# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_PDC-Pd-033
_database_code_depnum_ccdc_archive 'CCDC 2474009'
loop_
_audit_author_name
_audit_author_address
'Jordi Benet'
;ICIQ
Spain
;
_audit_update_record             
;
2025-07-18 deposited with the CCDC.	2026-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 O6'
_chemical_formula_weight         408.43

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.50047(6)
_cell_length_b                   16.40122(11)
_cell_length_c                   16.58919(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2040.75(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30214
_cell_measurement_theta_min      3.8720
_cell_measurement_theta_max      64.5860

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            129359
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.494
_diffrn_reflns_theta_max         65.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             34988
_reflns_number_gt                32350
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_structure_solution    Sir2019
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
'shelXle (H?bschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.2048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 14029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         34988
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   0.654
_refine_ls_restrained_S_all      0.654
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56528(3) 0.53508(2) 0.50879(2) 0.01641(3) Uani 1 1 d . . . . .
O2 O 0.28139(3) 0.54756(2) 0.48060(2) 0.01623(3) Uani 1 1 d . . . . .
O3 O 0.05677(3) 0.54702(2) 0.58128(2) 0.01509(3) Uani 1 1 d . . . . .
O4 O 0.11497(4) 0.53010(2) 0.70969(2) 0.01809(4) Uani 1 1 d . . . . .
O5 O 0.48337(5) 0.48721(2) 0.74674(2) 0.01852(4) Uani 1 1 d . . . . .
O6 O 0.19791(4) 0.15449(2) 0.59037(2) 0.01809(4) Uani 1 1 d . . . . .
C1 C 0.41504(4) 0.53947(2) 0.53391(2) 0.01170(3) Uani 1 1 d . . . . .
C2 C 0.10073(4) 0.52554(2) 0.50004(2) 0.01372(3) Uani 1 1 d . . . . .
C3 C 0.07599(7) 0.43456(2) 0.48938(3) 0.02148(6) Uani 1 1 d . . . . .
H3A H -0.049253 0.420363 0.498655 0.032 Uiso 1 1 calc R U . . .
H3B H 0.151260 0.405427 0.528136 0.032 Uiso 1 1 calc R U . . .
H3C H 0.109962 0.419006 0.434449 0.032 Uiso 1 1 calc R U . . .
C4 C -0.01671(5) 0.57642(3) 0.44638(2) 0.01883(5) Uani 1 1 d . . . . .
H4A H 0.012779 0.565570 0.389839 0.028 Uiso 1 1 calc R U . . .
H4B H 0.002503 0.634311 0.458145 0.028 Uiso 1 1 calc R U . . .
H4C H -0.141908 0.562509 0.456213 0.028 Uiso 1 1 calc R U . . .
C5 C 0.17274(4) 0.53597(2) 0.64239(2) 0.01220(3) Uani 1 1 d . . . . .
C6 C 0.37173(4) 0.53896(2) 0.62334(2) 0.01122(3) Uani 1 1 d . . . . .
C7 C 0.47583(4) 0.46718(2) 0.66379(2) 0.01357(3) Uani 1 1 d . . . . .
H7 H 0.600446 0.467923 0.642381 0.016 Uiso 1 1 calc R U . . .
C8 C 0.46675(5) 0.57337(2) 0.75735(2) 0.01669(4) Uani 1 1 d . . . . .
H8A H 0.571286 0.594786 0.787004 0.020 Uiso 1 1 calc R U . . .
H8B H 0.358093 0.585947 0.788869 0.020 Uiso 1 1 calc R U . . .
C9 C 0.45513(4) 0.61366(2) 0.67248(2) 0.01283(3) Uani 1 1 d . . . . .
C10 C 0.40055(4) 0.38340(2) 0.64930(2) 0.01338(3) Uani 1 1 d . . . . .
C11 C 0.46432(5) 0.33875(2) 0.58338(2) 0.01502(4) Uani 1 1 d . . . . .
H11 H 0.557524 0.360589 0.551171 0.018 Uiso 1 1 calc R U . . .
C12 C 0.39316(5) 0.26297(2) 0.56445(2) 0.01582(4) Uani 1 1 d . . . . .
