# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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).
# 
# 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_210320a_0m
_database_code_depnum_ccdc_archive 'CCDC 2104478'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-05-06
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O7, H2 O'
_chemical_formula_sum            'C20 H22 O8'
_chemical_formula_weight         390.37
_chemical_absolute_configuration ad
_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                   14.1584(16)
_cell_length_b                   4.6034(5)
_cell_length_c                   14.9562(16)
_cell_angle_alpha                90
_cell_angle_beta                 113.249(5)
_cell_angle_gamma                90
_cell_volume                     895.64(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      48.28
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19710
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        52.429
_diffrn_reflns_theta_max         52.429
_diffrn_reflns_theta_min         2.798
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2627
_reflns_number_total             3074
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.5(9)
_refine_ls_extinction_coef       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0851
_refine_ls_restrained_S_all      1.064
_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)+(0.1265P)²+2.0863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2271
_refine_ls_wR_factor_ref         0.2370
_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: 
 O8(H8C,H8D) 
2.b Ternary CH refined with riding coordinates: 
 C9(H9), C10(H10) 
2.c Secondary CH2 refined with riding coordinates: 
 C8(H8A,H8B), C11(H11A,H11B), C18(H18A,H18B) 
2.d Aromatic/amide H refined with riding coordinates: 
 C5(H5), C7(H7) 
2.e Idealised Me refined as rotating group: 
 C1'(H1'A,H1'B,H1'C), C17(H17C,H17A,H17B), C19(H19A,H19B,H19C) 
2.f Idealised tetrahedral OH refined as rotating group: 
 O2(H2) 
;
_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
C1 C -0.8066(6) -0.4231(19) -0.8457(5) 0.0332(17) Uani 1 1 d . . . . .
C1' C -0.7233(7) 0.094(2) -0.6432(6) 0.0406(19) Uani 1 1 d . . . . .
H1'A H -0.677400 -0.029503 -0.590438 0.061 Uiso 1 1 calc R U . . .
H1'B H -0.766584 0.209514 -0.619309 0.061 Uiso 1 1 calc R U . . .
H1'C H -0.682269 0.223237 -0.665605 0.061 Uiso 1 1 calc R U . . .
C2 C -0.7634(6) -0.5898(16) -0.8987(5) 0.0306(17) Uani 1 1 d . . . . .
C3 C -0.6587(6) -0.5753(17) -0.8803(5) 0.0308(16) Uani 1 1 d . . . . .
C4 C -0.5949(6) -0.4005(16) -0.8029(5) 0.0298(16) Uani 1 1 d . . . . .
C5 C -0.6344(6) -0.2373(17) -0.7475(5) 0.0344(18) Uani 1 1 d . . . . .
H5 H -0.590062 -0.123392 -0.694641 0.041 Uiso 1 1 calc R U . . .
C6 C -0.7408(6) -0.2424(18) -0.7704(5) 0.0323(17) Uani 1 1 d . . . . .
C7 C -0.9153(6) -0.4449(19) -0.8649(6) 0.0391(19) Uani 1 1 d . . . . .
H7 H -0.941955 -0.325749 -0.828462 0.047 Uiso 1 1 calc R U . . .
C8 C -0.6177(6) -0.7511(18) -0.9416(5) 0.0341(17) Uani 1 1 d . . . . .
H8A H -0.648547 -0.947641 -0.951267 0.041 Uiso 1 1 calc R U . . .
H8B H -0.638667 -0.658576 -1.006354 0.041 Uiso 1 1 calc R U . . .
C9 C -0.4802(6) -0.4031(17) -0.7780(5) 0.0298(16) Uani 1 1 d . . . . .
H9 H -0.452715 -0.201657 -0.760329 0.036 Uiso 1 1 calc R U . . .
C10 C -0.4619(6) -0.5021(17) -0.8676(5) 0.0332(17) Uani 1 1 d . . . . .
H10 H -0.493978 -0.358511 -0.921277 0.040 Uiso 1 1 calc R U . . .
C11 C -0.4247(6) -0.6056(17) -0.6920(5) 0.0328(17) Uani 1 1 d . . . . .
H11A H -0.411301 -0.499637 -0.630599 0.039 Uiso 1 1 calc R U . . .
H11B H -0.469969 -0.772319 -0.694916 0.039 Uiso 1 1 calc R U . . .
C12 C -0.3250(6) -0.7170(17) -0.6912(5) 0.0321(17) Uani 1 1 d . . . . .
C13 C -0.2584(6) -0.8860(17) -0.6101(6) 0.0351(18) Uani 1 1 d . . . . .
C14 C -0.1390(6) -0.9405(18) -0.6892(6) 0.0378(19) Uani 1 1 d . . . . .
C15 C -0.1992(6) -0.7790(18) -0.7665(5) 0.0338(17) Uani 1 1 d . . . . .
C16 C -0.2954(6) -0.6767(16) -0.7668(5) 0.0333(18) Uani 1 1 d . . . . .
C17 C -0.1715(7) -0.706(2) -0.8522(6) 0.045(2) Uani 1 1 d . . . . .
H17C H -0.220230 -0.801396 -0.910932 0.068 Uiso 1 1 calc R U . . .
H17A H -0.101771 -0.775260 -0.838946 0.068 Uiso 1 1 calc R U . . .
H17B H -0.174655 -0.495521 -0.862052 0.068 Uiso 1 1 calc R U . . .
C18 C -0.0389(7) -1.089(2) -0.6711(6) 0.045(2) Uani 1 1 d . . . . .
H18A H -0.021464 -1.061963 -0.728464 0.054 Uiso 1 1 calc R U . . .
H18B H -0.046633 -1.300001 -0.663015 0.054 Uiso 1 1 calc R U . . .
C19 C 0.0495(7) -0.971(2) -0.5801(7) 0.053(2) Uani 1 1 d . . . . .
H19A H 0.030541 -0.984592 -0.523921 0.079 Uiso 1 1 calc R U . . .
H19B H 0.062761 -0.768017 -0.590751 0.079 Uiso 1 1 calc R U . . .
H19C H 0.111659 -1.086634 -0.567669 0.079 Uiso 1 1 calc R U . . .
O1 O -0.9750(4) -0.6113(14) -0.9266(4) 0.0453(15) Uani 1 1 d . . . . .
O2 O -0.8216(4) -0.7663(13) -0.9722(4) 0.0374(13) Uani 1 1 d . . . . .
H2 H -0.882528 -0.764761 -0.976436 0.056 Uiso 1 1 calc R U . . .
O3 O -0.7867(4) -0.0846(12) -0.7218(4) 0.0386(14) Uani 1 1 d . . . . .
O4 O -0.5075(4) -0.7774(12) -0.8987(4) 0.0346(13) Uani 1 1 d . . . . .
O5 O -0.3555(4) -0.5315(12) -0.8498(3) 0.0339(12) Uani 1 1 d . . . . .
O6 O -0.1691(4) -0.9940(13) -0.6138(4) 0.0392(14) Uani 1 1 d . . . . .
O7 O -0.2744(4) -0.9540(14) -0.5375(4) 0.0429(15) Uani 1 1 d . . . . .
O8 O -0.5379(4) -0.5348(12) -0.4784(4) 0.0397(13) Uani 1 1 d G . . . .
H8C H -0.517578 -0.373894 -0.495686 0.060 Uiso 1 1 d G U . . .
H8D H -0.593897 -0.487619 -0.471043 0.060 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
C1 C2 1.405(11) . ?
C1 C6 1.414(11) . ?
C1 C7 1.454(11) . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C1' O3 1.424(10) . ?
C2 C3 1.398(10) . ?
C2 O2 1.354(9) . ?
C3 C4 1.406(11) . ?
C3 C8 1.502(10) . ?
C4 C5 1.390(11) . ?
C4 C9 1.516(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.407(11) . ?
C6 O3 1.361(9) . ?
C7 H7 0.9500 . ?
C7 O1 1.239(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 O4 1.439(9) . ?
C9 H9 1.0000 . ?
C9 C10 1.532(10) . ?
C9 C11 1.531(10) . ?
C10 H10 1.0000 . ?
C10 O4 1.415(10) . ?
C10 O5 1.428(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.497(11) . ?
C12 C13 1.436(11) . ?
C12 C16 1.364(11) . ?
C13 O6 1.380(9) . ?
C13 O7 1.235(10) . ?
C14 C15 1.356(11) . ?
C14 C18 1.498(12) . ?
C14 O6 1.376(10) . ?
C15 C16 1.440(11) . ?
C15 C17 1.519(11) . ?
C16 O5 1.370(9) . ?
C17 H17C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.539(12) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O2 H2 0.8400 . ?
O8 H8C 0.8701 . ?
O8 H8D 0.8695 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.3(7) . . ?
C2 C1 C7 120.9(7) . . ?
C6 C1 C7 120.8(7) . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
O3 C1' H1'A 109.5 . . ?
O3 C1' H1'B 109.5 . . ?
O3 C1' H1'C 109.5 . . ?
C3 C2 C1 121.8(7) . . ?
O2 C2 C1 121.7(7) . . ?
O2 C2 C3 116.5(6) . . ?
C2 C3 C4 118.5(7) . . ?
C2 C3 C8 119.3(7) . . ?
C4 C3 C8 122.2(7) . . ?
C3 C4 C9 118.4(6) . . ?
C5 C4 C3 121.4(7) . . ?
C5 C4 C9 120.1(7) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.3(7) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 120.7(7) . . ?
O3 C6 C1 115.8(7) . . ?
O3 C6 C5 123.5(7) . . ?
C1 C7 H7 118.4 . . ?
O1 C7 C1 123.2(8) . . ?
O1 C7 H7 118.4 . . ?
C3 C8 H8A 109.1 . . ?
C3 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O4 C8 C3 112.7(6) . . ?
O4 C8 H8A 109.1 . . ?
O4 C8 H8B 109.1 . . ?
C4 C9 H9 109.0 . . ?
C4 C9 C10 108.8(6) . . ?
C4 C9 C11 110.9(6) . . ?
C10 C9 H9 109.0 . . ?
C11 C9 H9 109.0 . . ?
C11 C9 C10 110.2(6) . . ?
C9 C10 H10 108.9 . . ?
O4 C10 C9 109.9(6) . . ?
O4 C10 H10 108.9 . . ?
O4 C10 O5 106.7(6) . . ?
O5 C10 C9 113.3(6) . . ?
O5 C10 H10 108.9 . . ?
C9 C11 H11A 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C9 112.6(6) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C13 C12 C11 119.7(7) . . ?
C16 C12 C11 122.9(7) . . ?
C16 C12 C13 117.4(7) . . ?
O6 C13 C12 117.9(7) . . ?
O7 C13 C12 126.4(7) . . ?
O7 C13 O6 115.7(7) . . ?
C15 C14 C18 129.5(7) . . ?
C15 C14 O6 120.2(7) . . ?
O6 C14 C18 110.3(7) . . ?
C14 C15 C16 117.3(7) . . ?
C14 C15 C17 123.7(7) . . ?
C16 C15 C17 119.0(7) . . ?
C12 C16 C15 123.5(7) . . ?
C12 C16 O5 122.2(7) . . ?
O5 C16 C15 114.3(6) . . ?
C15 C17 H17C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17C C17 H17A 109.5 . . ?
H17C C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C18 H18A 109.1 . . ?
C14 C18 H18B 109.1 . . ?
C14 C18 C19 112.4(7) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 O2 H2 109.5 . . ?
C6 O3 C1' 118.1(6) . . ?
C10 O4 C8 110.2(6) . . ?
C16 O5 C10 116.6(6) . . ?
C14 O6 C13 123.6(6) . . ?
H8C O8 H8D 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
_geom_hbond_publ_flag
O2 H2 O1 0.84 1.88 2.620(8) 145.9 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 3.6(11) . . . . ?
C1 C2 C3 C8 -177.9(7) . . . . ?
C1 C6 O3 C1' 178.0(7) . . . . ?
C2 C1 C6 C5 -1.9(11) . . . . ?
C2 C1 C6 O3 179.7(7) . . . . ?
C2 C1 C7 O1 1.2(13) . . . . ?
C2 C3 C4 C5 -2.1(11) . . . . ?
C2 C3 C4 C9 175.3(7) . . . . ?
C2 C3 C8 O4 -164.1(6) . . . . ?
C3 C4 C5 C6 -1.3(11) . . . . ?
C3 C4 C9 C10 22.7(9) . . . . ?
C3 C4 C9 C11 -98.6(7) . . . . ?
C3 C8 O4 C10 -48.0(8) . . . . ?
C4 C3 C8 O4 14.4(10) . . . . ?
C4 C5 C6 C1 3.3(11) . . . . ?
C4 C5 C6 O3 -178.4(7) . . . . ?
C4 C9 C10 O4 -56.6(8) . . . . ?
C4 C9 C10 O5 -175.9(6) . . . . ?
C4 C9 C11 C12 155.1(6) . . . . ?
C5 C4 C9 C10 -159.8(7) . . . . ?
C5 C4 C9 C11 78.8(9) . . . . ?
C5 C6 O3 C1' -0.4(11) . . . . ?
C6 C1 C2 C3 -1.6(11) . . . . ?
C6 C1 C2 O2 -179.6(7) . . . . ?
C6 C1 C7 O1 -176.1(8) . . . . ?
C7 C1 C2 C3 -179.0(7) . . . . ?
C7 C1 C2 O2 3.1(12) . . . . ?
C7 C1 C6 C5 175.5(8) . . . . ?
C7 C1 C6 O3 -2.9(11) . . . . ?
C8 C3 C4 C5 179.4(7) . . . . ?
C8 C3 C4 C9 -3.2(10) . . . . ?
C9 C4 C5 C6 -178.7(7) . . . . ?
C9 C10 O4 C8 71.5(7) . . . . ?
C9 C10 O5 C16 46.6(9) . . . . ?
C9 C11 C12 C13 173.7(7) . . . . ?
C9 C11 C12 C16 -9.3(10) . . . . ?
C10 C9 C11 C12 34.6(9) . . . . ?
C11 C9 C10 O4 65.1(8) . . . . ?
C11 C9 C10 O5 -54.1(8) . . . . ?
C11 C12 C13 O6 177.6(7) . . . . ?
C11 C12 C13 O7 0.1(12) . . . . ?
C11 C12 C16 C15 179.1(7) . . . . ?
C11 C12 C16 O5 -0.3(11) . . . . ?
C12 C13 O6 C14 2.2(11) . . . . ?
C12 C16 O5 C10 -18.8(10) . . . . ?
C13 C12 C16 C15 -3.9(11) . . . . ?
C13 C12 C16 O5 176.7(7) . . . . ?
C14 C15 C16 C12 4.6(12) . . . . ?
C14 C15 C16 O5 -175.9(7) . . . . ?
C15 C14 C18 C19 118.2(10) . . . . ?
C15 C14 O6 C13 -1.5(12) . . . . ?
C15 C16 O5 C10 161.7(7) . . . . ?
C16 C12 C13 O6 0.4(11) . . . . ?
C16 C12 C13 O7 -177.1(8) . . . . ?
C17 C15 C16 C12 -176.4(8) . . . . ?
C17 C15 C16 O5 3.0(11) . . . . ?
C18 C14 C15 C16 176.3(8) . . . . ?
C18 C14 C15 C17 -2.6(14) . . . . ?
C18 C14 O6 C13 -179.9(7) . . . . ?
O2 C2 C3 C4 -178.4(6) . . . . ?
O2 C2 C3 C8 0.2(10) . . . . ?
O4 C10 O5 C16 -74.5(7) . . . . ?
O5 C10 O4 C8 -165.4(5) . . . . ?
O6 C14 C15 C16 -1.8(12) . . . . ?
O6 C14 C15 C17 179.3(8) . . . . ?
O6 C14 C18 C19 -63.5(9) . . . . ?
O7 C13 O6 C14 180.0(7) . . . . ?

_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_210324a_0m
_database_code_depnum_ccdc_archive 'CCDC 2104481'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-04-23
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 O8'
_chemical_formula_sum            'C21 H22 O8'
_chemical_formula_weight         402.38
_chemical_absolute_configuration ad
_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      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.5507(10)
_cell_length_b                   17.161(4)
_cell_length_c                   48.011(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3749.4(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9704
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      49.71
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.7498
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1566 before and 0.0754 after correction. 
The Ratio of minimum to maximum transmission is 0.8870. 
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    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            53389
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        50.666
_diffrn_reflns_theta_max         50.666
_diffrn_reflns_theta_min         1.601
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                4872
_reflns_number_total             5725
_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         5725
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.058
_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)+(0.0559P)²+1.6945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1113
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_olex2_refinement_description    
; 
1. Twinned data refinement 
 Scales: 0.7(3) 
 0.3(3) 
2. 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 
3.a Ternary CH refined with riding coordinates: 
 C9A(H9A), C10A(H10A), C8A(H8A), C8(H8), C9(H9), C10(H10) 
3.b Secondary CH2 refined with riding coordinates: 
 C18A(H18A,H18B), C11A(H11A,H11B), C18(H18C,H18D), C11(H11C,H11D) 
3.c Aromatic/amide H refined with riding coordinates: 
 C5A(H5A), C7A(H7A), C7(H7), C5(H5) 
3.d Idealised Me refined as rotating group: 
 C19A(H19A,H19B,H19C), C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,H2BC), C17A(H17A, 
 H17B,H17C), C19(H19D,H19E,H19F), C1'(H1'A,H1'B,H1'C), C17(H17D,H17E,H17F), 
 C2'(H2'A,H2'B,H2'C) 
3.e Idealised tetrahedral OH refined as rotating group: 
 O2A(H2A), O2(H2) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O6A O 0.8682(7) 0.71237(15) 0.70060(5) 0.0260(7) Uani 1 1 d . . . . .
O3A O 0.3264(7) 0.42228(16) 0.80028(5) 0.0317(7) Uani 1 1 d . . . . .
O4A O 0.8759(7) 0.75173(15) 0.78319(5) 0.0310(7) Uani 1 1 d . . . . .
O5A O 1.0715(7) 0.69261(15) 0.74332(5) 0.0260(7) Uani 1 1 d . . . . .
O7A O 1.3540(7) 0.57713(15) 0.64828(5) 0.0259(7) Uani 1 1 d . . . . .
O8A O 1.2958(7) 0.47225(15) 0.67475(5) 0.0295(7) Uani 1 1 d . . . . .
O2A O 0.9842(8) 0.62444(17) 0.82590(5) 0.0353(8) Uani 1 1 d . . . . .
H2A H 0.958103 0.603682 0.841556 0.053 Uiso 1 1 calc R U . . .
O1A O 0.7777(9) 0.52519(19) 0.86130(6) 0.0489(10) Uani 1 1 d . . . . .
C19A C 1.2770(15) 0.6639(4) 0.59129(9) 0.070(2) Uani 1 1 d . . . . .
H19A H 1.382511 0.681068 0.574589 0.105 Uiso 1 1 calc R U . . .
H19B H 1.093899 0.693527 0.593106 0.105 Uiso 1 1 calc R U . . .
H19C H 1.231620 0.608246 0.589720 0.105 Uiso 1 1 calc R U . . .
C18A C 1.4659(11) 0.6775(2) 0.61657(7) 0.0302(11) Uani 1 1 d . . . . .
H18A H 1.648965 0.646710 0.614827 0.036 Uiso 1 1 calc R U . . .
H18B H 1.520709 0.733264 0.617489 0.036 Uiso 1 1 calc R U . . .
C14A C 1.3117(10) 0.6551(2) 0.64287(8) 0.0241(10) Uani 1 1 d . . . . .
C15A C 1.1512(10) 0.7003(2) 0.65974(7) 0.0249(10) Uani 1 1 d . . . . .
C16A C 1.0183(10) 0.6633(2) 0.68344(7) 0.0234(9) Uani 1 1 d . . . . .
C9A C 0.8035(10) 0.6848(2) 0.72810(8) 0.0241(9) Uani 1 1 d . . . . .
H9A H 0.650594 0.719063 0.736678 0.029 Uiso 1 1 calc R U . . .
C10A C 0.6990(10) 0.6018(2) 0.72879(7) 0.0226(9) Uani 1 1 d . . . . .
H10A H 0.499112 0.599484 0.720177 0.027 Uiso 1 1 calc R U . . .
C4A C 0.6745(10) 0.5764(2) 0.75888(7) 0.0221(9) Uani 1 1 d . . . . .
C5A C 0.5058(10) 0.5108(2) 0.76520(7) 0.0248(10) Uani 1 1 d . . . . .
H5A H 0.403342 0.484084 0.750860 0.030 Uiso 1 1 calc R U . . .
C6A C 0.4885(11) 0.4850(2) 0.79238(8) 0.0255(10) Uani 1 1 d . . . . .
C1A C 0.6497(11) 0.5226(2) 0.81369(7) 0.0274(10) Uani 1 1 d . . . . .
C7A C 0.6339(12) 0.4948(3) 0.84231(8) 0.0361(12) Uani 1 1 d . . . . .
H7A H 0.509365 0.451978 0.846537 0.043 Uiso 1 1 calc R U . . .
C1B C 0.1544(11) 0.3860(2) 0.77895(8) 0.0318(11) Uani 1 1 d . . . . .
H1BA H 0.285120 0.363402 0.764876 0.048 Uiso 1 1 calc R U . . .
H1BB H 0.027033 0.424978 0.770188 0.048 Uiso 1 1 calc R U . . .
H1BC H 0.033328 0.344752 0.787170 0.048 Uiso 1 1 calc R U . . .
C2A C 0.8220(10) 0.5872(2) 0.80677(8) 0.0265(10) Uani 1 1 d . . . . .
C3A C 0.8331(10) 0.6154(2) 0.77917(7) 0.0247(10) Uani 1 1 d . . . . .
C8A C 1.0195(11) 0.6852(2) 0.77272(7) 0.0256(10) Uani 1 1 d . . . . .
H8A H 1.212710 0.679383 0.782431 0.031 Uiso 1 1 calc R U . . .
C2B C 1.0722(13) 0.8156(2) 0.78838(9) 0.0388(13) Uani 1 1 d . . . . .
H2BA H 1.163630 0.831941 0.770844 0.058 Uiso 1 1 calc R U . . .
H2BB H 1.225109 0.799170 0.801502 0.058 Uiso 1 1 calc R U . . .
H2BC H 0.961961 0.859321 0.796338 0.058 Uiso 1 1 calc R U . . .
C11A C 0.9021(10) 0.5465(2) 0.71276(7) 0.0236(10) Uani 1 1 d . . . . .
H11A H 1.056672 0.526886 0.725461 0.028 Uiso 1 1 calc R U . . .
H11B H 0.787115 0.501222 0.706091 0.028 Uiso 1 1 calc R U . . .
C12A C 1.0433(10) 0.5859(2) 0.68844(7) 0.0221(9) Uani 1 1 d . . . . .
C13A C 1.2303(10) 0.5403(2) 0.67110(7) 0.0236(10) Uani 1 1 d . . . . .
C17A C 1.1071(12) 0.7864(2) 0.65503(9) 0.0348(12) Uani 1 1 d . . . . .
H17A H 1.212424 0.815762 0.669415 0.052 Uiso 1 1 calc R U . . .
H17B H 0.897050 0.798678 0.655991 0.052 Uiso 1 1 calc R U . . .
H17C H 1.183257 0.800705 0.636637 0.052 Uiso 1 1 calc R U . . .
O5 O 0.7845(7) 0.54126(14) 0.52865(5) 0.0223(7) Uani 1 1 d . . . . .
O6 O 1.0108(7) 0.47849(14) 0.56465(5) 0.0223(6) Uani 1 1 d . . . . .
O3 O 1.4345(7) 0.43157(16) 0.41801(5) 0.0303(8) Uani 1 1 d . . . . .
O1 O 1.0344(8) 0.62883(17) 0.39882(5) 0.0401(9) Uani 1 1 d . . . . .
