Selenium Dioxide As an Alternative Reagent for the Direct α-Selenoamidation of Aryl Methyl Ketones.
Shangpliang, O. Risuklang; Kshiar, Baskhemlang; Wanniang, Kmendashisha; Marpna, Ibakyntiew D.; Lipon, Tyrchain Mitre; Laloo, Badaker M.; Myrboh, Bekington; The Journal of organic chemistry 83 (2018) 5829–5835; doi:10.1021/acs.joc.8b00558

data_4034825
_publ_section_title
;
 Selenium Dioxide As an Alternative Reagent for the Direct
 \a-Selenoamidation of Aryl Methyl Ketones.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5829
_journal_page_last               5835
_journal_paper_doi               10.1021/acs.joc.8b00558
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H17 Br N O'
_chemical_formula_sum            'C17 H17 Br N O'
_chemical_formula_weight         331.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-05
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.536(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6786(8)
_cell_length_b                   10.5551(6)
_cell_length_c                   12.611(1)
_cell_measurement_reflns_used    1683
_cell_measurement_temperature    293.95(10)
_cell_measurement_theta_max      25.5000
_cell_measurement_theta_min      3.8370
_cell_volume                     1473.90(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9941
_diffrn_measured_fraction_theta_max 0.9930
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -25.00  16.00   1.00    5.21    --  -17.59 -99.00 150.00   41
  2  \w    -38.00  32.00   1.00    5.21    --   19.93 -57.00 -30.00   70
  3  \w     -3.00  87.00   1.00    5.21    --   19.93  37.00 150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0590045000
_diffrn_orient_matrix_UB_12      -0.0086100000
_diffrn_orient_matrix_UB_13      0.0032157000
_diffrn_orient_matrix_UB_21      0.0093000000
_diffrn_orient_matrix_UB_22      -0.0664898000
_diffrn_orient_matrix_UB_23      0.0036150000
_diffrn_orient_matrix_UB_31      0.0231618000
_diffrn_orient_matrix_UB_32      0.0045893000
_diffrn_orient_matrix_UB_33      0.0591436000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5797
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.47
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4926
_exptl_crystal_description       block
_exptl_crystal_F_000             675.1454
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.5708
_refine_diff_density_min         -0.5889
_refine_diff_density_rms         0.0918
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             5.8794
_refine_ls_goodness_of_fit_ref   1.0465
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0465
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.0066
_refine_ls_shift/su_mean         0.0015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.2541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2279
_reflns_number_total             2992
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b00558_si_003.cif
_cod_data_source_block           L4V
_cod_database_code               4034825
_chemical_oxdiff_formula         C20H18N4O4Br2V2
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b), C16(H16a,H16b), C19(H19a,H19b), C17(H17a,H17b), C18(H18a,H18b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C10(H10), C9(H9), C5(H5), C7(H7), C6(H6)
;
_olex2_date_sample_data_collection 2017-06-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.868