Tandem Radical Fluoroalkylation-Cyclization: Synthesis of Tetrafluoro Imidazopyridines.
Charpentier, Julie; Früh, Natalja; Foser, Simon; Togni, Antonio; Organic letters 18 (2016) 756–759; doi:10.1021/acs.orglett.6b00018

data_1542343
_publ_section_title
;
 Tandem Radical Fluoroalkylation-Cyclization: Synthesis of Tetrafluoro
 Imidazopyridines.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              756
_journal_page_last               759
_journal_paper_doi               10.1021/acs.orglett.6b00018
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C14 H10 F4 N2'
_chemical_formula_sum            'C14 H10 F4 N2'
_chemical_formula_weight         282.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_measurement_reflns_used    2172
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_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
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_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
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_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_av_unetI/netI     0.1495
_diffrn_reflns_Laue_measured_fraction_full 0.995
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_diffrn_reflns_limit_k_min       -23
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_diffrn_reflns_limit_l_min       -15
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_diffrn_reflns_theta_full        26.000
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_diffrn_reflns_theta_min         2.021
_diffrn_source                   'sealed tube'
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_exptl_crystal_colour            colourless
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_exptl_crystal_description       plate
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1609
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_reflns_number_gt                2115
_reflns_number_total             4791
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_depositor_comments
'Adding full bibliography for 1542341--1542344.cif.'
_cod_database_code               1542343
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C24(H24), C6(H6), C20(H20), C21(H21), C7(H7), C10(H10), C25(H25),
 C27(H27), C28(H28), C26(H26), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              73945
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_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'