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_4034829
_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         'C13 H17 N O2 Se'
_chemical_formula_sum            'C13 H17 N O2 Se'
_chemical_formula_weight         298.24
_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             2017-06-07
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.073(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6221(12)
_cell_length_b                   24.039(3)
_cell_length_c                   14.983(2)
_cell_measurement_reflns_used    1819
_cell_measurement_temperature    296.2(2)
_cell_measurement_theta_max      24.0950
_cell_measurement_theta_min      3.6860
_cell_volume                     2738.4(7)
_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      296.2(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9939
_diffrn_measured_fraction_theta_max 0.9931
_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    -44.00  23.00   1.00    4.92    --   19.93 -57.00   0.00   67
  2  \w     39.00  70.00   1.00    4.92    --   19.93 178.00-150.00   31
  3  \w    -48.00  57.00   1.00    4.92    --   19.93 -19.00-150.00  105
;
_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      -0.0861757000
_diffrn_orient_matrix_UB_12      -0.0049821000
_diffrn_orient_matrix_UB_13      -0.0196791000
_diffrn_orient_matrix_UB_21      -0.0324260000
_diffrn_orient_matrix_UB_22      0.0223269000
_diffrn_orient_matrix_UB_23      0.0249498000
_diffrn_orient_matrix_UB_31      0.0157634000
_diffrn_orient_matrix_UB_32      0.0185709000
_diffrn_orient_matrix_UB_33      -0.0352778000
_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  0.0363
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10934
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56857
_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    1.4468
_exptl_crystal_description       block
_exptl_crystal_F_000             1215.8596
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.5726
_refine_diff_density_min         -0.9247
_refine_diff_density_rms         0.1493
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             6.0358
_refine_ls_goodness_of_fit_ref   1.0366
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0366
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.0311
_refine_ls_shift/su_mean         0.0074
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0389P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3529
_reflns_number_total             5576
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b00558_si_002.cif
_cod_data_source_block           R-287
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C26 H34 N2 O4 Se2'
_cod_original_formula_weight         596.49
_cod_original_formula_moiety         '2(C13 H17 N O2 Se)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2738.3(7)
_cod_database_code               4034829
_chemical_oxdiff_formula         C17H17NOSe
_reflns_odcompleteness_completeness 99.20
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C29(H29a,H29b), C12(H12a,H12b), C10(H10a,H10b), C27(H27a,H27b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C20(H20), C23(H23), C3(H3), C5(H5), C21(H21), C4(H4), C22(H22)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C28(H28a,H28b,H28c), C30(H30a,H30b,H30c), C17(H17a,H17b,
 H17c), C13(H13a,H13b,H13c), C34(H34a,H34b,H34c)
;
_olex2_date_sample_data_collection 2017-06-07
_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 1.706
_oxdiff_exptl_absorpt_empirical_full_min 0.807