# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ar22m
_database_code_depnum_ccdc_archive 'CCDC 937572'
_audit_update_record             
;
2013-05-06 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 O6'
_chemical_formula_sum            'C24 H34 O6'
_chemical_formula_weight         418.51
_chemical_absolute_configuration rm

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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'

_cell_length_a                   11.987(3)
_cell_length_b                   12.551(3)
_cell_length_c                   14.454(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2174.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5607
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      20.42

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21307
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2185
_reflns_number_gt                1977
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0570P)²+0.4217P] 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         2185
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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
C1 C 0.4142(3) 0.6928(2) 0.4714(2) 0.0511(7) Uani 1 1 d . . .
H1A H 0.3908 0.6646 0.5308 0.061 Uiso 1 1 calc R . .
H1B H 0.4930 0.7096 0.4757 0.061 Uiso 1 1 calc R . .
C2 C 0.3976(3) 0.6079(2) 0.3977(2) 0.0559(8) Uani 1 1 d . . .
H2A H 0.4408 0.5453 0.4138 0.067 Uiso 1 1 calc R . .
H2B H 0.3195 0.5876 0.3960 0.067 Uiso 1 1 calc R . .
C3 C 0.4327(3) 0.6469(2) 0.3031(2) 0.0506(7) Uani 1 1 d . . .
H3 H 0.5132 0.6593 0.3075 0.061 Uiso 1 1 calc R . .
C4 C 0.3829(2) 0.7530(2) 0.27243(19) 0.0460(7) Uani 1 1 d . . .
C5 C 0.3836(2) 0.8347(2) 0.35379(18) 0.0414(6) Uani 1 1 d . . .
H5 H 0.4624 0.8539 0.3604 0.050 Uiso 1 1 calc R . .
C6 C 0.3272(3) 0.9393(2) 0.3290(2) 0.0561(8) Uani 1 1 d . . .
H6A H 0.2475 0.9277 0.3229 0.067 Uiso 1 1 calc R . .
H6B H 0.3552 0.9640 0.2698 0.067 Uiso 1 1 calc R . .
C7 C 0.3483(3) 1.0243(2) 0.4024(2) 0.0602(9) Uani 1 1 d . . .
H7A H 0.4260 1.0460 0.4000 0.072 Uiso 1 1 calc R . .
H7B H 0.3027 1.0863 0.3892 0.072 Uiso 1 1 calc R . .
C8 C 0.3219(3) 0.9841(2) 0.4967(2) 0.0553(8) Uani 1 1 d . . .
C9 C 0.3815(3) 0.8833(2) 0.52173(18) 0.0468(7) Uani 1 1 d . . .
H9 H 0.4608 0.8979 0.5113 0.056 Uiso 1 1 calc R . .
C10 C 0.3502(2) 0.7934(2) 0.45169(18) 0.0408(6) Uani 1 1 d . . .
C11 C 0.3719(3) 0.8512(3) 0.62464(19) 0.0597(9) Uani 1 1 d . . .
H11A H 0.2937 0.8428 0.6402 0.072 Uiso 1 1 calc R . .
H11B H 0.4079 0.7827 0.6334 0.072 Uiso 1 1 calc R . .
C12 C 0.4224(3) 0.9292(3) 0.6886(2) 0.0617(9) Uani 1 1 d . . .
H12 H 0.4287 0.9992 0.6681 0.074 Uiso 1 1 calc R . .
C13 C 0.4591(3) 0.9076(3) 0.7724(2) 0.0553(8) Uani 1 1 d . . .
C14 C 0.4639(3) 0.8060(3) 0.8235(2) 0.0534(8) Uani 1 1 d . . .
H14 H 0.5023 0.7507 0.7878 0.064 Uiso 1 1 calc R . .
C15 C 0.5273(3) 0.8349(4) 0.9093(2) 0.0733(11) Uani 1 1 d . . .
H15A H 0.4883 0.8089 0.9636 0.088 Uiso 1 1 calc R . .
H15B H 0.6010 0.8029 0.9079 0.088 Uiso 1 1 calc R . .
C16 C 0.5016(4) 0.9920(4) 0.8331(3) 0.0751(11) Uani 1 1 d . . .
C17 C 0.3449(3) 0.6805(3) 0.8904(2) 0.0613(9) Uani 1 1 d . . .
C18 C 0.2323(4) 0.6591(3) 0.9143(4) 0.0925(14) Uani 1 1 d . . .
