# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_cu_d8v21434_0m
_database_code_depnum_ccdc_archive 'CCDC 2090337'
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 O4'
_chemical_formula_weight         334.44

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.4700(4)
_cell_length_b                   7.6623(5)
_cell_length_c                   9.8461(6)
_cell_angle_alpha                78.5620(10)
_cell_angle_beta                 79.5560(10)
_cell_angle_gamma                70.392(2)
_cell_volume                     447.19(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      16.336
_cell_measurement_theta_max      140.220

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             182
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.678
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5201
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13755
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         8.167
_diffrn_reflns_theta_max         67.499
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.922
_reflns_number_total             2977
_reflns_number_gt                2966
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.972
_reflns_Friedel_fraction_max     0.913
_reflns_Friedel_fraction_full    0.909

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.0571P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.14(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1452 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.07(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     223
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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_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
O1 O 0.9593(2) 0.4727(3) 0.06189(15) 0.0463(4) Uani 1 1 d . . . . .
H1 H 0.9408 0.4729 -0.0183 0.070 Uiso 1 1 calc R U . . .
O2 O 0.2638(3) 0.6142(3) 0.10922(17) 0.0490(5) Uani 1 1 d . . . . .
H2 H 0.1564 0.5837 0.1028 0.073 Uiso 1 1 calc R U . . .
O3 O 0.0423(3) 0.7451(3) 0.2870(2) 0.0626(6) Uani 1 1 d . . . . .
O4 O 0.7931(3) 0.4902(2) 0.81655(16) 0.0508(5) Uani 1 1 d . . . . .
C1 C 0.8075(3) 0.4066(3) 0.2976(2) 0.0378(5) Uani 1 1 d . . . . .
H1A H 0.9155 0.4558 0.3195 0.045 Uiso 1 1 calc R U . . .
H1B H 0.8757 0.2726 0.2989 0.045 Uiso 1 1 calc R U . . .
C2 C 0.7511(3) 0.4951(3) 0.1515(2) 0.0352(5) Uani 1 1 d . . . . .
H2A H 0.6661 0.4288 0.1209 0.042 Uiso 1 1 calc R U . . .
C3 C 0.6215(3) 0.7002(3) 0.1431(2) 0.0376(5) Uani 1 1 d . . . . .
H3A H 0.5750 0.7445 0.0508 0.045 Uiso 1 1 calc R U . . .
H3B H 0.7194 0.7677 0.1532 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4171(3) 0.7502(3) 0.2513(2) 0.0344(5) Uani 1 1 d . . . . .
C5 C 0.4862(3) 0.6554(3) 0.3991(2) 0.0316(4) Uani 1 1 d . . . . .
H5 H 0.5985 0.7090 0.4108 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3073(4) 0.7034(3) 0.5229(2) 0.0442(6) Uani 1 1 d . . . . .
H6A H 0.2288 0.8367 0.5097 0.053 Uiso 1 1 calc R U . . .
H6B H 0.2017 0.6368 0.5282 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4111(4) 0.6492(3) 0.6587(2) 0.0472(6) Uani 1 1 d . . . . .
H7A H 0.5110 0.7209 0.6546 0.057 Uiso 1 1 calc R U . . .
H7B H 0.2956 0.6811 0.7359 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5378(3) 0.4411(3) 0.6857(2) 0.0357(5) Uani 1 1 d . . . . .
C9 C 0.7037(3) 0.3790(3) 0.55490(19) 0.0304(4) Uani 1 1 d . . . . .
H9 H 0.8113 0.4464 0.5460 0.036 Uiso 1 1 calc R U . . .
C10 C 0.6068(3) 0.4406(3) 0.41217(19) 0.0289(4) Uani 1 1 d . . . . .
C11 C 0.8400(4) 0.1686(3) 0.5864(2) 0.0456(6) Uani 1 1 d . . . . .
H11A H 0.8941 0.1206 0.4983 0.055 Uiso 1 1 calc R U . . .
H11B H 0.9679 0.1604 0.6286 0.055 Uiso 1 1 calc R U . . .
C12 C 0.7189(5) 0.0400(4) 0.6820(3) 0.0600(7) Uani 1 1 d . . . . .
H12A H 0.6324 0.0053 0.6272 0.072 Uiso 1 1 calc R U . . .
H12B H 0.8273 -0.0738 0.7190 0.072 Uiso 1 1 calc R U . . .
C13 C 0.5669(5) 0.1309(4) 0.8027(3) 0.0548(7) Uani 1 1 d . . . . .
H13 H 0.4939 0.0447 0.8624 0.066 Uiso 1 1 calc R U . . .
C14 C 0.6823(5) 0.2083(4) 0.8899(3) 0.0519(6) Uani 1 1 d . . . . .
H14 H 0.5788 0.2392 0.9740 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6854(4) 0.3942(3) 0.8011(2) 0.0399(5) Uani 1 1 d . . . . .
C16 C 0.3970(4) 0.3094(4) 0.7435(2) 0.0507(6) Uani 1 1 d . . . . .
H16A H 0.2808 0.3598 0.8158 0.061 Uiso 1 1 calc R U . . .
H16B H 0.3314 0.2874 0.6700 0.061 Uiso 1 1 calc R U . . .
C17 C 0.8988(6) 0.0855(5) 0.9397(3) 0.0690(8) Uani 1 1 d . . . . .
H17A H 1.0090 0.0579 0.8607 0.103 Uiso 1 1 calc R U . . .
H17B H 0.8808 -0.0292 0.9926 0.103 Uiso 1 1 calc R U . . .
H17C H 0.9446 0.1494 0.9976 0.103 Uiso 1 1 calc R U . . .
C18 C 0.4596(4) 0.3272(3) 0.3955(2) 0.0423(5) Uani 1 1 d . . . . .
H18A H 0.5321 0.1962 0.4227 0.064 Uiso 1 1 calc R U . . .
H18B H 0.4335 0.3489 0.2998 0.064 Uiso 1 1 calc R U . . .
H18C H 0.3211 0.3655 0.4537 0.064 Uiso 1 1 calc R U . . .
C19 C 0.2214(3) 0.7022(3) 0.2205(2) 0.0401(5) Uani 1 1 d . . . . .
C20 C 0.3386(5) 0.9650(3) 0.2442(3) 0.0556(6) Uani 1 1 d . . . . .
H20A H 0.4506 1.0031 0.2711 0.083 Uiso 1 1 calc R U . . .
H20B H 0.2045 1.0026 0.3066 0.083 Uiso 1 1 calc R U . . .
H20C H 0.3120 1.0232 0.1506 0.083 Uiso 1 1 calc R U . . .


_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 1.448(2) . ?
O1 H1 0.8200 . ?
O2 C19 1.338(3) . ?
O2 H2 0.8200 . ?
O3 C19 1.198(3) . ?
O4 C15 1.215(3) . ?
C1 C2 1.516(3) . ?
C1 C10 1.545(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.507(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C19 1.525(3) . ?
C4 C20 1.543(3) . ?
C4 C5 1.563(3) . ?
C5 C6 1.531(3) . ?
C5 C10 1.557(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.526(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.523(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C15 1.528(3) . ?
C8 C16 1.540(3) . ?
C8 C9 1.561(2) . ?
C9 C11 1.555(3) . ?
C9 C10 1.565(2) . ?
C9 H9 0.9800 . ?
C10 C18 1.535(3) . ?
C11 C12 1.534(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.520(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C16 1.526(4) . ?
C13 C14 1.542(4) . ?
C13 H13 0.9800 . ?
C14 C17 1.507(4) . ?
C14 C15 1.521(3) . ?
C14 H14 0.9800 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 H1 109.5 . . ?
C19 O2 H2 109.5 . . ?
C2 C1 C10 114.16(16) . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
O1 C2 C3 109.42(16) . . ?
O1 C2 C1 106.59(15) . . ?
C3 C2 C1 112.45(16) . . ?
O1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C2 C3 C4 115.73(16) . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C19 C4 C3 113.74(17) . . ?
C19 C4 C20 105.50(18) . . ?
C3 C4 C20 107.04(19) . . ?
C19 C4 C5 112.39(16) . . ?
C3 C4 C5 108.38(15) . . ?
C20 C4 C5 109.57(17) . . ?
C6 C5 C10 111.13(16) . . ?
C6 C5 C4 116.06(16) . . ?
C10 C5 C4 114.71(15) . . ?
C6 C5 H5 104.5 . . ?
C10 C5 H5 104.5 . . ?
C4 C5 H5 104.5 . . ?
C7 C6 C5 110.29(17) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 112.28(17) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C15 112.34(17) . . ?
C7 C8 C16 116.03(19) . . ?
C15 C8 C16 100.58(18) . . ?
C7 C8 C9 110.54(16) . . ?
C15 C8 C9 103.77(15) . . ?
C16 C8 C9 112.53(17) . . ?
C11 C9 C8 109.95(16) . . ?
C11 C9 C10 115.62(15) . . ?
C8 C9 C10 115.92(14) . . ?
C11 C9 H9 104.6 . . ?
C8 C9 H9 104.6 . . ?
C10 C9 H9 104.6 . . ?
C18 C10 C1 108.74(16) . . ?
C18 C10 C5 113.41(16) . . ?
C1 C10 C5 108.00(16) . . ?
C18 C10 C9 112.97(16) . . ?
C1 C10 C9 106.18(14) . . ?
C5 C10 C9 107.18(14) . . ?
C12 C11 C9 116.6(2) . . ?
C12 C11 H11A 108.1 . . ?
C9 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C9 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
C13 C12 C11 112.8(2) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C16 108.6(2) . . ?
C12 C13 C14 113.8(2) . . ?
C16 C13 C14 101.6(2) . . ?
C12 C13 H13 110.8 . . ?
C16 C13 H13 110.8 . . ?
C14 C13 H13 110.8 . . ?
C17 C14 C15 115.8(2) . . ?
C17 C14 C13 119.2(3) . . ?
C15 C14 C13 102.18(19) . . ?
C17 C14 H14 106.2 . . ?
C15 C14 H14 106.2 . . ?
C13 C14 H14 106.2 . . ?
O4 C15 C14 125.5(2) . . ?
O4 C15 C8 124.5(2) . . ?
C14 C15 C8 110.03(19) . . ?
C13 C16 C8 102.32(18) . . ?
C13 C16 H16A 111.3 . . ?
C8 C16 H16A 111.3 . . ?
C13 C16 H16B 111.3 . . ?
C8 C16 H16B 111.3 . . ?
H16A C16 H16B 109.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 O2 122.48(19) . . ?
O3 C19 C4 123.1(2) . . ?
O2 C19 C4 114.37(18) . . ?
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 . . ?

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 O1 171.99(17) . . . . ?
C10 C1 C2 C3 52.1(2) . . . . ?
O1 C2 C3 C4 -169.33(15) . . . . ?
C1 C2 C3 C4 -51.1(2) . . . . ?
C2 C3 C4 C19 -75.3(2) . . . . ?
C2 C3 C4 C20 168.58(18) . . . . ?
C2 C3 C4 C5 50.5(2) . . . . ?
C19 C4 C5 C6 -58.6(2) . . . . ?
C3 C4 C5 C6 174.82(18) . . . . ?
C20 C4 C5 C6 58.3(3) . . . . ?
C19 C4 C5 C10 73.2(2) . . . . ?
C3 C4 C5 C10 -53.4(2) . . . . ?
C20 C4 C5 C10 -169.84(18) . . . . ?
C10 C5 C6 C7 62.6(2) . . . . ?
C4 C5 C6 C7 -163.90(18) . . . . ?
C5 C6 C7 C8 -59.1(3) . . . . ?
C6 C7 C8 C15 166.56(19) . . . . ?
C6 C7 C8 C16 -78.5(2) . . . . ?
C6 C7 C8 C9 51.2(2) . . . . ?
C7 C8 C9 C11 177.26(18) . . . . ?
C15 C8 C9 C11 56.6(2) . . . . ?
C16 C8 C9 C11 -51.2(2) . . . . ?
C7 C8 C9 C10 -49.3(2) . . . . ?
C15 C8 C9 C10 -169.91(17) . . . . ?
C16 C8 C9 C10 82.2(2) . . . . ?
C2 C1 C10 C18 70.4(2) . . . . ?
C2 C1 C10 C5 -53.1(2) . . . . ?
C2 C1 C10 C9 -167.75(17) . . . . ?
C6 C5 C10 C18 68.4(2) . . . . ?
C4 C5 C10 C18 -65.7(2) . . . . ?
C6 C5 C10 C1 -171.02(16) . . . . ?
C4 C5 C10 C1 54.8(2) . . . . ?
C6 C5 C10 C9 -57.00(19) . . . . ?
C4 C5 C10 C9 168.86(15) . . . . ?
C11 C9 C10 C18 56.6(2) . . . . ?
C8 C9 C10 C18 -74.2(2) . . . . ?
C11 C9 C10 C1 -62.5(2) . . . . ?
C8 C9 C10 C1 166.68(16) . . . . ?
C11 C9 C10 C5 -177.73(17) . . . . ?
C8 C9 C10 C5 51.4(2) . . . . ?
C8 C9 C11 C12 34.9(3) . . . . ?
C10 C9 C11 C12 -98.7(2) . . . . ?
C9 C11 C12 C13 -39.9(3) . . . . ?
C11 C12 C13 C16 58.8(3) . . . . ?
C11 C12 C13 C14 -53.5(3) . . . . ?
C12 C13 C14 C17 -48.9(3) . . . . ?
C16 C13 C14 C17 -165.5(2) . . . . ?
C12 C13 C14 C15 80.2(3) . . . . ?
C16 C13 C14 C15 -36.4(2) . . . . ?
C17 C14 C15 O4 -35.7(4) . . . . ?
C13 C14 C15 O4 -166.9(2) . . . . ?
C17 C14 C15 C8 142.6(2) . . . . ?
C13 C14 C15 C8 11.4(3) . . . . ?
C7 C8 C15 O4 -39.9(3) . . . . ?
C16 C8 C15 O4 -163.9(2) . . . . ?
C9 C8 C15 O4 79.5(2) . . . . ?
C7 C8 C15 C14 141.8(2) . . . . ?
C16 C8 C15 C14 17.8(2) . . . . ?
C9 C8 C15 C14 -98.77(19) . . . . ?
C12 C13 C16 C8 -71.4(2) . . . . ?
C14 C13 C16 C8 48.9(2) . . . . ?
C7 C8 C16 C13 -161.91(18) . . . . ?
C15 C8 C16 C13 -40.5(2) . . . . ?
C9 C8 C16 C13 69.4(2) . . . . ?
C3 C4 C19 O3 -173.7(2) . . . . ?
C20 C4 C19 O3 -56.6(3) . . . . ?
C5 C4 C19 O3 62.7(3) . . . . ?
C3 C4 C19 O2 3.9(2) . . . . ?
C20 C4 C19 O2 120.9(2) . . . . ?
C5 C4 C19 O2 -119.8(2) . . . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.020

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cu_d8v21439_0m
_database_code_depnum_ccdc_archive 'CCDC 2090338'
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H34 O5'
_chemical_formula_weight         366.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

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

_cell_length_a                   11.7128(3)
_cell_length_b                   7.9920(2)
_cell_length_c                   11.8269(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.2240(10)
_cell_angle_gamma                90
_cell_volume                     1001.54(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      8.263
_cell_measurement_theta_max      140.188

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.685
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4092
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12397
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.132
_diffrn_reflns_theta_max         67.434
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             3447
_reflns_number_gt                3358
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.940