H12 H 0.435980 0.233756 0.518949 0.019 Uiso 1 1 calc R U . . .
C13 C 0.25815(5) 0.22969(2) 0.61258(2) 0.01421(4) Uani 1 1 d . . . . .
C14 C 0.19608(5) 0.27293(2) 0.67939(2) 0.01569(4) Uani 1 1 d . . . . .
H14 H 0.105650 0.250326 0.712686 0.019 Uiso 1 1 calc R U . . .
C15 C 0.26737(5) 0.34958(2) 0.69716(2) 0.01550(4) Uani 1 1 d . . . . .
H15 H 0.224345 0.378971 0.742513 0.019 Uiso 1 1 calc R U . . .
C16 C 0.05896(7) 0.11902(3) 0.63758(3) 0.02340(7) Uani 1 1 d . . . . .
H16A H -0.046117 0.154509 0.636323 0.035 Uiso 1 1 calc R U . . .
H16B H 0.099688 0.112728 0.693367 0.035 Uiso 1 1 calc R U . . .
H16C H 0.027914 0.065462 0.615461 0.035 Uiso 1 1 calc R U . . .
C17 C 0.64410(4) 0.63182(2) 0.64459(2) 0.01615(4) Uani 1 1 d . . . . .
H17 H 0.723707 0.586975 0.640325 0.019 Uiso 1 1 calc R U . . .
C18 C 0.70760(6) 0.70513(3) 0.62562(3) 0.02167(6) Uani 1 1 d . . . . .
H18A H 0.632600 0.751678 0.629026 0.026 Uiso 1 1 calc R U . . .
H18B H 0.827937 0.710908 0.608690 0.026 Uiso 1 1 calc R U . . .
C19 C 0.34140(4) 0.69044(2) 0.67161(2) 0.01356(3) Uani 1 1 d . . . . .
C20 C 0.32491(5) 0.73860(2) 0.74081(2) 0.01745(4) Uani 1 1 d . . . . .
H20 H 0.380015 0.721627 0.789565 0.021 Uiso 1 1 calc R U . . .
C21 C 0.22832(6) 0.81137(2) 0.73899(3) 0.02054(6) Uani 1 1 d . . . . .
H21 H 0.218450 0.843461 0.786448 0.025 Uiso 1 1 calc R U . . .
C22 C 0.14646(5) 0.83722(2) 0.66826(3) 0.02056(6) Uani 1 1 d . . . . .
H22 H 0.079255 0.886308 0.667385 0.025 Uiso 1 1 calc R U . . .
C23 C 0.16409(5) 0.79041(2) 0.59883(3) 0.01870(5) Uani 1 1 d . . . . .
H23 H 0.109257 0.807735 0.550126 0.022 Uiso 1 1 calc R U . . .
C24 C 0.26192(5) 0.71817(2) 0.60042(2) 0.01575(4) Uani 1 1 d . . . . .
H24 H 0.274834 0.687246 0.552353 0.019 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2036(4) . ?
O2 C1 1.3433(4) . ?
O2 C2 1.4389(4) . ?
O3 C5 1.3480(4) . ?
O3 C2 1.4315(4) . ?
O4 C5 1.2015(4) . ?
O5 C7 1.4158(4) . ?
O5 C8 1.4294(5) . ?
O6 C13 1.3642(4) . ?
O6 C16 1.4276(5) . ?
C1 C6 1.5188(4) . ?
C2 C4 1.5049(5) . ?
C2 C3 1.5140(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.5264(4) . ?
C6 C7 1.5640(4) . ?
C6 C9 1.5989(4) . ?
C7 C10 1.5049(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.5578(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C17 1.5204(5) . ?
C9 C19 1.5212(4) . ?
C10 C15 1.3914(4) . ?
C10 C11 1.4004(4) . ?
C11 C12 1.3886(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.4002(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.3958(5) . ?
C14 C15 1.3976(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3310(6) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19 C20 1.3990(4) . ?
C19 C24 1.3989(5) . ?
C20 C21 1.3964(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.3904(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.3905(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.3939(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
C1 O2 C2 122.03(2) . . ?
C5 O3 C2 121.76(2) . . ?
