# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ic17979
_audit_block_doi                 10.5517/ccdc.csd.cc207vpt
_database_code_depnum_ccdc_archive 'CCDC 1854596'
loop_
_audit_author_name
_audit_author_address
'Yuan-Bin Cheng'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-07-02 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Aleuritin
_chemical_name_common            ?
_chemical_melting_point          468-469
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 O6'
_chemical_formula_weight         348.38

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.4888(5)
_cell_length_b                   7.2783(3)
_cell_length_c                   12.9880(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.094(5)
_cell_angle_gamma                90
_cell_volume                     890.11(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1347
_cell_measurement_theta_min      5.4650
_cell_measurement_theta_max      73.3420

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.797
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1248
_diffrn_reflns_number            2787
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.429
_diffrn_reflns_theta_max         67.981
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.647
_diffrn_reflns_point_group_measured_fraction_full 0.648
_reflns_number_total             2104
_reflns_number_gt                1677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.215
_reflns_Friedel_fraction_max     0.250
_reflns_Friedel_fraction_full    0.252

_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0543P)²] 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 298 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.5(4)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2104
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.2243(3) 0.8105(4) 0.6670(2) 0.0345(7) Uani 1 1 d . . . . .
O2 O 0.1061(3) 1.0567(4) 0.6001(3) 0.0430(8) Uani 1 1 d . . . . .
O3 O 0.4310(3) 0.7564(5) 0.5081(3) 0.0419(8) Uani 1 1 d . . . . .
O4 O 0.6619(3) 0.7301(5) 0.5478(3) 0.0496(9) Uani 1 1 d . . . . .
O5 O 0.7803(4) 0.2614(8) 0.7757(5) 0.0879(16) Uani 1 1 d . . . . .
O6 O 0.7127(4) -0.0292(6) 0.7590(3) 0.0608(11) Uani 1 1 d . . . . .
C1' C 0.8579(6) -0.0818(11) 0.7486(5) 0.072(2) Uani 1 1 d . . . . .
H1'A H 0.862934 -0.215249 0.739700 0.108 Uiso 1 1 calc R U . . .
H1'B H 0.888535 -0.020390 0.688029 0.108 Uiso 1 1 calc R U . . .
H1'C H 0.920145 -0.045308 0.811139 0.108 Uiso 1 1 calc R U . . .
C1 C 0.5071(5) 0.3555(7) 0.8402(4) 0.0410(12) Uani 1 1 d . . . . .
H1A H 0.593007 0.434001 0.846871 0.049 Uiso 1 1 calc R U . . .
H1B H 0.495180 0.310415 0.910541 0.049 Uiso 1 1 calc R U . . .
C2 C 0.5340(5) 0.1892(7) 0.7727(4) 0.0426(12) Uani 1 1 d . . . . .
H2A H 0.487432 0.079916 0.798781 0.051 Uiso 1 1 calc R U . . .
H2B H 0.489952 0.212300 0.700716 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6888(6) 0.1491(9) 0.7718(4) 0.0490(14) Uani 1 1 d . . . . .
C4 C 0.2020(5) 0.2894(9) 0.8991(4) 0.0473(13) Uani 1 1 d . . . . .
C5 C 0.2390(4) 0.3595(6) 0.7956(4) 0.0330(10) Uani 1 1 d . . . . .
H5A H 0.256708 0.247719 0.754241 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1123(4) 0.4571(7) 0.7347(4) 0.0368(11) Uani 1 1 d . . . . .
H6A H 0.027185 0.377702 0.731507 0.044 Uiso 1 1 calc R U . . .
H6B H 0.092224 0.572461 0.770578 0.044 Uiso 1 1 calc R U . . .
C7 C 0.1436(4) 0.5000(7) 0.6263(3) 0.0345(10) Uani 1 1 d . . . . .
H7A H 0.058497 0.555176 0.586288 0.041 Uiso 1 1 calc R U . . .
H7B H 0.165860 0.384670 0.591221 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2680(4) 0.6319(6) 0.6276(3) 0.0308(10) Uani 1 1 d . . . . .
C9 C 0.3961(4) 0.5626(7) 0.6957(3) 0.0325(10) Uani 1 1 d . . . . .
C10 C 0.3779(5) 0.4765(6) 0.8017(3) 0.0332(10) Uani 1 1 d . . . . .
C11 C 0.5211(5) 0.5853(7) 0.6623(4) 0.0363(11) Uani 1 1 d . . . . .
H11A H 0.601176 0.529095 0.700964 0.044 Uiso 1 1 calc R U . . .
C12 C 0.5453(5) 0.6913(7) 0.5697(4) 0.0401(11) Uani 1 1 d . . . . .
C13 C 0.1848(5) 0.8233(7) 0.4847(4) 0.0364(10) Uani 1 1 d . . . . .
H13A H 0.220599 0.911542 0.436044 0.044 Uiso 1 1 calc R U . . .
H13B H 0.094863 0.768861 0.451555 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2938(5) 0.6761(6) 0.5172(3) 0.0348(11) Uani 1 1 d . . . . .
H14A H 0.277322 0.565329 0.471750 0.042 Uiso 1 1 calc R U . . .
C17 C 0.1648(4) 0.9146(7) 0.5859(4) 0.0338(10) Uani 1 1 d . . . . .
C18 C 0.2415(6) 0.1222(11) 0.9326(5) 0.073(2) Uani 1 1 d . . . . .
H18A H 0.210715 0.075620 0.994428 0.088 Uiso 1 1 calc R U . . .
H18B H 0.300481 0.049490 0.894821 0.088 Uiso 1 1 calc R U . . .
C19 C 0.1087(7) 0.4041(11) 0.9592(5) 0.080(2) Uani 1 1 d . . . . .
H19A H 0.089658 0.522394 0.924215 0.119 Uiso 1 1 calc R U . . .
H19B H 0.018799 0.339604 0.963106 0.119 Uiso 1 1 calc R U . . .
H19C H 0.156675 0.424911 1.029445 0.119 Uiso 1 1 calc R U . . .
C20 C 0.3772(6) 0.6382(8) 0.8794(4) 0.0483(13) Uani 1 1 d . . . . .
H20A H 0.365755 0.590105 0.948328 0.073 Uiso 1 1 calc R U . . .
H20B H 0.467054 0.705526 0.882600 0.073 Uiso 1 1 calc R U . . .
H20C H 0.298221 0.721213 0.856287 0.073 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 C17 1.362(5) . ?
O1 C8 1.475(5) . ?
O2 C17 1.200(5) . ?
O3 C12 1.351(6) . ?
O3 C14 1.445(5) . ?
O4 C12 1.209(5) . ?
O5 C3 1.189(7) . ?
O6 C3 1.331(7) . ?
O6 C1' 1.452(6) . ?
C1 C2 1.535(7) . ?
C1 C10 1.542(6) . ?
C2 C3 1.499(7) . ?
C4 C18 1.330(9) . ?
C4 C19 1.504(8) . ?
C4 C5 1.519(7) . ?
C5 C6 1.530(6) . ?
C5 C10 1.563(6) . ?
C6 C7 1.508(6) . ?
C7 C8 1.520(6) . ?
C8 C9 1.500(6) . ?
C8 C14 1.518(6) . ?
C9 C11 1.323(6) . ?
C9 C10 1.541(6) . ?
C10 C20 1.551(7) . ?
C11 C12 1.471(7) . ?
C13 C17 1.506(7) . ?
C13 C14 1.512(6) . ?

