Hypersonins A-D, Polycyclic Polyprenylated Acylphloroglucinols with a 1,2-<i>seco</i>-Homoadamantane Architecture from <i>Hypericum wilsonii</i>.
Xie, Shuangshuang; Tan, Xiaosheng; Liu, Yaping; Duan, Yulin; Chen, Gang; Feng, Hao; Sun, Lingjuan; Huang, Yingying; Guo, Yi; Shi, Zhengyi; Zhou, Yuan; Qi, Changxing; Zhang, Yonghui; Journal of natural products 83 (2020) 1804–1809; doi:10.1021/acs.jnatprod.9b01187

data_1558331
_publ_section_title
;
 Hypersonins A-D, Polycyclic Polyprenylated Acylphloroglucinols with a
 1,2-<i>seco</i>-Homoadamantane Architecture from <i>Hypericum
 wilsonii</i>.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1804
_journal_page_last               1809
_journal_paper_doi               10.1021/acs.jnatprod.9b01187
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H48 O6'
_chemical_formula_sum            'C31 H48 O6'
_chemical_formula_weight         516.69
_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
_audit_creation_date             2019-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.0033(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.90373(13)
_cell_length_b                   9.73486(11)
_cell_length_c                   14.2878(2)
_cell_measurement_reflns_used    30352
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6840
_cell_measurement_theta_min      3.1610
_cell_volume                     1483.44(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -60.00 -10.00   0.50    0.50    --    0.00 -31.00  24.00  100
  2  \w     36.00  61.00   0.50    0.50    --    0.00  31.00-175.00   50
  3  \w     94.00 132.00   0.50    0.50    --   94.60  31.00-175.00   76
  4  \w     31.00 106.00   0.50    0.50    --   94.60 -31.00  24.00  150
  5  \w     59.00  86.00   0.50    0.50    --    0.00  57.00-180.00   54
  6  \w    -21.00  52.00   0.50    0.50    --    0.00  57.00-180.00  146
  7  \w    -32.00  29.00   0.50    0.50    --    0.00 -82.00 -30.00  122
  8  \w    -23.00  15.00   0.50    0.50    --    0.00 -38.00 120.00   76
  9  \w    -88.00 -45.00   0.50    0.50    --    0.00 -38.00 120.00   86
 10  \w     39.00  88.00   0.50    0.50    --    0.00  38.00 -30.00   98
 11  \w    -17.00  30.00   0.50    0.50    --    0.00  38.00 -30.00   94
 12  \w    -24.00  30.00   0.50    0.50    --    0.00 -82.00  30.00  108
 13  \w    -32.00  30.00   0.50    0.50    --    0.00 -82.00-150.00  124
 14  \w    -16.00  62.00   0.50    0.50    --    0.00  38.00  60.00  156
 15  \w     67.00  93.00   0.50    0.50    --   94.60  71.00-171.63   52
 16  \w     77.00 184.00   0.50    0.50    --   94.60  50.00  57.91  214
 17  \w     67.00  93.00   0.50    0.50    --   94.60  71.00  85.48   52
 18  \w     67.00  93.00   0.50    0.50    --   94.60  71.00-138.48   52
 19  \w     41.00 125.00   0.50    0.50    --   94.60 -82.00 -60.00  168
 20  \w    156.00 181.00   0.50    0.50    --   94.60  59.00  70.44   50
 21  \w    101.00 174.00   0.50    0.50    --   94.60  66.00   9.56  146
 22  \w    159.00 184.00   0.50    0.50    --   94.60  63.00 -14.37   50
 23  \w     79.00 124.00   0.50    0.50    --   94.60 -82.00  90.00   90
 24  \w     70.00 108.00   0.50    0.50    --   94.60  63.00 -14.37   76
 25  \w     73.00 181.00   0.50    0.50    --   94.60  61.00  30.00  216
 26  \w     71.00 126.00   0.50    0.50    --   94.60 -82.00-150.00  110
 27  \w     72.00 116.00   0.50    0.50    --   94.60  61.00 -90.00   88
 28  \w     71.00  96.00   0.50    0.50    --   94.60  61.00   0.00   50
 29  \w     71.00 182.00   0.50    0.50    --   94.60  60.00 -40.72  222
