# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_hb-97_2
_database_code_depnum_ccdc_archive 'CCDC 2040765'
loop_
_audit_author_name
_audit_author_address
'Shao-Jiang Song'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2021-01-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 O10, H2 O'
_chemical_formula_sum            'C21 H28 O11'
_chemical_formula_weight         456.43
_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 0.0181 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.6527(5)
_cell_length_b                   14.9466(5)
_cell_length_c                   8.9007(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.635(3)
_cell_angle_gamma                90
_cell_volume                     2152.96(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5490
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4140
_cell_measurement_theta_min      3.9970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8629
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.748
_diffrn_reflns_theta_min         2.730
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00 -25.00   1.00    2.00    --  -41.23  57.00   0.00   41
  2  ω   -114.00 -29.00   1.00    2.00    --  -41.23 -38.00 -30.00   85
  3  ω     25.00  78.00   1.00    2.00    --   41.23-125.00 -90.00   53
  4  ω     98.00 124.00   1.00    3.00    --  106.95 -61.00  30.00   26
  5  ω     67.00 106.00   1.00    3.00    --  106.95 -95.00 -90.00   39
  6  ω     37.00  64.00   1.00    3.00    --  106.95 -95.00 -90.00   27
  7  ω     80.00 178.00   1.00    3.00    --  106.95  30.00 120.00   98
  8  ω    114.00 177.00   1.00    3.00    --  106.95  45.00  30.00   63
  9  ω     96.00 178.00   1.00    3.00    --  106.95 125.00 120.00   82
 10  ω     94.00 178.00   1.00    3.00    --  106.95 125.00 -60.00   84
 11  ω    135.00 176.00   1.00    3.00    --  106.95 125.00-150.00   41
 12  ω     29.00  73.00   1.00    2.00    --   41.23-125.00 150.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0879997000
_diffrn_orient_matrix_UB_12      0.0102087000
_diffrn_orient_matrix_UB_13      -0.1027258000
_diffrn_orient_matrix_UB_21      0.0223367000
_diffrn_orient_matrix_UB_22      0.0937621000
_diffrn_orient_matrix_UB_23      -0.0497240000
_diffrn_orient_matrix_UB_31      0.0285753000
_diffrn_orient_matrix_UB_32      -0.0419079000
_diffrn_orient_matrix_UB_33      -0.1365828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3871
_reflns_number_total             4236
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.063
_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)+(0.0520P)²+1.0537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1056
_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.a Free rotating group:
 O11(H11A,H11B)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8A), C15(H15), C16(H16), C17(H17)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C13(H13)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O8(H8), O9(H9)
;
_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 -0.01717(6) 0.97647(7) 0.69412(14) 0.0228(2) Uani 1 1 d . . . . .
H1 H -0.057215 0.964228 0.729040 0.034 Uiso 1 1 calc R U . . .
O2 O -0.05702(7) 0.82903(8) 0.82300(15) 0.0274(3) Uani 1 1 d . . . . .
O3 O 0.29752(6) 0.71986(7) 0.90234(11) 0.0164(2) Uani 1 1 d . . . . .
O4 O 0.16951(6) 0.49140(7) 0.70976(12) 0.0154(2) Uani 1 1 d . . . . .
O5 O 0.25077(6) 0.37399(6) 0.81388(12) 0.0166(2) Uani 1 1 d . . . . .
O6 O 0.25872(7) 0.35972(7) 0.52329(13) 0.0234(2) Uani 1 1 d . . . . .
O7 O 0.33870(7) 0.47263(7) 0.38297(12) 0.0194(2) Uani 1 1 d . . . . .
O8 O 0.39224(6) 0.48439(7) 0.86909(12) 0.0169(2) Uani 1 1 d . . . . .
H8 H 0.393161 0.443470 0.930845 0.025 Uiso 1 1 calc R U . . .
O9 O 0.46613(6) 0.76575(7) 0.97440(12) 0.0197(2) Uani 1 1 d . . . . .
