Synthesis of 3-aminoquinolines from α-imino rhodium carbenes and 2-aminobenzaldehydes.
Li, Jiani; Feng, Jing; Chen, Tao; Xu, Ze-Feng; Li, Chuan-Ying; Organic & biomolecular chemistry 21 (2023) 5935–5938; doi:10.1039/d3ob00843f

data_7159444
_publ_section_title
;
 Synthesis of 3-aminoquinolines from &#x3b1;-imino rhodium carbenes and
 2-aminobenzaldehydes.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5935
_journal_page_last               5938
_journal_paper_doi               10.1039/d3ob00843f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C22 H18 N2 O2 S'
_chemical_formula_weight         374.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-04-15 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.817(3)
_cell_length_b                   12.371(5)
_cell_length_c                   19.295(7)
_cell_measurement_reflns_used    4484
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.58
_cell_measurement_theta_min      2.68
_cell_volume                     1865.9(12)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11468
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         1.955
_exptl_absorpt_coefficient_mu    0.193
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3703
_reflns_number_total             4197
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00843f2.cif
_cod_data_source_block           20220603_0m_a
_cod_depositor_comments          'Adding full bibliography for 7159444.cif.'
_cod_original_cell_volume        1865.8(12)
_cod_database_code               7159444
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              93060