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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3166
https://doi.org/10.1107/S1600536810046222

1,2:3,5-Bis[(4-tert-butyl­phen­yl)boranedi­yl]-α-D-gluco­furan­ose

Marek Dąbrowski,a Sergiusz Luliński,a* Janusz Serwatowskia and Agnieszka Wilmowicza

aPhysical Chemistry Department, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
*Correspondence e-mail: serek@ch.pw.edu.pl

(Received 15 October 2010; accepted 9 November 2010; online 13 November 2010)

The crystal structure of the title compound, C26H34B2O6, comprises two crystallographically independent mol­ecules. In the crystal, the mol­ecules are linked by multiple inter­molecular O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional array.

Related literature

For the structural characterization of related monosaccharide boronates, see: Chandran & Nangia (2006)[Chandran, S. K. & Nangia, A. (2006). CrystEngComm, 8, 581-585.]; Draffin et al. (2004[Draffin, S. P., Duggan, P. J. & Fallon, G. D. (2004). Acta Cryst. E60, o1520-o1522.]). For complexes of boronic acids with glucose, see: Hall (2005[Hall, D. G. (2005). Boronic Acids. Weinheim: Wiley-VCH.]).

[Scheme 1]

Experimental

Crystal data

  • C26H34B2O6

  • Mr = 464.15

  • Monoclinic, P 21

  • a = 11.2372 (3) Å

  • b = 10.1910 (3) Å

  • c = 22.5084 (7) Å

  • β = 104.103 (3)°

  • V = 2499.93 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.60 × 0.30 × 0.22 mm
Data collection

  • Kuma KM-4-CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction 2005[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.95, Tmax = 0.98

  • 47322 measured reflections

  • 6519 independent reflections

  • 5409 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.072

  • S = 0.99

  • 6519 reflections

  • 627 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O6A—H6A⋯O6B 0.84 2.07 2.8660 (17) 158
O6B—H6B⋯O1Ai 0.84 2.47 3.1131 (17) 134
C1B—H1B⋯O6A 1.00 2.37 3.318 (2) 159
C2B—H2B⋯O4Bii 1.00 2.41 3.379 (2) 162
C4A—H4A⋯O5Biii 1.00 2.44 3.246 (2) 137
C4B—H4B⋯O6Aiv 1.00 2.51 3.231 (2) 129
C3A—H3A⋯O1Bi 1.00 2.55 3.480 (2) 155
C6A—H6A1⋯O4Ai 0.99 2.60 3.499 (2) 150
C1A—H1A⋯O6B 1.00 2.62 3.553 (2) 155
C2A—H2A⋯O4Ai 1.00 2.64 3.587 (2) 159
C14A—H14A⋯O2Ai 0.95 2.66 3.433 (2) 139
C3A—H3A⋯O4Bi 1.00 2.68 3.442 (2) 133
C3B—H3B⋯O4Av 1.00 2.72 3.522 (2) 137
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+1]; (ii) [-x-1, y+{\script{1\over 2}}, -z+1]; (iii) x+1, y, z; (iv) [-x-1, y-{\script{1\over 2}}, -z+1]; (v) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2005[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2005[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810046222/pb2045sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046222/pb2045Isup2.hkl

checkCIF report


Comment top

The interaction of boronic acids with sugars is of great importance due to potential applications in medicine. The work in the area is focused mainly on complexes of boronic acids with glucose (Hall, 2005). Despite a signifcant progress in the field only two crystal structures of 2:1 boronic acid–glucose complexes were reported (Chandran & Nangia, 2006). They involved simple phenylboronic acid and its 4-methyl congener. The molecule of the title compound (I) features the glucose backbone in its furanose form, which resembles the situation observed in crystal structures for analogous complexes. There are only slight differences in the metric parameters of two independent molecules. One of boron atoms is bonded to O4 and O5 atoms, which results in the formation of a 5-membered ring. The second boron atom is bonded to O2 and O3 atoms; as a result a 6-membered ring is formed. Both boron-containing heterocycles are approximately coplanar with the adjacent phenyl rings. The supramolecular arrangement in (I) is dictated by one relatively strong O–H···O hydrogen bond which links the terminal hydroxyl groups of two independent molecules. The weaker O–H···O hydrogen bond is formed between the H6B atom and the ring O1A atom. These two interactions are complemented by the set of multiple C–H···O contacts (Table 1). The shortest one (2.37 Å) is observed between the H1B and the O6A atoms. Unlike the tolyl groups in the related compound (Chandran & Nangia, 2006), the tert-butyl groups in (I) are not involved in C–H···O interactions. As a result, a two-dimensional array aligned parallel to the (001) plane is formed by atoms from central glucofuranose cores of both independent molecules whereas a further three-dimensional assembly is achieved only by weak van der Waals interactions of external tert-butyl groups.

Related literature top

For the structural characterization of related monosaccharide boronates, see: Chandran & Nangia (2006); Draffin et al. (2004). For complexes of boronic acids with glucose, see: Hall (2005).

Experimental top

A mixture of α-D-glucose (3.6 g) and 4-(tert-butyl)phenylboronic acid (3.55 g) in 1,4-dioxane (30 ml) was stirred for 6 hrs at 50 oC. The resulting solution was concentrated. The residue was extracted with benzene (2 x 30 ml). Combined extracts were filtered. Evaporation yielded a solid which was washed with pentane (20 ml). Yield of (I) 4.0 g, m.p. 410 K. 1H NMR (CDCl3): 7.79 (m, 4 H), 7.45 (d, 2 H), 7.40 (d, 2 H), 6.18 (d, 1 H), 5.00 (d, 1 H), 4.70 (d, 1 H), 4.47 (t, 1 H), 4.27 (d. 1H), 3.86 (m, 1 H), 3.73 (m, 1 H), 1.81 (t, 1 H),1.33 (s, 9 H), 1.32 (s, 9 H) p.p.m.; 11B NMR: 26.0 p.p.m.. Crystals suitable for single-crystal X-ray diffraction analysis were grown by slow evaporation of a solution of (I) (0.2 g) in benzene (10 ml).

Refinement top

All hydrogen atoms were located geometrically with C—H = 0.95—1.00 Å and O—H = 0.84 Å, and were included in the refinement in the riding model approximation with U(H) set to 1.2—1.5Ueq(C/O).

