Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts.
Huang, Jian; Kong, Han-Han; Li, Si-Jia; Zhang, Rui-Jin; Qian, Hao-Dong; Li, Dan-Ran; He, Jin-Yu; Zheng, Yi-Nuo; Xu, Hao; Chemical communications (Cambridge, England) 57 (2021) 4674–4677; doi:10.1039/d1cc00663k

data_7128147
_publ_section_title
;
 Asymmetric copper-catalyzed propargylic amination with amine
 hydrochloride salts.
;
_journal_issue                   38
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4674
_journal_page_last               4677
_journal_paper_doi               10.1039/d1cc00663k
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H16 Br N O4'
_chemical_formula_sum            'C15 H16 Br N O4'
_chemical_formula_weight         354.20
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-11
_audit_creation_method
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) 
;
_audit_update_record
;
2021-03-14 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.210(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6884(10)
_cell_length_b                   13.820(2)
_cell_length_c                   8.5300(13)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.33
_cell_measurement_theta_min      2.78
_cell_volume                     787.9(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.655
_diffrn_measured_fraction_theta_max 0.790
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.655
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11510
_diffrn_reflns_point_group_measured_fraction_full 0.596
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.333
_diffrn_reflns_theta_min         7.463
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.201
_refine_ls_abs_structure_details
; 
 Flack x determined using 1582 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.008(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0638
_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^)+(0.1122P)^2^+0.0264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1663
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.531
_reflns_Friedel_fraction_max     0.714
_reflns_number_gt                3558
_reflns_number_total             3566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00663k2.cif
_cod_data_source_block           210309c_0m
_cod_depositor_comments          'Adding full bibliography for 7128147.cif.'
_cod_database_code               7128147
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.793
_shelx_estimated_absorpt_t_min   0.642
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Ternary CH refined with riding coordinates: 
 C7(H7) 
2.b Secondary CH2 refined with riding coordinates: 
 C10(H10A,H10B), C13(H13A,H13B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6) 
2.d Idealised Me refined as rotating group: 
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C) 
2.e : 
 C9(H9) 
;
_shelx_res_checksum              81428
_olex2_submission_special_instructions 'No special instructions were received'