# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2299447'
loop_
_audit_author_name
_audit_author_address
'Shao Y.'
;Southwest University
China
;
_audit_update_record             
;
2023-10-05 deposited with the CCDC.	2023-12-10 downloaded from the CCDC.
;
_audit_creation_date             2018-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C32 H31 Br O6'
_chemical_formula_sum            'C32 H31 Br O6'
_chemical_formula_weight         591.48
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   10.8450(5)
_cell_length_b                   11.7874(6)
_cell_length_c                   11.0385(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.286(5)
_cell_angle_gamma                90.00
_cell_volume                     1399.71(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1481
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.4190
_cell_measurement_theta_min      3.9530
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_T_max  0.773
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5394
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.31
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   19.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00    5.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -46.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000 -180.0000 111

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00  101.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -120.0000 58
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0063172000
_diffrn_orient_matrix_UB_12      0.0546370000
_diffrn_orient_matrix_UB_13      0.0253888000
_diffrn_orient_matrix_UB_21      0.0218692000
_diffrn_orient_matrix_UB_22      0.0249664000
_diffrn_orient_matrix_UB_23      -0.0517234000
_diffrn_orient_matrix_UB_31      -0.0618886000
_diffrn_orient_matrix_UB_32      0.0032437000
_diffrn_orient_matrix_UB_33      -0.0296326000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3105
_reflns_number_total             3860
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0296P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0865
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C23(H23A,H23B), C24(H24A,H24B),
 C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19),
 C20(H20), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br -0.19920(4) -0.86347(5) -0.16860(4) 0.05300(17) Uani 1 d . . .
O1 O -0.3961(3) -1.3610(4) 0.0335(2) 0.0459(7) Uani 1 d . . .
O2 O -0.4508(3) -1.3792(4) 0.2285(3) 0.0571(9) Uani 1 d . . .
O3 O -0.4078(3) -1.1772(3) -0.1601(2) 0.0409(8) Uani 1 d . . .
O4 O -0.3516(3) -0.7059(3) 0.0461(3) 0.0525(9) Uani 1 d . . .
H4 H -0.4175 -0.7219 0.0711 0.079 Uiso 1 calc . . GR
O5 O 0.1734(3) -1.0513(3) 0.2328(3) 0.0473(9) Uani 1 d . . .
O6 O -0.0668(2) -1.0419(3) 0.2675(2) 0.0329(7) Uani 1 d . . .
C1 C -0.3290(3) -1.1619(4) 0.0517(3) 0.0281(10) Uani 1 d . . .
C2 C -0.3152(3) -1.0685(4) 0.1326(4) 0.0275(10) Uani 1 d . . .
C3 C -0.3495(4) -1.0805(4) 0.2500(4) 0.0375(11) Uani 1 d . . .
H3 H -0.3399 -1.0188 0.3028 0.045 Uiso 1 calc . . R
C4 C -0.3973(4) -1.1805(4) 0.2907(4) 0.0414(12) Uani 1 d . . .
H4A H -0.4217 -1.1859 0.3682 0.050 Uiso 1 calc . . R
C5 C -0.4069(4) -1.2702(4) 0.2131(4) 0.0393(12) Uani 1 d . . .
C6 C -0.3741(4) -1.2594(4) 0.0957(4) 0.0349(11) Uani 1 d . . .
C7 C -0.4291(5) -1.4386(5) 0.1234(5) 0.0563(15) Uani 1 d . . .
H7A H -0.5034 -1.4800 0.0912 0.068 Uiso 1 calc . . R
H7B H -0.3625 -1.4928 0.1437 0.068 Uiso 1 calc . . R
C8 C -0.2973(4) -1.1612(4) -0.0776(4) 0.0357(11) Uani 1 d . . .
H8A H -0.2592 -1.0894 -0.0944 0.043 Uiso 1 calc . . R
H8B H -0.2386 -1.2214 -0.0880 0.043 Uiso 1 calc . . R
C9 C -0.3833(5) -1.1758(7) -0.2834(4) 0.081(2) Uani 1 d . . .
H9A H -0.3159 -1.2277 -0.2931 0.097 Uiso 1 calc . . R
H9B H -0.3578 -1.1002 -0.3043 0.097 Uiso 1 calc . . R
C10 C -0.4957(4) -1.2094(5) -0.3668(4) 0.0454(13) Uani 1 d . . .
C11 C -0.5924(6) -1.1341(6) -0.3948(5) 0.0725(19) Uani 1 d . . .
H11 H -0.5846 -1.0608 -0.3637 0.087 Uiso 1 calc . . R
C12 C -0.6989(7) -1.1639(9) -0.4665(6) 0.104(3) Uani 1 d . . .
H12 H -0.7643 -1.1126 -0.4811 0.124 Uiso 1 calc . . R
C13 C -0.7087(7) -1.2683(10) -0.5160(6) 0.101(3) Uani 1 d . . .
H13 H -0.7813 -1.2881 -0.5657 0.121 Uiso 1 calc . . R
C14 C -0.6167(8) -1.3446(8) -0.4958(5) 0.089(3) Uani 1 d . . .
H14 H -0.6250 -1.4161 -0.5315 0.107 Uiso 1 calc . . R
C15 C -0.5079(6) -1.3152(6) -0.4203(5) 0.0665(18) Uani 1 d . . .
H15 H -0.4434 -1.3674 -0.4060 0.080 Uiso 1 calc . . R
C16 C -0.2601(4) -0.9570(4) 0.0949(4) 0.0315(11) Uani 1 d . . .
H16 H -0.3094 -0.9347 0.0180 0.038 Uiso 1 calc . . R
C17 C -0.1258(4) -0.9668(4) 0.0675(4) 0.0284(10) Uani 1 d . . .
C18 C -0.0850(4) -0.9268(4) -0.0401(4) 0.0355(11) Uani 1 d . . .