Structure description top

The interaction of boronic acids with sugars is of great importance due to potential applications in medicine. The work in the area is focused mainly on complexes of boronic acids with glucose (Hall, 2005). Despite a signifcant progress in the field only two crystal structures of 2:1 boronic acid–glucose complexes were reported (Chandran & Nangia, 2006). They involved simple phenylboronic acid and its 4-methyl congener. The molecule of the title compound (I) features the glucose backbone in its furanose form, which resembles the situation observed in crystal structures for analogous complexes. There are only slight differences in the metric parameters of two independent molecules. One of boron atoms is bonded to O4 and O5 atoms, which results in the formation of a 5-membered ring. The second boron atom is bonded to O2 and O3 atoms; as a result a 6-membered ring is formed. Both boron-containing heterocycles are approximately coplanar with the adjacent phenyl rings. The supramolecular arrangement in (I) is dictated by one relatively strong O–H···O hydrogen bond which links the terminal hydroxyl groups of two independent molecules. The weaker O–H···O hydrogen bond is formed between the H6B atom and the ring O1A atom. These two interactions are complemented by the set of multiple C–H···O contacts (Table 1). The shortest one (2.37 Å) is observed between the H1B and the O6A atoms. Unlike the tolyl groups in the related compound (Chandran & Nangia, 2006), the tert-butyl groups in (I) are not involved in C–H···O interactions. As a result, a two-dimensional array aligned parallel to the (001) plane is formed by atoms from central glucofuranose cores of both independent molecules whereas a further three-dimensional assembly is achieved only by weak van der Waals interactions of external tert-butyl groups.

