Diverse Polycyclic Polyprenylated Acylphloroglucinol Congeners with Anti-Nonalcoholic Steatohepatitis Activity from <i>Hypericum forrestii</i>.
Lu, Wei-Jia; Xu, Wen-Jun; Zhang, Mei-Hui; Zhang, Yan-Qiu; Li, Yi-Ran; Zhang, Hao; Luo, Jun; Kong, Ling-Yi; Journal of natural products  (2021) –; doi:10.1021/acs.jnatprod.0c01202

data_1561440
_publ_section_title
;
 Diverse Polycyclic Polyprenylated Acylphloroglucinol Congeners with
 Anti-Nonalcoholic Steatohepatitis Activity from <i>Hypericum
 forrestii</i>.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c01202
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C38 H48 O4'
_chemical_formula_sum            'C38 H48 O4'
_chemical_formula_weight         568.76
_space_group_crystal_system      hexagonal
_space_group_IT_number           179
_space_group_name_Hall           'P 65 2 (0 0 1)'
_space_group_name_H-M_alt        'P 65 2 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   12.3525(2)
_cell_length_b                   12.3525(2)
_cell_length_c                   79.6448(18)
_cell_measurement_reflns_used    9749
_cell_measurement_temperature    143
_cell_measurement_theta_max      74.651
_cell_measurement_theta_min      4.170
_cell_volume                     10524.4(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      143.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       99
_diffrn_reflns_limit_l_min       -89
_diffrn_reflns_number            129659
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.961
_diffrn_reflns_theta_min         3.329
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1386 before and 0.0860 after correction. The Ratio of minimum to maximum transmission is 0.8834. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_description       block
_exptl_crystal_F_000             3696
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
TITL 0515_0m_a.res in P6(5) New: P6522
CELL   12.3525   12.3525   79.6448     90.00     90.00    120.00
SPGR P6522
C101 0.268 0.153 0.839 !       4.78 eA-3
C102 0.952 0.826 0.335 !       3.64 eA-3
C103 0.187 0.264 0.683 !       3.23 eA-3
C104 0.095 0.999 0.000 !       0.90 eA-3
Q105 0.953 0.726 0.016 !       0.76 eA-3
C106 0.236 0.222 0.968 !       0.71 eA-3
Q107 0.359 0.124 0.997 !       0.68 eA-3
Q108 0.221 0.266 0.797 !       0.58 eA-3
Q109 0.671 0.778 0.464 !       0.57 eA-3
Q110 0.794 0.154 0.516 !       0.56 eA-3
C111 0.281 0.958 0.145 !       0.56 eA-3
C112 0.922 0.828 0.303 !       0.55 eA-3
Q113 0.981 0.099 0.519 !       0.55 eA-3
Q114 0.687 0.595 0.182 !       0.54 eA-3
Q115 0.162 0.340 0.695 !       0.53 eA-3
Q116 0.315 0.373 0.992 !       0.52 eA-3
;
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.236
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         7222
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.239
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0796
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0174P)^2^+21.8792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1810
_refine_ls_wR_factor_ref         0.1812
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                7164
_reflns_number_total             7222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01202_si_002.cif
_cod_data_source_block           0515_0m_sq
_cod_original_cell_volume        10524.4(4)
_cod_database_code               1561440
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.944
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C26) \\sim Ueq, Uanis(C1AA) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Others
 Fixed Sof: C1AA(0.75) H1AA(0.75) H1AB(0.75) H1AC(0.75) C26(0.25) H26A(0.25)
 H26B(0.25) H26C(0.25)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C28(H28)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C10(H10A,H10B), C11(H11A,H11B), C27(H27A,H27B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C38(H38), C17(H17), C23(H23), C35(H35), C36(H36), C37(H37)
4.d Idealised Me refined as rotating group:
 C1AA(H1AA,H1AB,H1AC), C21(H21A,H21B,H21C), C30(H30A,H30B,H30C), C14(H14A,H14B,
 H14C), C31(H31A,H31B,H31C), C15(H15A,H15B,H15C), C20(H20A,H20B,H20C), C19(H19A,
 H19B,H19C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'