# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1027038'
_audit_update_record             
;
2014-09-30 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 O9'
_chemical_formula_sum            'C28 H30 O9'
_chemical_formula_weight         510.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.7407(18)
_cell_length_b                   15.432(2)
_cell_length_c                   24.564(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5208.8(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2710
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      18.56

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2160
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9099
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48894
_diffrn_reflns_av_R_equivalents  0.1009
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4595
_reflns_number_gt                3082
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (APEX2, Bruker, 2006)'
_computing_data_reduction        'SAINT (APEX2, Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1401P)²+16.1292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4595
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.2417
_refine_ls_wR_factor_gt          0.2010
_refine_ls_goodness_of_fit_ref   0.792
_refine_ls_restrained_S_all      0.792
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8496(2) -0.0497(2) 0.69491(12) 0.0552(8) Uani 1 1 d . . .
O2 O 0.8221(3) 0.2795(2) 0.74736(15) 0.0690(10) Uani 1 1 d . . .
O3 O 0.5850(4) 0.2342(3) 0.94830(19) 0.1105(17) Uani 1 1 d . . .
O4 O 0.8015(3) 0.2414(2) 0.64292(13) 0.0647(10) Uani 1 1 d . . .
O5 O 0.8942(2) 0.0893(2) 0.99085(12) 0.0613(9) Uani 1 1 d . . .
O6 O 0.7174(2) 0.0665(2) 1.02383(12) 0.0638(10) Uani 1 1 d . . .
O7 O 0.5959(2) 0.01773(18) 0.64210(11) 0.0458(7) Uani 1 1 d . . .
O8 O 0.5643(3) 0.18132(19) 0.65195(13) 0.0588(9) Uani 1 1 d . . .
O9 O 0.6511(2) 0.2046(2) 0.86778(13) 0.0583(9) Uani 1 1 d . . .
C1 C 0.8322(3) 0.0257(3) 0.70693(16) 0.0383(9) Uani 1 1 d . . .
C2 C 0.8215(3) 0.0911(3) 0.66503(16) 0.0441(10) Uani 1 1 d . . .
H2 H 0.8211 0.0743 0.6287 0.053 Uiso 1 1 calc R . .
C3 C 0.8121(3) 0.1749(3) 0.67741(17) 0.0448(10) Uani 1 1 d . . .
C4 C 0.8169(3) 0.2034(3) 0.73530(18) 0.0440(10) Uani 1 1 d . . .
C5 C 0.8152(3) 0.1352(3) 0.77721(16) 0.0408(10) Uani 1 1 d . . .
H5 H 0.8101 0.1515 0.8135 0.049 Uiso 1 1 calc R . .
C6 C 0.8207(3) 0.0508(2) 0.76524(15) 0.0342(9) Uani 1 1 d . . .
C7 C 0.8196(3) -0.0210(3) 0.80636(15) 0.0380(9) Uani 1 1 d . . .
H7A H 0.8848 -0.0447 0.8090 0.046 Uiso 1 1 calc R . .
H7B H 0.7774 -0.0667 0.7930 0.046 Uiso 1 1 calc R . .
C8 C 0.7859(3) 0.0042(2) 0.86324(15) 0.0355(9) Uani 1 1 d . . .
C9 C 0.8556(3) 0.0342(3) 0.90028(16) 0.0405(10) Uani 1 1 d . . .
H9 H 0.9199 0.0394 0.8890 0.049 Uiso 1 1 calc R . .
C10 C 0.8318(3) 0.0563(3) 0.95308(16) 0.0435(10) Uani 1 1 d . . .
C11 C 0.7354(3) 0.0456(3) 0.97039(15) 0.0437(10) Uani 1 1 d . . .
C12 C 0.6661(3) 0.0170(3) 0.93381(16) 0.0454(11) Uani 1 1 d . . .
H12 H 0.6022 0.0101 0.9455 0.054 Uiso 1 1 calc R . .
C13 C 0.6893(3) -0.0018(3) 0.87949(15) 0.0360(9) Uani 1 1 d . . .
C14 C 0.6081(3) -0.0273(3) 0.84103(16) 0.0447(10) Uani 1 1 d . . .
H14A H 0.5479 -0.0299 0.8616 0.054 Uiso 1 1 calc R . .
H14B H 0.6214 -0.0852 0.8275 0.054 Uiso 1 1 calc R . .
C15 C 0.5927(3) 0.0321(3) 0.79254(16) 0.0369(9) Uani 1 1 d . . .
C16 C 0.5736(3) 0.1206(3) 0.79777(17) 0.0420(10) Uani 1 1 d . . .
C17 C 0.5648(3) 0.1709(3) 0.75099(19) 0.0453(10) Uani 1 1 d . . .
H17 H 0.5534 0.2300 0.7546 0.054 Uiso 1 1 calc R . .
C18 C 0.5724(3) 0.1366(3) 0.69989(17) 0.0422(10) Uani 1 1 d . . .
C19 C 0.5896(3) 0.0473(3) 0.69392(16) 0.0373(9) Uani 1 1 d . . .
C20 C 0.5987(3) -0.0029(3) 0.74053(16) 0.0372(9) Uani 1 1 d . . .
H20 H 0.6092 -0.0622 0.7368 0.045 Uiso 1 1 calc R . .
C21 C 0.5596(3) 0.1647(3) 0.8515(2) 0.0571(13) Uani 1 1 d . . .
H21A H 0.5093 0.2085 0.8485 0.068 Uiso 1 1 calc R . .
H21B H 0.5394 0.1228 0.8787 0.068 Uiso 1 1 calc R . .
C22 C 0.6530(5) 0.2387(3) 0.9172(2) 0.0696(15) Uani 1 1 d . . .
C23 C 0.7487(5) 0.2801(4) 0.9298(2) 0.094(2) Uani 1 1 d . . .
H23A H 0.7379 0.3357 0.9462 0.141 Uiso 1 1 calc R . .
H23B H 0.7851 0.2873 0.8967 0.141 Uiso 1 1 calc R . .
H23C H 0.7846 0.2439 0.9544 0.141 Uiso 1 1 calc R . .
C24 C 0.5439(5) 0.2710(3) 0.6554(3) 0.088(2) Uani 1 1 d . . .
H24A H 0.4846 0.2796 0.6754 0.132 Uiso 1 1 calc R . .
H24B H 0.5369 0.2945 0.6194 0.132 Uiso 1 1 calc R . .
H24C H 0.5964 0.2999 0.6737 0.132 Uiso 1 1 calc R . .
C25 C 0.6121(4) -0.0732(3) 0.63452(19) 0.0554(12) Uani 1 1 d . . .
H25A H 0.6701 -0.0902 0.6535 0.083 Uiso 1 1 calc R . .
H25B H 0.6195 -0.0853 0.5964 0.083 Uiso 1 1 calc R . .
H25C H 0.5576 -0.1050 0.6485 0.083 Uiso 1 1 calc R . .
C26 C 0.7929(5) 0.2209(4) 0.5861(2) 0.087(2) Uani 1 1 d . . .
H26A H 0.8518 0.1936 0.5738 0.131 Uiso 1 1 calc R . .
H26B H 0.7822 0.2731 0.5657 0.131 Uiso 1 1 calc R . .
H26C H 0.7391 0.1822 0.5808 0.131 Uiso 1 1 calc R . .
C27 C 0.9904(4) 0.1093(4) 0.9731(2) 0.0745(17) Uani 1 1 d . . .
H27A H 1.0240 0.0567 0.9641 0.112 Uiso 1 1 calc R . .
H27B H 1.0246 0.1388 1.0018 0.112 Uiso 1 1 calc R . .
H27C H 0.9873 0.1460 0.9416 0.112 Uiso 1 1 calc R . .
C28 C 0.6207(4) 0.0598(4) 1.04268(19) 0.0703(15) Uani 1 1 d . . .
H28A H 0.5800 0.0986 1.0223 0.105 Uiso 1 1 calc R . .
H28B H 0.6183 0.0749 1.0806 0.105 Uiso 1 1 calc R . .
H28C H 0.5981 0.0015 1.0379 0.105 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.224(5) . ?
O2 C4 1.214(5) . ?
O3 C22 1.208(7) . ?
O4 C3 1.340(5) . ?
O4 C26 1.437(6) . ?
O5 C10 1.362(5) . ?
O5 C27 1.425(6) . ?
O6 C11 1.374(5) . ?
O6 C28 1.411(6) . ?
O7 C19 1.355(5) . ?
O7 C25 1.433(5) . ?
O8 C18 1.369(5) . ?
O8 C24 1.415(6) . ?
O9 C22 1.324(6) . ?
O9 C21 1.456(5) . ?
C1 C2 1.449(6) . ?
C1 C6 1.492(5) . ?
C2 C3 1.334(6) . ?
C3 C4 1.490(6) . ?
C4 C5 1.472(6) . ?
C5 C6 1.337(6) . ?
C6 C7 1.500(5) . ?
C7 C8 1.522(5) . ?
C8 C13 1.389(5) . ?
C8 C9 1.399(5) . ?
C9 C10 1.380(6) . ?
C10 C11 1.401(6) . ?
C11 C12 1.382(6) . ?
C12 C13 1.403(6) . ?
C13 C14 1.514(5) . ?
C14 C15 1.518(6) . ?
C15 C20 1.389(5) . ?
C15 C16 1.397(6) . ?
C16 C17 1.391(6) . ?
C16 C21 1.498(6) . ?
C17 C18 1.366(6) . ?
C18 C19 1.407(6) . ?
C19 C20 1.388(6) . ?
C22 C23 1.494(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O4 C26 117.0(4) . . ?
C10 O5 C27 117.2(3) . . ?
C11 O6 C28 117.8(4) . . ?
C19 O7 C25 117.5(3) . . ?
C18 O8 C24 117.3(4) . . ?
C22 O9 C21 115.9(4) . . ?
O1 C1 C2 120.7(4) . . ?
O1 C1 C6 119.9(4) . . ?
C2 C1 C6 119.3(4) . . ?
C3 C2 C1 121.5(4) . . ?
C2 C3 O4 127.5(4) . . ?
C2 C3 C4 120.0(4) . . ?
O4 C3 C4 112.5(4) . . ?
O2 C4 C5 121.5(4) . . ?
O2 C4 C3 121.4(4) . . ?
C5 C4 C3 117.1(4) . . ?
C6 C5 C4 122.8(4) . . ?
C5 C6 C1 118.0(4) . . ?
C5 C6 C7 124.8(4) . . ?
C1 C6 C7 117.1(3) . . ?
C6 C7 C8 115.7(3) . . ?
C13 C8 C9 119.3(4) . . ?
C13 C8 C7 122.5(3) . . ?
C9 C8 C7 118.3(3) . . ?
C10 C9 C8 122.1(4) . . ?
O5 C10 C9 125.7(4) . . ?
O5 C10 C11 115.6(4) . . ?
C9 C10 C11 118.7(4) . . ?
O6 C11 C12 124.9(4) . . ?
O6 C11 C10 115.6(4) . . ?
