Photocatalyst-free, visible-light-induced regio- and stereoselective synthesis of phosphorylated enamines from <i>N</i>-allenamides <i>via</i> [1,3]-sulfonyl shift at room temperature.
Guo, Jia-Dong; Korsaye, Feven-Alemu; Schutz, Dorian; Ciofini, Ilaria; Miesch, Laurence; Chemical science 15 (2024) 17962–17970; doi:10.1039/d4sc05190d

data_1572748
_publ_section_title
;
 Photocatalyst-free, visible-light-induced regio- and stereoselective
 synthesis of phosphorylated enamines from <i>N</i>-allenamides <i>via</i>
 [1,3]-sulfonyl shift at room temperature.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              17962
_journal_page_last               17970
_journal_paper_doi               10.1039/d4sc05190d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C18 H18 F3 N O2 S'
_chemical_formula_sum            'C18 H18 F3 N O2 S'
_chemical_formula_weight         369.39
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-13 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.821(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.628(2)
_cell_length_b                   7.0992(10)
_cell_length_c                   13.6449(16)
_cell_measurement_reflns_used    1462
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.77
_cell_measurement_theta_min      2.99
_cell_volume                     1705.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19385
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.962
_diffrn_reflns_theta_min         1.157
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.856
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0443
_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^)+(0.1000P)^2^+0.2495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1459
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2773
_reflns_number_total             4081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05190d2.cif
_cod_data_source_block           elmjdg230207
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1572747--1572749.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572748
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              11601
_shelx_hkl_checksum              3701