Packing considerations of 10-oxa-9-bora­phenanthrene derivatives

Budanow, A.; Sinke, T.; Lerner, H.-W.; Bolte, M.

doi:10.1107/S205322961401290X

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Packing considerations of 10-oxa-9-boraphenanthrene derivatives

A. Budanow, T. Sinke, H.-W. Lerner and M. Bolte

The crystal structures of three products of the reaction of 2-phenylphenol and BCl₃ have been determined. The structures show intriguing packing patterns and an interesting case of pseudosymmetry. In addition, one of the two polymorphs has a primitive monoclinic crystal system, but it is twinned and emulates an orthorhombic C-centred structure. Tris(biphenyl-2-yl) borate, C₃₆H₂₇BO₃, (III), crystallizes with only one molecule in the asymmetric unit. The dihedral angles between the planes of the aromatic rings in the biphenyl moieties are 50.47 (13), 44.95 (13) and 42.60 (13)°. The boron centre is in a trigonal planar coordination with two of the biphenyl residues on one side of the BO₃ plane and the remaining biphenyl residue on the other side. One polymorph of 10-oxa-9-boraphenanthren-9-ol, C₁₂H₉BO₂, (Va), crystallizes with two almost identical molecules (r.m.s. deviation of all non-H atoms = 0.039 Å) in the asymmetric unit. All non-H atoms lie in a common plane (r.m.s. deviation = 0.015 Å for both molecules in the asymmetric unit). The two molecules in the asymmetric unit are connected into dimers via O—H

O hydrogen bonds. A second polymorph of 10-oxa-9-boraphenanthren-9-ol, (Vb), crystallizes as a pseudo-merohedral twin with two almost identical molecules (r.m.s. deviation of all non-H atoms = 0.035 Å) in the asymmetric unit. All non-H atoms lie in a common plane (r.m.s. deviation = 0.012 Å for molecule 1 and 0.014 Å for molecule A). Each of the two molecules in the asymmetric unit is connected into a centrosymmetric dimer via O—H

O hydrogen bonds. The main difference between the two polymorphic structures is that in (Va) the two molecules in the asymmetric unit are hydrogen bonded to each other, whereas in (Vb), each molecule in the asymmetric unit forms a hydrogen-bonded dimer with its centrosymmetric equivalent. 9-[(Biphenyl-2-yl)oxy]-10-oxa-9-boraphenanthrene, C₂₄H₁₇BO₂, (VI), crystallizes with four molecules in the asymmetric unit. The main differences between them are the dihedral angles between the ring planes. Apart from the biphenyl moiety, all non-H atoms lie in a common plane (r.m.s. deviations = 0.026, 0.0231, 0.019 and 0.033 Å for molecules 1, A, B and C, respectively). This structure shows pseudosymmetry; molecules 1 and A, as well as molecules B and C, are related by a pseudo-translation of about $1 \over 2$ in the direction of the b axis. Molecules 1 and B, as well as molecules A and C, are related by a pseudo-inversion centre at $1 \over 4$ , $1 \over 8$ , $1 \over 2$ . Neither between molecules 1 and C nor between molecules A and B can pseudosymmetry be found.

Keywords: crystal structure; hydrogen bonding; polymorphism; pseudosymmetry; twinning; packing considerations; 10-oxa-9-boraphenanthrene; organic electronics.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961401290X/sk3550sup1.cif Contains datablocks III, Va, Vb, VI, global
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961401290X/sk3550IIIsup2.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961401290X/sk3550Vasup3.hkl Contains datablock Va
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961401290X/sk3550Vbsup4.hkl Contains datablock Vb
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961401290X/sk3550VIsup5.hkl Contains datablock VI
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961401290X/sk3550IIIsup6.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961401290X/sk3550Vasup7.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961401290X/sk3550Vbsup8.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961401290X/sk3550VIsup9.cml Supplementary material

CCDC references: 1006553; 1006554; 1006555; 1006556

Computing details top

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(III) Tris(biphenyl-2-yl) borate top

Crystal data top

C₃₆H₂₇BO₃	F(000) = 1088
M_r = 518.39	D_x = 1.278 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8174 reflections
a = 13.9098 (17) Å	θ = 2.3–27.6°
b = 10.1293 (8) Å	µ = 0.08 mm⁻¹
c = 19.485 (2) Å	T = 173 K
β = 100.966 (10)°	Block, colourless
V = 2695.2 (5) Å³	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection top

Stoe IPDS II two-circle diffractometer	3289 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.112
Genix 3D multilayer optics monochromator	θ_max = 27.2°, θ_min = 2.3°
ω scans	h = −17→15
15600 measured reflections	k = −11→12
5830 independent reflections	l = −25→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0434P)²] where P = (F_o² + 2F_c²)/3
5830 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
B1	0.7260 (2)	0.5771 (3)	0.63846 (13)	0.0235 (6)
O1	0.81117 (13)	0.51654 (18)	0.63232 (8)	0.0286 (4)
O2	0.65190 (13)	0.58937 (18)	0.58340 (8)	0.0282 (4)
O3	0.71597 (13)	0.62411 (17)	0.70273 (8)	0.0283 (4)
C1	0.83438 (19)	0.4751 (3)	0.56939 (11)	0.0250 (5)
C2	0.83996 (19)	0.5637 (3)	0.51576 (12)	0.0264 (6)
C3	0.8710 (2)	0.5138 (3)	0.45687 (13)	0.0314 (6)
H3	0.8750	0.5715	0.4190	0.038*
C4	0.8961 (2)	0.3831 (3)	0.45228 (13)	0.0342 (6)
H4	0.9192	0.3523	0.4123	0.041*
C5	0.8878 (2)	0.2972 (3)	0.50529 (13)	0.0333 (6)
H5	0.9034	0.2064	0.5017	0.040*
C6	0.8563 (2)	0.3441 (3)	0.56422 (13)	0.0306 (6)
H6	0.8499	0.2852	0.6010	0.037*
C11	0.8143 (2)	0.7056 (3)	0.51816 (12)	0.0281 (6)
C12	0.7511 (2)	0.7614 (3)	0.46223 (13)	0.0327 (6)
H12	0.7247	0.7081	0.4230	0.039*
C13	0.7259 (2)	0.8932 (3)	0.46242 (14)	0.0390 (7)
H13	0.6828	0.9301	0.4235	0.047*
C14	0.7635 (2)	0.9714 (3)	0.51932 (16)	0.0403 (7)
H14	0.7459	1.0619	0.5198	0.048*
C15	0.8269 (2)	0.9173 (3)	0.57546 (15)	0.0387 (7)
H15	0.8531	0.9710	0.6145	0.046*
C16	0.8523 (2)	0.7851 (3)	0.57503 (13)	0.0326 (6)
H16	0.8960	0.7485	0.6138	0.039*
C21	0.56304 (19)	0.6449 (3)	0.58975 (12)	0.0276 (6)
C22	0.4901 (2)	0.5650 (3)	0.60773 (12)	0.0282 (6)
C23	0.4000 (2)	0.6259 (3)	0.60850 (14)	0.0363 (7)
H23	0.3479	0.5746	0.6196	0.044*
C24	0.3848 (2)	0.7583 (3)	0.59361 (15)	0.0426 (7)
H24	0.3228	0.7970	0.5944	0.051*
C25	0.4595 (2)	0.8338 (3)	0.57768 (15)	0.0402 (7)
H25	0.4496	0.9252	0.5680	0.048*
C26	0.5491 (2)	0.7770 (3)	0.57566 (13)	0.0347 (6)
H26	0.6008	0.8291	0.5646	0.042*
C31	0.5055 (2)	0.4246 (3)	0.62803 (12)	0.0286 (6)
C32	0.4716 (2)	0.3773 (3)	0.68588 (14)	0.0380 (7)
H32	0.4408	0.4368	0.7126	0.046*
C33	0.4812 (3)	0.2475 (3)	0.70578 (16)	0.0485 (8)
H33	0.4582	0.2180	0.7460	0.058*
C34	0.5248 (2)	0.1600 (3)	0.66666 (16)	0.0469 (8)
H34	0.5299	0.0693	0.6791	0.056*
C35	0.5608 (2)	0.2041 (3)	0.60975 (15)	0.0426 (7)
H35	0.5921	0.1440	0.5837	0.051*
C36	0.5516 (2)	0.3362 (3)	0.59020 (13)	0.0355 (7)
H36	0.5768	0.3661	0.5509	0.043*
C41	0.7820 (2)	0.5872 (3)	0.76225 (11)	0.0277 (6)
C42	0.84756 (19)	0.6795 (3)	0.79779 (12)	0.0283 (6)
C43	0.9119 (2)	0.6334 (3)	0.85699 (13)	0.0369 (7)
H43	0.9576	0.6932	0.8827	0.044*
C44	0.9114 (2)	0.5051 (3)	0.87920 (14)	0.0443 (8)
H44	0.9570	0.4770	0.9192	0.053*
C45	0.8450 (3)	0.4172 (3)	0.84366 (14)	0.0443 (8)
H45	0.8440	0.3285	0.8593	0.053*
C46	0.7796 (2)	0.4581 (3)	0.78483 (14)	0.0381 (7)
H46	0.7333	0.3978	0.7601	0.046*
C51	0.8516 (2)	0.8196 (3)	0.77710 (11)	0.0285 (6)
C52	0.7681 (2)	0.8952 (3)	0.75813 (14)	0.0359 (7)
H52	0.7057	0.8544	0.7534	0.043*
C53	0.7737 (2)	1.0292 (3)	0.74593 (15)	0.0414 (7)
H53	0.7155	1.0798	0.7338	0.050*
C54	0.8635 (3)	1.0894 (3)	0.75137 (14)	0.0428 (7)
H54	0.8674	1.1815	0.7429	0.051*
C55	0.9477 (2)	1.0158 (3)	0.76907 (14)	0.0426 (8)
H55	1.0098	1.0570	0.7723	0.051*
C56	0.9422 (2)	0.8822 (3)	0.78214 (12)	0.0367 (7)
H56	1.0007	0.8322	0.7947	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0253 (16)	0.0214 (14)	0.0248 (13)	−0.0017 (12)	0.0072 (11)	0.0017 (11)
O1	0.0286 (10)	0.0367 (10)	0.0212 (8)	0.0045 (9)	0.0067 (7)	0.0003 (7)
O2	0.0216 (10)	0.0364 (10)	0.0273 (8)	−0.0005 (8)	0.0066 (7)	−0.0018 (7)
O3	0.0285 (10)	0.0322 (10)	0.0247 (8)	0.0057 (8)	0.0065 (7)	−0.0007 (7)
C1	0.0200 (13)	0.0327 (14)	0.0215 (11)	0.0048 (11)	0.0017 (10)	−0.0041 (10)
C2	0.0209 (14)	0.0346 (15)	0.0231 (11)	−0.0015 (11)	0.0023 (10)	−0.0022 (10)
C3	0.0319 (16)	0.0358 (16)	0.0280 (13)	−0.0050 (13)	0.0094 (11)	−0.0015 (11)
C4	0.0310 (16)	0.0433 (17)	0.0298 (13)	−0.0011 (13)	0.0097 (11)	−0.0102 (12)
C5	0.0322 (16)	0.0291 (14)	0.0378 (14)	0.0032 (13)	0.0049 (12)	−0.0061 (11)
C6	0.0299 (16)	0.0330 (16)	0.0282 (12)	−0.0022 (12)	0.0035 (11)	0.0029 (10)
C11	0.0278 (15)	0.0298 (14)	0.0290 (12)	−0.0036 (12)	0.0113 (10)	0.0001 (10)
C12	0.0345 (16)	0.0367 (16)	0.0287 (13)	−0.0036 (13)	0.0107 (11)	0.0026 (11)
C13	0.0366 (17)	0.0399 (17)	0.0432 (15)	0.0013 (14)	0.0145 (13)	0.0109 (13)
C14	0.0416 (19)	0.0291 (15)	0.0564 (18)	0.0017 (14)	0.0250 (14)	0.0040 (13)
C15	0.0373 (18)	0.0342 (16)	0.0473 (16)	−0.0071 (14)	0.0150 (13)	−0.0083 (13)
C16	0.0297 (16)	0.0355 (16)	0.0335 (13)	−0.0037 (13)	0.0083 (11)	−0.0004 (11)
C21	0.0222 (14)	0.0370 (16)	0.0235 (11)	0.0014 (12)	0.0039 (10)	−0.0028 (10)
C22	0.0202 (13)	0.0371 (15)	0.0273 (12)	0.0016 (12)	0.0050 (10)	−0.0058 (10)
C23	0.0261 (16)	0.0433 (17)	0.0410 (14)	−0.0029 (13)	0.0103 (12)	−0.0005 (13)
C24	0.0309 (17)	0.0491 (19)	0.0482 (17)	0.0117 (15)	0.0086 (13)	0.0001 (14)
C25	0.0391 (18)	0.0340 (16)	0.0476 (16)	0.0089 (14)	0.0085 (13)	0.0003 (13)
C26	0.0338 (17)	0.0347 (16)	0.0356 (14)	−0.0042 (13)	0.0069 (12)	−0.0022 (11)
C31	0.0223 (14)	0.0352 (15)	0.0263 (12)	−0.0047 (12)	−0.0003 (10)	−0.0009 (10)
C32	0.0366 (17)	0.0427 (17)	0.0373 (14)	−0.0053 (14)	0.0133 (12)	−0.0007 (13)
C33	0.048 (2)	0.057 (2)	0.0422 (16)	−0.0020 (17)	0.0121 (14)	0.0145 (14)
C34	0.051 (2)	0.0377 (17)	0.0491 (17)	−0.0017 (15)	0.0034 (15)	0.0119 (14)
C35	0.047 (2)	0.0377 (17)	0.0432 (16)	0.0078 (15)	0.0089 (13)	0.0003 (13)
C36	0.0382 (17)	0.0404 (17)	0.0281 (13)	−0.0009 (14)	0.0070 (11)	0.0006 (11)
C41	0.0278 (15)	0.0364 (15)	0.0208 (11)	0.0055 (12)	0.0089 (10)	0.0012 (10)
C42	0.0257 (15)	0.0406 (16)	0.0208 (11)	0.0038 (12)	0.0099 (10)	−0.0034 (10)
C43	0.0288 (16)	0.0565 (19)	0.0256 (12)	0.0055 (14)	0.0054 (11)	0.0004 (12)
C44	0.0403 (18)	0.070 (2)	0.0236 (13)	0.0179 (17)	0.0091 (12)	0.0125 (14)
C45	0.060 (2)	0.0415 (17)	0.0354 (14)	0.0172 (17)	0.0191 (14)	0.0124 (13)
C46	0.0466 (19)	0.0382 (17)	0.0325 (14)	0.0065 (14)	0.0152 (13)	0.0012 (12)
C51	0.0247 (14)	0.0416 (16)	0.0198 (11)	0.0027 (12)	0.0058 (10)	−0.0031 (10)
C52	0.0252 (16)	0.0403 (17)	0.0431 (15)	−0.0001 (13)	0.0088 (12)	−0.0043 (12)
C53	0.0380 (19)	0.0376 (17)	0.0493 (17)	0.0022 (14)	0.0102 (14)	−0.0042 (13)
C54	0.052 (2)	0.0403 (17)	0.0380 (15)	−0.0095 (16)	0.0135 (14)	−0.0055 (13)
C55	0.0365 (18)	0.059 (2)	0.0343 (14)	−0.0188 (16)	0.0109 (12)	−0.0041 (13)
C56	0.0276 (16)	0.0546 (19)	0.0279 (13)	−0.0038 (14)	0.0050 (11)	−0.0006 (12)