C12 C11 C10 119.5(4) . . ?
C11 C12 C13 121.8(4) . . ?
C8 C13 C12 118.5(4) . . ?
C8 C13 C14 122.8(3) . . ?
C12 C13 C14 118.6(3) . . ?
C13 C14 C15 115.9(3) . . ?
C20 C15 C16 118.4(4) . . ?
C20 C15 C14 118.6(4) . . ?
C16 C15 C14 123.0(4) . . ?
C17 C16 C15 119.0(4) . . ?
C17 C16 C21 117.7(4) . . ?
C15 C16 C21 123.3(4) . . ?
C18 C17 C16 122.5(4) . . ?
C17 C18 O8 126.1(4) . . ?
C17 C18 C19 119.2(4) . . ?
O8 C18 C19 114.7(4) . . ?
O7 C19 C20 125.6(4) . . ?
O7 C19 C18 116.0(4) . . ?
C20 C19 C18 118.4(4) . . ?
C19 C20 C15 122.4(4) . . ?
O9 C21 C16 108.8(3) . . ?
O3 C22 O9 122.8(6) . . ?
O3 C22 C23 125.1(5) . . ?
O9 C22 C23 112.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -173.3(4) . . . . ?
C6 C1 C2 C3 7.4(6) . . . . ?
C1 C2 C3 O4 -179.8(4) . . . . ?
C1 C2 C3 C4 2.7(6) . . . . ?
C26 O4 C3 C2 4.3(7) . . . . ?
C26 O4 C3 C4 -178.0(4) . . . . ?
C2 C3 C4 O2 169.8(4) . . . . ?
O4 C3 C4 O2 -8.1(6) . . . . ?
C2 C3 C4 C5 -10.2(6) . . . . ?
O4 C3 C4 C5 172.0(4) . . . . ?
O2 C4 C5 C6 -172.2(4) . . . . ?
C3 C4 C5 C6 7.8(6) . . . . ?
C4 C5 C6 C1 1.9(6) . . . . ?
C4 C5 C6 C7 179.8(4) . . . . ?
O1 C1 C6 C5 170.9(4) . . . . ?
C2 C1 C6 C5 -9.7(5) . . . . ?
O1 C1 C6 C7 -7.1(5) . . . . ?
C2 C1 C6 C7 172.3(3) . . . . ?
C5 C6 C7 C8 15.0(6) . . . . ?
C1 C6 C7 C8 -167.1(3) . . . . ?
C6 C7 C8 C13 91.5(5) . . . . ?
C6 C7 C8 C9 -88.6(4) . . . . ?
C13 C8 C9 C10 1.5(6) . . . . ?
C7 C8 C9 C10 -178.3(4) . . . . ?
C27 O5 C10 C9 5.4(7) . . . . ?
C27 O5 C10 C11 -173.8(5) . . . . ?
C8 C9 C10 O5 -177.1(4) . . . . ?
C8 C9 C10 C11 2.1(6) . . . . ?
C28 O6 C11 C12 -1.2(7) . . . . ?
C28 O6 C11 C10 177.7(4) . . . . ?
O5 C10 C11 O6 -2.6(6) . . . . ?
C9 C10 C11 O6 178.2(4) . . . . ?
O5 C10 C11 C12 176.4(4) . . . . ?
C9 C10 C11 C12 -2.8(7) . . . . ?
O6 C11 C12 C13 178.9(4) . . . . ?
C10 C11 C12 C13 0.0(7) . . . . ?
C9 C8 C13 C12 -4.2(6) . . . . ?
C7 C8 C13 C12 175.6(4) . . . . ?
C9 C8 C13 C14 175.4(4) . . . . ?
C7 C8 C13 C14 -4.7(6) . . . . ?
C11 C12 C13 C8 3.5(6) . . . . ?
C11 C12 C13 C14 -176.1(4) . . . . ?
C8 C13 C14 C15 -60.9(5) . . . . ?
C12 C13 C14 C15 118.8(4) . . . . ?
C13 C14 C15 C20 122.3(4) . . . . ?
C13 C14 C15 C16 -57.0(5) . . . . ?
C20 C15 C16 C17 -2.3(5) . . . . ?
C14 C15 C16 C17 177.1(4) . . . . ?
C20 C15 C16 C21 176.3(4) . . . . ?
C14 C15 C16 C21 -4.4(6) . . . . ?
C15 C16 C17 C18 1.2(6) . . . . ?
C21 C16 C17 C18 -177.4(4) . . . . ?
C16 C17 C18 O8 179.7(4) . . . . ?
C16 C17 C18 C19 0.1(6) . . . . ?
C24 O8 C18 C17 -1.6(7) . . . . ?
C24 O8 C18 C19 178.1(4) . . . . ?
C25 O7 C19 C20 0.8(6) . . . . ?
C25 O7 C19 C18 -179.2(4) . . . . ?
C17 C18 C19 O7 179.7(4) . . . . ?
O8 C18 C19 O7 0.0(5) . . . . ?
C17 C18 C19 C20 -0.2(6) . . . . ?
O8 C18 C19 C20 -179.9(3) . . . . ?
O7 C19 C20 C15 179.1(4) . . . . ?
C18 C19 C20 C15 -0.9(6) . . . . ?
C16 C15 C20 C19 2.2(6) . . . . ?
C14 C15 C20 C19 -177.2(3) . . . . ?
C22 O9 C21 C16 -173.4(4) . . . . ?
C17 C16 C21 O9 -84.2(5) . . . . ?
C15 C16 C21 O9 97.2(5) . . . . ?
C21 O9 C22 O3 3.1(8) . . . . ?
C21 O9 C22 C23 -178.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate - Petroleum Ether'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 1027039'
_audit_update_record             
;
2014-09-30 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H32 O11, (CH3OH)'
_chemical_formula_sum            'C32 H36 O12'
_chemical_formula_weight         612.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9061(8)
_cell_length_b                   13.3097(10)
_cell_length_c                   21.2966(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.4670(10)
_cell_angle_gamma                90.00
_cell_volume                     3091.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4704
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      26.65

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            15301
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5436
_reflns_number_gt                4166
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0685P)²+1.1161P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5436
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50857(16) 0.33059(15) 0.20880(7) 0.0692(5) Uani 1 1 d . . .
O2 O 0.69239(14) 0.34165(13) 0.13458(7) 0.0568(4) Uani 1 1 d . . .
O3 O 0.17755(16) 0.41831(14) -0.23815(8) 0.0688(5) Uani 1 1 d . . .
O4 O 0.06734(17) 0.24929(15) -0.22618(8) 0.0748(6) Uani 1 1 d . . .
O5 O 0.07439(17) -0.09511(12) 0.07714(8) 0.0646(5) Uani 1 1 d . . .
O6 O -0.03598(16) 0.04167(13) 0.13970(8) 0.0684(5) Uani 1 1 d . . .
O7 O 0.34868(14) 0.06179(11) -0.07447(7) 0.0521(4) Uani 1 1 d . . .
O8 O 0.5455(2) 0.1000(2) -0.06994(18) 0.1475(14) Uani 1 1 d . . .
O9 O 0.13000(13) 0.37376(11) 0.07857(7) 0.0469(4) Uani 1 1 d . . .
O10 O 0.1699(3) 0.50873(17) 0.02079(11) 0.1101(9) Uani 1 1 d . . .
O11 O 0.51668(15) 0.41186(14) -0.07603(7) 0.0659(5) Uani 1 1 d . . .
C1 C 0.36379(19) 0.32279(16) 0.12177(10) 0.0456(5) Uani 1 1 d . . .
H1 H 0.2982 0.3136 0.1488 0.055 Uiso 1 1 calc R . .
C2 C 0.4798(2) 0.33099(17) 0.14668(10) 0.0474(5) Uani 1 1 d . . .
C3 C 0.57989(19) 0.34077(16) 0.10599(10) 0.0443(5) Uani 1 1 d . . .
C4 C 0.55851(19) 0.34960(16) 0.04280(10) 0.0432(5) Uani 1 1 d . . .
H4 H 0.6246 0.3597 0.0162 0.052 Uiso 1 1 calc R . .
C5 C 0.43469(19) 0.36182(16) -0.05252(10) 0.0447(5) Uani 1 1 d . . .
C6 C 0.3016(2) 0.38837(16) -0.14480(10) 0.0455(5) Uani 1 1 d . . .
H6 H 0.3409 0.4500 -0.1489 0.055 Uiso 1 1 calc R . .
C7 C 0.2128(2) 0.36164(17) -0.18756(10) 0.0480(5) Uani 1 1 d . . .
C8 C 0.1531(2) 0.26876(18) -0.18110(10) 0.0497(5) Uani 1 1 d . . .
C9 C 0.1855(2) 0.20488(17) -0.13267(9) 0.0464(5) Uani 1 1 d . . .
H9 H 0.1455 0.1436 -0.1285 0.056 Uiso 1 1 calc R . .
C10 C 0.3176(2) 0.15381(15) -0.04130(9) 0.0428(5) Uani 1 1 d . . .
H10 H 0.3911 0.1787 -0.0196 0.051 Uiso 1 1 calc R . .
C11 C 0.1898(2) 0.02843(16) 0.01790(10) 0.0453(5) Uani 1 1 d . . .
H11 H 0.2259 -0.0214 -0.0063 0.054 Uiso 1 1 calc R . .
C12 C 0.1066(2) 0.00154(16) 0.06327(10) 0.0467(5) Uani 1 1 d . . .
C13 C 0.0498(2) 0.07630(17) 0.09841(10) 0.0475(5) Uani 1 1 d . . .
C14 C 0.08245(19) 0.17538(17) 0.08986(10) 0.0453(5) Uani 1 1 d . . .
H14 H 0.0467 0.2246 0.1147 0.054 Uiso 1 1 calc R . .
C15 C 0.20688(18) 0.31339(15) 0.03748(10) 0.0413(5) Uani 1 1 d . . .
H15 H 0.1953 0.3348 -0.0062 0.050 Uiso 1 1 calc R . .
C16 C 0.34063(19) 0.32770(15) 0.05707(9) 0.0406(5) Uani 1 1 d . . .
C17 C 0.43953(18) 0.34383(15) 0.01686(9) 0.0409(5) Uani 1 1 d . . .
C18 C 0.33447(19) 0.32450(15) -0.09491(9) 0.0412(5) Uani 1 1 d . . .
C19 C 0.27772(19) 0.23114(16) -0.08985(9) 0.0415(5) Uani 1 1 d . . .
C20 C 0.22102(18) 0.12882(16) 0.00748(9) 0.0404(5) Uani 1 1 d . . .
C21 C 0.16833(18) 0.20368(16) 0.04457(9) 0.0399(5) Uani 1 1 d . . .
C22 C 0.4089(3) 0.3309(3) 0.25210(12) 0.0942(11) Uani 1 1 d . . .
H22A H 0.3573 0.3879 0.2440 0.141 Uiso 1 1 calc R . .
H22B H 0.4406 0.3346 0.2942 0.141 Uiso 1 1 calc R . .