C19 C 0.0367(4) -0.9332(4) -0.0608(4) 0.0456(13) Uani 1 d . . .
H19 H 0.0596 -0.9091 -0.1350 0.055 Uiso 1 calc . . R
C20 C 0.1252(4) -0.9753(5) 0.0282(4) 0.0485(14) Uani 1 d . . .
H20 H 0.2080 -0.9780 0.0147 0.058 Uiso 1 calc . . R
C21 C 0.0918(4) -1.0129(4) 0.1364(4) 0.0377(11) Uani 1 d . . .
C22 C -0.0337(4) -1.0103(4) 0.1554(4) 0.0305(10) Uani 1 d . . .
C23 C -0.2703(4) -0.8581(6) 0.1846(3) 0.0380(10) Uani 1 d . . .
H23A H -0.3518 -0.8608 0.2119 0.046 Uiso 1 calc . . R
H23B H -0.2092 -0.8695 0.2557 0.046 Uiso 1 calc . . R
C24 C -0.2513(5) -0.7404(5) 0.1332(5) 0.0444(14) Uani 1 d . . .
H24A H -0.2413 -0.6861 0.1997 0.053 Uiso 1 calc . . R
H24B H -0.1754 -0.7401 0.0952 0.053 Uiso 1 calc . . R
C25 C 0.3031(4) -1.0560(6) 0.2170(5) 0.0601(16) Uani 1 d . . .
H25A H 0.3144 -1.1076 0.1521 0.090 Uiso 1 calc . . GR
H25B H 0.3505 -1.0816 0.2914 0.090 Uiso 1 calc . . GR
H25C H 0.3310 -0.9817 0.1971 0.090 Uiso 1 calc . . GR
C26 C -0.0577(4) -1.1614(4) 0.2932(4) 0.0378(11) Uani 1 d . . .
H26A H 0.0202 -1.1905 0.2716 0.045 Uiso 1 calc . . R
H26B H -0.1252 -1.2013 0.2450 0.045 Uiso 1 calc . . R
C27 C -0.0642(4) -1.1810(4) 0.4268(4) 0.0383(12) Uani 1 d . . .
C28 C -0.0510(6) -1.0967(6) 0.5112(5) 0.0696(19) Uani 1 d . . .
H28 H -0.0426 -1.0222 0.4857 0.084 Uiso 1 calc . . R
C29 C -0.0498(6) -1.1195(7) 0.6357(5) 0.084(2) Uani 1 d . . .
H29 H -0.0407 -1.0607 0.6924 0.100 Uiso 1 calc . . R
C30 C -0.0621(6) -1.2286(9) 0.6733(6) 0.082(2) Uani 1 d . . .
H30 H -0.0579 -1.2450 0.7561 0.098 Uiso 1 calc . . R
C31 C -0.0807(7) -1.3135(7) 0.5894(6) 0.095(3) Uani 1 d . . .
H31 H -0.0930 -1.3875 0.6146 0.114 Uiso 1 calc . . R
C32 C -0.0811(6) -1.2897(6) 0.4669(5) 0.0760(19) Uani 1 d . . .
H32 H -0.0930 -1.3484 0.4103 0.091 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.912(4) . ?
O1 C6 1.386(6) . ?
O1 C7 1.428(6) . ?
O2 C5 1.388(6) . ?
O2 C7 1.400(6) . ?
O3 C8 1.422(4) . ?
O3 C9 1.419(5) . ?
O4 H4 0.8200 . ?
O4 C24 1.417(5) . ?
O5 C21 1.372(5) . ?
O5 C25 1.441(5) . ?
O6 C22 1.383(5) . ?
O6 C26 1.438(5) . ?
C1 C2 1.414(6) . ?
C1 C6 1.363(6) . ?
C1 C8 1.510(5) . ?
C2 C3 1.400(6) . ?
C2 C16 1.524(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(7) . ?
C4 H4A 0.9300 . ?
C4 C5 1.356(7) . ?
C5 C6 1.392(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.485(6) . ?
C10 C11 1.379(8) . ?
C10 C15 1.379(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.346(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.341(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.398(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C17 1.529(6) . ?
C16 C23 1.543(7) . ?
C17 C18 1.400(6) . ?
C17 C22 1.399(5) . ?
C18 C19 1.371(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.365(6) . ?
C21 C22 1.403(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.523(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.503(6) . ?
C27 C28 1.357(8) . ?
C27 C32 1.376(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.399(8) . ?
C29 H29 0.9300 . ?
C29 C30 1.363(10) . ?
C30 H30 0.9300 . ?
C30 C31 1.362(10) . ?
C31 H31 0.9300 . ?
C31 C32 1.380(7) . ?
C32 H32 0.9300 . ?

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
C6 O1 C7 104.5(4) . . ?
C5 O2 C7 105.4(4) . . ?
C9 O3 C8 111.5(3) . . ?
C24 O4 H4 109.5 . . ?
C21 O5 C25 117.5(4) . . ?
C22 O6 C26 115.0(3) . . ?
C2 C1 C8 125.1(4) . . ?
C6 C1 C2 116.4(4) . . ?
C6 C1 C8 118.5(4) . . ?
C1 C2 C16 120.8(4) . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 C16 120.0(4) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.7(5) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4A 121.3 . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 H4A 121.3 . . ?
O2 C5 C6 109.3(5) . . ?
C4 C5 O2 130.1(4) . . ?
C4 C5 C6 120.6(5) . . ?
O1 C6 C5 109.5(4) . . ?
C1 C6 O1 126.8(4) . . ?
C1 C6 C5 123.7(5) . . ?
O1 C7 H7A 109.7 . . ?
O1 C7 H7B 109.7 . . ?
O2 C7 O1 109.8(4) . . ?
O2 C7 H7A 109.7 . . ?
O2 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O3 C8 C1 109.3(3) . . ?
O3 C8 H8A 109.8 . . ?
O3 C8 H8B 109.8 . . ?
