#------------------------------------------------------------------------------
#$Date: 2020-11-06 15:09:24 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157710.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7157710
loop_
_publ_author_name
'Chang, Fang-Rong'
'Wang, Shih-Wei'
'Chen, Shu-Rong'
'Lee, Ching-Ying'
'Sheu, Jyh-Horng'
'Cheng, Yuan-Bin'
_publ_section_title
;
 Aleuritin, a novel dinor-diterpenoid from the twigs of Aleurites
 moluccanus with an anti-lymphangiogenic effect.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7892
_journal_page_last               7898
_journal_paper_doi               10.1039/d0ob01527j
_journal_volume                  18
_journal_year                    2020
_chemical_compound_source        'twigs of Aleurites moluccanus'
_chemical_formula_sum            'C19 H24 O6'
_chemical_formula_weight         348.38
_chemical_melting_point          468.5(5)
_chemical_name_systematic        Aleuritin
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc207vpt
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-02 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.094(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4888(5)
_cell_length_b                   7.2783(3)
_cell_length_c                   12.9880(7)
_cell_measurement_reflns_used    1347
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      73.3420
_cell_measurement_theta_min      5.4650
_cell_volume                     890.12(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 5.1248
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2787
_diffrn_reflns_point_group_measured_fraction_full 0.648
_diffrn_reflns_point_group_measured_fraction_max 0.647
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.981
_diffrn_reflns_theta_min         3.429
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74373
_exptl_absorpt_correction_type   multi-scan
_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_crystal_density_diffrn    1.300
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044
_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)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0543P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.215
_reflns_Friedel_fraction_full    0.252
_reflns_Friedel_fraction_max     0.250
_reflns_number_gt                1677
_reflns_number_total             2104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01527j2.cif
_cod_data_source_block           ic17979
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '468-469' was changed to
'468.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157710--7157712.cif.
;
_cod_original_cell_volume        890.11(8)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7157710
_shelx_shelxl_version_number     2018/3
_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'
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 . . .
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'
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) . . ?
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) . ?
