Palladium(II) Complexes Bearing an Indazole-Derived N-Heterocyclic Carbene and Phosphine Coligands as Catalysts for the Sonogashira Coupling and the Hydroamination of Alkynes
Bernhammer, Jan C.; Chong, Ning Xi; Jothibasu, Ramasamy; Zhou, Binbin; Huynh, Han Vinh; Organometallics  (2014) 140627160434001–; doi:10.1021/om500566n

data_4083783
_publ_section_title
;
 Palladium(II) Complexes Bearing an Indazole-Derived N-Heterocyclic
 Carbene and Phosphine Coligands as Catalysts for the Sonogashira
 Coupling and the Hydroamination of Alkynes
;
_journal_name_full               Organometallics
_journal_page_first              140627160434001
_journal_paper_doi               10.1021/om500566n
_journal_year                    2014
_chemical_formula_sum            'C17 H18 Br2 Cl3 N3 Pd'
_chemical_formula_weight         636.91
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.2789(6)
_cell_length_b                   9.4519(3)
_cell_length_c                   21.9379(7)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.55
_cell_volume                     4204.9(2)
_computing_cell_refinement       'APEX2 v2013.6-2 (Bruker AXS)'
_computing_data_collection       'APEX2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            49638
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.111
_diffrn_source                   'Sealed Microfocusing Source'
_exptl_absorpt_coefficient_mu    5.072
_exptl_absorpt_correction_T_max  0.77
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.012
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0239P)^2^+3.2190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0485
_refine_ls_wR_factor_ref         0.0513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4047
_reflns_number_total             4823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om500566n_si_002.cif
_cod_data_source_block           D637A
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4083783
_shelx_estimated_absorpt_t_min   0.381
_shelx_estimated_absorpt_t_max   0.771
_shelxl_version_number           2013-3
_shelx_res_checksum              83330
_shelx_hkl_checksum              91094