# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ic22450
_database_code_depnum_ccdc_archive 'CCDC 2323829'
loop_
_audit_author_name
_audit_author_address
'Ping-Jyun Sung'
;National Museum of Marine Biology and Aquarium
Taiwan
;
_audit_update_record             
;
2024-05-21 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        'Gemmacolide X'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H38 Cl O14.50'
_chemical_formula_weight         666.05

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'
Cl Cl 0.3639 0.7018 '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                   12.2945(2)
_cell_length_b                   12.4454(2)
_cell_length_c                   22.2997(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3412.08(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      5.33
_cell_measurement_theta_max      68.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             1404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.198
_exptl_absorpt_coefficient_mu    1.567
_shelx_estimated_absorpt_T_min   0.600
_shelx_estimated_absorpt_T_max   0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7879
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34394
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.068
_diffrn_reflns_theta_max         68.349
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6232
_reflns_number_gt                5969
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_max     0.997
_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       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_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)+(0.0460P)²+0.4359P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2514 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.000(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6232
_refine_ls_number_parameters     425
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.045
_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
Cl1 Cl 1.11149(5) 0.70688(5) 0.67449(3) 0.04891(16) Uani 1 1 d . . . . .
O1 O 0.75875(15) 0.24878(12) 0.60823(8) 0.0448(4) Uani 1 1 d . . . . .
O2 O 0.7107(2) 0.24834(19) 0.70534(10) 0.0702(6) Uani 1 1 d . . . . .
O3 O 0.93668(13) 0.32198(12) 0.65040(7) 0.0363(3) Uani 1 1 d . . . . .
O4 O 1.07954(15) 0.37519(16) 0.59447(9) 0.0523(5) Uani 1 1 d . . . . .
O5 O 0.77540(12) 0.56693(11) 0.66118(6) 0.0297(3) Uani 1 1 d . . . . .
O6 O 0.88410(13) 0.77499(12) 0.67714(6) 0.0362(3) Uani 1 1 d . . . . .
O7 O 0.88541(12) 0.56025(11) 0.52823(6) 0.0295(3) Uani 1 1 d . . . . .
O8 O 0.91325(15) 0.70015(15) 0.46604(9) 0.0532(5) Uani 1 1 d . . . . .
O9 O 0.61543(14) 0.66167(13) 0.47023(7) 0.0407(4) Uani 1 1 d . . . . .
O10 O 0.44700(13) 0.53013(14) 0.52884(7) 0.0393(4) Uani 1 1 d . . . . .
O11 O 0.32029(16) 0.58339(18) 0.46294(9) 0.0614(5) Uani 1 1 d . . . . .
O12 O 0.53809(13) 0.36534(13) 0.59533(7) 0.0383(4) Uani 1 1 d . . . . .
O13 O 0.4785(2) 0.19510(18) 0.60124(10) 0.0692(6) Uani 1 1 d . . . . .
O14 O 0.73909(16) 0.85232(13) 0.71797(7) 0.0460(4) Uani 1 1 d . . . . .
C1 C 0.71137(17) 0.39884(16) 0.54663(9) 0.0296(4) Uani 1 1 d . . . . .
C2 C 0.75680(18) 0.36474(16) 0.60878(9) 0.0322(4) Uani 1 1 d . . . . .
H2 H 0.704284 0.388640 0.640318 0.039 Uiso 1 1 calc R U . . .
C3 C 0.87108(18) 0.40733(16) 0.62557(9) 0.0313(4) Uani 1 1 d . . . . .
H3 H 0.907545 0.439762 0.589810 0.038 Uiso 1 1 calc R U . . .
C4 C 0.85926(18) 0.49085(16) 0.67594(9) 0.0322(4) Uani 1 1 d . . . . .
H4 H 0.833993 0.451141 0.712355 0.039 Uiso 1 1 calc R U . . .
C5 C 0.96380(19) 0.54494(18) 0.69252(9) 0.0363(5) Uani 1 1 d . . . . .
C6 C 0.99948(18) 0.62795(19) 0.64763(10) 0.0356(5) Uani 1 1 d . . . . .
