Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via an Organocatalytic Cascade Reaction.
Formánek, Bedřich; Tauchman, Jiří; Císařová, Ivana; Veselý, Jan; The Journal of organic chemistry 85 (2020) 8510–8521; doi:10.1021/acs.joc.0c00882

data_4038499
_publ_section_title
;
 Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via
 an Organocatalytic Cascade Reaction.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8510
_journal_page_last               8521
_journal_paper_doi               10.1021/acs.joc.0c00882
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C22 H19 Br O4 S'
_chemical_formula_sum            'C22 H19 Br O4 S'
_chemical_formula_weight         459.34
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0046(4)
_cell_length_b                   11.4721(4)
_cell_length_c                   15.6538(4)
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4877
_cell_measurement_theta_min      2.5647
_cell_volume                     1976.23(11)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28071
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         2.201
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.212
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1841 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0082(19)
_refine_ls_extinction_coef       0.0088(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0182
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.5626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0439
_refine_ls_wR_factor_ref         0.0445
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4374
_reflns_number_total             4526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00882_si_002.cif
_cod_data_source_block           mo_mp87_vesely
_cod_depositor_comments          'Adding full bibliography for 4038499.cif.'
_cod_database_code               4038499
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.562
_shelx_estimated_absorpt_t_max   0.816
_shelx_res_checksum              21140
_shelx_hkl_checksum              32618