Direct NF<sub>2</sub> functionalization of ketones: a mild strategy for accessing high-performance gem-difluoroamino compounds.
Wang, Yuehui; Wen, Lele; Ling, Lin; Xing, Chunhui; Lu, Long; Chemical communications (Cambridge, England) 62 (2026) 5429–5432; doi:10.1039/d6cc00009f

data_7135606
_publ_section_title
;
 Direct NF<sub>2</sub> functionalization of ketones: a mild strategy for
 accessing high-performance gem-difluoroamino compounds.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5429
_journal_page_last               5432
_journal_paper_doi               10.1039/d6cc00009f
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C10 H12 F8 N4'
_chemical_formula_sum            'C10 H12 F8 N4'
_chemical_formula_weight         340.24
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-20
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-12-25 deposited with the CCDC.	2026-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4094(4)
_cell_length_b                   7.8335(4)
_cell_length_c                   21.8556(11)
_cell_measurement_reflns_used    7948
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.631
_cell_measurement_theta_min      2.762
_cell_volume                     1268.53(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18161
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.917
_diffrn_reflns_theta_min         1.864
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1406 before and 0.0729 after correction.
The Ratio of minimum to maximum transmission is 0.8000.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.1575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                2746
_reflns_number_total             3928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00009f2.cif
_cod_data_source_block           mo_d8v25650_0m
_cod_database_code               7135606
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
;
_shelx_res_checksum              91263
_olex2_submission_special_instructions 'No special instructions were received'