Norsampsones A-D, Four New Decarbonyl Polycyclic Polyprenylated Acylphloroglucinols from Hypericum sampsonii.
Tian, Wen-Jing; Yu, Yang; Yao, Xiao-Jun; Chen, Hai-Feng; Dai, Yi; Zhang, Xiao-Kun; Yao, Xin-Sheng; Organic letters 16 (2014) 3448–3451; doi:10.1021/ol501333k

data_1516665
_publ_section_title
;
 Norsampsones A-D, Four New Decarbonyl Polycyclic Polyprenylated
 Acylphloroglucinols from Hypericum sampsonii.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3448
_journal_page_last               3451
_journal_paper_doi               10.1021/ol501333k
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H36 O4'
_chemical_formula_sum            'C30 H36 O4'
_chemical_formula_weight         460.59
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.410(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7866(4)
_cell_length_b                   7.7855(3)
_cell_length_c                   14.9348(7)
_cell_measurement_temperature    293(2)
_cell_volume                     1237.33(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11720
_diffrn_reflns_theta_full        62.48
_diffrn_reflns_theta_max         62.48
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.1456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                3443
_reflns_number_total             3752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501333k_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1516665.cif.'
_cod_database_code               1516665
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C19(H19A,H19B), C24(H24A,H24B), C25(H25A,H25B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C30(H30)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C)
;