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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 69| Part 1| January 2013| Pages o54-o55
https://doi.org/10.1107/S1600536812049203

(Z)-Ethyl 2-hy­dr­oxy-4-oxo-4-(1,4,5,6,8-penta­meth­­oxy­naphthalen-2-yl)but-2-enoate

Adushan Pillay,a Sanaz Khorasania and Charles B. de Koninga*

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
*Correspondence e-mail: charles.dekoning@wits.ac.za

(Received 28 November 2012; accepted 30 November 2012; online 8 December 2012)

The title compound, C21H24O9, crystallizes with two independent mol­ecules in the asymmetric unit which are almost centrosymmetrically related to each other. The ethano­ate group in one of the two mol­ecules is disordered over two positions with a site-occupation factor of 0.880 (7) for the major occupied site. In the crystal, the 1,3-diketone group exists in the keto–enol isomeric form due to the stabilizing effect of the intra­molecular O—H⋯O hydrogen bond present in this form. The compound packs as a layered structure in which C—H⋯π and C—H⋯O inter­actions are present within and between the layers.

Related literature

For the synthesis of the title compound, see: de Koning et al. (1991[Koning, C. B. de, Giles, R. G. F. & Green, I. R. (1991). J. Chem. Soc. Perkin Trans. 1, pp. 2743-2748.]). This forms part of our research programme directed towards the synthesis of the natural phytotoxic naphtho­quinone, marticin, see: Pillay et al. (2012[Pillay, A., Rousseau, A. L., Fernandes, M. A. & de Koning, C. B. (2012). Tetrahedron, 68, 7116-7121.]).

[Scheme 1]

Experimental

Crystal data

  • C21H24O9

  • Mr = 420.40

  • Triclinic, [P \overline 1]

  • a = 6.8019 (4) Å

  • b = 12.3042 (6) Å

  • c = 24.3971 (12) Å

  • α = 100.002 (4)°

  • β = 93.080 (4)°

  • γ = 98.748 (4)°

  • V = 1980.67 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 173 K

  • 0.39 × 0.16 × 0.07 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • 19594 measured reflections

  • 7793 independent reflections

  • 3172 reflections with I > 2σ(I)

  • Rint = 0.083
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.118

  • S = 0.84

  • 7793 reflections

  • 572 parameters

  • 54 restraints

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1A/C2A/C7A–C10A, C2A–C7A and C2B–C7B rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O7A—H7A⋯O6A 0.84 1.77 2.499 (3) 144
O7B—H7B⋯O6B 0.84 1.77 2.497 (3) 143
C17B—H17D⋯O6Bi 0.98 2.43 3.234 (4) 139
C19A—H19B⋯O9Bii 0.98 2.45 3.419 (4) 168
C19B—H19E⋯O9Aiii 0.98 2.47 3.440 (5) 172
C20A—H20B⋯O4Biv 0.98 2.50 3.384 (4) 150
C20B—H20E⋯O4Av 0.98 2.57 3.382 (4) 140
C20B—H20F⋯O9Bi 0.98 2.58 3.460 (4) 150
C18A—H18A⋯Cg3vi 0.98 2.66 3.486 (3) 142
C18A—H18C⋯Cg1vi 0.98 2.92 3.844 (3) 158
C18B—H18F⋯Cg2vii 0.98 2.66 3.522 (3) 147
C21A—H21A⋯Cg2vii 0.98 2.96 3.845 (3) 150
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x, -y+2, -z; (iv) x, y-1, z; (v) x, y+1, z; (vi) x+1, y, z; (vii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT-NT (includes XPREP and SADABS). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-NT (Bruker, 2005[Bruker (2005). APEX2 and SAINT-NT (includes XPREP and SADABS). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-NT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and SCHAKAL99 (Keller, 1999[Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812049203/bt6876sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049203/bt6876Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812049203/bt6876Isup3.cml

checkCIF report


Comment top

As part of our research programme directed towards the synthesis of the natural phytotoxic naphthoquinone, marticin (Pillay et al., 2012), we synthesized the title compound in one step from 1-(1,4,5,6,8-pentamethoxynaphthalen-2-yl)ethanone (1) (de Koning et al., 1991). This was achieved as shown in Fig. 4 by treating (1) with diethyl oxalate with sodium ethoxide in THF to afford the title compound (2) as a bright red crystalline solid.

The title organic compound crystallizes in the space group P -1 with two independent molecules in the asymmetric unit which are labelled as A and B in Fig. 1. The molecules are almost centrosymmetrically related to each other, with the symmetry being broken by the ethanoate group of molecule A being disordered over two positions. The crystal structure shows that the 1,3-diketone moiety exists as the keto-enol isomeric form, with the enol-ether form being occupied due to the presence of intramolecular hydrogen bonding (Table 1). Strong intermolecular hydrogen bonding is present between pairs of B molecules in which H7B, which is involved in the intramolecular hydrogen bond with O6B, also interacts with O6B of another molecule related by a centre of inversion (Fig. 2.; Table 1). Molecule A is not involved in any strong intermolecular hydrogen bonding. Molecules in the structure pack as a layers (Fig. 3) with C—H···O and C—H···π interactions acting within and between the layers.

Related literature top

For the synthesis of the title compound, see: de Koning et al. (1991). This forms part of our research programme directed towards the synthesis of the natural phytotoxic naphthoquinone, marticin, see: Pillay et al. (2012).

