Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.
Liu, En-Chih; Topczewski, Joseph J.; Journal of the American Chemical Society 141 (2019) 5135–5138; doi:10.1021/jacs.9b01091

data_4128383
_publ_section_title
;
 Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic
 Kinetic Resolution.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5135
_journal_page_last               5138
_journal_paper_doi               10.1021/jacs.9b01091
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C21 H20 Br N3 O'
_chemical_formula_weight         410.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4657(2)
_cell_length_b                   13.2961(5)
_cell_length_c                   25.2012(11)
_cell_measurement_temperature    100(2)
_cell_volume                     1831.43(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15051
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.519
_diffrn_reflns_theta_min         2.227
_exptl_absorpt_coefficient_mu    2.259
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         5544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0249P)^2^+0.5062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0607
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                5097
_reflns_number_total             5544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b01091_si_002.cif
_cod_data_source_block           18168z
_cod_database_code               4128383
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.661
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              90195
_shelx_hkl_checksum              19850