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_7228607
_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 ad
_chemical_formula_moiety         'C33 H42 O5'
_chemical_formula_sum            'C33 H42 O5'
_chemical_formula_weight         518.66
_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_creation_date             2017-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-05-23 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            8
_cell_length_a                   9.8352(5)
_cell_length_b                   11.5100(7)
_cell_length_c                   49.946(3)
_cell_measurement_reflns_used    5300
_cell_measurement_temperature    160.00(14)
_cell_measurement_theta_max      62.5490
_cell_measurement_theta_min      3.5300
_cell_volume                     5654.0(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      160.00(14)
_diffrn_detector_area_resol_mean 16.0855
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -110.00  -85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.2104 -179.0000  -60.0000 25

  2 omega   83.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2104  179.0000 -120.0000 26

  3 omega   21.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2104   57.0000  -60.0000 77

  4 omega   33.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2104   57.0000   30.0000 70

  5 omega   41.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -113.0000   -4.0000 30

  6 omega   43.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000    0.0000 26

  7 omega   65.00  127.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -91.0000   28.1685 62

  8 omega   19.00   73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -45.0000    0.0000 54

  9 omega   71.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -91.0000   -6.9035 26

 10 omega   19.00   75.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -45.0000  120.0000 56

 11 omega   18.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000 -180.0000 25

 12 omega   79.00  124.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  111.0000  120.0000 45

 13 omega   50.00   75.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -94.0000   60.0000 25

 14 omega   83.00  119.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   30.0000 -150.0000 36

 15 omega   82.00  112.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -61.0000    0.0000 30

 16 omega   80.00  149.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   61.0000    0.0000 69

 17 omega   38.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -61.0000    0.0000 26

 18 omega   34.00   78.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000 -180.0000 44

 19 omega   92.00  120.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000 -180.0000 28

 20 omega   75.00  101.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500    0.0000 -180.0000 26

 21 omega  138.00  163.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   30.0000 -150.0000 25

 22 omega   95.00  120.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  111.0000   30.0000 25

 23 omega   37.00   63.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -91.0000   -6.9035 26

 24 omega   31.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000 -120.0000 38

 25 omega   40.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -111.0000   30.0000 49

 26 omega   51.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -61.0000  -90.0000 53

 27 omega   66.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -61.0000  -30.0000 38

 28 omega   77.00  160.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   45.0000  -90.0000 83

 29 omega   67.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   15.0000 -180.0000 32

 30 omega  138.00  163.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   15.0000 -180.0000 25

 31 omega   29.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -91.0000   28.1685 26

 32 omega   81.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -93.0000  -78.1002 25
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0201846000
_diffrn_orient_matrix_UB_12      0.0986900000
_diffrn_orient_matrix_UB_13      0.0204579000
_diffrn_orient_matrix_UB_21      -0.0195070000
_diffrn_orient_matrix_UB_22      0.0872493000
_diffrn_orient_matrix_UB_23      -0.0230780000
_diffrn_orient_matrix_UB_31      -0.1540619000
_diffrn_orient_matrix_UB_32      -0.0239815000
_diffrn_orient_matrix_UB_33      0.0002496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            35128
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        62.626
_diffrn_reflns_theta_max         62.626
_diffrn_reflns_theta_min         3.540
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2627 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     702
_refine_ls_number_reflns         9014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0311P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                7333
_reflns_number_total             9014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra05947g2.cif
_cod_data_source_block           tianwenjing-a
_cod_original_cell_volume        5654.1(6)
_cod_database_code               7228607
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.894
_reflns_odcompleteness_completeness 89.90
_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:
 C7(H7), C20(H20), C7'(H7'), C20'(H20')
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C19(H19A,H19B), C24(H24A,H24B), C29(H29A,H29B), C6'(H6'A,H6'B),
 C19'(H19C,H19D), C24'(H24C,H24D), C29'(H29C,H29D)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C25(H25), C30(H30),
 C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C16'(H16'), C25'(H25'),
 C30'(H30')
2.d Tetrahedral OH refined with riding coordinates:
 O5'(H5')
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C), C17'(H17D,H17E,H17F), C18'(H18D,H18E,H18F), C22'(H22D,H22E,H22F),
 C23'(H23D,H23E,H23F), C27'(H27D,H27E,H27F), C28'(H28D,H28E,H28F), C32'(H32D,
 H32E,H32F), C33'(H33D,H33E,H33F)
2.f Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'