A Fluorine 1,2-Migration via Aryl Cation/Radical/Radical Anion/Radical Sequence.
Pretali, Luca; Dondi, Daniele; D'Angelantonio, Mila; Manet, Ilse; Fasani, Elisa; Monti, Sandra; Bovio, Bruna; Albini, Angelo; Organic letters 15 (2013) 3926–3929; doi:10.1021/ol401670p

data_1512202
_publ_contact_author
;
  Angelo Albini
  Dipartimento di Chimica
  University of Pavia
  via Taramelli 12, I-27100 Pavia, ITALY
;
_publ_section_title
;
 A Fluorine 1,2-Migration via Aryl Cation/Radical/Radical Anion/Radical
 Sequence.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3926
_journal_page_last               3929
_journal_paper_doi               10.1021/ol401670p
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C13 H11 F I N O3 '
_chemical_formula_sum            'C13 H11 F I N O3'
_chemical_formula_weight         375.13
_chemical_name_systematic
;
Methyl-7-fluoro-1,4-dihydro-1-(2-iodoethyl)-4-oxoquinoline-3-carboxylate 
;
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0
_cell_angle_beta                 96.68(1)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   8.665(1)
_cell_length_b                   6.883(4)
_cell_length_c                   21.851(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     1294.4(8)
_computing_cell_refinement       'CAD4 (Enraf Nonius, 1992)'
_computing_data_collection       'CAD4 (Enraf Nonius, 1992)'
_computing_data_reduction        'CAD4 (Enraf Nonius, 1992)'
_computing_molecular_graphics    'Ortep, (Johnson, 1965)'
_computing_publication_material  Geom
_computing_structure_refinement  'Shelxl-93 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxl-93 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Enraf Nonius CAD4'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710738
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  240
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.4900
_exptl_absorpt_correction_T_max  0.8812
_exptl_absorpt_correction_T_min  0.6102
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.184
_refine_diff_density_min         -1.484
_refine_diff_density_rms         0.183
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_reflns_number_gt                1900
_reflns_number_observed          2258
_reflns_number_total             2278
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401670p_si_002.cif
_cod_data_source_block           Compound_7a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'Difmap' changed to 'difmap'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_atom_sites_solution_secondary' value 'Difmap' changed
to 'difmap' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_matrix_type' value 'Full' changed to 'full'
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 21/n'
_cod_database_code               1512202
_refine_ls_r1_factor_all_obs     0.0495
_refine_ls_r1_factor_gt          0.0390
_refine_ls_wr2_factor_all_refl   0.1075