An unusual oligomerization/oxidation reaction of a 3-boron-substituted 1-phenyl­buta-1,3-diene produces 6,9,16,19-tetra­phenyl-5,15-distyryl-3,13,25,26-tetra­oxa-2,12-dibora­penta­cyclo­[16.2.2.2^8,11.1^2,5.1^12,15]hexa­cosa-1(20),7,10,17-tetra­ene

The unusual title macrocyclic structure, C₆₀H₅₄B₂O₄, has been isolated from exposure of 3-BF₃-1-phenyl­buta-1,3-diene to both air and moisture in an attempt to obtain crystals of the starting butadiene compound. Formation of the macrocycle from six mol­ecules of the starting butadiene material is rationalized and its structural features are compared with those of other B(OR)₂-substituted cyclo­hexane and benzene ring containing structures. Mol­ecules reside on crystallographic centers of inversion and there are no inter­molecular inter­actions of note in the crystal structure.

S1. Comment

We have recently begun to prepare 2-boron- (De & Welker, 2005) and 2-silicon-substituted 1,3-dienes and investigate their Diels–Alder/cross coupling reactions (Pidaparthi et al., 2007). Most recently, we reported the preparation of several halogen-substituted phenylbutadienes and their conversion into boron-substituted dienes (De et al., 2007). To our surprise, when we attempted to grow crystals of a BF₃ substituted diene, (I) (3-BF₃-1-phenylbuta-1,3-diene), in ethyl acetate/acetone under atmospheric conditions, a symmetrical structure, (II), derived from six molecules of (I), was isolated and characterized (Scheme 1).

We can rationalize the formation of (II) through the reactive units (III) and (IV) in Scheme 2. The rationalization requires protonolysis of some of the B—C bonds in (I) to generate 1-phenylbuta-1,3-diene. The terminal double bond of one 1-phenylbuta-1,3-diene molecule (labeled 1 in the first scheme below) appears to have been oxidized and to have participated in an electrophilic addition reaction with the internal alkene of a second molecule of 1-phenylbuta-1,3-diene (2 in the scheme below). The terminal double bond of this second molecule of 1-phenylbuta-1,3-diene has taken part in a Diels–Alder reaction with a boron-substituted diene (depicted as the boronic acid-substituted diene 3 in the scheme below). This rationalization also requires a hydrolysis of the starting dienyl trifluoroborate (I). Organotrifluoroborates are known to hydrolyze easily in mildly basic acetone/water mixtures (Yuen & Hutton, 2005). We suspect there may still be traces of methoxide present after the preparation of (I), and this catalyzes the hydrolysis required by the production of (II).

The molecular structure of (II) is depicted in Fig. 1 and selected geometric parameters are given in Table 1. Bond lengths and angles in or near the B-atom coordination sphere are normal (Table 1). The B1—C3 bonds in (II) are similar to other B—Csp² bonds in boronate ester compounds that have been reported recently (Scheme 3), for example, 1.555–1.588 Å in (V) (Coghlan et al., 2005), (VI) (Darwish et al., 2004) and (VII) (Pohl et al., 2004). Likewise the B—O and C—O bond lengths here are in the range of those reported for (V)–(VII) (1.35–1.38 Å and 1.45–1.47 Å). The O—B—O bond angles in (II) and (V)–(VII) are all 113 ± 1°, the C—C—B bond angles are all 119 ± 1° and the C—B—O bond angles are all 123 ± 1°.

There are no accessible voids in the molecular structure of (II). Steric factors seem to dictate the orientation of the styryl (C15—C16—Ph) group. Some nonbonded contacts are notable, involving the styryl C=C H15 atom on C15 with neighboring HC atoms (H15···H18 = 2.21 Å, H15···H2A = 2.65 Å and H15···C30' = 3.01 Å). Any rotation of the coplanar (to within 0.009 Å; C15 displaced by 0.31 Å) C16—Ph group that would elongate the 2.39 Å H16···O1 contact would simultaneously shorten the H15···H18, H15···H2A and H15···C2 contacts or the H15-to-aromatic ring (intramolecular) and H19-to-aromatic ring (intermolecular) contacts depending upon the direction of rotation. The styryl (C15/C16/Ph) group is distorted from planarity by 17° as determined by the angle between normals to the C15/C16/C17 and C17–C22 least-squares mean planes, respectively.

Related literature

For related literature, see: Coghlan et al. (2005); Darwish et al. (2004); De & Welker (2005); De et al. (2007); Pohl et al. (2004); Yuen & Hutton (2005).