H18A H 0.1976 0.7232 0.9363 0.139 Uiso 1 1 calc R . .
H18B H 0.2300 0.6059 0.9620 0.139 Uiso 1 1 calc R . .
H18C H 0.1930 0.6336 0.8608 0.139 Uiso 1 1 calc R . .
C19 C 0.2702(3) 0.7306(3) 0.2353(2) 0.0563(8) Uani 1 1 d . . .
H19A H 0.2220 0.7071 0.2852 0.068 Uiso 1 1 calc R . .
H19B H 0.2390 0.7955 0.2096 0.068 Uiso 1 1 calc R . .
C20 C 0.3133(3) 0.5544(3) 0.2031(3) 0.0623(9) Uani 1 1 d . . .
H20 H 0.2650 0.5319 0.2542 0.075 Uiso 1 1 calc R . .
C21 C 0.4516(3) 0.7968(3) 0.1926(2) 0.0713(10) Uani 1 1 d . . .
H21A H 0.4568 0.7442 0.1447 0.107 Uiso 1 1 calc R . .
H21B H 0.5251 0.8143 0.2142 0.107 Uiso 1 1 calc R . .
H21C H 0.4164 0.8597 0.1686 0.107 Uiso 1 1 calc R . .
C22 C 0.2294(3) 0.7709(3) 0.4623(2) 0.0567(8) Uani 1 1 d . . .
H22A H 0.2120 0.7623 0.5267 0.085 Uiso 1 1 calc R . .
H22B H 0.2110 0.7067 0.4295 0.085 Uiso 1 1 calc R . .
H22C H 0.1870 0.8292 0.4374 0.085 Uiso 1 1 calc R . .
C23 C 0.2493(4) 1.0304(3) 0.5485(3) 0.0863(12) Uani 1 1 d . . .
H23A H 0.2120 1.0905 0.5273 0.104 Uiso 1 1 calc R . .
H23B H 0.2343 1.0037 0.6072 0.104 Uiso 1 1 calc R . .
C24 C 0.3123(3) 0.4718(3) 0.1277(3) 0.0856(13) Uani 1 1 d . . .
H24A H 0.3414 0.4060 0.1513 0.128 Uiso 1 1 calc R . .
H24B H 0.3577 0.4957 0.0771 0.128 Uiso 1 1 calc R . .
H24C H 0.2372 0.4612 0.1067 0.128 Uiso 1 1 calc R . .
O1 O 0.41948(18) 0.56635(18) 0.23358(16) 0.0606(6) Uani 1 1 d . . .
O2 O 0.2740(2) 0.65044(19) 0.16524(15) 0.0643(7) Uani 1 1 d . . .
O3 O 0.5362(2) 0.9478(3) 0.91247(17) 0.0831(8) Uani 1 1 d . . .
O4 O 0.5066(4) 1.0857(2) 0.8205(2) 0.1136(13) Uani 1 1 d . . .
O5 O 0.35534(17) 0.77475(16) 0.84755(14) 0.0520(5) Uani 1 1 d . . .
O6 O 0.4193(3) 0.6246(2) 0.9082(2) 0.1063(11) Uani 1 1 d . . .


_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
C1 C10 1.505(4) . ?
C1 C2 1.520(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.512(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O1 1.434(3) . ?
C3 C4 1.525(4) . ?
C3 H3 0.9800 . ?
C4 C19 1.480(4) . ?
C4 C21 1.521(4) . ?
C4 C5 1.561(4) . ?
C5 C6 1.519(4) . ?
C5 C10 1.559(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.526(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.488(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C23 1.286(5) . ?
C8 C9 1.497(4) . ?
C9 C11 1.546(4) . ?
C9 C10 1.562(4) . ?
C9 H9 0.9800 . ?
C10 C22 1.483(4) . ?
C11 C12 1.476(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.317(4) . ?
C12 H12 0.9300 . ?
C13 C16 1.467(5) . ?
C13 C14 1.475(5) . ?
C14 O5 1.403(4) . ?
C14 C15 1.500(5) . ?
C14 H14 0.9800 . ?
C15 O3 1.422(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O4 1.191(5) . ?
C16 O3 1.340(5) . ?
C17 O6 1.164(4) . ?
C17 O5 1.341(4) . ?
C17 C18 1.420(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O2 1.428(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O1 1.355(4) . ?
C20 O2 1.405(4) . ?
C20 C24 1.504(5) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9300 . ?