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.0866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.09(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3447
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_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
O1 O 0.14110(16) 0.3895(2) 0.40975(15) 0.0584(4) Uani 1 1 d . . . . .
O2 O 0.13467(19) 0.6463(2) 0.33569(17) 0.0638(5) Uani 1 1 d . . . . .
H2 H 0.1190 0.6706 0.3950 0.096 Uiso 1 1 calc R U . . .
O3 O 0.83276(15) 0.5701(3) 0.39513(17) 0.0604(5) Uani 1 1 d . . . . .
O4 O 0.50107(17) 0.6609(2) -0.02513(14) 0.0598(4) Uani 1 1 d . . . . .
C1 C 0.40040(17) 0.2593(2) 0.27194(18) 0.0376(4) Uani 1 1 d . . . . .
H1A H 0.3916 0.2189 0.1913 0.045 Uiso 1 1 calc R U . . .
H1B H 0.4832 0.2262 0.3337 0.045 Uiso 1 1 calc R U . . .
C2 C 0.3008(2) 0.1759(3) 0.30319(19) 0.0444(5) Uani 1 1 d . . . . .
H2A H 0.3160 0.2040 0.3882 0.053 Uiso 1 1 calc R U . . .
H2B H 0.3075 0.0554 0.2982 0.053 Uiso 1 1 calc R U . . .
C3 C 0.16847(19) 0.2310(3) 0.21452(19) 0.0458(5) Uani 1 1 d . . . . .
H3A H 0.1084 0.1794 0.2403 0.055 Uiso 1 1 calc R U . . .
H3B H 0.1503 0.1909 0.1312 0.055 Uiso 1 1 calc R U . . .
C4 C 0.15007(17) 0.4210(3) 0.20973(18) 0.0394(4) Uani 1 1 d . . . . .
C5 C 0.25465(17) 0.5032(2) 0.17896(16) 0.0357(4) Uani 1 1 d . . . . .
H5 H 0.2414 0.4537 0.0985 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2435(2) 0.6912(3) 0.1534(2) 0.0472(5) Uani 1 1 d . . . . .
H6A H 0.2730 0.7518 0.2318 0.057 Uiso 1 1 calc R U . . .
H6B H 0.1557 0.7205 0.1038 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3218(2) 0.7409(3) 0.0834(2) 0.0507(5) Uani 1 1 d . . . . .
H7A H 0.2905 0.6822 0.0041 0.061 Uiso 1 1 calc R U . . .
H7B H 0.3127 0.8600 0.0661 0.061 Uiso 1 1 calc R U . . .
C8 C 0.46058(18) 0.6993(2) 0.15910(17) 0.0386(4) Uani 1 1 d . . . . .
C9 C 0.47903(16) 0.5143(2) 0.20541(15) 0.0311(4) Uani 1 1 d . . . . .
H9 H 0.4525 0.4475 0.1289 0.037 Uiso 1 1 calc R U . . .
C10 C 0.39264(16) 0.4526(2) 0.26796(15) 0.0319(4) Uani 1 1 d . . . . .
C11 C 0.62184(17) 0.4757(2) 0.27882(17) 0.0368(4) Uani 1 1 d . . . . .
H11A H 0.6309 0.3806 0.3329 0.044 Uiso 1 1 calc R U . . .
H11B H 0.6546 0.4426 0.2194 0.044 Uiso 1 1 calc R U . . .
C12 C 0.70355(19) 0.6178(3) 0.35846(18) 0.0450(5) Uani 1 1 d . . . . .
H12 H 0.6894 0.6260 0.4342 0.054 Uiso 1 1 calc R U . . .
C13 C 0.6704(2) 0.7860(3) 0.2917(2) 0.0470(5) Uani 1 1 d . . . . .
H13 H 0.7265 0.8742 0.3435 0.056 Uiso 1 1 calc R U . . .
C14 C 0.5336(2) 0.8233(2) 0.2646(2) 0.0481(5) Uani 1 1 d . . . . .
H14A H 0.5116 0.9381 0.2374 0.058 Uiso 1 1 calc R U . . .
H14B H 0.5178 0.8030 0.3375 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5369(2) 0.7103(2) 0.08064(18) 0.0426(4) Uani 1 1 d . . . . .
C16 C 0.6640(2) 0.7884(3) 0.15874(19) 0.0476(5) Uani 1 1 d . . . . .
H16 H 0.6561 0.9065 0.1341 0.057 Uiso 1 1 calc R U . . .
C17 C 0.7725(2) 0.7199(4) 0.1345(2) 0.0643(7) Uani 1 1 d . . . . .
H17A H 0.7848 0.6037 0.1573 0.096 Uiso 1 1 calc R U . . .
H17B H 0.8481 0.7811 0.1834 0.096 Uiso 1 1 calc R U . . .
H17C H 0.7531 0.7315 0.0474 0.096 Uiso 1 1 calc R U . . .
C18 C 0.43307(18) 0.5174(3) 0.40171(16) 0.0405(4) Uani 1 1 d . . . . .
H18A H 0.5222 0.5009 0.4488 0.061 Uiso 1 1 calc R U . . .
H18B H 0.3884 0.4573 0.4406 0.061 Uiso 1 1 calc R U . . .
H18C H 0.4139 0.6345 0.3994 0.061 Uiso 1 1 calc R U . . .
C19 C 0.0189(2) 0.4597(4) 0.1037(2) 0.0581(6) Uani 1 1 d . . . . .
H19A H 0.0005 0.5765 0.1051 0.087 Uiso 1 1 calc R U . . .
H19B H -0.0440 0.3945 0.1155 0.087 Uiso 1 1 calc R U . . .
H19C H 0.0188 0.4320 0.0247 0.087 Uiso 1 1 calc R U . . .
C20 C 0.14439(17) 0.4810(3) 0.33012(19) 0.0432(4) Uani 1 1 d . . . . .
O5 O 0.08663(19) 0.7485(3) 0.52969(18) 0.0672(5) Uani 1 1 d . . . . .
C21 C 0.1161(3) 0.6613(4) 0.6416(3) 0.0754(8) Uani 1 1 d . . . . .
H21A H 0.0922 0.5461 0.6233 0.113 Uiso 1 1 calc R U . . .
H21B H 0.0711 0.7098 0.6849 0.113 Uiso 1 1 calc R U . . .
H21C H 0.2052 0.6684 0.6930 0.113 Uiso 1 1 calc R U . . .
H5A H 0.116(4) 0.858(7) 0.548(4) 0.118(14) Uiso 1 1 d . . . . .
H3 H 0.864(4) 0.645(6) 0.436(4) 0.104(14) Uiso 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
O1 C20 1.206(3) . ?
O2 C20 1.330(3) . ?
O2 H2 0.8200 . ?
O3 C12 1.437(3) . ?
O3 H3 0.76(5) . ?
O4 C15 1.204(3) . ?
C1 C2 1.519(3) . ?
C1 C10 1.548(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.532(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C20 1.530(3) . ?
C4 C19 1.544(3) . ?
C4 C5 1.564(3) . ?
C5 C6 1.527(3) . ?
C5 C10 1.560(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.537(3) . ?
C8 C15 1.542(3) . ?
C8 C9 1.560(2) . ?
C9 C11 1.552(2) . ?
C9 C10 1.566(2) . ?
C9 H9 0.9800 . ?
C10 C18 1.535(2) . ?
C11 C12 1.524(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.523(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.523(3) . ?
C13 C16 1.543(3) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.512(3) . ?
C16 C17 1.519(3) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O5 C21 1.402(4) . ?
O5 H5A 0.93(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C20 O2 H2 109.5 . . ?
C12 O3 H3 98(3) . . ?
C2 C1 C10 113.83(16) . . ?
C2 C1 H1A 108.8 . . ?
C10 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
C10 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 C3 111.60(16) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 113.49(16) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C20 C4 C3 109.72(17) . . ?
C20 C4 C19 105.67(17) . . ?
C3 C4 C19 107.69(18) . . ?
C20 C4 C5 115.71(16) . . ?
C3 C4 C5 108.27(15) . . ?
C19 C4 C5 109.50(17) . . ?
C6 C5 C10 111.44(16) . . ?
C6 C5 C4 116.74(15) . . ?
C10 C5 C4 115.04(15) . . ?
C6 C5 H5 103.9 . . ?
C10 C5 H5 103.9 . . ?
C4 C5 H5 103.9 . . ?
C5 C6 C7 110.03(16) . . ?
C5 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 111.24(16) . . ?
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 . . ?
C7 C8 C14 115.00(17) . . ?
C7 C8 C15 112.44(15) . . ?
C14 C8 C15 100.78(16) . . ?
C7 C8 C9 111.54(16) . . ?
C14 C8 C9 112.36(15) . . ?
C15 C8 C9 103.67(14) . . ?
C11 C9 C8 109.86(14) . . ?
C11 C9 C10 115.63(13) . . ?
C8 C9 C10 116.32(14) . . ?
C11 C9 H9 104.5 . . ?
C8 C9 H9 104.5 . . ?
C10 C9 H9 104.5 . . ?
C18 C10 C1 108.48(15) . . ?
C18 C10 C5 112.57(14) . . ?
C1 C10 C5 108.05(14) . . ?
C18 C10 C9 113.78(14) . . ?
C1 C10 C9 106.68(13) . . ?
C5 C10 C9 106.98(13) . . ?
C12 C11 C9 116.16(15) . . ?
C12 C11 H11A 108.2 . . ?
C9 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C9 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
O3 C12 C13 113.19(17) . . ?
O3 C12 C11 107.00(18) . . ?
C13 C12 C11 112.51(16) . . ?
O3 C12 H12 108.0 . . ?
C13 C12 H12 108.0 . . ?
C11 C12 H12 108.0 . . ?
C14 C13 C12 107.18(17) . . ?
C14 C13 C16 101.16(17) . . ?
C12 C13 C16 115.47(17) . . ?
C14 C13 H13 110.8 . . ?
C12 C13 H13 110.8 . . ?
C16 C13 H13 110.8 . . ?
C13 C14 C8 102.50(16) . . ?
C13 C14 H14A 111.3 . . ?
C8 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
C8 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
O4 C15 C16 125.94(18) . . ?
O4 C15 C8 124.87(19) . . ?
C16 C15 C8 109.17(16) . . ?
C15 C16 C17 114.9(2) . . ?
C15 C16 C13 102.98(16) . . ?
C17 C16 C13 120.50(19) . . ?
C15 C16 H16 105.8 . . ?
C17 C16 H16 105.8 . . ?
C13 C16 H16 105.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 O2 122.13(19) . . ?
O1 C20 C4 124.4(2) . . ?
O2 C20 C4 113.32(18) . . ?
C21 O5 H5A 109(3) . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 C1 C2 C3 55.0(2) . . . . ?
C1 C2 C3 C4 -55.7(2) . . . . ?
C2 C3 C4 C20 -73.2(2) . . . . ?
C2 C3 C4 C19 172.26(17) . . . . ?
C2 C3 C4 C5 54.0(2) . . . . ?
C20 C4 C5 C6 -64.0(2) . . . . ?
C3 C4 C5 C6 172.43(17) . . . . ?
C19 C4 C5 C6 55.3(2) . . . . ?
C20 C4 C5 C10 69.4(2) . . . . ?
C3 C4 C5 C10 -54.2(2) . . . . ?
C19 C4 C5 C10 -171.32(17) . . . . ?
C10 C5 C6 C7 64.2(2) . . . . ?
C4 C5 C6 C7 -160.85(17) . . . . ?
C5 C6 C7 C8 -60.2(2) . . . . ?
C6 C7 C8 C14 -78.4(2) . . . . ?
C6 C7 C8 C15 167.07(18) . . . . ?
C6 C7 C8 C9 51.1(2) . . . . ?
C7 C8 C9 C11 178.38(15) . . . . ?
C14 C8 C9 C11 -50.79(19) . . . . ?
C15 C8 C9 C11 57.16(17) . . . . ?
C7 C8 C9 C10 -47.8(2) . . . . ?
C14 C8 C9 C10 82.98(19) . . . . ?
C15 C8 C9 C10 -169.07(15) . . . . ?
C2 C1 C10 C18 69.8(2) . . . . ?
C2 C1 C10 C5 -52.5(2) . . . . ?
C2 C1 C10 C9 -167.23(15) . . . . ?
C6 C5 C10 C18 69.22(19) . . . . ?
C4 C5 C10 C18 -66.6(2) . . . . ?
C6 C5 C10 C1 -171.01(15) . . . . ?
C4 C5 C10 C1 53.18(19) . . . . ?
C6 C5 C10 C9 -56.48(18) . . . . ?
C4 C5 C10 C9 167.71(14) . . . . ?
C11 C9 C10 C18 55.30(19) . . . . ?
C8 C9 C10 C18 -75.83(19) . . . . ?
C11 C9 C10 C1 -64.28(18) . . . . ?
C8 C9 C10 C1 164.59(14) . . . . ?
C11 C9 C10 C5 -179.73(14) . . . . ?
C8 C9 C10 C5 49.14(18) . . . . ?
C8 C9 C11 C12 36.1(2) . . . . ?
C10 C9 C11 C12 -98.07(18) . . . . ?
C9 C11 C12 O3 -167.53(15) . . . . ?
C9 C11 C12 C13 -42.6(2) . . . . ?
O3 C12 C13 C14 -177.28(17) . . . . ?
C11 C12 C13 C14 61.3(2) . . . . ?
O3 C12 C13 C16 70.9(2) . . . . ?
C11 C12 C13 C16 -50.6(2) . . . . ?
C12 C13 C14 C8 -72.43(19) . . . . ?
C16 C13 C14 C8 48.88(18) . . . . ?
C7 C8 C14 C13 -161.57(16) . . . . ?
C15 C8 C14 C13 -40.40(18) . . . . ?
C9 C8 C14 C13 69.38(19) . . . . ?
C7 C8 C15 O4 -41.2(3) . . . . ?
C14 C8 C15 O4 -164.2(2) . . . . ?
C9 C8 C15 O4 79.4(2) . . . . ?
C7 C8 C15 C16 140.21(18) . . . . ?
C14 C8 C15 C16 17.24(19) . . . . ?
C9 C8 C15 C16 -99.17(17) . . . . ?
O4 C15 C16 C17 -33.6(3) . . . . ?
C8 C15 C16 C17 144.97(18) . . . . ?
O4 C15 C16 C13 -166.5(2) . . . . ?
C8 C15 C16 C13 12.1(2) . . . . ?
C14 C13 C16 C15 -36.91(19) . . . . ?
C12 C13 C16 C15 78.4(2) . . . . ?
C14 C13 C16 C17 -166.4(2) . . . . ?
C12 C13 C16 C17 -51.1(3) . . . . ?
C3 C4 C20 O1 -7.4(3) . . . . ?
C19 C4 C20 O1 108.4(2) . . . . ?
C5 C4 C20 O1 -130.3(2) . . . . ?
C3 C4 C20 O2 176.91(16) . . . . ?
C19 C4 C20 O2 -67.3(2) . . . . ?
C5 C4 C20 O2 54.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O5 0.82 1.89 2.711(2) 174.5 .
O5 H5A O3 0.93(5) 1.83(5) 2.752(3) 171(4) 2_656
O3 H3 O5 0.76(5) 2.50(4) 3.062(3) 132(4) 1_655

_refine_diff_density_max         0.124
_refine_diff_density_min         -0.094
_refine_diff_density_rms         0.021