C7 O5 C8 110.22(2) . . ?
C13 O6 C16 117.53(3) . . ?
O1 C1 O2 118.47(3) . . ?
O1 C1 C6 122.55(3) . . ?
O2 C1 C6 118.95(2) . . ?
O3 C2 O2 111.48(2) . . ?
O3 C2 C4 106.59(3) . . ?
O2 C2 C4 106.23(3) . . ?
O3 C2 C3 108.92(3) . . ?
O2 C2 C3 109.67(3) . . ?
C4 C2 C3 113.93(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O4 C5 O3 118.49(3) . . ?
O4 C5 C6 123.20(3) . . ?
O3 C5 C6 118.10(2) . . ?
C1 C6 C5 114.30(2) . . ?
C1 C6 C7 108.45(2) . . ?
C5 C6 C7 112.03(2) . . ?
C1 C6 C9 114.21(2) . . ?
C5 C6 C9 107.56(2) . . ?
C7 C6 C9 99.36(2) . . ?
O5 C7 C10 112.47(3) . . ?
O5 C7 C6 105.21(2) . . ?
C10 C7 C6 115.56(2) . . ?
O5 C7 H7 107.8 . . ?
C10 C7 H7 107.8 . . ?
C6 C7 H7 107.8 . . ?
O5 C8 C9 108.23(3) . . ?
O5 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O5 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C17 C9 C19 110.96(3) . . ?
C17 C9 C8 107.82(3) . . ?
C19 C9 C8 113.02(3) . . ?
C17 C9 C6 111.08(2) . . ?
C19 C9 C6 114.21(2) . . ?
C8 C9 C6 99.07(2) . . ?
C15 C10 C11 118.84(3) . . ?
C15 C10 C7 122.83(3) . . ?
C11 C10 C7 118.31(3) . . ?
C12 C11 C10 120.89(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.86(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
O6 C13 C14 124.28(3) . . ?
O6 C13 C12 115.97(3) . . ?
C14 C13 C12 119.74(3) . . ?
C13 C14 C15 119.79(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.86(3) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C9 125.63(4) . . ?
C18 C17 H17 117.2 . . ?
C9 C17 H17 117.2 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C20 C19 C24 118.13(3) . . ?
C20 C19 C9 120.62(3) . . ?
C24 C19 C9 121.07(3) . . ?
C21 C20 C19 120.70(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 120.53(4) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.25(3) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C24 120.24(4) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 121.11(3) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O2 C1 O1 158.09(3) . . . . ?
C2 O2 C1 C6 -23.87(4) . . . . ?
C5 O3 C2 O2 -40.91(4) . . . . ?
C5 O3 C2 C4 -156.41(3) . . . . ?
C5 O3 C2 C3 80.24(4) . . . . ?
C1 O2 C2 O3 38.46(4) . . . . ?
C1 O2 C2 C4 154.19(3) . . . . ?
C1 O2 C2 C3 -82.26(4) . . . . ?
C2 O3 C5 O4 -156.85(3) . . . . ?
C2 O3 C5 C6 28.37(4) . . . . ?
O1 C1 C6 C5 -173.85(3) . . . . ?
O2 C1 C6 C5 8.19(4) . . . . ?
O1 C1 C6 C7 -48.08(4) . . . . ?
O2 C1 C6 C7 133.96(3) . . . . ?
O1 C1 C6 C9 61.68(4) . . . . ?
O2 C1 C6 C9 -116.28(3) . . . . ?
O4 C5 C6 C1 175.22(3) . . . . ?
O3 C5 C6 C1 -10.26(4) . . . . ?
O4 C5 C6 C7 51.35(4) . . . . ?
O3 C5 C6 C7 -134.13(3) . . . . ?
O4 C5 C6 C9 -56.84(4) . . . . ?
O3 C5 C6 C9 117.68(3) . . . . ?
C8 O5 C7 C10 -150.87(3) . . . . ?
C8 O5 C7 C6 -24.27(4) . . . . ?
C1 C6 C7 O5 159.35(3) . . . . ?
C5 C6 C7 O5 -73.57(3) . . . . ?
C9 C6 C7 O5 39.79(3) . . . . ?
