Copper-Catalyzed Three Component Regio- and Stereospecific Selenosulfonation of Alkynes: Synthesis of (E)-β-Selenovinyl Sulfones.
Liu, Yang; Zheng, Guangfan; Zhang, Qian; Li, Yan; Zhang, Qian; The Journal of organic chemistry 82 (2017) 2269–2275; doi:10.1021/acs.joc.6b03049

data_4032280
_publ_section_title
;
 Copper-Catalyzed Three Component Regio- and Stereospecific
 Selenosulfonation of Alkynes: Synthesis of (E)-\b-Selenovinyl Sulfones.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2269
_journal_page_last               2275
_journal_paper_doi               10.1021/acs.joc.6b03049
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C22 H20 O2 S Se'
_chemical_formula_sum            'C22 H20 O2 S Se'
_chemical_formula_weight         427.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.14
_cell_angle_beta                 95.54
_cell_angle_gamma                95.45
_cell_formula_units_Z            2
_cell_length_a                   8.642
_cell_length_b                   11.567
_cell_length_c                   11.642
_cell_measurement_reflns_used    1339
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3561
_cell_measurement_theta_min      2.7900
_cell_volume                     1128.777
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Smart ApexII CCD'
_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  0.0719
_diffrn_reflns_av_sigmaI/netI    0.1242
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6820
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    1.767
_exptl_absorpt_correction_T_max  0.590
_exptl_absorpt_correction_T_min  0.531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.669
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.0938
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1719P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2778
_refine_ls_wR_factor_ref         0.3363
_reflns_number_gt                1987
_reflns_number_total             3958
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo6b03049_si_001.cif
_cod_data_source_block           ly
_cod_original_cell_volume        1128.8
_cod_database_code               4032280