An EDA complex-driven multicomponent reaction of Br-R<sub>f</sub> with alkenes <i>via</i> radical-polar crossover.
Chen, Zhen; Lan, Jin-Xin; Zhang, Shu-Peng; Lu, Shuai-Xiao; Zhang, Yicheng; Yang, Wen-Chao; Chemical communications (Cambridge, England) 61 (2025) 16286–16289; doi:10.1039/d5cc03971a

data_1575715
_publ_section_title
;
 An EDA complex-driven multicomponent reaction of Br-R<sub>f</sub> with
 alkenes <i>via</i> radical-polar crossover.
;
_journal_issue                   83
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16286
_journal_page_last               16289
_journal_paper_doi               10.1039/d5cc03971a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C21 H20 F2 N2 O2'
_chemical_formula_sum            'C21 H20 F2 N2 O2'
_chemical_formula_weight         370.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-04-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-07-05 deposited with the CCDC.	2025-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.483(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6342(8)
_cell_length_b                   10.2128(5)
_cell_length_c                   15.7401(10)
_cell_measurement_reflns_used    6090
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      23.29
_cell_measurement_theta_min      2.42
_cell_volume                     1926.2(2)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53587
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.416
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1280 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.8868.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0479P)^2^+0.4192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1288
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3262
_reflns_number_total             4380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03971a2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 1575715.cif.'
_cod_database_code               1575715
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
O1 \\sim C11 \\sim C12 \\sim C11A \\sim C12A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 O1, C11, C12, C11A, C12A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Same fragment restrains
{O1, C11A, C12A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{O1, C11, C12}
5. Others
 Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
6.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12A(H12D,H12E,H12F)
;
_shelx_res_checksum              95364
_shelx_hkl_checksum              55134
_olex2_submission_special_instructions 'No special instructions were received'