A practical photocatalytic strategy for radical (deuterio)difluoromethylation using imidazolium reagents.
Sun, Chao; Shen, Yinpu; Li, Heyin; Wang, Zhen; Li, Yifan; Huang, Mengjun; Zou, Zhenlei; Liu, Jing; Liu, Ao; Pan, Yi; Zhang, Weigang; Wang, Yi; Chemical science 16 (2025) 16039–16046; doi:10.1039/d5sc02691a

data_1575337
_publ_section_title
;
 A practical photocatalytic strategy for radical
 (deuterio)difluoromethylation using imidazolium reagents.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              16039
_journal_page_last               16046
_journal_paper_doi               10.1039/d5sc02691a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C15 H12 D F2 N2 O2 S, C F3 O3 S'
_chemical_formula_sum            'C16 H12 D F5 N2 O5 S2'
_chemical_formula_weight         473.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2025-02-25 deposited with the CCDC.	2025-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1192(18)
_cell_length_b                   8.7748(11)
_cell_length_c                   13.7546(18)
_cell_measurement_reflns_used    7038
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      66.47
_cell_measurement_theta_min      4.23
_cell_volume                     1945.5(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10015
_diffrn_reflns_point_group_measured_fraction_full 0.803
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        66.479
_diffrn_reflns_theta_max         66.479
_diffrn_reflns_theta_min         5.489
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.237
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5075
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1498 before and 0.0906 after correction.
The Ratio of minimum to maximum transmission is 0.6741.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.101(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0591
_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^)+(0.1277P)^2^+0.2750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_full    0.603
_reflns_Friedel_fraction_max     0.603
_reflns_number_gt                2679
_reflns_number_total             2766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02691a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1575337--1575338.cif.'
_cod_database_code               1575337
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.782
_shelx_estimated_absorpt_t_min   0.697
_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. Restrained distances
 F2-C15 \\sim F1-C15
 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C15(D15)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              61195
_olex2_submission_special_instructions 'No special instructions were received'