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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o897.
Published online 2008 April 23. doi:  10.1107/S1600536808008222
PMCID: PMC2961327

Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor

Abstract

The title compound, C13H24O7, is the product of the ketalization of methyl l-(+)-rhamnopyran­oside with 2,3-butane­dione. It crystallizes with two mol­ecules in the asymmetric unit, which are connected by O—H(...)O hydrogen bonds. The C-3,4 diequatorial hydroxy groups of the methyl l-(+)-rhamnopyran­oside were protected, leaving the C-2 hydroxy group free. The l-(+)-rhamnopyran­oside and 2′,3′-dimethoxy­butane-2′,3′-diyl rings adopt chair conformations and all meth­oxy groups are in axial positions. The absolute configuration was assumed from the synthesis.

Related literature

For related literature, see: Duynstee et al. (1998 [triangle]); Lang & Wullbrandt (1999 [triangle]); Leisinger & Margraff (1979 [triangle]); Montchamp et al. (1996 [triangle]); Bauer et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o897-scheme1.jpg

Experimental

Crystal data

  • C13H24O7
  • M r = 292.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o897-efi1.jpg
  • a = 12.8743 (14) Å
  • b = 13.1182 (12) Å
  • c = 18.208 (3) Å
  • V = 3075.0 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 295 (2) K
  • 0.6 × 0.5 × 0.4 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.933, T max = 0.994
  • 3842 measured reflections
  • 3032 independent reflections
  • 2630 reflections with I > 2s(I)
  • R int = 0.020
  • 3 standard reflections every 97 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.106
  • S = 1.01
  • 3032 reflections
  • 362 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: XSCANS (Siemens, 1995 [triangle]); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808008222/bt2683sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008222/bt2683Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We gratefully acknowledge financial support in part from the National Science Council, Taiwan (NSC 96-2113-M-033-003) and in part from the Project of the Specific Research Fields of Chung Yuan Christian University, Taiwan (CYCU-95-CR-CH).

supplementary crystallographic information

Comment

L-Rhamnopyranse-containing glycolipids display a wide range of biological properties (Leisinger, & Margraff, 1979; Lang & Wullbrandt, 1999; Bauer et al., 2006). For the above reason, we were interesting to study on the total synthesis of rhamnolipids. The title compound, C13H24O7, which was synthesized by the ketalization of C-3,4 hydroxyl group of the methyl L-(+)-rhamnopyranoside, with 2,3-butanedione and chemoselectively protected the C-3,4 diequatorial hydroxyl group (Montchamp et al., 1996; Duynstee et al., 1998), was utilized as glycosyl acceptor in our synthetic strategy. The methyl L-(+)-rhamnopyranoside was prepared by acetalization of the commercial optical pure L-(+)-rhamnopyranose as starting material with methanol. The structure of L-rhamnopyranoside ring and 2',3'-dimethoxybutan-2',3'-diyl ring are chair conformation and all of methoxy groups are at axial position.

Experimental

A solution of methyl L-(+)-rhamnopyranose ([a]20D = + 8.2°) (638 mg, 3.58 mmol), trimeyhyl orthoformate (1.20 ml, 10.75 mmol) and 2,3-butanedione (0.35 ml, 3.98 mmol) in dried methanol (15 ml) was treated with camphersulfonic acid (50 mg, 0.22 mmol). The mixture was refluxed for 18 h. The cool reaction mixture was then treated with NEt3 and concentrated under reduced pressure to observe crude product. The crude product was purified via flash column chromatography on silica gel (EtOAc/n-hexane = 1:1) to obtain 874 mg (84%) of the title compound as white powder. The pure product was recrystalized from CH2Cl2 at room temperature.

Refinement

In the absence of anomalous scatterers Friedel pairs were merged prior to refinement. The C-bound H atoms were placed in calculated positions (C—H = 0.96–0.98 Å) and included in the refinement in the riding-model approximation, with Uiso(H) = 1.2 or 1.5Ueq(C). The hydroxy H atoms were constrained to ideal geometries with O(N)—H = 0.82 Å and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom numbering scheme. Displacement ellipsoids for non-H atoms are represented at the 30% probability level. The H atoms are drawn with an arbitrary radius.

