Pd/C-Catalyzed Carbonylative Synthesis of α-Carbonyl-α'-Amide Sulfoxonium Ylides from Azides.
Yuan, Yang; Chen, Bo; Zhang, Youcan; Wu, Xiao-Feng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00273

data_4038138
_publ_section_title
;
 Pd/C-Catalyzed Carbonylative Synthesis of \a-Carbonyl-\a'-Amide
 Sulfoxonium Ylides from Azides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00273
_journal_year                    2020
_chemical_formula_sum            'C12 H15 N O4 S'
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_space_group_crystal_system      monoclinic
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_atom_sites_solution_hydrogens   mixed
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_cell_angle_beta                 117.6173(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_c                   16.5749(9)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.43
_cell_volume                     2554.1(2)
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_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
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_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            41588
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         1.469
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0504P)^2^+0.9869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5292
_reflns_number_total             6172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00273_si_002.cif
_cod_data_source_block           AX1838
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038138
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              33846
_shelx_hkl_checksum              4368