Dehalogenation hydrolysis of CF<sub>2</sub>Br<sub>2</sub> enables four-component aminocarbonylation <i>via</i> photocatalytic radical-polar crossover.
Huang, Yinghong; Zheng, Renhua; Cheng, Xiaomeng; Geng, Xiao; Wang, Lei; Zhu, Bihong; Chemical communications (Cambridge, England) 61 (2025) 17033–17036; doi:10.1039/d5cc04462f

data_7135043
_publ_section_title
;
 Dehalogenation hydrolysis of CF<sub>2</sub>Br<sub>2</sub> enables
 four-component aminocarbonylation <i>via</i> photocatalytic radical-polar
 crossover.
;
_journal_issue                   87
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17033
_journal_page_last               17036
_journal_paper_doi               10.1039/d5cc04462f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C20 H22 N2 O3'
_chemical_formula_sum            'C20 H22 N2 O3'
_chemical_formula_weight         338.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-07-10 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8569(2)
_cell_length_b                   13.5366(2)
_cell_length_c                   13.7081(2)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.160
_cell_measurement_theta_min      4.486
_cell_volume                     1829.06(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0715
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14584
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.271
_diffrn_reflns_theta_min         4.591
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.2964
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1749 before and 0.1001 after correction.
The Ratio of minimum to maximum transmission is 0.3936.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0658
_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^)+(0.1217P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3061
_reflns_number_total             3281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04462f2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7135043.cif.'
_cod_database_code               7135043
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.866
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C2(H2), C3(H3), C15(H15), C7(H7), C4(H4), C11(H11), C9(H9),
 C10(H10), C8(H8)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              11537
_shelx_hkl_checksum              10755
_olex2_submission_special_instructions 'No special instructions were received'