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_7243644
_publ_section_title
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 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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-24
_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                90
_cell_angle_beta                 109.953(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.929(18)
_cell_length_b                   10.763(18)
_cell_length_c                   15.62(3)
_cell_measurement_reflns_used    3022
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.959
_cell_measurement_theta_min      2.346
_cell_volume                     1727(5)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.965
_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  0.0659
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9388
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.127
_diffrn_reflns_theta_min         1.982
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0904 before and 0.0559 after correction.
The Ratio of minimum to maximum transmission is 0.7064.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.1629
_refine_ls_R_factor_gt           0.0968
_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^)+6.0103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1990
_reflns_number_total             3319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra06330h2.cif
_cod_data_source_block           mo_052301_0m_a
_cod_original_cell_volume        1726(5)
_cod_database_code               7243644
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.975
_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.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C19(H19), C15(H15), C18(H18), C1(H1A), C6(H6),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              36049
_olex2_submission_special_instructions 'No special instructions were received'