# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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/access/V1 
# 
# 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_111
_audit_block_doi                 10.5517/ccdc.csd.cc1mz1g3
_database_code_depnum_ccdc_archive 'CCDC 1518425'
_audit_update_record             
;
2016-11-22 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ' meso-asaronan A'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H34 O9'
_chemical_formula_weight         466.51

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                   18.377(4)
_cell_length_b                   7.9014(16)
_cell_length_c                   17.239(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.43(3)
_cell_angle_gamma                90.00
_cell_volume                     2469.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2329
_cell_measurement_theta_min      2.9985
_cell_measurement_theta_max      29.5558

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10765
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4347
_reflns_number_gt                3359
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0669P)²+1.3191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4347
_refine_ls_number_parameters     308
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O5 O -0.32381(8) 0.83226(19) -0.28358(8) 0.0178(4) Uani 1 1 d . . .
O6 O -0.42561(9) 0.6005(2) -0.27198(9) 0.0228(4) Uani 1 1 d . . .
H6 H -0.4654 0.5518 -0.2830 0.034 Uiso 1 1 calc R . .
O4 O -0.43998(8) 0.9345(2) -0.21510(10) 0.0235(4) Uani 1 1 d . . .
H4 H -0.4324 0.8379 -0.2292 0.035 Uiso 1 1 calc R . .
O9 O -0.42222(9) 0.8451(2) -0.50956(9) 0.0270(4) Uani 1 1 d . . .
O2 O -0.08560(9) 1.1668(2) -0.12283(10) 0.0302(4) Uani 1 1 d . . .
O8 O -0.17840(9) 0.8313(2) -0.58766(9) 0.0308(5) Uani 1 1 d . . .
O3 O -0.29482(9) 1.2043(2) -0.39242(9) 0.0300(4) Uani 1 1 d . . .
O7 O -0.12072(9) 0.7378(2) -0.44022(10) 0.0323(5) Uani 1 1 d U . .
O1 O -0.05433(10) 1.3385(3) -0.24020(11) 0.0367(5) Uani 1 1 d . . .
C14 C -0.38570(13) 0.5862(3) -0.33652(13) 0.0202(5) Uani 1 1 d . . .
H14 H -0.3410 0.5195 -0.3194 0.024 Uiso 1 1 calc R . .
C1 C -0.03185(18) 1.4237(5) -0.3042(2) 0.0620(11) Uani 1 1 d . . .
H1A H -0.0296 1.3449 -0.3461 0.093 Uiso 1 1 calc R . .
H1B H 0.0160 1.4727 -0.2878 0.093 Uiso 1 1 calc R . .
H1C H -0.0666 1.5115 -0.3222 0.093 Uiso 1 1 calc R . .
C24 C -0.07696(17) 0.8873(5) -0.4245(2) 0.0554(9) Uani 1 1 d U . .
H24A H -0.0832 0.9574 -0.4706 0.083 Uiso 1 1 calc R . .
H24B H -0.0260 0.8565 -0.4105 0.083 Uiso 1 1 calc R . .
H24C H -0.0924 0.9485 -0.3819 0.083 Uiso 1 1 calc R . .
C11 C -0.37135(12) 1.0253(3) -0.19953(14) 0.0210(5) Uani 1 1 d . . .
H11 H -0.3400 0.9744 -0.1541 0.025 Uiso 1 1 calc R . .
C13 C -0.36321(12) 0.7650(3) -0.35557(12) 0.0182(5) Uani 1 1 d . . .
H13 H -0.4080 0.8325 -0.3712 0.022 Uiso 1 1 calc R . .
C5 C -0.25936(12) 1.1000(3) -0.26421(13) 0.0184(5) Uani 1 1 d . . .
C21 C -0.34741(13) 0.8204(3) -0.49695(13) 0.0200(5) Uani 1 1 d . . .
C16 C -0.31646(13) 0.7758(3) -0.41987(13) 0.0189(5) Uani 1 1 d . . .
C19 C -0.22735(13) 0.8139(3) -0.53594(13) 0.0222(5) Uani 1 1 d . . .
C10 C -0.33311(12) 1.0107(3) -0.27107(13) 0.0181(5) Uani 1 1 d . . .
H10 H -0.3660 1.0568 -0.3167 0.022 Uiso 1 1 calc R . .
C3 C -0.13910(13) 1.1671(3) -0.18880(14) 0.0222(5) Uani 1 1 d . . .
C4 C -0.20661(12) 1.0874(3) -0.19570(14) 0.0214(5) Uani 1 1 d . . .
H4A H -0.2175 1.0235 -0.1538 0.026 Uiso 1 1 calc R . .
C6 C -0.24158(13) 1.1944(3) -0.32643(14) 0.0228(6) Uani 1 1 d . . .
C22 C -0.45621(14) 0.9115(3) -0.58316(13) 0.0252(6) Uani 1 1 d . . .
H22A H -0.4525 0.8305 -0.6239 0.038 Uiso 1 1 calc R . .
H22B H -0.4318 1.0143 -0.5938 0.038 Uiso 1 1 calc R . .
H22C H -0.5072 0.9346 -0.5816 0.038 Uiso 1 1 calc R . .
C2 C -0.12240(13) 1.2615(3) -0.25205(15) 0.0257(6) Uani 1 1 d . . .
C17 C -0.24080(13) 0.7500(3) -0.40320(13) 0.0218(5) Uani 1 1 d . . .
H17 H -0.2197 0.7198 -0.3523 0.026 Uiso 1 1 calc R . .
C18 C -0.19602(13) 0.7675(3) -0.45913(13) 0.0223(5) Uani 1 1 d . . .
C20 C -0.30299(13) 0.8395(3) -0.55487(13) 0.0222(5) Uani 1 1 d . . .
H20 H -0.3240 0.8691 -0.6059 0.027 Uiso 1 1 calc R . .
C15 C -0.43103(14) 0.4991(3) -0.40654(14) 0.0263(6) Uani 1 1 d . . .
H15A H -0.4437 0.3871 -0.3918 0.039 Uiso 1 1 calc R . .
H15B H -0.4028 0.4923 -0.4486 0.039 Uiso 1 1 calc R . .
H15C H -0.4753 0.5627 -0.4235 0.039 Uiso 1 1 calc R . .
C7 C -0.17280(14) 1.2743(3) -0.32069(14) 0.0263(6) Uani 1 1 d . . .
H7 H -0.1611 1.3357 -0.3630 0.032 Uiso 1 1 calc R . .
C23 C -0.20444(15) 0.9091(4) -0.66182(14) 0.0304(6) Uani 1 1 d . . .
H23A H -0.1642 0.9214 -0.6906 0.046 Uiso 1 1 calc R . .
H23B H -0.2245 1.0185 -0.6535 0.046 Uiso 1 1 calc R . .
H23C H -0.2421 0.8395 -0.6912 0.046 Uiso 1 1 calc R . .
C12 C -0.38874(14) 1.2048(3) -0.18015(16) 0.0315(6) Uani 1 1 d . . .
H12A H -0.4173 1.2571 -0.2254 0.047 Uiso 1 1 calc R . .
H12B H -0.3436 1.2666 -0.1652 0.047 Uiso 1 1 calc R . .
H12C H -0.4164 1.2054 -0.1375 0.047 Uiso 1 1 calc R . .
C8 C -0.27259(15) 1.2653(4) -0.46290(14) 0.0319(6) Uani 1 1 d . . .
H8A H -0.3124 1.2517 -0.5060 0.048 Uiso 1 1 calc R . .
H8B H -0.2305 1.2022 -0.4732 0.048 Uiso 1 1 calc R . .
H8C H -0.2599 1.3829 -0.4569 0.048 Uiso 1 1 calc R . .
C9 C -0.09947(15) 1.0684(4) -0.05771(15) 0.0386(7) Uani 1 1 d . . .
H9A H -0.1062 0.9521 -0.0733 0.058 Uiso 1 1 calc R . .
H9B H -0.1432 1.1091 -0.0402 0.058 Uiso 1 1 calc R . .
H9C H -0.0584 1.0777 -0.0157 0.058 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
O5 C13 1.433(3) . ?
O5 C10 1.441(3) . ?
O6 C14 1.434(3) . ?
O6 H6 0.8200 . ?
O4 C11 1.437(3) . ?
O4 H4 0.8200 . ?
O9 C21 1.370(3) . ?
O9 C22 1.420(3) . ?
O2 C3 1.376(3) . ?
O2 C9 1.422(3) . ?
O8 C19 1.373(3) . ?
O8 C23 1.428(3) . ?
O3 C6 1.376(3) . ?
O3 C8 1.427(3) . ?
O7 C18 1.389(3) . ?
O7 C24 1.429(4) . ?
O1 C2 1.376(3) . ?
O1 C1 1.411(3) . ?
C14 C15 1.515(3) . ?
C14 C13 1.523(3) . ?
C14 H14 0.9800 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C11 C12 1.504(3) . ?
C11 C10 1.521(3) . ?
C11 H11 0.9800 . ?
C13 C16 1.512(3) . ?
C13 H13 0.9800 . ?
C5 C6 1.389(3) . ?
C5 C4 1.403(3) . ?
C5 C10 1.515(3) . ?
C21 C20 1.397(3) . ?
C21 C16 1.402(3) . ?
C16 C17 1.388(3) . ?
C19 C20 1.390(3) . ?
C19 C18 1.403(3) . ?
C10 H10 0.9800 . ?
C3 C4 1.379(3) . ?
C3 C2 1.396(3) . ?
C4 H4A 0.9300 . ?
C6 C7 1.402(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C2 C7 1.382(4) . ?
C17 C18 1.373(3) . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C7 H7 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C13 O5 C10 115.93(17) . . ?
C14 O6 H6 109.5 . . ?
C11 O4 H4 109.5 . . ?
C21 O9 C22 118.52(18) . . ?
C3 O2 C9 117.20(19) . . ?
C19 O8 C23 117.73(19) . . ?
C6 O3 C8 117.32(19) . . ?
C18 O7 C24 114.4(2) . . ?
C2 O1 C1 118.1(2) . . ?
O6 C14 C15 111.69(18) . . ?
O6 C14 C13 106.59(18) . . ?
C15 C14 C13 112.50(19) . . ?
O6 C14 H14 108.6 . . ?
C15 C14 H14 108.6 . . ?
C13 C14 H14 108.6 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O7 C24 H24A 109.5 . . ?
O7 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O7 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C11 C12 107.48(18) . . ?
O4 C11 C10 108.58(18) . . ?
C12 C11 C10 113.3(2) . . ?
O4 C11 H11 109.1 . . ?
C12 C11 H11 109.1 . . ?