Geometric parameters (Å, º) top

B1—O2	1.345 (3)	C25—C26	1.379 (4)
B1—O1	1.359 (4)	C25—H25	0.9500
B1—O3	1.372 (3)	C26—H26	0.9500
O1—C1	1.391 (3)	C31—C32	1.388 (4)
O2—C21	1.385 (3)	C31—C36	1.391 (4)
O3—C41	1.387 (3)	C32—C33	1.370 (4)
C1—C6	1.370 (4)	C32—H32	0.9500
C1—C2	1.391 (4)	C33—C34	1.382 (5)
C2—C3	1.396 (4)	C33—H33	0.9500
C2—C11	1.483 (4)	C34—C35	1.375 (4)
C3—C4	1.377 (4)	C34—H34	0.9500
C3—H3	0.9500	C35—C36	1.390 (4)
C4—C5	1.372 (4)	C35—H35	0.9500
C4—H4	0.9500	C36—H36	0.9500
C5—C6	1.389 (4)	C41—C46	1.381 (4)
C5—H5	0.9500	C41—C42	1.395 (4)
C6—H6	0.9500	C42—C43	1.399 (4)
C11—C12	1.384 (4)	C42—C51	1.480 (4)
C11—C16	1.390 (4)	C43—C44	1.370 (5)
C12—C13	1.380 (4)	C43—H43	0.9500
C12—H12	0.9500	C44—C45	1.371 (5)
C13—C14	1.382 (4)	C44—H44	0.9500
C13—H13	0.9500	C45—C46	1.385 (4)
C14—C15	1.380 (4)	C45—H45	0.9500
C14—H14	0.9500	C46—H46	0.9500
C15—C16	1.386 (4)	C51—C52	1.381 (4)
C15—H15	0.9500	C51—C56	1.397 (4)
C16—H16	0.9500	C52—C53	1.383 (4)
C21—C26	1.373 (4)	C52—H52	0.9500
C21—C22	1.393 (4)	C53—C54	1.376 (5)
C22—C23	1.399 (4)	C53—H53	0.9500
C22—C31	1.481 (4)	C54—C55	1.376 (5)
C23—C24	1.380 (4)	C54—H54	0.9500
C23—H23	0.9500	C55—C56	1.383 (4)
C24—C25	1.373 (4)	C55—H55	0.9500
C24—H24	0.9500	C56—H56	0.9500

O2—B1—O1	121.3 (2)	C21—C26—C25	119.7 (3)
O2—B1—O3	120.0 (2)	C21—C26—H26	120.2
O1—B1—O3	118.6 (2)	C25—C26—H26	120.2
B1—O1—C1	124.47 (19)	C32—C31—C36	118.0 (3)
B1—O2—C21	121.87 (19)	C32—C31—C22	119.6 (3)
B1—O3—C41	120.3 (2)	C36—C31—C22	122.3 (2)
C6—C1—C2	121.7 (2)	C33—C32—C31	122.1 (3)
C6—C1—O1	116.7 (2)	C33—C32—H32	118.9
C2—C1—O1	121.6 (2)	C31—C32—H32	118.9
C1—C2—C3	117.0 (2)	C32—C33—C34	119.2 (3)
C1—C2—C11	123.6 (2)	C32—C33—H33	120.4
C3—C2—C11	119.4 (2)	C34—C33—H33	120.4
C4—C3—C2	121.6 (2)	C35—C34—C33	120.1 (3)
C4—C3—H3	119.2	C35—C34—H34	119.9
C2—C3—H3	119.2	C33—C34—H34	119.9
C5—C4—C3	120.2 (2)	C34—C35—C36	120.3 (3)
C5—C4—H4	119.9	C34—C35—H35	119.8
C3—C4—H4	119.9	C36—C35—H35	119.8
C4—C5—C6	119.4 (3)	C35—C36—C31	120.1 (3)
C4—C5—H5	120.3	C35—C36—H36	119.9
C6—C5—H5	120.3	C31—C36—H36	119.9
C1—C6—C5	120.1 (2)	C46—C41—O3	118.0 (2)
C1—C6—H6	119.9	C46—C41—C42	121.9 (2)
C5—C6—H6	119.9	O3—C41—C42	120.0 (2)
C12—C11—C16	118.6 (2)	C41—C42—C43	116.2 (3)
C12—C11—C2	119.4 (2)	C41—C42—C51	124.3 (2)
C16—C11—C2	121.9 (2)	C43—C42—C51	119.6 (2)
C13—C12—C11	121.1 (3)	C44—C43—C42	122.4 (3)
C13—C12—H12	119.5	C44—C43—H43	118.8
C11—C12—H12	119.5	C42—C43—H43	118.8
C12—C13—C14	119.9 (3)	C43—C44—C45	120.0 (3)
C12—C13—H13	120.0	C43—C44—H44	120.0
C14—C13—H13	120.0	C45—C44—H44	120.0
C15—C14—C13	119.7 (3)	C44—C45—C46	119.8 (3)
C15—C14—H14	120.1	C44—C45—H45	120.1
C13—C14—H14	120.1	C46—C45—H45	120.1
C14—C15—C16	120.3 (3)	C41—C46—C45	119.7 (3)
C14—C15—H15	119.9	C41—C46—H46	120.2
C16—C15—H15	119.9	C45—C46—H46	120.2
C15—C16—C11	120.4 (3)	C52—C51—C56	118.0 (3)
C15—C16—H16	119.8	C52—C51—C42	122.1 (3)
C11—C16—H16	119.8	C56—C51—C42	119.8 (3)
C26—C21—O2	118.2 (3)	C51—C52—C53	121.2 (3)
C26—C21—C22	122.3 (3)	C51—C52—H52	119.4
O2—C21—C22	119.5 (2)	C53—C52—H52	119.4
C21—C22—C23	116.3 (3)	C54—C53—C52	120.1 (3)
C21—C22—C31	123.3 (2)	C54—C53—H53	119.9
C23—C22—C31	120.3 (3)	C52—C53—H53	119.9
C24—C23—C22	121.8 (3)	C53—C54—C55	119.8 (3)
C24—C23—H23	119.1	C53—C54—H54	120.1
C22—C23—H23	119.1	C55—C54—H54	120.1
C25—C24—C23	119.8 (3)	C54—C55—C56	120.2 (3)
C25—C24—H24	120.1	C54—C55—H55	119.9
C23—C24—H24	120.1	C56—C55—H55	119.9
C24—C25—C26	120.0 (3)	C55—C56—C51	120.8 (3)
C24—C25—H25	120.0	C55—C56—H56	119.6
C26—C25—H25	120.0	C51—C56—H56	119.6

O2—B1—O1—C1	7.2 (4)	O2—C21—C26—C25	176.4 (2)
O3—B1—O1—C1	−174.0 (2)	C22—C21—C26—C25	−1.4 (4)
O1—B1—O2—C21	176.7 (2)	C24—C25—C26—C21	−0.1 (4)
O3—B1—O2—C21	−2.2 (4)	C21—C22—C31—C32	134.5 (3)
O2—B1—O3—C41	165.8 (2)	C23—C22—C31—C32	−42.9 (3)
O1—B1—O3—C41	−13.0 (4)	C21—C22—C31—C36	−46.7 (4)
B1—O1—C1—C6	−122.8 (3)	C23—C22—C31—C36	135.8 (3)
B1—O1—C1—C2	60.4 (3)	C36—C31—C32—C33	−0.8 (4)
C6—C1—C2—C3	−1.4 (4)	C22—C31—C32—C33	178.0 (3)
O1—C1—C2—C3	175.2 (2)	C31—C32—C33—C34	−0.9 (5)
C6—C1—C2—C11	178.2 (2)	C32—C33—C34—C35	2.1 (5)
O1—C1—C2—C11	−5.2 (4)	C33—C34—C35—C36	−1.5 (5)
C1—C2—C3—C4	−0.7 (4)	C34—C35—C36—C31	−0.2 (4)
C11—C2—C3—C4	179.7 (3)	C32—C31—C36—C35	1.3 (4)
C2—C3—C4—C5	2.2 (4)	C22—C31—C36—C35	−177.4 (3)
C3—C4—C5—C6	−1.6 (4)	B1—O3—C41—C46	−70.0 (3)
C2—C1—C6—C5	2.0 (4)	B1—O3—C41—C42	110.6 (3)
O1—C1—C6—C5	−174.8 (2)	C46—C41—C42—C43	1.0 (4)
C4—C5—C6—C1	−0.4 (4)	O3—C41—C42—C43	−179.6 (2)
C1—C2—C11—C12	−129.9 (3)	C46—C41—C42—C51	−178.3 (3)
C3—C2—C11—C12	49.7 (4)	O3—C41—C42—C51	1.1 (4)
C1—C2—C11—C16	50.4 (4)	C41—C42—C43—C44	0.2 (4)
C3—C2—C11—C16	−130.0 (3)	C51—C42—C43—C44	179.5 (3)
C16—C11—C12—C13	0.0 (4)	C42—C43—C44—C45	−1.1 (5)
C2—C11—C12—C13	−179.7 (3)	C43—C44—C45—C46	0.8 (5)
C11—C12—C13—C14	−0.4 (4)	O3—C41—C46—C45	179.3 (3)
C12—C13—C14—C15	0.6 (5)	C42—C41—C46—C45	−1.2 (4)
C13—C14—C15—C16	−0.3 (5)	C44—C45—C46—C41	0.3 (5)
C14—C15—C16—C11	−0.1 (4)	C41—C42—C51—C52	44.7 (4)
C12—C11—C16—C15	0.2 (4)	C43—C42—C51—C52	−134.6 (3)
C2—C11—C16—C15	179.9 (3)	C41—C42—C51—C56	−140.7 (3)
B1—O2—C21—C26	94.4 (3)	C43—C42—C51—C56	40.0 (3)
B1—O2—C21—C22	−87.7 (3)	C56—C51—C52—C53	−1.4 (4)
C26—C21—C22—C23	2.0 (3)	C42—C51—C52—C53	173.3 (2)
O2—C21—C22—C23	−175.7 (2)	C51—C52—C53—C54	1.2 (4)
C26—C21—C22—C31	−175.5 (2)	C52—C53—C54—C55	−0.1 (4)
O2—C21—C22—C31	6.7 (3)	C53—C54—C55—C56	−0.7 (4)
C21—C22—C23—C24	−1.2 (4)	C54—C55—C56—C51	0.5 (4)
C31—C22—C23—C24	176.4 (2)	C52—C51—C56—C55	0.5 (4)
C22—C23—C24—C25	−0.2 (4)	C42—C51—C56—C55	−174.2 (2)
C23—C24—C25—C26	0.9 (4)

(Va) 10-oxa-9-boraphenanthren-9-ol top

Crystal data top

C₁₂H₉BO₂	F(000) = 816
M_r = 196.00	D_x = 1.394 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 7034 reflections
a = 14.7548 (11) Å	θ = 2.2–25.5°
b = 5.1497 (3) Å	µ = 0.09 mm⁻¹
c = 24.580 (2) Å	T = 173 K
V = 1867.7 (2) Å³	Plate, colourless
Z = 8	0.26 × 0.14 × 0.08 mm

Data collection top

Stoe IPDS II two-circle diffractometer	1247 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.105
Graphite monochromator	θ_max = 25.1°, θ_min = 2.8°
ω scans	h = −17→17
10071 measured reflections	k = −6→5
1687 independent reflections	l = −29→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0533P)²] where P = (F_o² + 2F_c²)/3
1687 reflections	(Δ/σ)_max = 0.013
279 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
B1	0.3167 (4)	0.6824 (12)	0.0409 (2)	0.0337 (11)
O1	0.3872 (2)	0.8313 (7)	0.06190 (12)	0.0363 (7)
O2	0.2889 (3)	0.7362 (6)	−0.01058 (19)	0.0388 (11)
H2	0.313 (6)	0.886 (17)	−0.027 (3)	0.12 (3)*
C1	0.2756 (3)	0.4643 (8)	0.07573 (17)	0.0337 (9)
C2	0.3124 (3)	0.4178 (8)	0.12725 (18)	0.0336 (10)
C3	0.2758 (4)	0.2209 (9)	0.1603 (3)	0.0371 (14)
H3	0.2997	0.1904	0.1956	0.044*
C4	0.2045 (3)	0.0715 (9)	0.1407 (2)	0.0449 (11)
H4	0.1801	−0.0624	0.1629	0.054*
C5	0.1683 (3)	0.1147 (8)	0.0893 (2)	0.0417 (10)
H5	0.1196	0.0105	0.0765	0.050*
C6	0.2033 (4)	0.3093 (10)	0.0567 (3)	0.0411 (12)
H6	0.1787	0.3387	0.0216	0.049*
C11	0.4220 (5)	0.7813 (9)	0.1138 (2)	0.0334 (14)
C12	0.3889 (3)	0.5825 (9)	0.14614 (16)	0.0330 (10)
C13	0.4301 (3)	0.5506 (9)	0.19729 (18)	0.0372 (10)
H13	0.4105	0.4146	0.2206	0.045*
C14	0.4981 (5)	0.7124 (11)	0.2140 (3)	0.0420 (14)
H14	0.5236	0.6898	0.2492	0.050*
C15	0.5305 (3)	0.9072 (9)	0.1810 (2)	0.0427 (11)
H15	0.5781	1.0169	0.1931	0.051*
C16	0.4927 (3)	0.9417 (9)	0.12993 (19)	0.0376 (10)
H16	0.5149	1.0730	0.1063	0.045*
B1A	0.5639 (4)	0.6762 (12)	0.4560 (2)	0.0351 (11)
O1A	0.6351 (2)	0.8215 (7)	0.43636 (12)	0.0343 (7)
O2A	0.5316 (3)	0.7246 (7)	0.50612 (18)	0.0429 (12)
H2A	0.558 (4)	0.872 (13)	0.523 (2)	0.065 (18)*
C1A	0.5252 (3)	0.4558 (8)	0.41985 (18)	0.0331 (9)
C2A	0.5651 (3)	0.4137 (8)	0.36860 (18)	0.0322 (9)
C3A	0.5300 (5)	0.2148 (9)	0.3357 (3)	0.0392 (14)
H3A	0.5559	0.1841	0.3009	0.047*
C4A	0.4585 (3)	0.0635 (9)	0.35299 (18)	0.0400 (11)
H4A	0.4361	−0.0710	0.3302	0.048*
C5A	0.4188 (3)	0.1056 (8)	0.40336 (19)	0.0403 (11)
H5A	0.3692	0.0020	0.4150	0.048*
C6A	0.4522 (4)	0.2991 (10)	0.4363 (2)	0.0364 (11)
H6A	0.4253	0.3276	0.4709	0.044*
C11A	0.6731 (4)	0.7762 (8)	0.3863 (2)	0.0296 (13)
C12A	0.6414 (3)	0.5792 (9)	0.35176 (16)	0.0317 (9)
C13A	0.6852 (3)	0.5554 (8)	0.30117 (18)	0.0365 (10)
H13A	0.6664	0.4213	0.2772	0.044*
C14A	0.7556 (5)	0.7212 (9)	0.2846 (3)	0.0393 (14)
H14A	0.7832	0.7020	0.2499	0.047*
C15A	0.7837 (3)	0.9139 (8)	0.32028 (18)	0.0376 (10)
H15A	0.8312	1.0281	0.3100	0.045*
C16A	0.7432 (3)	0.9414 (9)	0.37077 (18)	0.0369 (10)
H16A	0.7632	1.0735	0.3949	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.034 (3)	0.034 (2)	0.033 (3)	0.002 (3)	0.004 (2)	−0.001 (3)
O1	0.0390 (19)	0.0330 (16)	0.0368 (17)	−0.0034 (17)	0.0002 (14)	0.0049 (16)
O2	0.039 (2)	0.038 (2)	0.039 (2)	−0.0065 (13)	−0.0033 (19)	0.0063 (13)
C1	0.030 (2)	0.032 (2)	0.039 (2)	0.0048 (18)	0.0036 (17)	−0.0018 (17)
C2	0.028 (2)	0.031 (2)	0.042 (3)	0.0044 (18)	0.0076 (19)	0.0033 (18)
C3	0.028 (3)	0.043 (3)	0.040 (3)	0.003 (2)	0.004 (2)	0.005 (2)
C4	0.040 (3)	0.039 (3)	0.055 (3)	−0.002 (2)	0.012 (2)	0.007 (2)
C5	0.034 (2)	0.035 (3)	0.057 (3)	−0.002 (2)	0.005 (2)	−0.001 (2)
C6	0.035 (3)	0.037 (2)	0.051 (3)	0.000 (3)	0.006 (2)	0.004 (3)
C11	0.031 (3)	0.036 (3)	0.033 (3)	0.006 (2)	−0.001 (2)	0.001 (2)
C12	0.031 (2)	0.033 (2)	0.035 (2)	0.0069 (18)	0.0032 (18)	0.0010 (19)
C13	0.033 (2)	0.039 (3)	0.040 (3)	0.0081 (18)	0.0046 (18)	0.0040 (19)
C14	0.033 (3)	0.056 (3)	0.037 (3)	0.004 (2)	−0.005 (2)	−0.002 (3)
C15	0.031 (2)	0.041 (3)	0.056 (3)	0.003 (2)	−0.005 (2)	−0.007 (2)
C16	0.032 (2)	0.033 (2)	0.047 (3)	−0.0010 (18)	0.003 (2)	0.0026 (19)
B1A	0.031 (3)	0.034 (3)	0.041 (3)	0.004 (3)	−0.001 (2)	0.004 (3)
O1A	0.0306 (17)	0.0369 (16)	0.0354 (17)	−0.0011 (16)	0.0000 (13)	−0.0046 (16)
O2A	0.047 (3)	0.043 (2)	0.038 (2)	−0.0107 (16)	0.0060 (19)	−0.0089 (15)
C1A	0.028 (2)	0.031 (2)	0.040 (2)	0.0002 (18)	−0.0033 (18)	0.0011 (17)
C2A	0.026 (2)	0.032 (2)	0.038 (2)	0.0029 (17)	−0.0042 (18)	0.0020 (18)
C3A	0.039 (4)	0.035 (3)	0.043 (3)	−0.001 (2)	−0.007 (3)	−0.007 (2)
C4A	0.035 (3)	0.034 (2)	0.051 (3)	−0.0016 (18)	−0.0104 (19)	−0.0058 (19)
C5A	0.029 (2)	0.036 (2)	0.056 (3)	−0.0029 (19)	−0.005 (2)	−0.001 (2)
C6A	0.031 (3)	0.038 (2)	0.040 (3)	0.001 (2)	0.004 (2)	0.004 (2)
C11A	0.024 (3)	0.034 (3)	0.031 (3)	0.0034 (17)	−0.006 (2)	−0.0043 (18)
C12A	0.028 (2)	0.030 (2)	0.037 (2)	0.0028 (17)	−0.0031 (17)	−0.0032 (18)
C13A	0.035 (2)	0.035 (3)	0.039 (2)	0.0027 (18)	−0.0020 (17)	−0.0081 (18)
C14A	0.035 (3)	0.038 (3)	0.045 (3)	0.004 (2)	0.004 (3)	−0.006 (2)
C15A	0.032 (2)	0.035 (2)	0.046 (2)	−0.0041 (17)	−0.0001 (19)	−0.0033 (19)
C16A	0.027 (2)	0.038 (3)	0.045 (3)	0.0011 (18)	−0.005 (2)	−0.0066 (18)

