Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.
Lu, Deng-Fu; Zhu, Cheng-Liang; Sears, Jeffrey D.; Xu, Hao; Journal of the American Chemical Society 138 (2016) 11360–11367; doi:10.1021/jacs.6b07221

data_4130823
_publ_section_title
;
 Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized
 Olefins Using Fluoride Ion.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11360
_journal_page_last               11367
_journal_paper_doi               10.1021/jacs.6b07221
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C14 H18 F7 N O2'
_chemical_formula_sum            'C14 H18 F7 N O2'
_chemical_formula_weight         365.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-10-01
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5097)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.507(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.135(6)
_cell_length_b                   12.502(6)
_cell_length_c                   9.632(4)
_cell_measurement_reflns_used    9320
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.646
_cell_measurement_theta_min      2.191
_cell_volume                     1673.6(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0547
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20500
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.572
_diffrn_reflns_theta_min         2.191
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1750 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.6917.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.898
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4679
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0780P)^2^+1.0555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3019
_reflns_number_total             4679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07221_si_005.cif
_cod_data_source_block           af-beta-af2
_cod_original_cell_volume        1673.8(13)
_cod_database_code               4130823
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.879
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 C6-H6B
 0.999 with sigma of 0.02
 C5-H5
 0.995 with sigma of 0.02
 C10-H10
 0.999 with sigma of 0.02
 N1-H1
 0.995 with sigma of 0.02
 C6-H6A \\sim C6-H6B
 with sigma of 0.005
 C14-H14A \\sim C14-H14C \\sim C14-H14B
 with sigma of 0.003
 H14C-H14A \\sim H14C-H14B \\sim H14B-H14A
 with sigma of 0.006
 C13-H13A \\sim C13-H13B \\sim C13-H13C
 with sigma of 0.003
 H13C-H13B \\sim H13C-H13A \\sim H13B-H13A
 with sigma of 0.006
3. Uiso/Uaniso restraints and constraints
Uiso(H6A) = Uiso(H6B)
Uiso(H14C) = Uiso(H14B) = Uiso(H14A)
Uiso(H13C) = Uiso(H13B) = Uiso(H13A)
4. Rigid body (RIGU) restrains
 C1, C2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C1, C6
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C1, C7
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C7, C14
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C7, C13
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C5, C4, C8, C3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C3, C2, C1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C8, N1, C9
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C9, O2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C9, O1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O1, C10
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C10, C11, C12
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C12, F7
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 F4, C11
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C11, F3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C11, F2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C3(H3A,H3B), C2(H2A,H2B)
;
_shelx_res_checksum              52796
_shelx_hkl_checksum              79680
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id zhu-AF-beta-mestyrene_AF2
_olex2_submission_special_instructions 'No special instructions were received'