O7 O 0.5045(7) 0.28685(15) 0.57895(5) 0.0246(7) Uani 1 1 d . . . . .
O8 O 0.5262(8) 0.24843(16) 0.53499(5) 0.0320(7) Uani 1 1 d . . . . .
O4 O 0.9973(7) 0.65548(14) 0.51130(5) 0.0269(7) Uani 1 1 d . . . . .
O2 O 0.8532(8) 0.64163(15) 0.44997(5) 0.0315(8) Uani 1 1 d . . . . .
H2 H 0.863001 0.652064 0.432897 0.047 Uiso 1 1 calc R U . . .
C7 C 1.1649(12) 0.5684(2) 0.40596(8) 0.0330(11) Uani 1 1 d . . . . .
H7 H 1.279752 0.541890 0.392413 0.040 Uiso 1 1 calc R U . . .
C1 C 1.1516(10) 0.5362(2) 0.43368(7) 0.0242(10) Uani 1 1 d . . . . .
C2 C 0.9983(11) 0.5750(2) 0.45507(7) 0.0242(9) Uani 1 1 d . . . . .
C3 C 0.9972(10) 0.5454(2) 0.48230(7) 0.0215(9) Uani 1 1 d . . . . .
C8 C 0.8307(11) 0.5890(2) 0.50447(7) 0.0236(10) Uani 1 1 d . . . . .
H8 H 0.636101 0.605763 0.496854 0.028 Uiso 1 1 calc R U . . .
C9 C 1.0546(10) 0.5053(2) 0.53680(7) 0.0226(10) Uani 1 1 d . . . . .
H9 H 1.214538 0.545233 0.536674 0.027 Uiso 1 1 calc R U . . .
C16 C 0.8508(10) 0.4117(2) 0.56790(7) 0.0201(9) Uani 1 1 d . . . . .
C15 C 0.7497(10) 0.3991(2) 0.59591(7) 0.0216(10) Uani 1 1 d . . . . .
C14 C 0.5773(10) 0.3369(2) 0.60036(7) 0.0218(10) Uani 1 1 d . . . . .
C18 C 0.4375(11) 0.3101(2) 0.62678(7) 0.0274(10) Uani 1 1 d . . . . .
H18C H 0.229747 0.296575 0.623042 0.033 Uiso 1 1 calc R U . . .
H18D H 0.439797 0.353383 0.640399 0.033 Uiso 1 1 calc R U . . .
C19 C 0.5914(11) 0.2395(2) 0.63955(8) 0.0327(11) Uani 1 1 d . . . . .
H19D H 0.602242 0.197593 0.625732 0.049 Uiso 1 1 calc R U . . .
H19E H 0.480271 0.221501 0.655805 0.049 Uiso 1 1 calc R U . . .
H19F H 0.790448 0.254202 0.645313 0.049 Uiso 1 1 calc R U . . .
C1' C 1.6097(11) 0.3636(2) 0.42325(8) 0.0300(11) Uani 1 1 d . . . . .
H1'A H 1.716221 0.349263 0.406267 0.045 Uiso 1 1 calc R U . . .
H1'B H 1.481910 0.320431 0.428886 0.045 Uiso 1 1 calc R U . . .
H1'C H 1.750526 0.374728 0.438168 0.045 Uiso 1 1 calc R U . . .
C6 C 1.2980(10) 0.4657(2) 0.43995(7) 0.0246(10) Uani 1 1 d . . . . .
C17 C 0.8446(11) 0.4552(2) 0.61831(7) 0.0286(11) Uani 1 1 d . . . . .
H17D H 1.059614 0.455947 0.619425 0.043 Uiso 1 1 calc R U . . .
H17E H 0.763126 0.438636 0.636249 0.043 Uiso 1 1 calc R U . . .
H17F H 0.772776 0.507567 0.613818 0.043 Uiso 1 1 calc R U . . .
C13 C 0.6098(10) 0.2965(2) 0.55183(7) 0.0245(10) Uani 1 1 d . . . . .
C12 C 0.7932(10) 0.3620(2) 0.54672(7) 0.0201(9) Uani 1 1 d . . . . .
C11 C 0.9094(10) 0.3736(2) 0.51771(7) 0.0238(10) Uani 1 1 d . . . . .
H11C H 0.743870 0.384671 0.504936 0.029 Uiso 1 1 calc R U . . .
H11D H 1.006106 0.325044 0.511350 0.029 Uiso 1 1 calc R U . . .
C10 C 1.1311(10) 0.4412(2) 0.51659(7) 0.0218(10) Uani 1 1 d . . . . .
H10 H 1.330428 0.420588 0.521367 0.026 Uiso 1 1 calc R U . . .
C4 C 1.1422(10) 0.4761(2) 0.48758(7) 0.0204(9) Uani 1 1 d . . . . .
C5 C 1.2917(10) 0.4356(2) 0.46659(7) 0.0228(9) Uani 1 1 d . . . . .
H5 H 1.388000 0.387874 0.470666 0.027 Uiso 1 1 calc R U . . .
C2' C 0.8393(12) 0.7093(2) 0.52855(8) 0.0320(11) Uani 1 1 d . . . . .
H2'A H 0.647980 0.720604 0.520088 0.048 Uiso 1 1 calc R U . . .
H2'B H 0.952022 0.757745 0.530301 0.048 Uiso 1 1 calc R U . . .
H2'C H 0.809891 0.686458 0.547043 0.048 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
O6A C16A 1.362(5) . ?
O6A C9A 1.433(5) . ?
O3A C6A 1.359(5) . ?
O3A C1B 1.432(5) . ?
O4A C8A 1.409(5) . ?
O4A C2B 1.436(6) . ?
O5A C9A 1.428(5) . ?
O5A C8A 1.437(4) . ?
O7A C14A 1.377(5) . ?
O7A C13A 1.384(5) . ?
O8A C13A 1.218(5) . ?
O2A H2A 0.8400 . ?
O2A C2A 1.340(5) . ?
O1A C7A 1.237(6) . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C19A C18A 1.506(7) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C18A C14A 1.495(6) . ?
C14A C15A 1.338(6) . ?
C15A C16A 1.437(5) . ?
C15A C17A 1.509(5) . ?
C16A C12A 1.354(5) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.502(5) . ?
C10A H10A 1.0000 . ?
C10A C4A 1.513(5) . ?
C10A C11A 1.532(6) . ?
C4A C5A 1.395(6) . ?
C4A C3A 1.385(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.380(5) . ?
C6A C1A 1.414(6) . ?
C1A C7A 1.457(6) . ?
C1A C2A 1.398(6) . ?
C7A H7A 0.9500 . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C2A C3A 1.411(5) . ?
C3A C8A 1.500(6) . ?
C8A H8A 1.0000 . ?
C2B H2BA 0.9800 . ?
C2B H2BB 0.9800 . ?
C2B H2BC 0.9800 . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11A C12A 1.494(5) . ?
C12A C13A 1.425(6) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
O5 C8 1.437(4) . ?
O5 C9 1.430(5) . ?
O6 C9 1.428(4) . ?
O6 C16 1.366(5) . ?
O3 C1' 1.435(5) . ?
O3 C6 1.356(5) . ?
O1 C7 1.244(5) . ?
O7 C14 1.380(4) . ?
O7 C13 1.397(4) . ?
O8 C13 1.217(5) . ?
O4 C8 1.408(5) . ?
O4 C2' 1.434(5) . ?
O2 H2 0.8400 . ?
O2 C2 1.342(5) . ?
C7 H7 0.9500 . ?
C7 C1 1.441(5) . ?
C1 C2 1.409(6) . ?
C1 C6 1.415(6) . ?
C2 C3 1.403(5) . ?
C3 C8 1.506(6) . ?
C3 C4 1.384(5) . ?
C8 H8 1.0000 . ?
C9 H9 1.0000 . ?
C9 C10 1.508(5) . ?
C16 C15 1.438(5) . ?
C16 C12 1.353(5) . ?
C15 C14 1.341(6) . ?
C15 C17 1.507(5) . ?
C14 C18 1.492(5) . ?
C18 H18C 0.9900 . ?
C18 H18D 0.9900 . ?
C18 C19 1.527(6) . ?
C19 H19D 0.9800 . ?
C19 H19E 0.9800 . ?
C19 H19F 0.9800 . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C6 C5 1.379(5) . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C13 C12 1.421(6) . ?
C12 C11 1.503(5) . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 C10 1.539(6) . ?
C10 H10 1.0000 . ?
C10 C4 1.517(5) . ?
C4 C5 1.400(5) . ?
C5 H5 0.9500 . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16A O6A C9A 117.1(3) . . ?
C6A O3A C1B 116.2(3) . . ?
C8A O4A C2B 113.1(4) . . ?
C9A O5A C8A 110.7(3) . . ?
C14A O7A C13A 122.4(3) . . ?
C2A O2A H2A 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C18A C19A H19A 109.5 . . ?
C18A C19A H19B 109.5 . . ?
C18A C19A H19C 109.5 . . ?
C19A C18A H18A 109.2 . . ?
C19A C18A H18B 109.2 . . ?
H18A C18A H18B 107.9 . . ?
C14A C18A C19A 111.9(4) . . ?
C14A C18A H18A 109.2 . . ?
C14A C18A H18B 109.2 . . ?
O7A C14A C18A 110.1(3) . . ?
C15A C14A O7A 121.7(3) . . ?
C15A C14A C18A 128.2(4) . . ?
C14A C15A C16A 116.9(3) . . ?
C14A C15A C17A 123.3(4) . . ?
C16A C15A C17A 119.7(4) . . ?
O6A C16A C15A 114.6(3) . . ?
C12A C16A O6A 122.8(3) . . ?
C12A C16A C15A 122.6(4) . . ?
O6A C9A H9A 109.2 . . ?
O6A C9A C10A 113.5(3) . . ?
O5A C9A O6A 105.4(3) . . ?
O5A C9A H9A 109.2 . . ?
O5A C9A C10A 110.4(3) . . ?
C10A C9A H9A 109.2 . . ?
C9A C10A H10A 108.4 . . ?
C9A C10A C4A 108.5(3) . . ?
C9A C10A C11A 112.6(4) . . ?
C4A C10A H10A 108.4 . . ?
C4A C10A C11A 110.2(3) . . ?
C11A C10A H10A 108.4 . . ?
C5A C4A C10A 118.7(4) . . ?
C3A C4A C10A 119.6(4) . . ?
C3A C4A C5A 121.5(3) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A C4A 119.7(4) . . ?
C6A C5A H5A 120.1 . . ?
O3A C6A C5A 123.3(4) . . ?
O3A C6A C1A 116.2(3) . . ?
C5A C6A C1A 120.5(4) . . ?
C6A C1A C7A 120.5(4) . . ?
C2A C1A C6A 118.7(3) . . ?
C2A C1A C7A 120.8(4) . . ?
O1A C7A C1A 122.1(5) . . ?
O1A C7A H7A 119.0 . . ?
C1A C7A H7A 119.0 . . ?
O3A C1B H1BA 109.5 . . ?
O3A C1B H1BB 109.5 . . ?
O3A C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
O2A C2A C1A 121.6(3) . . ?
O2A C2A C3A 117.4(4) . . ?
C1A C2A C3A 121.0(4) . . ?
C4A C3A C2A 118.5(4) . . ?
C4A C3A C8A 122.4(3) . . ?
C2A C3A C8A 119.2(4) . . ?
O4A C8A O5A 110.8(3) . . ?
O4A C8A C3A 108.2(3) . . ?
O4A C8A H8A 108.8 . . ?
O5A C8A C3A 111.5(3) . . ?
O5A C8A H8A 108.8 . . ?
C3A C8A H8A 108.8 . . ?
O4A C2B H2BA 109.5 . . ?
O4A C2B H2BB 109.5 . . ?
O4A C2B H2BC 109.5 . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
C10A C11A H11A 109.2 . . ?
C10A C11A H11B 109.2 . . ?
H11A C11A H11B 107.9 . . ?
C12A C11A C10A 111.8(3) . . ?
C12A C11A H11A 109.2 . . ?
C12A C11A H11B 109.2 . . ?
C16A C12A C11A 123.1(4) . . ?
C16A C12A C13A 119.0(4) . . ?
C13A C12A C11A 117.7(3) . . ?
O7A C13A C12A 117.1(3) . . ?
O8A C13A O7A 116.9(4) . . ?
O8A C13A C12A 126.0(4) . . ?
C15A C17A H17A 109.5 . . ?
C15A C17A H17B 109.5 . . ?
C15A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C9 O5 C8 110.0(3) . . ?
C16 O6 C9 116.8(3) . . ?
C6 O3 C1' 118.0(3) . . ?
C14 O7 C13 122.5(3) . . ?
C8 O4 C2' 112.7(3) . . ?
C2 O2 H2 109.5 . . ?
O1 C7 H7 118.2 . . ?
O1 C7 C1 123.6(4) . . ?
C1 C7 H7 118.2 . . ?
C2 C1 C7 120.9(4) . . ?
C2 C1 C6 118.9(3) . . ?
C6 C1 C7 120.3(4) . . ?
O2 C2 C1 120.8(3) . . ?
O2 C2 C3 118.5(3) . . ?
C3 C2 C1 120.7(4) . . ?
C2 C3 C8 118.7(3) . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 C8 122.5(3) . . ?
O5 C8 C3 111.2(3) . . ?
O5 C8 H8 109.3 . . ?
O4 C8 O5 110.6(3) . . ?
O4 C8 C3 107.2(4) . . ?
O4 C8 H8 109.3 . . ?
C3 C8 H8 109.3 . . ?
O5 C9 H9 109.1 . . ?
O5 C9 C10 109.7(3) . . ?
O6 C9 O5 106.0(3) . . ?
O6 C9 H9 109.1 . . ?
O6 C9 C10 113.6(3) . . ?
C10 C9 H9 109.1 . . ?
O6 C16 C15 113.8(3) . . ?
C12 C16 O6 123.1(3) . . ?
C12 C16 C15 123.1(4) . . ?
C16 C15 C17 118.6(4) . . ?
C14 C15 C16 117.1(3) . . ?
C14 C15 C17 124.2(3) . . ?
O7 C14 C18 109.8(3) . . ?
C15 C14 O7 121.1(3) . . ?
C15 C14 C18 129.1(3) . . ?
C14 C18 H18C 109.0 . . ?
C14 C18 H18D 109.0 . . ?
C14 C18 C19 113.0(4) . . ?
H18C C18 H18D 107.8 . . ?
C19 C18 H18C 109.0 . . ?
C19 C18 H18D 109.0 . . ?
C18 C19 H19D 109.5 . . ?
C18 C19 H19E 109.5 . . ?
C18 C19 H19F 109.5 . . ?
H19D C19 H19E 109.5 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
O3 C1' H1'A 109.5 . . ?
O3 C1' H1'B 109.5 . . ?
O3 C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
O3 C6 C1 114.8(3) . . ?
O3 C6 C5 124.7(4) . . ?
C5 C6 C1 120.5(4) . . ?
C15 C17 H17D 109.5 . . ?
C15 C17 H17E 109.5 . . ?
C15 C17 H17F 109.5 . . ?
H17D C17 H17E 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
O7 C13 C12 117.2(3) . . ?
O8 C13 O7 115.6(4) . . ?
O8 C13 C12 127.3(3) . . ?
C16 C12 C13 118.9(3) . . ?
C16 C12 C11 123.0(4) . . ?
C13 C12 C11 118.1(3) . . ?
C12 C11 H11C 109.4 . . ?
C12 C11 H11D 109.4 . . ?
C12 C11 C10 111.3(3) . . ?
H11C C11 H11D 108.0 . . ?
C10 C11 H11C 109.4 . . ?
C10 C11 H11D 109.4 . . ?
C9 C10 C11 112.1(3) . . ?
C9 C10 H10 108.7 . . ?
C9 C10 C4 108.1(3) . . ?
C11 C10 H10 108.7 . . ?
C4 C10 C11 110.6(3) . . ?
C4 C10 H10 108.7 . . ?
C3 C4 C10 119.5(3) . . ?
C3 C4 C5 121.7(3) . . ?
C5 C4 C10 118.8(3) . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
O4 C2' H2'A 109.5 . . ?
O4 C2' H2'B 109.5 . . ?
O4 C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 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
O6A C16A C12A C11A 1.8(7) . . . . ?
O6A C16A C12A C13A -173.3(4) . . . . ?
O6A C9A C10A C4A 173.1(4) . . . . ?
O6A C9A C10A C11A 50.7(5) . . . . ?
O3A C6A C1A C7A -0.9(6) . . . . ?
O3A C6A C1A C2A 179.6(4) . . . . ?
O5A C9A C10A C4A 55.1(4) . . . . ?
O5A C9A C10A C11A -67.3(4) . . . . ?
O7A C14A C15A C16A -1.6(6) . . . . ?
O7A C14A C15A C17A 178.1(4) . . . . ?
O2A C2A C3A C4A 178.0(4) . . . . ?
O2A C2A C3A C8A -0.9(6) . . . . ?
C19A C18A C14A O7A 86.9(5) . . . . ?
C19A C18A C14A C15A -92.8(6) . . . . ?
C18A C14A C15A C16A 178.1(4) . . . . ?
C18A C14A C15A C17A -2.3(8) . . . . ?
C14A O7A C13A O8A -175.9(4) . . . . ?
C14A O7A C13A C12A 2.8(6) . . . . ?
C14A C15A C16A O6A 177.2(4) . . . . ?
C14A C15A C16A C12A -2.1(7) . . . . ?
C15A C16A C12A C11A -179.0(4) . . . . ?
C15A C16A C12A C13A 6.0(7) . . . . ?
C16A O6A C9A O5A 77.8(4) . . . . ?
C16A O6A C9A C10A -43.1(5) . . . . ?
C16A C12A C13A O7A -6.2(6) . . . . ?
C16A C12A C13A O8A 172.4(4) . . . . ?
C9A O6A C16A C15A -162.7(4) . . . . ?
C9A O6A C16A C12A 16.7(6) . . . . ?
C9A O5A C8A O4A -72.5(4) . . . . ?
C9A O5A C8A C3A 48.0(4) . . . . ?
C9A C10A C4A C5A 162.0(4) . . . . ?
C9A C10A C4A C3A -22.0(6) . . . . ?
C9A C10A C11A C12A -32.1(5) . . . . ?
C10A C4A C5A C6A 177.8(4) . . . . ?
C10A C4A C3A C2A -175.8(4) . . . . ?
C10A C4A C3A C8A 3.1(6) . . . . ?
C10A C11A C12A C16A 7.0(6) . . . . ?
C10A C11A C12A C13A -177.9(4) . . . . ?
C4A C10A C11A C12A -153.5(4) . . . . ?
C4A C5A C6A O3A 179.2(4) . . . . ?
C4A C5A C6A C1A -2.5(7) . . . . ?
C4A C3A C8A O4A 107.0(4) . . . . ?
C4A C3A C8A O5A -15.1(6) . . . . ?
C5A C4A C3A C2A 0.1(6) . . . . ?
C5A C4A C3A C8A 179.0(4) . . . . ?
C5A C6A C1A C7A -179.3(4) . . . . ?
C5A C6A C1A C2A 1.2(7) . . . . ?
C6A C1A C7A O1A 178.2(4) . . . . ?
C6A C1A C2A O2A -178.7(4) . . . . ?
C6A C1A C2A C3A 0.8(6) . . . . ?
C1A C2A C3A C4A -1.5(6) . . . . ?
C1A C2A C3A C8A 179.6(4) . . . . ?
C7A C1A C2A O2A 1.8(7) . . . . ?
C7A C1A C2A C3A -178.7(4) . . . . ?
C1B O3A C6A C5A -4.0(6) . . . . ?
C1B O3A C6A C1A 177.7(4) . . . . ?
C2A C1A C7A O1A -2.3(7) . . . . ?
C2A C3A C8A O4A -74.2(5) . . . . ?
C2A C3A C8A O5A 163.8(4) . . . . ?
C3A C4A C5A C6A 1.9(7) . . . . ?
C8A O5A C9A O6A 165.8(3) . . . . ?
C8A O5A C9A C10A -71.3(4) . . . . ?
C2B O4A C8A O5A -80.7(4) . . . . ?
C2B O4A C8A C3A 156.8(3) . . . . ?
C11A C10A C4A C5A -74.2(5) . . . . ?
C11A C10A C4A C3A 101.8(4) . . . . ?
C11A C12A C13A O7A 178.5(4) . . . . ?
C11A C12A C13A O8A -2.9(7) . . . . ?
C13A O7A C14A C18A -178.6(4) . . . . ?
C13A O7A C14A C15A 1.1(6) . . . . ?
C17A C15A C16A O6A -2.4(6) . . . . ?
C17A C15A C16A C12A 178.3(4) . . . . ?
O5 C9 C10 C11 -66.0(4) . . . . ?
O5 C9 C10 C4 56.2(4) . . . . ?
O6 C9 C10 C11 52.5(5) . . . . ?
O6 C9 C10 C4 174.6(4) . . . . ?
O6 C16 C15 C14 176.4(4) . . . . ?
O6 C16 C15 C17 -4.2(6) . . . . ?
O6 C16 C12 C13 -176.2(4) . . . . ?
O6 C16 C12 C11 2.5(6) . . . . ?
O3 C6 C5 C4 -179.8(4) . . . . ?
O1 C7 C1 C2 -3.5(8) . . . . ?
O1 C7 C1 C6 177.8(5) . . . . ?
O7 C14 C18 C19 75.5(5) . . . . ?
O7 C13 C12 C16 -1.3(6) . . . . ?
O7 C13 C12 C11 179.9(4) . . . . ?
O8 C13 C12 C16 176.6(4) . . . . ?
O8 C13 C12 C11 -2.3(7) . . . . ?
O2 C2 C3 C8 0.7(6) . . . . ?
O2 C2 C3 C4 178.9(4) . . . . ?
C7 C1 C2 O2 2.1(7) . . . . ?
C7 C1 C2 C3 -177.0(4) . . . . ?
C7 C1 C6 O3 -2.5(6) . . . . ?
C7 C1 C6 C5 178.5(4) . . . . ?
C1 C2 C3 C8 179.9(4) . . . . ?
C1 C2 C3 C4 -1.9(7) . . . . ?
C1 C6 C5 C4 -0.8(7) . . . . ?
C2 C1 C6 O3 178.7(4) . . . . ?
C2 C1 C6 C5 -0.3(7) . . . . ?
C2 C3 C8 O5 164.2(4) . . . . ?
C2 C3 C8 O4 -74.8(5) . . . . ?
C2 C3 C4 C10 -177.1(4) . . . . ?
C2 C3 C4 C5 0.8(7) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C8 O5 C9 O6 163.6(3) . . . . ?
C8 O5 C9 C10 -73.4(4) . . . . ?
C8 C3 C4 C10 1.0(6) . . . . ?
C8 C3 C4 C5 178.9(4) . . . . ?
C9 O5 C8 O4 -70.2(4) . . . . ?
C9 O5 C8 C3 48.8(4) . . . . ?
C9 O6 C16 C15 -164.5(3) . . . . ?
C9 O6 C16 C12 15.6(6) . . . . ?
C9 C10 C4 C3 -21.1(5) . . . . ?
C9 C10 C4 C5 161.0(4) . . . . ?
C16 O6 C9 O5 77.3(4) . . . . ?
C16 O6 C9 C10 -43.3(5) . . . . ?
C16 C15 C14 O7 0.9(6) . . . . ?
C16 C15 C14 C18 -179.0(4) . . . . ?
C16 C12 C11 C10 7.8(6) . . . . ?
C15 C16 C12 C13 3.8(6) . . . . ?
C15 C16 C12 C11 -177.4(4) . . . . ?
C15 C14 C18 C19 -104.6(5) . . . . ?
C14 O7 C13 O8 -179.4(4) . . . . ?
C14 O7 C13 C12 -1.4(6) . . . . ?
