Palladium-Catalyzed Domino Heck/Intermolecular C-H Bond Functionalization: Efficient Synthesis of Alkylated Polyfluoroarene Derivatives.
Wu, Xin-Xing; Chen, Wen-Long; Shen, Yi; Chen, Si; Xu, Peng-Fei; Liang, Yong-Min; Organic letters 18 (2016) 1784–1787; doi:10.1021/acs.orglett.6b00447

data_1542943
_publ_section_title
;
 Palladium-Catalyzed Domino Heck/Intermolecular C-H Bond
 Functionalization: Efficient Synthesis of Alkylated Polyfluoroarene
 Derivatives.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1784
_journal_page_last               1787
_journal_paper_doi               10.1021/acs.orglett.6b00447
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C23 H17 F4 N O'
_chemical_formula_sum            'C23 H17 F4 N O'
_chemical_formula_weight         399.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.862(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0334(6)
_cell_length_b                   8.6509(4)
_cell_length_c                   17.4221(11)
_cell_measurement_reflns_used    1060
_cell_measurement_temperature    293.60(10)
_cell_measurement_theta_max      20.9830
_cell_measurement_theta_min      3.5660
_cell_volume                     1922.41(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.60(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega   41.00   87.80   1.2000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000   90.0000 39

  2 omega  -51.00   93.00   1.2000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000 -180.0000 120

  3 omega   24.00   37.20   1.2000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000   90.0000 11
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0027969000
_diffrn_orient_matrix_UB_12      0.0353316000
_diffrn_orient_matrix_UB_13      0.0371078000
_diffrn_orient_matrix_UB_21      -0.0319661000
_diffrn_orient_matrix_UB_22      0.0614819000
_diffrn_orient_matrix_UB_23      -0.0182278000
_diffrn_orient_matrix_UB_31      -0.0454154000
_diffrn_orient_matrix_UB_32      -0.0411590000
_diffrn_orient_matrix_UB_33      0.0046422000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6691
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0674
_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^)+(0.0768P)^2^+0.1855P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.2076
_reflns_number_gt                1819
_reflns_number_total             3605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00447_si_003.cif
_cod_data_source_block           wuxx_53
_cod_depositor_comments
'Adding full bibliography for 1542943--1542944.cif.'
_cod_original_cell_volume        1922.42(17)
_cod_database_code               1542943
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C21(H21)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'