S2. Experimental

Complex (I) (3-BF₃-1-phenylbuta-1,3-diene) was prepared as described previously (De et al., 2007). Crystals of (II) were grown by evaporation of an ethyl acetate/acetone solution of (I) at 298 K with no precautions taken to exclude air or moisture.

S3. Refinement

Crystals of (II) diffracted poorly and only 54% of the reflections with 2θ < 46.5° were `observed' [I > 2σ(I)]. The final structural model incorporated anisotropic displacement parameters for all non-H atoms and isotropic parameters for all H atoms. H atoms were included in the structural model as idealized atoms (assuming sp²– or sp³-hybridization of the C atoms and C—H bond lengths of 0.95–1.00 Å). The isotropic displacement parameters of all H atoms were fixed at values of 1.2 times the equivalent parameter of the C atom to which they are covalently bonded. H-atom distances/angles not included in CIF data; please provide.

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures

Fig. 1. The molecular structure of (II) with non-H atoms depicted with 50% probability displacement ellipsoids. Hydrogen atoms are represented by arbitrarily small spheres. Atoms labeled with a prime (') are related to nonprimed atoms by a crystallographic inversion center.

6,9,16,19-tetraphenyl-5,15-distyryl-3,13,25,26-tetraoxa-2,12- diborapentacyclo[16.2.2.2^8,11.1^2,5.1^12,15]hexacosa-1(20),7,10,17-tetraene

Crystal data

C60H54B2O4	F(000) = 912
Mr = 860.65	Dx = 1.249 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1350 reflections
a = 13.212 (3) Å	θ = 3.8–18.8°
b = 6.0975 (13) Å	µ = 0.08 mm^−1
c = 29.028 (6) Å	T = 193 K
β = 101.764 (3)°	Plate, colourless
V = 2289.4 (9) Å^3	0.37 × 0.09 × 0.03 mm
Z = 2

Data collection

Bruker APEX CCD area-detector diffractometer	3260 independent reflections
Radiation source: fine-focus sealed tube	1769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
ϕ and ω scans	θmax = 23.3°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996))	h = −14→14
Tmin = 0.973, Tmax = 0.998	k = −6→6
13447 measured reflections	l = −32→31

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 0.85	w = 1/[σ^2(Fo^2) + (0.0438P)^2] where P = (Fo^2 + 2Fc^2)/3
3260 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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.

A full hemisphere of diffracted intensities (1868 30-second frames) was measured on a a single-domain specimen. X-rays were provided by a fine- focus sealed X-ray tube operated at 50 kV and 30 mA.