Crystal data

C13H24O7F000 = 1264
Mr = 292.32Dx = 1.263 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 27 reflections
a = 12.8743 (14) Åθ = 5.1–12.5º
b = 13.1182 (12) ŵ = 0.10 mm1
c = 18.208 (3) ÅT = 295 (2) K
V = 3075.0 (7) Å3Block, colourless
Z = 80.6 × 0.5 × 0.4 mm

Data collection

Bruker P4 diffractometerRint = 0.020
Radiation source: fine-focus sealed tubeθmax = 25.0º
Monochromator: graphiteθmin = 1.9º
T = 295(2) Kh = −1→15
ω scansk = −1→15
Absorption correction: ψ scan(North et al., 1968)l = −1→21
Tmin = 0.933, Tmax = 0.9943 standard reflections
3842 measured reflections every 97 reflections
3032 independent reflections intensity decay: none
2630 reflections with I > 2s(I)

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038  w = 1/[σ2(Fo2) + (0.0561P)2 + 0.7995P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.15 e Å3
3032 reflectionsΔρmin = −0.17 e Å3
362 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0063 (6)
Secondary atom site location: difference Fourier map

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.

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

xyzUiso*/Ueq
O10.29481 (18)0.87985 (15)0.88054 (10)0.0505 (5)
O20.1553 (2)0.8215 (2)0.95033 (13)0.0673 (7)
O30.35887 (18)0.66974 (18)0.87880 (14)0.0614 (6)
O40.20071 (17)0.70426 (15)0.82239 (11)0.0469 (5)
O50.38039 (16)0.96048 (16)0.74810 (11)0.0502 (5)
H5A0.41380.94810.78540.075*
O60.11031 (18)0.99268 (18)0.71133 (13)0.0626 (6)
O70.21798 (18)0.86713 (17)0.66048 (11)0.0529 (5)
O80.38389 (15)0.21315 (15)0.83116 (10)0.0426 (4)
O90.38270 (19)0.33878 (17)0.92121 (12)0.0564 (6)
O100.17861 (17)0.16879 (17)0.87757 (12)0.0548 (5)
O110.20194 (17)0.33159 (15)0.82917 (10)0.0470 (5)
O120.37676 (17)0.15454 (15)0.67829 (11)0.0481 (5)
H12A0.38810.11100.70960.072*
O130.43863 (16)0.41769 (15)0.66158 (12)0.0515 (5)
O140.27898 (16)0.34098 (16)0.63634 (10)0.0451 (5)
C10.2596 (3)0.8024 (3)0.92943 (17)0.0570 (9)
C20.3345 (4)0.8045 (3)0.99348 (19)0.0829 (13)
H2A0.33520.87141.01480.124*
H2B0.40300.78750.97660.124*
H2C0.31290.75581.02980.124*
C30.1350 (4)0.9160 (3)0.9869 (2)0.0932 (15)
H3A0.06220.92100.99770.140*
H3B0.15510.97160.95570.140*
H3C0.17400.91881.03170.140*
C40.2534 (3)0.6969 (2)0.89081 (17)0.0507 (8)
C50.3743 (3)0.5765 (3)0.8392 (3)0.0899 (15)
H5B0.44730.56410.83350.135*
H5C0.34250.58170.79160.135*
H5D0.34330.52110.86590.135*
C60.1952 (3)0.6187 (3)0.9353 (2)0.0671 (10)