H22C H 0.3621 0.2703 0.2472 0.141 Uiso 1 1 calc R . .
C23 C 0.7951(2) 0.3547(2) 0.09590(13) 0.0696(7) Uani 1 1 d . . .
H23A H 0.7974 0.3018 0.0652 0.104 Uiso 1 1 calc R . .
H23B H 0.8684 0.3527 0.1211 0.104 Uiso 1 1 calc R . .
H23C H 0.7895 0.4184 0.0750 0.104 Uiso 1 1 calc R . .
C24 C 0.2581(3) 0.4933(2) -0.25910(13) 0.0717(8) Uani 1 1 d . . .
H24A H 0.2558 0.5494 -0.2308 0.108 Uiso 1 1 calc R . .
H24B H 0.2336 0.5149 -0.3003 0.108 Uiso 1 1 calc R . .
H24C H 0.3399 0.4669 -0.2605 0.108 Uiso 1 1 calc R . .
C25 C 0.0126(4) 0.1535(3) -0.22710(15) 0.1037(13) Uani 1 1 d . . .
H25A H 0.0742 0.1034 -0.2344 0.155 Uiso 1 1 calc R . .
H25B H -0.0479 0.1508 -0.2601 0.155 Uiso 1 1 calc R . .
H25C H -0.0260 0.1410 -0.1875 0.155 Uiso 1 1 calc R . .
C26 C 0.1340(3) -0.17368(19) 0.04501(14) 0.0729(8) Uani 1 1 d . . .
H26A H 0.1172 -0.1682 0.0008 0.109 Uiso 1 1 calc R . .
H26B H 0.1047 -0.2372 0.0601 0.109 Uiso 1 1 calc R . .
H26C H 0.2209 -0.1691 0.0522 0.109 Uiso 1 1 calc R . .
C27 C -0.1037(3) 0.1117(2) 0.17480(14) 0.0769(8) Uani 1 1 d . . .
H27A H -0.0489 0.1500 0.2010 0.115 Uiso 1 1 calc R . .
H27B H -0.1615 0.0768 0.2006 0.115 Uiso 1 1 calc R . .
H27C H -0.1467 0.1561 0.1468 0.115 Uiso 1 1 calc R . .
C28 C 0.4659(3) 0.0421(2) -0.08347(14) 0.0703(7) Uani 1 1 d . . .
C29 C 0.4846(3) -0.0581(2) -0.11379(17) 0.0940(10) Uani 1 1 d . . .
H29A H 0.4504 -0.0571 -0.1555 0.141 Uiso 1 1 calc R . .
H29B H 0.4446 -0.1091 -0.0895 0.141 Uiso 1 1 calc R . .
H29C H 0.5707 -0.0724 -0.1158 0.141 Uiso 1 1 calc R . .
C30 C 0.1226(2) 0.47196(19) 0.06583(12) 0.0595(6) Uani 1 1 d . . .
C31 C 0.0543(3) 0.5298(2) 0.11382(15) 0.0773(8) Uani 1 1 d . . .
H31A H 0.1051 0.5387 0.1504 0.116 Uiso 1 1 calc R . .
H31B H -0.0186 0.4937 0.1250 0.116 Uiso 1 1 calc R . .
H31C H 0.0321 0.5942 0.0970 0.116 Uiso 1 1 calc R . .
C32 C 0.6733(6) 0.3208(5) 0.8024(3) 0.189(3) Uani 1 1 d . . .
H32A H 0.7328 0.3088 0.7703 0.284 Uiso 1 1 calc R . .
H32B H 0.5964 0.2914 0.7902 0.284 Uiso 1 1 calc R . .
H32C H 0.7010 0.2913 0.8411 0.284 Uiso 1 1 calc R . .
O12 O 0.6588(5) 0.4215(4) 0.8103(2) 0.1871(17) Uani 1 1 d . . .
H12A H 0.6099 0.4318 0.8387 0.281 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.357(3) . ?
O1 C22 1.431(3) . ?
O2 C3 1.365(3) . ?
O2 C23 1.406(3) . ?
O3 C7 1.368(3) . ?
O3 C24 1.405(3) . ?
O4 C8 1.360(3) . ?
O4 C25 1.408(3) . ?
O5 C12 1.366(3) . ?
O5 C26 1.412(3) . ?
O6 C13 1.369(3) . ?
O6 C27 1.408(3) . ?
O7 C28 1.320(3) . ?
O7 C10 1.455(2) . ?
O8 C28 1.194(4) . ?
O9 C30 1.337(3) . ?
O9 C15 1.458(2) . ?
O10 C30 1.197(3) . ?
O11 C5 1.225(2) . ?
C1 C2 1.372(3) . ?
C1 C16 1.400(3) . ?
C2 C3 1.405(3) . ?
C3 C4 1.369(3) . ?
C4 C17 1.408(3) . ?
C5 C18 1.497(3) . ?
C5 C17 1.497(3) . ?
C6 C7 1.371(3) . ?
C6 C18 1.405(3) . ?
C7 C8 1.405(3) . ?
C8 C9 1.381(3) . ?
C9 C19 1.396(3) . ?
C10 C19 1.520(3) . ?
C10 C20 1.522(3) . ?
C11 C12 1.378(3) . ?
C11 C20 1.397(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.378(3) . ?
C14 C21 1.401(3) . ?
C15 C16 1.526(3) . ?
C15 C21 1.527(3) . ?
C16 C17 1.399(3) . ?
C18 C19 1.393(3) . ?
C20 C21 1.398(3) . ?
C28 C29 1.497(4) . ?
C30 C31 1.485(4) . ?
C32 O12 1.360(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C22 117.2(2) . . ?
C3 O2 C23 117.19(18) . . ?
C7 O3 C24 118.00(19) . . ?
C8 O4 C25 118.1(2) . . ?
C12 O5 C26 118.19(18) . . ?
C13 O6 C27 118.81(19) . . ?
C28 O7 C10 117.87(19) . . ?
C30 O9 C15 116.80(17) . . ?
C2 C1 C16 122.35(19) . . ?
O1 C2 C1 125.6(2) . . ?
O1 C2 C3 115.26(19) . . ?
C1 C2 C3 119.16(19) . . ?
O2 C3 C4 125.65(19) . . ?
O2 C3 C2 115.20(18) . . ?
C4 C3 C2 119.15(19) . . ?
C3 C4 C17 121.99(19) . . ?
O11 C5 C18 117.76(19) . . ?
O11 C5 C17 118.04(19) . . ?
C18 C5 C17 124.18(18) . . ?
C7 C6 C18 121.3(2) . . ?
O3 C7 C6 124.9(2) . . ?
O3 C7 C8 115.8(2) . . ?
C6 C7 C8 119.3(2) . . ?
O4 C8 C9 125.5(2) . . ?
O4 C8 C7 114.54(19) . . ?
C9 C8 C7 119.9(2) . . ?
C8 C9 C19 120.8(2) . . ?
O7 C10 C19 107.83(16) . . ?
O7 C10 C20 108.23(16) . . ?
C19 C10 C20 114.64(17) . . ?
C12 C11 C20 121.5(2) . . ?
O5 C12 C11 124.6(2) . . ?
O5 C12 C13 116.11(19) . . ?
C11 C12 C13 119.3(2) . . ?
O6 C13 C14 125.8(2) . . ?
O6 C13 C12 114.4(2) . . ?
C14 C13 C12 119.72(19) . . ?
C13 C14 C21 121.5(2) . . ?
O9 C15 C16 108.67(16) . . ?
O9 C15 C21 107.91(15) . . ?
C16 C15 C21 110.83(17) . . ?
C17 C16 C1 118.39(19) . . ?
C17 C16 C15 126.29(18) . . ?
C1 C16 C15 115.31(17) . . ?
C16 C17 C4 118.74(19) . . ?
C16 C17 C5 127.39(19) . . ?
C4 C17 C5 113.78(17) . . ?
C19 C18 C6 119.18(19) . . ?
C19 C18 C5 124.91(19) . . ?
C6 C18 C5 115.84(19) . . ?
C18 C19 C9 119.40(19) . . ?
C18 C19 C10 122.15(19) . . ?
C9 C19 C10 118.36(19) . . ?
C11 C20 C21 119.35(18) . . ?
C11 C20 C10 119.23(19) . . ?
C21 C20 C10 121.31(18) . . ?
C20 C21 C14 118.51(19) . . ?
C20 C21 C15 120.72(17) . . ?
C14 C21 C15 120.73(18) . . ?
O8 C28 O7 122.7(3) . . ?
O8 C28 C29 125.3(3) . . ?
O7 C28 C29 112.0(3) . . ?
O10 C30 O9 122.5(2) . . ?
O10 C30 C31 124.2(3) . . ?
O9 C30 C31 113.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O1 C2 C1 -6.1(4) . . . . ?
C22 O1 C2 C3 174.0(3) . . . . ?
C16 C1 C2 O1 177.5(2) . . . . ?
C16 C1 C2 C3 -2.5(3) . . . . ?
C23 O2 C3 C4 1.3(3) . . . . ?
C23 O2 C3 C2 -177.9(2) . . . . ?
O1 C2 C3 O2 4.2(3) . . . . ?
C1 C2 C3 O2 -175.8(2) . . . . ?
O1 C2 C3 C4 -175.1(2) . . . . ?
C1 C2 C3 C4 5.0(3) . . . . ?
O2 C3 C4 C17 177.4(2) . . . . ?
C2 C3 C4 C17 -3.5(3) . . . . ?
C24 O3 C7 C6 19.5(3) . . . . ?
C24 O3 C7 C8 -159.4(2) . . . . ?
C18 C6 C7 O3 -178.4(2) . . . . ?
C18 C6 C7 C8 0.4(3) . . . . ?
C25 O4 C8 C9 -5.0(4) . . . . ?
C25 O4 C8 C7 173.3(3) . . . . ?
O3 C7 C8 O4 -0.6(3) . . . . ?
C6 C7 C8 O4 -179.5(2) . . . . ?
O3 C7 C8 C9 177.8(2) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
O4 C8 C9 C19 178.0(2) . . . . ?
C7 C8 C9 C19 -0.2(3) . . . . ?
C28 O7 C10 C19 101.3(2) . . . . ?
C28 O7 C10 C20 -134.2(2) . . . . ?
C26 O5 C12 C11 3.0(3) . . . . ?
C26 O5 C12 C13 -176.8(2) . . . . ?
C20 C11 C12 O5 -178.1(2) . . . . ?
C20 C11 C12 C13 1.8(3) . . . . ?
C27 O6 C13 C14 3.9(4) . . . . ?
C27 O6 C13 C12 -176.3(2) . . . . ?
O5 C12 C13 O6 -3.5(3) . . . . ?
C11 C12 C13 O6 176.6(2) . . . . ?
O5 C12 C13 C14 176.3(2) . . . . ?
C11 C12 C13 C14 -3.6(3) . . . . ?
O6 C13 C14 C21 -177.6(2) . . . . ?
C12 C13 C14 C21 2.7(3) . . . . ?
