Palladium-Catalyzed Coupling of Polyfluorinated Arenes with Heteroarenes via C-F/C-H Activation.
Yu, Daohong; Lu, Long; Shen, Qilong; Organic letters 15 (2013) 940–943; doi:10.1021/ol303567t

data_1508952
_publ_section_title
;
 Palladium-Catalyzed Coupling of Polyfluorinated Arenes with Heteroarenes
 via C-F/C-H Activation.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              940
_journal_page_last               943
_journal_paper_doi               10.1021/ol303567t
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C18 H10 F2 N2 O'
_chemical_formula_weight         308.28
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.883(2)
_cell_angle_beta                 105.781(2)
_cell_angle_gamma                98.414(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9035(6)
_cell_length_b                   9.5259(8)
_cell_length_c                   10.3445(8)
_cell_measurement_reflns_used    2529
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.372
_cell_measurement_theta_min      4.522
_cell_volume                     708.66(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4316
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62003
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.124(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0636P)^2^+0.0891P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                2439
_reflns_number_total             2779
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303567t_si_004.cif
_cod_data_source_block           cd212257
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1508952