C1' O3 C6 C1 174.5(4) . . . . ?
C1' O3 C6 C5 -6.6(7) . . . . ?
C6 C1 C2 O2 -179.1(4) . . . . ?
C6 C1 C2 C3 1.7(7) . . . . ?
C17 C15 C14 O7 -178.4(4) . . . . ?
C17 C15 C14 C18 1.6(7) . . . . ?
C13 O7 C14 C15 1.5(6) . . . . ?
C13 O7 C14 C18 -178.5(4) . . . . ?
C13 C12 C11 C10 -173.4(4) . . . . ?
C12 C16 C15 C14 -3.7(6) . . . . ?
C12 C16 C15 C17 175.7(4) . . . . ?
C12 C11 C10 C9 -33.7(5) . . . . ?
C12 C11 C10 C4 -154.4(3) . . . . ?
C11 C10 C4 C3 102.0(4) . . . . ?
C11 C10 C4 C5 -75.9(5) . . . . ?
C10 C4 C5 C6 178.5(4) . . . . ?
C4 C3 C8 O5 -13.9(6) . . . . ?
C4 C3 C8 O4 107.2(4) . . . . ?
C2' O4 C8 O5 -69.1(4) . . . . ?
C2' O4 C8 C3 169.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7(3)
2 0.3(3)

####################################################################### 
# 
# 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_210413k_0m
_database_code_depnum_ccdc_archive 'CCDC 2104479'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O7, H2 O'
_chemical_formula_sum            'C20 H22 O8'
_chemical_formula_weight         390.37
_chemical_absolute_configuration ad
_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                   14.126(4)
_cell_length_b                   4.5761(13)
_cell_length_c                   14.955(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.280(12)
_cell_angle_gamma                90
_cell_volume                     888.0(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8807
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      57.12
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16506
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.994
_diffrn_reflns_theta_min         2.798
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2898
_reflns_number_total             3317
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.097
_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)+(0.0733P)²+0.0060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1169
_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 Riding coordinates: 
 O8(H8C,H8D) 
2.b Ternary CH refined with riding coordinates: 
 C9(H9), C10(H10) 
2.c Secondary CH2 refined with riding coordinates: 
 C8(H8A,H8B), C11(H11A,H11B), C18(H18A,H18B) 
2.d Aromatic/amide H refined with riding coordinates: 
 C5(H5), C7(H7) 
2.e Idealised Me refined as rotating group: 
 C1'(H1'A,H1'B,H1'C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C) 
2.f Idealised tetrahedral OH refined as rotating group: 
 O2(H2) 
;
_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
C1 C 0.8066(2) 0.4234(8) 0.84570(19) 0.0196(7) Uani 1 1 d . . . . .
C1' C 0.7231(2) -0.0923(9) 0.6429(2) 0.0235(7) Uani 1 1 d . . . . .
H1'A H 0.678724 0.032542 0.589599 0.035 Uiso 1 1 calc R U . . .
H1'B H 0.680215 -0.218080 0.664777 0.035 Uiso 1 1 calc R U . . .
H1'C H 0.766221 -0.213836 0.620196 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7639(2) 0.5901(8) 0.89987(18) 0.0183(7) Uani 1 1 d . . . . .
C3 C 0.6585(2) 0.5761(8) 0.88033(18) 0.0179(7) Uani 1 1 d . . . . .
C4 C 0.5955(2) 0.4027(8) 0.80401(19) 0.0174(7) Uani 1 1 d . . . . .
C5 C 0.6353(2) 0.2370(8) 0.74775(19) 0.0189(7) Uani 1 1 d . . . . .
H5 H 0.590812 0.121294 0.695196 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7404(2) 0.2446(8) 0.76995(19) 0.0192(7) Uani 1 1 d . . . . .
C7 C 0.9153(2) 0.4466(9) 0.8658(2) 0.0250(8) Uani 1 1 d . . . . .
H7 H 0.942308 0.324612 0.830136 0.030 Uiso 1 1 calc R U . . .
C8 C 0.61743(19) 0.7525(8) 0.94215(19) 0.0195(7) Uani 1 1 d . . . . .
H8A H 0.638372 0.658793 1.006793 0.023 Uiso 1 1 calc R U . . .
H8B H 0.648224 0.950402 0.951988 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4798(2) 0.4025(8) 0.77827(18) 0.0168(6) Uani 1 1 d . . . . .
H9 H 0.452834 0.199192 0.760667 0.020 Uiso 1 1 calc R U . . .
C10 C 0.4617(2) 0.5001(8) 0.86767(19) 0.0175(7) Uani 1 1 d . . . . .
H10 H 0.493757 0.355305 0.921273 0.021 Uiso 1 1 calc R U . . .
C11 C 0.4243(2) 0.6053(7) 0.69132(18) 0.0170(7) Uani 1 1 d . . . . .
H11A H 0.469698 0.772541 0.693733 0.020 Uiso 1 1 calc R U . . .
H11B H 0.410424 0.497320 0.630058 0.020 Uiso 1 1 calc R U . . .
C12 C 0.3244(2) 0.7179(8) 0.69146(19) 0.0185(7) Uani 1 1 d . . . . .
C13 C 0.2586(2) 0.8883(8) 0.6103(2) 0.0200(7) Uani 1 1 d . . . . .
C14 C 0.1396(2) 0.9402(9) 0.6894(2) 0.0241(8) Uani 1 1 d . . . . .
C15 C 0.1989(2) 0.7803(8) 0.76632(19) 0.0206(7) Uani 1 1 d . . . . .
C16 C 0.2954(2) 0.6768(8) 0.76716(19) 0.0179(7) Uani 1 1 d . . . . .
C17 C 0.1717(2) 0.7074(9) 0.8518(2) 0.0269(9) Uani 1 1 d . . . . .
H17A H 0.222996 0.793668 0.911173 0.040 Uiso 1 1 calc R U . . .
H17B H 0.171024 0.494761 0.859333 0.040 Uiso 1 1 calc R U . . .
H17C H 0.103408 0.786500 0.840446 0.040 Uiso 1 1 calc R U . . .
C18 C 0.0387(2) 1.0861(9) 0.6704(2) 0.0297(9) Uani 1 1 d . . . . .
H18A H 0.046378 1.298640 0.662923 0.036 Uiso 1 1 calc R U . . .
H18B H 0.021217 1.057503 0.727688 0.036 Uiso 1 1 calc R U . . .
C19 C -0.0497(2) 0.9743(10) 0.5808(2) 0.0355(10) Uani 1 1 d . . . . .
H19A H -0.031674 0.991354 0.524089 0.053 Uiso 1 1 calc R U . . .
H19B H -0.111595 1.090366 0.569916 0.053 Uiso 1 1 calc R U . . .
H19C H -0.063036 0.768986 0.590361 0.053 Uiso 1 1 calc R U . . .
O1 O 0.97492(15) 0.6142(6) 0.92616(15) 0.0293(6) Uani 1 1 d . . . . .
O2 O 0.82194(14) 0.7673(6) 0.97257(13) 0.0226(5) Uani 1 1 d . . . . .
H2 H 0.882810 0.767202 0.976184 0.034 Uiso 1 1 calc R U . . .
O3 O 0.78740(14) 0.0864(5) 0.72220(14) 0.0233(6) Uani 1 1 d . . . . .
O4 O 0.50702(13) 0.7777(5) 0.89868(13) 0.0191(5) Uani 1 1 d . . . . .
O5 O 0.35554(14) 0.5317(5) 0.84966(13) 0.0194(5) Uani 1 1 d . . . . .
O6 O 0.16895(14) 0.9951(6) 0.61362(13) 0.0250(6) Uani 1 1 d . . . . .
O7 O 0.27468(14) 0.9536(6) 0.53826(14) 0.0272(6) Uani 1 1 d . . . . .
O8 O 0.53710(15) 0.5359(6) 0.47820(14) 0.0262(6) Uani 1 1 d . . . . .
H8C H 0.596354 0.501050 0.475279 0.039 Uiso 1 1 d R U . . .
H8D H 0.517304 0.367080 0.491359 0.039 Uiso 1 1 d 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
C1 C2 1.410(4) . ?
C1 C6 1.411(4) . ?
C1 C7 1.447(4) . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C1' O3 1.431(4) . ?
C2 C3 1.401(4) . ?
C2 O2 1.344(4) . ?
C3 C4 1.386(4) . ?
C3 C8 1.506(4) . ?
C4 C5 1.404(4) . ?
C4 C9 1.525(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(4) . ?
C6 O3 1.360(4) . ?
C7 H7 0.9500 . ?
C7 O1 1.229(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 O4 1.438(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.524(4) . ?
C9 C11 1.536(4) . ?
C10 H10 1.0000 . ?
C10 O4 1.416(4) . ?
C10 O5 1.422(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.503(4) . ?
C12 C13 1.433(4) . ?
C12 C16 1.361(4) . ?
C13 O6 1.377(3) . ?
C13 O7 1.222(3) . ?
C14 C15 1.341(4) . ?
C14 C18 1.496(4) . ?
C14 O6 1.375(3) . ?
C15 C16 1.438(4) . ?
C15 C17 1.511(4) . ?
C16 O5 1.363(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.514(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O2 H2 0.8400 . ?
O8 H8C 0.8699 . ?
O8 H8D 0.8701 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.4(2) . . ?
C2 C1 C7 120.1(3) . . ?
C6 C1 C7 121.5(3) . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
O3 C1' H1'A 109.5 . . ?
O3 C1' H1'B 109.5 . . ?
O3 C1' H1'C 109.5 . . ?
C3 C2 C1 121.1(3) . . ?
O2 C2 C1 121.9(2) . . ?
O2 C2 C3 117.0(3) . . ?
C2 C3 C8 118.9(3) . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 C8 122.3(2) . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 C9 118.9(2) . . ?
C5 C4 C9 119.4(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 120.9(3) . . ?
O3 C6 C1 115.1(2) . . ?
O3 C6 C5 124.0(3) . . ?
C1 C7 H7 117.9 . . ?
O1 C7 C1 124.1(3) . . ?
O1 C7 H7 117.9 . . ?
C3 C8 H8A 109.2 . . ?
C3 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O4 C8 C3 112.2(2) . . ?
O4 C8 H8A 109.2 . . ?
O4 C8 H8B 109.2 . . ?
C4 C9 H9 109.0 . . ?
C4 C9 C11 110.5(2) . . ?
C10 C9 C4 108.3(2) . . ?
C10 C9 H9 109.0 . . ?
C10 C9 C11 111.0(2) . . ?
C11 C9 H9 109.0 . . ?
C9 C10 H10 109.2 . . ?
O4 C10 C9 109.8(2) . . ?
O4 C10 H10 109.2 . . ?
O4 C10 O5 106.1(2) . . ?
O5 C10 C9 113.2(2) . . ?
O5 C10 H10 109.2 . . ?
C9 C11 H11A 109.3 . . ?
C9 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C9 111.8(2) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C13 C12 C11 118.7(2) . . ?
C16 C12 C11 123.1(3) . . ?
C16 C12 C13 118.2(3) . . ?
O6 C13 C12 117.4(2) . . ?
O7 C13 C12 126.5(3) . . ?
O7 C13 O6 116.0(3) . . ?
C15 C14 C18 129.2(3) . . ?
C15 C14 O6 121.1(3) . . ?
O6 C14 C18 109.7(3) . . ?
C14 C15 C16 117.1(2) . . ?
C14 C15 C17 124.4(3) . . ?
C16 C15 C17 118.5(3) . . ?
C12 C16 C15 122.9(3) . . ?
C12 C16 O5 122.3(2) . . ?
O5 C16 C15 114.7(2) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 108.7 . . ?
C14 C18 H18B 108.7 . . ?
C14 C18 C19 114.1(3) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 O2 H2 109.5 . . ?
C6 O3 C1' 117.2(2) . . ?
C10 O4 C8 110.2(2) . . ?
C16 O5 C10 117.1(2) . . ?
C14 O6 C13 123.1(2) . . ?
H8C O8 H8D 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -2.3(5) . . . . ?
C1 C2 C3 C8 178.4(3) . . . . ?
C1 C6 O3 C1' -178.3(3) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
C2 C1 C6 O3 -178.8(3) . . . . ?
C2 C1 C7 O1 -2.9(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C2 C3 C4 C9 -176.0(3) . . . . ?
C2 C3 C8 O4 164.7(3) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C3 C4 C9 C10 -22.8(4) . . . . ?
C3 C4 C9 C11 99.0(3) . . . . ?
C3 C8 O4 C10 48.2(3) . . . . ?
C4 C3 C8 O4 -14.6(4) . . . . ?
C4 C5 C6 C1 -2.2(5) . . . . ?
C4 C5 C6 O3 178.0(3) . . . . ?
C4 C9 C10 O4 56.7(3) . . . . ?
C4 C9 C10 O5 175.0(3) . . . . ?
C4 C9 C11 C12 -154.2(3) . . . . ?
C5 C4 C9 C10 159.7(3) . . . . ?
C5 C4 C9 C11 -78.5(4) . . . . ?
C5 C6 O3 C1' 1.5(5) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C6 C1 C2 O2 -179.4(3) . . . . ?
C6 C1 C7 O1 174.6(3) . . . . ?
C7 C1 C2 C3 178.6(3) . . . . ?
C7 C1 C2 O2 -1.8(5) . . . . ?
C7 C1 C6 C5 -176.3(3) . . . . ?
C7 C1 C6 O3 3.6(4) . . . . ?
C8 C3 C4 C5 -179.3(3) . . . . ?
C8 C3 C4 C9 3.2(4) . . . . ?
C9 C4 C5 C6 178.2(3) . . . . ?
C9 C10 O4 C8 -72.0(3) . . . . ?
C9 C10 O5 C16 -45.9(4) . . . . ?
C9 C11 C12 C13 -174.3(3) . . . . ?
C9 C11 C12 C16 8.7(4) . . . . ?
C10 C9 C11 C12 -34.1(4) . . . . ?
C11 C9 C10 O4 -64.8(3) . . . . ?
C11 C9 C10 O5 53.6(4) . . . . ?
C11 C12 C13 O6 -178.3(3) . . . . ?
C11 C12 C13 O7 0.4(5) . . . . ?
C11 C12 C16 C15 -178.8(3) . . . . ?
C11 C12 C16 O5 0.7(5) . . . . ?
C12 C13 O6 C14 -1.5(5) . . . . ?
C12 C16 O5 C10 18.4(4) . . . . ?
C13 C12 C16 C15 4.2(5) . . . . ?
C13 C12 C16 O5 -176.3(3) . . . . ?
C14 C15 C16 C12 -4.5(5) . . . . ?
C14 C15 C16 O5 176.0(3) . . . . ?
C15 C14 C18 C19 -118.2(4) . . . . ?
C15 C14 O6 C13 1.2(5) . . . . ?
C15 C16 O5 C10 -162.0(3) . . . . ?
C16 C12 C13 O6 -1.2(5) . . . . ?
C16 C12 C13 O7 177.6(3) . . . . ?
C17 C15 C16 C12 176.5(3) . . . . ?
C17 C15 C16 O5 -3.0(5) . . . . ?
C18 C14 C15 C16 -177.2(3) . . . . ?
C18 C14 C15 C17 1.8(6) . . . . ?
C18 C14 O6 C13 -179.7(3) . . . . ?
O2 C2 C3 C4 178.1(3) . . . . ?
O2 C2 C3 C8 -1.2(4) . . . . ?
O4 C10 O5 C16 74.6(3) . . . . ?
O5 C10 O4 C8 165.31(18) . . . . ?
O6 C14 C15 C16 1.7(5) . . . . ?
O6 C14 C15 C17 -179.3(3) . . . . ?
O6 C14 C18 C19 62.8(4) . . . . ?
O7 C13 O6 C14 179.7(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_210429c_0m
_database_code_depnum_ccdc_archive 'CCDC 2104482'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-05-06
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24 O6'
_chemical_formula_sum            'C20 H24 O6'
_chemical_formula_weight         360.39
_chemical_absolute_configuration ad
_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                   8.5427(4)
_cell_length_b                   15.2194(8)
_cell_length_c                   14.1219(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.418(2)
_cell_angle_gamma                90
_cell_volume                     1835.49(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      57.07
_cell_measurement_theta_min      3.72
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43116
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.066
_diffrn_reflns_theta_min         2.723
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                6911
_reflns_number_total             7371
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3044 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.10(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         7371
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.094
_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)+(0.0583P)²+0.2432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0970
_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 
2.a Ternary CH refined with riding coordinates: 
 C7(H7), C7A(H7A) 
2.b Secondary CH2 refined with riding coordinates: 
 C8(H8A,H8B), C9(H9A,H9B), C16(H16A,H16B), C8A(H8AA,H8AB), C9A(H9AA,H9AB), 
 C16A(H16C,H16D) 
2.c Aromatic/amide H refined with riding coordinates: 
 C3(H3), C6(H6), C3A(H3A), C6A(H6A) 
2.d Idealised Me refined as rotating group: 
 C1'(H1'A,H1'B,H1'C), C2'(H2'A,H2'B,H2'C), C3'(H3'A,H3'B,H3'C), C15(H15A,H15B, 
 H15C), C17(H17A,H17B,H17C), C1A'(H1AA,H1AB,H1AC), C2A'(H2AA,H2AB,H2AC), 
 C3A'(H3AA,H3AB,H3AC), C15A(H15D,H15E,H15F), C17A(H17D,H17E,H17F) 
;
_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
C1 C 0.3170(2) 0.79917(16) 0.72958(17) 0.0219(5) Uani 1 1 d . . . . .
C1' C 0.5150(3) 0.95853(18) 0.88427(19) 0.0305(6) Uani 1 1 d . . . . .
H1'A H 0.582059 0.979015 0.833454 0.046 Uiso 1 1 calc R U . . .
H1'B H 0.579540 0.946168 0.941057 0.046 Uiso 1 1 calc R U . . .
H1'C H 0.438067 1.004081 0.898602 0.046 Uiso 1 1 calc R U . . .
C2 C 0.3608(2) 0.88039(17) 0.76659(17) 0.0224(5) Uani 1 1 d . . . . .
C2' C 0.2799(3) 1.10717(17) 0.6009(2) 0.0322(6) Uani 1 1 d . . . . .
H2'A H 0.253114 1.151177 0.552479 0.048 Uiso 1 1 calc R U . . .
H2'B H 0.393929 1.100831 0.606031 0.048 Uiso 1 1 calc R U . . .
H2'C H 0.239620 1.126021 0.662006 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3289(3) 0.95747(17) 0.71619(18) 0.0243(5) Uani 1 1 d . . . . .
H3 H 0.360248 1.012702 0.741626 0.029 Uiso 1 1 calc R U . . .
C3' C 0.0720(3) 0.79317(18) 0.46660(19) 0.0321(6) Uani 1 1 d . . . . .
H3'A H 0.017071 0.803577 0.405890 0.048 Uiso 1 1 calc R U . . .
H3'B H -0.000697 0.767529 0.511535 0.048 Uiso 1 1 calc R U . . .
H3'C H 0.159341 0.752592 0.457219 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2512(3) 0.95323(16) 0.62871(18) 0.0229(5) Uani 1 1 d . . . . .
C5 C 0.2073(2) 0.87168(17) 0.59012(17) 0.0224(5) Uani 1 1 d . . . . .
C6 C 0.2412(2) 0.79593(16) 0.64046(18) 0.0226(5) Uani 1 1 d . . . . .
H6 H 0.212579 0.740586 0.614180 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3482(3) 0.71629(16) 0.78550(17) 0.0219(5) Uani 1 1 d . . . . .
H7 H 0.440394 0.726237 0.829198 0.026 Uiso 1 1 calc R U . . .
C8 C 0.2093(3) 0.68941(17) 0.84350(19) 0.0257(5) Uani 1 1 d . . . . .
H8A H 0.115012 0.685058 0.801576 0.031 Uiso 1 1 calc R U . . .
H8B H 0.189602 0.735037 0.891730 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2376(3) 0.60172(17) 0.89241(18) 0.0258(5) Uani 1 1 d . . . . .
H9A H 0.314442 0.609126 0.945460 0.031 Uiso 1 1 calc R U . . .
H9B H 0.138579 0.579663 0.918525 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2987(3) 0.53730(16) 0.82245(17) 0.0232(5) Uani 1 1 d . . . . .
C11 C 0.2777(3) 0.44557(18) 0.83858(19) 0.0294(5) Uani 1 1 d . . . . .
C12 C 0.4023(3) 0.41630(18) 0.68937(19) 0.0287(5) Uani 1 1 d . . . . .
C13 C 0.4268(3) 0.50255(17) 0.67259(18) 0.0242(5) Uani 1 1 d . . . . .
C14 C 0.3687(3) 0.56352(16) 0.74166(17) 0.0216(5) Uani 1 1 d . . . . .
C15 C 0.5097(3) 0.53702(18) 0.58807(18) 0.0282(5) Uani 1 1 d . . . . .
H15A H 0.433302 0.563232 0.543539 0.042 Uiso 1 1 calc R U . . .
H15B H 0.564091 0.488680 0.556931 0.042 Uiso 1 1 calc R U . . .
H15C H 0.586000 0.581693 0.608428 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4450(3) 0.33900(19) 0.6290(2) 0.0351(6) Uani 1 1 d . . . . .
H16A H 0.483060 0.360821 0.567617 0.042 Uiso 1 1 calc R U . . .
H16B H 0.349774 0.303554 0.615761 0.042 Uiso 1 1 calc R U . . .
C17 C 0.5695(4) 0.2804(2) 0.6741(2) 0.0425(7) Uani 1 1 d . . . . .
H17A H 0.587238 0.229581 0.633228 0.064 Uiso 1 1 calc R U . . .
H17B H 0.534483 0.260266 0.736027 0.064 Uiso 1 1 calc R U . . .
H17C H 0.667174 0.313634 0.682380 0.064 Uiso 1 1 calc R U . . .
O1 O 0.43513(19) 0.87997(12) 0.85454(12) 0.0271(4) Uani 1 1 d . . . . .
O2 O 0.2116(2) 1.02506(11) 0.57492(13) 0.0285(4) Uani 1 1 d . . . . .
O3 O 0.1311(2) 0.87499(12) 0.50345(12) 0.0282(4) Uani 1 1 d . . . . .
O4 O 0.38802(17) 0.64877(11) 0.71709(12) 0.0231(3) Uani 1 1 d . . . . .
O5 O 0.3289(2) 0.38795(12) 0.76928(14) 0.0327(4) Uani 1 1 d . . . . .
O6 O 0.2160(2) 0.41187(14) 0.90655(15) 0.0403(5) Uani 1 1 d . . . . .
C1A C 0.1903(2) 0.21724(16) 0.22337(17) 0.0203(5) Uani 1 1 d . . . . .
C1A' C 0.0257(3) 0.05046(17) 0.37690(19) 0.0282(5) Uani 1 1 d . . . . .
H1AA H -0.038203 0.025122 0.325165 0.042 Uiso 1 1 calc R U . . .
H1AB H -0.039812 0.060339 0.431915 0.042 Uiso 1 1 calc R U . . .
H1AC H 0.110711 0.009872 0.394194 0.042 Uiso 1 1 calc R U . . .
C2A C 0.1609(2) 0.13422(16) 0.26013(16) 0.0207(5) Uani 1 1 d . . . . .
C2A' C 0.2745(3) -0.08850(18) 0.1000(2) 0.0325(6) Uani 1 1 d . . . . .
H2AA H 0.303110 -0.131496 0.051700 0.049 Uiso 1 1 calc R U . . .
H2AB H 0.160705 -0.088734 0.107029 0.049 Uiso 1 1 calc R U . . .
H2AC H 0.325811 -0.103934 0.160535 0.049 Uiso 1 1 calc R U . . .
C3A C 0.2023(3) 0.05847(16) 0.21085(17) 0.0223(5) Uani 1 1 d . . . . .
