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_4032876
_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_sum            'C36 H29 Br N4 Ni'
_chemical_formula_weight         656.25
_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                 98.977(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6966(3)
_cell_length_b                   27.8406(7)
_cell_length_c                   8.1912(2)
_cell_measurement_reflns_used    10405
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      31.49
_cell_measurement_theta_min      2.18
_cell_volume                     2859.97(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23533
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.463
_exptl_absorpt_coefficient_mu    2.109
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.557
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         6513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.272
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+4.0513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6185
_reflns_number_total             6513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01899_si_002.cif
_cod_data_source_block           v161024-2BrNor_a_compound_2b
_cod_depositor_comments
'Adding full bibliography for 4032875--4032877.cif.'
_cod_database_code               4032876
_shelx_estimated_absorpt_t_min   0.580
_shelx_estimated_absorpt_t_max   0.902
_shelxl_version_number           2014-3
_shelx_res_checksum              64646
_shelx_hkl_checksum              39153