A 2 styryl­boronate ester

Acta Cryst.(2001). E57, o63±o65 DOI: 101107/S1600536800019097 William Clegget al. C₁₄H₁₁BO₂

o63

organic papers

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

A 2-styrylboronate ester

William Clegg,a_{* Todd B.}

Marder,b,c_{Andrew J. Scott,}a

Christian Wiesauerc,d_{and Walter}

Weissensteinerd

a_{Department of Chemistry, University of}

Newcastle upon Tyne, Newcastle upon Tyne NE1 7RU, England,b_{Department of Chemistry,}

University of Durham, South Road, Durham DH1 3LE, England,c_{Department of Chemistry,}

University of Waterloo, Waterloo, Ontario, Canada N2L 3G1, andd_{Institute of Organic}

Chemistry, University of Vienna, Waehringer-strasse 38, A-1090 Wien, Austria

Correspondence e-mail: w. [email protected]

Key indicators

Single-crystal X-ray study

T= 160 K

Mean(C±C) = 0.002 AÊ

Rfactor = 0.037

wRfactor = 0.095

Data-to-parameter ratio = 16.6

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2001 International Union of Crystallography Printed in Great Britain ± all rights reserved

Molecules of the title compound, (E)-2-(2-phenylethenyl)-1,3,2-benzodioxaborole, C14H11BO2, are essentially

comple-tely planar with a high degree of conjugation. They pack with a herring-bone pattern in the crystal structure. The compound is synthesized with high regioselectivity by hydroboration of phenylacetylene with catecholborane.

Comment

Alkenylboronic esters and acids are versatile synthetic inter-mediates (Lane & Kabalka, 1976) for products such as cis-alkenes and halocis-alkenes, and they have important applica-tions in palladium-catalysed cross-coupling reacapplica-tions and the formation of organometallic compounds (Suzuki, 1985, 1998; Oheet al., 1988; Larocket al., 1972; Pappo & Collins, 1972). The title compound, (I), was obtained by a hydroboration reaction of phenylacetylene with catecholborane (Brown & Gupta, 1972, 1975; Brown & Chandrasekharan, 1983). The ®rst reported preparation of this compound (Joyet al., 1966) involved treatment of cyclooctatetraene with boron trichloride, followed by reaction of the resulting (E)-styryl-boron dichloride with catechol. In order to study the in¯uence of electron-donating and electron-withdrawing substituents at the para-position of the phenyl ring on the reactivity of the double bond in catalysed hydroborations of styrylboronate esters, a series of para-substituted analogues has been prepared (Wiesauer, 1997).

The molecule (Fig. 1) is essentially completely planar, with an r.m.s. deviation of 0.071 AÊ from the least-squares plane through all atoms. All torsion angles are close to 0 and 180_,

the largest corresponding to a twist of about 6_{about the C2Ð}

C21 bond linking the phenyl group to the central alkene unit. Bond lengths and angles are normal, with BÐC somewhat shorter and C C longer than generally observed for single and double bonds, respectively (Allen et al., 1992); together with the planarity of the molecule, they indicate extensive delocalization.

It is instructive to compare the title compound with two closely related styryl bis(boronate) esters, (Z)-[(4-NC±C6H4)±

C(Bcat) CH(Bcat)] [(II); Bcat is 1,3,2-benzodioxaborole; cat = 1,2-O2C6H4; Clegget al., 1996] and (Z)-[(4-MeO±C6H4)±

organic papers

o64

C(Bcat) CH(Bcat)] [(III); Lesley et al., 1996]. These differ from (I) in having either a-acceptor or-donor substituent at the para-position of the phenyl ring attached to the -carbon of the alkene and also a second Bcat moiety at C. In

(II) and (III), the Bcat at the -position is approximately coplanar (dihedral angles approximately 9 and 7_,

respec-tively) with the alkene unit, as in (I), whereas the Bcat groups at Cin (II) and (III) are roughly perpendicular (80 and 84,

respectively) to the alkene plane. In both (II) and (III), the CÐB distances [1.535 (2) and 1.526 (2) AÊ] are signi®cantly

shorter than their CÐB distances [1.569 (2) and 1.566 (2) AÊ]

and are consistent with the CÐB distance in (I) of

1.5321 (17) AÊ. Presumably this is a re¯ection of the delocali-zation present when the Bcat group is coplanar with the alkene andtransto the aryl moiety. The C C distance in (I) [1.3368 (16) AÊ] is shorter than the corresponding distance in either (II) or (III) [1.349 (2) and 1.348 (2) AÊ, respectively] and is probably a result of less steric repulsion in the less substi-tuted alkene.

