Isoselenazolones as Catalysts for the Activation of Bromine: Bromolactonization of Alkenoic Acids and Oxidation of Alcohols
Shah Jaimin Balkrishna; Ch Durga Prasad; Piyush Panini; Michael R. Detty; Deepak Chopra; Sangit Kumar; Journal of Organic Chemistry 77 (2012) 9541–9552; doi:10.1021/jo301486c

data_4027630
_publ_section_title
;
 Isoselenazolones as Catalysts for the Activation of Bromine:
 Bromolactonization of Alkenoic Acids and Oxidation of Alcohols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9541
_journal_page_last               9552
_journal_paper_doi               10.1021/jo301486c
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C15 H11 F2 N O Se'
_chemical_formula_weight         338.21
_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   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            8
_cell_length_a                   10.4087(4)
_cell_length_b                   11.7630(3)
_cell_length_c                   22.0902(7)
_cell_measurement_temperature    292(2)
_cell_volume                     2704.67(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12829
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    2.794
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             1344
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0112P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0563
_reflns_number_gt                4849
_reflns_number_total             5983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301486c_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4027630