C10 C11 H11 109.1 . . ?
O5 C13 C16 110.29(18) . . ?
O5 C13 C14 105.90(17) . . ?
C16 C13 C14 114.67(19) . . ?
O5 C13 H13 108.6 . . ?
C16 C13 H13 108.6 . . ?
C14 C13 H13 108.6 . . ?
C6 C5 C4 118.1(2) . . ?
C6 C5 C10 120.7(2) . . ?
C4 C5 C10 121.2(2) . . ?
O9 C21 C20 124.0(2) . . ?
O9 C21 C16 115.3(2) . . ?
C20 C21 C16 120.7(2) . . ?
C17 C16 C21 118.0(2) . . ?
C17 C16 C13 120.7(2) . . ?
C21 C16 C13 121.2(2) . . ?
O8 C19 C20 124.7(2) . . ?
O8 C19 C18 115.3(2) . . ?
C20 C19 C18 120.0(2) . . ?
O5 C10 C5 109.91(17) . . ?
O5 C10 C11 106.12(18) . . ?
C5 C10 C11 115.32(18) . . ?
O5 C10 H10 108.4 . . ?
C5 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
O2 C3 C4 125.5(2) . . ?
O2 C3 C2 115.3(2) . . ?
C4 C3 C2 119.1(2) . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4A 119.1 . . ?
C5 C4 H4A 119.1 . . ?
O3 C6 C5 116.3(2) . . ?
O3 C6 C7 122.9(2) . . ?
C5 C6 C7 120.7(2) . . ?
O9 C22 H22A 109.5 . . ?
O9 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O9 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C2 C7 124.1(2) . . ?
O1 C2 C3 115.5(2) . . ?
C7 C2 C3 120.4(2) . . ?
C18 C17 C16 122.3(2) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 O7 120.5(2) . . ?
C17 C18 C19 119.2(2) . . ?
O7 C18 C19 120.3(2) . . ?
C19 C20 C21 119.7(2) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C7 C6 119.8(2) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O8 C23 H23A 109.5 . . ?
O8 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O8 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
C10 O5 C13 C16 89.9(2) . . . . ?
C10 O5 C13 C14 -145.49(18) . . . . ?
O6 C14 C13 O5 54.9(2) . . . . ?
C15 C14 C13 O5 177.69(18) . . . . ?
O6 C14 C13 C16 176.79(18) . . . . ?
C15 C14 C13 C16 -60.5(3) . . . . ?
C22 O9 C21 C20 -7.1(3) . . . . ?
C22 O9 C21 C16 172.0(2) . . . . ?
O9 C21 C16 C17 -179.6(2) . . . . ?
C20 C21 C16 C17 -0.5(3) . . . . ?
O9 C21 C16 C13 -2.8(3) . . . . ?
C20 C21 C16 C13 176.3(2) . . . . ?
O5 C13 C16 C17 36.5(3) . . . . ?
C14 C13 C16 C17 -83.0(3) . . . . ?
O5 C13 C16 C21 -140.3(2) . . . . ?
C14 C13 C16 C21 100.3(3) . . . . ?
C23 O8 C19 C20 11.5(4) . . . . ?
C23 O8 C19 C18 -168.3(2) . . . . ?
C13 O5 C10 C5 -119.02(19) . . . . ?
C13 O5 C10 C11 115.67(19) . . . . ?
C6 C5 C10 O5 103.4(2) . . . . ?
C4 C5 C10 O5 -75.4(3) . . . . ?
C6 C5 C10 C11 -136.7(2) . . . . ?
C4 C5 C10 C11 44.5(3) . . . . ?
O4 C11 C10 O5 -58.0(2) . . . . ?
C12 C11 C10 O5 -177.30(19) . . . . ?
O4 C11 C10 C5 -179.92(19) . . . . ?
C12 C11 C10 C5 60.8(3) . . . . ?
C9 O2 C3 C4 3.6(4) . . . . ?
C9 O2 C3 C2 -178.3(2) . . . . ?
O2 C3 C4 C5 177.3(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
C10 C5 C4 C3 179.6(2) . . . . ?
C8 O3 C6 C5 -165.6(2) . . . . ?
C8 O3 C6 C7 14.5(3) . . . . ?
C4 C5 C6 O3 -179.7(2) . . . . ?
C10 C5 C6 O3 1.4(3) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C10 C5 C6 C7 -178.7(2) . . . . ?
C1 O1 C2 C7 -5.7(4) . . . . ?
C1 O1 C2 C3 174.8(3) . . . . ?
O2 C3 C2 O1 1.2(3) . . . . ?
C4 C3 C2 O1 179.3(2) . . . . ?
O2 C3 C2 C7 -178.4(2) . . . . ?
C4 C3 C2 C7 -0.2(4) . . . . ?
C21 C16 C17 C18 0.3(4) . . . . ?
C13 C16 C17 C18 -176.5(2) . . . . ?
C16 C17 C18 O7 -179.0(2) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C24 O7 C18 C17 -99.1(3) . . . . ?
C24 O7 C18 C19 81.6(3) . . . . ?
O8 C19 C18 C17 178.9(2) . . . . ?
C20 C19 C18 C17 -0.8(4) . . . . ?
O8 C19 C18 O7 -1.8(3) . . . . ?
C20 C19 C18 O7 178.5(2) . . . . ?
O8 C19 C20 C21 -179.1(2) . . . . ?
C18 C19 C20 C21 0.7(4) . . . . ?
O9 C21 C20 C19 179.1(2) . . . . ?
C16 C21 C20 C19 0.0(4) . . . . ?
O1 C2 C7 C6 -178.5(2) . . . . ?
C3 C2 C7 C6 1.1(4) . . . . ?
O3 C6 C7 C2 178.8(2) . . . . ?
C5 C6 C7 C2 -1.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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/access/V1 
# 
# 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_exp_2223
_database_code_depnum_ccdc_archive 'CCDC 1518426'
_audit_update_record             
;
2016-11-22 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;
_audit_creation_date             2015-03-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.16 svn.r3037 for OlexSys, GUI svn.r4914)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        'asarolignan B'
_chemical_formula_moiety         '2(C24 H34 O9), 3(H2 O), C H4 O, 1.9(O)'
_chemical_formula_sum            'C49 H78 O23.90'
_chemical_formula_weight         1049.51
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n 21 a'
_space_group_name_Hall           'P -2ac -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.3231(5)
_cell_length_b                   23.3774(6)
_cell_length_c                   16.4367(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5503.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4654
_cell_measurement_temperature    107.0
_cell_measurement_theta_max      29.5695
_cell_measurement_theta_min      2.9688
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2253
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33662
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.635
_diffrn_reflns_theta_min         2.988
_diffrn_ambient_temperature      107.0
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -69.00   -8.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -37.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega  -61.00  -36.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  115.0000  166.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega   17.00   49.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   37.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -35.00   -4.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -77.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00   28.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega  -61.00  -36.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.1085  115.0000  -77.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -37.00    7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4210  -37.0000  -60.0000 44
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0260023000
_diffrn_orient_matrix_UB_12      -0.0013914000
_diffrn_orient_matrix_UB_13      -0.0366724000
_diffrn_orient_matrix_UB_21      0.0413879000
_diffrn_orient_matrix_UB_22      0.0048484000
_diffrn_orient_matrix_UB_23      -0.0226465000
_diffrn_orient_matrix_UB_31      0.0079207000
_diffrn_orient_matrix_UB_32      -0.0299273000
_diffrn_orient_matrix_UB_33      -0.0019709000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.737
_reflns_number_gt                9471
_reflns_number_total             12501
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 3340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     697
_refine_ls_number_reflns         12501
_refine_ls_number_restraints     165
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0697
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0872P)²+1.1110P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1815
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 H23D-O22
 2 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(O1B)=0.9*(1-FVAR(2))
 Sof(O1A)=0.9*FVAR(2)
5.a Free rotating group:
 O20(H20A,H20B), O22(H22D,H22E), O23(H23D,H23E)
5.b Ternary CH refined with riding coordinates:
 C15(H15A), C39(H39), C27(H27), C3(H3), C38(H38), C14(H14), C2(H2A), C26(H26)
5.c Aromatic/amide H refined with riding coordinates:
 C42(H42), C6(H6A), C45(H45), C30(H30), C18(H18), C33(H33), C21(H21), C9(H9)
5.d Tetrahedral OH refined with riding coordinates:
 O11(H11), O2(H2)
5.e Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C25(H25A,H25B,H25C), C46(H46A,H46B,H46C), C10(H10A,H10B,
 H10C), C23(H23A,H23B,H23C), C37(H37A,H37B,H37C), C35(H35A,H35B,H35C), C22(H22A,
 H22B,H22C), C36(H36A,H36B,H36C), C47(H47A,H47B,H47C), C1(H1A,H1B,H1C),
 C11(H11A,H11B,H11C), C24(H24A,H24B,H24C), C13(H13A,H13B,H13C), C12(H12A,H12B,
 H12C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C)
5.f Idealised tetrahedral OH refined as rotating group:
 O6(H6), O15(H15), O19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O10 O 0.9127(2) 0.54203(12) 0.40680(19) 0.0144(7) Uani 1 1 d . U . . .
O1 O 0.2471(2) 0.20919(13) 0.60085(19) 0.0138(7) Uani 1 1 d . U . . .
O3 O 0.3692(2) 0.35849(13) 0.5402(2) 0.0221(7) Uani 1 1 d . U . . .
O7 O 0.1229(3) 0.35776(13) 0.6118(2) 0.0235(8) Uani 1 1 d . U . . .
O4 O 0.2742(3) 0.32900(14) 0.2589(2) 0.0224(7) Uani 1 1 d . U . . .
O13 O 1.0503(2) 0.38969(15) 0.1109(2) 0.0236(8) Uani 1 1 d . U . . .
O6 O 0.0990(2) 0.16022(13) 0.5259(2) 0.0182(7) Uani 1 1 d . U . . .
H6 H 0.0503 0.1442 0.5128 0.027 Uiso 1 1 calc GR . . . .
O8 O 0.1267(2) 0.35603(15) 0.9076(2) 0.0246(8) Uani 1 1 d . U . . .
O12 O 1.0636(3) 0.40061(13) 0.4062(2) 0.0246(8) Uani 1 1 d . U . . .
O16 O 0.8210(2) 0.38664(13) 0.4539(2) 0.0217(7) Uani 1 1 d . U . . .
O15 O 0.7396(2) 0.58444(13) 0.4624(2) 0.0202(7) Uani 1 1 d . U . . .
H15 H 0.6947 0.6043 0.4499 0.030 Uiso 1 1 calc GR . . . .
