Natural and Semisynthetic Tigliane Diterpenoids with New Carbon Skeletons from Euphorbia dracunculoides as a Wnt Signaling Pathway Inhibitor.
Wang, Li; Yang, Jing; Kong, Ling-Mei; Deng, Jun; Xiong, Zijun; Huang, Jianping; Luo, Jianying; Yan, Yijun; Hu, Yikao; Li, Xiao-Nian; Li, Yan; Zhao, Yong; Huang, Sheng-Xiong; Organic letters 19 (2017) 3911–3914; doi:10.1021/acs.orglett.7b01813

data_1547115
_publ_section_title
;
 Natural and Semisynthetic Tigliane Diterpenoids with New Carbon Skeletons
 from Euphorbia dracunculoides as a Wnt Signaling Pathway Inhibitor.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3911
_journal_page_last               3914
_journal_paper_doi               10.1021/acs.orglett.7b01813
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H36 O7'
_chemical_formula_sum            'C30 H36 O7'
_chemical_formula_weight         508.59
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2009(4)
_cell_length_b                   17.7433(7)
_cell_length_c                   18.2546(7)
_cell_measurement_reflns_used    5127
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.59
_cell_measurement_theta_min      3.47
_cell_volume                     2656.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1032
_diffrn_reflns_av_unetI/netI     0.1046
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12138
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.474
_diffrn_reflns_theta_min         3.474
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.9644
_exptl_absorpt_correction_T_min  0.5927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       needle
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7532
_exptl_transmission_factor_min   0.4381
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.157
_refine_ls_abs_structure_details
;
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.426
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.435
_refine_ls_R_factor_all          0.1650
_refine_ls_R_factor_gt           0.1305
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3415
_refine_ls_wR_factor_ref         0.3880
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.814
_reflns_number_gt                3050
_reflns_number_total             4476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01813_si_002.cif
_cod_data_source_block           cu_sze46_0m
_cod_database_code               1547115
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.593
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              57673
_shelx_hkl_checksum              65102