Experimental top

To a stirred solution of 1-(1,4,5,6,8-pentamethoxynaphthalen-2-yl)ethanone (0.500 g, 1.62 mmol) and diethyl oxalate (0.474 g, 3.24 mmol, 2.0 equiv.) in dry tetrahydrofruan (50 ml) at 0 oC, sodium ethoxide (0.220 g, 3.24 mmol, 2.0 equiv.) was slowly added. The reaction mixture was then stirred vigorously for 3 h at RT before being acidified with an aqueous solution of hydrochloric acid (20 ml, 2.0 M). Ethyl acetate (20 ml) was then added to the mixture. The organic layer was then separated, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Column chromatography (eluant 10% ethyl acetate/hexane) of the residue afforded (Z)-ethyl 2-hydroxy-4-oxo-4-(1,4,5,6,8-pentamethoxynaphthalene-2-yl)but-2-enoate as a red solid (0.613 g, 90%); m.p. 117–118 oC; Rf 0.55 (20% ethyl acetate/hexane); IR (film): Vmax = 3120 cm-1 (w, br, OH), 2979 cm-1 (w, br, OH), 1818 cm-1 (s, C=O), 1594 cm-1 (m, C—OH), 1471 cm-1 (m, C=C), 1371 cm-1 (m, C=C), 1317 cm-1 (m, C=C), 1252 cm-1 (s, C—O—C), 1222 (s, C—O—C), 1183 cm-1 (s, C—O—C),; 1H NMR (300 MHz, CDCl3) δH 7.59 (1 H, s, H-2), 7.22 (1 H, s, H-6), 6.79 (1 H, s, COCH=C(OH)CO2CH2CH3), 4.38 (2 H, q, J 7.1, COCH=C(OH)CO2CH2CH3), 4.04, 4.02, 3.99, 3.82, 3.78 (each 3 H, s, OCH3), 1.38 (3 H, t, J 3.3, COCH=C(OH)CO2CH2CH3); 13C NMR (300 MHz, CDCl3) δC 192.5 (C=O), 166.7 (COCH=C(OH)CO2CH2CH3), 162.7 (COCH=C(OH)CO2CH2CH3), 154.8 (ArC-O), 154.1 (ArC-O), 153.1 (ArC-O), 152.2 (ArC-O), 138.2 (ArC-O), 126.7 (C-1), 123.6 (C-3a), 116.6 (C-7a), 105.0 (C-2), 103.8 (C-6), 97.9 (COCH=C(OH)CO2CH2CH3), 63.8 (OCH3), 62.3 (COCH=C(OH)CO2CH2CH3), 61.9, 56.9, 56.8, 56.7 (4 x OCH3), 14.1 (COCH=C(OH)CO2CH2CH3); HR-TOF-MS: m/z found 421.1499, [M—H]+ (calculated for C21H25O9, 421.1487).

Refinement top

All H atoms attached to carbon were positioned geometrically, and allowed to ride on their parent atoms, with C—H and O—H bond lengths of 0.95 Å (CH), 0.98 Å (CH3) or 0.84 Å (OH), and isotropic displacement parameters set to 1.2 (CH) or 1.5 times (CH3 and OH) the Ueq of the parent atom. The ethanoate group on molecule A was found to be disordered and as a consequence refined over two positions using SIMU, DELU, EXYZ, EADP and SADI constraints. The final occupancies for the two positions were 0.880 (7) and 0.120 (7).

Structure description top

As part of our research programme directed towards the synthesis of the natural phytotoxic naphthoquinone, marticin (Pillay et al., 2012), we synthesized the title compound in one step from 1-(1,4,5,6,8-pentamethoxynaphthalen-2-yl)ethanone (1) (de Koning et al., 1991). This was achieved as shown in Fig. 4 by treating (1) with diethyl oxalate with sodium ethoxide in THF to afford the title compound (2) as a bright red crystalline solid.

The title organic compound crystallizes in the space group P -1 with two independent molecules in the asymmetric unit which are labelled as A and B in Fig. 1. The molecules are almost centrosymmetrically related to each other, with the symmetry being broken by the ethanoate group of molecule A being disordered over two positions. The crystal structure shows that the 1,3-diketone moiety exists as the keto-enol isomeric form, with the enol-ether form being occupied due to the presence of intramolecular hydrogen bonding (Table 1). Strong intermolecular hydrogen bonding is present between pairs of B molecules in which H7B, which is involved in the intramolecular hydrogen bond with O6B, also interacts with O6B of another molecule related by a centre of inversion (Fig. 2.; Table 1). Molecule A is not involved in any strong intermolecular hydrogen bonding. Molecules in the structure pack as a layers (Fig. 3) with C—H···O and C—H···π interactions acting within and between the layers.

