A simple and efficient copper-catalyzed three-component reaction to synthesize (Z)-1,2-dihydro-2-iminoquinolines
Luo, Xiai; Zhao, Yu; Tao, Susu; Yang, Zhong-Tao; Luo, Hui; Yang, Weiguang; RSC Advances 11 (2021) 31152–31158; doi:10.1039/D1RA06330H

data_7243642
_publ_section_title
;
 A simple and efficient copper-catalyzed three-component reaction to
 synthesize (Z)-1,2-dihydro-2-iminoquinolines
;
_journal_issue                   50
_journal_name_full               'RSC Advances'
_journal_page_first              31152
_journal_page_last               31158
_journal_paper_doi               10.1039/D1RA06330H
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C19 H18 N2 O3 S'
_chemical_formula_sum            'C19 H18 N2 O3 S'
_chemical_formula_weight         354.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-25 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                104.844(2)
_cell_angle_beta                 98.140(2)
_cell_angle_gamma                92.385(2)
_cell_formula_units_Z            6
_cell_length_a                   7.7587(5)
_cell_length_b                   18.0168(12)
_cell_length_c                   19.7560(13)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.98
_cell_volume                     2633.8(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            42101
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.925
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1259 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.9264.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         9293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0549P)^2^+0.9095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6099
_reflns_number_total             9293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra06330h2.cif
_cod_data_source_block           12345
_cod_database_code               7243642
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.907
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N00A(H00A), N2(H2), N00F(H00F), C00P(H00P), C00T(H00T), C00X(H00X), C4(H4),
 C00Z(H00Z), C010(H010), C013(H013), C015(H015), C016(H016), C019(H019), C3(H3),
  C7(H7), C6(H6), C01H(H01k), C01J(H01J), C16(H16), C01L(H01L), C01N(H01N),
 C17(H17), C18(H18), C01T(H01T), C01Z(H01Z), C021(H021), C023(H023)
2.b Idealised Me refined as rotating group:
 C018(H01d,H01e,H01f), C01G(H01g,H01h,H01i), C8(H8a,H8b,H8c), C10(H10a,H10b,
 H10c), C1(H1a,H1b,H1c), C01X(H01a,H01b,H01c), C01Y(H01m,H01o,H01p), C020(H02a,
 H02b,H02c), C022(H02d,H02e,H02f)
;
_shelx_res_checksum              92783
_olex2_submission_special_instructions 'No special instructions were received'