C30 O9 C15 C16 79.4(2) . . . . ?
C30 O9 C15 C21 -160.34(19) . . . . ?
C2 C1 C16 C17 -1.5(3) . . . . ?
C2 C1 C16 C15 177.9(2) . . . . ?
O9 C15 C16 C17 -135.3(2) . . . . ?
C21 C15 C16 C17 106.3(2) . . . . ?
O9 C15 C16 C1 45.4(2) . . . . ?
C21 C15 C16 C1 -73.0(2) . . . . ?
C1 C16 C17 C4 3.0(3) . . . . ?
C15 C16 C17 C4 -176.28(19) . . . . ?
C1 C16 C17 C5 -173.4(2) . . . . ?
C15 C16 C17 C5 7.3(3) . . . . ?
C3 C4 C17 C16 -0.6(3) . . . . ?
C3 C4 C17 C5 176.31(19) . . . . ?
O11 C5 C17 C16 151.6(2) . . . . ?
C18 C5 C17 C16 -27.0(3) . . . . ?
O11 C5 C17 C4 -25.0(3) . . . . ?
C18 C5 C17 C4 156.5(2) . . . . ?
C7 C6 C18 C19 1.6(3) . . . . ?
C7 C6 C18 C5 178.65(19) . . . . ?
O11 C5 C18 C19 142.6(2) . . . . ?
C17 C5 C18 C19 -38.9(3) . . . . ?
O11 C5 C18 C6 -34.2(3) . . . . ?
C17 C5 C18 C6 144.3(2) . . . . ?
C6 C18 C19 C9 -2.9(3) . . . . ?
C5 C18 C19 C9 -179.64(19) . . . . ?
C6 C18 C19 C10 173.58(18) . . . . ?
C5 C18 C19 C10 -3.1(3) . . . . ?
C8 C9 C19 C18 2.2(3) . . . . ?
C8 C9 C19 C10 -174.39(19) . . . . ?
O7 C10 C19 C18 -123.5(2) . . . . ?
C20 C10 C19 C18 115.9(2) . . . . ?
O7 C10 C19 C9 53.0(2) . . . . ?
C20 C10 C19 C9 -67.6(2) . . . . ?
C12 C11 C20 C21 1.1(3) . . . . ?
C12 C11 C20 C10 177.37(19) . . . . ?
O7 C10 C20 C11 7.2(3) . . . . ?
C19 C10 C20 C11 127.6(2) . . . . ?
O7 C10 C20 C21 -176.62(17) . . . . ?
C19 C10 C20 C21 -56.2(3) . . . . ?
C11 C20 C21 C14 -2.0(3) . . . . ?
C10 C20 C21 C14 -178.23(18) . . . . ?
C11 C20 C21 C15 175.83(18) . . . . ?
C10 C20 C21 C15 -0.4(3) . . . . ?
C13 C14 C21 C20 0.2(3) . . . . ?
C13 C14 C21 C15 -177.7(2) . . . . ?
O9 C15 C21 C20 175.74(17) . . . . ?
C16 C15 C21 C20 -65.4(2) . . . . ?
O9 C15 C21 C14 -6.5(3) . . . . ?
C16 C15 C21 C14 112.4(2) . . . . ?
C10 O7 C28 O8 -5.9(5) . . . . ?
C10 O7 C28 C29 175.8(2) . . . . ?
C15 O9 C30 O10 4.6(4) . . . . ?
C15 O9 C30 C31 -173.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8
_database_code_depnum_ccdc_archive 'CCDC 1027040'
_audit_update_record             
;
2014-09-30 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H26 O7, 0.5(H2O)'
_chemical_formula_sum            'C27 H27 O7.50'
_chemical_formula_weight         471.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.2799(12)
_cell_length_b                   15.4053(14)
_cell_length_c                   26.172(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.352(2)
_cell_angle_gamma                90.00
_cell_volume                     5267.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    3569
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      21.57

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26214
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             9218
_reflns_number_gt                5913
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0744P)²+1.0783P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9218
_refine_ls_number_parameters     652
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05359(18) 0.27639(13) 0.32093(8) 0.0725(6) Uani 1 1 d . . .
O2 O 0.01235(14) 0.00245(11) 0.20513(7) 0.0518(5) Uani 1 1 d . . .
O3 O -0.00537(15) 0.05937(11) 0.11187(7) 0.0557(5) Uani 1 1 d . . .
O4 O -0.31843(15) 0.56446(13) 0.17879(9) 0.0683(6) Uani 1 1 d . . .
O5 O -0.30932(15) 0.40821(14) 0.21307(9) 0.0741(6) Uani 1 1 d . . .
O6 O 0.38489(13) 0.35478(10) 0.14249(7) 0.0476(5) Uani 1 1 d . . .
O7 O 0.37701(13) 0.51007(11) 0.11179(8) 0.0536(5) Uani 1 1 d . . .
C1 C 0.03816(17) 0.23805(15) 0.23192(9) 0.0374(6) Uani 1 1 d . . .
C2 C 0.02847(18) 0.26912(15) 0.18132(10) 0.0383(6) Uani 1 1 d . . .
C3 C 0.01421(19) 0.20945(15) 0.14041(10) 0.0419(6) Uani 1 1 d . . .
H3 H 0.0084 0.2297 0.1061 0.050 Uiso 1 1 calc R . .
C4 C 0.00852(19) 0.12174(16) 0.14934(10) 0.0408(6) Uani 1 1 d . . .
C5 C 0.01870(18) 0.09062(15) 0.20069(10) 0.0397(6) Uani 1 1 d . . .
C6 C 0.03269(18) 0.14837(16) 0.24099(10) 0.0411(6) Uani 1 1 d . . .
H6 H 0.0387 0.1279 0.2752 0.049 Uiso 1 1 calc R . .
C7 C -0.1525(2) 0.55323(17) 0.15305(11) 0.0508(7) Uani 1 1 d . . .
H7 H -0.1568 0.6101 0.1399 0.061 Uiso 1 1 calc R . .
C8 C -0.2307(2) 0.52114(18) 0.17396(12) 0.0538(7) Uani 1 1 d . . .
C9 C -0.2261(2) 0.43354(18) 0.19284(12) 0.0542(7) Uani 1 1 d . . .
C10 C -0.1449(2) 0.38239(17) 0.18890(11) 0.0499(7) Uani 1 1 d . . .
H10 H -0.1449 0.3242 0.1997 0.060 Uiso 1 1 calc R . .
C11 C -0.05944(18) 0.41461(15) 0.16878(10) 0.0408(6) Uani 1 1 d . . .
C12 C 0.02832(19) 0.36402(15) 0.16744(10) 0.0393(6) Uani 1 1 d . . .
C13 C 0.11413(18) 0.40071(15) 0.15127(9) 0.0368(6) Uani 1 1 d . . .
C14 C 0.20800(18) 0.35373(15) 0.15402(9) 0.0392(6) Uani 1 1 d . . .
H14 H 0.2118 0.2957 0.1652 0.047 Uiso 1 1 calc R . .
C15 C 0.29159(18) 0.39213(15) 0.14061(9) 0.0380(6) Uani 1 1 d . . .
C16 C 0.28683(19) 0.48043(15) 0.12254(9) 0.0392(6) Uani 1 1 d . . .
C17 C 0.19850(19) 0.52547(16) 0.11800(10) 0.0423(6) Uani 1 1 d . . .
H17 H 0.1954 0.5823 0.1048 0.051 Uiso 1 1 calc R . .
C18 C 0.10967(19) 0.48836(15) 0.13290(9) 0.0385(6) Uani 1 1 d . . .
C19 C 0.0200(2) 0.53599(16) 0.13187(10) 0.0441(6) Uani 1 1 d . . .
H4 H 0.0160 0.5925 0.1181 0.053 Uiso 1 1 calc R . .
C20 C -0.06360(19) 0.50259(16) 0.15056(10) 0.0427(6) Uani 1 1 d . . .
C21 C 0.0526(2) 0.29731(18) 0.27625(11) 0.0519(7) Uani 1 1 d . . .
H21 H 0.0617 0.3564 0.2695 0.062 Uiso 1 1 calc R . .
C22 C 0.0303(2) -0.03211(18) 0.25687(11) 0.0585(8) Uani 1 1 d . . .
H22A H 0.0948 -0.0101 0.2758 0.088 Uiso 1 1 calc R . .
H22B H 0.0331 -0.0950 0.2554 0.088 Uiso 1 1 calc R . .
H22C H -0.0248 -0.0146 0.2745 0.088 Uiso 1 1 calc R . .
C23 C -0.0173(3) 0.0883(2) 0.05939(11) 0.0732(10) Uani 1 1 d . . .
H23A H -0.0777 0.1247 0.0514 0.110 Uiso 1 1 calc R . .
H23B H -0.0249 0.0385 0.0363 0.110 Uiso 1 1 calc R . .
H23C H 0.0425 0.1213 0.0547 0.110 Uiso 1 1 calc R . .
C24 C -0.3284(2) 0.6510(2) 0.15940(15) 0.0780(10) Uani 1 1 d . . .
H24A H -0.2711 0.6855 0.1766 0.117 Uiso 1 1 calc R . .
H24B H -0.3918 0.6759 0.1661 0.117 Uiso 1 1 calc R . .
H24C H -0.3290 0.6505 0.1223 0.117 Uiso 1 1 calc R . .
C25 C -0.3116(3) 0.3192(3) 0.2285(2) 0.1164(17) Uani 1 1 d . . .
H25A H -0.3093 0.2821 0.1987 0.175 Uiso 1 1 calc R . .
H25B H -0.3741 0.3080 0.2417 0.175 Uiso 1 1 calc R . .
H25C H -0.2530 0.3072 0.2554 0.175 Uiso 1 1 calc R . .
C26 C 0.3957(2) 0.26577(16) 0.15818(13) 0.0614(8) Uani 1 1 d . . .
H26A H 0.3850 0.2604 0.1937 0.092 Uiso 1 1 calc R . .
H26B H 0.4639 0.2457 0.1558 0.092 Uiso 1 1 calc R . .
H26C H 0.3454 0.2309 0.1356 0.092 Uiso 1 1 calc R . .
C27 C 0.3795(2) 0.59805(17) 0.09512(13) 0.0636(8) Uani 1 1 d . . .
H27A H 0.3288 0.6064 0.0638 0.095 Uiso 1 1 calc R . .
H27B H 0.4470 0.6114 0.0879 0.095 Uiso 1 1 calc R . .
H27C H 0.3644 0.6362 0.1222 0.095 Uiso 1 1 calc R . .
O1' O 0.1765(2) 0.77971(14) 0.21721(9) 0.0946(8) Uani 1 1 d . . .
O2' O 0.30148(17) 1.08619(11) 0.18821(7) 0.0650(6) Uani 1 1 d . . .
O3' O 0.28310(18) 1.10170(12) 0.08847(8) 0.0740(7) Uani 1 1 d . . .
O4' O -0.25029(13) 0.68990(12) 0.03341(7) 0.0540(5) Uani 1 1 d . . .
