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_1542344
_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         'C10 H8 F4 N2 O2'
_chemical_formula_sum            'C10 H8 F4 N2 O2'
_chemical_formula_weight         264.18
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_Hall           '-P 4bc'
_space_group_name_H-M_alt        'P 42/n'
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-24
_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_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0066(9)
_cell_length_b                   20.0066(9)
_cell_length_c                   5.3686(3)
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    106(2)
_cell_measurement_theta_max      29.84
_cell_measurement_theta_min      2.87
_cell_volume                     2148.86(18)
_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)'
_diffrn_ambient_temperature      106
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1336
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            42588
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.880
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.217
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_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0705P)^2^+0.4019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1885
_reflns_number_total             2464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00018_si_002.cif
_cod_data_source_block           monoklin
_cod_depositor_comments
'Adding full bibliography for 1542341--1542344.cif.'
_cod_original_cell_volume        2148.9(2)
_cod_database_code               1542344
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              35238
_shelx_hkl_checksum              25703
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'