Pd-catalyzed highly regio-, diastereo-, and enantioselective allylic alkylation of alpha-fluorophosphonates
Ying Huang; Qing-Song Zhang; Ping Fang; Tie-Gen Chen; Jun Zhu; Xue-Long Hou; Chem.Commun. 50 (2014) 6751–; doi:10.1039/C4CC02158D

data_7113992
_publ_section_title
;
 Pd-catalyzed highly regio-, diastereo-, and enantioselective allylic
 alkylation of alpha-fluorophosphonates
;
_journal_name_full               Chem.Commun.
_journal_page_first              6751
_journal_paper_doi               10.1039/C4CC02158D
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H23 Br F N4 O7 P'
_chemical_formula_weight         573.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.205(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.4800(19)
_cell_length_b                   15.0402(13)
_cell_length_c                   15.6870(14)
_cell_measurement_reflns_used    4079
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.463
_cell_measurement_theta_min      5.215
_cell_volume                     5047.0(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9912
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.303
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6457
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2336
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
; 
 Flack x determined using 2407 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.162(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     722
_refine_ls_number_reflns         9731
_refine_ls_number_restraints     118
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0804P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                6327
_reflns_number_total             9731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc02158d2.cif
_cod_data_source_block           cd21452
_cod_database_code               7113992
_shelxl_version_number           2013-4
_shelx_res_checksum              55495
_shelx_hkl_checksum              28324