Radical Carbofluorination of Unactivated Alkenes with Fluoride Ions.
Liu, Zhonglin; Chen, He; Lv, Ying; Tan, Xinqiang; Shen, Haigen; Yu, Hai-Zhu; Li, Chaozhong; Journal of the American Chemical Society 140 (2018) 6169–6175; doi:10.1021/jacs.8b03077

data_4132363
_publ_section_title
;
 Radical Carbofluorination of Unactivated Alkenes with Fluoride Ions.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6169
_journal_page_last               6175
_journal_paper_doi               10.1021/jacs.8b03077
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C14 H12 Cu F2 N2 O4, 2(C H4 O)'
_chemical_formula_sum            'C16 H20 Cu F2 N2 O6'
_chemical_formula_weight         437.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.973(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.509(4)
_cell_length_b                   15.545(7)
_cell_length_c                   13.953(7)
_cell_measurement_reflns_used    1757
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.43
_cell_measurement_theta_min      2.56
_cell_volume                     1791.0(15)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14610
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.680
_diffrn_reflns_theta_min         1.995
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.276
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1006 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.8922.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.1155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2512
_reflns_number_total             4157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b03077_si_002.cif
_cod_data_source_block           mo_dm15811_0m
_cod_original_cell_volume        1791.1(14)
_cod_database_code               4132363
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.741
_shelx_estimated_absorpt_t_min   0.686
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C7(H7), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6)
;
_shelx_res_checksum              76148
_shelx_hkl_checksum              70137
_olex2_submission_special_instructions 'No special instructions were received'