Direct, Catalytic Monofluorination of sp(3) C-H Bonds: A Radical-Based Mechanism with Ionic Selectivity.
Pitts, Cody Ross; Bloom, Steven; Woltornist, Ryan; Auvenshine, Dillon Jay; Ryzhkov, Lev R.; Siegler, Maxime A.; Lectka, Thomas; Journal of the American Chemical Society 136 (2014) 9780–9791; doi:10.1021/ja505136j

data_4122108
_publ_section_title
;
 Direct, Catalytic Monofluorination of sp(3) C-H Bonds: A Radical-Based
 Mechanism with Ionic Selectivity.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9780
_journal_page_last               9791
_journal_paper_doi               10.1021/ja505136j
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C8 H6 Cl2 Cu I N'
_chemical_formula_sum            'C8 H6 Cl2 Cu I N'
_chemical_formula_weight         377.48
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.4721(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.25345(18)
_cell_length_b                   7.57776(17)
_cell_length_c                   17.1862(3)
_cell_measurement_reflns_used    6122
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.68
_cell_volume                     1071.60(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9111
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.377
_exptl_absorpt_coefficient_mu    5.368
_exptl_absorpt_correction_T_max  0.772
_exptl_absorpt_correction_T_min  0.420
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.340
_exptl_crystal_description       'irregular shape'
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0167
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0160P)^2^+0.8418P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0389
_refine_ls_wR_factor_ref         0.0398
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2319
_reflns_number_total             2467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja505136j_si_004.cif
_cod_data_source_block           Cu_complex
_cod_depositor_comments          'Adding full bibliography for 4122108.cif.'
_cod_database_code               4122108
_shelxl_version_number           2013-2
_shelx_res_checksum              21220
_shelx_hkl_checksum              76182