Bromination of the benzothioxanthene Bloc: toward new π-conjugated systems for organic electronic applications
Josse, Pierre; Li, Shi; Dayneko, Sergey; Joly, Damien; Labrunie, Antoine; Dabos-Seignon, Sylvie; Allain, Magali; Siegler, Benjamin; Demadrille, Renaud; Welch, Gregory C.; Risko, Chad; Blanchard, Philippe; Cabanetos, Clément; Journal of Materials Chemistry C 6 (2018) 761–; doi:10.1039/C7TC05245F

data_7237034
_publ_section_title
;
 Bromination of the benzothioxanthene Bloc: toward new \p-conjugated
 systems for organic electronic applications
;
_journal_issue                   4
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              761
_journal_paper_doi               10.1039/C7TC05245F
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         '2 (C23 H18 Br1 N1 O2 S1), C H Cl3'
_chemical_formula_sum            'C47 H37 Br2 Cl3 N2 O4 S2'
_chemical_formula_weight         1024.07
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      13
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-03-02T15:04:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-10-27 deposited with the CCDC.
2017-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.163(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5479(8)
_cell_length_b                   16.635(3)
_cell_length_c                   16.8090(18)
_cell_measurement_reflns_used    1882
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.175
_cell_measurement_theta_min      3.697
_cell_volume                     2105.0(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 5.199
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6506
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.637
_diffrn_reflns_theta_min         2.656
_exptl_absorpt_coefficient_mu    5.517
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.91311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       needle
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.023
_platon_squeeze_details
;
The unit cell contains disordered chloroform molecules which were not modelled
but the corresponding density was taken into account using SQUEEZE/PLATON
procedure. The unit cell contains 2 voids of 62 electrons/ 156 A3 which can be
each attributed to one chloroform molecule. The new composition (2 chloroform
molecules per cell) was included in the calculation of the empirical formula,
formula weight, density, linear absorption coefficient and F(000).
;
_refine_diff_density_max         1.85
_refine_diff_density_min         -1.062
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0899
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1839P)^2^+0.7328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2408
_refine_ls_wR_factor_ref         0.2581
_reflns_Friedel_coverage         0
_reflns_number_gt                2945
_reflns_number_total             3937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7tc05245f2.cif
_cod_data_source_block           platon_sqd
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               7237034
_platon_squeeze_void_probe_radius 1.2