This structure was recently used as a test of crystal structure prediction methods (Lommerseet al., 2000), and proved to be a considerable challenge to the currently available software systems, with only one prediction reasonably close to the experimentally observed structure.

Experimental

In a nitrogen-®lled glove-box, phenylacetylene (4.0 g, 39 mmol) and catecholborane (4.7 g, 39 mmol) were heated at 343 K for 2 h in a scintillation vial. On cooling, an orange solid was formed. The pure product was obtained as a colourless crystalline material by recrys-tallization from diethylether/hexane by solvent diffusion at 238 K, in 70% yield. Analysis calculated: C 75.73, H 4.99%; found: C 75.30, H 4.98%.1_{H NMR (200 MHz):6.48 (d, J= 18.5 Hz, 1H, CH CHB),}

7.08 (m, 2H, C6H4), 7.26 (m, 2H, C6H4), 7.38 (m, 3H, C6H5), 7.58 (m,

2H, C6H5), 7.77 (d, J = 18.5 Hz, 1H, CH CHB). 13C{1H} NMR

(50 MHz):112.3 (2C, C3and C6of C6H4), 122.6 (2C, C4and C5of

C6H4), 127.4 (2C, Ph), 128.7 (2C, Ph), 129.6 (1C, C4of Ph), 136.9 (1C,

C1of Ph), 148.3 (2C, C1and C2of C6H4), 152.0 (1C,CH CHB),

resonances of C bonded to B too broad to be observed.11_B{1_{H} NMR}

(64 MHz):31.3. MS: 222 (M+_{, 100), 207 (26), 196 (52), 179 (30), 178}

(30), 144 (68), 136 (78), 129 (21), 120 (84), 111 (60), 110 (79), 102 (77), 92 (48%).

Crystal data

C14H11BO2 Mr= 222.04

Monoclinic,P21/c a= 6.8351 (9) AÊ b= 7.6342 (10) AÊ c= 21.422 (3) AÊ

= 96.447 (3) V= 1110.8 (3) AÊ3 Z= 4

Dx= 1.328 Mg mÿ3

MoKradiation Cell parameters from 5221

re¯ections

= 2.8±28.6 = 0.09 mmÿ1 T= 160 (2) K Block, colourless 0.620.500.40 mm

Data collection

Bruker SMART 1K CCD diffract-ometer

!rotation with narrow frames 6709 measured re¯ections 2571 independent re¯ections 2326 re¯ections withI> 2(I)

Rint= 0.022 max= 28.6 h=ÿ9!8 k=ÿ6!10 l=ÿ28!28

Re®nement

Re®nement onF2 R[F2_{> 2(F}2_{)] = 0.037} wR(F2_{) = 0.095} S= 1.06 2571 re¯ections 155 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0389P)2

+ 0.3966P]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.001 max= 0.26 e AÊÿ3 min=ÿ0.15 e AÊÿ3

Extinction correction:SHELXTL Extinction coef®cient: 0.021 (2)

Table 1

Selected geometric parameters (AÊ,_).

