Ruthenium-Catalyzed Ortho C-H Arylation of Aromatic Nitriles with Arylboronates and Observation of Partial Para Arylation.
Koseki, Yuta; Kitazawa, Kentaroh; Miyake, Masashi; Kochi, Takuya; Kakiuchi, Fumitoshi; The Journal of organic chemistry  (2016) –; doi:10.1021/acs.joc.6b02623

data_4032082
_publ_section_title
;
 Ruthenium-Catalyzed Ortho C-H Arylation of Aromatic Nitriles with
 Arylboronates and Observation of Partial Para Arylation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.6b02623
_journal_year                    2016
_chemical_formula_sum            'C22 H10 F9 N'
_chemical_formula_weight         459.31
_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'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.526(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6541(6)
_cell_length_b                   28.474(4)
_cell_length_c                   14.0756(17)
_cell_measurement_reflns_used    8471
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.21
_cell_volume                     1864.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1465
_diffrn_reflns_av_sigmaI/netI    0.0888
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22313
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0602P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                1941
_reflns_number_total             3291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02623_si_002.cif
_cod_data_source_block           5ab
_cod_depositor_comments
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The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity' tag as specified in the
replacement file
'/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 4268 2015-11-12 08:31:59Z antanas 
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_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4032082