Antiproliferative Sesquiterpenoids from Ligularia rumicifolia with Diverse Skeletons.
Ye, Ye; Dawa, Drolma; Liu, Guang-Hui; Zhao, Min; Tseden, Dorje; Gu, Yu-Cheng; Ding, Li-Sheng; Cao, Zhi-Xing; Zhou, Yan; Journal of natural products 81 (2018) 1992–2003; doi:10.1021/acs.jnatprod.8b00197

data_1553364
_publ_section_title
;
 Antiproliferative Sesquiterpenoids from Ligularia rumicifolia with
 Diverse Skeletons.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              1992
_journal_page_last               2003
_journal_paper_doi               10.1021/acs.jnatprod.8b00197
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H54 O12'
_chemical_formula_sum            'C37 H54 O12'
_chemical_formula_weight         690.80
_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   mixed
_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                   12.5134(2)
_cell_length_b                   15.2070(2)
_cell_length_c                   20.2912(3)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.24
_cell_measurement_theta_min      3.63
_cell_volume                     3861.24(10)
_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 0.995
_diffrn_measured_fraction_theta_max 0.982
_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  0.0300
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23961
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.233
_diffrn_reflns_theta_min         3.632
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       prism
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.490
_exptl_crystal_size_min          0.220
_exptl_transmission_factor_max   0.5221
_exptl_transmission_factor_min   0.3253
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 3033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         7102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0454P)^2^+0.6679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                7082
_reflns_number_total             7102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00197_si_002.cif
_cod_data_source_block           cu_zy_lrd1_0m
_cod_database_code               1553364
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.612
_shelx_estimated_absorpt_t_max   0.857
_shelx_res_checksum              39094
_shelx_hkl_checksum              86603