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

	x	y	z	Uiso*/Ueq
O1	0.02916 (13)	0.9165 (3)	0.11343 (6)	0.0502 (5)
O2	0.02893 (14)	0.5719 (4)	0.08287 (6)	0.0554 (5)
B1	0.0560 (2)	0.7872 (7)	0.07959 (11)	0.0458 (9)
C1	−0.0352 (2)	0.7881 (5)	0.13841 (9)	0.0459 (8)
C2	−0.0126 (2)	0.5528 (5)	0.12540 (10)	0.0563 (9)
H2A	0.0383	0.4833	0.1510	0.068*
H2B	−0.0767	0.4639	0.1195	0.068*
C3	0.1148 (2)	0.8724 (5)	0.04198 (9)	0.0437 (8)
C4	0.1710 (2)	1.0525 (5)	0.05104 (9)	0.0462 (8)
H4	0.1725	1.1227	0.0804	0.055*
C5	0.23293 (19)	1.1552 (5)	0.01851 (8)	0.0428 (7)
H5	0.2153	1.3149	0.0164	0.051*
C6	0.20079 (18)	1.0614 (5)	−0.03082 (9)	0.0399 (7)
C7	0.1888 (2)	0.8187 (5)	−0.03085 (9)	0.0442 (7)
H7A	0.2556	0.7502	−0.0163	0.053*
H7B	0.1689	0.7656	−0.0637	0.053*
C8	0.1061 (2)	0.7512 (5)	−0.00349 (9)	0.0470 (8)
H8A	0.0369	0.7784	−0.0233	0.056*
H8B	0.1122	0.5919	0.0031	0.056*
C9	0.3491 (2)	1.1380 (5)	0.03802 (8)	0.0401 (7)
C10	0.4123 (2)	1.3111 (5)	0.03443 (9)	0.0546 (8)
H10	0.3833	1.4419	0.0196	0.066*
C11	0.5182 (3)	1.3005 (6)	0.05202 (10)	0.0656 (9)
H11	0.5610	1.4228	0.0492	0.079*
C12	0.5598 (2)	1.1134 (7)	0.07333 (10)	0.0635 (9)
H12	0.6322	1.1048	0.0853	0.076*
C13	0.4985 (2)	0.9381 (6)	0.07768 (10)	0.0611 (9)
H13	0.5282	0.8078	0.0925	0.073*
C14	0.3926 (2)	0.9502 (5)	0.06038 (9)	0.0542 (8)
H14	0.3498	0.8287	0.0639	0.065*
C15	−0.0009 (2)	0.8229 (5)	0.19025 (9)	0.0523 (8)
H15	−0.0349	0.7396	0.2102	0.063*
C16	0.0720 (2)	0.9580 (5)	0.21068 (10)	0.0567 (9)
H16	0.1015	1.0504	0.1906	0.068*
C17	0.1126 (2)	0.9806 (5)	0.26172 (10)	0.0527 (8)
C18	0.0972 (2)	0.8165 (6)	0.29293 (11)	0.0682 (10)
H18	0.0601	0.6880	0.2813	0.082*
C19	0.1352 (3)	0.8385 (7)	0.34062 (11)	0.0797 (11)
H19	0.1228	0.7268	0.3616	0.096*
C20	0.1906 (3)	1.0201 (7)	0.35771 (12)	0.0797 (11)
H20	0.2179	1.0343	0.3905	0.096*
C21	0.2066 (3)	1.1817 (7)	0.32733 (13)	0.0875 (12)
H21	0.2440	1.3096	0.3393	0.105*
C22	0.1694 (2)	1.1616 (6)	0.27949 (12)	0.0748 (10)
H22	0.1830	1.2733	0.2588	0.090*
C23	0.18342 (18)	1.1917 (5)	−0.06795 (9)	0.0424 (7)
H23	0.1947	1.3435	−0.0615	0.051*
C24	0.14816 (19)	1.1333 (5)	−0.11930 (8)	0.0454 (8)
H24	0.1465	0.9694	−0.1209	0.054*
C25	0.2251 (2)	1.2078 (5)	−0.14893 (9)	0.0445 (7)
C26	0.2732 (2)	1.4079 (5)	−0.14383 (10)	0.0541 (8)
H26	0.2571	1.5090	−0.1215	0.065*
C27	0.3450 (2)	1.4662 (6)	−0.17074 (11)	0.0630 (9)
H27	0.3782	1.6051	−0.1665	0.076*
C28	0.3672 (2)	1.3225 (7)	−0.20316 (12)	0.0700 (10)
H28	0.4161	1.3614	−0.2217	0.084*
C29	0.3199 (3)	1.1233 (7)	−0.20916 (11)	0.0697 (10)
H29	0.3357	1.0234	−0.2318	0.084*
