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_4518065
_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         'C18 H12 O3'
_chemical_formula_sum            'C18 H12 O3'
_chemical_formula_weight         276.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 101.3160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3333(4)
_cell_length_b                   11.1772(4)
_cell_length_c                   19.7023(6)
_cell_measurement_reflns_used    7974
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.07
_cell_measurement_theta_min      2.48
_cell_volume                     2663.20(15)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_publication_material
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_structure_solution
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       '\w shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            41459
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.000
_diffrn_reflns_theta_min         2.481
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_correction_T_min  0.7191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0577P)^2^+1.7684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3908
_reflns_number_total             5431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c02143_si_003.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 4518064--4518066.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4518065
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              82791
_shelx_hkl_checksum              54483