Diselenide-enabled photocatalytic hydroazolation of <i>gem</i>-difluoroalkenes.
Abd El-Gaber, Mohammed K; Herrick, Ryan M.; Sudhakar, Pranaya; Rana, Ashutosh; Roach, Brent A.; Dick, Jeffrey E.; Altman, Ryan A.; Chemical science 16 (2025) 22701–22710; doi:10.1039/d5sc04074d

data_1576054
_publ_section_title
;
 Diselenide-enabled photocatalytic hydroazolation of
 <i>gem</i>-difluoroalkenes.
;
_journal_issue                   47
_journal_name_full               'Chemical science'
_journal_page_first              22701
_journal_page_last               22710
_journal_paper_doi               10.1039/d5sc04074d
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H40 F2 N2 O5, 0.25(C6 H14)'
_chemical_formula_sum            'C43.5 H43.5 F2 N2 O5'
_chemical_formula_weight         712.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-01-03 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.925(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   43.884(9)
_cell_length_b                   5.5853(12)
_cell_length_c                   15.050(2)
_cell_measurement_reflns_used    7389
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.1913
_cell_measurement_theta_min      2.9401
_cell_volume                     3684.0(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'Apex5 v2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_refinement
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1613 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type
'PhotonIII_C14 charge-integrating and photon counting pixel array'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'HELIOS multilayer Montel optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18691
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.214
_diffrn_reflns_theta_min         2.016
_diffrn_source                   'I-mu-S 3.0 microsource X-ray tube'
_diffrn_source_current           '1.1 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             1506
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1376 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.23(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         7038
_refine_ls_number_restraints     292
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0848
_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^)+(0.0549P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.778
_reflns_number_gt                4584
_reflns_number_total             7038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04074d2.cif
_cod_data_source_block           RMH3_258_0m
_cod_depositor_comments
'Adding full bibliography for 1576054--1576058.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C43.50 H43.50 F2 N2 O5'
_cod_database_code               1576054
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.732
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              74933