For the synthesis of the title compound, see: de Koning et al. (1991). This forms part of our research programme directed towards the synthesis of the natural phytotoxic naphthoquinone, marticin, see: Pillay et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2005a); cell refinement: SAINT-NT (Bruker, 2005b); data reduction: SAINT-NT (Bruker, 2005b); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atomic numbering scheme and intramolecular hydrogen bonding. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Intermolecular hydrogen bonding between a pair of B molecules related by a centre of inversion. Also shown is the intramolecular hydrogen bonding within each molecule.
[Figure 3] Fig. 3. Diagram showing the layered packing of molecules in the structure. C—H···O and C—H···π interactions are present within and between the layers.
[Figure 4] Fig. 4. Reaction scheme for the synthesis of the title compound.
(Z)-Ethyl 2-hydroxy-4-oxo-4-(1,4,5,6,8-pentamethoxynaphthalen-2-yl)but- 2-enoate top
Crystal data top
C21H24O9Z = 4
Mr = 420.40F(000) = 888
Triclinic, P1Dx = 1.410 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8019 (4) ÅCell parameters from 1943 reflections
b = 12.3042 (6) Åθ = 2.6–25.0°
c = 24.3971 (12) ŵ = 0.11 mm−1
α = 100.002 (4)°T = 173 K
β = 93.080 (4)°Needle, red
γ = 98.748 (4)°0.39 × 0.16 × 0.07 mm
V = 1980.67 (18) Å3
Data collection top
Bruker APEXII CCD
diffractometer		3172 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.083
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
φ and ω scansh = −8→8
19594 measured reflectionsk = −15→15
7793 independent reflectionsl = −30→30
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.0343P)2]
where P = (Fo2 + 2Fc2)/3
7793 reflections(Δ/σ)max = 0.001
572 parametersΔρmax = 0.21 e Å−3
54 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C21H24O9γ = 98.748 (4)°
Mr = 420.40V = 1980.67 (18) Å3
Triclinic, P1Z = 4
a = 6.8019 (4) ÅMo Kα radiation
b = 12.3042 (6) ŵ = 0.11 mm−1
c = 24.3971 (12) ÅT = 173 K
α = 100.002 (4)°0.39 × 0.16 × 0.07 mm
β = 93.080 (4)°
Data collection top
Bruker APEXII CCD
diffractometer		3172 reflections with I > 2σ(I)
19594 measured reflectionsRint = 0.083
7793 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05354 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 0.84Δρmax = 0.21 e Å−3
7793 reflectionsΔρmin = −0.25 e Å−3
572 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*/UeqOcc. (<1)
C1A0.7086 (4)0.6467 (2)0.10802 (12)0.0245 (8)
C2A0.7846 (4)0.6053 (2)0.15505 (12)0.0247 (8)
C3A0.9780 (5)0.6484 (2)0.18382 (13)0.0274 (8)
C4A1.0511 (5)0.6025 (2)0.22628 (12)0.0293 (8)
H4A1.18050.63170.24410.035*
C5A0.9352 (5)0.5130 (3)0.24321 (13)0.0282 (8)
C6A0.7459 (5)0.4692 (2)0.21838 (12)0.0259 (8)
C7A0.6673 (4)0.5137 (2)0.17411 (12)0.0244 (8)
C8A0.4709 (5)0.4721 (3)0.14548 (13)0.0284 (8)
C9A0.4045 (5)0.5152 (2)0.10176 (12)0.0274 (8)
H9A0.27470.48590.08420.033*
C10A0.5233 (4)0.6030 (2)0.08142 (12)0.0244 (8)
C11A0.4404 (5)0.6341 (3)0.03013 (13)0.0269 (8)
C12A0.5123 (5)0.7360 (3)0.01041 (12)0.0320 (9)
H12A0.62400.78630.02990.038*
C13A0.4219 (5)0.7599 (3)−0.03533 (14)0.0363 (9)
C14A0.4888 (6)0.8667 (3)−0.05716 (15)0.0437 (9)0.880 (7)
C15A0.7626 (7)1.0144 (3)−0.0550 (2)0.0586 (16)0.880 (7)
H15A0.85051.0631−0.02380.070*0.880 (7)
H15B0.65431.0549−0.06480.070*0.880 (7)
C16A0.8787 (8)0.9900 (4)−0.1037 (2)0.0657 (18)0.880 (7)
H16A0.93491.0602−0.11500.099*0.880 (7)
H16B0.79120.9425−0.13470.099*0.880 (7)
H16C0.98710.9510−0.09380.099*0.880 (7)
O8A0.6766 (4)0.9106 (3)−0.03759 (16)0.0469 (10)0.880 (7)
O9A0.3818 (5)0.9035 (3)−0.08750 (19)0.0591 (13)0.880 (7)
C14C0.4888 (6)0.8667 (3)−0.05716 (15)0.0437 (9)0.120 (7)
C15C0.750 (2)0.971 (2)−0.0955 (11)0.035 (7)*0.120 (7)
H15E0.66421.0293−0.08800.042*0.120 (7)
H15F0.74280.9443−0.13630.042*0.120 (7)
C16C0.958 (4)1.018 (3)−0.0738 (15)0.069 (13)*0.120 (7)
H16G1.00931.0779−0.09340.103*0.120 (7)
H16H1.04070.9587−0.07990.103*0.120 (7)
H16I0.96271.0477−0.03380.103*0.120 (7)
O8C0.6804 (13)0.8774 (15)−0.0674 (10)0.046 (5)*0.120 (7)
O9C0.371 (3)0.924 (2)−0.0690 (15)0.059 (11)*0.120 (7)
C17A0.9644 (5)0.6896 (3)0.05027 (13)0.0385 (9)
H17A1.04900.64680.06880.058*
H17B1.04800.75280.03900.058*
H17C0.89020.64110.01710.058*
C18A1.2844 (4)0.7789 (3)0.19191 (13)0.0377 (9)
H18A1.28160.80590.23200.057*
H18B1.34550.84030.17440.057*
