Unprecedented Quassinoids from Eurycoma longifolia: Biogenetic Evidence and Antifeedant Effects
Yang, Wei-Qun; Shao, Xue-Hua; Deng, Fang; Hu, Li-Jun; Xiong, Yu; Huang, Xiao-Jun; Fan, Chun-Lin; Jiang, Ren-Wang; Ye, Wen-Cai; Wang, Ying; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00244

data_1557821
_publ_section_title
;
 Unprecedented Quassinoids from Eurycoma longifolia: Biogenetic Evidence
 and Antifeedant Effects
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00244
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H28 O8'
_chemical_formula_sum            'C20 H28 O8'
_chemical_formula_weight         396.42
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.26550(10)
_cell_length_b                   10.19270(10)
_cell_length_c                   24.3238(3)
_cell_measurement_reflns_used    9645
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6330
_cell_measurement_theta_min      4.2990
_cell_volume                     1801.30(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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -69.00  32.00   1.00    1.00    --  -41.11  57.00-180.00  101
  2  \w     23.00  97.00   1.00    1.00    --   41.11-125.00  90.00   74
  3  \w      1.00  82.00   1.00    1.00    --   41.11 -99.00 -60.00   81
  4  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 -30.00   84
  5  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  60.00   84
  6  \w     94.00 178.00   1.00    1.00    --  106.95 125.00-180.00   84
  7  \w     28.00 113.00   1.00    1.00    --  106.95-105.00 110.00   85
  8  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00-180.00  104
  9  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 150.00   97
 10  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00  60.00  100
 11  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00-150.00  100
 12  \w     79.00 178.00   1.00    1.00    --  106.95  30.00 -60.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11355
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.762
_diffrn_reflns_theta_min         3.634
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69247
_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    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0514P)^2^+0.4118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3526
_reflns_number_total             3565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00244_si_002.cif
_cod_data_source_block           19-el2
_cod_database_code               1557821
_shelx_shelxl_version_number     2017/1
_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:
 C1(H1), C4(H4), C5(H5), C9(H9), C11(H11), C12(H12), C13(H13), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O7(H7), O8(H8)
;
_shelx_res_checksum              56612
_shelx_hkl_checksum              32987
_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
;