For the structural characterization of related monosaccharide boronates, see: Chandran & Nangia (2006); Draffin et al. (2004). For complexes of boronic acids with glucose, see: Hall (2005).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of molecule A of (I) showing the atom-labelling scheme. Displacement ellipsoids for all non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing diagram for (I) showing hydrogen-bonding and C–H···O interactions (dashed lines).
1,2:3,5-Bis[(4-tert-butylphenyl)boranediyl]-α-D-glucofuranose top
Crystal data top
C26H34B2O6Dx = 1.233 Mg m−3
Mr = 464.15Melting point: 480 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.2372 (3) ÅCell parameters from 28404 reflections
b = 10.1910 (3) Åθ = 2.2–28.8°
c = 22.5084 (7) ŵ = 0.09 mm−1
β = 104.103 (3)°T = 100 K
V = 2499.93 (13) Å3Prismatic, colourless
Z = 40.60 × 0.30 × 0.22 mm
F(000) = 992
Data collection top
Kuma KM-4-CCD
diffractometer		6519 independent reflections
Radiation source: fine-focus sealed tube5409 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 8.6479 pixels mm-1θmax = 28.6°, θmin = 2.7°
ω scansh = −14→15
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction 2005)		k = −13→13
Tmin = 0.95, Tmax = 0.98l = −29→30
47322 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0459P)2]
where P = (Fo2 + 2Fc2)/3
6519 reflections(Δ/σ)max = 0.001
627 parametersΔρmax = 0.24 e Å−3
1 restraintΔρmin = −0.19 e Å−3
Crystal data top
C26H34B2O6V = 2499.93 (13) Å3
Mr = 464.15Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.2372 (3) ŵ = 0.09 mm−1
b = 10.1910 (3) ÅT = 100 K
c = 22.5084 (7) Å0.60 × 0.30 × 0.22 mm
β = 104.103 (3)°
Data collection top
Kuma KM-4-CCD
diffractometer		6519 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction 2005)		5409 reflections with I > 2σ(I)
Tmin = 0.95, Tmax = 0.98Rint = 0.025
47322 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0311 restraint
wR(F2) = 0.072H-atom parameters constrained
S = 0.99Δρmax = 0.24 e Å−3
6519 reflectionsΔρmin = −0.19 e Å−3
627 parameters
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
xyzUiso*/Ueq
B1A−0.05450 (17)0.11527 (19)0.33127 (9)0.0162 (4)
B2A0.15751 (16)0.0744 (2)0.57760 (9)0.0167 (4)
C1A−0.05567 (14)0.05711 (17)0.44985 (7)0.0152 (3)
H1A−0.07390.06530.49100.018*
C2A0.02250 (15)0.17288 (17)0.43916 (7)0.0163 (4)
H2A−0.00800.25770.45220.020*
C3A0.14809 (15)0.13639 (17)0.47939 (7)0.0164 (4)
H3A0.21720.16810.46230.020*
C4A0.14303 (15)−0.01529 (17)0.48322 (7)0.0170 (4)
H4A0.2092−0.05750.46710.020*
C5A−0.17374 (15)0.03966 (17)0.40139 (7)0.0153 (3)
H5A−0.2085−0.04860.40680.018*
C6A−0.26913 (15)0.14410 (17)0.40528 (7)0.0170 (3)
H6A1−0.23340.23220.40280.020*
H6A2−0.34080.13440.36990.020*
C7A−0.04092 (15)0.12469 (17)0.26366 (7)0.0165 (3)
C8A−0.13660 (15)0.08451 (17)0.21478 (8)0.0187 (4)
H8A−0.21030.05220.22300.022*
C9A−0.12639 (15)0.09073 (18)0.15468 (8)0.0190 (4)
H9A−0.19320.06260.12260.023*
C10A−0.01962 (15)0.13757 (17)0.14030 (8)0.0168 (3)
C11A0.07554 (15)0.17926 (17)0.18901 (8)0.0183 (4)
H11A0.14890.21230.18080.022*
C12A0.06513 (15)0.17350 (17)0.24947 (8)0.0180 (4)
H12A0.13120.20320.28150.022*
C13A0.14908 (14)0.08726 (17)0.64508 (7)0.0163 (4)
C14A0.14777 (15)0.21093 (18)0.67181 (8)0.0191 (4)
H14A0.16140.28670.64980.023*
C15A0.12716 (15)0.22555 (18)0.72956 (8)0.0193 (4)
H15A0.12730.31100.74640.023*
C16A0.10604 (14)0.11714 (17)0.76369 (7)0.0167 (4)
C17A0.10985 (15)−0.00752 (17)0.73780 (8)0.0186 (4)
H17A0.0977−0.08340.76010.022*
C18A0.13121 (15)−0.02131 (17)0.67968 (8)0.0188 (4)
H18A0.1337−0.10680.66320.023*
C19A0.07786 (15)0.13829 (17)0.82624 (7)0.0181 (4)
C20A0.18873 (16)0.2038 (2)0.87000 (8)0.0242 (4)
H20A0.26220.15020.87240.036*
H20B0.17310.21160.91080.036*
H20C0.20150.29130.85460.036*
C21A−0.03485 (16)0.22779 (19)0.81846 (8)0.0232 (4)
H21A−0.01690.31340.80280.035*
H21B−0.05490.23930.85810.035*
H21C−0.10470.18770.78940.035*
C22A0.05076 (17)0.00842 (19)0.85447 (8)0.0242 (4)
H22A−0.0199−0.03410.82700.036*
H22B0.03230.02540.89410.036*
H22C0.1225−0.04920.86030.036*
C23A−0.01052 (15)0.13871 (18)0.07325 (7)0.0176 (4)
C24A−0.11940 (17)0.2150 (2)0.03317 (8)0.0245 (4)
H24A−0.19660.17390.03620.037*
H24B−0.11360.2134−0.00960.037*
H24C−0.11720.30600.04740.037*
C25A−0.01485 (17)−0.00393 (19)0.04997 (8)0.0232 (4)
H25A−0.0914−0.04540.05370.035*
H25B0.0552−0.05280.07450.035*
H25C−0.0111−0.00420.00690.035*
C26A0.10810 (16)0.2025 (2)0.06552 (8)0.0243 (4)
H26A0.10890.20250.02210.036*
H26B0.17880.15290.08890.036*
H26C0.11260.29310.08060.036*
O1A0.02515 (10)−0.05418 (11)0.44963 (5)0.0169 (3)
O2A−0.15223 (10)0.04640 (12)0.34114 (5)0.0182 (3)
O3A0.03041 (10)0.17685 (12)0.37658 (5)0.0181 (3)
O4A0.15721 (10)−0.04286 (12)0.54725 (5)0.0186 (3)
O5A0.15740 (10)0.18162 (12)0.54097 (5)0.0181 (3)
O6A−0.30884 (10)0.13444 (13)0.46061 (5)0.0205 (3)
H6A−0.25470.16570.48970.031*
B1B−0.37416 (18)0.0014 (2)0.69984 (9)0.0191 (4)
B2B−0.50375 (17)−0.1162 (2)0.45330 (9)0.0172 (4)
C1B−0.32186 (15)−0.02484 (17)0.58744 (7)0.0162 (3)
H1B−0.30470.00280.54770.019*
C2B−0.45126 (15)0.01735 (17)0.58916 (7)0.0162 (3)
H2B−0.47060.10790.57250.019*
C3B−0.53087 (15)−0.08554 (17)0.54920 (7)0.0169 (4)