Geometric parameters (Å, º) top

B1—O2	1.360 (7)	B1A—O2A	1.344 (7)
B1—O1	1.391 (7)	B1A—O1A	1.377 (7)
B1—C1	1.537 (7)	B1A—C1A	1.550 (7)
O1—C11	1.400 (7)	O1A—C11A	1.373 (7)
O2—H2	0.94 (9)	O2A—H2A	0.96 (6)
C1—C2	1.399 (6)	C1A—C6A	1.405 (7)
C1—C6	1.411 (7)	C1A—C2A	1.407 (6)
C2—C3	1.407 (7)	C2A—C3A	1.404 (7)
C2—C12	1.485 (6)	C2A—C12A	1.472 (6)
C3—C4	1.389 (8)	C3A—C4A	1.380 (8)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C5	1.391 (7)	C4A—C5A	1.386 (6)
C4—H4	0.9500	C4A—H4A	0.9500
C5—C6	1.382 (7)	C5A—C6A	1.374 (7)
C5—H5	0.9500	C5A—H5A	0.9500
C6—H6	0.9500	C6A—H6A	0.9500
C11—C12	1.385 (7)	C11A—C16A	1.392 (7)
C11—C16	1.388 (7)	C11A—C12A	1.402 (7)
C12—C13	1.406 (6)	C12A—C13A	1.407 (6)
C13—C14	1.368 (8)	C13A—C14A	1.405 (8)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.376 (8)	C14A—C15A	1.387 (8)
C14—H14	0.9500	C14A—H14A	0.9500
C15—C16	1.384 (7)	C15A—C16A	1.385 (6)
C15—H15	0.9500	C15A—H15A	0.9500
C16—H16	0.9500	C16A—H16A	0.9500

O2—B1—O1	117.3 (5)	O2A—B1A—O1A	119.4 (5)
O2—B1—C1	123.2 (5)	O2A—B1A—C1A	122.0 (5)
O1—B1—C1	119.5 (4)	O1A—B1A—C1A	118.5 (4)
B1—O1—C11	120.7 (4)	C11A—O1A—B1A	122.3 (4)
B1—O2—H2	117 (5)	B1A—O2A—H2A	114 (3)
C2—C1—C6	119.8 (4)	C6A—C1A—C2A	119.3 (4)
C2—C1—B1	118.4 (4)	C6A—C1A—B1A	122.6 (4)
C6—C1—B1	121.9 (4)	C2A—C1A—B1A	118.2 (4)
C1—C2—C3	119.8 (5)	C3A—C2A—C1A	118.3 (5)
C1—C2—C12	118.7 (4)	C3A—C2A—C12A	122.8 (5)
C3—C2—C12	121.5 (4)	C1A—C2A—C12A	118.8 (4)
C4—C3—C2	119.3 (6)	C4A—C3A—C2A	121.0 (6)
C4—C3—H3	120.3	C4A—C3A—H3A	119.5
C2—C3—H3	120.3	C2A—C3A—H3A	119.5
C3—C4—C5	121.2 (5)	C3A—C4A—C5A	120.7 (5)
C3—C4—H4	119.4	C3A—C4A—H4A	119.7
C5—C4—H4	119.4	C5A—C4A—H4A	119.7
C6—C5—C4	119.9 (4)	C6A—C5A—C4A	119.2 (4)
C6—C5—H5	120.1	C6A—C5A—H5A	120.4
C4—C5—H5	120.1	C4A—C5A—H5A	120.4
C5—C6—C1	120.1 (5)	C5A—C6A—C1A	121.5 (5)
C5—C6—H6	120.0	C5A—C6A—H6A	119.3
C1—C6—H6	120.0	C1A—C6A—H6A	119.3
C12—C11—C16	122.8 (5)	O1A—C11A—C16A	116.4 (4)
C12—C11—O1	122.0 (5)	O1A—C11A—C12A	122.0 (5)
C16—C11—O1	115.2 (5)	C16A—C11A—C12A	121.6 (5)
C11—C12—C13	116.5 (4)	C11A—C12A—C13A	116.4 (4)
C11—C12—C2	120.7 (4)	C11A—C12A—C2A	120.2 (4)
C13—C12—C2	122.8 (4)	C13A—C12A—C2A	123.3 (4)
C14—C13—C12	121.0 (5)	C14A—C13A—C12A	122.9 (5)
C14—C13—H13	119.5	C14A—C13A—H13A	118.6
C12—C13—H13	119.5	C12A—C13A—H13A	118.6
C13—C14—C15	121.4 (6)	C15A—C14A—C13A	118.2 (6)
C13—C14—H14	119.3	C15A—C14A—H14A	120.9
C15—C14—H14	119.3	C13A—C14A—H14A	120.9
C14—C15—C16	119.3 (5)	C16A—C15A—C14A	120.7 (5)
C14—C15—H15	120.4	C16A—C15A—H15A	119.6
C16—C15—H15	120.4	C14A—C15A—H15A	119.6
C15—C16—C11	119.0 (4)	C15A—C16A—C11A	120.2 (4)
C15—C16—H16	120.5	C15A—C16A—H16A	119.9
C11—C16—H16	120.5	C11A—C16A—H16A	119.9

O2—B1—O1—C11	−177.6 (5)	O2A—B1A—O1A—C11A	177.8 (5)
C1—B1—O1—C11	1.2 (7)	C1A—B1A—O1A—C11A	−0.6 (7)
O2—B1—C1—C2	177.0 (5)	O2A—B1A—C1A—C6A	2.3 (8)
O1—B1—C1—C2	−1.8 (7)	O1A—B1A—C1A—C6A	−179.4 (4)
O2—B1—C1—C6	−2.0 (8)	O2A—B1A—C1A—C2A	−178.0 (4)
O1—B1—C1—C6	179.3 (4)	O1A—B1A—C1A—C2A	0.3 (7)
C6—C1—C2—C3	−1.5 (6)	C6A—C1A—C2A—C3A	−0.1 (6)
B1—C1—C2—C3	179.5 (5)	B1A—C1A—C2A—C3A	−179.8 (5)
C6—C1—C2—C12	179.6 (4)	C6A—C1A—C2A—C12A	179.9 (4)
B1—C1—C2—C12	0.6 (6)	B1A—C1A—C2A—C12A	0.2 (6)
C1—C2—C3—C4	1.3 (7)	C1A—C2A—C3A—C4A	−0.2 (8)
C12—C2—C3—C4	−179.8 (4)	C12A—C2A—C3A—C4A	179.8 (4)
C2—C3—C4—C5	−0.5 (8)	C2A—C3A—C4A—C5A	0.6 (8)
C3—C4—C5—C6	−0.1 (7)	C3A—C4A—C5A—C6A	−0.6 (7)
C4—C5—C6—C1	−0.1 (7)	C4A—C5A—C6A—C1A	0.3 (7)
C2—C1—C6—C5	0.9 (7)	C2A—C1A—C6A—C5A	0.0 (7)
B1—C1—C6—C5	179.8 (5)	B1A—C1A—C6A—C5A	179.7 (5)
B1—O1—C11—C12	0.6 (7)	B1A—O1A—C11A—C16A	178.5 (4)
B1—O1—C11—C16	179.4 (4)	B1A—O1A—C11A—C12A	0.3 (7)
C16—C11—C12—C13	0.7 (7)	O1A—C11A—C12A—C13A	179.0 (4)
O1—C11—C12—C13	179.4 (4)	C16A—C11A—C12A—C13A	1.0 (7)
C16—C11—C12—C2	179.4 (4)	O1A—C11A—C12A—C2A	0.2 (7)
O1—C11—C12—C2	−1.9 (7)	C16A—C11A—C12A—C2A	−177.8 (4)
C1—C2—C12—C11	1.2 (6)	C3A—C2A—C12A—C11A	179.5 (5)
C3—C2—C12—C11	−177.7 (5)	C1A—C2A—C12A—C11A	−0.4 (6)
C1—C2—C12—C13	179.9 (4)	C3A—C2A—C12A—C13A	0.8 (7)
C3—C2—C12—C13	0.9 (6)	C1A—C2A—C12A—C13A	−179.2 (4)
C11—C12—C13—C14	1.2 (7)	C11A—C12A—C13A—C14A	−1.4 (7)
C2—C12—C13—C14	−177.5 (5)	C2A—C12A—C13A—C14A	177.3 (5)
C12—C13—C14—C15	−1.8 (8)	C12A—C13A—C14A—C15A	1.0 (8)
C13—C14—C15—C16	0.6 (9)	C13A—C14A—C15A—C16A	−0.1 (8)
C14—C15—C16—C11	1.2 (7)	C14A—C15A—C16A—C11A	−0.3 (7)
C12—C11—C16—C15	−1.8 (8)	O1A—C11A—C16A—C15A	−178.3 (4)
O1—C11—C16—C15	179.3 (4)	C12A—C11A—C16A—C15A	−0.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1Aⁱ	0.94 (9)	1.92 (9)	2.854 (5)	177 (7)
O2A—H2A···O1ⁱⁱ	0.96 (6)	1.97 (7)	2.923 (5)	178 (5)

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

(Vb) 10-oxa-9-boraphenanthren-9-ol top

Crystal data top

C₁₂H₉BO₂	F(000) = 816
M_r = 196.00	D_x = 1.390 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11092 reflections
a = 25.627 (3) Å	θ = 2.8–25.8°
b = 5.1594 (4) Å	µ = 0.09 mm⁻¹
c = 14.7701 (12) Å	T = 173 K
β = 106.459 (7)°	Plate, colourless
V = 1872.9 (3) Å³	0.32 × 0.24 × 0.13 mm
Z = 8