H6 H 1.025038 0.588705 0.611127 0.043 Uiso 1 1 calc R U . . .
C7 C 0.90743(18) 0.70167(17) 0.62829(9) 0.0315(4) Uani 1 1 d . . . . .
H7 H 0.930035 0.743368 0.592037 0.038 Uiso 1 1 calc R U . . .
C8 C 0.79790(17) 0.64488(16) 0.61597(8) 0.0282(4) Uani 1 1 d . . . . .
C9 C 0.78413(16) 0.60451(16) 0.55084(8) 0.0271(4) Uani 1 1 d . . . . .
H9 H 0.766369 0.668540 0.525579 0.033 Uiso 1 1 calc R U . . .
C10 C 0.68934(16) 0.52350(16) 0.54340(8) 0.0272(4) Uani 1 1 d . . . . .
H10 H 0.638828 0.538920 0.577482 0.033 Uiso 1 1 calc R U . . .
C11 C 0.62378(18) 0.54995(17) 0.48643(9) 0.0310(4) Uani 1 1 d . . . . .
C12 C 0.51677(18) 0.49214(19) 0.48087(9) 0.0354(5) Uani 1 1 d . . . . .
H12 H 0.482845 0.508834 0.441193 0.042 Uiso 1 1 calc R U . . .
C13 C 0.53287(19) 0.3722(2) 0.48689(10) 0.0388(5) Uani 1 1 d . . . . .
H13A H 0.569623 0.344993 0.450419 0.047 Uiso 1 1 calc R U . . .
H13B H 0.460786 0.337022 0.489442 0.047 Uiso 1 1 calc R U . . .
C14 C 0.59946(18) 0.34100(18) 0.54136(9) 0.0348(5) Uani 1 1 d . . . . .
H14 H 0.612620 0.261743 0.539979 0.042 Uiso 1 1 calc R U . . .
C15 C 0.78327(19) 0.35522(18) 0.49545(9) 0.0362(5) Uani 1 1 d . . . . .
H15A H 0.753042 0.377714 0.456775 0.054 Uiso 1 1 calc R U . . .
H15B H 0.857203 0.383650 0.499686 0.054 Uiso 1 1 calc R U . . .
H15C H 0.785248 0.276575 0.497380 0.054 Uiso 1 1 calc R U . . .
C16 C 1.0193(2) 0.5142(2) 0.74045(12) 0.0513(7) Uani 1 1 d . . . . .
H16A H 0.992922 0.457224 0.764767 0.062 Uiso 1 1 calc R U . . .
H16B H 1.085564 0.549154 0.750499 0.062 Uiso 1 1 calc R U . . .
C17 C 0.71764(19) 0.73702(16) 0.62992(9) 0.0315(4) Uani 1 1 d . . . . .
H17 H 0.716685 0.786028 0.594390 0.038 Uiso 1 1 calc R U . . .
C18 C 0.60001(19) 0.7102(2) 0.64528(11) 0.0415(5) Uani 1 1 d . . . . .
H18A H 0.598312 0.651139 0.674352 0.062 Uiso 1 1 calc R U . . .
H18B H 0.561393 0.688555 0.608779 0.062 Uiso 1 1 calc R U . . .
H18C H 0.564637 0.773552 0.662600 0.062 Uiso 1 1 calc R U . . .
C19 C 0.77620(19) 0.79479(16) 0.67997(9) 0.0341(5) Uani 1 1 d . . . . .
C20 C 0.6724(2) 0.5893(2) 0.43061(10) 0.0404(5) Uani 1 1 d . . . . .
H20A H 0.752640 0.594772 0.428672 0.048 Uiso 1 1 calc R U . . .
H20B H 0.636627 0.569432 0.392405 0.048 Uiso 1 1 calc R U . . .
C21 C 0.7324(2) 0.2004(2) 0.66056(14) 0.0556(7) Uani 1 1 d . . . . .
C22 C 0.7335(4) 0.0813(2) 0.6540(2) 0.0915(14) Uani 1 1 d . . . . .
