). 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
O1	0.43507 (5)	0.58472 (6)	0.48595 (11)	0.047 (1)
O2	0.36278 (5)	0.59787 (6)	0.35542 (10)	0.042 (1)
O3	0.27573 (6)	0.63936 (7)	0.58510 (11)	0.047 (1)
O4	0.20608 (6)	0.34675 (6)	0.51257 (12)	0.055 (1)
O5	0.19209 (6)	0.76473 (6)	0.13399 (12)	0.054 (1)
N1	0.38255 (6)	0.58995 (8)	0.53435 (13)	0.042 (1)
C1	0.34457 (8)	0.59949 (9)	0.45817 (16)	0.037 (1)
C2	0.38079 (9)	0.58496 (10)	0.65829 (17)	0.046 (1)
C3	0.39859 (12)	0.51844 (12)	0.6972 (2)	0.057 (1)
C4	0.39464 (13)	0.51511 (15)	0.8258 (2)	0.068 (2)
C5	0.42963 (13)	0.56632 (16)	0.8798 (2)	0.077 (2)
C6	0.41336 (14)	0.63290 (15)	0.8395 (2)	0.074 (2)
C7	0.41586 (13)	0.63727 (14)	0.7105 (2)	0.061 (1)
C8	0.28233 (7)	0.60589 (9)	0.48028 (15)	0.038 (1)
C9	0.42251 (8)	0.49636 (10)	0.33347 (19)	0.045 (1)
C10	0.40276 (10)	0.47285 (13)	0.2310 (2)	0.062 (1)
C11	0.39484 (11)	0.40760 (14)	0.2117 (3)	0.078 (2)
C12	0.40714 (11)	0.36412 (15)	0.2945 (3)	0.081 (2)
C13	0.42861 (11)	0.38500 (13)	0.3948 (3)	0.072 (2)
C14	0.43610 (9)	0.45032 (11)	0.4138 (2)	0.054 (1)
C15	0.46392 (8)	0.61749 (10)	0.28625 (17)	0.048 (1)
C16	0.48860 (10)	0.59833 (13)	0.1863 (2)	0.063 (1)
C17	0.51942 (13)	0.64048 (16)	0.1198 (3)	0.084 (2)
C18	0.52716 (13)	0.70252 (16)	0.1540 (3)	0.092 (2)
C19	0.50430 (14)	0.72245 (14)	0.2539 (3)	0.098 (2)
C20	0.47331 (11)	0.68075 (12)	0.3190 (3)	0.078 (2)
C21	0.26087 (7)	0.53642 (9)	0.49016 (15)	0.038 (1)
C22	0.22888 (9)	0.51754 (10)	0.58098 (18)	0.047 (1)
C23	0.21003 (10)	0.45452 (10)	0.59107 (19)	0.050 (1)
C24	0.22316 (8)	0.40955 (9)	0.51017 (17)	0.043 (1)
C25	0.25597 (9)	0.42776 (10)	0.41950 (19)	0.051 (1)
C26	0.27445 (9)	0.48996 (10)	0.40964 (19)	0.047 (1)
C27	0.25587 (8)	0.64562 (9)	0.38566 (15)	0.038 (1)
C28	0.21429 (8)	0.62326 (10)	0.31629 (18)	0.047 (1)
C29	0.19115 (9)	0.66164 (10)	0.23249 (19)	0.051 (1)
C30	0.20999 (8)	0.72353 (9)	0.21760 (17)	0.042 (1)
C31	0.25089 (9)	0.74747 (10)	0.28844 (18)	0.047 (1)
C32	0.27338 (9)	0.70921 (9)	0.37074 (18)	0.045 (1)
C33	0.16474 (12)	0.32983 (14)	0.5937 (2)	0.061 (2)
C34	0.15439 (14)	0.73990 (16)	0.0515 (3)	0.070 (2)
B1	0.42515 (10)	0.57198 (11)	0.3613 (2)	0.044 (1)
