Ru(II)-catalyzed stereoselective C(7)-H α-fluoroalkenylation of indolines.
Liu, Xingwang; Xiao, Shunli; Huang, Hao; Bai, Lele; Lai, Wenze; Wu, Gaorong; Chemical communications (Cambridge, England) 61 (2025) 18850–18853; doi:10.1039/d5cc05503b

data_7135217
_publ_section_title
;
 Ru(II)-catalyzed stereoselective C(7)-H &#x3b1;-fluoroalkenylation of
 indolines.
;
_journal_issue                   95
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              18850
_journal_page_last               18853
_journal_paper_doi               10.1039/d5cc05503b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C27 H21 F N2'
_chemical_formula_sum            'C27 H21 F N2'
_chemical_formula_weight         392.46
_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_date             2025-01-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-08 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.3948(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.68938(11)
_cell_length_b                   17.62391(15)
_cell_length_c                   8.08000(7)
_cell_measurement_reflns_used    10894
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6050
_cell_measurement_theta_min      4.0680
_cell_volume                     1947.68(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     58.00  85.00   0.50    0.05    --   62.16  15.00 120.00   54
  2  \w     56.00  85.00   0.50    0.05    --   62.16  15.00  90.00   58
  3  \w     63.00 102.00   0.50    0.05    --   62.16  15.00  30.00   78
  4  \w     66.00  94.00   0.50    0.05    --   62.16  15.00   0.00   56
  5  \w     60.00  86.00   0.50    0.05    --   62.16  15.00 -30.00   52
  6  \w     55.00  94.00   0.50    0.05    --   62.16  15.00 -60.00   78
  7  \w     55.00  80.00   0.50    0.05    --   62.16  15.00 -90.00   50
  8  \w     73.00 111.00   0.50    0.05    --   71.22  15.00-150.00   76
  9  \w     57.00 100.00   0.50    0.05    --   62.16  15.00-180.00   86
 10  \w     82.00 113.00   0.50    0.05    --   74.38  15.00-120.00   62
 11  \w     67.00 113.00   0.50    0.05    --   74.38  15.00 -30.00   92
 12  \w     67.00 114.00   0.50    0.05    --   74.38  15.00  30.00   94
 13  \w     71.00  96.00   0.50    0.05    --   74.38  15.00  90.00   50
 14  \w     65.00  98.00   0.50    0.05    --   62.16  15.00 150.00   66
 15  \w     68.00 111.00   0.50    0.05    --   74.38  15.00 120.00   86
 16  \w     72.00  97.00   0.50    0.05    --   74.38  15.00  60.00   50
 17  \w     70.00 104.00   0.50    0.05    --   74.38  15.00-180.00   68
 18  \w     47.00  76.00   0.50    0.05    --   74.38-125.00-150.00   58
 19  \w     48.00  84.00   0.50    0.05    --   74.38-125.00-180.00   72
 20  \w     25.00  67.00   0.50    0.05    --   62.16-125.00-150.00   84
 21  \w     42.00  67.00   0.50    0.05    --   62.16-125.00-120.00   50
 22  \w     26.00  58.00   0.50    0.05    --   62.16-125.00   0.00   64
 23  \w     42.00  67.00   0.50    0.05    --   74.38-125.00 -30.00   50
 24  \w     39.00  65.00   0.50    0.05    --   74.38-125.00   0.00   52
 25  \w     44.00  71.00   0.50    0.05    --   74.38-125.00 120.00   54
 26  \w     50.00  86.00   0.50    0.05    --   74.38-125.00 150.00   72
 27  \w     26.00  66.00   0.50    0.05    --   62.16-125.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0539355000
_diffrn_orient_matrix_UB_12      0.0435393000
_diffrn_orient_matrix_UB_13      -0.1340456000
_diffrn_orient_matrix_UB_21      -0.0430207000
_diffrn_orient_matrix_UB_22      -0.0545306000
_diffrn_orient_matrix_UB_23      -0.1331590000
_diffrn_orient_matrix_UB_31      -0.0890503000
_diffrn_orient_matrix_UB_32      0.0525530000
_diffrn_orient_matrix_UB_33      -0.0276571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_unetI/netI     0.0100
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14326
_diffrn_reflns_theta_full        72.92
_diffrn_reflns_theta_max         72.92
_diffrn_reflns_theta_min         4.09
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.8259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                3595
_reflns_number_total             3758
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5cc05503b2.cif
_cod_data_source_block           bd4ph
_cod_database_code               7135217
_chemical_oxdiff_formula         'C H O N S Cl'
_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:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.595