H18C1.36260.71790.18610.057*
C19A1.1951 (5)0.5070 (3)0.31297 (14)0.0445 (10)
H19A1.29470.49880.28560.067*
H19B1.22080.46480.34240.067*
H19C1.20340.58620.32950.067*
C20A0.6807 (5)0.2757 (3)0.21377 (14)0.0409 (9)
H20A0.63510.26100.17400.061*
H20B0.60980.21790.23180.061*
H20C0.82450.27480.21800.061*
C21A0.1682 (4)0.3393 (3)0.13505 (13)0.0371 (9)
H21A0.08420.39760.13620.056*
H21B0.10330.27900.15260.056*
H21C0.18710.30940.09610.056*
O1A0.8265 (3)0.73063 (16)0.08806 (8)0.0274 (5)
O2A1.0851 (3)0.73912 (17)0.16741 (8)0.0352 (6)
O3A0.9989 (3)0.46456 (17)0.28566 (9)0.0378 (6)
O4A0.6406 (3)0.38328 (17)0.23943 (8)0.0311 (6)
O5A0.3595 (3)0.38650 (17)0.16480 (8)0.0360 (6)
O6A0.2923 (3)0.56832 (17)0.00277 (8)0.0317 (6)
O7A0.2659 (3)0.6961 (2)−0.06553 (9)0.0450 (7)
H7A0.23010.6399−0.05100.068*
C1B0.3209 (5)0.8636 (2)0.39125 (12)0.0268 (8)
C2B0.2118 (4)0.9010 (3)0.34798 (12)0.0260 (8)
C3B0.0137 (5)0.8495 (2)0.32514 (13)0.0276 (8)
C4B−0.0842 (4)0.8891 (2)0.28420 (12)0.0282 (8)
H4B−0.21630.85450.27040.034*
C5B0.0082 (5)0.9796 (3)0.26257 (13)0.0285 (8)
C6B0.2003 (4)1.0317 (2)0.28214 (12)0.0250 (8)
C7B0.3025 (4)0.9964 (2)0.32591 (12)0.0246 (8)
C8B0.4976 (4)1.0515 (3)0.35055 (12)0.0274 (8)
C9B0.5930 (4)1.0143 (2)0.39183 (12)0.0265 (8)
H9B0.72111.05310.40710.032*
C10B0.5082 (4)0.9193 (3)0.41316 (12)0.0266 (8)
C11B0.6317 (5)0.8932 (3)0.45984 (13)0.0318 (8)
C12B0.5872 (5)0.7955 (3)0.48512 (12)0.0317 (8)
H12B0.47730.73890.47010.038*
C13B0.7032 (5)0.7848 (3)0.53055 (13)0.0315 (8)
C14B0.6633 (5)0.6875 (3)0.55955 (14)0.0348 (9)
C15B0.4164 (5)0.5460 (3)0.57949 (14)0.0468 (10)
H15C0.43990.57350.62030.056*
H15D0.49600.48570.56910.056*
C16B0.1988 (5)0.5027 (3)0.56370 (15)0.0514 (11)
H16D0.12240.56400.57250.077*
H16E0.15350.44390.58470.077*
H16F0.17850.47200.52360.077*
C17B0.1232 (5)0.7820 (3)0.45533 (13)0.0405 (9)
H17D0.19550.84020.48530.061*
H17E0.09330.71160.46920.061*
H17F−0.00180.80460.44320.061*
C18B−0.2757 (4)0.7101 (3)0.32455 (13)0.0366 (9)
H18D−0.36200.76700.33230.055*
H18E−0.32150.64730.34300.055*
H18F−0.28130.68340.28420.055*
C19B−0.2761 (4)0.9696 (3)0.19809 (14)0.0422 (10)
H19D−0.27640.89020.18330.063*
H19E−0.31831.00640.16800.063*
H19F−0.36860.97650.22750.063*
C20B0.2339 (5)1.2213 (2)0.27309 (13)0.0403 (9)
H20D0.08851.21530.26800.060*
H20E0.29681.27430.25100.060*
H20F0.27881.24790.31270.060*
C21B0.7722 (4)1.2003 (3)0.35457 (13)0.0387 (9)
H21D0.76721.22720.39460.058*
H21E0.81541.26380.33630.058*
H21F0.86701.14760.34910.058*
O1B0.2440 (3)0.76673 (16)0.40899 (8)0.0307 (6)
O2B−0.0734 (3)0.75818 (17)0.34535 (8)0.0358 (6)
O3B−0.0784 (3)1.02174 (18)0.22093 (9)0.0380 (6)
O4B0.2889 (3)1.11377 (17)0.25499 (8)0.0293 (5)
O5B0.5775 (3)1.14496 (18)0.33067 (9)0.0376 (6)
O6B0.7876 (3)0.96174 (18)0.47859 (9)0.0434 (7)
O7B0.8649 (3)0.85584 (19)0.55340 (9)0.0433 (6)
H7B0.88470.90860.53560.065*
O8B0.4734 (3)0.63665 (18)0.54955 (9)0.0403 (6)
O9B0.7878 (4)0.6589 (2)0.58861 (10)0.0492 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.027 (2)0.0197 (18)0.0280 (19)0.0018 (15)0.0058 (16)0.0087 (15)
C2A0.0191 (18)0.0271 (19)0.0273 (19)0.0021 (15)−0.0025 (15)0.0064 (15)
C3A0.0266 (19)0.0256 (19)0.0281 (19)−0.0021 (15)−0.0009 (16)0.0067 (15)
C4A0.0240 (19)0.031 (2)0.0302 (19)−0.0008 (15)−0.0084 (16)0.0073 (16)
C5A0.031 (2)0.0256 (19)0.029 (2)0.0068 (16)−0.0031 (17)0.0074 (16)
C6A0.0255 (19)0.0254 (19)0.0271 (19)0.0006 (15)0.0037 (16)0.0081 (15)
C7A0.0235 (19)0.0233 (18)0.0247 (19)−0.0003 (15)0.0004 (16)0.0035 (15)
C8A0.026 (2)0.0273 (19)0.032 (2)0.0008 (15)0.0077 (17)0.0085 (16)
C9A0.0216 (19)0.0292 (19)0.030 (2)−0.0001 (15)0.0008 (16)0.0064 (16)
C10A0.0205 (18)0.0267 (18)0.0245 (19)0.0005 (15)−0.0021 (15)0.0048 (15)
C11A0.0246 (19)0.031 (2)0.0271 (19)0.0096 (15)0.0051 (16)0.0048 (16)
C12A0.036 (2)0.034 (2)0.027 (2)0.0022 (16)0.0009 (17)0.0113 (16)
C13A0.038 (2)0.042 (2)0.031 (2)0.0115 (18)0.0047 (19)0.0093 (18)
C14A0.062 (2)0.041 (2)0.035 (2)0.0180 (18)0.008 (2)0.0186 (19)
C15A0.079 (4)0.039 (3)0.066 (4)0.007 (2)0.023 (3)0.028 (3)
C16A0.092 (5)0.041 (3)0.066 (4)0.000 (3)0.029 (3)0.018 (3)
O8A0.0502 (18)0.0399 (18)0.058 (2)0.0060 (14)0.0111 (15)0.0283 (17)
O9A0.086 (3)0.056 (2)0.045 (3)0.0240 (19)−0.0081 (18)0.029 (2)
C14C0.062 (2)0.041 (2)0.035 (2)0.0180 (18)0.008 (2)0.0186 (19)
C17A0.031 (2)0.045 (2)0.037 (2)−0.0028 (17)0.0083 (18)0.0103 (17)
C18A0.0237 (19)0.039 (2)0.045 (2)−0.0125 (16)−0.0058 (17)0.0109 (17)