H1	0.2488 (11)	0.6672 (12)	0.578 (2)	0.071 (8)*
H2	0.3435	0.5915	0.6817	0.055*
H3	0.3749	0.4869	0.6646	0.068*
H4	0.4358	0.5107	0.6743	0.068*
H5	0.3571	0.5210	0.8479	0.082*
H6	0.4071	0.4740	0.8505	0.082*
H7	0.4251	0.5642	0.9596	0.092*
H8	0.4674	0.5588	0.8612	0.092*
H9	0.3766	0.6420	0.8638	0.089*
H10	0.4381	0.6636	0.8710	0.089*
H11	0.4532	0.6324	0.6864	0.073*
H12	0.4023	0.6781	0.6870	0.073*
H13	0.3944	0.5025	0.1722	0.074*
H14	0.3809	0.3932	0.1409	0.094*
H15	0.4008	0.3195	0.2824	0.097*
H16	0.4384	0.3548	0.4517	0.086*
H17	0.4510	0.4640	0.4841	0.065*
H18	0.4844	0.5550	0.1621	0.076*
H19	0.5351	0.6260	0.0506	0.101*
H20	0.5482	0.7315	0.1090	0.110*
H21	0.5098	0.7655	0.2787	0.118*
H22	0.4580	0.6957	0.3882	0.094*
H23	0.2196	0.5481	0.6377	0.056*
H24	0.1880	0.4425	0.6542	0.060*
H25	0.2658	0.3969	0.3636	0.061*
H26	0.2969	0.5016	0.3468	0.056*
H27	0.2011	0.5805	0.3260	0.056*
H28	0.1624	0.6452	0.1857	0.061*
H29	0.2634	0.7906	0.2798	0.056*
H30	0.3014	0.7262	0.4187	0.054*
H31	0.1782	0.3385	0.6677	0.073*
H32	0.1322	0.3544	0.5803	0.073*
H33	0.1563	0.2853	0.5871	0.073*
H34	0.1217	0.7252	0.0881	0.084*
H35	0.1452	0.7729	−0.0009	0.084*
H36	0.1713	0.7050	0.0125	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0374 (7)	0.0574 (9)	0.0456 (8)	0.0033 (6)	−0.0016 (6)	−0.0029 (7)
O2	0.0435 (8)	0.0450 (8)	0.0372 (8)	0.0057 (6)	−0.0001 (6)	−0.0025 (6)
O3	0.0546 (9)	0.0472 (8)	0.0392 (8)	0.0141 (7)	−0.0042 (7)	−0.0107 (6)
O4	0.0703 (10)	0.0392 (8)	0.0561 (9)	−0.0036 (7)	0.0102 (8)	0.0008 (7)
O5	0.0598 (9)	0.0470 (8)	0.0550 (9)	−0.0029 (7)	−0.0171 (8)	0.0111 (7)
N1	0.0394 (10)	0.0480 (10)	0.0398 (10)	0.0038 (7)	−0.0018 (8)	−0.0013 (8)
C1	0.0438 (11)	0.0306 (10)	0.0374 (11)	0.0029 (8)	−0.0033 (9)	−0.0027 (8)
C2	0.0430 (12)	0.0573 (13)	0.0378 (12)	0.0018 (10)	−0.0035 (10)	0.0022 (10)
C3	0.0648 (17)	0.0559 (15)	0.0507 (14)	0.0056 (13)	−0.0042 (12)	0.0049 (11)
C4	0.0722 (19)	0.077 (2)	0.0554 (16)	0.0092 (15)	−0.0006 (14)	0.0150 (14)
C5	0.073 (2)	0.114 (3)	0.0438 (16)	0.0030 (17)	−0.0077 (14)	0.0081 (14)
C6	0.083 (2)	0.093 (2)	0.0478 (15)	−0.0183 (17)	0.0009 (14)	−0.0148 (15)
C7	0.0742 (19)	0.0641 (17)	0.0458 (15)	−0.0082 (14)	−0.0010 (13)	−0.0066 (12)