C23 H23B 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C10 C1 C2 112.8(2) . . ?
C10 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
C10 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 111.8(2) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 C2 112.0(2) . . ?
O1 C3 C4 111.6(2) . . ?
C2 C3 C4 115.9(3) . . ?
O1 C3 H3 105.5 . . ?
C2 C3 H3 105.5 . . ?
C4 C3 H3 105.5 . . ?
C19 C4 C21 106.7(3) . . ?
C19 C4 C3 107.3(3) . . ?
C21 C4 C3 108.9(3) . . ?
C19 C4 C5 113.8(2) . . ?
C21 C4 C5 109.3(3) . . ?
C3 C4 C5 110.7(2) . . ?
C6 C5 C10 112.8(2) . . ?
C6 C5 C4 112.8(2) . . ?
C10 C5 C4 117.6(2) . . ?
C6 C5 H5 103.9 . . ?
C10 C5 H5 103.9 . . ?
C4 C5 H5 103.9 . . ?
C5 C6 C7 111.5(2) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 111.3(3) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C23 C8 C7 121.6(3) . . ?
C23 C8 C9 124.3(3) . . ?
C7 C8 C9 114.0(3) . . ?
C8 C9 C11 114.7(3) . . ?
C8 C9 C10 109.8(2) . . ?
C11 C9 C10 114.7(2) . . ?
C8 C9 H9 105.6 . . ?
C11 C9 H9 105.6 . . ?
C10 C9 H9 105.6 . . ?
C22 C10 C1 108.6(3) . . ?
C22 C10 C5 114.0(2) . . ?
C1 C10 C5 108.7(2) . . ?
C22 C10 C9 107.8(3) . . ?
C1 C10 C9 111.2(2) . . ?
C5 C10 C9 106.6(2) . . ?
C12 C11 C9 113.5(3) . . ?
C12 C11 H11A 108.9 . . ?
C9 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C9 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 125.2(3) . . ?
C13 C12 H12 117.4 . . ?
C11 C12 H12 117.4 . . ?
C12 C13 C16 121.2(3) . . ?
C12 C13 C14 130.6(3) . . ?
C16 C13 C14 108.1(3) . . ?
O5 C14 C13 109.3(3) . . ?
O5 C14 C15 109.4(3) . . ?
C13 C14 C15 103.0(3) . . ?
O5 C14 H14 111.6 . . ?
C13 C14 H14 111.6 . . ?
C15 C14 H14 111.6 . . ?
O3 C15 C14 107.8(3) . . ?
O3 C15 H15A 110.2 . . ?
C14 C15 H15A 110.2 . . ?
O3 C15 H15B 110.2 . . ?
C14 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
O4 C16 O3 121.6(4) . . ?
O4 C16 C13 129.7(4) . . ?
O3 C16 C13 108.7(3) . . ?
O6 C17 O5 124.3(4) . . ?
O6 C17 C18 124.1(4) . . ?
O5 C17 C18 111.6(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 C4 111.2(3) . . ?
O2 C19 H19A 109.4 . . ?
C4 C19 H19A 109.4 . . ?
O2 C19 H19B 109.4 . . ?
C4 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
O1 C20 O2 110.3(3) . . ?
O1 C20 C24 108.6(3) . . ?
O2 C20 C24 107.8(3) . . ?
O1 C20 H20 110.0 . . ?
O2 C20 H20 110.0 . . ?
C24 C20 H20 110.0 . . ?
C4 C21 H21A 109.5 . . ?
C4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 C23 H23A 120.0 . . ?
C8 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 O1 C3 114.2(2) . . ?
C20 O2 C19 109.8(2) . . ?
C16 O3 C15 111.2(3) . . ?
C17 O5 C14 116.6(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
C10 C1 C2 C3 58.7(4) . . . . ?
C1 C2 C3 O1 178.7(2) . . . . ?
C1 C2 C3 C4 -51.7(4) . . . . ?
O1 C3 C4 C19 47.6(3) . . . . ?
C2 C3 C4 C19 -82.2(3) . . . . ?
O1 C3 C4 C21 -67.5(3) . . . . ?
C2 C3 C4 C21 162.6(3) . . . . ?
O1 C3 C4 C5 172.3(2) . . . . ?
C2 C3 C4 C5 42.5(3) . . . . ?
C19 C4 C5 C6 -55.0(4) . . . . ?
C21 C4 C5 C6 64.2(3) . . . . ?
