A highly efficient anti­oxidant based on boron and a Schiff base bridged phenolic di­phenyl­amine: synthesis, crystal structure and thermal and anti­oxidant properties

Anti­oxidants can effectively protect vegetable-oil-based lubricants against oxidative degradation and prolong their service life. A novel com­pound, (E)-4-({3,5-di-tert-butyl-2-[(di­phenyl­boran­yl)­oxy]benzyl­idene}amino)-N-phenyl­aniline (BSPD) or {2-[(4-anilinophen­yl)imino­methyl-κN]-4,6-di-tert-butyl­phenolato-κO}di­phenyl­boron, C₃₉H₄₁BN₂O, was synthesized by a one-pot reaction of the Schiff base bridged phenolic di­phenyl­amine 2,4-di-tert-butyl-6-{N-[4-(phenyl­amino)­phen­yl]carboximido­yl}phenol (SPD) with phenyl­boronic acid. The corresponding single-crystal X-ray study revealed that the B atom in BSPD has a typical tetra­hedral geometry, and the N,O-chelated six-membered ring adopts a chair conformation. According to thermogravimetric analysis, the 5% weight-loss tem­per­ature of BSPD increases to 328 °C and the 95% weight-loss tem­per­ature is up to 414 °C. More importantly, the anti­oxidant capability of BSPD in vegetable oil is much better than that of commercial anti­oxidants [di­phenyl­amine (DPA) and 2,6-di-tert-butyl-4-methyl­phenol (BHT)] and un­modi­fied SPD.

Computing details

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2010); software used to prepare material for publication: SHELXTL (Bruker, 2010).

{2-[(4-Anilinophenyl)iminomethyl-κN]-4,6-di-tert-\ butylphenolato-κO}diphenylboron

Crystal data

C39H41BN2O	F(000) = 604
Mr = 564.55	Dx = 1.169 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 10.6730 (5) Å	Cell parameters from 9977 reflections
b = 10.0539 (4) Å	θ = 2.2–27.5°
c = 15.0271 (7) Å	µ = 0.07 mm^−1
β = 96.095 (1)°	T = 295 K
V = 1603.37 (12) Å^3	Prismatic, colorless
Z = 2	0.20 × 0.17 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer	5477 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.059
Absorption correction: multi-scan SADABS	θmax = 26.0°, θmin = 2.4°
Tmin = 0.614, Tmax = 0.745	h = −13→13
23747 measured reflections	k = −12→11
6249 independent reflections	l = −18→18

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0513P)^2 + 0.176P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.043	(Δ/σ)max < 0.001
wR(F^2) = 0.110	Δρmax = 0.15 e Å^−3
S = 1.03	Δρmin = −0.15 e Å^−3
6249 reflections	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
396 parameters	Extinction coefficient: 0.080 (10)
2 restraints	Absolute structure: Flack (1983), 3116 Friedel pairs The experimental value of the Flack parameter is unreliable, as it has a large s.u. The following item in the CIF and the Table is the refined Flack parameter, 0.1(4).
