Regioselective C(sp<sup>3</sup>)-H fluorination of ketones: from methyl to the monofluoromethyl group.
Wu, Qiu-Zi; Mao, Yang-Jie; Zhou, Kun; Hao, Hong-Yan; Chen, Lei; Wang, Shuang; Xu, Zhen-Yuan; Lou, Shao-Jie; Xu, Dan-Qian; Chemical communications (Cambridge, England) 57 (2021) 765–768; doi:10.1039/d0cc07093a

data_7127603
_publ_section_title
;
 Regioselective C(sp<sup>3</sup>)-H fluorination of ketones: from methyl
 to the monofluoromethyl group.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              765
_journal_page_last               768
_journal_paper_doi               10.1039/d0cc07093a
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_sum            'C25 H25 F7 N2 O4'
_chemical_formula_weight         550.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc25tx20
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-08-03 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7568(3)
_cell_length_b                   16.7646(6)
_cell_length_c                   17.6194(6)
_cell_measurement_reflns_used    4535
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.330
_cell_measurement_theta_min      5.195
_cell_volume                     2586.60(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_max 0.996
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13082
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_min         2.430
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0590P)^2^+0.5829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3666
_reflns_number_total             5052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07093a2.cif
_cod_data_source_block           mo_dd19398_0m
_cod_depositor_comments          'Adding full bibliography for 7127603.cif.'
_cod_database_code               7127603
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2013-4
_shelx_res_checksum              15118