C1 C6 C7 C10 -75.97(3) . . . . ?
C5 C6 C7 C10 51.11(3) . . . . ?
C9 C6 C7 C10 164.48(2) . . . . ?
C7 O5 C8 C9 -2.57(4) . . . . ?
O5 C8 C9 C17 -88.68(3) . . . . ?
O5 C8 C9 C19 148.31(3) . . . . ?
O5 C8 C9 C6 27.04(4) . . . . ?
C1 C6 C9 C17 -40.69(3) . . . . ?
C5 C6 C9 C17 -168.68(3) . . . . ?
C7 C6 C9 C17 74.51(3) . . . . ?
C1 C6 C9 C19 85.72(3) . . . . ?
C5 C6 C9 C19 -42.27(3) . . . . ?
C7 C6 C9 C19 -159.07(2) . . . . ?
C1 C6 C9 C8 -153.88(3) . . . . ?
C5 C6 C9 C8 78.13(3) . . . . ?
C7 C6 C9 C8 -38.67(3) . . . . ?
O5 C7 C10 C15 34.40(4) . . . . ?
C6 C7 C10 C15 -86.42(4) . . . . ?
O5 C7 C10 C11 -147.40(3) . . . . ?
C6 C7 C10 C11 91.77(3) . . . . ?
C15 C10 C11 C12 1.74(5) . . . . ?
C7 C10 C11 C12 -176.53(3) . . . . ?
C10 C11 C12 C13 -1.24(5) . . . . ?
C16 O6 C13 C14 1.75(6) . . . . ?
C16 O6 C13 C12 -179.37(4) . . . . ?
C11 C12 C13 O6 -179.01(3) . . . . ?
C11 C12 C13 C14 -0.08(5) . . . . ?
O6 C13 C14 C15 179.70(3) . . . . ?
C12 C13 C14 C15 0.86(5) . . . . ?
C11 C10 C15 C14 -0.94(5) . . . . ?
C7 C10 C15 C14 177.25(3) . . . . ?
C13 C14 C15 C10 -0.35(5) . . . . ?
C19 C9 C17 C18 3.27(5) . . . . ?
C8 C9 C17 C18 -121.00(4) . . . . ?
C6 C9 C17 C18 131.46(4) . . . . ?
C17 C9 C19 C20 -92.81(4) . . . . ?
C8 C9 C19 C20 28.44(4) . . . . ?
C6 C9 C19 C20 140.71(3) . . . . ?
C17 C9 C19 C24 82.25(4) . . . . ?
C8 C9 C19 C24 -156.50(3) . . . . ?
C6 C9 C19 C24 -44.24(4) . . . . ?
C24 C19 C20 C21 1.40(5) . . . . ?
C9 C19 C20 C21 176.59(3) . . . . ?
C19 C20 C21 C22 0.09(6) . . . . ?
C20 C21 C22 C23 -0.99(6) . . . . ?
C21 C22 C23 C24 0.38(6) . . . . ?
C22 C23 C24 C19 1.16(5) . . . . ?
C20 C19 C24 C23 -2.02(5) . . . . ?
C9 C19 C24 C23 -177.19(3) . . . . ?

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_iciqe_01a-24_jfpalt_jbb375
_database_code_depnum_ccdc_archive 'CCDC 2474010'
loop_
_audit_author_name
_audit_author_address
'Jordi Benet'
;ICIQ
Spain
;
_audit_update_record             
;
2025-07-18 deposited with the CCDC.	2026-05-11 downloaded from the CCDC.
