α-Fluoroamine synthesis <i>via</i> P(III)-mediated deoxygenative geminal fluorosulfonimidation of 1,2-diketones.
Son, Yeri; Hwang, Sunjoo; Bak, Sujin; Kim, Ha Eun; Choi, Jun-Ho; Chung, Won-Jin; Organic & biomolecular chemistry 20 (2022) 3263–3267; doi:10.1039/d2ob00498d

data_7158595
_publ_section_title
;
 \a-Fluoroamine synthesis <i>via</i> P(III)-mediated deoxygenative geminal
 fluorosulfonimidation of 1,2-diketones.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3263
_journal_page_last               3267
_journal_paper_doi               10.1039/d2ob00498d
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C28 H24 F N O5 S2'
_chemical_formula_sum            'C28 H24 F N O5 S2'
_chemical_formula_weight         537.60
_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     direct
_audit_creation_date             2021-09-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2021-09-18 deposited with the CCDC.	2022-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7215(2)
_cell_length_b                   18.6021(5)
_cell_length_c                   20.0805(5)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.776
_cell_measurement_theta_min      3.222
_cell_volume                     2510.75(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_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  0.0439
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31857
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.952
_diffrn_reflns_theta_min         3.809
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0742 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.8894.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.49(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.8221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4522
_reflns_number_total             4877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00498d2.cif
_cod_data_source_block           jwj05_0m
_cod_depositor_comments          'Adding full bibliography for 7158595.cif.'
_cod_database_code               7158595
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              90074
_olex2_submission_special_instructions 'No special instructions were received'