Synthesis of Quinoline Derivatives via Cu-Catalyzed Cascade Annulation of Heterocumulenes, Alkynes, and Diaryliodonium Salts
Chi, Yue; Yan, Haihan; Zhang, Wen-Xiong; Xi, Zhenfeng; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b01025

data_1546003
_publ_section_title
;
 Synthesis of Quinoline Derivatives via Cu-Catalyzed Cascade Annulation of
 Heterocumulenes, Alkynes, and Diaryliodonium Salts
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b01025
_journal_year                    2017
_chemical_formula_moiety         'C30 H25 N S'
_chemical_formula_sum            'C30 H25 N S'
_chemical_formula_weight         431.57
_chemical_name_systematic        Mes
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.307(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3505(9)
_cell_length_b                   8.6159(8)
_cell_length_c                   27.293(3)
_cell_measurement_reflns_used    1750
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      26.1960
_cell_measurement_theta_min      4.0270
_cell_volume                     2401.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   35.00  104.00   1.0000    5.2500
omega____ theta____ kappa____ phi______ frames
    -       13.6191  178.0000   60.0000 69

  2 omega  -60.00   42.00   1.0000    5.2500
omega____ theta____ kappa____ phi______ frames
    -       13.6191  -57.0000 -150.0000 102
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0178480000
_diffrn_orient_matrix_UB_12      0.0474285000
_diffrn_orient_matrix_UB_13      -0.0212442000
_diffrn_orient_matrix_UB_21      0.0653182000
_diffrn_orient_matrix_UB_22      -0.0028877000
_diffrn_orient_matrix_UB_23      -0.0047826000
_diffrn_orient_matrix_UB_31      -0.0153764000
_diffrn_orient_matrix_UB_32      -0.0672624000
_diffrn_orient_matrix_UB_33      -0.0147929000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8989
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.238
_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     292
_refine_ls_number_reflns         4725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.4909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1595
_reflns_number_gt                2779
_reflns_number_total             4725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b01025_si_002.cif
_cod_data_source_block           8f
_cod_database_code               1546003
_chemical_oxdiff_formula         'C20 H25 N3 Cl'
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C26(H26)
2.b Idealised Me refined as rotating group:
 C28(H28a,H28b,H28c), C29(H29a,H29b,H29c), C30(H30a,H30b,H30c)
;
_olex2_date_sample_data_collection 2016-06-02
_olex2_submission_special_instructions 'No special instructions were received'