“On-water” defluorophosphorylation of trifluoromethylated enones with phosphine oxides
Chu, Xue-Qiang; Sun, Li-Wen; Ma, Cheng; Chen, Jia-Wei; Chen, Yu-Lan; Ni, Shao-Fei; Zhu, Ming-Quan; Zhou, Jie; Ma, Mengtao; Shen, Zhi-Liang; Green Chemistry 25 (2023) 6489–6497; doi:10.1039/D3GC01565C

data_7247093
_publ_section_title
;
 &#x201C;On-water&#x201D; defluorophosphorylation of trifluoromethylated
 enones with phosphine oxides
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              6489
_journal_page_last               6497
_journal_paper_doi               10.1039/D3GC01565C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C36 H26 F2 N3 O4 P'
_chemical_formula_sum            'C36 H26 F2 N3 O4 P'
_chemical_formula_weight         633.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-17
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.198(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6060(3)
_cell_length_b                   16.1758(4)
_cell_length_c                   14.0833(3)
_cell_measurement_reflns_used    6919
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.0360
_cell_measurement_theta_min      4.1490
_cell_volume                     3067.89(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     12.00  69.00   1.00    1.00    --   40.92  77.00 -90.00   57
  2  \w    111.00 177.00   1.00    1.58    --  108.20  45.00 -90.00   66
  3  \w    107.00 133.00   1.00    1.58    --  108.20 101.00 101.00   26
  4  \w     47.00 135.00   1.00    1.58    --  108.20 -61.00  90.00   88
  5  \w     68.00 100.00   1.00    1.58    --  108.20 -94.00  60.00   32
  6  \w     36.00 121.00   1.00    1.58    --  108.20-125.00   0.00   85
  7  \w     53.00  79.00   1.00    1.00    --   40.92-125.00  60.00   26
  8  \w     26.00  52.00   1.00    1.58    --  108.20 -94.00  60.00   26
  9  \w     23.00  95.00   1.00    1.00    --   40.92-125.00-150.00   72
 10  \w     70.00 107.00   1.00    1.58    --  108.20 -94.00-180.00   37
 11  \w     36.00 110.00   1.00    1.58    --  108.20 -45.00-180.00   74
 12  \w   -112.00 -14.00   1.00    1.00    --  -40.92 -57.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0730273000
_diffrn_orient_matrix_UB_12      0.0595513000
_diffrn_orient_matrix_UB_13      -0.0592911000
_diffrn_orient_matrix_UB_21      0.0787629000
_diffrn_orient_matrix_UB_22      0.0690560000
_diffrn_orient_matrix_UB_23      0.0140519000
_diffrn_orient_matrix_UB_31      0.0394203000
_diffrn_orient_matrix_UB_32      -0.0275997000
_diffrn_orient_matrix_UB_33      -0.0921393000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12151
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.167
_diffrn_reflns_theta_min         4.187
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00099(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0545P)^2^+0.9764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5303
_reflns_number_total             6063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc01565c2.cif
_cod_data_source_block           862
_cod_depositor_comments
'Adding full bibliography for 7247092--7247093.cif.'
_cod_database_code               7247093
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34),
 C35(H35), C36(H36)
;
_shelx_res_checksum              76214
_shelx_hkl_checksum              81196
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.497