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mj21249_0m
_database_code_depnum_ccdc_archive 'CCDC 2090340'
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_audit_creation_date             2021-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H30 O4, H2 O'
_chemical_formula_sum            'C20 H32 O5'
_chemical_formula_weight         352.45
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0412 0.0250 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   7.42990(10)
_cell_length_b                   10.3592(2)
_cell_length_c                   23.4977(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1808.57(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.86
_cell_measurement_theta_min      3.27
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1122 before and 0.0752 after correction. The Ratio of minimum to maximum transmission is 0.8965. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12931
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.886
_diffrn_reflns_theta_min         3.273
_diffrn_ambient_temperature      173.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3293
_reflns_number_total             3420
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1266 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.095
_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)+(0.0710P)²+1.7217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1480
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O6) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Riding coordinates:
 O6(H6C,H6D)
3.b Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C13(H13), C15(H15)
3.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C14(H14A,H14B)
3.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O1 O 0.6481(4) 0.1535(3) 0.20575(12) 0.0327(7) Uani 1 1 d . . . . .
H1 H 0.728(10) 0.197(7) 0.187(3) 0.07(2) Uiso 1 1 d . . . . .
O2 O 0.7382(5) -0.1361(3) 0.31901(14) 0.0400(8) Uani 1 1 d . . . . .
H2 H 0.725197 -0.205257 0.337191 0.060 Uiso 1 1 calc GR . . . .
O3 O 0.5443(6) -0.0631(3) 0.38262(13) 0.0504(10) Uani 1 1 d . . . . .
O4 O 0.6499(4) 0.6389(3) 0.36277(12) 0.0306(7) Uani 1 1 d . . . . .
H4 H 0.550502 0.637811 0.345763 0.046 Uiso 1 1 calc GR . . . .
C1 C 0.9256(5) 0.2367(4) 0.29303(15) 0.0229(8) Uani 1 1 d . . . . .
H1A H 0.884422 0.305212 0.266726 0.027 Uiso 1 1 calc R . . . .
H1B H 1.052377 0.255159 0.303111 0.027 Uiso 1 1 calc R . . . .
C2 C 0.9168(5) 0.1063(4) 0.26222(16) 0.0267(8) Uani 1 1 d . . . . .
H2A H 0.989908 0.110965 0.227050 0.032 Uiso 1 1 calc R . . . .
H2B H 0.969795 0.038842 0.286939 0.032 Uiso 1 1 calc R . . . .
C3 C 0.7254(6) 0.0680(4) 0.24683(16) 0.0263(8) Uani 1 1 d . . . . .
H3 H 0.727405 -0.021152 0.230479 0.032 Uiso 1 1 calc R . . . .
C4 C 0.5995(5) 0.0686(3) 0.29908(15) 0.0236(8) Uani 1 1 d . . . . .
C5 C 0.6149(5) 0.2006(3) 0.33074(15) 0.0179(7) Uani 1 1 d . . . . .
H5 H 0.577275 0.266013 0.301798 0.021 Uiso 1 1 calc R . . . .
C6 C 0.4840(5) 0.2199(4) 0.37996(16) 0.0224(8) Uani 1 1 d . . . . .
H6A H 0.526102 0.171270 0.413706 0.027 Uiso 1 1 calc R . . . .
H6B H 0.363510 0.187077 0.369292 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4728(5) 0.3639(4) 0.39403(16) 0.0225(8) Uani 1 1 d . . . . .
H7A H 0.426101 0.410797 0.360420 0.027 Uiso 1 1 calc R . . . .
H7B H 0.386254 0.376444 0.425579 0.027 Uiso 1 1 calc R . . . .
C8 C 0.6533(5) 0.4215(3) 0.41097(14) 0.0178(7) Uani 1 1 d . . . . .
C9 C 0.8021(5) 0.3862(3) 0.36766(13) 0.0155(7) Uani 1 1 d . . . . .
H9 H 0.768952 0.435150 0.332518 0.019 Uiso 1 1 calc R . . . .
C10 C 0.8099(5) 0.2415(3) 0.34774(14) 0.0181(7) Uani 1 1 d . . . . .
C11 C 0.9853(5) 0.4449(4) 0.38599(15) 0.0215(8) Uani 1 1 d . . . . .
H11A H 1.082466 0.394529 0.367612 0.026 Uiso 1 1 calc R . . . .
H11B H 0.992191 0.534033 0.370962 0.026 Uiso 1 1 calc R . . . .
C12 C 1.0232(5) 0.4495(4) 0.45072(16) 0.0258(8) Uani 1 1 d . . . . .
H12A H 1.061209 0.362976 0.463954 0.031 Uiso 1 1 calc R . . . .
H12B H 1.122836 0.510622 0.458289 0.031 Uiso 1 1 calc R . . . .
C13 C 0.8560(6) 0.4919(4) 0.48375(14) 0.0246(8) Uani 1 1 d . . . . .
H13 H 0.881422 0.502798 0.525268 0.030 Uiso 1 1 calc R . . . .
C14 C 0.7076(5) 0.3927(4) 0.47293(14) 0.0227(8) Uani 1 1 d . . . . .
H14A H 0.605040 0.405219 0.499242 0.027 Uiso 1 1 calc R . . . .
H14B H 0.753647 0.303446 0.476988 0.027 Uiso 1 1 calc R . . . .
C15 C 0.6344(5) 0.5710(3) 0.41522(16) 0.0236(8) Uani 1 1 d . . . . .
H15 H 0.513813 0.590937 0.431980 0.028 Uiso 1 1 calc R . . . .
C16 C 0.7784(5) 0.6134(4) 0.45761(16) 0.0265(8) Uani 1 1 d . . . . .
C17 C 0.8214(6) 0.7336(4) 0.46952(19) 0.0373(11) Uani 1 1 d . . . . .
H17A H 0.910603 0.751479 0.497398 0.045 Uiso 1 1 calc R . . . .
H17B H 0.763253 0.802619 0.450233 0.045 Uiso 1 1 calc R . . . .
C18 C 0.4047(6) 0.0489(4) 0.27810(17) 0.0287(9) Uani 1 1 d . . . . .
H18A H 0.324646 0.037841 0.310894 0.043 Uiso 1 1 calc GR . . . .
H18B H 0.398983 -0.028257 0.254001 0.043 Uiso 1 1 calc GR . . . .
H18C H 0.366623 0.124402 0.256068 0.043 Uiso 1 1 calc GR . . . .
C19 C 0.6272(6) -0.0484(4) 0.33922(19) 0.0314(9) Uani 1 1 d . . . . .
C20 C 0.8940(6) 0.1511(4) 0.39268(15) 0.0239(8) Uani 1 1 d . . . . .
H20A H 1.009583 0.186634 0.405247 0.036 Uiso 1 1 calc GR . . . .
H20B H 0.913149 0.065519 0.375961 0.036 Uiso 1 1 calc GR . . . .
H20C H 0.812666 0.143754 0.425351 0.036 Uiso 1 1 calc GR . . . .
O6 O 0.8287(8) 0.3102(6) 0.1249(3) 0.124(2) Uani 1 1 d . U . . .
H6C H 0.894319 0.330495 0.095619 0.186 Uiso 1 1 d R . . . .
H6D H 0.730729 0.277985 0.110369 0.186 Uiso 1 1 d 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 H1 0.87(7) . ?
O1 C3 1.431(5) . ?
O2 H2 0.8400 . ?
O2 C19 1.315(5) . ?
O3 C19 1.201(6) . ?
O4 H4 0.8400 . ?
O4 C15 1.424(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.534(5) . ?
C1 C10 1.547(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.520(6) . ?
C3 H3 1.0000 . ?
C3 C4 1.544(6) . ?
C4 C5 1.560(5) . ?
C4 C18 1.543(5) . ?
C4 C19 1.550(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.524(5) . ?
C5 C10 1.561(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.531(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.521(5) . ?
C8 C9 1.547(5) . ?
C8 C14 1.540(5) . ?
C8 C15 1.558(5) . ?
C9 H9 1.0000 . ?
C9 C10 1.572(4) . ?
C9 C11 1.551(5) . ?
C10 C20 1.543(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.548(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.529(6) . ?
C13 H13 1.0000 . ?
C13 C14 1.529(6) . ?
C13 C16 1.515(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15 1.0000 . ?
C15 C16 1.527(5) . ?
C16 C17 1.316(6) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O6 H6C 0.8695 . ?
O6 H6D 0.8702 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 113(5) . . ?
C19 O2 H2 109.5 . . ?
C15 O4 H4 109.5 . . ?
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C2 C1 C10 113.4(3) . . ?
C10 C1 H1A 108.9 . . ?
C10 C1 H1B 108.9 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.5(3) . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
O1 C3 C2 112.0(3) . . ?
O1 C3 H3 108.6 . . ?
O1 C3 C4 106.9(3) . . ?
C2 C3 H3 108.6 . . ?
C2 C3 C4 112.1(3) . . ?
C4 C3 H3 108.6 . . ?
C3 C4 C5 109.8(3) . . ?
C3 C4 C19 113.6(3) . . ?
C18 C4 C3 108.3(3) . . ?
C18 C4 C5 109.7(3) . . ?
C18 C4 C19 102.4(3) . . ?
C19 C4 C5 112.7(3) . . ?
C4 C5 H5 104.4 . . ?
C4 C5 C10 115.3(3) . . ?
C6 C5 C4 115.5(3) . . ?
C6 C5 H5 104.4 . . ?
C6 C5 C10 111.2(3) . . ?
C10 C5 H5 104.4 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
C5 C6 C7 109.1(3) . . ?
H6A C6 H6B 108.3 . . ?
C7 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 113.0(3) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 C9 111.4(3) . . ?
C7 C8 C14 113.7(3) . . ?
C7 C8 C15 109.1(3) . . ?
C9 C8 C15 110.0(3) . . ?
C14 C8 C9 112.8(3) . . ?
C14 C8 C15 99.0(3) . . ?
C8 C9 H9 104.3 . . ?
C8 C9 C10 116.6(3) . . ?
C8 C9 C11 110.6(3) . . ?
C10 C9 H9 104.3 . . ?
C11 C9 H9 104.3 . . ?
C11 C9 C10 115.1(3) . . ?
C1 C10 C5 107.1(3) . . ?
C1 C10 C9 107.4(3) . . ?
C5 C10 C9 107.5(3) . . ?
C20 C10 C1 108.9(3) . . ?
C20 C10 C5 112.7(3) . . ?
C20 C10 C9 112.9(3) . . ?
C9 C11 H11A 108.2 . . ?
C9 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 C9 116.4(3) . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.1(3) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13 112.0 . . ?
C14 C13 C12 107.9(3) . . ?
C14 C13 H13 112.0 . . ?
C16 C13 C12 110.0(3) . . ?
C16 C13 H13 112.0 . . ?
C16 C13 C14 102.5(3) . . ?
C8 C14 H14A 111.3 . . ?
C8 C14 H14B 111.3 . . ?
C13 C14 C8 102.5(3) . . ?
C13 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
O4 C15 C8 115.4(3) . . ?
O4 C15 H15 108.1 . . ?
O4 C15 C16 111.4(3) . . ?
C8 C15 H15 108.1 . . ?
C16 C15 C8 105.4(3) . . ?
C16 C15 H15 108.1 . . ?
C13 C16 C15 107.0(3) . . ?
C17 C16 C13 127.4(4) . . ?
C17 C16 C15 125.6(4) . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 C4 113.8(4) . . ?
O3 C19 O2 122.7(4) . . ?
O3 C19 C4 123.2(4) . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H6C O6 H6D 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O4 0.84 1.81 2.631(4) 164.8 1_545
O4 H4 O1 0.84 1.92 2.742(4) 167.7 3_655

_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_mj22102_0m
_database_code_depnum_ccdc_archive 'CCDC 2156441'
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 O4'
_chemical_formula_sum            'C20 H28 O4'
_chemical_formula_weight         332.42
_chemical_absolute_configuration rmad
_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 0.0137 0.0067 '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 0.0389 0.0241 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.4502(3)
_cell_length_b                   14.2302(6)
_cell_length_c                   9.9729(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.573(2)
_cell_angle_gamma                90
_cell_volume                     905.16(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      54.977
_cell_measurement_theta_min      6.038
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1631 before and 0.0915 after correction.
The Ratio of minimum to maximum transmission is 0.7112.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11155
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.989
_diffrn_reflns_theta_min         6.036
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3334
_reflns_number_total             3409
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1535 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.0654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C5(H5), C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C14(H14A,H14B)
2.c X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O -0.1293(2) 0.50296(15) 0.31150(15) 0.0444(4) Uani 1 1 d . . . . .
H1 H -0.107916 0.503582 0.232485 0.067 Uiso 1 1 calc R U . . .
O2 O 0.5145(2) 0.43164(16) 0.37479(17) 0.0490(5) Uani 1 1 d . . . . .
H2 H 0.634179 0.443163 0.361184 0.073 Uiso 1 1 calc R U . . .
O3 O 0.6824(3) 0.37602(16) 0.5693(2) 0.0550(5) Uani 1 1 d . . . . .
O4 O 0.0110(3) 0.50839(15) 1.06457(18) 0.0547(5) Uani 1 1 d . . . . .
C1 C 0.0385(3) 0.54299(14) 0.5324(2) 0.0328(5) Uani 1 1 d . . . . .
H1A H -0.088899 0.519356 0.561194 0.039 Uiso 1 1 calc R U . . .
H1B H 0.019268 0.609696 0.514709 0.039 Uiso 1 1 calc R U . . .
C2 C 0.0688(3) 0.49413(17) 0.4010(2) 0.0340(5) Uani 1 1 d . . . . .
H2A H 0.179219 0.526094 0.360744 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1234(3) 0.39146(16) 0.4214(2) 0.0348(5) Uani 1 1 d . . . . .
H3A H 0.158508 0.366503 0.337071 0.042 Uiso 1 1 calc R U . . .
H3B H 0.000153 0.358210 0.441042 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3060(3) 0.37066(14) 0.5352(2) 0.0317(5) Uani 1 1 d . . . . .
C5 C 0.2646(3) 0.42274(12) 0.6661(2) 0.0276(4) Uani 1 1 d . . . . .
H5 H 0.132014 0.396379 0.685671 0.033 Uiso 1 1 calc R U . . .
C6 C 0.4207(4) 0.40218(18) 0.7933(2) 0.0444(6) Uani 1 1 d . . . . .
H6A H 0.549230 0.437040 0.790334 0.053 Uiso 1 1 calc R U . . .
H6B H 0.454471 0.335717 0.797339 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3260(5) 0.43052(19) 0.9187(2) 0.0481(6) Uani 1 1 d . . . . .
H7A H 0.198773 0.394735 0.921791 0.058 Uiso 1 1 calc R U . . .
H7B H 0.423993 0.415585 0.999429 0.058 Uiso 1 1 calc R U . . .
C8 C 0.2754(4) 0.53481(16) 0.9180(2) 0.0360(5) Uani 1 1 d . . . . .
C9 C 0.1400(3) 0.56434(13) 0.7815(2) 0.0283(4) Uani 1 1 d . . . . .
H9 H 0.006380 0.531539 0.781194 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2212(3) 0.52971(12) 0.6491(2) 0.0261(4) Uani 1 1 d . . . . .
C11 C 0.0826(5) 0.67051(16) 0.7831(3) 0.0479(6) Uani 1 1 d . . . . .
H11A H 0.050017 0.691885 0.689954 0.057 Uiso 1 1 calc R U . . .
H11B H -0.043964 0.676927 0.824054 0.057 Uiso 1 1 calc R U . . .
C12 C 0.2494(6) 0.73585(19) 0.8579(3) 0.0662(9) Uani 1 1 d . . . . .
H12A H 0.184720 0.794949 0.876894 0.079 Uiso 1 1 calc R U . . .
H12B H 0.354453 0.748951 0.800185 0.079 Uiso 1 1 calc R U . . .
C13 C 0.3554(5) 0.6924(2) 0.9909(3) 0.0600(8) Uani 1 1 d . . . . .
H13 H 0.454897 0.735997 1.042134 0.072 Uiso 1 1 calc R U . . .
C14 C 0.4624(5) 0.6011(2) 0.9581(3) 0.0558(7) Uani 1 1 d . . . . .
H14A H 0.554841 0.577594 1.036587 0.067 Uiso 1 1 calc R U . . .
H14B H 0.541939 0.609745 0.883808 0.067 Uiso 1 1 calc R U . . .
C15 C 0.1953(5) 0.6572(2) 1.0752(3) 0.0524(6) Uani 1 1 d . . . . .
C16 C 0.1404(4) 0.55984(17) 1.0266(2) 0.0411(5) Uani 1 1 d . . . . .
C17 C 0.1128(6) 0.7004(3) 1.1720(3) 0.0688(9) Uani 1 1 d . . . . .
H17A H 0.013232 0.669949 1.214846 0.083 Uiso 1 1 calc R U . . .
H17B H 0.154261 0.761273 1.197253 0.083 Uiso 1 1 calc R U . . .
C18 C 0.4102(4) 0.58613(16) 0.6157(2) 0.0387(5) Uani 1 1 d . . . . .
H18A H 0.533688 0.567869 0.676113 0.058 Uiso 1 1 calc R U . . .
H18B H 0.385013 0.652005 0.626339 0.058 Uiso 1 1 calc R U . . .
H18C H 0.429975 0.573742 0.523846 0.058 Uiso 1 1 calc R U . . .
C19 C 0.5207(3) 0.39309(17) 0.4969(2) 0.0354(5) Uani 1 1 d . . . . .
C20 C 0.3084(4) 0.26322(16) 0.5607(3) 0.0476(6) Uani 1 1 d . . . . .
H20A H 0.186899 0.245772 0.600020 0.071 Uiso 1 1 calc R U . . .
H20B H 0.432657 0.246639 0.621544 0.071 Uiso 1 1 calc R U . . .
H20C H 0.307150 0.230696 0.476217 0.071 Uiso 1 1 calc R U . . .


