Nickel-Catalyzed Annulations of ortho-Haloarylimines
Kolluru, Srinivas; Singh, Manvendra; Gaskins, Bryce; Boskovic, Zarko; ACS Catalysis 11 (2021) 10351–10361; doi:10.1021/acscatal.1c03092

data_4518994
_publ_section_title
;
 Nickel-Catalyzed Annulations of ortho-Haloarylimines
;
_journal_issue                   16
_journal_name_full               'ACS Catalysis'
_journal_page_first              10351
_journal_page_last               10361
_journal_paper_doi               10.1021/acscatal.1c03092
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C20 H20 Cl2 N2 Ni'
_chemical_formula_sum            'C20 H20 Cl2 N2 Ni'
_chemical_formula_weight         417.99
_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     dual
_audit_creation_date             2020-10-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-10-21 deposited with the CCDC.	2021-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                86.1170(10)
_cell_angle_beta                 80.3240(10)
_cell_angle_gamma                67.5320(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9273(3)
_cell_length_b                   9.4515(3)
_cell_length_c                   11.9381(4)
_cell_measurement_reflns_used    3224
_cell_measurement_temperature    199.99
_cell_measurement_theta_max      70.096
_cell_measurement_theta_min      3.756
_cell_volume                     917.58(5)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      199.99
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13498
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.096
_diffrn_reflns_theta_min         3.756
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_exptl_absorpt_coefficient_mu    4.228
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0343P)^2^+0.4975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3157
_reflns_number_total             3224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03092_si_006.cif
_cod_data_source_block           q95k
_cod_database_code               4518994
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.849
_shelx_estimated_absorpt_t_min   0.742
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00D), C00H(H00E,H00H), C00I(H00I,H00J), C00N(H00O,H00P), C00O(H00Q,
 H00R), C00P(H00S,H00T)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00F(H00F), C00G(H00G), C00J(H00K), C00K(H00L),
 C00L(H00M), C00M(H00N)
;
_shelx_res_checksum              2777
_shelx_hkl_checksum              63339
_olex2_submission_special_instructions 'No special instructions were received'