Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles.
Peshkov, Roman Yu; Wang, Chunyan; Panteleeva, Elena V.; Rybalova, Tatyana V.; Tretyakov, Evgeny V.; The Journal of organic chemistry 84 (2019) 963–972; doi:10.1021/acs.joc.8b02904

data_4035973
_publ_section_title
;
 Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of
 Fluorinated Benzonitriles.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              963
_journal_page_last               972
_journal_paper_doi               10.1021/acs.joc.8b02904
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H10 F N3'
_chemical_formula_sum            'C14 H10 F N3'
_chemical_formula_weight         239.25
_chemical_name_systematic
; 
 4-amino-2-phenyl-5-fluoroquinazoline 
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 90.007(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8638(3)
_cell_length_b                   12.3396(9)
_cell_length_c                   23.9712(19)
_cell_measurement_reflns_used    5396
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.83
_cell_measurement_theta_min      2.37
_cell_volume                     1142.89(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16923
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         0.85
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.8117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0904P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                3164
_reflns_number_total             4167
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02904_si_002.cif
_cod_data_source_block           rup170_10i
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               4035973