Jatrophane Diterpenoids from <i>Euphorbia esula</i> as Inhibitors of RANKL-Induced Osteoclastogenesis.
Yuan, Shengheng; Hua, Pei; Zhao, Chao; Zhou, Huihao; Xu, Jiake; Xu, Jun; Gu, Qiong; Journal of natural products 83 (2020) 1005–1017; doi:10.1021/acs.jnatprod.9b00929

data_1557705
_publ_section_title
;
 Jatrophane Diterpenoids from <i>Euphorbia esula</i> as Inhibitors of
 RANKL-Induced Osteoclastogenesis.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              1005
_journal_page_last               1017
_journal_paper_doi               10.1021/acs.jnatprod.9b00929
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H46 O13'
_chemical_formula_sum            'C37 H46 O13'
_chemical_formula_weight         698.74
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.32310(10)
_cell_length_b                   9.32310(10)
_cell_length_c                   42.7604(6)
_cell_measurement_reflns_used    15197
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      75.3030
_cell_measurement_theta_min      4.1210
_cell_volume                     3716.74(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     63.00 100.00   0.50    0.50    --   46.37-136.00  -4.00   74
  2  \w     21.00  61.00   0.50    0.50    --   46.37-136.00  -4.00   80
  3  \w     63.00 121.00   0.50    1.00    --  105.44 -51.00  44.00  116
  4  \w    -27.00   3.00   0.50    0.50    --  -46.37  38.00 -90.00   60
  5  \w   -100.00 -74.00   0.50    0.50    --  -46.37-125.00 150.00   52
  6  \w   -165.00-111.00   0.50    1.00    -- -100.00 -45.00 -60.00  108
  7  \w   -141.00 -85.00   0.50    1.00    -- -100.00 -51.00  44.00  112
  8  \w     50.00  76.00   0.50    1.00    --  105.44 -94.00-150.00   52
  9  \w     55.00 108.00   0.50    1.00    --  105.44 -94.00  30.00  106
 10  \w    -86.00 -41.00   0.50    1.00    --  -46.37 133.00-118.00   90
 11  \w   -117.00 -71.00   0.50    1.00    --  -46.37-125.00-180.00   92
 12  \w   -103.00 -77.00   0.50    1.00    --  -46.37-125.00 -60.00   52
 13  \w    -59.00 -31.00   0.50    1.00    --  -46.37  38.00 120.00   56
 14  \w   -170.00-124.00   0.50    2.00    -- -100.00 -45.00 120.00   92
 15  \w   -113.00 -85.00   0.50    2.00    -- -100.00 -45.00 120.00   56
 16  \w     86.00 119.00   0.50    2.00    --  107.00 -77.00-150.00   66
 17  \w     34.00  61.00   0.50    2.00    --  107.00 -77.00-150.00   54
 18  \w     35.00  69.00   0.50    2.00    --  107.00 -45.00-120.00   68
 19  \w     84.00 109.00   0.50    2.00    --  107.00 -94.00 -30.00   50
 20  \w     44.00  70.00   0.50    2.00    --  107.00 -94.00 -30.00   52
 21  \w     89.00 117.00   0.50    2.00    --  107.00  15.00  90.00   56
 22  \w    132.00 177.00   0.50    2.00    --  107.00  15.00  90.00   90
 23  \w    109.00 135.00   0.50    2.00    --  107.00  45.00-180.00   52
 24  \w    146.00 175.00   0.50    2.00    --  107.00  45.00-180.00   58
 25  \w     34.00  59.00   0.50    2.00    --  107.00 -94.00-180.00   50
 26  \w     34.00 115.00   0.50    2.00    --  107.00 -30.00 -90.00  162
 27  \w     90.00 121.00   0.50    2.00    --  107.00 -45.00-120.00   62
 28  \w     32.00 118.00   0.50    1.00    --   46.37  51.00-169.00  172
 29  \w     23.00 118.00   0.50    1.00    --   46.37  77.00 -60.00  190
 30  \w     30.00 118.00   0.50    1.00    --   46.37  57.00 -90.00  176
 31  \w     26.00 118.00   0.50    1.00    --   46.37  69.00   4.00  184
 32  \w     23.00 118.00   0.50    1.00    --   46.37  77.00  60.00  190
 33  \w     90.00 128.00   0.50    2.00    --  107.00  61.00 -30.00   76
 34  \w    -44.00 -19.00   0.50    1.00    --  -46.37  69.00   4.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0474425000
_diffrn_orient_matrix_UB_12      -0.0615035000
_diffrn_orient_matrix_UB_13      0.0317941000
_diffrn_orient_matrix_UB_21      0.0918317000
_diffrn_orient_matrix_UB_22      0.1134300000
_diffrn_orient_matrix_UB_23      0.0169510000
_diffrn_orient_matrix_UB_31      -0.1289079000
_diffrn_orient_matrix_UB_32      0.1032101000
_diffrn_orient_matrix_UB_33      0.0004041000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            39107
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.899
_diffrn_reflns_theta_min         4.135
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2351 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(13)
_refine_ls_extinction_coef       0.00133(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         7650
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.5328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.948
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                6084
_reflns_number_total             7650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00929_si_003.cif
_cod_data_source_block           yuanshh_191025
_cod_depositor_comments
'Adding full bibliography for 1557703--1557705.cif.'
_cod_original_cell_volume        3716.74(10)
_cod_database_code               1557705
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.925
_diffrn_oxdiff_digest_frames
;
01dbd4522d5ad3d922d37a63094e102c630076052cc
;
_diffrn_oxdiff_digest_hkl
;
01245e6e4c68f08d737b26592a812b4078bb20
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C1(H1), C3(H3), C14(H14), C12(H12), C7(H7), C13(H13), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C46(H46), C50(H50), C49(H49), C48(H48), C47(H47), C6(H6), C5(H5)
2.d Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C26(H26A,H26B,H26C), C30(H30A,H30B,H30C), C38(H38A,H38B,
 H38C), C22(H22A,H22B,H22C), C42(H42A,H42B,H42C), C34(H34A,H34B,H34C), C40(H40A,
 H40B,H40C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              71913
_shelx_hkl_checksum              30887
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.099
_oxdiff_exptl_absorpt_empirical_full_min 0.552