Palladium-Catalyzed Ligand-Controlled Regioselective Nucleophilic Aromatic Substitution of 1-(Chloromethyl)naphthalenes with Arylacetonitriles.
Zhang, Sheng; Yamamoto, Yoshinori; Bao, Ming; The Journal of organic chemistry 83 (2018) 13981–13990; doi:10.1021/acs.joc.8b02343

data_4034868
_publ_section_title
;
 Palladium-Catalyzed Ligand-Controlled Regioselective Nucleophilic
 Aromatic Substitution of 1-(Chloromethyl)naphthalenes with
 Arylacetonitriles.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13981
_journal_page_last               13990
_journal_paper_doi               10.1021/acs.joc.8b02343
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C50 H44 F3 O3.5 P2 Pd S'
_chemical_formula_weight         958.25
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.074(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2343(10)
_cell_length_b                   22.018(2)
_cell_length_c                   19.3300(19)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.30
_cell_volume                     4355.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      172(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            50173
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  0.8886
_exptl_absorpt_correction_T_min  0.8586
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1964
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.991
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         7629
_refine_ls_number_restraints     672
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0905
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+67.1814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2009
_refine_ls_wR_factor_ref         0.2124
_reflns_number_gt                6062
_reflns_number_total             7629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02343_si_004.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C50 H44 F3 O3.50 P2 Pd S'
_cod_database_code               4034868