Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent.
Aikawa, Kohsuke; Serizawa, Hiroki; Ishii, Koki; Mikami, Koichi; Organic letters 18 (2016) 3690–3693; doi:10.1021/acs.orglett.6b01734

data_1555644
_publ_section_title
;
 Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with
 (Difluoromethyl)zinc Reagent.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3690
_journal_page_last               3693
_journal_paper_doi               10.1021/acs.orglett.6b01734
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C20 H24 F4 N2 O2 Zn'
_chemical_formula_weight         465.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.541(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4380(5)
_cell_length_b                   8.4217(3)
_cell_length_c                   17.3621(6)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    90
_cell_measurement_theta_max      72.18
_cell_measurement_theta_min      4.11
_cell_volume                     2107.07(13)
_computing_cell_refinement       'APEX3 v2015.9 (Bruker AXS)'
_computing_data_collection
'Bruker Instrument Service V4.2.9 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS'
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_computing_publication_material
'Generate Report V2014.1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayered conforcal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         72.106
_diffrn_reflns_theta_min         4.109
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Bruker Turbo X-ray Source'
_exptl_absorpt_coefficient_mu    2.098
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0313P)^2^+1.6825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3585
_reflns_number_total             4139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01734_si_002.cif
_cod_data_source_block           fhc1_p21n_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1555644
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.818
_shelx_estimated_absorpt_t_max   0.884
_shelx_res_checksum              96828
_shelx_hkl_checksum              78557