C8	0.0416 (11)	0.0389 (11)	0.0339 (10)	0.0056 (8)	−0.0011 (9)	−0.0052 (8)
C9	0.0364 (11)	0.0471 (12)	0.0510 (13)	0.0055 (9)	0.0016 (10)	−0.0038 (10)
C10	0.0583 (15)	0.0576 (15)	0.0691 (17)	0.0099 (12)	−0.0043 (13)	−0.0117 (15)
C11	0.0659 (17)	0.071 (2)	0.097 (2)	0.0070 (14)	−0.0123 (16)	−0.0325 (18)
C12	0.0615 (17)	0.0506 (16)	0.132 (3)	0.0029 (13)	0.0008 (18)	−0.0219 (19)
C13	0.0638 (16)	0.0500 (16)	0.102 (2)	0.0069 (13)	0.0041 (16)	0.0069 (16)
C14	0.0488 (13)	0.0480 (14)	0.0653 (16)	0.0038 (10)	0.0044 (12)	0.0006 (12)
C15	0.0427 (12)	0.0453 (12)	0.0555 (13)	0.0058 (9)	0.0008 (10)	0.0010 (10)
C16	0.0712 (16)	0.0554 (15)	0.0633 (16)	−0.0017 (13)	0.0170 (13)	−0.0009 (13)
C17	0.093 (2)	0.082 (2)	0.078 (2)	−0.0038 (17)	0.0338 (17)	0.0077 (16)
C18	0.086 (2)	0.073 (2)	0.118 (3)	−0.0017 (17)	0.035 (2)	0.027 (2)
C19	0.095 (2)	0.0548 (17)	0.143 (3)	−0.0118 (16)	0.049 (2)	−0.002 (2)
C20	0.0770 (18)	0.0540 (15)	0.102 (2)	−0.0108 (12)	0.0340 (17)	−0.0109 (15)
C21	0.0396 (11)	0.0377 (11)	0.0352 (11)	0.0065 (8)	−0.0021 (9)	−0.0007 (8)
C22	0.0595 (13)	0.0439 (12)	0.0389 (11)	0.0060 (10)	0.0092 (11)	−0.0052 (10)
C23	0.0647 (14)	0.0447 (13)	0.0392 (12)	0.0024 (10)	0.0118 (11)	0.0047 (11)
C24	0.0493 (12)	0.0380 (11)	0.0431 (11)	0.0038 (9)	−0.0019 (10)	0.0033 (9)
C25	0.0604 (14)	0.0426 (13)	0.0487 (13)	0.0006 (10)	0.0107 (11)	−0.0108 (10)
C26	0.0533 (13)	0.0463 (13)	0.0422 (12)	−0.0015 (10)	0.0116 (11)	−0.0039 (10)
C27	0.0385 (11)	0.0350 (11)	0.0393 (11)	0.0036 (8)	0.0006 (9)	−0.0034 (8)
C28	0.0481 (13)	0.0367 (12)	0.0558 (13)	−0.0082 (10)	−0.0087 (11)	0.0057 (10)
C29	0.0467 (13)	0.0488 (13)	0.0574 (14)	−0.0082 (10)	−0.0163 (11)	0.0045 (11)
C30	0.0449 (12)	0.0386 (11)	0.0428 (11)	0.0037 (9)	−0.0025 (9)	0.0037 (9)
C31	0.0585 (13)	0.0325 (11)	0.0500 (13)	−0.0030 (11)	−0.0079 (11)	−0.0009 (10)
C32	0.0493 (12)	0.0376 (12)	0.0470 (12)	−0.0023 (9)	−0.0111 (11)	−0.0076 (9)
C33	0.080 (2)	0.0500 (15)	0.0526 (16)	−0.0088 (14)	0.0088 (14)	0.0071 (13)
C34	0.0689 (19)	0.073 (2)	0.0686 (18)	−0.0073 (16)	−0.0265 (16)	0.0153 (17)
B1	0.0404 (13)	0.0467 (14)	0.0444 (14)	0.0067 (10)	−0.0009 (11)	−0.0029 (11)

