Frustrated Lewis pair meditated selective single fluoride substitution in trifluoromethyl groups.
Mandal, Dipendu; Gupta, Richa; Jaiswal, Amit K.; Young, Rowan D.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b12167

data_4134007
_publ_section_title
;
 Frustrated Lewis pair meditated selective single fluoride substitution in
 trifluoromethyl groups.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12167
_journal_year                    2020
_chemical_formula_moiety         'C2 F6 N O4 S2, C H2 Cl2, C37 H28 F2 N'
_chemical_formula_sum            'C40 H30 Cl2 F8 N2 O4 S2'
_chemical_formula_weight         889.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.643(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8900(5)
_cell_length_b                   16.2559(7)
_cell_length_c                   20.0266(8)
_cell_measurement_reflns_used    8519
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.67
_cell_measurement_theta_min      2.70
_cell_volume                     3866.7(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.97
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1159
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            69681
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.680
_diffrn_reflns_theta_min         2.321
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1872 before and 0.0808 after correction. The Ratio of minimum to maximum transmission is 0.9509. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       block
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         9933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+5.2161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1741
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5874
_reflns_number_total             9933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12167_si_003.cif
_cod_data_source_block           mo_ry_dm_3_230_0m
_cod_database_code               4134007
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.940
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F7B(0.5) F8A(0.5) O4B(0.25) F6B(0.5) C39B(0.5) F8B(0.5) C39A(0.5)
 F6A(0.5) F7A(0.5) O4A(0.75)
3.a Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B)
3.b Aromatic/amide H refined with riding coordinates:
 C37(H37), C36(H36), C5(H5), C16(H16), C10(H10), C33(H33), C18(H18), C12(H12),
 C13(H13), C31(H31), C7(H7), C27(H27), C21(H21), C29(H29), C6(H6), C22(H22),
 C4(H4), C30(H30), C9(H9), C25(H25), C23(H23), C24(H24), C34(H34), C35(H35),
 C28(H28)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              99683
_shelx_hkl_checksum              45433
_olex2_submission_special_instructions 'No special instructions were received'