Copper-Catalyzed Construction of Eight-Membered Rings via Oxidative Ring Expansion and Intermolecular Cyclization Sequence of Indoles with Amidines: Efficient Synthesis of Benzo[1,3,5]triazocin-6(5H)-ones
Cao, Wen-Bing; Chu, Xue-Qiang; Zhou, Yu; Yin, Ling; Xu, Xiao-Ping; Ji, Shun-Jun; Chem. Commun.  (2017) –; doi:10.1039/C7CC02815F

data_7120190
_publ_section_title
;
 Copper-Catalyzed Construction of Eight-Membered Rings via Oxidative Ring
 Expansion and Intermolecular Cyclization Sequence of Indoles with
 Amidines: Efficient Synthesis of Benzo[1,3,5]triazocin-6(5H)-ones
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02815F
_journal_year                    2017
_chemical_formula_sum            'C21 H15 N3 O'
_chemical_formula_weight         325.36
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   '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
;
2017-01-11 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                95.734(5)
_cell_angle_beta                 98.239(4)
_cell_angle_gamma                112.608(6)
_cell_formula_units_Z            4
_cell_length_a                   10.6190(6)
_cell_length_b                   13.1044(9)
_cell_length_c                   13.2310(7)
_cell_measurement_temperature    293(2)
_cell_volume                     1657.76(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15489
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_refine_diff_density_max         2.088
_refine_diff_density_min         -0.957
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0824
_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^)+(0.1082P)^2^+1.9512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2188
_refine_ls_wR_factor_ref         0.2461
_reflns_number_gt                4747
_reflns_number_total             6786
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc02815f2.cif
_cod_data_source_block           g161128a
_cod_depositor_comments
;

2017-10-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1657.78(17)
_cod_original_formula_sum        'C42 H30 N6 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     650.72
_cod_database_code               7120190