C3 C4 C5 C6 -175.9(3) . . . . ?
C19 C4 C5 C10 79.0(3) . . . . ?
C21 C4 C5 C10 -161.8(3) . . . . ?
C3 C4 C5 C10 -41.9(3) . . . . ?
C10 C5 C6 C7 54.6(4) . . . . ?
C4 C5 C6 C7 -169.2(3) . . . . ?
C5 C6 C7 C8 -50.8(4) . . . . ?
C6 C7 C8 C23 -121.8(4) . . . . ?
C6 C7 C8 C9 54.7(4) . . . . ?
C23 C8 C9 C11 -14.1(5) . . . . ?
C7 C8 C9 C11 169.6(3) . . . . ?
C23 C8 C9 C10 116.8(4) . . . . ?
C7 C8 C9 C10 -59.6(3) . . . . ?
C2 C1 C10 C22 69.0(3) . . . . ?
C2 C1 C10 C5 -55.6(3) . . . . ?
C2 C1 C10 C9 -172.6(3) . . . . ?
C6 C5 C10 C22 61.4(3) . . . . ?
C4 C5 C10 C22 -72.6(3) . . . . ?
C6 C5 C10 C1 -177.4(2) . . . . ?
C4 C5 C10 C1 48.7(3) . . . . ?
C6 C5 C10 C9 -57.5(3) . . . . ?
C4 C5 C10 C9 168.6(2) . . . . ?
C8 C9 C10 C22 -64.6(3) . . . . ?
C11 C9 C10 C22 66.2(3) . . . . ?
C8 C9 C10 C1 176.5(3) . . . . ?
C11 C9 C10 C1 -52.7(4) . . . . ?
C8 C9 C10 C5 58.2(3) . . . . ?
C11 C9 C10 C5 -170.9(3) . . . . ?
C8 C9 C11 C12 -62.9(4) . . . . ?
C10 C9 C11 C12 168.7(3) . . . . ?
C9 C11 C12 C13 -155.9(4) . . . . ?
C11 C12 C13 C16 -176.1(4) . . . . ?
C11 C12 C13 C14 1.9(6) . . . . ?
C12 C13 C14 O5 -70.5(5) . . . . ?
C16 C13 C14 O5 107.7(3) . . . . ?
C12 C13 C14 C15 173.3(4) . . . . ?
C16 C13 C14 C15 -8.6(4) . . . . ?
O5 C14 C15 O3 -105.4(3) . . . . ?
C13 C14 C15 O3 10.7(4) . . . . ?
C12 C13 C16 O4 2.6(7) . . . . ?
C14 C13 C16 O4 -175.8(5) . . . . ?
C12 C13 C16 O3 -178.2(3) . . . . ?
C14 C13 C16 O3 3.4(4) . . . . ?
C21 C4 C19 O2 63.1(3) . . . . ?
C3 C4 C19 O2 -53.5(3) . . . . ?
C5 C4 C19 O2 -176.3(2) . . . . ?
O2 C20 O1 C3 59.3(4) . . . . ?
C24 C20 O1 C3 177.3(3) . . . . ?
C2 C3 O1 C20 79.3(3) . . . . ?
C4 C3 O1 C20 -52.5(4) . . . . ?
O1 C20 O2 C19 -63.3(4) . . . . ?
C24 C20 O2 C19 178.2(3) . . . . ?
C4 C19 O2 C20 62.3(4) . . . . ?
O4 C16 O3 C15 -176.9(5) . . . . ?
C13 C16 O3 C15 3.8(4) . . . . ?
C14 C15 O3 C16 -9.4(4) . . . . ?
O6 C17 O5 C14 0.0(5) . . . . ?
C18 C17 O5 C14 177.9(3) . . . . ?
C13 C14 O5 C17 176.6(2) . . . . ?
C15 C14 O5 C17 -71.3(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         0.176
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_as49
_audit_block_doi                 10.5517/cc10nms2
_database_code_depnum_ccdc_archive 'CCDC 943354'
_audit_update_record             
;
2013-06-07 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 O7'
_chemical_formula_sum            'C24 H34 O7'
_chemical_formula_weight         434.51

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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'

_cell_length_a                   12.4798(16)
_cell_length_b                   12.7207(17)
_cell_length_c                   14.3452(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2277.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5435
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.44
_chemical_absolute_configuration rm

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21934
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2280
_reflns_number_gt                2171
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0579P)²+0.2823P] 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         2280
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
C1 C 1.05342(16) 0.66347(19) 0.72292(15) 0.0522(5) Uani 1 1 d . . .