H22A H 0.720031 0.047829 0.693037 0.137 Uiso 1 1 calc R U . . .
H22B H 0.804559 0.058220 0.638771 0.137 Uiso 1 1 calc R U . . .
H22C H 0.676575 0.059445 0.625701 0.137 Uiso 1 1 calc R U . . .
C23 C 1.0417(2) 0.31819(18) 0.63261(10) 0.0380(5) Uani 1 1 d . . . . .
C24 C 1.1023(2) 0.2346(2) 0.66723(12) 0.0533(7) Uani 1 1 d . . . . .
H24A H 1.169447 0.216068 0.645914 0.080 Uiso 1 1 calc R U . . .
H24B H 1.056923 0.170275 0.671377 0.080 Uiso 1 1 calc R U . . .
H24C H 1.120294 0.262595 0.707083 0.080 Uiso 1 1 calc R U . . .
C25 C 0.94115(18) 0.61515(18) 0.48507(10) 0.0347(5) Uani 1 1 d . . . . .
C26 C 1.0376(2) 0.5515(2) 0.46536(13) 0.0513(6) Uani 1 1 d . . . . .
H26A H 1.018585 0.509429 0.429731 0.077 Uiso 1 1 calc R U . . .
H26B H 1.059938 0.502986 0.497683 0.077 Uiso 1 1 calc R U . . .
H26C H 1.097565 0.600433 0.455705 0.077 Uiso 1 1 calc R U . . .
C27 C 0.35006(19) 0.57105(19) 0.51384(12) 0.0409(5) Uani 1 1 d . . . . .
C28 C 0.2850(2) 0.5956(2) 0.56848(14) 0.0539(7) Uani 1 1 d . . . . .
H28A H 0.235664 0.655678 0.560124 0.081 Uiso 1 1 calc R U . . .
H28B H 0.333965 0.615197 0.601386 0.081 Uiso 1 1 calc R U . . .
H28C H 0.242466 0.532245 0.579888 0.081 Uiso 1 1 calc R U . . .
C29 C 0.4814(2) 0.2844(2) 0.62094(12) 0.0500(6) Uani 1 1 d . . . . .
C30 C 0.4264(3) 0.3227(3) 0.67645(15) 0.0805(11) Uani 1 1 d . . . . .
H30A H 0.398912 0.260906 0.699069 0.121 Uiso 1 1 calc R U . . .
H30B H 0.365619 0.369831 0.665637 0.121 Uiso 1 1 calc R U . . .
H30C H 0.478465 0.362614 0.701179 0.121 Uiso 1 1 calc R U . . .
O15 O 0.6829(11) 0.5507(10) 0.8431(6) 0.116(3) Uani 0.269(4) 1 d . U P . .
H15D H 0.641123 0.558766 0.876189 0.173 Uiso 0.269(4) 1 d R U P . .
H15E H 0.635797 0.519183 0.812041 0.173 Uiso 0.269(4) 1 d R U P . .
O15' O 0.6412(13) 0.3418(13) 0.8147(6) 0.116(3) Uani 0.231(4) 1 d . . P . .
H15F H 0.696929 0.298322 0.804095 0.173 Uiso 0.231(4) 1 d R U P . .
H15G H 0.672017 0.423998 0.803935 0.173 Uiso 0.231(4) 1 d R U P . .


_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
Cl1 C6 1.794(2) . ?
O1 C21 1.352(3) . ?
O1 C2 1.443(2) . ?
O2 C21 1.193(4) . ?
O3 C23 1.351(3) . ?
O3 C3 1.444(2) . ?
O4 C23 1.201(3) . ?
O5 C8 1.426(2) . ?
O5 C4 1.438(2) . ?
O6 C19 1.351(3) . ?
O6 C7 1.450(2) . ?
O7 C25 1.365(3) . ?
O7 C9 1.452(2) . ?
O8 C25 1.190(3) . ?
O9 C11 1.440(3) . ?
O9 C20 1.443(3) . ?
O10 C27 1.339(3) . ?
O10 C12 1.450(3) . ?
