Tricyclic Polyprenylated Acylphloroglucinols from St John's Wort, Hypericum perforatum.
Guo, Yi; Zhang, Na; Chen, Chunmei; Huang, Jinfeng; Li, Xiao-Nian; Liu, Junjun; Zhu, Hucheng; Tong, Qingyi; Zhang, Jinwen; Luo, Zengwei; Xue, Yongbo; Zhang, Yonghui; Journal of natural products  (2017) –; doi:10.1021/acs.jnatprod.6b01178

data_1545883
_publ_section_title
;
 Tricyclic Polyprenylated Acylphloroglucinols from St John's Wort,
 Hypericum perforatum.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.6b01178
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H54 O6'
_chemical_formula_sum            'C36 H54 O6'
_chemical_formula_weight         582.79
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   '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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8783(3)
_cell_length_b                   11.8013(3)
_cell_length_c                   26.1780(8)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.05
_cell_measurement_theta_min      4.06
_cell_volume                     3360.68(16)
_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 0.985
_diffrn_measured_fraction_theta_max 0.970
_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  0.0465
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21294
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.044
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.770
_exptl_crystal_size_mid          0.750
_exptl_crystal_size_min          0.240
_exptl_transmission_factor_max   0.7533
_exptl_transmission_factor_min   0.5676
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 2389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0503P)^2^+0.5586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.881
_reflns_number_gt                5887
_reflns_number_total             5945
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b01178_si_003.cif
_cod_data_source_block           cu_zyh_hp1364_0m
_cod_database_code               1545883
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.652
_shelx_estimated_absorpt_t_max   0.868
_shelx_res_checksum              53781
_shelx_hkl_checksum              75940