Experiment and Theory of Bimetallic Pd-Catalyzed α-Arylation and Annulation for Naphthalene Synthesis
Ence, Chloe C.; Martinez, Erin E.; Himes, Samuel R.; Nazari, S. Hadi; Moreno, Mariur Rodriguez; Matu, Manase F.; Larsen, Samantha G.; Gassaway, Kyle J.; Valdivia-Berroeta, Gabriel A.; Smith, Stacey J.; Ess, Daniel H.; Michaelis, David J.; ACS Catalysis 11 (2021) 10394–10404; doi:10.1021/acscatal.1c02731

data_4518977
_publ_section_title
;
 Experiment and Theory of Bimetallic Pd-Catalyzed \a-Arylation and
 Annulation for Naphthalene Synthesis
;
_journal_issue                   16
_journal_name_full               'ACS Catalysis'
_journal_page_first              10394
_journal_page_last               10404
_journal_paper_doi               10.1021/acscatal.1c02731
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety
;         
 'C56 H58 F6 I N4 O6 P2 Pd2 S2, 1.154(C F3 O3 S), 0.154 Ag, 0.69(C6 H6), =
  1.15(C H3 OH)'
;
_chemical_formula_sum
'C62.46 H62.16 Ag0.16 F9.46 I N4 O10.62 P2 Pd2 S3.16'
_chemical_formula_weight         1737.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                111.215(8)
_cell_angle_beta                 104.832(8)
_cell_angle_gamma                96.150(8)
_cell_formula_units_Z            2
_cell_length_a                   14.761(4)
_cell_length_b                   15.803(5)
_cell_length_c                   17.805(5)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.15
_cell_volume                     3649.7(19)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 853)'
_computing_publication_material  'Bruker APEX3'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            77211
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_min         1.294
_diffrn_source                   'Micro Focus Rotating Anode'
_exptl_absorpt_coefficient_mu    1.170
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Krause, 2015)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1735
_refine_diff_density_max         2.033
_refine_diff_density_min         -1.131
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1641
_refine_ls_number_reflns         14925
_refine_ls_number_restraints     5581
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0691P)^2^+25.5256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1707
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12270
_reflns_number_total             14925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02731_si_005.cif
_cod_data_source_block           20038_a
_cod_database_code               4518977
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              71233
_shelx_hkl_checksum              33974