Indole-Fused Acridone: Synthesis, Structures, Proton Transfer, and Hole-Transport Properties.
Jin, Ying-Ying; Fang, Qi; The Journal of organic chemistry 84 (2019) 3832–3842; doi:10.1021/acs.joc.8b02939

data_4034215
_publ_section_title
;
 Indole-Fused Acridone: Synthesis, Structures, Proton Transfer, and
 Hole-Transport Properties.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3832
_journal_page_last               3842
_journal_paper_doi               10.1021/acs.joc.8b02939
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C20 H13 Br N2 O'
_chemical_formula_weight         377.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                96.437(2)
_cell_angle_beta                 90.969(2)
_cell_angle_gamma                98.162(2)
_cell_formula_units_Z            4
_cell_length_a                   7.3885(10)
_cell_length_b                   11.9192(16)
_cell_length_c                   17.597(2)
_cell_measurement_reflns_used    5064
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.88
_cell_measurement_theta_min      2.74
_cell_volume                     1523.5(3)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_number            6946
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         1.165
_exptl_absorpt_coefficient_mu    2.707
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       bar
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         6946
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0781P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3855
_reflns_number_total             6946
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02939_si_006.cif
_cod_data_source_block           18fq04twin
_cod_depositor_comments
;

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1523.5(4)
_cod_original_formula_sum        'C40 H26 Br2 N4 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     754.47
_cod_database_code               4034215
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.326
_shelx_estimated_absorpt_t_max   0.863
_exptl_absorpt_special_details
; 
Scan width 0.5\% , Crystal to detector distance 5.960 cm, 
exposure time 90s, about 66 hours for data collection, without scale. 
The 7 omiga-run take the following 2theta, initial-omiga, phi values 
and the following sweep-ranges, respectively 
-27, -28, 0, 186 (negatively run)
-28, 146, 51.4, 186 (positively run)
-27, -28, 102.8, 186 (negatively run)
-28, 146, 154.2, 186 (positively run)
-27, -28, 205.6, 186 (negatively run)
-28, 146, 257, 186 (positively run)
-27, -28, 308.4, 186 (negatively run)  
;
_shelx_res_checksum              96105
_shelx_hkl_checksum              88385