O5' O -0.19242(13) 0.81409(13) 0.09563(8) 0.0585(5) Uani 1 1 d . . .
O6' O 0.49989(13) 0.76537(13) 0.01907(8) 0.0601(5) Uani 1 1 d . . .
O7' O 0.43768(14) 0.65386(14) -0.05041(8) 0.0707(6) Uani 1 1 d . . .
C1' C 0.20141(18) 0.86886(14) 0.14749(9) 0.0361(6) Uani 1 1 d . . .
C2' C 0.19125(17) 0.87664(15) 0.09388(9) 0.0362(6) Uani 1 1 d . . .
C3' C 0.21783(19) 0.95552(15) 0.07349(10) 0.0420(6) Uani 1 1 d . . .
H3' H 0.2108 0.9621 0.0373 0.050 Uiso 1 1 calc R . .
C4' C 0.2543(2) 1.02401(16) 0.10570(10) 0.0460(7) Uani 1 1 d . . .
C5' C 0.2641(2) 1.01561(15) 0.15970(10) 0.0441(6) Uani 1 1 d . . .
C6' C 0.23728(19) 0.93876(15) 0.17989(10) 0.0412(6) Uani 1 1 d . . .
H6' H 0.2431 0.9328 0.2161 0.049 Uiso 1 1 calc R . .
C7' C -0.08485(18) 0.67803(16) 0.00716(10) 0.0426(6) Uani 1 1 d . . .
H7' H -0.1075 0.6333 -0.0166 0.051 Uiso 1 1 calc R . .
C8' C -0.15067(18) 0.71313(16) 0.03532(10) 0.0416(6) Uani 1 1 d . . .
C9' C -0.11799(19) 0.78269(16) 0.07078(10) 0.0426(6) Uani 1 1 d . . .
C10' C -0.02095(18) 0.81372(16) 0.07670(10) 0.0410(6) Uani 1 1 d . . .
H10' H -0.0016 0.8608 0.0992 0.049 Uiso 1 1 calc R . .
C11' C 0.05209(18) 0.77623(15) 0.04946(9) 0.0369(6) Uani 1 1 d . . .
C12' C 0.15453(18) 0.80432(14) 0.05680(9) 0.0362(6) Uani 1 1 d . . .
C13' C 0.22439(18) 0.76619(15) 0.02877(9) 0.0367(6) Uani 1 1 d . . .
C14' C 0.33038(18) 0.78917(15) 0.03761(10) 0.0407(6) Uani 1 1 d . . .
H14' H 0.3545 0.8318 0.0625 0.049 Uiso 1 1 calc R . .
C15' C 0.39656(19) 0.75127(17) 0.01116(11) 0.0458(7) Uani 1 1 d . . .
C16' C 0.3620(2) 0.68722(17) -0.02784(11) 0.0492(7) Uani 1 1 d . . .
C17' C 0.2618(2) 0.66349(17) -0.03729(10) 0.0476(7) Uani 1 1 d . . .
H17' H 0.2393 0.6217 -0.0630 0.057 Uiso 1 1 calc R . .
C18' C 0.19015(19) 0.70048(15) -0.00910(10) 0.0405(6) Uani 1 1 d . . .
C19' C 0.08824(19) 0.67265(16) -0.01545(10) 0.0426(6) Uani 1 1 d . . .
H19' H 0.0659 0.6287 -0.0397 0.051 Uiso 1 1 calc R . .
C20' C 0.01869(18) 0.70789(15) 0.01299(9) 0.0364(6) Uani 1 1 d . . .
C21' C 0.1774(2) 0.78793(17) 0.17176(12) 0.0524(7) Uani 1 1 d . . .
H58 H 0.1615 0.7391 0.1503 0.063 Uiso 1 1 calc R . .
C22' C 0.3246(3) 1.07578(19) 0.24329(11) 0.0728(10) Uani 1 1 d . . .
H22D H 0.2622 1.0629 0.2562 0.109 Uiso 1 1 calc R . .
H22E H 0.3545 1.1290 0.2591 0.109 Uiso 1 1 calc R . .
H22F H 0.3728 1.0284 0.2519 0.109 Uiso 1 1 calc R . .
C23' C 0.2909(3) 1.1090(2) 0.03493(13) 0.0904(12) Uani 1 1 d . . .
H23D H 0.3333 1.0624 0.0257 0.136 Uiso 1 1 calc R . .
H23E H 0.3216 1.1645 0.0290 0.136 Uiso 1 1 calc R . .
H23F H 0.2232 1.1053 0.0137 0.136 Uiso 1 1 calc R . .
C24' C -0.2912(2) 0.6242(2) -0.00280(14) 0.0751(10) Uani 1 1 d . . .
H24E H -0.2866 0.6430 -0.0377 0.113 Uiso 1 1 calc R . .
H24F H -0.3623 0.6140 -0.0005 0.113 Uiso 1 1 calc R . .
H24D H -0.2525 0.5710 0.0052 0.113 Uiso 1 1 calc R . .
C25' C -0.1653(3) 0.8847(2) 0.13051(16) 0.0956(13) Uani 1 1 d . . .
H25D H -0.1085 0.8678 0.1574 0.143 Uiso 1 1 calc R . .
H25E H -0.2235 0.9003 0.1463 0.143 Uiso 1 1 calc R . .
H25F H -0.1454 0.9341 0.1116 0.143 Uiso 1 1 calc R . .
C26' C 0.5409(2) 0.8241(2) 0.05950(12) 0.0669(9) Uani 1 1 d . . .
H26F H 0.5158 0.8822 0.0503 0.100 Uiso 1 1 calc R . .
H26D H 0.6150 0.8237 0.0642 0.100 Uiso 1 1 calc R . .
H26E H 0.5197 0.8065 0.0915 0.100 Uiso 1 1 calc R . .
C27' C 0.4138(3) 0.5837(2) -0.08478(16) 0.0926(13) Uani 1 1 d . . .
H27E H 0.3887 0.5356 -0.0667 0.139 Uiso 1 1 calc R . .
H27D H 0.4747 0.5658 -0.0976 0.139 Uiso 1 1 calc R . .
H27F H 0.3615 0.6012 -0.1137 0.139 Uiso 1 1 calc R . .
O8 O 0.636(3) 0.0799(17) 0.0851(12) 0.40(2) Uani 0.25 1 d PU . .
O9 O 0.5687(13) 0.0084(15) 0.1701(7) 0.402(11) Uani 0.50 1 d PU . .
O10 O 0.7308(17) 0.1059(15) 0.1700(17) 0.39(2) Uani 0.25 1 d PU . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.210(3) . ?
O2 C5 1.367(3) . ?
O2 C22 1.435(3) . ?
O3 C4 1.361(3) . ?
O3 C23 1.425(3) . ?
O4 C8 1.368(3) . ?
O4 C24 1.424(3) . ?
O5 C9 1.365(3) . ?
O5 C25 1.431(4) . ?
O6 C15 1.359(3) . ?
O6 C26 1.431(3) . ?
O7 C16 1.358(3) . ?
O7 C27 1.426(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.406(3) . ?
C1 C21 1.462(4) . ?
C2 C3 1.398(3) . ?
C2 C12 1.506(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.410(3) . ?
C5 C6 1.367(3) . ?
C7 C8 1.351(4) . ?
C7 C20 1.427(3) . ?
C8 C9 1.435(4) . ?
C9 C10 1.355(4) . ?
C10 C11 1.423(3) . ?
C11 C12 1.408(3) . ?
C11 C20 1.435(3) . ?
C12 C13 1.404(3) . ?
C13 C18 1.431(3) . ?
C13 C14 1.432(3) . ?
C14 C15 1.358(3) . ?
C15 C16 1.438(3) . ?
C16 C17 1.350(3) . ?
C17 C18 1.427(3) . ?
C18 C19 1.395(3) . ?
C19 C20 1.390(3) . ?
O1' C21' 1.198(3) . ?
O2' C5' 1.361(3) . ?
O2' C22' 1.428(3) . ?
O3' C4' 1.358(3) . ?
O3' C23' 1.428(4) . ?
O4' C8' 1.363(3) . ?
O4' C24' 1.425(3) . ?
O5' C9' 1.366(3) . ?
O5' C25' 1.424(3) . ?
O6' C15' 1.368(3) . ?
O6' C26' 1.424(3) . ?
O7' C16' 1.355(3) . ?
O7' C27' 1.406(4) . ?
C1' C2' 1.390(3) . ?
C1' C6' 1.400(3) . ?
C1' C21' 1.460(3) . ?
C2' C3' 1.398(3) . ?
C2' C12' 1.500(3) . ?
C3' C4' 1.383(3) . ?
C4' C5' 1.402(4) . ?
C5' C6' 1.369(3) . ?
C7' C8' 1.353(3) . ?
C7' C20' 1.432(3) . ?
C8' C9' 1.433(3) . ?
C9' C10' 1.357(3) . ?
C10' C11' 1.425(3) . ?
C11' C12' 1.407(3) . ?
C11' C20' 1.437(3) . ?
C12' C13' 1.410(3) . ?
C13' C14' 1.429(3) . ?
C13' C18' 1.432(3) . ?
C14' C15' 1.346(3) . ?
C15' C16' 1.435(4) . ?
C16' C17' 1.359(3) . ?
C17' C18' 1.424(3) . ?
C18' C19' 1.401(3) . ?
C19' C20' 1.396(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C22 116.5(2) . . ?
C4 O3 C23 116.8(2) . . ?
C8 O4 C24 116.7(2) . . ?
C9 O5 C25 116.3(2) . . ?
C15 O6 C26 117.36(19) . . ?
C16 O7 C27 116.9(2) . . ?
C2 C1 C6 120.0(2) . . ?
C2 C1 C21 121.1(2) . . ?
C6 C1 C21 118.9(2) . . ?
C1 C2 C3 118.6(2) . . ?
C1 C2 C12 124.0(2) . . ?
C3 C2 C12 117.3(2) . . ?
C4 C3 C2 121.3(2) . . ?
O3 C4 C3 125.1(2) . . ?
O3 C4 C5 115.1(2) . . ?
C3 C4 C5 119.8(2) . . ?
C6 C5 O2 125.7(2) . . ?
C6 C5 C4 119.4(2) . . ?
O2 C5 C4 115.0(2) . . ?
C5 C6 C1 120.9(2) . . ?
C8 C7 C20 121.4(3) . . ?
C7 C8 O4 126.0(3) . . ?
C7 C8 C9 119.7(2) . . ?
O4 C8 C9 114.3(2) . . ?
C10 C9 O5 125.1(3) . . ?
C10 C9 C8 120.4(3) . . ?
O5 C9 C8 114.5(2) . . ?
C9 C10 C11 121.6(2) . . ?
C12 C11 C10 122.3(2) . . ?
C12 C11 C20 119.8(2) . . ?
C10 C11 C20 117.8(2) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 C2 119.8(2) . . ?
C11 C12 C2 119.8(2) . . ?
C12 C13 C18 119.6(2) . . ?
