Synthesis and Characterization of Two Unsymmetrical Indenofluorene Analogues: Benzo[5,6]-s-indaceno[1,2-b]thiophene and Benzo[5,6]-s-indaceno[2,1-b]thiophene.
Marshall, Jonathan L.; O'Neal, Nathaniel J; Zakharov, Lev N.; Haley, Michael M.; The Journal of organic chemistry 81 (2016) 3674–3680; doi:10.1021/acs.joc.6b00340

data_4036705
_publ_section_title
;
 Synthesis and Characterization of Two Unsymmetrical Indenofluorene
 Analogues: Benzo[5,6]-s-indaceno[1,2-b]thiophene and
 Benzo[5,6]-s-indaceno[2,1-b]thiophene.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3674
_journal_page_last               3680
_journal_paper_doi               10.1021/acs.joc.6b00340
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C78 H72 S2'
_chemical_formula_weight         1073.47
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 98.391(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4687(11)
_cell_length_b                   8.0770(8)
_cell_length_c                   30.511(3)
_cell_measurement_reflns_used    3796
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      65.99
_cell_measurement_theta_min      2.93
_cell_volume                     3039.9(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      223(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.988
_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  0.0418
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20006
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.889
_diffrn_reflns_theta_min         2.928
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_platon_squeeze_details
;
Solvent hexane molecule, C6H14 (50 electrons), disordred around 
an inversion centers was treated by SQUEEZE. 
;
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0586
_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^)+(0.1109P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3786
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00340_si_006.cif
_cod_data_source_block           cu_mh170_0m_sqd
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036705
_shelx_estimated_absorpt_t_min   0.868
_shelx_estimated_absorpt_t_max   0.989
_platon_squeeze_void_probe_radius 1.20
_shelxl_version_number           2013-4
_shelx_res_checksum              7445
_shelx_hkl_checksum              28446