# Supplementary Information (SI) for RSC Advances.
# 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_i19811
_database_code_depnum_ccdc_archive 'CCDC 2496063'
loop_
_audit_author_name
_audit_author_address
'Ping-Jyun Sung'
;National Museum of Marine Biology and Aquarium
Taiwan
;
_audit_update_record             
;
2025-10-17 deposited with the CCDC.	2026-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Dihydrosarsolenone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H32 O5'
_chemical_formula_weight         376.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   18.2228(7)
_cell_length_b                   5.8415(2)
_cell_length_c                   18.7272(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.551(2)
_cell_angle_gamma                90
_cell_volume                     1993.39(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6734
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      74.54

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    0.706
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6502
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   
; 
SADABS-2016/2 - Bruker AXS area detector scaling 
and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18724
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.359
_diffrn_reflns_theta_max         74.644
_diffrn_reflns_theta_full        67.679
_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 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4026
_reflns_number_gt                3799
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.992

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

_computing_data_collection       'Bruker Instrument Service V6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1765)'
_computing_publication_material  'Bruker APEX6 v2024.9-RC113'
_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)+(0.0600P)²+0.1856P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1626 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4026
_refine_ls_number_parameters     251
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.88596(8) 0.4898(3) 0.31946(9) 0.0190(4) Uani 1 1 d . . . . .
H1 H 0.8922(13) 0.491(4) 0.2742(18) 0.028 Uiso 1 1 calc R U . . .
O2 O 0.52635(8) 0.5235(3) 0.14154(8) 0.0160(3) Uani 1 1 d . . . . .
O3 O 0.47831(9) 0.8197(3) 0.20229(9) 0.0213(4) Uani 1 1 d . . . . .
O4 O 0.70672(8) 0.3538(3) 0.20883(8) 0.0132(3) Uani 1 1 d . . . . .
O5 O 0.83219(10) 0.7798(3) 0.07642(9) 0.0260(4) Uani 1 1 d . . . . .
C1 C 0.82752(12) 0.6437(4) 0.33760(11) 0.0150(5) Uani 1 1 d . . . . .
C2 C 0.75359(11) 0.5399(4) 0.31181(11) 0.0130(4) Uani 1 1 d . . . . .
H2 H 0.752113 0.377603 0.328704 0.016 Uiso 1 1 calc R U . . .
C3 C 0.68726(12) 0.6614(4) 0.34271(11) 0.0136(4) Uani 1 1 d . . . . .
H3 H 0.694798 0.815066 0.357723 0.016 Uiso 1 1 calc R U . . .
C4 C 0.61979(12) 0.5781(4) 0.35124(11) 0.0144(4) Uani 1 1 d . . . . .
C5 C 0.59602(12) 0.3430(4) 0.32696(12) 0.0160(4) Uani 1 1 d . . . . .
H5A H 0.568446 0.267636 0.365720 0.019 Uiso 1 1 calc R U . . .
H5B H 0.639998 0.249076 0.317096 0.019 Uiso 1 1 calc R U . . .
C6 C 0.54731(12) 0.3541(4) 0.25915(12) 0.0168(5) Uani 1 1 d . . . . .
H6A H 0.536742 0.196043 0.242984 0.020 Uiso 1 1 calc R U . . .
H6B H 0.499982 0.426520 0.271517 0.020 Uiso 1 1 calc R U . . .
C7 C 0.58125(11) 0.4865(4) 0.19753(11) 0.0132(4) Uani 1 1 d . . . . .
H7 H 0.598227 0.638785 0.215667 0.016 Uiso 1 1 calc R U . . .
C8 C 0.64521(11) 0.3705(4) 0.15811(11) 0.0135(4) Uani 1 1 d . . . . .
C9 C 0.66509(11) 0.5038(4) 0.09069(11) 0.0142(4) Uani 1 1 d . . . . .
H9A H 0.654021 0.668011 0.097916 0.017 Uiso 1 1 calc R U . . .
H9B H 0.634597 0.448333 0.050212 0.017 Uiso 1 1 calc R U . . .
C10 C 0.74629(12) 0.4765(4) 0.07228(11) 0.0159(5) Uani 1 1 d . . . . .
H10A H 0.763207 0.321758 0.086329 0.019 Uiso 1 1 calc R U . . .
H10B H 0.752596 0.492633 0.020071 0.019 Uiso 1 1 calc R U . . .
C11 C 0.79183(12) 0.6539(4) 0.11036(12) 0.0151(4) Uani 1 1 d . . . . .