C1ÐC2 1.3368 (16)

C1ÐB1 1.5321 (17)

C2ÐC21 1.4692 (15)

B1ÐO2 1.3909 (15)

B1ÐO1 1.3910 (15)

C2ÐC1ÐB1 124.72 (11)

C1ÐC2ÐC21 126.86 (11)

O2ÐB1ÐO1 111.54 (10)

O2ÐB1ÐC1 122.96 (11)

O1ÐB1ÐC1 125.50 (11)

C11ÐO1ÐB1 104.82 (9)

C12ÐO2ÐB1 105.06 (9)

B1ÐC1ÐC2ÐC21 ÿ178.83 (11) C2ÐC1ÐB1ÐO2 179.17 (11) C2ÐC1ÐB1ÐO1 ÿ1.22 (19)

C1ÐC2ÐC21ÐC22 173.52 (11) C1ÐC2ÐC21ÐC26 ÿ6.08 (18)

The data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures; each set had a different'angle for the crystal and each exposure covered 0.3

in !. H atoms were placed geometrically and re®ned with a riding model (including free rotation about CÐC bonds), and with Uiso

constrained to be 1.2Ueqof the carrier atom.

Data collection: SMART(Siemens, 1995); cell re®nement: local programs; data reduction:SAINT(Siemens, 1995); program(s) used to solve and re®ne structure:SHELXTL(Sheldrick, 1994); molecular graphics:SHELXTL; software used to prepare material for publi-cation:SHELXTLand local programs.

WC and AJS thank EPSRC (UK) for ®nancial support. TBM thanks NSERC of Canada for research support, and the University of Newcastle upon Tyne for a Visiting Senior Research Fellowship. TBM and WC thank NSERC and The Royal Society for support of this collaboration through the Bilateral Exchange Program. Financial support to WW by Fonds zur FoÈrderung der wissenschaftlichen Forschung

Figure 1

(project 10474-CHE) is fratefully acknowledged. CW thanks the Bundesministerium fuÈr Wissenschaft und Verkehr for supporting his six-month stay at the University of Waterloo.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1992).International Tables for Crystallography, Vol. C, pp. 685±706. Dordrecht: Kluwer Academic Publishers.

Brown, H. C. & Gupta, S. K. (1972).J. Am. Chem. Soc.94, 4370±4371. Brown, H. C. & Gupta, S. K. (1975).J. Am. Chem. Soc.97, 5249±5255. Brown, H. C. & Chandrasekharan, J. (1983). J. Org. Chem. 48, 5080±

5082.

Clegg, W., Scott, A. J., Lesley, G., Marder, T. B. & Norman, N. C. (1996).Acta Cryst.C52, 1991±1995.

Joy, F., Lappert, M. F. & Prokai, B. (1966).J. Organomet. Chem.5, 506± 519.

Lane, C. F. & Kabalka, G. W. (1976).Tetrahedron,32, 981±990.

Larock, R. C., Gupta, S. K. & Brown, H. C. (1972).J. Am. Chem. Soc.94, 4371± 4373.

Lesley, G., Nguyen, P., Taylor, N. J., Marder, T. B., Scott, A. J., Clegg, W. & Norman, N. C. (1996).Organometallics,15, 5137±5154.

Lommerse, J. P. M., Motherwell, W. D. S., Ammon, H. L., Dunitz, J. D., Gavezzotti, A., Hofmann, D. W. M., Leusen, F. J. J., Mooij, W. T. M., Price, S. L., Schweizer, B., Schmidt, M. U., van Eijck, B. P., Verwer, P. & Williams, D. E. (2000).Acta Cryst.B56, 697±714.

Ohe, T., Ohe, K., Uemura, S. & Sugita, N. (1988).J. Organomet. Chem.344, C5±7.

Pappo, R. & Collins, P. W. (1972).Tetrahedron Lett.pp. 2627±2630. Sheldrick, G. M. (1994).SHELXTL.Version 5. Siemens Analytical X-ray

Instruments Inc., Madison, Wisconsin, USA.

Siemens (1995).SMARTandSAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Suzuki, A. (1985).Pure Appl. Chem.57, 1749±1758.

Suzuki, A. (1998).Metal-Catalyzed Cross-Coupling Reactions, edited by F. Diederich & P. J. Stang, pp. 49±97. Weinheim: Wiley-VCH.

Wiesauer, C. (1997). Doctoral thesis, University of Vienna, Austria.