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.1 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.58291 (17)	0.29385 (18)	0.58531 (12)	0.0415 (4)
N1	0.4964 (2)	0.4678 (2)	0.47909 (15)	0.0425 (5)
N2	0.1371 (2)	0.8761 (3)	0.41632 (19)	0.0555 (7)
H2	0.069857	0.852951	0.383366	0.067*
C1	0.5142 (3)	0.3850 (3)	0.41515 (19)	0.0466 (6)
H1	0.480869	0.406135	0.357181	0.056*
C2	0.5825 (3)	0.2632 (3)	0.42938 (19)	0.0440 (6)
C3	0.6104 (2)	0.2174 (3)	0.51757 (17)	0.0383 (6)
C4	0.6587 (2)	0.0868 (3)	0.53326 (17)	0.0383 (6)
C5	0.6783 (2)	0.0130 (3)	0.45761 (19)	0.0418 (6)
H5	0.710546	−0.072473	0.466659	0.050*
C6	0.6533 (3)	0.0567 (3)	0.36887 (19)	0.0443 (7)
C7	0.6041 (3)	0.1826 (3)	0.35608 (19)	0.0485 (7)
H7	0.584944	0.214840	0.298223	0.058*
C8	0.6853 (3)	0.0302 (3)	0.62825 (18)	0.0413 (6)
C9	0.5610 (3)	0.0116 (4)	0.6682 (2)	0.0604 (8)
H9A	0.519887	0.096092	0.671495	0.091*
H9B	0.577082	−0.025465	0.727164	0.091*
H9C	0.507751	−0.047618	0.631018	0.091*
C10	0.7700 (3)	0.1236 (3)	0.6881 (2)	0.0574 (8)
H10A	0.844744	0.142770	0.660072	0.086*
H10B	0.792871	0.081776	0.744907	0.086*
H10C	0.725652	0.204802	0.696772	0.086*
C11	0.7525 (3)	−0.1039 (3)	0.6286 (2)	0.0577 (8)
H11A	0.700400	−0.166604	0.593653	0.087*
H11B	0.768454	−0.135614	0.689026	0.087*
H11C	0.830955	−0.093656	0.603480	0.087*
C12	0.6772 (3)	−0.0367 (3)	0.2911 (2)	0.0522 (7)
C13	0.8139 (3)	−0.0836 (5)	0.3025 (2)	0.0711 (11)
H13A	0.868894	−0.008303	0.300877	0.107*
H13B	0.827893	−0.143725	0.254940	0.107*
H13C	0.830972	−0.128355	0.358964	0.107*
C14	0.5937 (4)	−0.1619 (4)	0.2957 (3)	0.0755 (11)
H14A	0.619185	−0.209824	0.349898	0.113*
H14B	0.602955	−0.217905	0.245124	0.113*
H14C	0.507139	−0.135542	0.295062	0.113*
C15	0.6500 (5)	0.0301 (5)	0.2018 (3)	0.0904 (14)
H15A	0.563378	0.057609	0.193724	0.136*
H15B	0.665710	−0.031042	0.155155	0.136*
H15C	0.703463	0.106510	0.199271	0.136*
C16	0.7209 (3)	0.5006 (3)	0.57004 (19)	0.0454 (6)
C17	0.8123 (3)	0.4814 (4)	0.6419 (2)	0.0578 (8)
H17	0.789907	0.436802	0.692064	0.069*
C18	0.9353 (3)	0.5256 (4)	0.6421 (3)	0.0701 (10)
H18	0.993902	0.509222	0.691179	0.084*
C19	0.9706 (3)	0.5942 (4)	0.5690 (3)	0.0727 (11)
H19	1.052254	0.626532	0.568899	0.087*
C20	0.8841 (4)	0.6134 (4)	0.4976 (3)	0.0731 (11)
H20	0.907595	0.657729	0.447688	0.088*
C21	0.7608 (3)	0.5684 (3)	0.4973 (2)	0.0565 (8)