;
_audit_creation_date             2024-07-09
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 O5'
_chemical_formula_sum            'C21 H22 O5'
_chemical_formula_weight         354.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21H20O5  '
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'
O O 0.0106 0.0060 '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                   6.69025(8)
_cell_length_b                   10.33358(13)
_cell_length_c                   25.2815(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1747.82(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    35195
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      69.3660
_cell_measurement_theta_min      2.1540
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024)
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    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       67
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            110278
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         71.368
_diffrn_reflns_theta_min         2.129
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50   20.00    --    5.00  45.00  -3.00  356
  2  ω    -42.00 -17.00   0.50   20.00    --  -41.80  45.00  -3.00   50
  3  ω   -120.00 -94.00   0.50  200.00    -- -110.00  45.00  -3.00   52
  4  ω     36.00  62.00   0.50   20.00    --    5.00   0.00-150.00   52
  5  ω    -42.00 -17.00   0.50   20.00    --    5.00   0.00-150.00   50
  6  ω     -2.00  25.00   0.50   20.00    --  -41.80  37.00 120.00   54
  7  ω   -131.00  47.00   0.50   20.00    --  -41.80  18.00  90.00  356
  8  ω     23.00  48.00   0.50   20.00    --  -41.80  45.00  -3.00   50
  9  ω   -130.00 -65.00   0.50   20.00    --  -41.80  37.00 120.00  130
 10  ω    -60.00  -9.00   0.50   20.00    --  -41.80  37.00 120.00  102
 11  ω   -199.00 -80.00   0.50  200.00    -- -110.00   0.00  90.00  238
 12  ω    -58.00 -28.00   0.50  200.00    -- -110.00  46.00  60.00   60
 13  ω    -84.00 -24.00   0.50  200.00    -- -110.00  37.00  90.00  120
 14  ω   -166.00-138.00   0.50  200.00    -- -110.00  46.00  60.00   56
 15  ω   -196.00 -33.00   0.50  200.00    -- -110.00  28.00 150.00  326
 16  ω    -84.00 -21.00   0.50  200.00    -- -110.00  18.00  60.00  126
 17  ω    -68.00 -43.00   0.50  200.00    -- -110.00   0.00  90.00   50
 18  ω   -199.00-118.00   0.50  200.00    -- -110.00  28.00  30.00  162
 19  ω   -199.00 -92.00   0.50  200.00    -- -110.00  37.00-180.00  214
 20  ω    -84.00 -35.00   0.50  200.00    -- -110.00  28.00  30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1019736000
_diffrn_orient_matrix_UB_12      0.0186892000
_diffrn_orient_matrix_UB_13      0.0011012000
_diffrn_orient_matrix_UB_21      -0.0175847000
_diffrn_orient_matrix_UB_22      -0.0471434000
_diffrn_orient_matrix_UB_23      0.0198430000
_diffrn_orient_matrix_UB_31      0.0232871000
_diffrn_orient_matrix_UB_32      0.0462381000
_diffrn_orient_matrix_UB_33      0.0197934000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                24251
_reflns_number_total             34304
_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 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 8940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         34304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1079
_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 Riding coordinates:
 O2(H2)
2.b Ternary CH refined with riding coordinates:
 C2(H2A)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C12(H12), C9(H9), C17(H17), C8(H8), C21(H21), C18(H18),
 C19(H19), C20(H20)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
O4 O 0.02718(5) 0.38079(3) 0.77970(2) 0.01323(4) Uani 1 1 d . . . . .
H4 H -0.031280 0.449731 0.771302 0.020 Uiso 1 1 calc R U . . .
O3 O 0.29424(6) 0.48720(3) 0.74961(2) 0.01692(5) Uani 1 1 d . . . . .
O1 O 0.15521(6) 0.07927(4) 0.76239(2) 0.01647(5) Uani 1 1 d . . . . .
O2 O 0.62381(5) 0.39451(4) 0.82082(2) 0.01624(5) Uani 1 1 d . . . . .
H2 H 0.708613 0.375622 0.837839 0.024 Uiso 1 1 d R U . . .
O5 O 0.11067(8) 0.36023(6) 0.53750(2) 0.02434(8) Uani 1 1 d . . . . .
C6 C 0.22145(5) 0.39235(4) 0.77010(2) 0.01044(4) Uani 1 1 d . . . . .
C5 C 0.56552(6) 0.30211(4) 0.78220(2) 0.01250(5) Uani 1 1 d . . . . .
H5A H 0.642015 0.221256 0.787801 0.015 Uiso 1 1 calc R U . . .
H5B H 0.599413 0.335563 0.746616 0.015 Uiso 1 1 calc R U . . .
C7 C 0.24213(6) 0.21225(4) 0.68691(2) 0.01170(4) Uani 1 1 d . . . . .