C30	0.2482 (2)	1.0659 (6)	−0.18210 (10)	0.0573 (8)
H30	0.2149	0.9272	−0.1866	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0457 (12)	0.0705 (14)	0.0352 (11)	−0.0053 (11)	0.0101 (9)	−0.0040 (11)
O2	0.0543 (13)	0.0691 (15)	0.0431 (12)	0.0054 (11)	0.0102 (10)	0.0027 (11)
B1	0.035 (2)	0.060 (3)	0.037 (2)	0.0030 (19)	−0.0055 (16)	0.000 (2)
C1	0.0461 (19)	0.060 (2)	0.0322 (16)	−0.0059 (16)	0.0081 (14)	0.0023 (16)
C2	0.0517 (19)	0.073 (2)	0.0422 (19)	−0.0015 (17)	0.0045 (15)	0.0111 (17)
C3	0.0353 (17)	0.060 (2)	0.0333 (17)	0.0095 (15)	0.0011 (13)	0.0021 (15)
C4	0.0384 (17)	0.070 (2)	0.0292 (16)	0.0107 (17)	0.0040 (13)	−0.0004 (16)
C5	0.0405 (17)	0.055 (2)	0.0309 (15)	0.0091 (15)	0.0031 (13)	−0.0007 (14)
C6	0.0315 (16)	0.058 (2)	0.0291 (16)	0.0100 (15)	0.0043 (12)	−0.0019 (16)
C7	0.0462 (18)	0.055 (2)	0.0296 (15)	0.0054 (15)	0.0040 (13)	−0.0012 (15)
C8	0.0446 (18)	0.055 (2)	0.0400 (17)	0.0068 (15)	0.0060 (14)	0.0013 (15)
C9	0.0392 (17)	0.053 (2)	0.0262 (15)	0.0067 (16)	0.0026 (13)	−0.0047 (15)
C10	0.054 (2)	0.064 (2)	0.0441 (18)	0.0042 (19)	0.0057 (15)	0.0044 (17)
C11	0.050 (2)	0.092 (3)	0.054 (2)	−0.008 (2)	0.0092 (17)	0.006 (2)
C12	0.0356 (19)	0.103 (3)	0.050 (2)	0.009 (2)	0.0049 (16)	−0.007 (2)
C13	0.049 (2)	0.073 (2)	0.056 (2)	0.014 (2)	−0.0020 (17)	0.0005 (19)
C14	0.047 (2)	0.067 (2)	0.0452 (18)	0.0066 (17)	0.0002 (15)	0.0062 (17)
C15	0.0421 (19)	0.076 (2)	0.0366 (17)	−0.0058 (17)	0.0036 (14)	−0.0003 (17)
C16	0.0510 (19)	0.081 (2)	0.0387 (18)	−0.0022 (18)	0.0113 (15)	0.0008 (17)
C17	0.0452 (19)	0.073 (2)	0.0393 (19)	−0.0021 (17)	0.0080 (15)	−0.0054 (18)
C18	0.079 (2)	0.078 (3)	0.043 (2)	−0.004 (2)	0.0028 (17)	0.001 (2)
C19	0.099 (3)	0.093 (3)	0.040 (2)	−0.007 (2)	−0.0035 (19)	0.002 (2)
C20	0.087 (3)	0.103 (3)	0.044 (2)	−0.011 (2)	0.0021 (19)	−0.007 (2)
C21	0.096 (3)	0.108 (3)	0.053 (2)	−0.031 (2)	0.003 (2)	−0.013 (2)
C22	0.072 (2)	0.094 (3)	0.057 (2)	−0.028 (2)	0.0115 (18)	−0.010 (2)
C23	0.0371 (17)	0.056 (2)	0.0326 (16)	0.0019 (15)	0.0031 (13)	−0.0025 (16)
C24	0.0423 (18)	0.060 (2)	0.0318 (16)	0.0000 (15)	0.0033 (13)	0.0014 (15)
C25	0.0360 (17)	0.060 (2)	0.0339 (17)	−0.0016 (16)	−0.0005 (13)	0.0034 (16)
C26	0.0485 (19)	0.067 (2)	0.0462 (19)	0.0030 (18)	0.0074 (15)	0.0025 (17)
C27	0.059 (2)	0.075 (3)	0.054 (2)	−0.0067 (19)	0.0088 (18)	0.010 (2)
C28	0.054 (2)	0.106 (3)	0.053 (2)	−0.012 (2)	0.0185 (17)	0.010 (2)
C29	0.066 (2)	0.099 (3)	0.046 (2)	−0.001 (2)	0.0179 (18)	−0.005 (2)
C30	0.055 (2)	0.077 (2)	0.0413 (18)	−0.0027 (18)	0.0131 (16)	−0.0058 (18)