H3A H 0.181073 0.002069 0.236328 0.027 Uiso 1 1 calc R U . . .
C3A' C 0.4225(3) 0.23245(18) -0.03591(19) 0.0301(5) Uani 1 1 d . . . . .
H3AA H 0.480648 0.224033 -0.094154 0.045 Uiso 1 1 calc R U . . .
H3AB H 0.489194 0.262536 0.011299 0.045 Uiso 1 1 calc R U . . .
H3AC H 0.329070 0.268074 -0.049661 0.045 Uiso 1 1 calc R U . . .
C4A C 0.2748(2) 0.06628(16) 0.12428(17) 0.0208(5) Uani 1 1 d . . . . .
C5A C 0.3035(2) 0.14957(17) 0.08594(16) 0.0216(5) Uani 1 1 d . . . . .
C6A C 0.2599(2) 0.22376(16) 0.13518(17) 0.0206(5) Uani 1 1 d . . . . .
H6A H 0.277617 0.280131 0.108613 0.025 Uiso 1 1 calc R U . . .
C7A C 0.1513(2) 0.29762(16) 0.28018(17) 0.0214(5) Uani 1 1 d . . . . .
H7A H 0.058836 0.284421 0.319846 0.026 Uiso 1 1 calc R U . . .
C8A C 0.2874(3) 0.32590(16) 0.34473(17) 0.0227(5) Uani 1 1 d . . . . .
H8AA H 0.381435 0.335248 0.306403 0.027 Uiso 1 1 calc R U . . .
H8AB H 0.311244 0.278604 0.391002 0.027 Uiso 1 1 calc R U . . .
C9A C 0.2495(3) 0.41066(17) 0.39791(17) 0.0232(5) Uani 1 1 d . . . . .
H9AA H 0.180687 0.397229 0.451410 0.028 Uiso 1 1 calc R U . . .
H9AB H 0.347344 0.437053 0.423943 0.028 Uiso 1 1 calc R U . . .
C10A C 0.1690(3) 0.47458(16) 0.33174(17) 0.0216(5) Uani 1 1 d . . . . .
C11A C 0.1615(3) 0.56491(16) 0.35884(18) 0.0242(5) Uani 1 1 d . . . . .
C12A C 0.0179(3) 0.59477(17) 0.21200(18) 0.0258(5) Uani 1 1 d . . . . .
C13A C 0.0290(2) 0.51115(17) 0.18206(17) 0.0231(5) Uani 1 1 d . . . . .
C14A C 0.1059(2) 0.44965(16) 0.24589(17) 0.0198(4) Uani 1 1 d . . . . .
C15A C -0.0379(3) 0.47794(18) 0.08939(18) 0.0283(5) Uani 1 1 d . . . . .
H15D H -0.112020 0.430278 0.101279 0.042 Uiso 1 1 calc R U . . .
H15E H 0.046937 0.455952 0.050406 0.042 Uiso 1 1 calc R U . . .
H15F H -0.092327 0.525940 0.056063 0.042 Uiso 1 1 calc R U . . .
C16A C -0.0592(3) 0.67035(18) 0.1613(2) 0.0331(6) Uani 1 1 d . . . . .
H16C H -0.107493 0.709487 0.208395 0.040 Uiso 1 1 calc R U . . .
H16D H -0.143829 0.647644 0.118889 0.040 Uiso 1 1 calc R U . . .
C17A C 0.0538(4) 0.7227(2) 0.1039(3) 0.0506(8) Uani 1 1 d . . . . .
H17D H 0.099703 0.684685 0.055945 0.076 Uiso 1 1 calc R U . . .
H17E H 0.137041 0.746072 0.145697 0.076 Uiso 1 1 calc R U . . .
H17F H -0.001870 0.771419 0.072631 0.076 Uiso 1 1 calc R U . . .
O1' O 0.09039(19) 0.13243(12) 0.34683(12) 0.0269(4) Uani 1 1 d . . . . .
O2' O 0.32402(19) -0.00307(11) 0.07170(12) 0.0256(4) Uani 1 1 d . . . . .
O3' O 0.37653(19) 0.14908(12) 0.00016(12) 0.0254(4) Uani 1 1 d . . . . .
O4' O 0.10891(17) 0.36646(11) 0.21279(11) 0.0221(3) Uani 1 1 d . . . . .
O5' O 0.08343(19) 0.62182(11) 0.29745(13) 0.0278(4) Uani 1 1 d . . . . .
O6' O 0.2169(2) 0.59666(12) 0.43115(13) 0.0322(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.390(3) . ?
C1 C6 1.402(3) . ?
C1 C7 1.508(3) . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C1' O1 1.434(3) . ?
C2 C3 1.395(4) . ?
C2 O1 1.381(3) . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C2' O2 1.423(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C3' H3'C 0.9800 . ?
C3' O3 1.437(3) . ?
C4 C5 1.403(3) . ?
C4 O2 1.369(3) . ?
C5 C6 1.381(3) . ?
C5 O3 1.373(3) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.515(3) . ?
C7 O4 1.457(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.519(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.495(3) . ?
C10 C11 1.427(4) . ?
C10 C14 1.361(3) . ?
C11 O5 1.393(3) . ?
C11 O6 1.219(3) . ?
C12 C13 1.351(4) . ?
C12 C16 1.504(4) . ?
C12 O5 1.374(3) . ?
C13 C14 1.443(3) . ?
C13 C15 1.498(4) . ?
C14 O4 1.354(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.516(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C1A C2A 1.391(3) . ?
C1A C6A 1.397(3) . ?
C1A C7A 1.505(3) . ?
C1A' H1AA 0.9800 . ?
C1A' H1AB 0.9800 . ?
C1A' H1AC 0.9800 . ?
C1A' O1' 1.433(3) . ?
C2A C3A 1.397(3) . ?
C2A O1' 1.378(3) . ?
C2A' H2AA 0.9800 . ?
C2A' H2AB 0.9800 . ?
C2A' H2AC 0.9800 . ?
C2A' O2' 1.427(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.389(3) . ?
C3A' H3AA 0.9800 . ?
C3A' H3AB 0.9800 . ?
C3A' H3AC 0.9800 . ?
C3A' O3' 1.426(3) . ?
C4A C5A 1.402(3) . ?
C4A O2' 1.363(3) . ?
C5A C6A 1.382(3) . ?
C5A O3' 1.376(3) . ?
C6A H6A 0.9500 . ?
C7A H7A 1.0000 . ?
C7A C8A 1.522(3) . ?
C7A O4' 1.455(3) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.531(3) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.503(3) . ?
C10A C11A 1.429(3) . ?
C10A C14A 1.368(3) . ?
C11A O5' 1.385(3) . ?
C11A O6' 1.215(3) . ?
C12A C13A 1.345(4) . ?
C12A C16A 1.499(3) . ?
C12A O5' 1.380(3) . ?
C13A C14A 1.446(3) . ?
C13A C15A 1.503(3) . ?
C14A O4' 1.350(3) . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C16A C17A 1.504(4) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.9(2) . . ?
C2 C1 C7 120.3(2) . . ?
C6 C1 C7 120.8(2) . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
O1 C1' H1'A 109.5 . . ?
O1 C1' H1'B 109.5 . . ?
O1 C1' H1'C 109.5 . . ?
C1 C2 C3 120.6(2) . . ?
O1 C2 C1 116.6(2) . . ?
O1 C2 C3 122.8(2) . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
O2 C2' H2'A 109.5 . . ?
O2 C2' H2'B 109.5 . . ?
O2 C2' H2'C 109.5 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
H3'A C3' H3'B 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
O3 C3' H3'A 109.5 . . ?
O3 C3' H3'B 109.5 . . ?
O3 C3' H3'C 109.5 . . ?
C3 C4 C5 120.2(2) . . ?
O2 C4 C3 124.2(2) . . ?
O2 C4 C5 115.5(2) . . ?
C6 C5 C4 119.2(2) . . ?
O3 C5 C4 115.5(2) . . ?
O3 C5 C6 125.3(2) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.3(2) . . ?
C5 C6 H6 119.4 . . ?
C1 C7 H7 108.8 . . ?
C1 C7 C8 112.22(19) . . ?
C8 C7 H7 108.8 . . ?
O4 C7 C1 106.49(19) . . ?
O4 C7 H7 108.8 . . ?
O4 C7 C8 111.54(19) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C9 111.41(19) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 C8 109.3(2) . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C11 C10 C9 119.3(2) . . ?
C14 C10 C9 122.0(2) . . ?
C14 C10 C11 118.7(2) . . ?
O5 C11 C10 117.5(2) . . ?
O6 C11 C10 126.6(3) . . ?
O6 C11 O5 115.9(2) . . ?
C13 C12 C16 128.3(2) . . ?
C13 C12 O5 121.7(2) . . ?
O5 C12 C16 110.0(2) . . ?
C12 C13 C14 116.7(2) . . ?
C12 C13 C15 123.9(2) . . ?
C14 C13 C15 119.4(2) . . ?
C10 C14 C13 122.9(2) . . ?
O4 C14 C10 123.7(2) . . ?
O4 C14 C13 113.4(2) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 108.9 . . ?
C12 C16 H16B 108.9 . . ?
C12 C16 C17 113.5(2) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 O1 C1' 117.7(2) . . ?
C4 O2 C2' 117.64(19) . . ?
C5 O3 C3' 116.47(19) . . ?
C14 O4 C7 118.29(18) . . ?
C12 O5 C11 122.5(2) . . ?
C2A C1A C6A 118.8(2) . . ?
C2A C1A C7A 119.7(2) . . ?
C6A C1A C7A 121.5(2) . . ?
H1AA C1A' H1AB 109.5 . . ?
H1AA C1A' H1AC 109.5 . . ?
H1AB C1A' H1AC 109.5 . . ?
O1' C1A' H1AA 109.5 . . ?
O1' C1A' H1AB 109.5 . . ?
O1' C1A' H1AC 109.5 . . ?
C1A C2A C3A 120.9(2) . . ?
O1' C2A C1A 115.9(2) . . ?
O1' C2A C3A 123.2(2) . . ?
H2AA C2A' H2AB 109.5 . . ?
H2AA C2A' H2AC 109.5 . . ?
H2AB C2A' H2AC 109.5 . . ?
O2' C2A' H2AA 109.5 . . ?
O2' C2A' H2AB 109.5 . . ?
O2' C2A' H2AC 109.5 . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A C2A 119.5(2) . . ?
C4A C3A H3A 120.3 . . ?
H3AA C3A' H3AB 109.5 . . ?
H3AA C3A' H3AC 109.5 . . ?
H3AB C3A' H3AC 109.5 . . ?
O3' C3A' H3AA 109.5 . . ?
O3' C3A' H3AB 109.5 . . ?
O3' C3A' H3AC 109.5 . . ?
C3A C4A C5A 120.2(2) . . ?
O2' C4A C3A 124.3(2) . . ?
O2' C4A C5A 115.5(2) . . ?
C6A C5A C4A 119.5(2) . . ?
O3' C5A C4A 115.0(2) . . ?
O3' C5A C6A 125.5(2) . . ?
C1A C6A H6A 119.4 . . ?
C5A C6A C1A 121.1(2) . . ?
C5A C6A H6A 119.4 . . ?
C1A C7A H7A 108.9 . . ?
C1A C7A C8A 111.94(18) . . ?
C8A C7A H7A 108.9 . . ?
O4' C7A C1A 106.94(18) . . ?
O4' C7A H7A 108.9 . . ?
O4' C7A C8A 111.23(18) . . ?
C7A C8A H8AA 109.4 . . ?
C7A C8A H8AB 109.4 . . ?
C7A C8A C9A 111.37(18) . . ?
H8AA C8A H8AB 108.0 . . ?
C9A C8A H8AA 109.4 . . ?
C9A C8A H8AB 109.4 . . ?
C8A C9A H9AA 109.7 . . ?
C8A C9A H9AB 109.7 . . ?
H9AA C9A H9AB 108.2 . . ?
C10A C9A C8A 109.83(19) . . ?
C10A C9A H9AA 109.7 . . ?
C10A C9A H9AB 109.7 . . ?
C11A C10A C9A 118.6(2) . . ?
C14A C10A C9A 122.4(2) . . ?
C14A C10A C11A 119.0(2) . . ?
O5' C11A C10A 117.3(2) . . ?
O6' C11A C10A 126.0(2) . . ?
O6' C11A O5' 116.7(2) . . ?
C13A C12A C16A 127.6(2) . . ?
C13A C12A O5' 121.8(2) . . ?
O5' C12A C16A 110.6(2) . . ?
C12A C13A C14A 116.8(2) . . ?
C12A C13A C15A 124.3(2) . . ?
C14A C13A C15A 118.8(2) . . ?
C10A C14A C13A 122.4(2) . . ?
O4' C14A C10A 123.8(2) . . ?
O4' C14A C13A 113.8(2) . . ?
C13A C15A H15D 109.5 . . ?
C13A C15A H15E 109.5 . . ?
C13A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C12A C16A H16C 109.1 . . ?
C12A C16A H16D 109.1 . . ?
C12A C16A C17A 112.6(2) . . ?
H16C C16A H16D 107.8 . . ?
C17A C16A H16C 109.1 . . ?
C17A C16A H16D 109.1 . . ?
C16A C17A H17D 109.5 . . ?
C16A C17A H17E 109.5 . . ?
C16A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C2A O1' C1A' 117.45(19) . . ?
C4A O2' C2A' 117.11(19) . . ?
C5A O3' C3A' 116.38(19) . . ?
C14A O4' C7A 117.08(18) . . ?
C12A O5' C11A 122.62(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C2 O1 C1' 165.1(2) . . . . ?
C1 C7 C8 C9 175.0(2) . . . . ?
C1 C7 O4 C14 -157.44(18) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C7 C8 93.8(3) . . . . ?
C2 C1 C7 O4 -143.85(19) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 O2 178.5(2) . . . . ?
C3 C2 O1 C1' -15.3(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 O3 180.0(2) . . . . ?
C3 C4 O2 C2' 12.7(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 O3 C3' -174.3(2) . . . . ?
C5 C4 O2 C2' -167.6(2) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C6 C1 C2 O1 -179.97(19) . . . . ?
C6 C1 C7 C8 -85.1(3) . . . . ?
C6 C1 C7 O4 37.2(3) . . . . ?
C6 C5 O3 C3' 5.1(3) . . . . ?
C7 C1 C2 C3 -178.5(2) . . . . ?
C7 C1 C2 O1 1.1(3) . . . . ?
C7 C1 C6 C5 177.8(2) . . . . ?
C7 C8 C9 C10 -47.7(3) . . . . ?
C8 C7 O4 C14 -34.7(3) . . . . ?
C8 C9 C10 C11 -155.9(2) . . . . ?
C8 C9 C10 C14 21.5(3) . . . . ?
C9 C10 C11 O5 176.7(2) . . . . ?
C9 C10 C11 O6 -1.7(4) . . . . ?
C9 C10 C14 C13 -179.2(2) . . . . ?
C9 C10 C14 O4 -0.6(3) . . . . ?
C10 C11 O5 C12 2.3(3) . . . . ?
C10 C14 O4 C7 7.3(3) . . . . ?
C11 C10 C14 C13 -1.8(3) . . . . ?
C11 C10 C14 O4 176.8(2) . . . . ?
C12 C13 C14 C10 2.9(3) . . . . ?
C12 C13 C14 O4 -175.8(2) . . . . ?
C13 C12 C16 C17 113.6(3) . . . . ?
C13 C12 O5 C11 -1.2(4) . . . . ?
C13 C14 O4 C7 -173.97(17) . . . . ?
C14 C10 C11 O5 -0.8(3) . . . . ?
C14 C10 C11 O6 -179.2(2) . . . . ?
C15 C13 C14 C10 -176.9(2) . . . . ?
C15 C13 C14 O4 4.4(3) . . . . ?
C16 C12 C13 C14 178.0(2) . . . . ?
C16 C12 C13 C15 -2.2(4) . . . . ?
C16 C12 O5 C11 179.3(2) . . . . ?
O1 C2 C3 C4 -178.85(19) . . . . ?
O2 C4 C5 C6 -179.2(2) . . . . ?
O2 C4 C5 O3 0.3(3) . . . . ?
O3 C5 C6 C1 -178.7(2) . . . . ?
O4 C7 C8 C9 55.6(3) . . . . ?
O5 C12 C13 C14 -1.4(3) . . . . ?
O5 C12 C13 C15 178.4(2) . . . . ?
O5 C12 C16 C17 -67.0(3) . . . . ?
O6 C11 O5 C12 -179.1(2) . . . . ?
C1A C2A C3A C4A 0.5(3) . . . . ?
C1A C2A O1' C1A' 165.91(19) . . . . ?
C1A C7A C8A C9A 176.79(19) . . . . ?
C1A C7A O4' C14A -164.49(17) . . . . ?
C2A C1A C6A C5A -1.9(3) . . . . ?
C2A C1A C7A C8A 89.3(2) . . . . ?
C2A C1A C7A O4' -148.61(18) . . . . ?
C2A C3A C4A C5A -1.2(3) . . . . ?
C2A C3A C4A O2' 178.06(19) . . . . ?
C3A C2A O1' C1A' -14.4(3) . . . . ?
C3A C4A C5A C6A 0.3(3) . . . . ?
C3A C4A C5A O3' 179.71(18) . . . . ?
C3A C4A O2' C2A' 10.8(3) . . . . ?
C4A C5A C6A C1A 1.2(3) . . . . ?
C4A C5A O3' C3A' -173.54(19) . . . . ?
C5A C4A O2' C2A' -170.0(2) . . . . ?
C6A C1A C2A C3A 1.0(3) . . . . ?
C6A C1A C2A O1' -179.27(18) . . . . ?
C6A C1A C7A C8A -88.8(2) . . . . ?
C6A C1A C7A O4' 33.3(3) . . . . ?
C6A C5A O3' C3A' 5.8(3) . . . . ?
C7A C1A C2A C3A -177.12(19) . . . . ?
C7A C1A C2A O1' 2.6(3) . . . . ?
C7A C1A C6A C5A 176.24(18) . . . . ?
C7A C8A C9A C10A -42.7(3) . . . . ?
C8A C7A O4' C14A -42.0(2) . . . . ?
C8A C9A C10A C11A -163.3(2) . . . . ?
C8A C9A C10A C14A 15.3(3) . . . . ?
C9A C10A C11A O5' -178.52(19) . . . . ?
C9A C10A C11A O6' 1.2(4) . . . . ?
C9A C10A C14A C13A -179.8(2) . . . . ?
C9A C10A C14A O4' 0.3(3) . . . . ?
C10A C11A O5' C12A -1.6(3) . . . . ?
C10A C14A O4' C7A 13.5(3) . . . . ?
C11A C10A C14A C13A -1.2(3) . . . . ?
C11A C10A C14A O4' 178.9(2) . . . . ?
C12A C13A C14A C10A -1.8(3) . . . . ?
C12A C13A C14A O4' 178.11(19) . . . . ?
C13A C12A C16A C17A -93.7(3) . . . . ?
C13A C12A O5' C11A -1.5(3) . . . . ?
C13A C14A O4' C7A -166.44(17) . . . . ?
C14A C10A C11A O5' 2.8(3) . . . . ?
C14A C10A C11A O6' -177.4(2) . . . . ?
C15A C13A C14A C10A -179.6(2) . . . . ?
C15A C13A C14A O4' 0.3(3) . . . . ?
C16A C12A C13A C14A -178.2(2) . . . . ?
C16A C12A C13A C15A -0.5(4) . . . . ?
C16A C12A O5' C11A 179.7(2) . . . . ?
O1' C2A C3A C4A -179.22(19) . . . . ?
O2' C4A C5A C6A -178.94(19) . . . . ?
O2' C4A C5A O3' 0.4(3) . . . . ?
O3' C5A C6A C1A -178.11(19) . . . . ?
O4' C7A C8A C9A 57.2(3) . . . . ?
O5' C12A C13A C14A 3.1(3) . . . . ?
O5' C12A C13A C15A -179.2(2) . . . . ?
O5' C12A C16A C17A 85.1(3) . . . . ?
O6' C11A O5' C12A 178.6(2) . . . . ?

_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_210323f_0m
_database_code_depnum_ccdc_archive 'CCDC 2104480'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-04-23
# start Validation Reply Form
_vrf_THETM01_210323f_0m          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: This is due to the crystal quality which is very thin and small,
resulting a weak diffraction ability in the high angle.
;
# end Validation Reply Form

_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H22 O8)'
_chemical_formula_sum            'C42 H44 O16'
_chemical_formula_weight         804.77
_chemical_absolute_configuration ad
_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      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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.5505(2)
_cell_length_b                   17.1723(8)
_cell_length_c                   48.042(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3754.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8326
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      46.40
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.7492
_exptl_absorpt_correction_T_min  0.5846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            18403
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        46.474
_diffrn_reflns_theta_max         46.474
_diffrn_reflns_theta_min         1.600
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4303
_reflns_number_total             4878
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         4878
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.072
_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)+(0.0521P)²+0.3244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0981
_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:
 C8(H8), C9(H9), C10(H10), C8A(H8A), C9A(H9A), C10A(H10A)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C11A(H11C,H11D), C18A(H18C,H18D)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C5A(H5A), C7A(H7A)
2.d Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C2'(H2'A,H2'B,H2'C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,H2BC), C17A(H17D,H17E,H17F),
 C19A(H19D,H19E,H19F)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1A(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1520(9) 0.4637(2) 0.56634(8) 0.0274(10) Uani 1 1 d . . . . .
C1' C -0.6086(10) 0.6365(2) 0.57689(8) 0.0318(10) Uani 1 1 d . . . . .
H1'A H -0.753534 0.625266 0.562344 0.048 Uiso 1 1 calc R U . . .
H1'B H -0.481026 0.679200 0.570812 0.048 Uiso 1 1 calc R U . . .
H1'C H -0.710478 0.651547 0.594041 0.048 Uiso 1 1 calc R U . . .
C2 C -0.0001(9) 0.4253(2) 0.54484(8) 0.0259(9) Uani 1 1 d . . . . .
C2' C 0.1620(11) 0.2907(2) 0.47133(8) 0.0342(11) Uani 1 1 d . . . . .
H2'A H 0.192714 0.314121 0.452959 0.051 Uiso 1 1 calc R U . . .
H2'B H 0.048644 0.242508 0.469335 0.051 Uiso 1 1 calc R U . . .
H2'C H 0.352697 0.278984 0.479834 0.051 Uiso 1 1 calc R U . . .
C3 C 0.0040(9) 0.4545(2) 0.51773(8) 0.0240(9) Uani 1 1 d . . . . .
C4 C -0.1421(9) 0.5239(2) 0.51233(8) 0.0242(9) Uani 1 1 d . . . . .
C5 C -0.2912(9) 0.5644(2) 0.53346(8) 0.0247(9) Uani 1 1 d . . . . .
H5 H -0.387563 0.612174 0.529457 0.030 Uiso 1 1 calc R U . . .
C6 C -0.2966(9) 0.5343(2) 0.56004(8) 0.0264(10) Uani 1 1 d . . . . .
C7 C -0.1630(11) 0.4317(2) 0.59400(8) 0.0361(11) Uani 1 1 d . . . . .
H7 H -0.276069 0.458469 0.607598 0.043 Uiso 1 1 calc R U . . .
C8 C 0.1688(9) 0.4108(2) 0.49554(8) 0.0259(9) Uani 1 1 d . . . . .
H8 H 0.363529 0.394128 0.503124 0.031 Uiso 1 1 calc R U . . .
C9 C -0.1312(9) 0.5587(2) 0.48337(7) 0.0228(9) Uani 1 1 d . . . . .
H9 H -0.330566 0.579254 0.478569 0.027 Uiso 1 1 calc R U . . .