H3B−0.6026−0.11160.56550.020*
C4B−0.44075 (15)−0.20161 (17)0.54991 (8)0.0171 (4)
H4B−0.4734−0.28520.56300.020*
C5B−0.22174 (16)0.02487 (18)0.63990 (7)0.0195 (4)
H5B−0.1460−0.02800.64170.023*
C6B−0.19178 (16)0.16913 (19)0.63265 (8)0.0215 (4)
H6B1−0.26620.22310.63000.026*
H6B2−0.12820.19840.66890.026*
C7B−0.40312 (16)−0.01712 (18)0.76364 (7)0.0191 (4)
C8B−0.31073 (16)−0.00618 (19)0.81758 (8)0.0229 (4)
H8B−0.22940.01310.81510.028*
C9B−0.33471 (15)−0.02280 (19)0.87460 (8)0.0214 (4)
H9B−0.2702−0.01180.91040.026*
C10B−0.45185 (15)−0.05533 (17)0.88046 (7)0.0167 (3)
C11B−0.54493 (16)−0.06565 (19)0.82682 (8)0.0208 (4)
H11B−0.6260−0.08610.82930.025*
C12B−0.52069 (16)−0.04637 (19)0.76972 (8)0.0224 (4)
H12B−0.5859−0.05330.73400.027*
C13B−0.51855 (15)−0.10119 (17)0.38352 (8)0.0170 (4)
C14B−0.60372 (16)−0.01384 (18)0.34760 (8)0.0213 (4)
H14B−0.65390.03870.36650.026*
C15B−0.61530 (16)−0.00353 (19)0.28521 (8)0.0218 (4)
H15B−0.67350.05600.26200.026*
C16B−0.54304 (15)−0.07903 (17)0.25534 (8)0.0182 (4)
C17B−0.45914 (15)−0.16602 (18)0.29079 (8)0.0193 (4)
H17B−0.4094−0.21900.27180.023*
C18B−0.44731 (15)−0.17626 (17)0.35355 (8)0.0184 (4)
H18B−0.3891−0.23600.37660.022*
C19B−0.55901 (16)−0.06446 (19)0.18590 (8)0.0210 (4)
C20B−0.68993 (17)−0.1066 (2)0.15334 (8)0.0287 (4)
H20D−0.7015−0.19940.16200.043*
H20E−0.7025−0.09410.10910.043*
H20F−0.7492−0.05320.16820.043*
C21B−0.53829 (19)0.0793 (2)0.17082 (9)0.0302 (4)
H21D−0.59700.13520.18480.045*
H21E−0.55010.08920.12650.045*
H21F−0.45450.10540.19160.045*
C22B−0.46919 (18)−0.1506 (2)0.16226 (9)0.0292 (5)
H22D−0.3849−0.12550.18260.044*
H22E−0.4826−0.13870.11790.044*
H22F−0.4825−0.24280.17110.044*
C23B−0.47421 (15)−0.07315 (18)0.94441 (7)0.0180 (4)
C24B−0.46988 (18)0.0627 (2)0.97443 (9)0.0281 (4)
H24D−0.38980.10320.97670.042*
H24E−0.48240.05331.01580.042*
H24F−0.53470.11830.94990.042*
C25B−0.37355 (16)−0.1596 (2)0.98413 (8)0.0228 (4)
H25D−0.2933−0.11840.98760.034*
H25E−0.3746−0.24620.96510.034*
H25F−0.3886−0.16931.02500.034*
C26B−0.59886 (16)−0.1354 (2)0.94248 (8)0.0239 (4)
H26D−0.6063−0.15110.98440.036*
H26E−0.6058−0.21890.92030.036*
H26F−0.6644−0.07610.92150.036*
O1B−0.32857 (10)−0.16637 (12)0.58971 (5)0.0175 (3)
O2B−0.25412 (11)0.01234 (13)0.69747 (5)0.0232 (3)
O3B−0.47056 (10)0.00418 (12)0.64942 (5)0.0193 (3)
O4B−0.42916 (10)−0.20952 (12)0.48781 (5)0.0182 (3)
O5B−0.56770 (10)−0.04289 (12)0.48642 (5)0.0175 (3)
O6B−0.14817 (11)0.18677 (13)0.57813 (5)0.0233 (3)
H6B−0.08390.23230.58640.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B1A0.0159 (9)0.0133 (10)0.0197 (10)0.0036 (8)0.0051 (8)0.0009 (8)
B2A0.0104 (8)0.0175 (10)0.0217 (10)0.0003 (8)0.0032 (7)0.0000 (8)
C1A0.0170 (8)0.0136 (8)0.0164 (8)0.0015 (7)0.0069 (7)−0.0006 (7)
C2A0.0196 (8)0.0151 (9)0.0150 (8)−0.0001 (7)0.0058 (7)−0.0007 (7)
C3A0.0151 (8)0.0194 (9)0.0153 (8)−0.0024 (7)0.0048 (7)−0.0010 (7)
C4A0.0149 (8)0.0192 (9)0.0170 (8)0.0004 (7)0.0044 (7)−0.0009 (7)
C5A0.0162 (8)0.0172 (9)0.0137 (8)−0.0014 (7)0.0062 (6)0.0002 (7)
C6A0.0168 (8)0.0179 (9)0.0170 (8)0.0002 (7)0.0052 (7)0.0019 (7)
C7A0.0194 (8)0.0139 (8)0.0167 (8)0.0030 (7)0.0055 (7)−0.0001 (7)
C8A0.0170 (8)0.0175 (9)0.0231 (9)−0.0009 (7)0.0078 (7)0.0022 (7)
C9A0.0173 (8)0.0193 (9)0.0186 (9)−0.0015 (7)0.0013 (7)−0.0008 (7)
C10A0.0193 (8)0.0129 (8)0.0186 (9)0.0024 (7)0.0058 (7)0.0012 (7)
C11A0.0160 (8)0.0176 (9)0.0220 (9)0.0002 (7)0.0060 (7)0.0019 (7)
C12A0.0176 (8)0.0168 (9)0.0185 (9)0.0001 (7)0.0021 (7)−0.0011 (7)
C13A0.0112 (8)0.0193 (9)0.0176 (8)0.0003 (7)0.0016 (6)0.0015 (7)
C14A0.0185 (9)0.0175 (9)0.0214 (9)−0.0023 (7)0.0052 (7)0.0030 (7)
C15A0.0203 (9)0.0146 (9)0.0229 (9)−0.0028 (7)0.0051 (7)−0.0026 (7)
C16A0.0125 (8)0.0198 (9)0.0175 (9)−0.0012 (7)0.0030 (7)−0.0005 (7)
C17A0.0207 (9)0.0147 (9)0.0203 (9)−0.0007 (7)0.0048 (7)0.0031 (7)
C18A0.0200 (9)0.0150 (9)0.0209 (9)0.0011 (7)0.0038 (7)−0.0018 (7)
C19A0.0190 (8)0.0179 (9)0.0185 (9)−0.0034 (7)0.0067 (7)−0.0007 (7)
C20A0.0251 (9)0.0287 (11)0.0189 (9)−0.0051 (8)0.0054 (7)−0.0022 (8)
C21A0.0225 (9)0.0248 (10)0.0238 (10)0.0000 (8)0.0086 (8)−0.0025 (8)
C22A0.0287 (10)0.0258 (10)0.0206 (9)−0.0026 (8)0.0106 (8)0.0019 (8)
C23A0.0201 (8)0.0191 (9)0.0138 (8)−0.0005 (7)0.0045 (7)−0.0003 (7)
C24A0.0273 (10)0.0274 (10)0.0190 (9)0.0037 (8)0.0057 (8)0.0028 (8)
C25A0.0295 (10)0.0230 (10)0.0181 (9)−0.0008 (8)0.0079 (8)−0.0024 (7)
C26A0.0267 (10)0.0296 (11)0.0185 (9)−0.0036 (8)0.0091 (7)0.0032 (8)
O1A0.0167 (6)0.0136 (6)0.0208 (6)0.0008 (5)0.0053 (5)−0.0020 (5)
O2A0.0180 (6)0.0221 (7)0.0150 (6)−0.0032 (5)0.0052 (5)−0.0024 (5)
O3A0.0206 (6)0.0191 (6)0.0151 (6)−0.0036 (5)0.0054 (5)0.0015 (5)
O4A0.0199 (6)0.0183 (6)0.0175 (6)0.0021 (5)0.0041 (5)0.0015 (5)
O5A0.0194 (6)0.0180 (6)0.0168 (6)−0.0032 (5)0.0041 (5)−0.0017 (5)
O6A0.0182 (6)0.0268 (7)0.0178 (6)0.0000 (5)0.0069 (5)0.0002 (5)
B1B0.0200 (10)0.0185 (10)0.0183 (10)−0.0009 (8)0.0038 (8)−0.0008 (8)
B2B0.0138 (9)0.0154 (10)0.0219 (10)−0.0043 (8)0.0033 (8)−0.0025 (8)
C1B0.0160 (8)0.0172 (9)0.0163 (8)−0.0001 (7)0.0058 (7)0.0016 (7)
C2B0.0183 (8)0.0165 (9)0.0142 (8)0.0010 (7)0.0048 (7)0.0012 (7)
C3B0.0146 (8)0.0187 (9)0.0175 (8)−0.0003 (7)0.0043 (7)0.0011 (7)