H1A H 1.0330 0.7369 0.7264 0.063 Uiso 1 1 calc R . .
H1B H 1.0819 0.6433 0.7832 0.063 Uiso 1 1 calc R . .
C2 C 1.14043(17) 0.6507(2) 0.64964(16) 0.0561(6) Uani 1 1 d . . .
H2A H 1.2019 0.6932 0.6668 0.067 Uiso 1 1 calc R . .
H2B H 1.1632 0.5778 0.6479 0.067 Uiso 1 1 calc R . .
C3 C 1.10171(17) 0.68321(17) 0.55350(15) 0.0496(5) Uani 1 1 d . . .
H3 H 1.0868 0.7587 0.5572 0.060 Uiso 1 1 calc R . .
C4 C 0.99625(16) 0.63069(17) 0.52159(14) 0.0466(5) Uani 1 1 d . . .
C5 C 0.91285(15) 0.62943(16) 0.60279(13) 0.0417(4) Uani 1 1 d . . .
H5 H 0.8916 0.7032 0.6098 0.050 Uiso 1 1 calc R . .
C6 C 0.80853(18) 0.5726(2) 0.57643(15) 0.0576(6) Uani 1 1 d . . .
H6A H 0.7845 0.5968 0.5158 0.069 Uiso 1 1 calc R . .
H6B H 0.8219 0.4976 0.5722 0.069 Uiso 1 1 calc R . .
C7 C 0.72119(18) 0.5931(2) 0.64868(16) 0.0614(6) Uani 1 1 d . . .
H7A H 0.7008 0.6666 0.6469 0.074 Uiso 1 1 calc R . .
H7B H 0.6584 0.5513 0.6339 0.074 Uiso 1 1 calc R . .
C8 C 0.76038(17) 0.56547(19) 0.74478(15) 0.0529(5) Uani 1 1 d . . .
C9 C 0.86183(16) 0.62485(17) 0.77266(13) 0.0447(5) Uani 1 1 d . . .
H9 H 0.8461 0.6997 0.7638 0.054 Uiso 1 1 calc R . .
C10 C 0.95369(15) 0.59716(16) 0.70196(13) 0.0406(4) Uani 1 1 d . . .
C11 C 0.89263(19) 0.6116(2) 0.87650(14) 0.0593(6) Uani 1 1 d . . .
H11A H 0.8889 0.5376 0.8925 0.071 Uiso 1 1 calc R . .
H11B H 0.9663 0.6342 0.8848 0.071 Uiso 1 1 calc R . .
C12 C 0.82308(18) 0.6718(2) 0.94215(14) 0.0568(6) Uani 1 1 d . . .
H12 H 0.7525 0.6834 0.9241 0.068 Uiso 1 1 calc R . .
C13 C 0.85337(18) 0.71042(18) 1.02442(14) 0.0515(5) Uani 1 1 d . . .
C14 C 0.96042(18) 0.70961(17) 1.07106(14) 0.0498(5) Uani 1 1 d . . .
H14 H 1.0170 0.7371 1.0304 0.060 Uiso 1 1 calc R . .
C15 C 0.9412(2) 0.78034(19) 1.15534(17) 0.0637(6) Uani 1 1 d . . .
H15A H 0.9721 0.7490 1.2108 0.076 Uiso 1 1 calc R . .
H15B H 0.9742 0.8485 1.1455 0.076 Uiso 1 1 calc R . .
C16 C 0.7754(2) 0.7590(2) 1.08879(17) 0.0643(6) Uani 1 1 d . . .
C17 C 1.1990(2) 0.5662(2) 0.45412(19) 0.0618(6) Uani 1 1 d . . .
H17 H 1.2219 0.5227 0.5069 0.074 Uiso 1 1 calc R . .
C18 C 1.02157(19) 0.5201(2) 0.48479(17) 0.0593(6) Uani 1 1 d . . .
H18A H 1.0447 0.4757 0.5359 0.071 Uiso 1 1 calc R . .
H18B H 0.9574 0.4894 0.4580 0.071 Uiso 1 1 calc R . .
C19 C 0.9813(2) 0.47875(18) 0.71198(16) 0.0559(5) Uani 1 1 d . . .
H19A H 1.0481 0.4645 0.6812 0.084 Uiso 1 1 calc R . .