C12 C13 C14 121.9(2) . . ?
C18 C13 C14 118.5(2) . . ?
C15 C14 C13 120.8(2) . . ?
C14 C15 O6 126.0(2) . . ?
C14 C15 C16 120.5(2) . . ?
O6 C15 C16 113.5(2) . . ?
C17 C16 O7 126.4(2) . . ?
C17 C16 C15 120.1(2) . . ?
O7 C16 C15 113.5(2) . . ?
C16 C17 C18 121.2(2) . . ?
C19 C18 C17 121.9(2) . . ?
C19 C18 C13 119.1(2) . . ?
C17 C18 C13 118.9(2) . . ?
C20 C19 C18 122.1(2) . . ?
C19 C20 C7 122.3(2) . . ?
C19 C20 C11 118.8(2) . . ?
C7 C20 C11 119.0(2) . . ?
O1 C21 C1 125.3(3) . . ?
C5' O2' C22' 117.1(2) . . ?
C4' O3' C23' 118.0(2) . . ?
C8' O4' C24' 117.5(2) . . ?
C9' O5' C25' 117.0(2) . . ?
C15' O6' C26' 116.9(2) . . ?
C16' O7' C27' 118.1(2) . . ?
C2' C1' C6' 120.4(2) . . ?
C2' C1' C21' 121.6(2) . . ?
C6' C1' C21' 118.1(2) . . ?
C1' C2' C3' 118.4(2) . . ?
C1' C2' C12' 123.4(2) . . ?
C3' C2' C12' 118.3(2) . . ?
C4' C3' C2' 121.0(2) . . ?
O3' C4' C3' 124.0(2) . . ?
O3' C4' C5' 115.8(2) . . ?
C3' C4' C5' 120.2(2) . . ?
O2' C5' C6' 125.0(2) . . ?
O2' C5' C4' 115.9(2) . . ?
C6' C5' C4' 119.0(2) . . ?
C5' C6' C1' 121.0(2) . . ?
C8' C7' C20' 121.0(2) . . ?
C7' C8' O4' 126.4(2) . . ?
C7' C8' C9' 120.1(2) . . ?
O4' C8' C9' 113.5(2) . . ?
C10' C9' O5' 125.1(2) . . ?
C10' C9' C8' 120.6(2) . . ?
O5' C9' C8' 114.4(2) . . ?
C9' C10' C11' 121.2(2) . . ?
C12' C11' C10' 122.3(2) . . ?
C12' C11' C20' 119.4(2) . . ?
C10' C11' C20' 118.2(2) . . ?
C11' C12' C13' 120.7(2) . . ?
C11' C12' C2' 120.7(2) . . ?
C13' C12' C2' 118.6(2) . . ?
C12' C13' C14' 122.2(2) . . ?
C12' C13' C18' 119.8(2) . . ?
C14' C13' C18' 117.9(2) . . ?
C15' C14' C13' 121.6(2) . . ?
C14' C15' O6' 125.7(2) . . ?
C14' C15' C16' 120.6(2) . . ?
O6' C15' C16' 113.6(2) . . ?
O7' C16' C17' 126.7(3) . . ?
O7' C16' C15' 113.8(2) . . ?
C17' C16' C15' 119.5(2) . . ?
C16' C17' C18' 121.4(2) . . ?
C19' C18' C17' 122.5(2) . . ?
C19' C18' C13' 118.6(2) . . ?
C17' C18' C13' 118.9(2) . . ?
C20' C19' C18' 122.4(2) . . ?
C19' C20' C7' 122.2(2) . . ?
C19' C20' C11' 119.0(2) . . ?
C7' C20' C11' 118.8(2) . . ?
O1' C21' C1' 124.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.5(3) . . . . ?
C21 C1 C2 C3 -179.6(2) . . . . ?
C6 C1 C2 C12 177.0(2) . . . . ?
C21 C1 C2 C12 -2.1(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C12 C2 C3 C4 -177.0(2) . . . . ?
C23 O3 C4 C3 -1.6(4) . . . . ?
C23 O3 C4 C5 179.2(2) . . . . ?
C2 C3 C4 O3 179.9(2) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C22 O2 C5 C6 -5.4(3) . . . . ?
C22 O2 C5 C4 175.3(2) . . . . ?
O3 C4 C5 C6 -179.8(2) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
O3 C4 C5 O2 -0.5(3) . . . . ?
C3 C4 C5 O2 -179.7(2) . . . . ?
O2 C5 C6 C1 180.0(2) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C21 C1 C6 C5 179.6(2) . . . . ?
C20 C7 C8 O4 179.1(3) . . . . ?
C20 C7 C8 C9 -1.8(4) . . . . ?
C24 O4 C8 C7 0.8(4) . . . . ?
C24 O4 C8 C9 -178.4(3) . . . . ?
C25 O5 C9 C10 -3.5(5) . . . . ?
C25 O5 C9 C8 175.1(3) . . . . ?
C7 C8 C9 C10 -1.3(4) . . . . ?
O4 C8 C9 C10 177.9(3) . . . . ?
C7 C8 C9 O5 -180.0(3) . . . . ?
O4 C8 C9 O5 -0.8(4) . . . . ?
O5 C9 C10 C11 -178.0(3) . . . . ?
C8 C9 C10 C11 3.5(4) . . . . ?
C9 C10 C11 C12 175.9(3) . . . . ?
C9 C10 C11 C20 -2.6(4) . . . . ?
C10 C11 C12 C13 -174.7(2) . . . . ?
C20 C11 C12 C13 3.8(4) . . . . ?
C10 C11 C12 C2 7.8(4) . . . . ?
C20 C11 C12 C2 -173.7(2) . . . . ?
C1 C2 C12 C13 106.6(3) . . . . ?
C3 C2 C12 C13 -75.8(3) . . . . ?
C1 C2 C12 C11 -75.9(3) . . . . ?
C3 C2 C12 C11 101.7(3) . . . . ?
C11 C12 C13 C18 -4.1(4) . . . . ?
C2 C12 C13 C18 173.4(2) . . . . ?
C11 C12 C13 C14 174.0(2) . . . . ?
C2 C12 C13 C14 -8.5(4) . . . . ?
C12 C13 C14 C15 -176.6(2) . . . . ?
C18 C13 C14 C15 1.5(4) . . . . ?
C13 C14 C15 O6 178.8(2) . . . . ?
C13 C14 C15 C16 -1.0(4) . . . . ?
C26 O6 C15 C14 2.5(4) . . . . ?
C26 O6 C15 C16 -177.7(2) . . . . ?
C27 O7 C16 C17 1.5(4) . . . . ?
C27 O7 C16 C15 -178.2(2) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
O6 C15 C16 C17 179.1(2) . . . . ?
C14 C15 C16 O7 178.6(2) . . . . ?
O6 C15 C16 O7 -1.2(3) . . . . ?
O7 C16 C17 C18 -177.0(2) . . . . ?
C15 C16 C17 C18 2.6(4) . . . . ?
C16 C17 C18 C19 175.5(2) . . . . ?
C16 C17 C18 C13 -2.1(4) . . . . ?
C12 C13 C18 C19 0.6(3) . . . . ?
C14 C13 C18 C19 -177.6(2) . . . . ?
C12 C13 C18 C17 178.2(2) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
C17 C18 C19 C20 -174.3(2) . . . . ?
C13 C18 C19 C20 3.3(4) . . . . ?
C18 C19 C20 C7 175.4(2) . . . . ?
C18 C19 C20 C11 -3.5(4) . . . . ?
C8 C7 C20 C19 -176.3(3) . . . . ?
C8 C7 C20 C11 2.6(4) . . . . ?
C12 C11 C20 C19 0.0(4) . . . . ?
C10 C11 C20 C19 178.5(2) . . . . ?
C12 C11 C20 C7 -179.0(2) . . . . ?
C10 C11 C20 C7 -0.4(4) . . . . ?
C2 C1 C21 O1 173.9(3) . . . . ?
C6 C1 C21 O1 -5.2(4) . . . . ?
C6' C1' C2' C3' 0.1(3) . . . . ?
C21' C1' C2' C3' -178.6(2) . . . . ?
C6' C1' C2' C12' 179.3(2) . . . . ?
C21' C1' C2' C12' 0.6(4) . . . . ?
C1' C2' C3' C4' 0.7(4) . . . . ?
C12' C2' C3' C4' -178.6(2) . . . . ?
C23' O3' C4' C3' -9.8(4) . . . . ?
C23' O3' C4' C5' 169.8(3) . . . . ?
C2' C3' C4' O3' 178.8(2) . . . . ?
C2' C3' C4' C5' -0.8(4) . . . . ?
C22' O2' C5' C6' 7.1(4) . . . . ?
C22' O2' C5' C4' -172.1(3) . . . . ?
O3' C4' C5' O2' -0.2(4) . . . . ?
C3' C4' C5' O2' 179.5(2) . . . . ?
O3' C4' C5' C6' -179.5(2) . . . . ?
C3' C4' C5' C6' 0.2(4) . . . . ?
O2' C5' C6' C1' -178.6(2) . . . . ?
C4' C5' C6' C1' 0.6(4) . . . . ?
C2' C1' C6' C5' -0.7(4) . . . . ?
C21' C1' C6' C5' 178.0(2) . . . . ?
C20' C7' C8' O4' -179.6(2) . . . . ?
C20' C7' C8' C9' 1.5(4) . . . . ?
C24' O4' C8' C7' -2.2(4) . . . . ?
C24' O4' C8' C9' 176.8(2) . . . . ?
C25' O5' C9' C10' -0.2(4) . . . . ?
C25' O5' C9' C8' -178.6(3) . . . . ?
C7' C8' C9' C10' -0.3(4) . . . . ?
O4' C8' C9' C10' -179.4(2) . . . . ?
C7' C8' C9' O5' 178.1(2) . . . . ?
O4' C8' C9' O5' -1.0(3) . . . . ?
O5' C9' C10' C11' 179.4(2) . . . . ?
C8' C9' C10' C11' -2.3(4) . . . . ?
C9' C10' C11' C12' -176.8(2) . . . . ?
C9' C10' C11' C20' 3.7(4) . . . . ?
C10' C11' C12' C13' -179.4(2) . . . . ?
C20' C11' C12' C13' 0.0(3) . . . . ?
C10' C11' C12' C2' -0.6(3) . . . . ?
C20' C11' C12' C2' 178.9(2) . . . . ?
C1' C2' C12' C11' 69.3(3) . . . . ?
C3' C2' C12' C11' -111.5(3) . . . . ?
C1' C2' C12' C13' -111.8(3) . . . . ?
C3' C2' C12' C13' 67.4(3) . . . . ?
C11' C12' C13' C14' -175.9(2) . . . . ?
C2' C12' C13' C14' 5.2(3) . . . . ?
C11' C12' C13' C18' 2.5(3) . . . . ?
C2' C12' C13' C18' -176.4(2) . . . . ?
C12' C13' C14' C15' 178.9(2) . . . . ?
