NHC-Copper Mediated Ligand-Directed Radiofluorination of Aryl Halides.
Sharninghausen, Liam S.; Brooks, Allen F.; Winton, Wade P.; Makaravage, Katarina J.; Scott, Peter J. H.; Sanford, Melanie S.; Journal of the American Chemical Society 142 (2020) 7362–7367; doi:10.1021/jacs.0c02637

data_4134668
_publ_section_title
;
 NHC-Copper Mediated Ligand-Directed Radiofluorination of Aryl Halides.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7362
_journal_page_last               7367
_journal_paper_doi               10.1021/jacs.0c02637
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C23 H32 Cu F N2, C H2 Cl2'
_chemical_formula_sum            'C24 H34 Cl2 Cu F N2'
_chemical_formula_weight         503.97
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-21
_audit_creation_method
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                87.075(5)
_cell_angle_beta                 80.401(5)
_cell_angle_gamma                71.730(6)
_cell_formula_units_Z            2
_cell_length_a                   8.4835(6)
_cell_length_b                   11.9653(8)
_cell_length_c                   12.0408(7)
_cell_measurement_reflns_used    10843
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      69.1270
_cell_measurement_theta_min      3.8840
_cell_volume                     1144.37(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -110.00  70.00   1.00    1.00    --  -20.00   0.00-180.00  180
  2  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00   0.00   45
  3  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00   0.00   45
  4  \w    -25.00  43.00   1.00    1.00    --  -20.00  36.00 120.00   68
  5  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00-180.00   45
  6  \w   -173.00-128.00   1.00    6.00    --  -92.00 -36.00 120.00   45
  7  \w   -133.00 -88.00   1.00    6.00    --  -92.00 -36.00 -60.00   45
  8  \w   -104.00 -59.00   1.00    6.00    --  -92.00  36.00  60.00   45
  9  \w   -122.00 -77.00   1.00    6.00    --  -92.00 -72.00  60.00   45
 10  \w   -174.00 -78.00   1.00    6.00    --  -92.00 -72.00-120.00   96
 11  \w    -93.00 -35.00   1.00    6.00    --  -92.00  36.00-120.00   58
 12  \w   -176.00 -77.00   1.00    6.00    --  -92.00 -72.00 -60.00   99
 13  \w   -147.00 -75.00   1.00    6.00    --  -92.00 -72.00-180.00   72
 14  \w   -176.00 -77.00   1.00    6.00    --  -92.00 -72.00 120.00   99
 15  \w   -177.00-116.00   1.00    6.00    --  -92.00 -36.00  60.00   61
 16  \w    -87.00  -9.00   1.00    6.00    --  -92.00  36.00 -60.00   78
 17  \w   -102.00 -14.00   1.00    6.00    --  -92.00  36.00   0.00   88
 18  \w   -102.00 -21.00   1.00    6.00    --  -92.00  72.00 120.00   81
 19  \w   -175.00-104.00   1.00    6.00    --  -92.00 -36.00   0.00   71
 20  \w   -104.00 -52.00   1.00    6.00    --  -92.00  72.00  60.00   52
 21  \w   -109.00 -14.00   1.00    6.00    --  -92.00  72.00-120.00   95
 22  \w   -105.00 -24.00   1.00    6.00    --  -92.00  36.00-120.00   81
 23  \w   -105.00  -2.00   1.00    6.00    --  -92.00  36.00-180.00  103
 24  \w   -106.00  -2.00   1.00    6.00    --  -92.00  72.00 -60.00  104
 25  \w   -106.00  -2.00   1.00    6.00    --  -92.00  72.00 -60.00  104
 26  \w   -107.00 -29.00   1.00    6.00    --  -92.00  72.00   0.00   78
 27  \w   -117.00 -72.00   1.00    6.00    --  -92.00  72.00 180.00   45
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1398012000
_diffrn_orient_matrix_UB_12      0.0530631000
_diffrn_orient_matrix_UB_13      0.0993646000
_diffrn_orient_matrix_UB_21      -0.0712125000
_diffrn_orient_matrix_UB_22      0.1084558000
_diffrn_orient_matrix_UB_23      -0.0722030000
_diffrn_orient_matrix_UB_31      -0.1135931000
_diffrn_orient_matrix_UB_32      -0.0616905000
_diffrn_orient_matrix_UB_33      -0.0418506000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17545
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.355
_diffrn_reflns_theta_min         3.723
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0520P)^2^+1.3050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3872
_reflns_number_total             4140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02637_si_003.cif
_cod_data_source_block           ls2ad
_cod_depositor_comments
'Adding full bibliography for 4134667--4134668.cif.'
_cod_original_cell_volume        1144.37(13)
_cod_database_code               4134668
_chemical_oxdiff_formula         C23H32N2CuF
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.758
_reflns_odcompleteness_completeness 96.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.23
_shelx_res_checksum              2203
_shelx_hkl_checksum              37126
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.841
_oxdiff_exptl_absorpt_empirical_full_min 0.585