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_1576057
_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_formula_moiety         'C17 H17 F2 N3 O3'
_chemical_formula_sum            'C17 H17 F2 N3 O3'
_chemical_formula_weight         349.33
_chemical_name_systematic
1-(1,1-difluoro-2-(3,4,5-trimethoxyphenyl)ethyl)-1H-benzo[d][1,2,3]triazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-01-03 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.246(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.662(5)
_cell_length_b                   5.521(2)
_cell_length_c                   21.611(7)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.1716
_cell_measurement_theta_min      2.5671
_cell_volume                     1617.1(10)
_computing_cell_refinement       ' SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       ' Apex4 v2022.1-1 (Bruker, 2022) '
_computing_data_reduction        ' SAINT V8.40B (Bruker, 2020)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015a, 2018), 
SHELXLE Rev1428 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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 0.997
_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  0.0395
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            33368
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.194
_diffrn_reflns_theta_min         3.006
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D. (2015). J. Appl. Cryst. 48, 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.668
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.258
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         6182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.4244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4691
_reflns_number_total             6182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04074d2.cif
_cod_data_source_block           X_RCL_MAEK_5482_0m
_cod_depositor_comments
'Adding full bibliography for 1576054--1576058.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1576057
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              41114