Ni(ii)-catalyzed oxidative deamination of benzyl amines with water
Pal, Nilay Kumar; Singh, Kuldeep; Patra, Moumita; Yadav, Suman; Pandey, Prabhakar K.; Bera, Jitendra K.; Green Chemistry 25 (2023) 6212–6217; doi:10.1039/D3GC00672G

data_7247076
_publ_section_title
;
 Ni(ii)-catalyzed oxidative deamination of benzyl amines with water
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              6212
_journal_page_last               6217
_journal_paper_doi               10.1039/D3GC00672G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'Br, C20 H18 N3 Ni, C H2 Cl2'
_chemical_formula_sum            'C21 H20 Br Cl2 N3 Ni'
_chemical_formula_weight         523.92
_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   mixed
_audit_creation_date             2022-02-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-24 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0731(2)
_cell_length_b                   20.1087(5)
_cell_length_c                   10.8313(3)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.92
_cell_volume                     2115.28(9)
_computing_cell_refinement       'APEX2 v2010.7-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2010.7.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0541
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33907
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_min         2.657
_exptl_absorpt_coefficient_mu    3.071
_exptl_absorpt_correction_T_max  0.636
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5250
_refine_ls_number_restraints     682
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0227P)^2^+3.6219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4112
_reflns_number_total             5250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc00672g2.cif
_cod_data_source_block           Nickel_2
_cod_depositor_comments
'Adding full bibliography for 7247074--7247077.cif.'
_cod_database_code               7247076
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.656
_shelx_estimated_absorpt_t_min   0.565
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2-C3 \\sim C2-C3A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 C5-C7 \\sim C5A-C7
 with sigma of 0.04
 C2-C4 \\sim C2-C4A
 with sigma of 0.04
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
 C14-C17 \\sim C15A-C13A
 with sigma of 0.04
 C16-C15 \\sim C17A-C16A
 with sigma of 0.02
 C15-C17 \\sim C16A-C13A
 with sigma of 0.04
 C15-C14 \\sim C16A-C15A
 with sigma of 0.02
 C16-C13 \\sim C17A-C14A
 with sigma of 0.04
 C16-C17 \\sim C17A-C13A
 with sigma of 0.02
 C15-C13 \\sim C16A-C14A
 with sigma of 0.04
 C13-C17 \\sim C14A-C13A
 with sigma of 0.02
 Ni1-C16 \\sim Ni1-C17A
 with sigma of 0.04
 Ni1-C15 \\sim Ni1-C16A
 with sigma of 0.04
 Ni1-C14 \\sim Ni1-C15A
 with sigma of 0.04
 Ni1-C13 \\sim Ni1-C14A
 with sigma of 0.04
 Ni1-C17 \\sim Ni1-C13A
 with sigma of 0.04
 C14-C13 \\sim C15A-C14A
 with sigma of 0.02
 C16-C14 \\sim C17A-C15A
 with sigma of 0.04
 C11-C12A \\sim C11A-C12
 with sigma of 0.02
 C10-C12A \\sim C10-C12
 with sigma of 0.04
 C10-C11 \\sim C10-C11A
 with sigma of 0.02
 N3-C11 \\sim N3-C11A
 with sigma of 0.04
 N3-C12A \\sim N3-C12
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=1-FVAR(1)
 Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=FVAR(1)
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=Sof(C17A)=Sof(H17A)=1-FVAR(2)
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=
 Sof(C17)=Sof(H17)=FVAR(2)
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=1-FVAR(3)
 Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=FVAR(3)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=1-FVAR(4)
 Sof(Cl1)=Sof(Cl2)=Sof(C21)=Sof(H21A)=Sof(H21B)=FVAR(4)
 Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20A)=Sof(H20B)=1-FVAR(5)
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20C)=Sof(H20D)=FVAR(5)
6.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C21(H21A,H21B), C21A(H21C,H21D)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C3A(H3A), C4(H4), C4A(H4A), C5(H5), C5A(H5A), C6(H6), C6A(H6A),
 C9(H9), C10(H10), C11(H11), C11A(H11A), C12(H12), C12A(H12A), C13(H13),
 C13A(H13A), C14(H14), C14A(H14A), C15(H15), C15A(H15A), C16(H16), C16A(H16A),
 C17(H17), C17A(H17A)
;
_shelx_res_checksum              69038
_shelx_hkl_checksum              76977
_olex2_submission_special_instructions 'No special instructions were received'