Palladium-catalysed difluoroolefination of benzyl tosylates toward the synthesis of gem-difluoro-2-trifluromethyl styrene derivatives
Xu, Jie; Liu, Jiangjun; Chen, Gang; Xiong, Baojian; Zhang, Xuemei; Lian, Zhong; RSC Advances 12 (2022) 12983–12987; doi:10.1039/D2RA02473J

data_7244883
_publ_section_title
;
 Palladium-catalysed difluoroolefination of benzyl tosylates toward the
 synthesis of gem-difluoro-2-trifluromethyl styrene derivatives
;
_journal_issue                   21
_journal_name_full               'RSC Advances'
_journal_page_first              12983
_journal_page_last               12987
_journal_paper_doi               10.1039/D2RA02473J
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C13 H6 Br F5'
_chemical_formula_sum            'C13 H6 Br F5'
_chemical_formula_weight         337.09
_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             2021-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-01 deposited with the CCDC.	2022-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.106(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4671(16)
_cell_length_b                   5.8892(8)
_cell_length_c                   10.9041(12)
_cell_measurement_reflns_used    989
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2300
_cell_measurement_theta_min      3.9020
_cell_volume                     1217.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -35.00   53.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336   38.0000  -60.0000 88

  2 omega  -70.00  -31.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -57.0000  120.0000 39

  3 omega   36.00   90.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  178.0000  150.0000 54

  4 omega   42.00   85.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  178.0000   90.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0305306000
_diffrn_orient_matrix_UB_12      0.0577061000
_diffrn_orient_matrix_UB_13      0.0086685000
_diffrn_orient_matrix_UB_21      0.0057802000
_diffrn_orient_matrix_UB_22      0.0869094000
_diffrn_orient_matrix_UB_23      -0.0415253000
_diffrn_orient_matrix_UB_31      -0.0207759000
_diffrn_orient_matrix_UB_32      -0.0604735000
_diffrn_orient_matrix_UB_33      -0.0515636000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.1146
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5024
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.223
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.420
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1767
_refine_ls_R_factor_gt           0.0680
_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^)+(0.0767P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.2072
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1053
_reflns_number_total             2488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra02473j2.cif
_cod_data_source_block           210323_s1_xj
_cod_database_code               7244883
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3br1
_shelx_estimated_absorpt_t_max   0.482
_shelx_estimated_absorpt_t_min   0.381
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9)
;
_shelx_res_checksum              48990
_olex2_submission_special_instructions 'No special instructions were received'