H6A0.19330.55530.90890.101*
H6B0.12560.64200.94380.101*
H6C0.22970.60880.98150.101*
C70.2429 (2)0.7820 (2)0.77618 (15)0.0426 (7)
H7A0.31600.76700.76590.051*
C80.2344 (2)0.8829 (2)0.81437 (15)0.0436 (7)
H8A0.16150.89520.82710.052*
C90.2721 (2)0.9686 (2)0.76624 (16)0.0438 (7)
H9A0.25891.03400.79040.053*
C100.2127 (3)0.9639 (2)0.69401 (17)0.0497 (7)
H10A0.24201.01450.66030.060*
C110.0474 (3)1.0130 (4)0.6492 (3)0.1003 (16)
H11A−0.02091.03250.66510.150*
H11B0.04280.95290.61930.150*
H11C0.07761.06740.62110.150*
C120.1820 (3)0.7835 (2)0.70469 (16)0.0477 (7)
H12B0.10800.79240.71540.057*
C130.1975 (3)0.6876 (3)0.6604 (2)0.0698 (10)
H13A0.15750.69170.61600.105*
H13B0.17510.62980.68860.105*
H13C0.26970.68020.64840.105*
C140.3400 (3)0.2447 (2)0.89914 (15)0.0445 (7)
C150.3620 (3)0.1598 (3)0.95361 (17)0.0591 (9)
H15A0.43560.14970.95750.089*
H15B0.32970.09800.93700.089*
H15C0.33450.17801.00080.089*
C160.4938 (3)0.3455 (3)0.9215 (2)0.0743 (11)
H16A0.51440.41220.93750.111*
H16B0.51970.33350.87280.111*
H16C0.52160.29520.95440.111*
C170.2219 (3)0.2663 (2)0.89001 (16)0.0471 (7)
C180.0701 (3)0.1652 (3)0.8604 (2)0.0737 (11)
H18A0.04930.09560.85320.111*
H18B0.05740.20320.81620.111*
H18C0.03100.19430.90000.111*
C190.1755 (3)0.3204 (3)0.95614 (18)0.0642 (10)
H19A0.10280.33190.94790.096*
H19B0.20990.38450.96320.096*
H19C0.18440.27880.99910.096*
C200.2480 (2)0.2952 (2)0.76220 (15)0.0400 (6)
H20A0.21810.22900.74890.048*
C210.3632 (2)0.2850 (2)0.77310 (14)0.0388 (6)
H21A0.39170.35150.78690.047*
C220.4147 (2)0.2498 (2)0.70284 (15)0.0400 (6)
H22A0.49020.24670.70940.048*
C230.3874 (2)0.3265 (2)0.64348 (15)0.0425 (6)
H23A0.41470.30170.59650.051*
C240.4307 (3)0.4943 (3)0.6062 (2)0.0701 (10)
H24A0.46650.55460.62220.105*
H24B0.35890.51010.59780.105*
H24C0.46150.46990.56160.105*
C250.2258 (2)0.3727 (2)0.70230 (15)0.0430 (7)
H25A0.25110.43990.71750.052*
C260.1112 (3)0.3797 (3)0.6822 (2)0.0652 (10)
H26A0.10190.43040.64470.098*
H26B0.07180.39840.72490.098*
H26C0.08770.31490.66430.098*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0683 (14)0.0485 (11)0.0347 (10)−0.0162 (11)−0.0075 (10)0.0047 (9)
O20.0860 (18)0.0663 (15)0.0495 (12)−0.0112 (14)0.0156 (12)−0.0026 (12)
O30.0551 (14)0.0524 (12)0.0768 (15)−0.0051 (11)−0.0090 (12)0.0158 (12)
O40.0527 (12)0.0444 (10)0.0436 (10)−0.0123 (10)−0.0050 (10)0.0060 (9)
O50.0487 (12)0.0539 (12)0.0480 (11)−0.0057 (10)−0.0044 (10)0.0100 (10)