O11 O 1.0573(3) 0.59222(13) 0.4877(2) 0.0219(8) Uani 1 1 d . U . . .
H11 H 1.1035 0.5906 0.5171 0.033 Uiso 1 1 calc R . . . .
O2 O 0.4134(2) 0.15972(14) 0.5540(2) 0.0218(7) Uani 1 1 d . U . . .
H2 H 0.4533 0.1614 0.5182 0.033 Uiso 1 1 calc R . . . .
O17 O 0.8772(3) 0.41400(14) 0.7429(2) 0.0237(8) Uani 1 1 d . U . . .
O14 O 0.9929(3) 0.49367(14) 0.1033(2) 0.0245(8) Uani 1 1 d . U . . .
C15 C 0.1598(3) 0.23942(18) 0.6046(3) 0.0155(9) Uani 1 1 d . U . . .
H15A H 0.1560 0.2659 0.5585 0.019 Uiso 1 1 calc R . . . .
O9 O 0.1657(3) 0.24765(15) 0.9067(2) 0.0295(9) Uani 1 1 d . U . . .
C39 C 0.8365(3) 0.50363(18) 0.4236(3) 0.0150(9) Uani 1 1 d . U . . .
H39 H 0.8400 0.4719 0.3847 0.018 Uiso 1 1 calc R . . . .
C27 C 1.0012(3) 0.51392(18) 0.4050(3) 0.0148(9) Uani 1 1 d . U . . .
H27 H 1.0055 0.4883 0.4521 0.018 Uiso 1 1 calc R . . . .
C42 C 0.8483(3) 0.39647(19) 0.5993(3) 0.0173(10) Uani 1 1 d . U . . .
H42 H 0.8444 0.3571 0.6071 0.021 Uiso 1 1 calc R . . . .
C40 C 0.8437(3) 0.47886(18) 0.5083(3) 0.0154(9) Uani 1 1 d . U . . .
C3 C 0.3230(3) 0.24629(19) 0.5814(3) 0.0159(9) Uani 1 1 d . U . . .
H3 H 0.3209 0.2791 0.6185 0.019 Uiso 1 1 calc R . . . .
C6 C 0.3264(3) 0.3465(2) 0.3978(3) 0.0219(11) Uani 1 1 d . U . . .
H6A H 0.3414 0.3843 0.3861 0.026 Uiso 1 1 calc R . . . .
C34 C 1.0614(4) 0.33999(19) 0.4152(3) 0.0225(11) Uani 1 1 d . U . . .
H34A H 1.0628 0.3304 0.4720 0.034 Uiso 1 1 calc GR . . . .
H34B H 1.1146 0.3235 0.3886 0.034 Uiso 1 1 calc GR . . . .
H34C H 1.0052 0.3253 0.3912 0.034 Uiso 1 1 calc GR . . . .
C19 C 0.1360(3) 0.3315(2) 0.8319(3) 0.0185(10) Uani 1 1 d . U . . .
C45 C 0.8602(4) 0.51375(19) 0.5749(3) 0.0188(10) Uani 1 1 d . U . . .
H45 H 0.8659 0.5530 0.5673 0.023 Uiso 1 1 calc R . . . .
C38 C 0.7455(3) 0.5362(2) 0.4077(3) 0.0189(10) Uani 1 1 d . U . . .
H38 H 0.6930 0.5106 0.4189 0.023 Uiso 1 1 calc R . . . .
C4 C 0.3169(3) 0.26843(19) 0.4950(3) 0.0171(10) Uani 1 1 d . U . . .
C30 C 1.0554(3) 0.3907(2) 0.2590(3) 0.0189(10) Uani 1 1 d . U . . .
H30 H 1.0743 0.3527 0.2615 0.023 Uiso 1 1 calc R . . . .
C17 C 0.1337(3) 0.33149(19) 0.6850(3) 0.0170(9) Uani 1 1 d . U . . .
C18 C 0.1265(3) 0.3609(2) 0.7596(3) 0.0172(10) Uani 1 1 d . U . . .
H18 H 0.1153 0.4001 0.7601 0.021 Uiso 1 1 calc R . . . .
C29 C 1.0433(3) 0.42251(19) 0.3305(3) 0.0179(10) Uani 1 1 d . U . . .
C14 C 0.0829(3) 0.19457(18) 0.5963(3) 0.0146(9) Uani 1 1 d . U . . .
H14 H 0.0826 0.1701 0.6447 0.018 Uiso 1 1 calc R . . . .
C20 C 0.1562(4) 0.27242(19) 0.8318(3) 0.0192(10) Uani 1 1 d . U . . .
C41 C 0.8379(3) 0.41938(18) 0.5215(3) 0.0161(9) Uani 1 1 d . U . . .
C44 C 0.8683(4) 0.4913(2) 0.6528(3) 0.0210(11) Uani 1 1 d . U . . .
C2 C 0.4123(3) 0.2125(2) 0.5987(3) 0.0190(10) Uani 1 1 d . U . . .
H2A H 0.4659 0.2356 0.5816 0.023 Uiso 1 1 calc R . . . .
C26 C 1.0747(4) 0.56128(19) 0.4142(3) 0.0184(10) Uani 1 1 d . U . . .
H26 H 1.0699 0.5875 0.3678 0.022 Uiso 1 1 calc R . . . .
C43 C 0.8645(3) 0.4323(2) 0.6652(3) 0.0185(10) Uani 1 1 d . U . . .
C25 C 1.1724(4) 0.5378(2) 0.4183(4) 0.0265(12) Uani 1 1 d . U . . .
H25A H 1.1782 0.5134 0.4650 0.040 Uiso 1 1 calc GR . . . .
H25B H 1.2161 0.5688 0.4226 0.040 Uiso 1 1 calc GR . . . .
H25C H 1.1853 0.5162 0.3699 0.040 Uiso 1 1 calc GR . . . .
C16 C 0.1518(3) 0.27338(19) 0.6835(3) 0.0158(9) Uani 1 1 d . U . . .
C33 C 0.9953(3) 0.50331(19) 0.2519(3) 0.0179(10) Uani 1 1 d . U . . .
H33 H 0.9737 0.5408 0.2493 0.021 Uiso 1 1 calc R . . . .
O5 O 0.2306(3) 0.22256(14) 0.2913(2) 0.0259(8) Uani 1 1 d . U . . .
C31 C 1.0388(3) 0.41647(19) 0.1845(3) 0.0172(10) Uani 1 1 d . U . . .
C21 C 0.1645(3) 0.2448(2) 0.7587(3) 0.0193(10) Uani 1 1 d . U . . .
H21 H 0.1790 0.2060 0.7584 0.023 Uiso 1 1 calc R . . . .
C46 C 0.8120(4) 0.32611(18) 0.4647(3) 0.0211(10) Uani 1 1 d . U . . .
H46A H 0.7611 0.3183 0.5010 0.032 Uiso 1 1 calc GR . . . .
H46B H 0.8688 0.3111 0.4872 0.032 Uiso 1 1 calc GR . . . .
H46C H 0.8002 0.3084 0.4130 0.032 Uiso 1 1 calc GR . . . .
C10 C 0.3614(4) 0.4187(2) 0.5308(3) 0.0253(11) Uani 1 1 d . U . . .
H10A H 0.4068 0.4317 0.4920 0.038 Uiso 1 1 calc GR . . . .
H10B H 0.3722 0.4370 0.5822 0.038 Uiso 1 1 calc GR . . . .
H10C H 0.2999 0.4280 0.5118 0.038 Uiso 1 1 calc GR . . . .
C9 C 0.2829(3) 0.2336(2) 0.4324(3) 0.0192(10) Uani 1 1 d . U . . .
H9 H 0.2690 0.1956 0.4437 0.023 Uiso 1 1 calc R . . . .
C32 C 1.0084(3) 0.4727(2) 0.1803(3) 0.0180(10) Uani 1 1 d . U . . .
C28 C 1.0139(3) 0.47890(18) 0.3280(3) 0.0139(9) Uani 1 1 d . U . . .
C23 C 0.1062(4) 0.4155(2) 0.9106(3) 0.0291(12) Uani 1 1 d . U . . .
H23A H 0.0507 0.4231 0.8796 0.044 Uiso 1 1 calc GR . . . .
H23B H 0.1575 0.4367 0.8880 0.044 Uiso 1 1 calc GR . . . .
H23C H 0.0966 0.4269 0.9660 0.044 Uiso 1 1 calc GR . . . .
O18 O 0.8773(3) 0.52811(15) 0.7187(2) 0.0298(9) Uani 1 1 d . U . . .
C37 C 0.7380(4) 0.5567(2) 0.3197(3) 0.0231(11) Uani 1 1 d . U . . .
H37A H 0.7869 0.5836 0.3086 0.035 Uiso 1 1 calc GR . . . .
H37B H 0.6785 0.5748 0.3115 0.035 Uiso 1 1 calc GR . . . .
H37C H 0.7437 0.5246 0.2837 0.035 Uiso 1 1 calc GR . . . .
C35 C 1.0699(4) 0.3295(2) 0.1116(3) 0.0267(11) Uani 1 1 d . U . . .
H35A H 1.1294 0.3230 0.1369 0.040 Uiso 1 1 calc GR . . . .
H35B H 1.0713 0.3154 0.0568 0.040 Uiso 1 1 calc GR . . . .
H35C H 1.0222 0.3099 0.1417 0.040 Uiso 1 1 calc GR . . . .
C22 C 0.1144(4) 0.41864(19) 0.6095(3) 0.0241(11) Uani 1 1 d . U . . .
H22A H 0.1152 0.4314 0.5540 0.036 Uiso 1 1 calc GR . . . .
H22B H 0.1656 0.4356 0.6385 0.036 Uiso 1 1 calc GR . . . .
H22C H 0.0566 0.4298 0.6345 0.036 Uiso 1 1 calc GR . . . .
C36 C 0.9500(5) 0.5483(2) 0.0970(3) 0.0310(13) Uani 1 1 d . U . . .
H36A H 0.8964 0.5497 0.1321 0.047 Uiso 1 1 calc GR . . . .
H36B H 0.9307 0.5547 0.0418 0.047 Uiso 1 1 calc GR . . . .
H36C H 0.9937 0.5773 0.1129 0.047 Uiso 1 1 calc GR . . . .
C47 C 0.8837(4) 0.3535(2) 0.7553(3) 0.0208(10) Uani 1 1 d . U . . .
H47A H 0.9001 0.3459 0.8109 0.031 Uiso 1 1 calc GR . . . .
H47B H 0.9307 0.3379 0.7200 0.031 Uiso 1 1 calc GR . . . .
H47C H 0.8246 0.3360 0.7432 0.031 Uiso 1 1 calc GR . . . .
