Directing-Group-Free, Carbonyl Group-Promoted Catalytic C‒H Arylation of Bio-Based Furans
Karlinskii, Bogdan Ya.; Kostyukovich, Alexander Yu.; Kucherov, Fedor A.; Galkin, Konstantin I.; Kozlov, Kirill S.; Ananikov, Valentine P.; ACS Catalysis 10 (2020) 11466–11480; doi:10.1021/acscatal.0c02143

data_4518066
_publ_section_title
;
 Directing-Group-Free, Carbonyl Group-Promoted Catalytic C--H Arylation of
 Bio-Based Furans
;
_journal_issue                   19
_journal_name_full               'ACS Catalysis'
_journal_page_first              11466
_journal_page_last               11480
_journal_paper_doi               10.1021/acscatal.0c02143
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C13 H7 F3 O3'
_chemical_formula_sum            'C13 H7 F3 O3'
_chemical_formula_weight         268.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 101.1950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0065(3)
_cell_length_b                   13.6364(3)
_cell_length_c                   7.4223(2)
_cell_measurement_reflns_used    9701
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      44.29
_cell_measurement_theta_min      3.40
_cell_volume                     1092.81(5)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            137806
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.441
_diffrn_reflns_theta_min         2.406
_diffrn_source                   'X-Ray tube'
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_correction_T_min  0.7126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause <i>et al.</i>, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         9140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0795P)^2^+0.1644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6997
_reflns_number_total             9140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c02143_si_002.cif
_cod_data_source_block           3k
_cod_depositor_comments
'Adding full bibliography for 4518064--4518066.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518066
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.955
_shelx_res_checksum              40740
_shelx_hkl_checksum              83207