C19A0.048 (2)0.040 (2)0.045 (2)0.0006 (18)−0.0187 (19)0.0182 (18)
C20A0.040 (2)0.031 (2)0.053 (2)0.0025 (17)0.0037 (19)0.0159 (18)
C21A0.028 (2)0.037 (2)0.042 (2)−0.0104 (16)−0.0031 (18)0.0116 (17)
O1A0.0235 (13)0.0267 (13)0.0322 (13)−0.0008 (10)0.0002 (11)0.0111 (10)
O2A0.0262 (13)0.0358 (14)0.0401 (14)−0.0113 (11)−0.0106 (11)0.0162 (11)
O3A0.0353 (14)0.0366 (14)0.0402 (14)−0.0039 (11)−0.0151 (12)0.0174 (11)
O4A0.0312 (13)0.0305 (13)0.0328 (13)0.0010 (11)0.0014 (11)0.0129 (11)
O5A0.0242 (13)0.0392 (14)0.0430 (14)−0.0094 (11)−0.0072 (11)0.0190 (12)
O6A0.0270 (13)0.0345 (14)0.0308 (13)−0.0001 (11)−0.0059 (11)0.0056 (11)
O7A0.0474 (17)0.0515 (17)0.0362 (15)0.0041 (13)−0.0091 (13)0.0152 (12)
C1B0.031 (2)0.0235 (18)0.0268 (19)0.0050 (15)0.0044 (16)0.0065 (15)
C2B0.0217 (19)0.0299 (19)0.0254 (19)0.0014 (15)−0.0025 (15)0.0064 (15)
C3B0.027 (2)0.0275 (19)0.0281 (19)−0.0012 (16)0.0026 (16)0.0098 (16)
C4B0.0201 (19)0.032 (2)0.030 (2)−0.0015 (15)−0.0035 (16)0.0046 (16)
C5B0.025 (2)0.033 (2)0.0269 (19)0.0029 (16)−0.0060 (16)0.0098 (16)
C6B0.0258 (19)0.0270 (19)0.0212 (18)0.0006 (15)−0.0004 (15)0.0053 (15)
C7B0.0218 (19)0.0243 (19)0.0255 (19)−0.0010 (15)0.0015 (16)0.0032 (15)
C8B0.0250 (19)0.030 (2)0.0271 (19)0.0028 (16)−0.0025 (16)0.0072 (16)
C9B0.0215 (18)0.0274 (19)0.0268 (19)−0.0036 (15)−0.0034 (15)0.0030 (15)
C10B0.0207 (18)0.032 (2)0.0267 (19)0.0052 (15)−0.0044 (16)0.0043 (15)
C11B0.033 (2)0.031 (2)0.030 (2)0.0091 (17)−0.0041 (17)0.0023 (16)
C12B0.034 (2)0.032 (2)0.028 (2)0.0053 (16)−0.0066 (17)0.0047 (16)
C13B0.028 (2)0.037 (2)0.030 (2)0.0044 (17)0.0003 (17)0.0112 (17)
C14B0.030 (2)0.042 (2)0.030 (2)0.0056 (18)−0.0031 (18)0.0050 (17)
C15B0.052 (3)0.042 (2)0.050 (2)0.0017 (19)−0.004 (2)0.024 (2)
C16B0.046 (2)0.045 (2)0.060 (3)−0.0077 (19)−0.008 (2)0.017 (2)
C17B0.036 (2)0.046 (2)0.039 (2)−0.0042 (17)0.0026 (18)0.0185 (18)
C18B0.026 (2)0.036 (2)0.044 (2)−0.0084 (16)−0.0021 (18)0.0121 (17)
C19B0.029 (2)0.049 (2)0.047 (2)−0.0016 (18)−0.0154 (18)0.0145 (19)
C20B0.039 (2)0.033 (2)0.052 (2)0.0032 (17)0.0028 (19)0.0205 (18)
C21B0.0222 (19)0.045 (2)0.044 (2)−0.0104 (17)−0.0054 (17)0.0095 (18)
O1B0.0335 (14)0.0268 (13)0.0306 (13)−0.0009 (11)−0.0029 (11)0.0090 (10)
O2B0.0297 (14)0.0345 (14)0.0398 (14)−0.0104 (11)−0.0100 (11)0.0155 (11)
O3B0.0272 (13)0.0440 (15)0.0410 (15)−0.0067 (11)−0.0127 (11)0.0188 (12)
O4B0.0267 (13)0.0292 (13)0.0319 (13)−0.0029 (10)0.0003 (11)0.0125 (11)
O5B0.0281 (14)0.0398 (14)0.0428 (14)−0.0120 (11)−0.0098 (11)0.0210 (12)
O6B0.0365 (15)0.0402 (15)0.0485 (15)−0.0080 (12)−0.0234 (12)0.0146 (12)
O7B0.0422 (16)0.0465 (17)0.0394 (15)−0.0008 (12)−0.0118 (13)0.0148 (12)
O8B0.0370 (15)0.0413 (15)0.0463 (15)0.0024 (12)−0.0026 (12)0.0242 (12)
O9B0.0420 (16)0.0589 (17)0.0525 (17)0.0091 (13)−0.0066 (14)0.0289 (14)
Geometric parameters (Å, º) top
C1A—C10A1.373 (4)C21A—H21B0.9800
C1A—O1A1.382 (3)C21A—H21C0.9800
C1A—C2A1.436 (4)O7A—H7A0.8400
C2A—C3A1.437 (4)C1B—O1B1.377 (3)
C2A—C7A1.439 (4)C1B—C10B1.383 (4)
C3A—C4A1.368 (4)C1B—C2B1.437 (4)
C3A—O2A1.369 (3)C2B—C3B1.436 (4)
C4A—C5A1.391 (4)C2B—C7B1.444 (4)
C4A—H4A0.9500C3B—C4B1.369 (4)
C5A—O3A1.364 (3)C3B—O2B1.370 (3)
C5A—C6A1.381 (4)C4B—C5B1.393 (4)
C6A—O4A1.376 (3)C4B—H4B0.9500
C6A—C7A1.408 (4)C5B—O3B1.364 (3)
C7A—C8A1.450 (4)C5B—C6B1.385 (4)
C8A—C9A1.356 (4)C6B—O4B1.383 (3)
C8A—O5A1.369 (3)C6B—C7B1.409 (4)
C9A—C10A1.425 (4)C7B—C8B1.443 (4)
C9A—H9A0.9500C8B—C9B1.350 (4)
C10A—C11A1.479 (4)C8B—O5B1.373 (3)
C11A—O6A1.268 (3)C9B—C10B1.417 (4)
C11A—C12A1.446 (4)C9B—H9B0.9500
C12A—C13A1.343 (4)C10B—C11B1.488 (4)
C12A—H12A0.9500C11B—O6B1.260 (3)
C13A—O7A1.321 (4)C11B—C12B1.443 (4)
C13A—C14A1.518 (4)C12B—C13B1.362 (4)
C14A—O9A1.200 (4)C12B—H12B0.9500
C14A—O8A1.337 (4)C13B—O7B1.326 (4)
C15A—O8A1.465 (4)C13B—C14B1.492 (4)
C15A—C16A1.474 (5)C14B—O9B1.207 (4)
C15A—H15A0.9900C14B—O8B1.337 (4)
C15A—H15B0.9900C15B—O8B1.453 (3)
C16A—H16A0.9800C15B—C16B1.500 (4)
C16A—H16B0.9800C15B—H15C0.9900
C16A—H16C0.9800C15B—H15D0.9900
C15C—O8C1.470 (6)C16B—H16D0.9800
C15C—C16C1.478 (7)C16B—H16E0.9800
C15C—H15E0.9900C16B—H16F0.9800
C15C—H15F0.9900C17B—O1B1.436 (3)
C16C—H16G0.9800C17B—H17D0.9800
C16C—H16H0.9800C17B—H17E0.9800
C16C—H16I0.9800C17B—H17F0.9800
C17A—O1A1.435 (3)C18B—O2B1.440 (3)
C17A—H17A0.9800C18B—H18D0.9800
C17A—H17B0.9800C18B—H18E0.9800
C17A—H17C0.9800C18B—H18F0.9800
C18A—O2A1.429 (3)C19B—O3B1.437 (3)