H21	0.703633	0.583907	0.447221	0.068*
C22	0.5089 (3)	0.4983 (3)	0.65798 (19)	0.0424 (6)
C23	0.3979 (3)	0.4401 (4)	0.6792 (2)	0.0607 (8)
H23	0.365239	0.367485	0.646062	0.073*
C24	0.3347 (4)	0.4877 (5)	0.7484 (3)	0.0812 (12)
H24	0.260711	0.446715	0.761383	0.097*
C25	0.3807 (4)	0.5954 (4)	0.7983 (3)	0.0779 (11)
H25	0.336914	0.628389	0.843878	0.093*
C26	0.4911 (4)	0.6534 (4)	0.7804 (2)	0.0661 (9)
H26	0.523989	0.724856	0.814634	0.079*
C27	0.5535 (3)	0.6052 (3)	0.7111 (2)	0.0527 (7)
H27	0.628277	0.645808	0.699448	0.063*
C28	0.4063 (3)	0.5731 (3)	0.46099 (18)	0.0428 (6)
C29	0.2961 (3)	0.5542 (3)	0.4056 (2)	0.0481 (7)
H29	0.279566	0.471796	0.378836	0.058*
C30	0.2099 (3)	0.6561 (3)	0.3896 (2)	0.0489 (7)
H30	0.137514	0.642332	0.350431	0.059*
C31	0.2298 (3)	0.7792 (3)	0.43106 (19)	0.0448 (6)
C32	0.3398 (3)	0.7962 (3)	0.4880 (2)	0.0503 (7)
H32	0.354994	0.877312	0.516931	0.060*
C33	0.4271 (3)	0.6950 (3)	0.5026 (2)	0.0484 (7)
H33	0.500447	0.708916	0.540658	0.058*
C34	0.1399 (3)	1.0070 (3)	0.44859 (19)	0.0439 (6)
C35	0.0301 (3)	1.0620 (3)	0.4756 (2)	0.0501 (7)
H35	−0.042477	1.010437	0.473608	0.060*
C36	0.0278 (3)	1.1913 (3)	0.5050 (2)	0.0575 (8)
H36	−0.047157	1.227639	0.520253	0.069*
C37	0.1350 (4)	1.2669 (4)	0.5119 (3)	0.0655 (9)
H37	0.134259	1.353132	0.534314	0.079*
C38	0.2433 (3)	1.2142 (3)	0.4856 (3)	0.0634 (9)
H38	0.316224	1.265472	0.490443	0.076*
C39	0.2468 (3)	1.0867 (3)	0.4519 (2)	0.0554 (8)
H39	0.320265	1.054314	0.431500	0.066*
B1	0.5800 (3)	0.4425 (3)	0.5760 (2)	0.0411 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0529 (11)	0.0394 (10)	0.0332 (9)	0.0026 (8)	0.0094 (8)	−0.0035 (7)
N1	0.0505 (13)	0.0393 (12)	0.0386 (12)	0.0012 (10)	0.0086 (10)	0.0020 (10)
N2	0.0469 (14)	0.0479 (15)	0.0686 (17)	0.0042 (11)	−0.0090 (12)	−0.0054 (13)
C1	0.0573 (17)	0.0494 (16)	0.0336 (13)	0.0020 (13)	0.0071 (12)	0.0021 (12)
C2	0.0482 (15)	0.0447 (15)	0.0399 (14)	0.0023 (12)	0.0083 (12)	−0.0011 (12)
C3	0.0394 (14)	0.0421 (14)	0.0339 (13)	−0.0015 (11)	0.0070 (10)	−0.0051 (11)
C4	0.0350 (13)	0.0415 (14)	0.0387 (13)	−0.0018 (11)	0.0053 (11)	−0.0043 (11)
C5	0.0351 (13)	0.0469 (15)	0.0433 (14)	0.0021 (11)	0.0042 (11)	−0.0075 (12)
C6	0.0391 (14)	0.0541 (17)	0.0394 (15)	0.0039 (12)	0.0032 (11)	−0.0107 (12)
C7	0.0534 (17)	0.0600 (18)	0.0325 (13)	0.0053 (14)	0.0059 (12)	−0.0035 (12)