Data collection top

Stoe IPDS II two-circle diffractometer	2446 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.092
Graphite monochromator	θ_max = 25.4°, θ_min = 0.8°
ω scans	h = −30→28
14607 measured reflections	k = −6→6
3334 independent reflections	l = −17→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.091	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.230	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1752P)²] where P = (F_o² + 2F_c²)/3
3334 reflections	(Δ/σ)_max < 0.001
274 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
B1	0.45822 (18)	0.3199 (8)	0.4191 (4)	0.0531 (11)
O1	0.43671 (11)	0.1732 (5)	0.4786 (2)	0.0544 (7)
O2	0.50917 (11)	0.2669 (5)	0.4148 (3)	0.0611 (8)
H2	0.5192	0.1230	0.4405	0.092*
C1	0.42282 (16)	0.5375 (7)	0.3600 (3)	0.0527 (9)
C2	0.37066 (15)	0.5817 (7)	0.3721 (3)	0.0488 (9)
C3	0.33857 (17)	0.7773 (7)	0.3192 (3)	0.0540 (10)
H3	0.3032	0.8070	0.3256	0.065*
C4	0.35693 (18)	0.9279 (7)	0.2581 (3)	0.0604 (11)
H4	0.3344	1.0616	0.2236	0.073*
C5	0.40872 (19)	0.8862 (7)	0.2460 (3)	0.0612 (11)
H5	0.4212	0.9904	0.2033	0.073*
C6	0.44123 (18)	0.6927 (8)	0.2967 (3)	0.0585 (10)
H6	0.4763	0.6636	0.2890	0.070*
C11	0.38517 (15)	0.2231 (7)	0.4881 (3)	0.0484 (9)
C12	0.35141 (15)	0.4207 (6)	0.4378 (3)	0.0487 (9)
C13	0.30071 (16)	0.4488 (7)	0.4554 (3)	0.0545 (10)
H13	0.2774	0.5851	0.4247	0.065*
C14	0.28315 (17)	0.2885 (8)	0.5149 (3)	0.0566 (10)
H14	0.2478	0.3097	0.5225	0.068*
C15	0.31741 (18)	0.0950 (7)	0.5642 (3)	0.0595 (10)
H15	0.3059	−0.0142	0.6067	0.071*
C16	0.36872 (18)	0.0621 (7)	0.5508 (3)	0.0561 (10)
H16	0.3924	−0.0694	0.5843	0.067*
B1A	0.04310 (17)	0.3219 (8)	0.4624 (3)	0.0490 (10)
O1A	0.06230 (10)	0.1745 (5)	0.54320 (19)	0.0487 (7)
O2A	−0.00752 (10)	0.2676 (5)	0.4058 (2)	0.0541 (7)
H2A	−0.0196	0.1350	0.4259	0.081*
C1A	0.07900 (15)	0.5410 (6)	0.4415 (3)	0.0469 (8)
C2A	0.13036 (16)	0.5858 (6)	0.5072 (3)	0.0475 (9)
C3A	0.16333 (16)	0.7824 (7)	0.4894 (3)	0.0487 (9)
H3A	0.1981	0.8123	0.5326	0.058*
C4A	0.14571 (17)	0.9360 (7)	0.4088 (3)	0.0542 (10)
H4A	0.1683	1.0715	0.3978	0.065*
C5A	0.09572 (17)	0.8918 (7)	0.3451 (3)	0.0554 (10)
H5A	0.0841	0.9958	0.2899	0.066*
C6A	0.06233 (16)	0.6974 (7)	0.3607 (3)	0.0529 (9)
H6A	0.0278	0.6693	0.3165	0.063*
C11A	0.11276 (14)	0.2229 (6)	0.6064 (3)	0.0429 (9)
C12A	0.14670 (14)	0.4190 (6)	0.5919 (3)	0.0437 (8)
C13A	0.19703 (16)	0.4449 (7)	0.6611 (3)	0.0513 (9)
H13A	0.2209	0.5801	0.6549	0.062*
C14A	0.21292 (16)	0.2793 (7)	0.7384 (3)	0.0524 (10)
H14A	0.2476	0.2977	0.7832	0.063*
C15A	0.17764 (17)	0.0889 (7)	0.7488 (3)	0.0550 (9)
H15A	0.1879	−0.0238	0.8017	0.066*
C16A	0.12788 (16)	0.0588 (7)	0.6840 (3)	0.0518 (9)
H16A	0.1038	−0.0737	0.6920	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.047 (2)	0.051 (2)	0.057 (3)	0.0027 (18)	0.009 (2)	−0.004 (2)
O1	0.0481 (16)	0.0524 (15)	0.0595 (18)	0.0071 (11)	0.0101 (14)	0.0034 (12)
O2	0.0481 (16)	0.0583 (15)	0.076 (2)	0.0092 (11)	0.0169 (17)	0.0094 (14)
C1	0.057 (2)	0.0479 (18)	0.051 (2)	−0.0006 (16)	0.011 (2)	−0.0046 (16)
C2	0.048 (2)	0.0461 (17)	0.048 (2)	0.0037 (15)	0.0067 (18)	−0.0038 (15)
C3	0.052 (2)	0.0499 (18)	0.055 (3)	0.0065 (15)	0.007 (2)	−0.0001 (17)
C4	0.067 (3)	0.0513 (19)	0.055 (3)	0.0095 (18)	0.005 (2)	−0.0019 (17)
C5	0.073 (3)	0.0493 (19)	0.060 (3)	−0.0042 (17)	0.018 (2)	−0.0011 (18)
C6	0.063 (3)	0.055 (2)	0.059 (3)	0.0009 (18)	0.019 (2)	0.0007 (19)
C11	0.048 (2)	0.0446 (17)	0.050 (2)	0.0000 (14)	0.0089 (19)	−0.0040 (15)
C12	0.048 (2)	0.0434 (17)	0.051 (2)	0.0032 (14)	0.0076 (18)	−0.0038 (16)
C13	0.053 (2)	0.0503 (18)	0.055 (2)	0.0037 (15)	0.0077 (19)	−0.0055 (17)
C14	0.048 (2)	0.067 (2)	0.055 (3)	−0.0032 (18)	0.015 (2)	−0.0062 (18)
C15	0.068 (3)	0.056 (2)	0.058 (3)	−0.0071 (18)	0.023 (2)	−0.0020 (19)
C16	0.063 (2)	0.0481 (18)	0.055 (2)	0.0024 (17)	0.013 (2)	0.0005 (16)
B1A	0.046 (2)	0.047 (2)	0.054 (3)	0.0052 (17)	0.014 (2)	−0.0037 (18)
O1A	0.0457 (15)	0.0466 (13)	0.0511 (16)	−0.0035 (10)	0.0094 (12)	0.0007 (11)
O2A	0.0480 (15)	0.0478 (13)	0.0608 (19)	−0.0040 (11)	0.0061 (15)	0.0059 (12)
C1A	0.050 (2)	0.0406 (16)	0.051 (2)	0.0029 (14)	0.0158 (18)	−0.0015 (15)
C2A	0.053 (2)	0.0384 (16)	0.053 (2)	0.0001 (14)	0.0180 (18)	−0.0041 (15)
C3A	0.051 (2)	0.0467 (17)	0.050 (2)	−0.0061 (15)	0.017 (2)	−0.0023 (15)
C4A	0.065 (3)	0.0436 (17)	0.060 (3)	−0.0027 (16)	0.027 (2)	0.0023 (16)
C5A	0.069 (3)	0.0445 (17)	0.055 (2)	0.0043 (16)	0.021 (2)	0.0056 (17)
C6A	0.055 (2)	0.0508 (18)	0.052 (2)	0.0025 (16)	0.0131 (19)	0.0004 (17)
C11A	0.037 (2)	0.0417 (16)	0.049 (2)	−0.0016 (13)	0.0113 (17)	−0.0061 (14)
C12A	0.046 (2)	0.0389 (16)	0.047 (2)	−0.0007 (13)	0.0132 (17)	−0.0022 (14)
C13A	0.052 (2)	0.0458 (17)	0.056 (2)	−0.0076 (15)	0.0154 (19)	−0.0026 (16)
C14A	0.050 (2)	0.0558 (19)	0.050 (2)	−0.0048 (15)	0.0106 (19)	−0.0043 (16)
C15A	0.063 (2)	0.0461 (18)	0.054 (2)	−0.0042 (16)	0.014 (2)	0.0005 (16)
C16A	0.056 (2)	0.0435 (17)	0.057 (2)	−0.0063 (15)	0.017 (2)	−0.0011 (16)

Geometric parameters (Å, º) top

B1—O2	1.353 (5)	B1A—O2A	1.359 (5)
B1—O1	1.387 (6)	B1A—O1A	1.382 (5)
B1—C1	1.548 (6)	B1A—C1A	1.543 (6)
O1—C11	1.391 (5)	O1A—C11A	1.386 (4)
O2—H2	0.8400	O2A—H2A	0.8400
C1—C6	1.410 (6)	C1A—C6A	1.403 (6)
C1—C2	1.416 (5)	C1A—C2A	1.415 (6)
C2—C3	1.393 (5)	C2A—C3A	1.392 (5)
C2—C12	1.465 (6)	C2A—C12A	1.478 (5)
C3—C4	1.371 (6)	C3A—C4A	1.395 (6)
C3—H3	0.9500	C3A—H3A	0.9500
C4—C5	1.405 (6)	C4A—C5A	1.377 (6)
C4—H4	0.9500	C4A—H4A	0.9500
C5—C6	1.378 (6)	C5A—C6A	1.380 (6)
C5—H5	0.9500	C5A—H5A	0.9500
C6—H6	0.9500	C6A—H6A	0.9500
C11—C16	1.395 (6)	C11A—C16A	1.389 (6)
C11—C12	1.406 (5)	C11A—C12A	1.390 (5)
C12—C13	1.403 (5)	C12A—C13A	1.407 (6)
C13—C14	1.372 (6)	C13A—C14A	1.391 (6)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.391 (6)	C14A—C15A	1.373 (5)
C14—H14	0.9500	C14A—H14A	0.9500
C15—C16	1.394 (6)	C15A—C16A	1.369 (6)
C15—H15	0.9500	C15A—H15A	0.9500
C16—H16	0.9500	C16A—H16A	0.9500

O2—B1—O1	118.8 (4)	O2A—B1A—O1A	117.5 (4)
O2—B1—C1	122.7 (4)	O2A—B1A—C1A	123.2 (4)
O1—B1—C1	118.6 (3)	O1A—B1A—C1A	119.3 (4)
B1—O1—C11	121.5 (3)	B1A—O1A—C11A	121.2 (3)
B1—O2—H2	109.5	B1A—O2A—H2A	109.5
C6—C1—C2	119.8 (4)	C6A—C1A—C2A	119.3 (3)
C6—C1—B1	122.2 (4)	C6A—C1A—B1A	122.4 (4)
C2—C1—B1	118.0 (3)	C2A—C1A—B1A	118.3 (3)
C3—C2—C1	118.3 (4)	C3A—C2A—C1A	119.1 (4)
C3—C2—C12	121.7 (4)	C3A—C2A—C12A	122.8 (4)
C1—C2—C12	119.9 (3)	C1A—C2A—C12A	118.0 (3)
C4—C3—C2	121.4 (4)	C2A—C3A—C4A	120.5 (4)
C4—C3—H3	119.3	C2A—C3A—H3A	119.7
C2—C3—H3	119.3	C4A—C3A—H3A	119.7
C3—C4—C5	120.7 (4)	C5A—C4A—C3A	120.2 (4)
C3—C4—H4	119.7	C5A—C4A—H4A	119.9
C5—C4—H4	119.7	C3A—C4A—H4A	119.9
C6—C5—C4	119.3 (4)	C4A—C5A—C6A	120.4 (4)
C6—C5—H5	120.4	C4A—C5A—H5A	119.8
C4—C5—H5	120.4	C6A—C5A—H5A	119.8
C5—C6—C1	120.5 (4)	C5A—C6A—C1A	120.5 (4)
C5—C6—H6	119.7	C5A—C6A—H6A	119.8
C1—C6—H6	119.7	C1A—C6A—H6A	119.8
O1—C11—C16	115.5 (3)	O1A—C11A—C16A	115.8 (3)
O1—C11—C12	122.7 (4)	O1A—C11A—C12A	122.2 (4)
C16—C11—C12	121.8 (4)	C16A—C11A—C12A	122.0 (4)
C13—C12—C11	116.1 (4)	C11A—C12A—C13A	116.2 (3)
C13—C12—C2	124.6 (3)	C11A—C12A—C2A	121.0 (4)
C11—C12—C2	119.3 (4)	C13A—C12A—C2A	122.8 (3)
C14—C13—C12	123.1 (4)	C14A—C13A—C12A	122.2 (3)
C14—C13—H13	118.5	C14A—C13A—H13A	118.9
C12—C13—H13	118.5	C12A—C13A—H13A	118.9
C13—C14—C15	119.6 (4)	C15A—C14A—C13A	118.8 (4)
C13—C14—H14	120.2	C15A—C14A—H14A	120.6
C15—C14—H14	120.2	C13A—C14A—H14A	120.6
C14—C15—C16	119.6 (4)	C16A—C15A—C14A	121.0 (4)
C14—C15—H15	120.2	C16A—C15A—H15A	119.5
C16—C15—H15	120.2	C14A—C15A—H15A	119.5
C15—C16—C11	119.7 (4)	C15A—C16A—C11A	119.6 (3)
C15—C16—H16	120.1	C15A—C16A—H16A	120.2
C11—C16—H16	120.1	C11A—C16A—H16A	120.2

O2—B1—O1—C11	178.1 (4)	O2A—B1A—O1A—C11A	−177.8 (3)
C1—B1—O1—C11	−2.0 (6)	C1A—B1A—O1A—C11A	1.1 (5)
O2—B1—C1—C6	0.9 (7)	O2A—B1A—C1A—C6A	−1.5 (6)
O1—B1—C1—C6	−178.9 (4)	O1A—B1A—C1A—C6A	179.6 (3)
O2—B1—C1—C2	−178.1 (4)	O2A—B1A—C1A—C2A	177.9 (3)
O1—B1—C1—C2	2.0 (6)	O1A—B1A—C1A—C2A	−0.9 (5)
C6—C1—C2—C3	0.9 (6)	C6A—C1A—C2A—C3A	−0.6 (5)
B1—C1—C2—C3	180.0 (4)	B1A—C1A—C2A—C3A	179.9 (3)
C6—C1—C2—C12	180.0 (4)	C6A—C1A—C2A—C12A	179.6 (3)
B1—C1—C2—C12	−1.0 (5)	B1A—C1A—C2A—C12A	0.2 (5)
C1—C2—C3—C4	−1.2 (6)	C1A—C2A—C3A—C4A	0.9 (5)
C12—C2—C3—C4	179.7 (4)	C12A—C2A—C3A—C4A	−179.4 (3)
C2—C3—C4—C5	0.9 (7)	C2A—C3A—C4A—C5A	−0.9 (6)
C3—C4—C5—C6	−0.4 (7)	C3A—C4A—C5A—C6A	0.7 (6)
C4—C5—C6—C1	0.1 (7)	C4A—C5A—C6A—C1A	−0.4 (6)
C2—C1—C6—C5	−0.4 (6)	C2A—C1A—C6A—C5A	0.4 (6)
B1—C1—C6—C5	−179.4 (4)	B1A—C1A—C6A—C5A	179.8 (3)
B1—O1—C11—C16	−179.5 (4)	B1A—O1A—C11A—C16A	−178.9 (3)
B1—O1—C11—C12	0.9 (6)	B1A—O1A—C11A—C12A	−0.5 (5)
O1—C11—C12—C13	−179.6 (3)	O1A—C11A—C12A—C13A	−179.3 (3)
C16—C11—C12—C13	0.9 (6)	C16A—C11A—C12A—C13A	−1.0 (5)
O1—C11—C12—C2	0.2 (6)	O1A—C11A—C12A—C2A	−0.3 (5)
C16—C11—C12—C2	−179.3 (3)	C16A—C11A—C12A—C2A	178.0 (3)
C3—C2—C12—C13	−1.3 (6)	C3A—C2A—C12A—C11A	−179.4 (3)
C1—C2—C12—C13	179.6 (3)	C1A—C2A—C12A—C11A	0.4 (5)
C3—C2—C12—C11	178.9 (4)	C3A—C2A—C12A—C13A	−0.3 (5)
C1—C2—C12—C11	−0.1 (6)	C1A—C2A—C12A—C13A	179.4 (3)
C11—C12—C13—C14	−2.6 (6)	C11A—C12A—C13A—C14A	2.0 (5)
C2—C12—C13—C14	177.6 (4)	C2A—C12A—C13A—C14A	−177.1 (3)
C12—C13—C14—C15	3.0 (7)	C12A—C13A—C14A—C15A	−1.9 (6)
C13—C14—C15—C16	−1.5 (6)	C13A—C14A—C15A—C16A	0.8 (6)
C14—C15—C16—C11	−0.1 (6)	C14A—C15A—C16A—C11A	0.1 (6)
O1—C11—C16—C15	−179.2 (3)	O1A—C11A—C16A—C15A	178.5 (3)
C12—C11—C16—C15	0.4 (6)	C12A—C11A—C16A—C15A	0.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.84	2.07	2.884 (4)	164
O2A—H2A···O1Aⁱⁱ	0.84	2.06	2.888 (4)	170

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z+1.

