Synthetic Methodologies for Perfluoroaryl-Substituted (Diaryl)methylphosphonates, -Phosphinates via S<sub>N</sub>Ar Reaction.
Fujii, Kohei; Ito, Shigekazu; Mikami, Koichi; The Journal of organic chemistry 84 (2019) 12281–12291; doi:10.1021/acs.joc.9b01402

data_4033970
_publ_section_title
;
 Synthetic Methodologies for Perfluoroaryl-Substituted
 (Diaryl)methylphosphonates, -Phosphinates via S<sub>N</sub>Ar Reaction.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12281
_journal_page_last               12291
_journal_paper_doi               10.1021/acs.joc.9b01402
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_sum            'C37 H15 F16 O2 P'
_chemical_formula_weight         826.46
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 107.408(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.8387(14)
_cell_length_b                   8.7580(10)
_cell_length_c                   15.1578(18)
_cell_measurement_reflns_used    326
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      27.484
_cell_measurement_theta_min      3.200
_cell_volume                     1626.3(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      158(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  Raxis-Rapid
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15609
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.200
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_description       platelet
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7012
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0576
_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^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1901
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                4702
_reflns_number_total             7012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01402_si_002.cif
_cod_data_source_block           Fujii
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4033970
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.945
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              23032
_shelx_hkl_checksum              62765