C8	0.0425 (15)	0.0434 (14)	0.0386 (14)	−0.0021 (11)	0.0072 (11)	−0.0028 (11)
C9	0.0567 (19)	0.075 (2)	0.0520 (19)	−0.0026 (16)	0.0169 (15)	0.0066 (16)
C10	0.064 (2)	0.062 (2)	0.0436 (16)	−0.0053 (15)	−0.0077 (14)	0.0009 (14)
C11	0.072 (2)	0.0521 (18)	0.0491 (17)	0.0093 (15)	0.0068 (15)	0.0051 (14)
C12	0.0507 (17)	0.0650 (19)	0.0405 (15)	0.0053 (15)	0.0034 (13)	−0.0179 (14)
C13	0.0510 (18)	0.101 (3)	0.063 (2)	0.0097 (18)	0.0149 (16)	−0.029 (2)
C14	0.063 (2)	0.085 (3)	0.077 (2)	−0.0052 (19)	0.0000 (18)	−0.033 (2)
C15	0.135 (4)	0.094 (3)	0.0422 (19)	0.023 (3)	0.008 (2)	−0.0216 (19)
C16	0.0543 (16)	0.0384 (14)	0.0450 (15)	−0.0005 (12)	0.0128 (12)	−0.0073 (11)
C17	0.0563 (18)	0.066 (2)	0.0511 (17)	−0.0078 (15)	0.0068 (14)	−0.0074 (15)
C18	0.052 (2)	0.076 (2)	0.081 (3)	−0.0019 (17)	0.0029 (18)	−0.018 (2)
C19	0.051 (2)	0.073 (2)	0.099 (3)	−0.0093 (17)	0.026 (2)	−0.014 (2)
C20	0.069 (2)	0.068 (2)	0.088 (3)	−0.0081 (18)	0.036 (2)	0.004 (2)
C21	0.0581 (18)	0.0550 (18)	0.0591 (19)	0.0008 (15)	0.0193 (15)	0.0042 (14)
C22	0.0498 (16)	0.0393 (14)	0.0385 (14)	0.0029 (11)	0.0071 (11)	0.0004 (11)
C23	0.062 (2)	0.063 (2)	0.060 (2)	−0.0097 (16)	0.0218 (16)	−0.0112 (16)
C24	0.076 (2)	0.095 (3)	0.079 (3)	−0.012 (2)	0.042 (2)	−0.010 (2)
C25	0.098 (3)	0.076 (3)	0.067 (2)	0.012 (2)	0.043 (2)	−0.011 (2)
C26	0.098 (3)	0.0520 (19)	0.0509 (18)	0.0037 (18)	0.0201 (18)	−0.0124 (14)
C27	0.069 (2)	0.0449 (16)	0.0463 (16)	−0.0023 (14)	0.0168 (14)	−0.0045 (13)
C28	0.0496 (15)	0.0401 (14)	0.0389 (14)	0.0025 (12)	0.0058 (12)	0.0037 (11)
C29	0.0576 (17)	0.0402 (15)	0.0460 (15)	−0.0043 (12)	0.0034 (13)	−0.0027 (12)
C30	0.0489 (16)	0.0471 (16)	0.0484 (16)	−0.0023 (13)	−0.0051 (13)	−0.0014 (13)
C31	0.0471 (15)	0.0420 (15)	0.0451 (15)	0.0012 (12)	0.0042 (12)	0.0051 (12)
C32	0.0536 (17)	0.0385 (15)	0.0562 (17)	0.0010 (12)	−0.0069 (13)	−0.0048 (13)
C33	0.0497 (15)	0.0444 (15)	0.0491 (16)	−0.0004 (12)	−0.0047 (13)	−0.0016 (12)
C34	0.0457 (16)	0.0457 (16)	0.0399 (14)	0.0033 (12)	0.0020 (12)	0.0063 (12)
C35	0.0432 (15)	0.0612 (19)	0.0462 (16)	0.0017 (13)	0.0056 (13)	0.0041 (14)
C36	0.0582 (19)	0.064 (2)	0.0513 (18)	0.0149 (16)	0.0110 (14)	0.0012 (15)
C37	0.077 (2)	0.0468 (18)	0.072 (2)	0.0064 (17)	0.0078 (18)	−0.0009 (16)
C38	0.060 (2)	0.0457 (17)	0.085 (2)	−0.0051 (14)	0.0099 (17)	0.0073 (16)
