Thermal rearrangement of 2-bromooxazolines to 2-bromoisocyanates.
Foltz, Carole; Bellemin-Laponnaz, Stéphane; Enders, Markus; Wadepohl, Hubert; Gade, Lutz H.; Organic letters 10 (2008) 305–308; doi:10.1021/ol7027509

data_1504501
_publ_section_title
;
 Thermal rearrangement of 2-bromooxazolines to 2-bromoisocyanates.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              305
_journal_page_last               308
_journal_paper_doi               10.1021/ol7027509
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H8 Br N O'
_chemical_formula_weight         238.08
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_cf9
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8071(10)
_cell_length_b                   8.0417(10)
_cell_length_c                   14.2852(18)
_cell_measurement_temperature    100(2)
_cell_volume                     896.9(2)
_computing_cell_refinement       'SAINT (Bruker AXS, 1997-2006)'
_computing_data_collection       'SMART (Bruker AXS, 1997-2003)'
_computing_data_reduction        'SAINT (Bruker AXS, 1997-2006)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2005)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector (Bruker AXS Smart 1000)'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7904
_diffrn_reflns_theta_full        32.02
_diffrn_reflns_theta_max         32.02
_diffrn_reflns_theta_min         2.85
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.537
_exptl_absorpt_correction_T_max  0.5494
_exptl_absorpt_correction_T_min  0.3967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004-2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                2660
_reflns_number_total             3010
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7027509-file001.cif
_cod_data_source_block
(1R,2R)-2-bromo-1-isocyanato-2,3-dihydro-1H-indene
_cod_database_code               1504501
_audit_block_refno               231