C12 C 0.78794(12) 0.6768(4) 0.18867(12) 0.0135(4) Uani 1 1 d . . . . .
C13 C 0.83813(12) 0.8578(4) 0.22029(11) 0.0159(4) Uani 1 1 d . . . . .
H13A H 0.824485 1.008089 0.199647 0.019 Uiso 1 1 calc R U . . .
H13B H 0.889085 0.824158 0.205718 0.019 Uiso 1 1 calc R U . . .
C14 C 0.83638(12) 0.8767(4) 0.30171(12) 0.0167(5) Uani 1 1 d . . . . .
H14A H 0.882482 0.948616 0.318865 0.020 Uiso 1 1 calc R U . . .
H14B H 0.795152 0.977099 0.315628 0.020 Uiso 1 1 calc R U . . .
C15 C 0.83118(13) 0.6616(5) 0.42005(12) 0.0210(5) Uani 1 1 d . . . . .
H15 H 0.793862 0.777250 0.434902 0.025 Uiso 1 1 calc R U . . .
C16 C 0.90616(14) 0.7448(5) 0.44714(13) 0.0280(6) Uani 1 1 d . . . . .
H16A H 0.943863 0.632577 0.434594 0.042 Uiso 1 1 calc R U . . .
H16B H 0.904875 0.762803 0.499139 0.042 Uiso 1 1 calc R U . . .
H16C H 0.917692 0.892368 0.425005 0.042 Uiso 1 1 calc R U . . .
C17 C 0.81197(15) 0.4363(6) 0.45629(14) 0.0322(6) Uani 1 1 d . . . . .
H17A H 0.761271 0.394407 0.444236 0.048 Uiso 1 1 calc R U . . .
H17B H 0.817036 0.453464 0.508154 0.048 Uiso 1 1 calc R U . . .
H17C H 0.845252 0.316031 0.439781 0.048 Uiso 1 1 calc R U . . .
C18 C 0.56026(12) 0.7227(4) 0.38365(12) 0.0185(5) Uani 1 1 d . . . . .
H18A H 0.580925 0.869735 0.398999 0.028 Uiso 1 1 calc R U . . .
H18B H 0.539739 0.642980 0.424954 0.028 Uiso 1 1 calc R U . . .
H18C H 0.521405 0.749298 0.348072 0.028 Uiso 1 1 calc R U . . .
C19 C 0.62969(13) 0.1213(4) 0.13985(13) 0.0194(5) Uani 1 1 d . . . . .
H19A H 0.583038 0.110412 0.113594 0.029 Uiso 1 1 calc R U . . .
H19B H 0.626697 0.031679 0.183965 0.029 Uiso 1 1 calc R U . . .
H19C H 0.669329 0.061232 0.110223 0.029 Uiso 1 1 calc R U . . .
C20 C 0.74902(11) 0.5354(4) 0.23101(11) 0.0115(4) Uani 1 1 d . . . . .
C21 C 0.48025(12) 0.7032(4) 0.14939(12) 0.0158(4) Uani 1 1 d . . . . .
C22 C 0.43372(13) 0.7347(5) 0.08413(13) 0.0221(5) Uani 1 1 d . . . . .
H22A H 0.460189 0.678667 0.042307 0.033 Uiso 1 1 calc R U . . .
H22B H 0.422475 0.897571 0.077920 0.033 Uiso 1 1 calc R U . . .
H22C H 0.387941 0.648488 0.089297 0.033 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 1.437(3) . ?
O2 C21 1.353(3) . ?
O2 C7 1.458(3) . ?
O3 C21 1.203(3) . ?
O4 C20 1.374(3) . ?
O4 C8 1.465(3) . ?
O5 C11 1.223(3) . ?
C1 C14 1.527(3) . ?
C1 C15 1.548(3) . ?
C1 C2 1.550(3) . ?
C2 C20 1.515(3) . ?
C2 C3 1.521(3) . ?
C3 C4 1.333(3) . ?
C4 C18 1.507(3) . ?
C4 C5 1.509(3) . ?
C5 C6 1.544(3) . ?
C6 C7 1.525(3) . ?
C7 C8 1.542(3) . ?
C8 C19 1.522(3) . ?
C8 C9 1.530(3) . ?
C9 C10 1.531(3) . ?
C10 C11 1.503(3) . ?
C11 C12 1.475(3) . ?
C12 C20 1.351(3) . ?
C12 C13 1.515(3) . ?
C13 C14 1.529(3) . ?
C15 C17 1.523(4) . ?
C15 C16 1.532(3) . ?
