Metal Free C-C Coupling of an Allenyl Sulfone with Picolyl Amides to Access Vinyl Sulfones via Pyridine-Initiated In-Situ Generation of Sulfinate Anion.
Omer, Humair M.; Liu, Peng; Brummond, Kay M.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00788

data_4038451
_publ_section_title
;
 Metal Free C-C Coupling of an Allenyl Sulfone with Picolyl Amides to
 Access Vinyl Sulfones via Pyridine-Initiated In-Situ Generation of
 Sulfinate Anion.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00788
_journal_year                    2020
_chemical_formula_moiety         'C17 H18 O4 S2,C17 H18 O4 S2'
_chemical_formula_sum            'C34 H36 O8 S4'
_chemical_formula_weight         700.86
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 107.388(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9187(5)
_cell_length_b                   11.3060(4)
_cell_length_c                   19.6808(6)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      3.91
_cell_volume                     3380.22(19)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35966
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.418
_diffrn_reflns_theta_min         2.909
_diffrn_source                   'Bruker X8 Prospector Ultra Cu IMuS'
_exptl_absorpt_coefficient_mu    3.000
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.980
_refine_diff_density_min         -1.704
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.588
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         6179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.588
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0981
_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^)+(0.0680P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3149
_refine_ls_wR_factor_ref         0.3192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5687
_reflns_number_total             6179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00788_si_003.cif
_cod_data_source_block           Humair2071_minor_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038451
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.678
_shelx_estimated_absorpt_t_max   0.711
_shelx_res_checksum              21555
_shelx_hkl_checksum              82553