Regio- and Enantioselective Allylic Alkylation of Terminal Alkynes by Synergistic Rh/Cu Catalysis.
Huang, Wen-Yu; Lu, Chun-Hua; Ghorai, Samir; Li, Bing; Li, Changkun; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c08283

data_4135208
_publ_section_title
;
 Regio- and Enantioselective Allylic Alkylation of Terminal Alkynes by
 Synergistic Rh/Cu Catalysis.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c08283
_journal_year                    2020
_chemical_formula_moiety         'C30 H33 Cu I N2 O2 P'
_chemical_formula_sum            'C30 H33 Cu I N2 O2 P'
_chemical_formula_weight         674.99
_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-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 92.385(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5663(7)
_cell_length_b                   12.6322(8)
_cell_length_c                   22.8317(14)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      3.88
_cell_volume                     3044.8(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            28687
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         1.937
_exptl_absorpt_coefficient_mu    9.685
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.4892
_refine_diff_density_max         3.349
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.185
_refine_ls_abs_structure_details
;
 Flack x determined using 2597 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.130(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     675
_refine_ls_number_reflns         10380
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0890
_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^)+(0.1726P)^2^+3.8509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2510
_refine_ls_wR_factor_ref         0.2673
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                7912
_reflns_number_total             10380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c08283_si_003.cif
_cod_data_source_block           a_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4135208
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.205
_shelx_estimated_absorpt_t_max   0.224
_shelx_res_checksum              55571
_shelx_hkl_checksum              74655