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_4038655
_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            'C48 H44 O4 S2'
_chemical_formula_weight         748.95
_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-2014/7
_cell_angle_alpha                115.901(3)
_cell_angle_beta                 94.740(3)
_cell_angle_gamma                112.307(3)
_cell_formula_units_Z            2
_cell_length_a                   13.0977(14)
_cell_length_b                   15.0775(16)
_cell_length_c                   15.4634(15)
_cell_measurement_reflns_used    3394
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.57
_cell_volume                     2425.5(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.1257
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17634
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.534
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'deep blue/purple'
_exptl_crystal_density_diffrn    1.025
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_platon_squeeze_details
;
I mixture of solvent molecules, CH2Cl2/CHCl3/NCCH3, is highly 
disordered in an area around an inversion center. They were
treated by SQUEEZE and not included in the total formular 
of the compound.   
;
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         8491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1466
_refine_ls_R_factor_gt           0.0848
_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^)+(0.1102P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2035
_refine_ls_wR_factor_ref         0.2237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4288
_reflns_number_total             8491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01387_si_003.cif
_cod_data_source_block           mo_mh265_0m_a_sqd
_cod_original_cell_volume        2425.5(4)
_cod_database_code               4038655
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.999
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              49962
_shelx_hkl_checksum              84846