C10 C -0.0529(9) 0.4952(2) 0.46316(7) 0.0246(9) Uani 1 1 d . . . . .
H10 H -0.213069 0.455309 0.463285 0.030 Uiso 1 1 calc R U . . .
C11 C 0.0910(9) 0.6264(2) 0.48220(7) 0.0253(10) Uani 1 1 d . . . . .
H11A H -0.005607 0.674839 0.488586 0.030 Uiso 1 1 calc R U . . .
H11B H 0.256555 0.615216 0.494953 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2068(9) 0.6380(2) 0.45336(8) 0.0231(9) Uani 1 1 d . . . . .
C13 C 0.3926(9) 0.7034(2) 0.44824(8) 0.0277(10) Uani 1 1 d . . . . .
C14 C 0.4216(9) 0.6632(2) 0.39960(8) 0.0272(10) Uani 1 1 d . . . . .
C15 C 0.2504(9) 0.6008(2) 0.40407(8) 0.0249(10) Uani 1 1 d . . . . .
C16 C 0.1507(9) 0.5884(2) 0.43209(8) 0.0240(9) Uani 1 1 d . . . . .
C17 C 0.1549(10) 0.5449(2) 0.38163(8) 0.0320(10) Uani 1 1 d . . . . .
H17A H 0.235072 0.561765 0.363691 0.048 Uiso 1 1 calc R U . . .
H17B H -0.060221 0.543987 0.380630 0.048 Uiso 1 1 calc R U . . .
H17C H 0.227585 0.492576 0.385995 0.048 Uiso 1 1 calc R U . . .
C18 C 0.5616(10) 0.6901(2) 0.37325(8) 0.0311(10) Uani 1 1 d . . . . .
H18A H 0.559481 0.646816 0.359632 0.037 Uiso 1 1 calc R U . . .
H18B H 0.769404 0.703514 0.377017 0.037 Uiso 1 1 calc R U . . .
C19 C 0.4089(10) 0.7605(2) 0.36046(8) 0.0361(11) Uani 1 1 d . . . . .
H19A H 0.519584 0.778111 0.344134 0.054 Uiso 1 1 calc R U . . .
H19B H 0.399634 0.802587 0.374200 0.054 Uiso 1 1 calc R U . . .
H19C H 0.209261 0.746026 0.354817 0.054 Uiso 1 1 calc R U . . .
O1 O -0.0338(8) 0.37109(17) 0.60124(6) 0.0430(8) Uani 1 1 d . . . . .
O2 O 0.1469(7) 0.35832(15) 0.55003(6) 0.0338(7) Uani 1 1 d . . . . .
H2 H 0.131900 0.347103 0.566984 0.051 Uiso 1 1 calc R U . . .
O3 O -0.4343(6) 0.56838(15) 0.58198(5) 0.0324(7) Uani 1 1 d . . . . .
O4 O 0.0033(6) 0.34434(14) 0.48877(5) 0.0291(7) Uani 1 1 d . . . . .
O5 O 0.2156(6) 0.45864(14) 0.47139(5) 0.0264(7) Uani 1 1 d . . . . .
O6 O -0.0112(6) 0.52146(14) 0.43538(5) 0.0257(6) Uani 1 1 d . . . . .
O7 O 0.4955(6) 0.71302(15) 0.42102(5) 0.0284(7) Uani 1 1 d . . . . .
O8 O 0.4737(7) 0.75129(16) 0.46504(5) 0.0344(7) Uani 1 1 d . . . . .
C1A C 0.3520(9) 0.4774(2) 0.18627(8) 0.0297(10) Uani 1 1 d . . . . .
C1B C 0.8454(10) 0.6142(2) 0.22109(8) 0.0339(11) Uani 1 1 d . . . . .
H1BA H 0.966359 0.655404 0.212880 0.051 Uiso 1 1 calc R U . . .
H1BB H 0.972796 0.575245 0.229860 0.051 Uiso 1 1 calc R U . . .
H1BC H 0.714317 0.636695 0.235128 0.051 Uiso 1 1 calc R U . . .
C2A C 0.1792(9) 0.4127(2) 0.19336(8) 0.0301(10) Uani 1 1 d . . . . .
C2B C -0.0733(11) 0.1843(2) 0.21167(9) 0.0423(12) Uani 1 1 d . . . . .
H2BA H -0.220340 0.199767 0.197832 0.063 Uiso 1 1 calc R U . . .
H2BB H -0.172080 0.169897 0.229052 0.063 Uiso 1 1 calc R U . . .
H2BC H 0.038534 0.139653 0.204664 0.063 Uiso 1 1 calc R U . . .
C3A C 0.1666(9) 0.3845(2) 0.22081(8) 0.0266(10) Uani 1 1 d . . . . .
C4A C 0.3252(9) 0.4234(2) 0.24108(8) 0.0240(9) Uani 1 1 d . . . . .
C5A C 0.4938(9) 0.4893(2) 0.23483(8) 0.0266(9) Uani 1 1 d . . . . .
H5A H 0.595885 0.516184 0.249164 0.032 Uiso 1 1 calc R U . . .
C6A C 0.5103(9) 0.5149(2) 0.20765(8) 0.0272(10) Uani 1 1 d . . . . .
C7A C 0.3662(11) 0.5049(3) 0.15778(9) 0.0390(12) Uani 1 1 d . . . . .
H7A H 0.490990 0.547683 0.153565 0.047 Uiso 1 1 calc R U . . .
C8A C -0.0195(10) 0.3146(2) 0.22722(8) 0.0290(10) Uani 1 1 d . . . . .
H8A H -0.212727 0.320347 0.217520 0.035 Uiso 1 1 calc R U . . .
C9A C 0.1950(9) 0.3150(2) 0.27200(8) 0.0277(10) Uani 1 1 d . . . . .
H9A H 0.347743 0.280665 0.263419 0.033 Uiso 1 1 calc R U . . .
C10A C 0.3004(9) 0.3984(2) 0.27107(8) 0.0259(9) Uani 1 1 d . . . . .
H10A H 0.500387 0.400769 0.279649 0.031 Uiso 1 1 calc R U . . .
C11A C 0.0981(9) 0.4533(2) 0.28719(8) 0.0267(10) Uani 1 1 d . . . . .
H11C H 0.213299 0.498515 0.293819 0.032 Uiso 1 1 calc R U . . .
H11D H -0.056814 0.472911 0.274544 0.032 Uiso 1 1 calc R U . . .
C12A C -0.0428(9) 0.4142(2) 0.31153(7) 0.0246(9) Uani 1 1 d . . . . .
C13A C -0.2295(9) 0.4599(2) 0.32890(8) 0.0268(10) Uani 1 1 d . . . . .
C14A C -0.3132(10) 0.3446(2) 0.35708(8) 0.0298(10) Uani 1 1 d . . . . .
C15A C -0.1506(10) 0.2997(2) 0.34031(8) 0.0276(10) Uani 1 1 d . . . . .
C16A C -0.0189(9) 0.3367(2) 0.31660(8) 0.0262(10) Uani 1 1 d . . . . .
C17A C -0.1060(11) 0.2134(2) 0.34498(9) 0.0384(12) Uani 1 1 d . . . . .
H17D H -0.176896 0.199330 0.363572 0.058 Uiso 1 1 calc R U . . .
H17E H 0.103569 0.200992 0.343483 0.058 Uiso 1 1 calc R U . . .
H17F H -0.215815 0.184076 0.330918 0.058 Uiso 1 1 calc R U . . .
C18A C -0.4665(10) 0.3226(2) 0.38341(8) 0.0322(10) Uani 1 1 d . . . . .
H18C H -0.520836 0.266809 0.382596 0.039 Uiso 1 1 calc R U . . .
H18D H -0.649876 0.353235 0.385090 0.039 Uiso 1 1 calc R U . . .
C19A C -0.2776(13) 0.3366(4) 0.40885(9) 0.0732(19) Uani 1 1 d . . . . .
H19D H -0.094089 0.307167 0.407128 0.110 Uiso 1 1 calc R U . . .
H19E H -0.383497 0.319541 0.425530 0.110 Uiso 1 1 calc R U . . .
H19F H -0.232963 0.392304 0.410369 0.110 Uiso 1 1 calc R U . . .
O1A O 0.0159(7) 0.37580(16) 0.17410(6) 0.0366(7) Uani 1 1 d . . . . .
H1A H 0.049109 0.395150 0.158351 0.055 Uiso 1 1 calc R U . . .
O2A O 0.2221(8) 0.47495(18) 0.13870(6) 0.0508(9) Uani 1 1 d . . . . .
O3A O 0.6739(6) 0.57783(15) 0.19976(5) 0.0336(7) Uani 1 1 d . . . . .
O4A O 0.1239(7) 0.24847(16) 0.21678(5) 0.0349(7) Uani 1 1 d . . . . .
O5A O -0.0713(6) 0.30763(15) 0.25665(5) 0.0291(7) Uani 1 1 d . . . . .
O6A O 0.1330(6) 0.28784(14) 0.29941(5) 0.0298(7) Uani 1 1 d . . . . .
O7A O -0.3538(6) 0.42281(14) 0.35177(5) 0.0286(7) Uani 1 1 d . . . . .
O8A O -0.2969(6) 0.52767(15) 0.32527(5) 0.0318(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.407(5) . ?
C1 C6 1.411(5) . ?
C1 C7 1.439(5) . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C1' O3 1.434(5) . ?
C2 C3 1.395(5) . ?
C2 O2 1.354(4) . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C2' O4 1.439(4) . ?
C3 C4 1.389(5) . ?
C3 C8 1.504(5) . ?
C4 C5 1.405(5) . ?
C4 C9 1.515(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(5) . ?
C6 O3 1.359(5) . ?
C7 H7 0.9500 . ?
C7 O1 1.245(5) . ?
C8 H8 1.0000 . ?
C8 O4 1.406(5) . ?
C8 O5 1.438(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.504(5) . ?
C9 C11 1.541(5) . ?
C10 H10 1.0000 . ?
C10 O5 1.429(5) . ?
C10 O6 1.422(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.496(5) . ?
C12 C13 1.427(6) . ?
C12 C16 1.355(5) . ?
C13 O7 1.398(5) . ?
C13 O8 1.209(5) . ?
C14 C15 1.343(6) . ?
C14 C18 1.490(5) . ?
C14 O7 1.379(5) . ?
C15 C16 1.436(5) . ?
C15 C17 1.507(5) . ?
C16 O6 1.374(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.524(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O2 H2 0.8400 . ?
C1A C2A 1.403(6) . ?
C1A C6A 1.410(6) . ?
C1A C7A 1.449(6) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C1B O3A 1.431(5) . ?
C2A C3A 1.406(5) . ?
C2A O1A 1.346(5) . ?
C2B H2BA 0.9800 . ?
C2B H2BB 0.9800 . ?
C2B H2BC 0.9800 . ?
C2B O4A 1.442(5) . ?
C3A C4A 1.383(5) . ?
C3A C8A 1.501(5) . ?
C4A C5A 1.401(5) . ?
C4A C10A 1.507(5) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.380(5) . ?
C6A O3A 1.366(5) . ?
C7A H7A 0.9500 . ?
C7A O2A 1.239(5) . ?
C8A H8A 1.0000 . ?
C8A O4A 1.403(5) . ?
C8A O5A 1.438(5) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.512(5) . ?
C9A O5A 1.424(5) . ?
C9A O6A 1.425(5) . ?
C10A H10A 1.0000 . ?
C10A C11A 1.528(5) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11A C12A 1.493(5) . ?
C12A C13A 1.426(5) . ?
C12A C16A 1.358(5) . ?
C13A O7A 1.390(5) . ?
C13A O8A 1.216(5) . ?
C14A C15A 1.338(6) . ?
C14A C18A 1.493(6) . ?
C14A O7A 1.379(5) . ?
C15A C16A 1.435(5) . ?
C15A C17A 1.512(5) . ?
C16A O6A 1.365(5) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A C19A 1.513(6) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
O1A H1A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.3(3) . . ?
C2 C1 C7 121.0(4) . . ?
C6 C1 C7 120.7(4) . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
O3 C1' H1'A 109.5 . . ?
O3 C1' H1'B 109.5 . . ?
O3 C1' H1'C 109.5 . . ?
C3 C2 C1 121.5(3) . . ?
O2 C2 C1 120.4(3) . . ?
O2 C2 C3 118.1(3) . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
O4 C2' H2'A 109.5 . . ?
O4 C2' H2'B 109.5 . . ?
O4 C2' H2'C 109.5 . . ?
C2 C3 C8 119.3(3) . . ?
C4 C3 C2 118.5(4) . . ?
C4 C3 C8 122.3(3) . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 C9 119.7(3) . . ?
C5 C4 C9 119.0(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 120.8(4) . . ?
O3 C6 C1 114.7(3) . . ?
O3 C6 C5 124.4(3) . . ?
C1 C7 H7 117.9 . . ?
O1 C7 C1 124.1(4) . . ?
O1 C7 H7 117.9 . . ?
C3 C8 H8 109.1 . . ?
O4 C8 C3 107.6(3) . . ?
O4 C8 H8 109.1 . . ?
O4 C8 O5 110.9(3) . . ?
O5 C8 C3 111.2(3) . . ?
O5 C8 H8 109.1 . . ?
C4 C9 H9 108.7 . . ?
C4 C9 C11 110.6(3) . . ?
C10 C9 C4 108.3(3) . . ?
C10 C9 H9 108.7 . . ?
C10 C9 C11 111.6(3) . . ?
C11 C9 H9 108.7 . . ?
C9 C10 H10 108.7 . . ?
O5 C10 C9 110.0(3) . . ?
O5 C10 H10 108.7 . . ?
O6 C10 C9 114.1(3) . . ?
O6 C10 H10 108.7 . . ?
O6 C10 O5 106.5(3) . . ?
C9 C11 H11A 109.3 . . ?
C9 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C9 111.5(3) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C13 C12 C11 118.3(3) . . ?
C16 C12 C11 123.2(3) . . ?
C16 C12 C13 118.5(3) . . ?
O7 C13 C12 116.9(3) . . ?
O8 C13 C12 126.9(4) . . ?
O8 C13 O7 116.2(4) . . ?
C15 C14 C18 129.1(4) . . ?
C15 C14 O7 121.1(3) . . ?
O7 C14 C18 109.8(3) . . ?
C14 C15 C16 116.8(3) . . ?
C14 C15 C17 124.2(4) . . ?
C16 C15 C17 119.0(4) . . ?
C12 C16 C15 123.6(4) . . ?
C12 C16 O6 122.7(3) . . ?
O6 C16 C15 113.6(3) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.0 . . ?
C14 C18 H18B 109.0 . . ?
C14 C18 C19 113.1(3) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 O2 H2 109.5 . . ?
C6 O3 C1' 118.3(3) . . ?
C8 O4 C2' 112.7(3) . . ?
C10 O5 C8 110.3(3) . . ?
C16 O6 C10 116.4(3) . . ?
C14 O7 C13 122.9(3) . . ?
C2A C1A C6A 118.1(4) . . ?
C2A C1A C7A 120.8(4) . . ?
C6A C1A C7A 121.1(4) . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
O3A C1B H1BA 109.5 . . ?
O3A C1B H1BB 109.5 . . ?
O3A C1B H1BC 109.5 . . ?
C1A C2A C3A 121.6(4) . . ?
O1A C2A C1A 121.0(4) . . ?
O1A C2A C3A 117.4(4) . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
O4A C2B H2BA 109.5 . . ?
O4A C2B H2BB 109.5 . . ?
O4A C2B H2BC 109.5 . . ?
C2A C3A C8A 119.4(4) . . ?
C4A C3A C2A 118.2(4) . . ?
C4A C3A C8A 122.4(3) . . ?
C3A C4A C5A 121.7(3) . . ?
C3A C4A C10A 119.8(3) . . ?
C5A C4A C10A 118.4(3) . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A C4A 119.3(4) . . ?
C6A C5A H5A 120.3 . . ?
C5A C6A C1A 121.1(4) . . ?
O3A C6A C1A 115.9(3) . . ?
O3A C6A C5A 123.0(4) . . ?
C1A C7A H7A 118.7 . . ?
O2A C7A C1A 122.7(4) . . ?
O2A C7A H7A 118.7 . . ?
C3A C8A H8A 108.8 . . ?
O4A C8A C3A 108.2(3) . . ?
O4A C8A H8A 108.8 . . ?
O4A C8A O5A 111.1(3) . . ?
O5A C8A C3A 111.1(3) . . ?
O5A C8A H8A 108.8 . . ?
C10A C9A H9A 109.0 . . ?
O5A C9A H9A 109.0 . . ?
O5A C9A C10A 109.8(3) . . ?
O5A C9A O6A 106.3(3) . . ?
O6A C9A H9A 109.0 . . ?
O6A C9A C10A 113.6(3) . . ?
C4A C10A C9A 108.7(3) . . ?
C4A C10A H10A 108.3 . . ?
C4A C10A C11A 110.8(3) . . ?
C9A C10A H10A 108.3 . . ?
C9A C10A C11A 112.2(3) . . ?
C11A C10A H10A 108.3 . . ?
C10A C11A H11C 109.1 . . ?
C10A C11A H11D 109.1 . . ?
H11C C11A H11D 107.9 . . ?
C12A C11A C10A 112.3(3) . . ?
C12A C11A H11C 109.1 . . ?
C12A C11A H11D 109.1 . . ?
C13A C12A C11A 117.9(3) . . ?
C16A C12A C11A 123.1(4) . . ?
C16A C12A C13A 118.8(4) . . ?
O7A C13A C12A 117.0(3) . . ?
O8A C13A C12A 126.3(4) . . ?
O8A C13A O7A 116.7(3) . . ?
C15A C14A C18A 128.5(4) . . ?
C15A C14A O7A 121.6(4) . . ?
O7A C14A C18A 109.9(3) . . ?
C14A C15A C16A 117.0(3) . . ?
C14A C15A C17A 123.3(4) . . ?
C16A C15A C17A 119.7(4) . . ?
C12A C16A C15A 122.9(4) . . ?
C12A C16A O6A 122.3(3) . . ?
O6A C16A C15A 114.8(3) . . ?
C15A C17A H17D 109.5 . . ?
C15A C17A H17E 109.5 . . ?
C15A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C14A C18A H18C 109.2 . . ?
C14A C18A H18D 109.2 . . ?
C14A C18A C19A 112.2(4) . . ?
H18C C18A H18D 107.9 . . ?
C19A C18A H18C 109.2 . . ?
C19A C18A H18D 109.2 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C2A O1A H1A 109.5 . . ?
C6A O3A C1B 116.3(3) . . ?
C8A O4A C2B 113.0(3) . . ?
C9A O5A C8A 111.2(3) . . ?
C16A O6A C9A 117.3(3) . . ?
C14A O7A C13A 122.5(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
_geom_hbond_publ_flag
O2 H2 O1 0.84 1.86 2.604(4) 147.3 . yes
O1A H1A O2A 0.84 1.84 2.583(4) 146.4 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.2(6) . . . . ?
C1 C2 C3 C8 -179.7(4) . . . . ?
C1 C6 O3 C1' -174.5(4) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C2 C1 C6 O3 -179.1(4) . . . . ?
C2 C1 C7 O1 3.0(7) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C2 C3 C4 C9 177.5(4) . . . . ?
C2 C3 C8 O4 73.9(5) . . . . ?
C2 C3 C8 O5 -164.5(3) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C3 C4 C9 C10 20.9(5) . . . . ?
C3 C4 C9 C11 -101.7(4) . . . . ?
C3 C8 O4 C2' -169.7(3) . . . . ?
C3 C8 O5 C10 -48.9(4) . . . . ?
C4 C3 C8 O4 -107.0(4) . . . . ?
C4 C3 C8 O5 14.5(5) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C4 C5 C6 O3 -179.9(4) . . . . ?
C4 C9 C10 O5 -55.4(4) . . . . ?
C4 C9 C10 O6 -175.0(3) . . . . ?
C4 C9 C11 C12 154.5(3) . . . . ?
C5 C4 C9 C10 -161.5(3) . . . . ?
C5 C4 C9 C11 75.9(4) . . . . ?
C5 C6 O3 C1' 6.0(6) . . . . ?
C6 C1 C2 C3 -1.4(6) . . . . ?
C6 C1 C2 O2 178.6(4) . . . . ?
C6 C1 C7 O1 -177.8(4) . . . . ?
C7 C1 C2 C3 177.9(4) . . . . ?
C7 C1 C2 O2 -2.1(6) . . . . ?
C7 C1 C6 C5 -178.8(4) . . . . ?
C7 C1 C6 O3 1.7(6) . . . . ?
C8 C3 C4 C5 -179.1(4) . . . . ?
C8 C3 C4 C9 -1.5(6) . . . . ?
C9 C4 C5 C6 -178.4(4) . . . . ?
C9 C10 O5 C8 72.8(4) . . . . ?
C9 C10 O6 C16 44.1(4) . . . . ?
C9 C11 C12 C13 173.8(3) . . . . ?
C9 C11 C12 C16 -8.1(5) . . . . ?
C10 C9 C11 C12 33.8(4) . . . . ?
C11 C9 C10 O5 66.7(4) . . . . ?
C11 C9 C10 O6 -53.0(4) . . . . ?
C11 C12 C13 O7 -179.5(3) . . . . ?
C11 C12 C13 O8 1.3(6) . . . . ?
C11 C12 C16 C15 177.3(4) . . . . ?
C11 C12 C16 O6 -2.0(6) . . . . ?
C12 C13 O7 C14 0.9(5) . . . . ?
C12 C16 O6 C10 -16.2(5) . . . . ?
C13 C12 C16 C15 -4.7(6) . . . . ?
C13 C12 C16 O6 176.1(3) . . . . ?
C14 C15 C16 C12 3.7(6) . . . . ?
C14 C15 C16 O6 -177.0(3) . . . . ?
C15 C14 C18 C19 105.1(5) . . . . ?
C15 C14 O7 C13 -1.8(6) . . . . ?
C15 C16 O6 C10 164.5(3) . . . . ?
C16 C12 C13 O7 2.3(5) . . . . ?
C16 C12 C13 O8 -176.9(4) . . . . ?
C17 C15 C16 C12 -175.2(4) . . . . ?
C17 C15 C16 O6 4.0(5) . . . . ?
C18 C14 C15 C16 178.7(4) . . . . ?
C18 C14 C15 C17 -2.4(7) . . . . ?
C18 C14 O7 C13 179.0(3) . . . . ?
O2 C2 C3 C4 -178.9(3) . . . . ?
O2 C2 C3 C8 0.2(6) . . . . ?
O4 C8 O5 C10 70.7(4) . . . . ?
O5 C8 O4 C2' 68.5(4) . . . . ?
O5 C10 O6 C16 -77.5(4) . . . . ?
O6 C10 O5 C8 -163.1(3) . . . . ?
O7 C14 C15 C16 -0.4(6) . . . . ?
O7 C14 C15 C17 178.5(4) . . . . ?
O7 C14 C18 C19 -75.8(4) . . . . ?
O8 C13 O7 C14 -179.9(4) . . . . ?
C1A C2A C3A C4A 1.4(6) . . . . ?
C1A C2A C3A C8A -179.4(4) . . . . ?
C1A C6A O3A C1B -177.4(3) . . . . ?
C2A C1A C6A C5A -0.7(6) . . . . ?
C2A C1A C6A O3A -179.6(3) . . . . ?
C2A C1A C7A O2A 2.3(6) . . . . ?
C2A C3A C4A C5A 0.3(6) . . . . ?
C2A C3A C4A C10A 175.7(3) . . . . ?
C2A C3A C8A O4A 74.0(4) . . . . ?
C2A C3A C8A O5A -163.8(3) . . . . ?
C3A C4A C5A C6A -2.1(6) . . . . ?
C3A C4A C10A C9A 22.1(5) . . . . ?
C3A C4A C10A C11A -101.6(4) . . . . ?
