A new synthesis of indolo[2,3-b]quinolines from 3-acetyl-N-alkyl-2-chloroindoles with 2-aminobenzophenone
Zhang, Hong; Jiang, Yunhe; Sun, Xiaoxue; Liang, Tianyu; Wang, Xiang; Li, Yang; RSC Advances 14 (2024) 30707–30712; doi:10.1039/D4RA05176A

data_7249400
_publ_section_title
;
 A new synthesis of indolo[2,3-b]quinolines from
 3-acetyl-N-alkyl-2-chloroindoles with 2-aminobenzophenone
;
_journal_issue                   42
_journal_name_full               'RSC Advances'
_journal_page_first              30707
_journal_page_last               30712
_journal_paper_doi               10.1039/D4RA05176A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C24 H19 Cl N2'
_chemical_formula_sum            'C24 H19 Cl N2'
_chemical_formula_weight         370.86
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-07-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-07-03 deposited with the CCDC.	2024-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.5868(4)
_cell_length_b                   13.6623(6)
_cell_length_c                   31.9980(16)
_cell_measurement_reflns_used    5019
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.912
_cell_measurement_theta_min      2.546
_cell_volume                     3753.9(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            26661
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.502
_diffrn_reflns_theta_min         2.546
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0612
_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^)+(0.0660P)^2^+1.9746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1650
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3184
_reflns_number_total             4760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra05176a2.cif
_cod_data_source_block           2
_cod_database_code               7249400
_shelx_shelxl_version_number     2018/3
_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.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Me refined with riding coordinates:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C5(H5), C2(H2), C17(H17), C15(H15), C12(H12), C3(H3), C11(H11),
 C13(H13), C14(H14), C4(H4)
;
_shelx_res_checksum              36160
_shelx_hkl_checksum              79679
_olex2_submission_special_instructions 'No special instructions were received'