O11 C27 1.202(3) . ?
O12 C29 1.351(3) . ?
O12 C14 1.452(3) . ?
O13 C29 1.196(4) . ?
O14 C19 1.200(3) . ?
C1 C15 1.542(3) . ?
C1 C2 1.553(3) . ?
C1 C14 1.557(3) . ?
C1 C10 1.577(3) . ?
C2 C3 1.548(3) . ?
C3 C4 1.537(3) . ?
C4 C5 1.497(3) . ?
C5 C16 1.325(3) . ?
C5 C6 1.504(3) . ?
C6 C7 1.519(3) . ?
C7 C8 1.545(3) . ?
C8 C17 1.544(3) . ?
C8 C9 1.546(3) . ?
C9 C10 1.550(3) . ?
C10 C11 1.540(3) . ?
C11 C20 1.465(3) . ?
C11 C12 1.505(3) . ?
C12 C13 1.512(3) . ?
C13 C14 1.515(3) . ?
C17 C19 1.510(3) . ?
C17 C18 1.523(3) . ?
C21 C22 1.490(4) . ?
C23 C24 1.495(3) . ?
C25 C26 1.492(3) . ?
C27 C28 1.490(4) . ?
C29 C30 1.489(4) . ?

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 O1 C2 115.7(2) . . ?
C23 O3 C3 116.52(17) . . ?
C8 O5 C4 118.08(16) . . ?
C19 O6 C7 110.13(16) . . ?
C25 O7 C9 119.05(16) . . ?
C11 O9 C20 61.06(14) . . ?
C27 O10 C12 117.79(18) . . ?
C29 O12 C14 117.56(19) . . ?
C15 C1 C2 110.97(17) . . ?
C15 C1 C14 106.74(17) . . ?
C2 C1 C14 104.99(17) . . ?
C15 C1 C10 114.28(17) . . ?
C2 C1 C10 111.79(16) . . ?
C14 C1 C10 107.44(16) . . ?
O1 C2 C3 109.24(17) . . ?
O1 C2 C1 105.75(17) . . ?
C3 C2 C1 116.67(18) . . ?
O3 C3 C4 105.66(16) . . ?
O3 C3 C2 110.35(16) . . ?
C4 C3 C2 108.82(17) . . ?
O5 C4 C5 112.08(17) . . ?
O5 C4 C3 110.22(16) . . ?
C5 C4 C3 113.78(18) . . ?
C16 C5 C4 120.8(2) . . ?
C16 C5 C6 125.8(2) . . ?
C4 C5 C6 113.26(18) . . ?
C5 C6 C7 112.74(19) . . ?
C5 C6 Cl1 112.19(15) . . ?
C7 C6 Cl1 109.62(16) . . ?
O6 C7 C6 108.31(16) . . ?
O6 C7 C8 104.42(16) . . ?
C6 C7 C8 115.04(17) . . ?
O5 C8 C17 103.82(15) . . ?
O5 C8 C7 110.76(16) . . ?
C17 C8 C7 100.45(16) . . ?
O5 C8 C9 114.94(16) . . ?
C17 C8 C9 111.13(16) . . ?
C7 C8 C9 114.26(16) . . ?
O7 C9 C8 110.82(16) . . ?
O7 C9 C10 111.16(15) . . ?
C8 C9 C10 113.22(15) . . ?
C11 C10 C9 110.04(16) . . ?
C11 C10 C1 109.74(16) . . ?
C9 C10 C1 120.41(17) . . ?
O9 C11 C20 59.58(14) . . ?
O9 C11 C12 112.25(18) . . ?
C20 C11 C12 116.52(19) . . ?
O9 C11 C10 116.77(17) . . ?
C20 C11 C10 123.97(19) . . ?
C12 C11 C10 115.04(18) . . ?
O10 C12 C11 107.49(17) . . ?
O10 C12 C13 109.50(19) . . ?
C11 C12 C13 110.51(19) . . ?
C12 C13 C14 113.25(19) . . ?
O12 C14 C13 109.27(18) . . ?