Acta Cryst.(2001). E57, o63±o65 William Clegget al. C₁₄H₁₁BO₂

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supporting information

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Acta Cryst. (2001). E57, o63–o65

supporting information

Acta Cryst. (2001). E57, o63–o65 [doi:10.1107/S1600536800019097]

A 2-styrylboronate ester

William Clegg, Todd B. Marder, Andrew J. Scott, Christian Wiesauer and Walter Weissensteiner

S1. Comment

Alkenylboronic esters and acids are versatile synthetic intermediates (Lane & Kabalka, 1976) for products such as cis

-alkenes and halo-alkenes, and they have important applications in palladium-catalysed cross-coupling reactions and the

formation of organometallic compounds (Suzuki, 1985, 1998; Ohe et al., 1988; Larock et al., 1972; Pappo & Collins,

1972). The title compound, (I), was obtained by a hydroboration reaction of phenylacetylene with catecholborane (Brown

& Gupta, 1972, 1975; Brown & Chandrasekharan, 1983). The first reported preparation of this compound (Joy et al.,

1966) involved treatment of cyclooctatetraene with boron trichloride, followed by reaction of the resulting

(E)-styrylboron dichloride with catechol. In order to study the influence of electron-donating and electron-withdrawing

substituents at the para-position of the phenyl ring on the reactivity of the double bond in catalysed hydroborations of

styrylboronate esters, a series of para-substituted analogues has been prepared (Wiesauer, 1997).

The molecule (Fig. 1) is essentially completely planar, with an r.m.s. deviation of 0.071 Å from the least-squares plane

through all atoms. All torsion angles are close to 0 and 180°, the largest corresponding to a twist of about 6° about the C2

—C21 bond linking the phenyl group to the central alkene unit. Bond lengths and angles are normal, with B—C

somewhat shorter and C═C longer than generally observed for single and double bonds, respectively (Allen et al., 1992);

together with the planarity of the molecule, they indicate extensive delocalization.

It is instructive to compare the title compound with two closely related styryl bis(boronate) esters, (Z)-[(4-NC—C6H4

)-C(Bcat)═CH(Bcat)] [(II); Bcat is 1,3,2-benzodioxaborole; cat = 1,2-O2C6H4; Clegg et al., 1996] and (Z)-[(4-MeO-C6H4

)-C(Bcat)═CH(BCat)] [(III); Lesley et al., 1996]. These differ from (I) in having either a π-acceptor or π-donor substituent

at the para-position of the phenyl ring attached to the α-carbon of the alkene and also a second Bcat moiety at Cα. In (II)

and (III), the Bcat at the β-position is approximately coplanar (dihedral angles approximately 9 and 7°, respectively) with

the alkene unit, as in (I), whereas the Bcat groups at Cα in (II) and (III) are roughly perpendicular (80 and 84°,

respectively) to the alkene plane. In both (II) and (III), the Cβ—B distances [1.535 (2) and 1.526 (2) Å] are significantly

shorter than their Cα—B distances [1.569 (2) and 1.566 (2) Å] and are consistent with the Cβ—B distance in (I) of

1.5321 (17) Å. Presumably this is a reflection of the delocalization present when the Bcat group is coplanar with the

alkene and trans to the aryl moiety. The C═C distance in (I) [1.3368 (16) Å] is shorter than the corresponding distance in

either (II) or (III) [1.349 (2) and 1.348 (2) Å, respectively] and is probably a result of less steric repulsion in the less

substituted alkene.