O60.0520 (13)0.0695 (15)0.0662 (14)0.0071 (12)−0.0070 (12)0.0189 (12)
O70.0619 (13)0.0616 (13)0.0353 (10)−0.0092 (11)−0.0043 (10)0.0041 (10)
O80.0487 (11)0.0449 (10)0.0341 (9)0.0091 (9)−0.0015 (9)0.0017 (9)
O90.0694 (15)0.0526 (12)0.0473 (11)0.0022 (12)−0.0088 (11)−0.0066 (11)
O100.0536 (12)0.0520 (12)0.0587 (13)0.0000 (11)0.0034 (11)0.0075 (11)
O110.0538 (12)0.0503 (11)0.0368 (9)0.0139 (10)0.0053 (9)0.0036 (9)
O120.0582 (12)0.0424 (10)0.0436 (10)−0.0060 (10)0.0036 (10)−0.0028 (9)
O130.0543 (12)0.0473 (11)0.0530 (12)−0.0147 (10)−0.0035 (11)0.0055 (10)
O140.0481 (12)0.0549 (12)0.0323 (9)−0.0046 (10)−0.0023 (8)0.0026 (9)
C10.071 (2)0.062 (2)0.0384 (15)−0.0189 (18)−0.0021 (16)0.0082 (14)
C20.119 (3)0.086 (3)0.0434 (18)−0.035 (3)−0.025 (2)0.0195 (19)
C30.131 (4)0.087 (3)0.062 (2)−0.003 (3)0.024 (3)−0.012 (2)
C40.0558 (19)0.0491 (17)0.0472 (16)−0.0094 (15)−0.0059 (15)0.0139 (14)
C50.069 (2)0.0473 (19)0.154 (5)0.0036 (19)0.001 (3)0.009 (3)
C60.077 (2)0.063 (2)0.062 (2)−0.025 (2)−0.009 (2)0.0213 (17)
C70.0476 (16)0.0417 (14)0.0384 (14)−0.0063 (13)−0.0001 (13)0.0035 (13)
C80.0511 (17)0.0457 (15)0.0342 (14)−0.0060 (13)−0.0045 (13)0.0027 (13)
C90.0492 (16)0.0419 (15)0.0401 (15)−0.0013 (13)−0.0001 (13)0.0040 (12)
C100.0528 (18)0.0503 (17)0.0460 (16)−0.0033 (15)−0.0022 (15)0.0133 (14)
C110.066 (3)0.142 (4)0.093 (3)0.003 (3)−0.024 (2)0.051 (3)
C120.0505 (17)0.0518 (16)0.0409 (15)−0.0078 (15)−0.0031 (14)0.0011 (14)
C130.085 (3)0.069 (2)0.056 (2)−0.006 (2)−0.010 (2)−0.0167 (18)
C140.0571 (18)0.0438 (15)0.0327 (14)0.0051 (14)−0.0022 (13)−0.0014 (12)
C150.077 (2)0.0559 (18)0.0441 (16)0.0182 (18)−0.0011 (16)0.0077 (15)
C160.074 (2)0.075 (2)0.074 (2)−0.008 (2)−0.031 (2)0.000 (2)
C170.0574 (18)0.0465 (16)0.0373 (14)0.0096 (14)0.0063 (14)0.0057 (13)
C180.054 (2)0.087 (3)0.080 (2)−0.007 (2)0.0077 (18)0.008 (2)
C190.080 (2)0.066 (2)0.0462 (17)0.018 (2)0.0168 (17)0.0049 (17)
C200.0414 (15)0.0434 (15)0.0353 (14)0.0022 (13)0.0044 (12)−0.0009 (12)
C210.0415 (15)0.0402 (14)0.0347 (13)0.0003 (12)−0.0029 (12)0.0028 (12)
C220.0377 (14)0.0422 (15)0.0400 (14)−0.0043 (12)−0.0001 (12)−0.0015 (12)
C230.0424 (15)0.0470 (15)0.0381 (14)−0.0050 (14)0.0016 (12)−0.0020 (13)
C240.092 (3)0.057 (2)0.062 (2)−0.020 (2)0.002 (2)0.0159 (17)
C250.0452 (16)0.0478 (16)0.0361 (14)0.0033 (13)−0.0030 (13)0.0012 (12)
C260.0502 (19)0.089 (3)0.057 (2)0.0166 (19)−0.0059 (16)0.0103 (19)

