Palladium-Catalyzed C-F Activation of Polyfluoronitrobenzene Derivatives in Suzuki-Miyaura Coupling Reactions
Matthew R. Cargill; Graham Sandford; Andrezj J. Tadeusiak; Dmitrii S. Yufit; Judith A. K. Howard; Pinar Kilickiran; Gabrielle Nelles; Journal of Organic Chemistry 75 (2010) 5860–5866; doi:10.1021/jo100877j

data_4025615
_publ_contact_author_address
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
_publ_contact_author_email       d.s.yufit@durham.ac.uk
_publ_contact_author_name        'Dmitry Yufit'
_publ_section_title
;
 Palladium-Catalyzed C-F Activation of Polyfluoronitrobenzene Derivatives
 in Suzuki-Miyaura Coupling Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5860
_journal_page_last               5866
_journal_paper_doi               10.1021/jo100877j
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C42 H30 F5 N O2 P2 Pd'
_chemical_formula_sum            'C42 H30 F5 N O2 P2 Pd'
_chemical_formula_weight         844.01
_chemical_name_systematic
;
trans-fluoro-(2-nitro-3,4,5,6-tetrafluorophenyl)-bis(triphenylphosphino)-
palladium(ii) 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.49(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9604(4)
_cell_length_b                   13.9264(3)
_cell_length_c                   20.6986(5)
_cell_measurement_reflns_used    29439
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      35.8327
_cell_measurement_theta_min      1.6304
_cell_volume                     3600.2(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics
;
Olex2, Durham University (compiled Aug 12 2008 17:07:14)
;
_computing_publication_material
;
Olex2, Durham University (compiled Aug 12 2008 17:07:14)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Spider R-Axis IP'
_diffrn_measurement_method       /w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            62478
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.9546
_exptl_absorpt_correction_T_min  0.7265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FSProcess (Rigaku Inc., 2007)'
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.112
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         9547
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0450P)^2^+5.5000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                7823
_reflns_number_total             9547
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100877j_si_002.cif
_cod_data_source_block           1b_08S363
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025615