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_1559691
_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         'C39 H48 O11, H2 O'
_chemical_formula_sum            'C39 H50 O12'
_chemical_formula_weight         710.79
_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   mixed
_atom_sites_solution_primary     dual
_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                   13.75700(10)
_cell_length_b                   15.59590(10)
_cell_length_c                   16.8013(2)
_cell_measurement_reflns_used    21169
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5400
_cell_measurement_theta_min      3.8240
_cell_volume                     3604.77(6)
_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    'ShelXT (Sheldrick, 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 0.995
_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    --  -40.98 125.00-120.00   94
  2  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 150.00  100
  3  \w    -33.00  66.00   1.00    1.00    --   40.98 -38.00 -60.00   99
  4  \w     24.00 109.00   1.00    3.62    --  106.95 -94.00  30.00   85
  5  \w     81.00 178.00   1.00    3.62    --  106.95  45.00 150.00   97
  6  \w     35.00 136.00   1.00    3.62    --  106.95 -61.00 -30.00  101
  7  \w     94.00 178.00   1.00    3.62    --  106.95 125.00  90.00   84
  8  \w     94.00 178.00   1.00    3.62    --  106.95 125.00  60.00   84
  9  \w     78.00 178.00   1.00    3.62    --  106.95  61.00-180.00  100
 10  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00 -30.00  109
 11  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00  30.00   99
 12  \w     34.00 133.00   1.00    3.62    --  106.95 -45.00  90.00   99
 13  \w     81.00 178.00   1.00    3.62    --  106.95  45.00  30.00   97
 14  \w     81.00 178.00   1.00    3.62    --  106.95  45.00  90.00   97
 15  \w     48.00 178.00   1.00    3.62    --  106.95  14.00 -50.00  130
 16  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00-120.00  100
 17  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00 150.00   81
 18  \w     34.00 121.00   1.00    3.62    --  106.95-125.00 -90.00   87
 19  \w     24.00 107.00   1.00    3.62    --  106.95 -94.00 120.00   83
 20  \w     78.00 178.00   1.00    3.62    --  106.95  61.00 -30.00  100
;
_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      -0.0918965000
_diffrn_orient_matrix_UB_12      -0.0126301000
_diffrn_orient_matrix_UB_13      0.0510102000
_diffrn_orient_matrix_UB_21      -0.0608913000
_diffrn_orient_matrix_UB_22      -0.0126729000
_diffrn_orient_matrix_UB_23      -0.0760959000
_diffrn_orient_matrix_UB_31      0.0199238000
_diffrn_orient_matrix_UB_32      -0.0971407000
_diffrn_orient_matrix_UB_33      0.0031458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40758
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.766
_diffrn_reflns_theta_min         3.867
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81171
_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    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.00101(18)
_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   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         7211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0615P)^2^+0.4304P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                6926
_reflns_number_total             7211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01151_si_003.cif
_cod_data_source_block           e-f-9
_cod_database_code               1559691
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.910
_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, All O(H,H) groups
2.a Free rotating group:
 O00C(H00T,H00V)
2.b Ternary CH refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00I(H00I), C00K(H00K), C00O(H00O), C00R(H00R),
 C00U(H00U), C014(H014)
2.c Secondary CH2 refined with riding coordinates:
 C00W(H00D,H00F), C00Y(H00M,H00N), C00Z(H00P,H00S), C011(H01A,H01B)
2.d Aromatic/amide H refined with riding coordinates:
 C00Q(H00Q), C010(H010), C012(H012), C013(H013), C015(H015), C016(H016),
 C01A(H01I), C01D(H01P)
2.e Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00C), C00X(H00H,H00J,H00L), C018(H01C,H01D,H01E), C019(H01F,
 H01G,H01H), C01B(H01J,H01K,H01L), C01C(H01M,H01N,H01O), C01E(H01Q,H01R,H01S),
 C01F(H01T,H01U,H01V)
;
_shelx_res_checksum              30622
_shelx_hkl_checksum              38005
_olex2_submission_original_sample_id 'Meliazedarin B'
_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 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.703