Enantioselective A<sup>3</sup>-Coupling Reaction Employing Chiral Cu<sup>I</sup>- <sup>i</sup>PrpyboxdiPh/ N-Boc-(l)-Proline Complex under Cooperative Catalysis: Application in the Synthesis of (Indol-2-yl)methanamines.
Dhanasekaran, Sivasankaran; Kannaujiya, Vinod K.; Biswas, Rayhan G.; Singh, Vinod K.; The Journal of organic chemistry 84 (2019) 3275–3292; doi:10.1021/acs.joc.8b03225

data_4033891
_publ_section_title
;
 Enantioselective A<sup>3</sup>-Coupling Reaction Employing Chiral
 Cu<sup>I</sup>- <sup>i</sup>PrpyboxdiPh/ N-Boc-(l)-Proline Complex under
 Cooperative Catalysis: Application in the Synthesis of
 (Indol-2-yl)methanamines.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3275
_journal_page_last               3292
_journal_paper_doi               10.1021/acs.joc.8b03225
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_sum            'C29 H26 N2 O3 S'
_chemical_formula_weight         482.58
_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
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5820(2)
_cell_length_b                   10.6694(3)
_cell_length_c                   40.2605(10)
_cell_measurement_reflns_used    3047
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.242
_cell_measurement_theta_min      2.44
_cell_volume                     2397.78(12)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0609
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            23729
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.023
_diffrn_reflns_theta_min         2.023
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         6947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4909
_reflns_number_total             6947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03225_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4033891
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              26319
_shelx_hkl_checksum              54054