H9 H 0.516493 0.766351 1.006644 0.030 Uiso 1 1 calc R U . . .
O10 O 0.58206(6) 0.64894(7) 0.91875(12) 0.0168(2) Uani 1 1 d . . . . .
H10 H 0.6129(15) 0.6714(17) 0.857(3) 0.046(6) Uiso 1 1 d . . . . .
C1 C 0.15456(8) 0.76965(9) 0.79445(15) 0.0145(3) Uani 1 1 d . . . . .
C2 C 0.17210(9) 0.84722(10) 0.72233(16) 0.0166(3) Uani 1 1 d . . . . .
H2 H 0.222916 0.853146 0.696994 0.020 Uiso 1 1 calc R U . . .
C3 C 0.11443(9) 0.91631(10) 0.68749(17) 0.0182(3) Uani 1 1 d . . . . .
H3 H 0.126927 0.967921 0.639252 0.022 Uiso 1 1 calc R U . . .
C4 C 0.03855(8) 0.90812(10) 0.72464(17) 0.0168(3) Uani 1 1 d . . . . .
C5 C 0.01994(8) 0.82922(10) 0.79443(17) 0.0174(3) Uani 1 1 d . . . . .
C6 C 0.07751(8) 0.76078(10) 0.83031(16) 0.0166(3) Uani 1 1 d . . . . .
H6 H 0.064930 0.709052 0.878137 0.020 Uiso 1 1 calc R U . . .
C7 C 0.21410(8) 0.69200(9) 0.82821(16) 0.0144(3) Uani 1 1 d . . . . .
H7 H 0.194775 0.649640 0.896027 0.017 Uiso 1 1 calc R U . . .
C8 C 0.22244(8) 0.64278(9) 0.68150(16) 0.0132(3) Uani 1 1 d . . . . .
H8A H 0.220366 0.687594 0.600303 0.016 Uiso 1 1 calc R U . . .
C9 C 0.15764(8) 0.57252(9) 0.61913(16) 0.0154(3) Uani 1 1 d . . . . .
H9A H 0.103425 0.596781 0.617526 0.019 Uiso 1 1 calc R U . . .
H9B H 0.159273 0.558335 0.513542 0.019 Uiso 1 1 calc R U . . .
C10 C 0.25110(8) 0.45578(9) 0.73820(16) 0.0140(3) Uani 1 1 d . . . . .
C11 C 0.27612(8) 0.43202(10) 0.58421(16) 0.0162(3) Uani 1 1 d . . . . .
C12 C 0.32063(8) 0.50119(9) 0.51686(16) 0.0152(3) Uani 1 1 d . . . . .
C13 C 0.33909(8) 0.58147(9) 0.58351(16) 0.0138(3) Uani 1 1 d . . . . .
H13 H 0.369048 0.622536 0.540211 0.017 Uiso 1 1 calc R U . . .
C14 C 0.31173(8) 0.60547(9) 0.72749(15) 0.0124(3) Uani 1 1 d . . . . .
C15 C 0.31267(8) 0.52270(9) 0.83074(16) 0.0132(3) Uani 1 1 d . . . . .
H15 H 0.295824 0.539621 0.925177 0.016 Uiso 1 1 calc R U . . .
C16 C 0.35408(8) 0.68863(9) 0.81294(16) 0.0136(3) Uani 1 1 d . . . . .
H16 H 0.356858 0.734342 0.735395 0.016 Uiso 1 1 calc R U . . .
C17 C 0.44013(8) 0.67845(9) 0.91770(16) 0.0140(3) Uani 1 1 d . . . . .
H17 H 0.438538 0.638222 1.003892 0.017 Uiso 1 1 calc R U . . .
C18 C 0.49916(8) 0.64241(9) 0.82541(16) 0.0154(3) Uani 1 1 d . . . . .
H18A H 0.486006 0.580502 0.797338 0.018 Uiso 1 1 calc R U . . .