(VI) 9-[(Biphenyl-2-yl)oxy]-10-oxa-9-boraphenanthrene top

Crystal data top

C₂₄H₁₇BO₂	F(000) = 2912
M_r = 348.19	D_x = 1.317 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 13336 reflections
a = 20.7814 (10) Å	θ = 1.9–25.8°
b = 10.3740 (4) Å	µ = 0.08 mm⁻¹
c = 32.6452 (19) Å	T = 173 K
β = 93.427 (4)°	Block, colourless
V = 7025.3 (6) Å³	0.31 × 0.22 × 0.22 mm
Z = 16

Data collection top

Stoe IPDS II two-circle diffractometer	4375 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.086
Graphite monochromator	θ_max = 25.4°, θ_min = 2.0°
ω scans	h = −24→25
24449 measured reflections	k = −12→12
6439 independent reflections	l = −37→39

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0858P)²] where P = (F_o² + 2F_c²)/3
6439 reflections	(Δ/σ)_max < 0.001
973 parameters	Δρ_max = 0.35 e Å⁻³
650 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
B1	0.1150 (4)	0.9736 (6)	0.8472 (2)	0.0410 (16)
O1	0.1477 (2)	0.9796 (4)	0.81022 (13)	0.0403 (10)
O2	0.1336 (2)	0.8834 (4)	0.87583 (13)	0.0396 (9)
C1	0.0578 (3)	1.0662 (6)	0.85224 (19)	0.0385 (14)
C2	0.0439 (3)	1.1566 (5)	0.82208 (18)	0.0353 (13)
C3	−0.0077 (3)	1.2418 (6)	0.8276 (2)	0.0448 (16)
H3	−0.0191	1.3031	0.8068	0.054*
C4	−0.0410 (3)	1.2382 (6)	0.8614 (2)	0.0484 (16)
H4	−0.0747	1.2987	0.8645	0.058*
C5	−0.0275 (3)	1.1485 (6)	0.8918 (2)	0.0439 (14)
H5	−0.0523	1.1438	0.9152	0.053*
C6	0.0248 (3)	1.0635 (6)	0.8869 (2)	0.0491 (16)
H6	0.0369	1.0039	0.9080	0.059*
C11	0.1327 (3)	1.0724 (6)	0.78152 (19)	0.0388 (14)
C12	0.0813 (3)	1.1604 (5)	0.78538 (18)	0.0335 (13)
C13	0.0743 (3)	1.2533 (5)	0.7530 (2)	0.0436 (15)
H13	0.0422	1.3181	0.7544	0.052*
C14	0.1107 (4)	1.2525 (7)	0.7213 (2)	0.0495 (16)
H14	0.1032	1.3172	0.7009	0.059*
C15	0.1587 (3)	1.1645 (6)	0.7157 (2)	0.0447 (15)
H15	0.1828	1.1650	0.6918	0.054*
C16	0.1705 (3)	1.0721 (6)	0.74782 (19)	0.0415 (14)
H16	0.2041	1.0106	0.7461	0.050*
C21	0.1863 (3)	0.8016 (5)	0.87792 (19)	0.0373 (13)
C22	0.2048 (3)	0.7520 (5)	0.91842 (18)	0.0414 (14)
C23	0.2574 (3)	0.6715 (6)	0.9228 (2)	0.0595 (18)
H23	0.2724	0.6439	0.9494	0.071*
C24	0.2888 (4)	0.6300 (7)	0.8889 (2)	0.0603 (19)
H24	0.3227	0.5688	0.8922	0.072*
C25	0.2700 (4)	0.6792 (7)	0.8491 (2)	0.0519 (16)
H25	0.2927	0.6550	0.8259	0.062*
C26	0.2191 (3)	0.7613 (6)	0.8450 (2)	0.0421 (14)
H26	0.2057	0.7919	0.8185	0.051*
C31	0.1675 (3)	0.7857 (6)	0.95455 (19)	0.0451 (15)
C32	0.1042 (3)	0.7661 (5)	0.95595 (18)	0.0480 (13)
H32	0.0803	0.7369	0.9320	0.058*
C33	0.0722 (3)	0.7877 (5)	0.9919 (2)	0.0569 (15)
H33	0.0276	0.7678	0.9924	0.068*
C34	0.1032 (4)	0.8360 (6)	1.0257 (2)	0.0617 (19)
H34	0.0804	0.8537	1.0494	0.074*
C35	0.1705 (3)	0.8605 (5)	1.02578 (18)	0.0568 (14)
H35	0.1933	0.8927	1.0497	0.068*
C36	0.2024 (3)	0.8367 (5)	0.99043 (18)	0.0503 (13)
H36	0.2472	0.8541	0.9899	0.060*
B1A	0.1166 (4)	0.4720 (6)	0.8430 (2)	0.0416 (16)
O1A	0.1531 (2)	0.4801 (4)	0.80771 (12)	0.0370 (9)
O2A	0.1336 (2)	0.3824 (4)	0.87213 (12)	0.0390 (9)
C1A	0.0588 (3)	0.5625 (6)	0.84599 (18)	0.0371 (13)
C2A	0.0470 (3)	0.6550 (6)	0.81636 (18)	0.0365 (13)
C3A	−0.0034 (3)	0.7413 (6)	0.8209 (2)	0.0434 (15)
H3A	−0.0114	0.8067	0.8008	0.052*
C4A	−0.0411 (3)	0.7341 (6)	0.85302 (18)	0.0428 (14)
H4A	−0.0745	0.7956	0.8555	0.051*
C5A	−0.0319 (3)	0.6380 (6)	0.88267 (18)	0.0406 (13)
H5A	−0.0599	0.6288	0.9045	0.049*
C6A	0.0211 (3)	0.5550 (6)	0.87853 (18)	0.0437 (15)
H6A	0.0307	0.4920	0.8991	0.052*
C11A	0.1382 (3)	0.5717 (5)	0.77800 (18)	0.0338 (13)
C12A	0.0873 (3)	0.6586 (5)	0.78084 (17)	0.0333 (13)
C13A	0.0794 (3)	0.7486 (5)	0.74773 (19)	0.0383 (14)
H13A	0.0466	0.8122	0.7482	0.046*
C14A	0.1172 (4)	0.7447 (7)	0.7164 (2)	0.0503 (17)
H14A	0.1097	0.8069	0.6952	0.060*
C15A	0.1657 (3)	0.6586 (6)	0.71212 (18)	0.0416 (14)
H15A	0.1907	0.6581	0.6887	0.050*
C16A	0.1767 (3)	0.5696 (6)	0.74484 (19)	0.0404 (14)
H16A	0.2107	0.5085	0.7440	0.048*
C21A	0.1832 (3)	0.2934 (6)	0.87644 (18)	0.0385 (14)
C22A	0.1905 (3)	0.2305 (5)	0.91601 (18)	0.0392 (13)
C23A	0.2350 (3)	0.1334 (5)	0.92105 (19)	0.0474 (14)
H23A	0.2393	0.0886	0.9465	0.057*
C24A	0.2747 (3)	0.0986 (5)	0.8892 (2)	0.0472 (15)
H24A	0.3067	0.0338	0.8935	0.057*
C25A	0.2663 (4)	0.1611 (6)	0.8511 (2)	0.0558 (18)
H25A	0.2920	0.1375	0.8292	0.067*
C26A	0.2211 (3)	0.2557 (6)	0.8456 (2)	0.0429 (15)
H26A	0.2156	0.2968	0.8196	0.052*
C31A	0.1489 (3)	0.2653 (5)	0.95007 (16)	0.0365 (12)
C32A	0.1381 (3)	0.3951 (4)	0.96027 (17)	0.0442 (11)
H32A	0.1540	0.4623	0.9439	0.053*
C33A	0.1038 (3)	0.4245 (5)	0.99455 (18)	0.0580 (15)
H33A	0.0973	0.5120	1.0019	0.070*
C34A	0.0792 (3)	0.3267 (6)	1.0179 (2)	0.0571 (17)
H34A	0.0559	0.3467	1.0413	0.069*
C35A	0.0888 (4)	0.2020 (7)	1.0072 (2)	0.0739 (18)
H35A	0.0711	0.1352	1.0229	0.089*
C36A	0.1239 (3)	0.1700 (5)	0.97378 (17)	0.0550 (14)
H36A	0.1307	0.0820	0.9672	0.066*
B1B	0.3866 (3)	0.7185 (6)	0.6486 (2)	0.0380 (16)
O1B	0.3554 (2)	0.7261 (4)	0.68241 (13)	0.0433 (10)
O2B	0.37027 (19)	0.6327 (4)	0.61742 (12)	0.0401 (10)
C1B	0.4427 (3)	0.8111 (5)	0.64133 (17)	0.0340 (13)
C2B	0.4591 (3)	0.9058 (5)	0.67254 (19)	0.0374 (13)
C3B	0.5094 (3)	0.9924 (6)	0.6678 (2)	0.0408 (14)
H3B	0.5200	1.0552	0.6883	0.049*
C4B	0.5447 (3)	0.9854 (6)	0.6317 (2)	0.0463 (15)
H4B	0.5799	1.0423	0.6285	0.056*
C5B	0.5281 (3)	0.8962 (6)	0.6014 (2)	0.0521 (16)
H5B	0.5507	0.8960	0.5769	0.062*
C6B	0.4809 (3)	0.8100 (6)	0.60572 (18)	0.0412 (14)
H6B	0.4724	0.7469	0.5850	0.049*
C11B	0.3702 (3)	0.8171 (6)	0.71253 (19)	0.0414 (15)
C12B	0.4192 (3)	0.9067 (6)	0.7087 (2)	0.0396 (14)
C13B	0.4307 (3)	0.9944 (6)	0.74003 (19)	0.0418 (14)
H13B	0.4648	1.0547	0.7383	0.050*
C14B	0.3923 (3)	0.9974 (6)	0.7754 (2)	0.0435 (15)
H14B	0.4001	1.0572	0.7972	0.052*
C15B	0.3425 (3)	0.9054 (6)	0.77539 (19)	0.0444 (14)
H15B	0.3148	0.9063	0.7975	0.053*
C16B	0.3322 (3)	0.8170 (6)	0.7460 (2)	0.0476 (16)
H16B	0.2991	0.7546	0.7480	0.057*
C21B	0.3184 (3)	0.5465 (6)	0.61356 (19)	0.0377 (13)
C22B	0.3002 (3)	0.5078 (5)	0.5757 (2)	0.0437 (15)
C23B	0.2458 (3)	0.4235 (5)	0.57083 (19)	0.0479 (14)
H23B	0.2320	0.3938	0.5442	0.057*
C24B	0.2134 (3)	0.3848 (6)	0.6040 (2)	0.0569 (18)
H24B	0.1763	0.3317	0.6003	0.068*
C25B	0.2340 (3)	0.4220 (6)	0.6415 (2)	0.0466 (16)
H25B	0.2126	0.3905	0.6644	0.056*
C26B	0.2872 (3)	0.5074 (6)	0.6484 (2)	0.0455 (16)
H26B	0.3007	0.5364	0.6751	0.055*
C31B	0.3342 (3)	0.5423 (4)	0.53833 (16)	0.0370 (12)
C32B	0.4001 (3)	0.5170 (5)	0.53635 (18)	0.0473 (12)
H32B	0.4236	0.4833	0.5598	0.057*
C33B	0.4314 (3)	0.5398 (5)	0.5011 (2)	0.0539 (14)
H33B	0.4762	0.5221	0.5006	0.065*
C34B	0.3981 (3)	0.5887 (5)	0.46619 (19)	0.0507 (15)
H34B	0.4197	0.6045	0.4418	0.061*
C35B	0.3339 (3)	0.6132 (5)	0.46773 (18)	0.0581 (15)
H35B	0.3111	0.6479	0.4441	0.070*
C36B	0.3007 (3)	0.5894 (5)	0.50244 (17)	0.0502 (13)
H36B	0.2556	0.6047	0.5022	0.060*
B1C	0.3851 (3)	0.2221 (6)	0.65528 (19)	0.0296 (13)
O1C	0.3515 (2)	0.2320 (4)	0.68891 (13)	0.0406 (10)
O2C	0.36904 (19)	0.1389 (4)	0.62396 (12)	0.0392 (9)
C1C	0.4420 (3)	0.3140 (5)	0.64907 (18)	0.0353 (13)
C2C	0.4559 (3)	0.4101 (5)	0.68031 (17)	0.0337 (13)
C3C	0.5068 (3)	0.4990 (6)	0.67550 (19)	0.0375 (13)
H3C	0.5148	0.5656	0.6951	0.045*
C4C	0.5452 (3)	0.4885 (7)	0.6417 (2)	0.0486 (16)
H4C	0.5800	0.5464	0.6387	0.058*
C5C	0.5321 (3)	0.3943 (7)	0.6133 (2)	0.0521 (17)
H5C	0.5582	0.3897	0.5904	0.063*
C6C	0.4838 (3)	0.3062 (6)	0.61578 (19)	0.0414 (14)
H6C	0.4779	0.2405	0.5957	0.050*
C11C	0.3663 (3)	0.3208 (6)	0.71934 (18)	0.0368 (13)
C12C	0.4153 (3)	0.4135 (6)	0.71620 (18)	0.0367 (13)
C13C	0.4263 (3)	0.4988 (6)	0.7474 (2)	0.0422 (14)
H13C	0.4605	0.5590	0.7458	0.051*
C14C	0.3886 (3)	0.5011 (5)	0.78222 (18)	0.0356 (13)
H14C	0.3963	0.5613	0.8039	0.043*
C15C	0.3389 (3)	0.4085 (6)	0.7827 (2)	0.0482 (16)
H15C	0.3115	0.4085	0.8050	0.058*
C16C	0.3286 (3)	0.3205 (6)	0.75290 (19)	0.0442 (15)
H16C	0.2955	0.2580	0.7548	0.053*
C21C	0.3208 (3)	0.0459 (6)	0.6190 (2)	0.0400 (14)
C22C	0.3140 (3)	−0.0108 (5)	0.58218 (18)	0.0383 (13)
C23C	0.2655 (3)	−0.1077 (6)	0.5770 (2)	0.0542 (17)
H23C	0.2596	−0.1506	0.5514	0.065*
C24C	0.2271 (4)	−0.1406 (7)	0.6081 (3)	0.0620 (19)
