Radical photochemical difluorosulfoximination of alkenes and propellanes
Baldon, Simone; Paut, Julien; Anselmi, Elsa; Dagousset, Guillaume; Tuccio, Béatrice; Pelosi, Giorgio; Cuadros, Sara; Magnier, Emmanuel; Dell’Amico, Luca; Chemical Science 16 (2025) 6957–6964; doi:10.1039/D5SC01068C

data_1574158
_publ_section_title
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 Radical photochemical difluorosulfoximination of alkenes and propellanes
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_journal_issue                   16
_journal_name_full               'Chemical Science'
_journal_page_first              6957
_journal_page_last               6964
_journal_paper_doi               10.1039/D5SC01068C
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H12 Br F2 N O S'
_chemical_formula_sum            'C12 H12 Br F2 N O S'
_chemical_formula_weight         336.20
_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   geom
_audit_creation_date             2024-06-20
_audit_creation_method
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Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
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_audit_update_record
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2024-06-20 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
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_cell_angle_alpha                92.018(3)
_cell_angle_beta                 92.253(3)
_cell_angle_gamma                106.884(3)
_cell_formula_units_Z            4
_cell_length_a                   9.5072(6)
_cell_length_b                   11.2492(7)
_cell_length_c                   13.1335(9)
_cell_measurement_reflns_used    9686
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.80
_cell_measurement_theta_min      3.37
_cell_volume                     1341.42(15)
_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)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Advance'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            59085
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.054
_diffrn_reflns_theta_min         3.372
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.764
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          .03
_exptl_crystal_size_mid          .02
_exptl_crystal_size_min          .02
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details
;
 Flack x determined using 4140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     674
_refine_ls_number_reflns         9857
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0590
_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^)+(0.1201P)^2^+0.9804P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1753
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                9250
_reflns_number_total             9857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01068c2.cif
_cod_data_source_block           cu_sc574_a
_cod_depositor_comments          'Adding full bibliography for 1574158.cif.'
_cod_database_code               1574158
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H) groups
2. Restrained distances
 C8A-C9A \\sim C8A-C2
 with sigma of 0.02
 C8A-C10A \\sim C8A-C1
 with sigma of 0.02
 C8A-C11A \\sim C8A-C3
 with sigma of 0.02
 C9A-C12A \\sim C2-C12A
 with sigma of 0.02
 C10A-C12A \\sim C1-C12A
 with sigma of 0.02
 C11A-C12A \\sim C3-C12A
 with sigma of 0.02
 C8B-C9B \\sim C8B-C5
 with sigma of 0.02
 C8B-C10B \\sim C8B-C4
 with sigma of 0.02
 C8B-C11B \\sim C8B-C6
 with sigma of 0.02
 C9B-C12B \\sim C5-C12B
 with sigma of 0.02
 C10B-C12B \\sim C4-C12B
 with sigma of 0.02
 C11B-C12B \\sim C6-C12B
 with sigma of 0.02
 C7A-C8A \\sim C7-C8A
 with sigma of 0.02
 C7A-F1A \\sim C7-F1
 with sigma of 0.02
 C7A-F2A \\sim C7-F2
 with sigma of 0.02
 C7A-S1A \\sim C7-S1A
 with sigma of 0.02
 C8A-F1A \\sim C8A-F1
 with sigma of 0.04
 C8A-F2A \\sim C8A-F2
 with sigma of 0.04
 F1A-F2A \\sim F1-F2
 with sigma of 0.04
 F1A-S1A \\sim F1-S1A
 with sigma of 0.04
 F2A-S1A \\sim F2-S1A
 with sigma of 0.04
3. Others
 Fixed Sof: C7A(0.5) C9A(0.5) H9AA(0.5) H9AB(0.5) C10A(0.5) H10A(0.5)
 H10B(0.5) C11A(0.5) H11A(0.5) H11B(0.5) F1A(0.5) F2A(0.5) C9B(0.5) H9BA(0.5)
 H9BB(0.5) C10B(0.5) H10C(0.5) H10D(0.5) C11B(0.5) H11C(0.5) H11D(0.5) C1(0.5)
 H1B(0.5) H1C(0.5) C2(0.5) H2B(0.5) H2C(0.5) C3(0.5) H3B(0.5) H3C(0.5) C4(0.5)
 H4C(0.5) H4D(0.5) C5(0.5) H5C(0.5) H5D(0.5) C6(0.5) H6A(0.5) H6B(0.5) F1(0.5)
 F2(0.5) C7(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C10A(H10A,H10B), C11A(H11A,H11B), C9B(H9BA,H9BB), C10B(H10C,
 H10D), C11B(H11C,H11D), C9C(H9CA,H9CB), C10C(H10E,H10F), C11C(H11E,H11F),
 C9D(H9DA,H9DB), C10D(H10G,H10H), C11D(H11G,H11H), C1(H1B,H1C), C2(H2B,H2C),
 C3(H3B,H3C), C4(H4C,H4D), C5(H5C,H5D), C6(H6A,H6B)
4.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C1B(H1BA), C2B(H2BA),
 C3B(H3BA), C4B(H4B), C5B(H5B), C1C(H1CA), C2C(H2CA), C3C(H3CA), C4C(H4CA),
 C5C(H5CA), C1D(H1D), C2D(H2D), C3D(H3D), C4D(H4DA), C5D(H5DA)
4.c Idealised tetrahedral OH refined as rotating group:
 N1A(H1AA), N1B(H1BB), N1C(H1CB), N1D(H1DA)
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_shelx_res_checksum              81446
_olex2_submission_special_instructions 'No special instructions were received'