Hyperpatulones A–F, polycyclic polyprenylated acylphloroglucinols from Hypericum patulum and their cytotoxic activities
Wu, Zhong-Nan; Niu, Qian-Wen; Zhang, Yu-Bo; Luo, Ding; Li, Qing-Guo; Li, Ying-Ying; Kuang, Guang-Kai; He, Li-Jun; Wang, Guo-Cai; Li, Yao-Lan; RSC Advances 9 (2019) 7961–; doi:10.1039/C9RA00277D

data_7232491
_publ_section_title
;
 Hyperpatulones A--F, polycyclic polyprenylated acylphloroglucinols from
 Hypericum patulum and their cytotoxic activities
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              7961
_journal_paper_doi               10.1039/C9RA00277D
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H50 O6'
_chemical_formula_sum            'C38 H50 O6'
_chemical_formula_weight         602.78
_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
_audit_block_doi                 10.5517/ccdc.csd.cc20m2b2
_audit_creation_date             2018-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-09-02 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2963(4)
_cell_length_b                   16.3762(4)
_cell_length_c                   11.0039(2)
_cell_measurement_reflns_used    8830
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0340
_cell_measurement_theta_min      3.5080
_cell_volume                     3477.23(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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   -129.00  47.00   1.00    1.00    --  -41.11   0.00 -90.00  176
  2  \w     23.00  97.00   1.00    1.00    --   41.11-125.00 -30.00   74
  3  \w     94.00 178.00   1.00   13.30    --  107.58 125.00 -90.00   84
  4  \w     34.00 122.00   1.00   13.30    --  107.58-125.00   0.00   88
  5  \w     94.00 178.00   1.00   13.30    --  107.58 125.00 -60.00   84
  6  \w     35.00 133.00   1.00   13.30    --  107.58 -45.00   0.00   98
  7  \w     94.00 178.00   1.00   13.30    --  107.58 125.00   0.00   84
  8  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00-180.00  100
  9  \w      9.00 117.00   1.00    1.00    --   41.11  77.00  90.00  108
 10  \w     78.00 115.00   1.00   13.30    --  107.58  61.00 150.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0369414000
_diffrn_orient_matrix_UB_12      -0.0748180000
_diffrn_orient_matrix_UB_13      -0.0547319000
_diffrn_orient_matrix_UB_21      -0.0683170000
_diffrn_orient_matrix_UB_22      -0.0487650000
_diffrn_orient_matrix_UB_23      0.0051702000
_diffrn_orient_matrix_UB_31      -0.0184162000
_diffrn_orient_matrix_UB_32      0.0300785000
_diffrn_orient_matrix_UB_33      -0.1285290000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18143
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.878
_diffrn_reflns_theta_min         3.540
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 2119 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0809
_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^)+(0.0588P)^2^+7.2317P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2226
_refine_ls_wR_factor_ref         0.2310
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                5793
_reflns_number_total             6796
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra00277d2.cif
_cod_data_source_block           jf-53-1-2
_cod_database_code               7232491
_shelx_shelxl_version_number     2014/7
_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:
 C5DA(H5DA), C8AA(H8AA), C8CA(H8CA)
2.b Secondary CH2 refined with riding coordinates:
 C1AA(H1AA,H1AB), C5AA(H5AA,H5AB), C7AA(H7AA,H7AB), C0BA(H0BA,H0BB), C4BA(H4BA,
 H4BB), C7BA(H7BA,H7BB)
2.c Aromatic/amide H refined with riding coordinates:
 C6AA(H6AA), C6BA(H6BA), C9BA(H9BA), C0CA(H0CA), C3CA(H3CA), C0DA(H0DA),
 C3DA(H3DA)
2.d X=CH2 refined with riding coordinates:
 C2DA(H2DA,H2DB)
2.e Idealised Me refined as rotating group:
 C8BA(H8BA,H8BB,H8BC), C2CA(H2CA,H2CB,H2CC), C4CA(H4CA,H4CB,H4CC), C6CA(H6CA,
 H6CB,H6CC), C9CA(H9CA,H9CB,H9CC), C1DA(H1DA,H1DB,H1DC), C4DA(H4DA,H4DB,H4DC),
 C1(H1A,H1B,H1C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2AA(H2AA), O(H)
;
_shelx_res_checksum              63698
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.311