C1 C 0.4222(4) 0.1992(2) 0.6887(3) 0.0257(11) Uani 1 1 d . U . . .
H1A H 0.4795 0.1789 0.6978 0.039 Uiso 1 1 calc GR . . . .
H1B H 0.3706 0.1761 0.7061 0.039 Uiso 1 1 calc GR . . . .
H1C H 0.4229 0.2343 0.7191 0.039 Uiso 1 1 calc GR . . . .
C5 C 0.3382(3) 0.3250(2) 0.4773(3) 0.0177(9) Uani 1 1 d . U . . .
C7 C 0.2920(3) 0.3109(2) 0.3367(3) 0.0194(10) Uani 1 1 d . U . . .
C11 C 0.2887(4) 0.3881(2) 0.2422(3) 0.0233(11) Uani 1 1 d . U . . .
H11A H 0.2671 0.3967 0.1883 0.035 Uiso 1 1 calc GR . . . .
H11B H 0.3540 0.3968 0.2463 0.035 Uiso 1 1 calc GR . . . .
H11C H 0.2546 0.4107 0.2809 0.035 Uiso 1 1 calc GR . . . .
C8 C 0.2693(3) 0.2540(2) 0.3540(3) 0.0188(10) Uani 1 1 d . U . . .
C24 C 0.1910(6) 0.1885(2) 0.9079(4) 0.0472(18) Uani 1 1 d . U . . .
H24A H 0.1454 0.1667 0.8785 0.071 Uiso 1 1 calc GR . . . .
H24B H 0.1937 0.1753 0.9632 0.071 Uiso 1 1 calc GR . . . .
H24C H 0.2511 0.1838 0.8828 0.071 Uiso 1 1 calc GR . . . .
C13 C -0.0118(3) 0.2226(2) 0.5869(3) 0.0216(10) Uani 1 1 d . U . . .
H13A H -0.0591 0.1936 0.5833 0.032 Uiso 1 1 calc GR . . . .
H13B H -0.0125 0.2454 0.5383 0.032 Uiso 1 1 calc GR . . . .
H13C H -0.0240 0.2466 0.6331 0.032 Uiso 1 1 calc GR . . . .
C12 C 0.2024(5) 0.1652(2) 0.3107(3) 0.0363(14) Uani 1 1 d . U . . .
H12A H 0.1754 0.1477 0.2634 0.054 Uiso 1 1 calc GR . . . .
H12B H 0.1571 0.1661 0.3538 0.054 Uiso 1 1 calc GR . . . .
H12C H 0.2558 0.1436 0.3278 0.054 Uiso 1 1 calc GR . . . .
O20 O 0.1562(4) 0.6128(3) 0.6284(4) 0.0641(15) Uani 1 1 d . U . . .
H20A H 0.2145 0.6060 0.6291 0.096 Uiso 1 1 d G . . . .
H20B H 0.1472 0.6487 0.6297 0.096 Uiso 1 1 d G . . . .
O22 O 0.6292(4) 0.5572(2) 0.6010(4) 0.0596(14) Uani 1 1 d D U . . .
H22D H 0.5848 0.5806 0.6092 0.089 Uiso 1 1 d G . . . .
H22E H 0.6744 0.5744 0.5780 0.089 Uiso 1 1 d G . . . .
O19 O 0.5524(5) 0.6729(2) 0.7590(4) 0.0746(17) Uani 1 1 d . U . . .
H19 H 0.5397 0.6752 0.7105 0.112 Uiso 1 1 calc GR . . . .
O23 O 0.6868(5) 0.5283(3) 0.7606(4) 0.0772(18) Uani 1 1 d . U . . .
H23D H 0.6747 0.5290 0.7100 0.116 Uiso 1 1 d DG . . . .
H23E H 0.7456 0.5287 0.7676 0.116 Uiso 1 1 d G . . . .
O21 O 0.4973(4) 0.6530(3) 0.5969(4) 0.090(2) Uani 1 1 d . U . . .
C48 C 0.9671(5) 0.5328(3) 0.7507(5) 0.0520(18) Uani 1 1 d . U . . .
H48A H 0.9649 0.5542 0.8006 0.078 Uiso 1 1 calc GR . . . .
H48B H 1.0066 0.5522 0.7124 0.078 Uiso 1 1 calc GR . . . .
H48C H 0.9916 0.4953 0.7612 0.078 Uiso 1 1 calc GR . . . .
C49 C 0.5339(7) 0.7257(4) 0.7974(6) 0.074(3) Uani 1 1 d . U . . .
H49A H 0.5411 0.7216 0.8552 0.111 Uiso 1 1 calc GR . . . .
H49B H 0.4711 0.7374 0.7853 0.111 Uiso 1 1 calc GR . . . .
H49C H 0.5768 0.7541 0.7778 0.111 Uiso 1 1 calc GR . . . .
O1A O 0.3019(7) 0.7007(4) 0.6158(6) 0.074(4) Uani 0.626(15) 1 d . U P A 1
O1B O 0.3192(18) 0.6451(9) 0.5902(13) 0.076(9) Uani 0.274(15) 1 d . U P A 2


_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
O10 C39 1.439(5) . ?
O10 C27 1.429(5) . ?
O1 C15 1.438(5) . ?
O1 C3 1.426(5) . ?
O3 C10 1.419(6) . ?
O3 C5 1.371(6) . ?
O7 C17 1.360(6) . ?
O7 C22 1.429(5) . ?
O4 C7 1.372(6) . ?
O4 C11 1.425(6) . ?
O13 C31 1.372(6) . ?
O13 C35 1.434(6) . ?
O6 H6 0.8200 . ?
O6 C14 1.428(5) . ?
O8 C19 1.377(6) . ?
O8 C23 1.422(6) . ?
O12 C34 1.425(5) . ?
O12 C29 1.376(6) . ?
O16 C41 1.371(6) . ?
O16 C46 1.432(5) . ?
O15 H15 0.8200 . ?
O15 C38 1.444(6) . ?
O11 H11 0.8200 . ?
O11 C26 1.431(6) . ?
O2 H2 0.8200 . ?
O2 C2 1.436(6) . ?
O17 C43 1.360(6) . ?
O17 C47 1.433(5) . ?
O14 C32 1.375(6) . ?
O14 C36 1.421(6) . ?
C15 H15A 0.9800 . ?
C15 C14 1.526(6) . ?
C15 C16 1.525(6) . ?
O9 C20 1.368(6) . ?
O9 C24 1.430(7) . ?
C39 H39 0.9800 . ?
C39 C40 1.512(6) . ?
C39 C38 1.533(7) . ?
C27 H27 0.9800 . ?
C27 C26 1.535(6) . ?
C27 C28 1.519(6) . ?
C42 H42 0.9300 . ?
C42 C41 1.395(7) . ?
C42 C43 1.388(7) . ?
C40 C45 1.385(7) . ?
C40 C41 1.410(6) . ?
C3 H3 0.9800 . ?
C3 C4 1.514(7) . ?
C3 C2 1.530(7) . ?
C6 H6A 0.9300 . ?
C6 C5 1.410(7) . ?
C6 C7 1.394(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C19 C18 1.380(7) . ?
C19 C20 1.410(7) . ?
C45 H45 0.9300 . ?
C45 C44 1.388(7) . ?
C38 H38 0.9800 . ?
C38 C37 1.527(7) . ?
C4 C9 1.400(7) . ?
C4 C5 1.389(6) . ?
C30 H30 0.9300 . ?
C30 C29 1.403(7) . ?
C30 C31 1.385(7) . ?
C17 C18 1.410(6) . ?
C17 C16 1.383(6) . ?
C18 H18 0.9300 . ?
C29 C28 1.385(6) . ?
C14 H14 0.9800 . ?
C14 C13 1.515(7) . ?
C20 C21 1.369(7) . ?
C44 C43 1.395(7) . ?
C44 O18 1.390(6) . ?
C2 H2A 0.9800 . ?
C2 C1 1.519(7) . ?
C26 H26 0.9800 . ?
C26 C25 1.505(7) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C16 C21 1.417(7) . ?
C33 H33 0.9300 . ?
C33 C32 1.390(7) . ?
C33 C28 1.400(6) . ?
O5 C8 1.381(6) . ?
O5 C12 1.435(6) . ?
C31 C32 1.387(6) . ?
C21 H21 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C8 1.387(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O18 C48 1.393(8) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C7 C8 1.397(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O20 H20A 0.8495 . ?
O20 H20B 0.8505 . ?
O22 H22D 0.8495 . ?
O22 H22E 0.8513 . ?
O19 H19 0.8200 . ?
O19 C49 1.412(10) . ?
O23 H23D 0.8509 . ?
O23 H23E 0.8495 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?

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
C27 O10 C39 112.9(3) . . ?
C3 O1 C15 111.9(3) . . ?
C5 O3 C10 117.2(4) . . ?
C17 O7 C22 118.9(4) . . ?
C7 O4 C11 116.9(4) . . ?
C31 O13 C35 117.6(4) . . ?
C14 O6 H6 109.5 . . ?
C19 O8 C23 117.3(4) . . ?
C29 O12 C34 117.3(4) . . ?
C41 O16 C46 117.8(4) . . ?
C38 O15 H15 109.5 . . ?
C26 O11 H11 109.5 . . ?
C2 O2 H2 109.5 . . ?
C43 O17 C47 116.9(4) . . ?
C32 O14 C36 117.2(4) . . ?
O1 C15 H15A 109.0 . . ?
O1 C15 C14 106.6(3) . . ?
O1 C15 C16 110.9(4) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 C14 112.3(4) . . ?
C20 O9 C24 116.5(4) . . ?
O10 C39 H39 107.9 . . ?
O10 C39 C40 111.4(4) . . ?
O10 C39 C38 107.5(3) . . ?
C40 C39 H39 107.9 . . ?
C40 C39 C38 113.9(4) . . ?
C38 C39 H39 107.9 . . ?
O10 C27 H27 108.7 . . ?
O10 C27 C26 105.9(3) . . ?
O10 C27 C28 111.8(4) . . ?
C26 C27 H27 108.7 . . ?
C28 C27 H27 108.7 . . ?
C28 C27 C26 112.8(4) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C43 C42 C41 120.1(4) . . ?
C45 C40 C39 120.9(4) . . ?
C45 C40 C41 118.0(4) . . ?
C41 C40 C39 121.0(4) . . ?
O1 C3 H3 108.3 . . ?
O1 C3 C4 112.0(4) . . ?
O1 C3 C2 106.3(4) . . ?
C4 C3 H3 108.3 . . ?
C4 C3 C2 113.5(4) . . ?