Geometric parameters (Å, º) top

O1—N1	1.393 (2)	C10—C11	1.387 (4)
O1—B1	1.515 (3)	C11—C12	1.364 (5)
O2—C1	1.292 (2)	C12—C13	1.364 (5)
O2—B1	1.598 (3)	C13—C14	1.386 (4)
O3—C8	1.429 (2)	C15—C16	1.382 (3)
O3—H1	0.87 (3)	C15—C20	1.388 (3)
O4—C24	1.368 (2)	C15—B1	1.598 (3)
O4—C33	1.427 (3)	C16—C17	1.391 (4)
O5—C30	1.376 (2)	C17—C18	1.363 (5)
O5—C34	1.429 (3)	C18—C19	1.367 (5)
N1—C1	1.299 (2)	C19—C20	1.378 (4)
N1—C2	1.469 (2)	C21—C22	1.379 (3)
C1—C8	1.529 (3)	C21—C26	1.394 (3)
C2—C3	1.518 (3)	C22—C23	1.390 (3)
C2—C7	1.508 (4)	C23—C24	1.373 (3)
C3—C4	1.525 (4)	C24—C25	1.385 (3)
C4—C5	1.500 (4)	C25—C26	1.371 (3)
C5—C6	1.514 (4)	C27—C28	1.376 (3)
C6—C7	1.528 (4)	C27—C32	1.397 (3)
C8—C21	1.537 (3)	C28—C29	1.388 (3)
C8—C27	1.529 (3)	C29—C30	1.374 (3)
C9—C10	1.390 (4)	C30—C31	1.386 (3)
C9—C14	1.386 (3)	C31—C32	1.368 (3)
C9—B1	1.605 (3)

O1···C14ⁱ	3.403 (3)	O4···C31^iv	3.513 (2)
O2···C33ⁱⁱ	3.502 (3)	O4···C6ⁱⁱ	3.557 (4)
O3···O5ⁱⁱⁱ	2.892 (2)	O4···C29^v	3.595 (3)
O3···C31ⁱⁱⁱ	3.414 (2)	C10···C23ⁱⁱ	3.522 (4)
O4···C32^iv	3.348 (2)	C30···C33ⁱⁱ	3.534 (4)
O4···C30^v	3.478 (2)	C31···C33ⁱⁱ	3.466 (4)

N1—O1—B1	105.6 (1)	C16—C15—B1	123.8 (2)
C1—O2—B1	106.7 (1)	C20—C15—B1	120.0 (2)
C8—O3—H1	109 (2)	C15—C16—C17	122.1 (2)
C24—O4—C33	117.3 (2)	C16—C17—C18	120.0 (3)
C30—O5—C34	117.7 (2)	C17—C18—C19	119.1 (3)
O1—N1—C1	111.6 (1)	C18—C19—C20	120.7 (3)
O1—N1—C2	115.5 (1)	C15—C20—C19	121.8 (3)
C1—N1—C2	133.0 (2)	C8—C21—C22	121.0 (2)
O2—C1—N1	114.1 (2)	C8—C21—C26	121.2 (2)
O2—C1—C8	119.8 (2)	C22—C21—C26	117.8 (2)
N1—C1—C8	125.9 (2)	C21—C22—C23	121.1 (2)
N1—C2—C3	111.0 (2)	C22—C23—C24	120.3 (2)
N1—C2—C7	109.9 (2)	O4—C24—C23	124.4 (2)
C3—C2—C7	111.9 (2)	O4—C24—C25	116.6 (2)
C2—C3—C4	109.0 (2)	C23—C24—C25	119.0 (2)
C3—C4—C5	110.9 (2)	C24—C25—C26	120.6 (2)
C4—C5—C6	111.6 (3)	C21—C26—C25	121.2 (2)
C5—C6—C7	111.0 (2)	C8—C27—C28	123.9 (2)
C2—C7—C6	110.1 (2)	C8—C27—C32	118.4 (2)
O3—C8—C1	107.4 (1)	C28—C27—C32	117.6 (2)
O3—C8—C21	110.7 (1)	C27—C28—C29	121.6 (2)
O3—C8—C27	109.0 (1)	C28—C29—C30	119.7 (2)
C1—C8—C21	105.2 (1)	O5—C30—C29	124.7 (2)
C1—C8—C27	109.3 (1)	O5—C30—C31	115.7 (2)
C21—C8—C27	114.9 (1)	C29—C30—C31	119.6 (2)
C10—C9—C14	115.8 (2)	C30—C31—C32	120.2 (2)
C10—C9—B1	122.4 (2)	C27—C32—C31	121.2 (2)
C14—C9—B1	121.6 (2)	O1—B1—O2	97.6 (1)
C9—C10—C11	122.2 (3)	O1—B1—C9	112.1 (2)
C10—C11—C12	119.9 (3)	O1—B1—C15	110.1 (2)
C11—C12—C13	119.7 (3)	O2—B1—C9	106.4 (2)
C12—C13—C14	120.1 (3)	O2—B1—C15	109.1 (2)
C9—C14—C13	122.2 (3)	C9—B1—C15	119.2 (2)
C16—C15—C20	116.2 (2)