C2 C 0.30308(6) 0.16476(4) 0.74099(2) 0.01110(4) Uani 1 1 d . . . . .
H2A H 0.429627 0.114275 0.736819 0.013 Uiso 1 1 calc R U . . .
C11 C -0.00714(7) 0.28379(5) 0.62357(2) 0.01573(6) Uani 1 1 d . . . . .
H11 H -0.143211 0.299176 0.614854 0.019 Uiso 1 1 calc R U . . .
C10 C 0.14275(8) 0.31011(5) 0.58684(2) 0.01629(6) Uani 1 1 d . . . . .
C14 C 0.42738(7) 0.11316(4) 0.85642(2) 0.01385(5) Uani 1 1 d . . . . .
H14 H 0.464550 0.043064 0.834185 0.017 Uiso 1 1 calc R U . . .
C3 C 0.09485(6) 0.11636(4) 0.81423(2) 0.01210(5) Uani 1 1 d . . . . .
H3A H 0.076276 0.039063 0.836836 0.015 Uiso 1 1 calc R U . . .
H3B H -0.032659 0.164875 0.812913 0.015 Uiso 1 1 calc R U . . .
C12 C 0.04360(6) 0.23471(5) 0.67321(2) 0.01424(5) Uani 1 1 d . . . . .
H12 H -0.059036 0.216317 0.698064 0.017 Uiso 1 1 calc R U . . .
C16 C 0.18351(6) 0.28970(4) 0.88021(2) 0.01238(5) Uani 1 1 d . . . . .
C4 C 0.26381(5) 0.20284(4) 0.83633(2) 0.01021(4) Uani 1 1 d . . . . .
C9 C 0.34196(8) 0.28363(6) 0.59952(2) 0.01832(7) Uani 1 1 d . . . . .
H9 H 0.444286 0.299121 0.574249 0.022 Uiso 1 1 calc R U . . .
C17 C 0.26019(9) 0.41263(5) 0.89107(2) 0.01639(6) Uani 1 1 d . . . . .
H17 H 0.366349 0.445916 0.870150 0.020 Uiso 1 1 calc R U . . .
C8 C 0.39021(7) 0.23480(5) 0.64895(2) 0.01542(6) Uani 1 1 d . . . . .
H8 H 0.525812 0.216372 0.657178 0.018 Uiso 1 1 calc R U . . .
C1 C 0.34089(5) 0.27152(3) 0.78429(2) 0.00962(4) Uani 1 1 d . . . . .
C21 C 0.02888(9) 0.24323(7) 0.91239(2) 0.02072(9) Uani 1 1 d . . . . .
H21 H -0.024142 0.159346 0.906098 0.025 Uiso 1 1 calc R U . . .
C15 C 0.52294(9) 0.12406(6) 0.90229(2) 0.02022(8) Uani 1 1 d . . . . .
C13 C -0.08856(12) 0.39620(8) 0.52409(3) 0.02509(11) Uani 1 1 d . . . . .
H13A H -0.089793 0.435974 0.488900 0.038 Uiso 1 1 calc R U . . .
H13B H -0.139092 0.458264 0.550168 0.038 Uiso 1 1 calc R U . . .
H13C H -0.173841 0.319090 0.523969 0.038 Uiso 1 1 calc R U . . .
C18 C 0.18274(11) 0.48699(6) 0.93224(2) 0.02128(9) Uani 1 1 d . . . . .
H18 H 0.236358 0.570495 0.939002 0.026 Uiso 1 1 calc R U . . .
C19 C 0.02800(12) 0.44029(8) 0.96350(3) 0.02620(12) Uani 1 1 d . . . . .
H19 H -0.024815 0.491522 0.991398 0.031 Uiso 1 1 calc R U . . .
C20 C -0.04855(12) 0.31789(9) 0.95349(3) 0.02861(14) Uani 1 1 d . . . . .
H20 H -0.154061 0.284889 0.974711 0.034 Uiso 1 1 calc R U . . .
H15A H 0.626(2) 0.0553(14) 0.9109(6) 0.033(3) Uiso 1 1 d . . . . .
H15B H 0.507(2) 0.1909(12) 0.9267(5) 0.028(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 H4 0.8400 . ?