Geometric parameters (Å, °)

O1—C11.425 (4)C7—H7A0.9800
O1—C81.434 (3)C8—C91.505 (4)
O2—C11.419 (4)C8—H8A0.9800
O2—C31.430 (5)C9—C101.523 (4)
O3—C41.421 (4)C9—H9A0.9800
O3—C51.434 (5)C10—H10A0.9800
O4—C41.422 (4)C11—H11A0.9600
O4—C71.429 (3)C11—H11B0.9600
O5—C91.437 (4)C11—H11C0.9600
O5—H5A0.8200C12—C131.508 (5)
O6—C101.407 (4)C12—H12B0.9800
O6—C111.417 (5)C13—H13A0.9600
O7—C101.410 (4)C13—H13B0.9600
O7—C121.437 (4)C13—H13C0.9600
O8—C141.423 (3)C14—C151.519 (4)
O8—C211.441 (3)C14—C171.555 (4)
O9—C141.409 (4)C15—H15A0.9600
O9—C161.433 (4)C15—H15B0.9600
O10—C171.414 (4)C15—H15C0.9600
O10—C181.432 (4)C16—H16A0.9600
O11—C171.424 (3)C16—H16B0.9600
O11—C201.438 (3)C16—H16C0.9600
O12—C221.414 (3)C17—C191.520 (4)
O12—H12A0.8200C18—H18A0.9600
O13—C231.406 (3)C18—H18B0.9600
O13—C241.427 (4)C18—H18C0.9600
O14—C231.415 (4)C19—H19A0.9600
O14—C251.444 (3)C19—H19B0.9600
C1—C21.513 (5)C19—H19C0.9600
C1—C41.555 (5)C20—C211.501 (4)
C2—H2A0.9600C20—C251.519 (4)
C2—H2B0.9600C20—H20A0.9800
C2—H2C0.9600C21—C221.514 (4)
C3—H3A0.9600C21—H21A0.9800
C3—H3B0.9600C22—C231.518 (4)
C3—H3C0.9600C22—H22A0.9800
C4—C61.507 (4)C23—H23A0.9800
C5—H5B0.9600C24—H24A0.9600
C5—H5C0.9600C24—H24B0.9600
C5—H5D0.9600C24—H24C0.9600
C6—H6A0.9600C25—C261.522 (4)
C6—H6B0.9600C25—H25A0.9800
C6—H6C0.9600C26—H26A0.9600
C7—C81.500 (4)C26—H26B0.9600
C7—C121.519 (4)C26—H26C0.9600
C1—O1—C8111.9 (2)C7—C12—H12B109.5
C1—O2—C3116.8 (3)C12—C13—H13A109.5
C4—O3—C5115.0 (3)C12—C13—H13B109.5
C4—O4—C7112.5 (2)H13A—C13—H13B109.5
C9—O5—H5A109.5C12—C13—H13C109.5
C10—O6—C11114.0 (3)H13A—C13—H13C109.5
C10—O7—C12115.4 (2)H13B—C13—H13C109.5
C14—O8—C21112.0 (2)O9—C14—O8110.4 (2)
C14—O9—C16116.4 (3)O9—C14—C15112.5 (2)
C17—O10—C18116.7 (3)O8—C14—C15106.3 (2)
C17—O11—C20112.7 (2)O9—C14—C17104.6 (2)
C22—O12—H12A109.5O8—C14—C17110.4 (2)
C23—O13—C24113.6 (2)C15—C14—C17112.7 (3)
C23—O14—C25115.5 (2)C14—C15—H15A109.5
O2—C1—O1110.0 (3)C14—C15—H15B109.5
O2—C1—C2113.2 (3)H15A—C15—H15B109.5
O1—C1—C2105.4 (3)C14—C15—H15C109.5
O2—C1—C4103.3 (3)H15A—C15—H15C109.5
O1—C1—C4111.7 (2)H15B—C15—H15C109.5
C2—C1—C4113.4 (3)O9—C16—H16A109.5
C1—C2—H2A109.5O9—C16—H16B109.5
C1—C2—H2B109.5H16A—C16—H16B109.5
H2A—C2—H2B109.5O9—C16—H16C109.5
C1—C2—H2C109.5H16A—C16—H16C109.5
H2A—C2—H2C109.5H16B—C16—H16C109.5
H2B—C2—H2C109.5O10—C17—O11110.4 (3)
