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_7247077
_publ_section_title
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 Ni(ii)-catalyzed oxidative deamination of benzyl amines with water
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_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         'C30 H26 Br N6 Ni, Br, C H2 Cl2'
_chemical_formula_sum            'C31 H28 Br2 Cl2 N6 Ni'
_chemical_formula_weight         774.02
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-04-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
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_audit_update_record
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2022-09-24 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                65.764(7)
_cell_angle_beta                 69.468(6)
_cell_angle_gamma                74.898(5)
_cell_formula_units_Z            4
_cell_length_a                   13.746(3)
_cell_length_b                   16.148(4)
_cell_length_c                   16.995(4)
_cell_measurement_reflns_used    10394
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.463
_cell_measurement_theta_min      2.273
_cell_volume                     3191.2(13)
_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 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      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_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  0.0859
_diffrn_reflns_av_unetI/netI     0.0954
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47313
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.463
_diffrn_reflns_theta_min         2.273
_exptl_absorpt_coefficient_mu    3.311
_exptl_absorpt_correction_T_max  0.616
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         3.040
_refine_diff_density_min         -1.372
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     796
_refine_ls_number_reflns         15929
_refine_ls_number_restraints     814
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0655
_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^)+(0.1041P)^2^+3.8948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1726
_refine_ls_wR_factor_ref         0.2051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10394
_reflns_number_total             15929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc00672g2.cif
_cod_data_source_block           Nickel_3
_cod_depositor_comments
'Adding full bibliography for 7247074--7247077.cif.'
_cod_database_code               7247077
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.636
_shelx_estimated_absorpt_t_min   0.504
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C31-Cl2B
 1.7 with sigma of 0.001
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 within 2A
5. Rigid body (RIGU) restrains
 Cl1B, C31
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl2B, C31
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(Cl1B)=Sof(Cl2B)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=FVAR(1)
 Sof(Br3B)=1-FVAR(2)
 Sof(Br3)=FVAR(2)
 Sof(Br2)=1-FVAR(3)
 Sof(Br2B)=FVAR(3)
7.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C23(H23A,H23B), C8A(H8AA,H8AB), C23A(H23C,H23D), C31(H31A,H31B),
 C32(H32A,H32B)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C27(H27), C28(H28),
  C29(H29), C30(H30), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C9A(H9A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C18A(H18A), C19A(H19A),
 C20A(H20A), C21A(H21A), C24A(H24A), C27A(H27A), C28A(H28A), C29A(H29A),
 C30A(H30A)
7.c X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C25(H25A,H25B), C10A(H10C,H10D), C25A(H25C,H25D)
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_shelx_res_checksum              9770
_shelx_hkl_checksum              17771
_olex2_submission_special_instructions 'No special instructions were received'