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_7120191
_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            'C18 H15 N3 O'
_chemical_formula_weight         289.12
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
;
2017-04-02 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                82.497(4)
_cell_angle_beta                 88.246(4)
_cell_angle_gamma                74.495(4)
_cell_formula_units_Z            4
_cell_length_a                   8.6108(4)
_cell_length_b                   9.2715(3)
_cell_length_c                   19.9066(10)
_cell_measurement_reflns_used    4235
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1370
_cell_measurement_theta_min      3.2650
_cell_volume                     1518.28(12)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_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    0.0469
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12366
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0554P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1218
_reflns_number_gt                3838
_reflns_number_total             5331
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc02815f2.cif
_cod_data_source_block           cwb-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1518.28(11)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_original_formula_sum        'C18 H15 N3 O1'
_cod_database_code               7120191