Late-stage Modification of Electronic Properties of Antiaromatic and Diradicaloid Indeno[1,2-b]fluorene Analogues via Sulfur Oxidation.
Dressler, Justin; Barker, Joshua E.; Karas, Lucas J.; Hashimoto, Hannah; Kishi, Ryohei; Zakharov, Lev N.; MacMillan, Samantha N.; Gómez-García, Carlos J; Nakano, Masayoshi; Wu, Judy I.; Haley, Michael M.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01387

data_4038653
_publ_section_title
;
 Late-stage Modification of Electronic Properties of Antiaromatic and
 Diradicaloid Indeno[1,2-b]fluorene Analogues via Sulfur Oxidation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01387
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C54 H48 Cl6 N2 O4 S2'
_chemical_formula_weight         1065.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.21(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.949(3)
_cell_length_b                   25.877(6)
_cell_length_c                   16.528(5)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.75
_cell_measurement_theta_min      4.11
_cell_volume                     5058(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.1666
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17136
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.934
_diffrn_reflns_theta_min         3.416
_diffrn_source                   'incoatec i\mS'
_exptl_absorpt_coefficient_mu    4.257
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       cut-strip
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_platon_squeeze_details
;
Solvent molecule CHCl3, 58 electrons, is highly disordered
and was treated by SQUEEZE
;
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.28(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         6906
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0719
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0155P)^2^+2.4670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.2030
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4610
_reflns_number_total             6906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01387_si_005.cif
_cod_data_source_block           cu_mh263_0m_a_sqd
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4038653
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.587
_shelx_estimated_absorpt_t_max   0.920
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              73057
_shelx_hkl_checksum              34079