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_1557703
_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         'C41 H47 N O13'
_chemical_formula_sum            'C41 H47 N O13'
_chemical_formula_weight         761.79
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-22
_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                   13.5605(5)
_cell_length_b                   16.7746(6)
_cell_length_c                   17.6055(7)
_cell_measurement_reflns_used    17286
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1340
_cell_measurement_theta_min      3.6420
_cell_volume                     4004.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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    -25.00  62.00   0.50    0.20    --   46.62 -51.00  73.00  174
  2  \w   -173.00 -77.00   0.50    1.50    -- -100.00 -85.00-142.00  192
  3  \w   -173.00 -84.00   0.50    1.50    -- -100.00 -51.00  73.00  178
  4  \w     81.00 178.00   0.50    1.50    --  107.00  90.00  78.00  194
  5  \w   -119.00 -71.00   0.50    0.20    --  -46.62-125.00  60.00   96
  6  \w   -119.00 -71.00   0.50    0.20    --  -46.62-125.00  30.00   96
  7  \w   -119.00 -71.00   0.50    0.20    --  -46.62-125.00 -90.00   96
  8  \w   -119.00 -71.00   0.50    0.20    --  -46.62-125.00   0.00   96
  9  \w   -119.00 -71.00   0.50    0.20    --  -46.62-125.00 120.00   96
 10  \w     15.00  95.00   0.50    0.20    --   46.62-125.00 -30.00  160
 11  \w     32.00 123.00   0.50    1.50    --  107.00 -30.00 -60.00  182
 12  \w     76.00 178.00   0.50    1.50    --  107.00 125.00 -60.00  204
 13  \w     34.00 117.00   0.50    1.50    --  107.00-125.00 -30.00  166
 14  \w     92.00 178.00   0.50    1.50    --  107.00  30.00 150.00  172
 15  \w     36.00 122.00   0.50    1.50    --  107.00 -30.00  90.00  172
 16  \w    148.00 176.00   0.50    1.50    --  107.00  30.00 120.00   56
 17  \w     69.00 131.00   0.50    1.50    --  107.00 -77.00 -30.00  124
 18  \w     34.00  70.00   0.50    1.50    --  107.00-125.00 120.00   72
 19  \w     35.00  61.00   0.50    1.50    --  107.00 -77.00 -30.00   52
 20  \w     83.00 108.00   0.50    1.50    --  107.00-125.00 120.00   50
 21  \w     93.00 143.00   0.50    1.50    --  107.00  30.00 120.00  100
 22  \w    106.00 177.00   0.50    1.50    --  107.00  77.00  30.00  142
;
_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      0.0586544000
_diffrn_orient_matrix_UB_12      0.0778951000
_diffrn_orient_matrix_UB_13      -0.0102337000
_diffrn_orient_matrix_UB_21      -0.0394599000
_diffrn_orient_matrix_UB_22      0.0305817000
_diffrn_orient_matrix_UB_23      0.0767439000
_diffrn_orient_matrix_UB_31      0.0889224000
_diffrn_orient_matrix_UB_32      -0.0377798000
_diffrn_orient_matrix_UB_33      0.0408326000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37780
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.258
_diffrn_reflns_theta_min         3.640
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 2892 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         8218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0552
_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/[\s^2^(Fo^2^)+(0.0979P)^2^+1.9252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1745
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                7309
_reflns_number_total             8218
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00929_si_002.cif
_cod_data_source_block           yuanshh_190415_2
_cod_depositor_comments
'Adding full bibliography for 1557703--1557705.cif.'
_cod_database_code               1557703
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.799
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C12(H12), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C47(H47), C45(H45), C14(H14), C55(H55), C13(H13), C48(H48), C51(H51),
 C49(H49), C54(H54), C53(H53), C52(H52)
2.d X=CH2 refined with riding coordinates:
 C39(H39A,H39B)
2.e Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C40(H40A,H40B,H40C), C37(H37A,H37B,H37C), C29(H29A,H29B,
 H29C), C43(H43A,H43B,H43C), C33(H33A,H33B,H33C), C25(H25A,H25B,H25C), C42(H42A,
 H42B,H42C)
;
_shelx_res_checksum              37132
_shelx_hkl_checksum              23595
_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 1.940
_oxdiff_exptl_absorpt_empirical_full_min 0.690