Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines.
Lu, Deng-Fu; Zhu, Cheng-Liang; Jia, Zhen-Xin; Xu, Hao; Journal of the American Chemical Society 136 (2014) 13186–13189; doi:10.1021/ja508057u

data_4122620
_publ_section_title
;
 Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through
 the N-O bond cleavage of functionalized hydroxylamines.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13186
_journal_page_last               13189
_journal_paper_doi               10.1021/ja508057u
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C14 H12 Cl2 F3 N O5'
_chemical_formula_sum            'C14 H12 Cl2 F3 N O5'
_chemical_formula_weight         402.15
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-03-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796)
;
_cell_angle_alpha                99.955(2)
_cell_angle_beta                 96.953(2)
_cell_angle_gamma                90.633(2)
_cell_formula_units_Z            2
_cell_length_a                   4.8784(8)
_cell_length_b                   10.6424(17)
_cell_length_c                   15.881(3)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31.003
_cell_measurement_theta_min      2.529
_cell_volume                     805.7(2)
_computing_cell_refinement       'SAINT v8.34A (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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14822
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.011
_diffrn_reflns_theta_min         1.944
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.8391.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.985
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.53(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         9669
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0668P)^2^+0.0680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                8620
_reflns_number_total             9669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja508057u_si_002.cif
_cod_data_source_block           a008_0m
_cod_depositor_comments          'Adding full bibliography for 4122620.cif.'
_cod_database_code               4122620
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N1'(H1'), N1(H1)
2.b Ternary CH refined with riding coordinates:
 C8'(H8'), C11'(H11'), C11(H11), C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C10'(H10A,H10B), C13'(H13A,H13B), C9'(H9'A,H9'B), C10(H10C,H10D), C13(H13C,
 H13D), C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 C5'(H5'), C2'(H2'), C4'(H4'), C2(H2), C5(H5), C4(H4)
;
_olex2_computing_structure_refinement_long 'SHELXL-97 (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'