Highly enantioselective copper-catalyzed propargylic amination to access N-tethered 1,6-enynes
Li, Si-Jia; Huang, Jian; He, Jin-Yu; Zhang, Rui-Jin; Qian, Hao-Dong; Dai, Xue-Lin; Kong, Han-Han; Xu, Hao; RSC Advances 10 (2020) 38478–38483; doi:10.1039/D0RA07698H

data_7241421
_publ_section_title
;
 Highly enantioselective copper-catalyzed propargylic amination to access
 N-tethered 1,6-enynes
;
_journal_issue                   63
_journal_name_full               'RSC Advances'
_journal_page_first              38478
_journal_page_last               38483
_journal_paper_doi               10.1039/D0RA07698H
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H26 Cl Cu N3 P'
_chemical_formula_sum            'C31 H26 Cl Cu N3 P'
_chemical_formula_weight         570.51
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-15
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2020-01-07 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                87.751(3)
_cell_angle_beta                 68.299(2)
_cell_angle_gamma                82.837(3)
_cell_formula_units_Z            1
_cell_length_a                   8.8768(17)
_cell_length_b                   8.8907(18)
_cell_length_c                   9.3073(18)
_cell_measurement_reflns_used    2696
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.79
_cell_measurement_theta_min      2.31
_cell_volume                     677.1(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5695
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         2.309
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.989
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.041(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0377P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4106
_reflns_number_total             4709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra07698h2.cif
_cod_data_source_block           mo_191014a_0m
_cod_database_code               7241421
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.890
_olex2_refinement_description
; 
1. Twinned data refinement 
 Scales: 0.959(17) 
 0.041(17) 
2. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
3.a Ternary CH refined with riding coordinates: 
 C12(H12) 
3.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C10(H10), C9(H9), C8(H8), C16(H16), 
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), 
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31) 
3.c Fitted hexagon refined as free rotating group: 
 C7(N3,C11,C10,C9,C8) 
3.d Idealised Me refined as rotating group: 
 C13(H13A,H13B,H13C) 
;
_shelx_res_checksum              59768
_olex2_submission_special_instructions 'No special instructions were received'