Catalyst-Controlled Structural Divergence: Selective Intramolecular 7-endo-dig and 6-exo-dig Post-Ugi Cyclization for the Synthesis of Benzoxazepinones and Benzoxazinones.
Singh, Karandeep; Malviya, Bhanwar Kumar; Roy, Tapta Kanchan; Mithu, Venus Singh; Bhardwaj, Vimal K.; Verma, Ved Prakash; Chimni, Swapandeep Singh; Sharma, Siddharth; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02123

data_4033272
_publ_section_title
;
 Catalyst-Controlled Structural Divergence: Selective Intramolecular
 7-endo-dig and 6-exo-dig Post-Ugi Cyclization for the Synthesis of
 Benzoxazepinones and Benzoxazinones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02123
_journal_year                    2017
_chemical_formula_moiety         'C28 H25 N3 O3'
_chemical_formula_sum            'C28 H25 N3 O3'
_chemical_formula_weight         451.51
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.631(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.315(5)
_cell_length_b                   14.891(5)
_cell_length_c                   11.713(3)
_cell_measurement_reflns_used    993
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.31
_cell_measurement_theta_min      2.74
_cell_volume                     2445.5(13)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.863
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0762
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5352
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS - Bruker/Siemens area detector absorption and other corrections - V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0879P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1516
_reflns_number_gt                2199
_reflns_number_total             3028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02123_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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_sg_symbol_H-M      'P 21/c'
_cod_database_code               4033272