C39	0.0489 (17)	0.0484 (17)	0.071 (2)	0.0020 (13)	0.0151 (15)	0.0063 (15)
B1	0.0486 (17)	0.0391 (15)	0.0361 (15)	0.0012 (13)	0.0067 (13)	−0.0032 (12)

Geometric parameters (Å, º)

O1—C3	1.333 (3)	C16—C21	1.393 (4)
O1—B1	1.501 (4)	C16—B1	1.625 (4)
N1—C1	1.300 (4)	C17—C18	1.386 (5)
N1—C28	1.437 (4)	C17—H17	0.9300
N1—B1	1.644 (4)	C18—C19	1.383 (6)
N2—C31	1.389 (4)	C18—H18	0.9300
N2—C34	1.402 (4)	C19—C20	1.352 (6)
N2—H2	0.8600	C19—H19	0.9300
C1—C2	1.430 (4)	C20—C21	1.391 (5)
C1—H1	0.9300	C20—H20	0.9300
C2—C3	1.405 (4)	C21—H21	0.9300
C2—C7	1.406 (4)	C22—C23	1.388 (4)
C3—C4	1.421 (4)	C22—C27	1.392 (4)
C4—C5	1.392 (4)	C22—B1	1.615 (4)
C4—C8	1.535 (4)	C23—C24	1.385 (5)
C5—C6	1.402 (4)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.377 (6)
C6—C7	1.377 (4)	C24—H24	0.9300
C6—C12	1.541 (4)	C25—C26	1.367 (6)
C7—H7	0.9300	C25—H25	0.9300
C8—C9	1.524 (4)	C26—C27	1.383 (4)
C8—C11	1.527 (4)	C26—H26	0.9300
C8—C10	1.528 (4)	C27—H27	0.9300
C9—H9A	0.9600	C28—C29	1.380 (4)
C9—H9B	0.9600	C28—C33	1.383 (4)
C9—H9C	0.9600	C29—C30	1.381 (4)
C10—H10A	0.9600	C29—H29	0.9300
C10—H10B	0.9600	C30—C31	1.392 (4)
C10—H10C	0.9600	C30—H30	0.9300
C11—H11A	0.9600	C31—C32	1.388 (4)
C11—H11B	0.9600	C32—C33	1.382 (4)
C11—H11C	0.9600	C32—H32	0.9300
C12—C15	1.503 (5)	C33—H33	0.9300
C12—C13	1.526 (5)	C34—C39	1.391 (4)
C12—C14	1.548 (5)	C34—C35	1.394 (4)
C13—H13A	0.9600	C35—C36	1.374 (5)
C13—H13B	0.9600	C35—H35	0.9300
C13—H13C	0.9600	C36—C37	1.369 (5)
C14—H14A	0.9600	C36—H36	0.9300
C14—H14B	0.9600	C37—C38	1.368 (5)
C14—H14C	0.9600	C37—H37	0.9300
C15—H15A	0.9600	C38—C39	1.380 (5)
C15—H15B	0.9600	C38—H38	0.9300
C15—H15C	0.9600	C39—H39	0.9300
C16—C17	1.389 (5)
C3—O1—B1	120.5 (2)	C17—C16—B1	119.0 (3)
C1—N1—C28	118.6 (2)	C21—C16—B1	125.5 (3)
C1—N1—B1	116.6 (2)	C18—C17—C16	122.9 (3)
C28—N1—B1	124.8 (2)	C18—C17—H17	118.5
C31—N2—C34	127.9 (2)	C16—C17—H17	118.5
C31—N2—H2	116.0	C19—C18—C17	119.8 (4)
C34—N2—H2	116.0	C19—C18—H18	120.1
N1—C1—C2	123.4 (3)	C17—C18—H18	120.1
N1—C1—H1	118.3	C20—C19—C18	118.7 (3)
C2—C1—H1	118.3	C20—C19—H19	120.7
C3—C2—C7	121.0 (3)	C18—C19—H19	120.7
C3—C2—C1	118.4 (2)	C19—C20—C21	121.5 (4)
C7—C2—C1	120.0 (3)	C19—C20—H20	119.2
O1—C3—C2	119.3 (2)	C21—C20—H20	119.2
O1—C3—C4	120.8 (2)	C20—C21—C16	121.6 (4)
C2—C3—C4	119.7 (2)	C20—C21—H21	119.2
C5—C4—C3	116.1 (2)	C16—C21—H21	119.2
C5—C4—C8	122.2 (2)	C23—C22—C27	116.2 (3)