C21 C22 1.492(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
C21 O2 C7 117.32(17) . . ?
C20 O4 C8 124.59(16) . . ?
O1 C1 C14 111.82(17) . . ?
O1 C1 C15 104.66(18) . . ?
C14 C1 C15 112.02(19) . . ?
O1 C1 C2 109.00(17) . . ?
C14 C1 C2 107.86(18) . . ?
C15 C1 C2 111.47(16) . . ?
C20 C2 C3 110.60(17) . . ?
C20 C2 C1 110.93(16) . . ?
C3 C2 C1 112.98(17) . . ?
C4 C3 C2 127.8(2) . . ?
C3 C4 C18 120.8(2) . . ?
C3 C4 C5 124.0(2) . . ?
C18 C4 C5 115.20(19) . . ?
C4 C5 C6 111.76(18) . . ?
C7 C6 C5 114.18(17) . . ?
O2 C7 C6 109.80(16) . . ?
O2 C7 C8 103.73(16) . . ?
C6 C7 C8 116.94(18) . . ?
O4 C8 C19 102.77(17) . . ?
O4 C8 C9 112.54(16) . . ?
C19 C8 C9 110.26(18) . . ?
O4 C8 C7 107.22(16) . . ?
C19 C8 C7 112.84(18) . . ?
C9 C8 C7 110.95(17) . . ?
C8 C9 C10 111.72(17) . . ?
C11 C10 C9 110.60(18) . . ?
O5 C11 C12 119.8(2) . . ?
O5 C11 C10 120.0(2) . . ?
C12 C11 C10 120.17(18) . . ?
C20 C12 C11 124.0(2) . . ?
C20 C12 C13 121.05(19) . . ?
C11 C12 C13 114.66(18) . . ?
C12 C13 C14 114.95(17) . . ?
C1 C14 C13 112.19(18) . . ?
C17 C15 C16 109.6(2) . . ?
C17 C15 C1 112.2(2) . . ?
C16 C15 C1 112.42(18) . . ?
C12 C20 O4 126.24(19) . . ?
C12 C20 C2 123.48(19) . . ?
O4 C20 C2 109.92(17) . . ?
O3 C21 O2 123.5(2) . . ?
O3 C21 C22 125.7(2) . . ?
O2 C21 C22 110.79(19) . . ?

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_i19812
_database_code_depnum_ccdc_archive 'CCDC 2496064'
loop_
_audit_author_name
_audit_author_address
'Ping-Jyun Sung'
;National Museum of Marine Biology and Aquarium
Taiwan
;
_audit_update_record             
;
2025-10-17 deposited with the CCDC.	2026-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Sarcoglaucone A'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H34 O5'
_chemical_formula_sum            'C22 H34 O5'
_chemical_formula_weight         378.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.6754(4)
_cell_length_b                   12.6299(8)
_cell_length_c                   24.3212(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2050.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3062
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      68.59

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.017
_exptl_absorpt_coefficient_mu    0.687
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6176
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   
; 
SADABS-2016/2 - Bruker AXS area detector scaling 
and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28706
_diffrn_reflns_av_unetI/netI     0.1280
_diffrn_reflns_av_R_equivalents  0.1776
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.635
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_full        66.599
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3586
_reflns_number_gt                2134
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.990

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

_computing_data_collection       'Bruker Instrument Service V6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1765)'
_computing_publication_material  'Bruker APEX6 v2024.9-RC113'
_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)] 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 622 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.4(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3586
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5852(5) 0.6982(3) 0.53555(14) 0.0448(10) Uani 1 1 d . . . . .
H1 H 0.491194 0.734042 0.548994 0.067 Uiso 1 1 calc R U . . .
O2 O 0.3621(7) 0.2909(4) 0.30129(15) 0.0686(13) Uani 1 1 d . . . . .
O3 O 0.2010(6) 0.2138(4) 0.37163(19) 0.0665(12) Uani 1 1 d . . . . .
O4 O 0.5611(5) 0.5457(3) 0.33946(13) 0.0509(10) Uani 1 1 d . . . . .
O5 O 0.8059(6) 0.6519(3) 0.42241(14) 0.0481(10) Uani 1 1 d . . . . .
C1 C 0.5304(8) 0.5871(5) 0.5356(2) 0.0427(14) Uani 1 1 d . . . . .
C2 C 0.6810(8) 0.5404(5) 0.49430(19) 0.0429(14) Uani 1 1 d . . . . .
H2 H 0.818380 0.552299 0.509467 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6519(8) 0.4203(5) 0.4881(2) 0.0460(14) Uani 1 1 d . . . . .
