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_4036704
_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            'C36 H30 S'
_chemical_formula_weight         494.66
_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   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 108.148(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.4257(4)
_cell_length_b                   7.1547(2)
_cell_length_c                   13.5478(5)
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.57
_cell_measurement_theta_min      3.22
_cell_volume                     1328.73(7)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.994
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7749
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.572
_diffrn_reflns_theta_min         3.224
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.238
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.5008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1202
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2003
_reflns_number_total             2336
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00340_si_007.cif
_cod_data_source_block           mh171
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036704
_shelx_estimated_absorpt_t_min   0.856
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2013-4
_shelx_res_checksum              21248
_shelx_hkl_checksum              13340