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_1557823
_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         'C28 H36 O9, C H Cl3'
_chemical_formula_sum            'C29 H37 Cl3 O9'
_chemical_formula_weight         635.93
_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             2020-01-12
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2039(2)
_cell_length_b                   13.7078(5)
_cell_length_c                   24.7447(7)
_cell_measurement_reflns_used    7368
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.1860
_cell_measurement_theta_min      3.5470
_cell_volume                     3461.12(17)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (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 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     23.00  69.00   1.00    3.00    --   40.98 -99.00 -60.00   46
  2  \w     34.00  92.00   1.00    3.00    --   40.98-132.00 -85.00   58
  3  \w     43.00 134.00   1.00   10.00    --  106.95 -61.00  30.00   91
  4  \w     75.00 135.00   1.00   10.00    --  106.95 -30.00  60.00   60
  5  \w    106.00 145.00   1.00   10.00    --  106.95  45.00   0.00   39
  6  \w    139.00 164.00   1.00   10.00    --  106.95 125.00 120.00   25
  7  \w    108.00 174.00   1.00   10.00    --  106.95 125.00  60.00   66
  8  \w     80.00 178.00   1.00   10.00    --  106.95  30.00 120.00   98
  9  \w     80.00 149.00   1.00   10.00    --  106.95  30.00  60.00   69
 10  \w     68.00 109.00   1.00   10.00    --  106.95 -94.00 -30.00   41
 11  \w     93.00 120.00   1.00   10.00    --  106.95-125.00 -90.00   27
 12  \w     90.00 119.00   1.00   10.00    --  106.95-125.00-180.00   29
 13  \w     70.00 129.00   1.00   10.00    --  106.95 -45.00-120.00   59
 14  \w     33.00 105.00   1.00   10.00    --  106.95 -94.00  60.00   72
 15  \w     48.00 139.00   1.00   10.00    --  106.95 -77.00 150.00   91
 16  \w     43.00  90.00   1.00    3.00    --   40.98-137.00  97.00   47
 17  \w     45.00 119.00   1.00   10.00    --  106.95 -30.00 150.00   74
 18  \w     20.00 115.00   1.00    3.00    --   40.98  38.00-180.00   95
 19  \w   -127.00  40.00   1.00    3.00    --  -40.98   0.00   0.00  167
;
_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  0.0917
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25004
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.684
_diffrn_reflns_theta_min         4.688
_exptl_absorpt_coefficient_mu    2.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31461
_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    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.145
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details
;
 Flack x determined using 2172 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         6895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0838
_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^)+(0.1511P)^2^+2.9858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2269
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                6000
_reflns_number_total             6895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00244_si_004.cif
_cod_data_source_block           exp_1494
_cod_database_code               1557823
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.749
_shelx_estimated_absorpt_t_min   0.714
_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:
 C5(H5), C7(H7), C9(H9), C11(H11), C17(H17), C20(H20), C2S(H2S)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B), C21(H21A,H21B), C22(H22A,H22B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C32(H32A,H32B,H32C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O7(H7A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              43189
_shelx_hkl_checksum              3642
_shelx_fab_checksum              35521
_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
;