_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 H1 0.8200 . ?
O1 C2 1.451(2) . ?
O2 H2 0.8200 . ?
O2 C19 1.331(3) . ?
O3 C19 1.202(3) . ?
O4 C16 1.212(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.522(3) . ?
C1 C10 1.540(3) . ?
C2 H2A 0.9800 . ?
C2 C3 1.510(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.538(3) . ?
C4 C5 1.558(3) . ?
C4 C19 1.524(3) . ?
C4 C20 1.549(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.526(3) . ?
C5 C10 1.552(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.526(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.519(3) . ?
C8 C9 1.561(3) . ?
C8 C14 1.536(4) . ?
C8 C16 1.530(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.570(3) . ?
C9 C11 1.556(3) . ?
C10 C18 1.537(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.530(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.530(5) . ?
C13 H13 0.9800 . ?
C13 C14 1.529(5) . ?
C13 C15 1.510(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.493(4) . ?
C15 C17 1.321(4) . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 H1 109.5 . . ?
C19 O2 H2 109.5 . . ?
H1A C1 H1B 107.6 . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C2 C1 C10 114.38(16) . . ?
C10 C1 H1A 108.7 . . ?
C10 C1 H1B 108.7 . . ?
O1 C2 C1 106.00(16) . . ?
O1 C2 H2A 109.6 . . ?
O1 C2 C3 109.46(18) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 C1 112.56(17) . . ?
C3 C2 H2A 109.6 . . ?
C2 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C2 C3 C4 115.05(16) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C3 C4 C5 108.60(15) . . ?
C3 C4 C20 107.39(19) . . ?
C19 C4 C3 113.53(18) . . ?
C19 C4 C5 112.68(17) . . ?
C19 C4 C20 105.09(17) . . ?
C20 C4 C5 109.32(18) . . ?
C4 C5 H5 104.4 . . ?
C6 C5 C4 115.53(16) . . ?
C6 C5 H5 104.4 . . ?
C6 C5 C10 111.39(17) . . ?
C10 C5 C4 115.20(16) . . ?
C10 C5 H5 104.4 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C5 C6 C7 109.60(19) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.5(2) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 C9 111.04(18) . . ?
C7 C8 C14 116.0(2) . . ?
C7 C8 C16 111.60(19) . . ?
C14 C8 C9 112.2(2) . . ?
C16 C8 C9 104.57(18) . . ?
C16 C8 C14 100.37(19) . . ?
C8 C9 H9 104.6 . . ?
C8 C9 C10 115.80(16) . . ?
C10 C9 H9 104.6 . . ?
C11 C9 C8 110.82(17) . . ?
C11 C9 H9 104.6 . . ?
C11 C9 C10 115.04(17) . . ?
C1 C10 C5 107.95(15) . . ?
C1 C10 C9 106.47(15) . . ?
C5 C10 C9 107.07(15) . . ?
C18 C10 C1 108.33(17) . . ?
C18 C10 C5 113.56(17) . . ?
C18 C10 C9 113.13(16) . . ?
C9 C11 H11A 108.2 . . ?
C9 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 C9 116.3(2) . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C11 C12 C13 111.6(2) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C12 C13 H13 111.6 . . ?
C14 C13 C12 108.4(2) . . ?
C14 C13 H13 111.6 . . ?
C15 C13 C12 111.2(3) . . ?
C15 C13 H13 111.6 . . ?
C15 C13 C14 101.9(3) . . ?
C8 C14 H14A 111.3 . . ?
C8 C14 H14B 111.3 . . ?
C13 C14 C8 102.5(2) . . ?
C13 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C16 C15 C13 106.0(2) . . ?
C17 C15 C13 129.5(3) . . ?
C17 C15 C16 124.5(3) . . ?
O4 C16 C8 124.8(2) . . ?
O4 C16 C15 126.9(2) . . ?
C15 C16 C8 108.3(2) . . ?
C15 C17 H17A 120.0 . . ?
C15 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 C4 114.28(18) . . ?
O3 C19 O2 122.6(2) . . ?
O3 C19 C4 123.1(2) . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C2 C3 C4 -168.51(16) . . . . ?
C1 C2 C3 C4 -50.9(2) . . . . ?
C2 C1 C10 C5 -52.7(2) . . . . ?
C2 C1 C10 C9 -167.33(17) . . . . ?
C2 C1 C10 C18 70.7(2) . . . . ?
C2 C3 C4 C5 50.3(2) . . . . ?
C2 C3 C4 C19 -75.9(2) . . . . ?
C2 C3 C4 C20 168.43(17) . . . . ?
C3 C4 C5 C6 174.39(19) . . . . ?
C3 C4 C5 C10 -53.4(2) . . . . ?
C3 C4 C19 O2 3.5(3) . . . . ?
C3 C4 C19 O3 -175.2(2) . . . . ?
C4 C5 C6 C7 -161.7(2) . . . . ?
C4 C5 C10 C1 54.6(2) . . . . ?
C4 C5 C10 C9 168.87(15) . . . . ?
C4 C5 C10 C18 -65.5(2) . . . . ?
C5 C4 C19 O2 -120.5(2) . . . . ?
C5 C4 C19 O3 60.8(3) . . . . ?
C5 C6 C7 C8 -60.7(3) . . . . ?
C6 C5 C10 C1 -171.32(17) . . . . ?
C6 C5 C10 C9 -57.0(2) . . . . ?
C6 C5 C10 C18 68.6(2) . . . . ?
C6 C7 C8 C9 52.0(3) . . . . ?
C6 C7 C8 C14 -77.6(3) . . . . ?
C6 C7 C8 C16 168.3(2) . . . . ?
C7 C8 C9 C10 -48.5(3) . . . . ?
C7 C8 C9 C11 178.1(2) . . . . ?
C7 C8 C14 C13 -162.6(2) . . . . ?
C7 C8 C16 O4 -32.3(3) . . . . ?
C7 C8 C16 C15 148.1(2) . . . . ?
C8 C9 C10 C1 165.11(17) . . . . ?
C8 C9 C10 C5 49.8(2) . . . . ?
C8 C9 C10 C18 -76.0(2) . . . . ?
C8 C9 C11 C12 35.6(3) . . . . ?
C9 C8 C14 C13 68.3(3) . . . . ?
C9 C8 C16 O4 87.8(3) . . . . ?
C9 C8 C16 C15 -91.8(2) . . . . ?
C9 C11 C12 C13 -41.6(4) . . . . ?
C10 C1 C2 O1 171.79(17) . . . . ?
C10 C1 C2 C3 52.2(2) . . . . ?
C10 C5 C6 C7 64.3(3) . . . . ?
C10 C9 C11 C12 -98.1(3) . . . . ?
C11 C9 C10 C1 -63.5(2) . . . . ?
C11 C9 C10 C5 -178.75(18) . . . . ?
C11 C9 C10 C18 55.4(2) . . . . ?
C11 C12 C13 C14 60.9(3) . . . . ?
C11 C12 C13 C15 -50.4(3) . . . . ?
C12 C13 C14 C8 -72.6(3) . . . . ?
C12 C13 C15 C16 86.2(3) . . . . ?
C12 C13 C15 C17 -93.1(4) . . . . ?
C13 C15 C16 O4 -176.9(3) . . . . ?
C13 C15 C16 C8 2.7(3) . . . . ?
C14 C8 C9 C10 83.1(2) . . . . ?
C14 C8 C9 C11 -50.2(3) . . . . ?
C14 C8 C16 O4 -155.9(3) . . . . ?
C14 C8 C16 C15 24.5(3) . . . . ?
C14 C13 C15 C16 -29.1(3) . . . . ?
C14 C13 C15 C17 151.6(3) . . . . ?
C15 C13 C14 C8 44.8(3) . . . . ?
C16 C8 C9 C10 -169.00(17) . . . . ?
C16 C8 C9 C11 57.6(2) . . . . ?
C16 C8 C14 C13 -42.3(3) . . . . ?
C17 C15 C16 O4 2.5(5) . . . . ?
C17 C15 C16 C8 -178.0(3) . . . . ?
C19 C4 C5 C6 -58.9(2) . . . . ?
C19 C4 C5 C10 73.2(2) . . . . ?
C20 C4 C5 C6 57.5(2) . . . . ?
C20 C4 C5 C10 -170.32(18) . . . . ?
C20 C4 C19 O2 120.6(2) . . . . ?
C20 C4 C19 O3 -58.1(3) . . . . ?

_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_cu_d8v21936_0m
_database_code_depnum_ccdc_archive 'CCDC 2127069'
_audit_update_record             
;
2021-12-07 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H34 O7'
_chemical_formula_weight         386.47

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_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                   7.4300(3)
_cell_length_b                   12.1373(5)
_cell_length_c                   21.6486(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1952.27(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      7.283
_cell_measurement_theta_max      139.936

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.809
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15527
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.176
_diffrn_reflns_theta_max         67.970
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3520
_reflns_number_gt                3407
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.4277P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1397 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3520
_refine_ls_number_parameters     256
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.003

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
O1 O 0.3474(2) 0.11742(16) 0.20437(8) 0.0362(4) Uani 1 1 d . . . . .
O2 O 0.3595(3) 0.33300(18) 0.17497(10) 0.0475(6) Uani 1 1 d D . . . .
O3 O 0.5122(3) -0.08086(15) 0.21987(9) 0.0385(4) Uani 1 1 d . . . . .
O4 O 0.5000(3) -0.0024(2) -0.15834(10) 0.0587(7) Uani 1 1 d . . . . .
O5 O 0.7274(3) 0.02910(18) -0.09580(8) 0.0407(5) Uani 1 1 d . . . . .
H5 H 0.7639 0.0642 -0.1256 0.061 Uiso 1 1 calc R U . . .
C1 C 0.2220(3) 0.0287(3) 0.01741(12) 0.0364(6) Uani 1 1 d . . . . .
H1A H 0.1761 -0.0297 0.0437 0.044 Uiso 1 1 calc R U . . .
H1B H 0.1561 0.0954 0.0272 0.044 Uiso 1 1 calc R U . . .
C2 C 0.1872(3) -0.0017(3) -0.04987(13) 0.0418(7) Uani 1 1 d . . . . .
H2A H 0.0596 -0.0149 -0.0558 0.050 Uiso 1 1 calc R U . . .
H2B H 0.2220 0.0593 -0.0762 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2924(4) -0.1041(2) -0.06823(12) 0.0377(6) Uani 1 1 d . . . . .
H3A H 0.2686 -0.1207 -0.1113 0.045 Uiso 1 1 calc R U . . .
H3B H 0.2508 -0.1661 -0.0438 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4958(3) -0.0904(2) -0.05901(11) 0.0282(5) Uani 1 1 d . . . . .
C5 C 0.5305(3) -0.05624(19) 0.00936(10) 0.0250(5) Uani 1 1 d . . . . .
H5A H 0.4794 -0.1171 0.0334 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7279(3) -0.0518(2) 0.03021(11) 0.0294(5) Uani 1 1 d . . . . .
H6A H 0.7945 -0.1120 0.0115 0.035 Uiso 1 1 calc R U . . .
H6B H 0.7820 0.0170 0.0170 0.035 Uiso 1 1 calc R U . . .
C7 C 0.7367(3) -0.0609(2) 0.10041(11) 0.0314(5) Uani 1 1 d . . . . .
H7A H 0.6853 -0.1308 0.1131 0.038 Uiso 1 1 calc R U . . .
H7B H 0.8616 -0.0597 0.1134 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6364(3) 0.0319(2) 0.13192(11) 0.0259(5) Uani 1 1 d . . . . .
C9 C 0.4435(3) 0.04885(19) 0.10451(10) 0.0243(5) Uani 1 1 d . . . . .
H9 H 0.3763 -0.0161 0.1183 0.029 Uiso 1 1 calc R U . . .
C10 C 0.4238(3) 0.0470(2) 0.03209(10) 0.0256(5) Uani 1 1 d . . . . .
C11 C 0.3529(3) 0.1461(2) 0.13900(11) 0.0290(5) Uani 1 1 d . . . . .
H11 H 0.2320 0.1609 0.1228 0.035 Uiso 1 1 calc R U . . .
C12 C 0.4634(4) 0.2513(2) 0.14374(12) 0.0326(5) Uani 1 1 d . . . . .
H12 H 0.5009 0.2771 0.1028 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6234(3) 0.2091(2) 0.18065(12) 0.0306(5) Uani 1 1 d . . . . .
H13 H 0.6898 0.2673 0.2023 0.037 Uiso 1 1 calc R U . . .
C14 C 0.7408(3) 0.1406(2) 0.13611(12) 0.0314(5) Uani 1 1 d . . . . .
H14A H 0.7503 0.1758 0.0960 0.038 Uiso 1 1 calc R U . . .
H14B H 0.8605 0.1291 0.1528 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6149(3) 0.0128(2) 0.20221(11) 0.0290(5) Uani 1 1 d . . . . .
H15 H 0.7355 0.0048 0.2200 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5371(4) 0.1223(2) 0.22461(11) 0.0318(6) Uani 1 1 d . . . . .
C17 C 0.5397(5) 0.1416(3) 0.29269(12) 0.0428(6) Uani 1 1 d . . . . .
H17A H 0.4752 0.2081 0.3020 0.064 Uiso 1 1 calc R U . . .
H17B H 0.6619 0.1486 0.3065 0.064 Uiso 1 1 calc R U . . .
H17C H 0.4835 0.0807 0.3134 0.064 Uiso 1 1 calc R U . . .
C18 C 0.4833(3) 0.1540(2) 0.00056(11) 0.0319(5) Uani 1 1 d . . . . .
H18A H 0.6098 0.1649 0.0071 0.048 Uiso 1 1 calc R U . . .
H18B H 0.4177 0.2149 0.0177 0.048 Uiso 1 1 calc R U . . .
H18C H 0.4596 0.1493 -0.0430 0.048 Uiso 1 1 calc R U . . .
C19 C 0.5855(4) -0.2033(2) -0.07218(13) 0.0393(6) Uani 1 1 d . . . . .
H19A H 0.7137 -0.1942 -0.0742 0.059 Uiso 1 1 calc R U . . .
H19B H 0.5423 -0.2316 -0.1108 0.059 Uiso 1 1 calc R U . . .
H19C H 0.5559 -0.2540 -0.0397 0.059 Uiso 1 1 calc R U . . .
C20 C 0.5713(3) -0.0144(2) -0.10887(11) 0.0303(5) Uani 1 1 d . . . . .
O6 O 0.8699(3) 0.4089(3) 0.28008(15) 0.0771(8) Uani 1 1 d DG . . . .
H6C H 0.9536 0.3612 0.2787 0.116 Uiso 1 1 d DG U . . .
H6D H 0.8833 0.3985 0.2429 0.116 Uiso 1 1 d DG U . . .
O7 O 0.0426(3) 0.2064(3) 0.26620(15) 0.0920(11) Uani 1 1 d DG . . . .
H7C H 0.0535 0.1351 0.2885 0.138 Uiso 1 1 d DG U . . .
H7D H 0.1183 0.1871 0.2356 0.138 Uiso 1 1 d DG U . . .
H3 H 0.384(9) -0.065(5) 0.215(2) 0.106(18) Uiso 1 1 d . . . . .
H2 H 0.411(6) 0.354(4) 0.2056(15) 0.082(15) Uiso 1 1 d 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
O1 C11 1.458(3) . ?
O1 C16 1.477(3) . ?
O2 C12 1.427(3) . ?
O2 H2 0.81(2) . ?
O3 C15 1.421(3) . ?
O3 H3 0.97(6) . ?
O4 C20 1.204(3) . ?
O5 C20 1.305(3) . ?
O5 H5 0.8200 . ?
C1 C2 1.525(4) . ?
C1 C10 1.549(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.521(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.534(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C20 1.527(3) . ?
C4 C19 1.550(3) . ?
C4 C5 1.558(3) . ?
C5 C6 1.536(3) . ?
C5 C10 1.562(3) . ?
C5 H5A 0.9800 . ?
C6 C7 1.525(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.513(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.533(3) . ?
C8 C15 1.548(3) . ?
C8 C9 1.565(3) . ?
C9 C11 1.551(3) . ?
C9 C10 1.575(3) . ?
C9 H9 0.9800 . ?
C10 C18 1.533(3) . ?
C11 C12 1.522(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.521(4) . ?
C12 H12 0.9800 . ?
C13 C14 1.544(4) . ?
C13 C16 1.558(4) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.529(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.493(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O6 H6C 0.8499 . ?
O6 H6D 0.8214 . ?
O7 H7C 0.9944 . ?
O7 H7D 0.9001 . ?