H19B H 0.9256 0.4373 0.6841 0.084 Uiso 1 1 calc R . .
H19C H 0.9873 0.4612 0.7768 0.084 Uiso 1 1 calc R . .
C20 C 0.9516(2) 0.6965(3) 0.44012(17) 0.0746(8) Uani 1 1 d . . .
H20A H 0.9272 0.7631 0.4632 0.112 Uiso 1 1 calc R . .
H20B H 0.8928 0.6597 0.4118 0.112 Uiso 1 1 calc R . .
H20C H 1.0070 0.7075 0.3947 0.112 Uiso 1 1 calc R . .
C21 C 1.2843(2) 0.5654(2) 0.3797(2) 0.0846(9) Uani 1 1 d . . .
H21A H 1.2956 0.4947 0.3586 0.127 Uiso 1 1 calc R . .
H21B H 1.3498 0.5929 0.4048 0.127 Uiso 1 1 calc R . .
H21C H 1.2616 0.6083 0.3282 0.127 Uiso 1 1 calc R . .
C22 C 1.07864(19) 0.5849(2) 1.14033(17) 0.0591(6) Uani 1 1 d . . .
C23 C 1.0883(2) 0.4748(2) 1.1736(2) 0.0795(8) Uani 1 1 d . . .
H23A H 1.1420 0.4711 1.2215 0.119 Uiso 1 1 calc R . .
H23B H 1.1085 0.4302 1.1226 0.119 Uiso 1 1 calc R . .
H23C H 1.0208 0.4519 1.1983 0.119 Uiso 1 1 calc R . .
C24 C 0.7326(3) 0.4623(2) 0.7821(2) 0.0797(8) Uani 1 1 d . . .
H24A H 0.6945 0.4141 0.7415 0.096 Uiso 1 1 calc R . .
H24B H 0.7829 0.4293 0.8245 0.096 Uiso 1 1 calc R . .
O1 O 1.18440(13) 0.67110(13) 0.48369(12) 0.0607(4) Uani 1 1 d . . .
O2 O 1.10411(14) 0.52499(15) 0.41547(11) 0.0670(5) Uani 1 1 d . . .
O3 O 0.98199(11) 0.60225(11) 1.10051(10) 0.0502(4) Uani 1 1 d . . .
O4 O 1.14439(17) 0.6524(2) 1.14969(18) 0.0999(8) Uani 1 1 d . . .
O5 O 0.68043(17) 0.7670(2) 1.08091(15) 0.1026(8) Uani 1 1 d . . .
O6 O 0.82768(15) 0.79172(15) 1.16622(11) 0.0709(5) Uani 1 1 d . . .
O7 O 0.67643(14) 0.55415(17) 0.81416(13) 0.0771(5) Uani 1 1 d . . .


_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
C1 C2 1.520(3) . ?
C1 C10 1.533(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.519(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O1 1.446(2) . ?
C3 C4 1.545(3) . ?
C3 H3 0.9800 . ?
C4 C18 1.535(3) . ?
C4 C20 1.541(3) . ?
C4 C5 1.562(3) . ?
C5 C6 1.537(3) . ?
C5 C10 1.566(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.504(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O7 1.452(3) . ?
C8 C24 1.459(4) . ?
C8 C9 1.528(3) . ?
C9 C11 1.548(3) . ?
C9 C10 1.571(3) . ?
C9 H9 0.9800 . ?
C10 C19 1.552(3) . ?
C11 C12 1.492(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.333(3) . ?
C12 H12 0.9300 . ?
C13 C16 1.477(3) . ?
C13 C14 1.494(3) . ?
C14 O3 1.455(3) . ?
C14 C15 1.526(3) . ?
C14 H14 0.9800 . ?
C15 O6 1.432(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O5 1.195(3) . ?
C16 O6 1.354(3) . ?
C17 O2 1.409(3) . ?
C17 O1 1.412(3) . ?
C17 C21 1.507(3) . ?
C17 H17 0.9800 . ?
C18 O2 1.433(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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 O4 1.195(3) . ?
C22 O3 1.353(3) . ?
C22 C23 1.485(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O7 1.439(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

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 C1 C10 112.66(17) . . ?
C2 C1 H1A 109.1 . . ?
C10 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C10 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 111.81(17) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 C2 111.88(17) . . ?
O1 C3 C4 110.89(15) . . ?
C2 C3 C4 114.97(18) . . ?
