Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls via Suzuki-Miyaura Cross-Coupling in Water and Air.
Bunda, Szilvia; Udvardy, Antal; Voronova, Krisztina; Joó, Ferenc; The Journal of organic chemistry 83 (2018) 15486–15492; doi:10.1021/acs.joc.8b02340

data_4034761
_publ_section_title
;
 Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls
 via Suzuki-Miyaura Cross-Coupling in Water and Air.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15486
_journal_page_last               15492
_journal_paper_doi               10.1021/acs.joc.8b02340
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C13 H9 N O4, C3  H7  N  O'
_chemical_formula_sum            'C16 H16 N2 O5'
_chemical_formula_weight         316.31
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_date             2018-08-18T00:14:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                87.994(3)
_cell_angle_beta                 71.069(3)
_cell_angle_gamma                79.461(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9772(5)
_cell_length_b                   9.3301(5)
_cell_length_c                   11.0632(6)
_cell_measurement_reflns_used    379
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      79.92
_cell_measurement_theta_min      6.27
_cell_volume                     765.47(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  'PublCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.94
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5825
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.94
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.798
_diffrn_reflns_theta_min         4.823
_diffrn_source                   'INCOATEC I\mS 3.0,  microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.735
_exptl_absorpt_correction_T_min  0.408
_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    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.1081
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.288
_reflns_number_gt                2075
_reflns_number_total             2720
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {b948f9c6-1972-436a-b5be-7d7105834ad6}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            jo8b02340_si_004.cif
_cod_data_source_block           15
_cod_database_code               4034761