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
C11 O1 C16 104.59(18) . . ?
C12 O2 H2 110(4) . . ?
C15 O3 H3 110(3) . . ?
C20 O5 H5 109.5 . . ?
C2 C1 C10 113.3(2) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 111.1(2) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 112.5(2) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C20 C4 C3 109.6(2) . . ?
C20 C4 C19 104.3(2) . . ?
C3 C4 C19 107.7(2) . . ?
C20 C4 C5 116.8(2) . . ?
C3 C4 C5 108.38(19) . . ?
C19 C4 C5 109.8(2) . . ?
C6 C5 C4 116.49(19) . . ?
C6 C5 C10 111.36(19) . . ?
C4 C5 C10 115.38(18) . . ?
C6 C5 H5A 103.9 . . ?
C4 C5 H5A 103.9 . . ?
C10 C5 H5A 103.9 . . ?
C7 C6 C5 109.34(19) . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 C6 112.0(2) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C14 114.7(2) . . ?
C7 C8 C15 112.5(2) . . ?
C14 C8 C15 97.08(19) . . ?
C7 C8 C9 112.20(19) . . ?
C14 C8 C9 111.89(19) . . ?
C15 C8 C9 107.33(17) . . ?
C11 C9 C8 108.37(18) . . ?
C11 C9 C10 116.76(19) . . ?
C8 C9 C10 117.43(18) . . ?
C11 C9 H9 104.2 . . ?
C8 C9 H9 104.2 . . ?
C10 C9 H9 104.2 . . ?
C18 C10 C1 108.0(2) . . ?
C18 C10 C5 113.15(18) . . ?
C1 C10 C5 108.2(2) . . ?
C18 C10 C9 113.84(19) . . ?
C1 C10 C9 107.24(19) . . ?
C5 C10 C9 106.15(18) . . ?
O1 C11 C12 98.63(19) . . ?
O1 C11 C9 107.30(19) . . ?
C12 C11 C9 115.9(2) . . ?
O1 C11 H11 111.4 . . ?
C12 C11 H11 111.4 . . ?
C9 C11 H11 111.4 . . ?
O2 C12 C11 108.8(2) . . ?
O2 C12 C13 114.1(2) . . ?
C11 C12 C13 100.07(19) . . ?
O2 C12 H12 111.1 . . ?
C11 C12 H12 111.1 . . ?
C13 C12 H12 111.1 . . ?
C12 C13 C14 107.1(2) . . ?
C12 C13 C16 103.1(2) . . ?
C14 C13 C16 104.4(2) . . ?
C12 C13 H13 113.7 . . ?
C14 C13 H13 113.7 . . ?
C16 C13 H13 113.7 . . ?
C8 C14 C13 102.41(19) . . ?
C8 C14 H14A 111.3 . . ?
C13 C14 H14A 111.3 . . ?
C8 C14 H14B 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
O3 C15 C16 114.02(19) . . ?
O3 C15 C8 116.1(2) . . ?
C16 C15 C8 102.73(19) . . ?
O3 C15 H15 107.9 . . ?
C16 C15 H15 107.9 . . ?
C8 C15 H15 107.9 . . ?
O1 C16 C17 108.1(2) . . ?
O1 C16 C15 103.4(2) . . ?
C17 C16 C15 116.4(2) . . ?
O1 C16 C13 103.80(19) . . ?
C17 C16 C13 119.4(2) . . ?
C15 C16 C13 103.8(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 O5 122.3(2) . . ?
O4 C20 C4 122.7(2) . . ?
O5 C20 C4 114.7(2) . . ?
H6C O6 H6D 76.8 . . ?
H7C O7 H7D 94.6 . . ?

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 56.8(3) . . . . ?
C1 C2 C3 C4 -58.0(3) . . . . ?
C2 C3 C4 C20 -73.4(3) . . . . ?
C2 C3 C4 C19 173.8(2) . . . . ?
C2 C3 C4 C5 55.1(3) . . . . ?
C20 C4 C5 C6 -62.8(3) . . . . ?
C3 C4 C5 C6 172.9(2) . . . . ?
C19 C4 C5 C6 55.5(3) . . . . ?
C20 C4 C5 C10 70.5(3) . . . . ?
C3 C4 C5 C10 -53.7(3) . . . . ?
C19 C4 C5 C10 -171.1(2) . . . . ?
C4 C5 C6 C7 -158.6(2) . . . . ?
C10 C5 C6 C7 66.2(3) . . . . ?
C5 C6 C7 C8 -60.1(3) . . . . ?
C6 C7 C8 C14 -80.6(3) . . . . ?
C6 C7 C8 C15 169.7(2) . . . . ?
C6 C7 C8 C9 48.6(3) . . . . ?
C7 C8 C9 C11 -179.3(2) . . . . ?
C14 C8 C9 C11 -48.7(2) . . . . ?
C15 C8 C9 C11 56.7(2) . . . . ?
C7 C8 C9 C10 -44.3(3) . . . . ?
C14 C8 C9 C10 86.3(2) . . . . ?
C15 C8 C9 C10 -168.4(2) . . . . ?
C2 C1 C10 C18 70.4(3) . . . . ?
C2 C1 C10 C5 -52.4(3) . . . . ?
C2 C1 C10 C9 -166.5(2) . . . . ?
C6 C5 C10 C18 68.2(2) . . . . ?
C4 C5 C10 C18 -67.5(2) . . . . ?
C6 C5 C10 C1 -172.1(2) . . . . ?
C4 C5 C10 C1 52.2(3) . . . . ?
C6 C5 C10 C9 -57.3(2) . . . . ?
C4 C5 C10 C9 166.99(18) . . . . ?
C11 C9 C10 C18 53.3(3) . . . . ?
C8 C9 C10 C18 -77.9(3) . . . . ?
C11 C9 C10 C1 -66.1(3) . . . . ?
C8 C9 C10 C1 162.7(2) . . . . ?
C11 C9 C10 C5 178.47(19) . . . . ?
C8 C9 C10 C5 47.2(2) . . . . ?
C16 O1 C11 C12 -50.7(2) . . . . ?
C16 O1 C11 C9 70.0(2) . . . . ?
C8 C9 C11 O1 -58.9(2) . . . . ?
C10 C9 C11 O1 165.77(19) . . . . ?
C8 C9 C11 C12 50.1(3) . . . . ?
C10 C9 C11 C12 -85.2(3) . . . . ?
O1 C11 C12 O2 -67.6(2) . . . . ?
C9 C11 C12 O2 178.35(19) . . . . ?
O1 C11 C12 C13 52.3(2) . . . . ?
C9 C11 C12 C13 -61.8(3) . . . . ?
O2 C12 C13 C14 -168.8(2) . . . . ?
C11 C12 C13 C14 75.2(2) . . . . ?
O2 C12 C13 C16 81.3(3) . . . . ?
C11 C12 C13 C16 -34.7(2) . . . . ?
C7 C8 C14 C13 -169.1(2) . . . . ?
C15 C8 C14 C13 -50.4(2) . . . . ?
C9 C8 C14 C13 61.6(2) . . . . ?
C12 C13 C14 C8 -77.6(2) . . . . ?
C16 C13 C14 C8 31.3(2) . . . . ?
C7 C8 C15 O3 -62.9(3) . . . . ?
C14 C8 C15 O3 176.6(2) . . . . ?
C9 C8 C15 O3 61.0(3) . . . . ?
C7 C8 C15 C16 172.0(2) . . . . ?
C14 C8 C15 C16 51.5(2) . . . . ?
C9 C8 C15 C16 -64.2(2) . . . . ?
C11 O1 C16 C17 156.3(2) . . . . ?
C11 O1 C16 C15 -79.7(2) . . . . ?
C11 O1 C16 C13 28.5(2) . . . . ?
O3 C15 C16 O1 -51.0(2) . . . . ?
C8 C15 C16 O1 75.5(2) . . . . ?
O3 C15 C16 C17 67.4(3) . . . . ?
C8 C15 C16 C17 -166.1(2) . . . . ?
O3 C15 C16 C13 -159.2(2) . . . . ?
C8 C15 C16 C13 -32.7(2) . . . . ?
C12 C13 C16 O1 5.0(2) . . . . ?
C14 C13 C16 O1 -106.9(2) . . . . ?
C12 C13 C16 C17 -115.4(3) . . . . ?
C14 C13 C16 C17 132.7(2) . . . . ?
C12 C13 C16 C15 112.9(2) . . . . ?
C14 C13 C16 C15 1.0(2) . . . . ?
C3 C4 C20 O4 -25.1(4) . . . . ?
C19 C4 C20 O4 89.9(3) . . . . ?
C5 C4 C20 O4 -148.8(3) . . . . ?
C3 C4 C20 O5 160.7(2) . . . . ?
C19 C4 C20 O5 -84.3(3) . . . . ?
C5 C4 C20 O5 37.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O2 0.82 1.79 2.589(3) 164.6 4
C17 H17A O3 0.96 2.61 3.401(4) 140.4 3_655
O6 H6C O7 0.85 2.01 2.789 151.9 1_655
O7 H7D O1 0.90 2.02 2.844(3) 152.0 .
O3 H3 O1 0.97(6) 2.24(6) 2.721(3) 109(4) .
O3 H3 O6 0.97(6) 1.92(6) 2.842(3) 157(5) 3_645
O2 H2 O3 0.81(2) 1.88(3) 2.680(3) 168(5) 3_655
O6 H6D O4 0.82 2.39 3.028(4) 135.7 4

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cu_d8v21971_0m
_database_code_depnum_ccdc_archive 'CCDC 2127070'
_audit_update_record             
;
2021-12-07 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H32 O6'
_chemical_formula_weight         368.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

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

_cell_length_a                   6.6713(2)
_cell_length_b                   19.5694(7)
_cell_length_c                   7.1999(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.5510(10)
_cell_angle_gamma                90
_cell_volume                     939.04(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9771
_cell_measurement_theta_min      12.307
_cell_measurement_theta_max      140.274

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.776
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4501
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11475
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.153
_diffrn_reflns_theta_max         67.938
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3259
_reflns_number_gt                3181
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_max     0.938
_reflns_Friedel_fraction_full    0.938

