C(sp<sup>3</sup>)-H Fluorination with a Copper(II)/(III) Redox Couple.
Bower, Jamey K.; Cypcar, Andrew D.; Henriquez, Brenda; Stieber, S Chantal E; Zhang, Shiyu; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02583

data_4134779
_publ_section_title
;
 C(sp<sup>3</sup>)-H Fluorination with a Copper(II)/(III) Redox Couple.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02583
_journal_year                    2020
_chemical_formula_moiety         'C31 H37 Cu F N3 O2, 2(C6 H5 F)'
_chemical_formula_sum            'C43 H47 Cu F3 N3 O2'
_chemical_formula_weight         758.37
_chemical_name_systematic
;
['N,N'-Bis(2,6-diisopropylphenyl)-2,6-pyridinedicarboxamido]
copper fluoride fluorobenzene solvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-02-06
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.531(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1436(9)
_cell_length_b                   13.9372(13)
_cell_length_c                   15.6750(13)
_cell_measurement_reflns_used    4409
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.664
_cell_measurement_theta_min      2.998
_cell_volume                     1980.3(3)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_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      150.0
_diffrn_detector                 'Bruker Photon II area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Curved-Graphite, Bruker TRIUMPH'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7257
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.428
_diffrn_reflns_theta_min         3.002
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.258980
_exptl_absorpt_correction_T_min  0.223647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 43052 reflections, Rint = 0.0643
 (17922 with I > 3sig(I), Rint = 0.0382)
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             796
_exptl_crystal_recrystallization_method
'Grown from a dilute solution of fluorobenzene and pentane at -35 degrees C.'
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         7257
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0470P)^2^+0.2856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5861
_reflns_number_total             7257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02583_si_005.cif
_cod_data_source_block           pdacuf
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4134779
_shelx_shelxl_version_number     2018/1
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5889(14)
 0.4111(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 1*[Sof(F2B)+Sof(H3B)]+1*[Sof(F1B)+Sof(H1B)]=0.5 with esd of 0
 Sof(H3B)=1-FVAR(1)
 Sof(F2B)=FVAR(1)
 Sof(H1B)=1-FVAR(2)
 Sof(F1B)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C11(H11), C19(H19)
4.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C2(H2), C3(H3), C17(H17), C18(H18), C9(H9), C6A(H6A),
 C5A(H5A), C4A(H4A), C2A(H2A), C3A(H3A), C3B(H3B), C2B(H2B), C1B(H1B)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C20(H20A,H20B,
 H20C)
;
_shelx_res_checksum              81859
_shelx_hkl_checksum              54526
_olex2_exptl_crystal_mounting_method
'Mounted on a MiTeGen mount with Paratone oil'
_olex2_submission_original_sample_id PDACuF
_olex2_submission_special_instructions 'No special instructions were received'