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_1557824
_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 unk
_chemical_formula_moiety         'C20 H26 O10'
_chemical_formula_sum            'C20 H26 O10'
_chemical_formula_weight         426.41
_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     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                 103.943(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3686(3)
_cell_length_b                   6.6338(2)
_cell_length_c                   13.6339(4)
_cell_measurement_reflns_used    2622
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2670
_cell_measurement_theta_min      3.3130
_cell_volume                     910.15(5)
_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 0.978
_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    -65.00  12.00   1.00    2.00    --  -40.98  38.00-150.00   77
  2  \w   -113.00 -13.00   1.00    2.00    --  -40.98 -57.00-150.00  100
  3  \w    -79.00 -53.00   1.00    2.00    --  -40.98-158.00 -25.00   26
  4  \w     54.00 178.00   1.00    8.00    --  106.95  15.00-150.00  124
  5  \w    125.00 164.00   1.00    8.00    --  106.95 125.00-180.00   39
  6  \w    119.00 145.00   1.00    8.00    --  106.95 125.00 -90.00   26
  7  \w     79.00 143.00   1.00    8.00    --  106.95  61.00  90.00   64
  8  \w     36.00 114.00   1.00    8.00    --  106.95 -61.00 150.00   78
  9  \w     43.00 105.00   1.00    8.00    --  106.95 -95.00 120.00   62
 10  \w    -58.00 -21.00   1.00    2.00    --  -41.23 -77.00-150.00   37
 11  \w    -68.00 -14.00   1.00    2.00    --  -41.23 -57.00 120.00   54
 12  \w   -114.00 -88.00   1.00    2.00    --  -41.23 -77.00-150.00   26
 13  \w     23.00  55.00   1.00    2.00    --   41.23  38.00-180.00   32
 14  \w     21.00  47.00   1.00    2.00    --   41.23  38.00 -30.00   26
 15  \w     28.00  93.00   1.00    2.00    --   41.23-125.00 120.00   65
 16  \w     22.00  49.00   1.00    2.00    --   41.23 -99.00   0.00   27
 17  \w     51.00  77.00   1.00    2.00    --   41.23  38.00 -90.00   26
 18  \w     75.00 101.00   1.00    8.00    --  106.95  77.00-180.00   26
 19  \w     79.00 105.00   1.00    8.00    --  106.95  61.00 -60.00   26
 20  \w     75.00 101.00   1.00    8.00    --  106.95  77.00 -90.00   26
 21  \w     78.00 103.00   1.00    8.00    --  106.95  61.00-180.00   25
 22  \w     81.00 107.00   1.00    8.00    --  106.95  61.00-150.00   26
 23  \w     83.00 109.00   1.00    8.00    --  106.95  61.00 -90.00   26
 24  \w     80.00 106.00   1.00    8.00    --  106.95  61.00-120.00   26
 25  \w     82.00 108.00   1.00    8.00    --  106.95  45.00-150.00   26
 26  \w    142.00 176.00   1.00    8.00    --  106.95  77.00-150.00   34
 27  \w     79.00 104.00   1.00    8.00    --  106.95  61.00 150.00   25
 28  \w     74.00 100.00   1.00    8.00    --  106.95  77.00 150.00   26
 29  \w     81.00 106.00   1.00    8.00    --  106.95  45.00-180.00   25
;
_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  0.0511
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6342
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.380
_diffrn_reflns_theta_min         3.340
_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61878
_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    1.556
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0634P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.617
_reflns_Friedel_fraction_full    0.771
_reflns_Friedel_fraction_max     0.723
_reflns_number_gt                2881
_reflns_number_total             3151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00244_si_006.cif
_cod_data_source_block           dg_2
_cod_database_code               1557824
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.883
_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), C2(H2), C5(H5), C7(H7), C9(H9), C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C18(H18A,H18B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C29(H29A,H29B,H29C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A), O5(H5A), O6(H6), O8(H8), O9(H9A)
;
_shelx_res_checksum              28509
_shelx_hkl_checksum              37130
_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
;