Ni-catalyzed regioselective and site-divergent reductive arylalkylations of allylic amines.
Meng, Huan; Jia, Jun-Song; Yang, Peng-Fei; Li, Yu-Long; Yu, Qiong; Shu, Wei; Chemical science 16 (2025) 4442–4449; doi:10.1039/d4sc07728h

data_1573755
_publ_section_title
;
 Ni-catalyzed regioselective and site-divergent reductive arylalkylations
 of allylic amines.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              4442
_journal_page_last               4449
_journal_paper_doi               10.1039/d4sc07728h
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C27 H31 N O2'
_chemical_formula_sum            'C27 H31 N O2'
_chemical_formula_weight         401.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-11-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-06-10 deposited with the CCDC.	2025-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.104(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5383(6)
_cell_length_b                   9.5231(4)
_cell_length_c                   18.6900(10)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      72.12
_cell_measurement_theta_min      4.03
_cell_volume                     2214.52(18)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22110
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.257
_diffrn_reflns_theta_min         4.026
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.11
_diffrn_source_power             0.0555
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1673 before and 0.1056 after correction.
The Ratio of minimum to maximum transmission is 0.5426.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0837
_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^)+(0.1676P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2105
_refine_ls_wR_factor_ref         0.2218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3657
_reflns_number_total             4341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07728h2.cif
_cod_data_source_block           mh2023112301_0m
_cod_depositor_comments
'Adding full bibliography for 1573755--1573756.cif.'
_cod_database_code               1573755
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.983
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C20(H20A,H20B), C12(H12A,H12B), C13(H13A,H13B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C4(H4), C2(H2), C23(H23), C1(H1A), C19(H19), C24(H24), C3(H3),
 C22(H22), C18(H18), C17(H17), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C27(H27A,H27B,H27C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              94467
_olex2_submission_special_instructions 'No special instructions were received'