Palladium-catalyzed cross-coupling of aryl fluorides with N-tosylhydrazones via C-F bond activation
Haiqing Luo; Guojiao Wu; Shuai Xu; Kang Wang; Chaoqiang Wu; Yan Zhang; Jianbo Wang; Chem.Commun. 51 (2015) 13321–; doi:10.1039/C5cc05035A

data_7117644
_publ_section_title
;
 Palladium-catalyzed cross-coupling of aryl fluorides with
 N-tosylhydrazones via C-F bond activation
;
_journal_name_full               Chem.Commun.
_journal_page_first              13321
_journal_paper_doi               10.1039/C5cc05035A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C16 H12 F3 N O2'
_chemical_formula_sum            'C16 H12 F3 N O2'
_chemical_formula_weight         307.27
_chemical_name_systematic
(Z)-2-nitro-1-(1-phenylprop-1-enyl)-4-(trifluoromethyl)benzene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-16 deposited with the CCDC.
2015-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                75.880(7)
_cell_angle_beta                 72.823(8)
_cell_angle_gamma                67.507(9)
_cell_formula_units_Z            2
_cell_length_a                   8.1909(8)
_cell_length_b                   9.5693(9)
_cell_length_c                   10.5301(8)
_cell_measurement_reflns_used    1803
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      26.2040
_cell_measurement_theta_min      2.9720
_cell_volume                     720.50(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega  -81.00   17.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -57.0000  -30.0000 98

  2 omega -100.00  -75.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  178.0000 -150.0000 25

  3 omega  -87.00  -60.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954 -178.0000  -90.0000 27

  4 omega  -41.00   43.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954   57.0000  -90.0000 84

  5 omega  -91.00   22.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -77.0000  120.0000 113
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0412616000
_diffrn_orient_matrix_UB_12      -0.0572817000
_diffrn_orient_matrix_UB_13      0.0188816000
_diffrn_orient_matrix_UB_21      -0.0829139000
_diffrn_orient_matrix_UB_22      0.0559038000
_diffrn_orient_matrix_UB_23      -0.0120027000
_diffrn_orient_matrix_UB_31      0.0260340000
_diffrn_orient_matrix_UB_32      -0.0132129000
_diffrn_orient_matrix_UB_33      -0.0676918000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_laue_measured_fraction_full 0.977
_diffrn_reflns_laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5726
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.014
_diffrn_reflns_theta_min         2.864
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'Yellow '
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0893
_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^)+(0.1068P)^2^+0.9932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2252
_refine_ls_wR_factor_ref         0.2594
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                1803
_reflns_number_total             2770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05035a2.cif
_cod_data_source_block           exp_5136
_cod_original_cell_volume        720.49(12)
_cod_database_code               7117644
_audit_block_doi                 10.5517/cc1j703w
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C16 H12 O2 N1 F3'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'