Copper-Catalyzed Asymmetric Propargylation of Cyclic Aldimines.
Fandrick, Daniel R.; Hart, Christine A.; Okafor, Ifeanyi S.; Mercadante, Michael A.; Sanyal, Sanjit; Masters, James T.; Sarvestani, Max; Fandrick, Keith R.; Stockdill, Jennifer L.; Grinberg, Nelu; Gonnella, Nina; Lee, Heewon; Senanayake, Chris H.; Organic letters 18 (2016) 6192–6195; doi:10.1021/acs.orglett.6b03253

data_1555964
_publ_section_title
;
 Copper-Catalyzed Asymmetric Propargylation of Cyclic Aldimines.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6192
_journal_page_last               6195
_journal_paper_doi               10.1021/acs.orglett.6b03253
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C27 H27 N3'
_chemical_formula_sum            'C27 H27 N3'
_chemical_formula_weight         393.51
_chemical_name_common            SCX15_050
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                79.118(2)
_cell_angle_beta                 82.740(2)
_cell_angle_gamma                72.757(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8707(3)
_cell_length_b                   12.3272(3)
_cell_length_c                   16.2931(4)
_cell_measurement_reflns_used    6939
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.4994
_cell_measurement_theta_min      2.7695
_cell_volume                     2041.96(9)
_computing_cell_refinement       'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_data_collection
'Bruker Instrument Service, BIS (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT v8,37a (Bruker AXS Inc. 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 786)'
_computing_publication_material  'APEX3 v2016.5-0 (Bruker AXS inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker X8 PROSPECTOR diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14519
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         2.77
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. (2015). J. Appl.
Cryst. 48, 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0533P)^2^+0.6259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                5824
_reflns_number_total             6801
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03253_si_004.cif
_cod_data_source_block           SCX15_050
_cod_database_code               1555964
_shelx_res_checksum              32473
_shelx_hkl_checksum              64616