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_4025617
_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         'C18 H9 F4 N O2'
_chemical_formula_sum            'C18 H9 F4 N O2'
_chemical_formula_weight         347.26
_chemical_melting_point          422.6(5)
_chemical_name_systematic
;
2,3,4,5-tetrafluoro-6-nitro-[1,1':4',1"-terphenyl]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.398(10)
_cell_angle_beta                 85.577(10)
_cell_angle_gamma                72.896(10)
_cell_formula_units_Z            2
_cell_length_a                   6.2677(3)
_cell_length_b                   9.9095(5)
_cell_length_c                   12.4290(6)
_cell_measurement_reflns_used    6192
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.12
_cell_measurement_theta_min      2.17
_cell_volume                     730.74(7)
_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 Sep 3 2008 19:38:20)
;
_computing_publication_material
;
Olex2, Durham University (compiled Sep 3 2008 19:38:20)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS Spider IP'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18089
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FSProcess (Rigaku Inc., 2007)'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.1300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1882
_reflns_number_gt                2850
_reflns_number_total             4242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100877j_si_004.cif
_cod_data_source_block           9_08SRV380
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '149-150 C' was changed to '422.6(5)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_original_cell_volume        730.74(6)
_cod_database_code               4025617