O1—N1—C1—O2	4.2 (2)	C3—C4—C5—C6	57.2 (3)
O1—N1—C1—C8	178.5 (2)	C4—C3—C2—C7	58.2 (3)
O1—N1—C2—C3	−64.9 (2)	C4—C5—C6—C7	−55.5 (3)
O1—N1—C2—C7	59.4 (2)	C8—C1—O2—B1	−164.8 (2)
O1—B1—O2—C1	−18.1 (2)	C8—C21—C22—C23	−179.1 (2)
O1—B1—C9—C10	166.5 (2)	C8—C21—C26—C25	179.0 (2)
O1—B1—C9—C14	−8.7 (3)	C8—C27—C28—C29	179.1 (2)
O1—B1—C15—C16	142.9 (2)	C8—C27—C32—C31	−179.3 (2)
O1—B1—C15—C20	−38.7 (3)	C9—C10—C11—C12	−0.7 (4)
O2—C1—N1—C2	−177.0 (2)	C9—C14—C13—C12	−0.1 (4)
O2—C1—C8—O3	−149.9 (2)	C9—B1—C15—C16	11.3 (3)
O2—C1—C8—C21	92.1 (2)	C9—B1—C15—C20	−170.3 (2)
O2—C1—C8—C27	−31.8 (2)	C10—C9—C14—C13	−2.3 (3)
O2—B1—O1—N1	19.7 (2)	C10—C9—B1—C15	−62.8 (3)
O2—B1—C9—C10	60.9 (2)	C10—C11—C12—C13	−1.8 (4)
O2—B1—C9—C14	−114.3 (2)	C11—C10—C9—C14	2.7 (3)
O2—B1—C15—C16	−111.1 (2)	C11—C10—C9—B1	−172.8 (2)
O2—B1—C15—C20	67.3 (3)	C11—C12—C13—C14	2.2 (4)
O3—C8—C1—N1	36.2 (2)	C13—C14—C9—B1	173.2 (2)
O3—C8—C21—C22	13.4 (2)	C14—C9—B1—C15	122.0 (2)
O3—C8—C21—C26	−164.6 (2)	C15—C16—C17—C18	1.5 (4)
O3—C8—C27—C28	−122.2 (2)	C15—C20—C19—C18	−0.2 (5)
O3—C8—C27—C32	55.5 (2)	C16—C15—C20—C19	1.6 (4)
O4—C24—C23—C22	−179.4 (2)	C16—C17—C18—C19	0.0 (5)
O4—C24—C25—C26	179.3 (2)	C17—C16—C15—C20	−2.3 (4)
O5—C30—C29—C28	176.7 (2)	C17—C16—C15—B1	176.1 (2)
O5—C30—C31—C32	−176.8 (2)	C17—C18—C19—C20	−0.7 (5)
N1—O1—B1—C9	−91.5 (2)	C19—C20—C15—B1	−176.9 (3)
N1—O1—B1—C15	133.3 (2)	C21—C8—C27—C28	2.7 (3)
N1—C1—O2—B1	9.8 (2)	C21—C8—C27—C32	−179.7 (2)
N1—C1—C8—C21	−81.8 (2)	C21—C22—C23—C24	0.1 (3)
