Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines.
Wang, Ze-Shu; Chen, Yang-Bo; Zhang, Hao-Wen; Sun, Zhou; Zhu, Chunyin; Ye, Long-Wu; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b13975

data_4134156
_publ_section_title
;
 Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated
 Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized
 Indoles and Isoquinolines.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13975
_journal_year                    2020
_chemical_formula_moiety         'C28 H23 N'
_chemical_formula_sum            'C28 H23 N'
_chemical_formula_weight         373.47
_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             2018-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.615(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.248(2)
_cell_length_b                   10.033(2)
_cell_length_c                   21.131(5)
_cell_measurement_reflns_used    1970
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.46
_cell_measurement_theta_min      2.20
_cell_volume                     1958.6(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16560
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.248
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.1099 before and 0.0770 after correction.
The Ratio of minimum to maximum transmission is 0.8189.
The \l/2 correction factor is 0.0015.
;
_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    1.267
_exptl_crystal_density_meas      1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0837
_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^)+(0.0860P)^2^+0.1292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.2072
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2943
_reflns_number_total             4458
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13975_si_002.cif
_cod_data_source_block           y0510m
_cod_original_cell_volume        1958.6(8)
_cod_database_code               4134156
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.993
_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 Ternary CH refined with riding coordinates:
 C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C5(H5), C9(H9), C4(H4), C13(H13), C28(H28), C25(H25), C3(H3),
 C22(H22), C18(H18), C26(H26), C27(H27), C10(H10), C11(H11), C12(H12), C19(H19),
  C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              71470
_shelx_hkl_checksum              90657
_olex2_submission_special_instructions 'No special instructions were received'