Rhodium-Catalyzed Atroposelective C-H Fluoroallylation of Heteroarenes with gem-Difluocyclopropanes
Li, Junwei; Wang, Fen; He, Xian; Huang, Genping; Rong, Zi-Qiang; Li, Xingwei; Chemical Science  (2026) –; doi:10.1039/D5SC08914J

data_1577097
_publ_section_title
;
 Rhodium-Catalyzed Atroposelective C-H Fluoroallylation of Heteroarenes
 with gem-Difluocyclopropanes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC08914J
_journal_year                    2026
_chemical_formula_moiety         'C38 H24 F N'
_chemical_formula_sum            'C38 H24 F N'
_chemical_formula_weight         513.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-12
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-10-25 deposited with the CCDC.	2026-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.123(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5176(4)
_cell_length_b                   7.5220(4)
_cell_length_c                   20.2681(11)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    220.00
_cell_measurement_theta_max      68.44
_cell_measurement_theta_min      4.45
_cell_volume                     1274.17(11)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      220.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22138
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.556
_diffrn_reflns_theta_min         4.446
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1316 before and 0.0669 after correction.
The Ratio of minimum to maximum transmission is 0.8523.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1786 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4643
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0433P)^2^+0.0720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4241
_reflns_number_total             4643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08914j2.cif
_cod_data_source_block           s
_cod_database_code               1577097
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.830
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C14(H14), C16(H16), C17(H17), C18(H18), C22(H22),
 C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
;
_shelx_res_checksum              37678
_olex2_submission_special_instructions 'No special instructions were received'