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_4032433
_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         'C14 H12 F4 N3 O'
_chemical_formula_sum            'C14 H12 F4 N3 O'
_chemical_formula_weight         314.27
_chemical_melting_point          404
_chemical_name_systematic
; 
 4-(4,4,5,5-Tetramethyl-1-oxyl-4,5-dihydro-1H-imidazol-2-yl)-
 2,3,5,6-tetrafluorobenzonitrile 
;
_space_group_IT_number           73
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-I 2b 2c'
_symmetry_space_group_name_H-M   'I b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.3528(3)
_cell_length_b                   10.8047(3)
_cell_length_c                   26.1688(6)
_cell_measurement_reflns_used    6741
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.96
_cell_measurement_theta_min      3.11
_cell_volume                     2927.21(14)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            16298
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         1.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.020(2)
_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   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1452
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0975P)^2^+0.7773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1687
_reflns_number_gt                1167
_reflns_number_total             1452
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00144_si_002.cif
_cod_data_source_block           4_paf103
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      'Ibca '
_cod_database_code               4032433