H24C	0.1949	−0.2050	0.6038	0.074*
C25C	0.2351 (3)	−0.0824 (6)	0.6439 (2)	0.0498 (16)
H25C	0.2081	−0.1055	0.6652	0.060*
C26C	0.2832 (3)	0.0141 (6)	0.6516 (2)	0.0446 (15)
H26C	0.2893	0.0547	0.6776	0.054*
C31C	0.3514 (3)	0.0237 (6)	0.54633 (19)	0.0470 (16)
C32C	0.3646 (3)	0.1473 (5)	0.53533 (17)	0.0459 (12)
H32C	0.3499	0.2163	0.5515	0.055*
C33C	0.3990 (3)	0.1752 (5)	0.50110 (17)	0.0545 (14)
H33C	0.4073	0.2621	0.4940	0.065*
C34C	0.4208 (4)	0.0764 (8)	0.4776 (2)	0.075 (2)
H34C	0.4422	0.0951	0.4534	0.089*
C35C	0.4117 (3)	−0.0487 (6)	0.48888 (19)	0.0638 (16)
H35C	0.4291	−0.1162	0.4733	0.077*
C36C	0.3776 (3)	−0.0784 (5)	0.52258 (18)	0.0563 (14)
H36C	0.3715	−0.1658	0.5301	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.055 (4)	0.034 (3)	0.034 (3)	−0.005 (3)	−0.004 (3)	−0.005 (2)
O1	0.040 (2)	0.0369 (19)	0.044 (2)	0.0067 (18)	0.0008 (18)	0.0043 (17)
O2	0.037 (2)	0.0320 (18)	0.049 (2)	0.0041 (17)	−0.0071 (17)	−0.0039 (17)
C1	0.029 (3)	0.035 (3)	0.051 (3)	−0.001 (2)	−0.005 (3)	−0.007 (2)
C2	0.028 (3)	0.032 (3)	0.045 (3)	−0.005 (2)	−0.003 (2)	−0.007 (2)
C3	0.038 (3)	0.032 (3)	0.063 (4)	0.004 (2)	−0.012 (3)	−0.001 (3)
C4	0.043 (3)	0.028 (3)	0.074 (4)	0.008 (2)	−0.003 (3)	0.001 (3)
C5	0.043 (3)	0.040 (3)	0.050 (3)	0.006 (2)	0.009 (3)	−0.005 (2)
C6	0.049 (4)	0.038 (3)	0.058 (4)	0.007 (3)	−0.014 (3)	−0.005 (3)
C11	0.032 (3)	0.037 (3)	0.047 (3)	0.002 (2)	−0.007 (2)	−0.002 (2)
C12	0.025 (3)	0.026 (2)	0.048 (3)	0.002 (2)	−0.008 (2)	0.003 (2)
C13	0.044 (3)	0.026 (3)	0.058 (4)	0.003 (2)	−0.016 (3)	0.007 (2)
C14	0.047 (4)	0.050 (3)	0.051 (4)	−0.003 (3)	−0.005 (3)	0.016 (3)
C15	0.040 (3)	0.046 (3)	0.047 (3)	−0.008 (3)	−0.006 (3)	0.010 (2)
C16	0.039 (3)	0.035 (3)	0.050 (3)	0.007 (2)	−0.004 (3)	0.003 (2)
C21	0.039 (3)	0.024 (2)	0.047 (3)	0.002 (2)	−0.008 (3)	0.007 (2)
C22	0.034 (3)	0.039 (3)	0.049 (3)	−0.002 (2)	−0.008 (2)	0.011 (2)
C23	0.055 (4)	0.056 (4)	0.067 (4)	0.026 (3)	−0.003 (3)	0.015 (3)
C24	0.059 (4)	0.058 (4)	0.064 (4)	0.029 (3)	0.011 (3)	0.011 (3)
C25	0.056 (4)	0.044 (3)	0.055 (4)	0.010 (3)	0.000 (3)	0.002 (3)
C26	0.042 (3)	0.037 (3)	0.048 (4)	0.003 (3)	0.002 (3)	0.002 (3)
C31	0.045 (4)	0.039 (3)	0.051 (3)	0.013 (2)	0.001 (3)	0.010 (2)
C32	0.046 (3)	0.042 (3)	0.056 (3)	−0.001 (2)	−0.006 (3)	−0.005 (2)
C33	0.051 (3)	0.046 (3)	0.075 (4)	0.004 (3)	0.010 (3)	−0.005 (3)
C34	0.093 (6)	0.036 (3)	0.058 (4)	0.005 (3)	0.019 (4)	0.005 (3)
C35	0.072 (4)	0.041 (3)	0.054 (3)	−0.002 (3)	−0.014 (3)	0.008 (2)
C36	0.052 (3)	0.043 (3)	0.054 (3)	−0.002 (2)	−0.010 (2)	0.008 (2)
B1A	0.053 (4)	0.034 (3)	0.037 (3)	−0.014 (3)	0.000 (3)	0.003 (3)
O1A	0.041 (2)	0.0325 (18)	0.038 (2)	0.0022 (17)	0.0059 (17)	0.0066 (16)
O2A	0.039 (2)	0.0331 (18)	0.045 (2)	0.0009 (17)	−0.0010 (17)	0.0031 (16)
C1A	0.034 (3)	0.038 (3)	0.038 (3)	−0.006 (2)	−0.007 (2)	−0.003 (2)
C2A	0.033 (3)	0.034 (3)	0.042 (3)	−0.005 (2)	0.000 (2)	−0.004 (2)
C3A	0.049 (4)	0.030 (3)	0.049 (3)	0.007 (2)	−0.015 (3)	0.000 (2)
C4A	0.047 (3)	0.041 (3)	0.040 (3)	0.010 (2)	−0.006 (3)	−0.001 (2)
C5A	0.031 (3)	0.048 (3)	0.043 (3)	−0.001 (2)	−0.001 (2)	0.000 (2)
C6A	0.049 (4)	0.044 (3)	0.037 (3)	0.001 (3)	−0.007 (3)	0.001 (2)
C11A	0.031 (3)	0.030 (3)	0.040 (3)	−0.003 (2)	−0.002 (2)	0.002 (2)
C12A	0.036 (3)	0.023 (2)	0.040 (3)	−0.002 (2)	−0.010 (2)	0.003 (2)
C13A	0.036 (3)	0.029 (3)	0.048 (3)	0.000 (2)	−0.009 (3)	0.010 (2)
C14A	0.051 (4)	0.051 (4)	0.048 (3)	−0.010 (3)	−0.002 (3)	0.018 (3)
C15A	0.046 (3)	0.043 (3)	0.036 (3)	−0.006 (3)	0.005 (2)	0.010 (2)
C16A	0.044 (3)	0.030 (3)	0.047 (3)	0.002 (2)	0.002 (3)	0.003 (2)
C21A	0.040 (3)	0.034 (3)	0.041 (3)	0.005 (3)	−0.007 (2)	0.011 (2)
C22A	0.047 (3)	0.025 (2)	0.045 (3)	−0.001 (2)	0.001 (2)	0.009 (2)
C23A	0.047 (3)	0.033 (3)	0.061 (3)	−0.003 (2)	−0.006 (3)	0.009 (2)
C24A	0.041 (3)	0.032 (3)	0.068 (4)	0.003 (2)	0.002 (3)	0.000 (2)
C25A	0.062 (4)	0.043 (3)	0.061 (4)	0.008 (3)	−0.004 (3)	−0.008 (3)
C26A	0.041 (3)	0.038 (3)	0.050 (4)	−0.003 (3)	0.007 (3)	0.004 (3)
C31A	0.040 (3)	0.028 (2)	0.041 (3)	−0.007 (2)	−0.004 (2)	0.0025 (19)
C32A	0.046 (3)	0.042 (3)	0.045 (3)	−0.003 (2)	−0.002 (2)	0.001 (2)
C33A	0.067 (4)	0.053 (3)	0.054 (3)	0.005 (3)	0.005 (3)	0.008 (3)
C34A	0.070 (5)	0.058 (3)	0.043 (3)	−0.008 (3)	0.001 (3)	−0.001 (3)
C35A	0.102 (5)	0.069 (4)	0.051 (4)	−0.014 (4)	0.012 (3)	0.006 (3)
C36A	0.081 (4)	0.042 (3)	0.041 (3)	0.002 (3)	−0.001 (3)	0.010 (2)
B1B	0.024 (3)	0.033 (3)	0.055 (4)	−0.007 (3)	−0.013 (3)	0.000 (3)
O1B	0.046 (2)	0.035 (2)	0.048 (2)	−0.0097 (18)	−0.006 (2)	−0.0032 (18)
O2B	0.038 (2)	0.0381 (19)	0.044 (2)	−0.0135 (18)	−0.0038 (17)	−0.0079 (17)
C1B	0.036 (3)	0.028 (2)	0.037 (3)	−0.003 (2)	−0.007 (2)	−0.002 (2)
C2B	0.036 (3)	0.028 (3)	0.046 (3)	0.000 (2)	−0.016 (2)	0.003 (2)
C3B	0.034 (3)	0.034 (3)	0.054 (4)	−0.005 (2)	0.001 (3)	0.000 (3)
C4B	0.031 (3)	0.047 (3)	0.060 (4)	−0.003 (3)	0.001 (3)	0.011 (3)
C5B	0.051 (4)	0.052 (3)	0.052 (4)	−0.003 (3)	−0.001 (3)	0.002 (3)
C6B	0.041 (3)	0.039 (3)	0.044 (3)	0.003 (2)	0.007 (2)	−0.006 (2)
C11B	0.049 (4)	0.029 (3)	0.045 (3)	0.002 (3)	−0.008 (3)	−0.003 (2)
C12B	0.038 (3)	0.034 (3)	0.046 (3)	0.003 (2)	−0.007 (3)	0.003 (2)
C13B	0.031 (3)	0.043 (3)	0.051 (3)	0.006 (2)	0.002 (3)	0.004 (3)
C14B	0.043 (3)	0.032 (3)	0.054 (4)	0.003 (2)	−0.007 (3)	0.000 (2)
C15B	0.047 (3)	0.042 (3)	0.044 (3)	0.001 (3)	0.004 (3)	0.000 (2)
C16B	0.040 (4)	0.044 (3)	0.058 (4)	−0.002 (3)	0.004 (3)	0.001 (3)
C21B	0.025 (3)	0.034 (3)	0.055 (3)	−0.001 (2)	0.004 (2)	0.002 (2)
C22B	0.045 (3)	0.030 (3)	0.057 (3)	−0.005 (2)	0.008 (3)	−0.008 (2)
C23B	0.034 (3)	0.049 (3)	0.061 (3)	−0.006 (2)	0.002 (3)	−0.022 (3)
C24B	0.035 (3)	0.050 (3)	0.085 (5)	−0.012 (3)	0.004 (3)	−0.017 (3)
C25B	0.035 (3)	0.041 (3)	0.066 (4)	−0.009 (2)	0.020 (3)	−0.010 (3)
C26B	0.046 (4)	0.033 (3)	0.057 (4)	−0.009 (3)	−0.003 (3)	−0.004 (3)
C31B	0.038 (3)	0.024 (2)	0.048 (3)	0.005 (2)	−0.006 (2)	−0.0087 (19)
C32B	0.040 (3)	0.043 (3)	0.058 (3)	0.001 (2)	−0.004 (3)	0.007 (2)
C33B	0.042 (3)	0.048 (3)	0.071 (4)	0.002 (2)	0.004 (3)	0.001 (3)
C34B	0.057 (4)	0.042 (3)	0.054 (4)	−0.002 (3)	0.005 (3)	0.000 (2)
C35B	0.074 (4)	0.050 (3)	0.048 (3)	0.003 (3)	−0.012 (3)	−0.006 (2)
C36B	0.045 (3)	0.051 (3)	0.053 (3)	0.006 (2)	−0.011 (2)	−0.016 (2)
B1C	0.023 (3)	0.031 (3)	0.035 (3)	−0.005 (2)	−0.003 (2)	0.003 (2)
O1C	0.042 (2)	0.0347 (19)	0.044 (2)	−0.0072 (18)	−0.0048 (18)	−0.0008 (17)
O2C	0.036 (2)	0.039 (2)	0.043 (2)	−0.0076 (17)	0.0035 (17)	−0.0074 (17)
C1C	0.036 (3)	0.029 (2)	0.042 (3)	0.003 (2)	0.002 (2)	0.003 (2)
C2C	0.034 (3)	0.031 (3)	0.036 (3)	0.001 (2)	−0.006 (2)	0.003 (2)
C3C	0.034 (3)	0.038 (3)	0.040 (3)	−0.003 (2)	0.002 (2)	0.000 (2)
C4C	0.035 (3)	0.058 (4)	0.053 (4)	−0.001 (3)	0.005 (3)	0.013 (3)
C5C	0.043 (3)	0.070 (4)	0.045 (3)	0.001 (3)	0.014 (3)	0.013 (3)
C6C	0.036 (3)	0.044 (3)	0.044 (3)	0.005 (3)	0.008 (2)	0.002 (2)
C11C	0.043 (3)	0.031 (3)	0.037 (3)	−0.002 (2)	−0.001 (3)	0.002 (2)
C12C	0.029 (3)	0.040 (3)	0.041 (3)	0.008 (2)	0.006 (2)	0.007 (2)
C13C	0.034 (3)	0.041 (3)	0.051 (4)	0.000 (2)	0.005 (3)	0.003 (3)
C14C	0.038 (3)	0.029 (2)	0.039 (3)	0.001 (2)	0.001 (2)	−0.006 (2)
C15C	0.038 (3)	0.041 (3)	0.067 (4)	0.001 (3)	0.010 (3)	0.001 (3)
C16C	0.039 (3)	0.049 (3)	0.045 (3)	−0.001 (3)	0.008 (3)	0.004 (3)
C21C	0.028 (3)	0.032 (3)	0.059 (4)	0.003 (2)	0.002 (3)	0.009 (3)
C22C	0.031 (3)	0.035 (3)	0.047 (3)	−0.008 (2)	−0.008 (2)	0.000 (2)
C23C	0.066 (4)	0.042 (3)	0.053 (3)	−0.014 (3)	−0.008 (3)	−0.003 (3)
C24C	0.056 (4)	0.051 (3)	0.077 (5)	−0.027 (3)	−0.008 (3)	0.005 (3)
C25C	0.041 (4)	0.039 (3)	0.071 (4)	−0.009 (3)	0.020 (3)	−0.003 (3)
C26C	0.047 (4)	0.039 (3)	0.048 (4)	−0.004 (3)	0.001 (3)	0.001 (3)
C31C	0.055 (4)	0.042 (3)	0.043 (3)	−0.011 (3)	−0.003 (3)	−0.009 (2)
C32C	0.047 (3)	0.039 (2)	0.051 (3)	−0.006 (2)	−0.003 (2)	−0.008 (2)
C33C	0.063 (4)	0.055 (3)	0.046 (3)	−0.013 (3)	0.002 (3)	0.004 (2)
C34C	0.099 (6)	0.064 (4)	0.064 (4)	−0.015 (4)	0.033 (4)	−0.011 (4)
C35C	0.084 (5)	0.054 (3)	0.053 (3)	0.008 (3)	0.011 (3)	−0.006 (3)
C36C	0.078 (4)	0.044 (3)	0.047 (3)	0.006 (3)	0.005 (3)	−0.005 (2)