O2—C3—H3A109.5O10—C17—C19113.2 (3)
O2—C3—H3B109.5O11—C17—C19105.4 (2)
H3A—C3—H3B109.5O10—C17—C14103.8 (2)
O2—C3—H3C109.5O11—C17—C14111.7 (2)
H3A—C3—H3C109.5C19—C17—C14112.6 (3)
H3B—C3—H3C109.5O10—C18—H18A109.5
O3—C4—O4109.8 (3)O10—C18—H18B109.5
O3—C4—C6112.8 (3)H18A—C18—H18B109.5
O4—C4—C6106.3 (3)O10—C18—H18C109.5
O3—C4—C1104.1 (3)H18A—C18—H18C109.5
O4—C4—C1111.1 (2)H18B—C18—H18C109.5
C6—C4—C1112.9 (3)C17—C19—H19A109.5
O3—C5—H5B109.5C17—C19—H19B109.5
O3—C5—H5C109.5H19A—C19—H19B109.5
H5B—C5—H5C109.5C17—C19—H19C109.5
O3—C5—H5D109.5H19A—C19—H19C109.5
H5B—C5—H5D109.5H19B—C19—H19C109.5
H5C—C5—H5D109.5O11—C20—C21109.0 (2)
C4—C6—H6A109.5O11—C20—C25108.0 (2)
C4—C6—H6B109.5C21—C20—C25109.9 (2)
H6A—C6—H6B109.5O11—C20—H20A110.0
C4—C6—H6C109.5C21—C20—H20A110.0
H6A—C6—H6C109.5C25—C20—H20A110.0
H6B—C6—H6C109.5O8—C21—C20109.8 (2)
O4—C7—C8109.2 (2)O8—C21—C22109.8 (2)
O4—C7—C12108.5 (2)C20—C21—C22110.4 (2)
C8—C7—C12110.4 (2)O8—C21—H21A108.9
O4—C7—H7A109.6C20—C21—H21A108.9
C8—C7—H7A109.6C22—C21—H21A108.9
C12—C7—H7A109.6O12—C22—C21112.7 (2)
O1—C8—C9109.6 (2)O12—C22—C23106.3 (2)
O1—C8—C7109.0 (2)C21—C22—C23107.3 (2)
C9—C8—C7111.5 (2)O12—C22—H22A110.2
O1—C8—H8A108.9C21—C22—H22A110.2
C9—C8—H8A108.9C23—C22—H22A110.2
C7—C8—H8A108.9O13—C23—O14111.7 (2)
O5—C9—C8113.0 (2)O13—C23—C22106.8 (2)
O5—C9—C10106.6 (2)O14—C23—C22112.5 (2)
C8—C9—C10108.1 (2)O13—C23—H23A108.6
O5—C9—H9A109.7O14—C23—H23A108.6
C8—C9—H9A109.7C22—C23—H23A108.6
C10—C9—H9A109.7O13—C24—H24A109.5
O7—C10—O6112.6 (3)O13—C24—H24B109.5
O7—C10—C9112.7 (2)H24A—C24—H24B109.5
O6—C10—C9105.4 (3)O13—C24—H24C109.5
O7—C10—H10A108.6H24A—C24—H24C109.5
O6—C10—H10A108.6H24B—C24—H24C109.5
C9—C10—H10A108.6O14—C25—C20108.3 (2)
O6—C11—H11A109.5O14—C25—C26106.1 (2)
O6—C11—H11B109.5C20—C25—C26113.3 (3)
H11A—C11—H11B109.5O14—C25—H25A109.7
O6—C11—H11C109.5C20—C25—H25A109.7
H11A—C11—H11C109.5C26—C25—H25A109.7
H11B—C11—H11C109.5C25—C26—H26A109.5
O7—C12—C13107.1 (3)C25—C26—H26B109.5
O7—C12—C7108.9 (2)H26A—C26—H26B109.5
C13—C12—C7112.3 (3)C25—C26—H26C109.5
O7—C12—H12B109.5H26A—C26—H26C109.5
C13—C12—H12B109.5H26B—C26—H26C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5A···O13i0.822.172.907 (3)150
O12—H12A···O5ii0.822.102.846 (3)152

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2683).

References

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