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
C17 O1 C8 109.2(3) . . ?
C12 O3 C14 118.4(4) . . ?
C3 O6 C1' 116.5(5) . . ?
C2 C1 C10 116.5(4) . . ?
C3 C2 C1 113.0(4) . . ?
O5 C3 O6 122.8(5) . . ?
O5 C3 C2 125.2(6) . . ?
O6 C3 C2 111.9(5) . . ?
C18 C4 C19 119.8(5) . . ?
C18 C4 C5 120.7(5) . . ?
C19 C4 C5 119.2(5) . . ?
C4 C5 C6 111.1(3) . . ?
C4 C5 C10 115.1(4) . . ?
C6 C5 C10 112.2(4) . . ?
C7 C6 C5 110.2(4) . . ?
C6 C7 C8 111.3(4) . . ?
O1 C8 C9 109.5(4) . . ?
O1 C8 C14 103.1(4) . . ?
C9 C8 C14 114.5(4) . . ?
O1 C8 C7 108.0(3) . . ?
C9 C8 C7 111.4(4) . . ?
C14 C8 C7 109.8(4) . . ?
C11 C9 C8 117.3(4) . . ?
C11 C9 C10 123.2(4) . . ?
C8 C9 C10 119.4(4) . . ?
C9 C10 C1 110.5(4) . . ?
C9 C10 C20 106.4(4) . . ?
C1 C10 C20 106.8(4) . . ?
C9 C10 C5 111.3(3) . . ?
C1 C10 C5 109.7(4) . . ?
C20 C10 C5 112.0(4) . . ?
C9 C11 C12 124.8(4) . . ?
O4 C12 O3 118.1(5) . . ?
O4 C12 C11 123.6(5) . . ?
O3 C12 C11 118.3(4) . . ?
C17 C13 C14 103.0(4) . . ?
O3 C14 C13 106.4(4) . . ?
O3 C14 C8 114.5(4) . . ?
C13 C14 C8 103.2(4) . . ?
O2 C17 O1 121.1(4) . . ?
O2 C17 C13 128.7(4) . . ?
O1 C17 C13 110.2(4) . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044


_chemical_compound_source        'twigs of Aleurites moluccanus'
####################################################################### 
# 
# 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_ic18165
_audit_block_doi                 10.5517/ccdc.csd.cc25y3bl
_database_code_depnum_ccdc_archive 'CCDC 2023969'
loop_
_audit_author_name
_audit_author_address
'Yuan-Bin Cheng'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-08-18 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
rel-(5β,8α,10α)-8-hydroxy-13-methylpodocarpa-9(11),13-diene-3,12-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 O3'
_chemical_formula_weight         288.37

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                   7.0307(10)
_cell_length_b                   8.6660(10)
_cell_length_c                   25.171(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1533.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    607
_cell_measurement_theta_min      5.3830
_cell_measurement_theta_max      75.0170

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.664
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            4095
_diffrn_reflns_av_unetI/netI     0.0986
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         5.398
_diffrn_reflns_theta_max         67.965
_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 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             2626
_reflns_number_gt                1486
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.590
_reflns_Friedel_fraction_max     0.842
_reflns_Friedel_fraction_full    0.844