C18A—H18A0.9800C19B—H19D0.9800
C18A—H18B0.9800C19B—H19E0.9800
C18A—H18C0.9800C19B—H19F0.9800
C19A—O3A1.438 (3)C20B—O4B1.432 (3)
C19A—H19A0.9800C20B—H20D0.9800
C19A—H19B0.9800C20B—H20E0.9800
C19A—H19C0.9800C20B—H20F0.9800
C20A—O4A1.435 (3)C21B—O5B1.436 (3)
C20A—H20A0.9800C21B—H21D0.9800
C20A—H20B0.9800C21B—H21E0.9800
C20A—H20C0.9800C21B—H21F0.9800
C21A—O5A1.442 (3)O7B—H7B0.8400
C21A—H21A0.9800
C10A—C1A—O1A119.0 (3)C1A—O1A—C17A113.2 (2)
C10A—C1A—C2A121.5 (3)C3A—O2A—C18A118.5 (2)
O1A—C1A—C2A119.4 (3)C5A—O3A—C19A118.3 (2)
C1A—C2A—C3A123.2 (3)C6A—O4A—C20A112.5 (2)
C1A—C2A—C7A119.7 (3)C8A—O5A—C21A117.1 (2)
C3A—C2A—C7A117.0 (3)C13A—O7A—H7A109.5
C4A—C3A—O2A121.4 (3)O1B—C1B—C10B118.9 (3)
C4A—C3A—C2A121.8 (3)O1B—C1B—C2B119.7 (3)
O2A—C3A—C2A116.9 (3)C10B—C1B—C2B121.2 (3)
C3A—C4A—C5A119.8 (3)C3B—C2B—C1B123.8 (3)
C3A—C4A—H4A120.1C3B—C2B—C7B117.0 (3)
C5A—C4A—H4A120.1C1B—C2B—C7B119.2 (3)
O3A—C5A—C6A116.0 (3)C4B—C3B—O2B121.0 (3)
O3A—C5A—C4A122.5 (3)C4B—C3B—C2B121.5 (3)
C6A—C5A—C4A121.5 (3)O2B—C3B—C2B117.6 (3)
O4A—C6A—C5A117.1 (3)C3B—C4B—C5B120.5 (3)
O4A—C6A—C7A122.8 (3)C3B—C4B—H4B119.7
C5A—C6A—C7A120.1 (3)C5B—C4B—H4B119.7
C6A—C7A—C2A119.8 (3)O3B—C5B—C6B115.5 (3)
C6A—C7A—C8A123.7 (3)O3B—C5B—C4B123.7 (3)
C2A—C7A—C8A116.6 (3)C6B—C5B—C4B120.8 (3)
C9A—C8A—O5A122.6 (3)O4B—C6B—C5B117.4 (3)
C9A—C8A—C7A121.5 (3)O4B—C6B—C7B122.3 (3)
O5A—C8A—C7A115.9 (3)C5B—C6B—C7B120.3 (3)
C8A—C9A—C10A122.1 (3)C6B—C7B—C8B123.0 (3)
C8A—C9A—H9A119.0C6B—C7B—C2B119.8 (3)
C10A—C9A—H9A119.0C8B—C7B—C2B117.1 (3)
C1A—C10A—C9A118.5 (3)C9B—C8B—O5B122.3 (3)
C1A—C10A—C11A125.1 (3)C9B—C8B—C7B121.5 (3)
C9A—C10A—C11A116.3 (3)O5B—C8B—C7B116.2 (3)
O6A—C11A—C12A118.2 (3)C8B—C9B—C10B122.2 (3)
O6A—C11A—C10A117.4 (3)C8B—C9B—H9B118.9
C12A—C11A—C10A124.4 (3)C10B—C9B—H9B118.9
C13A—C12A—C11A120.3 (3)C1B—C10B—C9B118.8 (3)
C13A—C12A—H12A119.8C1B—C10B—C11B126.6 (3)
C11A—C12A—H12A119.8C9B—C10B—C11B114.6 (3)
O7A—C13A—C12A124.9 (3)O6B—C11B—C12B117.6 (3)
O7A—C13A—C14A112.6 (3)O6B—C11B—C10B117.2 (3)
C12A—C13A—C14A122.5 (3)C12B—C11B—C10B125.2 (3)
O9A—C14A—O8A127.0 (4)C13B—C12B—C11B119.9 (3)
O9A—C14A—C13A122.6 (4)C13B—C12B—H12B120.1
O8A—C14A—C13A110.4 (3)C11B—C12B—H12B120.1
O8A—C15A—C16A110.4 (3)O7B—C13B—C12B125.3 (3)
O8A—C15A—H15A109.6O7B—C13B—C14B112.0 (3)
C16A—C15A—H15A109.6C12B—C13B—C14B122.8 (3)
O8A—C15A—H15B109.6O9B—C14B—O8B124.5 (3)
C16A—C15A—H15B109.6O9B—C14B—C13B123.8 (3)
H15A—C15A—H15B108.1O8B—C14B—C13B111.7 (3)
C15A—C16A—H16A109.5O8B—C15B—C16B107.3 (3)
C15A—C16A—H16B109.5O8B—C15B—H15C110.3
H16A—C16A—H16B109.5C16B—C15B—H15C110.3
C15A—C16A—H16C109.5O8B—C15B—H15D110.3
H16A—C16A—H16C109.5C16B—C15B—H15D110.3
H16B—C16A—H16C109.5H15C—C15B—H15D108.5
C14A—O8A—C15A116.9 (3)C15B—C16B—H16D109.5
O8C—C15C—C16C108.3 (8)C15B—C16B—H16E109.5
O8C—C15C—H15E110.0H16D—C16B—H16E109.5
C16C—C15C—H15E110.0C15B—C16B—H16F109.5
O8C—C15C—H15F110.0H16D—C16B—H16F109.5
C16C—C15C—H15F110.0H16E—C16B—H16F109.5
H15E—C15C—H15F108.4O1B—C17B—H17D109.5
C15C—C16C—H16G109.5O1B—C17B—H17E109.5
C15C—C16C—H16H109.5H17D—C17B—H17E109.5
H16G—C16C—H16H109.5O1B—C17B—H17F109.5
C15C—C16C—H16I109.5H17D—C17B—H17F109.5
H16G—C16C—H16I109.5H17E—C17B—H17F109.5
H16H—C16C—H16I109.5O2B—C18B—H18D109.5
O1A—C17A—H17A109.5O2B—C18B—H18E109.5
O1A—C17A—H17B109.5H18D—C18B—H18E109.5
H17A—C17A—H17B109.5O2B—C18B—H18F109.5
O1A—C17A—H17C109.5H18D—C18B—H18F109.5
H17A—C17A—H17C109.5H18E—C18B—H18F109.5
H17B—C17A—H17C109.5O3B—C19B—H19D109.5
O2A—C18A—H18A109.5O3B—C19B—H19E109.5
O2A—C18A—H18B109.5H19D—C19B—H19E109.5
H18A—C18A—H18B109.5O3B—C19B—H19F109.5
O2A—C18A—H18C109.5H19D—C19B—H19F109.5
H18A—C18A—H18C109.5H19E—C19B—H19F109.5
H18B—C18A—H18C109.5O4B—C20B—H20D109.5
O3A—C19A—H19A109.5O4B—C20B—H20E109.5
O3A—C19A—H19B109.5H20D—C20B—H20E109.5
H19A—C19A—H19B109.5O4B—C20B—H20F109.5
O3A—C19A—H19C109.5H20D—C20B—H20F109.5
H19A—C19A—H19C109.5H20E—C20B—H20F109.5
H19B—C19A—H19C109.5O5B—C21B—H21D109.5
O4A—C20A—H20A109.5O5B—C21B—H21E109.5
O4A—C20A—H20B109.5H21D—C21B—H21E109.5
H20A—C20A—H20B109.5O5B—C21B—H21F109.5
O4A—C20A—H20C109.5H21D—C21B—H21F109.5
H20A—C20A—H20C109.5H21E—C21B—H21F109.5
H20B—C20A—H20C109.5C1B—O1B—C17B114.9 (2)
O5A—C21A—H21A109.5C3B—O2B—C18B117.6 (2)
O5A—C21A—H21B109.5C5B—O3B—C19B118.0 (2)
H21A—C21A—H21B109.5C6B—O4B—C20B113.9 (2)
O5A—C21A—H21C109.5C8B—O5B—C21B116.8 (2)
H21A—C21A—H21C109.5C13B—O7B—H7B109.5
H21B—C21A—H21C109.5C14B—O8B—C15B115.7 (3)
C10A—C1A—C2A—C3A179.7 (3)O1B—C1B—C2B—C3B6.8 (5)
