Enantioselective, Copper-Catalyzed Alkynylation of Ketimines To Deliver Isoquinolines with α-Diaryl Tetrasubstituted Stereocenters.
Dasgupta, Srimoyee; Liu, Jixin; Shoffler, Clarissa A.; Yap, Glenn P. A.; Watson, Mary P.; Organic letters 18 (2016) 6006–6009; doi:10.1021/acs.orglett.6b02787

data_1555871
_publ_section_title
;
 Enantioselective, Copper-Catalyzed Alkynylation of Ketimines To Deliver
 Isoquinolines with \a-Diaryl Tetrasubstituted Stereocenters.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6006
_journal_page_last               6009
_journal_paper_doi               10.1021/acs.orglett.6b02787
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         '3(C46 H38 Cu2 I N6 O4), Cu4 I7, 4(C H2 Cl2)'
_chemical_formula_sum            'C142 H123 Cl8 Cu10 I10 N18 O12'
_chemical_formula_weight         4461.58
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.4006(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.7926(13)
_cell_length_b                   23.6471(19)
_cell_length_c                   19.7202(15)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.09
_cell_measurement_theta_min      2.24
_cell_volume                     7828.5(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            110786
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         1.345
_exptl_absorpt_coefficient_mu    3.499
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2007)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_description       plate
_exptl_crystal_F_000             4306
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.186
_refine_diff_density_max         2.189
_refine_diff_density_min         -1.960
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1550
_refine_ls_number_reflns         32026
_refine_ls_number_restraints     3025
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0608P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                19173
_reflns_number_total             32026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02787_si_003.cif
_cod_data_source_block           mary022_sq
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555871
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.473
_shelx_estimated_absorpt_t_max   0.562
_shelx_res_checksum              99226
_shelx_hkl_checksum              34557
_shelx_fab_checksum              98779