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_1542944
_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         'C16 H11 F5 O'
_chemical_formula_sum            'C16 H11 F5 O'
_chemical_formula_weight         314.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.905(4)
_cell_length_b                   7.8263(9)
_cell_length_c                   15.6010(17)
_cell_measurement_reflns_used    549
_cell_measurement_temperature    273.77(10)
_cell_measurement_theta_max      19.0400
_cell_measurement_theta_min      3.7250
_cell_volume                     2796.7(7)
_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
;
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      273.77(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -7.00   25.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  120.0000 32

  2 omega   -1.00   87.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000  150.0000 88

  3 omega   39.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   19.0000   30.0000 37
;
_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      -0.0024847000
_diffrn_orient_matrix_UB_12      0.0149814000
_diffrn_orient_matrix_UB_13      -0.0447358000
_diffrn_orient_matrix_UB_21      0.0306825000
_diffrn_orient_matrix_UB_22      0.0114556000
_diffrn_orient_matrix_UB_23      -0.0029313000
_diffrn_orient_matrix_UB_31      0.0035923000
_diffrn_orient_matrix_UB_32      -0.0884628000
_diffrn_orient_matrix_UB_33      -0.0078815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6908
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18354
_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    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.2010
_refine_ls_R_factor_gt           0.0835
_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^)+(0.1209P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2207
_refine_ls_wR_factor_ref         0.2986
_reflns_number_gt                998
_reflns_number_total             2752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00447_si_002.cif
_cod_data_source_block           wuxx_1223
_cod_depositor_comments
;
Adding full bibliography for 1542943--1542944.cif.

2017-03-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C16 H11 F5 O)'
_cod_original_formula_sum        'C32 H22 F10 O2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     628.50
_cod_database_code               1542944
_reflns_odcompleteness_completeness 99.48
_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), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 2015-12-23
_olex2_submission_special_instructions 'No special instructions were received'