O4 C6 1.3275(5) . ?
O3 C6 1.2110(5) . ?
O1 C2 1.4324(5) . ?
O1 C3 1.4240(6) . ?
O2 H2 0.7383 . ?
O2 C5 1.4203(6) . ?
O5 C10 1.3676(7) . ?
O5 C13 1.4247(9) . ?
C6 C1 1.5251(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C1 1.5366(5) . ?
C7 C2 1.5089(6) . ?
C7 C12 1.3921(6) . ?
C7 C8 1.3988(6) . ?
C2 H2A 1.0000 . ?
C2 C1 1.5746(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.3934(7) . ?
C11 C12 1.3955(7) . ?
C10 C9 1.3978(8) . ?
C14 H14 0.9500 . ?
C14 C4 1.5213(5) . ?
C14 C15 1.3288(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5455(5) . ?
C12 H12 0.9500 . ?
C16 C4 1.5247(6) . ?
C16 C17 1.3972(7) . ?
C16 C21 1.4011(7) . ?
C4 C1 1.5815(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.3859(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.3937(7) . ?
C8 H8 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.3939(9) . ?
C15 H15A 1.014(15) . ?
C15 H15B 0.933(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.3889(10) . ?
C19 H19 0.9500 . ?
C19 C20 1.3878(12) . ?
C20 H20 0.9500 . ?

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 O4 H4 109.5 . . ?
C3 O1 C2 112.18(3) . . ?
C5 O2 H2 115.7 . . ?
C10 O5 C13 117.56(5) . . ?
O4 C6 C1 113.35(3) . . ?
O3 C6 O4 123.01(4) . . ?
O3 C6 C1 123.54(4) . . ?
O2 C5 H5A 109.1 . . ?
O2 C5 H5B 109.1 . . ?
O2 C5 C1 112.53(3) . . ?
H5A C5 H5B 107.8 . . ?
C1 C5 H5A 109.1 . . ?
C1 C5 H5B 109.1 . . ?
C12 C7 C2 122.52(4) . . ?
C12 C7 C8 118.51(4) . . ?
C8 C7 C2 118.97(4) . . ?
O1 C2 C7 110.86(3) . . ?
O1 C2 H2A 107.6 . . ?
O1 C2 C1 106.29(3) . . ?
C7 C2 H2A 107.6 . . ?
C7 C2 C1 116.45(3) . . ?
C1 C2 H2A 107.6 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.67(4) . . ?
C12 C11 H11 120.2 . . ?
O5 C10 C11 124.66(5) . . ?
O5 C10 C9 115.65(5) . . ?
C11 C10 C9 119.68(4) . . ?
C4 C14 H14 117.1 . . ?
C15 C14 H14 117.1 . . ?
C15 C14 C4 125.85(5) . . ?
O1 C3 H3A 110.5 . . ?
O1 C3 H3B 110.5 . . ?
O1 C3 C4 106.32(3) . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C7 C12 C11 121.09(4) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C17 C16 C4 123.29(4) . . ?
C17 C16 C21 117.94(4) . . ?
C21 C16 C4 118.74(4) . . ?
C14 C4 C3 107.13(3) . . ?
C14 C4 C16 111.66(3) . . ?
C14 C4 C1 108.46(3) . . ?
C3 C4 C1 101.37(3) . . ?
C16 C4 C3 110.22(3) . . ?
C16 C4 C1 117.13(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.01(4) . . ?
C8 C9 H9 120.0 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.77(5) . . ?
C18 C17 H17 119.6 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.95(4) . . ?
C9 C8 H8 119.5 . . ?
C6 C1 C5 109.63(3) . . ?
C6 C1 C2 109.03(3) . . ?
C6 C1 C4 113.09(3) . . ?
C5 C1 C2 106.10(3) . . ?
C5 C1 C4 116.09(3) . . ?
C2 C1 C4 102.21(3) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.17(6) . . ?
C20 C21 H21 119.4 . . ?
C14 C15 H15A 117.1(8) . . ?
C14 C15 H15B 125.9(8) . . ?
H15A C15 H15B 116.9(12) . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.70(6) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.20(5) . . ?
