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_4028812
_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_absolute_configuration rm
_chemical_formula_moiety         'C10 H8 Br N O2'
_chemical_formula_sum            'C10 H8 Br N O2'
_chemical_formula_weight         254.07
_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           'SHELXTL-NT2000 ver.6.12'
_cell_angle_alpha                90.00
_cell_angle_beta                 109.051(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.856(5)
_cell_length_b                   13.199(6)
_cell_length_c                   7.922(4)
_cell_measurement_reflns_used    5821
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.74
_cell_measurement_theta_min      2.25
_cell_volume                     974.1(8)
_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      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8564
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    4.190
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_description       Flake
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.897
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1025P)^2^+1.0476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.2038
_reflns_number_gt                1059
_reflns_number_total             1720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401985h_si_002.cif
_cod_data_source_block           vin7m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028812