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0709P)²+0.3079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1470 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3259
_refine_ls_number_parameters     254
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_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_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
O1 O 0.2327(4) 0.35499(14) 0.2191(5) 0.0506(7) Uani 1 1 d D . . . .
O2 O 0.8339(5) 0.37451(19) 0.1691(6) 0.0798(12) Uani 1 1 d . . . . .
H2 H 0.9569 0.3759 0.1713 0.120 Uiso 1 1 calc R U . . .
O3 O 0.8792(4) 0.4634(2) 0.3510(6) 0.0804(11) Uani 1 1 d . . . . .
O4 O 0.0105(3) 0.67406(11) 0.1130(3) 0.0361(5) Uani 1 1 d . . . . .
O5 O -0.0350(4) 0.64463(14) 0.4817(4) 0.0462(6) Uani 1 1 d D . . . .
C1 C 0.2875(5) 0.48196(16) 0.0071(4) 0.0352(7) Uani 1 1 d . . . . .
H1A H 0.1540 0.4727 0.0489 0.042 Uiso 1 1 calc R U . . .
H1B H 0.2733 0.5059 -0.1107 0.042 Uiso 1 1 calc R U . . .
C2 C 0.3951(6) 0.41433(17) -0.0224(5) 0.0419(8) Uani 1 1 d . . . . .
H2A H 0.3170 0.3870 -0.1116 0.050 Uiso 1 1 calc R U . . .
H2B H 0.5243 0.4233 -0.0740 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4265(5) 0.37435(17) 0.1560(5) 0.0399(8) Uani 1 1 d . . . . .
H3 H 0.5028 0.3329 0.1304 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5421(5) 0.41588(16) 0.3093(5) 0.0360(7) Uani 1 1 d . . . . .
C5 C 0.4390(5) 0.48627(15) 0.3340(4) 0.0302(6) Uani 1 1 d . . . . .
H5A H 0.3048 0.4750 0.3749 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5306(5) 0.53165(18) 0.4890(5) 0.0412(8) Uani 1 1 d . . . . .
H6A H 0.5622 0.5040 0.5983 0.049 Uiso 1 1 calc R U . . .
H6B H 0.6544 0.5516 0.4487 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3873(6) 0.58798(19) 0.5386(5) 0.0420(8) Uani 1 1 d . . . . .
H7A H 0.4523 0.6170 0.6325 0.050 Uiso 1 1 calc R U . . .
H7B H 0.2704 0.5677 0.5921 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3184(5) 0.63217(16) 0.3730(4) 0.0319(7) Uani 1 1 d . . . . .
C9 C 0.2525(4) 0.58720(14) 0.2015(4) 0.0264(6) Uani 1 1 d . . . . .
H9 H 0.1319 0.5635 0.2400 0.032 Uiso 1 1 calc R U . . .
C10 C 0.3999(4) 0.52838(14) 0.1507(4) 0.0276(6) Uani 1 1 d . . . . .
C11 C 0.1766(5) 0.63488(15) 0.0429(4) 0.0320(7) Uani 1 1 d . . . . .
H11 H 0.1343 0.6088 -0.0682 0.038 Uiso 1 1 calc R U . . .
C12 C 0.3150(6) 0.69355(17) -0.0054(5) 0.0387(7) Uani 1 1 d . . . . .
H12A H 0.4463 0.6774 -0.0382 0.046 Uiso 1 1 calc R U . . .
H12B H 0.2576 0.7216 -0.1053 0.046 Uiso 1 1 calc R U . . .
C13 C 0.3230(5) 0.73100(16) 0.1793(5) 0.0361(7) Uani 1 1 d . . . . .
H13 H 0.3614 0.7792 0.1693 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4592(5) 0.69008(16) 0.3175(5) 0.0364(7) Uani 1 1 d . . . . .
H14A H 0.5764 0.6724 0.2584 0.044 Uiso 1 1 calc R U . . .
H14B H 0.5019 0.7176 0.4241 0.044 Uiso 1 1 calc R U . . .
C15 C 0.1069(5) 0.72048(17) 0.2479(5) 0.0352(7) Uani 1 1 d . . . . .
C16 C 0.1396(5) 0.67820(17) 0.4234(4) 0.0357(7) Uani 1 1 d . . . . .
H16 H 0.1864 0.7090 0.5235 0.043 Uiso 1 1 calc R U . . .
C17 C -0.0245(6) 0.7836(2) 0.2622(6) 0.0481(9) Uani 1 1 d . . . . .
H17A H -0.0346 0.8063 0.1439 0.072 Uiso 1 1 calc R U . . .
H17B H 0.0339 0.8141 0.3540 0.072 Uiso 1 1 calc R U . . .
H17C H -0.1559 0.7702 0.2977 0.072 Uiso 1 1 calc R U . . .
C18 C 0.5952(5) 0.55254(18) 0.0658(5) 0.0369(7) Uani 1 1 d . . . . .
H18A H 0.5636 0.5793 -0.0432 0.055 Uiso 1 1 calc R U . . .
H18B H 0.6734 0.5135 0.0328 0.055 Uiso 1 1 calc R U . . .
H18C H 0.6707 0.5798 0.1550 0.055 Uiso 1 1 calc R U . . .
C19 C 0.5393(6) 0.3745(2) 0.4913(6) 0.0521(10) Uani 1 1 d . . . . .
H19A H 0.6282 0.3953 0.5834 0.078 Uiso 1 1 calc R U . . .
H19B H 0.5824 0.3285 0.4688 0.078 Uiso 1 1 calc R U . . .
H19C H 0.4055 0.3738 0.5352 0.078 Uiso 1 1 calc R U . . .
C20 C 0.7676(5) 0.4217(2) 0.2764(6) 0.0489(9) Uani 1 1 d . . . . .
O6 O 0.2131(4) 0.21559(15) 0.2219(4) 0.0507(7) Uani 1 1 d G . . . .
H6C H 0.1601 0.1900 0.3015 0.076 Uiso 1 1 d G U . . .
H1 H 0.231(9) 0.3144(16) 0.246(8) 0.076(18) Uiso 1 1 d D . . . .
H6D H 0.171(13) 0.198(5) 0.109(12) 0.13(3) Uiso 1 1 d . . . . .
H5 H -0.084(8) 0.622(3) 0.395(6) 0.076(17) Uiso 1 1 d 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
O1 C3 1.440(4) . ?
O1 H1 0.82(3) . ?
O2 C20 1.294(5) . ?
O2 H2 0.8200 . ?
O3 C20 1.215(5) . ?
O4 C11 1.456(4) . ?
O4 C15 1.458(4) . ?
O5 C16 1.417(4) . ?
O5 H5 0.82(3) . ?
C1 C2 1.525(4) . ?
C1 C10 1.546(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.510(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.548(5) . ?
C3 H3 0.9800 . ?
C4 C20 1.537(5) . ?
C4 C19 1.542(5) . ?
C4 C5 1.553(4) . ?
C5 C6 1.532(5) . ?
C5 C10 1.568(4) . ?
C5 H5A 0.9800 . ?
C6 C7 1.512(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.527(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.536(4) . ?
C8 C16 1.550(5) . ?
C8 C9 1.563(4) . ?
C9 C11 1.543(4) . ?
C9 C10 1.568(4) . ?
C9 H9 0.9800 . ?
C10 C18 1.538(4) . ?
C11 C12 1.523(5) . ?
C11 H11 0.9800 . ?
C12 C13 1.518(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.541(4) . ?
C13 C15 1.558(5) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.518(4) . ?
C15 C17 1.521(5) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O6 H6C 0.8498 . ?
O6 H6D 0.91(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 111(4) . . ?
C20 O2 H2 109.5 . . ?
C11 O4 C15 103.8(2) . . ?
C16 O5 H5 109(4) . . ?
C2 C1 C10 112.7(3) . . ?
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 112.3(3) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 C2 108.2(3) . . ?
O1 C3 C4 109.8(3) . . ?
C2 C3 C4 112.3(3) . . ?
O1 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
C20 C4 C19 102.6(3) . . ?
C20 C4 C3 112.9(3) . . ?
C19 C4 C3 107.8(3) . . ?
C20 C4 C5 113.2(3) . . ?
C19 C4 C5 110.3(3) . . ?
C3 C4 C5 109.7(2) . . ?
C6 C5 C4 115.7(3) . . ?
C6 C5 C10 110.8(2) . . ?
C4 C5 C10 115.3(2) . . ?
C6 C5 H5A 104.5 . . ?
C4 C5 H5A 104.5 . . ?
C10 C5 H5A 104.5 . . ?
C7 C6 C5 111.0(3) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 113.6(3) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C14 117.0(3) . . ?
C7 C8 C16 110.7(3) . . ?
C14 C8 C16 96.8(2) . . ?
C7 C8 C9 111.2(2) . . ?
C14 C8 C9 111.3(2) . . ?
C16 C8 C9 108.7(2) . . ?
C11 C9 C8 108.4(2) . . ?
C11 C9 C10 117.4(2) . . ?
C8 C9 C10 116.1(2) . . ?
C11 C9 H9 104.4 . . ?
C8 C9 H9 104.4 . . ?
C10 C9 H9 104.4 . . ?
C18 C10 C1 108.0(3) . . ?
C18 C10 C5 112.6(2) . . ?
C1 C10 C5 108.2(2) . . ?
C18 C10 C9 114.7(2) . . ?
C1 C10 C9 107.3(2) . . ?
C5 C10 C9 105.8(2) . . ?
O4 C11 C12 99.2(2) . . ?
O4 C11 C9 106.9(2) . . ?
C12 C11 C9 116.3(3) . . ?
O4 C11 H11 111.2 . . ?
C12 C11 H11 111.2 . . ?
C9 C11 H11 111.2 . . ?
C13 C12 C11 99.3(3) . . ?
C13 C12 H12A 111.9 . . ?
C11 C12 H12A 111.9 . . ?
C13 C12 H12B 111.9 . . ?
C11 C12 H12B 111.9 . . ?
H12A C12 H12B 109.6 . . ?
C12 C13 C14 108.2(3) . . ?
C12 C13 C15 102.5(3) . . ?
C14 C13 C15 104.7(3) . . ?
C12 C13 H13 113.5 . . ?
C14 C13 H13 113.5 . . ?
C15 C13 H13 113.5 . . ?
C8 C14 C13 101.6(2) . . ?
C8 C14 H14A 111.4 . . ?
C13 C14 H14A 111.4 . . ?
C8 C14 H14B 111.4 . . ?
C13 C14 H14B 111.4 . . ?
H14A C14 H14B 109.3 . . ?
O4 C15 C16 104.9(3) . . ?
O4 C15 C17 108.2(3) . . ?
C16 C15 C17 116.6(3) . . ?
O4 C15 C13 105.0(3) . . ?
C16 C15 C13 103.6(2) . . ?
C17 C15 C13 117.3(3) . . ?
O5 C16 C15 114.2(3) . . ?
O5 C16 C8 116.8(3) . . ?
C15 C16 C8 101.8(3) . . ?
O5 C16 H16 107.8 . . ?
C15 C16 H16 107.8 . . ?
C8 C16 H16 107.8 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 O2 121.6(3) . . ?
O3 C20 C4 124.5(4) . . ?
O2 C20 C4 113.7(3) . . ?
H6C O6 H6D 104.9 . . ?

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 57.7(4) . . . . ?
C1 C2 C3 O1 65.2(4) . . . . ?
C1 C2 C3 C4 -56.2(4) . . . . ?
O1 C3 C4 C20 164.3(3) . . . . ?
C2 C3 C4 C20 -75.3(3) . . . . ?
O1 C3 C4 C19 51.7(3) . . . . ?
C2 C3 C4 C19 172.1(3) . . . . ?
O1 C3 C4 C5 -68.4(3) . . . . ?
C2 C3 C4 C5 52.0(3) . . . . ?
C20 C4 C5 C6 -56.1(4) . . . . ?
C19 C4 C5 C6 58.2(4) . . . . ?
C3 C4 C5 C6 176.8(3) . . . . ?
C20 C4 C5 C10 75.4(4) . . . . ?
C19 C4 C5 C10 -170.3(3) . . . . ?
C3 C4 C5 C10 -51.7(3) . . . . ?
C4 C5 C6 C7 -163.3(3) . . . . ?
C10 C5 C6 C7 63.1(4) . . . . ?
C5 C6 C7 C8 -55.8(4) . . . . ?
C6 C7 C8 C14 -82.6(4) . . . . ?
C6 C7 C8 C16 167.9(3) . . . . ?
C6 C7 C8 C9 46.9(4) . . . . ?
C7 C8 C9 C11 177.6(3) . . . . ?
C14 C8 C9 C11 -49.9(3) . . . . ?
C16 C8 C9 C11 55.5(3) . . . . ?
C7 C8 C9 C10 -47.7(4) . . . . ?
C14 C8 C9 C10 84.8(3) . . . . ?
C16 C8 C9 C10 -169.8(3) . . . . ?
C2 C1 C10 C18 68.6(3) . . . . ?
C2 C1 C10 C5 -53.5(3) . . . . ?
C2 C1 C10 C9 -167.2(3) . . . . ?
C6 C5 C10 C18 66.7(3) . . . . ?
C4 C5 C10 C18 -67.1(3) . . . . ?
C6 C5 C10 C1 -174.1(3) . . . . ?
C4 C5 C10 C1 52.1(3) . . . . ?
C6 C5 C10 C9 -59.4(3) . . . . ?
C4 C5 C10 C9 166.8(2) . . . . ?
C11 C9 C10 C18 58.9(3) . . . . ?
C8 C9 C10 C18 -71.6(3) . . . . ?
C11 C9 C10 C1 -61.1(3) . . . . ?
C8 C9 C10 C1 168.4(2) . . . . ?
C11 C9 C10 C5 -176.4(2) . . . . ?
C8 C9 C10 C5 53.1(3) . . . . ?
C15 O4 C11 C12 -50.5(3) . . . . ?
C15 O4 C11 C9 70.7(3) . . . . ?
C8 C9 C11 O4 -58.7(3) . . . . ?
C10 C9 C11 O4 167.2(2) . . . . ?
C8 C9 C11 C12 51.0(3) . . . . ?
C10 C9 C11 C12 -83.1(3) . . . . ?
O4 C11 C12 C13 53.0(3) . . . . ?
C9 C11 C12 C13 -61.2(3) . . . . ?
C11 C12 C13 C14 74.9(3) . . . . ?
C11 C12 C13 C15 -35.3(3) . . . . ?
C7 C8 C14 C13 -168.5(3) . . . . ?
C16 C8 C14 C13 -51.0(3) . . . . ?
C9 C8 C14 C13 62.1(3) . . . . ?
C12 C13 C14 C8 -78.3(3) . . . . ?
C15 C13 C14 C8 30.5(3) . . . . ?
C11 O4 C15 C16 -81.2(3) . . . . ?
C11 O4 C15 C17 153.6(3) . . . . ?
C11 O4 C15 C13 27.6(3) . . . . ?
C12 C13 C15 O4 6.0(3) . . . . ?
C14 C13 C15 O4 -106.8(3) . . . . ?
C12 C13 C15 C16 115.9(3) . . . . ?
C14 C13 C15 C16 3.0(3) . . . . ?
C12 C13 C15 C17 -114.1(3) . . . . ?
C14 C13 C15 C17 133.0(3) . . . . ?
O4 C15 C16 O5 -52.1(3) . . . . ?
C17 C15 C16 O5 67.6(4) . . . . ?
C13 C15 C16 O5 -162.0(3) . . . . ?
O4 C15 C16 C8 74.7(3) . . . . ?
C17 C15 C16 C8 -165.6(3) . . . . ?
C13 C15 C16 C8 -35.2(3) . . . . ?
C7 C8 C16 O5 -59.0(4) . . . . ?
C14 C8 C16 O5 178.7(3) . . . . ?
C9 C8 C16 O5 63.5(3) . . . . ?
C7 C8 C16 C15 176.0(3) . . . . ?
C14 C8 C16 C15 53.7(3) . . . . ?
C9 C8 C16 C15 -61.6(3) . . . . ?
C19 C4 C20 O3 -81.8(5) . . . . ?
C3 C4 C20 O3 162.5(4) . . . . ?
C5 C4 C20 O3 37.1(5) . . . . ?
C19 C4 C20 O2 94.0(4) . . . . ?
C3 C4 C20 O2 -21.7(5) . . . . ?
C5 C4 C20 O2 -147.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6D O4 0.91(9) 2.02(9) 2.895(4) 160(8) 2_545
O1 H1 O6 0.82(3) 1.94(3) 2.731(4) 161(6) .
O6 H6C O5 0.85 2.01 2.850(4) 169.7 2_546
O2 H2 O1 0.82 1.90 2.696(4) 162.8 1_655

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cu_d8v21973_0m
_database_code_depnum_ccdc_archive 'CCDC 2127071'
_audit_update_record             
;
2021-12-07 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H32 O5'
_chemical_formula_weight         352.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

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

_cell_length_a                   8.4122(2)
_cell_length_b                   19.7326(6)
_cell_length_c                   11.0321(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.2360(10)
_cell_angle_gamma                90
_cell_volume                     1829.87(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9012
_cell_measurement_theta_min      9.189
_cell_measurement_theta_max      140.331

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.730
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5780
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21478
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.594
_diffrn_reflns_theta_max         67.495
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             6401
_reflns_number_gt                6271
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.958