_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0891P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 352 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2626
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.2208
_refine_ls_wR_factor_gt          0.1698
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.4446(8) 0.9394(7) 1.2079(2) 0.0628(16) Uani 1 1 d . . . . .
O2 O 1.0473(8) 0.4284(7) 1.0771(2) 0.0508(14) Uani 1 1 d . . . . .
O3 O 0.4687(7) 0.3800(6) 0.9542(2) 0.0514(14) Uani 1 1 d . . . . .
C1 C 0.4730(10) 0.5975(9) 1.1358(3) 0.0481(19) Uani 1 1 d . . . . .
H1A H 0.417325 0.663610 1.107785 0.058 Uiso 1 1 calc R U . . .
H1B H 0.409461 0.495615 1.134182 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4359(11) 0.6707(9) 1.1902(3) 0.050(2) Uani 1 1 d . . . . .
H2A H 0.297355 0.685370 1.195032 0.060 Uiso 1 1 calc R U . . .
H2B H 0.481249 0.600095 1.218424 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5350(12) 0.8240(9) 1.1957(3) 0.050(2) Uani 1 1 d . . . . .
C4 C 0.7474(11) 0.8295(9) 1.1834(3) 0.0479(19) Uani 1 1 d . . . . .
C5 C 0.7817(10) 0.7408(8) 1.1296(3) 0.0427(18) Uani 1 1 d . . . . .
H5A H 0.714793 0.804350 1.102211 0.051 Uiso 1 1 calc R U . . .
C6 C 0.9876(11) 0.7393(9) 1.1119(3) 0.0482(19) Uani 1 1 d . . . . .
H6A H 1.060828 0.667393 1.134644 0.058 Uiso 1 1 calc R U . . .
H6B H 1.042507 0.843716 1.116199 0.058 Uiso 1 1 calc R U . . .
C7 C 1.0047(11) 0.6894(8) 1.0541(3) 0.048(2) Uani 1 1 d . . . . .
H7A H 1.140099 0.690250 1.043234 0.058 Uiso 1 1 calc R U . . .
H7B H 0.934779 0.762709 1.031088 0.058 Uiso 1 1 calc R U . . .
C8 C 0.9228(11) 0.5267(8) 1.0471(3) 0.0448(18) Uani 1 1 d . . . . .
C9 C 0.7194(10) 0.5239(8) 1.0670(3) 0.0406(18) Uani 1 1 d . . . . .
C10 C 0.6877(9) 0.5767(8) 1.1252(3) 0.0401(17) Uani 1 1 d . . . . .
C11 C 0.5778(11) 0.4778(8) 1.0351(3) 0.0430(18) Uani 1 1 d . . . . .
H11A H 0.451774 0.478798 1.048743 0.052 Uiso 1 1 calc R U . . .
C12 C 0.6074(12) 0.4260(8) 0.9805(3) 0.0471(19) Uani 1 1 d . . . . .
C13 C 0.8014(10) 0.4307(8) 0.9585(3) 0.0435(18) Uani 1 1 d . . . . .
C14 C 0.9414(11) 0.4782(8) 0.9897(3) 0.0459(19) Uani 1 1 d . . . . .
H14A H 1.065077 0.482112 0.974553 0.055 Uiso 1 1 calc R U . . .
C17 C 0.8284(13) 0.3758(9) 0.9023(3) 0.055(2) Uani 1 1 d . . . . .
H17A H 0.704928 0.346784 0.887232 0.082 Uiso 1 1 calc R U . . .
H17B H 0.884574 0.458721 0.880977 0.082 Uiso 1 1 calc R U . . .
H17C H 0.913229 0.286069 0.902069 0.082 Uiso 1 1 calc R U . . .