C3A C8A O4A C2B -157.1(3) . . . . ?
C3A C8A O5A C9A -48.6(4) . . . . ?
C4A C3A C8A O4A -106.8(4) . . . . ?
C4A C3A C8A O5A 15.4(5) . . . . ?
C4A C5A C6A C1A 2.3(6) . . . . ?
C4A C5A C6A O3A -178.8(3) . . . . ?
C4A C10A C11A C12A 153.5(3) . . . . ?
C5A C4A C10A C9A -162.3(4) . . . . ?
C5A C4A C10A C11A 73.9(4) . . . . ?
C5A C6A O3A C1B 3.7(5) . . . . ?
C6A C1A C2A C3A -1.2(6) . . . . ?
C6A C1A C2A O1A 178.0(4) . . . . ?
C6A C1A C7A O2A -177.5(4) . . . . ?
C7A C1A C2A C3A 179.0(4) . . . . ?
C7A C1A C2A O1A -1.8(6) . . . . ?
C7A C1A C6A C5A 179.2(4) . . . . ?
C7A C1A C6A O3A 0.2(6) . . . . ?
C8A C3A C4A C5A -178.9(4) . . . . ?
C8A C3A C4A C10A -3.5(6) . . . . ?
C9A C10A C11A C12A 31.7(5) . . . . ?
C10A C4A C5A C6A -177.5(4) . . . . ?
C10A C9A O5A C8A 71.2(4) . . . . ?
C10A C9A O6A C16A 43.8(5) . . . . ?
C10A C11A C12A C13A 177.9(3) . . . . ?
C10A C11A C12A C16A -7.1(6) . . . . ?
C11A C12A C13A O7A -178.7(3) . . . . ?
C11A C12A C13A O8A 3.3(6) . . . . ?
C11A C12A C16A C15A 178.9(4) . . . . ?
C11A C12A C16A O6A -1.2(6) . . . . ?
C12A C13A O7A C14A -3.1(5) . . . . ?
C12A C16A O6A C9A -17.7(5) . . . . ?
C13A C12A C16A C15A -6.2(6) . . . . ?
C13A C12A C16A O6A 173.7(3) . . . . ?
C14A C15A C16A C12A 3.0(6) . . . . ?
C14A C15A C16A O6A -177.0(3) . . . . ?
C15A C14A C18A C19A 92.2(6) . . . . ?
C15A C14A O7A C13A -0.1(6) . . . . ?
C15A C16A O6A C9A 162.3(3) . . . . ?
C16A C12A C13A O7A 6.1(5) . . . . ?
C16A C12A C13A O8A -171.9(4) . . . . ?
C17A C15A C16A C12A -178.1(4) . . . . ?
C17A C15A C16A O6A 1.9(6) . . . . ?
C18A C14A C15A C16A -177.9(4) . . . . ?
C18A C14A C15A C17A 3.2(7) . . . . ?
C18A C14A O7A C13A 178.4(3) . . . . ?
O1A C2A C3A C4A -177.8(3) . . . . ?
O1A C2A C3A C8A 1.4(5) . . . . ?
O4A C8A O5A C9A 72.0(4) . . . . ?
O5A C8A O4A C2B 80.7(4) . . . . ?
O5A C9A C10A C4A -54.7(4) . . . . ?
O5A C9A C10A C11A 68.2(4) . . . . ?
O5A C9A O6A C16A -77.0(4) . . . . ?
O6A C9A C10A C4A -173.6(3) . . . . ?
O6A C9A C10A C11A -50.7(5) . . . . ?
O6A C9A O5A C8A -165.6(3) . . . . ?
O7A C14A C15A C16A 0.3(6) . . . . ?
O7A C14A C15A C17A -178.6(4) . . . . ?
O7A C14A C18A C19A -86.1(5) . . . . ?
O8A C13A O7A C14A 175.1(4) . . . . ?

_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_20201225_za-34
_database_code_depnum_ccdc_archive 'CCDC 2124876'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-11-29 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O7'
_chemical_formula_sum            'C20 H20 O7'
_chemical_formula_weight         372.36
_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                   13.66489(13)
_cell_length_b                   15.50084(13)
_cell_length_c                   8.21733(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.5797(9)
_cell_angle_gamma                90
_cell_volume                     1698.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11825
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4640
_cell_measurement_theta_min      3.3250
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.768
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (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    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.925
_diffrn_reflns_theta_min         3.314
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  -7.00   0.50    0.50    --    0.00 -76.00  44.00   88
  2  ω      8.00 107.00   0.50    0.50    --   94.60 -76.00  44.00  198
  3  ω     73.00 134.00   0.50    0.50    --   94.60  76.00 171.00  122
  4  ω    -25.00  29.00   0.50    0.50    --    0.00 -77.00  60.00  108
  5  ω    -29.00  27.00   0.50    0.50    --    0.00 -82.00-180.00  112
  6  ω    -25.00  27.00   0.50    0.50    --    0.00 -82.00 120.00  104
  7  ω    -20.00   6.00   0.50    0.50    --    0.00 -82.00 -90.00   52
  8  ω    -87.00  13.00   0.50    0.50    --    0.00 -19.00  60.00  200
  9  ω     98.00 181.00   0.50    0.50    --   94.60  30.00-120.00  166
 10  ω    123.00 148.00   0.50    0.50    --   94.60  82.00-150.00   50
 11  ω     78.00 184.00   0.50    0.50    --   94.60  30.00 -90.00  212
 12  ω     80.00 184.00   0.50    0.50    --   94.60  77.00 150.00  208
 13  ω     79.00 121.00   0.50    0.50    --   94.60  45.00 -30.00   84
 14  ω     15.00  65.00   0.50    0.50    --   94.60 -77.00 150.00  100
 15  ω     86.00 122.00   0.50    0.50    --   94.60 -77.00 150.00   72
 16  ω    158.00 184.00   0.50    0.50    --   94.60  82.00 120.00   52
 17  ω      9.00  58.00   0.50    0.50    --   94.60 -77.00 -30.00   98
 18  ω     47.00 117.00   0.50    0.50    --   94.60 -61.00  30.00  140
 19  ω    131.00 166.00   0.50    0.50    --   94.60  15.00 120.00   70
 20  ω     75.00 113.00   0.50    0.50    --   94.60 -77.00 -30.00   76
 21  ω      5.00  75.00   0.50    0.50    --   94.60 -30.00-120.00  140
 22  ω     89.00 119.00   0.50    0.50    --   94.60  15.00 120.00   60
 23  ω     77.00 179.00   0.50    0.50    --   94.60  45.00 -60.00  204
 24  ω    128.00 153.00   0.50    0.50    --   94.60  45.00 -30.00   50
 25  ω     86.00 112.00   0.50    0.50    --   94.60  77.00  90.00   52
 26  ω    140.00 182.00   0.50    0.50    --   94.60  82.00  90.00   84
 27  ω     79.00 104.00   0.50    0.50    --   94.60  77.00 120.00   50
 28  ω    100.00 125.00   0.50    0.50    --   94.60  82.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0045959000
_diffrn_orient_matrix_UB_12      -0.0260592000
_diffrn_orient_matrix_UB_13      0.1790938000
_diffrn_orient_matrix_UB_21      -0.0676182000
_diffrn_orient_matrix_UB_22      0.0783173000
_diffrn_orient_matrix_UB_23      0.0111543000
_diffrn_orient_matrix_UB_31      -0.0935387000
_diffrn_orient_matrix_UB_32      -0.0553797000
_diffrn_orient_matrix_UB_33      -0.0684695000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3166
_reflns_number_total             3396
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.7800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0900
_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:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7)
2.d Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 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 0.45724(7) 0.35012(6) 0.27143(12) 0.0277(2) Uani 1 1 d . . . . .
O2 O 0.53742(7) 0.50006(6) 0.36495(11) 0.0233(2) Uani 1 1 d . . . . .
H2 H 0.5027 0.4572 0.3686 0.035 Uiso 1 1 calc GR . . . .
O3 O 0.74787(6) 0.68495(5) 0.32237(10) 0.01805(19) Uani 1 1 d . . . . .
O4 O 0.60163(7) 0.34696(6) -0.10108(12) 0.0240(2) Uani 1 1 d . . . . .
O5 O 0.81707(6) 0.77452(5) 0.16349(10) 0.01643(19) Uani 1 1 d . . . . .
O6 O 1.08403(6) 0.59469(6) 0.08243(12) 0.0239(2) Uani 1 1 d . . . . .
O7 O 1.10383(6) 0.73556(6) 0.11715(11) 0.0220(2) Uani 1 1 d . . . . .
C1 C 0.56787(8) 0.42124(8) 0.12899(15) 0.0181(2) Uani 1 1 d . . . . .
C1' C 0.65123(10) 0.34226(9) -0.23763(18) 0.0268(3) Uani 1 1 d . . . . .
H1'A H 0.6272 0.3877 -0.3155 0.040 Uiso 1 1 calc GR . . . .
H1'B H 0.6375 0.2875 -0.2923 0.040 Uiso 1 1 calc GR . . . .
H1'C H 0.7222 0.3485 -0.1965 0.040 Uiso 1 1 calc GR . . . .
C2 C 0.58294(8) 0.49312(8) 0.23560(15) 0.0174(2) Uani 1 1 d . . . . .
C3 C 0.64660(8) 0.56055(7) 0.21374(14) 0.0167(2) Uani 1 1 d . . . . .
C4 C 0.69508(8) 0.55611(7) 0.08189(14) 0.0152(2) Uani 1 1 d . . . . .
C5 C 0.68144(8) 0.48553(8) -0.02747(15) 0.0171(2) Uani 1 1 d . . . . .
H5 H 0.7143 0.4837 -0.1153 0.021 Uiso 1 1 calc R . . . .
C6 C 0.61885(9) 0.41869(8) -0.00415(15) 0.0179(2) Uani 1 1 d . . . . .
C7 C 0.50100(9) 0.35245(8) 0.15477(17) 0.0219(3) Uani 1 1 d . . . . .
H7 H 0.4903 0.3072 0.0787 0.026 Uiso 1 1 calc R . . . .
C8 C 0.66093(9) 0.63597(8) 0.33272(15) 0.0195(3) Uani 1 1 d . . . . .
H8A H 0.6023 0.6729 0.3069 0.023 Uiso 1 1 calc R . . . .
H8B H 0.6675 0.6149 0.4457 0.023 Uiso 1 1 calc R . . . .
C9 C 0.76707(8) 0.62730(7) 0.05890(14) 0.0150(2) Uani 1 1 d . . . . .
H9 H 0.7566 0.6415 -0.0598 0.018 Uiso 1 1 calc R . . . .
C10 C 0.74611(8) 0.70690(7) 0.15495(14) 0.0154(2) Uani 1 1 d . . . . .
H10 H 0.6794 0.7291 0.1034 0.019 Uiso 1 1 calc R . . . .
C11 C 0.87619(8) 0.59874(7) 0.12371(15) 0.0169(2) Uani 1 1 d . . . . .
H11A H 0.8848 0.5761 0.2360 0.020 Uiso 1 1 calc R . . . .
H11B H 0.8932 0.5536 0.0529 0.020 Uiso 1 1 calc R . . . .
C12 C 0.94323(9) 0.67511(7) 0.12303(14) 0.0167(2) Uani 1 1 d . . . . .
C13 C 1.04423(9) 0.66240(8) 0.10453(15) 0.0188(3) Uani 1 1 d . . . . .
C14 C 1.06954(9) 0.81700(8) 0.13915(15) 0.0200(3) Uani 1 1 d . . . . .
C15 C 0.97351(9) 0.83153(8) 0.14765(15) 0.0185(3) Uani 1 1 d . . . . .
C16 C 0.91086(9) 0.75656(7) 0.14315(14) 0.0158(2) Uani 1 1 d . . . . .
C17 C 0.93084(10) 0.91960(8) 0.16573(17) 0.0229(3) Uani 1 1 d . . . . .
H17A H 0.9255 0.9281 0.2792 0.034 Uiso 1 1 calc GR . . . .
H17B H 0.8656 0.9241 0.0936 0.034 Uiso 1 1 calc GR . . . .
H17C H 0.9742 0.9628 0.1359 0.034 Uiso 1 1 calc GR . . . .
C18 C 1.15367(10) 0.88044(9) 0.15677(17) 0.0253(3) Uani 1 1 d . . . . .
H18A H 1.2016 0.8690 0.2603 0.030 Uiso 1 1 calc R . . . .
H18B H 1.1272 0.9381 0.1640 0.030 Uiso 1 1 calc R . . . .
C19 C 1.20788(10) 0.87788(9) 0.01431(18) 0.0278(3) Uani 1 1 d . . . . .
H19A H 1.1614 0.8905 -0.0885 0.042 Uiso 1 1 calc GR . . . .
H19B H 1.2359 0.8215 0.0080 0.042 Uiso 1 1 calc GR . . . .
H19C H 1.2607 0.9200 0.0332 0.042 Uiso 1 1 calc GR . . . .


_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 C7 1.2360(16) . ?
O2 H2 0.8200 . ?
O2 C2 1.3478(14) . ?
O3 C8 1.4279(14) . ?
O3 C10 1.4123(13) . ?
O4 C1' 1.4335(16) . ?
O4 C6 1.3581(14) . ?
O5 C10 1.4193(13) . ?
O5 C16 1.3569(14) . ?
O6 C13 1.2138(15) . ?
O7 C13 1.3867(14) . ?
O7 C14 1.3723(15) . ?
C1 C2 1.4045(17) . ?
C1 C6 1.4198(17) . ?
C1 C7 1.4495(16) . ?
C1' H1'A 0.9600 . ?
C1' H1'B 0.9600 . ?
C1' H1'C 0.9600 . ?
C2 C3 1.3963(16) . ?
C3 C4 1.3894(16) . ?
C3 C8 1.5092(16) . ?
C4 C5 1.4022(16) . ?
C4 C9 1.5172(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.3833(16) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9800 . ?
C9 C10 1.5251(15) . ?
C9 C11 1.5352(15) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.4976(15) . ?
C12 C13 1.4346(17) . ?
C12 C16 1.3597(16) . ?
C14 C15 1.3481(17) . ?
C14 C18 1.4957(16) . ?
C15 C16 1.4392(16) . ?
C15 C17 1.5045(16) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.5161(18) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 O2 H2 109.5 . . ?
C10 O3 C8 110.38(8) . . ?
C6 O4 C1' 116.72(9) . . ?
C16 O5 C10 119.72(9) . . ?
C14 O7 C13 123.39(9) . . ?
C2 C1 C6 118.22(10) . . ?
C2 C1 C7 120.26(11) . . ?
C6 C1 C7 121.52(11) . . ?
O4 C1' H1'A 109.5 . . ?
O4 C1' H1'B 109.5 . . ?
O4 C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
O2 C2 C1 121.68(11) . . ?
O2 C2 C3 116.69(11) . . ?
C3 C2 C1 121.63(11) . . ?
C2 C3 C8 119.55(10) . . ?
C4 C3 C2 118.65(11) . . ?
C4 C3 C8 121.80(10) . . ?
C3 C4 C5 121.27(10) . . ?
C3 C4 C9 119.55(10) . . ?
C5 C4 C9 119.14(10) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.70(11) . . ?
C6 C5 H5 120.1 . . ?
O4 C6 C1 115.05(10) . . ?
O4 C6 C5 124.43(11) . . ?
C5 C6 C1 120.52(11) . . ?
O1 C7 C1 124.18(12) . . ?
O1 C7 H7 117.9 . . ?
C1 C7 H7 117.9 . . ?
O3 C8 C3 111.44(9) . . ?
O3 C8 H8A 109.3 . . ?
O3 C8 H8B 109.3 . . ?
C3 C8 H8A 109.3 . . ?
C3 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C4 C9 H9 109.3 . . ?
C4 C9 C10 108.91(9) . . ?
C4 C9 C11 110.75(9) . . ?
C10 C9 H9 109.3 . . ?
C10 C9 C11 109.35(9) . . ?
C11 C9 H9 109.3 . . ?
O3 C10 O5 105.26(9) . . ?
O3 C10 C9 110.12(9) . . ?
O3 C10 H10 108.8 . . ?
O5 C10 C9 114.83(9) . . ?
O5 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C9 C11 H11A 110.0 . . ?
C9 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 C9 108.64(9) . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C13 C12 C11 119.69(10) . . ?
C16 C12 C11 121.20(11) . . ?
C16 C12 C13 119.10(11) . . ?
O6 C13 O7 116.32(10) . . ?
O6 C13 C12 127.39(11) . . ?
O7 C13 C12 116.27(10) . . ?
O7 C14 C18 109.90(10) . . ?
C15 C14 O7 121.64(11) . . ?
C15 C14 C18 128.43(11) . . ?
C14 C15 C16 116.37(11) . . ?
C14 C15 C17 124.00(11) . . ?
C16 C15 C17 119.61(11) . . ?
O5 C16 C12 123.13(11) . . ?
O5 C16 C15 113.81(10) . . ?
C12 C16 C15 123.05(11) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 108.8 . . ?
C14 C18 H18B 108.8 . . ?
C14 C18 C19 113.74(11) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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 O1 0.82 1.89 2.6128(13) 146.8 .

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
O2 C2 C3 C4 -179.97(10) . . . . ?
O2 C2 C3 C8 -0.05(16) . . . . ?
O7 C14 C15 C16 3.84(18) . . . . ?
O7 C14 C15 C17 -177.82(11) . . . . ?
O7 C14 C18 C19 54.40(15) . . . . ?
C1 C2 C3 C4 0.62(17) . . . . ?
C1 C2 C3 C8 -179.45(11) . . . . ?
C1' O4 C6 C1 179.57(10) . . . . ?
C1' O4 C6 C5 -1.05(17) . . . . ?
C2 C1 C6 O4 179.33(10) . . . . ?
C2 C1 C6 C5 -0.08(17) . . . . ?
C2 C1 C7 O1 -3.00(19) . . . . ?
C2 C3 C4 C5 -0.32(17) . . . . ?
C2 C3 C4 C9 -178.12(10) . . . . ?
C2 C3 C8 O3 163.19(10) . . . . ?
C3 C4 C5 C6 -0.18(17) . . . . ?
C3 C4 C9 C10 -18.86(14) . . . . ?
C3 C4 C9 C11 101.43(12) . . . . ?
C4 C3 C8 O3 -16.89(16) . . . . ?
C4 C5 C6 O4 -178.98(11) . . . . ?
C4 C5 C6 C1 0.38(17) . . . . ?
C4 C9 C10 O3 53.05(12) . . . . ?
C4 C9 C10 O5 171.63(9) . . . . ?
C4 C9 C11 C12 -171.28(9) . . . . ?
C5 C4 C9 C10 163.28(10) . . . . ?
C5 C4 C9 C11 -76.43(13) . . . . ?
C6 C1 C2 O2 -179.81(10) . . . . ?
C6 C1 C2 C3 -0.43(17) . . . . ?
C6 C1 C7 O1 177.66(11) . . . . ?
C7 C1 C2 O2 0.83(17) . . . . ?
C7 C1 C2 C3 -179.79(11) . . . . ?
C7 C1 C6 O4 -1.31(16) . . . . ?
C7 C1 C6 C5 179.27(11) . . . . ?
C8 O3 C10 O5 163.34(9) . . . . ?
C8 O3 C10 C9 -72.36(11) . . . . ?
C8 C3 C4 C5 179.76(11) . . . . ?
C8 C3 C4 C9 1.95(16) . . . . ?
C9 C4 C5 C6 177.64(10) . . . . ?
C9 C11 C12 C13 -152.27(11) . . . . ?
C9 C11 C12 C16 29.11(15) . . . . ?
C10 O3 C8 C3 51.43(12) . . . . ?
C10 O5 C16 C12 -3.54(16) . . . . ?
C10 O5 C16 C15 177.46(9) . . . . ?
C10 C9 C11 C12 -51.25(12) . . . . ?
C11 C9 C10 O3 -68.10(11) . . . . ?
C11 C9 C10 O5 50.48(12) . . . . ?
C11 C12 C13 O6 2.9(2) . . . . ?
C11 C12 C13 O7 -175.50(10) . . . . ?
C11 C12 C16 O5 -0.58(18) . . . . ?
C11 C12 C16 C15 178.33(11) . . . . ?
C13 O7 C14 C15 -0.99(18) . . . . ?
C13 O7 C14 C18 177.04(11) . . . . ?
C13 C12 C16 O5 -179.20(10) . . . . ?
C13 C12 C16 C15 -0.29(18) . . . . ?
C14 O7 C13 O6 178.79(11) . . . . ?
C14 O7 C13 C12 -2.64(17) . . . . ?
C14 C15 C16 O5 175.76(10) . . . . ?
C14 C15 C16 C12 -3.25(18) . . . . ?
C15 C14 C18 C19 -127.75(14) . . . . ?
C16 O5 C10 O3 98.51(11) . . . . ?
C16 O5 C10 C9 -22.76(14) . . . . ?
C16 C12 C13 O6 -178.47(12) . . . . ?
C16 C12 C13 O7 3.14(17) . . . . ?
C17 C15 C16 O5 -2.65(16) . . . . ?
C17 C15 C16 C12 178.34(11) . . . . ?
C18 C14 C15 C16 -173.79(12) . . . . ?
C18 C14 C15 C17 4.5(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 2.638
_oxdiff_exptl_absorpt_empirical_full_min 0.630
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 2104483'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-04-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24 O6'
_chemical_formula_sum            'C20 H24 O6'
_chemical_formula_weight         360.39
_chemical_absolute_configuration ad
_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      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.6051(4)
_cell_length_b                   14.1919(6)
_cell_length_c                   15.2989(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1868.34(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      58.751
_cell_measurement_theta_min      2.513
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32268
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.078
_diffrn_reflns_theta_min         5.131
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3931
_reflns_number_total             4055
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 1651 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.049
_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)+(0.0499P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0793
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C13 \\sim C12A-C13
 with sigma of 0.02
 C12-C16 \\sim C12A-C16A
 with sigma of 0.02
 C11-C12 \\sim C11-C12A
 with sigma of 0.04
 C13-C16 \\sim C13-C16A
 with sigma of 0.04
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 C12-C17 \\sim C12A-C17A
 with sigma of 0.04
 O5-C11 \\sim O5A-C11
 with sigma of 0.02
 O5-C12 \\sim O5A-C12A
 with sigma of 0.02
 O5-C13 \\sim O5A-C13
 with sigma of 0.04
 O5-C16 \\sim O5A-C16A
 with sigma of 0.04
 O6-C11 \\sim O6A-C11
 with sigma of 0.02
3. Others
 Sof(O5A)=Sof(C12A)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C17A)=Sof(H17D)=
 Sof(H17E)=Sof(H17F)=Sof(O6A)=1-FVAR(1)
 Sof(O5)=Sof(O6)=Sof(C12)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=
 Sof(H17B)=Sof(H17C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16A(H16C,H16D)
4.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17A(H17D,H17E,H17F)
;
_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
O3 O 0.38217(15) 0.49834(7) 0.38849(7) 0.0515(3) Uani 1 1 d . . . . .
O2 O 0.44548(16) 0.42808(8) 0.23729(7) 0.0555(3) Uani 1 1 d . . . . .
O1 O 0.67444(15) 0.15153(8) 0.37498(8) 0.0534(3) Uani 1 1 d . . . . .
O4 O 0.64218(12) 0.28491(7) 0.60699(6) 0.0427(2) Uani 1 1 d . . . . .
O5 O 0.5880(6) 0.2253(3) 0.8671(2) 0.0616(9) Uani 0.557(6) 1 d D . P A 1
O6 O 0.5189(14) 0.0763(7) 0.8392(7) 0.0637(16) Uani 0.557(6) 1 d D . P A 1
C1 C 0.56672(15) 0.27431(10) 0.45794(9) 0.0388(3) Uani 1 1 d . . . . .