O1A—C1A—C2A—C3A1.4 (5)C10B—C1B—C2B—C3B−177.4 (3)
C10A—C1A—C2A—C7A1.8 (4)O1B—C1B—C2B—C7B−174.0 (3)
O1A—C1A—C2A—C7A−176.5 (3)C10B—C1B—C2B—C7B1.9 (4)
C1A—C2A—C3A—C4A−175.9 (3)C1B—C2B—C3B—C4B179.5 (3)
C7A—C2A—C3A—C4A2.1 (5)C7B—C2B—C3B—C4B0.2 (5)
C1A—C2A—C3A—O2A5.2 (4)C1B—C2B—C3B—O2B−1.3 (5)
C7A—C2A—C3A—O2A−176.8 (3)C7B—C2B—C3B—O2B179.4 (3)
O2A—C3A—C4A—C5A177.6 (3)O2B—C3B—C4B—C5B−177.8 (3)
C2A—C3A—C4A—C5A−1.2 (5)C2B—C3B—C4B—C5B1.4 (5)
C3A—C4A—C5A—O3A−179.3 (3)C3B—C4B—C5B—O3B178.5 (3)
C3A—C4A—C5A—C6A−0.5 (5)C3B—C4B—C5B—C6B−0.3 (5)
O3A—C5A—C6A—O4A1.1 (4)O3B—C5B—C6B—O4B−4.9 (4)
C4A—C5A—C6A—O4A−177.8 (3)C4B—C5B—C6B—O4B173.9 (3)
O3A—C5A—C6A—C7A−179.9 (3)O3B—C5B—C6B—C7B178.7 (3)
C4A—C5A—C6A—C7A1.3 (5)C4B—C5B—C6B—C7B−2.5 (5)
O4A—C6A—C7A—C2A178.7 (3)O4B—C6B—C7B—C8B7.8 (5)
C5A—C6A—C7A—C2A−0.3 (5)C5B—C6B—C7B—C8B−176.0 (3)
O4A—C6A—C7A—C8A−1.5 (5)O4B—C6B—C7B—C2B−172.2 (3)
C5A—C6A—C7A—C8A179.5 (3)C5B—C6B—C7B—C2B4.0 (4)
C1A—C2A—C7A—C6A176.7 (3)C3B—C2B—C7B—C6B−2.9 (4)
C3A—C2A—C7A—C6A−1.3 (4)C1B—C2B—C7B—C6B177.8 (3)
C1A—C2A—C7A—C8A−3.1 (4)C3B—C2B—C7B—C8B177.2 (3)
C3A—C2A—C7A—C8A178.9 (3)C1B—C2B—C7B—C8B−2.1 (4)
C6A—C7A—C8A—C9A−177.7 (3)C6B—C7B—C8B—C9B−178.8 (3)
C2A—C7A—C8A—C9A2.1 (4)C2B—C7B—C8B—C9B1.1 (4)
C6A—C7A—C8A—O5A1.5 (4)C6B—C7B—C8B—O5B2.8 (4)
C2A—C7A—C8A—O5A−178.7 (3)C2B—C7B—C8B—O5B−177.2 (3)
O5A—C8A—C9A—C10A−178.9 (3)O5B—C8B—C9B—C10B178.5 (3)
C7A—C8A—C9A—C10A0.2 (5)C7B—C8B—C9B—C10B0.3 (5)
O1A—C1A—C10A—C9A178.9 (3)O1B—C1B—C10B—C9B175.4 (3)
C2A—C1A—C10A—C9A0.6 (4)C2B—C1B—C10B—C9B−0.5 (5)
O1A—C1A—C10A—C11A3.6 (5)O1B—C1B—C10B—C11B−7.6 (5)
C2A—C1A—C10A—C11A−174.8 (3)C2B—C1B—C10B—C11B176.5 (3)
C8A—C9A—C10A—C1A−1.6 (5)C8B—C9B—C10B—C1B−0.6 (5)
C8A—C9A—C10A—C11A174.2 (3)C8B—C9B—C10B—C11B−178.0 (3)
C1A—C10A—C11A—O6A162.6 (3)C1B—C10B—C11B—O6B−171.3 (3)
C9A—C10A—C11A—O6A−12.9 (4)C9B—C10B—C11B—O6B5.8 (4)
C1A—C10A—C11A—C12A−19.7 (5)C1B—C10B—C11B—C12B8.8 (5)
C9A—C10A—C11A—C12A164.8 (3)C9B—C10B—C11B—C12B−174.0 (3)
O6A—C11A—C12A—C13A0.7 (5)O6B—C11B—C12B—C13B5.3 (5)
C10A—C11A—C12A—C13A−177.0 (3)C10B—C11B—C12B—C13B−174.9 (3)
C11A—C12A—C13A—O7A0.0 (5)C11B—C12B—C13B—O7B−3.2 (5)
C11A—C12A—C13A—C14A178.8 (3)C11B—C12B—C13B—C14B178.6 (3)
O7A—C13A—C14A—O9A19.6 (6)O7B—C13B—C14B—O9B−20.1 (5)
C12A—C13A—C14A—O9A−159.3 (4)C12B—C13B—C14B—O9B158.3 (3)
O7A—C13A—C14A—O8A−160.7 (3)O7B—C13B—C14B—O8B159.6 (3)
C12A—C13A—C14A—O8A20.4 (5)C12B—C13B—C14B—O8B−21.9 (4)
O9A—C14A—O8A—C15A−0.3 (7)C10B—C1B—O1B—C17B92.4 (3)
C13A—C14A—O8A—C15A−180.0 (3)C2B—C1B—O1B—C17B−91.6 (3)
C16A—C15A—O8A—C14A−95.6 (5)C4B—C3B—O2B—C18B−3.9 (4)
C10A—C1A—O1A—C17A−94.7 (3)C2B—C3B—O2B—C18B176.9 (3)
C2A—C1A—O1A—C17A83.7 (3)C6B—C5B—O3B—C19B178.7 (3)
C4A—C3A—O2A—C18A6.0 (4)C4B—C5B—O3B—C19B−0.1 (5)
C2A—C3A—O2A—C18A−175.1 (3)C5B—C6B—O4B—C20B82.7 (3)
C6A—C5A—O3A—C19A180.0 (3)C7B—C6B—O4B—C20B−101.0 (3)
C4A—C5A—O3A—C19A−1.2 (4)C9B—C8B—O5B—C21B2.1 (4)
C5A—C6A—O4A—C20A−87.5 (3)C7B—C8B—O5B—C21B−179.6 (3)
C7A—C6A—O4A—C20A93.5 (3)O9B—C14B—O8B—C15B4.2 (5)
C9A—C8A—O5A—C21A2.6 (4)C13B—C14B—O8B—C15B−175.5 (3)
C7A—C8A—O5A—C21A−176.6 (3)C16B—C15B—O8B—C14B178.6 (3)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C1A/C2A/C7A–C10A, C2A–C7A and C2B–C7B rings, respectively.
D—H···AD—HH···AD···AD—H···A
O7A—H7A···O6A0.841.772.499 (3)144
O7B—H7B···O6B0.841.772.497 (3)143
C17B—H17D···O6Bi0.982.433.234 (4)139
C19A—H19B···O9Bii0.982.453.419 (4)168
C19B—H19E···O9Aiii0.982.473.440 (5)172
C20A—H20B···O4Biv0.982.503.384 (4)150
C20B—H20E···O4Av0.982.573.382 (4)140
C20B—H20F···O9Bi0.982.583.460 (4)150
C18A—H18A···Cg3vi0.982.663.486 (3)142
C18A—H18C···Cg1vi0.982.923.844 (3)158
C18B—H18F···Cg2vii0.982.663.522 (3)147
C21A—H21A···Cg2vii0.982.963.845 (3)150
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x, −y+2, −z; (iv) x, y−1, z; (v) x, y+1, z; (vi) x+1, y, z; (vii) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC21H24O9
Mr420.40
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.8019 (4), 12.3042 (6), 24.3971 (12)
α, β, γ (°)100.002 (4), 93.080 (4), 98.748 (4)
V (Å3)1980.67 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.39 × 0.16 × 0.07
Data collection
DiffractometerBruker APEXII CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		19594, 7793, 3172
Rint0.083
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.118, 0.84
No. of reflections7793
No. of parameters572
No. of restraints54
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.25