C20 C19 H19 120.4 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.22(6) . . ?
C19 C20 H20 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C6 C1 C5 -169.11(4) . . . . ?
O4 C6 C1 C2 75.14(4) . . . . ?
O4 C6 C1 C4 -37.83(5) . . . . ?
O3 C6 C1 C5 14.47(6) . . . . ?
O3 C6 C1 C2 -101.28(5) . . . . ?
O3 C6 C1 C4 145.75(4) . . . . ?
O1 C2 C1 C6 -98.89(4) . . . . ?
O1 C2 C1 C5 143.11(4) . . . . ?
O1 C2 C1 C4 21.04(4) . . . . ?
O1 C3 C4 C14 -81.00(4) . . . . ?
O1 C3 C4 C16 157.31(3) . . . . ?
O1 C3 C4 C1 32.58(4) . . . . ?
O2 C5 C1 C6 64.57(5) . . . . ?
O2 C5 C1 C2 -177.83(4) . . . . ?
O2 C5 C1 C4 -65.10(5) . . . . ?
O5 C10 C9 C8 178.85(5) . . . . ?
C7 C2 C1 C6 25.15(4) . . . . ?
C7 C2 C1 C5 -92.85(4) . . . . ?
C7 C2 C1 C4 145.09(3) . . . . ?
C2 O1 C3 C4 -20.71(5) . . . . ?
C2 C7 C12 C11 177.29(4) . . . . ?
C2 C7 C8 C9 -177.24(5) . . . . ?
C11 C10 C9 C8 -1.78(9) . . . . ?
C10 C11 C12 C7 0.43(8) . . . . ?
C10 C9 C8 C7 -0.52(9) . . . . ?
C14 C4 C1 C6 -162.01(3) . . . . ?
C14 C4 C1 C5 -34.03(4) . . . . ?
C14 C4 C1 C2 80.93(4) . . . . ?
C3 O1 C2 C7 -128.22(4) . . . . ?
C3 O1 C2 C1 -0.78(5) . . . . ?
C3 C4 C1 C6 85.41(4) . . . . ?
C3 C4 C1 C5 -146.61(3) . . . . ?
C3 C4 C1 C2 -31.65(3) . . . . ?
C12 C7 C2 O1 33.95(5) . . . . ?
C12 C7 C2 C1 -87.72(5) . . . . ?
C12 C7 C8 C9 2.72(7) . . . . ?
C12 C11 C10 O5 -178.86(5) . . . . ?
C12 C11 C10 C9 1.82(8) . . . . ?
C16 C4 C1 C6 -34.55(4) . . . . ?
C16 C4 C1 C5 93.44(4) . . . . ?
C16 C4 C1 C2 -151.60(3) . . . . ?
C16 C17 C18 C19 0.22(10) . . . . ?
C16 C21 C20 C19 -0.45(12) . . . . ?
C4 C16 C17 C18 -179.01(5) . . . . ?
C4 C16 C21 C20 179.22(6) . . . . ?
C17 C16 C4 C14 91.58(5) . . . . ?
C17 C16 C4 C3 -149.46(4) . . . . ?
C17 C16 C4 C1 -34.31(6) . . . . ?
C17 C16 C21 C20 0.99(9) . . . . ?
C17 C18 C19 C20 0.35(11) . . . . ?
C8 C7 C2 O1 -146.10(4) . . . . ?
C8 C7 C2 C1 92.24(5) . . . . ?
C8 C7 C12 C11 -2.67(7) . . . . ?
C21 C16 C4 C14 -86.55(5) . . . . ?
C21 C16 C4 C3 32.41(6) . . . . ?
C21 C16 C4 C1 147.56(5) . . . . ?
C21 C16 C17 C18 -0.87(8) . . . . ?
C15 C14 C4 C3 -134.60(5) . . . . ?
C15 C14 C4 C16 -13.82(7) . . . . ?
C15 C14 C4 C1 116.71(6) . . . . ?
C13 O5 C10 C11 4.47(9) . . . . ?
C13 O5 C10 C9 -176.19(6) . . . . ?
C18 C19 C20 C21 -0.23(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.506
_oxdiff_exptl_absorpt_empirical_full_min 0.671