C4B0.0161 (8)0.0164 (9)0.0189 (9)−0.0012 (7)0.0048 (7)−0.0003 (7)
C5B0.0183 (9)0.0257 (10)0.0152 (8)−0.0014 (7)0.0051 (7)0.0007 (7)
C6B0.0210 (9)0.0255 (10)0.0178 (9)−0.0038 (8)0.0046 (7)−0.0030 (8)
C7B0.0209 (9)0.0188 (9)0.0174 (9)0.0006 (7)0.0042 (7)0.0015 (7)
C8B0.0176 (9)0.0287 (10)0.0230 (9)−0.0034 (8)0.0057 (7)0.0039 (8)
C9B0.0178 (9)0.0276 (10)0.0162 (9)−0.0016 (8)−0.0007 (7)0.0015 (7)
C10B0.0202 (8)0.0131 (8)0.0173 (8)0.0015 (7)0.0054 (7)0.0001 (7)
C11B0.0162 (8)0.0268 (11)0.0200 (9)−0.0018 (8)0.0056 (7)0.0001 (7)
C12B0.0194 (9)0.0281 (10)0.0174 (9)−0.0007 (8)−0.0001 (7)−0.0002 (8)
C13B0.0152 (8)0.0164 (9)0.0192 (9)−0.0030 (7)0.0034 (7)−0.0023 (7)
C14B0.0205 (9)0.0208 (10)0.0232 (9)0.0019 (8)0.0066 (7)−0.0043 (7)
C15B0.0185 (9)0.0218 (10)0.0234 (9)0.0065 (8)0.0018 (7)0.0009 (8)
C16B0.0178 (8)0.0182 (9)0.0191 (9)−0.0009 (7)0.0054 (7)−0.0003 (7)
C17B0.0178 (9)0.0206 (9)0.0199 (9)0.0016 (7)0.0056 (7)−0.0026 (7)
C18B0.0147 (8)0.0164 (9)0.0233 (9)0.0007 (7)0.0031 (7)0.0015 (7)
C19B0.0216 (9)0.0251 (10)0.0168 (9)0.0031 (8)0.0057 (7)0.0007 (7)
C20B0.0269 (10)0.0390 (12)0.0186 (10)0.0013 (9)0.0024 (8)−0.0013 (9)
C21B0.0335 (11)0.0312 (11)0.0263 (10)−0.0010 (9)0.0082 (8)0.0059 (9)
C22B0.0312 (11)0.0383 (12)0.0200 (10)0.0076 (9)0.0098 (8)0.0002 (9)
C23B0.0188 (8)0.0203 (9)0.0152 (8)0.0004 (7)0.0051 (7)0.0020 (7)
C24B0.0347 (11)0.0248 (10)0.0266 (10)0.0016 (9)0.0110 (8)−0.0043 (8)
C25B0.0192 (9)0.0303 (11)0.0199 (9)0.0001 (8)0.0066 (7)0.0053 (8)
C26B0.0197 (9)0.0307 (11)0.0227 (10)−0.0004 (8)0.0076 (8)0.0050 (8)
O1B0.0158 (6)0.0157 (6)0.0201 (6)0.0010 (5)0.0026 (5)0.0009 (5)
O2B0.0206 (6)0.0344 (8)0.0143 (6)−0.0040 (6)0.0039 (5)0.0018 (5)
O3B0.0184 (6)0.0241 (7)0.0159 (6)0.0038 (5)0.0053 (5)0.0005 (5)
O4B0.0202 (6)0.0170 (6)0.0172 (6)0.0022 (5)0.0044 (5)−0.0017 (5)
O5B0.0166 (6)0.0205 (6)0.0147 (6)0.0016 (5)0.0021 (5)0.0003 (5)
O6B0.0229 (7)0.0261 (7)0.0214 (7)−0.0094 (6)0.0062 (5)0.0011 (5)
Geometric parameters (Å, º) top
B1A—O2A1.366 (2)B1B—O3B1.365 (2)
B1A—O3A1.368 (2)B1B—O2B1.367 (2)
B1A—C7A1.569 (2)B1B—C7B1.559 (2)
B2A—O5A1.369 (2)B2B—O5B1.375 (2)
B2A—O4A1.376 (2)B2B—O4B1.376 (2)
B2A—C13A1.550 (2)B2B—C13B1.546 (2)
C1A—O1A1.454 (2)C1B—O1B1.446 (2)
C1A—C5A1.509 (2)C1B—C5B1.506 (2)
C1A—C2A1.525 (2)C1B—C2B1.526 (2)
C1A—H1A1.0000C1B—H1B1.0000
C2A—O3A1.4334 (18)C2B—O3B1.4310 (18)
C2A—C3A1.526 (2)C2B—C3B1.522 (2)
C2A—H2A1.0000C2B—H2B1.0000
C3A—O5A1.4400 (19)C3B—O5B1.4392 (19)
C3A—C4A1.550 (2)C3B—C4B1.555 (2)
C3A—H3A1.0000C3B—H3B1.0000
C4A—O1A1.4125 (19)C4B—O1B1.404 (2)
C4A—O4A1.4386 (19)C4B—O4B1.4373 (19)
C4A—H4A1.0000C4B—H4B1.0000
C5A—O2A1.4362 (18)C5B—O2B1.4344 (19)
C5A—C6A1.528 (2)C5B—C6B1.526 (3)
C5A—H5A1.0000C5B—H5B1.0000
C6A—O6A1.4248 (18)C6B—O6B1.4394 (19)
C6A—H6A10.9900C6B—H6B10.9900
C6A—H6A20.9900C6B—H6B20.9900
C7A—C12A1.398 (2)C7B—C12B1.393 (2)
C7A—C8A1.399 (2)C7B—C8B1.397 (2)
C8A—C9A1.387 (2)C8B—C9B1.385 (2)
C8A—H8A0.9500C8B—H8B0.9500
C9A—C10A1.401 (2)C9B—C10B1.394 (2)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.398 (2)C10B—C11B1.395 (2)
C10A—C23A1.537 (2)C10B—C23B1.531 (2)
C11A—C12A1.395 (2)C11B—C12B1.391 (2)
C11A—H11A0.9500C11B—H11B0.9500
C12A—H12A0.9500C12B—H12B0.9500
C13A—C18A1.395 (2)C13B—C18B1.394 (2)
C13A—C14A1.398 (2)C13B—C14B1.409 (2)
C14A—C15A1.383 (2)C14B—C15B1.382 (2)
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.399 (2)C15B—C16B1.403 (2)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.403 (2)C16B—C17B1.395 (2)
C16A—C19A1.532 (2)C16B—C19B1.536 (2)
C17A—C18A1.393 (2)C17B—C18B1.390 (2)
C17A—H17A0.9500C17B—H17B0.9500
C18A—H18A0.9500C18B—H18B0.9500
C19A—C22A1.530 (2)C19B—C22B1.528 (3)
C19A—C21A1.536 (2)C19B—C21B1.534 (3)
C19A—C20A1.539 (2)C19B—C20B1.536 (3)
C20A—H20A0.9800C20B—H20D0.9800
C20A—H20B0.9800C20B—H20E0.9800
C20A—H20C0.9800C20B—H20F0.9800
C21A—H21A0.9800C21B—H21D0.9800
C21A—H21B0.9800C21B—H21E0.9800
C21A—H21C0.9800C21B—H21F0.9800
C22A—H22A0.9800C22B—H22D0.9800
C22A—H22B0.9800C22B—H22E0.9800
C22A—H22C0.9800C22B—H22F0.9800
C23A—C26A1.531 (2)C23B—C26B1.529 (2)
C23A—C24A1.542 (2)C23B—C24B1.536 (3)
C23A—C25A1.542 (3)C23B—C25B1.537 (2)
C24A—H24A0.9800C24B—H24D0.9800
C24A—H24B0.9800C24B—H24E0.9800
C24A—H24C0.9800C24B—H24F0.9800
C25A—H25A0.9800C25B—H25D0.9800
C25A—H25B0.9800C25B—H25E0.9800
C25A—H25C0.9800C25B—H25F0.9800
C26A—H26A0.9800C26B—H26D0.9800
C26A—H26B0.9800C26B—H26E0.9800
C26A—H26C0.9800C26B—H26F0.9800
O6A—H6A0.8400O6B—H6B0.8400
O2A—B1A—O3A123.84 (15)O3B—B1B—O2B123.81 (16)
O2A—B1A—C7A117.46 (15)O3B—B1B—C7B117.83 (15)
O3A—B1A—C7A118.70 (15)O2B—B1B—C7B118.36 (15)
O5A—B2A—O4A113.24 (14)O5B—B2B—O4B113.35 (15)
O5A—B2A—C13A122.11 (16)O5B—B2B—C13B123.78 (16)
O4A—B2A—C13A124.50 (16)O4B—B2B—C13B122.80 (16)
O1A—C1A—C5A110.22 (13)O1B—C1B—C5B110.08 (14)
O1A—C1A—C2A102.63 (12)O1B—C1B—C2B102.82 (13)
C5A—C1A—C2A114.59 (14)C5B—C1B—C2B114.82 (14)
O1A—C1A—H1A109.7O1B—C1B—H1B109.6
C5A—C1A—H1A109.7C5B—C1B—H1B109.6
C2A—C1A—H1A109.7C2B—C1B—H1B109.6
O3A—C2A—C1A110.67 (13)O3B—C2B—C3B107.02 (13)
O3A—C2A—C3A108.68 (12)O3B—C2B—C1B111.29 (13)
C1A—C2A—C3A101.71 (13)C3B—C2B—C1B102.56 (13)
O3A—C2A—H2A111.8O3B—C2B—H2B111.8
C1A—C2A—H2A111.8C3B—C2B—H2B111.8
C3A—C2A—H2A111.8C1B—C2B—H2B111.8