C18 C 0.8505(12) 0.7622(10) 1.2325(3) 0.057(2) Uani 1 1 d . . . . .
H18A H 0.988154 0.763408 1.226336 0.086 Uiso 1 1 calc R U . . .
H18B H 0.820493 0.824782 1.263789 0.086 Uiso 1 1 calc R U . . .
H18C H 0.808210 0.655834 1.238349 0.086 Uiso 1 1 calc R U . . .
C19 C 0.8118(13) 0.9984(8) 1.1768(4) 0.060(2) Uani 1 1 d . . . . .
H19A H 0.948243 1.001304 1.168910 0.090 Uiso 1 1 calc R U . . .
H19B H 0.741114 1.046274 1.147571 0.090 Uiso 1 1 calc R U . . .
H19C H 0.786985 1.055165 1.209770 0.090 Uiso 1 1 calc R U . . .
C20 C 0.7680(11) 0.4532(9) 1.1631(3) 0.053(2) Uani 1 1 d . . . . .
H20A H 0.904341 0.439827 1.156397 0.079 Uiso 1 1 calc R U . . .
H20B H 0.748676 0.486127 1.199959 0.079 Uiso 1 1 calc R U . . .
H20C H 0.702120 0.355079 1.157093 0.079 Uiso 1 1 calc R U . . .
H2 H 1.002(12) 0.353(10) 1.072(3) 0.06(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
O1 C3 1.225(9) . ?
O2 C8 1.437(9) . ?
O3 C12 1.243(9) . ?
C1 C2 1.531(10) . ?
C1 C10 1.544(9) . ?
C2 C3 1.507(11) . ?
C3 C4 1.526(11) . ?
C4 C19 1.541(10) . ?
C4 C18 1.546(11) . ?
C4 C5 1.575(10) . ?
C5 C6 1.515(10) . ?
C5 C10 1.572(9) . ?
C6 C7 1.524(10) . ?
C7 C8 1.533(9) . ?
C8 C14 1.509(10) . ?
C8 C9 1.516(10) . ?
C9 C11 1.340(10) . ?
C9 C10 1.549(10) . ?
C10 C20 1.542(10) . ?
C11 C12 1.462(10) . ?
C12 C13 1.473(10) . ?
C13 C14 1.325(10) . ?
C13 C17 1.504(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 111.7(6) . . ?
C3 C2 C1 111.6(6) . . ?
O1 C3 C2 120.2(7) . . ?
O1 C3 C4 122.3(8) . . ?
C2 C3 C4 117.5(7) . . ?
C3 C4 C19 109.8(7) . . ?
C3 C4 C18 106.5(7) . . ?
C19 C4 C18 107.8(7) . . ?
C3 C4 C5 108.0(6) . . ?
C19 C4 C5 109.1(7) . . ?
C18 C4 C5 115.5(6) . . ?
C6 C5 C10 111.9(6) . . ?
C6 C5 C4 113.8(6) . . ?
C10 C5 C4 116.0(6) . . ?
C5 C6 C7 111.0(6) . . ?
C6 C7 C8 109.9(6) . . ?
O2 C8 C14 106.7(6) . . ?
O2 C8 C9 113.0(6) . . ?
C14 C8 C9 113.2(6) . . ?
O2 C8 C7 104.8(6) . . ?
C14 C8 C7 109.5(6) . . ?
C9 C8 C7 109.3(6) . . ?
C11 C9 C8 120.5(7) . . ?
C11 C9 C10 123.2(6) . . ?
C8 C9 C10 116.4(6) . . ?
C20 C10 C1 109.3(6) . . ?
C20 C10 C9 109.1(6) . . ?
C1 C10 C9 109.8(6) . . ?
C20 C10 C5 115.5(6) . . ?
C1 C10 C5 107.0(6) . . ?
C9 C10 C5 105.9(6) . . ?
C9 C11 C12 123.4(7) . . ?
O3 C12 C11 119.1(7) . . ?
O3 C12 C13 122.4(7) . . ?
C11 C12 C13 118.5(7) . . ?
C14 C13 C12 118.3(7) . . ?
C14 C13 C17 124.2(7) . . ?
C12 C13 C17 117.5(7) . . ?
C13 C14 C8 126.1(7) . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.066


