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_7159277
_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 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-09-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-09-13 deposited with the CCDC.	2023-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.739(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9864(5)
_cell_length_b                   4.87230(14)
_cell_length_c                   18.6483(6)
_cell_measurement_reflns_used    5600
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.4870
_cell_measurement_theta_min      3.8790
_cell_volume                     1328.15(7)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.920
_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    -20.00  30.00   1.00   13.56    --  -10.77 -99.00-120.00   50
  2  \w    -52.00  69.00   1.00   13.56    --  -10.77  19.00-180.00  121
  3  \w    -83.00  17.00   1.00   13.56    --  -10.77 -57.00   0.00  100
  4  \w    -14.00  83.00   1.00   13.56    --   10.69  37.00-150.00   97
  5  \w    -20.00  52.00   1.00   13.56    --   10.69 -99.00  30.00   72
;
_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      0.0433478000
_diffrn_orient_matrix_UB_12      -0.0446969000
_diffrn_orient_matrix_UB_13      0.0201889000
_diffrn_orient_matrix_UB_21      0.0167041000
_diffrn_orient_matrix_UB_22      -0.0002524000
_diffrn_orient_matrix_UB_23      -0.0327591000
_diffrn_orient_matrix_UB_31      0.0140042000
_diffrn_orient_matrix_UB_32      0.1384894000
_diffrn_orient_matrix_UB_33      0.0064480000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15671
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.706
_diffrn_reflns_theta_min         3.342
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.689
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.762
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0526P)^2^+0.7209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2761
_reflns_number_total             3460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00348e2.cif
_cod_data_source_block           yi5n
_cod_depositor_comments
'Adding full bibliography for 7159276--7159277.cif.'
_cod_original_cell_volume        1328.16(7)
_cod_database_code               7159277
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C17 H15 N O3'
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C3(H3A), C6(H6), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              76969
_olex2_date_sample_data_collection 2021-01-12
_olex2_date_sample_submission    2021-01-11
_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 1.132
_oxdiff_exptl_absorpt_empirical_full_min 0.839