Unprecedented Polycyclic Polyprenylated Acylphloroglucinols with Anti-Alzheimer’s Activity from St. John’s Wort
Guo, Yi; Huang, Fang; Sun, Weiguang; Zhou, Yuan; Chen, Chunmei; Qi, Changxing; Yang, Jing; Li, Xiao-Nian; Luo, Zengwei; Zhu, Hucheng; Wang, Xiaochuan; Zhang, Yonghui; Chemical Science  (2021) –; doi:10.1039/D1SC03356E

data_1564251
_publ_section_title
;
 Unprecedented Polycyclic Polyprenylated Acylphloroglucinols with
 Anti-Alzheimer&#x2019;s Activity from St. John&#x2019;s Wort
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03356E
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H44 O4'
_chemical_formula_sum            'C28 H44 O4'
_chemical_formula_weight         444.63
_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
_audit_update_record
;
2019-06-26 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.98470(10)
_cell_length_b                   43.8208(7)
_cell_length_c                   8.69360(10)
_cell_measurement_reflns_used    26921
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      73.2450
_cell_measurement_theta_min      5.1530
_cell_volume                     2660.89(6)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_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  0.0496
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            57480
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.906
_diffrn_reflns_theta_min         2.016
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.6356
_exptl_transmission_factor_min   0.4523
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 4066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         10576
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+2.3995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.1978
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                9624
_reflns_number_total             10576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03356e2.cif
_cod_data_source_block           20181019-GY-1-90-12
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1564251
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.765
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              86301
_shelx_hkl_checksum              53835