O12 C14 C1 107.46(16) . . ?
C13 C14 C1 114.80(18) . . ?
C19 C17 C18 113.01(18) . . ?
C19 C17 C8 101.41(17) . . ?
C18 C17 C8 119.27(18) . . ?
O14 C19 O6 121.0(2) . . ?
O14 C19 C17 128.7(2) . . ?
O6 C19 C17 110.29(18) . . ?
O9 C20 C11 59.37(13) . . ?
O2 C21 O1 123.6(3) . . ?
O2 C21 C22 125.6(3) . . ?
O1 C21 C22 110.8(3) . . ?
O4 C23 O3 123.9(2) . . ?
O4 C23 C24 125.7(2) . . ?
O3 C23 C24 110.4(2) . . ?
O8 C25 O7 123.5(2) . . ?
O8 C25 C26 126.5(2) . . ?
O7 C25 C26 110.0(2) . . ?
O11 C27 O10 123.7(2) . . ?
O11 C27 C28 125.6(2) . . ?
O10 C27 C28 110.6(2) . . ?
O13 C29 O12 123.6(3) . . ?
O13 C29 C30 126.1(3) . . ?
O12 C29 C30 110.3(3) . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_ic22479_sq
_database_code_depnum_ccdc_archive 'CCDC 2326820'
loop_
_audit_author_name
_audit_author_address
'Ping-Jyun Sung'
;National Museum of Marine Biology and Aquarium
Taiwan
;
_audit_update_record             
;
2024-05-20 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        'Frajunolide I'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H35 Cl O12'
_chemical_formula_weight         599.01

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'
Cl Cl 0.3639 0.7018 '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      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   22.8317(3)
_cell_length_b                   22.8317(3)
_cell_length_c                   10.2937(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4647.06(15)
_cell_formula_units_Z            6
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      72.91

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    1.605
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8637
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47636
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.872
_diffrn_reflns_theta_max         74.402
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6221
_reflns_number_gt                5789
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_max     0.962
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _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 vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_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)+(0.0660P)²+0.4273P] 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 2491 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.002(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6221
_refine_ls_number_parameters     377
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Cl1 Cl 0.83784(4) 0.67622(4) 0.03974(7) 0.04572(18) Uani 1 1 d . . . . .
O1 O 0.81988(10) 0.72004(9) 0.65271(19) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.76949(17) 0.76086(16) 0.5234(3) 0.0767(9) Uani 1 1 d . . . . .
O3 O 0.85508(12) 0.55639(11) 0.05363(19) 0.0432(5) Uani 1 1 d . . . . .
O4 O 0.76265(9) 0.57208(10) 0.26345(17) 0.0307(4) Uani 1 1 d . . . . .
H4 H 0.745196 0.564304 0.189083 0.046 Uiso 1 1 calc R U . . .
O5 O 0.90041(9) 0.60404(9) 0.43973(17) 0.0306(4) Uani 1 1 d . . . . .
O6 O 0.94225(12) 0.53359(13) 0.4238(3) 0.0584(6) Uani 1 1 d . . . . .
O7 O 0.74970(11) 0.42368(10) 0.5296(2) 0.0447(5) Uani 1 1 d . . . . .
O8 O 0.64470(9) 0.50247(10) 0.83712(18) 0.0341(4) Uani 1 1 d . . . . .
O9 O 0.69804(13) 0.54113(15) 1.0248(2) 0.0602(7) Uani 1 1 d . . . . .
O10 O 0.68282(8) 0.58687(9) 0.63930(17) 0.0298(4) Uani 1 1 d . . . . .
O11 O 0.66815(12) 0.64448(12) 0.8025(3) 0.0544(6) Uani 1 1 d . . . . .
O12 O 0.78283(16) 0.45482(14) -0.0225(2) 0.0604(6) Uani 1 1 d . . . . .
C1 C 0.79914(11) 0.60622(12) 0.6199(2) 0.0250(5) Uani 1 1 d . . . . .
C2 C 0.81220(12) 0.67224(12) 0.5506(2) 0.0288(5) Uani 1 1 d . . . . .
