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_1572747
_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         'C30 H26 Br F3 N O3 P S'
_chemical_formula_sum            'C30 H26 Br F3 N O3 P S'
_chemical_formula_weight         648.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                112.2560(10)
_cell_angle_beta                 111.385(2)
_cell_angle_gamma                90.4840(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2345(4)
_cell_length_b                   12.0047(4)
_cell_length_c                   13.9944(6)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.93
_cell_measurement_theta_min      2.16
_cell_volume                     1460.15(10)
_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-2019/3(Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       '\f and \w shuterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            79769
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.122
_diffrn_reflns_theta_min         1.945
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_exptl_absorpt_coefficient_mu    1.585
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.611
_refine_diff_density_min         -1.708
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         8606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+1.5957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7140
_reflns_number_total             8606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05190d2.cif
_cod_data_source_block           elmjd230705
_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_database_code               1572747
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.742
_shelx_estimated_absorpt_t_max   0.833
_shelx_res_checksum              52685
_shelx_hkl_checksum              12927