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_4130825
_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         'C30 H38 Fe N6 O4, 2(B F4), C2 H3 N'
_chemical_formula_sum            'C32 H41 B2 F8 Fe N7 O4'
_chemical_formula_weight         817.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-12
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.8624(11)
_cell_length_b                   18.8653(13)
_cell_length_c                   22.9188(16)
_cell_measurement_reflns_used    9596
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31.073
_cell_measurement_theta_min      2.335
_cell_volume                     7290.8(9)
_computing_cell_refinement       'SAINT v8.32B (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0361
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            96694
_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         31.087
_diffrn_reflns_theta_min         1.848
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0644 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.9191.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       prism
_exptl_crystal_F_000             3376
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by solvent layering'
_exptl_crystal_size_max          0.557
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.309
_refine_diff_density_max         1.456
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         11698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0731P)^2^+4.3297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9719
_reflns_number_total             11698
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07221_si_003.cif
_cod_data_source_block           fe2f2_1
_cod_database_code               4130825
_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 Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C17(H17A,H17B), C2(H2A,H2B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C29(H29), C14(H14), C28(H28), C30(H30), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C),
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C20(H20A,H20B,H20C), C12(H12A,H12B,
 H12C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              37772
_shelx_hkl_checksum              17498
_shelx_shelxl_version_number     2014/7
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'