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_1546002
_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         'C28 H30 N2'
_chemical_formula_sum            'C28 H30 N2'
_chemical_formula_weight         394.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                87.324(9)
_cell_angle_beta                 66.406(9)
_cell_angle_gamma                79.801(8)
_cell_formula_units_Z            2
_cell_length_a                   10.3930(7)
_cell_length_b                   11.0108(13)
_cell_length_c                   11.0248(12)
_cell_measurement_reflns_used    1188
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      22.2950
_cell_measurement_theta_min      3.5060
_cell_volume                     1137.5(2)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9906
_diffrn_measured_fraction_theta_max 0.7670
_diffrn_measurement_details
;
  1 omega    7.00   40.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -       -0.6234  -99.0000   60.0000 33

  2 omega    4.00   68.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -       -0.6234   38.0000  -60.0000 64

  3 omega  -38.00   76.00   1.0000    9.5000
omega____ theta____ kappa____ phi______ frames
    -       -0.6234   19.0000 -120.0000 114
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0035873000
_diffrn_orient_matrix_UB_12      -0.0101492000
_diffrn_orient_matrix_UB_13      -0.0644250000
_diffrn_orient_matrix_UB_21      0.0214088000
_diffrn_orient_matrix_UB_22      0.0580738000
_diffrn_orient_matrix_UB_23      -0.0191361000
_diffrn_orient_matrix_UB_31      0.0724316000
_diffrn_orient_matrix_UB_32      -0.0284892000
_diffrn_orient_matrix_UB_33      -0.0203859000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5842
_diffrn_reflns_theta_full        25.1375
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71588
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.1519
_exptl_crystal_description       block
_exptl_crystal_F_000             424.1511
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2886
_refine_diff_density_min         -0.2860
_refine_diff_density_rms         0.0745
_refine_ls_d_res_high            0.8366
_refine_ls_d_res_low             6.5524
_refine_ls_goodness_of_fit_ref   1.0650
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0650
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.3459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2083
_reflns_number_total             3111
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol7b01025_si_002.cif
_cod_data_source_block           4j
_cod_database_code               1546002
_chemical_oxdiff_formula         'C20 H20 N2'
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     17.19
_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 Ternary CH refined with riding coordinates:
 C26(H26), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C15(H15), C25(H25), C16(H16), C3(H3), C21(H21), C22(H22),
 C23(H23), C24(H24), C19(H19), C18(H18), C17(H17)
2.c Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c), C7(H7a,H7b,H7c), C12(H12a,H12b,H12c), C13(H13a,H13b,
 H13c), C28(H28a,H28b,H28c)
;
_olex2_date_sample_data_collection 2016-09-08
_olex2_submission_special_instructions 'No special instructions were received'