Concise synthesis of 2,3-disubstituted quinoline derivatives <i>via</i> ruthenium-catalyzed three-component deaminative coupling reaction of anilines, aldehydes and amines.
Shakenov, Aldiyar; Gnyawali, Krishna Prasad; Yi, Chae S.; Organic & biomolecular chemistry 21 (2023) 3582–3587; doi:10.1039/d3ob00348e

data_7159276
_publ_section_title
;
 Concise synthesis of 2,3-disubstituted quinoline derivatives <i>via</i>
 ruthenium-catalyzed three-component deaminative coupling reaction of
 anilines, aldehydes and amines.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3582
_journal_page_last               3587
_journal_paper_doi               10.1039/d3ob00348e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C17 H14 F N O2'
_chemical_formula_sum            'C17 H14 F N O2'
_chemical_formula_weight         283.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-09-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-09-13 deposited with the CCDC.	2023-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.4637(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.2945(5)
_cell_length_b                   3.86139(6)
_cell_length_c                   25.3106(4)
_cell_measurement_reflns_used    5693
_cell_measurement_temperature    99.95(10)
_cell_measurement_theta_max      70.2600
_cell_measurement_theta_min      4.6230
_cell_volume                     2562.07(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -67.00  32.00   1.00    5.00    --  -42.46  37.00  60.00   99
  2  \w   -131.00  46.00   1.00    5.00    --  -42.46   0.00-180.00  177
  3  \w     71.00 172.00   1.00   20.00    --  100.00  61.00 -30.00  101
  4  \w     27.00 126.00   1.00   20.00    --  100.00 -45.00-180.00   99
  5  \w     72.00 176.00   1.00   20.00    --  100.00  30.00  60.00  104
  6  \w     94.00 173.00   1.00   20.00    --  100.00 125.00  90.00   79
  7  \w     94.00 173.00   1.00   20.00    --  100.00 125.00-150.00   79
  8  \w     27.00 118.00   1.00   20.00    --  100.00-125.00 150.00   91
  9  \w   -119.00 -10.00   1.00    5.00    --  -42.46 -77.00  90.00  109
 10  \w     10.00 119.00   1.00    5.00    --   42.46  77.00 -30.00  109
 11  \w     71.00 172.00   1.00   20.00    --  100.00  61.00 150.00  101
 12  \w     67.00 176.00   1.00   20.00    --  100.00  77.00-180.00  109
 13  \w     17.00 110.00   1.00   20.00    --  100.00 -94.00-180.00   93
 14  \w     71.00 172.00   1.00   20.00    --  100.00  61.00 -90.00  101
 15  \w   -115.00 -14.00   1.00    5.00    --  -42.46 -57.00-180.00  101
 16  \w     23.00  98.00   1.00    5.00    --   42.46-125.00-150.00   75
 17  \w     71.00 118.00   1.00   20.00    --  100.00  61.00  90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0181606000
_diffrn_orient_matrix_UB_12      0.1332812000
_diffrn_orient_matrix_UB_13      0.0527450000
_diffrn_orient_matrix_UB_21      0.0475181000
_diffrn_orient_matrix_UB_22      0.2334195000
_diffrn_orient_matrix_UB_23      0.0075634000
_diffrn_orient_matrix_UB_31      -0.0293994000
_diffrn_orient_matrix_UB_32      0.2948258000
_diffrn_orient_matrix_UB_33      -0.0298248000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12360
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        70.411
_diffrn_reflns_theta_max         70.411
_diffrn_reflns_theta_min         3.503
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0509P)^2^+1.9539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2207
_reflns_number_total             2437
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00348e2.cif
_cod_data_source_block           yi5f
_cod_depositor_comments
'Adding full bibliography for 7159276--7159277.cif.'
_cod_original_cell_volume        2562.08(8)
_cod_database_code               7159276
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C17 H14 F N O2'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              88664
_olex2_date_sample_data_collection 2020-09-01
_olex2_date_sample_submission    2020-08-31
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.822