Enantioselective Synthesis of 2-Amino-1,1-diarylalkanes Bearing a Carbocyclic Ring Substituted Indole through Asymmetric Catalytic Reaction of Hydroxyindoles with Nitroalkenes.
Vila, Carlos; Rostoll-Berenguer, Jaume; Sánchez-García, Rubén; Blay, Gonzalo; Fernández, Isabel; Muñoz, M Carmen; Pedro, José R; The Journal of organic chemistry 83 (2018) 6397–6407; doi:10.1021/acs.joc.8b00612

data_4035852
_publ_section_title
;
 Enantioselective Synthesis of 2-Amino-1,1-diarylalkanes Bearing a
 Carbocyclic Ring Substituted Indole through Asymmetric Catalytic Reaction
 of Hydroxyindoles with Nitroalkenes.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6397
_journal_page_last               6407
_journal_paper_doi               10.1021/acs.joc.8b00612
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H12 Br N2 O3'
_chemical_formula_weight         360.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 103.299(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2991(3)
_cell_length_b                   5.68602(17)
_cell_length_c                   15.9291(4)
_cell_measurement_reflns_used    3391
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      23.1970
_cell_measurement_theta_min      3.8040
_cell_volume                     731.52(4)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'SuperNova Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11372
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.912
_diffrn_reflns_theta_min         3.817
_exptl_absorpt_coefficient_mu    2.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical absorption correction'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 1082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0304P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                3019
_reflns_number_total             3814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00612_si_003.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035852
_shelx_estimated_absorpt_t_min   0.677
_shelx_estimated_absorpt_t_max   0.849
_shelxl_version_number           2014-1
_shelx_res_checksum              15090
_shelx_hkl_checksum              18767