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_7043205
_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 H39 Cl2 N4 P Pd, 2(C2 H3 N)'
_chemical_formula_sum            'C45 H45 Cl2 N6 P Pd'
_chemical_formula_weight         878.14
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_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_date             2014-07-23
_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                90.00
_cell_angle_beta                 93.177(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5933(3)
_cell_length_b                   15.7459(4)
_cell_length_c                   25.1218(15)
_cell_measurement_reflns_used    9652
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1236
_cell_measurement_theta_min      3.5568
_cell_volume                     4183.9(3)
_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 0.862
_diffrn_measurement_details
;
  1 omega  -85.00   12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000    0.0000 97

  2 omega  -43.00   46.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000  120.0000 89

  3 omega  -23.00   17.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -120.0000 40

  4 omega  -93.00  -68.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  120.0000 25

  5 omega  -53.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -37.0000  -60.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0481235000
_diffrn_orient_matrix_UB_12      0.0012203000
_diffrn_orient_matrix_UB_13      0.0185317000
_diffrn_orient_matrix_UB_21      0.0395082000
_diffrn_orient_matrix_UB_22      -0.0229461000
_diffrn_orient_matrix_UB_23      0.0186514000
_diffrn_orient_matrix_UB_31      0.0249197000
_diffrn_orient_matrix_UB_32      0.0387408000
_diffrn_orient_matrix_UB_33      0.0104844000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27806
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         3.56
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94251
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         9765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0240P)^2^+2.3419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                7770
_reflns_number_total             9765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7dt01433c2.cif
_cod_data_source_block           2a
_cod_database_code               7043205
_chemical_oxdiff_formula         'C20 H20 Cl2 N3 P1 Pd1'
_chemical_oxdiff_usercomment     '150K, YELLOW, BLOCK, .42, .32 .24'
_reflns_odcompleteness_completeness 99.16
_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:
 C3(H3), C29(H29), C34(H34), C32(H32), C1(H1), C35(H35), C33(H33), C15(H15),
 C8(H8), C31(H31), C27(H27), C28(H28), C7(H7), C41(H41), C37(H37), C2(H2),
 C40(H40), C25(H25), C10(H10), C26(H26), C14(H14), C16(H16), C9(H9), C39(H39),
 C38(H38)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C19(H19A,H19B,
 H19C), C42(H42A,H42B,H42C), C44(H44A,H44B,H44C)
;
_olex2_submission_special_instructions 'No special instructions were received'