H3 H 0.590272 0.388273 0.519165 0.055 Uiso 1 1 calc R U . . .
C4 C 0.6945(8) 0.3529(5) 0.4488(2) 0.0482(15) Uani 1 1 d . . . . .
C5 C 0.7926(9) 0.3767(5) 0.3946(2) 0.0535(16) Uani 1 1 d . . . . .
H5A H 0.931143 0.348749 0.395351 0.064 Uiso 1 1 calc R U . . .
H5B H 0.801037 0.454474 0.390152 0.064 Uiso 1 1 calc R U . . .
C6 C 0.6829(9) 0.3298(5) 0.3444(2) 0.0598(17) Uani 1 1 d . . . . .
H6A H 0.758676 0.348938 0.310859 0.072 Uiso 1 1 calc R U . . .
H6B H 0.684637 0.251660 0.347524 0.072 Uiso 1 1 calc R U . . .
C7 C 0.4661(9) 0.3657(6) 0.3371(2) 0.0579(17) Uani 1 1 d . . . . .
H7 H 0.399122 0.365465 0.373894 0.070 Uiso 1 1 calc R U . . .
C8 C 0.4333(9) 0.4727(6) 0.3106(2) 0.0504(15) Uani 1 1 d . . . . .
C9 C 0.2206(8) 0.5157(6) 0.3196(2) 0.0578(17) Uani 1 1 d . . . . .
H9A H 0.137394 0.505394 0.286337 0.069 Uiso 1 1 calc R U . . .
H9B H 0.155177 0.479852 0.351051 0.069 Uiso 1 1 calc R U . . .
C10 C 0.2506(9) 0.6330(6) 0.3315(2) 0.0577(17) Uani 1 1 d . . . . .
H10A H 0.143740 0.660469 0.355849 0.069 Uiso 1 1 calc R U . . .
H10B H 0.251827 0.674810 0.297038 0.069 Uiso 1 1 calc R U . . .
C11 C 0.4540(8) 0.6369(5) 0.3599(2) 0.0469(15) Uani 1 1 d . . . . .
H11 H 0.525895 0.702425 0.347959 0.056 Uiso 1 1 calc R U . . .
C12 C 0.4502(8) 0.6333(5) 0.4230(2) 0.0440(14) Uani 1 1 d . . . . .
H12 H 0.419680 0.707163 0.435157 0.053 Uiso 1 1 calc R U . . .
C13 C 0.2979(8) 0.5635(5) 0.45151(19) 0.0436(14) Uani 1 1 d . . . . .
H13A H 0.319269 0.489000 0.440376 0.052 Uiso 1 1 calc R U . . .
H13B H 0.161437 0.584503 0.439845 0.052 Uiso 1 1 calc R U . . .
C14 C 0.3141(8) 0.5723(5) 0.5140(2) 0.0442(14) Uani 1 1 d . . . . .
H14A H 0.256909 0.507535 0.530659 0.053 Uiso 1 1 calc R U . . .
H14B H 0.231996 0.633082 0.526382 0.053 Uiso 1 1 calc R U . . .
C15 C 0.5547(8) 0.5439(5) 0.5948(2) 0.0464(15) Uani 1 1 d . . . . .
H15 H 0.518389 0.467073 0.594027 0.056 Uiso 1 1 calc R U . . .
C16 C 0.4097(9) 0.5989(5) 0.6350(2) 0.0586(17) Uani 1 1 d . . . . .
H16A H 0.423992 0.567622 0.671644 0.088 Uiso 1 1 calc R U . . .
H16B H 0.271708 0.589452 0.622105 0.088 Uiso 1 1 calc R U . . .
H16C H 0.441031 0.674627 0.636715 0.088 Uiso 1 1 calc R U . . .
C17 C 0.7707(8) 0.5517(6) 0.6156(2) 0.0587(17) Uani 1 1 d . . . . .
H17A H 0.776167 0.530288 0.654269 0.088 Uiso 1 1 calc R U . . .
H17B H 0.817696 0.624900 0.612010 0.088 Uiso 1 1 calc R U . . .
H17C H 0.856596 0.504947 0.593696 0.088 Uiso 1 1 calc R U . . .
C18 C 0.6538(9) 0.2357(5) 0.4585(2) 0.0596(17) Uani 1 1 d . . . . .
H18A H 0.774378 0.194714 0.449768 0.089 Uiso 1 1 calc R U . . .
H18B H 0.543391 0.212575 0.434795 0.089 Uiso 1 1 calc R U . . .
