A Highly Efficient, Recyclable Catalyst for C-C Coupling Reactions in Ionic Liquids: Pyrazolyl-Functionalized N-Heterocyclic Carbene Complex of Palladium(II)
Ruihu Wang; Brendan Twamley; Jean'ne M. Shreeve; Journal of Organic Chemistry 71 (2006) 426–429; doi:10.1021/jo052098b

data_4021372
_publ_section_title
;
 A Highly Efficient, Recyclable Catalyst for C-C Coupling Reactions
 in Ionic Liquids: Pyrazolyl-Functionalized
 N-Heterocyclic Carbene Complex of Palladium(II)
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              426
_journal_page_last               429
_journal_paper_doi               10.1021/jo052098b
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C17 H21 Cl N4 Pd, 0.5 (CH2 Cl2)'
_chemical_formula_sum            'C17.5 H22 Cl2 N4 Pd'
_chemical_formula_weight         465.69
_chemical_name_common            'C17 H21 Cl N4 Pd, 0.5 (CH2 Cl2)'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.621(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1482(4)
_cell_length_b                   18.4592(8)
_cell_length_c                   12.9869(6)
_cell_measurement_reflns_used    6992
_cell_measurement_temperature    87(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.73
_cell_volume                     1953.24(16)
_computing_cell_refinement       'Bruker SAINT+ v. 6.45a'
_computing_data_collection       'Bruker SMART v. 5.626'
_computing_data_reduction        'Bruker SAINT+ v. 6.45a'
_computing_molecular_graphics    'XP, Bruker SHELXTL v. 6.12'
_computing_publication_material  'XCIF, Bruker SHELXTL v. 6.12'
_computing_structure_refinement  'XL, Bruker SHELXTL v. 6.12'
_computing_structure_solution    'XS, Bruker SHELXTL v. 6.12'
_diffrn_ambient_temperature      87(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker/Siemens SMART APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29697
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.231
_exptl_absorpt_correction_T_max  0.8089
_exptl_absorpt_correction_T_min  0.6388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2004'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.452
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0162P)^2^+5.2253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0633
_reflns_number_gt                3435
_reflns_number_total             3535
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo052098bsi20051007_040446.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C17.50 H22 Cl2 N4 Pd'
_cod_database_code               4021372