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_7232582
_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_formula_moiety         'C16 H14 Br2 F N3 O2'
_chemical_formula_sum            'C16 H14 Br2 F N3 O2'
_chemical_formula_weight         459.12
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-12 deposited with the CCDC.    2019-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.4350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9939(3)
_cell_length_b                   16.3893(3)
_cell_length_c                   6.87860(10)
_cell_measurement_reflns_used    12299
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      2.97
_cell_volume                     1676.13(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1423
_diffrn_reflns_av_unetI/netI     0.1057
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17388
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         2.972
_exptl_absorpt_coefficient_mu    6.365
_exptl_absorpt_correction_T_max  0.529
_exptl_absorpt_correction_T_min  0.322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.407
_refine_diff_density_min         -1.103
_refine_diff_density_rms         0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1536
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2340
_reflns_number_total             3021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra02413a2.cif
_cod_data_source_block           sample4
_cod_database_code               7232582
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.569
_shelx_estimated_absorpt_t_min   0.569
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(F1)=1-FVAR(1)
 Sof(F2)=FVAR(1)
 Sof(H009)=1-FVAR(2)
 Sof(H00G)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C11(H00A,H00B), C13(H00C,H00D), C12(H00E,H00F), C14(H00H,H00I), C15(H00M,H00N)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H009), C3(H00G)
3.c Idealised Me refined as rotating group:
 C16(H00J,H00K,H00L)
;
_shelx_res_checksum              67410
_olex2_submission_special_instructions 'No special instructions were received'