Anion Ligand Promoted Selective C-F Bond Reductive Elimination Enables C(sp2)-H Fluorination
Mao, Yang-Jie; Luo, Gen; Hao, Hong-Yan; Xu, Zhen Yuan; Lou, Shao-Jie; Xu, Dan-Qian; Chemical Communications  (2019) –; doi:10.1039/C9CC07726J

data_7124450
_publ_section_title
;
 Anion Ligand Promoted Selective C-F Bond Reductive Elimination Enables
 C(sp2)-H Fluorination
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07726J
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H28 F N O2'
_chemical_formula_sum            'C24 H28 F N O2'
_chemical_formula_weight         381.47
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-23 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                73.1920(10)
_cell_angle_beta                 85.0490(10)
_cell_angle_gamma                75.3100(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3870(2)
_cell_length_b                   9.3722(2)
_cell_length_c                   15.5339(4)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.90
_cell_measurement_theta_min      5.18
_cell_volume                     995.76(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.97
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18763
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.900
_diffrn_reflns_theta_min         5.176
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1229 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.8660. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 3360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     521
_refine_ls_number_reflns         7233
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+0.1523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                7113
_reflns_number_total             7233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07726j2.cif
_cod_data_source_block           1905055737_0m
_cod_database_code               7124450
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N1A(H1AA,H1AB)
2.b Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C15(H15), C4A(H4A), C5A(H5A), C10A(H10A), C15A(H15A)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C16(H16A,H16B), C17(H17A,
 H17B), C1A(H1AC,H1AD), C2A(H2AB,H2AC), C6A(H6AA,H6AB), C7A(H7AA,H7AB),
 C16A(H16C,H16D), C17A(H17C,H17D)
2.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C20(H20), C21(H21), C24(H24), C11A(H11A),
 C12A(H12A), C14A(H14A), C20A(H20A), C21A(H21A), C24A(H24A)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              15561
_olex2_submission_special_instructions 'No special instructions were received'