This structure was recently used as a test of crystal structure prediction methods (Lommerse et al., 2000), and proved to

be a considerable challenge to the currently available software systems, with only one prediction reasonably close to the

supporting information

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Acta Cryst. (2001). E57, o63–o65 S2. Experimental

In a nitrogen-filled glove-box, phenylacetylene (4.0 g, 39 mmol) and catecholborane (4.7 g, 39 mmol) were heated at 343

K for 2 h in a scintillation vial. On cooling, an orange solid was formed. The pure product was obtained as a colourless

crystalline material by recrystallization from diethylether/hexane by solvent diffusion at 238 K, in 70% yield. Analysis

calculated: C 75.73, H 4.99%; found: C 75.30, H 4.98%. 1_{H NMR (200 MHz): δ 6.48 (d, J = 18.5 Hz, 1H, PhCH), 7.08}

(m, 2H, C6H4), 7.26 (m, 2H, C6H4), 7.38 (m, 3H, C6H5), 7.58 (m, 2H, C6H5), 7.77 (d, J = 18.5 Hz, 1H, BCH). 13C{1H}

NMR (50 MHz): δ 112.3 (2 C, C3 and C6 of C6H4), 122.6 (2 C, C4 and C5 of C6H4), 127.4 (2 C, Ph), 128.7 (2 C, Ph), 129.6

(1 C, C4 of Ph), 136.9 (1 C, C1 of Ph), 148.3 (2 C, C1 and C2 of C6H4), 152.0 (1 C, PhCH), resonances of C bonded to B

too broad to be observed. 11_B{1_{H} NMR (64 MHz): δ 31.3. MS: 222 (M}+_{, 100%), 207 (26%), 196 (52%), 179 (30%), 178}

(30%), 144 (68%), 136 (78%), 129 (21%), 120 (84%), 111 (60%), 110 (79%), 102 (77%), 92 (48%).

S3. Refinement

The data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of

exposures; each set had a different φ angle for the crystal and each exposure covered 0.3° in ω. H atoms were placed

geometrically and refined with a riding model (including free rotation about C—C bonds), and with Uiso constrained to be

1.2Ueq of the carrier atom.

Figure 1

The molecular structure of (I) with atom labels and 50% probability ellipsoids for non-H atoms.

(E)-2-(2-phenylethenyl)-1,3,2-benzodioxaborole

Crystal data

C14H11BO2

Mr = 222.04

Monoclinic, P21/c

a = 6.8351 (9) Å

b = 7.6342 (10) Å

c = 21.422 (3) Å

β = 96.447 (3)°

V = 1110.8 (3) Å3

Z = 4

F(000) = 464

Dx = 1.328 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 5221 reflections

θ = 2.8–28.6°

µ = 0.09 mm−1

T = 160 K Block, colourless 0.62 × 0.50 × 0.40 mm

Data collection

Bruker SMART 1K CCD diffractometer

Radiation source: sealed tube Graphite monochromator

Detector resolution: 8.192 pixels mm-1

ω rotation with narrow frames scans 6709 measured reflections

supporting information

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Acta Cryst. (2001). E57, o63–o65

2326 reflections with I > 2σ(I)

Rint = 0.022

θmax = 28.6°, θmin = 1.9°

h = −9→8

k = −6→10

l = −28→28

Refinement

Refinement on F2 Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.037}

wR(F2_{) = 0.095}

S = 1.06 2571 reflections 155 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0389P)2 + 0.3966P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001 Δρmax = 0.26 e Å−3 Δρmin = −0.15 e Å−3

Extinction correction: SHELXTL, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4 Extinction coefficient: 0.021 (2)

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

x y z Uiso*/Ueq

C1 0.28827 (17) 0.60351 (16) 0.42739 (5) 0.0297 (3)

H1 0.1941 0.5390 0.4006 0.036*

C2 0.47581 (16) 0.59715 (14) 0.41531 (5) 0.0259 (2)

H2 0.5685 0.6606 0.4430 0.031*

B1 0.21424 (19) 0.70732 (17) 0.48127 (6) 0.0273 (3)

O1 0.33111 (11) 0.80614 (10) 0.52550 (4) 0.0274 (2)

O2 0.01719 (12) 0.71233 (11) 0.49180 (4) 0.0284 (2)

C11 0.20129 (15) 0.87370 (14) 0.56460 (5) 0.0242 (2)

C12 0.01226 (16) 0.81736 (14) 0.54409 (5) 0.0244 (2)

C13 −0.14856 (16) 0.86350 (15) 0.57367 (5) 0.0284 (2)