Geometric parameters (Å, º) top

B1—O2	1.363 (8)	B1B—O1B	1.317 (8)
B1—O1	1.420 (8)	B1B—O2B	1.378 (8)
B1—C1	1.546 (10)	B1B—C1B	1.539 (9)
O1—C11	1.366 (7)	O1B—C11B	1.384 (7)
O2—C21	1.384 (7)	O2B—C21B	1.400 (7)
C1—C6	1.357 (9)	C1B—C2B	1.441 (8)
C1—C2	1.378 (9)	C1B—C6B	1.447 (8)
C2—C3	1.409 (9)	C2B—C3B	1.394 (9)
C2—C12	1.466 (8)	C2B—C12B	1.484 (9)
C3—C4	1.338 (10)	C3B—C4B	1.427 (9)
C3—H3	0.9500	C3B—H3B	0.9500
C4—C5	1.377 (9)	C4B—C5B	1.385 (9)
C4—H4	0.9500	C4B—H4B	0.9500
C5—C6	1.416 (9)	C5B—C6B	1.341 (9)
C5—H5	0.9500	C5B—H5B	0.9500
C6—H6	0.9500	C6B—H6B	0.9500
C11—C16	1.389 (9)	C11B—C16B	1.385 (9)
C11—C12	1.417 (8)	C11B—C12B	1.390 (9)
C12—C13	1.432 (8)	C12B—C13B	1.378 (9)
C13—C14	1.318 (9)	C13B—C14B	1.442 (9)
C13—H13	0.9500	C13B—H13B	0.9500
C14—C15	1.373 (10)	C14B—C15B	1.407 (9)
C14—H14	0.9500	C14B—H14B	0.9500
C15—C16	1.432 (8)	C15B—C16B	1.336 (9)
C15—H15	0.9500	C15B—H15B	0.9500
C16—H16	0.9500	C16B—H16B	0.9500
C21—C26	1.371 (9)	C21B—C22B	1.334 (9)
C21—C22	1.449 (8)	C21B—C26B	1.402 (9)
C22—C23	1.377 (8)	C22B—C23B	1.430 (8)
C22—C31	1.491 (9)	C22B—C31B	1.489 (8)
C23—C24	1.384 (10)	C23B—C24B	1.370 (9)
C23—H23	0.9500	C23B—H23B	0.9500
C24—C25	1.429 (10)	C24B—C25B	1.329 (10)
C24—H24	0.9500	C24B—H24B	0.9500
C25—C26	1.359 (10)	C25B—C26B	1.423 (9)
C25—H25	0.9500	C25B—H25B	0.9500
C26—H26	0.9500	C26B—H26B	0.9500
C31—C32	1.334 (8)	C31B—C32B	1.398 (7)
C31—C36	1.441 (8)	C31B—C36B	1.414 (7)
C32—C33	1.402 (8)	C32B—C33B	1.375 (8)
C32—H32	0.9500	C32B—H32B	0.9500
C33—C34	1.340 (10)	C33B—C34B	1.395 (8)
C33—H33	0.9500	C33B—H33B	0.9500
C34—C35	1.422 (9)	C34B—C35B	1.361 (9)
C34—H34	0.9500	C34B—H34B	0.9500
C35—C36	1.387 (8)	C35B—C36B	1.384 (8)
C35—H35	0.9500	C35B—H35B	0.9500
C36—H36	0.9500	C36B—H36B	0.9500
B1A—O2A	1.361 (8)	B1C—O1C	1.341 (7)
B1A—O1A	1.420 (8)	B1C—O2C	1.364 (7)
B1A—C1A	1.532 (10)	B1C—C1C	1.541 (8)
O1A—C11A	1.380 (7)	O1C—C11C	1.376 (7)
O2A—C21A	1.383 (7)	O2C—C21C	1.394 (7)
C1A—C6A	1.360 (8)	C1C—C6C	1.433 (8)
C1A—C2A	1.375 (9)	C1C—C2C	1.443 (8)
C2A—C3A	1.392 (9)	C2C—C3C	1.419 (8)
C2A—C12A	1.470 (8)	C2C—C12C	1.485 (8)
C3A—C4A	1.349 (9)	C3C—C4C	1.404 (9)
C3A—H3A	0.9500	C3C—H3C	0.9500
C4A—C5A	1.395 (8)	C4C—C5C	1.364 (10)
C4A—H4A	0.9500	C4C—H4C	0.9500
C5A—C6A	1.412 (9)	C5C—C6C	1.363 (9)
C5A—H5A	0.9500	C5C—H5C	0.9500
C6A—H6A	0.9500	C6C—H6C	0.9500
C11A—C16A	1.385 (8)	C11C—C16C	1.384 (9)
C11A—C12A	1.398 (8)	C11C—C12C	1.408 (9)
C12A—C13A	1.430 (8)	C12C—C13C	1.359 (9)
C13A—C14A	1.328 (9)	C13C—C14C	1.420 (9)
C13A—H13A	0.9500	C13C—H13C	0.9500
C14A—C15A	1.360 (10)	C14C—C15C	1.412 (9)
C14A—H14A	0.9500	C14C—H14C	0.9500
C15A—C16A	1.420 (8)	C15C—C16C	1.341 (9)
C15A—H15A	0.9500	C15C—H15C	0.9500
C16A—H16A	0.9500	C16C—H16C	0.9500
C21A—C26A	1.372 (9)	C21C—C22C	1.339 (9)
C21A—C22A	1.447 (8)	C21C—C26C	1.397 (9)
C22A—C23A	1.371 (8)	C22C—C23C	1.428 (8)
C22A—C31A	1.493 (8)	C22C—C31C	1.486 (8)
C23A—C24A	1.412 (9)	C23C—C24C	1.369 (10)
C23A—H23A	0.9500	C23C—H23C	0.9500
C24A—C25A	1.404 (10)	C24C—C25C	1.319 (11)
C24A—H24A	0.9500	C24C—H24C	0.9500
C25A—C26A	1.363 (10)	C25C—C26C	1.426 (9)
C25A—H25A	0.9500	C25C—H25C	0.9500
C26A—H26A	0.9500	C26C—H26C	0.9500
C31A—C36A	1.377 (7)	C31C—C32C	1.364 (8)
C31A—C32A	1.408 (7)	C31C—C36C	1.439 (8)
C32A—C33A	1.395 (7)	C32C—C33C	1.393 (7)
C32A—H32A	0.9500	C32C—H32C	0.9500
C33A—C34A	1.386 (8)	C33C—C34C	1.373 (9)
C33A—H33A	0.9500	C33C—H33C	0.9500
C34A—C35A	1.358 (9)	C34C—C35C	1.364 (10)
C34A—H34A	0.9500	C34C—H34C	0.9500
C35A—C36A	1.388 (8)	C35C—C36C	1.378 (8)
C35A—H35A	0.9500	C35C—H35C	0.9500
C36A—H36A	0.9500	C36C—H36C	0.9500

O2—B1—O1	118.9 (6)	O1B—B1B—O2B	123.1 (5)
O2—B1—C1	122.8 (6)	O1B—B1B—C1B	120.4 (5)
O1—B1—C1	118.3 (6)	O2B—B1B—C1B	116.5 (6)
C11—O1—B1	120.8 (5)	B1B—O1B—C11B	122.5 (5)
B1—O2—C21	130.2 (5)	B1B—O2B—C21B	129.3 (5)
C6—C1—C2	121.0 (6)	C2B—C1B—C6B	117.1 (5)
C6—C1—B1	120.5 (6)	C2B—C1B—B1B	117.8 (5)
C2—C1—B1	118.4 (6)	C6B—C1B—B1B	125.1 (5)
C1—C2—C3	117.7 (6)	C3B—C2B—C1B	120.6 (6)
C1—C2—C12	120.2 (5)	C3B—C2B—C12B	122.8 (5)
C3—C2—C12	122.1 (5)	C1B—C2B—C12B	116.6 (5)
C4—C3—C2	121.5 (6)	C2B—C3B—C4B	119.0 (6)
C4—C3—H3	119.2	C2B—C3B—H3B	120.5
C2—C3—H3	119.2	C4B—C3B—H3B	120.5
C3—C4—C5	121.3 (6)	C5B—C4B—C3B	120.4 (6)
C3—C4—H4	119.4	C5B—C4B—H4B	119.8
C5—C4—H4	119.4	C3B—C4B—H4B	119.8
C4—C5—C6	117.7 (6)	C6B—C5B—C4B	121.5 (6)
C4—C5—H5	121.2	C6B—C5B—H5B	119.3
C6—C5—H5	121.2	C4B—C5B—H5B	119.3
C1—C6—C5	120.7 (6)	C5B—C6B—C1B	121.4 (6)
C1—C6—H6	119.6	C5B—C6B—H6B	119.3
C5—C6—H6	119.6	C1B—C6B—H6B	119.3
O1—C11—C16	115.2 (5)	O1B—C11B—C16B	116.6 (6)
O1—C11—C12	122.3 (5)	O1B—C11B—C12B	121.7 (6)
C16—C11—C12	122.5 (6)	C16B—C11B—C12B	121.7 (6)
C11—C12—C13	114.3 (6)	C13B—C12B—C11B	118.1 (6)
C11—C12—C2	119.7 (5)	C13B—C12B—C2B	120.9 (6)
C13—C12—C2	125.9 (5)	C11B—C12B—C2B	120.9 (6)
C14—C13—C12	122.5 (6)	C12B—C13B—C14B	121.8 (6)
C14—C13—H13	118.7	C12B—C13B—H13B	119.1
C12—C13—H13	118.7	C14B—C13B—H13B	119.1
C13—C14—C15	124.4 (6)	C15B—C14B—C13B	115.3 (6)
C13—C14—H14	117.8	C15B—C14B—H14B	122.3
C15—C14—H14	117.8	C13B—C14B—H14B	122.3
C14—C15—C16	116.2 (6)	C16B—C15B—C14B	123.5 (6)
C14—C15—H15	121.9	C16B—C15B—H15B	118.3
C16—C15—H15	121.9	C14B—C15B—H15B	118.3
C11—C16—C15	119.9 (6)	C15B—C16B—C11B	119.5 (6)
C11—C16—H16	120.0	C15B—C16B—H16B	120.3
C15—C16—H16	120.0	C11B—C16B—H16B	120.3
C26—C21—O2	125.3 (5)	C22B—C21B—O2B	116.8 (5)
C26—C21—C22	119.3 (5)	C22B—C21B—C26B	123.0 (6)
O2—C21—C22	115.4 (5)	O2B—C21B—C26B	120.2 (5)
C23—C22—C21	118.4 (6)	C21B—C22B—C23B	117.7 (6)
C23—C22—C31	120.5 (5)	C21B—C22B—C31B	124.3 (5)
C21—C22—C31	121.1 (5)	C23B—C22B—C31B	117.9 (5)
C22—C23—C24	121.0 (6)	C24B—C23B—C22B	121.0 (6)
C22—C23—H23	119.5	C24B—C23B—H23B	119.5
C24—C23—H23	119.5	C22B—C23B—H23B	119.5
C23—C24—C25	119.9 (6)	C25B—C24B—C23B	119.7 (6)
C23—C24—H24	120.0	C25B—C24B—H24B	120.1
C25—C24—H24	120.0	C23B—C24B—H24B	120.1
C26—C25—C24	118.8 (7)	C24B—C25B—C26B	122.1 (6)
C26—C25—H25	120.6	C24B—C25B—H25B	119.0
C24—C25—H25	120.6	C26B—C25B—H25B	119.0
C25—C26—C21	122.4 (6)	C21B—C26B—C25B	116.4 (6)
C25—C26—H26	118.8	C21B—C26B—H26B	121.8
C21—C26—H26	118.8	C25B—C26B—H26B	121.8
C32—C31—C36	118.5 (6)	C32B—C31B—C36B	117.5 (5)
C32—C31—C22	123.5 (6)	C32B—C31B—C22B	120.4 (5)
C36—C31—C22	118.0 (5)	C36B—C31B—C22B	121.8 (5)
C31—C32—C33	121.5 (6)	C33B—C32B—C31B	121.4 (5)
C31—C32—H32	119.2	C33B—C32B—H32B	119.3
C33—C32—H32	119.2	C31B—C32B—H32B	119.3
C34—C33—C32	121.3 (6)	C32B—C33B—C34B	120.6 (6)
C34—C33—H33	119.3	C32B—C33B—H33B	119.7
C32—C33—H33	119.3	C34B—C33B—H33B	119.7
C33—C34—C35	119.6 (6)	C35B—C34B—C33B	118.5 (6)
C33—C34—H34	120.2	C35B—C34B—H34B	120.7
C35—C34—H34	120.2	C33B—C34B—H34B	120.7
C36—C35—C34	119.0 (6)	C34B—C35B—C36B	122.3 (6)
C36—C35—H35	120.5	C34B—C35B—H35B	118.8
C34—C35—H35	120.5	C36B—C35B—H35B	118.8
C35—C36—C31	120.0 (5)	C35B—C36B—C31B	119.7 (5)
C35—C36—H36	120.0	C35B—C36B—H36B	120.2
C31—C36—H36	120.0	C31B—C36B—H36B	120.2
O2A—B1A—O1A	118.5 (6)	O1C—B1C—O2C	123.0 (5)
O2A—B1A—C1A	123.1 (6)	O1C—B1C—C1C	120.2 (5)
O1A—B1A—C1A	118.3 (5)	O2C—B1C—C1C	116.6 (5)
C11A—O1A—B1A	120.2 (5)	B1C—O1C—C11C	122.5 (5)
B1A—O2A—C21A	133.4 (5)	B1C—O2C—C21C	131.8 (5)
C6A—C1A—C2A	120.2 (6)	C6C—C1C—C2C	118.1 (5)
C6A—C1A—B1A	120.3 (6)	C6C—C1C—B1C	124.7 (5)
C2A—C1A—B1A	119.4 (5)	C2C—C1C—B1C	117.1 (5)
C1A—C2A—C3A	118.6 (6)	C3C—C2C—C1C	119.3 (5)
C1A—C2A—C12A	119.1 (5)	C3C—C2C—C12C	122.3 (5)
C3A—C2A—C12A	122.3 (5)	C1C—C2C—C12C	118.4 (5)
C4A—C3A—C2A	121.5 (6)	C4C—C3C—C2C	120.0 (6)
C4A—C3A—H3A	119.3	C4C—C3C—H3C	120.0
C2A—C3A—H3A	119.3	C2C—C3C—H3C	120.0
C3A—C4A—C5A	121.2 (6)	C5C—C4C—C3C	119.4 (6)
C3A—C4A—H4A	119.4	C5C—C4C—H4C	120.3
C5A—C4A—H4A	119.4	C3C—C4C—H4C	120.3
C4A—C5A—C6A	116.4 (6)	C6C—C5C—C4C	123.9 (6)
C4A—C5A—H5A	121.8	C6C—C5C—H5C	118.1
C6A—C5A—H5A	121.8	C4C—C5C—H5C	118.1
C1A—C6A—C5A	122.0 (6)	C5C—C6C—C1C	119.3 (6)
C1A—C6A—H6A	119.0	C5C—C6C—H6C	120.3
C5A—C6A—H6A	119.0	C1C—C6C—H6C	120.3
O1A—C11A—C16A	115.0 (5)	O1C—C11C—C16C	117.2 (6)
O1A—C11A—C12A	122.5 (5)	O1C—C11C—C12C	122.4 (5)
C16A—C11A—C12A	122.5 (5)	C16C—C11C—C12C	120.3 (6)
C11A—C12A—C13A	115.1 (5)	C13C—C12C—C11C	118.8 (5)
C11A—C12A—C2A	120.3 (5)	C13C—C12C—C2C	121.9 (6)
C13A—C12A—C2A	124.6 (5)	C11C—C12C—C2C	119.2 (5)
C14A—C13A—C12A	121.1 (6)	C12C—C13C—C14C	122.3 (6)
C14A—C13A—H13A	119.4	C12C—C13C—H13C	118.9
C12A—C13A—H13A	119.4	C14C—C13C—H13C	118.9
C13A—C14A—C15A	125.1 (6)	C15C—C14C—C13C	115.9 (6)
C13A—C14A—H14A	117.5	C15C—C14C—H14C	122.0
C15A—C14A—H14A	117.5	C13C—C14C—H14C	122.0
C14A—C15A—C16A	116.0 (6)	C16C—C15C—C14C	122.7 (6)
C14A—C15A—H15A	122.0	C16C—C15C—H15C	118.7
C16A—C15A—H15A	122.0	C14C—C15C—H15C	118.7
C11A—C16A—C15A	120.2 (6)	C15C—C16C—C11C	120.0 (6)
C11A—C16A—H16A	119.9	C15C—C16C—H16C	120.0
C15A—C16A—H16A	119.9	C11C—C16C—H16C	120.0
C26A—C21A—O2A	124.9 (5)	C22C—C21C—O2C	116.3 (5)
C26A—C21A—C22A	119.5 (5)	C22C—C21C—C26C	123.2 (6)
O2A—C21A—C22A	115.4 (5)	O2C—C21C—C26C	120.5 (6)
C23A—C22A—C21A	118.2 (6)	C21C—C22C—C23C	116.8 (6)
C23A—C22A—C31A	120.3 (5)	C21C—C22C—C31C	124.8 (5)
C21A—C22A—C31A	121.4 (5)	C23C—C22C—C31C	118.4 (5)
C22A—C23A—C24A	121.2 (6)	C24C—C23C—C22C	121.8 (6)
C22A—C23A—H23A	119.4	C24C—C23C—H23C	119.1
C24A—C23A—H23A	119.4	C22C—C23C—H23C	119.1
C25A—C24A—C23A	119.2 (6)	C25C—C24C—C23C	119.7 (6)
C25A—C24A—H24A	120.4	C25C—C24C—H24C	120.2
C23A—C24A—H24A	120.4	C23C—C24C—H24C	120.2
C26A—C25A—C24A	119.8 (7)	C24C—C25C—C26C	121.8 (6)
C26A—C25A—H25A	120.1	C24C—C25C—H25C	119.1
C24A—C25A—H25A	120.1	C26C—C25C—H25C	119.1
C25A—C26A—C21A	122.1 (6)	C21C—C26C—C25C	116.7 (6)
C25A—C26A—H26A	119.0	C21C—C26C—H26C	121.6
C21A—C26A—H26A	119.0	C25C—C26C—H26C	121.6
C36A—C31A—C32A	118.9 (5)	C32C—C31C—C36C	117.5 (5)
C36A—C31A—C22A	120.0 (4)	C32C—C31C—C22C	123.8 (5)
C32A—C31A—C22A	121.0 (4)	C36C—C31C—C22C	118.7 (5)
C33A—C32A—C31A	119.7 (5)	C31C—C32C—C33C	121.8 (5)
C33A—C32A—H32A	120.2	C31C—C32C—H32C	119.1
C31A—C32A—H32A	120.2	C33C—C32C—H32C	119.1
C34A—C33A—C32A	120.3 (5)	C34C—C33C—C32C	119.7 (5)
C34A—C33A—H33A	119.9	C34C—C33C—H33C	120.1
C32A—C33A—H33A	119.9	C32C—C33C—H33C	120.1
C35A—C34A—C33A	119.4 (6)	C35C—C34C—C33C	120.2 (7)
C35A—C34A—H34A	120.3	C35C—C34C—H34C	119.9
C33A—C34A—H34A	120.3	C33C—C34C—H34C	119.9
C34A—C35A—C36A	121.6 (6)	C34C—C35C—C36C	120.9 (6)
C34A—C35A—H35A	119.2	C34C—C35C—H35C	119.6
C36A—C35A—H35A	119.2	C36C—C35C—H35C	119.6
C31A—C36A—C35A	120.2 (5)	C35C—C36C—C31C	119.7 (5)
C31A—C36A—H36A	119.9	C35C—C36C—H36C	120.2
C35A—C36A—H36A	119.9	C31C—C36C—H36C	120.2