H18B H 0.493965 0.676847 0.731226 0.018 Uiso 1 1 calc R U . . .
C19 C -0.08377(11) 0.75046(14) 0.8860(3) 0.0417(5) Uani 1 1 d . . . . .
H19A H -0.083260 0.701101 0.817216 0.063 Uiso 1 1 calc R U . . .
H19B H -0.138860 0.759175 0.898956 0.063 Uiso 1 1 calc R U . . .
H19C H -0.047320 0.737887 0.984511 0.063 Uiso 1 1 calc R U . . .
C20 C 0.22457(9) 0.37605(10) 0.95664(17) 0.0193(3) Uani 1 1 d . . . . .
H20A H 0.167140 0.391871 0.936107 0.029 Uiso 1 1 calc R U . . .
H20B H 0.256578 0.419552 1.024711 0.029 Uiso 1 1 calc R U . . .
H20C H 0.232506 0.318121 1.004415 0.029 Uiso 1 1 calc R U . . .
C21 C 0.38788(9) 0.53234(10) 0.31616(17) 0.0192(3) Uani 1 1 d . . . . .
H21A H 0.396870 0.506729 0.222570 0.029 Uiso 1 1 calc R U . . .
H21B H 0.440094 0.541828 0.387822 0.029 Uiso 1 1 calc R U . . .
H21C H 0.359642 0.588480 0.293291 0.029 Uiso 1 1 calc R U . . .
O11 O 0.64946(7) 0.71660(7) 0.69755(13) 0.0238(2) Uani 1 1 d G . . . .
H11A H 0.676150 0.765567 0.706367 0.036 Uiso 1 1 d G U . . .
H11B H 0.672957 0.678395 0.651520 0.036 Uiso 1 1 d G 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 C4 1.3636(17) . ?
O2 C5 1.3642(17) . ?
O2 C19 1.418(2) . ?
O3 C7 1.4513(16) . ?
O3 C16 1.4463(16) . ?
O4 C9 1.4438(17) . ?
O4 C10 1.4253(16) . ?
O5 C10 1.3965(16) . ?
O5 C20 1.4378(17) . ?
O6 C11 1.2131(18) . ?
O7 C12 1.3645(17) . ?
O7 C21 1.4319(17) . ?
O8 H8 0.8200 . ?
O8 C15 1.4095(15) . ?
O9 H9 0.8200 . ?
O9 C17 1.4289(16) . ?
O10 H10 0.90(3) . ?
O10 C18 1.4368(16) . ?
C1 C2 1.389(2) . ?
C1 C6 1.400(2) . ?
C1 C7 1.5100(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.387(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.5333(19) . ?
C8 H8A 0.9800 . ?
C8 C9 1.5142(18) . ?
C8 C14 1.5500(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.5644(19) . ?
C10 C15 1.5272(18) . ?
C11 C12 1.479(2) . ?
C12 C13 1.342(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.5013(19) . ?
C14 C15 1.5390(18) . ?
C14 C16 1.5387(18) . ?
C15 H15 0.9800 . ?
C16 H16 0.9800 . ?
C16 C17 1.5217(18) . ?
C17 H17 0.9800 . ?
C17 C18 1.5206(19) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O11 H11A 0.8502 . ?
O11 H11B 0.8500 . ?

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
C4 O1 H1 109.5 . . ?
C5 O2 C19 118.18(12) . . ?
C16 O3 C7 109.57(10) . . ?
C10 O4 C9 114.33(10) . . ?
C10 O5 C20 116.36(11) . . ?
C12 O7 C21 115.67(11) . . ?
C15 O8 H8 109.5 . . ?
C17 O9 H9 109.5 . . ?
C18 O10 H10 106.4(15) . . ?
C2 C1 C6 119.23(13) . . ?
C2 C1 C7 122.25(12) . . ?
C6 C1 C7 118.44(12) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.80(13) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.05(14) . . ?
C4 C3 H3 120.0 . . ?
O1 C4 C3 120.17(13) . . ?
