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_4518995
_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 H21 Br N2 Ni, C3 H3'
_chemical_formula_sum            'C23 H24 Br N2 Ni'
_chemical_formula_weight         467.06
_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             2020-11-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-11-04 deposited with the CCDC.	2021-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                105.435(2)
_cell_angle_beta                 91.184(2)
_cell_angle_gamma                91.402(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0773(4)
_cell_length_b                   9.9718(5)
_cell_length_c                   13.0748(6)
_cell_measurement_reflns_used    3568
_cell_measurement_temperature    199.99
_cell_measurement_theta_max      70.159
_cell_measurement_theta_min      3.508
_cell_volume                     1014.42(9)
_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 0.954
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13289
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.159
_diffrn_reflns_theta_min         3.508
_exptl_absorpt_coefficient_mu    3.744
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0357P)^2^+0.3949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3390
_reflns_number_total             3568
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03092_si_007.cif
_cod_data_source_block           q08l
_cod_database_code               4518995
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.793
_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(H00E,H00F), C00F(H00G,H00H), C00H(H00J,H00K), C00J(H00M,H00N), C00O(H00Q,
 H00R), C00P(H00S,H00T)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00I), C00I(H00L),
 C00K(H00O), C00L(H00V), C00M(H00W), C00N(H00P), C00Q(H00X), C00R(H00U)
;
_shelx_res_checksum              35428
_shelx_hkl_checksum              49837
_olex2_submission_special_instructions 'No special instructions were received'