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_7043209
_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         'C38 H33 Cl2 N4 P Pd, 2(C2 H3 N)'
_chemical_formula_sum            'C42 H39 Cl2 N6 P Pd'
_chemical_formula_weight         836.06
_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                87.426(2)
_cell_angle_beta                 88.905(2)
_cell_angle_gamma                66.105(3)
_cell_formula_units_Z            4
_cell_length_a                   13.3244(4)
_cell_length_b                   15.4366(4)
_cell_length_c                   20.4811(6)
_cell_measurement_reflns_used    15432
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1444
_cell_measurement_theta_min      3.5683
_cell_volume                     3847.7(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details
;
  1 omega  -37.00   55.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000  -90.0000 92

  2 omega  -85.00    1.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  120.0000 86

  3 omega  -17.00   25.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   30.0000 42

  4 omega  -38.00   49.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000   30.0000 87

  5 omega  -86.00  -11.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  -90.0000 75

  6 omega  -25.00   25.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -30.0000 50

  7 omega  -93.00  -35.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000   30.0000 58

  8 omega   32.00   85.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9803 -178.0000   60.0000 53
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0393172000
_diffrn_orient_matrix_UB_12      0.0226809000
_diffrn_orient_matrix_UB_13      -0.0249200000
_diffrn_orient_matrix_UB_21      -0.0426461000
_diffrn_orient_matrix_UB_22      0.0015747000
_diffrn_orient_matrix_UB_23      0.0218104000
_diffrn_orient_matrix_UB_31      -0.0050421000
_diffrn_orient_matrix_UB_32      0.0448665000
_diffrn_orient_matrix_UB_33      0.0102516000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40083
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.58
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81525
_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    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         3.126
_refine_diff_density_min         -2.126
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     947
_refine_ls_number_reflns         17709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0674
_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^)+(0.0369P)^2^+29.3530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1718
_reflns_number_gt                13400
_reflns_number_total             17709
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7dt01433c2.cif
_cod_data_source_block           2b
_cod_original_cell_volume        3847.69(19)
_cod_database_code               7043209
_chemical_oxdiff_formula         'C12 H14 N2 Pd1 Cl1 P1'
_chemical_oxdiff_usercomment     'AT 150 K, YELLOW, BLOCK'
_reflns_odcompleteness_completeness 99.25
_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 Aromatic/amide H refined with riding coordinates:
 C28(H28), C75(H75), C23(H23), C76(H76), C24(H24), C68(H68), C3(H3), C8(H8),
 C64(H64), C9(H9), C2(H2), C40(H40), C47(H47), C45(H45), C22(H22), C38(H38),
 C1(H1), C34(H34), C29(H29), C10(H10), C70(H70), C39(H39), C67(H67), C46(H46),
 C69(H69), C30(H30), C7(H7), C54(H54), C74(H74), C63(H63), C25(H25), C41(H41),
 C72(H72), C26(H26), C31(H31), C35(H35), C32(H32), C60(H60), C52(H52), C66(H66),
  C48(H48), C73(H73), C36(H36), C16(H16), C61(H61), C14(H14), C62(H62), C37(H37)
2.b Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C57(H57A,H57B,H57C), C56(H56A,H56B,H56C), C83(H83A,H83B,
 H83C), C20(H20A,H20B,H20C), C79(H79A,H79B,H79C), C81(H81A,H81B,H81C), C18(H18A,
 H18B,H18C), C19(H19A,H19B,H19C), C77(H77A,H77B,H77C)
;
_olex2_submission_special_instructions 'No special instructions were received'