Computer programs: APEX2 (Bruker, 2005a), SAINT-NT (Bruker, 2005b), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and SCHAKAL99 (Keller, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C1A/C2A/C7A–C10A, C2A–C7A and C2B–C7B rings, respectively.
D—H···AD—HH···AD···AD—H···A
O7A—H7A···O6A0.841.772.499 (3)144
O7B—H7B···O6B0.841.772.497 (3)143
C17B—H17D···O6Bi0.982.433.234 (4)139
C19A—H19B···O9Bii0.982.453.419 (4)168
C19B—H19E···O9Aiii0.982.473.440 (5)172
C20A—H20B···O4Biv0.982.503.384 (4)150
C20B—H20E···O4Av0.982.573.382 (4)140
C20B—H20F···O9Bi0.982.583.460 (4)150
C18A—H18A···Cg3vi0.982.663.486 (3)142
C18A—H18C···Cg1vi0.982.923.844 (3)158
C18B—H18F···Cg2vii0.982.663.522 (3)147
C21A—H21A···Cg2vii0.982.963.845 (3)150
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x, −y+2, −z; (iv) x, y−1, z; (v) x, y+1, z; (vi) x+1, y, z; (vii) x−1, y, z.
 

Acknowledgements

This work was supported by SABINA (Southern African Biochemistry and Informatics for Natural Products Network), the National Research Foundation [NRF, GUN 2053652 and IRDP of the NRF (South Africa) for financial support provided by the Research Niche Areas programme], Pretoria, and the University of the Witwatersrand (Science Faculty Research Council).

References

First citationBruker (2005). APEX2 and SAINT-NT (includes XPREP and SADABS). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationKeller, E. (1999). SCHAKAL99. University of Freiberg, Germany.  Google Scholar
 First citationKoning, C. B. de, Giles, R. G. F. & Green, I. R. (1991). J. Chem. Soc. Perkin Trans. 1, pp. 2743–2748.  Google Scholar
 First citationPillay, A., Rousseau, A. L., Fernandes, M. A. & de Koning, C. B. (2012). Tetrahedron, 68, 7116–7121.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 69| Part 1| January 2013| Pages o54-o55
https://doi.org/10.1107/S1600536812049203
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