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_7249050
_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 H50 F5 N1 Si1'
_chemical_formula_sum            'C35 H50 F5 N Si'
_chemical_formula_weight         607.86
_chemical_name_common
'Butan-1-aminium, N,N,N-tributyl, (TB-5-11)-difluorodiphenyl[(4-trifluoromethyl)phenyl]silicate(1-)'
_chemical_name_systematic
'Tetrabutylammonium difluorodiphenyl[(4-trifluoromethyl)phenyl]silicate'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.7602(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6166(3)
_cell_length_b                   16.7413(5)
_cell_length_c                   20.8563(6)
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    180
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.32
_cell_volume                     3357.45(17)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex4'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_unetI/netI     0.048
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            94800
_diffrn_reflns_theta_full        27.102
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.953
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.56
_refine_ls_extinction_coef       170(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         7320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.0004185
_refine_ls_shift/su_mean         0.0000486
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 3.41P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1229
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1194
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                6034
_reflns_number_total             7413
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.43
_oxford_diffrn_Wilson_scale      152.89
_oxford_refine_ls_scale          0.11980(4)
_cod_data_source_file            d4ra04332d2.cif
_cod_data_source_block           I_CCDC1
_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/n 1 '
_cod_original_formula_sum        'C35 H50 F5 N1 Si1'
_cod_database_code               7249050
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_r_factor_ref          0.0599
_reflns_number_all               7407