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_4038656
_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_formula_sum            'C43 H33 Cl3 O4 S2'
_chemical_formula_weight         784.16
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                75.860(2)
_cell_angle_beta                 73.582(2)
_cell_angle_gamma                84.176(2)
_cell_formula_units_Z            1
_cell_length_a                   8.1459(3)
_cell_length_b                   9.0608(4)
_cell_length_c                   13.5621(5)
_cell_measurement_reflns_used    5252
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      5.04
_cell_volume                     930.52(6)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8785
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.525
_diffrn_reflns_theta_max         66.525
_diffrn_reflns_theta_min         3.487
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    3.628
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       prizm
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0563P)^2^+1.4494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3005
_reflns_number_total             3229
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01387_si_002.cif
_cod_data_source_block           cu_mh236_0m_a
_cod_database_code               4038656
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.736
_shelx_estimated_absorpt_t_max   0.899
_shelx_res_checksum              4802
_shelx_hkl_checksum              31472