Rhodium-catalyzed C-H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones.
Song, Jia-Lin; Yang, Zi-Feng; Fang, Sheng; Chen, Wang-Liang; Ye, Lian-Bao; Liu, Xiang; Shu, Bing; Chemical communications (Cambridge, England) 60 (2024) 15000–15003; doi:10.1039/d4cc05621c

data_7133995
_publ_section_title
;
 Rhodium-catalyzed C-H &#x3b1;-fluoroalkenylation/annulation of
 &#x3b2;-ketosulfoxonium ylides with 2,2-difluorovinyl
 tosylate/oxadiazolones.
;
_journal_issue                   100
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15000
_journal_page_last               15003
_journal_paper_doi               10.1039/d4cc05621c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C24 H16 Br2 N2 O4'
_chemical_formula_sum            'C24 H16 Br2 N2 O4'
_chemical_formula_weight         556.21
_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     dual
_audit_creation_date             2023-11-04
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-09-11 deposited with the CCDC.	2024-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.2430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.02870(10)
_cell_length_b                   20.8713(2)
_cell_length_c                   8.81380(10)
_cell_measurement_reflns_used    8930
_cell_measurement_temperature    220.00(10)
_cell_measurement_theta_max      74.0850
_cell_measurement_theta_min      3.4630
_cell_volume                     2342.19(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_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    -30.00  31.00   0.50    0.50    --    0.00 -82.00-180.00  122
  2  \w    -33.00  -2.00   0.50    0.50    --    0.00 -82.00   0.00   62
  3  \w    -33.00  23.00   0.50    0.50    --    0.00 -82.00  60.00  112
  4  \w    -14.00  11.00   0.50    0.50    --    0.00 -82.00-150.00   50
  5  \w     84.00 185.00   0.50    0.50    --   95.80  45.00 150.00  202
  6  \w      6.00 119.00   0.50    0.50    --   95.80 -61.00-120.00  226
  7  \w     79.00 110.00   0.50    0.50    --   95.80  30.00  90.00   62
  8  \w     76.00 152.00   0.50    0.50    --   95.80  45.00-180.00  152
  9  \w     90.00 116.00   0.50    0.50    --   95.80 -61.00  30.00   52
 10  \w    142.00 183.00   0.50    0.50    --   95.80  30.00  90.00   82
 11  \w     52.00 115.00   0.50    0.50    --   95.80 -45.00   0.00  126
 12  \w     79.00 162.00   0.50    0.50    --   95.80  30.00 120.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0319502000
_diffrn_orient_matrix_UB_12      0.0318152000
_diffrn_orient_matrix_UB_13      0.1407901000
_diffrn_orient_matrix_UB_21      -0.1081933000
_diffrn_orient_matrix_UB_22      -0.0327630000
_diffrn_orient_matrix_UB_23      -0.0428351000
_diffrn_orient_matrix_UB_31      0.0436513000
_diffrn_orient_matrix_UB_32      -0.0580033000
_diffrn_orient_matrix_UB_33      0.1016389000
_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  0.0227
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12255
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.302
_diffrn_reflns_theta_min         4.067
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00143(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0508P)^2^+1.6403P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4300
_reflns_number_total             4631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05621c2.cif
_cod_data_source_block           sjl-1
_cod_depositor_comments          'Adding full bibliography for 7133995.cif.'
_cod_database_code               7133995
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Br'
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C19(H19),
 C20(H20), C22(H22), C23(H23)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              82908
_shelx_hkl_checksum              90154
_shelx_fab_checksum              43937
_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 1.790
_oxdiff_exptl_absorpt_empirical_full_min 0.721