Secondary Interactions Arrest the Hemiaminal Intermediate To Invert the Modus Operandi of Schiff Base Reaction: A Route to Benzoxazinones.
Patel, Ketan; Deshmukh, Satej S.; Bodkhe, Dnyaneshwar; Mane, Manoj; Vanka, Kumar; Shinde, Dinesh; Rajamohanan, Pattuparambil R.; Nandi, Shyamapada; Vaidhyanathan, Ramanathan; Chikkali, Samir H.; The Journal of organic chemistry 82 (2017) 4342–4351; doi:10.1021/acs.joc.7b00352

data_4032461
_publ_section_title
;
 Secondary Interactions Arrest the Hemiaminal Intermediate To Invert the
 Modus Operandi of Schiff Base Reaction: A Route to Benzoxazinones.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4342
_journal_page_last               4351
_journal_paper_doi               10.1021/acs.joc.7b00352
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C15 H8 F5 N O2'
_chemical_formula_sum            'C15 H8 F5 N O2'
_chemical_formula_weight         329.22
_chemical_name_common            Benzoxazinone
_chemical_name_systematic
; 
 'Pentafluoro benzoxazinone'
;
_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                 95.854(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.971(3)
_cell_length_b                   9.801(2)
_cell_length_c                   24.597(5)
_cell_measurement_reflns_used    4833
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.012
_cell_measurement_theta_min      3.613
_cell_volume                     2631.0(10)
_computing_cell_refinement       'SHELXTL Suite'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Diamond 3.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'fine-focus sealed tube'
_diffrn_measurement_method       APEXII
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23991
_diffrn_reflns_theta_full        69.01
_diffrn_reflns_theta_max         69.01
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  0.755
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,2008
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flaky
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.066
_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     417
_refine_ls_number_reflns         4833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0802
_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^)+(0.0474P)^2^+5.6948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1936
_reflns_number_gt                3030
_reflns_number_total             4833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00352_si_003.cif
_cod_data_source_block           test_a
_cod_original_cell_volume        2631.1(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4032461