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_4135207
_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_absolute_configuration ad
_chemical_formula_moiety         'C19 H13 Br N2 O6'
_chemical_formula_sum            'C19 H13 Br N2 O6'
_chemical_formula_weight         445.22
_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                 106.859(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6391(6)
_cell_length_b                   7.6769(3)
_cell_length_c                   18.8407(8)
_cell_measurement_reflns_used    7232
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      68.07
_cell_measurement_theta_min      2.45
_cell_volume                     1887.95(14)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0638
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17959
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.571
_diffrn_reflns_theta_min         2.450
_exptl_absorpt_coefficient_mu    3.324
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.5543
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1555 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.055(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         6691
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0516
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1715
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                4672
_reflns_number_total             6691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c08283_si_002.cif
_cod_data_source_block           t_b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4135207
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.503
_shelx_estimated_absorpt_t_max   0.556
_shelx_res_checksum              3090
_shelx_hkl_checksum              58153