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_4025619
_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         'C12 H6 F3 N O2'
_chemical_formula_sum            'C12 H6 F3 N O2'
_chemical_formula_weight         253.18
_chemical_melting_point          378.1(10)
_chemical_name_systematic        2,3,4-trifluoro-6-nitrobiphenyl
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.89(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5365(7)
_cell_length_b                   7.5063(4)
_cell_length_c                   11.0598(6)
_cell_measurement_reflns_used    4612
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.439
_cell_measurement_theta_min      2.713
_cell_volume                     1030.90(11)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
Olex2, Durham University (compiled Jan 16 2009 19:16:02)
;
_computing_publication_material
;
Olex2, Durham University (compiled Jan 16 2009 19:16:02)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10164
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.64
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.4884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2006/1 (Bruker,2006) was used for absorption correction.
 R(int) was 0.0728 before and 0.0180 after correction.
 The Ratio of minimum to maximum transmission is 0.503349479542.
 The \l/2 correction factor is 0.0015
;
_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    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0600P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2282
_reflns_number_total             2740
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100877j_si_006.cif
_cod_data_source_block           15_09srv036_SAD
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '104-106 C' was changed to
'378.1(10)' - 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 '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_original_cell_volume        1030.90(10)
_cod_database_code               4025619