N1—C1—C8—C27	154.3 (2)	C21—C26—C25—C24	0.0 (3)
N1—C2—C3—C4	−178.5 (2)	C22—C21—C8—C27	−110.5 (2)
N1—C2—C7—C6	179.1 (2)	C22—C21—C26—C25	0.9 (3)
C1—O2—B1—C9	97.7 (2)	C22—C23—C24—C25	0.8 (3)
C1—O2—B1—C15	−132.5 (2)	C23—C22—C21—C26	−1.0 (3)
C1—N1—O1—B1	−16.9 (2)	C23—C24—O4—C33	10.8 (3)
C1—N1—C2—C3	116.4 (2)	C23—C24—C25—C26	−0.9 (3)
C1—N1—C2—C7	−119.3 (2)	C25—C24—O4—C33	−169.4 (2)
C1—C8—C21—C22	129.2 (2)	C26—C21—C8—C27	71.5 (2)
C1—C8—C21—C26	−48.8 (2)	C27—C28—C29—C30	0.1 (3)
C1—C8—C27—C28	120.6 (2)	C27—C32—C31—C30	−0.1 (3)
C1—C8—C27—C32	−61.7 (2)	C28—C27—C32—C31	−1.4 (3)
C2—N1—O1—B1	164.2 (2)	C28—C29—C30—C31	−1.7 (3)
C2—N1—C1—C8	−2.8 (3)	C29—C28—C27—C32	1.4 (3)
C2—C3—C4—C5	−57.6 (3)	C29—C30—O5—C34	−5.0 (3)
C2—C7—C6—C5	54.7 (3)	C29—C30—C31—C32	1.7 (3)
C3—C2—C7—C6	−57.1 (3)	C31—C30—O5—C34	173.4 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, −y+1, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1/2, y−1/2, z; (v) −x+1/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₄H₃₆BNO₅
M_r	549.45
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	294
a, b, c (Å)	24.106 (2), 20.763 (2), 11.8193 (7)
V (Å³)	5915.7 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	ψ scan (Rettig, 1978)
T_min, T_max	0.97, 0.98
No. of measured, independent and observed [I > 3σ(I)] reflections	6740, 6740, 3752
R_int	0.0
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.038, 1.96
No. of reflections	3752
No. of parameters	375
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.22