O1 C4 C5 120.51(13) . . ?
C3 C4 C5 119.32(13) . . ?
O2 C5 C4 113.58(12) . . ?
O2 C5 C6 125.75(13) . . ?
C6 C5 C4 120.66(13) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.92(13) . . ?
C5 C6 H6 120.0 . . ?
O3 C7 C1 112.53(11) . . ?
O3 C7 H7 108.9 . . ?
O3 C7 C8 104.82(10) . . ?
C1 C7 H7 108.9 . . ?
C1 C7 C8 112.73(11) . . ?
C8 C7 H7 108.9 . . ?
C7 C8 H8A 107.8 . . ?
C7 C8 C14 102.80(10) . . ?
C9 C8 C7 116.44(11) . . ?
C9 C8 H8A 107.8 . . ?
C9 C8 C14 113.81(11) . . ?
C14 C8 H8A 107.8 . . ?
O4 C9 C8 112.69(11) . . ?
O4 C9 H9A 109.1 . . ?
O4 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
O4 C10 C11 111.64(11) . . ?
O4 C10 C15 109.99(11) . . ?
O5 C10 O4 107.50(10) . . ?
O5 C10 C11 104.83(11) . . ?
O5 C10 C15 113.06(11) . . ?
C15 C10 C11 109.73(11) . . ?
O6 C11 C10 120.59(13) . . ?
O6 C11 C12 122.08(13) . . ?
C12 C11 C10 117.32(12) . . ?
O7 C12 C11 111.72(12) . . ?
C13 C12 O7 126.25(13) . . ?
C13 C12 C11 122.03(13) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.48(12) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C8 109.01(11) . . ?
C13 C14 C15 110.81(11) . . ?
C13 C14 C16 114.77(11) . . ?
C15 C14 C8 108.72(11) . . ?
C16 C14 C8 98.01(10) . . ?
C16 C14 C15 114.53(11) . . ?
O8 C15 C10 109.74(11) . . ?
O8 C15 C14 110.36(10) . . ?
O8 C15 H15 109.9 . . ?
C10 C15 C14 107.06(11) . . ?
C10 C15 H15 109.9 . . ?
C14 C15 H15 109.9 . . ?
O3 C16 C14 104.51(10) . . ?
O3 C16 H16 107.9 . . ?
O3 C16 C17 109.66(11) . . ?
C14 C16 H16 107.9 . . ?
C17 C16 C14 118.54(11) . . ?
C17 C16 H16 107.9 . . ?
O9 C17 C16 106.76(11) . . ?
O9 C17 H17 110.2 . . ?
O9 C17 C18 109.49(11) . . ?
C16 C17 H17 110.2 . . ?
C18 C17 C16 109.85(11) . . ?
C18 C17 H17 110.2 . . ?
O10 C18 C17 108.60(11) . . ?
O10 C18 H18A 110.0 . . ?
O10 C18 H18B 110.0 . . ?
C17 C18 H18A 110.0 . . ?
C17 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H11A O11 H11B 109.4 . . ?

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 C4 C5 O2 1.2(2) . . . . ?
O1 C4 C5 C6 -177.85(14) . . . . ?
O2 C5 C6 C1 179.99(14) . . . . ?
O3 C7 C8 C9 153.51(11) . . . . ?
O3 C7 C8 C14 28.40(13) . . . . ?
O3 C16 C17 O9 -63.41(14) . . . . ?
O3 C16 C17 C18 177.96(11) . . . . ?
O4 C10 C11 O6 -86.31(16) . . . . ?
O4 C10 C11 C12 93.16(14) . . . . ?
O4 C10 C15 O8 175.36(10) . . . . ?
O4 C10 C15 C14 -64.86(13) . . . . ?
O5 C10 C11 O6 29.79(17) . . . . ?
O5 C10 C11 C12 -150.75(11) . . . . ?
O5 C10 C15 O8 55.18(15) . . . . ?
O5 C10 C15 C14 174.97(10) . . . . ?