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.2120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2929 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6401
_refine_ls_number_parameters     489
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.056
_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_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
O1 O 0.5237(2) 0.59653(9) 0.56774(15) 0.0459(4) Uani 1 1 d . . . . .
H1 H 0.4543 0.6153 0.5257 0.069 Uiso 1 1 calc R U . . .
O2 O 0.6266(2) 0.71774(9) 0.79257(16) 0.0416(4) Uani 1 1 d D . . . .
O4 O 0.3223(3) 0.26711(10) 0.97817(18) 0.0545(5) Uani 1 1 d . . . . .
H4 H 0.3393 0.2582 1.0501 0.082 Uiso 1 1 calc R U . . .
O5 O 0.2773(3) 0.36939(10) 1.05344(17) 0.0529(5) Uani 1 1 d . . . . .
C1 C 0.5384(3) 0.36591(12) 0.6976(2) 0.0388(5) Uani 1 1 d . . . . .
H1A H 0.5005 0.3796 0.6172 0.047 Uiso 1 1 calc R U . . .
H1B H 0.6530 0.3611 0.6961 0.047 Uiso 1 1 calc R U . . .
C2 C 0.4665(3) 0.29730(12) 0.7265(2) 0.0429(5) Uani 1 1 d . . . . .
H2A H 0.4876 0.2659 0.6613 0.051 Uiso 1 1 calc R U . . .
H2B H 0.5174 0.2797 0.8003 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2884(3) 0.30121(12) 0.7422(2) 0.0405(5) Uani 1 1 d . . . . .
H3A H 0.2503 0.2570 0.7665 0.049 Uiso 1 1 calc R U . . .
H3B H 0.2363 0.3124 0.6648 0.049 Uiso 1 1 calc R U . . .
C4 C 0.2415(3) 0.35391(12) 0.8368(2) 0.0353(5) Uani 1 1 d . . . . .
C5 C 0.3153(2) 0.42348(11) 0.8003(2) 0.0316(4) Uani 1 1 d . . . . .
H5 H 0.2738 0.4308 0.7171 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2607(3) 0.48615(12) 0.8688(2) 0.0387(5) Uani 1 1 d . . . . .
H6A H 0.1471 0.4838 0.8802 0.046 Uiso 1 1 calc R U . . .
H6B H 0.3147 0.4883 0.9480 0.046 Uiso 1 1 calc R U . . .
C7 C 0.2996(3) 0.54910(12) 0.7954(2) 0.0378(5) Uani 1 1 d . . . . .
H7A H 0.2598 0.5889 0.8361 0.045 Uiso 1 1 calc R U . . .
H7B H 0.2455 0.5462 0.7162 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4779(2) 0.55726(11) 0.77891(19) 0.0293(4) Uani 1 1 d . . . . .
C9 C 0.5491(2) 0.49092(11) 0.72886(18) 0.0294(4) Uani 1 1 d . . . . .
H9 H 0.5046 0.4880 0.6456 0.035 Uiso 1 1 calc R U . . .
C10 C 0.4991(2) 0.42264(11) 0.78833(19) 0.0305(4) Uani 1 1 d . . . . .
C11 C 0.7302(2) 0.49991(12) 0.7134(2) 0.0348(5) Uani 1 1 d . . . . .
H11A H 0.7792 0.4554 0.7162 0.042 Uiso 1 1 calc R U . . .
H11B H 0.7457 0.5185 0.6333 0.042 Uiso 1 1 calc R U . . .
C12 C 0.8186(3) 0.54528(13) 0.8067(2) 0.0407(5) Uani 1 1 d . . . . .
H12A H 0.8459 0.5185 0.8782 0.049 Uiso 1 1 calc R U . . .
H12B H 0.9172 0.5604 0.7728 0.049 Uiso 1 1 calc R U . . .
C13 C 0.7241(3) 0.60741(12) 0.8451(2) 0.0362(5) Uani 1 1 d . . . . .
H13 H 0.7846 0.6338 0.9063 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5677(3) 0.58261(12) 0.8947(2) 0.0341(5) Uani 1 1 d . . . . .
H14A H 0.5106 0.6192 0.9326 0.041 Uiso 1 1 calc R U . . .
H14B H 0.5851 0.5462 0.9529 0.041 Uiso 1 1 calc R U . . .
C15 C 0.5113(3) 0.61715(11) 0.69079(19) 0.0322(4) Uani 1 1 d . . . . .
H15 H 0.4235 0.6496 0.6948 0.039 Uiso 1 1 calc R U . . .
C16 C 0.6659(3) 0.65253(12) 0.7399(2) 0.0349(5) Uani 1 1 d D . . . .
O3 O 0.9236(3) 0.69581(12) 0.6840(3) 0.0502(6) Uani 0.75 1 d D U P A 1
H3 H 0.9073 0.7303 0.7231 0.075 Uiso 0.75 1 calc R U P A 1
C17 C 0.7718(16) 0.6694(11) 0.6333(14) 0.041(2) Uani 0.5 1 d D U P A 1
H17A H 0.7900 0.6289 0.5857 0.050 Uiso 0.5 1 calc R U P A 1
H17B H 0.7204 0.7030 0.5809 0.050 Uiso 0.5 1 calc R U P A 1
O3' O 0.7695(9) 0.7115(4) 0.5654(7) 0.0502(16) Uani 0.25 1 d D U P A 2
H3' H 0.8464 0.7143 0.5223 0.075 Uiso 0.25 1 calc R U P A 2
C17' C 0.7982(18) 0.6634(10) 0.6521(14) 0.043(2) Uani 0.5 1 d D U P A 2
H17C H 0.8941 0.6758 0.6984 0.051 Uiso 0.5 1 calc R U P A 2
H17D H 0.8187 0.6207 0.6121 0.051 Uiso 0.5 1 calc R U P A 2
C18 C 0.5901(3) 0.40851(13) 0.9096(2) 0.0391(5) Uani 1 1 d . . . . .
H18A H 0.7012 0.4177 0.9011 0.059 Uiso 1 1 calc R U . . .
H18B H 0.5765 0.3619 0.9317 0.059 Uiso 1 1 calc R U . . .
H18C H 0.5494 0.4371 0.9716 0.059 Uiso 1 1 calc R U . . .
C19 C 0.0577(3) 0.35897(14) 0.8342(3) 0.0485(6) Uani 1 1 d . . . . .
H19A H 0.0131 0.3146 0.8440 0.073 Uiso 1 1 calc R U . . .
H19B H 0.0204 0.3777 0.7580 0.073 Uiso 1 1 calc R U . . .
H19C H 0.0257 0.3877 0.8991 0.073 Uiso 1 1 calc R U . . .
C20 C 0.2855(3) 0.33209(12) 0.9663(2) 0.0388(5) Uani 1 1 d . . . . .
O6 O 0.0234(2) 0.33214(10) 0.19219(16) 0.0473(4) Uani 1 1 d . . . . .
H6 H 0.1018 0.3463 0.1582 0.071 Uiso 1 1 calc R U . . .
O7 O -0.0745(2) 0.28554(9) 0.47952(17) 0.0458(4) Uani 1 1 d D . . . .
O8 O -0.3819(2) 0.27629(10) 0.36854(19) 0.0493(4) Uani 1 1 d . . . . .
O9 O 0.2968(2) 0.66711(9) 0.44657(16) 0.0492(4) Uani 1 1 d . . . . .
O10 O 0.1679(2) 0.73244(8) 0.31452(15) 0.0402(4) Uani 1 1 d . . . . .
H10 H 0.1480 0.7530 0.3767 0.060 Uiso 1 1 calc R U . . .
C21 C -0.0298(3) 0.58169(13) 0.1226(2) 0.0408(5) Uani 1 1 d . . . . .
H21A H 0.0064 0.5519 0.0594 0.049 Uiso 1 1 calc R U . . .
H21B H -0.1451 0.5827 0.1165 0.049 Uiso 1 1 calc R U . . .
C22 C 0.0329(3) 0.65300(13) 0.0997(2) 0.0440(6) Uani 1 1 d . . . . .
H22A H 0.0016 0.6668 0.0178 0.053 Uiso 1 1 calc R U . . .
H22B H -0.0145 0.6844 0.1555 0.053 Uiso 1 1 calc R U . . .
C23 C 0.2130(3) 0.65632(13) 0.1159(2) 0.0395(5) Uani 1 1 d . . . . .
H23A H 0.2462 0.7031 0.1078 0.047 Uiso 1 1 calc R U . . .
H23B H 0.2595 0.6307 0.0512 0.047 Uiso 1 1 calc R U . . .
C24 C 0.2793(2) 0.62897(11) 0.23824(19) 0.0314(4) Uani 1 1 d . . . . .
C25 C 0.2074(2) 0.55656(11) 0.25829(19) 0.0289(4) Uani 1 1 d . . . . .
H25 H 0.2431 0.5302 0.1891 0.035 Uiso 1 1 calc R U . . .
C26 C 0.2751(2) 0.51809(11) 0.3688(2) 0.0328(4) Uani 1 1 d . . . . .
H26A H 0.3893 0.5248 0.3765 0.039 Uiso 1 1 calc R U . . .
H26B H 0.2282 0.5351 0.4418 0.039 Uiso 1 1 calc R U . . .
C27 C 0.2382(2) 0.44309(11) 0.3540(2) 0.0335(5) Uani 1 1 d . . . . .
H27A H 0.2836 0.4186 0.4234 0.040 Uiso 1 1 calc R U . . .
H27B H 0.2879 0.4263 0.2821 0.040 Uiso 1 1 calc R U . . .
C28 C 0.0599(2) 0.42911(11) 0.34314(19) 0.0299(4) Uani 1 1 d . . . . .
C29 C -0.0216(2) 0.47445(11) 0.24438(19) 0.0306(4) Uani 1 1 d . . . . .
H29 H 0.0192 0.4578 0.1679 0.037 Uiso 1 1 calc R U . . .
C30 C 0.0227(2) 0.55178(11) 0.24716(19) 0.0304(4) Uani 1 1 d . . . . .
C31 C -0.2029(3) 0.45935(13) 0.2346(2) 0.0400(5) Uani 1 1 d . . . . .
H31A H -0.2564 0.4989 0.2005 0.048 Uiso 1 1 calc R U . . .
H31B H -0.2203 0.4224 0.1777 0.048 Uiso 1 1 calc R U . . .
C32 C -0.2823(3) 0.44075(13) 0.3534(3) 0.0432(6) Uani 1 1 d . . . . .
H32A H -0.3088 0.4821 0.3956 0.052 Uiso 1 1 calc R U . . .
H32B H -0.3809 0.4169 0.3339 0.052 Uiso 1 1 calc R U . . .
C33 C -0.1785(3) 0.39652(12) 0.4385(2) 0.0372(5) Uani 1 1 d . . . . .
H33 H -0.2328 0.3870 0.5136 0.045 Uiso 1 1 calc R U . . .
C34 C -0.0221(3) 0.43374(12) 0.4654(2) 0.0352(5) Uani 1 1 d . . . . .
H34A H 0.0405 0.4115 0.5296 0.042 Uiso 1 1 calc R U . . .
H34B H -0.0404 0.4805 0.4881 0.042 Uiso 1 1 calc R U . . .
C35 C 0.0320(3) 0.35222(11) 0.3157(2) 0.0342(5) Uani 1 1 d . . . . .
H35 H 0.1209 0.3274 0.3548 0.041 Uiso 1 1 calc R U . . .
C36 C -0.1214(3) 0.33063(11) 0.3805(2) 0.0354(5) Uani 1 1 d . . . . .
C37 C -0.2448(3) 0.29274(14) 0.3009(2) 0.0451(6) Uani 1 1 d . . . . .
H37A H -0.2767 0.3207 0.2318 0.054 Uiso 1 1 calc R U . . .
H37B H -0.1981 0.2514 0.2706 0.054 Uiso 1 1 calc R U . . .
C38 C -0.0595(3) 0.59134(12) 0.3478(2) 0.0381(5) Uani 1 1 d . . . . .
H38A H -0.1688 0.5776 0.3502 0.057 Uiso 1 1 calc R U . . .
H38B H -0.0543 0.6390 0.3312 0.057 Uiso 1 1 calc R U . . .
H38C H -0.0066 0.5820 0.4247 0.057 Uiso 1 1 calc R U . . .
C39 C 0.4623(3) 0.62230(12) 0.2306(2) 0.0397(5) Uani 1 1 d . . . . .
H39A H 0.5092 0.6167 0.3107 0.060 Uiso 1 1 calc R U . . .
H39B H 0.5041 0.6624 0.1944 0.060 Uiso 1 1 calc R U . . .
H39C H 0.4868 0.5836 0.1820 0.060 Uiso 1 1 calc R U . . .
C40 C 0.2483(2) 0.67717(11) 0.34272(19) 0.0314(4) Uani 1 1 d . . . . .
H2 H 0.562(4) 0.7367(17) 0.741(3) 0.054(9) Uiso 1 1 d D . . . .
H7 H -0.033(6) 0.253(2) 0.445(5) 0.117(19) Uiso 1 1 d D . . . .
H8 H -0.344(5) 0.251(3) 0.433(4) 0.084(13) Uiso 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
O1 C15 1.425(3) . ?
O1 H1 0.8200 . ?
O2 C16 1.455(3) . ?
O2 H2 0.86(2) . ?
O4 C20 1.324(3) . ?
O4 H4 0.8200 . ?
O5 C20 1.214(3) . ?
C1 C2 1.521(3) . ?
C1 C10 1.546(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.517(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.536(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C20 1.524(3) . ?
C4 C19 1.549(3) . ?
C4 C5 1.566(3) . ?
C5 C6 1.529(3) . ?
C5 C10 1.557(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.525(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.527(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.542(3) . ?
C8 C9 1.550(3) . ?
C8 C15 1.563(3) . ?
C9 C11 1.550(3) . ?
C9 C10 1.563(3) . ?
C9 H9 0.9800 . ?
C10 C18 1.541(3) . ?
C11 C12 1.535(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.530(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.525(3) . ?
C13 C16 1.528(3) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.554(3) . ?
C15 H15 0.9800 . ?
C16 C17' 1.519(15) . ?
C16 C17 1.540(15) . ?
O3 C17 1.470(15) . ?
O3 H3 0.8200 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O3' C17' 1.362(15) . ?
O3' H3' 0.8200 . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O6 C35 1.418(3) . ?
O6 H6 0.8200 . ?
O7 C36 1.452(3) . ?
O7 H7 0.83(3) . ?
O8 C37 1.435(3) . ?
O8 H8 0.92(5) . ?
O9 C40 1.217(3) . ?
O10 C40 1.314(3) . ?
O10 H10 0.8200 . ?
C21 C22 1.527(3) . ?
C21 C30 1.544(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.520(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.538(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C40 1.525(3) . ?
C24 C39 1.550(3) . ?
C24 C25 1.571(3) . ?
C25 C26 1.528(3) . ?
C25 C30 1.556(3) . ?
C25 H25 0.9800 . ?
C26 C27 1.520(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.525(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C34 1.541(3) . ?
C28 C29 1.549(3) . ?
C28 C35 1.563(3) . ?
C29 C31 1.554(3) . ?
C29 C30 1.571(3) . ?
C29 H29 0.9800 . ?
C30 C38 1.543(3) . ?
C31 C32 1.539(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.530(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.526(3) . ?
C33 C36 1.535(3) . ?
C33 H33 0.9800 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.558(3) . ?
C35 H35 0.9800 . ?
C36 C37 1.529(3) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 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
C15 O1 H1 109.5 . . ?
C16 O2 H2 106(2) . . ?
C20 O4 H4 109.5 . . ?
C2 C1 C10 114.37(19) . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 112.4(2) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 113.16(19) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
C20 C4 C3 112.7(2) . . ?
C20 C4 C19 103.95(19) . . ?
C3 C4 C19 108.3(2) . . ?
C20 C4 C5 113.90(18) . . ?
C3 C4 C5 107.69(18) . . ?
C19 C4 C5 110.13(19) . . ?
C6 C5 C10 111.65(18) . . ?
C6 C5 C4 116.87(18) . . ?
C10 C5 C4 114.66(17) . . ?
C6 C5 H5 103.9 . . ?
C10 C5 H5 103.9 . . ?
C4 C5 H5 103.9 . . ?
C7 C6 C5 108.74(19) . . ?
C7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C6 C7 C8 112.38(18) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C14 112.79(18) . . ?
C7 C8 C9 110.38(17) . . ?
C14 C8 C9 112.70(16) . . ?
C7 C8 C15 110.79(17) . . ?
C14 C8 C15 100.14(17) . . ?
C9 C8 C15 109.62(17) . . ?
C8 C9 C11 109.72(17) . . ?
C8 C9 C10 117.67(16) . . ?
C11 C9 C10 115.26(16) . . ?
C8 C9 H9 104.1 . . ?
C11 C9 H9 104.1 . . ?
C10 C9 H9 104.1 . . ?
C18 C10 C1 108.62(19) . . ?
C18 C10 C5 112.95(17) . . ?
C1 C10 C5 107.51(18) . . ?
C18 C10 C9 112.80(18) . . ?
C1 C10 C9 106.54(17) . . ?
C5 C10 C9 108.10(16) . . ?
C12 C11 C9 116.46(18) . . ?
C12 C11 H11A 108.2 . . ?
C9 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C9 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C13 C12 C11 114.19(18) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C16 101.77(17) . . ?
C14 C13 C12 107.89(19) . . ?
C16 C13 C12 114.30(19) . . ?
C14 C13 H13 110.8 . . ?
C16 C13 H13 110.8 . . ?
C12 C13 H13 110.8 . . ?
C13 C14 C8 102.01(17) . . ?
C13 C14 H14A 111.4 . . ?
C8 C14 H14A 111.4 . . ?
C13 C14 H14B 111.4 . . ?
C8 C14 H14B 111.4 . . ?
H14A C14 H14B 109.2 . . ?
O1 C15 C16 111.67(19) . . ?
O1 C15 C8 113.47(18) . . ?
C16 C15 C8 106.91(16) . . ?
O1 C15 H15 108.2 . . ?
C16 C15 H15 108.2 . . ?
C8 C15 H15 108.2 . . ?
O2 C16 C17' 108.2(8) . . ?
O2 C16 C13 106.45(18) . . ?
C17' C16 C13 110.2(6) . . ?
O2 C16 C17 105.1(8) . . ?
C13 C16 C17 121.9(6) . . ?
O2 C16 C15 109.68(17) . . ?
C17' C16 C15 117.7(7) . . ?
C13 C16 C15 104.00(18) . . ?
C17 C16 C15 109.4(6) . . ?
C17 O3 H3 109.5 . . ?
O3 C17 C16 107.8(9) . . ?
O3 C17 H17A 110.1 . . ?
C16 C17 H17A 110.1 . . ?
O3 C17 H17B 110.1 . . ?
C16 C17 H17B 110.1 . . ?
H17A C17 H17B 108.5 . . ?
C17' O3' H3' 109.5 . . ?
O3' C17' C16 115.6(12) . . ?
O3' C17' H17C 108.4 . . ?
C16 C17' H17C 108.4 . . ?
O3' C17' H17D 108.4 . . ?
C16 C17' H17D 108.4 . . ?
H17C C17' H17D 107.4 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 O4 121.9(2) . . ?
O5 C20 C4 123.5(2) . . ?
O4 C20 C4 114.4(2) . . ?
C35 O6 H6 109.5 . . ?
C36 O7 H7 104(4) . . ?
C37 O8 H8 105(3) . . ?
C40 O10 H10 109.5 . . ?
C22 C21 C30 114.26(19) . . ?
C22 C21 H21A 108.7 . . ?
C30 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C30 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C21 111.7(2) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 114.47(19) . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C40 C24 C23 112.18(18) . . ?
C40 C24 C39 107.06(17) . . ?
C23 C24 C39 108.02(19) . . ?
C40 C24 C25 112.51(17) . . ?
C23 C24 C25 108.31(17) . . ?
C39 C24 C25 108.62(17) . . ?
C26 C25 C30 111.89(17) . . ?
C26 C25 C24 115.51(16) . . ?
C30 C25 C24 115.66(17) . . ?
C26 C25 H25 104.0 . . ?
C30 C25 H25 104.0 . . ?
C24 C25 H25 104.0 . . ?
C27 C26 C25 109.27(18) . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
C26 C27 C28 112.37(18) . . ?
C26 C27 H27A 109.1 . . ?
C28 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
C28 C27 H27B 109.1 . . ?
H27A C27 H27B 107.9 . . ?
C27 C28 C34 113.10(18) . . ?
C27 C28 C29 110.95(17) . . ?
C34 C28 C29 112.38(17) . . ?
C27 C28 C35 109.31(17) . . ?
C34 C28 C35 99.11(17) . . ?
C29 C28 C35 111.43(17) . . ?
C28 C29 C31 110.14(17) . . ?
C28 C29 C30 116.70(16) . . ?
C31 C29 C30 114.78(17) . . ?
C28 C29 H29 104.6 . . ?
C31 C29 H29 104.6 . . ?
C30 C29 H29 104.6 . . ?
C38 C30 C21 109.05(19) . . ?
C38 C30 C25 112.75(17) . . ?
C21 C30 C25 107.28(17) . . ?
C38 C30 C29 113.13(18) . . ?
C21 C30 C29 107.13(17) . . ?
C25 C30 C29 107.20(16) . . ?
C32 C31 C29 116.37(19) . . ?
C32 C31 H31A 108.2 . . ?
C29 C31 H31A 108.2 . . ?
C32 C31 H31B 108.2 . . ?
C29 C31 H31B 108.2 . . ?
H31A C31 H31B 107.3 . . ?
C33 C32 C31 113.71(19) . . ?
C33 C32 H32A 108.8 . . ?
C31 C32 H32A 108.8 . . ?
C33 C32 H32B 108.8 . . ?
C31 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C34 C33 C32 108.19(19) . . ?
C34 C33 C36 101.96(18) . . ?
C32 C33 C36 114.1(2) . . ?
C34 C33 H33 110.8 . . ?
C32 C33 H33 110.8 . . ?
C36 C33 H33 110.8 . . ?
C33 C34 C28 102.29(17) . . ?
C33 C34 H34A 111.3 . . ?
C28 C34 H34A 111.3 . . ?
C33 C34 H34B 111.3 . . ?
C28 C34 H34B 111.3 . . ?
H34A C34 H34B 109.2 . . ?
O6 C35 C36 110.65(18) . . ?
O6 C35 C28 117.32(19) . . ?
C36 C35 C28 107.29(17) . . ?
O6 C35 H35 107.0 . . ?
C36 C35 H35 107.0 . . ?
C28 C35 H35 107.0 . . ?
O7 C36 C37 106.92(19) . . ?
O7 C36 C33 106.60(18) . . ?
C37 C36 C33 115.9(2) . . ?
O7 C36 C35 107.88(18) . . ?
C37 C36 C35 115.23(19) . . ?
C33 C36 C35 103.76(17) . . ?
O8 C37 C36 110.7(2) . . ?
O8 C37 H37A 109.5 . . ?
C36 C37 H37A 109.5 . . ?
O8 C37 H37B 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 108.1 . . ?
C30 C38 H38A 109.5 . . ?
C30 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C30 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C24 C39 H39A 109.5 . . ?
C24 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C24 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O9 C40 O10 120.6(2) . . ?
O9 C40 C24 123.3(2) . . ?
O10 C40 C24 116.13(18) . . ?