C1 C8 H8A 109.8 . . ?
C1 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 C10 110.7(4) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C11 C10 C9 120.5(6) . . ?
C11 C10 C15 117.2(5) . . ?
C15 C10 C9 122.3(6) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.0(7) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.3(8) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.8(8) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.2(8) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 C14 120.5(7) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C2 C16 H16 106.1 . . ?
C2 C16 C17 113.9(4) . . ?
C2 C16 C23 114.4(4) . . ?
C17 C16 H16 106.1 . . ?
C17 C16 C23 109.4(3) . . ?
C23 C16 H16 106.1 . . ?
C18 C17 C16 123.6(4) . . ?
C22 C17 C16 120.3(4) . . ?
C22 C17 C18 115.9(4) . . ?
C17 C18 Br1 121.1(3) . . ?
C19 C18 Br1 116.4(3) . . ?
C19 C18 C17 122.5(4) . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
O5 C21 C22 115.7(4) . . ?
C20 C21 O5 124.7(4) . . ?
C20 C21 C22 119.6(4) . . ?
O6 C22 C17 118.4(4) . . ?
O6 C22 C21 119.6(4) . . ?
C17 C22 C21 121.7(4) . . ?
C16 C23 H23A 108.5 . . ?
C16 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
C24 C23 C16 115.1(4) . . ?
C24 C23 H23A 108.5 . . ?
C24 C23 H23B 108.5 . . ?
O4 C24 C23 112.7(4) . . ?
O4 C24 H24A 109.1 . . ?
O4 C24 H24B 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O6 C26 H26A 109.8 . . ?
O6 C26 H26B 109.8 . . ?
O6 C26 C27 109.5(4) . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C28 C27 C26 123.2(5) . . ?
C28 C27 C32 117.9(5) . . ?
C32 C27 C26 118.9(5) . . ?
C27 C28 H28 119.3 . . ?
C27 C28 C29 121.4(6) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.4(7) . . ?
C30 C29 H29 120.3 . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.9(6) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 119.9(7) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 121.4(7) . . ?
C27 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C18 C19 C20 178.5(4) . . . . ?
O2 C5 C6 O1 0.0(5) . . . . ?
O2 C5 C6 C1 179.2(4) . . . . ?
O3 C9 C10 C11 76.6(7) . . . . ?
O3 C9 C10 C15 -104.0(6) . . . . ?
O5 C21 C22 O6 1.9(6) . . . . ?
O5 C21 C22 C17 176.2(4) . . . . ?
O6 C26 C27 C28 -14.0(6) . . . . ?
O6 C26 C27 C32 167.7(5) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C1 C2 C16 C17 -62.3(5) . . . . ?
C1 C2 C16 C23 170.8(3) . . . . ?
C2 C1 C6 O1 179.6(4) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C2 C1 C8 O3 -115.4(4) . . . . ?
C2 C3 C4 C5 1.9(7) . . . . ?
C2 C16 C17 C18 128.5(4) . . . . ?
C2 C16 C17 C22 -56.1(5) . . . . ?
C2 C16 C23 C24 -163.1(4) . . . . ?
C3 C2 C16 C17 115.8(4) . . . . ?
C3 C2 C16 C23 -11.0(5) . . . . ?
C3 C4 C5 O2 -179.9(4) . . . . ?
C3 C4 C5 C6 -2.4(7) . . . . ?
C4 C5 C6 O1 -178.0(4) . . . . ?
C4 C5 C6 C1 1.2(7) . . . . ?
C5 O2 C7 O1 -11.9(5) . . . . ?
C6 O1 C7 O2 11.8(5) . . . . ?
C6 C1 C2 C3 -1.0(6) . . . . ?
C6 C1 C2 C16 177.2(4) . . . . ?
C6 C1 C8 O3 64.8(5) . . . . ?
C7 O1 C6 C1 173.7(4) . . . . ?
C7 O1 C6 C5 -7.1(5) . . . . ?
C7 O2 C5 C4 -175.0(5) . . . . ?
C7 O2 C5 C6 7.3(5) . . . . ?
C8 O3 C9 C10 171.7(5) . . . . ?
C8 C1 C2 C3 179.3(4) . . . . ?
C8 C1 C2 C16 -2.5(6) . . . . ?
C8 C1 C6 O1 -0.7(6) . . . . ?
C8 C1 C6 C5 -179.7(4) . . . . ?
C9 O3 C8 C1 179.2(5) . . . . ?
C9 C10 C11 C12 -177.0(5) . . . . ?
C9 C10 C15 C14 178.3(5) . . . . ?
C10 C11 C12 C13 -2.8(11) . . . . ?
C11 C10 C15 C14 -2.3(8) . . . . ?
C11 C12 C13 C14 0.7(12) . . . . ?
C12 C13 C14 C15 0.5(11) . . . . ?
C13 C14 C15 C10 0.3(9) . . . . ?
C15 C10 C11 C12 3.6(9) . . . . ?
C16 C2 C3 C4 -178.4(4) . . . . ?
C16 C17 C18 Br1 -3.9(6) . . . . ?
C16 C17 C18 C19 177.8(4) . . . . ?
C16 C17 C22 O6 -1.2(6) . . . . ?
C16 C17 C22 C21 -175.5(4) . . . . ?
C16 C23 C24 O4 71.1(5) . . . . ?
C17 C16 C23 C24 67.8(4) . . . . ?
C17 C18 C19 C20 -3.1(8) . . . . ?
C18 C17 C22 O6 174.5(4) . . . . ?
C18 C17 C22 C21 0.3(6) . . . . ?
C18 C19 C20 C21 1.3(8) . . . . ?
C19 C20 C21 O5 -176.8(5) . . . . ?
C19 C20 C21 C22 1.1(8) . . . . ?
C20 C21 C22 O6 -176.1(4) . . . . ?
C20 C21 C22 C17 -1.9(7) . . . . ?