C3—C4—C8	121.6 (2)	C23—C22—B1	120.7 (3)
C4—C5—C6	125.4 (3)	C27—C22—B1	123.1 (3)
C4—C5—H5	117.3	C24—C23—C22	121.5 (3)
C6—C5—H5	117.3	C24—C23—H23	119.3
C7—C6—C5	116.9 (2)	C22—C23—H23	119.3
C7—C6—C12	123.1 (3)	C25—C24—C23	120.5 (4)
C5—C6—C12	120.0 (3)	C25—C24—H24	119.7
C6—C7—C2	120.8 (3)	C23—C24—H24	119.7
C6—C7—H7	119.6	C26—C25—C24	119.5 (3)
C2—C7—H7	119.6	C26—C25—H25	120.2
C9—C8—C11	108.6 (3)	C24—C25—H25	120.2
C9—C8—C10	109.2 (3)	C25—C26—C27	119.5 (3)
C11—C8—C10	107.0 (3)	C25—C26—H26	120.2
C9—C8—C4	109.2 (2)	C27—C26—H26	120.2
C11—C8—C4	111.8 (2)	C26—C27—C22	122.7 (3)
C10—C8—C4	111.0 (2)	C26—C27—H27	118.6
C8—C9—H9A	109.5	C22—C27—H27	118.6
C8—C9—H9B	109.5	C29—C28—C33	118.7 (3)
H9A—C9—H9B	109.5	C29—C28—N1	121.6 (2)
C8—C9—H9C	109.5	C33—C28—N1	119.7 (2)
H9A—C9—H9C	109.5	C28—C29—C30	120.9 (3)
H9B—C9—H9C	109.5	C28—C29—H29	119.6
C8—C10—H10A	109.5	C30—C29—H29	119.6
C8—C10—H10B	109.5	C29—C30—C31	120.9 (3)
H10A—C10—H10B	109.5	C29—C30—H30	119.5
C8—C10—H10C	109.5	C31—C30—H30	119.5
H10A—C10—H10C	109.5	C32—C31—N2	123.6 (3)
H10B—C10—H10C	109.5	C32—C31—C30	117.7 (3)
C8—C11—H11A	109.5	N2—C31—C30	118.7 (3)
C8—C11—H11B	109.5	C33—C32—C31	121.3 (3)
H11A—C11—H11B	109.5	C33—C32—H32	119.4
C8—C11—H11C	109.5	C31—C32—H32	119.4
H11A—C11—H11C	109.5	C32—C33—C28	120.5 (3)
H11B—C11—H11C	109.5	C32—C33—H33	119.7
C15—C12—C13	109.3 (3)	C28—C33—H33	119.7
C15—C12—C6	111.9 (3)	C39—C34—C35	118.2 (3)
C13—C12—C6	109.7 (2)	C39—C34—N2	122.7 (3)
C15—C12—C14	110.2 (3)	C35—C34—N2	119.0 (3)
C13—C12—C14	107.0 (3)	C36—C35—C34	120.9 (3)
C6—C12—C14	108.6 (3)	C36—C35—H35	119.6
C12—C13—H13A	109.5	C34—C35—H35	119.6
C12—C13—H13B	109.5	C37—C36—C35	120.4 (3)
H13A—C13—H13B	109.5	C37—C36—H36	119.8
C12—C13—H13C	109.5	C35—C36—H36	119.8
H13A—C13—H13C	109.5	C38—C37—C36	119.2 (3)
H13B—C13—H13C	109.5	C38—C37—H37	120.4
C12—C14—H14A	109.5	C36—C37—H37	120.4
C12—C14—H14B	109.5	C37—C38—C39	121.5 (3)
H14A—C14—H14B	109.5	C37—C38—H38	119.2
C12—C14—H14C	109.5	C39—C38—H38	119.2
H14A—C14—H14C	109.5	C38—C39—C34	119.6 (3)
H14B—C14—H14C	109.5	C38—C39—H39	120.2
C12—C15—H15A	109.5	C34—C39—H39	120.2
C12—C15—H15B	109.5	O1—B1—C22	106.3 (2)
H15A—C15—H15B	109.5	O1—B1—C16	110.6 (2)
C12—C15—H15C	109.5	C22—B1—C16	115.5 (2)
H15A—C15—H15C	109.5	O1—B1—N1	103.9 (2)
H15B—C15—H15C	109.5	C22—B1—N1	111.6 (2)
C17—C16—C21	115.5 (3)	C16—B1—N1	108.3 (2)