C2 C3 H3 108.3 . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C7 C6 C5 119.8(4) . . ?
O12 C34 H34A 109.5 . . ?
O12 C34 H34B 109.5 . . ?
O12 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O8 C19 C18 124.1(4) . . ?
O8 C19 C20 115.4(4) . . ?
C18 C19 C20 120.5(4) . . ?
C40 C45 H45 119.3 . . ?
C40 C45 C44 121.3(4) . . ?
C44 C45 H45 119.3 . . ?
O15 C38 C39 109.3(4) . . ?
O15 C38 H38 108.4 . . ?
O15 C38 C37 109.9(4) . . ?
C39 C38 H38 108.4 . . ?
C37 C38 C39 112.2(4) . . ?
C37 C38 H38 108.4 . . ?
C9 C4 C3 120.7(4) . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 C9 118.4(4) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C31 C30 C29 119.3(4) . . ?
O7 C17 C18 122.8(4) . . ?
O7 C17 C16 116.7(4) . . ?
C16 C17 C18 120.6(4) . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
O12 C29 C30 122.3(4) . . ?
O12 C29 C28 116.5(4) . . ?
C28 C29 C30 121.1(4) . . ?
O6 C14 C15 110.0(4) . . ?
O6 C14 H14 109.4 . . ?
O6 C14 C13 107.7(4) . . ?
C15 C14 H14 109.4 . . ?
C13 C14 C15 111.0(4) . . ?
C13 C14 H14 109.4 . . ?
O9 C20 C19 115.7(4) . . ?
O9 C20 C21 125.6(4) . . ?
C21 C20 C19 118.7(4) . . ?
O16 C41 C42 123.2(4) . . ?
O16 C41 C40 115.9(4) . . ?
C42 C41 C40 120.9(4) . . ?
C45 C44 C43 120.4(4) . . ?
C45 C44 O18 119.5(4) . . ?
O18 C44 C43 120.1(4) . . ?
O2 C2 C3 111.0(4) . . ?
O2 C2 H2A 108.6 . . ?
O2 C2 C1 108.8(4) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 C3 111.4(4) . . ?
C1 C2 H2A 108.6 . . ?
O11 C26 C27 109.1(4) . . ?
O11 C26 H26 109.2 . . ?
O11 C26 C25 108.0(4) . . ?
C27 C26 H26 109.2 . . ?
C25 C26 C27 112.2(4) . . ?
C25 C26 H26 109.2 . . ?
O17 C43 C42 124.4(4) . . ?
O17 C43 C44 116.3(4) . . ?
C42 C43 C44 119.3(4) . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C17 C16 C15 122.7(4) . . ?
C17 C16 C21 118.1(4) . . ?
C21 C16 C15 119.1(4) . . ?
C32 C33 H33 119.3 . . ?
C32 C33 C28 121.4(4) . . ?
C28 C33 H33 119.3 . . ?
C8 O5 C12 116.4(4) . . ?
O13 C31 C30 124.0(4) . . ?
O13 C31 C32 115.3(4) . . ?
C30 C31 C32 120.7(4) . . ?
C20 C21 C16 122.1(4) . . ?
C20 C21 H21 118.9 . . ?
C16 C21 H21 118.9 . . ?
O16 C46 H46A 109.5 . . ?
O16 C46 H46B 109.5 . . ?
O16 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C9 H9 118.9 . . ?
C8 C9 C4 122.1(4) . . ?
C8 C9 H9 118.9 . . ?
O14 C32 C33 125.1(4) . . ?
O14 C32 C31 115.7(4) . . ?
C31 C32 C33 119.2(4) . . ?
C29 C28 C27 121.6(4) . . ?
C29 C28 C33 118.3(4) . . ?
C33 C28 C27 120.1(4) . . ?
O8 C23 H23A 109.5 . . ?
O8 C23 H23B 109.5 . . ?
O8 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C44 O18 C48 115.4(5) . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O13 C35 H35A 109.5 . . ?
O13 C35 H35B 109.5 . . ?
O13 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
O7 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O14 C36 H36A 109.5 . . ?
O14 C36 H36B 109.5 . . ?
O14 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O17 C47 H47A 109.5 . . ?
O17 C47 H47B 109.5 . . ?
O17 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C5 C6 122.4(4) . . ?
O3 C5 C4 117.2(4) . . ?
C4 C5 C6 120.5(4) . . ?
O4 C7 C6 123.5(4) . . ?
O4 C7 C8 116.1(4) . . ?
C6 C7 C8 120.3(4) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C8 C9 124.5(4) . . ?
O5 C8 C7 116.6(4) . . ?
C9 C8 C7 118.9(4) . . ?
O9 C24 H24A 109.5 . . ?
O9 C24 H24B 109.5 . . ?
O9 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H20A O20 H20B 109.5 . . ?
H22D O22 H22E 109.5 . . ?
C49 O19 H19 109.5 . . ?
H23D O23 H23E 109.5 . . ?
O18 C48 H48A 109.5 . . ?
O18 C48 H48B 109.5 . . ?
O18 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
O19 C49 H49A 109.5 . . ?
O19 C49 H49B 109.5 . . ?
O19 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 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
O10 C39 C40 C45 48.3(6) . . . . ?
O10 C39 C40 C41 -129.0(4) . . . . ?
O10 C39 C38 O15 -62.0(5) . . . . ?
O10 C39 C38 C37 60.3(5) . . . . ?
O10 C27 C26 O11 57.0(4) . . . . ?
O10 C27 C26 C25 176.7(4) . . . . ?
O10 C27 C28 C29 -130.4(4) . . . . ?
O10 C27 C28 C33 49.2(5) . . . . ?
O1 C15 C14 O6 -52.4(5) . . . . ?
O1 C15 C14 C13 -171.6(4) . . . . ?
O1 C15 C16 C17 125.2(5) . . . . ?
O1 C15 C16 C21 -53.9(5) . . . . ?
O1 C3 C4 C9 -36.0(6) . . . . ?
O1 C3 C4 C5 139.1(4) . . . . ?
O1 C3 C2 O2 56.0(5) . . . . ?
O1 C3 C2 C1 -65.3(5) . . . . ?
O7 C17 C18 C19 178.5(4) . . . . ?
O7 C17 C16 C15 0.1(7) . . . . ?
O7 C17 C16 C21 179.2(4) . . . . ?
O4 C7 C8 O5 -0.8(6) . . . . ?
O4 C7 C8 C9 -178.0(4) . . . . ?
O13 C31 C32 O14 0.8(6) . . . . ?
O13 C31 C32 C33 -179.7(4) . . . . ?
O8 C19 C18 C17 -177.5(4) . . . . ?
O8 C19 C20 O9 -1.3(6) . . . . ?
O8 C19 C20 C21 178.6(4) . . . . ?
O12 C29 C28 C27 -2.3(6) . . . . ?
O12 C29 C28 C33 178.1(4) . . . . ?
C15 O1 C3 C4 -68.4(5) . . . . ?
C15 O1 C3 C2 167.2(3) . . . . ?
C15 C16 C21 C20 -178.5(4) . . . . ?
O9 C20 C21 C16 178.7(5) . . . . ?
C39 O10 C27 C26 -162.3(4) . . . . ?
C39 O10 C27 C28 74.4(4) . . . . ?
C39 C40 C45 C44 -179.0(5) . . . . ?
C39 C40 C41 O16 -3.0(6) . . . . ?
C39 C40 C41 C42 177.4(4) . . . . ?
C27 O10 C39 C40 65.2(4) . . . . ?
C27 O10 C39 C38 -169.3(4) . . . . ?
C40 C39 C38 O15 62.0(5) . . . . ?
C40 C39 C38 C37 -175.8(4) . . . . ?
C40 C45 C44 C43 3.2(8) . . . . ?
C40 C45 C44 O18 -174.9(5) . . . . ?
C3 O1 C15 C14 161.0(4) . . . . ?
C3 O1 C15 C16 -76.5(4) . . . . ?
C3 C4 C9 C8 174.6(4) . . . . ?
C3 C4 C5 O3 3.2(7) . . . . ?
C3 C4 C5 C6 -175.6(4) . . . . ?
C6 C7 C8 O5 176.3(4) . . . . ?
C6 C7 C8 C9 -0.9(7) . . . . ?
C34 O12 C29 C30 -24.6(7) . . . . ?
C34 O12 C29 C28 158.2(4) . . . . ?
C19 C20 C21 C16 -1.2(7) . . . . ?
C45 C40 C41 O16 179.6(4) . . . . ?
C45 C40 C41 C42 0.0(7) . . . . ?
C45 C44 C43 O17 177.2(5) . . . . ?
C45 C44 C43 C42 -2.9(8) . . . . ?
C45 C44 O18 C48 -103.5(6) . . . . ?
C38 C39 C40 C45 -73.6(5) . . . . ?
C38 C39 C40 C41 109.1(5) . . . . ?
C4 C3 C2 O2 -67.5(5) . . . . ?
C4 C3 C2 C1 171.2(4) . . . . ?
C4 C9 C8 O5 -175.8(5) . . . . ?
C4 C9 C8 C7 1.2(7) . . . . ?
C30 C29 C28 C27 -179.6(4) . . . . ?
C30 C29 C28 C33 0.8(7) . . . . ?
C30 C31 C32 O14 -179.1(4) . . . . ?
C30 C31 C32 C33 0.4(7) . . . . ?
C17 C16 C21 C20 2.3(7) . . . . ?
C18 C19 C20 O9 179.0(4) . . . . ?
C18 C19 C20 C21 -1.1(7) . . . . ?
C18 C17 C16 C15 179.7(4) . . . . ?
C18 C17 C16 C21 -1.1(7) . . . . ?
C29 C30 C31 O13 178.6(4) . . . . ?
C29 C30 C31 C32 -1.5(7) . . . . ?
C14 C15 C16 C17 -115.6(5) . . . . ?
C14 C15 C16 C21 65.3(5) . . . . ?
C20 C19 C18 C17 2.2(7) . . . . ?
C41 C42 C43 O17 -178.8(4) . . . . ?
C41 C42 C43 C44 1.3(7) . . . . ?
C41 C40 C45 C44 -1.7(7) . . . . ?
C2 C3 C4 C9 84.4(5) . . . . ?
C2 C3 C4 C5 -100.5(5) . . . . ?
C26 C27 C28 C29 110.3(5) . . . . ?
C26 C27 C28 C33 -70.1(5) . . . . ?
C43 C42 C41 O16 -179.4(4) . . . . ?
C43 C42 C41 C40 0.2(7) . . . . ?
C43 C44 O18 C48 78.4(7) . . . . ?
C16 C15 C14 O6 -174.1(3) . . . . ?