C22 O6 C26 C27 165.8(3) . . . . ?
C22 C17 C18 Br1 -179.4(3) . . . . ?
C22 C17 C18 C19 2.2(7) . . . . ?
C23 C16 C17 C18 -102.0(5) . . . . ?
C23 C16 C17 C22 73.4(5) . . . . ?
C25 O5 C21 C20 -2.4(7) . . . . ?
C25 O5 C21 C22 179.7(4) . . . . ?
C26 O6 C22 C17 113.7(4) . . . . ?
C26 O6 C22 C21 -71.9(5) . . . . ?
C26 C27 C28 C29 -175.9(5) . . . . ?
C26 C27 C32 C31 176.3(5) . . . . ?
C27 C28 C29 C30 0.0(10) . . . . ?
C28 C27 C32 C31 -2.1(9) . . . . ?
C28 C29 C30 C31 -2.7(10) . . . . ?
C29 C30 C31 C32 3.0(10) . . . . ?
C30 C31 C32 C27 -0.6(10) . . . . ?
C32 C27 C28 C29 2.4(9) . . . . ?


_olex2_date_sample_data_collection 2018-08-21
_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_11b
_database_code_depnum_ccdc_archive 'CCDC 2299448'
loop_
_audit_author_name
_audit_author_address
'Shao Y.'
;Southwest University
China
;
_audit_update_record             
;
2023-10-05 deposited with the CCDC.	2023-12-10 downloaded from the CCDC.
;
_audit_creation_date             2022-06-09
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
shaoylc@lzu.edu.cn
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 O6'
_chemical_formula_sum            'C22 H22 O6'
_chemical_formula_weight         382.39
_chemical_absolute_configuration rm
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.41567(15)
_cell_length_b                   11.8302(3)
_cell_length_c                   18.4063(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1832.52(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5342
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.0250
_cell_measurement_theta_min      4.4200
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7110
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.392
_diffrn_reflns_theta_min         4.443
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  60.00   0.50    0.10    --  107.75 -57.00  60.00   50
  2  ω     36.00  61.00   0.50    0.10    --  107.75 -57.00  30.00   50
  3  ω    -16.00  22.00   0.50    0.05    --   47.57 -19.00-120.00   76
  4  ω    -27.00  -2.00   0.50    0.05    --   47.57 -19.00   0.00   50
  5  ω     35.00  60.00   0.50    0.10    --  107.75 -57.00 -60.00   50
  6  ω     38.00  63.00   0.50    0.10    --  107.75 -57.00 -90.00   50
  7  ω     36.00  61.00   0.50    0.10    --  107.75 -57.00-120.00   50
  8  ω     41.00  67.00   0.50    0.10    --  107.75 -99.00 -60.00   52
  9  ω     76.00 106.00   0.50    0.10    --  107.75 -99.00 -60.00   60
 10  ω    -75.00 -23.00   0.50    0.05    --  -47.57  99.00 102.00  104
 11  ω    -27.00  24.00   0.50    0.05    --  -47.57  19.00 -30.00  102
 12  ω    -57.00 -31.00   0.50    0.10    -- -100.00  57.00   0.00   52
 13  ω   -170.00-104.00   0.50    0.10    -- -100.00 -39.00  99.00  132
 14  ω   -144.00-102.00   0.50    0.10    -- -100.00 -99.00  -3.00   84
 15  ω   -169.00 -91.00   0.50    0.10    -- -100.00 -94.00-103.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1136794000
_diffrn_orient_matrix_UB_12      0.0800414000
_diffrn_orient_matrix_UB_13      0.0407861000
_diffrn_orient_matrix_UB_21      -0.1264535000
_diffrn_orient_matrix_UB_22      0.0942346000
_diffrn_orient_matrix_UB_23      -0.0025038000
_diffrn_orient_matrix_UB_31      -0.0679530000
_diffrn_orient_matrix_UB_32      -0.0414080000
_diffrn_orient_matrix_UB_33      0.0728897000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.572
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     0.726
_reflns_number_gt                3113
_reflns_number_total             3323
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1089 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(12)
_refine_ls_extinction_coef       0.0016(3)
_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   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.069
_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)+(0.0409P)²+0.1626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0870
_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), C8(H8), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3581(3) 0.28087(14) 0.55955(9) 0.0371(4) Uani 1 1 d . . . . .
O2 O 0.1011(2) 0.73061(15) 0.25145(9) 0.0332(4) Uani 1 1 d . . . . .
O3 O 0.3530(2) 0.80768(15) 0.26892(10) 0.0388(4) Uani 1 1 d . . . . .
O4 O 0.34708(18) 0.50120(13) 0.52722(8) 0.0245(3) Uani 1 1 d . . . . .
O5 O 0.83525(19) 0.58899(16) 0.54739(8) 0.0319(4) Uani 1 1 d . . . . .
O6 O 0.9973(2) 0.66728(17) 0.45915(9) 0.0361(4) Uani 1 1 d . . . . .
C1 C 0.2816(3) 0.38504(19) 0.34578(12) 0.0271(5) Uani 1 1 d . . . . .
C2 C 0.2796(3) 0.2707(2) 0.36264(13) 0.0319(5) Uani 1 1 d . . . . .
H2 H 0.256553 0.217844 0.325258 0.038 Uiso 1 1 calc R . . . .
C3 C 0.3100(3) 0.2309(2) 0.43226(13) 0.0341(5) Uani 1 1 d . . . . .
H3 H 0.313681 0.151979 0.441541 0.041 Uiso 1 1 calc R . . . .
C4 C 0.3349(3) 0.3075(2) 0.48800(12) 0.0299(5) Uani 1 1 d . . . . .
C5 C 0.3375(3) 0.42256(18) 0.47142(11) 0.0251(4) Uani 1 1 d . . . . .
C6 C 0.3211(3) 0.46213(19) 0.40107(11) 0.0241(4) Uani 1 1 d . . . . .