O5A—C3A—C2A109.46 (13)O5B—C3B—C2B111.05 (14)
O5A—C3A—C4A105.12 (13)O5B—C3B—C4B105.70 (13)
C2A—C3A—C4A103.59 (14)C2B—C3B—C4B103.33 (13)
O5A—C3A—H3A112.7O5B—C3B—H3B112.1
C2A—C3A—H3A112.7C2B—C3B—H3B112.1
C4A—C3A—H3A112.7C4B—C3B—H3B112.1
O1A—C4A—O4A110.00 (12)O1B—C4B—O4B110.79 (13)
O1A—C4A—C3A107.00 (13)O1B—C4B—C3B107.05 (13)
O4A—C4A—C3A104.70 (13)O4B—C4B—C3B104.23 (13)
O1A—C4A—H4A111.6O1B—C4B—H4B111.5
O4A—C4A—H4A111.6O4B—C4B—H4B111.5
C3A—C4A—H4A111.6C3B—C4B—H4B111.5
O2A—C5A—C1A110.87 (12)O2B—C5B—C1B111.88 (13)
O2A—C5A—C6A107.62 (12)O2B—C5B—C6B107.07 (14)
C1A—C5A—C6A112.46 (14)C1B—C5B—C6B112.48 (15)
O2A—C5A—H5A108.6O2B—C5B—H5B108.4
C1A—C5A—H5A108.6C1B—C5B—H5B108.4
C6A—C5A—H5A108.6C6B—C5B—H5B108.4
O6A—C6A—C5A112.05 (13)O6B—C6B—C5B109.96 (14)
O6A—C6A—H6A1109.2O6B—C6B—H6B1109.7
C5A—C6A—H6A1109.2C5B—C6B—H6B1109.7
O6A—C6A—H6A2109.2O6B—C6B—H6B2109.7
C5A—C6A—H6A2109.2C5B—C6B—H6B2109.7
H6A1—C6A—H6A2107.9H6B1—C6B—H6B2108.2
C12A—C7A—C8A117.31 (15)C12B—C7B—C8B116.97 (15)
C12A—C7A—B1A122.22 (15)C12B—C7B—B1B122.14 (15)
C8A—C7A—B1A120.47 (15)C8B—C7B—B1B120.88 (15)
C9A—C8A—C7A121.56 (15)C9B—C8B—C7B121.65 (16)
C9A—C8A—H8A119.2C9B—C8B—H8B119.2
C7A—C8A—H8A119.2C7B—C8B—H8B119.2
C8A—C9A—C10A121.35 (15)C8B—C9B—C10B121.21 (15)
C8A—C9A—H9A119.3C8B—C9B—H9B119.4
C10A—C9A—H9A119.3C10B—C9B—H9B119.4
C11A—C10A—C9A117.20 (15)C9B—C10B—C11B117.51 (15)
C11A—C10A—C23A123.11 (14)C9B—C10B—C23B119.47 (14)
C9A—C10A—C23A119.68 (14)C11B—C10B—C23B122.97 (15)
C12A—C11A—C10A121.47 (15)C12B—C11B—C10B120.96 (16)
C12A—C11A—H11A119.3C12B—C11B—H11B119.5
C10A—C11A—H11A119.3C10B—C11B—H11B119.5
C11A—C12A—C7A121.10 (15)C11B—C12B—C7B121.66 (15)
C11A—C12A—H12A119.4C11B—C12B—H12B119.2
C7A—C12A—H12A119.4C7B—C12B—H12B119.2
C18A—C13A—C14A117.17 (15)C18B—C13B—C14B117.31 (15)
C18A—C13A—B2A122.09 (15)C18B—C13B—B2B120.32 (15)
C14A—C13A—B2A120.48 (15)C14B—C13B—B2B122.36 (15)
C15A—C14A—C13A121.55 (16)C15B—C14B—C13B120.90 (16)
C15A—C14A—H14A119.2C15B—C14B—H14B119.6
C13A—C14A—H14A119.2C13B—C14B—H14B119.6
C14A—C15A—C16A121.40 (16)C14B—C15B—C16B121.53 (16)
C14A—C15A—H15A119.3C14B—C15B—H15B119.2
C16A—C15A—H15A119.3C16B—C15B—H15B119.2
C15A—C16A—C17A117.44 (15)C17B—C16B—C15B117.62 (16)
C15A—C16A—C19A119.64 (15)C17B—C16B—C19B122.60 (15)
C17A—C16A—C19A122.91 (15)C15B—C16B—C19B119.78 (15)
C18A—C17A—C16A120.74 (15)C18B—C17B—C16B120.88 (16)
C18A—C17A—H17A119.6C18B—C17B—H17B119.6
C16A—C17A—H17A119.6C16B—C17B—H17B119.6
C17A—C18A—C13A121.67 (16)C17B—C18B—C13B121.76 (16)
C17A—C18A—H18A119.2C17B—C18B—H18B119.1
C13A—C18A—H18A119.2C13B—C18B—H18B119.1
C22A—C19A—C16A111.50 (14)C22B—C19B—C21B108.83 (15)
C22A—C19A—C21A108.60 (14)C22B—C19B—C16B112.05 (15)
C16A—C19A—C21A109.16 (14)C21B—C19B—C16B109.33 (15)
C22A—C19A—C20A108.73 (14)C22B—C19B—C20B108.07 (15)
C16A—C19A—C20A109.43 (13)C21B—C19B—C20B109.92 (16)
C21A—C19A—C20A109.38 (15)C16B—C19B—C20B108.62 (14)
C19A—C20A—H20A109.5C19B—C20B—H20D109.5
C19A—C20A—H20B109.5C19B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
C19A—C20A—H20C109.5C19B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
C19A—C21A—H21A109.5C19B—C21B—H21D109.5
C19A—C21A—H21B109.5C19B—C21B—H21E109.5
H21A—C21A—H21B109.5H21D—C21B—H21E109.5
C19A—C21A—H21C109.5C19B—C21B—H21F109.5
H21A—C21A—H21C109.5H21D—C21B—H21F109.5
H21B—C21A—H21C109.5H21E—C21B—H21F109.5
C19A—C22A—H22A109.5C19B—C22B—H22D109.5
C19A—C22A—H22B109.5C19B—C22B—H22E109.5
H22A—C22A—H22B109.5H22D—C22B—H22E109.5
C19A—C22A—H22C109.5C19B—C22B—H22F109.5
H22A—C22A—H22C109.5H22D—C22B—H22F109.5
H22B—C22A—H22C109.5H22E—C22B—H22F109.5
C26A—C23A—C10A112.52 (13)C26B—C23B—C10B112.44 (14)
C26A—C23A—C24A107.95 (15)C26B—C23B—C24B108.49 (15)
C10A—C23A—C24A110.19 (14)C10B—C23B—C24B108.16 (14)
C26A—C23A—C25A108.55 (15)C26B—C23B—C25B108.54 (15)
C10A—C23A—C25A108.81 (14)C10B—C23B—C25B110.41 (13)
C24A—C23A—C25A108.75 (14)C24B—C23B—C25B108.72 (14)
C23A—C24A—H24A109.5C23B—C24B—H24D109.5
C23A—C24A—H24B109.5C23B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
C23A—C24A—H24C109.5C23B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
C23A—C25A—H25A109.5C23B—C25B—H25D109.5
C23A—C25A—H25B109.5C23B—C25B—H25E109.5
H25A—C25A—H25B109.5H25D—C25B—H25E109.5
C23A—C25A—H25C109.5C23B—C25B—H25F109.5
H25A—C25A—H25C109.5H25D—C25B—H25F109.5
H25B—C25A—H25C109.5H25E—C25B—H25F109.5
C23A—C26A—H26A109.5C23B—C26B—H26D109.5
C23A—C26A—H26B109.5C23B—C26B—H26E109.5
H26A—C26A—H26B109.5H26D—C26B—H26E109.5
C23A—C26A—H26C109.5C23B—C26B—H26F109.5
H26A—C26A—H26C109.5H26D—C26B—H26F109.5
H26B—C26A—H26C109.5H26E—C26B—H26F109.5
C4A—O1A—C1A106.52 (12)C4B—O1B—C1B106.21 (13)
B1A—O2A—C5A120.33 (13)B1B—O2B—C5B120.82 (13)
B1A—O3A—C2A121.39 (13)B1B—O3B—C2B121.14 (13)
B2A—O4A—C4A108.30 (13)B2B—O4B—C4B108.85 (13)
B2A—O5A—C3A108.27 (13)B2B—O5B—C3B107.75 (13)
C6A—O6A—H6A109.5C6B—O6B—H6B109.5
O1A—C1A—C2A—O3A74.30 (15)O1B—C1B—C2B—O3B75.41 (16)
C5A—C1A—C2A—O3A−45.18 (18)C5B—C1B—C2B—O3B−44.13 (19)
O1A—C1A—C2A—C3A−41.03 (15)O1B—C1B—C2B—C3B−38.70 (15)
C5A—C1A—C2A—C3A−160.51 (13)C5B—C1B—C2B—C3B−158.24 (14)
O3A—C2A—C3A—O5A157.08 (13)O3B—C2B—C3B—O5B150.91 (12)
C1A—C2A—C3A—O5A−86.13 (16)C1B—C2B—C3B—O5B−91.89 (15)
O3A—C2A—C3A—C4A−91.21 (15)O3B—C2B—C3B—C4B−96.18 (14)
C1A—C2A—C3A—C4A25.58 (16)C1B—C2B—C3B—C4B21.02 (16)
