Enantioselective synthesis of 3-(<i>N</i>-indolyl)quinolines containing axial and central chiralities.
Yamanomoto, Ken; Yamamoto, Kota; Yoshida, Satoshi; Sato, Sota; Akiyama, Takahiko; Chemical communications (Cambridge, England) 60 (2024) 582–585; doi:10.1039/d3cc05142k

data_7132453
_publ_section_title
;
 Enantioselective synthesis of 3-(<i>N</i>-indolyl)quinolines containing
 axial and central chiralities.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              582
_journal_page_last               585
_journal_paper_doi               10.1039/d3cc05142k
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C27 H23 N3 O), C H2 Cl2'
_chemical_formula_sum            'C55 H48 Cl2 N6 O2'
_chemical_formula_weight         895.89
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-03-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-08-03 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.0150(13)
_cell_length_b                   17.560(2)
_cell_length_c                   7.712(2)
_cell_measurement_reflns_used    13164
_cell_measurement_temperature    95.15
_cell_measurement_theta_max      32.822
_cell_measurement_theta_min      2.110
_cell_volume                     2304.2(7)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'KEK UGUIS'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      95.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'PAD EIGER X 16M(Dectris)'
_diffrn_measurement_method       'oscillation method, \w scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.900
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            29161
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        32.684
_diffrn_reflns_theta_max         32.822
_diffrn_reflns_theta_min         2.110
_diffrn_source                   'KEK PF BL17A beamline'
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0584P)^2^+0.4760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4044
_reflns_number_total             4204
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05142k2.cif
_cod_data_source_block           yamanomoto_ind_ala_maj_sy309_data01_a
_cod_depositor_comments          'Adding full bibliography for 7132453.cif.'
_cod_database_code               7132453
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H28A(0.5) H28B(0.5)
3.a Ternary CH refined with riding coordinates:
 C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C23(H23), C8(H8), C17(H17), C14(H14), C4(H4), C13(H13), C15(H15),
 C11(H11), C1(H1), C16(H16), C2(H2), C10(H10), C3(H3A), C12(H12)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              69977
_shelx_hkl_checksum              71949
_olex2_submission_special_instructions 'No special instructions were received'