C7 C 0.3493(3) 0.58841(18) 0.38913(11) 0.0232(4) Uani 1 1 d . . . . .
H7 H 0.281442 0.630643 0.424540 0.028 Uiso 1 1 calc R . . . .
C8 C 0.2957(3) 0.62138(19) 0.31226(11) 0.0249(5) Uani 1 1 d . . . . .
H8 H 0.388062 0.609872 0.278893 0.030 Uiso 1 1 calc R . . . .
C9 C 0.1601(3) 0.5471(2) 0.28525(12) 0.0280(5) Uani 1 1 d . . . . .
H9 H 0.075546 0.544572 0.323397 0.034 Uiso 1 1 calc R . . . .
C10 C 0.2216(3) 0.4282(2) 0.27281(12) 0.0301(5) Uani 1 1 d . . . . .
H10A H 0.308979 0.428799 0.236773 0.036 Uiso 1 1 calc R . . . .
H10B H 0.135509 0.378903 0.254379 0.036 Uiso 1 1 calc R . . . .
C11 C 0.1010(3) 0.6175(2) 0.22226(13) 0.0350(5) Uani 1 1 d . . . . .
H11A H 0.173089 0.611381 0.179949 0.042 Uiso 1 1 calc R . . . .
H11B H -0.007302 0.594303 0.207446 0.042 Uiso 1 1 calc R . . . .
C12 C 0.2334(3) 0.7406(2) 0.30006(12) 0.0278(5) Uani 1 1 d . . . . .
H12 H 0.198042 0.774229 0.347207 0.033 Uiso 1 1 calc R . . . .
C13 C 0.5241(3) 0.61584(18) 0.40634(11) 0.0236(4) Uani 1 1 d . . . . .
C14 C 0.6236(3) 0.66535(18) 0.35488(12) 0.0261(5) Uani 1 1 d . . . . .
H14 H 0.579110 0.686103 0.309366 0.031 Uiso 1 1 calc R . . . .
C15 C 0.7860(3) 0.6863(2) 0.36640(13) 0.0297(5) Uani 1 1 d . . . . .
H15 H 0.851098 0.719936 0.330165 0.036 Uiso 1 1 calc R . . . .
C16 C 0.8449(3) 0.65574(19) 0.43257(12) 0.0278(5) Uani 1 1 d . . . . .
C17 C 0.7484(3) 0.60860(19) 0.48466(11) 0.0247(4) Uani 1 1 d . . . . .
C18 C 0.5894(3) 0.58734(18) 0.47560(11) 0.0233(4) Uani 1 1 d . . . . .
C19 C 0.5044(3) 0.5391(2) 0.54067(12) 0.0269(5) Uani 1 1 d . . . . .
H19A H 0.571(3) 0.475(2) 0.5623(14) 0.028(6) Uiso 1 1 d . . . . .
H19B H 0.494(3) 0.602(2) 0.5770(14) 0.029(6) Uiso 1 1 d . . . . .
C20 C 0.9978(3) 0.6065(2) 0.52662(13) 0.0331(5) Uani 1 1 d . . . . .
H20A H 1.054156 0.650579 0.564392 0.040 Uiso 1 1 calc R . . . .
H20B H 1.052483 0.533019 0.520663 0.040 Uiso 1 1 calc R . . . .
C21 C 0.3607(5) 0.1646(2) 0.57826(14) 0.0526(8) Uani 1 1 d . . . . .
H21A H 0.444595 0.126317 0.550701 0.079 Uiso 1 1 calc GR . . . .
H21B H 0.257731 0.130400 0.566607 0.079 Uiso 1 1 calc GR . . . .
H21C H 0.381591 0.156636 0.630387 0.079 Uiso 1 1 calc GR . . . .
C22 C 0.3106(3) 0.9235(2) 0.26266(16) 0.0448(7) Uani 1 1 d . . . . .
H22A H 0.210083 0.930065 0.236124 0.067 Uiso 1 1 calc GR . . . .
H22B H 0.394105 0.964158 0.236286 0.067 Uiso 1 1 calc GR . . . .
H22C H 0.298434 0.956248 0.311253 0.067 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 C4 1.368(3) . ?
O1 C21 1.419(3) . ?
O2 C11 1.442(3) . ?
O2 C12 1.433(3) . ?
O3 C12 1.404(3) . ?
O3 C22 1.421(3) . ?
O4 C5 1.388(3) . ?
O4 C19 1.420(3) . ?
O5 C17 1.386(3) . ?
O5 C20 1.435(3) . ?
O6 C16 1.379(3) . ?
O6 C20 1.435(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.406(3) . ?
C1 C10 1.523(3) . ?
C2 C3 1.389(4) . ?
C3 C4 1.385(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.529(3) . ?
C7 C8 1.535(3) . ?
C7 C13 1.540(3) . ?
C8 C9 1.524(3) . ?
C8 C12 1.521(3) . ?
C9 C10 1.517(3) . ?
C9 C11 1.512(3) . ?
C13 C14 1.393(3) . ?
C13 C18 1.429(3) . ?
C14 C15 1.405(3) . ?
C15 C16 1.364(3) . ?
C16 C17 1.375(3) . ?
C17 C18 1.372(3) . ?
C18 C19 1.507(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C21 117.34(19) . . ?
C12 O2 C11 108.05(17) . . ?
C12 O3 C22 113.5(2) . . ?
C5 O4 C19 113.24(17) . . ?
C17 O5 C20 104.87(17) . . ?
C16 O6 C20 105.08(18) . . ?
C2 C1 C6 118.2(2) . . ?
C2 C1 C10 121.3(2) . . ?
C6 C1 C10 120.0(2) . . ?
C1 C2 C3 122.3(2) . . ?
C4 C3 C2 119.3(2) . . ?
O1 C4 C3 125.7(2) . . ?