O5A—C3A—C4A—O1A113.46 (13)O5B—C3B—C4B—O1B120.61 (14)
C2A—C3A—C4A—O1A−1.40 (17)C2B—C3B—C4B—O1B3.86 (17)
O5A—C3A—C4A—O4A−3.28 (16)O5B—C3B—C4B—O4B3.17 (16)
C2A—C3A—C4A—O4A−118.13 (13)C2B—C3B—C4B—O4B−113.58 (13)
O1A—C1A—C5A—O2A−67.31 (16)O1B—C1B—C5B—O2B−71.57 (18)
C2A—C1A—C5A—O2A47.83 (19)C2B—C1B—C5B—O2B43.9 (2)
O1A—C1A—C5A—C6A172.15 (13)O1B—C1B—C5B—C6B167.87 (13)
C2A—C1A—C5A—C6A−72.71 (17)C2B—C1B—C5B—C6B−76.71 (18)
O2A—C5A—C6A—O6A172.42 (12)O2B—C5B—C6B—O6B175.05 (12)
C1A—C5A—C6A—O6A−65.18 (17)C1B—C5B—C6B—O6B−61.65 (18)
O2A—B1A—C7A—C12A−169.26 (16)O3B—B1B—C7B—C12B8.0 (3)
O3A—B1A—C7A—C12A11.4 (2)O2B—B1B—C7B—C12B−171.35 (18)
O2A—B1A—C7A—C8A11.1 (2)O3B—B1B—C7B—C8B−172.72 (17)
O3A—B1A—C7A—C8A−168.20 (16)O2B—B1B—C7B—C8B8.0 (3)
C12A—C7A—C8A—C9A1.0 (3)C12B—C7B—C8B—C9B−0.4 (3)
B1A—C7A—C8A—C9A−179.39 (15)B1B—C7B—C8B—C9B−179.74 (18)
C7A—C8A—C9A—C10A0.0 (3)C7B—C8B—C9B—C10B2.0 (3)
C8A—C9A—C10A—C11A−0.8 (3)C8B—C9B—C10B—C11B−2.3 (3)
C8A—C9A—C10A—C23A178.05 (16)C8B—C9B—C10B—C23B179.83 (17)
C9A—C10A—C11A—C12A0.5 (3)C9B—C10B—C11B—C12B1.1 (3)
C23A—C10A—C11A—C12A−178.26 (16)C23B—C10B—C11B—C12B178.85 (17)
C10A—C11A—C12A—C7A0.5 (3)C10B—C11B—C12B—C7B0.5 (3)
C8A—C7A—C12A—C11A−1.2 (3)C8B—C7B—C12B—C11B−0.9 (3)
B1A—C7A—C12A—C11A179.16 (15)B1B—C7B—C12B—C11B178.49 (18)
O5A—B2A—C13A—C18A170.46 (16)O5B—B2B—C13B—C18B177.87 (16)
O4A—B2A—C13A—C18A−4.8 (2)O4B—B2B—C13B—C18B−5.5 (2)
O5A—B2A—C13A—C14A−3.5 (2)O5B—B2B—C13B—C14B−2.8 (3)
O4A—B2A—C13A—C14A−178.82 (16)O4B—B2B—C13B—C14B173.86 (16)
C18A—C13A—C14A—C15A−1.3 (2)C18B—C13B—C14B—C15B−0.1 (3)
B2A—C13A—C14A—C15A172.97 (14)B2B—C13B—C14B—C15B−179.50 (16)
C13A—C14A—C15A—C16A−0.3 (3)C13B—C14B—C15B—C16B−0.1 (3)
C14A—C15A—C16A—C17A1.7 (2)C14B—C15B—C16B—C17B0.4 (3)
C14A—C15A—C16A—C19A−177.24 (15)C14B—C15B—C16B—C19B179.98 (16)
C15A—C16A—C17A—C18A−1.4 (2)C15B—C16B—C17B—C18B−0.5 (2)
C19A—C16A—C17A—C18A177.48 (15)C19B—C16B—C17B—C18B179.93 (16)
C16A—C17A—C18A—C13A−0.2 (2)C16B—C17B—C18B—C13B0.3 (3)
C14A—C13A—C18A—C17A1.6 (2)C14B—C13B—C18B—C17B0.0 (2)
B2A—C13A—C18A—C17A−172.60 (15)B2B—C13B—C18B—C17B179.41 (16)
C15A—C16A—C19A—C22A176.87 (15)C17B—C16B—C19B—C22B−2.6 (2)
C17A—C16A—C19A—C22A−2.0 (2)C15B—C16B—C19B—C22B177.82 (16)
C15A—C16A—C19A—C21A56.9 (2)C17B—C16B—C19B—C21B−123.37 (18)
C17A—C16A—C19A—C21A−121.98 (17)C15B—C16B—C19B—C21B57.1 (2)
C15A—C16A—C19A—C20A−62.8 (2)C17B—C16B—C19B—C20B116.68 (19)
C17A—C16A—C19A—C20A118.34 (18)C15B—C16B—C19B—C20B−62.9 (2)
C11A—C10A—C23A—C26A−5.6 (2)C9B—C10B—C23B—C26B−168.22 (16)
C9A—C10A—C23A—C26A175.65 (16)C11B—C10B—C23B—C26B14.1 (2)
C11A—C10A—C23A—C24A−126.13 (18)C9B—C10B—C23B—C24B72.0 (2)
C9A—C10A—C23A—C24A55.1 (2)C11B—C10B—C23B—C24B−105.69 (19)
C11A—C10A—C23A—C25A114.73 (18)C9B—C10B—C23B—C25B−46.8 (2)
C9A—C10A—C23A—C25A−64.0 (2)C11B—C10B—C23B—C25B135.47 (18)
O4A—C4A—O1A—C1A87.99 (15)O4B—C4B—O1B—C1B83.90 (15)
C3A—C4A—O1A—C1A−25.19 (16)C3B—C4B—O1B—C1B−29.15 (16)
C5A—C1A—O1A—C4A164.40 (13)C5B—C1B—O1B—C4B165.60 (12)
C2A—C1A—O1A—C4A41.93 (15)C2B—C1B—O1B—C4B42.82 (15)
O3A—B1A—O2A—C5A2.6 (2)O3B—B1B—O2B—C5B−1.5 (3)
C7A—B1A—O2A—C5A−176.74 (14)C7B—B1B—O2B—C5B177.80 (15)
C1A—C5A—O2A—B1A−26.3 (2)C1B—C5B—O2B—B1B−21.1 (2)
C6A—C5A—O2A—B1A97.08 (16)C6B—C5B—O2B—B1B102.53 (18)
O2A—B1A—O3A—C2A0.2 (2)O2B—B1B—O3B—C2B0.9 (3)
C7A—B1A—O3A—C2A179.45 (14)C7B—B1B—O3B—C2B−178.35 (15)
C1A—C2A—O3A—B1A21.1 (2)C3B—C2B—O3B—B1B133.04 (16)
C3A—C2A—O3A—B1A131.94 (16)C1B—C2B—O3B—B1B21.7 (2)
O5A—B2A—O4A—C4A−6.34 (18)O5B—B2B—O4B—C4B−0.18 (19)
C13A—B2A—O4A—C4A169.33 (15)C13B—B2B—O4B—C4B−177.13 (15)
O1A—C4A—O4A—B2A−109.01 (15)O1B—C4B—O4B—B2B−116.70 (15)
C3A—C4A—O4A—B2A5.65 (16)C3B—C4B—O4B—B2B−1.87 (16)
O4A—B2A—O5A—C3A4.07 (18)O4B—B2B—O5B—C3B2.35 (19)
C13A—B2A—O5A—C3A−171.72 (14)C13B—B2B—O5B—C3B179.26 (15)
C2A—C3A—O5A—B2A110.44 (15)C2B—C3B—O5B—B2B108.06 (15)
C4A—C3A—O5A—B2A−0.26 (17)C4B—C3B—O5B—B2B−3.34 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6A—H6A···O6B0.842.072.8660 (17)158
O6B—H6B···O1Ai0.842.473.1131 (17)134
C1B—H1B···O6A1.002.373.318 (2)159
C2B—H2B···O4Bii1.002.413.379 (2)162
C4A—H4A···O5Biii1.002.443.246 (2)137
C4B—H4B···O6Aiv1.002.513.231 (2)129
C3A—H3A···O1Bi1.002.553.480 (2)155
C6A—H6A1···O4Ai0.992.603.499 (2)150
C1A—H1A···O6B1.002.623.553 (2)155
C2A—H2A···O4Ai1.002.643.587 (2)159
C14A—H14A···O2Ai0.952.663.433 (2)139
C3A—H3A···O4Bi1.002.683.442 (2)133
C3B—H3B···O4Av1.002.723.522 (2)137
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x−1, y+1/2, −z+1; (iii) x+1, y, z; (iv) −x−1, y−1/2, −z+1; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC26H34B2O6
Mr464.15
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)11.2372 (3), 10.1910 (3), 22.5084 (7)
β (°) 104.103 (3)
V (Å3)2499.93 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.60 × 0.30 × 0.22
Data collection
DiffractometerKuma KM-4-CCD
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction 2005)
Tmin, Tmax0.95, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections		47322, 6519, 5409
Rint0.025
(sin θ/λ)max (Å−1)0.674
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.072, 0.99
No. of reflections6519
No. of parameters627
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.24, −0.19

