Norsampsone E, an unprecedented decarbonyl polycyclic polyprenylated acylphloroglucinol with a homoadamantyl core from Hypericum sampsonii
Tian, Wen-Jing; Qiu, Yu-Qin; Chen, Jun-Jie; Yao, Xiao-Jun; Wang, Guang-Hui; Dai, Yi; Chen, Hai-Feng; Yao, Xin-Sheng; RSC Adv. 7 (2017) 33113–; doi:10.1039/C7RA05947G

data_7228605
_publ_section_title
;
 Norsampsone E, an unprecedented decarbonyl polycyclic polyprenylated
 acylphloroglucinol with a homoadamantyl core from Hypericum sampsonii
;
_journal_issue                   53
_journal_name_full               'RSC Adv.'
_journal_page_first              33113
_journal_paper_doi               10.1039/C7RA05947G
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ukn
_chemical_formula_moiety         'C33 H40 O4'
_chemical_formula_sum            'C33 H40 O4'
_chemical_formula_weight         500.65
_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
_audit_creation_date             2017-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-05-22 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7835(6)
_cell_length_b                   12.1558(8)
_cell_length_c                   28.405(3)
_cell_measurement_reflns_used    3442
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6780
_cell_measurement_theta_min      3.9470
_cell_volume                     2687.5(4)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.992
_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   -121.00   0.00   1.00   22.31    --  -41.23 -19.00 150.00  121
  2  \w    -66.00  33.00   1.00   22.31    --  -41.23  37.00  30.00   99
  3  \w     23.00  97.00   1.00   22.31    --   41.23-125.00  30.00   74
  4  \w     24.00 109.00   1.00   50.00    --  106.95 -94.00-120.00   85
  5  \w     31.00 135.00   1.00   50.00    --  106.95 -30.00 150.00  104
  6  \w     24.00 109.00   1.00   50.00    --  106.95 -94.00  90.00   85
  7  \w     81.00 178.00   1.00   50.00    --  106.95  45.00 -30.00   97
  8  \w     24.00 109.00   1.00   50.00    --  106.95 -94.00 -30.00   85
  9  \w     79.00 178.00   1.00   50.00    --  106.95  30.00  60.00   99
 10  \w   -117.00  -9.00   1.00   22.31    --  -41.23 -77.00 -30.00  108
 11  \w   -113.00 -13.00   1.00   22.31    --  -41.23 -57.00  60.00  100
 12  \w     54.00 178.00   1.00   50.00    --  106.95  15.00-150.00  124
 13  \w     78.00 178.00   1.00   50.00    --  106.95  61.00 120.00  100
;
_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      -0.0688428000
_diffrn_orient_matrix_UB_12      -0.1004005000
_diffrn_orient_matrix_UB_13      -0.0273698000
_diffrn_orient_matrix_UB_21      -0.1149287000
_diffrn_orient_matrix_UB_22      -0.0305647000
_diffrn_orient_matrix_UB_23      0.0421805000
_diffrn_orient_matrix_UB_31      -0.1456196000
_diffrn_orient_matrix_UB_32      0.0710159000
_diffrn_orient_matrix_UB_33      -0.0203821000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_unetI/netI     0.1166
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19267
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.564
_diffrn_reflns_theta_min         3.956
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41853
_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            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 914 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       0.0056(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5321
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0977
_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^)+(0.1084P)^2^+3.5280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2371
_refine_ls_wR_factor_ref         0.2750
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3449
_reflns_number_total             5321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra05947g2.cif
_cod_data_source_block           exp_320
_cod_original_cell_volume        2687.6(4)
_cod_database_code               7228605
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.859
_reflns_odcompleteness_completeness 99.89
_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
2. Rigid bond restraints
 C26, C27
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C26 \\sim C27: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.01
4.a Ternary CH refined with riding coordinates:
 C7(H7), C20(H20), C25(H25)
4.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C29(H29A,H29B), C6(H6A,H6B), C19(H19A,H19B)
4.c Aromatic/amide H refined with riding coordinates:
 C30(H30), C12(H12), C14(H14), C16(H16), C15(H15), C13(H13)
4.d X=CH2 refined with riding coordinates:
 C27(H27A,H27B)
4.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C32(H32A,H32B,H32C), C23(H23A,H23B,
 H23C), C22(H22A,H22B,H22C), C33(H33A,H33B,H33C), C28(H28A,H28B,H28C)
;
_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 1.846
_oxdiff_exptl_absorpt_empirical_full_min 0.561