C18' C13' C14' C15' 0.5(4) . . . . ?
C13' C14' C15' O6' -176.0(2) . . . . ?
C13' C14' C15' C16' 1.3(4) . . . . ?
C26' O6' C15' C14' 1.2(4) . . . . ?
C26' O6' C15' C16' -176.2(2) . . . . ?
C27' O7' C16' C17' -4.4(5) . . . . ?
C27' O7' C16' C15' 172.8(3) . . . . ?
C14' C15' C16' O7' -178.9(2) . . . . ?
O6' C15' C16' O7' -1.3(3) . . . . ?
C14' C15' C16' C17' -1.4(4) . . . . ?
O6' C15' C16' C17' 176.2(2) . . . . ?
O7' C16' C17' C18' 176.8(3) . . . . ?
C15' C16' C17' C18' -0.3(4) . . . . ?
C16' C17' C18' C19' -175.3(2) . . . . ?
C16' C17' C18' C13' 2.1(4) . . . . ?
C12' C13' C18' C19' -3.1(3) . . . . ?
C14' C13' C18' C19' 175.3(2) . . . . ?
C12' C13' C18' C17' 179.4(2) . . . . ?
C14' C13' C18' C17' -2.2(3) . . . . ?
C17' C18' C19' C20' 178.7(2) . . . . ?
C13' C18' C19' C20' 1.3(4) . . . . ?
C18' C19' C20' C7' -178.7(2) . . . . ?
C18' C19' C20' C11' 1.1(4) . . . . ?
C8' C7' C20' C19' 179.8(2) . . . . ?
C8' C7' C20' C11' 0.0(4) . . . . ?
C12' C11' C20' C19' -1.8(3) . . . . ?
C10' C11' C20' C19' 177.6(2) . . . . ?
C12' C11' C20' C7' 178.0(2) . . . . ?
C10' C11' C20' C7' -2.6(3) . . . . ?
C2' C1' C21' O1' -173.5(3) . . . . ?
C6' C1' C21' O1' 7.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate - Petroleum Ether'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_18
_database_code_depnum_ccdc_archive 'CCDC 1027041'
_audit_update_record             
;
2014-09-30 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H34 O10'
_chemical_formula_sum            'C30 H34 O10'
_chemical_formula_weight         554.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5941(13)
_cell_length_b                   10.9801(12)
_cell_length_c                   23.784(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.074(6)
_cell_angle_gamma                90.00
_cell_volume                     2805.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.54

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9533
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35678
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4927
_reflns_number_gt                4692
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (APEX2, Bruker, 2006)'
_computing_data_reduction        'SAINT (APEX2, Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4927
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0862
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   2.770
_refine_ls_restrained_S_all      2.770
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62828(15) 0.94138(16) 0.56513(7) 0.0294(4) Uani 1 1 d . . .
O2 O 0.78304(16) 0.81017(15) 0.52811(7) 0.0285(4) Uani 1 1 d . . .
O3 O 0.99595(15) 0.71198(14) 0.61012(7) 0.0238(4) Uani 1 1 d . . .
O4 O 1.35924(16) 1.00172(15) 0.87673(7) 0.0317(5) Uani 1 1 d . . .
O5 O 1.32280(17) 0.89198(16) 0.96879(7) 0.0355(5) Uani 1 1 d . . .
O6 O 1.15483(16) 0.69835(15) 0.94791(7) 0.0294(4) Uani 1 1 d . . .
O7 O 0.65863(16) 0.45601(15) 0.85560(8) 0.0314(5) Uani 1 1 d . . .
O8 O 0.54712(15) 0.67488(16) 0.83369(8) 0.0310(5) Uani 1 1 d . . .
O9 O 0.65456(16) 0.86946(15) 0.80085(8) 0.0294(5) Uani 1 1 d . . .
O10 O 1.00776(14) 0.59772(14) 0.75576(7) 0.0201(4) Uani 1 1 d . . .
C1 C 0.7287(2) 0.8896(2) 0.60943(10) 0.0208(6) Uani 1 1 d . . .
C2 C 0.8091(2) 0.8246(2) 0.58935(10) 0.0206(6) Uani 1 1 d . . .
C3 C 0.9142(2) 0.7713(2) 0.63151(10) 0.0188(6) Uani 1 1 d . . .
C4 C 0.9429(2) 0.7782(2) 0.69408(10) 0.0175(5) Uani 1 1 d . . .
C5 C 1.0532(2) 0.7053(2) 0.73598(10) 0.0187(6) Uani 1 1 d . . .
H5 H 1.1053 0.6797 0.7128 0.022 Uiso 1 1 calc R . .
C6 C 1.2784(2) 0.9054(2) 0.86170(11) 0.0239(6) Uani 1 1 d . . .
C7 C 1.2613(2) 0.8481(2) 0.91085(11) 0.0254(6) Uani 1 1 d . . .
C8 C 1.1783(2) 0.7517(2) 0.90062(11) 0.0214(6) Uani 1 1 d . . .
C9 C 1.1177(2) 0.7095(2) 0.84198(10) 0.0183(6) Uani 1 1 d . . .
C10 C 1.0205(2) 0.6111(2) 0.81807(10) 0.0187(6) Uani 1 1 d . . .
H10 H 1.0544 0.5336 0.8402 0.022 Uiso 1 1 calc R . .
C11 C 0.7218(2) 0.5491(2) 0.84160(10) 0.0219(6) Uani 1 1 d . . .
C12 C 0.6605(2) 0.6607(2) 0.82848(11) 0.0232(6) Uani 1 1 d . . .
C13 C 0.7166(2) 0.7587(2) 0.81197(10) 0.0205(6) Uani 1 1 d . . .
C14 C 0.8324(2) 0.7487(2) 0.80584(10) 0.0187(6) Uani 1 1 d . . .
C15 C 0.8786(2) 0.8572(2) 0.78032(10) 0.0184(6) Uani 1 1 d . . .
H15A H 0.9683 0.8692 0.8045 0.022 Uiso 1 1 calc R . .
H15B H 0.8342 0.9312 0.7850 0.022 Uiso 1 1 calc R . .
C16 C 0.8603(2) 0.8436(2) 0.71357(10) 0.0169(5) Uani 1 1 d . . .
C17 C 0.7551(2) 0.8979(2) 0.67132(10) 0.0193(6) Uani 1 1 d . . .
H17 H 0.7001 0.9417 0.6851 0.023 Uiso 1 1 calc R . .
C18 C 1.1362(2) 0.7650(2) 0.79424(10) 0.0177(6) Uani 1 1 d . . .
C19 C 1.2148(2) 0.8649(2) 0.80271(11) 0.0212(6) Uani 1 1 d . . .
H19 H 1.2247 0.9042 0.7692 0.025 Uiso 1 1 calc R . .
C20 C 0.8946(2) 0.6366(2) 0.82187(10) 0.0173(6) Uani 1 1 d . . .
C21 C 0.8394(2) 0.5393(2) 0.83999(10) 0.0195(6) Uani 1 1 d . . .
H21 H 0.8835 0.4647 0.8515 0.023 Uiso 1 1 calc R . .
C22 C 0.5543(2) 1.0233(3) 0.58460(12) 0.0348(7) Uani 1 1 d . . .
H22A H 0.5177 0.9790 0.6096 0.052 Uiso 1 1 calc R . .
H22B H 0.4878 1.0574 0.5490 0.052 Uiso 1 1 calc R . .
H22C H 0.6070 1.0894 0.6084 0.052 Uiso 1 1 calc R . .
C23 C 0.8179(3) 0.9125(2) 0.50116(12) 0.0392(8) Uani 1 1 d . . .
H23A H 0.7696 0.9839 0.5041 0.059 Uiso 1 1 calc R . .
H23B H 0.8011 0.8951 0.4584 0.059 Uiso 1 1 calc R . .
H23C H 0.9068 0.9290 0.5225 0.059 Uiso 1 1 calc R . .
C24 C 0.9527(3) 0.5936(2) 0.58568(12) 0.0359(7) Uani 1 1 d . . .
H24A H 0.9436 0.5421 0.6174 0.054 Uiso 1 1 calc R . .
H24B H 1.0129 0.5565 0.5709 0.054 Uiso 1 1 calc R . .
H24C H 0.8720 0.6014 0.5520 0.054 Uiso 1 1 calc R . .
C25 C 1.3551(3) 1.0799(2) 0.82833(12) 0.0375(7) Uani 1 1 d . . .
H25A H 1.3842 1.0356 0.8004 0.056 Uiso 1 1 calc R . .
H25B H 1.4088 1.1506 0.8447 0.056 Uiso 1 1 calc R . .
H25C H 1.2694 1.1074 0.8065 0.056 Uiso 1 1 calc R . .
C26 C 1.4438(3) 0.8398(3) 0.99800(14) 0.0625(11) Uani 1 1 d . . .
H26A H 1.4357 0.7535 1.0062 0.094 Uiso 1 1 calc R . .
H26B H 1.4879 0.8825 1.0363 0.094 Uiso 1 1 calc R . .
H26C H 1.4909 0.8478 0.9715 0.094 Uiso 1 1 calc R . .
C27 C 1.0804(3) 0.7735(3) 0.97011(13) 0.0414(8) Uani 1 1 d . . .
H27A H 1.1269 0.8472 0.9885 0.062 Uiso 1 1 calc R . .
H27B H 1.0596 0.7285 1.0007 0.062 Uiso 1 1 calc R . .
H27C H 1.0036 0.7961 0.9364 0.062 Uiso 1 1 calc R . .
C28 C 0.7232(3) 0.3442(2) 0.87459(14) 0.0431(8) Uani 1 1 d . . .
H28A H 0.7448 0.3107 0.8416 0.065 Uiso 1 1 calc R . .
H28B H 0.6700 0.2864 0.8850 0.065 Uiso 1 1 calc R . .
H28C H 0.7994 0.3585 0.9102 0.065 Uiso 1 1 calc R . .
C29 C 0.4444(3) 0.6566(3) 0.77763(13) 0.0477(8) Uani 1 1 d . . .
H29A H 0.4513 0.7125 0.7470 0.072 Uiso 1 1 calc R . .
H29B H 0.3664 0.6723 0.7835 0.072 Uiso 1 1 calc R . .
H29C H 0.4450 0.5724 0.7641 0.072 Uiso 1 1 calc R . .
C30 C 0.6635(3) 0.9299(3) 0.85584(14) 0.0523(9) Uani 1 1 d . . .
H30A H 0.6196 0.8822 0.8764 0.078 Uiso 1 1 calc R . .
H30B H 0.6259 1.0110 0.8462 0.078 Uiso 1 1 calc R . .
H30C H 0.7513 0.9379 0.8825 0.078 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.366(3) . ?
O1 C22 1.434(3) . ?
O2 C2 1.381(3) . ?
O2 C23 1.425(3) . ?
O3 C3 1.394(3) . ?
O3 C24 1.435(3) . ?
O4 C6 1.369(3) . ?
O4 C25 1.422(3) . ?
O5 C7 1.379(3) . ?
