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_4034219
_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 H14 N2 O'
_chemical_formula_weight         298.33
_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                76.7700(10)
_cell_angle_beta                 76.1270(10)
_cell_angle_gamma                89.6810(10)
_cell_formula_units_Z            16
_cell_length_a                   15.5365(7)
_cell_length_b                   15.5527(7)
_cell_length_c                   25.5575(11)
_cell_measurement_reflns_used    9258
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.63
_cell_measurement_theta_min      2.39
_cell_volume                     5828.4(4)
_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      296(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  0.0908
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            108818
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.467
_diffrn_reflns_theta_min         0.844
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.714
_exptl_crystal_size_mid          0.557
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00208(11)
_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   0.846
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2014
_refine_ls_number_reflns         28907
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.847
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0494P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13127
_reflns_number_total             28907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02939_si_003.cif
_cod_data_source_block           17fq18raw
_cod_depositor_comments
;

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C160 H112 N16 O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     2386.65
_cod_database_code               4034219
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.991
_exptl_absorpt_special_details
; 
Scan width 0.5\% , Crystal to detector distance 5.960 cm, 
exposure time 14 s, about 25 hours for data collection,  without scale. 
The 6 omiga-run take the following 2theta, initial-omiga, phi values 
and the following sweep-ranges, respectively.
-18.6, -219.601,-105.0, 223.0 (positively run)
-27.0,  -28.0,     0.0, 186.0 (negatively run)
-29.0,  146.0,    72.0, 186.0 (positively run)
-29.0,  -28.0,   144.0, 186.0 (negatively run)
-29.0,  146.0,   216.0, 186.0 (positively run)
-30.0,  -28.0,   288.0, 200.0 (negatively run)
;
_shelx_res_checksum              20284
_shelx_hkl_checksum              77011