NHC Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions of Aryl Boronate Esters with Perfluorobenzenes.
Zhou, Jing; Berthel, Johannes H. J.; Kuntze-Fechner, Maximilian W; Friedrich, Alexandra; Marder, Todd B.; Radius, Udo; The Journal of organic chemistry 81 (2016) 5789–5794; doi:10.1021/acs.joc.6b01041

data_4036944
_publ_section_title
;
 NHC Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions of Aryl
 Boronate Esters with Perfluorobenzenes.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5789
_journal_page_last               5794
_journal_paper_doi               10.1021/acs.joc.6b01041
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H10 F6'
_chemical_formula_sum            'C22 H10 F6'
_chemical_formula_weight         388.30
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-C 2yc'
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_atom_sites_solution_hydrogens   geom
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_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.893(19)
_cell_angle_gamma                90
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_cell_length_a                   21.524(12)
_cell_length_b                   6.136(3)
_cell_length_c                   11.931(8)
_cell_measurement_reflns_used    7466
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.290
_cell_measurement_theta_min      3.420
_cell_volume                     1573.7(16)
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.11-0 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_molecular_graphics    'shelXle (Huebschle et al., 2011)'
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_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
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_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
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_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
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_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8800
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         1.895
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.746
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_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_preparation
'Crystal fragment soaked in perfluoro polyether oil.'
_exptl_crystal_recrystallization_method
'recrystallised from deuterated chloroform by evaporation'
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.254
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0349P)^2^+1.6190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1471
_reflns_number_total             1558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01041_si_002.cif
_cod_data_source_block           AF011_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4036944
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              79584
_shelx_hkl_checksum              59283