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_1555872
_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_sum            'C25 H19 N O2'
_chemical_formula_weight         365.41
_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                 93.365(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7464(4)
_cell_length_b                   9.4368(4)
_cell_length_c                   11.5501(6)
_cell_measurement_reflns_used    5095
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.89
_cell_measurement_theta_min      3.83
_cell_volume                     951.68(8)
_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'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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 0.988
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11079
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.952
_diffrn_reflns_theta_min         3.834
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 (Bruker, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1441 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.08(18)
_refine_ls_extinction_coef       0.0120(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0635P)^2^+0.1087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                3425
_reflns_number_total             3807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02787_si_002.cif
_cod_data_source_block           mary033
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555872
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              94239
_shelx_hkl_checksum              5973