Diastereoselective Bromocyclization of O-Allyl-N-tosyl-hydroxylamines
Boris Egart; Dieter Lentz; Constantin Czekelius; Journal of Organic Chemistry 78 (2013) 2490–2499; doi:10.1021/jo3026725

data_4028039
_publ_section_title
;
 Diastereoselective Bromocyclization of O-Allyl-N-tosyl-hydroxylamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2490
_journal_page_last               2499
_journal_paper_doi               10.1021/jo3026725
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C16 H16 Br N O3 S'
_chemical_formula_weight         382.27
_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'
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_cell_angle_alpha                90.00
_cell_angle_beta                 94.162(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.412(5)
_cell_length_b                   11.143(8)
_cell_length_c                   18.737(12)
_cell_measurement_reflns_used    949
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.85
_cell_volume                     1543.4(18)
_computing_cell_refinement       'SAINT (BRUKER-AXS)'
_computing_data_collection       'SMART (BRUKER-AXS)'
_computing_data_reduction        'SAINT (BRUKER-AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'BRUKER-AXS SMART CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13797
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    2.810
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       platelett
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         13797
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_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0445P)^2^+1.9489P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1115
_reflns_number_gt                11493
_reflns_number_total             13797
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo3026725_si_002.cif
_cod_data_source_block           be452_1a
_cod_original_cell_volume        1543.3(18)
_cod_database_code               4028039