H2 H 0.771895 0.662209 0.496367 0.035 Uiso 1 1 calc R U . . .
C3 C 0.87406(13) 0.70469(13) 0.4670(3) 0.0323(5) Uani 1 1 d . . . . .
H3 H 0.917609 0.723500 0.505440 0.039 Uiso 1 1 calc R U . . .
C4 C 0.86815(14) 0.70720(13) 0.3398(3) 0.0338(5) Uani 1 1 d . . . . .
H4A H 0.827220 0.702356 0.306055 0.041 Uiso 1 1 calc R U . . .
C5 C 0.92159(14) 0.71711(14) 0.2473(3) 0.0385(6) Uani 1 1 d . . . . .
C6 C 0.89893(14) 0.66719(15) 0.1382(3) 0.0381(6) Uani 1 1 d . . . . .
H6 H 0.939450 0.681008 0.081872 0.046 Uiso 1 1 calc R U . . .
C7 C 0.87274(14) 0.59303(14) 0.1756(2) 0.0331(5) Uani 1 1 d . . . . .
H7 H 0.912022 0.590529 0.212141 0.040 Uiso 1 1 calc R U . . .
C8 C 0.81105(12) 0.55100(13) 0.2688(2) 0.0285(5) Uani 1 1 d . . . . .
C9 C 0.83177(12) 0.55010(12) 0.4146(2) 0.0257(5) Uani 1 1 d . . . . .
H9 H 0.832722 0.507046 0.425139 0.031 Uiso 1 1 calc R U . . .
C10 C 0.77997(12) 0.54711(12) 0.5185(2) 0.0254(5) Uani 1 1 d . . . . .
H10 H 0.740806 0.543304 0.467987 0.031 Uiso 1 1 calc R U . . .
C11 C 0.75208(14) 0.48025(13) 0.5952(3) 0.0321(5) Uani 1 1 d . . . . .
C12 C 0.68917(14) 0.46236(13) 0.6721(3) 0.0355(6) Uani 1 1 d . . . . .
H12A H 0.672110 0.417929 0.714917 0.043 Uiso 1 1 calc R U . . .
H12B H 0.653376 0.459725 0.613980 0.043 Uiso 1 1 calc R U . . .
C13 C 0.70751(12) 0.51691(13) 0.7727(2) 0.0299(5) Uani 1 1 d . . . . .
H13 H 0.739827 0.516122 0.837262 0.036 Uiso 1 1 calc R U . . .
C14 C 0.73754(11) 0.58674(12) 0.7114(2) 0.0259(5) Uani 1 1 d . . . . .
H14 H 0.752069 0.621151 0.782381 0.031 Uiso 1 1 calc R U . . .
C15 C 0.85829(12) 0.61904(14) 0.7094(3) 0.0320(5) Uani 1 1 d . . . . .
H15A H 0.899698 0.635843 0.657838 0.048 Uiso 1 1 calc R U . . .
H15B H 0.848313 0.576719 0.752332 0.048 Uiso 1 1 calc R U . . .
H15C H 0.864567 0.652731 0.775213 0.048 Uiso 1 1 calc R U . . .
C16 C 0.98641(19) 0.7627(2) 0.2586(4) 0.0622(10) Uani 1 1 d . . . . .
H16A H 1.001738 0.792497 0.331060 0.075 Uiso 1 1 calc R U . . .
H16B H 1.017659 0.765745 0.194354 0.075 Uiso 1 1 calc R U . . .
C17 C 0.78291(14) 0.47919(14) 0.2088(3) 0.0361(6) Uani 1 1 d . . . . .
H17 H 0.808602 0.459023 0.249299 0.043 Uiso 1 1 calc R U . . .
C18 C 0.70810(17) 0.42855(16) 0.2276(3) 0.0479(7) Uani 1 1 d . . . . .
H18A H 0.681039 0.446351 0.188474 0.072 Uiso 1 1 calc R U . . .
H18B H 0.698030 0.421025 0.320676 0.072 Uiso 1 1 calc R U . . .
