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_1564248
_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         'C31 H46 O6'
_chemical_formula_sum            'C31 H46 O6'
_chemical_formula_weight         514.68
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-12-18 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7265(2)
_cell_length_b                   15.4183(3)
_cell_length_c                   16.9237(3)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.37
_cell_measurement_theta_min      3.88
_cell_volume                     2798.92(9)
_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 0.990
_diffrn_measured_fraction_theta_max 0.975
_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  0.0333
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18027
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.367
_diffrn_reflns_theta_min         3.878
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.480
_exptl_transmission_factor_max   0.7533
_exptl_transmission_factor_min   0.5318
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1999 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0433P)^2^+0.5852P] 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         0.689
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                4953
_reflns_number_total             4965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03356e2.cif
_cod_data_source_block           cu_zyh_hp14616_0m
_cod_database_code               1564248
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.619
_shelx_estimated_absorpt_t_max   0.741
_shelx_res_checksum              95503
_shelx_hkl_checksum              10142