Gold-Catalyzed Enantio- and Diastereoselective Syntheses of Left Fragments of Azadirachtin/Meliacarpin-Type Limonoids.
Shi, Hang; Tan, Ceheng; Zhang, Weibin; Zhang, Zichun; Long, Rong; Gong, Jianxian; Luo, Tuoping; Yang, Zhen; The Journal of organic chemistry 81 (2016) 751–771; doi:10.1021/acs.joc.5b02560

data_4031816
_publ_section_title
;
 Gold-Catalyzed Enantio- and Diastereoselective Syntheses of Left
 Fragments of Azadirachtin/Meliacarpin-Type Limonoids.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              751
_journal_page_last               771
_journal_paper_doi               10.1021/acs.joc.5b02560
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H36 O4 Si'
_chemical_formula_sum            'C23 H36 O4 Si'
_chemical_formula_weight         404.61
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.71330(10)
_cell_length_b                   12.5483(2)
_cell_length_c                   25.0132(17)
_cell_measurement_reflns_used    10536
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      6.70
_cell_volume                     2421.00(17)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11489
_diffrn_reflns_theta_full        68.16
_diffrn_reflns_theta_max         68.16
_diffrn_reflns_theta_min         6.74
_exptl_absorpt_coefficient_mu    1.037
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1777 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.230
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1678
_reflns_number_gt                3534
_reflns_number_total             4263
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo5b02560_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4031812--4031816.cif.'
_cod_database_code               4031816