Approach to Vicinalt-Boc-amino Dibromides via Catalytic Aminobromination of Nitrostyrenes without Using Chromatography and Recrystallization
Hao Sun; Jianlin Han; Padmanabha V. Kattamuri; Yi Pan; Guigen Li; Journal of Organic Chemistry 78 (2013) 1171–1175; doi:10.1021/jo302727v

data_4027933
_publ_section_title
;
 Approach to Vicinalt-Boc-amino Dibromides via Catalytic Aminobromination
 of Nitrostyrenes without Using Chromatography and Recrystallization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1171
_journal_page_last               1175
_journal_paper_doi               10.1021/jo302727v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C13 H16 Br2 N2 O4'
_chemical_formula_weight         424.10
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0202(10)
_cell_length_b                   9.5695(15)
_cell_length_c                   28.790(5)
_cell_measurement_reflns_used    2903
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.61
_cell_measurement_theta_min      2.24
_cell_volume                     1658.6(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0916
_diffrn_reflns_av_sigmaI/netI    0.0886
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10467
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    4.903
_exptl_absorpt_correction_T_max  0.6399
_exptl_absorpt_correction_T_min  0.3209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.169(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.749
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.749
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0682P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                2656
_reflns_number_total             3988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302727v_si_002.cif
_cod_data_source_block           lgc1
_cod_original_formula_sum        'C2.60 H3.20 Br0.40 N0.40 O0.80'
_cod_database_code               4027933