C3' C 0.3313(3) 0.53441(13) 0.47028(12) 0.0596(4) Uani 1 1 d . . . . .
H3'A H 0.277(3) 0.5941(17) 0.4545(15) 0.071(6) Uiso 1 1 d . . . . .
H3'B H 0.417(3) 0.5436(16) 0.5079(16) 0.065(6) Uiso 1 1 d . . . . .
H3'C H 0.259(3) 0.4850(18) 0.4981(17) 0.079(7) Uiso 1 1 d . . . . .
C2 C 0.60225(16) 0.23783(10) 0.37589(10) 0.0414(3) Uani 1 1 d . . . . .
C2' C 0.5007(4) 0.40087(16) 0.15334(11) 0.0757(7) Uani 1 1 d . . . . .
H2'A H 0.473(3) 0.4509(19) 0.1146(17) 0.084(7) Uiso 1 1 d . . . . .
H2'B H 0.443(3) 0.3468(19) 0.1335(17) 0.082(8) Uiso 1 1 d . . . . .
H2'C H 0.618(4) 0.388(2) 0.153(2) 0.109(10) Uiso 1 1 d . . . . .
C3 C 0.56500(19) 0.28820(11) 0.30062(9) 0.0457(3) Uani 1 1 d . . . . .
H3 H 0.588(2) 0.2621(13) 0.2442(12) 0.047(4) Uiso 1 1 d . . . . .
C1' C 0.7445(3) 0.12163(13) 0.29493(13) 0.0589(4) Uani 1 1 d . . . . .
H1'A H 0.667(3) 0.1064(16) 0.2524(15) 0.065(6) Uiso 1 1 d . . . . .
H1'B H 0.808(3) 0.0675(19) 0.3103(17) 0.081(7) Uiso 1 1 d . . . . .
H1'C H 0.811(3) 0.1738(18) 0.2674(16) 0.076(7) Uiso 1 1 d . . . . .
C4 C 0.49079(17) 0.37472(10) 0.30717(9) 0.0426(3) Uani 1 1 d . . . . .
C5 C 0.45543(16) 0.41235(10) 0.38930(9) 0.0408(3) Uani 1 1 d . . . . .
C6 C 0.49456(16) 0.36201(10) 0.46358(9) 0.0397(3) Uani 1 1 d . . . . .
H6 H 0.474(2) 0.3878(13) 0.5214(12) 0.045(4) Uiso 1 1 d . . . . .
C7 C 0.60167(15) 0.21754(10) 0.53888(9) 0.0393(3) Uani 1 1 d . . . . .
H7 H 0.697(2) 0.1782(12) 0.5296(11) 0.038(4) Uiso 1 1 d . . . . .
C8 C 0.46523(17) 0.15639(11) 0.56624(10) 0.0437(3) Uani 1 1 d . . . . .
H8A H 0.446(2) 0.1112(14) 0.5205(14) 0.059(5) Uiso 1 1 d . . . . .
H8B H 0.370(2) 0.2008(14) 0.5739(13) 0.053(5) Uiso 1 1 d . . . . .
C9 C 0.49864(19) 0.10519(11) 0.65172(10) 0.0459(3) Uani 1 1 d . . . . .
H9A H 0.406(2) 0.0791(14) 0.6767(13) 0.056(5) Uiso 1 1 d . . . . .
H9B H 0.576(3) 0.0527(16) 0.6441(14) 0.062(6) Uiso 1 1 d . . . . .
C10 C 0.56720(19) 0.17315(10) 0.71576(10) 0.0448(3) Uani 1 1 d . . . . .
C11 C 0.5601(3) 0.15091(13) 0.80639(12) 0.0653(5) Uani 1 1 d D . . . .
C12 C 0.6587(6) 0.3073(3) 0.8400(3) 0.0528(9) Uani 0.557(6) 1 d D . P A 1
C13 C 0.6973(2) 0.32260(12) 0.75178(11) 0.0540(4) Uani 1 1 d D . . . .
C14 C 0.63253(16) 0.25616(10) 0.69045(9) 0.0408(3) Uani 1 1 d . . . . .
C15 C 0.7712(2) 0.41108(13) 0.71842(13) 0.0568(4) Uani 1 1 d . . . . .
H15A H 0.692(3) 0.4515(18) 0.6903(17) 0.076(7) Uiso 1 1 d . . . . .
H15B H 0.845(3) 0.3995(19) 0.6716(17) 0.085(8) Uiso 1 1 d . . . . .
H15C H 0.823(3) 0.4431(18) 0.7626(17) 0.078(7) Uiso 1 1 d . . . . .
C16 C 0.6984(6) 0.3674(3) 0.9180(3) 0.0673(12) Uani 0.557(6) 1 d D . P A 1
H16A H 0.7435 0.4275 0.8972 0.081 Uiso 0.557(6) 1 calc R . P A 1
H16B H 0.6014 0.3825 0.9499 0.081 Uiso 0.557(6) 1 calc R . P A 1
C17 C 0.8093(6) 0.3228(3) 0.9798(3) 0.0835(15) Uani 0.557(6) 1 d D . P A 1
H17A H 0.9084 0.3115 0.9501 0.125 Uiso 0.557(6) 1 calc GR . P A 1
H17B H 0.7665 0.2628 1.0004 0.125 Uiso 0.557(6) 1 calc GR . P A 1
H17C H 0.8262 0.3648 1.0298 0.125 Uiso 0.557(6) 1 calc GR . P A 1
O5A O 0.6588(5) 0.2064(3) 0.8595(2) 0.0507(8) Uani 0.443(6) 1 d D . P A 2
C12A C 0.7251(6) 0.2893(4) 0.8316(3) 0.0475(10) Uani 0.443(6) 1 d D . P A 2
C16A C 0.8007(6) 0.3393(4) 0.9069(3) 0.0583(13) Uani 0.443(6) 1 d D . P A 2
H16C H 0.8581 0.2925 0.9425 0.070 Uiso 0.443(6) 1 calc R . P A 2
H16D H 0.8774 0.3848 0.8836 0.070 Uiso 0.443(6) 1 calc R . P A 2
C17A C 0.6900(8) 0.3905(5) 0.9645(4) 0.092(2) Uani 0.443(6) 1 d D . P A 2
H17D H 0.6385 0.4404 0.9310 0.138 Uiso 0.443(6) 1 calc GR . P A 2
H17E H 0.7467 0.4185 1.0136 0.138 Uiso 0.443(6) 1 calc GR . P A 2
H17F H 0.6119 0.3463 0.9868 0.138 Uiso 0.443(6) 1 calc GR . P A 2
O6A O 0.4802(19) 0.0884(9) 0.8383(10) 0.085(4) Uani 0.443(6) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C3' 1.421(2) . ?
O3 C5 1.3736(18) . ?
O2 C2' 1.423(2) . ?
O2 C4 1.3670(17) . ?
O1 C2 1.3733(18) . ?
O1 C1' 1.430(2) . ?
O4 C7 1.4566(17) . ?
O4 C14 1.3430(17) . ?
O5 C11 1.426(4) . ?
O5 C12 1.378(5) . ?
O6 C11 1.225(10) . ?
C1 C2 1.3918(19) . ?
C1 C6 1.394(2) . ?
C1 C7 1.5077(18) . ?
C2 C3 1.393(2) . ?
C3 C4 1.388(2) . ?
C4 C5 1.399(2) . ?
C5 C6 1.3839(19) . ?
C7 C8 1.5187(19) . ?
C8 C9 1.523(2) . ?
C9 C10 1.496(2) . ?
C10 C11 1.423(2) . ?
C10 C14 1.362(2) . ?
C11 O5A 1.414(4) . ?
C11 O6A 1.224(13) . ?
C12 C13 1.406(5) . ?
C12 C16 1.507(6) . ?
C13 C14 1.442(2) . ?
C13 C15 1.497(2) . ?
C13 C12A 1.331(5) . ?
C16 C17 1.485(6) . ?
O5A C12A 1.376(6) . ?
C12A C16A 1.501(6) . ?
C16A C17A 1.487(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C3' 116.97(12) . . ?
C4 O2 C2' 117.41(14) . . ?
C2 O1 C1' 117.67(13) . . ?
C14 O4 C7 117.77(11) . . ?
C12 O5 C11 120.3(3) . . ?
C2 C1 C6 119.08(12) . . ?
C2 C1 C7 119.87(12) . . ?
C6 C1 C7 121.02(12) . . ?
O1 C2 C1 116.13(12) . . ?
O1 C2 C3 123.60(13) . . ?
C1 C2 C3 120.27(13) . . ?
C4 C3 C2 120.02(13) . . ?
O2 C4 C3 124.40(13) . . ?
O2 C4 C5 115.41(13) . . ?
C3 C4 C5 120.19(12) . . ?
O3 C5 C4 115.53(12) . . ?
O3 C5 C6 125.29(13) . . ?
C6 C5 C4 119.18(13) . . ?
C5 C6 C1 121.24(13) . . ?
O4 C7 C1 106.53(11) . . ?
O4 C7 C8 111.28(11) . . ?
C1 C7 C8 112.18(11) . . ?
C7 C8 C9 111.30(12) . . ?
C10 C9 C8 109.21(12) . . ?
C11 C10 C9 118.56(14) . . ?
C14 C10 C9 122.31(13) . . ?
C14 C10 C11 119.12(14) . . ?
O6 C11 O5 115.0(5) . . ?
O6 C11 C10 127.1(5) . . ?
C10 C11 O5 117.58(19) . . ?
O5A C11 C10 114.2(2) . . ?
O6A C11 C10 125.0(8) . . ?
O6A C11 O5A 120.7(8) . . ?
O5 C12 C13 121.5(3) . . ?
O5 C12 C16 109.9(3) . . ?
C13 C12 C16 128.3(3) . . ?
C12 C13 C14 115.6(2) . . ?
C12 C13 C15 123.8(2) . . ?
C14 C13 C15 119.39(15) . . ?
C12A C13 C14 115.7(2) . . ?
C12A C13 C15 122.3(2) . . ?
O4 C14 C10 123.97(13) . . ?
O4 C14 C13 113.32(13) . . ?
C10 C14 C13 122.70(14) . . ?
C17 C16 C12 114.1(4) . . ?
C12A O5A C11 123.2(3) . . ?
C13 C12A O5A 120.9(4) . . ?
C13 C12A C16A 127.9(4) . . ?
O5A C12A C16A 110.3(4) . . ?
C17A C16A C12A 114.0(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20201229_za-39
_database_code_depnum_ccdc_archive 'CCDC 2124877'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2021-11-29 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 O8'
_chemical_formula_sum            'C21 H22 O8'
_chemical_formula_weight         402.38
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.53147(10)
_cell_length_b                   14.6487(2)
_cell_length_c                   28.5217(4)
_cell_angle_alpha                85.4988(12)
_cell_angle_beta                 85.9500(14)
_cell_angle_gamma                88.2776(15)
_cell_volume                     1882.16(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17086
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.5280
_cell_measurement_theta_min      3.0090
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.710
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            39721
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.327
_diffrn_reflns_theta_min         3.027
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  38.00   0.50    0.50    --   12.00  71.00 -70.39  104
  2  ω    -43.00  54.00   0.50    0.50    --   32.00 -55.00-174.28  194
  3  ω     14.00  46.00   0.50    0.50    --   40.00  72.00  13.53   64
  4  ω    100.00 127.00   0.50    0.50    --   40.00  72.00  13.53   54
  5  ω     25.00  78.00   0.50    1.00    --   48.00  72.00 -77.24  106
  6  ω    112.00 137.00   0.50    1.00    --   48.00  72.00 -77.24   50
  7  ω     29.00  55.00   0.50    1.00    --   56.00  73.00  52.88   52
  8  ω     94.00 121.00   0.50    1.00    --   56.00  72.00  88.61   54
  9  ω     29.00  55.00   0.50    1.00    --   56.00  72.00  88.61   52
 10  ω     29.00 104.00   0.50    1.00    --   56.00  73.00-140.54  150
 11  ω    106.00 145.00   0.50    1.00    --   56.00  73.00-140.54   78
 12  ω     32.00  61.00   0.50    1.00    --   60.00  74.00 164.91   58
 13  ω     32.00  57.00   0.50    1.00    --   60.00  74.00 143.19   50
 14  ω     32.00  59.00   0.50    1.00    --   60.00  75.00 105.93   54
 15  ω     36.00  75.00   0.50    1.00    --   64.00  74.00  73.59   78
 16  ω     37.00  72.00   0.50    1.00    --   64.00  75.00   4.37   70
 17  ω     46.00  72.00   0.50    1.00    --   72.00  73.00-178.42   52
 18  ω     44.00  87.00   0.50    1.00    --   72.00  74.00 131.32   86
 19  ω     44.00  70.00   0.50    1.00    --   72.00  75.00 -59.34   52
 20  ω     44.00  70.00   0.50    1.00    --   72.00  74.00  92.34   52
 21  ω     49.00  75.00   0.50    1.00    --   76.00  71.00 158.10   52
 22  ω     48.00  82.00   0.50    1.00    --   76.00  75.00 -36.68   68
 23  ω     57.00 100.00   0.50    1.00    --   84.00  73.00  95.84   86
 24  ω    136.00 171.00   0.50    1.00    --   84.00  73.00  95.84   70
 25  ω     69.00 117.00   0.50    1.00    --   94.60  69.00 -60.57   96
 26  ω     45.00 125.00   0.50    1.00    --   94.60 -82.00 -60.00  160
 27  ω    140.00 181.00   0.50    1.00    --   94.60  45.00 -90.00   82
 28  ω     69.00 174.00   0.50    1.00    --   94.60  68.00 -19.24  210
 29  ω     75.00 122.00   0.50    1.00    --   94.60  45.00 -90.00   94
 30  ω    147.00 173.00   0.50    1.00    --   94.60  62.00  10.40   52
 31  ω    124.00 179.00   0.50    1.00    --   94.60  74.00 155.96  110
 32  ω     66.00 121.00   0.50    1.00    --   94.60  75.00 170.69  110
 33  ω     75.00 117.00   0.50    1.00    --   94.60  62.00  10.40   84
 34  ω    148.00 175.00   0.50    1.00    --   94.60  45.00 120.00   54
 35  ω     66.00 100.00   0.50    1.00    --   94.60  74.00 155.96   68
 36  ω     45.00 119.00   0.50    1.00    --   94.60 -77.00   0.00  148
 37  ω    140.00 178.00   0.50    1.00    --   94.60  61.00  46.85   76
 38  ω    142.00 184.00   0.50    1.00    --   94.60  61.00  60.00   84
 39  ω     72.00  98.00   0.50    1.00    --   94.60  61.00  60.00   52
 40  ω     71.00 126.00   0.50    1.00    --   94.60  61.00-150.00  110
 41  ω     71.00 135.00   0.50    1.00    --   94.60  61.00  46.85  128
 42  ω    147.00 182.00   0.50    1.00    --   94.60  57.00 131.82   70
 43  ω     78.00 142.00   0.50    1.00    --   94.60  57.00 131.82  128
 44  ω     78.00 126.00   0.50    1.00    --   94.60 -82.00 150.00   96
 45  ω     71.00 182.00   0.50    1.00    --   94.60  61.00  30.00  222
 46  ω     83.00 143.00   0.50    1.00    --   94.60  45.00 120.00  120
 47  ω     71.00 168.00   0.50    1.00    --   94.60  61.00 -30.00  194
 48  ω      5.00  57.00   0.50    1.00    --   94.60 -82.00 150.00  104
 49  ω     67.00 148.00   0.50    1.00    --   94.60  73.00 -91.28  162
 50  ω    140.00 179.00   0.50    1.00    --   94.60  75.00 170.69   78
 51  ω     76.00 109.00   0.50    1.00    --   94.60 -82.00-150.00   66
 52  ω     71.00 159.00   0.50    1.00    --   94.60  60.00-128.18  176
 53  ω      9.00 125.00   0.50    1.00    --   94.60 -82.00  90.00  232
 54  ω     35.00 114.00   0.50    1.00    --   94.60 -61.00  90.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0092741000
_diffrn_orient_matrix_UB_12      -0.1027649000
_diffrn_orient_matrix_UB_13      -0.0077092000
_diffrn_orient_matrix_UB_21      0.0613672000
_diffrn_orient_matrix_UB_22      -0.0239488000
_diffrn_orient_matrix_UB_23      0.0520300000
_diffrn_orient_matrix_UB_31      -0.3352272000
_diffrn_orient_matrix_UB_32      0.0011044000
_diffrn_orient_matrix_UB_33      0.0135218000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6500
_reflns_number_total             7433
_reflns_odcompleteness_completeness 99.29
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         7433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+1.3664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1604
_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:
 C8(H8), C9(H9), C10(H10), C8A(H8A), C9A(H9A), C10A(H10A)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C11A(H11C,H11D), C18A(H18C,H18D)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C5A(H5A), C7A(H7A)
2.d Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C2"(H2"A,H2"B,H2"C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,H1CC), C17A(H17D,H17E,H17F),
 C19A(H19D,H19E,H19F)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2A)
;
_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 0.9872(5) -0.41189(11) 0.33494(6) 0.0489(5) Uani 1 1 d . . . . .
O2 O 1.1256(4) -0.24771(10) 0.30046(5) 0.0360(4) Uani 1 1 d . . . . .
H2 H 1.1457 -0.3035 0.3046 0.054 Uiso 1 1 calc GR . . . .
O3 O 0.9527(4) -0.05575(10) 0.26096(5) 0.0344(4) Uani 1 1 d . . . . .
O4 O 0.4448(3) -0.30485(9) 0.43304(5) 0.0306(3) Uani 1 1 d . . . . .
O5 O 1.1100(3) 0.02979(9) 0.31988(5) 0.0248(3) Uani 1 1 d . . . . .
O6 O 0.8410(3) 0.15896(9) 0.33701(5) 0.0260(3) Uani 1 1 d . . . . .
O7 O 1.2681(4) 0.12458(10) 0.48431(5) 0.0330(3) Uani 1 1 d . . . . .
O8 O 1.2792(3) 0.25736(9) 0.44128(5) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.7821(5) -0.27810(13) 0.36741(7) 0.0272(4) Uani 1 1 d . . . . .
C1' C 0.2431(5) -0.27070(14) 0.46899(7) 0.0313(5) Uani 1 1 d . . . . .
H1'A H 0.1006 -0.2296 0.4547 0.047 Uiso 1 1 calc GR . . . .
H1'B H 0.3509 -0.2387 0.4901 0.047 Uiso 1 1 calc GR . . . .
H1'C H 0.1429 -0.3210 0.4862 0.047 Uiso 1 1 calc GR . . . .
C2 C 0.9425(5) -0.21687(13) 0.33522(7) 0.0267(4) Uani 1 1 d . . . . .
C2" C 1.1331(7) -0.01426(19) 0.22208(8) 0.0522(7) Uani 1 1 d . . . . .
H2"A H 1.0262 -0.0110 0.1941 0.078 Uiso 1 1 calc GR . . . .
H2"B H 1.3114 -0.0504 0.2173 0.078 Uiso 1 1 calc GR . . . .
H2"C H 1.1825 0.0464 0.2289 0.078 Uiso 1 1 calc GR . . . .
C3 C 0.9176(4) -0.12224(13) 0.33875(7) 0.0243(4) Uani 1 1 d . . . . .
C4 C 0.7351(4) -0.08914(12) 0.37538(7) 0.0226(4) Uani 1 1 d . . . . .
C5 C 0.5732(4) -0.14842(13) 0.40774(7) 0.0237(4) Uani 1 1 d . . . . .
H5 H 0.4524 -0.1251 0.4320 0.028 Uiso 1 1 calc R . . . .
C6 C 0.5942(4) -0.24188(13) 0.40344(7) 0.0249(4) Uani 1 1 d . . . . .
C7 C 0.8190(6) -0.37576(15) 0.36412(8) 0.0388(5) Uani 1 1 d . . . . .
H7 H 0.7073 -0.4140 0.3856 0.047 Uiso 1 1 calc R . . . .
C8 C 1.0919(5) -0.05958(13) 0.30319(7) 0.0262(4) Uani 1 1 d . . . . .
H8 H 1.2924 -0.0855 0.2980 0.031 Uiso 1 1 calc R . . . .
C9 C 0.7256(4) 0.01278(12) 0.38182(7) 0.0227(4) Uani 1 1 d . . . . .
H9 H 0.5210 0.0316 0.3906 0.027 Uiso 1 1 calc R . . . .
C10 C 0.8224(4) 0.06250(12) 0.33510(7) 0.0241(4) Uani 1 1 d . . . . .
H10 H 0.6831 0.0501 0.3117 0.029 Uiso 1 1 calc R . . . .
C11 C 0.9215(4) 0.03556(12) 0.42084(7) 0.0239(4) Uani 1 1 d . . . . .
H11A H 0.8107 0.0270 0.4512 0.029 Uiso 1 1 calc R . . . .
H11B H 1.0919 -0.0061 0.4212 0.029 Uiso 1 1 calc R . . . .
C12 C 1.0248(4) 0.13253(12) 0.41352(7) 0.0232(4) Uani 1 1 d . . . . .
C13 C 1.1911(5) 0.16660(13) 0.44877(7) 0.0259(4) Uani 1 1 d . . . . .
C14 C 1.2108(5) 0.31358(13) 0.40244(7) 0.0263(4) Uani 1 1 d . . . . .
C15 C 1.0601(4) 0.28290(12) 0.36801(7) 0.0253(4) Uani 1 1 d . . . . .
C16 C 0.9760(4) 0.18801(13) 0.37403(7) 0.0234(4) Uani 1 1 d . . . . .
C17 C 0.9749(5) 0.34036(14) 0.32465(8) 0.0324(5) Uani 1 1 d . . . . .
H17A H 1.0307 0.4025 0.3268 0.049 Uiso 1 1 calc GR . . . .
H17B H 0.7649 0.3384 0.3224 0.049 Uiso 1 1 calc GR . . . .
H17C H 1.0749 0.3168 0.2972 0.049 Uiso 1 1 calc GR . . . .
C18 C 1.3349(5) 0.40665(13) 0.40509(8) 0.0305(5) Uani 1 1 d . . . . .
H18A H 1.2854 0.4452 0.3774 0.037 Uiso 1 1 calc R . . . .
H18B H 1.5489 0.4009 0.4046 0.037 Uiso 1 1 calc R . . . .
C19 C 1.2199(6) 0.45352(15) 0.44923(8) 0.0372(5) Uani 1 1 d . . . . .
H19A H 1.3044 0.5129 0.4486 0.056 Uiso 1 1 calc GR . . . .
H19B H 1.2751 0.4170 0.4768 0.056 Uiso 1 1 calc GR . . . .
H19C H 1.0083 0.4599 0.4499 0.056 Uiso 1 1 calc GR . . . .
O1A O 0.4343(5) -0.03054(13) 0.06652(8) 0.0564(5) Uani 1 1 d . . . . .
O2A O 0.5347(4) 0.07677(10) 0.13032(6) 0.0364(4) Uani 1 1 d . . . . .
H2A H 0.5480 0.0300 0.1162 0.055 Uiso 1 1 calc GR . . . .
O3A O 0.3480(3) 0.20704(10) 0.20646(5) 0.0313(3) Uani 1 1 d . . . . .
O4A O -0.0899(4) 0.16033(11) 0.00678(6) 0.0378(4) Uani 1 1 d . . . . .
O5A O 0.5264(3) 0.34282(10) 0.16864(5) 0.0308(3) Uani 1 1 d . . . . .
O6A O 0.2775(4) 0.47655(10) 0.18122(5) 0.0368(4) Uani 1 1 d . . . . .
O7A O 0.7350(4) 0.59376(12) 0.03568(6) 0.0463(4) Uani 1 1 d . . . . .
O8A O 0.7758(4) 0.66361(11) 0.10096(6) 0.0437(4) Uani 1 1 d . . . . .