O1 C4 C5 115.7(2) . . ?
C3 C4 C5 118.6(2) . . ?
O4 C5 C4 119.53(19) . . ?
C6 C5 O4 118.13(19) . . ?
C6 C5 C4 122.2(2) . . ?
C1 C6 C7 124.51(19) . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 116.72(18) . . ?
C6 C7 C8 109.59(17) . . ?
C6 C7 C13 108.95(17) . . ?
C8 C7 C13 114.62(17) . . ?
C9 C8 C7 111.97(18) . . ?
C12 C8 C7 118.21(18) . . ?
C12 C8 C9 103.20(18) . . ?
C10 C9 C8 109.16(19) . . ?
C11 C9 C8 100.31(19) . . ?
C11 C9 C10 120.52(19) . . ?
C9 C10 C1 106.90(18) . . ?
O2 C11 C9 103.01(18) . . ?
O2 C12 C8 106.45(18) . . ?
O3 C12 O2 110.41(17) . . ?
O3 C12 C8 109.72(19) . . ?
C14 C13 C7 121.55(19) . . ?
C14 C13 C18 118.3(2) . . ?
C18 C13 C7 120.08(18) . . ?
C13 C14 C15 123.8(2) . . ?
C16 C15 C14 116.2(2) . . ?
C15 C16 O6 128.9(2) . . ?
C15 C16 C17 121.1(2) . . ?
C17 C16 O6 110.0(2) . . ?
C16 C17 O5 109.70(19) . . ?
C18 C17 O5 125.8(2) . . ?
C18 C17 C16 124.5(2) . . ?
C13 C18 C19 128.04(19) . . ?
C17 C18 C13 116.1(2) . . ?
C17 C18 C19 115.83(19) . . ?
O4 C19 C18 115.06(18) . . ?
O6 C20 O5 107.46(18) . . ?


_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 2.709
_oxdiff_exptl_absorpt_empirical_full_min 0.699
####################################################################### 
# 
# 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_12a
_database_code_depnum_ccdc_archive 'CCDC 2299449'
loop_
_audit_author_name
_audit_author_address
'Shao Y.'
;Southwest University
China
;
_audit_update_record             
;
2023-10-05 deposited with the CCDC.	2023-12-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H18 O6'
_chemical_formula_sum            'C21 H18 O6'
_chemical_formula_weight         366.35
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.60702(16)
_cell_length_b                   8.8987(2)
_cell_length_c                   25.6270(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1734.75(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3623
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7440
_cell_measurement_theta_min      4.8740
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5783
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         5.26
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -28.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -86.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega  -66.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega   64.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   66.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   41.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 67

#__ type_ start__ end____ width___ exp.time_
  8 omega   58.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   51.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
 10 omega   51.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   73.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega   79.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   43.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 14 omega   60.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega  -77.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega   50.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 17 omega   63.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 18 omega  141.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  139.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
 20 omega   86.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 21 omega   59.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 22 omega   52.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   35.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1271762000
_diffrn_orient_matrix_UB_12      0.1195772000
_diffrn_orient_matrix_UB_13      0.0214584000
_diffrn_orient_matrix_UB_21      -0.1454658000
_diffrn_orient_matrix_UB_22      -0.1198953000
_diffrn_orient_matrix_UB_23      0.0044736000
_diffrn_orient_matrix_UB_31      0.0603745000
_diffrn_orient_matrix_UB_32      -0.0362855000
_diffrn_orient_matrix_UB_33      0.0559822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2763
_reflns_number_total             2905
_reflns_odcompleteness_completeness 95.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(18)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2905
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.1770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C13(H13A,H13B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.81867(17) 0.41387(15) 0.23038(4) 0.0435(3) Uani 1 d . . .
O2 O 1.09571(19) 0.50460(17) 0.25086(5) 0.0561(4) Uani 1 d . . .
O3 O 0.68678(14) 0.10429(13) 0.10904(4) 0.0368(3) Uani 1 d . . .
O4 O 1.0088(2) 0.1073(2) -0.04279(5) 0.0632(4) Uani 1 d . . .
O5 O 1.2826(2) 0.0193(2) -0.04082(5) 0.0598(4) Uani 1 d . . .
O6 O 0.56215(18) -0.13942(17) 0.15976(6) 0.0571(4) Uani 1 d . . .
C1 C 0.9048(2) 0.26938(17) 0.15310(6) 0.0282(3) Uani 1 d . . .
C2 C 1.0502(2) 0.23399(17) 0.12057(6) 0.0282(3) Uani 1 d . . .
C3 C 1.2165(2) 0.28702(19) 0.13396(7) 0.0355(4) Uani 1 d . . .
H3 H 1.3112 0.2617 0.1128 0.043 Uiso 1 calc . . R
C3AA C 0.9402(2) 0.35981(18) 0.19516(6) 0.0318(3) Uani 1 d . . .
C4 C 1.2477(2) 0.3770(2) 0.17806(7) 0.0413(4) Uani 1 d . . .
H4 H 1.3600 0.4098 0.1867 0.050 Uiso 1 calc . . R
C5 C 1.1049(2) 0.41376(18) 0.20750(6) 0.0366(4) Uani 1 d . . .
C6 C 0.9204(3) 0.4898(3) 0.26926(7) 0.0542(5) Uani 1 d . . .
H6A H 0.8708 0.5883 0.2760 0.065 Uiso 1 calc . . R
H6B H 0.9190 0.4329 0.3015 0.065 Uiso 1 calc . . R
C7 C 0.7169(2) 0.2191(2) 0.14671(7) 0.0366(4) Uani 1 d . . .
H7A H 0.6749 0.1835 0.1802 0.044 Uiso 1 calc . . R
H7B H 0.6466 0.3058 0.1373 0.044 Uiso 1 calc . . R
C8 C 0.7915(2) -0.02192(19) 0.11404(6) 0.0337(3) Uani 1 d . . .
