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_4034828
_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         'C12 H12 Br N2 O4'
_chemical_formula_sum            'C12 H12 Br N2 O4'
_chemical_formula_weight         328.14
_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             2017-04-20
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.442(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3016(7)
_cell_length_b                   11.2744(10)
_cell_length_c                   16.0710(17)
_cell_measurement_reflns_used    922
_cell_measurement_temperature    293.07(12)
_cell_measurement_theta_max      27.6820
_cell_measurement_theta_min      3.8160
_cell_volume                     1291.9(2)
_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      293.07(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.8309
_diffrn_measured_fraction_theta_max 0.8293
_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    -18.00  17.00   1.00    6.21    --  -17.51 -99.00  60.00   35
  2  \w     35.00  63.00   1.00    6.21    --   19.93 178.00-150.00   28
  3  \w     -6.00  73.00   1.00    6.21    --   19.93  37.00  30.00   79
;
_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      -0.0308989000
_diffrn_orient_matrix_UB_12      -0.0014958000
_diffrn_orient_matrix_UB_13      -0.0449620000
_diffrn_orient_matrix_UB_21      0.0920557000
_diffrn_orient_matrix_UB_22      0.0138099000
_diffrn_orient_matrix_UB_23      -0.0046127000
_diffrn_orient_matrix_UB_31      0.0213436000
_diffrn_orient_matrix_UB_32      -0.0613905000
_diffrn_orient_matrix_UB_33      0.0000824000
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3541
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50146
_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    1.6870
_exptl_crystal_description       needle
_exptl_crystal_F_000             659.2321
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.5117
_refine_diff_density_min         -0.6318
_refine_diff_density_rms         0.1404
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             6.0034
_refine_ls_goodness_of_fit_ref   1.0607
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0607
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.0973
_refine_ls_shift/su_mean         0.0189
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                1711
_reflns_number_total             2186
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b00558_si_004.cif
_cod_data_source_block           R-204
_cod_database_code               4034828
_chemical_oxdiff_formula         C12H14N2O4
_reflns_odcompleteness_completeness 82.27
_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:
 C15(H15a,H15b), C19(H19a,H19b), C18(H18a,H18b), C16(H16a,H16b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C5(H5)
;
_olex2_date_sample_data_collection 2017-04-20
_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 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.769