O5 C26 1.431(3) . ?
O6 C8 1.383(3) . ?
O6 C27 1.431(3) . ?
O7 C11 1.370(3) . ?
O7 C28 1.420(3) . ?
O8 C12 1.375(3) . ?
O8 C29 1.430(3) . ?
O9 C13 1.387(3) . ?
O9 C30 1.435(3) . ?
O10 C10 1.441(3) . ?
O10 C5 1.443(3) . ?
C1 C17 1.389(3) . ?
C1 C2 1.394(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.400(3) . ?
C4 C16 1.407(3) . ?
C4 C5 1.520(3) . ?
C5 C18 1.508(3) . ?
C5 H5 1.0000 . ?
C6 C19 1.390(3) . ?
C6 C7 1.405(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.385(3) . ?
C9 C18 1.375(3) . ?
C9 C10 1.510(3) . ?
C10 C20 1.522(3) . ?
C10 H10 1.0000 . ?
C11 C21 1.382(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.408(3) . ?
C14 C20 1.405(3) . ?
C14 C15 1.523(3) . ?
C15 C16 1.528(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(3) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C22 116.84(19) . . ?
C2 O2 C23 113.38(19) . . ?
C3 O3 C24 112.89(19) . . ?
C6 O4 C25 116.34(19) . . ?
C7 O5 C26 113.0(2) . . ?
C8 O6 C27 112.74(19) . . ?
C11 O7 C28 117.1(2) . . ?
C12 O8 C29 112.95(19) . . ?
C13 O9 C30 112.14(19) . . ?
C10 O10 C5 110.06(16) . . ?
O1 C1 C17 125.1(2) . . ?
O1 C1 C2 115.8(2) . . ?
C17 C1 C2 119.2(2) . . ?
O2 C2 C3 120.0(2) . . ?
O2 C2 C1 120.7(2) . . ?
C3 C2 C1 119.3(2) . . ?
C2 C3 O3 117.9(2) . . ?
C2 C3 C4 122.7(2) . . ?
O3 C3 C4 119.4(2) . . ?
C3 C4 C16 117.3(2) . . ?
C3 C4 C5 118.3(2) . . ?
C16 C4 C5 124.1(2) . . ?
O10 C5 C18 103.99(18) . . ?
O10 C5 C4 108.96(18) . . ?
C18 C5 C4 117.56(19) . . ?
O10 C5 H5 108.7 . . ?
C18 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
O4 C6 C19 124.2(2) . . ?
O4 C6 C7 115.2(2) . . ?
C19 C6 C7 120.6(2) . . ?
O5 C7 C8 120.3(2) . . ?
O5 C7 C6 119.6(2) . . ?
C8 C7 C6 120.0(2) . . ?
O6 C8 C9 119.8(2) . . ?
O6 C8 C7 121.0(2) . . ?
C9 C8 C7 119.1(2) . . ?
C18 C9 C8 120.4(2) . . ?
C18 C9 C10 109.4(2) . . ?
C8 C9 C10 130.0(2) . . ?
O10 C10 C9 103.54(18) . . ?
O10 C10 C20 110.49(18) . . ?
C9 C10 C20 116.25(19) . . ?
O10 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C20 C10 H10 108.8 . . ?
O7 C11 C21 124.9(2) . . ?
O7 C11 C12 115.9(2) . . ?
C21 C11 C12 119.2(2) . . ?
O8 C12 C13 120.2(2) . . ?
O8 C12 C11 120.3(2) . . ?
C13 C12 C11 119.4(2) . . ?
O9 C13 C12 118.0(2) . . ?
O9 C13 C14 119.6(2) . . ?
C12 C13 C14 122.4(2) . . ?
C20 C14 C13 116.9(2) . . ?
C20 C14 C15 124.9(2) . . ?
C13 C14 C15 118.2(2) . . ?
C14 C15 C16 113.90(19) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C4 120.1(2) . . ?
C17 C16 C15 116.8(2) . . ?
C4 C16 C15 123.1(2) . . ?
C1 C17 C16 121.4(2) . . ?
C1 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C9 C18 C19 121.8(2) . . ?
C9 C18 C5 108.8(2) . . ?
C19 C18 C5 129.3(2) . . ?
C6 C19 C18 117.9(2) . . ?
C6 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C21 C20 C14 120.5(2) . . ?
C21 C20 C10 116.0(2) . . ?
C14 C20 C10 123.4(2) . . ?
C11 C21 C20 121.4(2) . . ?
C11 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 C26 H26A 109.5 . . ?
O5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O6 C27 H27A 109.5 . . ?
O6 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O6 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O7 C28 H28A 109.5 . . ?
O7 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O7 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O8 C29 H29A 109.5 . . ?
O8 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O8 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O9 C30 H30A 109.5 . . ?
O9 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O9 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O1 C1 C17 8.6(3) . . . . ?
C22 O1 C1 C2 -171.1(2) . . . . ?
C23 O2 C2 C3 -100.1(3) . . . . ?
C23 O2 C2 C1 81.7(3) . . . . ?
O1 C1 C2 O2 -3.0(3) . . . . ?
C17 C1 C2 O2 177.3(2) . . . . ?
O1 C1 C2 C3 178.9(2) . . . . ?
C17 C1 C2 C3 -0.9(3) . . . . ?
O2 C2 C3 O3 4.9(3) . . . . ?
C1 C2 C3 O3 -176.9(2) . . . . ?
O2 C2 C3 C4 -177.2(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C24 O3 C3 C2 -77.9(3) . . . . ?
C24 O3 C3 C4 104.1(2) . . . . ?
C2 C3 C4 C16 -0.6(3) . . . . ?
O3 C3 C4 C16 177.30(19) . . . . ?
C2 C3 C4 C5 173.7(2) . . . . ?
O3 C3 C4 C5 -8.5(3) . . . . ?
C10 O10 C5 C18 20.1(2) . . . . ?
C10 O10 C5 C4 -106.0(2) . . . . ?
C3 C4 C5 O10 -102.4(2) . . . . ?
C16 C4 C5 O10 71.4(3) . . . . ?
C3 C4 C5 C18 139.8(2) . . . . ?
C16 C4 C5 C18 -46.4(3) . . . . ?
C25 O4 C6 C19 14.7(3) . . . . ?
C25 O4 C6 C7 -164.6(2) . . . . ?
C26 O5 C7 C8 95.2(3) . . . . ?
C26 O5 C7 C6 -87.9(3) . . . . ?
O4 C6 C7 O5 1.1(3) . . . . ?
C19 C6 C7 O5 -178.2(2) . . . . ?
O4 C6 C7 C8 178.0(2) . . . . ?
C19 C6 C7 C8 -1.3(4) . . . . ?
C27 O6 C8 C9 -106.2(3) . . . . ?
C27 O6 C8 C7 73.2(3) . . . . ?
O5 C7 C8 O6 0.5(4) . . . . ?
C6 C7 C8 O6 -176.4(2) . . . . ?
O5 C7 C8 C9 179.9(2) . . . . ?
C6 C7 C8 C9 3.0(4) . . . . ?
O6 C8 C9 C18 177.3(2) . . . . ?
C7 C8 C9 C18 -2.1(3) . . . . ?
O6 C8 C9 C10 2.2(4) . . . . ?
C7 C8 C9 C10 -177.2(2) . . . . ?
C5 O10 C10 C9 -20.4(2) . . . . ?
C5 O10 C10 C20 104.8(2) . . . . ?
C18 C9 C10 O10 12.6(2) . . . . ?
C8 C9 C10 O10 -171.9(2) . . . . ?
C18 C9 C10 C20 -108.7(2) . . . . ?
C8 C9 C10 C20 66.8(3) . . . . ?
C28 O7 C11 C21 5.4(4) . . . . ?
C28 O7 C11 C12 -174.4(2) . . . . ?
C29 O8 C12 C13 87.4(3) . . . . ?
C29 O8 C12 C11 -94.7(3) . . . . ?
O7 C11 C12 O8 4.1(3) . . . . ?
C21 C11 C12 O8 -175.7(2) . . . . ?
O7 C11 C12 C13 -178.0(2) . . . . ?
C21 C11 C12 C13 2.2(4) . . . . ?
C30 O9 C13 C12 76.2(3) . . . . ?
C30 O9 C13 C14 -104.3(3) . . . . ?
O8 C12 C13 O9 -0.3(3) . . . . ?
C11 C12 C13 O9 -178.2(2) . . . . ?
O8 C12 C13 C14 -179.8(2) . . . . ?
C11 C12 C13 C14 2.3(4) . . . . ?
O9 C13 C14 C20 175.6(2) . . . . ?
C12 C13 C14 C20 -4.9(3) . . . . ?
O9 C13 C14 C15 -6.6(3) . . . . ?
C12 C13 C14 C15 172.8(2) . . . . ?
C20 C14 C15 C16 76.2(3) . . . . ?
C13 C14 C15 C16 -101.4(2) . . . . ?
C3 C4 C16 C17 0.1(3) . . . . ?
C5 C4 C16 C17 -173.8(2) . . . . ?
C3 C4 C16 C15 179.1(2) . . . . ?
C5 C4 C16 C15 5.2(3) . . . . ?
C14 C15 C16 C17 96.8(2) . . . . ?
C14 C15 C16 C4 -82.2(3) . . . . ?
O1 C1 C17 C16 -179.3(2) . . . . ?
C2 C1 C17 C16 0.4(4) . . . . ?
C4 C16 C17 C1 0.0(4) . . . . ?
C15 C16 C17 C1 -179.1(2) . . . . ?
C8 C9 C18 C19 -0.5(3) . . . . ?
C10 C9 C18 C19 175.5(2) . . . . ?
C8 C9 C18 C5 -176.6(2) . . . . ?
C10 C9 C18 C5 -0.6(3) . . . . ?
O10 C5 C18 C9 -11.6(2) . . . . ?
C4 C5 C18 C9 108.9(2) . . . . ?
O10 C5 C18 C19 172.6(2) . . . . ?
C4 C5 C18 C19 -66.9(3) . . . . ?
O4 C6 C19 C18 179.5(2) . . . . ?
C7 C6 C19 C18 -1.3(3) . . . . ?
C9 C18 C19 C6 2.2(3) . . . . ?
C5 C18 C19 C6 177.5(2) . . . . ?
C13 C14 C20 C21 3.1(3) . . . . ?
C15 C14 C20 C21 -174.5(2) . . . . ?
C13 C14 C20 C10 -179.8(2) . . . . ?
C15 C14 C20 C10 2.6(3) . . . . ?
O10 C10 C20 C21 104.1(2) . . . . ?
C9 C10 C20 C21 -138.4(2) . . . . ?
O10 C10 C20 C14 -73.1(3) . . . . ?
C9 C10 C20 C14 44.4(3) . . . . ?
O7 C11 C21 C20 176.2(2) . . . . ?
C12 C11 C21 C20 -4.0(3) . . . . ?
C14 C20 C21 C11 1.3(3) . . . . ?
C10 C20 C21 C11 -176.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate - Petroleum Ether'