C28—N1—C1—C2	−167.8 (3)	B1—C22—C27—C26	179.1 (3)
B1—N1—C1—C2	12.0 (4)	C1—N1—C28—C29	36.4 (4)
N1—C1—C2—C3	12.9 (4)	B1—N1—C28—C29	−143.3 (3)
N1—C1—C2—C7	−176.3 (3)	C1—N1—C28—C33	−146.4 (3)
B1—O1—C3—C2	−28.1 (3)	B1—N1—C28—C33	33.9 (4)
B1—O1—C3—C4	156.6 (2)	C33—C28—C29—C30	2.2 (4)
C7—C2—C3—O1	−176.7 (2)	N1—C28—C29—C30	179.4 (3)
C1—C2—C3—O1	−6.0 (4)	C28—C29—C30—C31	−2.2 (5)
C7—C2—C3—C4	−1.3 (4)	C34—N2—C31—C32	5.2 (5)
C1—C2—C3—C4	169.4 (3)	C34—N2—C31—C30	−177.5 (3)
O1—C3—C4—C5	176.9 (2)	C29—C30—C31—C32	0.9 (5)
C2—C3—C4—C5	1.6 (4)	C29—C30—C31—N2	−176.6 (3)
O1—C3—C4—C8	−2.1 (4)	N2—C31—C32—C33	177.9 (3)
C2—C3—C4—C8	−177.3 (2)	C30—C31—C32—C33	0.5 (5)
C3—C4—C5—C6	−0.5 (4)	C31—C32—C33—C28	−0.5 (5)
C8—C4—C5—C6	178.4 (3)	C29—C28—C33—C32	−0.8 (4)
C4—C5—C6—C7	−0.8 (4)	N1—C28—C33—C32	−178.1 (3)
C4—C5—C6—C12	−178.9 (3)	C31—N2—C34—C39	41.0 (5)
C5—C6—C7—C2	1.1 (4)	C31—N2—C34—C35	−141.5 (3)
C12—C6—C7—C2	179.1 (3)	C39—C34—C35—C36	−0.3 (4)
C3—C2—C7—C6	0.0 (4)	N2—C34—C35—C36	−178.0 (3)
C1—C2—C7—C6	−170.6 (3)	C34—C35—C36—C37	−2.8 (5)
C5—C4—C8—C9	−111.5 (3)	C35—C36—C37—C38	2.8 (5)
C3—C4—C8—C9	67.4 (3)	C36—C37—C38—C39	0.2 (6)
C5—C4—C8—C11	8.7 (4)	C37—C38—C39—C34	−3.3 (5)
C3—C4—C8—C11	−172.5 (2)	C35—C34—C39—C38	3.2 (5)
C5—C4—C8—C10	128.0 (3)	N2—C34—C39—C38	−179.2 (3)
C3—C4—C8—C10	−53.1 (3)	C3—O1—B1—C22	165.3 (2)
C7—C6—C12—C15	4.4 (5)	C3—O1—B1—C16	−68.7 (3)
C5—C6—C12—C15	−177.6 (3)	C3—O1—B1—N1	47.4 (3)
C7—C6—C12—C13	125.9 (3)	C23—C22—B1—O1	−45.9 (4)
C5—C6—C12—C13	−56.1 (4)	C27—C22—B1—O1	134.1 (3)
C7—C6—C12—C14	−117.5 (3)	C23—C22—B1—C16	−169.0 (3)
C5—C6—C12—C14	60.5 (4)	C27—C22—B1—C16	10.9 (4)
C21—C16—C17—C18	−0.2 (5)	C23—C22—B1—N1	66.8 (3)
B1—C16—C17—C18	179.0 (3)	C27—C22—B1—N1	−113.3 (3)
C16—C17—C18—C19	1.2 (5)	C17—C16—B1—O1	−61.7 (3)
C17—C18—C19—C20	−1.7 (6)	C21—C16—B1—O1	117.4 (3)
C18—C19—C20—C21	1.4 (6)	C17—C16—B1—C22	59.1 (4)
C19—C20—C21—C16	−0.5 (6)	C21—C16—B1—C22	−121.8 (3)
C17—C16—C21—C20	−0.1 (4)	C17—C16—B1—N1	−175.0 (2)
B1—C16—C21—C20	−179.3 (3)	C21—C16—B1—N1	4.1 (4)
C27—C22—C23—C24	1.0 (5)	C1—N1—B1—O1	−38.5 (3)
B1—C22—C23—C24	−179.1 (3)	C28—N1—B1—O1	141.2 (2)
C22—C23—C24—C25	0.2 (7)	C1—N1—B1—C22	−152.7 (2)
C23—C24—C25—C26	−1.5 (7)	C28—N1—B1—C22	27.0 (4)
C24—C25—C26—C27	1.5 (6)	C1—N1—B1—C16	79.1 (3)
C25—C26—C27—C22	−0.3 (5)	C28—N1—B1—C16	−101.1 (3)
C23—C22—C27—C26	−1.0 (5)