Computer programs: CAD-4 Diffractometer Control Software (Enraf-Nonius, 1978), CAD-4 Diffractometer Control Software, local programs (Rettig, 1978), MULTAN80 (Main et al., 1980), ORFLS (Busing et al., 1962), TEXSAN (Molecular Structure Corporation, 1989).

Selected geometric parameters (Å, º) top

O1—N1	1.393 (2)	C10—C11	1.387 (4)
O1—B1	1.515 (3)	C11—C12	1.364 (5)
O2—C1	1.292 (2)	C12—C13	1.364 (5)
O2—B1	1.598 (3)	C13—C14	1.386 (4)
O3—C8	1.429 (2)	C15—C16	1.382 (3)
O4—C24	1.368 (2)	C15—C20	1.388 (3)
O4—C33	1.427 (3)	C15—B1	1.598 (3)
O5—C30	1.376 (2)	C16—C17	1.391 (4)
O5—C34	1.429 (3)	C17—C18	1.363 (5)
N1—C1	1.299 (2)	C18—C19	1.367 (5)
N1—C2	1.469 (2)	C19—C20	1.378 (4)
C1—C8	1.529 (3)	C21—C22	1.379 (3)
C2—C3	1.518 (3)	C21—C26	1.394 (3)
C2—C7	1.508 (4)	C22—C23	1.390 (3)
C3—C4	1.525 (4)	C23—C24	1.373 (3)
C4—C5	1.500 (4)	C24—C25	1.385 (3)
C5—C6	1.514 (4)	C25—C26	1.371 (3)
C6—C7	1.528 (4)	C27—C28	1.376 (3)
C8—C21	1.537 (3)	C27—C32	1.397 (3)
C8—C27	1.529 (3)	C28—C29	1.388 (3)
C9—C10	1.390 (4)	C29—C30	1.374 (3)
C9—C14	1.386 (3)	C30—C31	1.386 (3)
C9—B1	1.605 (3)	C31—C32	1.368 (3)

N1—O1—B1	105.6 (1)	C16—C15—B1	123.8 (2)
C1—O2—B1	106.7 (1)	C20—C15—B1	120.0 (2)
C24—O4—C33	117.3 (2)	C15—C16—C17	122.1 (2)
C30—O5—C34	117.7 (2)	C16—C17—C18	120.0 (3)
O1—N1—C1	111.6 (1)	C17—C18—C19	119.1 (3)
O1—N1—C2	115.5 (1)	C18—C19—C20	120.7 (3)
C1—N1—C2	133.0 (2)	C15—C20—C19	121.8 (3)
O2—C1—N1	114.1 (2)	C8—C21—C22	121.0 (2)
O2—C1—C8	119.8 (2)	C8—C21—C26	121.2 (2)
N1—C1—C8	125.9 (2)	C22—C21—C26	117.8 (2)
N1—C2—C3	111.0 (2)	C21—C22—C23	121.1 (2)
N1—C2—C7	109.9 (2)	C22—C23—C24	120.3 (2)
C3—C2—C7	111.9 (2)	O4—C24—C23	124.4 (2)
C2—C3—C4	109.0 (2)	O4—C24—C25	116.6 (2)
C3—C4—C5	110.9 (2)	C23—C24—C25	119.0 (2)
C4—C5—C6	111.6 (3)	C24—C25—C26	120.6 (2)
C5—C6—C7	111.0 (2)	C21—C26—C25	121.2 (2)
C2—C7—C6	110.1 (2)	C8—C27—C28	123.9 (2)
O3—C8—C1	107.4 (1)	C8—C27—C32	118.4 (2)
O3—C8—C21	110.7 (1)	C28—C27—C32	117.6 (2)
O3—C8—C27	109.0 (1)	C27—C28—C29	121.6 (2)
C1—C8—C21	105.2 (1)	C28—C29—C30	119.7 (2)
C1—C8—C27	109.3 (1)	O5—C30—C29	124.7 (2)
C21—C8—C27	114.9 (1)	O5—C30—C31	115.7 (2)
C10—C9—C14	115.8 (2)	C29—C30—C31	119.6 (2)
C10—C9—B1	122.4 (2)	C30—C31—C32	120.2 (2)
C14—C9—B1	121.6 (2)	C27—C32—C31	121.2 (2)
C9—C10—C11	122.2 (3)	O1—B1—O2	97.6 (1)
C10—C11—C12	119.9 (3)	O1—B1—C9	112.1 (2)
C11—C12—C13	119.7 (3)	O1—B1—C15	110.1 (2)
C12—C13—C14	120.1 (3)	O2—B1—C9	106.4 (2)
C9—C14—C13	122.2 (3)	O2—B1—C15	109.1 (2)
C16—C15—C20	116.2 (2)	C9—B1—C15	119.2 (2)

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A di­phenyl­boron chelate of an N-alkyl-2,2-di­aryl­glycolo­hydro­xamic acid

Supporting information

Key indicators

checkCIF results

A diphenylboron chelate of an N-alkyl-2,2-diarylglycolohydroxamic acid