C16 C15 C14 C13 66.7(5) . . . . ?
C16 C17 C18 C19 -1.1(7) . . . . ?
C31 C30 C29 O12 -176.2(4) . . . . ?
C31 C30 C29 C28 0.9(7) . . . . ?
C46 O16 C41 C42 1.2(7) . . . . ?
C46 O16 C41 C40 -178.4(4) . . . . ?
C10 O3 C5 C6 19.4(7) . . . . ?
C10 O3 C5 C4 -159.4(4) . . . . ?
C9 C4 C5 O3 178.5(4) . . . . ?
C9 C4 C5 C6 -0.4(7) . . . . ?
C32 C33 C28 C27 178.5(4) . . . . ?
C32 C33 C28 C29 -2.0(7) . . . . ?
C28 C27 C26 O11 179.7(4) . . . . ?
C28 C27 C26 C25 -60.7(5) . . . . ?
C28 C33 C32 O14 -179.2(4) . . . . ?
C28 C33 C32 C31 1.4(7) . . . . ?
C23 O8 C19 C18 -0.2(7) . . . . ?
C23 O8 C19 C20 -179.9(4) . . . . ?
O18 C44 C43 O17 -4.7(7) . . . . ?
O18 C44 C43 C42 175.1(5) . . . . ?
C35 O13 C31 C30 7.7(7) . . . . ?
C35 O13 C31 C32 -172.2(4) . . . . ?
C22 O7 C17 C18 7.2(7) . . . . ?
C22 O7 C17 C16 -173.2(4) . . . . ?
C36 O14 C32 C33 -7.7(7) . . . . ?
C36 O14 C32 C31 171.7(4) . . . . ?
C47 O17 C43 C42 6.7(7) . . . . ?
C47 O17 C43 C44 -173.4(4) . . . . ?
C5 C6 C7 O4 176.9(4) . . . . ?
C5 C6 C7 C8 0.0(7) . . . . ?
C5 C4 C9 C8 -0.6(7) . . . . ?
C7 C6 C5 O3 -178.1(4) . . . . ?
C7 C6 C5 C4 0.7(7) . . . . ?
C11 O4 C7 C6 -2.7(7) . . . . ?
C11 O4 C7 C8 174.3(4) . . . . ?
C24 O9 C20 C19 -176.8(5) . . . . ?
C24 O9 C20 C21 3.3(8) . . . . ?
C12 O5 C8 C9 0.6(7) . . . . ?
C12 O5 C8 C7 -176.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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/access/V1 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 1518428'
_audit_update_record             
;
2016-11-22 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'asaroquinone A'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 O6'
_chemical_formula_weight         384.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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                   7.5710(2)
_cell_length_b                   15.1433(4)
_cell_length_c                   18.9868(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.489(3)
_cell_angle_gamma                90.00
_cell_volume                     2011.29(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3611
_cell_measurement_theta_min      3.8310
_cell_measurement_theta_max      62.6990

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8508
_exptl_absorpt_correction_T_max  0.9211
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8905
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.86
_diffrn_reflns_theta_max         62.76
_reflns_number_total             3208
_reflns_number_gt                2720
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0491P)²+0.5089P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3208
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 -0.00795(17) -0.54585(8) -0.18519(8) 0.0568(3) Uani 1 1 d . . .
O2 O 0.64439(15) -0.43927(7) -0.05828(6) 0.0455(3) Uani 1 1 d . . .
O3 O -0.13398(15) -0.37967(9) -0.17942(7) 0.0563(3) Uani 1 1 d . . .
O4 O 0.4889(2) -0.27902(8) 0.09666(7) 0.0573(3) Uani 1 1 d . . .
O5 O 0.30322(17) -0.16913(8) 0.14942(6) 0.0526(3) Uani 1 1 d . . .
O6 O 0.2108(2) 0.00959(9) -0.06549(8) 0.0738(4) Uani 1 1 d . . .
C1 C 0.0481(3) -0.63454(13) -0.17584(18) 0.0915(9) Uani 1 1 d . . .
H1A H 0.1371 -0.6451 -0.1998 0.137 Uiso 1 1 calc R . .
H1B H -0.0621 -0.6715 -0.1988 0.137 Uiso 1 1 calc R . .
H1C H 0.1078 -0.6479 -0.1225 0.137 Uiso 1 1 calc R . .
C2 C 0.1278(2) -0.48246(10) -0.15278(9) 0.0398(4) Uani 1 1 d . . .
C3 C 0.3239(2) -0.49820(10) -0.12216(9) 0.0390(4) Uani 1 1 d . . .
H3 H 0.3703 -0.5548 -0.1235 0.047 Uiso 1 1 calc R . .
C4 C 0.4500(2) -0.42953(9) -0.08963(8) 0.0348(3) Uani 1 1 d . . .
C5 C 0.3837(2) -0.34405(9) -0.08564(8) 0.0341(3) Uani 1 1 d . . .
C6 C 0.1881(2) -0.33025(10) -0.11774(8) 0.0382(3) Uani 1 1 d . . .
H6 H 0.1413 -0.2737 -0.1165 0.046 Uiso 1 1 calc R . .
C7 C 0.0601(2) -0.39705(10) -0.15136(9) 0.0393(4) Uani 1 1 d . . .
C8 C -0.2189(3) -0.37006(18) -0.25862(13) 0.0838(7) Uani 1 1 d . . .
H8A H -0.1954 -0.4220 -0.2827 0.126 Uiso 1 1 calc R . .
H8B H -0.1654 -0.3196 -0.2738 0.126 Uiso 1 1 calc R . .
H8C H -0.3542 -0.3620 -0.2737 0.126 Uiso 1 1 calc R . .
C9 C 0.7233(2) -0.52143(11) -0.06699(11) 0.0519(4) Uani 1 1 d . . .
H9A H 0.6777 -0.5365 -0.1201 0.078 Uiso 1 1 calc R . .
H9B H 0.6856 -0.5663 -0.0398 0.078 Uiso 1 1 calc R . .
H9C H 0.8602 -0.5171 -0.0469 0.078 Uiso 1 1 calc R . .
C10 C 0.5285(2) -0.27178(10) -0.04667(8) 0.0369(3) Uani 1 1 d . . .
H10 H 0.6300 -0.2989 -0.0029 0.044 Uiso 1 1 calc R . .
C11 C 0.6238(2) -0.23327(11) -0.09909(10) 0.0446(4) Uani 1 1 d . . .
H11 H 0.6384 -0.2813 -0.1310 0.054 Uiso 1 1 calc R . .
C12 C 0.5041(3) -0.16194(11) -0.15105(9) 0.0485(4) Uani 1 1 d . . .
C13 C 0.3903(3) -0.11117(11) -0.12902(9) 0.0479(4) Uani 1 1 d . . .
H13 H 0.3214 -0.0659 -0.1608 0.057 Uiso 1 1 calc R . .
C14 C 0.3722(2) -0.12539(10) -0.05650(9) 0.0391(4) Uani 1 1 d . . .
C15 C 0.4397(2) -0.19968(9) -0.01608(8) 0.0352(3) Uani 1 1 d . . .
C16 C 0.4213(2) -0.21441(10) 0.05723(8) 0.0382(4) Uani 1 1 d . . .
C17 C 0.3171(2) -0.14578(10) 0.08358(8) 0.0390(4) Uani 1 1 d . . .
C18 C 0.2519(2) -0.07204(11) 0.04380(9) 0.0453(4) Uani 1 1 d . . .
H18 H 0.1914 -0.0297 0.0622 0.054 Uiso 1 1 calc R . .
C19 C 0.2742(2) -0.05699(11) -0.02806(10) 0.0454(4) Uani 1 1 d . . .
C20 C 0.2170(4) -0.10689(17) 0.18368(12) 0.0788(7) Uani 1 1 d . . .
H20A H 0.0860 -0.0977 0.1506 0.118 Uiso 1 1 calc R . .
H20B H 0.2847 -0.0518 0.1916 0.118 Uiso 1 1 calc R . .
H20C H 0.2227 -0.1295 0.2317 0.118 Uiso 1 1 calc R . .
C21 C 0.5276(4) -0.14730(16) -0.22522(12) 0.0762(7) Uani 1 1 d . . .
H21A H 0.6602 -0.1374 -0.2155 0.114 Uiso 1 1 calc R . .
H21B H 0.4543 -0.0967 -0.2505 0.114 Uiso 1 1 calc R . .
H21C H 0.4836 -0.1984 -0.2570 0.114 Uiso 1 1 calc R . .
C22 C 0.8232(3) -0.19760(14) -0.05149(13) 0.0637(5) Uani 1 1 d . . .
H22A H 0.8135 -0.1537 -0.0167 0.096 Uiso 1 1 calc R . .
H22B H 0.8779 -0.1716 -0.0846 0.096 Uiso 1 1 calc R . .
H22C H 0.9031 -0.2451 -0.0233 0.096 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 1.3684(19) . ?
O1 C1 1.399(2) . ?
O2 C4 1.3678(18) . ?
O2 C9 1.4172(19) . ?
O3 C7 1.3835(18) . ?
O3 C8 1.399(3) . ?
O4 C16 1.2192(19) . ?
O5 C17 1.3413(19) . ?
O5 C20 1.436(2) . ?
O6 C19 1.221(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.393(2) . ?
C2 C7 1.395(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(2) . ?
C5 C6 1.385(2) . ?
C5 C10 1.525(2) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.510(2) . ?
C10 C11 1.549(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.509(3) . ?
C11 C22 1.531(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.336(2) . ?
C12 C21 1.502(2) . ?
C13 C14 1.451(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.348(2) . ?
C14 C19 1.491(2) . ?
C15 C16 1.468(2) . ?
C16 C17 1.502(2) . ?
C17 C18 1.333(2) . ?
C18 C19 1.455(2) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 C1 118.48(14) . . ?
C4 O2 C9 118.39(12) . . ?
C7 O3 C8 114.68(14) . . ?
C17 O5 C20 117.40(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.42(14) . . ?
O1 C2 C7 116.16(14) . . ?
C3 C2 C7 119.42(14) . . ?
C4 C3 C2 120.02(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O2 C4 C3 123.76(13) . . ?
O2 C4 C5 115.10(13) . . ?
C3 C4 C5 121.13(13) . . ?
C6 C5 C4 117.43(14) . . ?
C6 C5 C10 123.68(13) . . ?
C4 C5 C10 118.90(13) . . ?
C7 C6 C5 122.51(14) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 O3 119.61(14) . . ?
C6 C7 C2 119.45(14) . . ?
O3 C7 C2 120.84(14) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C5 111.22(12) . . ?
C15 C10 C11 111.11(12) . . ?
