Copper-Catalyzed Direct C-H Alkylation of Polyfluoroarenes by Using Hydrocarbons as an Alkylating Source.
Xie, Weilong; Heo, Joon; Kim, Dongwook; Chang, Sukbok; Journal of the American Chemical Society 142 (2020) 7487–7496; doi:10.1021/jacs.0c00169

data_4134683
_publ_section_title
;
 Copper-Catalyzed Direct C-H Alkylation of Polyfluoroarenes by Using
 Hydrocarbons as an Alkylating Source.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7487
_journal_page_last               7496
_journal_paper_doi               10.1021/jacs.0c00169
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_sum            'C36 H38 F4 O5'
_chemical_formula_weight         626.66
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.609(4)
_cell_length_b                   15.344(6)
_cell_length_c                   21.494(9)
_cell_measurement_reflns_used    9147
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      3.14
_cell_volume                     3169(2)
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_collection       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1391
_diffrn_reflns_av_unetI/netI     0.0878
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            43714
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.844
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7250
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1063 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 _refine_ls_abs_structure_Flack    0.2(6)
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         5583
_refine_ls_number_restraints     522
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.1053
_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^)+(0.0437P)^2^+5.4612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.2036
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3852
_reflns_number_total             5583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Prod-40.cif
_cod_data_source_block           A19105_019
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4134682--4134685.cif.
;
_cod_database_code               4134683
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              24721
_shelx_hkl_checksum              21849