Synthesis of Zwitterionic Palladium Complexes and Their Application as Catalysts in Cross-Coupling Reactions of Aryl, Heteroaryl and Benzyl Bromides with Organoboron Reagents in Neat Water
Visannagari, Ramakrishna; Nareddula, Dastagiri Reddy; Dalton Trans.  (2017) –; doi:10.1039/C7DT01433C

data_7043207
_publ_section_title
;
 Synthesis of Zwitterionic Palladium Complexes and Their Application as
 Catalysts in Cross-Coupling Reactions of Aryl, Heteroaryl and Benzyl
 Bromides with Organoboron Reagents in Neat Water
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01433C
_journal_year                    2017
_chemical_formula_moiety         'C41 H38 Cl N4 P Pd'
_chemical_formula_sum            'C41 H38 Cl N4 P Pd'
_chemical_formula_weight         759.57
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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   difmap
_audit_creation_date             2014-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-07-24 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                83.401(5)
_cell_angle_beta                 88.501(5)
_cell_angle_gamma                70.238(6)
_cell_formula_units_Z            2
_cell_length_a                   9.2199(5)
_cell_length_b                   11.5698(7)
_cell_length_c                   17.5646(10)
_cell_measurement_reflns_used    4773
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.7509
_cell_measurement_theta_min      3.9941
_cell_volume                     1751.47(19)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details
;
  1 omega   36.00  111.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1301  178.0000   90.0000 75

  2 omega  -50.00   60.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1301  -77.0000   60.0000 110

  3 omega  -11.00   99.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1301   77.0000  -90.0000 110

  4 omega  -47.00   45.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1301  -57.0000  150.0000 92

  5 omega  -25.00   27.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5676  -99.0000  -30.0000 52

  6 omega   35.00   60.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1301  178.0000    0.0000 25

  7 omega   -5.00   97.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1301   57.0000  120.0000 102
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0435458000
_diffrn_orient_matrix_UB_12      -0.0313355000
_diffrn_orient_matrix_UB_13      -0.0163174000
_diffrn_orient_matrix_UB_21      0.0012565000
_diffrn_orient_matrix_UB_22      -0.0356547000
_diffrn_orient_matrix_UB_23      0.0357933000
_diffrn_orient_matrix_UB_31      -0.0691792000
_diffrn_orient_matrix_UB_32      0.0452215000
_diffrn_orient_matrix_UB_33      0.0102689000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16836
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.81
_diffrn_reflns_theta_min         4.00
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.078
_refine_diff_density_min         -1.069
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                6142
_reflns_number_total             7873
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7dt01433c2.cif
_cod_data_source_block           3
_cod_original_cell_volume        1751.48(18)
_cod_database_code               7043207
_chemical_oxdiff_formula         'C12 H14 N2 Pd2'
_chemical_oxdiff_usercomment     'AT 150 K COLORLESS, PLATE'
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C40(H40), C31(H31), C33(H33), C2(H2), C1(H1), C26(H26), C35(H35), C32(H32),
 C14(H14), C25(H25), C29(H29), C38(H38), C39(H39), C28(H28), C15(H15), C8(H8),
 C37(H37), C41(H41), C10(H10), C27(H27), C7(H7), C9(H9), C34(H34), C16(H16)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C19(H19A,H19B,
 H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'