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_compound_source        'Aleurites moluccanus'
####################################################################### 
# 
# 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_ic17860
_audit_block_doi                 10.5517/ccdc.csd.cc207vqv
_database_code_depnum_ccdc_archive 'CCDC 1854597'
loop_
_audit_author_name
_audit_author_address
'Yuan-Bin Cheng'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-07-02 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        aleuritone
_chemical_name_common            ?
_chemical_melting_point          438-439
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42

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                   7.5260(4)
_cell_length_b                   13.1519(7)
_cell_length_c                   17.4059(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1722.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1148
_cell_measurement_theta_min      4.1890
_cell_measurement_theta_max      69.0260

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.563
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1248
_diffrn_reflns_number            3770
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.213
_diffrn_reflns_theta_max         67.997
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.879
_reflns_number_total             2750
_reflns_number_gt                2111
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.541
_reflns_Friedel_fraction_max     0.733
_reflns_Friedel_fraction_full    0.735

_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0763P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 555 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.6(5)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2750
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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 1.0542(6) 0.6252(4) 0.5964(2) 0.0833(13) Uani 1 1 d . . . . .
H1 H 0.949(11) 0.631(7) 0.611(5) 0.125 Uiso 1 1 d . U . . .
O2 O 0.7609(6) 0.3070(4) 0.1652(2) 0.0886(13) Uani 1 1 d . . . . .
C1 C 0.8399(6) 0.4518(4) 0.4480(3) 0.0581(12) Uani 1 1 d . . . . .
H1A H 0.745184 0.400076 0.453116 0.070 Uiso 1 1 calc R U . . .
H1B H 0.798443 0.504234 0.411312 0.070 Uiso 1 1 calc R U . . .
C2 C 0.8745(6) 0.5017(5) 0.5271(3) 0.0706(16) Uani 1 1 d . . . . .
H2A H 0.764155 0.534709 0.545475 0.085 Uiso 1 1 calc R U . . .
H2B H 0.907753 0.448511 0.564744 0.085 Uiso 1 1 calc R U . . .
C3 C 1.0213(7) 0.5800(4) 0.5225(3) 0.0613(12) Uani 1 1 d . . . . .
H3A H 0.982261 0.634912 0.486594 0.074 Uiso 1 1 calc R U . . .
C4 C 1.1982(6) 0.5382(3) 0.4937(2) 0.0485(10) Uani 1 1 d . . . . .
C5 C 1.1634(5) 0.4805(3) 0.4163(2) 0.0415(9) Uani 1 1 d . . . . .
H5A H 1.124222 0.534544 0.379590 0.050 Uiso 1 1 calc R U . . .
C6 C 1.3306(5) 0.4348(3) 0.3795(3) 0.0485(10) Uani 1 1 d . . . . .
