Fluorination and chlorination effects on quinoxalineimides as an electron-deficient building block for n-channel organic semiconductors
Hasegawa, Tsukasa; Ashizawa, Minoru; Kawauchi, Susumu; Masunaga, Hiroyasu; Ohta, Noboru; Matsumoto, Hidetoshi; RSC Advances 9 (2019) 10807–; doi:10.1039/C9RA02413A

data_7232585
_publ_section_title
;
 Fluorination and chlorination effects on quinoxalineimides as an
 electron-deficient building block for n-channel organic semiconductors
;
_journal_issue                   19
_journal_name_full               'RSC Advances'
_journal_page_first              10807
_journal_paper_doi               10.1039/C9RA02413A
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C16 H15 Br2 N3 O2'
_chemical_formula_sum            'C16 H15 Br2 N3 O2'
_chemical_formula_weight         441.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-02-12 deposited with the CCDC.    2019-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.574(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   5.7237(2)
_cell_length_b                   16.2252(7)
_cell_length_c                   8.9938(4)
_cell_measurement_reflns_used    4851
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.01
_cell_measurement_theta_min      4.96
_cell_volume                     827.95(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_av_unetI/netI     0.0995
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9347
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.102
_diffrn_reflns_theta_min         5.453
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.328
_exptl_absorpt_correction_T_max  0.531
_exptl_absorpt_correction_T_min  0.335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             436.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.25
_refine_diff_density_min         -0.64
_refine_ls_abs_structure_details
;
 Flack x determined using 837 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     348
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0717
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1053P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.1893
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                2378
_reflns_number_total             2729
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9ra02413a2.cif
_cod_data_source_block           SAMPLE8
_cod_database_code               7232585
_shelx_res_checksum              90743