H13 −0.2778 0.8253 0.5590 0.034*

C14 −0.11031 (18) 0.96985 (15) 0.62656 (5) 0.0303 (3)

H14 −0.2163 1.0045 0.6489 0.036*

C15 0.07932 (18) 1.02632 (15) 0.64730 (5) 0.0308 (3)

H15 0.0998 1.0983 0.6836 0.037*

C16 0.24022 (17) 0.98000 (15) 0.61615 (5) 0.0290 (2)

H16 0.3696 1.0198 0.6299 0.035*

C21 0.55373 (15) 0.50245 (14) 0.36375 (5) 0.0232 (2)

C22 0.75132 (16) 0.52442 (15) 0.35424 (5) 0.0273 (2)

H22 0.8336 0.5975 0.3818 0.033*

C23 0.82871 (17) 0.44080 (16) 0.30499 (5) 0.0310 (3)

H23 0.9625 0.4589 0.2986 0.037*

C24 0.71196 (18) 0.33125 (16) 0.26518 (5) 0.0303 (3)

H24 0.7654 0.2734 0.2317 0.036*

C25 0.51591 (17) 0.30617 (15) 0.27446 (5) 0.0295 (3)

H25 0.4354 0.2306 0.2473 0.035*

C26 0.43755 (16) 0.39075 (15) 0.32302 (5) 0.0266 (2)

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Acta Cryst. (2001). E57, o63–o65 Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

C1 0.0290 (6) 0.0314 (6) 0.0286 (6) 0.0024 (4) 0.0026 (4) −0.0029 (5)

C2 0.0299 (5) 0.0247 (5) 0.0229 (5) 0.0012 (4) 0.0017 (4) 0.0011 (4)

B1 0.0278 (6) 0.0272 (6) 0.0270 (6) 0.0034 (5) 0.0034 (5) 0.0025 (5)

O1 0.0242 (4) 0.0310 (4) 0.0275 (4) 0.0029 (3) 0.0045 (3) 0.0003 (3)

O2 0.0267 (4) 0.0309 (4) 0.0279 (4) 0.0006 (3) 0.0042 (3) −0.0055 (3)

C11 0.0245 (5) 0.0236 (5) 0.0249 (5) 0.0032 (4) 0.0047 (4) 0.0047 (4)

C12 0.0289 (5) 0.0217 (5) 0.0226 (5) 0.0013 (4) 0.0027 (4) 0.0012 (4)

C13 0.0251 (5) 0.0293 (6) 0.0312 (6) 0.0006 (4) 0.0051 (4) 0.0012 (5)

C14 0.0334 (6) 0.0283 (6) 0.0309 (6) 0.0042 (5) 0.0105 (5) 0.0012 (5)

C15 0.0396 (6) 0.0273 (5) 0.0256 (5) 0.0003 (5) 0.0045 (4) −0.0016 (4)

C16 0.0298 (6) 0.0282 (6) 0.0283 (5) −0.0018 (4) 0.0000 (4) 0.0013 (4)

C21 0.0244 (5) 0.0230 (5) 0.0220 (5) 0.0029 (4) 0.0023 (4) 0.0040 (4)

C22 0.0248 (5) 0.0288 (5) 0.0276 (5) −0.0003 (4) 0.0006 (4) 0.0018 (4)

C23 0.0248 (5) 0.0362 (6) 0.0330 (6) 0.0026 (5) 0.0077 (4) 0.0044 (5)

C24 0.0368 (6) 0.0293 (6) 0.0259 (5) 0.0059 (5) 0.0087 (4) 0.0016 (4)

C25 0.0338 (6) 0.0273 (6) 0.0270 (5) −0.0003 (4) 0.0010 (4) −0.0017 (4)

C26 0.0240 (5) 0.0275 (5) 0.0284 (5) −0.0009 (4) 0.0031 (4) 0.0002 (4)

Geometric parameters (Å, º)

C1—C2 1.3368 (16) C14—H14 0.950

C1—B1 1.5321 (17) C15—C16 1.3945 (17)