C5 C10 C11 112.55(12) . . ?
C15 C10 H10 107.2 . . ?
C5 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C12 C11 C22 110.08(14) . . ?
C12 C11 C10 112.26(13) . . ?
C22 C11 C10 110.47(15) . . ?
C12 C11 H11 108.0 . . ?
C22 C11 H11 108.0 . . ?
C10 C11 H11 108.0 . . ?
C13 C12 C21 122.05(18) . . ?
C13 C12 C11 120.34(15) . . ?
C21 C12 C11 117.50(16) . . ?
C12 C13 C14 121.21(16) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.76(14) . . ?
C15 C14 C19 120.44(14) . . ?
C13 C14 C19 118.79(14) . . ?
C14 C15 C16 120.94(14) . . ?
C14 C15 C10 120.81(13) . . ?
C16 C15 C10 118.20(13) . . ?
O4 C16 C15 122.31(14) . . ?
O4 C16 C17 120.09(14) . . ?
C15 C16 C17 117.60(13) . . ?
C18 C17 O5 127.23(14) . . ?
C18 C17 C16 121.27(14) . . ?
O5 C17 C16 111.50(13) . . ?
C17 C18 C19 120.79(14) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
O6 C19 C18 120.93(15) . . ?
O6 C19 C14 120.15(16) . . ?
C18 C19 C14 118.90(14) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C22 H22A 109.5 . . ?
C11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C1 O1 C2 C3 11.6(3) . . . . ?
C1 O1 C2 C7 -168.4(2) . . . . ?
O1 C2 C3 C4 -179.16(14) . . . . ?
C7 C2 C3 C4 0.9(2) . . . . ?
C9 O2 C4 C3 7.5(2) . . . . ?
C9 O2 C4 C5 -173.64(14) . . . . ?
C2 C3 C4 O2 179.95(14) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
O2 C4 C5 C6 178.92(13) . . . . ?
C3 C4 C5 C6 -2.2(2) . . . . ?
O2 C4 C5 C10 -1.10(19) . . . . ?
C3 C4 C5 C10 177.81(14) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
C10 C5 C6 C7 -178.77(14) . . . . ?
C5 C6 C7 O3 177.19(14) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C8 O3 C7 C6 102.3(2) . . . . ?
C8 O3 C7 C2 -81.4(2) . . . . ?
O1 C2 C7 C6 178.21(14) . . . . ?
C3 C2 C7 C6 -1.9(2) . . . . ?
O1 C2 C7 O3 1.9(2) . . . . ?
C3 C2 C7 O3 -178.22(14) . . . . ?
C6 C5 C10 C15 25.7(2) . . . . ?
C4 C5 C10 C15 -154.31(13) . . . . ?
C6 C5 C10 C11 -99.76(17) . . . . ?
C4 C5 C10 C11 80.27(17) . . . . ?
C15 C10 C11 C12 -41.48(17) . . . . ?
C5 C10 C11 C12 84.00(16) . . . . ?
C15 C10 C11 C22 81.80(16) . . . . ?
C5 C10 C11 C22 -152.71(14) . . . . ?
C22 C11 C12 C13 -93.33(19) . . . . ?
C10 C11 C12 C13 30.2(2) . . . . ?
C22 C11 C12 C21 83.1(2) . . . . ?
C10 C11 C12 C21 -153.44(16) . . . . ?
C21 C12 C13 C14 -178.86(17) . . . . ?
C11 C12 C13 C14 -2.6(3) . . . . ?
C12 C13 C14 C15 -12.8(3) . . . . ?
C12 C13 C14 C19 168.33(15) . . . . ?
C13 C14 C15 C16 -179.87(14) . . . . ?
C19 C14 C15 C16 -1.0(2) . . . . ?
C13 C14 C15 C10 -2.6(2) . . . . ?
C19 C14 C15 C10 176.29(13) . . . . ?
C5 C10 C15 C14 -96.58(16) . . . . ?
C11 C10 C15 C14 29.64(19) . . . . ?
C5 C10 C15 C16 80.80(16) . . . . ?
C11 C10 C15 C16 -152.98(13) . . . . ?
C14 C15 C16 O4 -176.49(15) . . . . ?
C10 C15 C16 O4 6.1(2) . . . . ?
C14 C15 C16 C17 2.7(2) . . . . ?
C10 C15 C16 C17 -174.67(12) . . . . ?
C20 O5 C17 C18 -3.2(3) . . . . ?
C20 O5 C17 C16 176.24(16) . . . . ?
O4 C16 C17 C18 175.94(16) . . . . ?
C15 C16 C17 C18 -3.3(2) . . . . ?
O4 C16 C17 O5 -3.5(2) . . . . ?
C15 C16 C17 O5 177.24(13) . . . . ?
O5 C17 C18 C19 -178.54(15) . . . . ?
C16 C17 C18 C19 2.1(2) . . . . ?
C17 C18 C19 O6 178.32(17) . . . . ?
C17 C18 C19 C14 -0.3(2) . . . . ?
C15 C14 C19 O6 -178.89(16) . . . . ?
C13 C14 C19 O6 0.0(2) . . . . ?
C15 C14 C19 C18 -0.3(2) . . . . ?
C13 C14 C19 C18 178.58(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        62.76
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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/access/V1 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 1518427'
_audit_update_record             
;
2016-11-22 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'asarolignan D'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H36 O7'
_chemical_formula_weight         448.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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                   11.7316(5)
_cell_length_b                   25.2812(8)
_cell_length_c                   8.4293(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.814(3)
_cell_angle_gamma                90.00
_cell_volume                     2476.82(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3062
_cell_measurement_theta_min      4.1960
_cell_measurement_theta_max      62.8030

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8046
_exptl_absorpt_correction_T_max  0.9133
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11344
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         62.72
_reflns_number_total             3954
_reflns_number_gt                3014
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0688P)²+0.5641P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3954
_refine_ls_number_parameters     303
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.009
_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 0.29574(18) -0.20042(6) 0.4100(2) 0.0755(5) Uani 1 1 d . . .
O2 O 0.27488(16) -0.17228(6) 0.10138(19) 0.0691(5) Uani 1 1 d . A .
O3 O 0.22044(15) 0.01001(6) 0.25870(17) 0.0623(4) Uani 1 1 d . A .
O4 O 0.19685(14) -0.03779(6) 0.71562(16) 0.0576(4) Uani 1 1 d . A .
O5 O 0.12675(16) 0.10618(7) 0.80995(19) 0.0742(5) Uani 1 1 d . A .
O6 O 0.03303(18) 0.20739(7) 0.3207(2) 0.0785(5) Uani 1 1 d . A .
O7 O 0.2278(2) 0.16806(7) 0.2171(2) 0.0868(6) Uani 1 1 d . . .
C2 C 0.2764(2) -0.14773(8) 0.3703(3) 0.0554(5) Uani 1 1 d . A .
C3 C 0.2639(2) -0.11023(8) 0.4856(3) 0.0551(5) Uani 1 1 d . . .
H3 H 0.2689 -0.1209 0.5920 0.066 Uiso 1 1 calc R A .
C4 C 0.24418(19) -0.05737(8) 0.4490(2) 0.0498(5) Uani 1 1 d . A .
C5 C 0.23698(19) -0.04271(8) 0.2881(2) 0.0502(5) Uani 1 1 d . . .
C6 C 0.24644(19) -0.08002(8) 0.1696(2) 0.0523(5) Uani 1 1 d . A .
H6 H 0.2401 -0.0696 0.0629 0.063 Uiso 1 1 calc R . .
C7 C 0.26530(19) -0.13262(8) 0.2099(2) 0.0528(5) Uani 1 1 d . . .
C8 C 0.2537(3) -0.15903(12) -0.0630(3) 0.0895(9) Uani 1 1 d . . .
H8A H 0.2619 -0.1900 -0.1263 0.134 Uiso 1 1 calc R A .
H8B H 0.3079 -0.1327 -0.0865 0.134 Uiso 1 1 calc R . .
H8C H 0.1770 -0.1454 -0.0879 0.134 Uiso 1 1 calc R . .
C9 C 0.2203(3) 0.02896(10) 0.1018(3) 0.0778(8) Uani 1 1 d . . .
H9A H 0.1548 0.0151 0.0340 0.117 Uiso 1 1 calc R A .
H9B H 0.2895 0.0179 0.0624 0.117 Uiso 1 1 calc R . .
H9C H 0.2166 0.0669 0.1019 0.117 Uiso 1 1 calc R . .
C10 C 0.23465(19) -0.01544(8) 0.5753(2) 0.0491(5) Uani 1 1 d . . .
H10 H 0.1775 0.0107 0.5304 0.059 Uiso 1 1 calc R A .
C11 C 0.0765(2) -0.04318(12) 0.7015(3) 0.0744(7) Uani 1 1 d . . .
H11A H 0.0502 -0.0651 0.6109 0.112 Uiso 1 1 calc R A .
H11B H 0.0413 -0.0089 0.6871 0.112 Uiso 1 1 calc R . .
H11C H 0.0560 -0.0592 0.7969 0.112 Uiso 1 1 calc R . .
C12 C 0.34923(19) 0.01345(8) 0.6256(2) 0.0508(5) Uani 1 1 d . A .
H12 H 0.3808 0.0227 0.5274 0.061 Uiso 1 1 calc R . .
C13 C 0.4366(2) -0.02264(10) 0.7235(3) 0.0661(6) Uani 1 1 d . . .
H13A H 0.4141 -0.0281 0.8277 0.099 Uiso 1 1 calc R A .
H13B H 0.5112 -0.0064 0.7346 0.099 Uiso 1 1 calc R . .
H13C H 0.4393 -0.0560 0.6700 0.099 Uiso 1 1 calc R . .
C14 C 0.32847(19) 0.06566(8) 0.7124(2) 0.0511(5) Uani 1 1 d . . .
H14 H 0.2910 0.0563 0.8057 0.061 Uiso 1 1 calc R A .
C15 C 0.4403(2) 0.09442(10) 0.7759(3) 0.0712(7) Uani 1 1 d . A .
H15A H 0.4897 0.0705 0.8439 0.085 Uiso 1 1 calc R . .
H15B H 0.4799 0.1040 0.6863 0.085 Uiso 1 1 calc R . .
C16 C 0.4204(3) 0.14389(13) 0.8704(5) 0.1027(11) Uani 1 1 d . . .
H16A H 0.3773 0.1691 0.8012 0.154 Uiso 1 1 calc R A .
H16B H 0.4932 0.1590 0.9132 0.154 Uiso 1 1 calc R . .
H16C H 0.3782 0.1349 0.9565 0.154 Uiso 1 1 calc R . .
