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_1576056
_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_sum            'C18 H17 Br F2 N2 O3'
_chemical_formula_weight         427.24
_chemical_melting_point          452
_chemical_name_systematic
3-bromo-7-(1,1-difluoro-2-(3,4,5-trimethoxyphenyl)ethyl)-7H-pyrrolo[2,3-b]pyridine
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2025/1
_audit_update_record
;
2025-10-01 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.449(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.4790(12)
_cell_length_b                   5.0337(2)
_cell_length_c                   13.4427(7)
_cell_measurement_reflns_used    8746
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.1527
_cell_measurement_theta_min      3.1029
_cell_volume                     1683.54(14)
_computing_cell_refinement       'SAINT V8.41 (Bruker, 2025)'
_computing_data_collection       'Apex6 v2024.9-1 (Bruker, 2025)'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2025)'
_computing_structure_refinement
;  
SHELXL-2025/1 (Sheldrick, 2015a, 2025), 
SHELXLE Rev1737 (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
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15420
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.219
_diffrn_reflns_theta_min         3.104
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    2.485
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.4815
_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            yellow
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes and ethyl acetate (2:3 hexanes:ethyl acetate)'
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.029(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5499
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0402
_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^)+0.5231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                4688
_reflns_number_total             5499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04074d2.cif
_cod_data_source_block           RMH3_611_0m
_cod_depositor_comments
'Adding full bibliography for 1576054--1576058.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1576056
_shelx_shelxl_version_number     2025/1
_shelx_estimated_absorpt_t_min   0.376
_shelx_estimated_absorpt_t_max   0.886
_shelx_res_checksum              82122