O2—B1—O1—C11	−176.9 (5)	O2B—B1B—O1B—C11B	−176.6 (5)
C1—B1—O1—C11	5.8 (8)	C1B—B1B—O1B—C11B	1.1 (9)
O1—B1—O2—C21	9.1 (9)	O1B—B1B—O2B—C21B	4.3 (10)
C1—B1—O2—C21	−173.7 (5)	C1B—B1B—O2B—C21B	−173.4 (5)
O2—B1—C1—C6	2.3 (9)	O1B—B1B—C1B—C2B	−0.5 (8)
O1—B1—C1—C6	179.5 (5)	O2B—B1B—C1B—C2B	177.4 (5)
O2—B1—C1—C2	178.2 (5)	O1B—B1B—C1B—C6B	178.8 (5)
O1—B1—C1—C2	−4.5 (8)	O2B—B1B—C1B—C6B	−3.3 (9)
C6—C1—C2—C3	−3.0 (8)	C6B—C1B—C2B—C3B	0.6 (8)
B1—C1—C2—C3	−178.9 (5)	B1B—C1B—C2B—C3B	180.0 (5)
C6—C1—C2—C12	178.3 (5)	C6B—C1B—C2B—C12B	179.5 (5)
B1—C1—C2—C12	2.4 (8)	B1B—C1B—C2B—C12B	−1.2 (8)
C1—C2—C3—C4	2.0 (9)	C1B—C2B—C3B—C4B	−0.5 (9)
C12—C2—C3—C4	−179.4 (6)	C12B—C2B—C3B—C4B	−179.2 (5)
C2—C3—C4—C5	−1.9 (10)	C2B—C3B—C4B—C5B	1.8 (9)
C3—C4—C5—C6	2.6 (10)	C3B—C4B—C5B—C6B	−3.4 (10)
C2—C1—C6—C5	3.9 (9)	C4B—C5B—C6B—C1B	3.6 (10)
B1—C1—C6—C5	179.7 (6)	C2B—C1B—C6B—C5B	−2.2 (8)
C4—C5—C6—C1	−3.6 (9)	B1B—C1B—C6B—C5B	178.5 (6)
B1—O1—C11—C16	176.7 (5)	B1B—O1B—C11B—C16B	177.9 (6)
B1—O1—C11—C12	−5.0 (8)	B1B—O1B—C11B—C12B	0.1 (9)
O1—C11—C12—C13	178.0 (5)	O1B—C11B—C12B—C13B	179.8 (5)
C16—C11—C12—C13	−3.7 (8)	C16B—C11B—C12B—C13B	2.0 (9)
O1—C11—C12—C2	2.6 (8)	O1B—C11B—C12B—C2B	−1.8 (9)
C16—C11—C12—C2	−179.1 (5)	C16B—C11B—C12B—C2B	−179.6 (6)
C1—C2—C12—C11	−1.4 (8)	C3B—C2B—C12B—C13B	−0.5 (9)
C3—C2—C12—C11	179.9 (5)	C1B—C2B—C12B—C13B	−179.3 (5)
C1—C2—C12—C13	−176.3 (5)	C3B—C2B—C12B—C11B	−178.9 (6)
C3—C2—C12—C13	5.1 (9)	C1B—C2B—C12B—C11B	2.3 (8)
C11—C12—C13—C14	3.3 (9)	C11B—C12B—C13B—C14B	−1.8 (9)
C2—C12—C13—C14	178.4 (6)	C2B—C12B—C13B—C14B	179.7 (5)
C12—C13—C14—C15	−0.2 (11)	C12B—C13B—C14B—C15B	−0.4 (9)
C13—C14—C15—C16	−2.6 (10)	C13B—C14B—C15B—C16B	2.8 (9)
O1—C11—C16—C15	179.5 (5)	C14B—C15B—C16B—C11B	−2.7 (10)
C12—C11—C16—C15	1.1 (9)	O1B—C11B—C16B—C15B	−177.6 (6)
C14—C15—C16—C11	2.1 (9)	C12B—C11B—C16B—C15B	0.2 (10)
B1—O2—C21—C26	−24.5 (9)	B1B—O2B—C21B—C22B	157.2 (6)
B1—O2—C21—C22	158.6 (6)	B1B—O2B—C21B—C26B	−21.1 (9)
C26—C21—C22—C23	3.7 (9)	O2B—C21B—C22B—C23B	−177.7 (5)
O2—C21—C22—C23	−179.1 (5)	C26B—C21B—C22B—C23B	0.5 (9)
C26—C21—C22—C31	−175.5 (6)	O2B—C21B—C22B—C31B	4.8 (9)
O2—C21—C22—C31	1.6 (8)	C26B—C21B—C22B—C31B	−176.9 (6)
C21—C22—C23—C24	−5.3 (10)	C21B—C22B—C23B—C24B	0.5 (9)
C31—C22—C23—C24	174.0 (6)	C31B—C22B—C23B—C24B	178.2 (5)
C22—C23—C24—C25	5.2 (11)	C22B—C23B—C24B—C25B	−2.6 (9)
C23—C24—C25—C26	−3.5 (11)	C23B—C24B—C25B—C26B	3.6 (10)
C24—C25—C26—C21	2.0 (11)	C22B—C21B—C26B—C25B	0.4 (9)
O2—C21—C26—C25	−179.0 (6)	O2B—C21B—C26B—C25B	178.6 (5)
C22—C21—C26—C25	−2.2 (10)	C24B—C25B—C26B—C21B	−2.5 (10)
C23—C22—C31—C32	−124.1 (7)	C21B—C22B—C31B—C32B	54.8 (8)
C21—C22—C31—C32	55.2 (8)	C23B—C22B—C31B—C32B	−122.7 (6)
C23—C22—C31—C36	53.1 (8)	C21B—C22B—C31B—C36B	−131.6 (6)
C21—C22—C31—C36	−127.7 (6)	C23B—C22B—C31B—C36B	50.9 (7)
C36—C31—C32—C33	−3.3 (8)	C36B—C31B—C32B—C33B	1.5 (7)
C22—C31—C32—C33	173.8 (5)	C22B—C31B—C32B—C33B	175.4 (5)
C31—C32—C33—C34	3.9 (8)	C31B—C32B—C33B—C34B	−0.3 (8)
C32—C33—C34—C35	−2.9 (9)	C32B—C33B—C34B—C35B	0.0 (8)
C33—C34—C35—C36	1.6 (8)	C33B—C34B—C35B—C36B	−1.1 (8)
C34—C35—C36—C31	−1.1 (7)	C34B—C35B—C36B—C31B	2.3 (8)
C32—C31—C36—C35	2.0 (8)	C32B—C31B—C36B—C35B	−2.5 (7)
C22—C31—C36—C35	−175.3 (5)	C22B—C31B—C36B—C35B	−176.3 (5)
O2A—B1A—O1A—C11A	−178.6 (5)	O2C—B1C—O1C—C11C	−176.7 (5)
C1A—B1A—O1A—C11A	2.9 (8)	C1C—B1C—O1C—C11C	−1.3 (8)
O1A—B1A—O2A—C21A	2.8 (10)	O1C—B1C—O2C—C21C	−3.5 (9)
C1A—B1A—O2A—C21A	−178.8 (6)	C1C—B1C—O2C—C21C	−179.0 (5)
O2A—B1A—C1A—C6A	−0.8 (9)	O1C—B1C—C1C—C6C	175.6 (5)
O1A—B1A—C1A—C6A	177.7 (5)	O2C—B1C—C1C—C6C	−8.7 (8)
O2A—B1A—C1A—C2A	176.5 (5)	O1C—B1C—C1C—C2C	−1.1 (8)
O1A—B1A—C1A—C2A	−5.0 (8)	O2C—B1C—C1C—C2C	174.6 (5)
C6A—C1A—C2A—C3A	1.1 (9)	C6C—C1C—C2C—C3C	4.7 (8)
B1A—C1A—C2A—C3A	−176.3 (6)	B1C—C1C—C2C—C3C	−178.5 (5)
C6A—C1A—C2A—C12A	−178.2 (5)	C6C—C1C—C2C—C12C	−176.3 (5)
B1A—C1A—C2A—C12A	4.5 (8)	B1C—C1C—C2C—C12C	0.6 (7)
C1A—C2A—C3A—C4A	−1.3 (9)	C1C—C2C—C3C—C4C	−3.4 (9)
C12A—C2A—C3A—C4A	177.9 (6)	C12C—C2C—C3C—C4C	177.6 (5)
C2A—C3A—C4A—C5A	−1.4 (10)	C2C—C3C—C4C—C5C	1.5 (9)
C3A—C4A—C5A—C6A	4.0 (9)	C3C—C4C—C5C—C6C	−1.1 (10)
C2A—C1A—C6A—C5A	1.7 (9)	C4C—C5C—C6C—C1C	2.5 (10)
B1A—C1A—C6A—C5A	179.0 (6)	C2C—C1C—C6C—C5C	−4.2 (8)
C4A—C5A—C6A—C1A	−4.2 (9)	B1C—C1C—C6C—C5C	179.1 (6)
B1A—O1A—C11A—C16A	−179.4 (5)	B1C—O1C—C11C—C16C	−179.1 (5)
B1A—O1A—C11A—C12A	−0.4 (8)	B1C—O1C—C11C—C12C	4.3 (9)
O1A—C11A—C12A—C13A	178.8 (5)	O1C—C11C—C12C—C13C	179.1 (5)
C16A—C11A—C12A—C13A	−2.2 (8)	C16C—C11C—C12C—C13C	2.6 (9)
O1A—C11A—C12A—C2A	−0.2 (8)	O1C—C11C—C12C—C2C	−4.7 (8)
C16A—C11A—C12A—C2A	178.8 (5)	C16C—C11C—C12C—C2C	178.8 (6)
C1A—C2A—C12A—C11A	−2.0 (8)	C3C—C2C—C12C—C13C	−2.8 (9)
C3A—C2A—C12A—C11A	178.7 (6)	C1C—C2C—C12C—C13C	178.2 (6)
C1A—C2A—C12A—C13A	179.1 (5)	C3C—C2C—C12C—C11C	−178.8 (5)
C3A—C2A—C12A—C13A	−0.1 (9)	C1C—C2C—C12C—C11C	2.1 (8)
C11A—C12A—C13A—C14A	2.0 (8)	C11C—C12C—C13C—C14C	−2.6 (9)
C2A—C12A—C13A—C14A	−179.1 (6)	C2C—C12C—C13C—C14C	−178.7 (5)
C12A—C13A—C14A—C15A	0.0 (10)	C12C—C13C—C14C—C15C	0.4 (9)
C13A—C14A—C15A—C16A	−1.9 (10)	C13C—C14C—C15C—C16C	2.0 (9)
O1A—C11A—C16A—C15A	179.5 (5)	C14C—C15C—C16C—C11C	−2.1 (10)
C12A—C11A—C16A—C15A	0.5 (9)	O1C—C11C—C16C—C15C	−177.0 (6)
C14A—C15A—C16A—C11A	1.6 (9)	C12C—C11C—C16C—C15C	−0.3 (10)
B1A—O2A—C21A—C26A	−15.5 (10)	B1C—O2C—C21C—C22C	173.2 (6)
B1A—O2A—C21A—C22A	169.6 (6)	B1C—O2C—C21C—C26C	−7.9 (9)
C26A—C21A—C22A—C23A	−0.8 (9)	O2C—C21C—C22C—C23C	179.0 (5)
O2A—C21A—C22A—C23A	174.4 (5)	C26C—C21C—C22C—C23C	0.2 (9)
C26A—C21A—C22A—C31A	−178.0 (5)	O2C—C21C—C22C—C31C	−3.6 (9)
O2A—C21A—C22A—C31A	−2.8 (8)	C26C—C21C—C22C—C31C	177.6 (6)
C21A—C22A—C23A—C24A	2.5 (8)	C21C—C22C—C23C—C24C	0.6 (9)
C31A—C22A—C23A—C24A	179.8 (5)	C31C—C22C—C23C—C24C	−177.0 (6)
C22A—C23A—C24A—C25A	−2.8 (9)	C22C—C23C—C24C—C25C	−0.5 (11)
C23A—C24A—C25A—C26A	1.3 (10)	C23C—C24C—C25C—C26C	−0.4 (11)
C24A—C25A—C26A—C21A	0.5 (11)	C22C—C21C—C26C—C25C	−1.0 (10)
O2A—C21A—C26A—C25A	−175.4 (6)	O2C—C21C—C26C—C25C	−179.8 (5)
C22A—C21A—C26A—C25A	−0.7 (10)	C24C—C25C—C26C—C21C	1.1 (10)
C23A—C22A—C31A—C36A	−40.0 (8)	C21C—C22C—C31C—C32C	−42.2 (9)
C21A—C22A—C31A—C36A	137.2 (6)	C23C—C22C—C31C—C32C	135.2 (6)
C23A—C22A—C31A—C32A	135.8 (6)	C21C—C22C—C31C—C36C	135.1 (6)
C21A—C22A—C31A—C32A	−47.0 (8)	C23C—C22C—C31C—C36C	−47.5 (8)
C36A—C31A—C32A—C33A	1.6 (8)	C36C—C31C—C32C—C33C	3.6 (9)
C22A—C31A—C32A—C33A	−174.3 (5)	C22C—C31C—C32C—C33C	−179.1 (5)
C31A—C32A—C33A—C34A	−1.5 (8)	C31C—C32C—C33C—C34C	−0.3 (9)
C32A—C33A—C34A—C35A	0.0 (10)	C32C—C33C—C34C—C35C	−3.4 (11)
C33A—C34A—C35A—C36A	1.4 (11)	C33C—C34C—C35C—C36C	3.6 (12)
C32A—C31A—C36A—C35A	−0.2 (9)	C34C—C35C—C36C—C31C	−0.2 (10)
C22A—C31A—C36A—C35A	175.7 (6)	C32C—C31C—C36C—C35C	−3.4 (9)
C34A—C35A—C36A—C31A	−1.3 (10)	C22C—C31C—C36C—C35C	179.2 (6)

Comparative table of dihedral angles (°) in the four molecules in the asymmetric unit of (Vb). DA1 is the dihedral angle between the 10-oxa-9-boraphenanthrene moiety and the phenyl ring attached to the O atom, and DA2 is the dihedral angle between the two rings of the biphenyl residue. top

Molecule	DA1	DA2
1	20.4 (3)	55.17 (16)
A	11.4 (3)	44.3 (2)
B	22.5 (2)	53.44 (15)
C	10.8 (3)	45.4 (2)

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Packing considerations of 10-oxa-9-bora­phenanthrene derivatives

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Packing considerations of 10-oxa-9-boraphenanthrene derivatives