Bioactive Limonoids and Triterpenoids from the Fruits of <i>Melia azedarach</i>.
Song, Min; Zhang, Jian; Chan, Ging; Hou, Ying; Chen, Xiu-Ping; Zhang, Xiao-Qi; Ye, Wen-Cai; Zhang, Qing-Wen; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.9b01151

data_1559690
_publ_section_title
;
 Bioactive Limonoids and Triterpenoids from the Fruits of <i>Melia
 azedarach</i>.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.9b01151
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C37 H50 O11'
_chemical_formula_sum            'C37 H50 O11'
_chemical_formula_weight         670.77
_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             2019-05-16
_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                   9.15490(10)
_cell_length_b                   17.17110(10)
_cell_length_c                   21.80800(10)
_cell_measurement_reflns_used    29783
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4960
_cell_measurement_theta_min      2.0210
_cell_volume                     3428.21(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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.990
_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    -96.00  -2.00   1.00    1.00    --  -41.11 125.00-180.00   94
  2  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00-150.00  100
  3  \w    -69.00  32.00   1.00    1.00    --  -41.11  57.00   0.00  101
  4  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00-120.00   99
  5  \w     79.00 178.00   1.00    1.00    --  106.95  30.00-120.00   99
  6  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00  90.00   85
  7  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00  60.00   99
  8  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 150.00   84
  9  \w     94.00 178.00   1.00    1.00    --  106.95 125.00   0.00   84
 10  \w    -69.00  32.00   1.00    1.00    --  -41.11  57.00 120.00  101
 11  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00  90.00  100
 12  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00 -30.00  100
 13  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 150.00   97
 14  \w     79.00 178.00   1.00    1.00    --  106.95  30.00 -30.00   99
 15  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -30.00  104
 16  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00 -90.00   85
 17  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 -90.00  100
 18  \w     54.00 178.00   1.00    1.00    --  106.95  15.00  90.00  124
 19  \w   -117.00 -60.00   1.00    1.00    --  -41.11 -77.00-180.00   57
 20  \w   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00  60.00  108
;
_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      -0.0089721000
_diffrn_orient_matrix_UB_12      -0.0893371000
_diffrn_orient_matrix_UB_13      -0.0055253000
_diffrn_orient_matrix_UB_21      -0.0207452000
_diffrn_orient_matrix_UB_22      -0.0063752000
_diffrn_orient_matrix_UB_23      0.0699505000
_diffrn_orient_matrix_UB_31      -0.1666440000
_diffrn_orient_matrix_UB_32      0.0055630000
_diffrn_orient_matrix_UB_33      -0.0084259000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            39305
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.601
_diffrn_reflns_theta_min         3.276
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65752
_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    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.00169(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         6817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.7989P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                6689
_reflns_number_total             6817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01151_si_002.cif
_cod_data_source_block           e-f-10
_cod_database_code               1559690
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.892
_reflns_odcompleteness_completeness 100.00
_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.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I), C00K(H00K), C00O(H00O),
 C012(H012), C013(H013)
2.b Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00B), C010(H01A,H01B), C015(H01F,H01G), C016(H01H,H01I)
2.c Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C011(H011), C01A(H01S), C01B(H01T)
2.d Idealised Me refined as rotating group:
 C00U(H00C,H00D,H00H), C00V(H00J,H00L,H00N), C00W(H00P,H00Q,H00R), C00X(H00S,
 H00T,H00U), C00Z(H00V,H00W,H00X), C014(H01C,H01D,H01E), C017(H01J,H01K,H01L),
 C018(H01M,H01N,H01O), C019(H01P,H01Q,H01R), C01C(H01U,H01V,H01W)
;
_shelx_res_checksum              36102
_shelx_hkl_checksum              26689
_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 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.600