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_4034217
_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            'C26 H17 N3 O'
_chemical_formula_weight         387.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6465(8)
_cell_length_b                   10.1339(15)
_cell_length_c                   31.872(5)
_cell_measurement_reflns_used    5070
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.99
_cell_measurement_theta_min      2.38
_cell_volume                     1823.7(5)
_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      294(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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  0.0566
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            26021
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.484
_diffrn_reflns_theta_min         1.278
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       massive
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 798 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_coef       0.050(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         4481
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0772
_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^)+(0.1490P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1929
_refine_ls_wR_factor_ref         0.2199
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                2409
_reflns_number_total             4481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02939_si_008.cif
_cod_data_source_block           17fq17raw-p212121
_cod_database_code               4034217
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.986
_exptl_absorpt_special_details
; 
Scan width 0.5\% , Crystal to detector distance 5.960 cm, 
exposure time 42s, about 23 hours for data collection,  without scale. 
The 5 omiga-run take the following 2theta, initial-omiga, phi values 
and the following sweep-ranges, respectively.
-27.0, -28.0,   0.0, 186.0 (negatively run)
-27.0, 146.0,  72.0, 186.0 (positively run)
-28.0, -28.0, 144.0, 186.0 (negatively run)
-28.0, 146.0, 216.0, 186.0 (positively run)
-28.0, -28.0, 288.0, 200.0 (negatively run)
;
_shelx_res_checksum              25317
_shelx_hkl_checksum              78790