H6A H 1.429818 0.484021 0.383222 0.058 Uiso 1 1 calc R U . . .
H6B H 1.365337 0.372410 0.407588 0.058 Uiso 1 1 calc R U . . .
C7 C 1.2960(6) 0.4091(4) 0.2951(3) 0.0526(10) Uani 1 1 d . . . . .
H7A H 1.274069 0.472578 0.266057 0.063 Uiso 1 1 calc R U . . .
H7B H 1.402347 0.375807 0.273039 0.063 Uiso 1 1 calc R U . . .
C8 C 1.1383(6) 0.3396(3) 0.2869(2) 0.0436(9) Uani 1 1 d . . . . .
C9 C 0.9806(5) 0.3687(3) 0.3341(2) 0.0407(8) Uani 1 1 d . . . . .
C10 C 1.0079(5) 0.4018(3) 0.4169(2) 0.0412(9) Uani 1 1 d . . . . .
C11 C 0.8308(6) 0.3588(4) 0.2944(3) 0.0573(11) Uani 1 1 d . . . . .
H11A H 0.715726 0.374151 0.313542 0.069 Uiso 1 1 calc R U . . .
C12 C 0.8682(7) 0.3209(4) 0.2166(3) 0.0602(12) Uani 1 1 d . . . . .
C13 C 1.0628(7) 0.3059(3) 0.2109(2) 0.0540(11) Uani 1 1 d . . . . .
H13A H 1.124912 0.326556 0.162590 0.065 Uiso 1 1 calc R U . . .
C14 C 1.1505(6) 0.2260(3) 0.2633(2) 0.0511(10) Uani 1 1 d . . . . .
C15 C 1.3279(8) 0.1941(4) 0.2358(3) 0.0670(13) Uani 1 1 d . . . . .
H15A H 1.385194 0.238847 0.200890 0.080 Uiso 1 1 calc R U . . .
C16 C 1.4134(10) 0.1135(5) 0.2535(4) 0.097(2) Uani 1 1 d . . . . .
H16A H 1.363001 0.065770 0.288163 0.116 Uiso 1 1 calc R U . . .
H16B H 1.527389 0.101295 0.231914 0.116 Uiso 1 1 calc R U . . .
C17 C 1.0409(7) 0.1444(3) 0.3005(3) 0.0601(12) Uani 1 1 d . . . . .
H17A H 0.926474 0.172948 0.316588 0.090 Uiso 1 1 calc R U . . .
H17B H 1.020565 0.089228 0.263707 0.090 Uiso 1 1 calc R U . . .
H17C H 1.103938 0.117880 0.345469 0.090 Uiso 1 1 calc R U . . .
C18 C 1.3223(8) 0.6286(4) 0.4771(3) 0.0642(13) Uani 1 1 d . . . . .
H18A H 1.436893 0.603217 0.458426 0.096 Uiso 1 1 calc R U . . .
H18B H 1.268453 0.672333 0.437889 0.096 Uiso 1 1 calc R U . . .
H18C H 1.340545 0.667734 0.524316 0.096 Uiso 1 1 calc R U . . .
C19 C 1.2881(6) 0.4720(4) 0.5549(3) 0.0545(11) Uani 1 1 d . . . . .
H19C H 1.401141 0.446152 0.534975 0.082 Uiso 1 1 calc R U . . .
H19D H 1.310077 0.512785 0.601067 0.082 Uiso 1 1 calc R U . . .
H19A H 1.210366 0.414686 0.567897 0.082 Uiso 1 1 calc R U . . .
C20 C 1.0454(6) 0.3031(3) 0.4622(2) 0.0498(10) Uani 1 1 d . . . . .
H20D H 1.064293 0.319513 0.516475 0.075 Uiso 1 1 calc R U . . .
H20A H 0.943681 0.256977 0.457306 0.075 Uiso 1 1 calc R U . . .
H20B H 1.151885 0.270103 0.441474 0.075 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 C3 1.439(5) . ?
O2 C12 1.218(6) . ?
C1 C10 1.525(6) . ?
C1 C2 1.548(7) . ?
C2 C3 1.512(8) . ?
C3 C4 1.525(7) . ?
C4 C19 1.534(6) . ?
C4 C18 1.540(6) . ?
C4 C5 1.568(5) . ?
C5 C6 1.534(6) . ?
C5 C10 1.562(5) . ?
C6 C7 1.530(6) . ?
C7 C8 1.504(6) . ?
C8 C9 1.493(6) . ?
C8 C13 1.506(6) . ?
C8 C14 1.553(6) . ?
C9 C11 1.329(6) . ?
C9 C10 1.519(5) . ?
C10 C20 1.545(6) . ?
C11 C12 1.470(7) . ?
C12 C13 1.481(7) . ?
C13 C14 1.540(7) . ?
C14 C15 1.479(7) . ?
C14 C17 1.500(7) . ?
C15 C16 1.277(8) . ?