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 53.1(3) . . . . ?
C1 C2 C3 C4 -54.3(3) . . . . ?
C2 C3 C4 C20 -71.9(3) . . . . ?
C2 C3 C4 C19 173.7(2) . . . . ?
C2 C3 C4 C5 54.6(3) . . . . ?
C20 C4 C5 C6 -64.5(3) . . . . ?
C3 C4 C5 C6 169.72(19) . . . . ?
C19 C4 C5 C6 51.8(3) . . . . ?
C20 C4 C5 C10 69.0(2) . . . . ?
C3 C4 C5 C10 -56.8(2) . . . . ?
C19 C4 C5 C10 -174.7(2) . . . . ?
C10 C5 C6 C7 63.8(2) . . . . ?
C4 C5 C6 C7 -161.43(18) . . . . ?
C5 C6 C7 C8 -62.0(2) . . . . ?
C6 C7 C8 C14 -75.4(2) . . . . ?
C6 C7 C8 C9 51.7(2) . . . . ?
C6 C7 C8 C15 173.30(19) . . . . ?
C7 C8 C9 C11 -179.69(18) . . . . ?
C14 C8 C9 C11 -52.6(2) . . . . ?
C15 C8 C9 C11 58.0(2) . . . . ?
C7 C8 C9 C10 -45.3(2) . . . . ?
C14 C8 C9 C10 81.8(2) . . . . ?
C15 C8 C9 C10 -167.59(17) . . . . ?
C2 C1 C10 C18 70.6(3) . . . . ?
C2 C1 C10 C5 -51.9(3) . . . . ?
C2 C1 C10 C9 -167.57(19) . . . . ?
C6 C5 C10 C18 71.0(2) . . . . ?
C4 C5 C10 C18 -64.8(2) . . . . ?
C6 C5 C10 C1 -169.15(19) . . . . ?
C4 C5 C10 C1 55.0(2) . . . . ?
C6 C5 C10 C9 -54.5(2) . . . . ?
C4 C5 C10 C9 169.67(18) . . . . ?
C8 C9 C10 C18 -79.4(2) . . . . ?
C11 C9 C10 C18 52.6(2) . . . . ?
C8 C9 C10 C1 161.55(18) . . . . ?
C11 C9 C10 C1 -66.5(2) . . . . ?
C8 C9 C10 C5 46.3(2) . . . . ?
C11 C9 C10 C5 178.22(17) . . . . ?
C8 C9 C11 C12 34.0(2) . . . . ?
C10 C9 C11 C12 -101.6(2) . . . . ?
C9 C11 C12 C13 -37.8(3) . . . . ?
C11 C12 C13 C14 56.9(3) . . . . ?
C11 C12 C13 C16 -55.5(3) . . . . ?
C16 C13 C14 C8 50.1(2) . . . . ?
C12 C13 C14 C8 -70.5(2) . . . . ?
C7 C8 C14 C13 -162.78(18) . . . . ?
C9 C8 C14 C13 71.4(2) . . . . ?
C15 C8 C14 C13 -45.0(2) . . . . ?
C7 C8 C15 O1 -93.4(2) . . . . ?
C14 C8 C15 O1 147.37(18) . . . . ?
C9 C8 C15 O1 28.7(2) . . . . ?
C7 C8 C15 C16 143.07(18) . . . . ?
C14 C8 C15 C16 23.8(2) . . . . ?
C9 C8 C15 C16 -94.88(19) . . . . ?
C14 C13 C16 O2 82.1(2) . . . . ?
C12 C13 C16 O2 -161.94(18) . . . . ?
C14 C13 C16 C17' -160.8(9) . . . . ?
C12 C13 C16 C17' -44.8(9) . . . . ?
C14 C13 C16 C17 -157.6(9) . . . . ?
C12 C13 C16 C17 -41.6(9) . . . . ?
C14 C13 C16 C15 -33.8(2) . . . . ?
C12 C13 C16 C15 82.2(2) . . . . ?
O1 C15 C16 O2 127.66(19) . . . . ?
C8 C15 C16 O2 -107.67(19) . . . . ?
O1 C15 C16 C17' 3.4(8) . . . . ?
C8 C15 C16 C17' 128.1(8) . . . . ?
O1 C15 C16 C13 -118.81(19) . . . . ?
C8 C15 C16 C13 5.9(2) . . . . ?
O1 C15 C16 C17 12.8(8) . . . . ?
C8 C15 C16 C17 137.5(8) . . . . ?
O2 C16 C17 O3 68.4(11) . . . . ?
C17' C16 C17 O3 -38(7) . . . . ?
C13 C16 C17 O3 -52.5(15) . . . . ?
C15 C16 C17 O3 -173.9(8) . . . . ?
O2 C16 C17' O3' -53.7(15) . . . . ?
C13 C16 C17' O3' -169.7(11) . . . . ?
C17 C16 C17' O3' 23(6) . . . . ?
C15 C16 C17' O3' 71.3(16) . . . . ?
C3 C4 C20 O5 170.5(2) . . . . ?
C19 C4 C20 O5 -72.4(3) . . . . ?
C5 C4 C20 O5 47.4(3) . . . . ?
C3 C4 C20 O4 -14.4(3) . . . . ?
C19 C4 C20 O4 102.7(2) . . . . ?
C5 C4 C20 O4 -137.5(2) . . . . ?
C30 C21 C22 C23 54.7(3) . . . . ?
C21 C22 C23 C24 -53.3(3) . . . . ?
C22 C23 C24 C40 -73.5(3) . . . . ?
C22 C23 C24 C39 168.8(2) . . . . ?
C22 C23 C24 C25 51.3(3) . . . . ?
C40 C24 C25 C26 -62.2(2) . . . . ?
C23 C24 C25 C26 173.23(18) . . . . ?
C39 C24 C25 C26 56.1(2) . . . . ?
C40 C24 C25 C30 71.2(2) . . . . ?
C23 C24 C25 C30 -53.3(2) . . . . ?
C39 C24 C25 C30 -170.43(18) . . . . ?
C30 C25 C26 C27 63.6(2) . . . . ?
C24 C25 C26 C27 -161.27(17) . . . . ?
C25 C26 C27 C28 -60.2(2) . . . . ?
C26 C27 C28 C34 -76.1(2) . . . . ?
C26 C27 C28 C29 51.3(2) . . . . ?
C26 C27 C28 C35 174.55(19) . . . . ?
C27 C28 C29 C31 179.91(19) . . . . ?
C34 C28 C29 C31 -52.4(2) . . . . ?
C35 C28 C29 C31 57.9(2) . . . . ?
C27 C28 C29 C30 -46.9(2) . . . . ?
C34 C28 C29 C30 80.8(2) . . . . ?
C35 C28 C29 C30 -168.98(17) . . . . ?
C22 C21 C30 C38 68.6(3) . . . . ?
C22 C21 C30 C25 -53.8(3) . . . . ?
C22 C21 C30 C29 -168.6(2) . . . . ?
C26 C25 C30 C38 69.2(2) . . . . ?
C24 C25 C30 C38 -65.8(2) . . . . ?
C26 C25 C30 C21 -170.72(18) . . . . ?
C24 C25 C30 C21 54.2(2) . . . . ?
C26 C25 C30 C29 -55.9(2) . . . . ?
C24 C25 C30 C29 169.01(17) . . . . ?
C28 C29 C30 C38 -76.5(2) . . . . ?
C31 C29 C30 C38 54.6(2) . . . . ?
C28 C29 C30 C21 163.33(18) . . . . ?
C31 C29 C30 C21 -65.6(2) . . . . ?
C28 C29 C30 C25 48.4(2) . . . . ?
C31 C29 C30 C25 179.49(18) . . . . ?
C28 C29 C31 C32 34.3(3) . . . . ?
C30 C29 C31 C32 -99.9(2) . . . . ?
C29 C31 C32 C33 -37.9(3) . . . . ?
C31 C32 C33 C34 57.0(3) . . . . ?
C31 C32 C33 C36 -55.7(3) . . . . ?
C32 C33 C34 C28 -70.8(2) . . . . ?
C36 C33 C34 C28 49.8(2) . . . . ?
C27 C28 C34 C33 -162.42(18) . . . . ?
C29 C28 C34 C33 71.0(2) . . . . ?
C35 C28 C34 C33 -46.8(2) . . . . ?
C27 C28 C35 O6 -89.1(2) . . . . ?
C34 C28 C35 O6 152.38(19) . . . . ?
C29 C28 C35 O6 33.9(3) . . . . ?
C27 C28 C35 C36 145.67(18) . . . . ?
C34 C28 C35 C36 27.2(2) . . . . ?
C29 C28 C35 C36 -91.3(2) . . . . ?
C34 C33 C36 O7 82.8(2) . . . . ?
C32 C33 C36 O7 -160.86(18) . . . . ?
C34 C33 C36 C37 -158.4(2) . . . . ?
C32 C33 C36 C37 -42.0(3) . . . . ?
C34 C33 C36 C35 -31.0(2) . . . . ?
C32 C33 C36 C35 85.4(2) . . . . ?
O6 C35 C36 O7 120.0(2) . . . . ?
C28 C35 C36 O7 -110.8(2) . . . . ?
O6 C35 C36 C37 0.7(3) . . . . ?
C28 C35 C36 C37 129.8(2) . . . . ?
O6 C35 C36 C33 -127.1(2) . . . . ?
C28 C35 C36 C33 2.0(2) . . . . ?
O7 C36 C37 O8 61.1(3) . . . . ?
C33 C36 C37 O8 -57.6(3) . . . . ?
C35 C36 C37 O8 -179.0(2) . . . . ?
C23 C24 C40 O9 -176.6(2) . . . . ?
C39 C24 C40 O9 -58.2(3) . . . . ?
C25 C24 C40 O9 61.0(3) . . . . ?
C23 C24 C40 O10 1.8(3) . . . . ?
C39 C24 C40 O10 120.2(2) . . . . ?
C25 C24 C40 O10 -120.6(2) . . . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.026

_shelxl_version_number           2013-4

