Synthesis of 3-Alkylbenzoxazolones from N-Alkyl-N-arylhydroxylamines by Contiguous O-Trichloroacetylation, Trichloroacetoxy ortho-Shift, and Cyclization Sequence
Ram N. Ram; Vineet Kumar Soni; Journal of Organic Chemistry 78 (2013) 11935–11947; doi:10.1021/jo401985h

data_4028815
_publ_contact_author_address
; 
      Department of Chemistry 
      Indian Institute of Technology
      Hauz Khas, New Delhi 110016
      India
;
_publ_contact_author_email       rnram@chemistry.iitd.ac.in
_publ_contact_author_fax         +91-11-26582037
_publ_contact_author_name        'R.N. Ram and Vineet Kumar Soni'
_publ_contact_author_phone       +91-11-26591508
_publ_section_title
;
 Synthesis of 3-Alkylbenzoxazolones from N-Alkyl-N-arylhydroxylamines by
 Contiguous O-Trichloroacetylation, Trichloroacetoxy ortho-Shift, and
 Cyclization Sequence
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11935
_journal_page_last               11947
_journal_paper_doi               10.1021/jo401985h
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C14 H10 Br N O2'
_chemical_formula_sum            'C14 H10 Br N O2'
_chemical_formula_weight         304.13
_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           'SHELXTL-NT2000 ver.6.12'
_cell_angle_alpha                109.051(2)
_cell_angle_beta                 101.812(2)
_cell_angle_gamma                92.026(2)
_cell_formula_units_Z            2
_cell_length_a                   5.3310(8)
_cell_length_b                   10.0858(14)
_cell_length_c                   11.7987(17)
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.32
_cell_volume                     583.35(15)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5581
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    3.515
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       Block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0197
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+0.2491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0535
_reflns_number_gt                1965
_reflns_number_total             2058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401985h_si_005.cif
_cod_data_source_block           rjc2m
_cod_database_code               4028815