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_4134782
_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 Br Cu N3 O2, 2(C4 H10 O)'
_chemical_formula_sum            'C39 H57 Br Cu N3 O4'
_chemical_formula_weight         775.32
_chemical_name_common            PDACuBr
_chemical_name_systematic
;       
 [N,N'-Bis(2,6-diisopropylphenyl)-2,6-pyridinedicarboxamido]
 copper bromide diethyl ether solvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.521(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5193(18)
_cell_length_b                   13.3270(13)
_cell_length_c                   15.3535(14)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.393
_cell_measurement_theta_min      2.329
_cell_volume                     3981.5(6)
_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      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa APEX II'
_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  0.0293
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33300
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.393
_diffrn_reflns_theta_min         1.852
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.593
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;   
 SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
 wR2(int) was 0.0717 before and 0.0411 after correction.
 The Ratio of minimum to maximum transmission is 0.7431.
 The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       needle
_exptl_crystal_F_000             1632
_exptl_crystal_recrystallization_method
'Grown from a concentrated solution of diethyl ether at -35 degrees C'
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.262
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0244
_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^)+(0.0339P)^2^+4.9144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3654
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02583_si_007.cif
_cod_data_source_block           pdacubr
_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               4134782
_shelx_shelxl_version_number     2018/1
_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:
 C14(H14), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C1A(H1AA,H1AB)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C8(H8), C7(H7)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C12(H12A,H12B,H12C), C4A(H4AA,H4AB,H4AC), C15(H15A,H15B,
 H15C), C13(H13A,H13B,H13C), C2A(H2AA,H2AB,H2AC)
;
_shelx_res_checksum              60336
_shelx_hkl_checksum              82435
_olex2_exptl_crystal_mounting_method
'Mounted on a MiTeGen mount with Paratone oil'
_olex2_submission_original_sample_id PDACuBr
_olex2_submission_special_instructions 'No special instructions were received'