H18C H 0.697063 0.385669 0.185828 0.072 Uiso 1 1 calc R U . . .
C19 C 0.80389(17) 0.49235(16) 0.0681(3) 0.0434(7) Uani 1 1 d . . . . .
C20 C 0.79493(17) 0.45319(17) 0.6380(3) 0.0455(7) Uani 1 1 d . . . . .
H20A H 0.843995 0.480191 0.619700 0.055 Uiso 1 1 calc R U . . .
H20B H 0.783026 0.427406 0.720463 0.055 Uiso 1 1 calc R U . . .
C21 C 0.79836(17) 0.76364(16) 0.6217(4) 0.0491(8) Uani 1 1 d . . . . .
C22 C 0.8173(3) 0.8157(2) 0.7267(5) 0.0738(12) Uani 1 1 d . . . . .
H22A H 0.862753 0.853745 0.709889 0.111 Uiso 1 1 calc R U . . .
H22B H 0.816694 0.795414 0.810943 0.111 Uiso 1 1 calc R U . . .
H22C H 0.784804 0.831839 0.727726 0.111 Uiso 1 1 calc R U . . .
C23 C 0.95031(14) 0.58882(16) 0.4421(3) 0.0366(6) Uani 1 1 d . . . . .
C24 C 1.01722(15) 0.65142(19) 0.4651(3) 0.0490(7) Uani 1 1 d . . . . .
H24A H 1.049411 0.638808 0.499516 0.074 Uiso 1 1 calc R U . . .
H24B H 1.011556 0.680504 0.527832 0.074 Uiso 1 1 calc R U . . .
H24C H 1.034399 0.675853 0.383008 0.074 Uiso 1 1 calc R U . . .
C25 C 0.64818(14) 0.52053(14) 0.9608(3) 0.0371(6) Uani 1 1 d . . . . .
C26 C 0.58264(17) 0.51290(19) 1.0077(4) 0.0555(9) Uani 1 1 d . . . . .
H26A H 0.568563 0.485550 1.087106 0.083 Uiso 1 1 calc R U . . .
H26B H 0.547951 0.490523 0.940635 0.083 Uiso 1 1 calc R U . . .
H26C H 0.588502 0.557640 1.026125 0.083 Uiso 1 1 calc R U . . .
C27 C 0.64809(13) 0.61151(14) 0.7050(3) 0.0368(6) Uani 1 1 d . . . . .
C28 C 0.58088(16) 0.58890(19) 0.6434(4) 0.0505(8) Uani 1 1 d . . . . .
H28A H 0.549824 0.541466 0.665727 0.076 Uiso 1 1 calc R U . . .
H28B H 0.586209 0.593474 0.548854 0.076 Uiso 1 1 calc R U . . .
H28C H 0.562515 0.616903 0.675252 0.076 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
Cl1 C6 1.818(3) . ?
O1 C21 1.351(4) . ?
O1 C2 1.461(3) . ?
O2 C21 1.192(5) . ?
O3 C19 1.348(4) . ?
O3 C7 1.450(3) . ?
O4 C8 1.410(3) . ?
O5 C23 1.347(3) . ?
O5 C9 1.452(3) . ?
O6 C23 1.195(4) . ?
O7 C11 1.434(3) . ?
O7 C20 1.439(4) . ?
O8 C25 1.328(3) . ?
O8 C13 1.460(3) . ?
O9 C25 1.190(4) . ?
O10 C27 1.360(3) . ?
O10 C14 1.455(3) . ?
O11 C27 1.199(4) . ?
O12 C19 1.193(4) . ?
C1 C15 1.537(3) . ?
C1 C2 1.556(3) . ?
C1 C14 1.561(3) . ?
C1 C10 1.585(3) . ?
C2 C3 1.496(4) . ?
C3 C4 1.321(4) . ?
C4 C5 1.473(4) . ?
C5 C16 1.322(5) . ?
C5 C6 1.496(4) . ?
C6 C7 1.536(4) . ?
C7 C8 1.572(3) . ?
C8 C17 1.558(4) . ?
