Efficient Synthesis of Cyclic P-Stereogenic Phosphinamides from Acyclic Chiral Precursors via Radical Oxidative Intramolecular Aryl C–H Phosphinamidation
Chen, Yuan-Hui; Xu, Xu-Long; Han, Fu-She; Chem. Commun.  (2017) –; doi:10.1039/C7CC02263H

data_7120073
_publ_section_title
;
 Efficient Synthesis of Cyclic P-Stereogenic Phosphinamides from Acyclic
 Chiral Precursors via Radical Oxidative Intramolecular Aryl C--H
 Phosphinamidation
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02263H
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H19 F5 N1 P1 S1'
_chemical_formula_sum            'C27 H19 F5 N P S'
_chemical_formula_weight         515.46
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-10-09 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.676(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.8922(4)
_cell_length_b                   14.6238(3)
_cell_length_c                   10.6886(2)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      4.09
_cell_volume                     2501.35(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.997
_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  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12514
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         4.09
_exptl_absorpt_coefficient_mu    2.231
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0571P)^2^+1.5692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                3978
_reflns_number_total             4366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc02263h2.cif
_cod_data_source_block           hanfs01_0m_sq_d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      C2
_cod_original_formula_sum        'C27 H19 F5 N1 P1 S1'
_cod_database_code               7120073