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_7043208
_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         'Cl, 2(H2 O), C15 H14 Cl N4'
_chemical_formula_sum            'C15 H18 Cl2 N4 O2'
_chemical_formula_weight         357.23
_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             2014-09-05
_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                86.782(5)
_cell_angle_beta                 77.574(5)
_cell_angle_gamma                70.405(5)
_cell_formula_units_Z            2
_cell_length_a                   7.2346(4)
_cell_length_b                   9.1795(5)
_cell_length_c                   13.2726(8)
_cell_measurement_reflns_used    3249
_cell_measurement_temperature    128(17)
_cell_measurement_theta_max      29.0488
_cell_measurement_theta_min      4.4279
_cell_volume                     810.81(9)
_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      128(17)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.861
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_details
;
  1 omega  -58.00   41.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397    0.0000  -90.0000 99

  2 omega  -22.00   25.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  150.0000 47

  3 omega  -25.00   20.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000    0.0000 45

  4 omega  -85.00    7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000 -120.0000 92

  5 omega   38.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366  178.0000 -150.0000 55

  6 omega  -47.00   53.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000  -30.0000 100

  7 omega   -2.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000  120.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0760540000
_diffrn_orient_matrix_UB_12      -0.0680921000
_diffrn_orient_matrix_UB_13      -0.0226611000
_diffrn_orient_matrix_UB_21      -0.0282832000
_diffrn_orient_matrix_UB_22      -0.0430414000
_diffrn_orient_matrix_UB_23      0.0430566000
_diffrn_orient_matrix_UB_31      -0.0688472000
_diffrn_orient_matrix_UB_32      -0.0154972000
_diffrn_orient_matrix_UB_33      -0.0250619000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8635
_diffrn_reflns_theta_full        29.11
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         4.44
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96554
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0460P)^2^+0.4320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                3214
_reflns_number_total             3752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7dt01433c2.cif
_cod_data_source_block           4
_cod_original_cell_volume        810.81(8)
_cod_database_code               7043208
_chemical_oxdiff_formula         'C12 H14 N3 Cl1'
_chemical_oxdiff_usercomment     'AT 120 K, YELLOW BLOCK'
_reflns_odcompleteness_completeness 98.88
_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, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C2(H2), C12(H12), C1(H1), C9(H9), C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'