C9 C 0.9577(2) -0.01893(18) 0.09193(6) 0.0304(3) Uani 1 d . . .
C10 C 1.0224(2) 0.13296(17) 0.07285(6) 0.0294(3) Uani 1 d . . .
H10 H 0.9277 0.1776 0.0521 0.035 Uiso 1 calc . . R
C11 C 1.1824(2) 0.11902(19) 0.03757(6) 0.0346(3) Uani 1 d . . .
H11 H 1.2437 0.2159 0.0382 0.042 Uiso 1 calc . . R
C12 C 1.3180(2) -0.0031(2) 0.05015(7) 0.0390(4) Uani 1 d . . .
H12 H 1.3947 0.0272 0.0790 0.047 Uiso 1 calc . . R
C13 C 1.2308(2) -0.1547(2) 0.06092(7) 0.0439(4) Uani 1 d . . .
H13A H 1.2083 -0.2037 0.0278 0.053 Uiso 1 calc . . R
H13B H 1.3133 -0.2170 0.0800 0.053 Uiso 1 calc . . R
C14 C 1.0611(2) -0.14881(19) 0.09110(6) 0.0353(3) Uani 1 d . . .
C15 C 0.9946(3) -0.2768(2) 0.11504(7) 0.0445(4) Uani 1 d . . .
H15 H 1.0621 -0.3640 0.1151 0.053 Uiso 1 calc . . R
C16 C 0.8311(3) -0.2787(2) 0.13875(8) 0.0474(4) Uani 1 d . . .
H16 H 0.7913 -0.3656 0.1551 0.057 Uiso 1 calc . . R
C17 C 0.7265(2) -0.1506(2) 0.13809(7) 0.0413(4) Uani 1 d . . .
C18 C 1.4169(3) -0.0062(3) -0.00129(8) 0.0528(5) Uani 1 d . . .
H18A H 1.5054 0.0723 -0.0024 0.063 Uiso 1 calc . . R
H18B H 1.4738 -0.1026 -0.0065 0.063 Uiso 1 calc . . R
C19 C 1.1412(3) 0.0832(2) -0.01850(7) 0.0455(4) Uani 1 d . . .
C20 C 0.4951(3) -0.2678(3) 0.18526(12) 0.0852(9) Uani 1 d . . .
H20A H 0.4913 -0.3504 0.1612 0.128 Uiso 1 calc . . GR
H20B H 0.3786 -0.2472 0.1978 0.128 Uiso 1 calc . . GR
H20C H 0.5697 -0.2931 0.2142 0.128 Uiso 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 C3AA 1.379(2) . ?
O1 C6 1.431(2) . ?
O2 C5 1.376(2) . ?
O2 C6 1.421(2) . ?
O3 C7 1.424(2) . ?
O3 C8 1.383(2) . ?
O4 C19 1.203(2) . ?
O5 C18 1.456(2) . ?
O5 C19 1.345(2) . ?
O6 C17 1.371(2) . ?
O6 C20 1.412(3) . ?
C1 C2 1.420(2) . ?
C1 C3AA 1.372(2) . ?
C1 C7 1.507(2) . ?
C2 C3 1.393(2) . ?
C2 C10 1.532(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(2) . ?
C3AA C5 1.379(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.386(2) . ?
C8 C17 1.391(2) . ?
C9 C10 1.519(2) . ?
C9 C14 1.398(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.521(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.532(2) . ?
C11 C19 1.505(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.529(3) . ?
C12 C18 1.518(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.505(3) . ?
C14 C15 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3AA O1 C6 104.96(14) . . ?
C5 O2 C6 105.16(14) . . ?
C8 O3 C7 115.27(12) . . ?
C19 O5 C18 109.35(14) . . ?
C17 O6 C20 117.27(18) . . ?
C2 C1 C7 127.51(14) . . ?
C3AA C1 C2 116.01(14) . . ?
C3AA C1 C7 116.48(14) . . ?
C1 C2 C10 119.40(13) . . ?
C3 C2 C1 119.17(14) . . ?
C3 C2 C10 121.38(14) . . ?
C2 C3 H3 118.5 . . ?
C2 C3 C4 122.98(15) . . ?
C4 C3 H3 118.5 . . ?
O1 C3AA C5 109.73(14) . . ?
C1 C3AA O1 125.99(15) . . ?
C1 C3AA C5 124.26(15) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 C3 116.60(15) . . ?
C5 C4 H4 121.7 . . ?
O2 C5 C3AA 110.10(15) . . ?
C4 C5 O2 128.97(16) . . ?
C4 C5 C3AA 120.92(14) . . ?
O1 C6 H6A 110.0 . . ?
O1 C6 H6B 110.0 . . ?
O2 C6 O1 108.68(14) . . ?
O2 C6 H6A 110.0 . . ?
O2 C6 H6B 110.0 . . ?
H6A C6 H6B 108.3 . . ?
O3 C7 C1 116.09(13) . . ?
O3 C7 H7A 108.3 . . ?
O3 C7 H7B 108.3 . . ?
C1 C7 H7A 108.3 . . ?
C1 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
O3 C8 C9 118.18(14) . . ?
O3 C8 C17 120.30(15) . . ?
C9 C8 C17 121.42(15) . . ?
C8 C9 C10 116.36(14) . . ?
C8 C9 C14 120.24(15) . . ?
C14 C9 C10 123.26(14) . . ?
C2 C10 H10 107.3 . . ?
C9 C10 C2 108.05(12) . . ?
C9 C10 H10 107.3 . . ?
C9 C10 C11 112.19(13) . . ?
C11 C10 C2 114.30(13) . . ?
C11 C10 H10 107.3 . . ?
C10 C11 H11 107.5 . . ?
C10 C11 C12 118.13(13) . . ?
C12 C11 H11 107.5 . . ?
C19 C11 C10 114.70(14) . . ?