O1 C3 H3 106.1 . . ?
C2 C3 H3 106.1 . . ?
C4 C3 H3 106.1 . . ?
C18 C4 C20 108.12(19) . . ?
C18 C4 C3 108.82(17) . . ?
C20 C4 C3 107.33(19) . . ?
C18 C4 C5 112.59(17) . . ?
C20 C4 C5 109.27(17) . . ?
C3 C4 C5 110.55(15) . . ?
C6 C5 C4 112.69(16) . . ?
C6 C5 C10 112.08(17) . . ?
C4 C5 C10 117.60(15) . . ?
C6 C5 H5 104.3 . . ?
C4 C5 H5 104.3 . . ?
C10 C5 H5 104.3 . . ?
C7 C6 C5 110.95(18) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 110.50(19) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O7 C8 C24 59.24(16) . . ?
O7 C8 C7 114.62(18) . . ?
C24 C8 C7 117.9(2) . . ?
O7 C8 C9 117.88(17) . . ?
C24 C8 C9 123.1(2) . . ?
C7 C8 C9 113.20(19) . . ?
C8 C9 C11 113.8(2) . . ?
C8 C9 C10 108.96(15) . . ?
C11 C9 C10 114.58(16) . . ?
C8 C9 H9 106.3 . . ?
C11 C9 H9 106.3 . . ?
C10 C9 H9 106.3 . . ?
C1 C10 C19 109.61(18) . . ?
C1 C10 C5 107.34(17) . . ?
C19 C10 C5 114.27(16) . . ?
C1 C10 C9 110.02(15) . . ?
C19 C10 C9 108.66(17) . . ?
C5 C10 C9 106.88(15) . . ?
C12 C11 C9 114.02(18) . . ?
C12 C11 H11A 108.7 . . ?
C9 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C9 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 125.6(2) . . ?
C13 C12 H12 117.2 . . ?
C11 C12 H12 117.2 . . ?
C12 C13 C16 121.4(2) . . ?
C12 C13 C14 130.4(2) . . ?
C16 C13 C14 108.19(19) . . ?
O3 C14 C13 107.57(18) . . ?
O3 C14 C15 110.64(17) . . ?
C13 C14 C15 102.12(18) . . ?
O3 C14 H14 112.0 . . ?
C13 C14 H14 112.0 . . ?
C15 C14 H14 112.0 . . ?
O6 C15 C14 107.55(19) . . ?
O6 C15 H15A 110.2 . . ?
C14 C15 H15A 110.2 . . ?
O6 C15 H15B 110.2 . . ?
C14 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
O5 C16 O6 122.0(2) . . ?
O5 C16 C13 129.1(3) . . ?
O6 C16 C13 108.9(2) . . ?
O2 C17 O1 111.2(2) . . ?
O2 C17 C21 108.2(2) . . ?
O1 C17 C21 108.1(2) . . ?
O2 C17 H17 109.8 . . ?
O1 C17 H17 109.8 . . ?
C21 C17 H17 109.8 . . ?
O2 C18 C4 110.30(18) . . ?
O2 C18 H18A 109.6 . . ?
C4 C18 H18A 109.6 . . ?
O2 C18 H18B 109.6 . . ?
C4 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 O3 122.8(2) . . ?
O4 C22 C23 125.9(2) . . ?
O3 C22 C23 111.2(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O7 C24 C8 60.14(16) . . ?
O7 C24 H24A 117.8 . . ?
C8 C24 H24A 117.8 . . ?
O7 C24 H24B 117.8 . . ?
C8 C24 H24B 117.8 . . ?
H24A C24 H24B 114.9 . . ?
C17 O1 C3 113.64(16) . . ?
C17 O2 C18 110.33(16) . . ?
C22 O3 C14 116.16(18) . . ?
C16 O6 C15 110.87(18) . . ?
C24 O7 C8 60.63(16) . . ?

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 C1 C2 C3 59.9(3) . . . . ?
C1 C2 C3 O1 179.99(18) . . . . ?
C1 C2 C3 C4 -52.4(3) . . . . ?
O1 C3 C4 C18 47.5(2) . . . . ?
C2 C3 C4 C18 -80.7(2) . . . . ?
O1 C3 C4 C20 -69.3(2) . . . . ?
C2 C3 C4 C20 162.56(19) . . . . ?
O1 C3 C4 C5 171.62(16) . . . . ?
C2 C3 C4 C5 43.5(2) . . . . ?
