Copper/DTBP-Promoted Oxyselenation of Propargylic Amines with Diselenides and CO<sub>2</sub>: Synthesis of Selenyl 2-Oxazolidinones.
Chen, Jia-Min; Qi, Lin; Zhang, Linlin; Li, Li-Jun; Hou, Cong-Ying; Li, Wei; Wang, Li-Jing; The Journal of organic chemistry 85 (2020) 10924–10933; doi:10.1021/acs.joc.0c01519

data_4038690
_publ_section_title
;
 Copper/DTBP-Promoted Oxyselenation of Propargylic Amines with Diselenides
 and CO<sub>2</sub>: Synthesis of Selenyl 2-Oxazolidinones.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10924
_journal_page_last               10933
_journal_paper_doi               10.1021/acs.joc.0c01519
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C17 H15 N O2 Se'
_chemical_formula_weight         344.26
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_atom_sites_solution_hydrogens   geom
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_cell_angle_gamma                90
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_cell_length_b                   5.6852(9)
_cell_length_c                   29.015(4)
_cell_measurement_reflns_used    1515
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.17
_cell_measurement_theta_min      2.17
_cell_volume                     3096.1(8)
_computing_cell_refinement       'Bruker SAINT'
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_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_unetI/netI     0.1186
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
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_diffrn_reflns_number            18425
_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_max         26.389
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_diffrn_source                   'sealed tube'
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_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
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_exptl_crystal_description       sheets
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
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_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.837(16)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.1420
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_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0565
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_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2627
_reflns_number_total             5797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01519_si_001.cif
_cod_data_source_block           cjm190906
_cod_depositor_comments          'Adding full bibliography for 4038690.cif.'
_cod_database_code               4038690
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.655
_shelx_estimated_absorpt_t_max   0.931
_shelx_res_checksum              87846
_shelx_hkl_checksum              45787