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_4083786
_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            'C33 H27 F6 N2 O4 P Pd'
_chemical_formula_weight         766.93
_chemical_name_common            NX013
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.674(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.868(10)
_cell_length_b                   16.543(15)
_cell_length_c                   17.842(16)
_cell_measurement_reflns_used    4672
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      25.5329
_cell_measurement_theta_min      2.4275
_cell_volume                     3186(5)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_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_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22944
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              MoK\a
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  0.56
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1544
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_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.140
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_refine_diff_density_min         -1.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         7325
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+3.6611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                6069
_reflns_number_total             7325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om500566n_si_002.cif
_cod_data_source_block           I
_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_original_cell_volume        3186.(5)
_cod_database_code               4083786
_shelx_res_checksum              97360
_shelx_hkl_checksum              53934