Callicarpins, Two Classes of Rearranged <i>ent</i>-Clerodane Diterpenoids from <i>Callicarpa</i> Plants Blocking NLRP3 Inflammasome-Induced Pyroptosis.
Pu, De-Bing; Zhang, Xing-Jie; Bi, De-Wen; Gao, Jun-Bo; Yang, Yan; Li, Xiao-Li; Lin, Jing; Li, Xiao-Nian; Zhang, Rui-Han; Xiao, Wei-Lie; Journal of natural products 83 (2020) 2191–2199; doi:10.1021/acs.jnatprod.0c00288

data_1558521
_publ_section_title
;
 Callicarpins, Two Classes of Rearranged <i>ent</i>-Clerodane Diterpenoids
 from <i>Callicarpa</i> Plants Blocking NLRP3 Inflammasome-Induced
 Pyroptosis.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              2191
_journal_page_last               2199
_journal_paper_doi               10.1021/acs.jnatprod.0c00288
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H30 O6'
_chemical_formula_sum            'C20 H30 O6'
_chemical_formula_weight         366.44
_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                   7.9639(2)
_cell_length_b                   8.3386(2)
_cell_length_c                   28.4084(8)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.19
_cell_measurement_theta_min      5.30
_cell_volume                     1886.54(8)
_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 0.982
_diffrn_measured_fraction_theta_max 0.972
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11673
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.181
_diffrn_reflns_theta_min         3.111
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.530
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.5221
_exptl_transmission_factor_min   0.3486
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0552P)^2^+0.4497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.626
_reflns_Friedel_fraction_full    0.883
_reflns_Friedel_fraction_max     0.849
_reflns_number_gt                3278
_reflns_number_total             3300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00288_si_002.cif
_cod_data_source_block           cu_xpc36_0m
_cod_depositor_comments
'Adding full bibliography for 1558521--1558525.cif.'
_cod_database_code               1558521
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.577
_shelx_estimated_absorpt_t_max   0.941
_shelx_res_checksum              77026
_shelx_hkl_checksum              56245