C8 C9 1.577(3) . ?
C9 C10 1.570(3) . ?
C10 C11 1.545(3) . ?
C11 C20 1.462(4) . ?
C11 C12 1.507(4) . ?
C12 C13 1.509(4) . ?
C13 C14 1.522(4) . ?
C17 C19 1.508(4) . ?
C17 C18 1.522(4) . ?
C21 C22 1.501(5) . ?
C23 C24 1.500(4) . ?
C25 C26 1.498(4) . ?
C27 C28 1.493(4) . ?

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 O1 C2 115.4(2) . . ?
C19 O3 C7 111.7(2) . . ?
C23 O5 C9 118.5(2) . . ?
C11 O7 C20 61.18(19) . . ?
C25 O8 C13 117.8(2) . . ?
C27 O10 C14 115.2(2) . . ?
C15 C1 C2 111.5(2) . . ?
C15 C1 C14 105.85(19) . . ?
C2 C1 C14 105.17(18) . . ?
C15 C1 C10 113.53(19) . . ?
C2 C1 C10 111.12(19) . . ?
C14 C1 C10 109.20(18) . . ?
O1 C2 C3 108.2(2) . . ?
O1 C2 C1 106.66(19) . . ?
C3 C2 C1 114.8(2) . . ?
C4 C3 C2 120.0(2) . . ?
C3 C4 C5 123.5(3) . . ?
C16 C5 C4 125.4(3) . . ?
C16 C5 C6 119.4(3) . . ?
C4 C5 C6 115.1(2) . . ?
C5 C6 C7 116.6(2) . . ?
C5 C6 Cl1 109.0(2) . . ?
C7 C6 Cl1 111.5(2) . . ?
O3 C7 C6 105.2(2) . . ?
O3 C7 C8 105.7(2) . . ?
C6 C7 C8 124.2(2) . . ?
O4 C8 C17 111.3(2) . . ?
O4 C8 C7 112.6(2) . . ?
C17 C8 C7 100.0(2) . . ?
O4 C8 C9 109.43(19) . . ?
C17 C8 C9 109.4(2) . . ?
C7 C8 C9 113.9(2) . . ?
O5 C9 C10 112.68(18) . . ?
O5 C9 C8 111.21(18) . . ?
C10 C9 C8 115.12(19) . . ?
C11 C10 C9 108.67(19) . . ?
C11 C10 C1 107.88(19) . . ?
C9 C10 C1 122.02(19) . . ?
O7 C11 C20 59.6(2) . . ?
O7 C11 C12 113.7(2) . . ?
C20 C11 C12 118.4(2) . . ?
O7 C11 C10 117.4(2) . . ?
C20 C11 C10 122.6(2) . . ?
C12 C11 C10 113.7(2) . . ?
C11 C12 C13 107.7(2) . . ?
O8 C13 C12 106.8(2) . . ?
O8 C13 C14 107.6(2) . . ?
C12 C13 C14 112.0(2) . . ?
O10 C14 C13 106.02(19) . . ?
O10 C14 C1 110.11(18) . . ?
C13 C14 C1 114.71(19) . . ?
C19 C17 C18 113.4(2) . . ?
C19 C17 C8 104.4(2) . . ?
C18 C17 C8 117.7(2) . . ?
O12 C19 O3 120.8(3) . . ?
O12 C19 C17 129.4(3) . . ?
O3 C19 C17 109.8(2) . . ?
O7 C20 C11 59.24(19) . . ?
O2 C21 O1 123.8(3) . . ?
O2 C21 C22 125.9(3) . . ?
O1 C21 C22 110.3(3) . . ?
O6 C23 O5 124.4(3) . . ?
O6 C23 C24 125.2(3) . . ?
O5 C23 C24 110.3(3) . . ?
O9 C25 O8 123.4(3) . . ?
O9 C25 C26 124.7(3) . . ?
O8 C25 C26 111.8(3) . . ?
O11 C27 O10 123.8(3) . . ?
O11 C27 C28 125.2(3) . . ?
O10 C27 C28 110.9(3) . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.035




