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_7117645
_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         'C15 H10 F3 N O2'
_chemical_formula_sum            'C15 H10 F3 N O2'
_chemical_formula_weight         293.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/cc1j704x
_audit_creation_date             2015-05-28
_audit_creation_method
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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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8037(6)
_cell_length_b                   15.0490(14)
_cell_length_c                   15.033(2)
_cell_measurement_reflns_used    1478
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      23.8550
_cell_measurement_theta_min      3.7350
_cell_volume                     1313.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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)
;
_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 0.930
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
  1 omega  -61.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -38.0000 -180.0000 80

  2 omega   -5.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -99.0000   60.0000 26

  3 omega  -89.00  -63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  178.0000 -180.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0081124000
_diffrn_orient_matrix_UB_12      0.0389456000
_diffrn_orient_matrix_UB_13      -0.0263712000
_diffrn_orient_matrix_UB_21      -0.0446600000
_diffrn_orient_matrix_UB_22      0.0255753000
_diffrn_orient_matrix_UB_23      0.0356861000
_diffrn_orient_matrix_UB_31      0.1134877000
_diffrn_orient_matrix_UB_32      0.0072929000
_diffrn_orient_matrix_UB_33      0.0159440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.930
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3792
_diffrn_reflns_point_group_measured_fraction_full 0.796
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.027
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70205
_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_density_diffrn    1.483
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0516P)^2^+0.0594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1036
_reflns_Friedel_coverage         0.449
_reflns_Friedel_fraction_full    0.602
_reflns_Friedel_fraction_max     0.618
_reflns_number_gt                1605
_reflns_number_total             1889
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05035a2.cif
_cod_data_source_block           exp_5108
_cod_original_cell_volume        1313.0(2)
_cod_database_code               7117645
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C15 H4910 N1 O2 F3'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.981
_reflns_odcompleteness_completeness 94.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.b X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
;
_olex2_submission_special_instructions 'No special instructions were received'