C1—H1 0.950 C15—H15 0.950

C2—C21 1.4692 (15) C16—H16 0.950

C2—H2 0.950 C21—C22 1.3983 (15)

B1—O2 1.3909 (15) C21—C26 1.4013 (15)

B1—O1 1.3910 (15) C22—C23 1.3877 (16)

O1—C11 1.3864 (13) C22—H22 0.950

O2—C12 1.3811 (13) C23—C24 1.3823 (17)

C11—C16 1.3722 (16) C23—H23 0.950

C11—C12 1.3856 (15) C24—C25 1.3898 (16)

C12—C13 1.3749 (15) C24—H24 0.950

C13—C14 1.3944 (16) C25—C26 1.3824 (16)

C13—H13 0.950 C25—H25 0.950

C14—C15 1.3907 (17) C26—H26 0.950

C2—C1—B1 124.72 (11) C14—C15—H15 119.2

C2—C1—H1 117.6 C16—C15—H15 119.2

B1—C1—H1 117.6 C11—C16—C15 116.29 (11)

C1—C2—C21 126.86 (11) C11—C16—H16 121.9

C1—C2—H2 116.6 C15—C16—H16 121.9

C21—C2—H2 116.6 C22—C21—C26 118.12 (10)

O2—B1—O1 111.54 (10) C22—C21—C2 119.22 (10)

O2—B1—C1 122.96 (11) C26—C21—C2 122.66 (10)

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Acta Cryst. (2001). E57, o63–o65

C11—O1—B1 104.82 (9) C23—C22—H22 119.6

C12—O2—B1 105.06 (9) C21—C22—H22 119.6

C16—C11—C12 121.90 (10) C24—C23—C22 120.29 (10)

C16—C11—O1 128.82 (10) C24—C23—H23 119.9

C12—C11—O1 109.28 (9) C22—C23—H23 119.9

C13—C12—O2 128.04 (10) C23—C24—C25 119.63 (10)

C13—C12—C11 122.66 (10) C23—C24—H24 120.2

O2—C12—C11 109.30 (9) C25—C24—H24 120.2

C12—C13—C14 115.91 (11) C26—C25—C24 120.29 (11)

C12—C13—H13 122.0 C26—C25—H25 119.9

C14—C13—H13 122.0 C24—C25—H25 119.9

C15—C14—C13 121.54 (11) C25—C26—C21 120.83 (10)

C15—C14—H14 119.2 C25—C26—H26 119.6

C13—C14—H14 119.2 C21—C26—H26 119.6

C14—C15—C16 121.69 (11)

B1—C1—C2—C21 −178.83 (11) C11—C12—C13—C14 −0.71 (17)

C2—C1—B1—O2 179.17 (11) C12—C13—C14—C15 0.58 (17)

C2—C1—B1—O1 −1.22 (19) C13—C14—C15—C16 0.25 (18)

O2—B1—O1—C11 0.16 (12) C12—C11—C16—C15 0.84 (17)

C1—B1—O1—C11 −179.49 (11) O1—C11—C16—C15 −179.21 (10)

O1—B1—O2—C12 0.00 (12) C14—C15—C16—C11 −0.96 (17)

C1—B1—O2—C12 179.65 (10) C1—C2—C21—C22 173.52 (11)

B1—O1—C11—C16 179.80 (11) C1—C2—C21—C26 −6.08 (18)

B1—O1—C11—C12 −0.25 (12) C26—C21—C22—C23 1.36 (16)

B1—O2—C12—C13 −179.91 (11) C2—C21—C22—C23 −178.25 (10)

B1—O2—C12—C11 −0.16 (12) C21—C22—C23—C24 −1.30 (17)

C16—C11—C12—C13 −0.01 (17) C22—C23—C24—C25 0.46 (18)

O1—C11—C12—C13 −179.97 (10) C23—C24—C25—C26 0.28 (17)

C16—C11—C12—O2 −179.78 (10) C24—C25—C26—C21 −0.20 (17)

O1—C11—C12—O2 0.26 (12) C22—C21—C26—C25 −0.62 (16)