Acid-Mediated Migration of Bromide in an Antiaromatic Porphyrinoid: Preparation of Two Regioisomeric Ni(II) Bromonorcorroles.
Kawashima, Hiroyuki; Hiroto, Satoru; Shinokubo, Hiroshi; The Journal of organic chemistry 82 (2017) 10425–10432; doi:10.1021/acs.joc.7b01899

data_4032877
_publ_section_title
;
 Acid-Mediated Migration of Bromide in an Antiaromatic Porphyrinoid:
 Preparation of Two Regioisomeric Ni(II) Bromonorcorroles.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10425
_journal_page_last               10432
_journal_paper_doi               10.1021/acs.joc.7b01899
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C45 H41 Cl2 N5 Ni'
_chemical_formula_sum            'C45 H41 Cl2 N5 Ni'
_chemical_formula_weight         781.44
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 106.565(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7230(4)
_cell_length_b                   25.4861(11)
_cell_length_c                   15.9516(5)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      25.0781
_cell_measurement_theta_min      2.3513
_cell_volume                     3788.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
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_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  ImuS
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27047
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.080
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.691
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         6576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0617P)^2^+5.4942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5513
_reflns_number_total             6576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01899_si_002.cif
_cod_data_source_block           kawashima20160614_1_a_compound_3ab
_cod_depositor_comments
'Adding full bibliography for 4032875--4032877.cif.'
_cod_database_code               4032877
_shelx_estimated_absorpt_t_min   0.736
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2014-3
_shelx_res_checksum              31215
_shelx_hkl_checksum              55609