Chiral Holmium Complex-Catalyzed Synthesis of Hydrocarbazole from Siloxyvinylindole and Its Application to the Enantioselective Total Synthesis of (-)-Minovincine.
Morikawa, Takahiro; Harada, Shinji; Nishida, Atsushi; The Journal of organic chemistry 80 (2015) 8859–8867; doi:10.1021/acs.joc.5b01393

data_4036279
_publ_section_title
;
 Chiral Holmium Complex-Catalyzed Synthesis of Hydrocarbazole from
 Siloxyvinylindole and Its Application to the Enantioselective Total
 Synthesis of (-)-Minovincine.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8859
_journal_page_last               8867
_journal_paper_doi               10.1021/acs.joc.5b01393
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C31 H30 N3 O4 S3, 1/4(C4 H8 O2)'
_chemical_formula_sum            'C32 H32 N3 O4.5 S3'
_chemical_formula_weight         612.79
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                88.992(4)
_cell_angle_beta                 89.512(4)
_cell_angle_gamma                82.169(4)
_cell_formula_units_Z            4
_cell_length_a                   8.8195(7)
_cell_length_b                   16.5259(13)
_cell_length_c                   20.684(2)
_cell_measurement_reflns_used    9126
_cell_measurement_temperature    93
_cell_measurement_theta_max      67.02
_cell_measurement_theta_min      3.42
_cell_volume                     2986.1(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32283
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.160
_refine_diff_density_min         -0.570
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  6973 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.050(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     1497
_refine_ls_number_reflns         17669
_refine_ls_number_restraints     3
_refine_ls_R_factor_gt           0.1577
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.4305
_reflns_number_gt                6356
_reflns_number_total             17669
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo5b01393_si_002.cif
_cod_data_source_block           141113morikawa01
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C128 H128 N8 O18 S12'
_cod_original_formula_weight         2451.18
_cod_original_formula_moiety         'C128 H128 N8 O18 S12'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        2986.1(5)
_cod_database_code               4036279