Visible Light-Induced Co- or Cu-Catalyzed Selenosulfonylation of Alkynes: Synthesis of β-(Seleno)vinyl Sulfones.
Zhang, Rong; Xu, Pei; Wang, Shun-Yi; Ji, Shun-Jun; The Journal of organic chemistry 84 (2019) 12324–12333; doi:10.1021/acs.joc.9b01626

data_4033963
_publ_section_title
;
 Visible Light-Induced Co- or Cu-Catalyzed Selenosulfonylation of Alkynes:
 Synthesis of \b-(Seleno)vinyl Sulfones.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12324
_journal_page_last               12333
_journal_paper_doi               10.1021/acs.joc.9b01626
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C25 H25 N O3 S Se'
_chemical_formula_sum            'C25 H25 N O3 S Se'
_chemical_formula_weight         498.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 92.701(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8819(12)
_cell_length_b                   11.2677(13)
_cell_length_c                   19.934(2)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.3950
_cell_measurement_theta_min      2.6036
_cell_volume                     2441.5(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0741
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            46916
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.730
_exptl_absorpt_coefficient_mu    1.649
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.252
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4449
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0737P)^2^+4.6169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1773
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3224
_reflns_number_total             4449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01626_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        2441.4(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4033963
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.734
_shelx_estimated_absorpt_t_max   0.879
_shelx_res_checksum              1620
_shelx_hkl_checksum              46108