Controlled Synthesis of Enantioselective 1-Aminoindenes via Cobalt-Catalyzed [3 + 2] Annulation Reaction
Chen, Min-Hsien; Hsieh, Jen-Chieh; Lee, Yi-Hsien; Cheng, Chien-Hong; ACS Catalysis 8 (2018) 9364–; doi:10.1021/acscatal.8b02566

data_4515547
_publ_section_title
;
 Controlled Synthesis of Enantioselective 1-Aminoindenes via
 Cobalt-Catalyzed [3 + 2] Annulation Reaction
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9364
_journal_paper_doi               10.1021/acscatal.8b02566
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_sum            'C28 H23 N S'
_chemical_formula_weight         405.53
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                73.570(4)
_cell_angle_beta                 71.546(4)
_cell_angle_gamma                61.603(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0820(6)
_cell_length_b                   10.3160(7)
_cell_length_c                   12.2470(8)
_cell_measurement_reflns_used    3149
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.1636
_cell_measurement_theta_min      2.3518
_cell_volume                     1049.43(12)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13383
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.450
_diffrn_reflns_theta_min         1.775
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 1710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         7451
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1560
_refine_ls_R_factor_gt           0.1083
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1818P)^2^+1.1537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2803
_refine_ls_wR_factor_ref         0.3236
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.808
_reflns_Friedel_fraction_max     0.785
_reflns_number_gt                4725
_reflns_number_total             7451
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b02566_si_002.cif
_cod_data_source_block           140512LT_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4515547
_shelxl_version_number           2013-4
_shelx_res_checksum              31611
_shelx_hkl_checksum              55333