A competitive and highly selective 7-, 6- and 5-annulation with 1,3-migration through C-H and N-H - alkyne coupling.
Ajarul, Sk; Kayet, Anirban; Pati, Tanmay K.; Maiti, Dilip K.; Chemical communications (Cambridge, England) 56 (2020) 474–477; doi:10.1039/c9cc07360d

data_7125639
_publ_section_title
;
 A competitive and highly selective 7-, 6- and 5-annulation with
 1,3-migration through C-H and N-H - alkyne coupling.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              474
_journal_page_last               477
_journal_paper_doi               10.1039/c9cc07360d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C24 H19 N O3'
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.41
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-04-19 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                80.88(4)
_cell_angle_beta                 85.50(3)
_cell_angle_gamma                69.03(3)
_cell_formula_units_Z            2
_cell_length_a                   8.893(9)
_cell_length_b                   10.210(11)
_cell_length_c                   11.258(10)
_cell_measurement_reflns_used    5090
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.09
_cell_measurement_theta_min      2.45
_cell_volume                     942.2(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1795
_diffrn_reflns_av_sigmaI/netI    0.1363
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30258
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       crystalline
_exptl_crystal_F_000             438
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.0729
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.2081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1759
_refine_ls_wR_factor_ref         0.2191
_reflns_number_gt                2257
_reflns_number_total             4725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc07360d2.cif
_cod_data_source_block           ajarul_0m_a
_cod_depositor_comments
'Adding full bibliography for 7125638--7125639.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7125639