Total synthesis of (+)-isatisine a: application of a silicon-directed mukaiyama-type [3 + 2]-annulation.
Lee, Jihoon; Panek, James S.; The Journal of organic chemistry 80 (2015) 2959–2971; doi:10.1021/acs.joc.5b00051

data_4036118
_publ_section_title
;
 Total synthesis of (+)-isatisine a: application of a silicon-directed
 mukaiyama-type [3 + 2]-annulation.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2959
_journal_page_last               2971
_journal_paper_doi               10.1021/acs.joc.5b00051
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C26 H25 Br N2 O6'
_chemical_formula_sum            'C26 H25 Br N2 O6'
_chemical_formula_weight         541.39
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-07-20 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.6910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2080(3)
_cell_length_b                   14.4061(5)
_cell_length_c                   10.6072(4)
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      132.095
_cell_measurement_theta_min      8.855
_cell_volume                     1180.91(7)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\w & \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28807
_diffrn_reflns_theta_full        66.43
_diffrn_reflns_theta_max         66.43
_diffrn_reflns_theta_min         4.43
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.765
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.073
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.769
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4086
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.769
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.002
_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          0.0763
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                4076
_reflns_number_total             4086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00051_si_001.cif
_cod_data_source_block           jihoon1_0m
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4036118