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_7249399
_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         'C23 H18 N2'
_chemical_formula_sum            'C23 H18 N2'
_chemical_formula_weight         322.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   9.851(5)
_cell_length_b                   10.127(5)
_cell_length_c                   16.933(5)
_cell_measurement_reflns_used    4219
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.332
_cell_measurement_theta_min      2.343
_cell_volume                     1689.3(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10973
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         2.343
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             680.0
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1045 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0663
_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^)+(0.1020P)^2^+0.2898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.1923
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.837
_reflns_number_gt                2906
_reflns_number_total             4219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra05176a2.cif
_cod_data_source_block           1
_cod_database_code               7249399
_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:
 C11(H11A,H11B)
2.b Me refined with riding coordinates:
 C4(H4A,H4B,H4C)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C15(H15), C14(H14), C13(H13), C10(H10), C9(H9), C8(H8), C7(H7),
 C6(H6), C5(H5), C3(H3), C2(H2), C1(H1)
;
_shelx_res_checksum              63417
_shelx_hkl_checksum              71345
_olex2_submission_special_instructions 'No special instructions were received'