C19 C11 H11 107.5 . . ?
C19 C11 C12 101.02(13) . . ?
C11 C12 H12 111.4 . . ?
C13 C12 C11 111.82(14) . . ?
C13 C12 H12 111.4 . . ?
C18 C12 C11 99.43(14) . . ?
C18 C12 H12 111.4 . . ?
C18 C12 C13 110.85(16) . . ?
C12 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 C12 115.73(15) . . ?
C14 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C9 C14 C13 121.26(15) . . ?
C15 C14 C9 117.79(16) . . ?
C15 C14 C13 120.69(16) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.07(17) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.93(17) . . ?
C17 C16 H16 120.0 . . ?
O6 C17 C8 116.34(17) . . ?
O6 C17 C16 125.19(17) . . ?
C16 C17 C8 118.47(16) . . ?
O5 C18 C12 104.67(15) . . ?
O5 C18 H18A 110.8 . . ?
O5 C18 H18B 110.8 . . ?
C12 C18 H18A 110.8 . . ?
C12 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
O4 C19 O5 121.65(16) . . ?
O4 C19 C11 129.13(17) . . ?
O5 C19 C11 109.20(16) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3AA C5 O2 -0.19(19) . . . . ?
O1 C3AA C5 C4 -179.49(16) . . . . ?
O3 C8 C9 C10 10.90(19) . . . . ?
O3 C8 C9 C14 -173.20(13) . . . . ?
O3 C8 C17 O6 -5.3(2) . . . . ?
O3 C8 C17 C16 175.13(15) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C1 C2 C10 C9 -61.46(17) . . . . ?
C1 C2 C10 C11 172.88(13) . . . . ?
C1 C3AA C5 O2 178.18(15) . . . . ?
C1 C3AA C5 C4 -1.1(3) . . . . ?
C2 C1 C3AA O1 176.84(14) . . . . ?
C2 C1 C3AA C5 -1.3(2) . . . . ?
C2 C1 C7 O3 11.0(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C10 C11 C12 87.22(18) . . . . ?
C2 C10 C11 C19 -153.80(14) . . . . ?
C3 C2 C10 C9 115.90(16) . . . . ?
C3 C2 C10 C11 -9.8(2) . . . . ?
C3 C4 C5 O2 -176.85(17) . . . . ?
C3 C4 C5 C3AA 2.3(3) . . . . ?
C3AA O1 C6 O2 11.4(2) . . . . ?
C3AA C1 C2 C3 2.3(2) . . . . ?
C3AA C1 C2 C10 179.73(13) . . . . ?
C3AA C1 C7 O3 -168.94(14) . . . . ?
C5 O2 C6 O1 -11.5(2) . . . . ?
C6 O1 C3AA C1 174.76(17) . . . . ?
C6 O1 C3AA C5 -6.91(19) . . . . ?
C6 O2 C5 C3AA 7.3(2) . . . . ?
C6 O2 C5 C4 -173.51(19) . . . . ?
C7 O3 C8 C9 -83.85(17) . . . . ?
C7 O3 C8 C17 99.73(18) . . . . ?
C7 C1 C2 C3 -177.67(16) . . . . ?
C7 C1 C2 C10 -0.2(2) . . . . ?
C7 C1 C3AA O1 -3.2(2) . . . . ?
C7 C1 C3AA C5 178.72(15) . . . . ?
C8 O3 C7 C1 51.74(19) . . . . ?
C8 C9 C10 C2 67.47(16) . . . . ?
C8 C9 C10 C11 -165.63(13) . . . . ?
C8 C9 C14 C13 171.39(15) . . . . ?
C8 C9 C14 C15 -2.8(2) . . . . ?
C9 C8 C17 O6 178.41(15) . . . . ?
C9 C8 C17 C16 -1.2(3) . . . . ?
C9 C10 C11 C12 -36.23(19) . . . . ?
C9 C10 C11 C19 82.74(17) . . . . ?
C9 C14 C15 C16 0.6(3) . . . . ?
C10 C2 C3 C4 -178.53(16) . . . . ?
C10 C9 C14 C13 -13.0(2) . . . . ?
C10 C9 C14 C15 172.79(15) . . . . ?
C10 C11 C12 C13 47.1(2) . . . . ?
C10 C11 C12 C18 164.14(15) . . . . ?
C10 C11 C19 O4 24.7(3) . . . . ?
C10 C11 C19 O5 -157.04(16) . . . . ?
C11 C12 C13 C14 -38.4(2) . . . . ?
C11 C12 C18 O5 -36.18(19) . . . . ?
C12 C11 C19 O4 152.9(2) . . . . ?
C12 C11 C19 O5 -28.85(19) . . . . ?
C12 C13 C14 C9 23.2(2) . . . . ?
C12 C13 C14 C15 -162.79(16) . . . . ?
C13 C12 C18 O5 81.62(19) . . . . ?
C13 C14 C15 C16 -173.66(17) . . . . ?
C14 C9 C10 C2 -108.29(16) . . . . ?
C14 C9 C10 C11 18.6(2) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 C16 C17 O6 179.37(17) . . . . ?
C15 C16 C17 C8 -1.1(3) . . . . ?
C17 C8 C9 C10 -172.72(15) . . . . ?
C17 C8 C9 C14 3.2(2) . . . . ?
C18 O5 C19 O4 -175.7(2) . . . . ?
C18 O5 C19 C11 5.9(2) . . . . ?
C18 C12 C13 C14 -148.41(16) . . . . ?
C19 O5 C18 C12 20.0(2) . . . . ?
C19 C11 C12 C13 -78.88(17) . . . . ?
C19 C11 C12 C18 38.20(17) . . . . ?
C20 O6 C17 C8 -178.8(2) . . . . ?
C20 O6 C17 C16 0.8(3) . . . . ?


_olex2_date_sample_data_collection 2018-07-20
_olex2_submission_special_instructions 'No special instructions were received'
