Ligand-free copper-catalyzed efficient one-pot access of benzo[b]pyrido[3,2-f][1,4]oxazepinones through O-heteroarylation-Smiles rearrangement-cyclization cascade
Ganguly, Nemai C.; Mondal, Pallab; Roy, Sushmita; Mitra, Partha; RSC Adv. 4 (2014) 55640–; doi:10.1039/C4RA11128A

data_7218632
_publ_section_title
;
 Ligand-free copper-catalyzed efficient one-pot access of
 benzo[b]pyrido[3,2-f][1,4]oxazepinones through O-heteroarylation-Smiles
 rearrangement-cyclization cascade
;
_journal_issue                   98
_journal_name_full               'RSC Adv.'
_journal_page_first              55640
_journal_paper_doi               10.1039/C4RA11128A
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C19 H14 N2 O2'
_chemical_formula_weight         302.32
_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
_cell_angle_alpha                101.512(5)
_cell_angle_beta                 95.264(6)
_cell_angle_gamma                101.942(5)
_cell_formula_units_Z            2
_cell_length_a                   7.983(2)
_cell_length_b                   8.944(3)
_cell_length_c                   10.904(3)
_cell_measurement_reflns_used    5060
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.91
_cell_measurement_theta_min      2.39
_cell_volume                     739.2(4)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5949
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  .985
_exptl_absorpt_correction_T_min  .980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .19
_exptl_crystal_size_min          .17
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.924
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0698
_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^)+(0.1780P)^2^+0.7277P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2157
_reflns_number_gt                2259
_reflns_number_total             2483
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra11128a2.cif
_cod_data_source_block           sb0613_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/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 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_cell_volume        739.1(4)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7218632