Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character
Marshall, Jonathan L.; Uchida, Kazuyuki; Frederickson, Conerd K.; Schütt, Christian; Zeidell, Andrew M.; Goetz, Katelyn P.; Finn, Tristan W.; Jarolimek, Karol; Zakharov, Lev N.; Risko, Chad; Herges, Rainer; Jurchescu, Oana D.; Haley, Michael M.; Chem. Sci. 7 (2016) 5547–; doi:10.1039/C6SC00950F

data_1543326
_publ_section_title
;
 Indacenodibenzothiophenes: synthesis, optoelectronic properties and
 materials applications of molecules with strong antiaromatic character
;
_journal_issue                   8
_journal_name_full               'Chem. Sci.'
_journal_page_first              5547
_journal_paper_doi               10.1039/C6SC00950F
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C44.5 H36.5 Cl1.5 S2'
_chemical_formula_weight         688.53
_chemical_name_systematic
;
 ?
;
_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-2013
_audit_update_record
;
2016-02-01 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.313(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7863(11)
_cell_length_b                   37.373(3)
_cell_length_c                   7.0980(6)
_cell_measurement_reflns_used    2247
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      49.04
_cell_measurement_theta_min      2.36
_cell_volume                     3598.1(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-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.617
_diffrn_measured_fraction_theta_max 0.923
_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  0.0648
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_Laue_measured_fraction_full 0.617
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13782
_diffrn_reflns_point_group_measured_fraction_full 0.617
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         53.935
_diffrn_reflns_theta_min         2.364
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    2.593
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'royal blue'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       plate
_exptl_crystal_F_000             1444
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0737
_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^)+(0.1084P)^2^+8.4172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.2203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2714
_reflns_number_total             4023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00950f2.cif
_cod_data_source_block           mh132_a
_cod_depositor_comments
'Adding full bibliography for 1543324--1543327.cif.'
_cod_original_formula_sum        'C44.50 H36.50 Cl1.50 S2'
_cod_database_code               1543326
_shelx_estimated_absorpt_t_min   0.800
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2013-4
_shelx_res_checksum              57565
_shelx_hkl_checksum              2523