Enantioselective Friedel–Crafts Alkylation Reaction of Indoles with α-Trifluoromethylated β-Nitrostyrenes Catalyzed by Chiral BINOL Metal Phosphate
Ibáñez, Ignacio; Kaneko, Mio; Kamei, Yuto; Tsutsumi, Ryosuke; Yamanaka, Masahiro; Akiyama, Takahiko; ACS Catalysis 9 (2019) 6903–; doi:10.1021/acscatal.9b01811

data_4514669
_publ_section_title
;
 Enantioselective Friedel--Crafts Alkylation Reaction of Indoles with
 \a-Trifluoromethylated \b-Nitrostyrenes Catalyzed by Chiral BINOL Metal
 Phosphate
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              6903
_journal_paper_doi               10.1021/acscatal.9b01811
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H25 Br N2 O2 S'
_chemical_formula_weight         497.44
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7248(16)
_cell_length_b                   9.7248
_cell_length_c                   48.320(8)
_cell_measurement_reflns_used    1318
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      17.00
_cell_measurement_theta_min      2.26
_cell_volume                     4569.7(11)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1234
_diffrn_reflns_av_unetI/netI     0.1673
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            21953
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.686
_exptl_absorpt_coefficient_mu    1.915
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 1553 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         7910
_refine_ls_number_restraints     409
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                4910
_reflns_number_total             7910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01811_si_004.cif
_cod_data_source_block           1221
_cod_depositor_comments
;

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4569.7(17)
_cod_original_formula_sum        'C50 H50 Br2 N4 O4 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     994.88
_cod_database_code               4514669
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.832
_shelx_estimated_absorpt_t_max   0.832
_shelx_res_checksum              66214
_shelx_hkl_checksum              27205