Axially and Helically Chiral Cationic Radical Bicarbazoles: SOMO-HOMO Level Inversion and Chirality Impact on the Stability of Mono- and Diradical Cations.
Kasemthaveechok, Sitthichok; Abella, Laura; Jean, Marion; Cordier, Marie; Roisnel, Thierry; Vanthuyne, Nicolas; Guizouarn, Thierry; Cador, Olivier; Autschbach, Jochen; Crassous, Jeanne; Favereau, Ludovic; Journal of the American Chemical Society 142 (2020) 20409–20418; doi:10.1021/jacs.0c08948

data_4135369
_publ_section_title
;
 Axially and Helically Chiral Cationic Radical Bicarbazoles: SOMO-HOMO
 Level Inversion and Chirality Impact on the Stability of Mono- and
 Diradical Cations.
;
_journal_issue                   48
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20409
_journal_page_last               20418
_journal_paper_doi               10.1021/jacs.0c08948
_journal_volume                  142
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C35 H36 N2 O2'
_chemical_formula_sum            'C35 H36 N2 O2'
_chemical_formula_weight         516.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
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_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 99.900(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.902(3)
_cell_length_b                   9.9528(18)
_cell_length_c                   17.758(2)
_cell_measurement_reflns_used    9820
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.5700
_cell_measurement_theta_min      2.3840
_cell_measurement_wavelength     0.71073
_cell_volume                     2942.8(8)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'PLATON, A.L.Spek, Acta Cryst. 2009, D65, 148-155'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
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_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
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_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
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_diffrn_orient_matrix_UB_12      0.0181772
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_diffrn_orient_matrix_UB_22      -0.0887938
_diffrn_orient_matrix_UB_23      -0.0260369
_diffrn_orient_matrix_UB_31      -0.0260461
_diffrn_orient_matrix_UB_32      -0.0433618
_diffrn_orient_matrix_UB_33      0.0402795
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23327
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         2.354
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.650
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6630
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.0917
_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^)+(0.1367P)^2^+1.6888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2346
_refine_ls_wR_factor_ref         0.2641
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4505
_reflns_number_total             6630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0c08948_si_004.cif
_cod_data_source_block           SCK129
_cod_depositor_comments
'Adding full bibliography for 4135368--4135371.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4135369
_shelx_res_checksum              21615
_shelx_hkl_checksum              52741