Modified aryldifluorophenylsilicates with improved activity and selectivity in nucleophilic fluorination of secondary substrates
Trojan, Michal; Hroch, Adam; Gruden, Evelin; Cvačka, Josef; Čejka, Jan; Tavčar, Gašper; Rybáčková, Markéta; Kvíčala, Jaroslav; RSC Advances 14 (2024) 22326–22334; doi:10.1039/D4RA04332D

data_7249049
_publ_section_title
;
 Modified aryldifluorophenylsilicates with improved activity and
 selectivity in nucleophilic fluorination of secondary substrates
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              22326
_journal_page_last               22334
_journal_paper_doi               10.1039/D4RA04332D
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C35 H53.00 F2 N1 O1 Si1'
_chemical_formula_sum            'C35 H53 F2 N O Si'
_chemical_formula_weight         569.89
_chemical_name_common
'Butan-1-aminium, N,N,N-tributyl, (TB-5-11)-difluoro(4-methoxyphenyl)diphenylsilicate(1-)'
_chemical_name_systematic
'Tetrabutylammonium difluoro(4-methoxyphenyl)diphenylsilicate'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.4507(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6320(2)
_cell_length_b                   18.7983(4)
_cell_length_c                   19.1207(4)
_cell_measurement_reflns_used    9121
_cell_measurement_temperature    180
_cell_measurement_theta_max      74.53
_cell_measurement_theta_min      2.37
_cell_volume                     3380.67(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Apex4 (Bruker AXS, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex4'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_unetI/netI     0.068
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            67833
_diffrn_reflns_theta_full        68.241
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.336
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1239.987
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.0007401
_refine_ls_shift/su_mean         0.0000609
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 1.02P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1119
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1119
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                5558
_reflns_number_total             6188
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.28
_oxford_diffrn_Wilson_scale      53.12
_oxford_refine_ls_scale          0.14223(6)
_cod_data_source_file            d4ra04332d2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C35 H53.00 F2 N1 O1 Si1'
_cod_database_code               7249049
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_r_factor_ref          0.0425
_reflns_number_all               6188