 30  \w     75.00 120.00   0.50    0.50    --   94.60  45.00-180.00   90
 31  \w     74.00 184.00   0.50    0.50    --   94.60  51.00  95.59  220
 32  \w     72.00 183.00   0.50    0.50    --   94.60  58.00 130.32  222
 33  \w     72.00 102.00   0.50    0.50    --   94.60  61.00-150.00   60
 34  \w     67.00  93.00   0.50    0.50    --   94.60  72.00  41.64   52
 35  \w     71.00 148.00   0.50    0.50    --   94.60  59.00  70.44  154
 36  \w     53.00  78.00   0.50    0.50    --   94.60 -82.00  90.00   50
 37  \w     72.00 183.00   0.50    0.50    --   94.60  57.00 -71.37  222
 38  \w     69.00  96.00   0.50    0.50    --   94.60  66.00 138.04   54
 39  \w     69.00 139.00   0.50    0.50    --   94.60  71.00-116.48  140
 40  \w     12.00 126.00   0.50    0.50    --   94.60 -82.00   0.00  228
 41  \w     69.00 183.00   0.50    0.50    --   94.60  66.00 173.48  228
 42  \w     71.00  96.00   0.50    0.50    --   94.60  61.00  90.00   50
 43  \w     75.00 120.00   0.50    0.50    --   94.60  45.00-120.00   90
 44  \w     67.00 101.00   0.50    0.50    --   94.60  72.00-127.04   68
 45  \w    156.00 182.00   0.50    0.50    --   94.60  71.00-138.48   52
 46  \w    109.00 178.00   0.50    0.50    --   94.60  71.00-171.63  138
 47  \w     68.00 102.00   0.50    0.50    --   94.60 -82.00 -30.00   68
 48  \w      9.00  96.00   0.50    0.50    --   94.60 -82.00-180.00  174
 49  \w     69.00  95.00   0.50    0.50    --   94.60  66.00   9.56   52
 50  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 120.00   52
 51  \w     69.00  95.00   0.50    0.50    --   94.60  67.00 -69.14   52
 52  \w    120.00 146.00   0.50    0.50    --   94.60  67.00 -69.14   52
 53  \w     11.00  81.00   0.50    0.50    --   94.60 -77.00 120.00  140
 54  \w     93.00 119.00   0.50    0.50    --   94.60 -77.00 120.00   52
 55  \w     71.00 119.00   0.50    0.50    --   94.60  61.00 -30.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1376765000
_diffrn_orient_matrix_UB_12      -0.0061033000
_diffrn_orient_matrix_UB_13      0.0105306000
_diffrn_orient_matrix_UB_21      -0.0120453000
_diffrn_orient_matrix_UB_22      -0.1460159000
_diffrn_orient_matrix_UB_23      -0.0423930000
_diffrn_orient_matrix_UB_31      0.0419526000
_diffrn_orient_matrix_UB_32      -0.0606765000
_diffrn_orient_matrix_UB_33      0.1012271000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33591
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.036
_diffrn_reflns_theta_min         3.162
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2719 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_coef       0.0117(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5937
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0431P)^2^+0.2554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                5912
_reflns_number_total             5937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01187_si_002.cif
_cod_data_source_block           20190308_xss30_5
_cod_depositor_comments          'Adding full bibliography for 1558331.cif.'
_cod_database_code               1558331
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.929
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C25(H25), C7(H7), C15(H15), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C14(H14A,H14B), C6(H6A,H6B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C28(H28A,H28B,H28C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,
 H31B,H31C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C30(H30A,H30B,H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.580
_oxdiff_exptl_absorpt_empirical_full_min 0.746