Gold-Catalyzed Ascorbic Acid-Induced Arylative Carbocyclization of Alkynes with Aryldiazonium Tetrafluoroborates
Medina-Mercado, Ignacio; Colin-Molina, Abraham; Barquera-Lozada, José Enrique; Rodríguez-Molina, Braulio; Porcel, Susana; ACS Catalysis  (2021) 8968–8977; doi:10.1021/acscatal.1c01826

data_4518870
_publ_contact_author
;
      'Susana Porcel'
      Instituto de Qu\'imica,
      Universidad Aut\'onoma de M\'exico,
      Circuito Exterior,
      Cuidad Universitaria.
      04510 Ciudad de M\'exico,
      M\'exico  
      
;
_publ_section_title
;
 Gold-Catalyzed Ascorbic Acid-Induced Arylative Carbocyclization of
 Alkynes with Aryldiazonium Tetrafluoroborates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              8968
_journal_page_last               8977
_journal_paper_doi               10.1021/acscatal.1c01826
_journal_year                    2021
_chemical_formula_sum            'C22 H17 N O4'
_chemical_formula_weight         359.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.8710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9302(3)
_cell_length_b                   21.3945(10)
_cell_length_c                   13.9168(6)
_cell_measurement_reflns_used    9679
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      2.41
_cell_volume                     1756.41(14)
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_collection       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_molecular_graphics
'SHELXLe (H&#x00C2;&#x00B8;bschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker D8 Venture \k geometry diffractometer 208039-1'
_diffrn_measurement_method       '\f and \w-scans'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_radiation_source         'micro-focus X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44739
_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         29.574
_diffrn_reflns_theta_min         2.406
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2402 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         9844
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0484P)^2^+0.3969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6591
_reflns_number_total             9844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01826_si_003.cif
_cod_data_source_block           034RMB20_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4518870
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              45100
_shelx_hkl_checksum              10246