In(OTf)3-catalyzed N-α phosphonylation of N,O-acetals with triethyl phosphite
Sun, Jian-Ting; Li, Xin; Yang, Tian-Yu; Lv, Min; Chen, Ling-Yan; Wei, Bang-Guo; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01196D

data_7158804
_publ_section_title
;
 In(OTf)3-catalyzed N-\a phosphonylation of N,O-acetals with triethyl
 phosphite
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01196D
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H24 N O4 P'
_chemical_formula_weight         313.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-05-29 deposited with the CCDC.	2022-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2351(3)
_cell_length_b                   8.1643(2)
_cell_length_c                   20.5765(5)
_cell_measurement_reflns_used    9610
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.930
_cell_measurement_theta_min      4.738
_cell_volume                     1702.00(8)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26255
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.627
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 2587 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.20(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6651
_refine_ls_number_restraints     83
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0887P)^2^+0.5003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                6114
_reflns_number_total             6651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01196d2.cif
_cod_data_source_block           mo_dd21111_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7158804
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
_shelx_res_checksum              42143