H18C H 0.617477 0.224380 0.497073 0.089 Uiso 1 1 calc R U . . .
C19 C 0.4922(9) 0.4754(6) 0.2496(2) 0.065(2) Uani 1 1 d . . . . .
H19A H 0.410877 0.424100 0.229145 0.098 Uiso 1 1 calc R U . . .
H19B H 0.634246 0.457159 0.245766 0.098 Uiso 1 1 calc R U . . .
H19C H 0.469055 0.546536 0.234821 0.098 Uiso 1 1 calc R U . . .
C20 C 0.6591(8) 0.6096(5) 0.4442(2) 0.0414(14) Uani 1 1 d . . . . .
C21 C 0.2258(9) 0.2237(6) 0.3231(3) 0.0603(18) Uani 1 1 d . . . . .
C22 C 0.1117(10) 0.1697(6) 0.2785(3) 0.072(2) Uani 1 1 d . . . . .
H22A H 0.024394 0.115469 0.294502 0.108 Uiso 1 1 calc R U . . .
H22B H 0.205634 0.136343 0.252817 0.108 Uiso 1 1 calc R U . . .
H22C H 0.029983 0.221815 0.258760 0.108 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 1.450(7) . ?
O2 C21 1.353(8) . ?
O2 C7 1.461(7) . ?
O3 C21 1.197(7) . ?
O4 C8 1.439(7) . ?
O4 C11 1.444(7) . ?
O5 C20 1.235(6) . ?
C1 C2 1.539(7) . ?
C1 C14 1.548(7) . ?
C1 C15 1.548(7) . ?
C2 C20 1.507(8) . ?
C2 C3 1.537(8) . ?
C3 C4 1.311(8) . ?
C4 C5 1.502(8) . ?
C4 C18 1.523(9) . ?
C5 C6 1.543(8) . ?
C6 C7 1.527(8) . ?
C7 C8 1.513(9) . ?
C8 C9 1.536(8) . ?
C8 C19 1.537(8) . ?
C9 C10 1.524(9) . ?
C10 C11 1.524(8) . ?
C11 C12 1.536(7) . ?
C12 C13 1.513(8) . ?
C12 C20 1.516(7) . ?
C13 C14 1.527(7) . ?
C15 C17 1.531(8) . ?
C15 C16 1.541(8) . ?
C21 C22 1.492(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C7 119.4(5) . . ?
C8 O4 C11 112.7(4) . . ?
O1 C1 C2 101.8(4) . . ?
O1 C1 C14 110.5(5) . . ?
C2 C1 C14 109.9(4) . . ?
O1 C1 C15 108.4(4) . . ?
C2 C1 C15 113.9(4) . . ?
C14 C1 C15 111.8(5) . . ?
C20 C2 C3 118.7(4) . . ?
C20 C2 C1 104.1(4) . . ?
C3 C2 C1 111.1(5) . . ?
C4 C3 C2 133.2(5) . . ?
C3 C4 C5 127.2(6) . . ?
C3 C4 C18 118.7(5) . . ?
C5 C4 C18 114.1(5) . . ?
C4 C5 C6 114.3(5) . . ?
C7 C6 C5 115.3(5) . . ?
O2 C7 C8 104.8(5) . . ?
O2 C7 C6 109.1(5) . . ?
C8 C7 C6 116.9(5) . . ?
O4 C8 C7 106.2(4) . . ?
O4 C8 C9 104.6(5) . . ?
C7 C8 C9 112.9(5) . . ?
O4 C8 C19 107.8(5) . . ?
C7 C8 C19 113.2(6) . . ?
C9 C8 C19 111.5(5) . . ?
C10 C9 C8 104.4(5) . . ?
C9 C10 C11 103.5(5) . . ?
O4 C11 C10 105.1(5) . . ?
O4 C11 C12 109.2(5) . . ?
C10 C11 C12 115.9(5) . . ?
C13 C12 C20 110.3(4) . . ?
C13 C12 C11 119.1(5) . . ?
C20 C12 C11 109.3(5) . . ?
C12 C13 C14 111.5(5) . . ?
C13 C14 C1 114.4(4) . . ?
C17 C15 C16 110.8(5) . . ?
C17 C15 C1 112.5(4) . . ?
C16 C15 C1 111.4(5) . . ?
O5 C20 C2 121.4(5) . . ?
O5 C20 C12 119.9(5) . . ?
C2 C20 C12 118.6(5) . . ?
O3 C21 O2 123.0(6) . . ?
O3 C21 C22 126.8(7) . . ?
O2 C21 C22 110.1(6) . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045

