Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction
Li, Huaifeng; Lupp, Daniel; Das, Pradip K.; Yang, Li; Gonçalves, Théo P.; Huang, Mei-Hui; El Hajoui, Marwa; Liang, Lan-Chang; Huang, Kuo-Wei; ACS Catalysis 11 (2021) 4071–4076; doi:10.1021/acscatal.1c00379

data_4518566
_publ_section_title
;
 Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative
 to the Staudinger/Aza-Wittig Reaction
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              4071
_journal_page_last               4076
_journal_paper_doi               10.1021/acscatal.1c00379
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C18 H25 Cl N3 Ni P'
_chemical_formula_sum            'C18 H25 Cl N3 Ni P'
_chemical_formula_weight         408.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-02-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 118.179(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1382(15)
_cell_length_b                   8.1442(8)
_cell_length_c                   16.0627(18)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.54
_cell_volume                     1860.9(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      119.99
_diffrn_measured_fraction_theta_full 0.854
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.854
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51312
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.926
_diffrn_reflns_theta_min         2.537
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.277
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1584 before and 0.0972 after correction.
The Ratio of minimum to maximum transmission is 0.8354.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       Block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0350P)^2^+2.0596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2817
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c00379_si_005.cif
_cod_data_source_block           kkk_a
_cod_depositor_comments
'Adding full bibliography for 4518564--4518568.cif.'
_cod_database_code               4518566
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.803
_shelx_estimated_absorpt_t_min   0.766
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C2(H2), C4(H4), C9(H9), C8(H8), C3(H3)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'