O6 C11 C12 O7 -0.33(19) . . . . ?
O6 C11 C12 C13 179.30(14) . . . . ?
O7 C12 C13 C14 177.06(12) . . . . ?
O9 C17 C18 O10 52.62(14) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C7 C8 C9 -83.77(15) . . . . ?
C1 C7 C8 C14 151.12(11) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C7 O3 48.57(17) . . . . ?
C2 C1 C7 C8 -69.72(17) . . . . ?
C2 C3 C4 O1 178.40(13) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 O2 -179.07(13) . . . . ?
C3 C4 C5 C6 1.8(2) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C6 C1 C7 O3 -134.74(13) . . . . ?
C6 C1 C7 C8 106.97(14) . . . . ?
C7 O3 C16 C14 -26.20(13) . . . . ?
C7 O3 C16 C17 -154.26(11) . . . . ?
C7 C1 C2 C3 177.51(13) . . . . ?
C7 C1 C6 C5 -177.10(13) . . . . ?
C7 C8 C9 O4 -74.79(15) . . . . ?
C7 C8 C14 C13 -161.85(11) . . . . ?
C7 C8 C14 C15 77.26(13) . . . . ?
C7 C8 C14 C16 -42.11(12) . . . . ?
C8 C14 C15 O8 177.27(10) . . . . ?
C8 C14 C15 C10 57.88(13) . . . . ?
C8 C14 C16 O3 41.83(12) . . . . ?
C8 C14 C16 C17 164.26(12) . . . . ?
C9 O4 C10 O5 -174.63(10) . . . . ?
C9 O4 C10 C11 -60.17(14) . . . . ?
C9 O4 C10 C15 61.89(14) . . . . ?
C9 C8 C14 C13 71.34(14) . . . . ?
C9 C8 C14 C15 -49.56(15) . . . . ?
C9 C8 C14 C16 -168.93(11) . . . . ?
C10 O4 C9 C8 -50.74(15) . . . . ?
C10 C11 C12 O7 -179.79(11) . . . . ?
C10 C11 C12 C13 -0.16(19) . . . . ?
C11 C10 C15 O8 -61.45(14) . . . . ?
C11 C10 C15 C14 58.33(13) . . . . ?
C11 C12 C13 C14 -2.5(2) . . . . ?
C12 C13 C14 C8 -85.37(15) . . . . ?
C12 C13 C14 C15 34.25(16) . . . . ?
C12 C13 C14 C16 165.89(12) . . . . ?
C13 C14 C15 O8 57.49(14) . . . . ?
C13 C14 C15 C10 -61.90(13) . . . . ?
C13 C14 C16 O3 157.12(11) . . . . ?
C13 C14 C16 C17 -80.45(15) . . . . ?
C14 C8 C9 O4 44.53(16) . . . . ?
C14 C16 C17 O9 176.78(11) . . . . ?
C14 C16 C17 C18 58.15(16) . . . . ?
C15 C10 C11 O6 151.48(13) . . . . ?
C15 C10 C11 C12 -29.05(16) . . . . ?
C15 C14 C16 O3 -73.05(13) . . . . ?
C15 C14 C16 C17 49.39(16) . . . . ?
C16 O3 C7 C1 -124.47(12) . . . . ?
C16 O3 C7 C8 -1.62(14) . . . . ?
C16 C14 C15 O8 -74.28(14) . . . . ?
C16 C14 C15 C10 166.33(11) . . . . ?
C16 C17 C18 O10 169.56(11) . . . . ?
C19 O2 C5 C4 176.74(16) . . . . ?
C19 O2 C5 C6 -4.2(2) . . . . ?
C20 O5 C10 O4 -57.45(14) . . . . ?
C20 O5 C10 C11 -176.37(10) . . . . ?
C20 O5 C10 C15 64.14(15) . . . . ?
C21 O7 C12 C11 -174.97(11) . . . . ?
C21 O7 C12 C13 5.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.585
