Iron(II)-Catalyzed Intramolecular Olefin Aminofluorination.
Lu, Deng-Fu; Liu, Guan-Sai; Zhu, Cheng-Liang; Yuan, Bo; Xu, Hao; Organic letters 16 (2014) 2912–2915; doi:10.1021/ol501051p

data_1516113
_publ_section_title
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 Iron(II)-Catalyzed Intramolecular Olefin Aminofluorination.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2912
_journal_page_last               2915
_journal_paper_doi               10.1021/ol501051p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C11 H12 F N O2'
_chemical_formula_sum            'C11 H12 F N O2'
_chemical_formula_weight         209.22
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-07-03
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.477(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.272(2)
_cell_length_b                   5.8049(10)
_cell_length_c                   16.158(3)
_cell_measurement_reflns_used    4721
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.055
_cell_measurement_theta_min      2.646
_cell_volume                     1002.8(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 v2011.2-4 (Bruker, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX2 detector'
_diffrn_measurement_method       '\f and \w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8274
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.112
_diffrn_reflns_theta_min         1.947
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0917 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.8720.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.806
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0816P)^2^+0.1012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2397
_reflns_number_total             3131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501051p_si_002.cif
_cod_data_source_block           gsl
_cod_depositor_comments          'Adding full bibliography for 1516113.cif.'
_cod_database_code               1516113
_olex2_refinement_description
;
1. Restrained distances
 N1-H1
 0.98 with sigma of 0.01
 C5-H5C
 0.995 with sigma of 0.01
 C7-H7 = C8-H8 = C9-H9
 0.995 with sigma of 0.01
 C1-H1A \\sim C1-H1B
 with sigma of 0.005
 C5-H5B \\sim C5-H5C \\sim C5-H5A
 with sigma of 0.005
 C10-H10 \\sim C11-H11
 with sigma of 0.005
;
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.918
_shelxl_version_number           2013-3