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
C10 C1 C2 111.1(4) . . ?
C3 C2 C1 111.3(4) . . ?
O1 C3 C2 111.1(4) . . ?
O1 C3 C4 107.0(4) . . ?
C2 C3 C4 114.2(4) . . ?
C3 C4 C19 111.1(4) . . ?
C3 C4 C18 108.2(4) . . ?
C19 C4 C18 107.5(4) . . ?
C3 C4 C5 108.2(3) . . ?
C19 C4 C5 113.3(3) . . ?
C18 C4 C5 108.3(4) . . ?
C6 C5 C10 111.0(3) . . ?
C6 C5 C4 114.2(3) . . ?
C10 C5 C4 116.1(3) . . ?
C7 C6 C5 110.3(3) . . ?
C8 C7 C6 111.1(3) . . ?
C9 C8 C7 114.7(3) . . ?
C9 C8 C13 105.0(4) . . ?
C7 C8 C13 124.1(4) . . ?
C9 C8 C14 116.1(3) . . ?
C7 C8 C14 124.3(4) . . ?
C13 C8 C14 60.4(3) . . ?
C11 C9 C8 111.3(4) . . ?
C11 C9 C10 129.5(4) . . ?
C8 C9 C10 119.2(3) . . ?
C9 C10 C1 110.4(3) . . ?
C9 C10 C20 105.5(3) . . ?
C1 C10 C20 109.4(4) . . ?
C9 C10 C5 106.6(3) . . ?
C1 C10 C5 109.7(3) . . ?
C20 C10 C5 115.0(3) . . ?
C9 C11 C12 110.5(4) . . ?
O2 C12 C11 126.8(5) . . ?
O2 C12 C13 125.9(5) . . ?
C11 C12 C13 107.2(4) . . ?
C12 C13 C8 106.0(4) . . ?
C12 C13 C14 118.4(4) . . ?
C8 C13 C14 61.3(3) . . ?
C15 C14 C17 115.7(4) . . ?
C15 C14 C13 113.0(4) . . ?
C17 C14 C13 120.5(4) . . ?
C15 C14 C8 114.4(4) . . ?
C17 C14 C8 122.7(4) . . ?
C13 C14 C8 58.3(3) . . ?
C16 C15 C14 127.8(6) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/H2O'
_chemical_compound_source        'twigs of Aleurites moluccanus'