Geometric parameters (Å, º)

O1—B1	1.361 (4)	C25—C26	1.369 (4)
O1—C1	1.454 (3)	C25—C30	1.374 (4)
O2—B1	1.369 (4)	C26—C27	1.393 (4)
O2—C2	1.455 (3)	C27—C28	1.361 (4)
B1—C3	1.553 (4)	C28—C29	1.361 (4)
C1—C15	1.496 (3)	C29—C30	1.392 (4)
C1—C2	1.528 (4)	C2—H2A	0.9900
C1—C24^i	1.558 (3)	C2—H2B	0.9900
C3—C4	1.322 (4)	C4—H4	0.9500
C3—C8	1.496 (3)	C5—H5	1.0000
C4—C5	1.506 (3)	C7—H7A	0.9900
C5—C6	1.520 (3)	C7—H7B	0.9900
C5—C9	1.528 (3)	C8—H8A	0.9900
C6—C23	1.321 (3)	C8—H8B	0.9900
C6—C7	1.488 (4)	C10—H10	0.9500
C7—C8	1.532 (3)	C11—H11	0.9500
C9—C10	1.362 (4)	C12—H12	0.9500
C9—C14	1.382 (4)	C13—H13	0.9500
C10—C11	1.389 (4)	C14—H14	0.9500
C11—C12	1.360 (4)	C15—H15	0.9500
C12—C13	1.362 (4)	C16—H16	0.9500
C13—C14	1.389 (4)	C18—H18	0.9500
C15—C16	1.313 (4)	C19—H19	0.9500
C16—C17	1.476 (4)	C20—H20	0.9500
C17—C22	1.374 (4)	C21—H21	0.9500
C17—C18	1.392 (4)	C22—H22	0.9500
C18—C19	1.380 (4)	C23—H23	0.9500
C19—C20	1.364 (4)	C24—H24	1.0000
C20—C21	1.367 (4)	C26—H26	0.9500
C21—C22	1.381 (4)	C27—H27	0.9500
C23—C24	1.511 (3)	C28—H28	0.9500
C24—C25	1.529 (4)	C29—H29	0.9500
C24—C1^i	1.558 (3)	C30—H30	0.9500
B1—O1—C1	108.2 (2)	C1—C2—H2B	110.7
B1—O2—C2	106.6 (2)	H2A—C2—H2B	108.8
O1—B1—O2	113.3 (3)	C3—C4—H4	117.4
O1—B1—C3	123.7 (3)	C5—C4—H4	117.4
O2—B1—C3	123.0 (3)	C4—C5—H5	107.0
O1—C1—C15	109.7 (2)	C6—C5—H5	107.0
O1—C1—C2	102.6 (2)	C9—C5—H5	107.0
C15—C1—C2	110.3 (2)	C6—C7—H7A	109.5
O1—C1—C24^i	105.8 (2)	C8—C7—H7A	109.5
C15—C1—C24^i	112.8 (2)	C6—C7—H7B	109.5
C2—C1—C24^i	115.0 (2)	C8—C7—H7B	109.5
O2—C2—C1	105.1 (2)	H7A—C7—H7B	108.1
C4—C3—C8	121.6 (3)	C3—C8—H8A	109.0
C4—C3—B1	118.6 (3)	C7—C8—H8A	109.0
C8—C3—B1	119.7 (3)	C3—C8—H8B	109.0
C3—C4—C5	125.2 (3)	C7—C8—H8B	109.0
C4—C5—C6	110.5 (2)	H8A—C8—H8B	107.8
C4—C5—C9	111.8 (2)	C9—C10—H10	119.3
C6—C5—C9	113.0 (2)	C11—C10—H10	119.3
C23—C6—C7	126.6 (2)	C12—C11—H11	120.3
C23—C6—C5	120.7 (3)	C10—C11—H11	120.3
C7—C6—C5	112.6 (2)	C11—C12—H12	119.8
C6—C7—C8	110.7 (2)	C13—C12—H12	119.8
C3—C8—C7	113.0 (2)	C12—C13—H13	120.0
C10—C9—C14	118.4 (3)	C14—C13—H13	120.0
C10—C9—C5	120.2 (3)	C9—C14—H14	119.8
C14—C9—C5	121.4 (3)	C13—C14—H14	119.8
C9—C10—C11	121.5 (3)	C16—C15—H15	117.0
C12—C11—C10	119.3 (3)	C1—C15—H15	117.0
C11—C12—C13	120.5 (3)	C15—C16—H16	116.7
C12—C13—C14	120.0 (3)	C17—C16—H16	116.7
C9—C14—C13	120.3 (3)	C19—C18—H18	119.6
C16—C15—C1	126.0 (3)	C17—C18—H18	119.6
C15—C16—C17	126.5 (3)	C20—C19—H19	119.9
C22—C17—C18	118.3 (3)	C18—C19—H19	119.9
C22—C17—C16	120.7 (3)	C19—C20—H20	120.2
C18—C17—C16	121.0 (3)	C21—C20—H20	120.2