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Selected geometric parameters (Å, º) top
B1A—O2A1.366 (2)B1B—O3B1.365 (2)
B1A—O3A1.368 (2)B1B—O2B1.367 (2)
B1A—C7A1.569 (2)B1B—C7B1.559 (2)
B2A—O5A1.369 (2)B2B—O5B1.375 (2)
B2A—O4A1.376 (2)B2B—O4B1.376 (2)
B2A—C13A1.550 (2)B2B—C13B1.546 (2)
O2A—B1A—O3A123.84 (15)O3B—B1B—O2B123.81 (16)
O2A—B1A—C7A117.46 (15)O3B—B1B—C7B117.83 (15)
O3A—B1A—C7A118.70 (15)O2B—B1B—C7B118.36 (15)
O5A—B2A—O4A113.24 (14)O5B—B2B—O4B113.35 (15)
O5A—B2A—C13A122.11 (16)O5B—B2B—C13B123.78 (16)
O4A—B2A—C13A124.50 (16)O4B—B2B—C13B122.80 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6A—H6A···O6B0.842.072.8660 (17)158.2
O6B—H6B···O1Ai0.842.473.1131 (17)134.4
C1B—H1B···O6A1.002.373.3180 (21)158.6
C2B—H2B···O4Bii1.002.413.3794 (20)162.0
C4A—H4A···O5Biii1.002.443.2460 (21)136.9
C4B—H4B···O6Aiv1.002.513.2313 (21)128.6
C3A—H3A···O1Bi1.002.553.4799 (22)154.7
C6A—H6A1···O4Ai0.992.603.4994 (21)150.3
C1A—H1A···O6B1.002.623.5533 (21)155.1
C2A—H2A···O4Ai1.002.643.5867 (21)158.7
C14A—H14A···O2Ai0.952.663.4326 (22)139.0
C3A—H3A···O4Bi1.002.683.4424 (20)133.1
C3B—H3B···O4Av1.002.723.5216 (21)137.3
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x−1, y+1/2, −z+1; (iii) x+1, y, z; (iv) −x−1, y−1/2, −z+1; (v) x−1, y, z.
 

Acknowledgements

The X-ray measurements were undertaken in the Crystallographic Unit of the Physical Chemistry Laboratory at the Chemistry Department of the University of Warsaw. This work was supported by the Aldrich Chemical Co. through donation of chemicals and equipment and by the Warsaw University of Technology.

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationChandran, S. K. & Nangia, A. (2006). CrystEngComm, 8, 581–585.  Web of Science CSD CrossRef CAS Google Scholar
 First citationDraffin, S. P., Duggan, P. J. & Fallon, G. D. (2004). Acta Cryst. E60, o1520–o1522.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationHall, D. G. (2005). Boronic Acids. Weinheim: Wiley–VCH.  Google Scholar
 First citationOxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3166
https://doi.org/10.1107/S1600536810046222
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