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_4514668
_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            'C38 H27 Br3 N2 O3'
_chemical_formula_weight         799.35
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8271(10)
_cell_length_b                   16.060(2)
_cell_length_c                   29.396(4)
_cell_measurement_reflns_used    5448
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.43
_cell_volume                     3223.1(8)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
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_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    3.797
_exptl_absorpt_correction_T_max  0.7027
_exptl_absorpt_correction_T_min  0.5173
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.20
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_refine_diff_density_max         1.221
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
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_refine_ls_matrix_type           full
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_refine_ls_number_reflns         7536
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_refine_ls_restrained_S_all      0.816
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0490
_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          0.1245
_refine_ls_wR_factor_ref         0.1481
_reflns_number_gt                5995
_reflns_number_total             7536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs9b01811_si_003.cif
_cod_data_source_block           p21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        3223.0(8)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4514668