C19—C18—C17	120.8 (3)	C20—C21—H21	119.5
C20—C19—C18	120.2 (3)	C22—C21—H21	119.5
C19—C20—C21	119.5 (3)	C17—C22—H22	119.9
C20—C21—C22	121.0 (4)	C21—C22—H22	119.9
C17—C22—C21	120.3 (3)	C6—C23—H23	115.5
C6—C23—C24	129.1 (3)	C24—C23—H23	115.5
C23—C24—C25	112.2 (2)	C23—C24—H24	106.3
C23—C24—C1^i	111.0 (2)	C25—C24—H24	106.3
C25—C24—C1^i	114.0 (2)	C1^i—C24—H24	106.3
C26—C25—C30	118.2 (3)	C25—C26—H26	119.3
C26—C25—C24	123.4 (3)	C27—C26—H26	119.3
C30—C25—C24	118.4 (3)	C28—C27—H27	120.3
C25—C26—C27	121.4 (3)	C26—C27—H27	120.3
C28—C27—C26	119.4 (3)	C29—C28—H28	119.9
C29—C28—C27	120.3 (3)	C27—C28—H28	119.9
C28—C29—C30	120.0 (3)	C28—C29—H29	120.0
C25—C30—C29	120.7 (3)	C30—C29—H29	120.0
O2—C2—H2A	110.7	C25—C30—H30	119.6
C1—C2—H2A	110.7	C29—C30—H30	119.6
O2—C2—H2B	110.7
C1—O1—B1—O2	−8.9 (3)	C10—C11—C12—C13	−0.4 (5)
C1—O1—B1—C3	173.2 (2)	C11—C12—C13—C14	−0.2 (5)
C2—O2—B1—O1	−4.9 (3)	C10—C9—C14—C13	−1.4 (4)
C2—O2—B1—C3	173.1 (2)	C5—C9—C14—C13	179.8 (2)
B1—O1—C1—C15	135.0 (2)	C12—C13—C14—C9	1.1 (4)
B1—O1—C1—C2	17.8 (3)	O1—C1—C15—C16	3.8 (4)
B1—O1—C1—C24^i	−103.1 (2)	C2—C1—C15—C16	116.1 (3)
B1—O2—C2—C1	15.8 (3)	C24^i—C1—C15—C16	−113.8 (3)
O1—C1—C2—O2	−20.2 (3)	C1—C15—C16—C17	−174.5 (3)
C15—C1—C2—O2	−137.0 (2)	C15—C16—C17—C22	−163.7 (3)
C24^i—C1—C2—O2	94.1 (2)	C15—C16—C17—C18	18.3 (5)
O1—B1—C3—C4	23.0 (4)	C22—C17—C18—C19	2.0 (5)
O2—B1—C3—C4	−154.8 (3)	C16—C17—C18—C19	−179.9 (3)
O1—B1—C3—C8	−156.5 (2)	C17—C18—C19—C20	−1.4 (5)
O2—B1—C3—C8	25.7 (4)	C18—C19—C20—C21	1.1 (5)
C8—C3—C4—C5	−0.9 (4)	C19—C20—C21—C22	−1.3 (6)
B1—C3—C4—C5	179.6 (2)	C18—C17—C22—C21	−2.2 (5)
C3—C4—C5—C6	14.8 (4)	C16—C17—C22—C21	179.7 (3)
C3—C4—C5—C9	−112.0 (3)	C20—C21—C22—C17	1.9 (5)
C4—C5—C6—C23	133.7 (3)	C7—C6—C23—C24	−0.4 (4)
C9—C5—C6—C23	−100.1 (3)	C5—C6—C23—C24	−178.0 (2)
C4—C5—C6—C7	−44.2 (3)	C6—C23—C24—C25	−121.4 (3)
C9—C5—C6—C7	82.0 (3)	C6—C23—C24—C1^i	109.7 (3)
C23—C6—C7—C8	−117.8 (3)	C23—C24—C25—C26	−42.7 (4)
C5—C6—C7—C8	60.0 (3)	C1^i—C24—C25—C26	84.7 (3)
C4—C3—C8—C7	15.4 (4)	C23—C24—C25—C30	136.7 (3)
B1—C3—C8—C7	−165.1 (2)	C1^i—C24—C25—C30	−96.0 (3)
C6—C7—C8—C3	−44.1 (3)	C30—C25—C26—C27	−1.2 (4)
C4—C5—C9—C10	−138.7 (3)	C24—C25—C26—C27	178.1 (2)
C6—C5—C9—C10	95.9 (3)	C25—C26—C27—C28	0.7 (4)
C4—C5—C9—C14	40.1 (3)	C26—C27—C28—C29	−0.2 (5)
C6—C5—C9—C14	−85.4 (3)	C27—C28—C29—C30	0.1 (5)
C14—C9—C10—C11	0.9 (4)	C26—C25—C30—C29	1.1 (4)
C5—C9—C10—C11	179.7 (2)	C24—C25—C30—C29	−178.3 (3)
C9—C10—C11—C12	0.0 (4)	C28—C29—C30—C25	−0.6 (5)

Symmetry code: (i) −x, −y+2, −z.