C17 C 0.24755(19) 0.10241(8) 0.6099(2) 0.0507(5) Uani 1 1 d . A .
C18 C 0.2709(2) 0.11993(9) 0.4610(3) 0.0589(6) Uani 1 1 d . . .
H18 H 0.3368 0.1076 0.4229 0.071 Uiso 1 1 calc R A .
C19 C 0.2004(2) 0.15481(9) 0.3676(3) 0.0621(6) Uani 1 1 d . A .
C20 C 0.1014(2) 0.17361(9) 0.4205(3) 0.0594(6) Uani 1 1 d . . .
C21 C 0.0758(2) 0.15764(9) 0.5690(3) 0.0595(6) Uani 1 1 d . A .
H21 H 0.0100 0.1702 0.6068 0.071 Uiso 1 1 calc R . .
C22 C 0.1490(2) 0.12268(8) 0.6615(2) 0.0533(5) Uani 1 1 d . . .
C23 C 0.0453(3) 0.13295(17) 0.8832(4) 0.1085(13) Uani 1 1 d . . .
H23A H -0.0301 0.1251 0.8287 0.163 Uiso 1 1 calc R A .
H23B H 0.0591 0.1703 0.8787 0.163 Uiso 1 1 calc R . .
H23C H 0.0503 0.1220 0.9929 0.163 Uiso 1 1 calc R . .
C24 C -0.0635(3) 0.22972(11) 0.3795(4) 0.0808(8) Uani 1 1 d . . .
H24A H -0.1036 0.2525 0.2996 0.121 Uiso 1 1 calc R A .
H24B H -0.0383 0.2498 0.4745 0.121 Uiso 1 1 calc R . .
H24C H -0.1141 0.2020 0.4044 0.121 Uiso 1 1 calc R . .
C25 C 0.2708(4) 0.21979(13) 0.2049(4) 0.1078(12) Uani 1 1 d . . .
H25A H 0.2751 0.2278 0.0946 0.162 Uiso 1 1 calc R . .
H25B H 0.3462 0.2222 0.2652 0.162 Uiso 1 1 calc R . .
H25C H 0.2204 0.2445 0.2466 0.162 Uiso 1 1 calc R . .
C1B C 0.4085(16) -0.2146(6) 0.441(2) 0.091(2) Uani 0.399(17) 1 d PU A 2
H1BA H 0.4434 -0.2121 0.3450 0.136 Uiso 0.399(17) 1 calc PR A 2
H1BB H 0.4140 -0.2503 0.4801 0.136 Uiso 0.399(17) 1 calc PR A 2
H1BC H 0.4475 -0.1914 0.5210 0.136 Uiso 0.399(17) 1 calc PR A 2
C1A C 0.3975(10) -0.2105(4) 0.5167(16) 0.091(2) Uani 0.601(17) 1 d PU A 1
H1AA H 0.4612 -0.1931 0.4789 0.136 Uiso 0.601(17) 1 calc PR A 1
H1AB H 0.4115 -0.2480 0.5223 0.136 Uiso 0.601(17) 1 calc PR A 1
H1AC H 0.3886 -0.1975 0.6213 0.136 Uiso 0.601(17) 1 calc PR A 1


_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 C1B 1.361(18) . ?
O1 C2 1.385(3) . ?
O1 C1A 1.417(11) . ?
O2 C7 1.372(3) . ?
O2 C8 1.414(3) . ?
O3 C5 1.365(2) . ?
O3 C9 1.407(3) . ?
O4 C11 1.407(3) . ?
O4 C10 1.435(2) . ?
O5 C22 1.377(3) . ?
O5 C23 1.383(3) . ?
O6 C20 1.378(3) . ?
O6 C24 1.414(3) . ?
O7 C19 1.392(3) . ?
O7 C25 1.410(4) . ?
C2 C3 1.380(3) . ?
C2 C7 1.394(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(3) . ?
C4 C10 1.518(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12 1.538(3) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.528(3) . ?
C12 C14 1.545(3) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C17 1.513(3) . ?
C14 C15 1.531(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.518(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.387(3) . ?
C17 C18 1.393(3) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(4) . ?
C20 C21 1.387(3) . ?
C21 C22 1.394(3) . ?
C21 H21 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?

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
C1B O1 C2 115.0(7) . . ?
C1B O1 C1A 28.0(6) . . ?
C2 O1 C1A 115.1(4) . . ?
C7 O2 C8 117.43(19) . . ?
C5 O3 C9 119.04(17) . . ?
C11 O4 C10 112.79(17) . . ?
C22 O5 C23 119.0(2) . . ?
C20 O6 C24 117.45(19) . . ?
C19 O7 C25 114.8(2) . . ?
C3 C2 O1 121.32(19) . . ?
C3 C2 C7 119.36(19) . . ?
O1 C2 C7 119.28(19) . . ?
C2 C3 C4 122.44(19) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 117.34(19) . . ?
C3 C4 C10 122.94(18) . . ?
C5 C4 C10 119.68(18) . . ?
O3 C5 C6 123.76(18) . . ?
O3 C5 C4 115.08(17) . . ?
C6 C5 C4 121.16(19) . . ?
C7 C6 C5 120.13(18) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O2 C7 C6 124.32(19) . . ?
O2 C7 C2 116.16(19) . . ?
C6 C7 C2 119.52(19) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 C4 111.34(16) . . ?
O4 C10 C12 108.46(16) . . ?
C4 C10 C12 112.34(17) . . ?
O4 C10 H10 108.2 . . ?
C4 C10 H10 108.2 . . ?
C12 C10 H10 108.2 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 111.24(18) . . ?
C13 C12 C14 113.03(18) . . ?
C10 C12 C14 110.37(17) . . ?
C13 C12 H12 107.3 . . ?
C10 C12 H12 107.3 . . ?
C14 C12 H12 107.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C14 C15 110.43(18) . . ?
C17 C14 C12 112.40(17) . . ?
C15 C14 C12 112.86(19) . . ?
C17 C14 H14 106.9 . . ?
C15 C14 H14 106.9 . . ?
C12 C14 H14 106.9 . . ?
C16 C15 C14 112.9(2) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 116.0(2) . . ?
C22 C17 C14 122.20(18) . . ?
C18 C17 C14 121.68(19) . . ?
C19 C18 C17 122.8(2) . . ?
C19 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 O7 118.6(2) . . ?
C20 C19 O7 121.3(2) . . ?
O6 C20 C19 117.4(2) . . ?
O6 C20 C21 123.5(2) . . ?
C19 C20 C21 119.0(2) . . ?
C20 C21 C22 119.8(2) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
O5 C22 C17 116.21(19) . . ?
O5 C22 C21 121.4(2) . . ?
C17 C22 C21 122.36(19) . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 H25A 109.5 . . ?
O7 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O7 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 C1B H1BA 109.5 . . ?
O1 C1B H1BB 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
O1 C1B H1BC 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
O1 C1A H1AA 109.5 . . ?
O1 C1A H1AB 109.5 . . ?
O1 C1A H1AC 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
C1B O1 C2 C3 -91.4(9) . . . . ?
C1A O1 C2 C3 -60.4(7) . . . . ?
C1B O1 C2 C7 91.0(9) . . . . ?
C1A O1 C2 C7 121.9(7) . . . . ?
O1 C2 C3 C4 -179.8(2) . . . . ?
C7 C2 C3 C4 -2.2(4) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C10 -177.7(2) . . . . ?
C9 O3 C5 C6 -4.4(3) . . . . ?
C9 O3 C5 C4 175.5(2) . . . . ?
C3 C4 C5 O3 -178.4(2) . . . . ?
C10 C4 C5 O3 -0.5(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C10 C4 C5 C6 179.4(2) . . . . ?
O3 C5 C6 C7 178.8(2) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C8 O2 C7 C6 -6.0(4) . . . . ?
C8 O2 C7 C2 174.4(2) . . . . ?
C5 C6 C7 O2 179.4(2) . . . . ?
C5 C6 C7 C2 -1.0(3) . . . . ?
C3 C2 C7 O2 -177.8(2) . . . . ?
O1 C2 C7 O2 -0.1(3) . . . . ?
C3 C2 C7 C6 2.6(3) . . . . ?
O1 C2 C7 C6 -179.8(2) . . . . ?
C11 O4 C10 C4 -83.4(2) . . . . ?
C11 O4 C10 C12 152.54(19) . . . . ?
C3 C4 C10 O4 -26.2(3) . . . . ?
C5 C4 C10 O4 156.12(19) . . . . ?
C3 C4 C10 C12 95.7(2) . . . . ?
C5 C4 C10 C12 -82.0(2) . . . . ?
O4 C10 C12 C13 52.7(2) . . . . ?
C4 C10 C12 C13 -70.8(2) . . . . ?
O4 C10 C12 C14 -73.6(2) . . . . ?
C4 C10 C12 C14 162.89(16) . . . . ?
C13 C12 C14 C17 176.41(18) . . . . ?
C10 C12 C14 C17 -58.3(2) . . . . ?
C13 C12 C14 C15 50.7(3) . . . . ?
C10 C12 C14 C15 176.00(18) . . . . ?
C17 C14 C15 C16 56.9(3) . . . . ?
C12 C14 C15 C16 -176.3(2) . . . . ?
C15 C14 C17 C22 -107.6(2) . . . . ?
C12 C14 C17 C22 125.4(2) . . . . ?
C15 C14 C17 C18 69.2(3) . . . . ?
C12 C14 C17 C18 -57.9(3) . . . . ?
C22 C17 C18 C19 -0.9(3) . . . . ?
C14 C17 C18 C19 -177.8(2) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C17 C18 C19 O7 -176.9(2) . . . . ?
C25 O7 C19 C18 -107.6(3) . . . . ?
C25 O7 C19 C20 75.9(4) . . . . ?
C24 O6 C20 C19 -175.4(2) . . . . ?
C24 O6 C20 C21 4.9(4) . . . . ?
C18 C19 C20 O6 -178.6(2) . . . . ?
O7 C19 C20 O6 -2.1(3) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
O7 C19 C20 C21 177.6(2) . . . . ?
O6 C20 C21 C22 179.1(2) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
C23 O5 C22 C17 166.3(3) . . . . ?
C23 O5 C22 C21 -13.9(4) . . . . ?
C18 C17 C22 O5 -178.9(2) . . . . ?
C14 C17 C22 O5 -1.9(3) . . . . ?
C18 C17 C22 C21 1.4(3) . . . . ?
C14 C17 C22 C21 178.3(2) . . . . ?
C20 C21 C22 O5 179.6(2) . . . . ?
C20 C21 C22 C17 -0.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        62.72
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.037
