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_4134780
_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 Cl Cu N3 O2, 2(C4 H10 O)'
_chemical_formula_sum            'C39 H57 Cl Cu N3 O4'
_chemical_formula_weight         730.86
_chemical_name_systematic
; 
 [N,N'-Bis(2,6-diisopropylphenyl)-2,6-pyridinedicarboxamido] 
 copper chloride 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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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                 95.551(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3809(9)
_cell_length_b                   13.1487(6)
_cell_length_c                   15.3938(7)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.060
_cell_measurement_theta_min      2.238
_cell_volume                     3904.5(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      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  0.0466
_diffrn_reflns_av_unetI/netI     0.0200
_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            64529
_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         26.502
_diffrn_reflns_theta_min         1.874
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
 wR2(int) was 0.0564 before and 0.0524 after correction. 
 The Ratio of minimum to maximum transmission is 0.8701. 
 The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             1560
_exptl_crystal_recrystallization_method
'Grown from a concentrated diethyl ether solution at -35 degrees C.'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4051
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0466P)^2^+6.9095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3512
_reflns_number_total             4051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02583_si_006.cif
_cod_data_source_block           pdacucl
_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               4134780
_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. Rigid body (RIGU) restrains
 C2B, O1B, C1B, C3B, C4B, C1A, C2A, O1A, C3A, C4A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Sof(C1A)=Sof(H1Aa)=Sof(H1Ab)=Sof(C2A)=Sof(H2Aa)=Sof(H2Ab)=Sof(H2Ac)=Sof(O1A)=
 Sof(C3A)=Sof(H3Aa)=Sof(H3Ab)=Sof(C4A)=Sof(H4Aa)=Sof(H4Ab)=Sof(H4Ac)=1-FVAR(1)
 Sof(O1B)=Sof(C4B)=Sof(H4Ba)=Sof(H4Bb)=Sof(H4Bc)=Sof(C1B)=Sof(H1Ba)=Sof(H1Bb)=
 Sof(C3B)=Sof(H3Ba)=Sof(H3Bb)=Sof(C2B)=Sof(H2Ba)=Sof(H2Bb)=Sof(H2Bc)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C1B(H1Ba,H1Bb), C3B(H3Ba,H3Bb), C1A(H1Aa,H1Ab), C3A(H3Aa,H3Ab)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C7(H7), C8(H8), C9(H9)
4.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C13(H13a,H13b,H13c), C4B(H4Ba,H4Bb,H4Bc), C15(H15a,H15b,
 H15c), C12(H12a,H12b,H12c), C2B(H2Ba,H2Bb,H2Bc), C2A(H2Aa,H2Ab,H2Ac), C4A(H4Aa,
 H4Ab,H4Ac)
;
_shelx_res_checksum              51024
_shelx_hkl_checksum              84274
_olex2_exptl_crystal_mounting_method
'Mounted on a MiTeGen mount with Paratone oil'
_olex2_submission_original_sample_id PDACuCl
_olex2_submission_special_instructions 'No special instructions were received'