Gentianelloids A and B: Immunosuppressive 10,11-<i>seco</i>-Gentianellane Sesterterpenoids from the Traditional Uighur Medicine <i>Gentianella turkestanorum</i>.
Guo, Kai; Liu, Xin; Zhou, Ting-Ting; Liu, Yan-Chun; Liu, Yan; Shi, Qiu-Mei; Li, Xiao-Nian; Li, Sheng-Hong; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00272

data_4038174
_publ_section_title
;
 Gentianelloids A and B: Immunosuppressive 10,11-<i>seco</i>-Gentianellane
 Sesterterpenoids from the Traditional Uighur Medicine <i>Gentianella
 turkestanorum</i>.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00272
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H40 O4'
_chemical_formula_sum            'C25 H40 O4'
_chemical_formula_weight         404.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 91.513(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1564(14)
_cell_length_b                   11.762(3)
_cell_length_c                   16.182(4)
_cell_measurement_reflns_used    8036
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.40
_cell_measurement_theta_min      2.73
_cell_volume                     1171.4(5)
_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 0.970
_diffrn_measured_fraction_theta_max 0.952
_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  0.0590
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8087
_diffrn_reflns_point_group_measured_fraction_full 0.824
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.601
_diffrn_reflns_theta_min         2.732
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.7532
_exptl_transmission_factor_min   0.5015
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details
;
 Flack x determined using 1166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.346
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.346
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.1046
_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          0.2668
_refine_ls_wR_factor_ref         0.2909
_reflns_Friedel_coverage         0.601
_reflns_Friedel_fraction_full    0.662
_reflns_Friedel_fraction_max     0.636
_reflns_number_gt                3372
_reflns_number_total             3553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00272_si_003.cif
_cod_data_source_block           cu_gt421_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038174
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.709
_shelx_estimated_absorpt_t_max   0.954
_shelx_res_checksum              3645
_shelx_hkl_checksum              80540