C1A C 0.2223(5) 0.11799(15) 0.06730(8) 0.0328(5) Uani 1 1 d . . . . .
C1B C -0.2680(5) 0.22796(16) -0.01837(8) 0.0382(5) Uani 1 1 d . . . . .
H1BA H -0.3598 0.2002 -0.0429 0.057 Uiso 1 1 calc GR . . . .
H1BB H -0.1451 0.2767 -0.0321 0.057 Uiso 1 1 calc GR . . . .
H1BC H -0.4181 0.2522 0.0030 0.057 Uiso 1 1 calc GR . . . .
C1C C 0.5200(5) 0.20513(17) 0.24637(8) 0.0369(5) Uani 1 1 d . . . . .
H1CA H 0.7030 0.1722 0.2400 0.055 Uiso 1 1 calc GR . . . .
H1CB H 0.4125 0.1752 0.2732 0.055 Uiso 1 1 calc GR . . . .
H1CC H 0.5605 0.2667 0.2529 0.055 Uiso 1 1 calc GR . . . .
C2A C 0.3641(5) 0.13948(14) 0.10716(7) 0.0302(4) Uani 1 1 d . . . . .
C3A C 0.3371(5) 0.22709(14) 0.12356(7) 0.0296(4) Uani 1 1 d . . . . .
C4A C 0.1699(5) 0.29397(14) 0.09914(7) 0.0295(4) Uani 1 1 d . . . . .
C5A C 0.0238(5) 0.27432(15) 0.05961(7) 0.0310(5) Uani 1 1 d . . . . .
H5A H -0.0871 0.3197 0.0437 0.037 Uiso 1 1 calc R . . . .
C6A C 0.0457(5) 0.18666(15) 0.04426(7) 0.0310(5) Uani 1 1 d . . . . .
C7A C 0.2751(6) 0.03024(17) 0.04880(10) 0.0468(6) Uani 1 1 d . . . . .
H7A H 0.1834 0.0186 0.0218 0.056 Uiso 1 1 calc R . . . .
C8A C 0.4988(5) 0.24698(14) 0.16546(7) 0.0300(4) Uani 1 1 d . . . . .
H8A H 0.6976 0.2189 0.1624 0.036 Uiso 1 1 calc R . . . .
C9A C 0.1605(5) 0.39123(14) 0.11409(7) 0.0303(4) Uani 1 1 d . . . . .
H9A H -0.0422 0.4160 0.1126 0.036 Uiso 1 1 calc R . . . .
C10A C 0.2462(5) 0.38909(14) 0.16450(8) 0.0318(5) Uani 1 1 d . . . . .
H10A H 0.0967 0.3557 0.1850 0.038 Uiso 1 1 calc R . . . .
C11A C 0.3680(5) 0.45175(14) 0.08063(8) 0.0313(5) Uani 1 1 d . . . . .
H11C H 0.5336 0.4146 0.0688 0.038 Uiso 1 1 calc R . . . .
H11D H 0.2618 0.4764 0.0539 0.038 Uiso 1 1 calc R . . . .
C12A C 0.4820(5) 0.52913(14) 0.10510(8) 0.0322(5) Uani 1 1 d . . . . .
C13A C 0.6647(6) 0.59410(15) 0.07754(8) 0.0368(5) Uani 1 1 d . . . . .
C14A C 0.7247(6) 0.67093(17) 0.14868(9) 0.0417(6) Uani 1 1 d . . . . .
C15A C 0.5576(6) 0.61035(16) 0.17575(9) 0.0393(5) Uani 1 1 d . . . . .
C16A C 0.4366(5) 0.53721(15) 0.15209(8) 0.0330(5) Uani 1 1 d . . . . .
C17A C 0.4970(7) 0.6124(2) 0.22807(10) 0.0526(7) Uani 1 1 d . . . . .
H17D H 0.6105 0.5644 0.2438 0.079 Uiso 1 1 calc GR . . . .
H17E H 0.2901 0.6034 0.2362 0.079 Uiso 1 1 calc GR . . . .
H17F H 0.5515 0.6706 0.2377 0.079 Uiso 1 1 calc GR . . . .
C18A C 0.8778(7) 0.75292(19) 0.16233(11) 0.0527(7) Uani 1 1 d . . . . .
H18C H 1.0897 0.7446 0.1560 0.063 Uiso 1 1 calc R . . . .
H18D H 0.8392 0.7585 0.1959 0.063 Uiso 1 1 calc R . . . .
C19A C 0.7752(9) 0.8395(2) 0.13569(14) 0.0700(9) Uani 1 1 d . . . . .
H19D H 0.7885 0.8312 0.1025 0.105 Uiso 1 1 calc GR . . . .
H19E H 0.8980 0.8890 0.1416 0.105 Uiso 1 1 calc GR . . . .
H19F H 0.5736 0.8535 0.1459 0.105 Uiso 1 1 calc GR . . . .


_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 C7 1.228(3) . ?
O2 H2 0.8200 . ?
O2 C2 1.344(2) . ?
O3 C2" 1.436(3) . ?
O3 C8 1.395(3) . ?
O4 C1' 1.434(2) . ?
O4 C6 1.362(2) . ?
O5 C8 1.434(2) . ?
O5 C10 1.425(2) . ?
O6 C10 1.424(2) . ?
O6 C16 1.359(2) . ?
O7 C13 1.211(3) . ?
O8 C13 1.396(2) . ?
O8 C14 1.375(2) . ?
C1 C2 1.411(3) . ?
C1 C6 1.413(3) . ?
C1 C7 1.445(3) . ?
C1' H1'A 0.9600 . ?
C1' H1'B 0.9600 . ?
C1' H1'C 0.9600 . ?
C2 C3 1.398(3) . ?
C2" H2"A 0.9600 . ?
C2" H2"B 0.9600 . ?
C2" H2"C 0.9600 . ?
C3 C4 1.394(3) . ?
C3 C8 1.510(3) . ?
C4 C5 1.400(3) . ?
C4 C9 1.517(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9800 . ?
C9 H9 0.9800 . ?
C9 C10 1.511(3) . ?
C9 C11 1.534(3) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.503(2) . ?
C12 C13 1.427(3) . ?
C12 C16 1.364(3) . ?
C14 C15 1.347(3) . ?
C14 C18 1.500(3) . ?
C15 C16 1.446(3) . ?
C15 C17 1.507(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.533(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O1A C7A 1.229(3) . ?
O2A H2A 0.8200 . ?
O2A C2A 1.346(3) . ?
O3A C1C 1.422(3) . ?
O3A C8A 1.407(2) . ?
O4A C1B 1.439(3) . ?
O4A C6A 1.357(3) . ?
O5A C8A 1.424(2) . ?
O5A C10A 1.429(3) . ?
O6A C10A 1.416(3) . ?
O6A C16A 1.356(3) . ?
O7A C13A 1.214(3) . ?
O8A C13A 1.386(3) . ?
O8A C14A 1.376(3) . ?
C1A C2A 1.406(3) . ?
C1A C6A 1.416(3) . ?
C1A C7A 1.435(3) . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?
C1C H1CA 0.9600 . ?
C1C H1CB 0.9600 . ?
C1C H1CC 0.9600 . ?
C2A C3A 1.399(3) . ?
C3A C4A 1.393(3) . ?
C3A C8A 1.497(3) . ?
C4A C5A 1.400(3) . ?
C4A C9A 1.517(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.387(3) . ?
C7A H7A 0.9300 . ?
C8A H8A 0.9800 . ?
C9A H9A 0.9800 . ?
C9A C10A 1.513(3) . ?
C9A C11A 1.540(3) . ?
C10A H10A 0.9800 . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.500(3) . ?
C12A C13A 1.431(3) . ?
C12A C16A 1.355(3) . ?
C14A C15A 1.344(4) . ?
C14A C18A 1.496(4) . ?
C15A C16A 1.451(3) . ?
C15A C17A 1.500(4) . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?
C18A C19A 1.505(4) . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 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 O2 H2 109.5 . . ?
C8 O3 C2" 112.34(18) . . ?
C6 O4 C1' 117.20(15) . . ?
C10 O5 C8 109.98(14) . . ?
C16 O6 C10 116.56(15) . . ?
C14 O8 C13 123.14(16) . . ?
C2 C1 C6 118.63(17) . . ?
C2 C1 C7 120.06(19) . . ?
C6 C1 C7 121.27(19) . . ?
O4 C1' H1'A 109.5 . . ?
O4 C1' H1'B 109.5 . . ?
O4 C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
O2 C2 C1 121.06(18) . . ?
O2 C2 C3 117.95(18) . . ?
C3 C2 C1 120.98(18) . . ?
O3 C2" H2"A 109.5 . . ?
O3 C2" H2"B 109.5 . . ?
O3 C2" H2"C 109.5 . . ?
H2"A C2" H2"B 109.5 . . ?
H2"A C2" H2"C 109.5 . . ?
H2"B C2" H2"C 109.5 . . ?
C2 C3 C8 118.94(17) . . ?
C4 C3 C2 118.75(18) . . ?
C4 C3 C8 122.31(17) . . ?
C3 C4 C5 121.39(17) . . ?
C3 C4 C9 119.10(17) . . ?
C5 C4 C9 119.41(17) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.52(18) . . ?
C6 C5 H5 120.2 . . ?
O4 C6 C1 115.47(17) . . ?
O4 C6 C5 123.83(18) . . ?
C5 C6 C1 120.69(18) . . ?
O1 C7 C1 124.7(2) . . ?
O1 C7 H7 117.7 . . ?
C1 C7 H7 117.7 . . ?
O3 C8 O5 111.28(16) . . ?
O3 C8 C3 107.86(16) . . ?
O3 C8 H8 109.0 . . ?
O5 C8 C3 110.75(15) . . ?
O5 C8 H8 109.0 . . ?
C3 C8 H8 109.0 . . ?
C4 C9 H9 108.7 . . ?
C4 C9 C11 111.34(15) . . ?
C10 C9 C4 107.95(15) . . ?
C10 C9 H9 108.7 . . ?
C10 C9 C11 111.43(16) . . ?
C11 C9 H9 108.7 . . ?
O5 C10 C9 109.32(15) . . ?
O5 C10 H10 109.0 . . ?
O6 C10 O5 106.74(14) . . ?
O6 C10 C9 113.66(15) . . ?
O6 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C9 C11 H11A 109.3 . . ?
C9 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C9 111.42(16) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C13 C12 C11 118.30(17) . . ?
C16 C12 C11 122.95(18) . . ?
C16 C12 C13 118.70(17) . . ?
O7 C13 O8 116.32(18) . . ?
O7 C13 C12 126.83(18) . . ?
O8 C13 C12 116.84(17) . . ?
O8 C14 C18 110.04(17) . . ?
C15 C14 O8 121.47(17) . . ?
C15 C14 C18 128.46(19) . . ?
C14 C15 C16 116.49(18) . . ?
C14 C15 C17 124.60(17) . . ?
C16 C15 C17 118.91(18) . . ?
O6 C16 C12 122.73(17) . . ?
O6 C16 C15 114.15(17) . . ?
C12 C16 C15 123.11(18) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 108.9 . . ?
C14 C18 H18B 108.9 . . ?
C14 C18 C19 113.43(17) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2A O2A H2A 109.5 . . ?
C8A O3A C1C 112.19(16) . . ?
C6A O4A C1B 117.54(17) . . ?
C8A O5A C10A 110.54(16) . . ?
C16A O6A C10A 116.01(16) . . ?
C14A O8A C13A 123.32(19) . . ?
C2A C1A C6A 118.60(19) . . ?
C2A C1A C7A 119.9(2) . . ?
C6A C1A C7A 121.3(2) . . ?
O4A C1B H1BA 109.5 . . ?
O4A C1B H1BB 109.5 . . ?
O4A C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
O3A C1C H1CA 109.5 . . ?
O3A C1C H1CB 109.5 . . ?
O3A C1C H1CC 109.5 . . ?
H1CA C1C H1CB 109.5 . . ?
H1CA C1C H1CC 109.5 . . ?
H1CB C1C H1CC 109.5 . . ?
O2A C2A C1A 120.99(19) . . ?
O2A C2A C3A 117.8(2) . . ?
C3A C2A C1A 121.2(2) . . ?
C2A C3A C8A 119.00(19) . . ?
C4A C3A C2A 118.8(2) . . ?
C4A C3A C8A 122.18(19) . . ?
C3A C4A C5A 121.3(2) . . ?
C3A C4A C9A 119.20(19) . . ?
C5A C4A C9A 119.40(19) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A C4A 119.6(2) . . ?
C6A C5A H5A 120.2 . . ?
O4A C6A C1A 115.30(19) . . ?
O4A C6A C5A 124.2(2) . . ?
C5A C6A C1A 120.5(2) . . ?
O1A C7A C1A 123.9(2) . . ?
O1A C7A H7A 118.0 . . ?
C1A C7A H7A 118.0 . . ?
O3A C8A O5A 110.49(16) . . ?
O3A C8A C3A 108.88(17) . . ?
O3A C8A H8A 108.5 . . ?
O5A C8A C3A 111.75(17) . . ?
O5A C8A H8A 108.5 . . ?
C3A C8A H8A 108.5 . . ?
C4A C9A H9A 108.8 . . ?
C4A C9A C11A 110.27(17) . . ?
C10A C9A C4A 108.68(17) . . ?
C10A C9A H9A 108.8 . . ?
C10A C9A C11A 111.49(18) . . ?
C11A C9A H9A 108.8 . . ?
O5A C10A C9A 109.74(17) . . ?
O5A C10A H10A 108.9 . . ?
O6A C10A O5A 105.94(17) . . ?
O6A C10A C9A 114.43(17) . . ?
O6A C10A H10A 108.9 . . ?
C9A C10A H10A 108.9 . . ?
C9A C11A H11C 109.3 . . ?
C9A C11A H11D 109.3 . . ?
H11C C11A H11D 108.0 . . ?
C12A C11A C9A 111.48(18) . . ?
C12A C11A H11C 109.3 . . ?
C12A C11A H11D 109.3 . . ?
C13A C12A C11A 117.64(19) . . ?
C16A C12A C11A 123.5(2) . . ?
C16A C12A C13A 118.7(2) . . ?
O7A C13A O8A 116.7(2) . . ?
O7A C13A C12A 126.4(2) . . ?
O8A C13A C12A 117.0(2) . . ?
O8A C14A C18A 109.4(2) . . ?
C15A C14A O8A 121.3(2) . . ?
C15A C14A C18A 129.3(2) . . ?
C14A C15A C16A 116.6(2) . . ?
C14A C15A C17A 124.5(2) . . ?
C16A C15A C17A 118.9(2) . . ?
O6A C16A C15A 114.1(2) . . ?
C12A C16A O6A 122.7(2) . . ?
C12A C16A C15A 123.1(2) . . ?
C15A C17A H17D 109.5 . . ?
C15A C17A H17E 109.5 . . ?
C15A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C14A C18A H18C 109.3 . . ?
C14A C18A H18D 109.3 . . ?
C14A C18A C19A 111.7(2) . . ?
H18C C18A H18D 107.9 . . ?
C19A C18A H18C 109.3 . . ?
C19A C18A H18D 109.3 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?

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 O1 0.82 1.88 2.603(2) 145.7 .
O2A H2A O1A 0.82 1.84 2.569(2) 147.1 .

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
O2 C2 C3 C4 -178.25(18) . . . . ?
O2 C2 C3 C8 1.0(3) . . . . ?
O8 C14 C15 C16 -0.2(3) . . . . ?
O8 C14 C15 C17 179.52(18) . . . . ?
O8 C14 C18 C19 -58.9(2) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C3 C8 -179.48(19) . . . . ?
C1' O4 C6 C1 -177.69(18) . . . . ?
C1' O4 C6 C5 3.4(3) . . . . ?
C2 C1 C6 O4 179.59(18) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C2 C1 C7 O1 1.0(4) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 C9 175.18(18) . . . . ?
C2 C3 C8 O3 75.2(2) . . . . ?
C2 C3 C8 O5 -162.76(18) . . . . ?
C2" O3 C8 O5 70.9(2) . . . . ?
C2" O3 C8 C3 -167.46(19) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C9 C10 23.1(2) . . . . ?
C3 C4 C9 C11 -99.5(2) . . . . ?
C4 C3 C8 O3 -105.5(2) . . . . ?
C4 C3 C8 O5 16.5(3) . . . . ?
C4 C5 C6 O4 -179.76(18) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C4 C9 C10 O5 -57.2(2) . . . . ?
C4 C9 C10 O6 -176.32(15) . . . . ?
C4 C9 C11 C12 154.19(16) . . . . ?
C5 C4 C9 C10 -160.26(18) . . . . ?
C5 C4 C9 C11 77.1(2) . . . . ?
C6 C1 C2 O2 179.62(19) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C1 C7 O1 -177.0(2) . . . . ?
C7 C1 C2 O2 1.6(3) . . . . ?
C7 C1 C2 C3 -177.8(2) . . . . ?
C7 C1 C6 O4 -2.4(3) . . . . ?
C7 C1 C6 C5 176.5(2) . . . . ?
C8 O5 C10 O6 -162.25(14) . . . . ?
C8 O5 C10 C9 74.41(19) . . . . ?
C8 C3 C4 C5 179.40(18) . . . . ?
C8 C3 C4 C9 -4.1(3) . . . . ?
C9 C4 C5 C6 -176.49(18) . . . . ?
C9 C11 C12 C13 175.36(17) . . . . ?
C9 C11 C12 C16 -7.1(3) . . . . ?
C10 O5 C8 O3 69.51(19) . . . . ?
C10 O5 C8 C3 -50.5(2) . . . . ?
C10 O6 C16 C12 -16.4(3) . . . . ?
C10 O6 C16 C15 164.22(16) . . . . ?
C10 C9 C11 C12 33.6(2) . . . . ?
C11 C9 C10 O5 65.38(19) . . . . ?
C11 C9 C10 O6 -53.8(2) . . . . ?
C11 C12 C13 O7 2.3(3) . . . . ?
C11 C12 C13 O8 -178.93(16) . . . . ?
C11 C12 C16 O6 -3.0(3) . . . . ?
C11 C12 C16 C15 176.36(18) . . . . ?
C13 O8 C14 C15 -2.2(3) . . . . ?
C13 O8 C14 C18 179.50(17) . . . . ?
C13 C12 C16 O6 174.57(17) . . . . ?
C13 C12 C16 C15 -6.1(3) . . . . ?
C14 O8 C13 O7 179.53(18) . . . . ?
C14 O8 C13 C12 0.6(3) . . . . ?
C14 C15 C16 O6 -176.10(17) . . . . ?
C14 C15 C16 C12 4.5(3) . . . . ?
C15 C14 C18 C19 123.0(2) . . . . ?
C16 O6 C10 O5 -75.47(19) . . . . ?
C16 O6 C10 C9 45.1(2) . . . . ?
C16 C12 C13 O7 -175.4(2) . . . . ?
C16 C12 C13 O8 3.4(3) . . . . ?
C17 C15 C16 O6 4.1(3) . . . . ?
C17 C15 C16 C12 -175.28(19) . . . . ?
C18 C14 C15 C16 177.70(19) . . . . ?
C18 C14 C15 C17 -2.5(3) . . . . ?
O2A C2A C3A C4A 177.78(18) . . . . ?
O2A C2A C3A C8A 0.3(3) . . . . ?
O8A C14A C15A C16A 0.3(4) . . . . ?
O8A C14A C15A C17A 178.6(2) . . . . ?
O8A C14A C18A C19A 58.2(3) . . . . ?
C1A C2A C3A C4A -1.1(3) . . . . ?
C1A C2A C3A C8A -178.49(18) . . . . ?
C1B O4A C6A C1A -178.98(18) . . . . ?
C1B O4A C6A C5A -0.2(3) . . . . ?
C1C O3A C8A O5A -70.0(2) . . . . ?
C1C O3A C8A C3A 166.96(18) . . . . ?
C2A C1A C6A O4A -178.45(18) . . . . ?
C2A C1A C6A C5A 2.7(3) . . . . ?
C2A C1A C7A O1A 2.1(4) . . . . ?
C2A C3A C4A C5A 1.7(3) . . . . ?
C2A C3A C4A C9A -174.83(18) . . . . ?
C2A C3A C8A O3A -76.2(2) . . . . ?
C2A C3A C8A O5A 161.51(18) . . . . ?
C3A C4A C5A C6A -0.1(3) . . . . ?
C3A C4A C9A C10A -21.0(3) . . . . ?
C3A C4A C9A C11A 101.5(2) . . . . ?
C4A C3A C8A O3A 106.5(2) . . . . ?
C4A C3A C8A O5A -15.8(3) . . . . ?
C4A C5A C6A O4A 179.15(19) . . . . ?
C4A C5A C6A C1A -2.1(3) . . . . ?
C4A C9A C10A O5A 54.6(2) . . . . ?
C4A C9A C10A O6A 173.49(17) . . . . ?
C4A C9A C11A C12A -151.87(19) . . . . ?
C5A C4A C9A C10A 162.39(18) . . . . ?
C5A C4A C9A C11A -75.1(2) . . . . ?
C6A C1A C2A O2A -179.90(19) . . . . ?
C6A C1A C2A C3A -1.1(3) . . . . ?
C6A C1A C7A O1A 177.5(3) . . . . ?
C7A C1A C2A O2A -4.4(3) . . . . ?
C7A C1A C2A C3A 174.4(2) . . . . ?
C7A C1A C6A O4A 6.1(3) . . . . ?
C7A C1A C6A C5A -172.8(2) . . . . ?
C8A O5A C10A O6A 163.76(15) . . . . ?
C8A O5A C10A C9A -72.2(2) . . . . ?
C8A C3A C4A C5A 179.04(18) . . . . ?
C8A C3A C4A C9A 2.5(3) . . . . ?
C9A C4A C5A C6A 176.39(18) . . . . ?
C9A C11A C12A C13A -176.59(19) . . . . ?
C9A C11A C12A C16A 7.7(3) . . . . ?
C10A O5A C8A O3A -71.6(2) . . . . ?
C10A O5A C8A C3A 49.8(2) . . . . ?
C10A O6A C16A C12A 21.0(3) . . . . ?
C10A O6A C16A C15A -158.0(2) . . . . ?
C10A C9A C11A C12A -31.0(2) . . . . ?
C11A C9A C10A O5A -67.2(2) . . . . ?
C11A C9A C10A O6A 51.7(2) . . . . ?
C11A C12A C13A O7A 1.0(4) . . . . ?
C11A C12A C13A O8A -178.1(2) . . . . ?
C11A C12A C16A O6A -1.4(4) . . . . ?
C11A C12A C16A C15A 177.5(2) . . . . ?
C13A O8A C14A C15A -0.8(4) . . . . ?
C13A O8A C14A C18A 179.6(2) . . . . ?
C13A C12A C16A O6A -177.1(2) . . . . ?
C13A C12A C16A C15A 1.9(3) . . . . ?
C14A O8A C13A O7A -177.5(2) . . . . ?
C14A O8A C13A C12A 1.7(3) . . . . ?
C14A C15A C16A O6A 178.1(2) . . . . ?
C14A C15A C16A C12A -0.9(4) . . . . ?
C15A C14A C18A C19A -121.4(3) . . . . ?
C16A O6A C10A O5A 74.4(2) . . . . ?
C16A O6A C10A C9A -46.7(3) . . . . ?
C16A C12A C13A O7A 176.9(2) . . . . ?
C16A C12A C13A O8A -2.2(3) . . . . ?
C17A C15A C16A O6A -0.3(3) . . . . ?
C17A C15A C16A C12A -179.3(2) . . . . ?
C18A C14A C15A C16A 179.8(3) . . . . ?
C18A C14A C15A C17A -1.9(5) . . . . ?

_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 2.857
_oxdiff_exptl_absorpt_empirical_full_min 0.343
