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_7043206
_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_absolute_configuration ad
_chemical_formula_moiety         'F6 P, C20 H18 Cl N4'
_chemical_formula_sum            'C20 H18 Cl F6 N4 P'
_chemical_formula_weight         494.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.3122(14)
_cell_length_b                   8.5288(6)
_cell_length_c                   10.4839(8)
_cell_measurement_reflns_used    3551
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.0854
_cell_measurement_theta_min      3.9680
_cell_volume                     2173.9(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-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_details
;
  1 omega  -68.00   -2.00   1.0000   53.0600
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000 -120.0000 66

  2 omega  -87.00    4.00   1.0000   53.0600
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000    0.0000 91

  3 omega  -14.00   25.00   1.0000   53.0600
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  150.0000 39

  4 omega   36.00   65.00   1.0000   53.0600
omega____ theta____ kappa____ phi______ frames
    -       19.0585  178.0000  -60.0000 29

  5 omega  -93.00  -68.00   1.0000   53.0600
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000   30.0000 25

  6 omega  -47.00   53.00   1.0000   53.0600
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000    0.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0288063000
_diffrn_orient_matrix_UB_12      0.0128756000
_diffrn_orient_matrix_UB_13      0.0017757000
_diffrn_orient_matrix_UB_21      -0.0006687000
_diffrn_orient_matrix_UB_22      -0.0260605000
_diffrn_orient_matrix_UB_23      0.0642113000
_diffrn_orient_matrix_UB_31      0.0045388000
_diffrn_orient_matrix_UB_32      0.0779392000
_diffrn_orient_matrix_UB_33      0.0212179000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14085
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         3.98
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90650
_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    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5084
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0778
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1167P)^2^+0.5785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2391
_reflns_number_gt                2950
_reflns_number_total             5084
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7dt01433c2.cif
_cod_data_source_block           1
_cod_database_code               7043206
_chemical_oxdiff_formula         'C20 H30 N4 P1 F6'
_reflns_odcompleteness_completeness 99.18
_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:
 C3(H3), C1(H1), C2(H2), C16(H16), C14(H14), C10(H10), C7(H7), C9(H9), C8(H8)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'