C18 C4 C5 C6 -54.9(2) . . . . ?
C20 C4 C5 C6 65.2(2) . . . . ?
C3 C4 C5 C6 -176.85(18) . . . . ?
C18 C4 C5 C10 77.8(2) . . . . ?
C20 C4 C5 C10 -162.04(19) . . . . ?
C3 C4 C5 C10 -44.1(2) . . . . ?
C4 C5 C6 C7 -167.85(19) . . . . ?
C10 C5 C6 C7 56.8(2) . . . . ?
C5 C6 C7 C8 -53.8(3) . . . . ?
C6 C7 C8 O7 -163.8(2) . . . . ?
C6 C7 C8 C24 -97.0(3) . . . . ?
C6 C7 C8 C9 57.1(3) . . . . ?
O7 C8 C9 C11 32.7(3) . . . . ?
C24 C8 C9 C11 -37.0(3) . . . . ?
C7 C8 C9 C11 170.4(2) . . . . ?
O7 C8 C9 C10 161.97(19) . . . . ?
C24 C8 C9 C10 92.2(2) . . . . ?
C7 C8 C9 C10 -60.3(2) . . . . ?
C2 C1 C10 C19 67.8(2) . . . . ?
C2 C1 C10 C5 -56.8(2) . . . . ?
C2 C1 C10 C9 -172.73(18) . . . . ?
C6 C5 C10 C1 -176.54(17) . . . . ?
C4 C5 C10 C1 50.5(2) . . . . ?
C6 C5 C10 C19 61.7(2) . . . . ?
C4 C5 C10 C19 -71.3(2) . . . . ?
C6 C5 C10 C9 -58.5(2) . . . . ?
C4 C5 C10 C9 168.49(17) . . . . ?
C8 C9 C10 C1 174.78(17) . . . . ?
C11 C9 C10 C1 -56.4(3) . . . . ?
C8 C9 C10 C19 -65.2(2) . . . . ?
C11 C9 C10 C19 63.6(2) . . . . ?
C8 C9 C10 C5 58.5(2) . . . . ?
C11 C9 C10 C5 -172.64(19) . . . . ?
C8 C9 C11 C12 -74.2(3) . . . . ?
C10 C9 C11 C12 159.5(2) . . . . ?
C9 C11 C12 C13 -150.4(2) . . . . ?
C11 C12 C13 C16 -173.3(2) . . . . ?
C11 C12 C13 C14 3.0(4) . . . . ?
C12 C13 C14 O3 -71.4(3) . . . . ?
C16 C13 C14 O3 105.3(2) . . . . ?
C12 C13 C14 C15 172.1(3) . . . . ?
C16 C13 C14 C15 -11.2(2) . . . . ?
O3 C14 C15 O6 -99.0(2) . . . . ?
C13 C14 C15 O6 15.2(2) . . . . ?
C12 C13 C16 O5 3.4(5) . . . . ?
C14 C13 C16 O5 -173.6(3) . . . . ?
C12 C13 C16 O6 -179.6(2) . . . . ?
C14 C13 C16 O6 3.3(3) . . . . ?
C20 C4 C18 O2 63.5(2) . . . . ?
C3 C4 C18 O2 -52.8(2) . . . . ?
C5 C4 C18 O2 -175.67(17) . . . . ?
C7 C8 C24 O7 -103.5(2) . . . . ?
C9 C8 C24 O7 105.2(2) . . . . ?
O2 C17 O1 C3 59.6(3) . . . . ?
C21 C17 O1 C3 178.1(2) . . . . ?
C2 C3 O1 C17 78.1(2) . . . . ?
C4 C3 O1 C17 -51.7(3) . . . . ?
O1 C17 O2 C18 -63.8(3) . . . . ?
C21 C17 O2 C18 177.7(2) . . . . ?
C4 C18 O2 C17 61.2(3) . . . . ?
O4 C22 O3 C14 -1.5(4) . . . . ?
C23 C22 O3 C14 175.9(2) . . . . ?
C13 C14 O3 C22 176.79(17) . . . . ?
C15 C14 O3 C22 -72.4(2) . . . . ?
O5 C16 O6 C15 -175.8(3) . . . . ?
C13 C16 O6 C15 7.0(3) . . . . ?
C14 C15 O6 C16 -14.4(3) . . . . ?
C7 C8 O7 C24 109.1(3) . . . . ?
C9 C8 O7 C24 -113.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.033
