Substitution of a Fluorine Atom in Perfluorobenzonitrile by a Lithiated Nitronyl Nitroxide.
Tretyakov, Evgeny V.; Fedyushin, Pavel A.; Panteleeva, Elena V.; Stass, Dmitri V.; Bagryanskaya, Irina Yu; Beregovaya, Irina V.; Bogomyakov, Artem S.; The Journal of organic chemistry 82 (2017) 4179–4185; doi:10.1021/acs.joc.7b00144

data_4032434
_publ_section_title
;
 Substitution of a Fluorine Atom in Perfluorobenzonitrile by a Lithiated
 Nitronyl Nitroxide.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4179
_journal_page_last               4185
_journal_paper_doi               10.1021/acs.joc.7b00144
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C28 H24 F9 N6 O4'
_chemical_formula_sum            'C28 H24 F9 N6 O4'
_chemical_formula_weight         679.53
_chemical_name_systematic
; 
 4-((di(4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyle-yl)
 (perfluorophenyl)methyl)amino)-2,3,5,6-tetrafluoro-benzonitrile  
;
_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                76.259(2)
_cell_angle_beta                 78.474(2)
_cell_angle_gamma                87.054(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0863(6)
_cell_length_b                   12.4846(7)
_cell_length_c                   13.1297(7)
_cell_measurement_reflns_used    9222
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.79
_cell_measurement_theta_min      3.36
_cell_volume                     1573.62(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28664
_diffrn_reflns_theta_full        25.74
_diffrn_reflns_theta_max         25.74
_diffrn_reflns_theta_min         1.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.8151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             694
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         5991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.235
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1220P)^2^+0.7079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.2495
_reflns_number_gt                4112
_reflns_number_total             5991
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00144_si_002.cif
_cod_data_source_block           5_paf140
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032432--4032434.cif.
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4032434